data_global #============================================================================== # 1. SUBMISSION DETAILS #============================================================================== _publ_contact_author_name 'Denis Spasyuk' _publ_contact_author_address ; Universit\'e de Montr\'eal D\'epartement de Chimie C.P. 6128, Succ. Centre-ville Montr\'eal, Qu\'ebec Canada, H3C 3J7 ; _publ_contact_author_phone '+1 514 343 6111 3936' _publ_contact_author_fax '+1 514 343 7586' _publ_contact_author_email 'denis.spasyuk@umontreal.ca' #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) #============================================================================== _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST #============================================================================== _publ_section_title ; Structures of Ni(-iPrPOCsp2NRNi)Br ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Spasyuk, Denis' ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville, Montr\'eal, Qu\'ebec Canada H3C 3J7 ; 'Zargarian, Davit' ; D\'epartement de Chimie Universit\'e de Montr\'eal C.P. 6128, Succ. Centre-ville, Montr\'eal, Qu\'ebec Canada H3C 3J7 ; #============================================================================== # 4. TEXT #============================================================================== _publ_section_abstract ; Here should be written a short abstract ; _publ_section_comment ; Here should be written the text of the article ; _publ_section_exptl_prep ; Small details about the preparation of the compound. ; _publ_section_exptl_refinement ; All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters. The H atoms were generated geometrically (C-H 0.93 to 0.98, N-H 0.86 and O-H 0.82\%A) and were included in the refinement in the riding model approximation; their temperature factors were set to 1.5 times those of the equivalent isotropic temperature factors of the parent site (methyl) and 1.2 times for others. A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 2000). ; _publ_section_figure_captions ; Fig 1 Ortep view of the title compound. Thermal ellipsoids are shown at 30% probability levels. ; _publ_section_table_legends ; Table 1. Selected geometric parameters (\%A, \%) for the title compound. ; _publ_section_references ; Bruker (1997). SHELXTL (1997). Release 5.10; The Complete Software Package for Single Crystal Structure Determination. Bruker AXS Inc., Madison, USA. Bruker (1999a). SAINT Release 6.06. Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, USA. Bruker (1999b). SMART Release 5.059; Bruker Molecular Analysis Research Tool, Bruker AXS Inc., Madison, USA. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Flack, H. D. and Schwarzenbach, D. (1988). Acta Cryst. A44, 499-506. Sheldrick, G. M. (1986). SHELXS86. Program for Crystal Structure solution. University of G\"ottingen, Germany. Sheldrick, G. M. (1996). SADABS, Bruker Area Detector Absorption Corrections. Bruker AXS Inc., Madison, USA. Sheldrick, G. M. (1997a). SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany. Sheldrick, G. M. (1997b). SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. Spek, A. L. (2000). PLATON, 2000 version; Molecular Geometry Program, University of Utrecht, Utrecht, Holland. ; _publ_section_acknowledgements ; We are grateful to the Natural Sciences and Engineering Research Council of Canada and the Minist\`ere de l'Education du Qu\'ebec for financial support. ; data_61 _vrf_PLAT029_dens31 ; PROBLEM: PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.89 RESPONSE: Due to geometrical constraints of the instrument and the use of copper radiation, we obtain consistently a data completeness lower than 100% in dependence of the crystal system and the orientation of the mounted crystal, even with appropriate data collection routines. Typical values for data completeness range from 83-92% for triclinic, 85-97% for monoclinic and 85-98% for all other crystal systems. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H25 Br N Ni O P, 0.5(C6 H6)' _chemical_formula_sum 'C22 H28 Br N Ni O P' _chemical_formula_weight 492.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Triclinic' _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9115(2) _cell_length_b 10.2997(3) _cell_length_c 12.6496(3) _cell_angle_alpha 90.7330(10) _cell_angle_beta 98.8630(10) _cell_angle_gamma 110.6710(10) _cell_volume 1070.50(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9887 _cell_measurement_theta_min 7.092 _cell_measurement_theta_max 120.100 _exptl_crystal_description 'Block' _exptl_crystal_colour 'Yellow' _exptl_crystal_size_max 0.080 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas 'not mesured' _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 4.281 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6821 _exptl_absorpt_correction_T_max 0.8724 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker microstar diffractometer equiped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over three different parts of the reciprocal space (99 frames total). Due to geometrical constraints of the instrument and the use of copper radiation, we obtain consistently a data completeness lower than 100% in dependence of the crystal system and the orientation of the mounted crystal, even with appropriate data collection routines. Typical values for data completeness range from 83-92% for triclinic, 85-97% for monoclinic and 85-98% for all other crystal systems. ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 16909 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 60.48 _reflns_number_total 2875 _reflns_number_gt 2838 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Platon Ortep' _computing_publication_material 'LinXTL v. 1.09' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.7112P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2875 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0777 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.43774(4) 0.64349(4) 0.32438(3) 0.01880(14) Uani 1 1 d . . . Br1 Br 0.50373(3) 0.44316(2) 0.305614(18) 0.02540(13) Uani 1 1 d . . . P1 P 0.54351(7) 0.74085(6) 0.19474(4) 0.01996(17) Uani 1 1 d . . . O1 O 0.5407(2) 0.90044(17) 0.19705(13) 0.0247(4) Uani 1 1 d . . . N1 N 0.3027(2) 0.5828(2) 0.44088(16) 0.0199(4) Uani 1 1 d . . . H1 H 0.363(3) 0.558(3) 0.497(2) 0.014(6) Uiso 1 1 d . . . C1 C 0.4001(3) 0.8078(2) 0.33938(18) 0.0197(5) Uani 1 1 d . . . C2 C 0.4572(3) 0.9206(3) 0.27718(18) 0.0213(5) Uani 1 1 d . . . C3 C 0.4358(3) 1.0443(2) 0.29294(19) 0.0234(6) Uani 1 1 d . . . H3 H 0.4766 1.1192 0.2495 0.028 Uiso 1 1 calc R . . C4 C 0.3524(3) 1.0567(3) 0.3746(2) 0.0264(6) Uani 1 1 d . . . H4 H 0.3367 1.1416 0.3875 0.032 Uiso 1 1 calc R . . C5 C 0.2917(3) 0.9468(3) 0.43761(19) 0.0239(6) Uani 1 1 d . . . H5 H 0.2344 0.9567 0.4928 0.029 Uiso 1 1 calc R . . C6 C 0.3149(3) 0.8223(2) 0.41967(18) 0.0205(5) Uani 1 1 d . . . C7 C 0.2615(3) 0.6995(3) 0.48606(19) 0.0233(5) Uani 1 1 d . . . H7A H 0.1427 0.6690 0.4850 0.028 Uiso 1 1 calc R . . H7B H 0.3173 0.7259 0.5613 0.028 Uiso 1 1 calc R . . C20 C 0.4241(3) 0.6620(3) 0.06376(18) 0.0252(6) Uani 1 1 d . . . H20 H 0.4459 0.5753 0.0488 0.030 Uiso 1 1 calc R . . C21 C 0.2416(3) 0.6191(3) 0.0675(2) 0.0324(6) Uani 1 1 d . . . H21A H 0.2184 0.7005 0.0899 0.049 Uiso 1 1 calc R . . H21B H 0.2111 0.5477 0.1187 0.049 Uiso 1 1 calc R . . H21C H 0.1789 0.5817 -0.0040 0.049 Uiso 1 1 calc R . . C22 C 0.4731(3) 0.7564(3) -0.0268(2) 0.0399(7) Uani 1 1 d . . . H22A H 0.4151 0.7059 -0.0959 0.060 Uiso 1 1 calc R . . H22B H 0.5907 0.7847 -0.0251 0.060 Uiso 1 1 calc R . . H22C H 0.4449 0.8391 -0.0176 0.060 Uiso 1 1 calc R . . C23 C 0.7573(3) 0.7794(3) 0.18508(19) 0.0246(6) Uani 1 1 d . . . H23 H 0.7919 0.8608 0.1404 0.029 Uiso 1 1 calc R . . C24 C 0.8596(3) 0.8225(3) 0.2976(2) 0.0367(7) Uani 1 1 d . . . H24A H 0.8427 0.7403 0.3391 0.055 Uiso 1 1 calc R . . H24B H 0.8266 0.8901 0.3339 0.055 Uiso 1 1 calc R . . H24C H 0.9750 0.8647 0.2917 0.055 Uiso 1 1 calc R . . C25 C 0.7888(3) 0.6594(3) 0.1323(2) 0.0336(6) Uani 1 1 d . . . H25A H 0.9063 0.6823 0.1375 0.050 Uiso 1 1 calc R . . H25B H 0.7376 0.6442 0.0566 0.050 Uiso 1 1 calc R . . H25C H 0.7426 0.5747 0.1689 0.050 Uiso 1 1 calc R . . C30 C 0.1637(3) 0.4607(3) 0.39660(18) 0.0205(5) Uani 1 1 d . . . C31 C 0.0388(3) 0.4741(3) 0.32216(19) 0.0275(6) Uani 1 1 d . . . H31 H 0.0403 0.5635 0.3034 0.033 Uiso 1 1 calc R . . C32 C -0.0884(3) 0.3546(3) 0.2755(2) 0.0328(7) Uani 1 1 d . . . H32 H -0.1741 0.3630 0.2246 0.039 Uiso 1 1 calc R . . C33 C -0.0917(3) 0.2243(3) 0.3023(2) 0.0336(7) Uani 1 1 d . . . H33 H -0.1782 0.1434 0.2691 0.040 Uiso 1 1 calc R . . C34 C 0.0321(3) 0.2123(3) 0.3777(2) 0.0306(6) Uani 1 1 d . . . H34 H 0.0303 0.1230 0.3970 0.037 Uiso 1 1 calc R . . C35 C 0.1587(3) 0.3310(3) 0.4252(2) 0.0252(6) Uani 1 1 d . . . H35 H 0.2425 0.3226 0.4778 0.030 Uiso 1 1 calc R . . C40 C -0.0358(3) 0.1105(3) 0.0372(2) 0.0373(7) Uani 1 1 d . . . H40 H -0.0605 0.1866 0.0625 0.045 Uiso 1 1 calc R . . C41 C 0.0882(3) 0.0759(3) 0.0947(2) 0.0357(7) Uani 1 1 d . . . H41 H 0.1485 0.1278 0.1598 0.043 Uiso 1 1 calc R . . C42 C 0.1237(3) -0.0338(3) 0.0572(2) 0.0373(7) Uani 1 1 d . . . H42 H 0.2092 -0.0573 0.0964 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0210(2) 0.0164(2) 0.0197(2) 0.00185(17) 0.00516(16) 0.00686(17) Br1 0.03094(17) 0.02101(19) 0.02929(17) 0.00481(12) 0.01062(11) 0.01312(12) P1 0.0217(3) 0.0182(3) 0.0195(3) 0.0009(2) 0.0043(2) 0.0063(2) O1 0.0341(9) 0.0198(9) 0.0235(8) 0.0047(7) 0.0097(7) 0.0117(7) N1 0.0211(10) 0.0193(11) 0.0205(10) 0.0026(8) 0.0033(8) 0.0088(9) C1 0.0204(11) 0.0167(13) 0.0212(11) -0.0007(10) 0.0007(9) 0.0068(10) C2 0.0209(11) 0.0223(13) 0.0195(11) -0.0007(10) 0.0003(9) 0.0075(10) C3 0.0250(11) 0.0163(14) 0.0276(12) 0.0021(10) -0.0008(10) 0.0080(10) C4 0.0231(12) 0.0220(14) 0.0336(13) -0.0036(11) -0.0002(10) 0.0097(10) C5 0.0190(11) 0.0239(14) 0.0288(12) -0.0030(11) 0.0032(9) 0.0082(10) C6 0.0171(11) 0.0194(13) 0.0229(11) -0.0021(10) -0.0009(9) 0.0059(9) C7 0.0247(12) 0.0206(13) 0.0256(12) -0.0015(10) 0.0078(9) 0.0080(10) C20 0.0236(12) 0.0267(14) 0.0240(12) -0.0024(10) 0.0033(9) 0.0079(10) C21 0.0242(13) 0.0390(17) 0.0304(13) -0.0014(12) 0.0007(10) 0.0088(12) C22 0.0377(15) 0.0488(19) 0.0231(13) 0.0028(12) 0.0033(11) 0.0040(13) C23 0.0205(11) 0.0248(14) 0.0269(12) 0.0037(10) 0.0048(9) 0.0059(10) C24 0.0260(13) 0.0412(17) 0.0339(14) 0.0010(12) -0.0013(11) 0.0037(12) C25 0.0277(13) 0.0318(15) 0.0439(15) 0.0036(13) 0.0139(11) 0.0105(11) C30 0.0190(11) 0.0225(14) 0.0205(11) 0.0004(10) 0.0077(9) 0.0063(10) C31 0.0278(12) 0.0274(14) 0.0272(12) 0.0049(11) 0.0054(10) 0.0095(11) C32 0.0246(13) 0.0417(19) 0.0274(13) -0.0010(12) 0.0001(10) 0.0079(12) C33 0.0258(13) 0.0321(17) 0.0368(14) -0.0109(12) 0.0097(11) 0.0015(11) C34 0.0292(13) 0.0194(14) 0.0455(15) 0.0000(12) 0.0158(12) 0.0077(11) C35 0.0235(12) 0.0238(15) 0.0302(13) 0.0033(11) 0.0086(10) 0.0092(10) C40 0.0408(15) 0.0371(17) 0.0350(14) 0.0061(13) 0.0097(12) 0.0135(13) C41 0.0334(14) 0.0387(17) 0.0290(13) 0.0041(12) 0.0037(11) 0.0062(12) C42 0.0309(14) 0.0443(18) 0.0347(14) 0.0102(13) 0.0022(11) 0.0123(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 C1 1.851(3) . ? Ni1 N1 2.0124(19) . ? Ni1 P1 2.1058(7) . ? Ni1 Br1 2.3552(5) . ? P1 O1 1.6526(19) . ? P1 C23 1.828(2) . ? P1 C20 1.830(2) . ? O1 C2 1.400(3) . ? N1 C30 1.449(3) . ? N1 C7 1.505(3) . ? N1 H1 0.92(3) . ? C1 C6 1.394(3) . ? C1 C2 1.399(3) . ? C2 C3 1.370(4) . ? C3 C4 1.391(3) . ? C3 H3 0.9500 . ? C4 C5 1.390(4) . ? C4 H4 0.9500 . ? C5 C6 1.390(4) . ? C5 H5 0.9500 . ? C6 C7 1.502(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C20 C22 1.527(4) . ? C20 C21 1.536(3) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C25 1.528(4) . ? C23 C24 1.534(3) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C30 C35 1.376(4) . ? C30 C31 1.390(4) . ? C31 C32 1.392(4) . ? C31 H31 0.9500 . ? C32 C33 1.380(4) . ? C32 H32 0.9500 . ? C33 C34 1.385(4) . ? C33 H33 0.9500 . ? C34 C35 1.388(4) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C40 C41 1.383(4) . ? C40 C42 1.384(4) 2 ? C40 H40 0.9500 . ? C41 C42 1.374(4) . ? C41 H41 0.9500 . ? C42 C40 1.384(4) 2 ? C42 H42 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 N1 84.57(9) . . ? C1 Ni1 P1 81.95(7) . . ? N1 Ni1 P1 165.03(7) . . ? C1 Ni1 Br1 176.26(7) . . ? N1 Ni1 Br1 97.96(6) . . ? P1 Ni1 Br1 95.83(2) . . ? O1 P1 C23 99.64(10) . . ? O1 P1 C20 103.65(11) . . ? C23 P1 C20 107.01(11) . . ? O1 P1 Ni1 107.78(6) . . ? C23 P1 Ni1 123.01(9) . . ? C20 P1 Ni1 113.27(8) . . ? C2 O1 P1 110.46(15) . . ? C30 N1 C7 114.95(18) . . ? C30 N1 Ni1 106.75(13) . . ? C7 N1 Ni1 111.99(15) . . ? C30 N1 H1 108.7(16) . . ? C7 N1 H1 105.5(15) . . ? Ni1 N1 H1 108.7(14) . . ? C6 C1 C2 117.9(2) . . ? C6 C1 Ni1 118.30(18) . . ? C2 C1 Ni1 123.73(18) . . ? C3 C2 C1 123.1(2) . . ? C3 C2 O1 121.2(2) . . ? C1 C2 O1 115.7(2) . . ? C2 C3 C4 117.8(2) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C5 C4 C3 121.1(2) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.8(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 120.2(2) . . ? C5 C6 C7 124.3(2) . . ? C1 C6 C7 115.4(2) . . ? C6 C7 N1 109.14(18) . . ? C6 C7 H7A 109.9 . . ? N1 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? N1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C22 C20 C21 111.6(2) . . ? C22 C20 P1 112.43(17) . . ? C21 C20 P1 110.04(16) . . ? C22 C20 H20 107.5 . . ? C21 C20 H20 107.5 . . ? P1 C20 H20 107.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C25 C23 C24 110.8(2) . . ? C25 C23 P1 113.63(16) . . ? C24 C23 P1 108.85(16) . . ? C25 C23 H23 107.8 . . ? C24 C23 H23 107.8 . . ? P1 C23 H23 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C35 C30 C31 120.1(2) . . ? C35 C30 N1 119.8(2) . . ? C31 C30 N1 120.0(2) . . ? C30 C31 C32 119.0(3) . . ? C30 C31 H31 120.5 . . ? C32 C31 H31 120.5 . . ? C33 C32 C31 120.9(3) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C32 C33 C34 119.5(2) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? C33 C34 C35 119.9(3) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C30 C35 C34 120.5(2) . . ? C30 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C41 C40 C42 119.8(3) . 2 ? C41 C40 H40 120.1 . . ? C42 C40 H40 120.1 2 . ? C42 C41 C40 119.7(2) . . ? C42 C41 H41 120.2 . . ? C40 C41 H41 120.2 . . ? C41 C42 C40 120.5(3) . 2 ? C41 C42 H42 119.7 . . ? C40 C42 H42 119.7 2 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ni1 P1 O1 5.17(9) . . . . ? N1 Ni1 P1 O1 31.2(2) . . . . ? Br1 Ni1 P1 O1 -171.80(6) . . . . ? C1 Ni1 P1 C23 119.89(12) . . . . ? N1 Ni1 P1 C23 145.9(2) . . . . ? Br1 Ni1 P1 C23 -57.08(10) . . . . ? C1 Ni1 P1 C20 -108.88(12) . . . . ? N1 Ni1 P1 C20 -82.9(2) . . . . ? Br1 Ni1 P1 C20 74.15(10) . . . . ? C23 P1 O1 C2 -134.64(15) . . . . ? C20 P1 O1 C2 115.08(15) . . . . ? Ni1 P1 O1 C2 -5.23(15) . . . . ? C1 Ni1 N1 C30 120.04(17) . . . . ? P1 Ni1 N1 C30 94.2(3) . . . . ? Br1 Ni1 N1 C30 -62.73(15) . . . . ? C1 Ni1 N1 C7 -6.60(15) . . . . ? P1 Ni1 N1 C7 -32.5(3) . . . . ? Br1 Ni1 N1 C7 170.63(14) . . . . ? N1 Ni1 C1 C6 3.94(17) . . . . ? P1 Ni1 C1 C6 177.40(18) . . . . ? N1 Ni1 C1 C2 -178.4(2) . . . . ? P1 Ni1 C1 C2 -4.97(18) . . . . ? C6 C1 C2 C3 1.2(3) . . . . ? Ni1 C1 C2 C3 -176.42(18) . . . . ? C6 C1 C2 O1 -179.48(19) . . . . ? Ni1 C1 C2 O1 2.9(3) . . . . ? P1 O1 C2 C3 -178.56(17) . . . . ? P1 O1 C2 C1 2.1(2) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? O1 C2 C3 C4 -179.6(2) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C4 C5 C6 C7 177.0(2) . . . . ? C2 C1 C6 C5 -1.3(3) . . . . ? Ni1 C1 C6 C5 176.46(16) . . . . ? C2 C1 C6 C7 -178.07(19) . . . . ? Ni1 C1 C6 C7 -0.3(3) . . . . ? C5 C6 C7 N1 178.3(2) . . . . ? C1 C6 C7 N1 -5.0(3) . . . . ? C30 N1 C7 C6 -114.4(2) . . . . ? Ni1 N1 C7 C6 7.7(2) . . . . ? O1 P1 C20 C22 46.7(2) . . . . ? C23 P1 C20 C22 -58.0(2) . . . . ? Ni1 P1 C20 C22 163.23(18) . . . . ? O1 P1 C20 C21 -78.4(2) . . . . ? C23 P1 C20 C21 176.89(19) . . . . ? Ni1 P1 C20 C21 38.2(2) . . . . ? O1 P1 C23 C25 -154.13(19) . . . . ? C20 P1 C23 C25 -46.5(2) . . . . ? Ni1 P1 C23 C25 87.20(19) . . . . ? O1 P1 C23 C24 81.9(2) . . . . ? C20 P1 C23 C24 -170.47(19) . . . . ? Ni1 P1 C23 C24 -36.7(2) . . . . ? C7 N1 C30 C35 -131.3(2) . . . . ? Ni1 N1 C30 C35 103.9(2) . . . . ? C7 N1 C30 C31 51.3(3) . . . . ? Ni1 N1 C30 C31 -73.5(2) . . . . ? C35 C30 C31 C32 -1.5(3) . . . . ? N1 C30 C31 C32 175.9(2) . . . . ? C30 C31 C32 C33 0.0(4) . . . . ? C31 C32 C33 C34 1.0(4) . . . . ? C32 C33 C34 C35 -0.5(4) . . . . ? C31 C30 C35 C34 2.0(3) . . . . ? N1 C30 C35 C34 -175.4(2) . . . . ? C33 C34 C35 C30 -1.0(3) . . . . ? C42 C40 C41 C42 0.4(4) 2 . . . ? C40 C41 C42 C40 -0.4(4) . . . 2 ? _diffrn_measured_fraction_theta_max 0.890 _diffrn_reflns_theta_full 60.48 _diffrn_measured_fraction_theta_full 0.890 _refine_diff_density_max 0.441 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.066 data_ds62 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H33 Br N Ni O P' _chemical_formula_sum 'C19 H33 Br N Ni O P' _chemical_formula_weight 461.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Triclinic' _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9840(2) _cell_length_b 10.8172(3) _cell_length_c 13.0862(3) _cell_angle_alpha 106.6630(10) _cell_angle_beta 92.9220(10) _cell_angle_gamma 94.6940(10) _cell_volume 1075.81(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9649 _cell_measurement_theta_min 3.54 _cell_measurement_theta_max 72.40 _exptl_crystal_description 'Block' _exptl_crystal_colour 'Yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not mesured' _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 4.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6821 _exptl_absorpt_correction_T_max 0.8724 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 14325 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 72.68 _reflns_number_total 4089 _reflns_number_gt 3778 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Platon Ortep' _computing_publication_material 'LinXTL v. 1.09' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+0.0001P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4089 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.44108(4) 0.78507(3) 0.30308(3) 0.0421(7) Uani 1 1 d . . . Br1 Br 0.57315(3) 0.79287(2) 0.470990(17) 0.0557(7) Uani 1 1 d . . . P1 P 0.32603(6) 0.58888(5) 0.25452(4) 0.0413(7) Uani 1 1 d . . . O1 O 0.20720(19) 0.56946(14) 0.14192(11) 0.0481(7) Uani 1 1 d . . . N1 N 0.5375(2) 0.96481(17) 0.30298(15) 0.0484(8) Uani 1 1 d . . . C1 C 0.3056(3) 0.7914(2) 0.18553(16) 0.0453(8) Uani 1 1 d . . . C2 C 0.2032(3) 0.6864(2) 0.11785(16) 0.0464(8) Uani 1 1 d . . . C3 C 0.1020(3) 0.6961(2) 0.03222(17) 0.0527(8) Uani 1 1 d . . . H3 H 0.0336 0.6229 -0.0129 0.063 Uiso 1 1 calc R . . C4 C 0.1038(3) 0.8180(3) 0.01432(19) 0.0573(8) Uani 1 1 d . . . H4 H 0.0380 0.8270 -0.0452 0.069 Uiso 1 1 calc R . . C5 C 0.2000(3) 0.9257(2) 0.08203(19) 0.0565(8) Uani 1 1 d . . . H5 H 0.1980 1.0079 0.0697 0.068 Uiso 1 1 calc R . . C6 C 0.2996(3) 0.9128(2) 0.16827(17) 0.0493(8) Uani 1 1 d . . . C7 C 0.4036(3) 1.0210(2) 0.25073(19) 0.0533(8) Uani 1 1 d . . . H7A H 0.3311 1.0678 0.3051 0.064 Uiso 1 1 calc R . . H7B H 0.4563 1.0834 0.2164 0.064 Uiso 1 1 calc R . . C20 C 0.4757(3) 0.4657(2) 0.20590(17) 0.0486(8) Uani 1 1 d . . . C21 C 0.6030(3) 0.5305(3) 0.1481(2) 0.0655(9) Uani 1 1 d . . . H21A H 0.6713 0.6025 0.2006 0.098 Uiso 1 1 calc R . . H21B H 0.5423 0.5635 0.0961 0.098 Uiso 1 1 calc R . . H21C H 0.6766 0.4668 0.1109 0.098 Uiso 1 1 calc R . . C22 C 0.3916(4) 0.3392(2) 0.1265(2) 0.0644(9) Uani 1 1 d . . . H22A H 0.4787 0.2851 0.0940 0.097 Uiso 1 1 calc R . . H22B H 0.3229 0.3597 0.0704 0.097 Uiso 1 1 calc R . . H22C H 0.3196 0.2923 0.1644 0.097 Uiso 1 1 calc R . . C23 C 0.5698(4) 0.4361(3) 0.2993(2) 0.0650(9) Uani 1 1 d . . . H23A H 0.6645 0.3867 0.2733 0.097 Uiso 1 1 calc R . . H23B H 0.4929 0.3850 0.3312 0.097 Uiso 1 1 calc R . . H23C H 0.6124 0.5175 0.3532 0.097 Uiso 1 1 calc R . . C24 C 0.1646(3) 0.5411(2) 0.33787(17) 0.0494(8) Uani 1 1 d . . . C25 C 0.0631(4) 0.4113(3) 0.2808(2) 0.0717(10) Uani 1 1 d . . . H25A H -0.0290 0.3959 0.3238 0.108 Uiso 1 1 calc R . . H25B H 0.1369 0.3414 0.2714 0.108 Uiso 1 1 calc R . . H25C H 0.0163 0.4133 0.2107 0.108 Uiso 1 1 calc R . . C26 C 0.2428(3) 0.5361(3) 0.4456(2) 0.0688(9) Uani 1 1 d . . . H26A H 0.3154 0.6165 0.4796 0.103 Uiso 1 1 calc R . . H26B H 0.3101 0.4621 0.4342 0.103 Uiso 1 1 calc R . . H26C H 0.1532 0.5263 0.4920 0.103 Uiso 1 1 calc R . . C27 C 0.0487(3) 0.6494(3) 0.3575(3) 0.0728(10) Uani 1 1 d . . . H27A H -0.0008 0.6542 0.2888 0.109 Uiso 1 1 calc R . . H27B H 0.1137 0.7322 0.3953 0.109 Uiso 1 1 calc R . . H27C H -0.0414 0.6315 0.4009 0.109 Uiso 1 1 calc R . . C30 C 0.7080(3) 0.9772(2) 0.2582(2) 0.0573(8) Uani 1 1 d . . . C31 C 0.8329(3) 0.9147(3) 0.3140(3) 0.0739(10) Uani 1 1 d . . . H31A H 0.8360 0.9543 0.3915 0.111 Uiso 1 1 calc R . . H31B H 0.9453 0.9279 0.2897 0.111 Uiso 1 1 calc R . . H31C H 0.7983 0.8216 0.2967 0.111 Uiso 1 1 calc R . . C32 C 0.6925(4) 0.9081(3) 0.1380(2) 0.0713(10) Uani 1 1 d . . . H32A H 0.8042 0.9099 0.1104 0.107 Uiso 1 1 calc R . . H32B H 0.6178 0.9523 0.1015 0.107 Uiso 1 1 calc R . . H32C H 0.6455 0.8179 0.1252 0.107 Uiso 1 1 calc R . . C33 C 0.7721(4) 1.1203(3) 0.2793(3) 0.0823(11) Uani 1 1 d . . . H33A H 0.7708 1.1655 0.3557 0.123 Uiso 1 1 calc R . . H33B H 0.6990 1.1599 0.2378 0.123 Uiso 1 1 calc R . . H33C H 0.8875 1.1270 0.2578 0.123 Uiso 1 1 calc R . . H1 H 0.555(3) 1.019(3) 0.378(2) 0.059(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0466(7) 0.0381(7) 0.0416(7) 0.0120(2) 0.00101(16) 0.00524(16) Br1 0.0675(7) 0.0501(7) 0.0472(7) 0.0129(2) -0.00774(12) 0.00436(13) P1 0.0441(7) 0.0397(7) 0.0406(7) 0.0131(3) -0.0002(2) 0.0040(2) O1 0.0538(10) 0.0441(10) 0.0459(10) 0.0149(6) -0.0065(6) 0.0020(6) N1 0.0542(12) 0.0405(10) 0.0506(11) 0.0135(7) 0.0032(8) 0.0060(7) C1 0.0499(12) 0.0448(12) 0.0429(11) 0.0143(8) 0.0035(8) 0.0091(8) C2 0.0504(12) 0.0462(12) 0.0457(12) 0.0169(9) 0.0041(8) 0.0097(9) C3 0.0561(13) 0.0566(14) 0.0465(12) 0.0168(9) -0.0013(9) 0.0094(10) C4 0.0620(14) 0.0639(15) 0.0511(13) 0.0228(10) -0.0005(10) 0.0176(11) C5 0.0683(15) 0.0530(13) 0.0559(14) 0.0252(10) 0.0054(10) 0.0169(11) C6 0.0572(13) 0.0462(12) 0.0473(12) 0.0158(9) 0.0070(9) 0.0127(9) C7 0.0650(15) 0.0416(12) 0.0554(13) 0.0156(9) 0.0034(10) 0.0120(9) C20 0.0526(12) 0.0417(12) 0.0497(12) 0.0097(8) 0.0016(9) 0.0089(9) C21 0.0644(16) 0.0583(15) 0.0726(17) 0.0129(12) 0.0219(12) 0.0123(11) C22 0.0711(16) 0.0474(14) 0.0655(16) 0.0026(11) -0.0016(12) 0.0082(11) C23 0.0709(16) 0.0587(15) 0.0646(15) 0.0144(12) -0.0075(12) 0.0235(12) C24 0.0467(12) 0.0540(13) 0.0497(12) 0.0195(9) 0.0035(8) 0.0017(9) C25 0.0677(16) 0.0716(17) 0.0712(17) 0.0193(13) 0.0103(13) -0.0169(13) C26 0.0582(14) 0.099(2) 0.0583(15) 0.0405(14) 0.0033(11) -0.0031(13) C27 0.0629(16) 0.0755(18) 0.092(2) 0.0362(16) 0.0269(14) 0.0201(13) C30 0.0580(14) 0.0463(13) 0.0701(15) 0.0199(11) 0.0140(11) 0.0039(10) C31 0.0534(15) 0.0753(18) 0.101(2) 0.0382(16) 0.0071(14) 0.0061(12) C32 0.0746(18) 0.0713(17) 0.0689(17) 0.0184(13) 0.0258(13) 0.0076(13) C33 0.0792(19) 0.0500(15) 0.117(3) 0.0245(15) 0.0176(18) -0.0042(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 C1 1.856(2) . ? Ni1 N1 2.0320(18) . ? Ni1 P1 2.1446(6) . ? Ni1 Br1 2.3644(4) . ? P1 O1 1.6622(15) . ? P1 C20 1.860(2) . ? P1 C24 1.865(2) . ? O1 C2 1.391(2) . ? N1 C7 1.500(3) . ? N1 C30 1.520(3) . ? N1 H1 0.98(3) . ? C1 C2 1.393(3) . ? C1 C6 1.399(3) . ? C2 C3 1.382(3) . ? C3 C4 1.403(3) . ? C3 H3 0.9500 . ? C4 C5 1.387(4) . ? C4 H4 0.9500 . ? C5 C6 1.394(3) . ? C5 H5 0.9500 . ? C6 C7 1.500(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C20 C23 1.527(3) . ? C20 C21 1.537(3) . ? C20 C22 1.538(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C27 1.525(3) . ? C24 C25 1.528(3) . ? C24 C26 1.530(3) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C30 C31 1.517(4) . ? C30 C32 1.529(4) . ? C30 C33 1.532(3) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 N1 84.08(8) . . ? C1 Ni1 P1 81.16(7) . . ? N1 Ni1 P1 163.30(6) . . ? C1 Ni1 Br1 169.58(6) . . ? N1 Ni1 Br1 96.11(6) . . ? P1 Ni1 Br1 99.820(18) . . ? O1 P1 C20 100.08(9) . . ? O1 P1 C24 99.94(9) . . ? C20 P1 C24 114.18(10) . . ? O1 P1 Ni1 106.93(6) . . ? C20 P1 Ni1 113.98(7) . . ? C24 P1 Ni1 118.44(8) . . ? C2 O1 P1 110.88(13) . . ? C7 N1 C30 112.84(18) . . ? C7 N1 Ni1 107.19(13) . . ? C30 N1 Ni1 117.64(13) . . ? C7 N1 H1 106.4(16) . . ? C30 N1 H1 104.3(16) . . ? Ni1 N1 H1 107.8(16) . . ? C2 C1 C6 118.21(19) . . ? C2 C1 Ni1 124.81(16) . . ? C6 C1 Ni1 116.87(16) . . ? C3 C2 O1 121.24(19) . . ? C3 C2 C1 122.8(2) . . ? O1 C2 C1 115.91(18) . . ? C2 C3 C4 117.6(2) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 121.2(2) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.8(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 120.3(2) . . ? C5 C6 C7 125.7(2) . . ? C1 C6 C7 113.95(19) . . ? C6 C7 N1 108.73(17) . . ? C6 C7 H7A 109.9 . . ? N1 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? N1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C23 C20 C21 108.6(2) . . ? C23 C20 C22 110.03(19) . . ? C21 C20 C22 108.9(2) . . ? C23 C20 P1 111.02(16) . . ? C21 C20 P1 104.61(15) . . ? C22 C20 P1 113.44(16) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C27 C24 C25 109.7(2) . . ? C27 C24 C26 108.9(2) . . ? C25 C24 C26 109.4(2) . . ? C27 C24 P1 104.07(15) . . ? C25 C24 P1 112.66(16) . . ? C26 C24 P1 111.92(15) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C31 C30 N1 108.8(2) . . ? C31 C30 C32 109.5(2) . . ? N1 C30 C32 109.6(2) . . ? C31 C30 C33 108.4(2) . . ? N1 C30 C33 110.4(2) . . ? C32 C30 C33 110.1(2) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ni1 P1 O1 4.28(8) . . . . ? N1 Ni1 P1 O1 -23.9(2) . . . . ? Br1 Ni1 P1 O1 173.76(6) . . . . ? C1 Ni1 P1 C20 113.89(10) . . . . ? N1 Ni1 P1 C20 85.7(2) . . . . ? Br1 Ni1 P1 C20 -76.62(8) . . . . ? C1 Ni1 P1 C24 -107.45(10) . . . . ? N1 Ni1 P1 C24 -135.6(2) . . . . ? Br1 Ni1 P1 C24 62.04(8) . . . . ? C20 P1 O1 C2 -124.87(14) . . . . ? C24 P1 O1 C2 118.17(14) . . . . ? Ni1 P1 O1 C2 -5.81(14) . . . . ? C1 Ni1 N1 C7 25.63(14) . . . . ? P1 Ni1 N1 C7 53.6(3) . . . . ? Br1 Ni1 N1 C7 -143.89(13) . . . . ? C1 Ni1 N1 C30 -102.73(17) . . . . ? P1 Ni1 N1 C30 -74.8(3) . . . . ? Br1 Ni1 N1 C30 87.74(16) . . . . ? N1 Ni1 C1 C2 169.62(19) . . . . ? P1 Ni1 C1 C2 -2.55(17) . . . . ? Br1 Ni1 C1 C2 -98.8(4) . . . . ? N1 Ni1 C1 C6 -14.27(16) . . . . ? P1 Ni1 C1 C6 173.57(17) . . . . ? Br1 Ni1 C1 C6 77.3(4) . . . . ? P1 O1 C2 C3 -174.97(16) . . . . ? P1 O1 C2 C1 4.5(2) . . . . ? C6 C1 C2 C3 2.7(3) . . . . ? Ni1 C1 C2 C3 178.81(17) . . . . ? C6 C1 C2 O1 -176.70(17) . . . . ? Ni1 C1 C2 O1 -0.6(3) . . . . ? O1 C2 C3 C4 179.20(19) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -1.9(3) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C4 C5 C6 C1 1.3(3) . . . . ? C4 C5 C6 C7 -177.0(2) . . . . ? C2 C1 C6 C5 -3.3(3) . . . . ? Ni1 C1 C6 C5 -179.63(17) . . . . ? C2 C1 C6 C7 175.26(18) . . . . ? Ni1 C1 C6 C7 -1.1(3) . . . . ? C5 C6 C7 N1 -159.1(2) . . . . ? C1 C6 C7 N1 22.5(3) . . . . ? C30 N1 C7 C6 99.7(2) . . . . ? Ni1 N1 C7 C6 -31.4(2) . . . . ? O1 P1 C20 C23 -164.30(17) . . . . ? C24 P1 C20 C23 -58.5(2) . . . . ? Ni1 P1 C20 C23 81.94(17) . . . . ? O1 P1 C20 C21 78.70(17) . . . . ? C24 P1 C20 C21 -175.52(16) . . . . ? Ni1 P1 C20 C21 -35.06(17) . . . . ? O1 P1 C20 C22 -39.79(19) . . . . ? C24 P1 C20 C22 66.0(2) . . . . ? Ni1 P1 C20 C22 -153.55(16) . . . . ? O1 P1 C24 C27 -68.48(18) . . . . ? C20 P1 C24 C27 -174.35(17) . . . . ? Ni1 P1 C24 C27 47.07(19) . . . . ? O1 P1 C24 C25 50.3(2) . . . . ? C20 P1 C24 C25 -55.6(2) . . . . ? Ni1 P1 C24 C25 165.86(16) . . . . ? O1 P1 C24 C26 174.09(18) . . . . ? C20 P1 C24 C26 68.2(2) . . . . ? Ni1 P1 C24 C26 -70.37(19) . . . . ? C7 N1 C30 C31 -178.6(2) . . . . ? Ni1 N1 C30 C31 -52.9(3) . . . . ? C7 N1 C30 C32 -58.9(2) . . . . ? Ni1 N1 C30 C32 66.8(2) . . . . ? C7 N1 C30 C33 62.6(3) . . . . ? Ni1 N1 C30 C33 -171.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Br1 0.98(3) 2.71(3) 3.5495(18) 144(2) 2_676 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 72.68 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.012 _refine_diff_density_min -0.023 _refine_diff_density_rms 0.005 data_63 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H29 Br N Ni O P ' _chemical_formula_sum 'C17 H29 Br N Ni O P' _chemical_formula_weight 433.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3629(3) _cell_length_b 21.4243(6) _cell_length_c 11.3528(3) _cell_angle_alpha 90.00 _cell_angle_beta 121.931(2) _cell_angle_gamma 90.00 _cell_volume 1932.71(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9870 _cell_measurement_theta_min 4.13 _cell_measurement_theta_max 72.02 _exptl_crystal_description 'Block' _exptl_crystal_colour 'Yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 4.649 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6821 _exptl_absorpt_correction_T_max 0.8724 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 20888 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 72.83 _reflns_number_total 3640 _reflns_number_gt 3399 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Platon Ortep' _computing_publication_material 'LinXTL v. 1.09' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+2.4879P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0059(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3640 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.60655(6) 0.14283(2) 0.32681(5) 0.02307(16) Uani 1 1 d . . . Br1 Br 0.70327(4) 0.106786(14) 0.55293(3) 0.03389(15) Uani 1 1 d . . . P1 P 0.49190(9) 0.05823(3) 0.22454(7) 0.02555(19) Uani 1 1 d . . . O1 O 0.3905(3) 0.07149(9) 0.0544(2) 0.0296(5) Uani 1 1 d . . . N1 N 0.7130(3) 0.22876(11) 0.3724(3) 0.0242(5) Uani 1 1 d . . . C1 C 0.4901(4) 0.17232(13) 0.1459(3) 0.0255(6) Uani 1 1 d . . . C2 C 0.3935(4) 0.13529(13) 0.0293(3) 0.0256(6) Uani 1 1 d . . . C3 C 0.3065(4) 0.15900(14) -0.1037(3) 0.0287(6) Uani 1 1 d . . . H3 H 0.2434 0.1325 -0.1818 0.034 Uiso 1 1 calc R . . C4 C 0.3144(4) 0.22343(15) -0.1194(3) 0.0288(6) Uani 1 1 d . . . H4 H 0.2564 0.2410 -0.2099 0.035 Uiso 1 1 calc R . . C5 C 0.4053(4) 0.26236(13) -0.0052(3) 0.0279(6) Uani 1 1 d . . . H5 H 0.4079 0.3061 -0.0178 0.033 Uiso 1 1 calc R . . C6 C 0.4928(3) 0.23678(13) 0.1283(3) 0.0252(6) Uani 1 1 d . . . C7 C 0.5934(4) 0.27327(13) 0.2605(3) 0.0275(6) Uani 1 1 d . . . H7A H 0.5176 0.2926 0.2863 0.033 Uiso 1 1 calc R . . H7B H 0.6570 0.3069 0.2483 0.033 Uiso 1 1 calc R . . C20 C 0.3269(4) 0.02407(14) 0.2438(3) 0.0324(7) Uani 1 1 d . . . H20 H 0.3814 0.0067 0.3399 0.039 Uiso 1 1 calc R . . C21 C 0.2023(5) 0.07501(17) 0.2288(4) 0.0445(8) Uani 1 1 d . . . H21A H 0.1443 0.0920 0.1344 0.067 Uiso 1 1 calc R . . H21B H 0.2637 0.1085 0.2957 0.067 Uiso 1 1 calc R . . H21C H 0.1195 0.0569 0.2468 0.067 Uiso 1 1 calc R . . C22 C 0.2346(4) -0.02944(16) 0.1418(4) 0.0388(8) Uani 1 1 d . . . H22A H 0.1481 -0.0463 0.1567 0.058 Uiso 1 1 calc R . . H22B H 0.3151 -0.0624 0.1569 0.058 Uiso 1 1 calc R . . H22C H 0.1815 -0.0138 0.0465 0.058 Uiso 1 1 calc R . . C23 C 0.6324(4) -0.00561(14) 0.2424(3) 0.0331(7) Uani 1 1 d . . . H23 H 0.5667 -0.0347 0.1626 0.040 Uiso 1 1 calc R . . C24 C 0.6947(5) -0.04281(17) 0.3765(4) 0.0494(10) Uani 1 1 d . . . H24A H 0.7737 -0.0751 0.3848 0.074 Uiso 1 1 calc R . . H24B H 0.5987 -0.0625 0.3740 0.074 Uiso 1 1 calc R . . H24C H 0.7516 -0.0146 0.4564 0.074 Uiso 1 1 calc R . . C25 C 0.7780(5) 0.02056(18) 0.2322(4) 0.0483(9) Uani 1 1 d . . . H25A H 0.8505 0.0464 0.3138 0.073 Uiso 1 1 calc R . . H25B H 0.7327 0.0460 0.1481 0.073 Uiso 1 1 calc R . . H25C H 0.8438 -0.0140 0.2282 0.073 Uiso 1 1 calc R . . C30 C 0.8901(4) 0.23252(13) 0.4011(3) 0.0253(6) Uani 1 1 d . . . C31 C 0.8876(4) 0.22117(16) 0.2670(3) 0.0322(7) Uani 1 1 d . . . H31A H 0.8223 0.2542 0.2000 0.048 Uiso 1 1 calc R . . H31B H 0.8358 0.1806 0.2281 0.048 Uiso 1 1 calc R . . H31C H 1.0031 0.2215 0.2871 0.048 Uiso 1 1 calc R . . C32 C 0.9673(4) 0.29652(15) 0.4620(3) 0.0333(7) Uani 1 1 d . . . H32A H 1.0868 0.2963 0.4927 0.050 Uiso 1 1 calc R . . H32B H 0.9558 0.3054 0.5412 0.050 Uiso 1 1 calc R . . H32C H 0.9087 0.3287 0.3909 0.050 Uiso 1 1 calc R . . C33 C 0.9970(4) 0.18225(15) 0.5067(3) 0.0333(7) Uani 1 1 d . . . H33A H 1.1147 0.1872 0.5341 0.050 Uiso 1 1 calc R . . H33B H 0.9566 0.1409 0.4651 0.050 Uiso 1 1 calc R . . H33C H 0.9882 0.1863 0.5886 0.050 Uiso 1 1 calc R . . H1 H 0.717(4) 0.2394(17) 0.443(4) 0.028(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0279(3) 0.0184(3) 0.0214(3) 0.00068(18) 0.0120(2) -0.00128(18) Br1 0.0467(2) 0.0274(2) 0.0279(2) 0.00248(11) 0.01996(17) -0.00093(12) P1 0.0309(4) 0.0189(3) 0.0235(4) 0.0001(3) 0.0121(3) -0.0007(3) O1 0.0385(11) 0.0226(10) 0.0231(10) -0.0008(8) 0.0131(9) -0.0033(8) N1 0.0279(12) 0.0230(11) 0.0220(12) 0.0005(9) 0.0134(10) 0.0004(9) C1 0.0254(13) 0.0240(13) 0.0254(14) 0.0021(11) 0.0124(11) 0.0012(11) C2 0.0265(13) 0.0231(13) 0.0282(15) 0.0006(11) 0.0152(12) -0.0006(11) C3 0.0286(14) 0.0307(15) 0.0260(14) 0.0011(12) 0.0138(12) 0.0007(12) C4 0.0249(13) 0.0349(15) 0.0247(14) 0.0075(12) 0.0119(11) 0.0037(12) C5 0.0298(14) 0.0242(13) 0.0304(15) 0.0062(12) 0.0164(12) 0.0018(11) C6 0.0235(13) 0.0258(14) 0.0260(14) 0.0007(11) 0.0130(11) 0.0010(11) C7 0.0321(14) 0.0199(12) 0.0288(15) 0.0025(11) 0.0150(12) 0.0014(11) C20 0.0399(17) 0.0258(14) 0.0275(15) 0.0022(12) 0.0151(13) -0.0057(12) C21 0.0452(19) 0.0398(18) 0.051(2) -0.0024(16) 0.0271(17) -0.0037(15) C22 0.0401(17) 0.0327(16) 0.0372(17) -0.0013(14) 0.0161(14) -0.0127(14) C23 0.0333(15) 0.0259(14) 0.0338(16) -0.0049(12) 0.0135(13) 0.0037(12) C24 0.061(2) 0.0358(18) 0.0390(19) 0.0051(15) 0.0179(17) 0.0209(17) C25 0.0411(19) 0.044(2) 0.059(2) -0.0166(18) 0.0253(17) 0.0006(16) C30 0.0246(13) 0.0239(13) 0.0253(14) -0.0019(11) 0.0119(11) -0.0038(11) C31 0.0281(15) 0.0398(16) 0.0303(15) -0.0029(13) 0.0165(12) -0.0012(13) C32 0.0336(16) 0.0303(15) 0.0344(16) -0.0049(13) 0.0169(13) -0.0090(13) C33 0.0257(14) 0.0317(15) 0.0339(16) 0.0039(13) 0.0098(12) 0.0015(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 C1 1.854(3) . ? Ni1 N1 2.026(2) . ? Ni1 P1 2.1135(8) . ? Ni1 Br1 2.3553(6) . ? P1 O1 1.666(2) . ? P1 C20 1.824(3) . ? P1 C23 1.833(3) . ? O1 C2 1.399(3) . ? N1 C7 1.507(4) . ? N1 C30 1.514(4) . ? N1 H1 0.81(4) . ? C1 C2 1.391(4) . ? C1 C6 1.397(4) . ? C2 C3 1.378(4) . ? C3 C4 1.399(4) . ? C3 H3 0.9500 . ? C4 C5 1.391(4) . ? C4 H4 0.9500 . ? C5 C6 1.398(4) . ? C5 H5 0.9500 . ? C6 C7 1.502(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C20 C22 1.531(4) . ? C20 C21 1.540(5) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.534(5) . ? C23 C25 1.535(5) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C30 C33 1.526(4) . ? C30 C31 1.529(4) . ? C30 C32 1.533(4) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 N1 83.98(11) . . ? C1 Ni1 P1 81.58(9) . . ? N1 Ni1 P1 163.33(8) . . ? C1 Ni1 Br1 168.79(9) . . ? N1 Ni1 Br1 99.53(7) . . ? P1 Ni1 Br1 96.22(3) . . ? O1 P1 C20 102.00(13) . . ? O1 P1 C23 101.03(13) . . ? C20 P1 C23 106.92(15) . . ? O1 P1 Ni1 107.65(8) . . ? C20 P1 Ni1 119.64(11) . . ? C23 P1 Ni1 116.92(11) . . ? C2 O1 P1 110.01(17) . . ? C7 N1 C30 112.8(2) . . ? C7 N1 Ni1 108.29(17) . . ? C30 N1 Ni1 115.98(17) . . ? C7 N1 H1 106(3) . . ? C30 N1 H1 107(3) . . ? Ni1 N1 H1 106(3) . . ? C2 C1 C6 118.6(3) . . ? C2 C1 Ni1 124.4(2) . . ? C6 C1 Ni1 116.8(2) . . ? C3 C2 C1 122.9(3) . . ? C3 C2 O1 121.3(3) . . ? C1 C2 O1 115.9(3) . . ? C2 C3 C4 117.6(3) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 121.4(3) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 119.9(3) . . ? C1 C6 C7 114.9(3) . . ? C5 C6 C7 125.3(3) . . ? C6 C7 N1 107.9(2) . . ? C6 C7 H7A 110.1 . . ? N1 C7 H7A 110.1 . . ? C6 C7 H7B 110.1 . . ? N1 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? C22 C20 C21 110.8(3) . . ? C22 C20 P1 112.6(2) . . ? C21 C20 P1 110.0(2) . . ? C22 C20 H20 107.7 . . ? C21 C20 H20 107.7 . . ? P1 C20 H20 107.7 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C25 112.2(3) . . ? C24 C23 P1 111.8(2) . . ? C25 C23 P1 109.5(2) . . ? C24 C23 H23 107.7 . . ? C25 C23 H23 107.7 . . ? P1 C23 H23 107.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N1 C30 C33 108.6(2) . . ? N1 C30 C31 109.8(2) . . ? C33 C30 C31 109.2(3) . . ? N1 C30 C32 110.2(2) . . ? C33 C30 C32 108.7(2) . . ? C31 C30 C32 110.3(2) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ni1 P1 O1 4.99(12) . . . . ? N1 Ni1 P1 O1 -25.2(3) . . . . ? Br1 Ni1 P1 O1 173.91(9) . . . . ? C1 Ni1 P1 C20 -110.61(15) . . . . ? N1 Ni1 P1 C20 -140.8(3) . . . . ? Br1 Ni1 P1 C20 58.31(12) . . . . ? C1 Ni1 P1 C23 117.75(16) . . . . ? N1 Ni1 P1 C23 87.5(3) . . . . ? Br1 Ni1 P1 C23 -73.34(13) . . . . ? C20 P1 O1 C2 119.6(2) . . . . ? C23 P1 O1 C2 -130.2(2) . . . . ? Ni1 P1 O1 C2 -7.1(2) . . . . ? C1 Ni1 N1 C7 25.0(2) . . . . ? P1 Ni1 N1 C7 55.1(4) . . . . ? Br1 Ni1 N1 C7 -144.26(17) . . . . ? C1 Ni1 N1 C30 -103.0(2) . . . . ? P1 Ni1 N1 C30 -73.0(3) . . . . ? Br1 Ni1 N1 C30 87.73(19) . . . . ? N1 Ni1 C1 C2 169.1(3) . . . . ? P1 Ni1 C1 C2 -2.5(2) . . . . ? Br1 Ni1 C1 C2 -81.9(6) . . . . ? N1 Ni1 C1 C6 -14.9(2) . . . . ? P1 Ni1 C1 C6 173.4(2) . . . . ? Br1 Ni1 C1 C6 94.0(5) . . . . ? C6 C1 C2 C3 3.1(4) . . . . ? Ni1 C1 C2 C3 179.0(2) . . . . ? C6 C1 C2 O1 -177.4(3) . . . . ? Ni1 C1 C2 O1 -1.6(4) . . . . ? P1 O1 C2 C3 -174.7(2) . . . . ? P1 O1 C2 C1 5.8(3) . . . . ? C1 C2 C3 C4 -1.5(4) . . . . ? O1 C2 C3 C4 179.1(3) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C2 C1 C6 C5 -2.7(4) . . . . ? Ni1 C1 C6 C5 -178.9(2) . . . . ? C2 C1 C6 C7 177.1(3) . . . . ? Ni1 C1 C6 C7 0.9(3) . . . . ? C4 C5 C6 C1 0.8(4) . . . . ? C4 C5 C6 C7 -179.0(3) . . . . ? C1 C6 C7 N1 19.7(3) . . . . ? C5 C6 C7 N1 -160.5(3) . . . . ? C30 N1 C7 C6 100.5(3) . . . . ? Ni1 N1 C7 C6 -29.3(3) . . . . ? O1 P1 C20 C22 50.3(2) . . . . ? C23 P1 C20 C22 -55.4(3) . . . . ? Ni1 P1 C20 C22 168.78(19) . . . . ? O1 P1 C20 C21 -73.9(2) . . . . ? C23 P1 C20 C21 -179.6(2) . . . . ? Ni1 P1 C20 C21 44.6(3) . . . . ? O1 P1 C23 C24 -159.4(2) . . . . ? C20 P1 C23 C24 -53.1(3) . . . . ? Ni1 P1 C23 C24 84.2(3) . . . . ? O1 P1 C23 C25 75.6(2) . . . . ? C20 P1 C23 C25 -178.1(2) . . . . ? Ni1 P1 C23 C25 -40.8(3) . . . . ? C7 N1 C30 C33 -175.4(2) . . . . ? Ni1 N1 C30 C33 -49.7(3) . . . . ? C7 N1 C30 C31 -56.1(3) . . . . ? Ni1 N1 C30 C31 69.6(3) . . . . ? C7 N1 C30 C32 65.6(3) . . . . ? Ni1 N1 C30 C32 -168.66(19) . . . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 72.83 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.456 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.127 data_64 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H27 Br N Ni O P ' _chemical_formula_sum 'C16 H27 Br N Ni O P' _chemical_formula_weight 418.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'Pbca' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.8825(2) _cell_length_b 16.0131(3) _cell_length_c 21.0574(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3669.52(12) _cell_formula_units_Z 8.00 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9833 _cell_measurement_theta_min 4.20 _cell_measurement_theta_max 72.05 _exptl_crystal_description 'Block' _exptl_crystal_colour 'Yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not mesured' _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 4.878 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6821 _exptl_absorpt_correction_T_max 0.8724 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 45256 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0123 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.20 _diffrn_reflns_theta_max 72.34 _reflns_number_total 3626 _reflns_number_gt 3311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Platon Ortep' _computing_publication_material 'LinXTL v. 1.09' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+1.0636P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3626 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.28972(3) 0.104968(19) 0.646850(14) 0.02950(11) Uani 1 1 d . . . Br1 Br 0.45720(2) 0.171327(16) 0.598003(11) 0.04893(10) Uani 1 1 d . . . P1 P 0.21786(4) 0.05106(3) 0.56290(2) 0.03212(12) Uani 1 1 d . . . O1 O 0.09920(13) -0.00806(9) 0.58402(6) 0.0390(3) Uani 1 1 d . . . N1 N 0.33137(15) 0.13773(10) 0.73621(7) 0.0304(3) Uani 1 1 d . . . C1 C 0.16492(17) 0.04294(11) 0.68368(9) 0.0303(4) Uani 1 1 d . . . C2 C 0.08470(18) -0.00797(12) 0.64980(9) 0.0330(4) Uani 1 1 d . . . C3 C -0.0045(2) -0.05585(13) 0.67842(10) 0.0399(4) Uani 1 1 d . . . H3 H -0.0583 -0.0899 0.6541 0.048 Uiso 1 1 calc R . . C4 C -0.0130(2) -0.05253(13) 0.74470(11) 0.0420(5) Uani 1 1 d . . . H4 H -0.0744 -0.0845 0.7657 0.050 Uiso 1 1 calc R . . C5 C 0.06598(19) -0.00364(12) 0.78018(10) 0.0377(4) Uani 1 1 d . . . H5 H 0.0597 -0.0029 0.8252 0.045 Uiso 1 1 calc R . . C6 C 0.15542(17) 0.04482(11) 0.74964(9) 0.0313(4) Uani 1 1 d . . . C7 C 0.2415(2) 0.10213(13) 0.78358(9) 0.0381(4) Uani 1 1 d . . . H7A H 0.2862 0.0711 0.8170 0.046 Uiso 1 1 calc R . . H7B H 0.1948 0.1479 0.8040 0.046 Uiso 1 1 calc R . . C20 C 0.3141(2) -0.02330(14) 0.51986(10) 0.0426(5) Uani 1 1 d . . . H20 H 0.3811 0.0088 0.4984 0.051 Uiso 1 1 calc R . . C21 C 0.3736(3) -0.08375(15) 0.56651(12) 0.0553(6) Uani 1 1 d . . . H21A H 0.3097 -0.1165 0.5878 0.083 Uiso 1 1 calc R . . H21B H 0.4205 -0.0523 0.5982 0.083 Uiso 1 1 calc R . . H21C H 0.4289 -0.1214 0.5435 0.083 Uiso 1 1 calc R . . C22 C 0.2426(3) -0.0710(2) 0.46874(14) 0.0724(9) Uani 1 1 d . . . H22A H 0.2974 -0.1110 0.4478 0.109 Uiso 1 1 calc R . . H22B H 0.2106 -0.0315 0.4373 0.109 Uiso 1 1 calc R . . H22C H 0.1741 -0.1011 0.4885 0.109 Uiso 1 1 calc R . . C23 C 0.1445(2) 0.11815(14) 0.50372(10) 0.0409(5) Uani 1 1 d . . . H23 H 0.0882 0.0826 0.4777 0.049 Uiso 1 1 calc R . . C24 C 0.2359(3) 0.1603(2) 0.45845(12) 0.0639(7) Uani 1 1 d . . . H24A H 0.1909 0.1942 0.4275 0.096 Uiso 1 1 calc R . . H24B H 0.2836 0.1175 0.4362 0.096 Uiso 1 1 calc R . . H24C H 0.2916 0.1962 0.4828 0.096 Uiso 1 1 calc R . . C25 C 0.0661(3) 0.18247(15) 0.53891(12) 0.0535(6) Uani 1 1 d . . . H25A H 0.1195 0.2193 0.5638 0.080 Uiso 1 1 calc R . . H25B H 0.0089 0.1536 0.5674 0.080 Uiso 1 1 calc R . . H25C H 0.0196 0.2157 0.5081 0.080 Uiso 1 1 calc R . . C30 C 0.36337(18) 0.22732(11) 0.74896(10) 0.0349(4) Uani 1 1 d . . . H30 H 0.4304 0.2428 0.7187 0.042 Uiso 1 1 calc R . . C31 C 0.4139(2) 0.23927(15) 0.81564(11) 0.0467(5) Uani 1 1 d . . . H31A H 0.3500 0.2256 0.8468 0.070 Uiso 1 1 calc R . . H31B H 0.4394 0.2975 0.8212 0.070 Uiso 1 1 calc R . . H31C H 0.4847 0.2024 0.8219 0.070 Uiso 1 1 calc R . . C32 C 0.2550(2) 0.28368(15) 0.73457(13) 0.0536(6) Uani 1 1 d . . . H32A H 0.2264 0.2734 0.6911 0.080 Uiso 1 1 calc R . . H32B H 0.2801 0.3422 0.7388 0.080 Uiso 1 1 calc R . . H32C H 0.1882 0.2719 0.7645 0.080 Uiso 1 1 calc R . . H1 H 0.396(2) 0.1120(12) 0.7401(10) 0.025(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.03169(19) 0.03175(18) 0.02505(18) 0.00150(12) 0.00227(11) -0.00386(12) Br1 0.04738(16) 0.06133(18) 0.03808(15) 0.00462(10) 0.00971(9) -0.01839(10) P1 0.0347(3) 0.0362(3) 0.0254(2) 0.00087(18) -0.00038(17) -0.00188(19) O1 0.0418(8) 0.0437(7) 0.0313(7) 0.0003(6) -0.0028(6) -0.0095(6) N1 0.0306(8) 0.0321(8) 0.0285(8) 0.0003(6) 0.0019(6) 0.0006(7) C1 0.0313(9) 0.0279(8) 0.0318(9) 0.0032(7) 0.0033(7) 0.0020(7) C2 0.0341(9) 0.0329(9) 0.0319(9) 0.0029(7) 0.0008(7) 0.0012(7) C3 0.0353(10) 0.0376(10) 0.0469(12) 0.0019(8) -0.0002(9) -0.0064(8) C4 0.0384(10) 0.0386(10) 0.0489(12) 0.0086(9) 0.0115(9) -0.0049(8) C5 0.0414(10) 0.0369(10) 0.0349(10) 0.0061(8) 0.0096(8) 0.0014(8) C6 0.0329(9) 0.0296(8) 0.0316(9) 0.0029(7) 0.0042(7) 0.0038(7) C7 0.0453(11) 0.0413(11) 0.0275(9) -0.0010(8) 0.0073(8) -0.0052(8) C20 0.0426(11) 0.0500(12) 0.0353(11) -0.0087(9) -0.0017(9) 0.0037(9) C21 0.0666(16) 0.0444(12) 0.0549(14) -0.0066(10) -0.0064(12) 0.0127(11) C22 0.0671(17) 0.093(2) 0.0568(16) -0.0434(16) -0.0150(14) 0.0214(16) C23 0.0421(11) 0.0485(11) 0.0319(10) 0.0076(8) -0.0045(8) -0.0002(9) C24 0.0608(16) 0.0841(19) 0.0466(14) 0.0293(13) -0.0014(12) -0.0053(14) C25 0.0609(15) 0.0504(13) 0.0492(14) 0.0050(10) -0.0068(11) 0.0124(11) C30 0.0342(9) 0.0337(9) 0.0368(10) -0.0029(8) -0.0033(8) -0.0026(8) C31 0.0470(12) 0.0519(12) 0.0414(12) -0.0084(9) -0.0058(9) -0.0068(10) C32 0.0515(13) 0.0381(11) 0.0714(17) -0.0016(11) -0.0111(12) 0.0076(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 C1 1.8527(18) . ? Ni1 N1 2.0054(16) . ? Ni1 P1 2.1170(6) . ? Ni1 Br1 2.3471(4) . ? P1 O1 1.6618(15) . ? P1 C20 1.827(2) . ? P1 C23 1.829(2) . ? O1 C2 1.394(2) . ? N1 C30 1.500(2) . ? N1 C7 1.509(2) . ? N1 H1 0.82(2) . ? C1 C2 1.391(3) . ? C1 C6 1.393(3) . ? C2 C3 1.376(3) . ? C3 C4 1.400(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(3) . ? C4 H4 0.9500 . ? C5 C6 1.401(3) . ? C5 H5 0.9500 . ? C6 C7 1.493(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C20 C21 1.523(3) . ? C20 C22 1.532(3) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C25 1.529(3) . ? C23 C24 1.534(3) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C30 C32 1.516(3) . ? C30 C31 1.520(3) . ? C30 H30 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 N1 85.02(7) . . ? C1 Ni1 P1 81.96(6) . . ? N1 Ni1 P1 166.83(5) . . ? C1 Ni1 Br1 174.49(6) . . ? N1 Ni1 Br1 96.73(5) . . ? P1 Ni1 Br1 96.054(18) . . ? O1 P1 C20 101.96(9) . . ? O1 P1 C23 100.25(9) . . ? C20 P1 C23 107.17(10) . . ? O1 P1 Ni1 107.21(5) . . ? C20 P1 Ni1 117.92(7) . . ? C23 P1 Ni1 119.38(7) . . ? C2 O1 P1 110.69(12) . . ? C30 N1 C7 113.17(15) . . ? C30 N1 Ni1 118.06(12) . . ? C7 N1 Ni1 112.01(12) . . ? C30 N1 H1 105.2(14) . . ? C7 N1 H1 107.6(14) . . ? Ni1 N1 H1 98.9(15) . . ? C2 C1 C6 118.51(17) . . ? C2 C1 Ni1 124.02(14) . . ? C6 C1 Ni1 117.40(14) . . ? C3 C2 C1 123.00(18) . . ? C3 C2 O1 120.96(18) . . ? C1 C2 O1 116.04(17) . . ? C2 C3 C4 117.55(19) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 121.26(19) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.86(19) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.81(18) . . ? C1 C6 C7 116.36(16) . . ? C5 C6 C7 123.80(18) . . ? C6 C7 N1 108.80(15) . . ? C6 C7 H7A 109.9 . . ? N1 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? N1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C21 C20 C22 110.6(2) . . ? C21 C20 P1 109.75(15) . . ? C22 C20 P1 112.48(17) . . ? C21 C20 H20 108.0 . . ? C22 C20 H20 108.0 . . ? P1 C20 H20 108.0 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C25 C23 C24 111.5(2) . . ? C25 C23 P1 108.01(15) . . ? C24 C23 P1 113.52(17) . . ? C25 C23 H23 107.9 . . ? C24 C23 H23 107.9 . . ? P1 C23 H23 107.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N1 C30 C32 110.66(17) . . ? N1 C30 C31 111.69(16) . . ? C32 C30 C31 113.02(18) . . ? N1 C30 H30 107.0 . . ? C32 C30 H30 107.0 . . ? C31 C30 H30 107.0 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ni1 P1 O1 1.01(8) . . . . ? N1 Ni1 P1 O1 9.6(2) . . . . ? Br1 Ni1 P1 O1 175.84(6) . . . . ? C1 Ni1 P1 C20 -113.16(10) . . . . ? N1 Ni1 P1 C20 -104.5(2) . . . . ? Br1 Ni1 P1 C20 61.66(9) . . . . ? C1 Ni1 P1 C23 113.85(10) . . . . ? N1 Ni1 P1 C23 122.5(2) . . . . ? Br1 Ni1 P1 C23 -71.32(8) . . . . ? C20 P1 O1 C2 122.03(14) . . . . ? C23 P1 O1 C2 -127.80(14) . . . . ? Ni1 P1 O1 C2 -2.49(14) . . . . ? C1 Ni1 N1 C30 -137.56(14) . . . . ? P1 Ni1 N1 C30 -146.13(18) . . . . ? Br1 Ni1 N1 C30 47.69(13) . . . . ? C1 Ni1 N1 C7 -3.40(14) . . . . ? P1 Ni1 N1 C7 -12.0(3) . . . . ? Br1 Ni1 N1 C7 -178.16(13) . . . . ? N1 Ni1 C1 C2 -177.37(16) . . . . ? P1 Ni1 C1 C2 0.66(15) . . . . ? P1 Ni1 C1 C6 177.51(14) . . . . ? C6 C1 C2 C3 0.7(3) . . . . ? Ni1 C1 C2 C3 177.55(16) . . . . ? C6 C1 C2 O1 -179.35(16) . . . . ? Ni1 C1 C2 O1 -2.5(2) . . . . ? P1 O1 C2 C3 -176.96(16) . . . . ? P1 O1 C2 C1 3.1(2) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? O1 C2 C3 C4 179.85(19) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? Ni1 C1 C6 C5 -177.36(14) . . . . ? C2 C1 C6 C7 -178.46(17) . . . . ? Ni1 C1 C6 C7 4.5(2) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C4 C5 C6 C7 177.44(19) . . . . ? C1 C6 C7 N1 -6.9(2) . . . . ? C5 C6 C7 N1 175.06(17) . . . . ? C30 N1 C7 C6 142.66(16) . . . . ? Ni1 N1 C7 C6 6.2(2) . . . . ? O1 P1 C20 C21 -72.66(17) . . . . ? C23 P1 C20 C21 -177.48(17) . . . . ? Ni1 P1 C20 C21 44.37(19) . . . . ? O1 P1 C20 C22 50.9(2) . . . . ? C23 P1 C20 C22 -53.9(2) . . . . ? Ni1 P1 C20 C22 167.94(18) . . . . ? O1 P1 C23 C25 75.47(17) . . . . ? C20 P1 C23 C25 -178.50(16) . . . . ? Ni1 P1 C23 C25 -41.07(18) . . . . ? O1 P1 C23 C24 -160.34(18) . . . . ? C20 P1 C23 C24 -54.3(2) . . . . ? Ni1 P1 C23 C24 83.12(19) . . . . ? C7 N1 C30 C32 -70.6(2) . . . . ? Ni1 N1 C30 C32 63.1(2) . . . . ? C7 N1 C30 C31 56.3(2) . . . . ? Ni1 N1 C30 C31 -170.05(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 72.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.548 _refine_diff_density_min -0.904 _refine_diff_density_rms 0.130 data_65 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C38 H48 N2 Ni2 O2 P2' _chemical_formula_sum 'C38 H48 N2 Ni2 O2 P2' _chemical_formula_weight 744.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Triclinic' _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1174(2) _cell_length_b 12.0007(2) _cell_length_c 14.0031(3) _cell_angle_alpha 107.4250(10) _cell_angle_beta 90.6000(10) _cell_angle_gamma 101.8910(10) _cell_volume 1739.04(6) _cell_formula_units_Z 2.00 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9892 _cell_measurement_theta_min 6.636 _cell_measurement_theta_max 135.172 _exptl_crystal_description 'block' _exptl_crystal_colour 'Yellow' _exptl_crystal_size_max 0.026 _exptl_crystal_size_mid 0.024 _exptl_crystal_size_min 0.023 _exptl_crystal_density_meas 'not mesured' _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 2.494 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6821 _exptl_absorpt_correction_T_max 0.8724 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 25347 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 67.87 _reflns_number_total 5461 _reflns_number_gt 4564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Platon Ortep' _computing_publication_material 'LinXTL v. 1.09' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5461 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.47780(3) 0.87440(3) 0.48184(3) 0.01736(12) Uani 1 1 d . . . Ni2 Ni 0.96662(3) 0.61321(3) 0.01785(3) 0.02052(12) Uani 1 1 d . . . P1 P 0.52445(5) 0.70476(4) 0.42994(5) 0.02092(16) Uani 1 1 d . . . P2 P 0.89874(5) 0.74437(5) -0.02827(5) 0.02217(16) Uani 1 1 d . . . O1 O 0.39897(13) 0.60226(12) 0.43154(14) 0.0268(4) Uani 1 1 d . . . O2 O 0.90148(14) 0.85929(13) 0.07413(13) 0.0267(4) Uani 1 1 d . . . N1 N 0.58409(15) 0.99059(14) 0.42618(15) 0.0180(4) Uani 1 1 d . . . N2 N 0.99982(16) 0.51260(15) 0.10177(15) 0.0218(5) Uani 1 1 d . . . C1 C 0.33340(19) 0.78139(18) 0.50607(18) 0.0193(5) Uani 1 1 d . . . C2 C 0.3050(2) 0.65654(18) 0.47372(19) 0.0225(5) Uani 1 1 d . . . C3 C 0.1896(2) 0.59075(19) 0.4806(2) 0.0297(6) Uani 1 1 d . . . H3 H 0.1722 0.5057 0.4583 0.036 Uiso 1 1 calc R . . C4 C 0.0999(2) 0.6524(2) 0.5212(2) 0.0295(6) Uani 1 1 d . . . H4 H 0.0204 0.6088 0.5276 0.035 Uiso 1 1 calc R . . C5 C 0.1243(2) 0.77727(19) 0.5526(2) 0.0244(6) Uani 1 1 d . . . H5 H 0.0618 0.8182 0.5797 0.029 Uiso 1 1 calc R . . C6 C 0.24044(19) 0.84117(18) 0.54398(18) 0.0191(5) Uani 1 1 d . . . C7 C 0.27959(18) 0.97522(17) 0.5626(2) 0.0209(5) Uani 1 1 d . . . H7A H 0.2481 0.9966 0.5056 0.025 Uiso 1 1 calc R . . H7B H 0.2454 1.0184 0.6243 0.025 Uiso 1 1 calc R . . C30 C 0.53314(19) 0.98105(17) 0.32996(19) 0.0192(6) Uani 1 1 d . . . C31 C 0.4045(2) 0.94025(19) 0.3077(2) 0.0245(6) Uani 1 1 d . . . H31 H 0.3543 0.9217 0.3577 0.029 Uiso 1 1 calc R . . C32 C 0.3501(2) 0.9268(2) 0.2143(2) 0.0294(6) Uani 1 1 d . . . H32 H 0.2635 0.8977 0.2009 0.035 Uiso 1 1 calc R . . C33 C 0.4194(2) 0.9548(2) 0.1411(2) 0.0326(7) Uani 1 1 d . . . H33 H 0.3816 0.9451 0.0771 0.039 Uiso 1 1 calc R . . C34 C 0.5457(2) 0.9974(2) 0.1617(2) 0.0342(6) Uani 1 1 d . . . H34 H 0.5946 1.0177 0.1116 0.041 Uiso 1 1 calc R . . C35 C 0.6013(2) 1.0107(2) 0.2549(2) 0.0278(6) Uani 1 1 d . . . H35 H 0.6879 1.0408 0.2677 0.033 Uiso 1 1 calc R . . C20 C 0.5659(2) 0.63419(19) 0.3040(2) 0.0296(6) Uani 1 1 d . . . H20 H 0.5743 0.5516 0.3001 0.036 Uiso 1 1 calc R . . C21 C 0.4622(3) 0.6227(3) 0.2266(2) 0.0461(8) Uani 1 1 d . . . H21A H 0.4579 0.7024 0.2237 0.069 Uiso 1 1 calc R . . H21B H 0.3835 0.5847 0.2459 0.069 Uiso 1 1 calc R . . H21C H 0.4787 0.5736 0.1604 0.069 Uiso 1 1 calc R . . C22 C 0.6873(3) 0.6996(2) 0.2786(2) 0.0429(8) Uani 1 1 d . . . H22A H 0.7097 0.6521 0.2140 0.064 Uiso 1 1 calc R . . H22B H 0.7518 0.7112 0.3311 0.064 Uiso 1 1 calc R . . H22C H 0.6786 0.7776 0.2744 0.064 Uiso 1 1 calc R . . C25 C 0.7545(3) 0.7684(3) 0.5397(3) 0.0566(10) Uani 1 1 d . . . H25A H 0.7419 0.8496 0.5704 0.085 Uiso 1 1 calc R . . H25B H 0.7926 0.7636 0.4762 0.085 Uiso 1 1 calc R . . H25C H 0.8085 0.7491 0.5853 0.085 Uiso 1 1 calc R . . C23 C 0.6304(2) 0.6794(2) 0.5196(2) 0.0281(7) Uani 1 1 d . . . H23 H 0.6455 0.5970 0.4906 0.034 Uiso 1 1 calc R . . C24 C 0.5717(3) 0.6861(2) 0.6175(2) 0.0392(8) Uani 1 1 d . . . H24A H 0.6271 0.6691 0.6636 0.059 Uiso 1 1 calc R . . H24B H 0.4934 0.6270 0.6048 0.059 Uiso 1 1 calc R . . H24C H 0.5567 0.7664 0.6474 0.059 Uiso 1 1 calc R . . C41 C 0.98677(19) 0.73231(18) 0.1410(2) 0.0231(6) Uani 1 1 d . . . C42 C 0.9540(2) 0.84093(18) 0.15722(19) 0.0235(6) Uani 1 1 d . . . C43 C 0.9733(2) 0.9274(2) 0.2502(2) 0.0284(6) Uani 1 1 d . . . H43 H 0.9482 1.0009 0.2605 0.034 Uiso 1 1 calc R . . C44 C 1.0306(2) 0.9034(2) 0.3282(2) 0.0307(6) Uani 1 1 d . . . H44 H 1.0432 0.9608 0.3931 0.037 Uiso 1 1 calc R . . C45 C 1.0696(2) 0.7971(2) 0.3131(2) 0.0294(6) Uani 1 1 d . . . H45 H 1.1109 0.7831 0.3668 0.035 Uiso 1 1 calc R . . C46 C 1.0480(2) 0.71165(19) 0.2195(2) 0.0246(6) Uani 1 1 d . . . C47 C 1.0872(2) 0.59281(19) 0.18700(19) 0.0239(6) Uani 1 1 d . . . H47A H 1.1725 0.6039 0.1659 0.029 Uiso 1 1 calc R . . H47B H 1.0843 0.5583 0.2431 0.029 Uiso 1 1 calc R . . C60 C 0.8845(2) 0.46247(18) 0.1327(2) 0.0223(6) Uani 1 1 d . . . C61 C 0.8611(2) 0.4685(2) 0.2315(2) 0.0277(6) Uani 1 1 d . . . H61 H 0.9218 0.5155 0.2843 0.033 Uiso 1 1 calc R . . C62 C 0.7512(2) 0.4075(2) 0.2541(2) 0.0342(6) Uani 1 1 d . . . H62 H 0.7388 0.4113 0.3219 0.041 Uiso 1 1 calc R . . C63 C 0.6591(2) 0.3411(2) 0.1801(3) 0.0359(7) Uani 1 1 d . . . H63 H 0.5844 0.2980 0.1960 0.043 Uiso 1 1 calc R . . C64 C 0.6781(2) 0.3387(2) 0.0821(2) 0.0304(7) Uani 1 1 d . . . H64 H 0.6147 0.2957 0.0304 0.036 Uiso 1 1 calc R . . C65 C 0.7882(2) 0.39816(19) 0.0585(2) 0.0268(6) Uani 1 1 d . . . H65 H 0.7991 0.3956 -0.0093 0.032 Uiso 1 1 calc R . . C53 C 0.7345(2) 0.7043(2) -0.0725(2) 0.0276(6) Uani 1 1 d . . . H53 H 0.7236 0.6398 -0.1385 0.033 Uiso 1 1 calc R . . C54 C 0.6594(2) 0.6541(2) 0.0010(2) 0.0380(7) Uani 1 1 d . . . H54A H 0.6645 0.7173 0.0653 0.057 Uiso 1 1 calc R . . H54B H 0.6920 0.5883 0.0113 0.057 Uiso 1 1 calc R . . H54C H 0.5731 0.6244 -0.0260 0.057 Uiso 1 1 calc R . . C55 C 0.6891(2) 0.8098(2) -0.0879(2) 0.0366(7) Uani 1 1 d . . . H55A H 0.6002 0.7859 -0.1067 0.055 Uiso 1 1 calc R . . H55B H 0.7322 0.8343 -0.1415 0.055 Uiso 1 1 calc R . . H55C H 0.7057 0.8769 -0.0255 0.055 Uiso 1 1 calc R . . C50 C 0.9770(2) 0.8231(2) -0.1111(2) 0.0305(6) Uani 1 1 d . . . H50 H 0.9421 0.8952 -0.1045 0.037 Uiso 1 1 calc R . . C51 C 1.1147(2) 0.8659(2) -0.0786(3) 0.0407(8) Uani 1 1 d . . . H51A H 1.1532 0.7967 -0.0930 0.061 Uiso 1 1 calc R . . H51B H 1.1261 0.9086 -0.0065 0.061 Uiso 1 1 calc R . . H51C H 1.1532 0.9197 -0.1157 0.061 Uiso 1 1 calc R . . C52 C 0.9519(3) 0.7434(2) -0.2201(2) 0.0414(7) Uani 1 1 d . . . H52A H 1.0052 0.7806 -0.2625 0.062 Uiso 1 1 calc R . . H52B H 0.8653 0.7335 -0.2422 0.062 Uiso 1 1 calc R . . H52C H 0.9690 0.6649 -0.2255 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01590(18) 0.01477(17) 0.0205(3) 0.00520(15) 0.00434(17) 0.00153(13) Ni2 0.0219(2) 0.02053(19) 0.0203(3) 0.00702(16) 0.00119(18) 0.00603(14) P1 0.0194(3) 0.0167(2) 0.0259(4) 0.0060(2) 0.0051(3) 0.0028(2) P2 0.0237(3) 0.0224(3) 0.0221(4) 0.0075(2) 0.0019(3) 0.0078(2) O1 0.0231(8) 0.0158(7) 0.0391(12) 0.0064(7) 0.0082(8) 0.0019(6) O2 0.0336(8) 0.0237(7) 0.0236(11) 0.0058(7) 0.0001(8) 0.0106(6) N1 0.0151(8) 0.0209(8) 0.0179(13) 0.0066(8) 0.0054(8) 0.0022(7) N2 0.0215(9) 0.0246(9) 0.0207(13) 0.0087(8) 0.0013(9) 0.0059(7) C1 0.0208(10) 0.0196(10) 0.0172(15) 0.0067(9) 0.0027(10) 0.0020(8) C2 0.0207(10) 0.0217(10) 0.0247(16) 0.0080(10) 0.0050(11) 0.0023(8) C3 0.0266(12) 0.0202(10) 0.0387(19) 0.0092(10) 0.0056(12) -0.0029(9) C4 0.0205(11) 0.0296(12) 0.0353(19) 0.0120(11) 0.0070(12) -0.0048(9) C5 0.0178(10) 0.0295(11) 0.0254(17) 0.0096(10) 0.0067(11) 0.0025(9) C6 0.0203(10) 0.0204(10) 0.0156(15) 0.0069(9) 0.0027(10) 0.0002(8) C7 0.0137(10) 0.0224(10) 0.0255(16) 0.0067(9) 0.0040(10) 0.0027(8) C30 0.0219(10) 0.0153(9) 0.0196(16) 0.0036(9) 0.0039(11) 0.0048(8) C31 0.0230(11) 0.0265(11) 0.0244(17) 0.0099(10) 0.0053(11) 0.0032(9) C32 0.0271(12) 0.0331(12) 0.0278(18) 0.0104(11) -0.0012(13) 0.0051(10) C33 0.0401(14) 0.0365(13) 0.0230(18) 0.0101(11) -0.0004(14) 0.0111(11) C34 0.0393(14) 0.0436(14) 0.0222(18) 0.0150(12) 0.0116(13) 0.0070(11) C35 0.0251(12) 0.0344(12) 0.0228(18) 0.0096(11) 0.0059(12) 0.0027(10) C20 0.0324(12) 0.0199(10) 0.0327(18) 0.0019(10) 0.0076(12) 0.0063(9) C21 0.0475(16) 0.0512(16) 0.029(2) -0.0019(13) 0.0008(15) 0.0081(13) C22 0.0413(15) 0.0452(15) 0.035(2) 0.0047(13) 0.0172(14) 0.0046(12) C25 0.0329(15) 0.083(2) 0.058(3) 0.0444(19) -0.0108(16) -0.0102(15) C23 0.0280(12) 0.0264(11) 0.0337(19) 0.0139(11) 0.0052(13) 0.0073(9) C24 0.0451(15) 0.0407(14) 0.037(2) 0.0190(13) 0.0033(15) 0.0114(12) C41 0.0196(10) 0.0237(11) 0.0243(16) 0.0067(10) 0.0022(11) 0.0019(8) C42 0.0227(11) 0.0254(11) 0.0218(16) 0.0076(10) 0.0016(11) 0.0033(9) C43 0.0290(12) 0.0238(11) 0.0287(18) 0.0038(10) 0.0039(12) 0.0037(9) C44 0.0331(13) 0.0315(12) 0.0203(17) 0.0017(10) 0.0025(12) 0.0006(10) C45 0.0277(12) 0.0331(12) 0.0234(17) 0.0084(11) -0.0031(12) -0.0013(10) C46 0.0214(11) 0.0256(11) 0.0252(17) 0.0082(10) 0.0002(11) 0.0015(9) C47 0.0247(11) 0.0278(11) 0.0197(16) 0.0079(10) 0.0003(11) 0.0059(9) C60 0.0241(11) 0.0193(10) 0.0257(18) 0.0085(9) 0.0049(11) 0.0072(8) C61 0.0293(12) 0.0329(12) 0.0221(19) 0.0093(11) 0.0052(12) 0.0083(10) C62 0.0378(14) 0.0440(14) 0.0278(19) 0.0172(12) 0.0156(13) 0.0151(11) C63 0.0260(12) 0.0370(13) 0.046(2) 0.0153(12) 0.0129(13) 0.0058(10) C64 0.0224(11) 0.0316(12) 0.036(2) 0.0084(11) 0.0036(12) 0.0074(9) C65 0.0272(12) 0.0284(11) 0.0265(17) 0.0093(10) 0.0020(11) 0.0083(9) C53 0.0270(12) 0.0288(11) 0.0257(17) 0.0050(10) -0.0013(12) 0.0086(9) C54 0.0286(13) 0.0406(14) 0.046(2) 0.0140(13) 0.0053(13) 0.0079(11) C55 0.0312(13) 0.0385(13) 0.042(2) 0.0128(12) -0.0060(13) 0.0118(11) C50 0.0342(13) 0.0300(12) 0.0354(19) 0.0168(11) 0.0111(12) 0.0141(10) C51 0.0337(13) 0.0339(13) 0.064(2) 0.0266(14) 0.0143(14) 0.0096(11) C52 0.0561(17) 0.0462(15) 0.034(2) 0.0219(13) 0.0164(15) 0.0224(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 C1 1.854(2) . ? Ni1 N1 1.9847(19) . ? Ni1 N1 1.9964(18) 2_676 ? Ni1 P1 2.1210(6) . ? Ni1 Ni1 2.8377(6) 2_676 ? Ni2 C41 1.858(2) . ? Ni2 N2 1.989(2) 2_765 ? Ni2 N2 1.9998(19) . ? Ni2 P2 2.1336(6) . ? Ni2 Ni2 2.8651(6) 2_765 ? P1 O1 1.6643(15) . ? P1 C20 1.823(3) . ? P1 C23 1.845(2) . ? P2 O2 1.6603(17) . ? P2 C50 1.826(3) . ? P2 C53 1.839(2) . ? O1 C2 1.388(3) . ? O2 C42 1.391(3) . ? N1 C30 1.419(3) . ? N1 C7 1.480(2) 2_676 ? N1 Ni1 1.9964(18) 2_676 ? N2 C60 1.429(3) . ? N2 C47 1.482(3) . ? N2 Ni2 1.989(2) 2_765 ? C1 C2 1.395(3) . ? C1 C6 1.398(3) . ? C2 C3 1.382(3) . ? C3 C4 1.390(3) . ? C3 H3 0.9500 . ? C4 C5 1.395(3) . ? C4 H4 0.9500 . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 C7 1.518(3) . ? C7 N1 1.480(2) 2_676 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C30 C35 1.392(4) . ? C30 C31 1.412(3) . ? C31 C32 1.384(4) . ? C31 H31 0.9500 . ? C32 C33 1.370(4) . ? C32 H32 0.9500 . ? C33 C34 1.386(4) . ? C33 H33 0.9500 . ? C34 C35 1.389(4) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C20 C22 1.518(4) . ? C20 C21 1.532(4) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C25 C23 1.525(3) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C23 C24 1.511(4) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C41 C42 1.380(3) . ? C41 C46 1.397(3) . ? C42 C43 1.383(3) . ? C43 C44 1.389(4) . ? C43 H43 0.9500 . ? C44 C45 1.389(3) . ? C44 H44 0.9500 . ? C45 C46 1.384(3) . ? C45 H45 0.9500 . ? C46 C47 1.518(3) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C60 C61 1.393(4) . ? C60 C65 1.407(3) . ? C61 C62 1.380(4) . ? C61 H61 0.9500 . ? C62 C63 1.380(4) . ? C62 H62 0.9500 . ? C63 C64 1.384(4) . ? C63 H63 0.9500 . ? C64 C65 1.380(4) . ? C64 H64 0.9500 . ? C65 H65 0.9500 . ? C53 C54 1.517(4) . ? C53 C55 1.526(3) . ? C53 H53 1.0000 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C50 C52 1.526(4) . ? C50 C51 1.529(3) . ? C50 H50 1.0000 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 N1 157.68(8) . . ? C1 Ni1 N1 83.79(8) . 2_676 ? N1 Ni1 N1 89.07(8) . 2_676 ? C1 Ni1 P1 81.38(7) . . ? N1 Ni1 P1 110.45(6) . . ? N1 Ni1 P1 158.06(6) 2_676 . ? C1 Ni1 Ni1 124.81(7) . 2_676 ? N1 Ni1 Ni1 44.70(5) . 2_676 ? N1 Ni1 Ni1 44.37(5) 2_676 2_676 ? P1 Ni1 Ni1 153.76(3) . 2_676 ? C41 Ni2 N2 161.79(8) . 2_765 ? C41 Ni2 N2 83.17(9) . . ? N2 Ni2 N2 88.16(9) 2_765 . ? C41 Ni2 P2 81.37(7) . . ? N2 Ni2 P2 109.91(6) 2_765 . ? N2 Ni2 P2 160.46(6) . . ? C41 Ni2 Ni2 125.19(7) . 2_765 ? N2 Ni2 Ni2 44.23(5) 2_765 2_765 ? N2 Ni2 Ni2 43.93(6) . 2_765 ? P2 Ni2 Ni2 153.40(3) . 2_765 ? O1 P1 C20 98.29(10) . . ? O1 P1 C23 100.25(10) . . ? C20 P1 C23 107.38(12) . . ? O1 P1 Ni1 107.24(6) . . ? C20 P1 Ni1 126.19(8) . . ? C23 P1 Ni1 113.29(8) . . ? O2 P2 C50 100.00(10) . . ? O2 P2 C53 101.22(10) . . ? C50 P2 C53 105.38(12) . . ? O2 P2 Ni2 106.88(6) . . ? C50 P2 Ni2 123.88(8) . . ? C53 P2 Ni2 115.98(8) . . ? C2 O1 P1 110.61(12) . . ? C42 O2 P2 110.86(13) . . ? C30 N1 C7 113.57(19) . 2_676 ? C30 N1 Ni1 109.92(13) . . ? C7 N1 Ni1 126.48(14) 2_676 . ? C30 N1 Ni1 103.52(12) . 2_676 ? C7 N1 Ni1 107.28(12) 2_676 2_676 ? Ni1 N1 Ni1 90.92(8) . 2_676 ? C60 N2 C47 113.1(2) . . ? C60 N2 Ni2 105.89(13) . 2_765 ? C47 N2 Ni2 128.29(14) . 2_765 ? C60 N2 Ni2 107.77(13) . . ? C47 N2 Ni2 106.54(13) . . ? Ni2 N2 Ni2 91.83(9) 2_765 . ? C2 C1 C6 118.5(2) . . ? C2 C1 Ni1 124.14(18) . . ? C6 C1 Ni1 116.47(15) . . ? C3 C2 O1 121.93(18) . . ? C3 C2 C1 122.2(2) . . ? O1 C2 C1 115.84(19) . . ? C2 C3 C4 118.1(2) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C3 C4 C5 121.2(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 119.5(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 120.40(19) . . ? C5 C6 C7 126.9(2) . . ? C1 C6 C7 112.44(19) . . ? N1 C7 C6 108.41(16) 2_676 . ? N1 C7 H7A 110.0 2_676 . ? C6 C7 H7A 110.0 . . ? N1 C7 H7B 110.0 2_676 . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? C35 C30 C31 116.7(2) . . ? C35 C30 N1 124.47(19) . . ? C31 C30 N1 118.8(2) . . ? C32 C31 C30 121.3(2) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C33 C32 C31 120.9(2) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C32 C33 C34 119.0(2) . . ? C32 C33 H33 120.5 . . ? C34 C33 H33 120.5 . . ? C33 C34 C35 120.6(3) . . ? C33 C34 H34 119.7 . . ? C35 C34 H34 119.7 . . ? C34 C35 C30 121.4(2) . . ? C34 C35 H35 119.3 . . ? C30 C35 H35 119.3 . . ? C22 C20 C21 110.2(3) . . ? C22 C20 P1 113.36(17) . . ? C21 C20 P1 109.80(18) . . ? C22 C20 H20 107.8 . . ? C21 C20 H20 107.8 . . ? P1 C20 H20 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C23 C25 109.6(2) . . ? C24 C23 P1 110.00(17) . . ? C25 C23 P1 112.58(18) . . ? C24 C23 H23 108.2 . . ? C25 C23 H23 108.2 . . ? P1 C23 H23 108.2 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C42 C41 C46 118.9(2) . . ? C42 C41 Ni2 124.61(19) . . ? C46 C41 Ni2 116.25(16) . . ? C41 C42 C43 122.2(2) . . ? C41 C42 O2 116.1(2) . . ? C43 C42 O2 121.69(19) . . ? C42 C43 C44 117.9(2) . . ? C42 C43 H43 121.1 . . ? C44 C43 H43 121.1 . . ? C43 C44 C45 121.3(2) . . ? C43 C44 H44 119.3 . . ? C45 C44 H44 119.3 . . ? C46 C45 C44 119.5(2) . . ? C46 C45 H45 120.2 . . ? C44 C45 H45 120.2 . . ? C45 C46 C41 120.0(2) . . ? C45 C46 C47 127.6(2) . . ? C41 C46 C47 112.4(2) . . ? N2 C47 C46 106.88(16) . . ? N2 C47 H47A 110.3 . . ? C46 C47 H47A 110.3 . . ? N2 C47 H47B 110.3 . . ? C46 C47 H47B 110.3 . . ? H47A C47 H47B 108.6 . . ? C61 C60 C65 116.8(2) . . ? C61 C60 N2 124.8(2) . . ? C65 C60 N2 118.3(2) . . ? C62 C61 C60 121.2(2) . . ? C62 C61 H61 119.4 . . ? C60 C61 H61 119.4 . . ? C61 C62 C63 121.3(3) . . ? C61 C62 H62 119.3 . . ? C63 C62 H62 119.3 . . ? C62 C63 C64 118.4(3) . . ? C62 C63 H63 120.8 . . ? C64 C63 H63 120.8 . . ? C65 C64 C63 120.8(2) . . ? C65 C64 H64 119.6 . . ? C63 C64 H64 119.6 . . ? C64 C65 C60 121.4(3) . . ? C64 C65 H65 119.3 . . ? C60 C65 H65 119.3 . . ? C54 C53 C55 111.1(2) . . ? C54 C53 P2 109.24(17) . . ? C55 C53 P2 112.40(16) . . ? C54 C53 H53 108.0 . . ? C55 C53 H53 108.0 . . ? P2 C53 H53 108.0 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C53 C55 H55A 109.5 . . ? C53 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C53 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C52 C50 C51 112.4(2) . . ? C52 C50 P2 110.15(18) . . ? C51 C50 P2 110.18(19) . . ? C52 C50 H50 108.0 . . ? C51 C50 H50 108.0 . . ? P2 C50 H50 108.0 . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C50 C52 H52A 109.5 . . ? C50 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C50 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ni1 P1 O1 6.83(10) . . . . ? N1 Ni1 P1 O1 -153.57(9) . . . . ? N1 Ni1 P1 O1 54.84(16) 2_676 . . . ? Ni1 Ni1 P1 O1 -170.00(8) 2_676 . . . ? C1 Ni1 P1 C20 121.29(12) . . . . ? N1 Ni1 P1 C20 -39.11(11) . . . . ? N1 Ni1 P1 C20 169.30(16) 2_676 . . . ? Ni1 Ni1 P1 C20 -55.54(12) 2_676 . . . ? C1 Ni1 P1 C23 -102.83(12) . . . . ? N1 Ni1 P1 C23 96.77(11) . . . . ? N1 Ni1 P1 C23 -54.82(17) 2_676 . . . ? Ni1 Ni1 P1 C23 80.34(12) 2_676 . . . ? C41 Ni2 P2 O2 -2.97(10) . . . . ? N2 Ni2 P2 O2 -168.19(8) 2_765 . . . ? N2 Ni2 P2 O2 35.08(18) . . . . ? Ni2 Ni2 P2 O2 179.93(8) 2_765 . . . ? C41 Ni2 P2 C50 112.01(13) . . . . ? N2 Ni2 P2 C50 -53.21(12) 2_765 . . . ? N2 Ni2 P2 C50 150.05(19) . . . . ? Ni2 Ni2 P2 C50 -65.10(12) 2_765 . . . ? C41 Ni2 P2 C53 -114.94(12) . . . . ? N2 Ni2 P2 C53 79.84(12) 2_765 . . . ? N2 Ni2 P2 C53 -76.89(19) . . . . ? Ni2 Ni2 P2 C53 67.96(12) 2_765 . . . ? C20 P1 O1 C2 -137.18(17) . . . . ? C23 P1 O1 C2 113.36(17) . . . . ? Ni1 P1 O1 C2 -5.12(17) . . . . ? C50 P2 O2 C42 -126.07(16) . . . . ? C53 P2 O2 C42 125.90(16) . . . . ? Ni2 P2 O2 C42 4.10(16) . . . . ? C1 Ni1 N1 C30 -33.7(3) . . . . ? N1 Ni1 N1 C30 -104.74(14) 2_676 . . . ? P1 Ni1 N1 C30 85.50(13) . . . . ? Ni1 Ni1 N1 C30 -104.74(14) 2_676 . . . ? C1 Ni1 N1 C7 -176.5(2) . . . 2_676 ? N1 Ni1 N1 C7 112.42(19) 2_676 . . 2_676 ? P1 Ni1 N1 C7 -57.34(18) . . . 2_676 ? Ni1 Ni1 N1 C7 112.42(19) 2_676 . . 2_676 ? C1 Ni1 N1 Ni1 71.1(2) . . . 2_676 ? N1 Ni1 N1 Ni1 0.0 2_676 . . 2_676 ? P1 Ni1 N1 Ni1 -169.76(4) . . . 2_676 ? C41 Ni2 N2 C60 88.71(16) . . . . ? N2 Ni2 N2 C60 -107.34(15) 2_765 . . . ? P2 Ni2 N2 C60 50.9(2) . . . . ? Ni2 Ni2 N2 C60 -107.34(15) 2_765 . . . ? C41 Ni2 N2 C47 -32.95(15) . . . . ? N2 Ni2 N2 C47 131.01(17) 2_765 . . . ? P2 Ni2 N2 C47 -70.8(2) . . . . ? Ni2 Ni2 N2 C47 131.01(17) 2_765 . . . ? C41 Ni2 N2 Ni2 -163.96(9) . . . 2_765 ? N2 Ni2 N2 Ni2 -0.002(1) 2_765 . . 2_765 ? P2 Ni2 N2 Ni2 158.19(12) . . . 2_765 ? N1 Ni1 C1 C2 115.4(2) . . . . ? N1 Ni1 C1 C2 -172.5(2) 2_676 . . . ? P1 Ni1 C1 C2 -8.73(19) . . . . ? Ni1 Ni1 C1 C2 169.56(17) 2_676 . . . ? N1 Ni1 C1 C6 -53.4(3) . . . . ? N1 Ni1 C1 C6 18.64(18) 2_676 . . . ? P1 Ni1 C1 C6 -177.58(19) . . . . ? Ni1 Ni1 C1 C6 0.7(2) 2_676 . . . ? P1 O1 C2 C3 177.8(2) . . . . ? P1 O1 C2 C1 -0.6(3) . . . . ? C6 C1 C2 C3 -1.9(4) . . . . ? Ni1 C1 C2 C3 -170.5(2) . . . . ? C6 C1 C2 O1 176.4(2) . . . . ? Ni1 C1 C2 O1 7.8(3) . . . . ? O1 C2 C3 C4 -178.1(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 1.1(4) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C1 -1.3(4) . . . . ? C4 C5 C6 C7 172.4(2) . . . . ? C2 C1 C6 C5 2.5(4) . . . . ? Ni1 C1 C6 C5 171.96(18) . . . . ? C2 C1 C6 C7 -172.1(2) . . . . ? Ni1 C1 C6 C7 -2.6(3) . . . . ? C5 C6 C7 N1 163.7(2) . . . 2_676 ? C1 C6 C7 N1 -22.1(3) . . . 2_676 ? C7 N1 C30 C35 -5.5(3) 2_676 . . . ? Ni1 N1 C30 C35 -153.52(17) . . . . ? Ni1 N1 C30 C35 110.5(2) 2_676 . . . ? C7 N1 C30 C31 175.30(17) 2_676 . . . ? Ni1 N1 C30 C31 27.3(2) . . . . ? Ni1 N1 C30 C31 -68.71(19) 2_676 . . . ? C35 C30 C31 C32 2.2(3) . . . . ? N1 C30 C31 C32 -178.60(19) . . . . ? C30 C31 C32 C33 -1.2(3) . . . . ? C31 C32 C33 C34 -0.2(4) . . . . ? C32 C33 C34 C35 0.5(4) . . . . ? C33 C34 C35 C30 0.6(4) . . . . ? C31 C30 C35 C34 -1.8(3) . . . . ? N1 C30 C35 C34 179.0(2) . . . . ? O1 P1 C20 C22 -174.82(18) . . . . ? C23 P1 C20 C22 -71.3(2) . . . . ? Ni1 P1 C20 C22 66.7(2) . . . . ? O1 P1 C20 C21 61.49(19) . . . . ? C23 P1 C20 C21 165.02(18) . . . . ? Ni1 P1 C20 C21 -57.0(2) . . . . ? O1 P1 C23 C24 -53.70(18) . . . . ? C20 P1 C23 C24 -155.82(17) . . . . ? Ni1 P1 C23 C24 60.24(18) . . . . ? O1 P1 C23 C25 -176.2(2) . . . . ? C20 P1 C23 C25 81.7(2) . . . . ? Ni1 P1 C23 C25 -62.2(2) . . . . ? N2 Ni2 C41 C42 131.5(3) 2_765 . . . ? N2 Ni2 C41 C42 -166.3(2) . . . . ? P2 Ni2 C41 C42 1.7(2) . . . . ? Ni2 Ni2 C41 C42 -179.90(17) 2_765 . . . ? N2 Ni2 C41 C46 -43.4(4) 2_765 . . . ? N2 Ni2 C41 C46 18.70(18) . . . . ? P2 Ni2 C41 C46 -173.29(19) . . . . ? Ni2 Ni2 C41 C46 5.1(2) 2_765 . . . ? C46 C41 C42 C43 -3.9(4) . . . . ? Ni2 C41 C42 C43 -178.73(19) . . . . ? C46 C41 C42 O2 175.4(2) . . . . ? Ni2 C41 C42 O2 0.6(3) . . . . ? P2 O2 C42 C41 -3.2(3) . . . . ? P2 O2 C42 C43 176.08(19) . . . . ? C41 C42 C43 C44 1.7(4) . . . . ? O2 C42 C43 C44 -177.6(2) . . . . ? C42 C43 C44 C45 1.3(4) . . . . ? C43 C44 C45 C46 -2.0(4) . . . . ? C44 C45 C46 C41 -0.3(4) . . . . ? C44 C45 C46 C47 177.5(2) . . . . ? C42 C41 C46 C45 3.1(4) . . . . ? Ni2 C41 C46 C45 178.40(19) . . . . ? C42 C41 C46 C47 -175.0(2) . . . . ? Ni2 C41 C46 C47 0.3(3) . . . . ? C60 N2 C47 C46 -78.7(2) . . . . ? Ni2 N2 C47 C46 145.54(17) 2_765 . . . ? Ni2 N2 C47 C46 39.5(2) . . . . ? C45 C46 C47 N2 154.9(2) . . . . ? C41 C46 C47 N2 -27.2(3) . . . . ? C47 N2 C60 C61 -11.1(3) . . . . ? Ni2 N2 C60 C61 134.20(19) 2_765 . . . ? Ni2 N2 C60 C61 -128.55(19) . . . . ? C47 N2 C60 C65 171.45(18) . . . . ? Ni2 N2 C60 C65 -43.3(2) 2_765 . . . ? Ni2 N2 C60 C65 54.0(2) . . . . ? C65 C60 C61 C62 4.1(3) . . . . ? N2 C60 C61 C62 -173.4(2) . . . . ? C60 C61 C62 C63 -1.9(4) . . . . ? C61 C62 C63 C64 -1.3(4) . . . . ? C62 C63 C64 C65 2.1(3) . . . . ? C63 C64 C65 C60 0.3(3) . . . . ? C61 C60 C65 C64 -3.4(3) . . . . ? N2 C60 C65 C64 174.34(19) . . . . ? O2 P2 C53 C54 -68.15(17) . . . . ? C50 P2 C53 C54 -171.92(16) . . . . ? Ni2 P2 C53 C54 47.07(18) . . . . ? O2 P2 C53 C55 55.6(2) . . . . ? C50 P2 C53 C55 -48.1(2) . . . . ? Ni2 P2 C53 C55 170.86(17) . . . . ? O2 P2 C50 C52 -162.48(16) . . . . ? C53 P2 C50 C52 -57.80(19) . . . . ? Ni2 P2 C50 C52 79.25(18) . . . . ? O2 P2 C50 C51 72.94(18) . . . . ? C53 P2 C50 C51 177.62(17) . . . . ? Ni2 P2 C50 C51 -45.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.862 _diffrn_reflns_theta_full 67.87 _diffrn_measured_fraction_theta_full 0.862 _refine_diff_density_max 0.374 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.059