# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email lcliang@mail.nsysu.edu.tw _publ_contact_author_name 'Lan-Chang Liang' _publ_author_name 'Lan-Chang Liang' data_a7162 _database_code_depnum_ccdc_archive 'CCDC 834550' #TrackingRef '- [PNN]Ni_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H48 Li2 N4 P2' _chemical_formula_sum 'C44 H48 Li2 N4 P2' _chemical_formula_weight 708.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 16.1085(4) _cell_length_b 14.1250(5) _cell_length_c 18.6374(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.3690(10) _cell_angle_gamma 90.00 _cell_volume 4000.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.951 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26529 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.02 _reflns_number_total 7006 _reflns_number_gt 5194 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1232P)^2^+9.3579P] 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 7006 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1512 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 0.629 _refine_ls_restrained_S_all 0.629 _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 C1 C 0.02280(16) -0.04125(18) 0.16372(13) 0.0336(5) Uani 1 1 d . . . C2 C 0.01035(17) -0.13823(19) 0.15235(14) 0.0369(6) Uani 1 1 d . . . H2 H 0.0565 -0.1793 0.1757 0.044 Uiso 1 1 calc R . . C3 C -0.0696(2) -0.1747(2) 0.10679(16) 0.0527(8) Uani 1 1 d . . . H3 H -0.0771 -0.2397 0.1001 0.063 Uiso 1 1 calc R . . C4 C -0.1378(2) -0.1141(3) 0.07155(17) 0.0637(10) Uani 1 1 d . . . H4 H -0.1919 -0.1382 0.0416 0.076 Uiso 1 1 calc R . . C5 C -0.1260(2) -0.0181(3) 0.08065(18) 0.0650(10) Uani 1 1 d . . . H5 H -0.1721 0.0227 0.0564 0.078 Uiso 1 1 calc R . . C6 C -0.04601(18) 0.0185(2) 0.12573(16) 0.0506(7) Uani 1 1 d . . . H6 H -0.0383 0.0837 0.1306 0.061 Uiso 1 1 calc R . . C7 C 0.13586(16) 0.12139(17) 0.20023(14) 0.0326(5) Uani 1 1 d . . . C8 C 0.1483(2) 0.1374(2) 0.13079(16) 0.0479(7) Uani 1 1 d . . . H8 H 0.1519 0.0863 0.1005 0.057 Uiso 1 1 calc R . . C9 C 0.1553(2) 0.2288(2) 0.10650(17) 0.0585(8) Uani 1 1 d . . . H9 H 0.1629 0.2386 0.0597 0.070 Uiso 1 1 calc R . . C10 C 0.1513(2) 0.3049(2) 0.15086(17) 0.0532(8) Uani 1 1 d . . . H10 H 0.1564 0.3661 0.1345 0.064 Uiso 1 1 calc R . . C11 C 0.1396(2) 0.2901(2) 0.21953(17) 0.0527(8) Uani 1 1 d . . . H11 H 0.1369 0.3415 0.2498 0.063 Uiso 1 1 calc R . . C12 C 0.13187(19) 0.19909(18) 0.24416(15) 0.0440(7) Uani 1 1 d . . . H12 H 0.1239 0.1901 0.2909 0.053 Uiso 1 1 calc R . . C13 C 0.09999(16) 0.01829(16) 0.31794(13) 0.0308(5) Uani 1 1 d . . . C14 C 0.01478(17) 0.01663(18) 0.32020(15) 0.0392(6) Uani 1 1 d . . . H14 H -0.0314 0.0006 0.2765 0.047 Uiso 1 1 calc R . . C15 C -0.0031(2) 0.0383(2) 0.38624(17) 0.0475(7) Uani 1 1 d . . . H15 H -0.0603 0.0363 0.3874 0.057 Uiso 1 1 calc R . . C16 C 0.0663(2) 0.0630(2) 0.45024(16) 0.0470(7) Uani 1 1 d . . . H16 H 0.0549 0.0786 0.4946 0.056 Uiso 1 1 calc R . . C17 C 0.15131(19) 0.06518(18) 0.45019(15) 0.0414(6) Uani 1 1 d . . . H17 H 0.1960 0.0823 0.4945 0.050 Uiso 1 1 calc R . . C18 C 0.17337(17) 0.04197(16) 0.38420(13) 0.0320(5) Uani 1 1 d . . . C19 C 0.32306(19) 0.0805(2) 0.44404(16) 0.0515(7) Uani 1 1 d . . . H19A H 0.3246 0.0444 0.4888 0.062 Uiso 1 1 calc R . . H19B H 0.3102 0.1459 0.4523 0.062 Uiso 1 1 calc R . . C20 C 0.4115(2) 0.0749(3) 0.43313(18) 0.0595(8) Uani 1 1 d . . . H20A H 0.4525 0.1152 0.4705 0.071 Uiso 1 1 calc R . . H20B H 0.4330 0.0104 0.4426 0.071 Uiso 1 1 calc R . . C21 C 0.4992(2) 0.0954(3) 0.3549(3) 0.0800(12) Uani 1 1 d . . . H21A H 0.5189 0.0311 0.3654 0.120 Uiso 1 1 calc R . . H21B H 0.5373 0.1364 0.3928 0.120 Uiso 1 1 calc R . . H21C H 0.5004 0.1133 0.3056 0.120 Uiso 1 1 calc R . . C22 C 0.3777(3) 0.1994(2) 0.3407(2) 0.0749(11) Uani 1 1 d . . . H22A H 0.3187 0.2023 0.3419 0.112 Uiso 1 1 calc R . . H22B H 0.3783 0.2181 0.2914 0.112 Uiso 1 1 calc R . . H22C H 0.4146 0.2413 0.3785 0.112 Uiso 1 1 calc R . . C23 C 0.27277(16) -0.16031(17) 0.12408(13) 0.0327(5) Uani 1 1 d . . . C24 C 0.31162(19) -0.24888(19) 0.13517(17) 0.0460(7) Uani 1 1 d . . . H24 H 0.3700 -0.2552 0.1660 0.055 Uiso 1 1 calc R . . C25 C 0.2644(2) -0.3283(2) 0.10077(19) 0.0562(8) Uani 1 1 d . . . H25 H 0.2915 -0.3873 0.1085 0.067 Uiso 1 1 calc R . . C26 C 0.1777(2) -0.3202(2) 0.05512(18) 0.0556(8) Uani 1 1 d . . . H26 H 0.1465 -0.3734 0.0313 0.067 Uiso 1 1 calc R . . C27 C 0.13773(19) -0.2332(2) 0.04510(17) 0.0536(8) Uani 1 1 d . . . H27 H 0.0789 -0.2276 0.0151 0.064 Uiso 1 1 calc R . . C28 C 0.18404(16) -0.1539(2) 0.07925(15) 0.0403(6) Uani 1 1 d . . . H28 H 0.1559 -0.0954 0.0724 0.048 Uiso 1 1 calc R . . C29 C 0.35541(15) -0.00307(17) 0.08205(13) 0.0318(5) Uani 1 1 d . . . C30 C 0.36729(17) -0.05966(18) 0.02520(15) 0.0380(6) Uani 1 1 d . . . H30 H 0.3636 -0.1251 0.0285 0.046 Uiso 1 1 calc R . . C31 C 0.38441(18) -0.0201(2) -0.03602(16) 0.0454(7) Uani 1 1 d . . . H31 H 0.3916 -0.0588 -0.0739 0.054 Uiso 1 1 calc R . . C32 C 0.39080(18) 0.0765(2) -0.04106(16) 0.0465(7) Uani 1 1 d . . . H32 H 0.4019 0.1033 -0.0826 0.056 Uiso 1 1 calc R . . C33 C 0.38079(19) 0.1336(2) 0.01511(17) 0.0480(7) Uani 1 1 d . . . H33 H 0.3861 0.1989 0.0120 0.058 Uiso 1 1 calc R . . C34 C 0.36278(17) 0.09434(18) 0.07656(15) 0.0401(6) Uani 1 1 d . . . H34 H 0.3556 0.1334 0.1142 0.048 Uiso 1 1 calc R . . C35 C 0.43659(15) -0.09051(17) 0.22682(14) 0.0318(5) Uani 1 1 d . . . C36 C 0.51575(17) -0.07353(19) 0.21471(16) 0.0412(6) Uani 1 1 d . . . H36 H 0.5151 -0.0435 0.1701 0.049 Uiso 1 1 calc R . . C37 C 0.59583(18) -0.1000(2) 0.26719(17) 0.0486(7) Uani 1 1 d . . . H37 H 0.6485 -0.0867 0.2589 0.058 Uiso 1 1 calc R . . C38 C 0.59510(18) -0.1464(2) 0.33193(18) 0.0513(8) Uani 1 1 d . . . H38 H 0.6481 -0.1666 0.3668 0.062 Uiso 1 1 calc R . . C39 C 0.51786(18) -0.1638(2) 0.34637(16) 0.0456(7) Uani 1 1 d . . . H39 H 0.5200 -0.1961 0.3904 0.055 Uiso 1 1 calc R . . C40 C 0.43518(16) -0.13359(16) 0.29562(14) 0.0338(5) Uani 1 1 d . . . C41 C 0.36039(18) -0.19516(19) 0.37631(15) 0.0428(6) Uani 1 1 d . . . H41A H 0.3988 -0.1626 0.4208 0.051 Uiso 1 1 calc R . . H41B H 0.3851 -0.2573 0.3742 0.051 Uiso 1 1 calc R . . C42 C 0.27031(18) -0.2061(2) 0.38357(15) 0.0438(7) Uani 1 1 d . . . H42A H 0.2747 -0.2480 0.4259 0.053 Uiso 1 1 calc R . . H42B H 0.2508 -0.1448 0.3953 0.053 Uiso 1 1 calc R . . C43 C 0.2254(2) -0.3402(2) 0.29709(19) 0.0580(8) Uani 1 1 d . . . H43A H 0.2801 -0.3391 0.2871 0.087 Uiso 1 1 calc R . . H43B H 0.1797 -0.3636 0.2531 0.087 Uiso 1 1 calc R . . H43C H 0.2307 -0.3809 0.3396 0.087 Uiso 1 1 calc R . . C44 C 0.1188(2) -0.2456(2) 0.32857(19) 0.0572(8) Uani 1 1 d . . . H44A H 0.1043 -0.1827 0.3401 0.086 Uiso 1 1 calc R . . H44B H 0.1232 -0.2867 0.3707 0.086 Uiso 1 1 calc R . . H44C H 0.0736 -0.2684 0.2841 0.086 Uiso 1 1 calc R . . N1 N 0.25447(13) 0.04365(14) 0.37846(11) 0.0351(5) Uani 1 1 d . . . N2 N 0.41052(15) 0.10342(16) 0.35651(13) 0.0437(5) Uani 1 1 d . . . N3 N 0.35637(13) -0.14185(14) 0.30807(11) 0.0328(5) Uani 1 1 d . . . N4 N 0.20323(15) -0.24399(15) 0.31452(13) 0.0415(5) Uani 1 1 d . . . P1 P 0.12697(4) -0.00073(4) 0.23189(3) 0.02873(17) Uani 1 1 d . . . P2 P 0.33073(4) -0.04987(4) 0.16437(4) 0.03049(17) Uani 1 1 d . . . Li1 Li 0.3149(3) 0.0042(3) 0.3069(3) 0.0396(10) Uani 1 1 d . . . Li2 Li 0.2326(3) -0.1517(3) 0.2425(2) 0.0376(9) Uani 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 C1 0.0319(13) 0.0411(14) 0.0285(12) -0.0053(11) 0.0111(10) 0.0025(11) C2 0.0388(14) 0.0414(14) 0.0310(13) -0.0036(11) 0.0124(11) -0.0044(11) C3 0.0540(18) 0.065(2) 0.0408(16) -0.0135(14) 0.0175(14) -0.0223(16) C4 0.0379(16) 0.106(3) 0.0431(17) -0.0250(19) 0.0077(14) -0.0141(18) C5 0.0374(16) 0.103(3) 0.0450(18) -0.0135(18) 0.0011(13) 0.0222(17) C6 0.0410(16) 0.0559(18) 0.0469(16) -0.0091(14) 0.0039(13) 0.0158(13) C7 0.0362(13) 0.0265(12) 0.0344(13) 0.0035(10) 0.0108(11) 0.0044(10) C8 0.073(2) 0.0373(15) 0.0386(15) 0.0009(12) 0.0258(14) 0.0080(14) C9 0.094(2) 0.0452(17) 0.0444(17) 0.0100(14) 0.0333(17) 0.0069(16) C10 0.074(2) 0.0336(15) 0.0526(18) 0.0108(13) 0.0216(16) 0.0062(14) C11 0.080(2) 0.0305(14) 0.0507(17) -0.0011(13) 0.0250(16) 0.0082(14) C12 0.0635(18) 0.0339(14) 0.0381(15) 0.0008(12) 0.0213(13) 0.0083(13) C13 0.0379(13) 0.0250(11) 0.0318(12) -0.0004(10) 0.0147(11) -0.0001(10) C14 0.0417(14) 0.0376(14) 0.0417(14) -0.0038(12) 0.0182(12) -0.0037(11) C15 0.0538(17) 0.0469(16) 0.0529(17) -0.0055(14) 0.0325(15) -0.0072(13) C16 0.072(2) 0.0411(15) 0.0404(15) -0.0031(12) 0.0353(15) -0.0062(14) C17 0.0597(17) 0.0347(14) 0.0312(13) -0.0030(11) 0.0168(13) -0.0071(12) C18 0.0441(14) 0.0230(12) 0.0284(12) 0.0005(9) 0.0112(11) -0.0011(10) C19 0.0505(17) 0.0624(19) 0.0352(15) -0.0102(14) 0.0055(13) -0.0101(15) C20 0.0470(17) 0.063(2) 0.0554(19) -0.0088(16) -0.0008(14) -0.0104(15) C21 0.052(2) 0.075(2) 0.118(3) -0.048(2) 0.034(2) -0.0243(18) C22 0.089(3) 0.0413(18) 0.101(3) -0.0047(19) 0.040(2) -0.0084(18) C23 0.0349(13) 0.0333(13) 0.0312(13) -0.0029(10) 0.0128(10) -0.0050(10) C24 0.0469(16) 0.0348(14) 0.0538(17) -0.0034(13) 0.0134(13) -0.0014(12) C25 0.068(2) 0.0341(15) 0.068(2) -0.0081(14) 0.0249(17) -0.0064(14) C26 0.064(2) 0.0536(19) 0.0579(19) -0.0242(15) 0.0326(16) -0.0286(16) C27 0.0392(15) 0.072(2) 0.0513(18) -0.0188(16) 0.0172(13) -0.0153(15) C28 0.0319(13) 0.0479(16) 0.0400(14) -0.0066(12) 0.0106(11) -0.0014(11) C29 0.0276(12) 0.0318(13) 0.0330(13) -0.0013(10) 0.0061(10) -0.0005(10) C30 0.0394(14) 0.0327(13) 0.0420(15) -0.0037(11) 0.0134(12) -0.0038(11) C31 0.0481(16) 0.0524(17) 0.0392(15) -0.0080(13) 0.0193(13) -0.0072(13) C32 0.0467(16) 0.0520(17) 0.0424(16) 0.0077(13) 0.0169(13) -0.0056(13) C33 0.0524(17) 0.0344(14) 0.0570(18) 0.0085(13) 0.0180(14) -0.0044(12) C34 0.0452(15) 0.0332(14) 0.0405(15) -0.0018(11) 0.0122(12) -0.0015(11) C35 0.0280(12) 0.0283(12) 0.0364(13) -0.0052(10) 0.0070(10) 0.0009(10) C36 0.0374(14) 0.0426(15) 0.0425(15) -0.0073(12) 0.0119(12) -0.0001(12) C37 0.0327(14) 0.0553(18) 0.0555(18) -0.0123(15) 0.0114(13) 0.0011(13) C38 0.0314(14) 0.0553(18) 0.0563(18) -0.0070(15) 0.0002(13) 0.0106(13) C39 0.0424(15) 0.0416(15) 0.0446(16) 0.0019(12) 0.0034(12) 0.0085(12) C40 0.0330(13) 0.0268(12) 0.0362(13) -0.0025(10) 0.0042(11) 0.0036(10) C41 0.0475(16) 0.0356(14) 0.0372(14) 0.0070(12) 0.0031(12) -0.0007(12) C42 0.0540(17) 0.0389(15) 0.0361(14) 0.0110(12) 0.0117(13) -0.0033(12) C43 0.073(2) 0.0392(16) 0.0581(19) 0.0008(14) 0.0169(16) -0.0086(15) C44 0.0531(18) 0.0561(19) 0.063(2) 0.0221(16) 0.0201(16) -0.0074(15) N1 0.0374(11) 0.0362(12) 0.0285(11) -0.0045(9) 0.0067(9) -0.0023(9) N2 0.0412(12) 0.0348(12) 0.0533(14) -0.0101(10) 0.0134(11) -0.0074(10) N3 0.0341(11) 0.0296(11) 0.0318(11) 0.0037(9) 0.0068(9) 0.0038(8) N4 0.0439(12) 0.0339(12) 0.0433(13) 0.0088(10) 0.0100(10) -0.0066(10) P1 0.0314(3) 0.0268(3) 0.0275(3) -0.0013(2) 0.0091(3) 0.0025(2) P2 0.0307(3) 0.0276(3) 0.0322(3) -0.0005(3) 0.0092(3) 0.0012(2) Li1 0.041(2) 0.033(2) 0.043(2) -0.0038(19) 0.012(2) -0.0015(18) Li2 0.039(2) 0.034(2) 0.037(2) 0.0080(18) 0.0090(18) -0.0020(18) _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 C1 C6 1.386(4) . ? C1 C2 1.390(4) . ? C1 P1 1.829(2) . ? C2 C3 1.385(4) . ? C2 H2 0.9300 . ? C3 C4 1.376(5) . ? C3 H3 0.9300 . ? C4 C5 1.372(5) . ? C4 H4 0.9300 . ? C5 C6 1.384(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.383(4) . ? C7 C8 1.392(4) . ? C7 P1 1.844(2) . ? C8 C9 1.386(4) . ? C8 H8 0.9300 . ? C9 C10 1.371(4) . ? C9 H9 0.9300 . ? C10 C11 1.370(4) . ? C10 H10 0.9300 . ? C11 C12 1.385(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.387(3) . ? C13 C18 1.437(3) . ? C13 P1 1.815(2) . ? C14 C15 1.388(4) . ? C14 H14 0.9300 . ? C15 C16 1.381(4) . ? C15 H15 0.9300 . ? C16 C17 1.371(4) . ? C16 H16 0.9300 . ? C17 C18 1.427(3) . ? C17 H17 0.9300 . ? C18 N1 1.346(3) . ? C19 N1 1.446(3) . ? C19 C20 1.507(4) . ? C19 Li1 2.736(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 N2 1.479(4) . ? C20 Li1 2.554(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N2 1.443(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 N2 1.449(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.383(4) . ? C23 C28 1.399(3) . ? C23 P2 1.845(2) . ? C23 Li2 2.500(5) . ? C24 C25 1.387(4) . ? C24 H24 0.9300 . ? C25 C26 1.379(4) . ? C25 H25 0.9300 . ? C26 C27 1.371(5) . ? C26 H26 0.9300 . ? C27 C28 1.379(4) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.390(3) . ? C29 C34 1.388(4) . ? C29 P2 1.831(2) . ? C30 C31 1.378(4) . ? C30 H30 0.9300 . ? C31 C32 1.375(4) . ? C31 H31 0.9300 . ? C32 C33 1.372(4) . ? C32 H32 0.9300 . ? C33 C34 1.387(4) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 C36 1.388(3) . ? C35 C40 1.426(3) . ? C35 P2 1.810(2) . ? C36 C37 1.387(4) . ? C36 H36 0.9300 . ? C37 C38 1.377(4) . ? C37 H37 0.9300 . ? C38 C39 1.379(4) . ? C38 H38 0.9300 . ? C39 C40 1.419(3) . ? C39 H39 0.9300 . ? C40 N3 1.369(3) . ? C41 N3 1.461(3) . ? C41 C42 1.509(4) . ? C41 Li2 2.726(5) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 N4 1.479(3) . ? C42 Li2 2.611(5) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 N4 1.469(4) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 N4 1.469(4) . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? N1 Li1 1.974(5) . ? N2 Li1 2.061(5) . ? N3 Li2 1.967(5) . ? N3 Li1 2.166(5) . ? N4 Li2 2.037(5) . ? P1 Li2 2.694(4) . ? P1 Li1 2.884(4) . ? P2 Li2 2.865(4) . ? P2 Li1 2.856(4) . ? Li1 Li2 2.644(6) . ? 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 C6 C1 C2 118.1(2) . . ? C6 C1 P1 123.9(2) . . ? C2 C1 P1 117.84(19) . . ? C3 C2 C1 121.1(3) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.4(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 120.6(3) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C12 C7 C8 118.1(2) . . ? C12 C7 P1 121.94(19) . . ? C8 C7 P1 119.98(19) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 119.5(3) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 120.9(3) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? C14 C13 C18 121.2(2) . . ? C14 C13 P1 123.61(19) . . ? C18 C13 P1 115.09(18) . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 118.4(3) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C17 C16 C15 121.8(2) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C16 C17 C18 122.0(3) . . ? C16 C17 H17 119.0 . . ? C18 C17 H17 119.0 . . ? N1 C18 C17 126.2(2) . . ? N1 C18 C13 118.6(2) . . ? C17 C18 C13 115.2(2) . . ? N1 C19 C20 111.0(2) . . ? N1 C19 Li1 44.11(15) . . ? C20 C19 Li1 66.92(18) . . ? N1 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? Li1 C19 H19A 125.2 . . ? N1 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? Li1 C19 H19B 125.2 . . ? H19A C19 H19B 108.0 . . ? N2 C20 C19 114.1(2) . . ? N2 C20 Li1 53.77(16) . . ? C19 C20 Li1 80.22(19) . . ? N2 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? Li1 C20 H20A 162.4 . . ? N2 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? Li1 C20 H20B 82.7 . . ? H20A C20 H20B 107.6 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 118.0(2) . . ? C24 C23 P2 124.14(19) . . ? C28 C23 P2 117.85(19) . . ? C24 C23 Li2 98.6(2) . . ? C28 C23 Li2 90.69(18) . . ? P2 C23 Li2 81.00(13) . . ? C23 C24 C25 120.7(3) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C26 C25 C24 120.4(3) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C27 C26 C25 119.5(3) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C26 C27 C28 120.5(3) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C23 120.8(3) . . ? C27 C28 H28 119.6 . . ? C23 C28 H28 119.6 . . ? C30 C29 C34 118.5(2) . . ? C30 C29 P2 123.64(19) . . ? C34 C29 P2 117.86(19) . . ? C29 C30 C31 120.9(2) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C32 C31 C30 120.0(3) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C33 C32 C31 120.0(3) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 120.3(3) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C29 C34 C33 120.3(3) . . ? C29 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C36 C35 C40 120.6(2) . . ? C36 C35 P2 124.1(2) . . ? C40 C35 P2 114.90(17) . . ? C35 C36 C37 121.9(3) . . ? C35 C36 H36 119.0 . . ? C37 C36 H36 119.0 . . ? C38 C37 C36 118.0(3) . . ? C38 C37 H37 121.0 . . ? C36 C37 H37 121.0 . . ? C37 C38 C39 121.8(3) . . ? C37 C38 H38 119.1 . . ? C39 C38 H38 119.1 . . ? C38 C39 C40 121.6(3) . . ? C38 C39 H39 119.2 . . ? C40 C39 H39 119.2 . . ? N3 C40 C39 125.4(2) . . ? N3 C40 C35 118.7(2) . . ? C39 C40 C35 115.9(2) . . ? N3 C41 C42 111.4(2) . . ? N3 C41 Li2 44.36(14) . . ? C42 C41 Li2 69.42(16) . . ? N3 C41 H41A 109.4 . . ? C42 C41 H41A 109.4 . . ? Li2 C41 H41A 138.5 . . ? N3 C41 H41B 109.4 . . ? C42 C41 H41B 109.4 . . ? Li2 C41 H41B 111.3 . . ? H41A C41 H41B 108.0 . . ? N4 C42 C41 113.9(2) . . ? N4 C42 Li2 51.07(14) . . ? C41 C42 Li2 77.81(17) . . ? N4 C42 H42A 108.8 . . ? C41 C42 H42A 108.8 . . ? Li2 C42 H42A 158.2 . . ? N4 C42 H42B 108.8 . . ? C41 C42 H42B 108.8 . . ? Li2 C42 H42B 88.9 . . ? H42A C42 H42B 107.7 . . ? N4 C43 H43A 109.5 . . ? N4 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? N4 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? N4 C44 H44A 109.5 . . ? N4 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? N4 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C18 N1 C19 115.4(2) . . ? C18 N1 Li1 139.3(2) . . ? C19 N1 Li1 105.2(2) . . ? C22 N2 C21 111.5(3) . . ? C22 N2 C20 109.7(3) . . ? C21 N2 C20 107.7(3) . . ? C22 N2 Li1 112.2(2) . . ? C21 N2 Li1 122.4(2) . . ? C20 N2 Li1 90.9(2) . . ? C40 N3 C41 114.6(2) . . ? C40 N3 Li2 134.9(2) . . ? C41 N3 Li2 104.36(19) . . ? C40 N3 Li1 102.55(18) . . ? C41 N3 Li1 115.1(2) . . ? Li2 N3 Li1 79.36(18) . . ? C43 N4 C44 109.4(2) . . ? C43 N4 C42 111.5(2) . . ? C44 N4 C42 107.6(2) . . ? C43 N4 Li2 108.7(2) . . ? C44 N4 Li2 124.0(2) . . ? C42 N4 Li2 94.54(19) . . ? C13 P1 C1 103.11(11) . . ? C13 P1 C7 102.18(11) . . ? C1 P1 C7 102.78(11) . . ? C13 P1 Li2 112.52(12) . . ? C1 P1 Li2 102.42(12) . . ? C7 P1 Li2 130.50(12) . . ? C13 P1 Li1 95.07(12) . . ? C1 P1 Li1 156.68(12) . . ? C7 P1 Li1 87.26(11) . . ? Li2 P1 Li1 56.46(12) . . ? C35 P2 C29 103.49(11) . . ? C35 P2 C23 103.60(11) . . ? C29 P2 C23 100.69(11) . . ? C35 P2 Li2 94.29(12) . . ? C29 P2 Li2 156.41(11) . . ? C23 P2 Li2 59.51(11) . . ? C35 P2 Li1 80.93(12) . . ? C29 P2 Li1 142.56(12) . . ? C23 P2 Li1 114.55(12) . . ? Li2 P2 Li1 55.05(12) . . ? N1 Li1 N2 88.15(19) . . ? N1 Li1 N3 118.8(2) . . ? N2 Li1 N3 117.5(2) . . ? N1 Li1 C20 63.51(15) . . ? N2 Li1 C20 35.37(12) . . ? N3 Li1 C20 105.74(19) . . ? N1 Li1 Li2 104.9(2) . . ? N2 Li1 Li2 163.2(2) . . ? N3 Li1 Li2 47.00(13) . . ? C20 Li1 Li2 143.5(2) . . ? N1 Li1 C19 30.64(11) . . ? N2 Li1 C19 61.06(14) . . ? N3 Li1 C19 116.5(2) . . ? C20 Li1 C19 32.87(11) . . ? Li2 Li1 C19 127.9(2) . . ? N1 Li1 P2 156.9(2) . . ? N2 Li1 P2 108.37(19) . . ? N3 Li1 P2 68.42(13) . . ? C20 Li1 P2 138.26(19) . . ? Li2 Li1 P2 62.65(13) . . ? C19 Li1 P2 169.35(19) . . ? N1 Li1 P1 70.17(14) . . ? N2 Li1 P1 137.9(2) . . ? N3 Li1 P1 104.62(16) . . ? C20 Li1 P1 132.61(19) . . ? Li2 Li1 P1 58.14(13) . . ? C19 Li1 P1 100.36(15) . . ? P2 Li1 P1 86.89(12) . . ? N3 Li2 N4 92.55(19) . . ? N3 Li2 C23 92.68(18) . . ? N4 Li2 C23 137.3(2) . . ? N3 Li2 C42 62.98(14) . . ? N4 Li2 C42 34.39(11) . . ? C23 Li2 C42 146.4(2) . . ? N3 Li2 Li1 53.65(15) . . ? N4 Li2 Li1 115.1(2) . . ? C23 Li2 Li1 101.79(18) . . ? C42 Li2 Li1 82.74(17) . . ? N3 Li2 P1 118.37(19) . . ? N4 Li2 P1 105.99(19) . . ? C23 Li2 P1 108.43(16) . . ? C42 Li2 P1 103.70(16) . . ? Li1 Li2 P1 65.40(14) . . ? N3 Li2 C41 31.28(10) . . ? N4 Li2 C41 61.48(13) . . ? C23 Li2 C41 117.32(18) . . ? C42 Li2 C41 32.77(10) . . ? Li1 Li2 C41 70.09(15) . . ? P1 Li2 C41 120.82(17) . . ? N3 Li2 P2 70.41(13) . . ? N4 Li2 P2 160.8(2) . . ? C23 Li2 P2 39.50(8) . . ? C42 Li2 P2 132.57(17) . . ? Li1 Li2 P2 62.30(13) . . ? P1 Li2 P2 90.41(12) . . ? C41 Li2 P2 101.65(14) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.398 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.097 #===END data_a7129 _database_code_depnum_ccdc_archive 'CCDC 834551' #TrackingRef '- [PNN]Ni_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 Cl N2 Ni P' _chemical_formula_sum 'C22 H24 Cl N2 Ni P' _chemical_formula_weight 441.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 10.034(3) _cell_length_b 10.622(3) _cell_length_c 19.542(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.008(13) _cell_angle_gamma 90.00 _cell_volume 2051.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.163 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.792 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10908 _diffrn_reflns_av_R_equivalents 0.1551 _diffrn_reflns_av_sigmaI/netI 0.1221 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 20.11 _reflns_number_total 1943 _reflns_number_gt 1198 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0350P)^2^+3.7606P] 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 1943 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1238 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 C1 C 0.4216(10) 0.2157(9) 0.6500(4) 0.0230(19) Uani 1 1 d . . . C2 C 0.4831(12) 0.1027(9) 0.6745(5) 0.033(3) Uani 1 1 d . . . H2 H 0.4425 0.0265 0.6596 0.040 Uiso 1 1 calc R . . C3 C 0.6048(13) 0.1035(10) 0.7212(5) 0.039(3) Uani 1 1 d . . . H3 H 0.6443 0.0280 0.7382 0.047 Uiso 1 1 calc R . . C4 C 0.6660(12) 0.2147(13) 0.7418(4) 0.047(3) Uani 1 1 d . . . H4 H 0.7490 0.2148 0.7716 0.056 Uiso 1 1 calc R . . C5 C 0.6057(14) 0.3279(11) 0.7189(5) 0.053(4) Uani 1 1 d . . . H5 H 0.6453 0.4040 0.7348 0.064 Uiso 1 1 calc R . . C6 C 0.4868(12) 0.3259(9) 0.6723(5) 0.038(3) Uani 1 1 d . . . H6 H 0.4488 0.4018 0.6551 0.046 Uiso 1 1 calc R . . C7 C 0.1561(10) 0.3165(8) 0.6268(4) 0.0230(19) Uani 1 1 d . . . C8 C 0.1388(11) 0.2955(9) 0.6954(5) 0.036(3) Uani 1 1 d . . . H8 H 0.1865 0.2306 0.7206 0.044 Uiso 1 1 calc R . . C9 C 0.0518(11) 0.3697(10) 0.7269(5) 0.041(3) Uani 1 1 d . . . H9 H 0.0415 0.3543 0.7726 0.049 Uiso 1 1 calc R . . C10 C -0.0185(11) 0.4657(10) 0.6899(5) 0.042(3) Uani 1 1 d . . . H10 H -0.0773 0.5146 0.7106 0.050 Uiso 1 1 calc R . . C11 C -0.0033(10) 0.4908(8) 0.6226(5) 0.031(3) Uani 1 1 d . . . H11 H -0.0510 0.5560 0.5976 0.037 Uiso 1 1 calc R . . C12 C 0.0851(10) 0.4165(8) 0.5929(5) 0.026(3) Uani 1 1 d . . . H12 H 0.0972 0.4350 0.5479 0.032 Uiso 1 1 calc R . . C13 C 0.2947(10) 0.2859(10) 0.5088(4) 0.026(3) Uani 1 1 d . . . C14 C 0.3354(10) 0.4075(8) 0.4977(5) 0.028(3) Uani 1 1 d . . . H14 H 0.3481 0.4649 0.5342 0.034 Uiso 1 1 calc R . . C15 C 0.3570(10) 0.4440(9) 0.4332(5) 0.032(3) Uani 1 1 d . . . H15 H 0.3791 0.5270 0.4248 0.039 Uiso 1 1 calc R . . C16 C 0.3455(10) 0.3559(11) 0.3814(5) 0.035(3) Uani 1 1 d . . . H16 H 0.3642 0.3801 0.3384 0.042 Uiso 1 1 calc R . . C17 C 0.3073(11) 0.2326(10) 0.3901(5) 0.036(3) Uani 1 1 d . . . H17 H 0.3013 0.1752 0.3538 0.043 Uiso 1 1 calc R . . C18 C 0.2776(10) 0.1959(9) 0.4552(5) 0.026(3) Uani 1 1 d . . . C19 C 0.2303(11) -0.0208(9) 0.4175(4) 0.042(3) Uani 1 1 d . . . H19A H 0.3222 -0.0413 0.4121 0.050 Uiso 1 1 calc R . . H19B H 0.1813 0.0074 0.3729 0.050 Uiso 1 1 calc R . . C20 C 0.1631(11) -0.1335(8) 0.4414(5) 0.033(3) Uani 1 1 d . . . H20A H 0.0656 -0.1244 0.4298 0.040 Uiso 1 1 calc R . . H20B H 0.1890 -0.2083 0.4184 0.040 Uiso 1 1 calc R . . C21 C 0.1164(11) -0.2416(8) 0.5437(5) 0.047(3) Uani 1 1 d . . . H21A H 0.1432 -0.2504 0.5931 0.071 Uiso 1 1 calc R . . H21B H 0.1256 -0.3211 0.5217 0.071 Uiso 1 1 calc R . . H21C H 0.0238 -0.2145 0.5334 0.071 Uiso 1 1 calc R . . C22 C 0.3447(12) -0.1919(9) 0.5351(5) 0.051(3) Uani 1 1 d . . . H22A H 0.3697 -0.1993 0.5846 0.076 Uiso 1 1 calc R . . H22B H 0.4040 -0.1332 0.5181 0.076 Uiso 1 1 calc R . . H22C H 0.3520 -0.2726 0.5140 0.076 Uiso 1 1 calc R . . N1 N 0.2313(8) 0.0771(7) 0.4690(3) 0.028(2) Uani 1 1 d . . . N2 N 0.2042(9) -0.1467(7) 0.5176(4) 0.029(2) Uani 1 1 d . . . P1 P 0.2642(3) 0.2144(2) 0.58817(11) 0.0265(8) Uani 1 1 d . . . Cl1 Cl 0.1538(3) -0.0229(2) 0.65457(11) 0.0378(8) Uani 1 1 d . . . Ni1 Ni 0.20701(14) 0.02714(10) 0.55539(6) 0.0261(4) Uani 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 C1 0.030(6) 0.019(5) 0.022(4) -0.005(4) 0.010(4) -0.003(4) C2 0.031(9) 0.030(7) 0.042(7) -0.012(5) 0.015(6) -0.008(6) C3 0.038(10) 0.033(8) 0.046(8) -0.002(6) 0.006(7) 0.003(7) C4 0.040(9) 0.071(9) 0.025(6) 0.000(7) -0.004(6) -0.002(9) C5 0.068(12) 0.046(9) 0.039(8) 0.008(6) -0.010(7) -0.019(8) C6 0.054(10) 0.026(7) 0.029(6) 0.005(5) -0.008(6) 0.006(7) C7 0.030(6) 0.019(5) 0.022(4) -0.005(4) 0.010(4) -0.003(4) C8 0.043(9) 0.030(6) 0.038(7) -0.003(5) 0.012(6) 0.008(6) C9 0.038(9) 0.061(8) 0.024(6) -0.001(6) 0.004(6) 0.006(7) C10 0.032(8) 0.049(8) 0.047(7) -0.006(6) 0.017(6) 0.016(7) C11 0.034(8) 0.017(6) 0.043(7) -0.003(5) 0.010(6) 0.009(6) C12 0.029(8) 0.021(6) 0.032(6) -0.004(5) 0.013(6) -0.004(6) C13 0.025(7) 0.031(7) 0.023(6) -0.005(6) 0.009(5) -0.008(6) C14 0.039(8) 0.017(7) 0.030(7) -0.007(5) 0.008(6) -0.011(6) C15 0.033(8) 0.023(7) 0.040(7) 0.010(6) 0.004(6) -0.010(6) C16 0.020(8) 0.050(8) 0.035(7) 0.008(7) 0.008(5) -0.013(6) C17 0.047(9) 0.023(7) 0.036(7) -0.006(5) 0.002(6) 0.005(6) C18 0.022(7) 0.031(7) 0.023(7) 0.008(6) 0.001(5) 0.003(6) C19 0.042(8) 0.044(7) 0.039(6) 0.001(6) 0.003(5) -0.012(7) C20 0.032(9) 0.022(7) 0.040(7) -0.013(5) -0.008(6) 0.004(6) C21 0.041(9) 0.037(7) 0.063(8) 0.008(6) 0.005(6) -0.002(7) C22 0.053(10) 0.032(7) 0.068(8) -0.008(6) 0.014(7) 0.006(7) N1 0.040(7) 0.022(6) 0.020(5) -0.005(4) -0.005(4) 0.008(5) N2 0.030(7) 0.022(5) 0.033(6) -0.001(4) 0.000(5) 0.018(5) P1 0.031(2) 0.0233(16) 0.0261(16) -0.0009(12) 0.0070(14) 0.0010(15) Cl1 0.042(2) 0.0377(16) 0.0351(15) 0.0063(13) 0.0110(13) 0.0003(15) Ni1 0.0276(9) 0.0221(8) 0.0287(8) -0.0004(6) 0.0055(6) 0.0005(8) _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 C1 C6 1.374(12) . ? C1 C2 1.395(12) . ? C1 P1 1.815(10) . ? C2 C3 1.391(13) . ? C2 H2 0.9300 . ? C3 C4 1.360(13) . ? C3 H3 0.9300 . ? C4 C5 1.385(13) . ? C4 H4 0.9300 . ? C5 C6 1.369(13) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.382(11) . ? C7 C8 1.400(11) . ? C7 P1 1.791(9) . ? C8 C9 1.396(13) . ? C8 H8 0.9300 . ? C9 C10 1.372(12) . ? C9 H9 0.9300 . ? C10 C11 1.376(11) . ? C10 H10 0.9300 . ? C11 C12 1.387(12) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.383(11) . ? C13 C18 1.406(11) . ? C13 P1 1.801(9) . ? C14 C15 1.372(11) . ? C14 H14 0.9300 . ? C15 C16 1.368(11) . ? C15 H15 0.9300 . ? C16 C17 1.383(12) . ? C16 H16 0.9300 . ? C17 C18 1.411(11) . ? C17 H17 0.9300 . ? C18 N1 1.387(10) . ? C19 N1 1.447(10) . ? C19 C20 1.489(11) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 N2 1.479(10) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N2 1.487(11) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 N2 1.472(12) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? N1 Ni1 1.826(7) . ? N2 Ni1 1.987(7) . ? P1 Ni1 2.138(3) . ? Cl1 Ni1 2.164(2) . ? 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 C6 C1 C2 117.8(9) . . ? C6 C1 P1 121.9(8) . . ? C2 C1 P1 120.3(8) . . ? C3 C2 C1 120.3(9) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 120.0(10) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.6(11) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 118.9(10) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C1 122.4(9) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? C12 C7 C8 116.2(8) . . ? C12 C7 P1 124.3(7) . . ? C8 C7 P1 119.5(7) . . ? C9 C8 C7 121.6(9) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C10 C9 C8 119.4(9) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 121.1(9) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C12 118.3(9) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C7 C12 C11 123.4(9) . . ? C7 C12 H12 118.3 . . ? C11 C12 H12 118.3 . . ? C14 C13 C18 121.3(8) . . ? C14 C13 P1 128.9(7) . . ? C18 C13 P1 109.8(7) . . ? C15 C14 C13 120.4(8) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 118.6(9) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C17 123.1(9) . . ? C15 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C16 C17 C18 118.6(9) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? N1 C18 C13 118.4(8) . . ? N1 C18 C17 123.9(9) . . ? C13 C18 C17 117.8(9) . . ? N1 C19 C20 107.9(7) . . ? N1 C19 H19A 110.1 . . ? C20 C19 H19A 110.1 . . ? N1 C19 H19B 110.1 . . ? C20 C19 H19B 110.1 . . ? H19A C19 H19B 108.4 . . ? N2 C20 C19 109.3(7) . . ? N2 C20 H20A 109.8 . . ? C19 C20 H20A 109.8 . . ? N2 C20 H20B 109.8 . . ? C19 C20 H20B 109.8 . . ? H20A C20 H20B 108.3 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C18 N1 C19 118.7(7) . . ? C18 N1 Ni1 123.2(6) . . ? C19 N1 Ni1 116.7(6) . . ? C22 N2 C20 110.7(7) . . ? C22 N2 C21 107.4(7) . . ? C20 N2 C21 109.4(8) . . ? C22 N2 Ni1 105.4(6) . . ? C20 N2 Ni1 105.7(5) . . ? C21 N2 Ni1 118.2(6) . . ? C7 P1 C13 108.3(4) . . ? C7 P1 C1 103.6(4) . . ? C13 P1 C1 108.2(4) . . ? C7 P1 Ni1 122.6(3) . . ? C13 P1 Ni1 102.2(3) . . ? C1 P1 Ni1 111.3(3) . . ? N1 Ni1 N2 85.5(3) . . ? N1 Ni1 P1 86.2(3) . . ? N2 Ni1 P1 164.1(3) . . ? N1 Ni1 Cl1 173.1(3) . . ? N2 Ni1 Cl1 96.6(2) . . ? P1 Ni1 Cl1 93.17(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 20.11 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.533 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.091 #===END data_3145 _database_code_depnum_ccdc_archive 'CCDC 834552' #TrackingRef '- [PNN]Ni_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N2 Ni P' _chemical_formula_sum 'C23 H27 N2 Ni P' _chemical_formula_weight 421.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3899(3) _cell_length_b 10.5707(3) _cell_length_c 11.3703(5) _cell_angle_alpha 102.5040(10) _cell_angle_beta 92.234(2) _cell_angle_gamma 117.474(2) _cell_volume 1067.67(6) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9607 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.993 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8735 _exptl_absorpt_correction_T_max 0.9428 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10003 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0768 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3727 _reflns_number_gt 2547 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1009P)^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 3727 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1004 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1883 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 C1 C 0.6472(6) 1.0145(6) 0.2072(5) 0.0602(15) Uani 1 1 d . . . H1A H 0.7470 1.0276 0.2069 0.090 Uiso 1 1 calc R . . H1B H 0.6524 1.1096 0.2450 0.090 Uiso 1 1 calc R . . H1C H 0.5954 0.9773 0.1231 0.090 Uiso 1 1 calc R . . C2 C 0.3764(6) 0.6821(5) 0.0055(4) 0.0441(12) Uani 1 1 d . . . C3 C 0.4991(7) 0.6653(7) -0.0137(5) 0.0616(15) Uani 1 1 d . . . H3 H 0.5726 0.6930 0.0534 0.074 Uiso 1 1 calc R . . C4 C 0.5148(8) 0.6080(7) -0.1309(6) 0.0726(18) Uani 1 1 d . . . H4 H 0.5983 0.5952 -0.1435 0.087 Uiso 1 1 calc R . . C5 C 0.4109(8) 0.5701(7) -0.2277(6) 0.0710(18) Uani 1 1 d . . . H5 H 0.4224 0.5306 -0.3075 0.085 Uiso 1 1 calc R . . C6 C 0.2899(8) 0.5885(7) -0.2112(5) 0.0704(17) Uani 1 1 d . . . H6 H 0.2179 0.5624 -0.2791 0.084 Uiso 1 1 calc R . . C7 C 0.2738(6) 0.6460(6) -0.0933(5) 0.0570(14) Uani 1 1 d . . . H7 H 0.1910 0.6604 -0.0812 0.068 Uiso 1 1 calc R . . C8 C 0.2245(6) 0.8130(5) 0.1499(4) 0.0443(12) Uani 1 1 d . . . C9 C 0.2708(7) 0.9469(6) 0.1199(5) 0.0592(14) Uani 1 1 d . . . H9 H 0.3678 0.9990 0.1033 0.071 Uiso 1 1 calc R . . C10 C 0.1760(8) 1.0035(7) 0.1143(6) 0.0713(17) Uani 1 1 d . . . H10 H 0.2086 1.0951 0.0945 0.086 Uiso 1 1 calc R . . C11 C 0.0341(8) 0.9295(7) 0.1370(6) 0.0703(17) Uani 1 1 d . . . H11 H -0.0306 0.9694 0.1319 0.084 Uiso 1 1 calc R . . C12 C -0.0129(7) 0.7975(7) 0.1671(5) 0.0644(16) Uani 1 1 d . . . H12 H -0.1103 0.7458 0.1830 0.077 Uiso 1 1 calc R . . C13 C 0.0826(6) 0.7403(6) 0.1740(5) 0.0511(13) Uani 1 1 d . . . H13 H 0.0501 0.6497 0.1957 0.061 Uiso 1 1 calc R . . C14 C 0.2595(5) 0.5772(5) 0.2135(4) 0.0406(11) Uani 1 1 d . . . C15 C 0.1390(6) 0.4439(5) 0.1484(5) 0.0531(13) Uani 1 1 d . . . H15 H 0.0979 0.4351 0.0690 0.064 Uiso 1 1 calc R . . C16 C 0.0790(7) 0.3249(6) 0.1982(6) 0.0677(17) Uani 1 1 d . . . H16 H -0.0033 0.2342 0.1542 0.081 Uiso 1 1 calc R . . C17 C 0.1410(7) 0.3408(7) 0.3126(7) 0.0733(18) Uani 1 1 d . . . H17 H 0.1004 0.2589 0.3469 0.088 Uiso 1 1 calc R . . C18 C 0.2603(7) 0.4709(7) 0.3805(5) 0.0620(15) Uani 1 1 d . . . H18 H 0.2987 0.4768 0.4599 0.074 Uiso 1 1 calc R . . C19 C 0.3251(6) 0.5946(6) 0.3327(5) 0.0476(13) Uani 1 1 d . . . C20 C 0.5165(7) 0.7475(7) 0.5054(5) 0.0642(15) Uani 1 1 d . . . H20A H 0.5642 0.6845 0.4997 0.077 Uiso 1 1 calc R . . H20B H 0.4456 0.7219 0.5632 0.077 Uiso 1 1 calc R . . C21 C 0.6301(7) 0.9093(7) 0.5467(5) 0.0686(17) Uani 1 1 d . . . H21A H 0.5821 0.9683 0.5801 0.082 Uiso 1 1 calc R . . H21B H 0.7050 0.9243 0.6125 0.082 Uiso 1 1 calc R . . C22 C 0.7973(7) 0.8934(9) 0.4089(7) 0.093(2) Uani 1 1 d . . . H22A H 0.8449 0.9275 0.3408 0.140 Uiso 1 1 calc R . . H22B H 0.7371 0.7855 0.3840 0.140 Uiso 1 1 calc R . . H22C H 0.8724 0.9224 0.4788 0.140 Uiso 1 1 calc R . . C23 C 0.7956(7) 1.1252(7) 0.4837(6) 0.083(2) Uani 1 1 d . . . H23A H 0.7337 1.1708 0.5069 0.125 Uiso 1 1 calc R . . H23B H 0.8447 1.1604 0.4165 0.125 Uiso 1 1 calc R . . H23C H 0.8697 1.1523 0.5538 0.125 Uiso 1 1 calc R . . N1 N 0.4435(5) 0.7272(5) 0.3871(4) 0.0491(10) Uani 1 1 d . . . N2 N 0.7025(5) 0.9612(5) 0.4438(4) 0.0597(12) Uani 1 1 d . . . Ni1 Ni 0.54016(7) 0.87095(7) 0.30109(6) 0.0476(3) Uani 1 1 d . . . P1 P 0.35397(14) 0.74222(14) 0.16309(11) 0.0409(3) Uani 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 C1 0.052(3) 0.044(3) 0.048(3) 0.011(2) 0.002(3) -0.006(3) C2 0.057(3) 0.040(3) 0.038(3) 0.013(2) 0.010(2) 0.024(3) C3 0.066(4) 0.079(4) 0.056(4) 0.022(3) 0.017(3) 0.047(3) C4 0.094(5) 0.085(4) 0.071(4) 0.033(4) 0.040(4) 0.062(4) C5 0.106(5) 0.071(4) 0.054(4) 0.022(3) 0.031(4) 0.053(4) C6 0.088(5) 0.081(4) 0.035(3) 0.009(3) 0.004(3) 0.038(4) C7 0.062(4) 0.065(4) 0.045(3) 0.012(3) 0.007(3) 0.032(3) C8 0.058(3) 0.043(3) 0.036(3) 0.007(2) 0.007(2) 0.028(3) C9 0.072(4) 0.059(3) 0.052(3) 0.018(3) 0.016(3) 0.033(3) C10 0.102(5) 0.065(4) 0.068(4) 0.028(3) 0.013(4) 0.053(4) C11 0.090(5) 0.080(5) 0.065(4) 0.017(3) 0.009(4) 0.061(4) C12 0.062(4) 0.071(4) 0.068(4) 0.011(3) 0.012(3) 0.041(3) C13 0.059(3) 0.047(3) 0.048(3) 0.009(2) 0.008(3) 0.027(3) C14 0.038(3) 0.042(3) 0.045(3) 0.014(2) 0.009(2) 0.021(2) C15 0.049(3) 0.047(3) 0.065(4) 0.015(3) 0.009(3) 0.025(3) C16 0.059(4) 0.042(3) 0.094(5) 0.016(3) 0.010(3) 0.018(3) C17 0.077(4) 0.058(4) 0.091(5) 0.039(4) 0.026(4) 0.028(4) C18 0.075(4) 0.072(4) 0.055(3) 0.035(3) 0.014(3) 0.041(4) C19 0.054(3) 0.058(3) 0.046(3) 0.021(3) 0.016(3) 0.035(3) C20 0.071(4) 0.083(4) 0.040(3) 0.013(3) -0.002(3) 0.041(4) C21 0.067(4) 0.098(5) 0.041(3) 0.003(3) -0.006(3) 0.047(4) C22 0.062(4) 0.120(6) 0.092(5) -0.006(4) 0.008(4) 0.054(4) C23 0.056(4) 0.081(5) 0.065(4) -0.019(3) -0.003(3) 0.011(3) N1 0.049(3) 0.059(3) 0.036(2) 0.012(2) 0.002(2) 0.024(2) N2 0.042(3) 0.074(3) 0.047(3) -0.009(2) 0.001(2) 0.027(2) Ni1 0.0411(4) 0.0515(5) 0.0394(4) 0.0058(3) 0.0047(3) 0.0165(3) P1 0.0427(7) 0.0430(7) 0.0347(7) 0.0095(5) 0.0051(6) 0.0192(6) _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 C1 Ni1 1.979(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C7 1.375(7) . ? C2 C3 1.384(7) . ? C2 P1 1.829(5) . ? C3 C4 1.388(8) . ? C3 H3 0.9500 . ? C4 C5 1.362(9) . ? C4 H4 0.9500 . ? C5 C6 1.372(9) . ? C5 H5 0.9500 . ? C6 C7 1.398(8) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.384(7) . ? C8 C9 1.395(7) . ? C8 P1 1.831(5) . ? C9 C10 1.374(8) . ? C9 H9 0.9500 . ? C10 C11 1.380(9) . ? C10 H10 0.9500 . ? C11 C12 1.376(8) . ? C11 H11 0.9500 . ? C12 C13 1.388(7) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.396(7) . ? C14 C19 1.428(7) . ? C14 P1 1.798(5) . ? C15 C16 1.380(8) . ? C15 H15 0.9500 . ? C16 C17 1.370(9) . ? C16 H16 0.9500 . ? C17 C18 1.385(9) . ? C17 H17 0.9500 . ? C18 C19 1.408(7) . ? C18 H18 0.9500 . ? C19 N1 1.354(7) . ? C20 N1 1.441(7) . ? C20 C21 1.512(9) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 N2 1.483(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N2 1.483(7) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N2 1.492(8) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N1 Ni1 1.894(4) . ? N2 Ni1 2.005(4) . ? Ni1 P1 2.1133(14) . ? 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 Ni1 C1 H1A 109.5 . . ? Ni1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Ni1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 C3 119.1(5) . . ? C7 C2 P1 122.9(4) . . ? C3 C2 P1 117.9(4) . . ? C2 C3 C4 120.1(6) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.3(5) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.7(5) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C7 119.1(6) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C2 C7 C6 120.8(5) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C13 C8 C9 118.5(5) . . ? C13 C8 P1 121.8(4) . . ? C9 C8 P1 119.6(4) . . ? C10 C9 C8 120.0(6) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 121.2(6) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 119.5(5) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 119.7(6) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C8 C13 C12 121.2(5) . . ? C8 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C19 121.4(5) . . ? C15 C14 P1 127.0(4) . . ? C19 C14 P1 111.6(4) . . ? C16 C15 C14 120.7(5) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 118.3(6) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C16 C17 C18 123.0(6) . . ? C16 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C17 C18 C19 120.4(5) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? N1 C19 C18 127.0(5) . . ? N1 C19 C14 116.8(4) . . ? C18 C19 C14 116.2(5) . . ? N1 C20 C21 105.5(5) . . ? N1 C20 H20A 110.6 . . ? C21 C20 H20A 110.6 . . ? N1 C20 H20B 110.6 . . ? C21 C20 H20B 110.6 . . ? H20A C20 H20B 108.8 . . ? N2 C21 C20 110.9(5) . . ? N2 C21 H21A 109.5 . . ? C20 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 108.0 . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N2 C23 H23A 109.5 . . ? N2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 N1 C20 118.6(5) . . ? C19 N1 Ni1 122.1(3) . . ? C20 N1 Ni1 118.0(4) . . ? C22 N2 C21 109.5(5) . . ? C22 N2 C23 109.0(5) . . ? C21 N2 C23 108.9(4) . . ? C22 N2 Ni1 104.7(4) . . ? C21 N2 Ni1 105.3(3) . . ? C23 N2 Ni1 119.0(4) . . ? N1 Ni1 C1 176.5(2) . . ? N1 Ni1 N2 83.96(19) . . ? C1 Ni1 N2 95.7(2) . . ? N1 Ni1 P1 86.09(13) . . ? C1 Ni1 P1 94.11(17) . . ? N2 Ni1 P1 169.74(16) . . ? C14 P1 C2 106.2(2) . . ? C14 P1 C8 106.6(2) . . ? C2 P1 C8 104.1(2) . . ? C14 P1 Ni1 101.53(16) . . ? C2 P1 Ni1 120.12(17) . . ? C8 P1 Ni1 117.04(16) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.589 _refine_diff_density_min -0.932 _refine_diff_density_rms 0.257 data_3374 _database_code_depnum_ccdc_archive 'CCDC 834553' #TrackingRef '3374_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety '4(C24 H29 N2 Ni P), C4 H10 O' _chemical_formula_sum 'C24 H29 N2 Ni O P' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 200(2) _chemical_formula_weight 451.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.2700(2) _cell_length_b 9.27600(10) _cell_length_c 32.8820(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.7350(10) _cell_angle_gamma 90.00 _cell_volume 4590.49(10) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 44467 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 0.932 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5925 _exptl_absorpt_correction_T_max 0.8161 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 31891 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.02 _reflns_number_total 8024 _reflns_number_gt 7026 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1636P)^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 SHELXL _refine_ls_extinction_coef 0.0304(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8024 _refine_ls_number_parameters 554 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1675 _refine_ls_wR_factor_gt 0.1432 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.890 _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 0.38985(2) 0.46205(4) 0.175984(10) 0.01917(17) Uani 1 1 d . . . P1 P 0.36453(5) 0.47884(8) 0.11138(2) 0.0177(2) Uani 1 1 d . . . N1 N 0.41336(17) 0.2639(3) 0.16779(7) 0.0213(5) Uani 1 1 d . . . N2 N 0.43694(17) 0.4191(3) 0.23544(7) 0.0262(6) Uani 1 1 d . . . C1 C 0.2650(2) 0.6869(4) 0.18832(11) 0.0381(8) Uani 1 1 d . . . H1A H 0.2531 0.7900 0.1910 0.057 Uiso 1 1 calc R . . H1B H 0.2559 0.6368 0.2135 0.057 Uiso 1 1 calc R . . H1C H 0.2244 0.6474 0.1647 0.057 Uiso 1 1 calc R . . C2 C 0.3605(2) 0.6659(3) 0.18183(9) 0.0262(7) Uani 1 1 d . . . H2A H 0.4012 0.7073 0.2056 0.031 Uiso 1 1 calc R . . H2B H 0.3697 0.7187 0.1567 0.031 Uiso 1 1 calc R . . C3 C 0.5338(2) 0.4538(4) 0.24008(10) 0.0347(8) Uani 1 1 d . . . H3A H 0.5640 0.4222 0.2673 0.052 Uiso 1 1 calc R . . H3B H 0.5414 0.5581 0.2374 0.052 Uiso 1 1 calc R . . H3C H 0.5594 0.4038 0.2186 0.052 Uiso 1 1 calc R . . C4 C 0.3990(3) 0.4950(4) 0.26836(9) 0.0373(8) Uani 1 1 d . . . H4A H 0.4278 0.4598 0.2954 0.056 Uiso 1 1 calc R . . H4B H 0.3350 0.4762 0.2648 0.056 Uiso 1 1 calc R . . H4C H 0.4092 0.5989 0.2665 0.056 Uiso 1 1 calc R . . C5 C 0.4245(2) 0.2614(3) 0.24068(9) 0.0274(7) Uani 1 1 d . . . H5A H 0.3620 0.2420 0.2433 0.033 Uiso 1 1 calc R . . H5B H 0.4629 0.2285 0.2663 0.033 Uiso 1 1 calc R . . C6 C 0.4476(2) 0.1778(3) 0.20415(8) 0.0246(6) Uani 1 1 d . . . H6A H 0.5127 0.1654 0.2068 0.029 Uiso 1 1 calc R . . H6B H 0.4194 0.0814 0.2023 0.029 Uiso 1 1 calc R . . C7 C 0.40778(18) 0.2030(3) 0.12977(8) 0.0198(6) Uani 1 1 d . . . C8 C 0.4272(2) 0.0586(3) 0.12090(9) 0.0241(6) Uani 1 1 d . . . H8 H 0.4483 -0.0056 0.1429 0.029 Uiso 1 1 calc R . . C9 C 0.4161(2) 0.0096(3) 0.08081(9) 0.0265(7) Uani 1 1 d . . . H9 H 0.4303 -0.0877 0.0756 0.032 Uiso 1 1 calc R . . C10 C 0.3841(2) 0.1006(3) 0.04754(9) 0.0261(7) Uani 1 1 d . . . H10 H 0.3760 0.0650 0.0201 0.031 Uiso 1 1 calc R . . C11 C 0.36449(19) 0.2424(3) 0.05511(8) 0.0231(6) Uani 1 1 d . . . H11 H 0.3427 0.3046 0.0327 0.028 Uiso 1 1 calc R . . C12 C 0.37647(18) 0.2947(3) 0.09520(8) 0.0188(6) Uani 1 1 d . . . C13 C 0.2595(2) 0.5452(3) 0.08281(8) 0.0221(6) Uani 1 1 d . . . C14 C 0.1878(2) 0.4510(4) 0.07273(9) 0.0275(7) Uani 1 1 d . . . H14 H 0.1949 0.3515 0.0793 0.033 Uiso 1 1 calc R . . C15 C 0.1064(2) 0.5019(4) 0.05326(10) 0.0373(8) Uani 1 1 d . . . H15 H 0.0576 0.4376 0.0467 0.045 Uiso 1 1 calc R . . C16 C 0.0957(2) 0.6469(5) 0.04323(10) 0.0454(10) Uani 1 1 d . . . H16 H 0.0400 0.6817 0.0295 0.054 Uiso 1 1 calc R . . C17 C 0.1658(3) 0.7394(5) 0.05323(11) 0.0462(10) Uani 1 1 d . . . H17 H 0.1579 0.8388 0.0466 0.055 Uiso 1 1 calc R . . C18 C 0.2479(2) 0.6910(4) 0.07276(10) 0.0319(7) Uani 1 1 d . . . H18 H 0.2961 0.7565 0.0793 0.038 Uiso 1 1 calc R . . C19 C 0.44912(19) 0.5810(3) 0.09047(8) 0.0196(6) Uani 1 1 d . . . C20 C 0.44543(19) 0.6006(3) 0.04811(8) 0.0222(6) Uani 1 1 d . . . H20 H 0.3954 0.5666 0.0294 0.027 Uiso 1 1 calc R . . C21 C 0.5141(2) 0.6693(3) 0.03297(8) 0.0231(6) Uani 1 1 d . . . H21 H 0.5107 0.6816 0.0041 0.028 Uiso 1 1 calc R . . C22 C 0.5873(2) 0.7198(3) 0.05968(9) 0.0250(6) Uani 1 1 d . . . H22 H 0.6344 0.7662 0.0492 0.030 Uiso 1 1 calc R . . C23 C 0.5915(2) 0.7022(3) 0.10204(9) 0.0245(6) Uani 1 1 d . . . H23 H 0.6416 0.7371 0.1205 0.029 Uiso 1 1 calc R . . C24 C 0.5232(2) 0.6340(3) 0.11752(8) 0.0220(6) Uani 1 1 d . . . H24 H 0.5265 0.6232 0.1465 0.026 Uiso 1 1 calc R . . Ni2 Ni 0.80315(2) 0.27920(4) 0.113609(10) 0.01947(17) Uani 1 1 d . . . P2 P 0.91210(5) 0.36782(8) 0.15319(2) 0.0195(2) Uani 1 1 d . . . N3 N 0.76930(16) 0.1984(3) 0.16209(7) 0.0228(5) Uani 1 1 d . . . N4 N 0.68534(16) 0.2000(3) 0.08536(7) 0.0236(5) Uani 1 1 d . . . C25 C 0.7948(2) 0.4999(4) 0.04829(10) 0.0367(8) Uani 1 1 d . . . H25A H 0.8188 0.5348 0.0243 0.055 Uiso 1 1 calc R . . H25B H 0.8025 0.5741 0.0698 0.055 Uiso 1 1 calc R . . H25C H 0.7314 0.4785 0.0401 0.055 Uiso 1 1 calc R . . C26 C 0.8444(2) 0.3621(3) 0.06499(8) 0.0265(7) Uani 1 1 d . . . H26A H 0.9085 0.3843 0.0724 0.032 Uiso 1 1 calc R . . H26B H 0.8373 0.2889 0.0428 0.032 Uiso 1 1 calc R . . C27 C 0.6161(2) 0.3106(3) 0.08837(9) 0.0274(7) Uani 1 1 d . . . H27A H 0.5572 0.2698 0.0783 0.041 Uiso 1 1 calc R . . H27B H 0.6258 0.3945 0.0716 0.041 Uiso 1 1 calc R . . H27C H 0.6197 0.3402 0.1172 0.041 Uiso 1 1 calc R . . C28 C 0.6759(2) 0.1517(4) 0.04176(9) 0.0327(7) Uani 1 1 d . . . H28A H 0.6166 0.1107 0.0330 0.049 Uiso 1 1 calc R . . H28B H 0.7209 0.0783 0.0393 0.049 Uiso 1 1 calc R . . H28C H 0.6840 0.2342 0.0241 0.049 Uiso 1 1 calc R . . C29 C 0.6697(2) 0.0734(3) 0.11133(9) 0.0258(7) Uani 1 1 d . . . H29A H 0.7091 -0.0070 0.1063 0.031 Uiso 1 1 calc R . . H29B H 0.6074 0.0406 0.1037 0.031 Uiso 1 1 calc R . . C30 C 0.68802(19) 0.1143(3) 0.15646(9) 0.0255(6) Uani 1 1 d . . . H30A H 0.6384 0.1720 0.1637 0.031 Uiso 1 1 calc R . . H30B H 0.6957 0.0270 0.1740 0.031 Uiso 1 1 calc R . . C31 C 0.80985(19) 0.2367(3) 0.20063(8) 0.0203(6) Uani 1 1 d . . . C32 C 0.7811(2) 0.1971(3) 0.23798(9) 0.0254(7) Uani 1 1 d . . . H32 H 0.7297 0.1390 0.2373 0.030 Uiso 1 1 calc R . . C33 C 0.8289(2) 0.2442(3) 0.27558(9) 0.0267(7) Uani 1 1 d . . . H33 H 0.8095 0.2161 0.3004 0.032 Uiso 1 1 calc R . . C34 C 0.9037(2) 0.3306(3) 0.27792(9) 0.0275(7) Uani 1 1 d . . . H34 H 0.9347 0.3622 0.3039 0.033 Uiso 1 1 calc R . . C35 C 0.93268(19) 0.3700(3) 0.24168(9) 0.0231(6) Uani 1 1 d . . . H35 H 0.9839 0.4288 0.2427 0.028 Uiso 1 1 calc R . . C36 C 0.88668(19) 0.3234(3) 0.20381(8) 0.0210(6) Uani 1 1 d . . . C37 C 1.0239(2) 0.3028(3) 0.15124(9) 0.0250(6) Uani 1 1 d . . . C38 C 1.0345(2) 0.1882(4) 0.12514(11) 0.0340(8) Uani 1 1 d . . . H38 H 0.9850 0.1521 0.1065 0.041 Uiso 1 1 calc R . . C39 C 1.1190(3) 0.1261(4) 0.12651(13) 0.0454(10) Uani 1 1 d . . . H39 H 1.1263 0.0457 0.1095 0.055 Uiso 1 1 calc R . . C40 C 1.1916(3) 0.1822(4) 0.15264(14) 0.0506(11) Uani 1 1 d . . . H40 H 1.2485 0.1398 0.1536 0.061 Uiso 1 1 calc R . . C41 C 1.1818(2) 0.2983(4) 0.17704(12) 0.0417(9) Uani 1 1 d . . . H41 H 1.2324 0.3378 0.1942 0.050 Uiso 1 1 calc R . . C42 C 1.0989(2) 0.3590(4) 0.17708(10) 0.0340(8) Uani 1 1 d . . . H42 H 1.0928 0.4386 0.1946 0.041 Uiso 1 1 calc R . . C43 C 0.91901(19) 0.5635(3) 0.15165(8) 0.0228(6) Uani 1 1 d . . . C44 C 0.9818(2) 0.6368(3) 0.13292(9) 0.0273(7) Uani 1 1 d . . . H44 H 1.0275 0.5845 0.1231 0.033 Uiso 1 1 calc R . . C45 C 0.9775(2) 0.7859(3) 0.12863(10) 0.0329(8) Uani 1 1 d . . . H45 H 1.0206 0.8349 0.1160 0.039 Uiso 1 1 calc R . . C46 C 0.9111(2) 0.8633(4) 0.14253(9) 0.0320(7) Uani 1 1 d . . . H46 H 0.9079 0.9650 0.1392 0.038 Uiso 1 1 calc R . . C47 C 0.8491(2) 0.7909(3) 0.16141(10) 0.0296(7) Uani 1 1 d . . . H47 H 0.8036 0.8438 0.1712 0.036 Uiso 1 1 calc R . . C48 C 0.8529(2) 0.6433(3) 0.16607(9) 0.0271(7) Uani 1 1 d . . . H48 H 0.8102 0.5954 0.1792 0.032 Uiso 1 1 calc R . . O1 O 1.0000 0.0000 0.0000 0.0681(14) Uani 1 2 d S . . C49 C 0.8536(15) -0.135(2) 0.0025(7) 0.073(6) Uani 0.50 1 d P A -1 H49A H 0.8070 -0.1448 0.0195 0.110 Uiso 0.50 1 calc PR A -1 H49B H 0.8805 -0.2298 -0.0004 0.110 Uiso 0.50 1 calc PR A -1 H49C H 0.8275 -0.0985 -0.0248 0.110 Uiso 0.50 1 calc PR A -1 C50 C 0.9240(7) -0.0316(9) 0.0229(2) 0.045(2) Uani 0.50 1 d P A -1 H50A H 0.9494 -0.0707 0.0504 0.054 Uiso 0.50 1 calc PR A -1 H50B H 0.8947 0.0608 0.0274 0.054 Uiso 0.50 1 calc PR A -1 C51 C 1.0560(5) 0.0895(9) 0.0123(2) 0.0446(18) Uani 0.50 1 d P A -1 H51A H 1.0867 0.0614 0.0401 0.054 Uiso 0.50 1 calc PR A -1 H51B H 1.0265 0.1833 0.0147 0.054 Uiso 0.50 1 calc PR A -1 C49A C 1.1221(11) 0.1065(16) -0.0149(5) 0.052(4) Uani 0.50 1 d P A -1 H49D H 1.1642 0.1824 -0.0041 0.078 Uiso 0.50 1 calc PR A -1 H49E H 1.0921 0.1330 -0.0427 0.078 Uiso 0.50 1 calc PR A -1 H49F H 1.1540 0.0155 -0.0162 0.078 Uiso 0.50 1 calc PR A -1 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 0.0232(3) 0.0172(3) 0.0172(2) 0.00009(12) 0.00354(16) 0.00066(14) P1 0.0189(4) 0.0154(4) 0.0186(4) 0.0011(3) 0.0027(3) 0.0009(3) N1 0.0246(13) 0.0204(13) 0.0181(11) 0.0042(9) 0.0011(9) 0.0026(10) N2 0.0291(14) 0.0284(14) 0.0203(12) -0.0011(10) 0.0022(10) -0.0028(11) C1 0.045(2) 0.0307(18) 0.0419(19) -0.0003(14) 0.0149(16) 0.0117(15) C2 0.0329(17) 0.0227(16) 0.0229(14) -0.0014(11) 0.0044(12) -0.0001(13) C3 0.0306(18) 0.042(2) 0.0292(17) 0.0030(13) -0.0028(13) -0.0080(15) C4 0.052(2) 0.039(2) 0.0208(16) -0.0037(14) 0.0081(14) 0.0042(17) C5 0.0315(17) 0.0275(17) 0.0229(15) 0.0064(12) 0.0041(12) -0.0007(13) C6 0.0272(16) 0.0205(15) 0.0257(15) 0.0056(12) 0.0038(12) 0.0040(12) C7 0.0154(14) 0.0200(15) 0.0243(14) 0.0024(11) 0.0039(11) -0.0002(11) C8 0.0246(16) 0.0190(15) 0.0282(15) 0.0024(11) 0.0031(12) 0.0007(12) C9 0.0265(16) 0.0158(15) 0.0372(17) -0.0054(12) 0.0058(13) -0.0016(12) C10 0.0286(16) 0.0235(16) 0.0260(14) -0.0089(12) 0.0040(12) -0.0036(13) C11 0.0219(15) 0.0271(16) 0.0193(14) 0.0004(11) 0.0008(11) -0.0031(12) C12 0.0186(14) 0.0139(14) 0.0234(14) 0.0011(10) 0.0026(11) -0.0008(11) C13 0.0228(15) 0.0242(16) 0.0200(14) 0.0035(11) 0.0054(11) 0.0045(12) C14 0.0251(16) 0.0338(18) 0.0243(15) 0.0015(12) 0.0058(12) -0.0018(13) C15 0.0233(17) 0.059(2) 0.0302(17) -0.0044(16) 0.0056(13) 0.0047(16) C16 0.032(2) 0.070(3) 0.0319(18) -0.0045(17) -0.0006(14) 0.0246(19) C17 0.055(3) 0.046(2) 0.038(2) 0.0081(16) 0.0049(17) 0.028(2) C18 0.0377(19) 0.0239(16) 0.0337(17) 0.0032(13) 0.0052(14) 0.0093(14) C19 0.0221(15) 0.0123(13) 0.0247(14) 0.0005(10) 0.0053(11) 0.0015(11) C20 0.0240(15) 0.0214(15) 0.0199(13) -0.0022(11) 0.0001(11) 0.0009(12) C21 0.0319(17) 0.0178(14) 0.0210(14) 0.0003(11) 0.0087(12) -0.0003(12) C22 0.0278(16) 0.0179(15) 0.0302(16) 0.0008(11) 0.0072(12) -0.0021(12) C23 0.0242(16) 0.0196(15) 0.0278(15) -0.0001(11) -0.0014(12) -0.0018(12) C24 0.0286(16) 0.0157(14) 0.0207(13) -0.0006(10) 0.0012(11) 0.0023(12) Ni2 0.0189(3) 0.0189(3) 0.0198(2) -0.00037(13) 0.00089(16) -0.00134(14) P2 0.0173(4) 0.0187(4) 0.0222(4) 0.0011(3) 0.0028(3) -0.0019(3) N3 0.0209(13) 0.0200(13) 0.0261(12) 0.0013(9) -0.0001(10) -0.0054(10) N4 0.0216(13) 0.0219(13) 0.0257(12) -0.0045(9) -0.0008(10) 0.0009(10) C25 0.043(2) 0.0364(19) 0.0322(18) 0.0077(15) 0.0099(15) 0.0042(16) C26 0.0292(17) 0.0284(17) 0.0210(14) 0.0005(12) 0.0019(12) 0.0000(13) C27 0.0235(16) 0.0241(16) 0.0326(16) -0.0018(12) -0.0012(12) 0.0032(12) C28 0.0306(18) 0.0359(19) 0.0295(16) -0.0086(13) -0.0010(13) -0.0020(14) C29 0.0214(15) 0.0164(15) 0.0372(17) -0.0037(12) -0.0024(12) -0.0004(12) C30 0.0192(15) 0.0207(15) 0.0354(16) 0.0023(12) 0.0013(12) -0.0001(12) C31 0.0184(15) 0.0175(14) 0.0248(14) 0.0012(11) 0.0035(11) 0.0036(11) C32 0.0249(16) 0.0234(16) 0.0288(15) 0.0036(12) 0.0071(12) -0.0014(12) C33 0.0286(17) 0.0276(16) 0.0245(15) 0.0013(12) 0.0068(12) 0.0053(13) C34 0.0355(18) 0.0242(16) 0.0217(14) -0.0024(11) 0.0019(12) 0.0030(13) C35 0.0232(15) 0.0193(15) 0.0259(14) -0.0037(11) 0.0018(11) 0.0008(12) C36 0.0224(15) 0.0191(15) 0.0211(14) 0.0018(11) 0.0028(11) 0.0020(11) C37 0.0211(15) 0.0245(16) 0.0311(15) 0.0082(12) 0.0092(12) -0.0003(12) C38 0.0323(18) 0.0223(16) 0.051(2) 0.0058(14) 0.0189(15) -0.0034(13) C39 0.043(2) 0.0258(19) 0.077(3) 0.0111(17) 0.036(2) 0.0054(16) C40 0.0267(19) 0.042(2) 0.088(3) 0.034(2) 0.025(2) 0.0077(17) C41 0.0215(17) 0.053(2) 0.051(2) 0.0255(18) 0.0060(15) 0.0038(15) C42 0.0226(16) 0.044(2) 0.0341(17) 0.0162(14) 0.0027(13) -0.0032(14) C43 0.0224(15) 0.0230(15) 0.0203(14) 0.0013(11) -0.0045(11) -0.0027(12) C44 0.0291(17) 0.0280(17) 0.0252(15) -0.0004(12) 0.0054(12) -0.0055(13) C45 0.0386(19) 0.0247(17) 0.0359(17) 0.0016(13) 0.0077(14) -0.0102(14) C46 0.0386(19) 0.0227(16) 0.0322(16) 0.0037(12) -0.0013(13) -0.0057(14) C47 0.0244(16) 0.0275(17) 0.0358(17) 0.0002(13) 0.0018(13) 0.0015(13) C48 0.0226(16) 0.0262(17) 0.0318(16) 0.0039(12) 0.0028(12) -0.0040(13) O1 0.112(4) 0.042(3) 0.059(3) -0.001(2) 0.043(3) 0.011(3) C49 0.076(13) 0.040(7) 0.107(16) -0.019(8) 0.027(10) -0.005(7) C50 0.073(6) 0.028(4) 0.033(4) 0.005(3) 0.004(4) 0.016(4) C51 0.048(5) 0.039(5) 0.041(4) 0.008(3) -0.008(3) 0.016(4) C49A 0.055(10) 0.030(9) 0.070(9) 0.004(7) 0.003(7) 0.016(7) _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 N1 1.901(2) . ? Ni1 C2 1.960(3) . ? Ni1 N2 2.006(2) . ? Ni1 P1 2.0996(8) . ? P1 C12 1.807(3) . ? P1 C13 1.823(3) . ? P1 C19 1.827(3) . ? N1 C7 1.361(4) . ? N1 C6 1.459(3) . ? N2 C4 1.489(4) . ? N2 C5 1.489(4) . ? N2 C3 1.496(4) . ? C1 C2 1.522(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.521(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.413(4) . ? C7 C12 1.436(4) . ? C8 C9 1.378(4) . ? C8 H8 0.9500 . ? C9 C10 1.403(4) . ? C9 H9 0.9500 . ? C10 C11 1.382(4) . ? C10 H10 0.9500 . ? C11 C12 1.387(4) . ? C11 H11 0.9500 . ? C13 C14 1.396(4) . ? C13 C18 1.397(4) . ? C14 C15 1.381(5) . ? C14 H14 0.9500 . ? C15 C16 1.388(6) . ? C15 H15 0.9500 . ? C16 C17 1.367(6) . ? C16 H16 0.9500 . ? C17 C18 1.384(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.396(4) . ? C19 C24 1.404(4) . ? C20 C21 1.389(4) . ? C20 H20 0.9500 . ? C21 C22 1.382(4) . ? C21 H21 0.9500 . ? C22 C23 1.393(4) . ? C22 H22 0.9500 . ? C23 C24 1.389(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? Ni2 N3 1.911(2) . ? Ni2 C26 1.971(3) . ? Ni2 N4 2.018(2) . ? Ni2 P2 2.0988(8) . ? P2 C36 1.819(3) . ? P2 C43 1.819(3) . ? P2 C37 1.821(3) . ? N3 C31 1.360(4) . ? N3 C30 1.451(4) . ? N4 C28 1.486(4) . ? N4 C27 1.488(4) . ? N4 C29 1.495(4) . ? C25 C26 1.539(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.511(4) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C36 1.411(4) . ? C31 C32 1.420(4) . ? C32 C33 1.395(4) . ? C32 H32 0.9500 . ? C33 C34 1.387(5) . ? C33 H33 0.9500 . ? C34 C35 1.388(4) . ? C34 H34 0.9500 . ? C35 C36 1.391(4) . ? C35 H35 0.9500 . ? C37 C38 1.394(5) . ? C37 C42 1.406(5) . ? C38 C39 1.407(5) . ? C38 H38 0.9500 . ? C39 C40 1.383(6) . ? C39 H39 0.9500 . ? C40 C41 1.366(6) . ? C40 H40 0.9500 . ? C41 C42 1.385(5) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? C43 C48 1.398(4) . ? C43 C44 1.400(4) . ? C44 C45 1.390(5) . ? C44 H44 0.9500 . ? C45 C46 1.381(5) . ? C45 H45 0.9500 . ? C46 C47 1.390(5) . ? C46 H46 0.9500 . ? C47 C48 1.378(5) . ? C47 H47 0.9500 . ? C48 H48 0.9500 . ? O1 C51 1.211(9) . ? O1 C51 1.211(9) 3_755 ? O1 C50 1.515(10) 3_755 ? O1 C50 1.515(10) . ? C49 C50 1.513(16) . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 C49A 1.46(2) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C49A H49D 0.9800 . ? C49A H49E 0.9800 . ? C49A H49F 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 N1 Ni1 C2 176.90(11) . . ? N1 Ni1 N2 84.31(10) . . ? C2 Ni1 N2 98.42(11) . . ? N1 Ni1 P1 86.28(7) . . ? C2 Ni1 P1 91.24(9) . . ? N2 Ni1 P1 167.23(8) . . ? C12 P1 C13 106.91(13) . . ? C12 P1 C19 105.45(13) . . ? C13 P1 C19 104.32(13) . . ? C12 P1 Ni1 102.55(9) . . ? C13 P1 Ni1 122.81(9) . . ? C19 P1 Ni1 113.46(9) . . ? C7 N1 C6 118.9(2) . . ? C7 N1 Ni1 123.21(18) . . ? C6 N1 Ni1 117.61(18) . . ? C4 N2 C5 107.9(2) . . ? C4 N2 C3 108.9(3) . . ? C5 N2 C3 110.0(3) . . ? C4 N2 Ni1 119.7(2) . . ? C5 N2 Ni1 106.05(17) . . ? C3 N2 Ni1 104.00(18) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 Ni1 112.2(2) . . ? C1 C2 H2A 109.2 . . ? Ni1 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? Ni1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 C6 111.0(2) . . ? N2 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N2 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N1 C6 C5 105.6(2) . . ? N1 C6 H6A 110.6 . . ? C5 C6 H6A 110.6 . . ? N1 C6 H6B 110.6 . . ? C5 C6 H6B 110.6 . . ? H6A C6 H6B 108.8 . . ? N1 C7 C8 126.9(3) . . ? N1 C7 C12 116.2(3) . . ? C8 C7 C12 116.8(2) . . ? C9 C8 C7 121.0(3) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 121.2(3) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 119.4(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 120.4(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 121.2(3) . . ? C11 C12 P1 127.3(2) . . ? C7 C12 P1 111.3(2) . . ? C14 C13 C18 119.1(3) . . ? C14 C13 P1 119.9(2) . . ? C18 C13 P1 120.9(2) . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 119.7(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 121.2(4) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C13 119.5(3) . . ? C17 C18 H18 120.2 . . ? C13 C18 H18 120.2 . . ? C20 C19 C24 118.6(3) . . ? C20 C19 P1 122.1(2) . . ? C24 C19 P1 119.2(2) . . ? C21 C20 C19 120.8(3) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C20 120.4(3) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 119.4(3) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C19 120.1(3) . . ? C23 C24 H24 119.9 . . ? C19 C24 H24 119.9 . . ? N3 Ni2 C26 177.11(11) . . ? N3 Ni2 N4 83.99(10) . . ? C26 Ni2 N4 98.67(11) . . ? N3 Ni2 P2 86.23(7) . . ? C26 Ni2 P2 91.25(9) . . ? N4 Ni2 P2 168.32(8) . . ? C36 P2 C43 105.90(13) . . ? C36 P2 C37 107.66(13) . . ? C43 P2 C37 105.67(14) . . ? C36 P2 Ni2 102.08(10) . . ? C43 P2 Ni2 114.65(9) . . ? C37 P2 Ni2 119.85(11) . . ? C31 N3 C30 120.3(2) . . ? C31 N3 Ni2 122.0(2) . . ? C30 N3 Ni2 116.79(18) . . ? C28 N4 C27 108.5(2) . . ? C28 N4 C29 108.4(2) . . ? C27 N4 C29 108.6(2) . . ? C28 N4 Ni2 119.17(19) . . ? C27 N4 Ni2 107.84(18) . . ? C29 N4 Ni2 103.83(16) . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C25 C26 Ni2 114.1(2) . . ? C25 C26 H26A 108.7 . . ? Ni2 C26 H26A 108.7 . . ? C25 C26 H26B 108.7 . . ? Ni2 C26 H26B 108.7 . . ? H26A C26 H26B 107.6 . . ? N4 C27 H27A 109.5 . . ? N4 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N4 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N4 C28 H28A 109.5 . . ? N4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N4 C29 C30 110.0(2) . . ? N4 C29 H29A 109.7 . . ? C30 C29 H29A 109.7 . . ? N4 C29 H29B 109.7 . . ? C30 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? N3 C30 C29 105.8(2) . . ? N3 C30 H30A 110.6 . . ? C29 C30 H30A 110.6 . . ? N3 C30 H30B 110.6 . . ? C29 C30 H30B 110.6 . . ? H30A C30 H30B 108.7 . . ? N3 C31 C36 117.4(3) . . ? N3 C31 C32 125.4(3) . . ? C36 C31 C32 117.2(3) . . ? C33 C32 C31 119.6(3) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C34 C33 C32 122.2(3) . . ? C34 C33 H33 118.9 . . ? C32 C33 H33 118.9 . . ? C33 C34 C35 118.9(3) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.5 . . ? C34 C35 C36 120.0(3) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 C31 122.1(3) . . ? C35 C36 P2 126.5(2) . . ? C31 C36 P2 111.4(2) . . ? C38 C37 C42 119.1(3) . . ? C38 C37 P2 118.8(2) . . ? C42 C37 P2 121.9(3) . . ? C37 C38 C39 119.7(3) . . ? C37 C38 H38 120.2 . . ? C39 C38 H38 120.2 . . ? C40 C39 C38 120.0(4) . . ? C40 C39 H39 120.0 . . ? C38 C39 H39 120.0 . . ? C41 C40 C39 120.4(3) . . ? C41 C40 H40 119.8 . . ? C39 C40 H40 119.8 . . ? C40 C41 C42 120.8(4) . . ? C40 C41 H41 119.6 . . ? C42 C41 H41 119.6 . . ? C41 C42 C37 120.0(4) . . ? C41 C42 H42 120.0 . . ? C37 C42 H42 120.0 . . ? C48 C43 C44 118.7(3) . . ? C48 C43 P2 118.0(2) . . ? C44 C43 P2 123.0(2) . . ? C45 C44 C43 120.3(3) . . ? C45 C44 H44 119.9 . . ? C43 C44 H44 119.9 . . ? C46 C45 C44 120.5(3) . . ? C46 C45 H45 119.7 . . ? C44 C45 H45 119.7 . . ? C45 C46 C47 119.4(3) . . ? C45 C46 H46 120.3 . . ? C47 C46 H46 120.3 . . ? C48 C47 C46 120.7(3) . . ? C48 C47 H47 119.6 . . ? C46 C47 H47 119.6 . . ? C47 C48 C43 120.5(3) . . ? C47 C48 H48 119.8 . . ? C43 C48 H48 119.8 . . ? C51 O1 C51 179.999(2) . 3_755 ? C51 O1 C50 58.4(5) . 3_755 ? C51 O1 C50 121.6(5) 3_755 3_755 ? C51 O1 C50 121.6(5) . . ? C51 O1 C50 58.4(5) 3_755 . ? C50 O1 C50 179.998(2) 3_755 . ? C50 C49 H49A 109.5 . . ? C50 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C50 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C49 C50 O1 116.7(12) . . ? C49 C50 H50A 108.1 . . ? O1 C50 H50A 108.1 . . ? C49 C50 H50B 108.1 . . ? O1 C50 H50B 108.1 . . ? H50A C50 H50B 107.3 . . ? O1 C51 C49A 113.0(8) . . ? O1 C51 H51A 109.0 . . ? C49A C51 H51A 109.0 . . ? O1 C51 H51B 109.0 . . ? C49A C51 H51B 109.0 . . ? H51A C51 H51B 107.8 . . ? C51 C49A H49D 109.5 . . ? C51 C49A H49E 109.5 . . ? H49D C49A H49E 109.5 . . ? C51 C49A H49F 109.5 . . ? H49D C49A H49F 109.5 . . ? H49E C49A H49F 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 N1 Ni1 P1 C12 3.32(12) . . . . ? C2 Ni1 P1 C12 -174.83(13) . . . . ? N2 Ni1 P1 C12 45.9(4) . . . . ? N1 Ni1 P1 C13 123.19(14) . . . . ? C2 Ni1 P1 C13 -54.95(15) . . . . ? N2 Ni1 P1 C13 165.8(4) . . . . ? N1 Ni1 P1 C19 -109.89(13) . . . . ? C2 Ni1 P1 C19 71.96(14) . . . . ? N2 Ni1 P1 C19 -67.3(4) . . . . ? C2 Ni1 N1 C7 37(2) . . . . ? N2 Ni1 N1 C7 -171.4(2) . . . . ? P1 Ni1 N1 C7 -0.1(2) . . . . ? C2 Ni1 N1 C6 -150(2) . . . . ? N2 Ni1 N1 C6 2.2(2) . . . . ? P1 Ni1 N1 C6 173.5(2) . . . . ? N1 Ni1 N2 C4 -145.9(3) . . . . ? C2 Ni1 N2 C4 32.6(3) . . . . ? P1 Ni1 N2 C4 171.4(3) . . . . ? N1 Ni1 N2 C5 -23.72(19) . . . . ? C2 Ni1 N2 C5 154.8(2) . . . . ? P1 Ni1 N2 C5 -66.5(4) . . . . ? N1 Ni1 N2 C3 92.3(2) . . . . ? C2 Ni1 N2 C3 -89.1(2) . . . . ? P1 Ni1 N2 C3 49.6(5) . . . . ? N1 Ni1 C2 C1 60(2) . . . . ? N2 Ni1 C2 C1 -91.7(2) . . . . ? P1 Ni1 C2 C1 96.7(2) . . . . ? C4 N2 C5 C6 170.6(3) . . . . ? C3 N2 C5 C6 -70.7(3) . . . . ? Ni1 N2 C5 C6 41.2(3) . . . . ? C7 N1 C6 C5 -166.6(2) . . . . ? Ni1 N1 C6 C5 19.5(3) . . . . ? N2 C5 C6 N1 -39.5(3) . . . . ? C6 N1 C7 C8 3.9(4) . . . . ? Ni1 N1 C7 C8 177.5(2) . . . . ? C6 N1 C7 C12 -177.9(3) . . . . ? Ni1 N1 C7 C12 -4.4(4) . . . . ? N1 C7 C8 C9 178.0(3) . . . . ? C12 C7 C8 C9 -0.2(4) . . . . ? C7 C8 C9 C10 -0.8(5) . . . . ? C8 C9 C10 C11 0.8(5) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C10 C11 C12 C7 -1.1(4) . . . . ? C10 C11 C12 P1 174.0(2) . . . . ? N1 C7 C12 C11 -177.2(3) . . . . ? C8 C7 C12 C11 1.1(4) . . . . ? N1 C7 C12 P1 7.0(3) . . . . ? C8 C7 C12 P1 -174.7(2) . . . . ? C13 P1 C12 C11 47.8(3) . . . . ? C19 P1 C12 C11 -62.8(3) . . . . ? Ni1 P1 C12 C11 178.2(2) . . . . ? C13 P1 C12 C7 -136.7(2) . . . . ? C19 P1 C12 C7 112.7(2) . . . . ? Ni1 P1 C12 C7 -6.3(2) . . . . ? C12 P1 C13 C14 33.6(3) . . . . ? C19 P1 C13 C14 145.0(2) . . . . ? Ni1 P1 C13 C14 -84.2(2) . . . . ? C12 P1 C13 C18 -150.1(2) . . . . ? C19 P1 C13 C18 -38.7(3) . . . . ? Ni1 P1 C13 C18 92.2(3) . . . . ? C18 C13 C14 C15 -0.3(4) . . . . ? P1 C13 C14 C15 176.1(2) . . . . ? C13 C14 C15 C16 0.6(5) . . . . ? C14 C15 C16 C17 -0.9(5) . . . . ? C15 C16 C17 C18 0.9(5) . . . . ? C16 C17 C18 C13 -0.6(5) . . . . ? C14 C13 C18 C17 0.3(5) . . . . ? P1 C13 C18 C17 -176.1(2) . . . . ? C12 P1 C19 C20 66.7(3) . . . . ? C13 P1 C19 C20 -45.8(3) . . . . ? Ni1 P1 C19 C20 178.2(2) . . . . ? C12 P1 C19 C24 -109.2(2) . . . . ? C13 P1 C19 C24 138.3(2) . . . . ? Ni1 P1 C19 C24 2.2(3) . . . . ? C24 C19 C20 C21 0.9(4) . . . . ? P1 C19 C20 C21 -175.1(2) . . . . ? C19 C20 C21 C22 -0.2(4) . . . . ? C20 C21 C22 C23 -0.4(4) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? C22 C23 C24 C19 0.5(4) . . . . ? C20 C19 C24 C23 -1.0(4) . . . . ? P1 C19 C24 C23 175.0(2) . . . . ? N3 Ni2 P2 C36 -7.05(12) . . . . ? C26 Ni2 P2 C36 174.37(13) . . . . ? N4 Ni2 P2 C36 26.1(4) . . . . ? N3 Ni2 P2 C43 -121.03(13) . . . . ? C26 Ni2 P2 C43 60.38(14) . . . . ? N4 Ni2 P2 C43 -87.9(4) . . . . ? N3 Ni2 P2 C37 111.67(13) . . . . ? C26 Ni2 P2 C37 -66.91(14) . . . . ? N4 Ni2 P2 C37 144.8(4) . . . . ? C26 Ni2 N3 C31 39(2) . . . . ? N4 Ni2 N3 C31 -163.7(2) . . . . ? P2 Ni2 N3 C31 10.0(2) . . . . ? C26 Ni2 N3 C30 -152(2) . . . . ? N4 Ni2 N3 C30 5.4(2) . . . . ? P2 Ni2 N3 C30 179.0(2) . . . . ? N3 Ni2 N4 C28 -148.7(2) . . . . ? C26 Ni2 N4 C28 30.1(2) . . . . ? P2 Ni2 N4 C28 178.0(3) . . . . ? N3 Ni2 N4 C27 87.07(19) . . . . ? C26 Ni2 N4 C27 -94.1(2) . . . . ? P2 Ni2 N4 C27 53.8(5) . . . . ? N3 Ni2 N4 C29 -28.09(18) . . . . ? C26 Ni2 N4 C29 150.78(18) . . . . ? P2 Ni2 N4 C29 -61.3(4) . . . . ? N3 Ni2 C26 C25 -130(2) . . . . ? N4 Ni2 C26 C25 72.6(2) . . . . ? P2 Ni2 C26 C25 -101.2(2) . . . . ? C28 N4 C29 C30 174.2(2) . . . . ? C27 N4 C29 C30 -68.1(3) . . . . ? Ni2 N4 C29 C30 46.5(2) . . . . ? C31 N3 C30 C29 -171.9(2) . . . . ? Ni2 N3 C30 C29 18.9(3) . . . . ? N4 C29 C30 N3 -43.2(3) . . . . ? C30 N3 C31 C36 -177.5(3) . . . . ? Ni2 N3 C31 C36 -8.9(4) . . . . ? C30 N3 C31 C32 2.3(4) . . . . ? Ni2 N3 C31 C32 171.0(2) . . . . ? N3 C31 C32 C33 -179.9(3) . . . . ? C36 C31 C32 C33 -0.1(4) . . . . ? C31 C32 C33 C34 0.7(5) . . . . ? C32 C33 C34 C35 -0.8(5) . . . . ? C33 C34 C35 C36 0.2(4) . . . . ? C34 C35 C36 C31 0.5(4) . . . . ? C34 C35 C36 P2 178.0(2) . . . . ? N3 C31 C36 C35 179.3(3) . . . . ? C32 C31 C36 C35 -0.5(4) . . . . ? N3 C31 C36 P2 1.4(3) . . . . ? C32 C31 C36 P2 -178.4(2) . . . . ? C43 P2 C36 C35 -52.5(3) . . . . ? C37 P2 C36 C35 60.2(3) . . . . ? Ni2 P2 C36 C35 -172.8(2) . . . . ? C43 P2 C36 C31 125.3(2) . . . . ? C37 P2 C36 C31 -122.0(2) . . . . ? Ni2 P2 C36 C31 5.0(2) . . . . ? C36 P2 C37 C38 111.8(3) . . . . ? C43 P2 C37 C38 -135.4(2) . . . . ? Ni2 P2 C37 C38 -4.1(3) . . . . ? C36 P2 C37 C42 -64.3(3) . . . . ? C43 P2 C37 C42 48.6(3) . . . . ? Ni2 P2 C37 C42 179.9(2) . . . . ? C42 C37 C38 C39 3.1(5) . . . . ? P2 C37 C38 C39 -173.0(2) . . . . ? C37 C38 C39 C40 -2.3(5) . . . . ? C38 C39 C40 C41 -0.3(5) . . . . ? C39 C40 C41 C42 2.0(5) . . . . ? C40 C41 C42 C37 -1.1(5) . . . . ? C38 C37 C42 C41 -1.5(4) . . . . ? P2 C37 C42 C41 174.6(2) . . . . ? C36 P2 C43 C48 -45.3(2) . . . . ? C37 P2 C43 C48 -159.3(2) . . . . ? Ni2 P2 C43 C48 66.4(2) . . . . ? C36 P2 C43 C44 141.5(2) . . . . ? C37 P2 C43 C44 27.4(3) . . . . ? Ni2 P2 C43 C44 -106.8(2) . . . . ? C48 C43 C44 C45 -0.5(4) . . . . ? P2 C43 C44 C45 172.7(2) . . . . ? C43 C44 C45 C46 -0.4(5) . . . . ? C44 C45 C46 C47 0.9(5) . . . . ? C45 C46 C47 C48 -0.5(5) . . . . ? C46 C47 C48 C43 -0.4(5) . . . . ? C44 C43 C48 C47 0.8(4) . . . . ? P2 C43 C48 C47 -172.7(2) . . . . ? C51 O1 C50 C49 174.4(12) . . . . ? C51 O1 C50 C49 -5.6(12) 3_755 . . . ? C50 O1 C50 C49 -153(6) 3_755 . . . ? C51 O1 C51 C49A -176(59) 3_755 . . . ? C50 O1 C51 C49A 1.7(7) 3_755 . . . ? C50 O1 C51 C49A -178.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.892 _refine_diff_density_min -1.283 _refine_diff_density_rms 0.313 #===END data_8383 _database_code_depnum_ccdc_archive 'CCDC 834554' #TrackingRef '- [PNN]Ni_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H37 N2 Ni P' _chemical_formula_sum 'C28 H37 N2 Ni P' _chemical_formula_weight 491.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7598(3) _cell_length_b 10.5483(2) _cell_length_c 14.2416(4) _cell_angle_alpha 68.739(2) _cell_angle_beta 73.9460(10) _cell_angle_gamma 89.1460(10) _cell_volume 1307.11(6) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 12346 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour 'red brown' _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.821 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8183 _exptl_absorpt_correction_T_max 0.9291 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16017 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.42 _reflns_number_total 4792 _reflns_number_gt 3609 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1229P)^2^+0.0564P] 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 SHELXL _refine_ls_extinction_coef 0.085(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4792 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.2051 _refine_ls_wR_factor_gt 0.1673 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0.003 _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 0.64898(5) 0.44740(5) 0.64222(4) 0.0449(3) Uani 1 1 d . . . P1 P 0.69217(11) 0.61625(11) 0.67785(8) 0.0403(3) Uani 1 1 d . . . N1 N 0.7403(4) 0.5593(4) 0.5002(3) 0.0514(9) Uani 1 1 d . . . N2 N 0.6509(4) 0.2965(4) 0.5870(3) 0.0562(10) Uani 1 1 d . . . C1 C 0.8240(4) 0.5925(4) 0.7517(3) 0.0419(9) Uani 1 1 d . . . C2 C 0.8828(5) 0.4697(5) 0.7799(3) 0.0501(10) Uani 1 1 d . . . H2 H 0.8520 0.3986 0.7644 0.060 Uiso 1 1 calc R . . C3 C 0.9883(5) 0.4510(5) 0.8316(4) 0.0591(12) Uani 1 1 d . . . H3 H 1.0275 0.3678 0.8504 0.071 Uiso 1 1 calc R . . C4 C 1.0340(5) 0.5545(5) 0.8546(4) 0.0567(12) Uani 1 1 d . . . H4 H 1.1047 0.5421 0.8887 0.068 Uiso 1 1 calc R . . C5 C 0.9752(5) 0.6784(5) 0.8274(4) 0.0617(12) Uani 1 1 d . . . H5 H 1.0067 0.7493 0.8428 0.074 Uiso 1 1 calc R . . C6 C 0.8698(5) 0.6962(5) 0.7773(4) 0.0564(11) Uani 1 1 d . . . H6 H 0.8289 0.7787 0.7606 0.068 Uiso 1 1 calc R . . C7 C 0.5495(4) 0.6922(4) 0.7466(3) 0.0435(9) Uani 1 1 d . . . C8 C 0.5070(5) 0.6498(5) 0.8554(4) 0.0636(13) Uani 1 1 d . . . H8 H 0.5570 0.5865 0.8946 0.076 Uiso 1 1 calc R . . C9 C 0.3907(6) 0.7009(7) 0.9063(4) 0.0757(16) Uani 1 1 d . . . H9 H 0.3611 0.6694 0.9795 0.091 Uiso 1 1 calc R . . C10 C 0.3195(5) 0.7966(6) 0.8503(5) 0.0702(15) Uani 1 1 d . . . H10 H 0.2430 0.8322 0.8850 0.084 Uiso 1 1 calc R . . C11 C 0.3603(5) 0.8411(5) 0.7424(5) 0.0657(14) Uani 1 1 d . . . H11 H 0.3106 0.9061 0.7044 0.079 Uiso 1 1 calc R . . C12 C 0.4747(5) 0.7899(5) 0.6897(4) 0.0526(11) Uani 1 1 d . . . H12 H 0.5018 0.8205 0.6165 0.063 Uiso 1 1 calc R . . C13 C 0.7745(4) 0.7450(4) 0.5493(3) 0.0429(9) Uani 1 1 d . . . C14 C 0.8170(5) 0.8809(5) 0.5246(4) 0.0522(11) Uani 1 1 d . . . H14 H 0.8001 0.9153 0.5779 0.063 Uiso 1 1 calc R . . C15 C 0.8843(5) 0.9659(5) 0.4220(4) 0.0591(12) Uani 1 1 d . . . H15 H 0.9123 1.0571 0.4057 0.071 Uiso 1 1 calc R . . C16 C 0.9088(5) 0.9130(5) 0.3441(4) 0.0594(12) Uani 1 1 d . . . H16 H 0.9552 0.9695 0.2750 0.071 Uiso 1 1 calc R . . C17 C 0.8670(5) 0.7794(5) 0.3652(3) 0.0567(12) Uani 1 1 d . . . H17 H 0.8865 0.7472 0.3106 0.068 Uiso 1 1 calc R . . C18 C 0.7947(4) 0.6900(5) 0.4690(3) 0.0477(10) Uani 1 1 d . . . C19 C 0.7698(6) 0.4912(6) 0.4250(4) 0.0679(14) Uani 1 1 d . . . H19A H 0.8669 0.4651 0.4134 0.081 Uiso 1 1 calc R . . H19B H 0.7584 0.5515 0.3581 0.081 Uiso 1 1 calc R . . C20 C 0.6652(6) 0.3683(6) 0.4717(5) 0.0734(15) Uani 1 1 d . . . H20A H 0.6968 0.3063 0.4353 0.088 Uiso 1 1 calc R . . H20B H 0.5727 0.3951 0.4628 0.088 Uiso 1 1 calc R . . C21 C 0.5301(7) 0.1917(6) 0.6301(6) 0.0882(19) Uani 1 1 d . . . H21A H 0.4442 0.2344 0.6225 0.132 Uiso 1 1 calc R . . H21B H 0.5195 0.1413 0.7034 0.132 Uiso 1 1 calc R . . H21C H 0.5473 0.1307 0.5928 0.132 Uiso 1 1 calc R . . C22 C 0.7837(6) 0.2326(6) 0.5986(5) 0.0732(15) Uani 1 1 d . . . H22A H 0.8622 0.3023 0.5703 0.110 Uiso 1 1 calc R . . H22B H 0.8020 0.1717 0.5612 0.110 Uiso 1 1 calc R . . H22C H 0.7732 0.1823 0.6718 0.110 Uiso 1 1 calc R . . C23 C 0.5493(5) 0.3403(5) 0.7895(4) 0.0525(11) Uani 1 1 d . . . H23A H 0.5682 0.2455 0.8048 0.063 Uiso 1 1 calc R . . H23B H 0.5871 0.3726 0.8339 0.063 Uiso 1 1 calc R . . C24 C 0.3859(5) 0.3492(6) 0.8167(4) 0.0660(13) Uani 1 1 d . . . H24A H 0.3678 0.4446 0.7981 0.079 Uiso 1 1 calc R . . H24B H 0.3483 0.3138 0.7738 0.079 Uiso 1 1 calc R . . C25 C 0.3049(6) 0.2719(7) 0.9316(5) 0.0881(19) Uani 1 1 d . . . H25A H 0.3535 0.2942 0.9754 0.106 Uiso 1 1 calc R . . H25B H 0.2095 0.3019 0.9458 0.106 Uiso 1 1 calc R . . C26 C 0.2927(13) 0.1195(9) 0.9612(9) 0.177(4) Uani 1 1 d . . . H26A H 0.2553 0.0994 0.9113 0.212 Uiso 1 1 calc R . . H26B H 0.3883 0.0895 0.9536 0.212 Uiso 1 1 calc R . . C27 C 0.2057(13) 0.0410(9) 1.0641(9) 0.177(4) Uani 1 1 d . . . H27A H 0.2528 0.0476 1.1141 0.212 Uiso 1 1 calc R . . H27B H 0.1160 0.0818 1.0764 0.212 Uiso 1 1 calc R . . C28 C 0.1750(13) -0.0949(9) 1.0852(7) 0.151(4) Uani 1 1 d . . . H28A H 0.1181 -0.1389 1.1572 0.227 Uiso 1 1 calc R . . H28B H 0.2627 -0.1372 1.0739 0.227 Uiso 1 1 calc R . . H28C H 0.1229 -0.1035 1.0394 0.227 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 0.0385(4) 0.0467(4) 0.0588(4) -0.0278(3) -0.0178(3) 0.0074(2) P1 0.0396(6) 0.0412(6) 0.0454(6) -0.0203(5) -0.0152(4) 0.0077(4) N1 0.051(2) 0.065(3) 0.053(2) -0.0361(19) -0.0204(17) 0.0116(18) N2 0.048(2) 0.057(2) 0.086(3) -0.046(2) -0.0279(19) 0.0127(18) C1 0.038(2) 0.049(2) 0.041(2) -0.0199(19) -0.0105(16) 0.0070(18) C2 0.046(2) 0.055(3) 0.056(2) -0.027(2) -0.018(2) 0.010(2) C3 0.050(3) 0.065(3) 0.065(3) -0.022(2) -0.024(2) 0.023(2) C4 0.047(3) 0.072(3) 0.059(3) -0.027(2) -0.025(2) 0.013(2) C5 0.063(3) 0.064(3) 0.072(3) -0.032(3) -0.031(2) 0.004(2) C6 0.057(3) 0.056(3) 0.069(3) -0.028(2) -0.032(2) 0.012(2) C7 0.040(2) 0.047(2) 0.053(2) -0.026(2) -0.0180(18) 0.0088(18) C8 0.062(3) 0.082(4) 0.057(3) -0.035(3) -0.022(2) 0.025(3) C9 0.064(3) 0.110(5) 0.066(3) -0.051(3) -0.014(3) 0.027(3) C10 0.049(3) 0.094(4) 0.093(4) -0.062(4) -0.023(3) 0.027(3) C11 0.049(3) 0.057(3) 0.102(4) -0.034(3) -0.033(3) 0.018(2) C12 0.046(2) 0.056(3) 0.068(3) -0.029(2) -0.025(2) 0.011(2) C13 0.037(2) 0.050(2) 0.046(2) -0.0180(19) -0.0169(17) 0.0069(18) C14 0.054(3) 0.053(3) 0.055(2) -0.021(2) -0.024(2) 0.009(2) C15 0.054(3) 0.052(3) 0.062(3) -0.007(2) -0.022(2) 0.006(2) C16 0.048(3) 0.064(3) 0.051(2) -0.005(2) -0.014(2) 0.011(2) C17 0.047(3) 0.080(4) 0.043(2) -0.020(2) -0.0160(19) 0.019(2) C18 0.039(2) 0.061(3) 0.052(2) -0.026(2) -0.0203(18) 0.014(2) C19 0.077(3) 0.081(4) 0.067(3) -0.048(3) -0.028(3) 0.021(3) C20 0.078(4) 0.082(4) 0.099(4) -0.062(3) -0.048(3) 0.027(3) C21 0.077(4) 0.081(4) 0.129(5) -0.062(4) -0.032(4) -0.010(3) C22 0.068(3) 0.068(3) 0.107(4) -0.047(3) -0.042(3) 0.029(3) C23 0.046(2) 0.049(3) 0.065(3) -0.022(2) -0.018(2) 0.003(2) C24 0.047(3) 0.069(3) 0.079(3) -0.023(3) -0.019(2) 0.002(2) C25 0.052(3) 0.100(5) 0.086(4) -0.013(4) -0.007(3) 0.001(3) C26 0.169(7) 0.092(5) 0.166(7) 0.006(4) 0.036(5) -0.001(4) C27 0.169(7) 0.092(5) 0.166(7) 0.006(4) 0.036(5) -0.001(4) C28 0.197(10) 0.108(7) 0.120(7) -0.050(6) 0.009(7) -0.001(7) _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 N1 1.892(4) . ? Ni1 C23 1.951(5) . ? Ni1 N2 2.013(3) . ? Ni1 P1 2.0985(11) . ? P1 C13 1.804(4) . ? P1 C7 1.822(4) . ? P1 C1 1.836(4) . ? N1 C18 1.351(6) . ? N1 C19 1.458(6) . ? N2 C21 1.461(7) . ? N2 C22 1.474(6) . ? N2 C20 1.505(7) . ? C1 C2 1.377(6) . ? C1 C6 1.387(6) . ? C2 C3 1.397(6) . ? C2 H2 0.9300 . ? C3 C4 1.361(7) . ? C3 H3 0.9300 . ? C4 C5 1.386(7) . ? C4 H4 0.9300 . ? C5 C6 1.380(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.387(6) . ? C7 C12 1.397(6) . ? C8 C9 1.384(7) . ? C8 H8 0.9300 . ? C9 C10 1.356(8) . ? C9 H9 0.9300 . ? C10 C11 1.372(8) . ? C10 H10 0.9300 . ? C11 C12 1.384(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.387(6) . ? C13 C18 1.427(6) . ? C14 C15 1.381(6) . ? C14 H14 0.9300 . ? C15 C16 1.377(7) . ? C15 H15 0.9300 . ? C16 C17 1.373(7) . ? C16 H16 0.9300 . ? C17 C18 1.416(6) . ? C17 H17 0.9300 . ? C19 C20 1.485(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.544(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.517(8) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.505(10) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.417(12) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.373(11) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 N1 Ni1 C23 176.92(16) . . ? N1 Ni1 N2 84.98(16) . . ? C23 Ni1 N2 97.52(18) . . ? N1 Ni1 P1 85.90(11) . . ? C23 Ni1 P1 91.89(14) . . ? N2 Ni1 P1 167.62(12) . . ? C13 P1 C7 107.13(19) . . ? C13 P1 C1 106.51(18) . . ? C7 P1 C1 103.54(17) . . ? C13 P1 Ni1 102.58(14) . . ? C7 P1 Ni1 121.60(14) . . ? C1 P1 Ni1 114.49(13) . . ? C18 N1 C19 119.6(4) . . ? C18 N1 Ni1 123.7(3) . . ? C19 N1 Ni1 116.1(3) . . ? C21 N2 C22 110.1(4) . . ? C21 N2 C20 106.9(4) . . ? C22 N2 C20 109.0(4) . . ? C21 N2 Ni1 120.7(3) . . ? C22 N2 Ni1 104.7(3) . . ? C20 N2 Ni1 104.9(3) . . ? C2 C1 C6 118.7(4) . . ? C2 C1 P1 119.3(3) . . ? C6 C1 P1 121.9(3) . . ? C1 C2 C3 120.5(4) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.1(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.1(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.8(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 120.8(4) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C12 118.5(4) . . ? C8 C7 P1 121.6(3) . . ? C12 C7 P1 119.8(3) . . ? C9 C8 C7 120.5(5) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.5(5) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.1(4) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 120.6(5) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 119.8(4) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C14 C13 C18 120.9(4) . . ? C14 C13 P1 127.9(3) . . ? C18 C13 P1 111.2(3) . . ? C15 C14 C13 121.0(4) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C16 C15 C14 118.6(5) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C17 C16 C15 122.1(4) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C18 120.9(4) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? N1 C18 C17 127.3(4) . . ? N1 C18 C13 116.4(4) . . ? C17 C18 C13 116.3(4) . . ? N1 C19 C20 106.6(4) . . ? N1 C19 H19A 110.4 . . ? C20 C19 H19A 110.4 . . ? N1 C19 H19B 110.4 . . ? C20 C19 H19B 110.4 . . ? H19A C19 H19B 108.6 . . ? C19 C20 N2 110.6(4) . . ? C19 C20 H20A 109.5 . . ? N2 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? N2 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 Ni1 112.8(3) . . ? C24 C23 H23A 109.0 . . ? Ni1 C23 H23A 109.0 . . ? C24 C23 H23B 109.0 . . ? Ni1 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C25 C24 C23 114.5(4) . . ? C25 C24 H24A 108.6 . . ? C23 C24 H24A 108.6 . . ? C25 C24 H24B 108.6 . . ? C23 C24 H24B 108.6 . . ? H24A C24 H24B 107.6 . . ? C26 C25 C24 113.0(6) . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25B 109.0 . . ? C24 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C27 C26 C25 116.3(9) . . ? C27 C26 H26A 108.2 . . ? C25 C26 H26A 108.2 . . ? C27 C26 H26B 108.2 . . ? C25 C26 H26B 108.2 . . ? H26A C26 H26B 107.4 . . ? C28 C27 C26 116.2(10) . . ? C28 C27 H27A 108.2 . . ? C26 C27 H27A 108.2 . . ? C28 C27 H27B 108.2 . . ? C26 C27 H27B 108.2 . . ? H27A C27 H27B 107.4 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.42 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.891 _refine_diff_density_min -0.962 _refine_diff_density_rms 0.235 #===END data_8776 _database_code_depnum_ccdc_archive 'CCDC 834555' #TrackingRef '- [PNN]Ni_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 Br N2 Ni P' _chemical_formula_sum 'C22 H24 Br N2 Ni P' _chemical_formula_weight 486.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 9.1844(4) _cell_length_b 11.8541(5) _cell_length_c 18.9047(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.546(2) _cell_angle_gamma 90.00 _cell_volume 2057.46(17) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 14045 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 2.972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6856 _exptl_absorpt_correction_T_max 0.8354 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13481 _diffrn_reflns_av_R_equivalents 0.1238 _diffrn_reflns_av_sigmaI/netI 0.1201 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3619 _reflns_number_gt 2130 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1162P)^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 SHELXL _refine_ls_extinction_coef 0.0182(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3619 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1434 _refine_ls_R_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.2308 _refine_ls_wR_factor_gt 0.1742 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 Br1 Br 0.77071(12) 0.18191(9) 0.03121(5) 0.0482(4) Uani 1 1 d . . . Ni1 Ni 0.72637(12) 0.19651(10) 0.15063(6) 0.0305(4) Uani 1 1 d . . . P1 P 0.8428(2) 0.0441(2) 0.17242(13) 0.0294(6) Uani 1 1 d . . . N1 N 0.6936(8) 0.2025(6) 0.2486(4) 0.0310(18) Uani 1 1 d . . . N2 N 0.6368(8) 0.3519(6) 0.1468(4) 0.035(2) Uani 1 1 d . . . C1 C 1.0383(9) 0.0677(7) 0.1643(5) 0.030(2) Uani 1 1 d . . . C2 C 1.1172(10) 0.1146(8) 0.2215(5) 0.040(2) Uani 1 1 d . . . H2 H 1.0704 0.1310 0.2633 0.048 Uiso 1 1 calc R . . C3 C 1.2657(10) 0.1366(8) 0.2161(6) 0.041(3) Uani 1 1 d . . . H3 H 1.3170 0.1685 0.2542 0.049 Uiso 1 1 calc R . . C4 C 1.3364(10) 0.1120(8) 0.1557(6) 0.042(3) Uani 1 1 d . . . H4 H 1.4356 0.1263 0.1527 0.050 Uiso 1 1 calc R . . C5 C 1.2592(10) 0.0651(10) 0.0982(5) 0.045(3) Uani 1 1 d . . . H5 H 1.3069 0.0478 0.0568 0.054 Uiso 1 1 calc R . . C6 C 1.1107(10) 0.0444(9) 0.1029(5) 0.040(2) Uani 1 1 d . . . H6 H 1.0594 0.0144 0.0642 0.048 Uiso 1 1 calc R . . C7 C 0.7998(9) -0.0861(7) 0.1265(5) 0.029(2) Uani 1 1 d . . . C8 C 0.6586(9) -0.1021(8) 0.0988(5) 0.034(2) Uani 1 1 d . . . H8 H 0.5901 -0.0452 0.1041 0.041 Uiso 1 1 calc R . . C9 C 0.6179(11) -0.1998(9) 0.0640(5) 0.041(3) Uani 1 1 d . . . H9 H 0.5244 -0.2077 0.0444 0.049 Uiso 1 1 calc R . . C10 C 0.7184(11) -0.2855(9) 0.0586(5) 0.040(2) Uani 1 1 d . . . H10 H 0.6918 -0.3529 0.0366 0.048 Uiso 1 1 calc R . . C11 C 0.8579(12) -0.2719(8) 0.0856(6) 0.045(3) Uani 1 1 d . . . H11 H 0.9260 -0.3293 0.0807 0.054 Uiso 1 1 calc R . . C12 C 0.8967(11) -0.1738(9) 0.1198(6) 0.045(3) Uani 1 1 d . . . H12 H 0.9906 -0.1664 0.1389 0.053 Uiso 1 1 calc R . . C13 C 0.8123(9) 0.0248(8) 0.2664(5) 0.028(2) Uani 1 1 d . . . C14 C 0.8580(10) -0.0645(9) 0.3075(5) 0.043(3) Uani 1 1 d . . . H14 H 0.8954 -0.1290 0.2867 0.052 Uiso 1 1 calc R . . C15 C 0.8477(11) -0.0573(9) 0.3813(5) 0.044(3) Uani 1 1 d . . . H15 H 0.8751 -0.1172 0.4105 0.052 Uiso 1 1 calc R . . C16 C 0.7954(11) 0.0417(10) 0.4088(5) 0.046(3) Uani 1 1 d . . . H16 H 0.7934 0.0489 0.4577 0.055 Uiso 1 1 calc R . . C17 C 0.7461(11) 0.1304(9) 0.3682(5) 0.043(3) Uani 1 1 d . . . H17 H 0.7113 0.1949 0.3899 0.052 Uiso 1 1 calc R . . C18 C 0.7479(10) 0.1244(9) 0.2927(5) 0.037(2) Uani 1 1 d . . . C19 C 0.6459(12) 0.3113(8) 0.2747(6) 0.044(3) Uani 1 1 d . . . H19A H 0.7289 0.3579 0.2881 0.052 Uiso 1 1 calc R . . H19B H 0.5855 0.3017 0.3156 0.052 Uiso 1 1 calc R . . C20 C 0.5590(10) 0.3651(9) 0.2141(6) 0.043(3) Uani 1 1 d . . . H20A H 0.4639 0.3298 0.2098 0.052 Uiso 1 1 calc R . . H20B H 0.5449 0.4447 0.2238 0.052 Uiso 1 1 calc R . . C21 C 0.5353(10) 0.3773(9) 0.0871(5) 0.044(3) Uani 1 1 d . . . H21A H 0.5846 0.3684 0.0433 0.066 Uiso 1 1 calc R . . H21B H 0.5012 0.4536 0.0910 0.066 Uiso 1 1 calc R . . H21C H 0.4539 0.3266 0.0881 0.066 Uiso 1 1 calc R . . C22 C 0.7599(10) 0.4330(9) 0.1430(6) 0.046(3) Uani 1 1 d . . . H22A H 0.8091 0.4223 0.0993 0.068 Uiso 1 1 calc R . . H22B H 0.8268 0.4203 0.1820 0.068 Uiso 1 1 calc R . . H22C H 0.7231 0.5087 0.1451 0.068 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 Br1 0.0644(8) 0.0487(7) 0.0316(6) 0.0024(5) 0.0009(5) 0.0159(6) Ni1 0.0314(7) 0.0290(7) 0.0310(7) -0.0019(5) -0.0005(5) 0.0035(6) P1 0.0295(13) 0.0307(14) 0.0279(13) -0.0035(11) 0.0018(10) 0.0013(12) N1 0.037(4) 0.028(4) 0.029(4) -0.010(3) 0.003(3) 0.007(4) N2 0.028(4) 0.027(4) 0.049(5) -0.003(4) 0.002(4) 0.004(4) C1 0.033(5) 0.029(5) 0.027(5) 0.004(4) -0.002(4) 0.000(4) C2 0.047(6) 0.032(6) 0.042(6) -0.001(5) 0.004(5) -0.007(5) C3 0.037(6) 0.036(6) 0.051(7) -0.005(5) 0.000(5) -0.011(5) C4 0.029(5) 0.032(6) 0.063(8) -0.003(5) -0.002(5) -0.002(5) C5 0.041(6) 0.054(7) 0.041(6) 0.003(5) 0.020(5) 0.007(5) C6 0.040(6) 0.047(6) 0.033(6) -0.007(5) 0.003(4) 0.002(5) C7 0.024(5) 0.024(5) 0.038(6) 0.002(4) -0.001(4) 0.001(4) C8 0.032(5) 0.035(6) 0.036(6) 0.002(4) 0.007(4) 0.007(5) C9 0.041(6) 0.049(7) 0.033(6) -0.003(5) -0.004(5) -0.008(5) C10 0.055(7) 0.035(6) 0.029(6) -0.007(4) -0.001(5) 0.003(5) C11 0.061(7) 0.025(5) 0.050(7) -0.006(5) 0.005(6) 0.019(5) C12 0.044(6) 0.045(6) 0.045(7) 0.001(5) 0.005(5) 0.000(6) C13 0.022(4) 0.032(5) 0.029(5) 0.000(4) -0.005(4) -0.010(4) C14 0.043(6) 0.045(6) 0.041(6) 0.000(5) 0.001(5) -0.002(5) C15 0.048(6) 0.047(7) 0.035(6) 0.012(5) -0.006(5) -0.007(6) C16 0.045(6) 0.067(8) 0.025(6) -0.003(5) 0.010(5) -0.016(6) C17 0.050(6) 0.045(6) 0.035(6) -0.002(5) 0.010(5) -0.016(5) C18 0.030(5) 0.045(6) 0.035(6) -0.011(5) 0.004(4) -0.013(5) C19 0.058(7) 0.029(6) 0.045(6) -0.010(5) 0.021(5) 0.005(5) C20 0.035(5) 0.033(6) 0.062(7) -0.007(5) 0.007(5) 0.008(5) C21 0.039(6) 0.041(6) 0.051(7) 0.001(5) -0.010(5) 0.005(5) C22 0.048(6) 0.037(6) 0.052(7) -0.007(5) -0.002(5) -0.013(5) _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 Br1 Ni1 2.3112(16) . ? Ni1 N1 1.885(8) . ? Ni1 N2 2.018(7) . ? Ni1 P1 2.134(3) . ? P1 C7 1.809(9) . ? P1 C13 1.821(9) . ? P1 C1 1.828(9) . ? N1 C18 1.333(13) . ? N1 C19 1.453(11) . ? N2 C21 1.476(11) . ? N2 C20 1.484(12) . ? N2 C22 1.487(12) . ? C1 C6 1.381(12) . ? C1 C2 1.400(12) . ? C2 C3 1.395(13) . ? C2 H2 0.9300 . ? C3 C4 1.361(14) . ? C3 H3 0.9300 . ? C4 C5 1.397(13) . ? C4 H4 0.9300 . ? C5 C6 1.391(13) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.376(13) . ? C7 C8 1.399(12) . ? C8 C9 1.378(13) . ? C8 H8 0.9300 . ? C9 C10 1.379(13) . ? C9 H9 0.9300 . ? C10 C11 1.375(14) . ? C10 H10 0.9300 . ? C11 C12 1.374(14) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.372(13) . ? C13 C18 1.417(13) . ? C14 C15 1.404(13) . ? C14 H14 0.9300 . ? C15 C16 1.376(15) . ? C15 H15 0.9300 . ? C16 C17 1.371(14) . ? C16 H16 0.9300 . ? C17 C18 1.429(14) . ? C17 H17 0.9300 . ? C19 C20 1.519(14) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 N1 Ni1 N2 85.7(3) . . ? N1 Ni1 P1 86.3(2) . . ? N2 Ni1 P1 169.0(2) . . ? N1 Ni1 Br1 177.6(2) . . ? N2 Ni1 Br1 96.6(2) . . ? P1 Ni1 Br1 91.41(8) . . ? C7 P1 C13 108.9(4) . . ? C7 P1 C1 107.0(4) . . ? C13 P1 C1 106.1(4) . . ? C7 P1 Ni1 121.9(3) . . ? C13 P1 Ni1 101.9(3) . . ? C1 P1 Ni1 110.0(3) . . ? C18 N1 C19 120.9(8) . . ? C18 N1 Ni1 121.5(6) . . ? C19 N1 Ni1 115.2(6) . . ? C21 N2 C20 109.0(7) . . ? C21 N2 C22 107.2(8) . . ? C20 N2 C22 111.0(8) . . ? C21 N2 Ni1 117.5(6) . . ? C20 N2 Ni1 105.7(6) . . ? C22 N2 Ni1 106.4(6) . . ? C6 C1 C2 118.5(8) . . ? C6 C1 P1 122.4(7) . . ? C2 C1 P1 119.0(7) . . ? C3 C2 C1 120.2(9) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 120.8(9) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.6(9) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 119.9(9) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C1 C6 C5 120.9(9) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C12 C7 C8 117.3(9) . . ? C12 C7 P1 123.7(7) . . ? C8 C7 P1 118.9(7) . . ? C9 C8 C7 122.0(9) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 118.8(9) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 120.3(9) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.1(10) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 121.5(10) . . ? C11 C12 H12 119.2 . . ? C7 C12 H12 119.2 . . ? C14 C13 C18 124.7(9) . . ? C14 C13 P1 126.6(8) . . ? C18 C13 P1 108.3(7) . . ? C13 C14 C15 119.2(10) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 117.4(10) . . ? C16 C15 H15 121.3 . . ? C14 C15 H15 121.3 . . ? C17 C16 C15 123.8(10) . . ? C17 C16 H16 118.1 . . ? C15 C16 H16 118.1 . . ? C16 C17 C18 120.6(10) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? N1 C18 C13 120.8(9) . . ? N1 C18 C17 125.2(10) . . ? C13 C18 C17 114.0(10) . . ? N1 C19 C20 105.9(8) . . ? N1 C19 H19A 110.6 . . ? C20 C19 H19A 110.6 . . ? N1 C19 H19B 110.6 . . ? C20 C19 H19B 110.6 . . ? H19A C19 H19B 108.7 . . ? N2 C20 C19 110.3(7) . . ? N2 C20 H20A 109.6 . . ? C19 C20 H20A 109.6 . . ? N2 C20 H20B 109.6 . . ? C19 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.298 _refine_diff_density_min -1.145 _refine_diff_density_rms 0.418 #===END