data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jwu-Ting Chen' _publ_contact_author_email JTCHEN@NTU.EDU.TW _publ_section_title ; Nickel Catalysts Bearing Bidentate alpha-Amino-Aldimines for Ethylene Polymerization - Independent and Cooperative Structure/Reactivity Relationship Resulting from Unsymmetric Square-Planar Coordination ; loop_ _publ_author_name 'Jwu-Ting Chen.' 'Yi-Chun Chen.' 'Ya-Fan Lin.' 'Yi-Hung Liu.' ; Shiuh-Tzung Liu ; 'Yu Wang.' 'Feng-Zhao Yang.' 'Kuo-Hsuan Yu.' data_ic10089 _database_code_depnum_ccdc_archive 'CCDC 682282' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 Br2 N2 Ni' _chemical_formula_weight 436.87 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 17.3020(4) _cell_length_b 13.8610(3) _cell_length_c 15.2240(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.879(2) _cell_angle_gamma 90.00 _cell_volume 3454.65(13) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 43909 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 5.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.260 _exptl_absorpt_correction_T_max 0.446 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26721 _diffrn_reflns_av_R_equivalents 0.0970 _diffrn_reflns_av_sigmaI/netI 0.0868 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 27.47 _reflns_number_total 7918 _reflns_number_gt 4122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens constr _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0062(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7918 _refine_ls_number_parameters 335 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1728 _refine_ls_R_factor_gt 0.0942 _refine_ls_wR_factor_ref 0.2911 _refine_ls_wR_factor_gt 0.2648 _refine_ls_goodness_of_fit_ref 1.543 _refine_ls_restrained_S_all 1.545 _refine_ls_shift/su_max 0.040 _refine_ls_shift/su_mean 0.007 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 0.40320(7) 0.81143(9) 0.12639(9) 0.0706(4) Uani 1 1 d . . . Br2 Br 0.51328(9) 0.70103(12) 0.37776(9) 0.0852(5) Uani 1 1 d . . . Ni1 Ni 0.51587(8) 0.73061(10) 0.22737(9) 0.0513(4) Uani 1 1 d . . . N1 N 0.6287(5) 0.7773(5) 0.2414(5) 0.0445(18) Uani 1 1 d . . . N2 N 0.5546(5) 0.6137(6) 0.1704(5) 0.0469(19) Uani 1 1 d . . . C1 C 0.6742(6) 0.7113(7) 0.2310(8) 0.053(3) Uani 1 1 d . . . H1A H 0.7277 0.7263 0.2356 0.064 Uiso 1 1 calc R . . C2 C 0.6459(6) 0.6086(7) 0.2115(8) 0.052(3) Uani 1 1 d . . . C3 C 0.6737(8) 0.5586(8) 0.3058(9) 0.074(3) Uani 1 1 d . . . H3A H 0.6476 0.5882 0.3458 0.112 Uiso 1 1 calc R . . H3B H 0.7319 0.5646 0.3329 0.112 Uiso 1 1 calc R . . H3C H 0.6591 0.4916 0.2980 0.112 Uiso 1 1 calc R . . C4 C 0.6875(8) 0.5584(8) 0.1468(10) 0.077(4) Uani 1 1 d . . . H4A H 0.6704 0.5893 0.0872 0.115 Uiso 1 1 calc R . . H4B H 0.6719 0.4916 0.1396 0.115 Uiso 1 1 calc R . . H4C H 0.7458 0.5632 0.1738 0.115 Uiso 1 1 calc R . . C5 C 0.5144(7) 0.5205(8) 0.1823(9) 0.069(3) Uani 1 1 d . . . H5A H 0.5351 0.4688 0.1543 0.104 Uiso 1 1 calc R . . H5B H 0.4564 0.5257 0.1529 0.104 Uiso 1 1 calc R . . H5C H 0.5260 0.5075 0.2472 0.104 Uiso 1 1 calc R . . C6 C 0.5293(8) 0.6321(8) 0.0690(7) 0.067(3) Uani 1 1 d . . . H6A H 0.5463 0.5792 0.0388 0.101 Uiso 1 1 calc R . . H6B H 0.5543 0.6905 0.0576 0.101 Uiso 1 1 calc R . . H6C H 0.4709 0.6383 0.0448 0.101 Uiso 1 1 calc R . . C21 C 0.6598(6) 0.8734(7) 0.2717(7) 0.045(2) Uani 1 1 d . . . C22 C 0.7026(6) 0.8870(7) 0.3663(7) 0.052(2) Uani 1 1 d . . . C23 C 0.7251(7) 0.9803(9) 0.3945(9) 0.067(3) Uani 1 1 d . . . H23A H 0.7542 0.9923 0.4565 0.081 Uiso 1 1 calc R . . C24 C 0.7054(7) 1.0556(8) 0.3330(9) 0.066(3) Uani 1 1 d . . . H24A H 0.7197 1.1182 0.3539 0.079 Uiso 1 1 calc R . . C25 C 0.6647(7) 1.0394(7) 0.2407(9) 0.061(3) Uani 1 1 d . . . H25A H 0.6536 1.0912 0.1997 0.073 Uiso 1 1 calc R . . C26 C 0.6402(6) 0.9493(7) 0.2074(8) 0.052(3) Uani 1 1 d . . . C27 C 0.7273(7) 0.8037(9) 0.4329(8) 0.074(3) Uani 1 1 d . . . H27A H 0.7561 0.8275 0.4939 0.111 Uiso 1 1 calc R . . H27B H 0.7622 0.7610 0.4131 0.111 Uiso 1 1 calc R . . H27C H 0.6794 0.7694 0.4340 0.111 Uiso 1 1 calc R . . C28 C 0.5962(7) 0.9315(8) 0.1066(8) 0.066(3) Uani 1 1 d . . . H28A H 0.5886 0.9916 0.0734 0.099 Uiso 1 1 calc R . . H28B H 0.5440 0.9029 0.0993 0.099 Uiso 1 1 calc R . . H28C H 0.6279 0.8886 0.0823 0.099 Uiso 1 1 calc R . . Br3 Br 0.08656(10) 1.14125(11) 0.16339(13) 0.0946(5) Uani 1 1 d . B . Br4 Br 0.04747(11) 1.12657(11) 0.40554(12) 0.0992(6) Uani 1 1 d . B . Ni2 Ni 0.03270(9) 1.05188(9) 0.26277(13) 0.0720(5) Uani 1 1 d . . . N3 N 0.0539(4) 0.9106(5) 0.2612(5) 0.0384(17) Uani 1 1 d . B . C31 C -0.0114(7) 0.8647(7) 0.2246(9) 0.068(3) Uani 1 1 d . . . H31A H -0.0098 0.8003 0.2083 0.081 Uiso 1 1 calc R A 1 N4 N -0.0827(9) 1.0110(10) 0.1747(11) 0.037(4) Uiso 0.50(2) 1 d PD B 1 C32 C -0.0958(11) 0.9174(13) 0.2067(11) 0.040(5) Uiso 0.50(2) 1 d PD B 1 C33 C -0.1595(14) 0.8525(16) 0.1330(18) 0.047(6) Uiso 0.50(2) 1 d P B 1 H33A H -0.2129 0.8805 0.1186 0.070 Uiso 0.50(2) 1 calc PR B 1 H33B H -0.1597 0.7890 0.1580 0.070 Uiso 0.50(2) 1 calc PR B 1 H33C H -0.1446 0.8486 0.0776 0.070 Uiso 0.50(2) 1 calc PR B 1 C34 C -0.1151(14) 0.920(2) 0.2970(13) 0.059(6) Uiso 0.50(2) 1 d PD B 1 H34A H -0.0805 0.9665 0.3381 0.088 Uiso 0.50(2) 1 calc PR B 1 H34B H -0.1058 0.8574 0.3255 0.088 Uiso 0.50(2) 1 calc PR B 1 H34C H -0.1713 0.9379 0.2846 0.088 Uiso 0.50(2) 1 calc PR B 1 C35 C -0.1431(8) 1.0838(10) 0.1743(10) 0.080(4) Uiso 0.50(2) 1 d P B 1 H35A H -0.1956 1.0641 0.1334 0.121 Uiso 0.50(2) 1 calc PR B 1 H35B H -0.1281 1.1441 0.1531 0.121 Uiso 0.50(2) 1 calc PR B 1 H35C H -0.1456 1.0916 0.2360 0.121 Uiso 0.50(2) 1 calc PR B 1 C36 C -0.0839(17) 1.000(2) 0.0824(13) 0.079(8) Uiso 0.50(2) 1 d PD B 1 H36A H -0.1375 0.9810 0.0442 0.119 Uiso 0.50(2) 1 calc PR B 1 H36B H -0.0449 0.9522 0.0796 0.119 Uiso 0.50(2) 1 calc PR B 1 H36C H -0.0701 1.0608 0.0603 0.119 Uiso 0.50(2) 1 calc PR B 1 N4' N -0.0861(10) 1.0049(12) 0.2222(13) 0.045(5) Uiso 0.50(2) 1 d P B 2 C32' C -0.0889(13) 0.9139(16) 0.1625(17) 0.054(6) Uiso 0.50(2) 1 d P B 2 C33' C -0.1635(16) 0.8508(18) 0.163(2) 0.058(8) Uiso 0.50(2) 1 d P B 2 H33D H -0.1582 0.8337 0.2261 0.087 Uiso 0.50(2) 1 calc PR B 2 H33E H -0.1651 0.7933 0.1277 0.087 Uiso 0.50(2) 1 calc PR B 2 H33F H -0.2130 0.8867 0.1366 0.087 Uiso 0.50(2) 1 calc PR B 2 C34' C -0.0845(15) 0.949(2) 0.0639(18) 0.067(7) Uiso 0.50(2) 1 d P B 2 H34D H -0.0852 0.8945 0.0253 0.101 Uiso 0.50(2) 1 calc PR B 2 H34E H -0.0349 0.9852 0.0730 0.101 Uiso 0.50(2) 1 calc PR B 2 H34F H -0.1306 0.9900 0.0344 0.101 Uiso 0.50(2) 1 calc PR B 2 C35' C -0.1431(8) 1.0838(10) 0.1743(10) 0.080(4) Uiso 0.50(2) 1 d P B 2 H35D H -0.1983 1.0606 0.1560 0.121 Uiso 0.50(2) 1 calc PR B 2 H35E H -0.1303 1.1041 0.1202 0.121 Uiso 0.50(2) 1 calc PR B 2 H35F H -0.1373 1.1375 0.2158 0.121 Uiso 0.50(2) 1 calc PR B 2 C36' C -0.1122(14) 0.973(2) 0.3072(16) 0.063(7) Uiso 0.50(2) 1 d P B 2 H36D H -0.1682 0.9522 0.2858 0.094 Uiso 0.50(2) 1 calc PR B 2 H36E H -0.1061 1.0257 0.3493 0.094 Uiso 0.50(2) 1 calc PR B 2 H36F H -0.0782 0.9200 0.3385 0.094 Uiso 0.50(2) 1 calc PR B 2 C37 C 0.1310(5) 0.8624(6) 0.2988(7) 0.041(2) Uani 1 1 d . . . C38 C 0.1581(6) 0.8389(7) 0.3938(7) 0.053(3) Uani 1 1 d . B . C39 C 0.2366(6) 0.8000(7) 0.4289(9) 0.060(3) Uani 1 1 d . . . H39A H 0.2571 0.7858 0.4920 0.072 Uiso 1 1 calc R B . C40 C 0.2835(7) 0.7821(8) 0.3768(9) 0.065(3) Uani 1 1 d . B . H40A H 0.3351 0.7551 0.4032 0.078 Uiso 1 1 calc R . . C41 C 0.2550(6) 0.8042(7) 0.2818(10) 0.062(3) Uani 1 1 d . . . H41A H 0.2878 0.7922 0.2452 0.074 Uiso 1 1 calc R B . C42 C 0.1782(6) 0.8440(6) 0.2424(7) 0.045(2) Uani 1 1 d . B . C43 C 0.1040(7) 0.8546(8) 0.4535(8) 0.062(3) Uani 1 1 d . . . H43A H 0.1326 0.8348 0.5160 0.093 Uiso 1 1 calc R B . H43B H 0.0550 0.8172 0.4293 0.093 Uiso 1 1 calc R . . H43C H 0.0903 0.9217 0.4529 0.093 Uiso 1 1 calc R . . C44 C 0.1494(8) 0.8686(10) 0.1411(9) 0.079(4) Uani 1 1 d . . . H44A H 0.0955 0.8958 0.1244 0.118 Uiso 1 1 calc R B . H44B H 0.1481 0.8112 0.1054 0.118 Uiso 1 1 calc R . . H44C H 0.1860 0.9146 0.1286 0.118 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 0.0526(7) 0.0700(8) 0.0809(9) -0.0076(6) 0.0103(6) 0.0062(6) Br2 0.0777(9) 0.1250(13) 0.0593(8) -0.0238(7) 0.0310(7) -0.0253(8) Ni1 0.0410(7) 0.0543(8) 0.0580(8) -0.0161(6) 0.0149(6) -0.0037(6) N1 0.045(4) 0.037(4) 0.052(5) 0.002(4) 0.016(4) -0.001(4) N2 0.048(5) 0.042(4) 0.052(5) -0.004(4) 0.017(4) -0.005(4) C1 0.050(6) 0.042(6) 0.075(7) 0.002(5) 0.029(5) -0.002(5) C2 0.052(6) 0.038(5) 0.076(7) -0.001(5) 0.034(5) -0.006(4) C3 0.074(8) 0.043(6) 0.102(10) 0.011(6) 0.022(7) 0.004(6) C4 0.077(8) 0.053(7) 0.112(11) -0.013(7) 0.048(8) 0.003(6) C5 0.075(8) 0.048(6) 0.086(9) -0.009(6) 0.030(7) -0.007(6) C6 0.090(9) 0.054(7) 0.057(7) -0.010(5) 0.022(6) -0.003(6) C21 0.039(5) 0.040(5) 0.059(6) -0.007(5) 0.020(5) 0.004(4) C22 0.051(6) 0.045(6) 0.064(7) -0.007(5) 0.026(5) -0.002(5) C23 0.058(7) 0.072(8) 0.075(8) -0.010(7) 0.026(6) -0.003(6) C24 0.055(7) 0.052(7) 0.097(10) -0.020(7) 0.033(7) -0.009(5) C25 0.058(7) 0.040(6) 0.083(9) 0.011(5) 0.018(6) 0.002(5) C26 0.037(5) 0.047(6) 0.068(7) 0.006(5) 0.013(5) -0.009(4) C27 0.067(8) 0.082(9) 0.061(7) 0.000(6) 0.006(6) -0.018(6) C28 0.063(7) 0.063(7) 0.061(7) 0.005(6) 0.005(6) -0.014(6) Br3 0.0910(11) 0.0705(9) 0.1274(13) -0.0030(8) 0.0421(10) -0.0038(7) Br4 0.1224(13) 0.0691(9) 0.1061(12) 0.0054(8) 0.0372(10) -0.0101(8) Ni2 0.0464(8) 0.0323(7) 0.1247(14) -0.0054(8) 0.0104(8) -0.0011(6) N3 0.038(4) 0.033(4) 0.043(4) 0.000(3) 0.012(3) -0.005(3) C31 0.048(6) 0.032(5) 0.106(10) -0.002(6) 0.001(6) 0.010(5) C37 0.042(5) 0.021(4) 0.059(6) -0.008(4) 0.013(4) -0.008(4) C38 0.051(6) 0.042(5) 0.058(6) -0.010(5) 0.007(5) 0.001(5) C39 0.049(6) 0.037(6) 0.073(7) -0.004(5) -0.010(6) 0.004(5) C40 0.050(6) 0.046(6) 0.089(9) -0.014(6) 0.010(6) 0.007(5) C41 0.047(6) 0.037(5) 0.113(11) -0.013(6) 0.043(7) -0.005(5) C42 0.041(5) 0.032(5) 0.064(6) -0.014(4) 0.021(5) -0.006(4) C43 0.064(7) 0.066(7) 0.056(7) 0.006(5) 0.020(6) 0.003(6) C44 0.086(9) 0.080(9) 0.083(9) -0.005(7) 0.044(8) 0.006(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 Br1 Ni1 2.3408(18) . ? Br2 Ni1 2.3405(18) . ? Ni1 N1 2.001(8) . ? Ni1 N2 2.050(8) . ? N1 C1 1.250(12) . ? N1 C21 1.455(12) . ? N2 C6 1.484(13) . ? N2 C2 1.500(13) . ? N2 C5 1.507(13) . ? C1 C2 1.503(13) . ? C1 H1A 0.9300 . ? C2 C3 1.525(16) . ? C2 C4 1.560(15) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C21 C26 1.402(14) . ? C21 C22 1.403(14) . ? C22 C23 1.377(15) . ? C22 C27 1.504(15) . ? C23 C24 1.370(17) . ? C23 H23A 0.9300 . ? C24 C25 1.371(16) . ? C24 H24A 0.9300 . ? C25 C26 1.362(14) . ? C25 H25A 0.9300 . ? C26 C28 1.497(15) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? Br3 Ni2 2.367(2) . ? Br4 Ni2 2.346(3) . ? Ni2 N3 1.993(7) . ? Ni2 N4' 2.051(16) . ? Ni2 N4 2.091(14) . ? N3 C31 1.259(13) . ? N3 C37 1.435(12) . ? C31 C32' 1.53(2) . ? C31 C32 1.57(2) . ? C31 H31A 0.9300 . ? N4 C36 1.406(18) . ? N4 C32 1.43(2) . ? N4 C35 1.452(19) . ? C32 C34 1.518(17) . ? C32 C33 1.57(3) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? N4' C32' 1.55(3) . ? N4' C36' 1.57(3) . ? C32' C33' 1.56(3) . ? C32' C34' 1.61(3) . ? C33' H33D 0.9600 . ? C33' H33E 0.9600 . ? C33' H33F 0.9600 . ? C34' H34D 0.9600 . ? C34' H34E 0.9600 . ? C34' H34F 0.9600 . ? C36' H36D 0.9600 . ? C36' H36E 0.9600 . ? C36' H36F 0.9600 . ? C37 C42 1.388(13) . ? C37 C38 1.406(14) . ? C38 C39 1.396(14) . ? C38 C43 1.516(15) . ? C39 C40 1.329(17) . ? C39 H39A 0.9300 . ? C40 C41 1.403(17) . ? C40 H40A 0.9300 . ? C41 C42 1.383(15) . ? C41 H41A 0.9300 . ? C42 C44 1.498(16) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 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 81.9(3) . . ? N1 Ni1 Br2 106.2(2) . . ? N2 Ni1 Br2 112.8(2) . . ? N1 Ni1 Br1 119.4(2) . . ? N2 Ni1 Br1 114.7(2) . . ? Br2 Ni1 Br1 116.80(7) . . ? C1 N1 C21 121.8(8) . . ? C1 N1 Ni1 112.5(7) . . ? C21 N1 Ni1 125.3(6) . . ? C6 N2 C2 111.0(8) . . ? C6 N2 C5 106.2(8) . . ? C2 N2 C5 112.0(8) . . ? C6 N2 Ni1 106.1(6) . . ? C2 N2 Ni1 107.8(6) . . ? C5 N2 Ni1 113.6(6) . . ? N1 C1 C2 122.7(9) . . ? N1 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? N2 C2 C1 105.6(8) . . ? N2 C2 C3 112.5(8) . . ? C1 C2 C3 105.1(9) . . ? N2 C2 C4 113.3(9) . . ? C1 C2 C4 111.1(8) . . ? C3 C2 C4 108.8(9) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C26 C21 C22 123.0(9) . . ? C26 C21 N1 119.0(9) . . ? C22 C21 N1 117.8(9) . . ? C23 C22 C21 116.6(10) . . ? C23 C22 C27 121.4(11) . . ? C21 C22 C27 121.9(9) . . ? C24 C23 C22 121.3(12) . . ? C24 C23 H23A 119.4 . . ? C22 C23 H23A 119.4 . . ? C23 C24 C25 120.5(11) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? C26 C25 C24 121.7(11) . . ? C26 C25 H25A 119.1 . . ? C24 C25 H25A 119.1 . . ? C25 C26 C21 116.9(10) . . ? C25 C26 C28 121.8(10) . . ? C21 C26 C28 121.4(9) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N3 Ni2 N4' 81.7(5) . . ? N3 Ni2 N4 82.4(4) . . ? N4' Ni2 N4 20.8(5) . . ? N3 Ni2 Br4 118.6(2) . . ? N4' Ni2 Br4 102.5(5) . . ? N4 Ni2 Br4 120.6(4) . . ? N3 Ni2 Br3 113.2(2) . . ? N4' Ni2 Br3 122.5(5) . . ? N4 Ni2 Br3 102.9(4) . . ? Br4 Ni2 Br3 114.45(8) . . ? C31 N3 C37 121.7(8) . . ? C31 N3 Ni2 111.1(6) . . ? C37 N3 Ni2 127.1(5) . . ? N3 C31 C32' 122.0(12) . . ? N3 C31 C32 119.4(11) . . ? C32' C31 C32 26.8(9) . . ? N3 C31 H31A 120.3 . . ? C32' C31 H31A 111.0 . . ? C32 C31 H31A 120.3 . . ? C36 N4 C32 107.0(15) . . ? C36 N4 C35 106.9(16) . . ? C32 N4 C35 116.1(14) . . ? C36 N4 Ni2 111.8(14) . . ? C32 N4 Ni2 104.6(11) . . ? C35 N4 Ni2 110.5(10) . . ? N4 C32 C34 113.1(18) . . ? N4 C32 C31 103.8(12) . . ? C34 C32 C31 108.6(15) . . ? N4 C32 C33 115.3(15) . . ? C34 C32 C33 110.5(17) . . ? C31 C32 C33 104.8(14) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.4 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N4 C35 H35A 109.5 . . ? N4 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N4 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N4 C36 H36A 109.5 . . ? N4 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? N4 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C32' N4' C36' 106.8(18) . . ? C32' N4' Ni2 105.9(12) . . ? C36' N4' Ni2 111.8(13) . . ? C31 C32' C33' 107.9(17) . . ? C31 C32' N4' 98.3(16) . . ? C33' C32' N4' 109(2) . . ? C31 C32' C34' 114.7(18) . . ? C33' C32' C34' 118(2) . . ? N4' C32' C34' 107.3(19) . . ? C32' C33' H33D 109.5 . . ? C32' C33' H33E 109.4 . . ? H33D C33' H33E 109.5 . . ? C32' C33' H33F 109.5 . . ? H33D C33' H33F 109.5 . . ? H33E C33' H33F 109.5 . . ? C32' C34' H34D 109.5 . . ? C32' C34' H34E 109.5 . . ? H34D C34' H34E 109.5 . . ? C32' C34' H34F 109.5 . . ? H34D C34' H34F 109.5 . . ? H34E C34' H34F 109.5 . . ? N4' C36' H36D 109.5 . . ? N4' C36' H36E 109.5 . . ? H36D C36' H36E 109.5 . . ? N4' C36' H36F 109.5 . . ? H36D C36' H36F 109.5 . . ? H36E C36' H36F 109.5 . . ? C42 C37 C38 121.7(9) . . ? C42 C37 N3 119.7(9) . . ? C38 C37 N3 118.5(8) . . ? C39 C38 C37 116.3(10) . . ? C39 C38 C43 122.6(10) . . ? C37 C38 C43 121.1(9) . . ? C40 C39 C38 123.3(12) . . ? C40 C39 H39A 118.3 . . ? C38 C39 H39A 118.3 . . ? C39 C40 C41 119.7(10) . . ? C39 C40 H40A 120.2 . . ? C41 C40 H40A 120.2 . . ? C42 C41 C40 120.2(10) . . ? C42 C41 H41A 119.9 . . ? C40 C41 H41A 119.9 . . ? C37 C42 C41 118.7(10) . . ? C37 C42 C44 121.9(9) . . ? C41 C42 C44 119.4(10) . . ? C38 C43 H43A 109.5 . . ? C38 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C38 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C42 C44 H44A 109.5 . . ? C42 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C42 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.518 _refine_diff_density_min -0.939 _refine_diff_density_rms 0.260 # Attachment 'Ni-1c.cif' data_ic10071 _database_code_depnum_ccdc_archive 'CCDC 699109' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H30 Br2 N2 Ni' _chemical_formula_weight 492.97 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 15.225(3) _cell_length_b 10.217(2) _cell_length_c 14.312(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2226.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 24112 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 4.462 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.403 _exptl_absorpt_correction_T_max 0.519 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12969 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4515 _reflns_number_gt 2734 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1000P)^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 0.0098(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.010(16) _refine_ls_number_reflns 4515 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1057 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1713 _refine_ls_wR_factor_gt 0.1458 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 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 1.09205(7) -0.42997(9) -0.29395(8) 0.1095(4) Uani 1 1 d . . . Br2 Br 1.11234(9) -0.07993(15) -0.41986(9) 0.1356(6) Uani 1 1 d . . . Ni1 Ni 1.05263(6) -0.20988(9) -0.29999(7) 0.0698(3) Uani 1 1 d . . . N2 N 0.9198(4) -0.1775(6) -0.2839(5) 0.0791(18) Uani 1 1 d . . . N1 N 1.0561(3) -0.1253(5) -0.1732(3) 0.0471(11) Uani 1 1 d . . . C1 C 0.9836(4) -0.0709(6) -0.1535(5) 0.0611(16) Uani 1 1 d . . . H1A H 0.9774 -0.0314 -0.0953 0.073 Uiso 1 1 calc R . . C2 C 0.9079(5) -0.0676(9) -0.2196(5) 0.075(2) Uani 1 1 d . . . C3 C 0.8226(6) -0.0588(12) -0.1686(7) 0.122(4) Uani 1 1 d . . . H3A H 0.8130 -0.1381 -0.1341 0.183 Uiso 1 1 calc R . . H3B H 0.7757 -0.0467 -0.2126 0.183 Uiso 1 1 calc R . . H3C H 0.8242 0.0140 -0.1262 0.183 Uiso 1 1 calc R . . C4 C 0.9192(7) 0.0646(9) -0.2739(8) 0.107(3) Uani 1 1 d . . . H4A H 0.9737 0.0635 -0.3076 0.160 Uiso 1 1 calc R . . H4B H 0.9194 0.1360 -0.2303 0.160 Uiso 1 1 calc R . . H4C H 0.8714 0.0753 -0.3169 0.160 Uiso 1 1 calc R . . C5 C 0.8724(7) -0.1684(12) -0.3761(7) 0.112(4) Uani 1 1 d . . . H5A H 0.8110 -0.1532 -0.3651 0.168 Uiso 1 1 calc R . . H5B H 0.8797 -0.2488 -0.4099 0.168 Uiso 1 1 calc R . . H5C H 0.8962 -0.0973 -0.4119 0.168 Uiso 1 1 calc R . . C6 C 0.8827(6) -0.3026(11) -0.2372(10) 0.114(4) Uani 1 1 d . . . H6A H 0.8205 -0.2929 -0.2280 0.171 Uiso 1 1 calc R . . H6B H 0.9108 -0.3157 -0.1779 0.171 Uiso 1 1 calc R . . H6C H 0.8936 -0.3768 -0.2766 0.171 Uiso 1 1 calc R . . C21 C 1.1285(3) -0.1194(6) -0.1087(4) 0.0463(12) Uani 1 1 d . . . C22 C 1.1858(4) -0.0098(6) -0.1130(5) 0.0615(16) Uani 1 1 d . . . C23 C 1.2545(4) -0.0088(8) -0.0483(6) 0.076(2) Uani 1 1 d . . . H23A H 1.2938 0.0609 -0.0488 0.091 Uiso 1 1 calc R . . C24 C 1.2660(4) -0.1066(9) 0.0156(6) 0.077(2) Uani 1 1 d . . . H24A H 1.3121 -0.1019 0.0581 0.092 Uiso 1 1 calc R . . C25 C 1.2105(4) -0.2108(7) 0.0176(5) 0.0618(16) Uani 1 1 d . . . H25A H 1.2194 -0.2772 0.0610 0.074 Uiso 1 1 calc R . . C26 C 1.1398(4) -0.2194(5) -0.0453(4) 0.0472(13) Uani 1 1 d . . . C27 C 1.1730(7) 0.0982(7) -0.1829(6) 0.091(3) Uani 1 1 d . . . H27A H 1.1329 0.0647 -0.2309 0.109 Uiso 1 1 calc R . . C28 C 1.0738(4) -0.3313(5) -0.0361(5) 0.0538(14) Uani 1 1 d . . . H28A H 1.0425 -0.3390 -0.0957 0.065 Uiso 1 1 calc R . . C29 C 1.2541(8) 0.1399(11) -0.2314(9) 0.134(5) Uani 1 1 d . . . H29A H 1.2816 0.0652 -0.2597 0.202 Uiso 1 1 calc R . . H29B H 1.2937 0.1787 -0.1872 0.202 Uiso 1 1 calc R . . H29C H 1.2397 0.2028 -0.2788 0.202 Uiso 1 1 calc R . . C30 C 1.1257(10) 0.2181(9) -0.1351(9) 0.139(5) Uani 1 1 d . . . H30A H 1.1179 0.2868 -0.1802 0.209 Uiso 1 1 calc R . . H30B H 1.1610 0.2496 -0.0843 0.209 Uiso 1 1 calc R . . H30C H 1.0694 0.1910 -0.1119 0.209 Uiso 1 1 calc R . . C31 C 1.0070(5) -0.3018(8) 0.0385(8) 0.092(3) Uani 1 1 d . . . H31A H 0.9803 -0.2184 0.0262 0.138 Uiso 1 1 calc R . . H31B H 1.0354 -0.2995 0.0983 0.138 Uiso 1 1 calc R . . H31C H 0.9627 -0.3686 0.0386 0.138 Uiso 1 1 calc R . . C32 C 1.1158(6) -0.4644(8) -0.0148(8) 0.090(3) Uani 1 1 d . . . H32A H 1.0707 -0.5297 -0.0100 0.135 Uiso 1 1 calc R . . H32B H 1.1474 -0.4593 0.0431 0.135 Uiso 1 1 calc R . . H32C H 1.1555 -0.4873 -0.0643 0.135 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 0.1345(8) 0.0970(6) 0.0969(8) -0.0363(6) -0.0222(6) 0.0414(5) Br2 0.1453(10) 0.1856(14) 0.0760(7) 0.0317(7) 0.0264(7) 0.0140(8) Ni1 0.0723(5) 0.0935(6) 0.0436(4) -0.0113(5) -0.0050(5) 0.0242(4) N2 0.069(3) 0.105(4) 0.063(5) -0.011(4) -0.014(3) 0.024(3) N1 0.057(3) 0.046(3) 0.039(2) 0.007(2) 0.007(2) 0.010(2) C1 0.074(4) 0.067(4) 0.042(3) 0.002(3) 0.005(3) 0.016(3) C2 0.065(4) 0.112(6) 0.049(4) 0.005(4) 0.002(3) 0.028(4) C3 0.071(5) 0.214(13) 0.081(7) -0.009(7) 0.006(5) 0.049(7) C4 0.125(7) 0.095(6) 0.099(8) 0.030(5) 0.002(6) 0.035(5) C5 0.094(6) 0.170(10) 0.071(6) -0.005(6) -0.032(5) 0.041(6) C6 0.080(5) 0.119(8) 0.143(11) 0.023(7) -0.029(6) -0.010(5) C21 0.046(3) 0.052(3) 0.040(3) -0.007(3) 0.004(2) 0.001(2) C22 0.069(4) 0.058(4) 0.057(4) -0.014(3) 0.021(3) -0.011(3) C23 0.060(4) 0.087(5) 0.080(5) -0.024(4) 0.020(4) -0.032(4) C24 0.050(4) 0.111(6) 0.070(5) -0.034(5) -0.003(3) 0.000(4) C25 0.052(3) 0.084(5) 0.049(4) -0.006(3) -0.004(3) 0.005(3) C26 0.048(3) 0.051(3) 0.043(3) 0.000(3) 0.001(2) 0.003(2) C27 0.149(7) 0.054(4) 0.069(5) -0.003(3) 0.035(5) -0.024(5) C28 0.072(4) 0.045(3) 0.044(3) 0.008(3) -0.015(3) -0.001(3) C29 0.166(10) 0.117(8) 0.120(10) 0.016(7) 0.070(8) -0.046(8) C30 0.249(16) 0.067(5) 0.101(8) 0.023(5) 0.039(9) 0.045(7) C31 0.083(5) 0.081(5) 0.112(8) 0.007(5) 0.035(5) -0.013(4) C32 0.093(5) 0.057(4) 0.118(8) 0.017(5) 0.003(5) -0.002(4) _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 2.3290(13) . ? Br2 Ni1 2.3521(17) . ? Ni1 N1 2.011(5) . ? Ni1 N2 2.061(6) . ? N2 C2 1.463(11) . ? N2 C5 1.507(11) . ? N2 C6 1.550(13) . ? N1 C1 1.267(8) . ? N1 C21 1.439(8) . ? C1 C2 1.492(10) . ? C1 H1A 0.9300 . ? C2 C3 1.493(11) . ? C2 C4 1.567(12) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C21 C26 1.376(8) . ? C21 C22 1.420(8) . ? C22 C23 1.398(11) . ? C22 C27 1.502(11) . ? C23 C24 1.366(13) . ? C23 H23A 0.9300 . ? C24 C25 1.360(10) . ? C24 H24A 0.9300 . ? C25 C26 1.406(9) . ? C25 H25A 0.9300 . ? C26 C28 1.528(8) . ? C27 C29 1.479(12) . ? C27 C30 1.577(13) . ? C27 H27A 0.9800 . ? C28 C31 1.505(11) . ? C28 C32 1.533(10) . ? C28 H28A 0.9800 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 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 81.7(2) . . ? N1 Ni1 Br1 112.01(14) . . ? N2 Ni1 Br1 113.8(2) . . ? N1 Ni1 Br2 113.91(15) . . ? N2 Ni1 Br2 111.7(2) . . ? Br1 Ni1 Br2 118.20(6) . . ? C2 N2 C5 116.3(7) . . ? C2 N2 C6 108.4(8) . . ? C5 N2 C6 104.7(8) . . ? C2 N2 Ni1 108.3(5) . . ? C5 N2 Ni1 112.5(6) . . ? C6 N2 Ni1 105.9(5) . . ? C1 N1 C21 120.4(5) . . ? C1 N1 Ni1 111.5(4) . . ? C21 N1 Ni1 128.1(3) . . ? N1 C1 C2 122.8(6) . . ? N1 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? N2 C2 C1 106.6(5) . . ? N2 C2 C3 117.5(8) . . ? C1 C2 C3 111.3(7) . . ? N2 C2 C4 109.7(7) . . ? C1 C2 C4 104.5(7) . . ? C3 C2 C4 106.6(7) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C26 C21 C22 122.5(6) . . ? C26 C21 N1 119.2(5) . . ? C22 C21 N1 118.3(6) . . ? C23 C22 C21 115.9(7) . . ? C23 C22 C27 122.2(7) . . ? C21 C22 C27 121.9(7) . . ? C24 C23 C22 122.3(6) . . ? C24 C23 H23A 118.9 . . ? C22 C23 H23A 118.9 . . ? C25 C24 C23 120.4(7) . . ? C25 C24 H24A 119.8 . . ? C23 C24 H24A 119.8 . . ? C24 C25 C26 120.8(7) . . ? C24 C25 H25A 119.6 . . ? C26 C25 H25A 119.6 . . ? C21 C26 C25 118.1(5) . . ? C21 C26 C28 122.0(5) . . ? C25 C26 C28 119.7(5) . . ? C29 C27 C22 114.6(9) . . ? C29 C27 C30 111.1(8) . . ? C22 C27 C30 110.0(7) . . ? C29 C27 H27A 106.9 . . ? C22 C27 H27A 106.9 . . ? C30 C27 H27A 106.9 . . ? C31 C28 C26 110.8(6) . . ? C31 C28 C32 108.6(6) . . ? C26 C28 C32 114.0(5) . . ? C31 C28 H28A 107.8 . . ? C26 C28 H28A 107.8 . . ? C32 C28 H28A 107.8 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C28 C32 H32A 109.5 . . ? C28 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C28 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.698 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.205 # Attachment 'Ni-2a.cif' data_ic6904 _database_code_depnum_ccdc_archive 'CCDC 699110' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 Br2 N2 Ni' _chemical_formula_weight 436.87 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.3858(3) _cell_length_b 14.1749(4) _cell_length_c 16.5775(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.737(1) _cell_angle_gamma 90.00 _cell_volume 1726.85(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6765 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue-purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 5.741 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3691 _exptl_absorpt_correction_T_max 0.4921 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10220 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3919 _reflns_number_gt 3222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SAINT' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0591P)^2^+3.3412P] 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 3919 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 Ni Ni 0.61630(7) 0.55074(4) 0.72677(3) 0.01774(15) Uani 1 1 d . . . Br1 Br 0.81039(6) 0.65448(4) 0.80530(3) 0.02755(14) Uani 1 1 d . . . Br2 Br 0.38365(7) 0.62857(3) 0.64226(3) 0.02950(15) Uani 1 1 d . . . N1 N 0.4954(5) 0.4403(3) 0.7737(2) 0.0167(7) Uani 1 1 d . . . N2 N 0.7340(5) 0.4468(3) 0.6628(2) 0.0188(8) Uani 1 1 d . . . C1 C 0.5142(6) 0.3634(3) 0.7370(3) 0.0186(9) Uani 1 1 d . . . H1 H 0.4734 0.3060 0.7585 0.022 Uiso 1 1 calc R . . C2 C 0.6018(6) 0.3634(3) 0.6586(3) 0.0187(9) Uani 1 1 d . . . C3 C 0.6902(7) 0.2679(3) 0.6420(3) 0.0262(10) Uani 1 1 d . . . H3A H 0.7847 0.2535 0.6861 0.039 Uiso 1 1 calc R . . H3B H 0.7448 0.2711 0.5906 0.039 Uiso 1 1 calc R . . H3C H 0.5973 0.2183 0.6389 0.039 Uiso 1 1 calc R . . C4 C 0.4385(6) 0.3765(3) 0.5934(3) 0.0215(9) Uani 1 1 d . . . H4A H 0.3423 0.3316 0.6033 0.032 Uiso 1 1 calc R . . H4B H 0.4782 0.3652 0.5396 0.032 Uiso 1 1 calc R . . H4C H 0.3917 0.4410 0.5962 0.032 Uiso 1 1 calc R . . C5 C 0.9141(6) 0.4214(3) 0.7083(3) 0.0229(10) Uani 1 1 d . . . H5A H 0.9924 0.4782 0.7108 0.027 Uiso 1 1 calc R . . H5B H 0.9729 0.3733 0.6764 0.027 Uiso 1 1 calc R . . C6 C 0.7659(6) 0.4804(4) 0.5796(3) 0.0243(10) Uani 1 1 d . . . H6A H 0.6468 0.4927 0.5484 0.029 Uiso 1 1 calc R . . H6B H 0.8269 0.4297 0.5514 0.029 Uiso 1 1 calc R . . C7 C 0.9104(6) 0.3840(4) 0.7941(3) 0.0281(11) Uani 1 1 d . . . H7A H 0.8618 0.4327 0.8280 0.042 Uiso 1 1 calc R . . H7B H 1.0342 0.3675 0.8164 0.042 Uiso 1 1 calc R . . H7C H 0.8329 0.3279 0.7932 0.042 Uiso 1 1 calc R . . C8 C 0.8808(7) 0.5693(4) 0.5797(3) 0.0326(12) Uani 1 1 d . . . H8A H 0.8236 0.6195 0.6089 0.049 Uiso 1 1 calc R . . H8B H 0.8905 0.5894 0.5237 0.049 Uiso 1 1 calc R . . H8C H 1.0027 0.5564 0.6065 0.049 Uiso 1 1 calc R . . C21 C 0.4060(5) 0.4447(3) 0.8465(3) 0.0180(9) Uani 1 1 d . . . C22 C 0.4291(6) 0.3748(3) 0.9053(3) 0.0245(10) Uani 1 1 d . . . H22 H 0.5029 0.3213 0.8974 0.029 Uiso 1 1 calc R . . C23 C 0.3432(7) 0.3839(4) 0.9756(3) 0.0291(11) Uani 1 1 d . . . H23 H 0.3564 0.3357 1.0156 0.035 Uiso 1 1 calc R . . C24 C 0.2391(6) 0.4619(4) 0.9877(3) 0.0269(11) Uani 1 1 d . . . H24 H 0.1827 0.4682 1.0364 0.032 Uiso 1 1 calc R . . C25 C 0.2163(6) 0.5316(3) 0.9289(3) 0.0245(10) Uani 1 1 d . . . H25 H 0.1429 0.5851 0.9372 0.029 Uiso 1 1 calc R . . C26 C 0.3000(6) 0.5234(3) 0.8582(3) 0.0202(9) Uani 1 1 d . . . H26 H 0.2850 0.5713 0.8181 0.024 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 Ni 0.0134(3) 0.0169(3) 0.0234(3) -0.0017(2) 0.0043(2) -0.0024(2) Br1 0.0207(2) 0.0276(3) 0.0331(3) -0.0040(2) -0.00348(19) -0.00187(19) Br2 0.0234(2) 0.0265(3) 0.0377(3) 0.0009(2) -0.0009(2) -0.00036(19) N1 0.0140(16) 0.0186(18) 0.0178(18) 0.0013(15) 0.0025(14) -0.0009(14) N2 0.0121(17) 0.024(2) 0.0202(19) -0.0015(16) 0.0040(14) -0.0006(14) C1 0.0138(19) 0.019(2) 0.022(2) 0.0059(17) -0.0036(17) -0.0025(16) C2 0.0136(19) 0.017(2) 0.025(2) -0.0023(17) 0.0008(17) -0.0024(16) C3 0.025(2) 0.020(2) 0.032(3) -0.009(2) 0.001(2) 0.0033(19) C4 0.018(2) 0.024(2) 0.023(2) -0.0027(19) -0.0003(18) -0.0020(18) C5 0.0093(18) 0.028(2) 0.031(3) 0.000(2) 0.0000(17) 0.0070(18) C6 0.017(2) 0.032(3) 0.025(2) 0.000(2) 0.0088(18) -0.0008(19) C7 0.020(2) 0.027(2) 0.035(3) 0.002(2) -0.007(2) 0.0019(19) C8 0.024(2) 0.044(3) 0.030(3) 0.007(2) 0.009(2) -0.014(2) C21 0.0106(18) 0.023(2) 0.021(2) 0.0000(18) 0.0014(16) -0.0018(17) C22 0.020(2) 0.026(2) 0.028(3) 0.003(2) 0.0029(19) 0.0046(19) C23 0.028(3) 0.035(3) 0.024(3) 0.009(2) 0.002(2) 0.001(2) C24 0.020(2) 0.040(3) 0.022(2) -0.001(2) 0.0050(18) -0.003(2) C25 0.017(2) 0.025(2) 0.031(3) -0.004(2) 0.0048(19) 0.0012(18) C26 0.013(2) 0.020(2) 0.027(2) -0.0006(19) 0.0023(17) -0.0007(17) _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 Ni N1 1.997(4) . ? Ni N2 2.058(4) . ? Ni Br1 2.3535(7) . ? Ni Br2 2.3772(7) . ? N1 C1 1.263(6) . ? N1 C21 1.434(6) . ? N2 C6 1.500(6) . ? N2 C5 1.505(5) . ? N2 C2 1.530(5) . ? C1 C2 1.508(7) . ? C2 C3 1.539(6) . ? C2 C4 1.548(6) . ? C5 C7 1.521(7) . ? C6 C8 1.519(7) . ? C21 C26 1.388(6) . ? C21 C22 1.388(6) . ? C22 C23 1.388(7) . ? C23 C24 1.373(7) . ? C24 C25 1.386(7) . ? C25 C26 1.383(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 N1 Ni N2 82.41(15) . . ? N1 Ni Br1 123.06(11) . . ? N2 Ni Br1 117.84(10) . . ? N1 Ni Br2 105.55(10) . . ? N2 Ni Br2 110.26(11) . . ? Br1 Ni Br2 113.61(3) . . ? C1 N1 C21 121.6(4) . . ? C1 N1 Ni 114.5(3) . . ? C21 N1 Ni 123.7(3) . . ? C6 N2 C5 109.0(3) . . ? C6 N2 C2 111.2(3) . . ? C5 N2 C2 111.5(3) . . ? C6 N2 Ni 111.0(3) . . ? C5 N2 Ni 108.1(3) . . ? C2 N2 Ni 106.0(3) . . ? N1 C1 C2 119.5(4) . . ? C1 C2 N2 106.7(3) . . ? C1 C2 C3 112.3(4) . . ? N2 C2 C3 114.0(4) . . ? C1 C2 C4 103.3(3) . . ? N2 C2 C4 112.8(4) . . ? C3 C2 C4 107.2(4) . . ? N2 C5 C7 117.1(4) . . ? N2 C6 C8 113.7(4) . . ? C26 C21 C22 120.4(4) . . ? C26 C21 N1 117.8(4) . . ? C22 C21 N1 121.7(4) . . ? C23 C22 C21 119.3(4) . . ? C24 C23 C22 120.5(5) . . ? C23 C24 C25 120.1(5) . . ? C26 C25 C24 120.1(4) . . ? C25 C26 C21 119.5(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.727 _refine_diff_density_min -1.442 _refine_diff_density_rms 0.149 # Attachment 'Ni-2b.cif' data_ic7092 _database_code_depnum_ccdc_archive 'CCDC 699111' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H26 Br2 N2 Ni' _chemical_formula_weight 464.92 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' Br Br -0.2901 2.4595 '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 7.9039(3) _cell_length_b 8.6754(3) _cell_length_c 15.4932(6) _cell_angle_alpha 102.012(1) _cell_angle_beta 95.157(1) _cell_angle_gamma 113.542(1) _cell_volume 934.71(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4790 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 5.308 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4790 _exptl_absorpt_correction_T_max 0.6944 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10492 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4155 _reflns_number_gt 3243 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SAINT' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0326P)^2^+0.4155P] 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 4155 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.006 _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 Ni Ni 0.82049(7) 0.60620(6) 0.73113(3) 0.01929(12) Uani 1 1 d . . . Br1 Br 0.86886(6) 0.80364(5) 0.64095(3) 0.03478(13) Uani 1 1 d . . . Br2 Br 1.08502(6) 0.59194(6) 0.80489(3) 0.03203(12) Uani 1 1 d . . . N1 N 0.6521(4) 0.6034(4) 0.81956(18) 0.0155(6) Uani 1 1 d . . . N2 N 0.5974(4) 0.3681(4) 0.66381(18) 0.0167(6) Uani 1 1 d . . . C1 C 0.4818(5) 0.4980(5) 0.7859(2) 0.0182(8) Uani 1 1 d . . . H1 H 0.3892 0.4848 0.8224 0.022 Uiso 1 1 calc R . . C2 C 0.4241(5) 0.3931(5) 0.6882(2) 0.0184(8) Uani 1 1 d . . . C3 C 0.2474(5) 0.2232(5) 0.6781(3) 0.0283(9) Uani 1 1 d . . . H3A H 0.2729 0.1594 0.7190 0.042 Uiso 1 1 calc R . . H3B H 0.2136 0.1508 0.6159 0.042 Uiso 1 1 calc R . . H3C H 0.1432 0.2512 0.6928 0.042 Uiso 1 1 calc R . . C4 C 0.3712(5) 0.5019(5) 0.6337(2) 0.0239(9) Uani 1 1 d . . . H4A H 0.2824 0.5398 0.6611 0.036 Uiso 1 1 calc R . . H4B H 0.3127 0.4309 0.5718 0.036 Uiso 1 1 calc R . . H4C H 0.4847 0.6044 0.6335 0.036 Uiso 1 1 calc R . . C5 C 0.6252(6) 0.2319(5) 0.7017(3) 0.0269(9) Uani 1 1 d . . . H5A H 0.5921 0.2434 0.7621 0.032 Uiso 1 1 calc R . . H5B H 0.7609 0.2598 0.7101 0.032 Uiso 1 1 calc R . . C6 C 0.5982(6) 0.3330(5) 0.5650(2) 0.0230(8) Uani 1 1 d . . . H6A H 0.5821 0.4260 0.5424 0.028 Uiso 1 1 calc R . . H6B H 0.4907 0.2206 0.5331 0.028 Uiso 1 1 calc R . . C7 C 0.5159(7) 0.0399(5) 0.6480(3) 0.0369(11) Uani 1 1 d . . . H7A H 0.3806 0.0069 0.6415 0.055 Uiso 1 1 calc R . . H7B H 0.5485 -0.0340 0.6798 0.055 Uiso 1 1 calc R . . H7C H 0.5488 0.0241 0.5883 0.055 Uiso 1 1 calc R . . C8 C 0.7798(6) 0.3260(6) 0.5443(3) 0.0326(10) Uani 1 1 d . . . H8A H 0.8870 0.4352 0.5779 0.049 Uiso 1 1 calc R . . H8B H 0.7783 0.3102 0.4797 0.049 Uiso 1 1 calc R . . H8C H 0.7911 0.2280 0.5621 0.049 Uiso 1 1 calc R . . C21 C 0.7032(5) 0.7059(4) 0.9124(2) 0.0169(7) Uani 1 1 d . . . C22 C 0.7548(5) 0.6384(5) 0.9792(2) 0.0187(8) Uani 1 1 d . . . C23 C 0.8163(5) 0.7455(5) 1.0674(2) 0.0256(9) Uani 1 1 d . . . H23 H 0.8560 0.7047 1.1142 0.031 Uiso 1 1 calc R . . C24 C 0.8200(6) 0.9095(5) 1.0874(3) 0.0292(10) Uani 1 1 d . . . H24 H 0.8628 0.9805 1.1477 0.035 Uiso 1 1 calc R . . C25 C 0.7622(6) 0.9719(5) 1.0209(3) 0.0285(9) Uani 1 1 d . . . H25 H 0.7609 1.0832 1.0361 0.034 Uiso 1 1 calc R . . C26 C 0.7055(5) 0.8716(5) 0.9310(2) 0.0208(8) Uani 1 1 d . . . C27 C 0.7406(6) 0.4551(5) 0.9590(3) 0.0234(8) Uani 1 1 d . . . H27A H 0.6078 0.3711 0.9438 0.035 Uiso 1 1 calc R . . H27B H 0.8029 0.4396 1.0120 0.035 Uiso 1 1 calc R . . H27C H 0.8017 0.4356 0.9082 0.035 Uiso 1 1 calc R . . C28 C 0.6476(6) 0.9410(5) 0.8573(3) 0.0306(10) Uani 1 1 d . . . H28A H 0.7235 0.9377 0.8109 0.046 Uiso 1 1 calc R . . H28B H 0.6673 1.0615 0.8827 0.046 Uiso 1 1 calc R . . H28C H 0.5143 0.8686 0.8305 0.046 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 Ni 0.0172(3) 0.0193(2) 0.0163(2) 0.00082(19) 0.00357(19) 0.0046(2) Br1 0.0350(3) 0.0243(2) 0.0350(3) 0.01202(18) 0.00528(19) 0.00099(19) Br2 0.0266(2) 0.0425(3) 0.0271(2) 0.00317(19) 0.00221(17) 0.0185(2) N1 0.0172(16) 0.0140(14) 0.0123(15) 0.0010(12) -0.0004(12) 0.0055(13) N2 0.0235(17) 0.0149(15) 0.0106(14) 0.0034(12) 0.0014(12) 0.0075(13) C1 0.024(2) 0.0222(19) 0.0138(18) 0.0099(15) 0.0076(15) 0.0114(17) C2 0.0192(19) 0.0197(18) 0.0142(18) 0.0056(15) 0.0041(15) 0.0054(16) C3 0.022(2) 0.028(2) 0.022(2) 0.0040(17) 0.0026(17) 0.0000(18) C4 0.024(2) 0.031(2) 0.0184(19) 0.0072(17) 0.0034(16) 0.0132(18) C5 0.040(3) 0.0192(19) 0.019(2) 0.0042(16) -0.0006(18) 0.0121(19) C6 0.032(2) 0.0212(19) 0.0119(18) 0.0014(15) 0.0039(16) 0.0096(17) C7 0.060(3) 0.018(2) 0.026(2) 0.0003(17) -0.002(2) 0.015(2) C8 0.037(3) 0.038(2) 0.021(2) 0.0004(18) 0.0073(19) 0.017(2) C21 0.0162(18) 0.0180(18) 0.0113(17) 0.0009(14) 0.0039(14) 0.0034(15) C22 0.0137(19) 0.0181(18) 0.0206(19) 0.0039(15) 0.0050(15) 0.0033(15) C23 0.025(2) 0.028(2) 0.0149(19) 0.0064(16) 0.0023(16) 0.0025(18) C24 0.031(2) 0.026(2) 0.016(2) -0.0007(17) 0.0029(17) 0.0012(18) C25 0.033(2) 0.022(2) 0.023(2) -0.0005(17) 0.0073(18) 0.0075(18) C26 0.021(2) 0.0191(19) 0.0198(19) 0.0048(15) 0.0071(16) 0.0051(16) C27 0.025(2) 0.027(2) 0.020(2) 0.0096(16) 0.0029(16) 0.0112(17) C28 0.039(3) 0.025(2) 0.028(2) 0.0037(18) 0.0052(19) 0.015(2) _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 Ni N1 1.991(3) . ? Ni N2 2.080(3) . ? Ni Br2 2.3514(6) . ? Ni Br1 2.3666(6) . ? N1 C1 1.270(4) . ? N1 C21 1.449(4) . ? N2 C6 1.499(4) . ? N2 C5 1.504(5) . ? N2 C2 1.537(5) . ? C1 C2 1.516(5) . ? C2 C4 1.537(5) . ? C2 C3 1.538(5) . ? C5 C7 1.536(5) . ? C6 C8 1.520(5) . ? C21 C22 1.395(5) . ? C21 C26 1.398(5) . ? C22 C23 1.400(5) . ? C22 C27 1.512(5) . ? C23 C24 1.379(6) . ? C24 C25 1.381(6) . ? C25 C26 1.403(5) . ? C26 C28 1.513(5) . ? 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 Ni N2 82.66(11) . . ? N1 Ni Br2 106.62(9) . . ? N2 Ni Br2 116.00(8) . . ? N1 Ni Br1 118.66(8) . . ? N2 Ni Br1 109.55(8) . . ? Br2 Ni Br1 118.33(2) . . ? C1 N1 C21 119.9(3) . . ? C1 N1 Ni 112.3(2) . . ? C21 N1 Ni 127.7(2) . . ? C6 N2 C5 111.3(3) . . ? C6 N2 C2 113.5(3) . . ? C5 N2 C2 112.1(3) . . ? C6 N2 Ni 109.5(2) . . ? C5 N2 Ni 106.7(2) . . ? C2 N2 Ni 103.34(19) . . ? N1 C1 C2 120.9(3) . . ? C1 C2 N2 105.8(3) . . ? C1 C2 C4 106.8(3) . . ? N2 C2 C4 112.0(3) . . ? C1 C2 C3 108.8(3) . . ? N2 C2 C3 115.0(3) . . ? C4 C2 C3 108.1(3) . . ? N2 C5 C7 118.1(3) . . ? N2 C6 C8 111.9(3) . . ? C22 C21 C26 122.6(3) . . ? C22 C21 N1 118.9(3) . . ? C26 C21 N1 118.5(3) . . ? C21 C22 C23 117.5(3) . . ? C21 C22 C27 122.1(3) . . ? C23 C22 C27 120.4(3) . . ? C24 C23 C22 120.9(4) . . ? C23 C24 C25 120.8(4) . . ? C24 C25 C26 120.3(4) . . ? C21 C26 C25 117.8(3) . . ? C21 C26 C28 121.5(3) . . ? C25 C26 C28 120.7(3) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.473 _refine_diff_density_min -0.634 _refine_diff_density_rms 0.104 # Attachment 'Ni-4c.cif' data_ic10403 _database_code_depnum_ccdc_archive 'CCDC 699112' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H30 Br2 N2 Ni' _chemical_formula_weight 504.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 15.1090(3) _cell_length_b 10.4250(3) _cell_length_c 14.4930(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2282.81(9) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 22183 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 4.354 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.338 _exptl_absorpt_correction_T_max 0.533 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13320 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4895 _reflns_number_gt 3227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0514P)^2^+1.2698P] 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 0.0010(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.016(14) _refine_ls_number_reflns 4895 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0814 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 0.61570(5) 0.53028(10) 0.30180(5) 0.1031(3) Uani 1 1 d . . . Br2 Br 0.61081(5) 0.88803(8) 0.20600(7) 0.1061(3) Uani 1 1 d . . . Ni1 Ni 0.56136(4) 0.67719(6) 0.19171(5) 0.0600(2) Uani 1 1 d . . . N1 N 0.5655(2) 0.6144(3) 0.0613(2) 0.0397(8) Uani 1 1 d . . . N2 N 0.4286(2) 0.6441(4) 0.1750(3) 0.0543(11) Uani 1 1 d . . . C1 C 0.4937(3) 0.5601(5) 0.0364(3) 0.0520(12) Uani 1 1 d . . . H1A H 0.4882 0.5303 -0.0238 0.062 Uiso 1 1 calc R . . C2 C 0.4181(3) 0.5434(5) 0.1018(4) 0.0559(13) Uani 1 1 d . . . C3 C 0.4303(5) 0.4098(6) 0.1476(5) 0.088(2) Uani 1 1 d . . . H3A H 0.4857 0.4077 0.1800 0.132 Uiso 1 1 calc R . . H3B H 0.4299 0.3445 0.1010 0.132 Uiso 1 1 calc R . . H3C H 0.3828 0.3948 0.1903 0.132 Uiso 1 1 calc R . . C4 C 0.3305(4) 0.5499(8) 0.0497(4) 0.089(2) Uani 1 1 d . . . H4A H 0.3242 0.6330 0.0219 0.134 Uiso 1 1 calc R . . H4B H 0.2825 0.5356 0.0919 0.134 Uiso 1 1 calc R . . H4C H 0.3296 0.4853 0.0025 0.134 Uiso 1 1 calc R . . C5 C 0.3761(4) 0.6294(7) 0.2636(4) 0.0752(18) Uani 1 1 d . . . H5A H 0.3213 0.5821 0.2562 0.090 Uiso 1 1 calc R . . H5B H 0.4105 0.5960 0.3148 0.090 Uiso 1 1 calc R . . C6 C 0.3642(5) 0.7700(9) 0.2660(6) 0.104(3) Uani 1 1 d . . . H6A H 0.4081 0.8147 0.3027 0.124 Uiso 1 1 calc R . . H6B H 0.3048 0.7970 0.2821 0.124 Uiso 1 1 calc R . . C7 C 0.3833(4) 0.7711(7) 0.1617(5) 0.0787(18) Uani 1 1 d . . . H7A H 0.3307 0.7671 0.1234 0.094 Uiso 1 1 calc R . . H7B H 0.4224 0.8396 0.1420 0.094 Uiso 1 1 calc R . . C21 C 0.6371(3) 0.6255(5) -0.0042(3) 0.0453(11) Uani 1 1 d . . . C22 C 0.7030(3) 0.5306(5) -0.0035(4) 0.0593(13) Uani 1 1 d . . . C23 C 0.7693(4) 0.5416(6) -0.0698(5) 0.0730(17) Uani 1 1 d . . . H23A H 0.8128 0.4786 -0.0729 0.088 Uiso 1 1 calc R . . C24 C 0.7726(4) 0.6411(7) -0.1298(4) 0.0785(19) Uani 1 1 d . . . H24A H 0.8180 0.6464 -0.1730 0.094 Uiso 1 1 calc R . . C25 C 0.7084(4) 0.7343(6) -0.1265(4) 0.0660(15) Uani 1 1 d . . . H25A H 0.7118 0.8029 -0.1673 0.079 Uiso 1 1 calc R . . C26 C 0.6385(3) 0.7297(5) -0.0643(3) 0.0486(11) Uani 1 1 d . . . C27 C 0.6997(4) 0.4179(5) 0.0618(4) 0.0703(16) Uani 1 1 d . . . H27A H 0.6568 0.4389 0.1102 0.084 Uiso 1 1 calc R . . C28 C 0.5686(3) 0.8333(5) -0.0662(4) 0.0611(14) Uani 1 1 d . . . H28A H 0.5278 0.8178 -0.0149 0.073 Uiso 1 1 calc R . . C29 C 0.6671(8) 0.2967(7) 0.0141(7) 0.126(3) Uani 1 1 d . . . H29A H 0.6113 0.3135 -0.0152 0.189 Uiso 1 1 calc R . . H29B H 0.6599 0.2297 0.0589 0.189 Uiso 1 1 calc R . . H29C H 0.7095 0.2704 -0.0314 0.189 Uiso 1 1 calc R . . C30 C 0.7886(6) 0.3938(8) 0.1092(7) 0.117(3) Uani 1 1 d . . . H30A H 0.8081 0.4711 0.1389 0.175 Uiso 1 1 calc R . . H30B H 0.8315 0.3680 0.0641 0.175 Uiso 1 1 calc R . . H30D H 0.7819 0.3272 0.1545 0.175 Uiso 1 1 calc R . . C31 C 0.6058(5) 0.9677(7) -0.0556(7) 0.099(2) Uani 1 1 d . . . H31A H 0.6390 0.9731 0.0007 0.148 Uiso 1 1 calc R . . H31D H 0.5580 1.0284 -0.0539 0.148 Uiso 1 1 calc R . . H31B H 0.6437 0.9868 -0.1069 0.148 Uiso 1 1 calc R . . C32 C 0.5151(5) 0.8256(8) -0.1570(6) 0.102(2) Uani 1 1 d . . . H32D H 0.4915 0.7407 -0.1640 0.153 Uiso 1 1 calc R . . H32A H 0.5532 0.8448 -0.2082 0.153 Uiso 1 1 calc R . . H32B H 0.4675 0.8865 -0.1551 0.153 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 0.0899(5) 0.1565(8) 0.0627(3) 0.0291(5) -0.0123(4) 0.0017(5) Br2 0.1006(5) 0.1014(5) 0.1164(7) -0.0422(5) 0.0137(5) -0.0370(4) Ni1 0.0526(3) 0.0863(4) 0.0409(3) -0.0096(4) 0.0008(3) -0.0139(3) N1 0.049(2) 0.0383(19) 0.0316(17) 0.0009(16) -0.0001(16) 0.0002(17) N2 0.049(2) 0.068(2) 0.046(3) -0.002(2) 0.0081(18) -0.0054(19) C1 0.060(3) 0.057(3) 0.039(2) -0.006(2) -0.002(2) -0.004(3) C2 0.047(3) 0.071(3) 0.050(3) -0.006(3) -0.003(2) -0.015(3) C3 0.101(5) 0.073(4) 0.090(5) 0.006(4) 0.014(4) -0.030(4) C4 0.050(3) 0.153(6) 0.065(4) -0.023(4) -0.001(3) -0.023(4) C5 0.066(4) 0.115(6) 0.045(3) -0.005(3) 0.015(3) -0.014(4) C6 0.083(4) 0.135(8) 0.093(5) -0.041(5) 0.027(4) 0.001(5) C7 0.067(3) 0.089(5) 0.081(4) -0.006(4) 0.007(3) 0.012(3) C21 0.048(3) 0.049(3) 0.039(2) -0.003(2) -0.001(2) -0.002(2) C22 0.055(3) 0.072(3) 0.050(3) -0.004(3) -0.004(2) 0.015(3) C23 0.054(3) 0.093(5) 0.072(4) -0.007(4) -0.003(3) 0.027(3) C24 0.046(3) 0.119(6) 0.070(4) 0.000(4) 0.013(3) 0.003(3) C25 0.053(3) 0.085(4) 0.060(3) 0.016(3) 0.009(3) -0.005(3) C26 0.049(3) 0.052(3) 0.044(3) 0.001(2) 0.004(2) 0.003(2) C27 0.088(4) 0.059(3) 0.064(3) 0.003(3) -0.016(3) 0.024(3) C28 0.054(3) 0.058(3) 0.072(3) 0.015(3) 0.007(3) 0.000(3) C29 0.194(10) 0.077(5) 0.108(7) 0.010(5) -0.034(7) -0.018(5) C30 0.118(6) 0.108(6) 0.123(7) 0.028(5) -0.038(6) 0.024(5) C31 0.102(5) 0.063(4) 0.130(7) 0.017(4) -0.021(5) 0.001(4) C32 0.074(4) 0.106(5) 0.127(6) -0.012(5) -0.033(4) 0.011(4) _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 2.3591(10) . ? Br2 Ni1 2.3307(10) . ? Ni1 N1 2.002(3) . ? Ni1 N2 2.049(4) . ? N1 C1 1.276(6) . ? N1 C21 1.443(6) . ? N2 C2 1.501(7) . ? N2 C7 1.504(8) . ? N2 C5 1.517(7) . ? C1 C2 1.494(7) . ? C1 H1A 0.9300 . ? C2 C4 1.525(8) . ? C2 C3 1.554(8) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.477(11) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.539(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C21 C26 1.393(7) . ? C21 C22 1.403(7) . ? C22 C23 1.393(8) . ? C22 C27 1.510(8) . ? C23 C24 1.355(9) . ? C23 H23A 0.9300 . ? C24 C25 1.373(9) . ? C24 H24A 0.9300 . ? C25 C26 1.389(7) . ? C25 H25A 0.9300 . ? C26 C28 1.511(7) . ? C27 C29 1.523(10) . ? C27 C30 1.528(10) . ? C27 H27A 0.9800 . ? C28 C31 1.518(9) . ? C28 C32 1.546(9) . ? C28 H28A 0.9800 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30D 0.9600 . ? C31 H31A 0.9600 . ? C31 H31D 0.9600 . ? C31 H31B 0.9600 . ? C32 H32D 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 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 82.20(16) . . ? N1 Ni1 Br2 112.47(10) . . ? N2 Ni1 Br2 118.89(12) . . ? N1 Ni1 Br1 114.55(11) . . ? N2 Ni1 Br1 108.12(12) . . ? Br2 Ni1 Br1 116.14(4) . . ? C1 N1 C21 119.2(4) . . ? C1 N1 Ni1 112.6(3) . . ? C21 N1 Ni1 128.2(3) . . ? C2 N2 C7 118.4(4) . . ? C2 N2 C5 118.2(4) . . ? C7 N2 C5 87.7(4) . . ? C2 N2 Ni1 107.8(3) . . ? C7 N2 Ni1 108.2(4) . . ? C5 N2 Ni1 115.4(3) . . ? N1 C1 C2 121.6(4) . . ? N1 C1 H1A 119.2 . . ? C2 C1 H1A 119.2 . . ? C1 C2 N2 106.6(4) . . ? C1 C2 C4 110.2(4) . . ? N2 C2 C4 114.3(5) . . ? C1 C2 C3 106.6(5) . . ? N2 C2 C3 108.1(5) . . ? C4 C2 C3 110.8(5) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 N2 89.1(5) . . ? C6 C5 H5A 113.8 . . ? N2 C5 H5A 113.8 . . ? C6 C5 H5B 113.8 . . ? N2 C5 H5B 113.8 . . ? H5A C5 H5B 111.0 . . ? C5 C6 C7 87.8(6) . . ? C5 C6 H6A 114.0 . . ? C7 C6 H6A 114.0 . . ? C5 C6 H6B 114.0 . . ? C7 C6 H6B 114.0 . . ? H6A C6 H6B 111.2 . . ? N2 C7 C6 87.2(6) . . ? N2 C7 H7A 114.1 . . ? C6 C7 H7A 114.1 . . ? N2 C7 H7B 114.1 . . ? C6 C7 H7B 114.1 . . ? H7A C7 H7B 111.3 . . ? C26 C21 C22 122.9(4) . . ? C26 C21 N1 119.0(4) . . ? C22 C21 N1 118.1(4) . . ? C23 C22 C21 116.6(5) . . ? C23 C22 C27 121.3(5) . . ? C21 C22 C27 122.0(5) . . ? C24 C23 C22 122.1(5) . . ? C24 C23 H23A 118.9 . . ? C22 C23 H23A 118.9 . . ? C23 C24 C25 119.5(5) . . ? C23 C24 H24A 120.2 . . ? C25 C24 H24A 120.2 . . ? C24 C25 C26 122.4(6) . . ? C24 C25 H25A 118.8 . . ? C26 C25 H25A 118.8 . . ? C25 C26 C21 116.4(5) . . ? C25 C26 C28 119.6(5) . . ? C21 C26 C28 124.0(4) . . ? C22 C27 C29 111.8(5) . . ? C22 C27 C30 112.4(6) . . ? C29 C27 C30 110.6(6) . . ? C22 C27 H27A 107.2 . . ? C29 C27 H27A 107.2 . . ? C30 C27 H27A 107.2 . . ? C26 C28 C31 113.6(5) . . ? C26 C28 C32 110.1(5) . . ? C31 C28 C32 109.1(6) . . ? C26 C28 H28A 107.9 . . ? C31 C28 H28A 107.9 . . ? C32 C28 H28A 107.9 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30D 109.5 . . ? H30A C30 H30D 109.5 . . ? H30B C30 H30D 109.5 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31D 109.5 . . ? H31A C31 H31D 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? H31D C31 H31B 109.5 . . ? C28 C32 H32D 109.5 . . ? C28 C32 H32A 109.5 . . ? H32D C32 H32A 109.5 . . ? C28 C32 H32B 109.5 . . ? H32D C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.585 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.057 # Attachment 'Ni-5c.cif' data_ic9412 _database_code_depnum_ccdc_archive 'CCDC 699113' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H32 Br2 N2 Ni' _chemical_formula_weight 519.01 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.66900(10) _cell_length_b 14.1770(2) _cell_length_c 19.0860(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.9170(10) _cell_angle_gamma 90.00 _cell_volume 2295.12(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 38432 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 4.333 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.325 _exptl_absorpt_correction_T_max 0.534 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17428 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5242 _reflns_number_gt 3673 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0546P)^2^+1.2503P] 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 0.0041(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5242 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 Br1 Br 0.70494(5) 0.17740(3) 0.92189(2) 0.07948(17) Uani 1 1 d . . . Br2 Br 0.90776(7) 0.03339(3) 0.78625(3) 0.1061(2) Uani 1 1 d . . . Ni1 Ni 0.90462(5) 0.16749(3) 0.85659(2) 0.05598(15) Uani 1 1 d . . . N1 N 0.9053(3) 0.29617(17) 0.81426(13) 0.0495(5) Uani 1 1 d . . . N2 N 1.1405(3) 0.19696(19) 0.89752(16) 0.0578(6) Uani 1 1 d . . . C1 C 1.0432(4) 0.3280(2) 0.81848(19) 0.0602(8) Uani 1 1 d . . . H1A H 1.0555 0.3888 0.8023 0.072 Uiso 1 1 calc R . . C2 C 1.1878(4) 0.2709(2) 0.8488(2) 0.0651(9) Uani 1 1 d . . . C3 C 1.2353(6) 0.2236(3) 0.7840(3) 0.0917(13) Uani 1 1 d . . . H3A H 1.1525 0.1821 0.7612 0.138 Uiso 1 1 calc R . . H3B H 1.3304 0.1880 0.7997 0.138 Uiso 1 1 calc R . . H3C H 1.2527 0.2711 0.7506 0.138 Uiso 1 1 calc R . . C4 C 1.3203(5) 0.3370(3) 0.8849(3) 0.0932(15) Uani 1 1 d . . . H4A H 1.2911 0.3668 0.9255 0.140 Uiso 1 1 calc R . . H4B H 1.3376 0.3844 0.8514 0.140 Uiso 1 1 calc R . . H4C H 1.4154 0.3014 0.9006 0.140 Uiso 1 1 calc R . . C5 C 1.1444(5) 0.2308(3) 0.9723(2) 0.0757(10) Uani 1 1 d . . . H5A H 1.0536 0.2700 0.9741 0.091 Uiso 1 1 calc R . . H5B H 1.2396 0.2666 0.9905 0.091 Uiso 1 1 calc R . . C6 C 1.2485(5) 0.1131(3) 0.9093(3) 0.0820(12) Uani 1 1 d . . . H6A H 1.3582 0.1325 0.9194 0.098 Uiso 1 1 calc R . . H6B H 1.2295 0.0718 0.8679 0.098 Uiso 1 1 calc R . . C7 C 1.1411(6) 0.1410(4) 1.0150(3) 0.1037(16) Uani 1 1 d . . . H7A H 1.2059 0.1475 1.0627 0.124 Uiso 1 1 calc R . . H7B H 1.0341 0.1261 1.0193 0.124 Uiso 1 1 calc R . . C8 C 1.2053(7) 0.0650(4) 0.9740(3) 0.1155(19) Uani 1 1 d . . . H8A H 1.1265 0.0166 0.9588 0.139 Uiso 1 1 calc R . . H8B H 1.2976 0.0361 1.0036 0.139 Uiso 1 1 calc R . . C21 C 0.7728(4) 0.3543(2) 0.78259(18) 0.0541(7) Uani 1 1 d . . . C22 C 0.7266(4) 0.4294(2) 0.82073(19) 0.0608(8) Uani 1 1 d . . . C23 C 0.5994(5) 0.4833(3) 0.7861(3) 0.0822(11) Uani 1 1 d . . . H23A H 0.5658 0.5337 0.8104 0.099 Uiso 1 1 calc R . . C24 C 0.5220(5) 0.4644(4) 0.7172(3) 0.0950(15) Uani 1 1 d . . . H24A H 0.4390 0.5025 0.6949 0.114 Uiso 1 1 calc R . . C25 C 0.5679(5) 0.3893(4) 0.6817(2) 0.0873(13) Uani 1 1 d . . . H25A H 0.5138 0.3762 0.6353 0.105 Uiso 1 1 calc R . . C26 C 0.6938(5) 0.3314(3) 0.7130(2) 0.0680(9) Uani 1 1 d . . . C27 C 0.8101(4) 0.4560(3) 0.8961(2) 0.0666(9) Uani 1 1 d . . . H27A H 0.8878 0.4067 0.9136 0.080 Uiso 1 1 calc R . . C28 C 0.7474(6) 0.2513(3) 0.6717(2) 0.0841(12) Uani 1 1 d . . . H28A H 0.8053 0.2066 0.7067 0.101 Uiso 1 1 calc R . . C29 C 0.8990(7) 0.5492(3) 0.8962(3) 0.1008(15) Uani 1 1 d . . . H29A H 0.9698 0.5449 0.8637 0.151 Uiso 1 1 calc R . . H29B H 0.9580 0.5620 0.9436 0.151 Uiso 1 1 calc R . . H29C H 0.8250 0.5993 0.8813 0.151 Uiso 1 1 calc R . . C30 C 0.6968(6) 0.4616(4) 0.9476(3) 0.0920(13) Uani 1 1 d . . . H30A H 0.6417 0.4027 0.9471 0.138 Uiso 1 1 calc R . . H30B H 0.6222 0.5114 0.9329 0.138 Uiso 1 1 calc R . . H30C H 0.7552 0.4740 0.9952 0.138 Uiso 1 1 calc R . . C31 C 0.8607(7) 0.2862(4) 0.6259(3) 0.1082(16) Uani 1 1 d . . . H31A H 0.9458 0.3202 0.6554 0.162 Uiso 1 1 calc R . . H31B H 0.8055 0.3272 0.5890 0.162 Uiso 1 1 calc R . . H31C H 0.9022 0.2333 0.6043 0.162 Uiso 1 1 calc R . . C32 C 0.6125(9) 0.1974(5) 0.6247(4) 0.145(3) Uani 1 1 d . . . H32A H 0.5411 0.1754 0.6534 0.217 Uiso 1 1 calc R . . H32B H 0.6540 0.1444 0.6032 0.217 Uiso 1 1 calc R . . H32C H 0.5574 0.2383 0.5878 0.217 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 0.0632(3) 0.0905(3) 0.0909(3) 0.0174(2) 0.0302(2) 0.01215(19) Br2 0.1159(4) 0.0640(3) 0.1449(5) -0.0390(3) 0.0425(4) -0.0092(2) Ni1 0.0519(3) 0.0409(2) 0.0771(3) 0.00160(18) 0.0179(2) 0.00058(16) N1 0.0508(14) 0.0438(12) 0.0549(14) 0.0011(11) 0.0135(11) 0.0021(11) N2 0.0512(15) 0.0470(13) 0.0764(17) 0.0056(12) 0.0161(13) 0.0062(11) C1 0.0592(19) 0.0498(17) 0.073(2) 0.0076(15) 0.0164(16) -0.0011(14) C2 0.0521(18) 0.0533(18) 0.093(3) 0.0075(17) 0.0214(18) 0.0001(14) C3 0.088(3) 0.095(3) 0.106(3) 0.012(3) 0.052(3) 0.012(2) C4 0.056(2) 0.075(3) 0.144(4) 0.016(3) 0.010(3) -0.0115(19) C5 0.067(2) 0.080(3) 0.075(2) -0.001(2) 0.0023(18) 0.0043(19) C6 0.062(2) 0.060(2) 0.126(3) 0.016(2) 0.024(2) 0.0175(17) C7 0.091(3) 0.125(4) 0.094(3) 0.040(3) 0.016(3) 0.023(3) C8 0.117(4) 0.088(3) 0.143(5) 0.050(3) 0.032(4) 0.024(3) C21 0.0516(17) 0.0493(16) 0.0604(18) 0.0065(13) 0.0090(14) -0.0028(13) C22 0.0551(18) 0.0566(18) 0.070(2) 0.0095(15) 0.0111(15) 0.0076(15) C23 0.075(3) 0.075(3) 0.097(3) 0.013(2) 0.021(2) 0.021(2) C24 0.067(3) 0.107(4) 0.105(4) 0.034(3) 0.001(2) 0.016(2) C25 0.080(3) 0.098(3) 0.073(3) 0.019(2) -0.010(2) -0.005(2) C26 0.071(2) 0.063(2) 0.067(2) 0.0102(16) 0.0071(18) -0.0107(17) C27 0.068(2) 0.0573(19) 0.073(2) -0.0034(16) 0.0114(18) 0.0097(16) C28 0.122(4) 0.067(2) 0.059(2) -0.0006(18) 0.008(2) -0.016(2) C29 0.116(4) 0.086(3) 0.101(3) -0.012(3) 0.024(3) -0.026(3) C30 0.095(3) 0.102(3) 0.084(3) -0.013(2) 0.028(2) 0.000(3) C31 0.132(5) 0.105(4) 0.094(3) -0.011(3) 0.040(3) 0.000(3) C32 0.180(7) 0.127(5) 0.121(5) -0.036(4) 0.018(5) -0.066(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 2.3368(6) . ? Br2 Ni1 2.3307(6) . ? Ni1 N1 1.996(2) . ? Ni1 N2 2.076(3) . ? N1 C1 1.264(4) . ? N1 C21 1.441(4) . ? N2 C6 1.501(4) . ? N2 C5 1.500(5) . ? N2 C2 1.513(4) . ? C1 C2 1.504(5) . ? C1 H1A 0.9300 . ? C2 C4 1.532(5) . ? C2 C3 1.536(6) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C7 1.515(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C8 1.523(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.504(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C21 C22 1.395(5) . ? C21 C26 1.402(5) . ? C22 C23 1.391(5) . ? C22 C27 1.519(5) . ? C23 C24 1.374(7) . ? C23 H23A 0.9300 . ? C24 C25 1.365(7) . ? C24 H24A 0.9300 . ? C25 C26 1.397(6) . ? C25 H25A 0.9300 . ? C26 C28 1.509(6) . ? C27 C29 1.529(6) . ? C27 C30 1.528(6) . ? C27 H27A 0.9800 . ? C28 C32 1.524(7) . ? C28 C31 1.527(7) . ? C28 H28A 0.9800 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 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 83.30(11) . . ? N1 Ni1 Br2 120.74(8) . . ? N2 Ni1 Br2 104.67(8) . . ? N1 Ni1 Br1 103.03(7) . . ? N2 Ni1 Br1 124.61(8) . . ? Br2 Ni1 Br1 117.02(2) . . ? C1 N1 C21 118.9(3) . . ? C1 N1 Ni1 112.5(2) . . ? C21 N1 Ni1 128.6(2) . . ? C6 N2 C5 102.7(3) . . ? C6 N2 C2 113.7(3) . . ? C5 N2 C2 114.1(3) . . ? C6 N2 Ni1 115.6(2) . . ? C5 N2 Ni1 104.4(2) . . ? C2 N2 Ni1 106.2(2) . . ? N1 C1 C2 122.3(3) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C1 C2 N2 107.4(3) . . ? C1 C2 C4 109.4(3) . . ? N2 C2 C4 114.8(3) . . ? C1 C2 C3 105.4(3) . . ? N2 C2 C3 110.1(3) . . ? C4 C2 C3 109.2(3) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 C7 104.1(4) . . ? N2 C5 H5A 110.9 . . ? C7 C5 H5A 110.9 . . ? N2 C5 H5B 110.9 . . ? C7 C5 H5B 110.9 . . ? H5A C5 H5B 109.0 . . ? N2 C6 C8 103.0(3) . . ? N2 C6 H6A 111.2 . . ? C8 C6 H6A 111.2 . . ? N2 C6 H6B 111.2 . . ? C8 C6 H6B 111.2 . . ? H6A C6 H6B 109.1 . . ? C8 C7 C5 105.8(4) . . ? C8 C7 H7A 110.6 . . ? C5 C7 H7A 110.6 . . ? C8 C7 H7B 110.6 . . ? C5 C7 H7B 110.6 . . ? H7A C7 H7B 108.7 . . ? C7 C8 C6 106.3(4) . . ? C7 C8 H8A 110.5 . . ? C6 C8 H8A 110.5 . . ? C7 C8 H8B 110.5 . . ? C6 C8 H8B 110.5 . . ? H8A C8 H8B 108.7 . . ? C22 C21 C26 122.3(3) . . ? C22 C21 N1 120.5(3) . . ? C26 C21 N1 117.2(3) . . ? C23 C22 C21 117.2(4) . . ? C23 C22 C27 119.3(3) . . ? C21 C22 C27 123.5(3) . . ? C24 C23 C22 122.0(4) . . ? C24 C23 H23A 119.0 . . ? C22 C23 H23A 119.0 . . ? C25 C24 C23 119.6(4) . . ? C25 C24 H24A 120.2 . . ? C23 C24 H24A 120.2 . . ? C24 C25 C26 121.9(4) . . ? C24 C25 H25A 119.1 . . ? C26 C25 H25A 119.1 . . ? C25 C26 C21 117.1(4) . . ? C25 C26 C28 121.1(4) . . ? C21 C26 C28 121.8(3) . . ? C22 C27 C29 110.9(3) . . ? C22 C27 C30 112.2(3) . . ? C29 C27 C30 110.2(3) . . ? C22 C27 H27A 107.8 . . ? C29 C27 H27A 107.8 . . ? C30 C27 H27A 107.8 . . ? C26 C28 C32 113.8(5) . . ? C26 C28 C31 111.0(4) . . ? C32 C28 C31 109.4(4) . . ? C26 C28 H28A 107.5 . . ? C32 C28 H28A 107.5 . . ? C31 C28 H28A 107.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C28 C32 H32A 109.5 . . ? C28 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C28 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.467 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.056