# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Gao, Haiyang' 'Hu, Haibin' 'Fangming, Zhu' 'Qing, Wu' _publ_contact_author_name 'Gao, Haiyang' _publ_contact_author_email gaohy@mail.sysu.edu.cn _publ_section_title ; Thermally Robust Amine-Imine Nickel Catalyst Precursor for Living Polymerization of Ethylene above Room Temperature ; # Attachment 'IAHH.cif' data_g102709m _database_code_depnum_ccdc_archive 'CCDC 867170' #TrackingRef 'IAHH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 Br2 N2 Ni' _chemical_formula_weight 470.88 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' 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' _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 12.487(4) _cell_length_b 8.246(2) _cell_length_c 18.729(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.359(5) _cell_angle_gamma 90.00 _cell_volume 1890.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 5.250 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2010 _exptl_absorpt_correction_T_max 0.3655 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14392 _diffrn_reflns_av_R_equivalents 0.0940 _diffrn_reflns_av_sigmaI/netI 0.0859 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3697 _reflns_number_gt 1849 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XSCANS' _computing_publication_material 'Bruker XSCANS' _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^)+(0.0710P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3697 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1173 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1470 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.932 _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 Br1 Br 0.62218(6) 1.24580(9) 0.03958(4) 0.0700(3) Uani 1 1 d . . . Br2 Br 0.94118(7) 1.23270(9) 0.00147(5) 0.0802(3) Uani 1 1 d . . . C1 C 0.8607(5) 0.9325(7) 0.1625(3) 0.0487(15) Uani 1 1 d . . . C2 C 0.9548(6) 0.8614(8) 0.2007(4) 0.0656(19) Uani 1 1 d . . . H2 H 1.0006 0.8045 0.1760 0.079 Uiso 1 1 calc R . . C3 C 0.9809(6) 0.8750(9) 0.2758(4) 0.077(2) Uani 1 1 d . . . H3 H 1.0441 0.8274 0.3019 0.093 Uiso 1 1 calc R . . C4 C 0.9125(7) 0.9596(10) 0.3114(4) 0.080(2) Uani 1 1 d . . . H4 H 0.9284 0.9660 0.3620 0.096 Uiso 1 1 calc R . . C5 C 0.8224(7) 1.0335(10) 0.2738(4) 0.076(2) Uani 1 1 d . . . H5 H 0.7780 1.0936 0.2984 0.091 Uiso 1 1 calc R . . C6 C 0.7956(6) 1.0201(8) 0.1984(3) 0.0593(18) Uani 1 1 d . . . H6 H 0.7334 1.0709 0.1726 0.071 Uiso 1 1 calc R . . C7 C 0.7626(5) 0.7726(7) 0.0562(3) 0.0497(16) Uani 1 1 d . . . C8 C 0.6581(6) 0.7712(8) 0.0873(4) 0.072(2) Uani 1 1 d . . . H8A H 0.6219 0.8740 0.0782 0.107 Uiso 1 1 calc R . . H8B H 0.6763 0.7521 0.1389 0.107 Uiso 1 1 calc R . . H8C H 0.6106 0.6867 0.0644 0.107 Uiso 1 1 calc R . . C9 C 0.8230(6) 0.6133(8) 0.0784(4) 0.070(2) Uani 1 1 d . . . H9A H 0.7723 0.5246 0.0694 0.106 Uiso 1 1 calc R . . H9B H 0.8555 0.6168 0.1293 0.106 Uiso 1 1 calc R . . H9C H 0.8790 0.5986 0.0505 0.106 Uiso 1 1 calc R . . C10 C 0.7277(5) 0.7911(8) -0.0248(4) 0.0542(17) Uani 1 1 d . . . C11 C 0.6877(8) 0.6447(10) -0.0692(4) 0.101(3) Uani 1 1 d . . . H11A H 0.6400 0.6778 -0.1135 0.151 Uiso 1 1 calc R . . H11B H 0.6487 0.5754 -0.0420 0.151 Uiso 1 1 calc R . . H11C H 0.7489 0.5869 -0.0808 0.151 Uiso 1 1 calc R . . C12 C 0.6922(7) 0.9757(9) -0.1256(4) 0.066(2) Uani 1 1 d . . . C13 C 0.5883(8) 1.0214(14) -0.1485(4) 0.123(4) Uani 1 1 d . . . H13 H 0.5414 1.0238 -0.1156 0.147 Uiso 1 1 calc R . . C14 C 0.5497(9) 1.0645(16) -0.2195(5) 0.150(5) Uani 1 1 d . . . H14 H 0.4765 1.0912 -0.2350 0.180 Uiso 1 1 calc R . . C15 C 0.6191(12) 1.0683(13) -0.2672(5) 0.117(4) Uani 1 1 d . . . H15 H 0.5936 1.0997 -0.3152 0.140 Uiso 1 1 calc R . . C16 C 0.7216(11) 1.0277(15) -0.2454(5) 0.117(4) Uani 1 1 d . . . H16 H 0.7681 1.0286 -0.2786 0.140 Uiso 1 1 calc R . . C17 C 0.7622(7) 0.9832(11) -0.1736(4) 0.098(3) Uani 1 1 d . . . H17 H 0.8359 0.9589 -0.1583 0.118 Uiso 1 1 calc R . . N1 N 0.8323(4) 0.9152(6) 0.0833(3) 0.0505(13) Uani 1 1 d . . . N2 N 0.7326(5) 0.9363(7) -0.0501(3) 0.0660(16) Uani 1 1 d . . . H1N H 0.894(5) 0.915(8) 0.062(3) 0.08(2) Uiso 1 1 d . . . Ni Ni 0.77957(7) 1.11037(9) 0.02102(4) 0.0523(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 Br1 0.0671(5) 0.0700(5) 0.0737(5) -0.0035(4) 0.0158(4) 0.0079(4) Br2 0.0805(6) 0.0631(5) 0.1088(6) -0.0079(4) 0.0474(5) -0.0091(4) C1 0.047(4) 0.045(4) 0.051(4) 0.000(3) 0.004(3) -0.008(3) C2 0.056(5) 0.058(5) 0.080(5) 0.002(4) 0.007(4) -0.006(4) C3 0.064(5) 0.083(6) 0.076(5) 0.005(5) -0.009(4) -0.012(4) C4 0.085(6) 0.086(6) 0.060(5) -0.001(4) -0.008(5) -0.024(5) C5 0.093(6) 0.081(6) 0.054(5) -0.008(4) 0.013(4) -0.006(5) C6 0.063(5) 0.061(4) 0.052(4) 0.000(3) 0.007(3) 0.005(4) C7 0.044(4) 0.055(4) 0.051(4) -0.005(3) 0.014(3) -0.001(3) C8 0.069(5) 0.073(5) 0.074(5) 0.009(4) 0.020(4) 0.002(4) C9 0.065(5) 0.047(4) 0.096(5) 0.006(4) 0.008(4) -0.003(4) C10 0.042(4) 0.052(4) 0.073(5) -0.002(4) 0.021(3) -0.002(3) C11 0.160(9) 0.070(6) 0.070(5) -0.026(5) 0.017(5) -0.006(6) C12 0.089(6) 0.059(5) 0.052(4) -0.009(3) 0.020(4) -0.001(4) C13 0.114(8) 0.211(11) 0.050(5) 0.040(6) 0.033(5) 0.073(8) C14 0.143(10) 0.235(14) 0.069(6) 0.038(8) 0.016(6) 0.067(9) C15 0.178(12) 0.122(8) 0.052(5) 0.017(5) 0.026(7) -0.017(9) C16 0.154(10) 0.147(10) 0.061(6) -0.017(6) 0.048(7) -0.060(9) C17 0.085(6) 0.142(8) 0.073(6) -0.034(6) 0.030(5) -0.038(6) N1 0.046(3) 0.051(3) 0.055(3) 0.000(3) 0.011(3) -0.003(3) N2 0.091(5) 0.059(4) 0.046(3) -0.008(3) 0.007(3) 0.004(3) Ni 0.0637(6) 0.0437(5) 0.0506(5) 0.0001(4) 0.0137(4) -0.0004(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 Ni 2.3451(12) . ? Br2 Ni 2.3485(12) . ? C1 C6 1.360(8) . ? C1 C2 1.380(9) . ? C1 N1 1.462(7) . ? C2 C3 1.384(9) . ? C2 H2 0.9300 . ? C3 C4 1.373(10) . ? C3 H3 0.9300 . ? C4 C5 1.350(10) . ? C4 H4 0.9300 . ? C5 C6 1.390(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.492(7) . ? C7 C10 1.501(9) . ? C7 C8 1.530(9) . ? C7 C9 1.531(8) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N2 1.293(8) . ? C10 C11 1.495(9) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.337(10) . ? C12 C17 1.374(9) . ? C12 N2 1.443(8) . ? C13 C14 1.368(11) . ? C13 H13 0.9300 . ? C14 C15 1.362(14) . ? C14 H14 0.9300 . ? C15 C16 1.309(14) . ? C15 H15 0.9300 . ? C16 C17 1.389(12) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N1 Ni 2.020(5) . ? N1 H1N 0.94(6) . ? N2 Ni 1.967(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 C6 C1 C2 120.0(6) . . ? C6 C1 N1 120.3(6) . . ? C2 C1 N1 119.7(6) . . ? C1 C2 C3 119.9(7) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 119.4(7) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.6(7) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.2(7) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 119.8(7) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? N1 C7 C10 107.3(5) . . ? N1 C7 C8 111.1(5) . . ? C10 C7 C8 106.6(5) . . ? N1 C7 C9 111.2(5) . . ? C10 C7 C9 113.0(5) . . ? C8 C7 C9 107.5(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 125.3(6) . . ? N2 C10 C7 116.0(6) . . ? C11 C10 C7 118.6(6) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 118.7(8) . . ? C13 C12 N2 120.5(6) . . ? C17 C12 N2 120.5(8) . . ? C12 C13 C14 121.2(8) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 119.7(10) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 119.9(10) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 121.2(9) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C12 C17 C16 119.2(9) . . ? C12 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C1 N1 C7 115.5(5) . . ? C1 N1 Ni 119.6(4) . . ? C7 N1 Ni 109.2(4) . . ? C1 N1 H1N 112(4) . . ? C7 N1 H1N 109(4) . . ? Ni N1 H1N 88(4) . . ? C10 N2 C12 122.4(6) . . ? C10 N2 Ni 117.2(4) . . ? C12 N2 Ni 119.9(5) . . ? N2 Ni N1 80.2(2) . . ? N2 Ni Br1 107.52(18) . . ? N1 Ni Br1 118.75(15) . . ? N2 Ni Br2 111.03(18) . . ? N1 Ni Br2 103.87(16) . . ? Br1 Ni Br2 126.13(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 C6 C1 C2 C3 2.1(10) . . . . ? N1 C1 C2 C3 -178.8(6) . . . . ? C1 C2 C3 C4 0.0(11) . . . . ? C2 C3 C4 C5 -2.1(12) . . . . ? C3 C4 C5 C6 2.2(12) . . . . ? C2 C1 C6 C5 -2.0(10) . . . . ? N1 C1 C6 C5 178.9(6) . . . . ? C4 C5 C6 C1 -0.2(11) . . . . ? N1 C7 C10 N2 -20.7(7) . . . . ? C8 C7 C10 N2 98.5(6) . . . . ? C9 C7 C10 N2 -143.6(6) . . . . ? N1 C7 C10 C11 160.9(6) . . . . ? C8 C7 C10 C11 -80.0(7) . . . . ? C9 C7 C10 C11 38.0(8) . . . . ? C17 C12 C13 C14 4.3(17) . . . . ? N2 C12 C13 C14 177.7(10) . . . . ? C12 C13 C14 C15 -3(2) . . . . ? C13 C14 C15 C16 1(2) . . . . ? C14 C15 C16 C17 -1(2) . . . . ? C13 C12 C17 C16 -4.1(14) . . . . ? N2 C12 C17 C16 -177.5(8) . . . . ? C15 C16 C17 C12 2.6(17) . . . . ? C6 C1 N1 C7 -90.3(7) . . . . ? C2 C1 N1 C7 90.6(7) . . . . ? C6 C1 N1 Ni 43.4(7) . . . . ? C2 C1 N1 Ni -135.7(5) . . . . ? C10 C7 N1 C1 170.9(5) . . . . ? C8 C7 N1 C1 54.7(7) . . . . ? C9 C7 N1 C1 -65.0(7) . . . . ? C10 C7 N1 Ni 32.6(5) . . . . ? C8 C7 N1 Ni -83.6(5) . . . . ? C9 C7 N1 Ni 156.7(4) . . . . ? C11 C10 N2 C12 4.2(11) . . . . ? C7 C10 N2 C12 -174.0(6) . . . . ? C11 C10 N2 Ni 176.2(6) . . . . ? C7 C10 N2 Ni -2.1(7) . . . . ? C13 C12 N2 C10 89.5(10) . . . . ? C17 C12 N2 C10 -97.3(9) . . . . ? C13 C12 N2 Ni -82.2(9) . . . . ? C17 C12 N2 Ni 91.0(8) . . . . ? C10 N2 Ni N1 17.2(5) . . . . ? C12 N2 Ni N1 -170.7(6) . . . . ? C10 N2 Ni Br1 -100.0(5) . . . . ? C12 N2 Ni Br1 72.1(5) . . . . ? C10 N2 Ni Br2 118.4(5) . . . . ? C12 N2 Ni Br2 -69.5(5) . . . . ? C1 N1 Ni N2 -163.7(5) . . . . ? C7 N1 Ni N2 -27.4(4) . . . . ? C1 N1 Ni Br1 -59.1(5) . . . . ? C7 N1 Ni Br1 77.3(4) . . . . ? C1 N1 Ni Br2 86.8(4) . . . . ? C7 N1 Ni Br2 -136.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.565 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.093 # Attachment 'IAMM.cif' data_g101309 _database_code_depnum_ccdc_archive 'CCDC 867171' #TrackingRef 'IAMM.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H29 Br2 N2 Ni' _chemical_formula_weight 527.99 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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 15.230(5) _cell_length_b 17.385(5) _cell_length_c 8.388(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2220.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1068 _exptl_absorpt_coefficient_mu 4.479 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2610 _exptl_absorpt_correction_T_max 0.4531 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 13452 _diffrn_reflns_av_R_equivalents 0.0807 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2249 _reflns_number_gt 1440 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0607P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0045(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2249 _refine_ls_number_parameters 141 _refine_ls_number_restraints 55 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 1.264 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.98764(6) 0.2500 0.18366(9) 0.0513(3) Uani 1 2 d S . . Br2 Br 1.08019(7) 0.2500 0.61489(13) 0.0675(4) Uani 1 2 d S . . C1 C 0.8665(4) 0.4021(3) 0.5300(8) 0.0447(15) Uani 1 1 d . . . C2 C 0.8709(4) 0.4621(4) 0.4195(8) 0.0521(17) Uani 1 1 d . . . C3 C 0.8867(4) 0.5350(4) 0.4785(12) 0.071(2) Uani 1 1 d . . . H3 H 0.8894 0.5761 0.4077 0.085 Uiso 1 1 calc RU . . C4 C 0.8982(5) 0.5484(5) 0.6354(12) 0.078(3) Uani 1 1 d . . . H4 H 0.9098 0.5979 0.6717 0.093 Uiso 1 1 calc RU . . C5 C 0.8928(5) 0.4890(5) 0.7398(11) 0.075(2) Uani 1 1 d . . . H5 H 0.8995 0.4987 0.8482 0.090 Uiso 1 1 calc RU . . C6 C 0.8774(4) 0.4143(4) 0.6896(9) 0.0614(19) Uani 1 1 d . . . C7 C 0.8584(6) 0.4501(6) 0.2453(11) 0.106(3) Uani 1 1 d . . . H7A H 0.8702 0.4973 0.1897 0.159 Uiso 1 1 calc RU . . H7B H 0.7990 0.4344 0.2252 0.159 Uiso 1 1 calc RU . . H7C H 0.8980 0.4109 0.2087 0.159 Uiso 1 1 calc RU . . C8 C 0.8732(7) 0.3488(6) 0.8099(11) 0.113(4) Uani 1 1 d . . . H8A H 0.9240 0.3506 0.8774 0.169 Uiso 1 1 calc RU . . H8B H 0.8716 0.3005 0.7545 0.169 Uiso 1 1 calc RU . . H8C H 0.8212 0.3541 0.8737 0.169 Uiso 1 1 calc RU . . C9 C 0.7704(4) 0.2902(3) 0.4524(9) 0.069(2) Uani 1 1 d D . . C10 C 0.6962(4) 0.3359(3) 0.5229(8) 0.0522(16) Uani 1 1 d . . . H10A H 0.6413 0.3136 0.4909 0.078 Uiso 1 1 calc RU . . H10B H 0.6994 0.3880 0.4859 0.078 Uiso 1 1 calc RU . . H10C H 0.7005 0.3350 0.6371 0.078 Uiso 1 1 calc RU . . C11 C 0.7410(8) 0.2808(7) 0.2705(11) 0.051(4) Uani 0.50 1 d PD . . H11A H 0.733(4) 0.3270(14) 0.210(7) 0.110(4) Uiso 0.50 1 d PDU . . H11B H 0.787(3) 0.2500 0.221(11) 0.108(5) Uiso 1 2 d SDU . . H11C H 0.6875(12) 0.2500 0.262(11) 0.098(5) Uiso 1 2 d SDU . . N N 0.8554(3) 0.3241(3) 0.4715(9) 0.0715(19) Uani 1 1 d . . . H1N H 0.8600 0.3378 0.3671 0.086 Uiso 1 1 calc RU . . Ni Ni 0.95401(7) 0.2500 0.46165(12) 0.0369(3) Uani 1 2 d S . . 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 0.0423(5) 0.0671(7) 0.0443(5) 0.000 0.0060(4) 0.000 Br2 0.0717(7) 0.0562(7) 0.0746(7) 0.000 -0.0419(6) 0.000 C1 0.039(3) 0.028(3) 0.067(4) -0.009(3) 0.003(3) 0.002(3) C2 0.042(3) 0.049(4) 0.065(4) -0.002(3) 0.003(3) 0.008(3) C3 0.061(5) 0.035(4) 0.117(7) 0.014(4) 0.018(4) 0.001(3) C4 0.064(5) 0.046(5) 0.123(8) -0.039(5) 0.008(5) -0.004(4) C5 0.074(5) 0.081(6) 0.071(5) -0.039(5) -0.003(4) 0.012(5) C6 0.064(5) 0.060(5) 0.061(4) 0.002(4) 0.007(3) 0.014(4) C7 0.103(7) 0.146(9) 0.068(5) -0.009(6) -0.013(5) 0.046(6) C8 0.143(10) 0.097(7) 0.099(7) 0.040(6) 0.020(6) 0.026(7) C9 0.048(4) 0.033(4) 0.126(7) 0.009(4) 0.028(4) 0.001(3) C10 0.047(4) 0.040(4) 0.070(4) -0.001(3) 0.011(3) 0.005(3) C11 0.047(7) 0.070(11) 0.037(6) 0.023(5) -0.009(5) 0.001(5) N 0.041(3) 0.038(3) 0.135(6) -0.031(3) -0.003(3) 0.000(3) Ni 0.0362(6) 0.0335(6) 0.0409(6) 0.000 -0.0059(4) 0.000 _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 Ni 2.3875(15) . ? Br2 Ni 2.3120(14) . ? C1 C6 1.365(9) . ? C1 C2 1.397(9) . ? C1 N 1.452(7) . ? C2 C3 1.380(10) . ? C2 C7 1.488(11) . ? C3 C4 1.349(11) . ? C3 H3 0.9300 . ? C4 C5 1.357(12) . ? C4 H4 0.9300 . ? C5 C6 1.385(10) . ? C5 H5 0.9300 . ? C6 C8 1.522(10) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C9 1.398(12) 7_565 ? C9 N 1.430(8) . ? C9 C10 1.503(8) . ? C9 C11 1.599(10) . ? C9 C11 2.013(12) 7_565 ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C11 1.07(2) 7_565 ? C11 C9 2.013(12) 7_565 ? C11 H11A 0.956(13) . ? C11 H11B 0.975(13) . ? C11 H11C 0.978(13) . ? N Ni 1.981(5) . ? N H1N 0.9100 . ? Ni N 1.981(5) 7_565 ? 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 121.9(6) . . ? C6 C1 N 119.4(6) . . ? C2 C1 N 118.6(6) . . ? C3 C2 C1 117.2(7) . . ? C3 C2 C7 120.2(7) . . ? C1 C2 C7 122.7(7) . . ? C4 C3 C2 122.1(7) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 119.4(7) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 121.8(8) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C1 C6 C5 117.6(7) . . ? C1 C6 C8 122.0(7) . . ? C5 C6 C8 120.4(8) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 C9 N 114.3(3) 7_565 . ? C9 C9 C10 121.9(3) 7_565 . ? N C9 C10 114.8(5) . . ? C9 C9 C11 84.1(5) 7_565 . ? N C9 C11 113.7(7) . . ? C10 C9 C11 102.6(7) . . ? C9 C9 C11 52.2(4) 7_565 7_565 ? N C9 C11 122.6(6) . 7_565 ? C10 C9 C11 117.0(6) . 7_565 ? C11 C9 C11 32.0(7) . 7_565 ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11 C11 C9 95.9(5) 7_565 . ? C11 C11 C9 52.2(4) 7_565 7_565 ? C9 C11 C9 43.7(4) . 7_565 ? C11 C11 H11A 147(4) 7_565 . ? C9 C11 H11A 117(4) . . ? C9 C11 H11A 161(4) 7_565 . ? C11 C11 H11B 56.7(10) 7_565 . ? C9 C11 H11B 105(6) . . ? C9 C11 H11B 80(5) 7_565 . ? H11A C11 H11B 109(2) . . ? C11 C11 H11C 56.8(10) 7_565 . ? C9 C11 H11C 111(6) . . ? C9 C11 H11C 85(5) 7_565 . ? H11A C11 H11C 108(2) . . ? H11B C11 H11C 105.5(17) . . ? C9 N C1 121.9(5) . . ? C9 N Ni 114.4(4) . . ? C1 N Ni 122.2(4) . . ? C9 N H1N 94.1 . . ? C1 N H1N 94.1 . . ? Ni N H1N 94.1 . . ? N Ni N 81.2(3) 7_565 . ? N Ni Br2 127.39(18) 7_565 . ? N Ni Br2 127.39(18) . . ? N Ni Br1 101.7(2) 7_565 . ? N Ni Br1 101.7(2) . . ? Br2 Ni Br1 111.39(6) . . ? 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 C6 C1 C2 C3 -0.1(9) . . . . ? N C1 C2 C3 -176.3(5) . . . . ? C6 C1 C2 C7 -179.4(6) . . . . ? N C1 C2 C7 4.4(9) . . . . ? C1 C2 C3 C4 0.6(10) . . . . ? C7 C2 C3 C4 179.9(7) . . . . ? C2 C3 C4 C5 -1.2(12) . . . . ? C3 C4 C5 C6 1.3(12) . . . . ? C2 C1 C6 C5 0.3(10) . . . . ? N C1 C6 C5 176.5(6) . . . . ? C2 C1 C6 C8 -179.6(7) . . . . ? N C1 C6 C8 -3.4(10) . . . . ? C4 C5 C6 C1 -0.9(11) . . . . ? C4 C5 C6 C8 179.0(8) . . . . ? C9 C9 C11 C11 0.000(2) 7_565 . . 7_565 ? N C9 C11 C11 114.0(4) . . . 7_565 ? C10 C9 C11 C11 -121.4(4) . . . 7_565 ? N C9 C11 C9 114.0(4) . . . 7_565 ? C10 C9 C11 C9 -121.4(4) . . . 7_565 ? C11 C9 C11 C9 0.000(4) 7_565 . . 7_565 ? C9 C9 N C1 -157.8(5) 7_565 . . . ? C10 C9 N C1 -9.9(10) . . . . ? C11 C9 N C1 107.9(8) . . . . ? C11 C9 N C1 142.9(7) 7_565 . . . ? C9 C9 N Ni 8.5(6) 7_565 . . . ? C10 C9 N Ni 156.4(5) . . . . ? C11 C9 N Ni -85.9(7) . . . . ? C11 C9 N Ni -50.9(8) 7_565 . . . ? C6 C1 N C9 91.8(8) . . . . ? C2 C1 N C9 -91.8(8) . . . . ? C6 C1 N Ni -73.3(8) . . . . ? C2 C1 N Ni 103.0(6) . . . . ? C9 N Ni N -10.2(7) . . . 7_565 ? C1 N Ni N 156.0(4) . . . 7_565 ? C9 N Ni Br2 -141.1(5) . . . . ? C1 N Ni Br2 25.1(7) . . . . ? C9 N Ni Br1 90.1(5) . . . . ? C1 N Ni Br1 -103.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.675 _refine_diff_density_min -0.867 _refine_diff_density_rms 0.093 # Attachment 'IAPP.cif' data_g101409 _database_code_depnum_ccdc_archive 'CCDC 867172' #TrackingRef 'IAPP.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H44 Br2 N2 Ni' _chemical_formula_weight 639.19 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 10.803(2) _cell_length_b 20.726(5) _cell_length_c 13.844(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.466(4) _cell_angle_gamma 90.00 _cell_volume 3037.8(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 3.288 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4193 _exptl_absorpt_correction_T_max 0.5316 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 19080 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 23.27 _reflns_number_total 4116 _reflns_number_gt 2891 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0693P)^2^+0.4895P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4116 _refine_ls_number_parameters 335 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.100 _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 0.71115(6) 0.17580(3) 0.99589(5) 0.0650(2) Uani 1 1 d . . . Br2 Br 0.48353(7) 0.18055(4) 1.17535(4) 0.0755(3) Uani 1 1 d . . . C1 C 0.3303(5) 0.1039(2) 0.8772(4) 0.0477(13) Uani 1 1 d . . . C2 C 0.3764(6) 0.0485(3) 0.8402(4) 0.0544(15) Uani 1 1 d . . . C3 C 0.3073(7) -0.0077(3) 0.8380(5) 0.0718(18) Uani 1 1 d . . . H3 H 0.3381 -0.0456 0.8155 0.086 Uiso 1 1 calc R . . C4 C 0.1937(7) -0.0086(3) 0.8684(5) 0.078(2) Uani 1 1 d . . . H4 H 0.1472 -0.0466 0.8652 0.094 Uiso 1 1 calc R . . C5 C 0.1493(6) 0.0465(3) 0.9035(4) 0.0724(18) Uani 1 1 d . . . H5 H 0.0721 0.0455 0.9236 0.087 Uiso 1 1 calc R . . C6 C 0.2167(6) 0.1043(3) 0.9100(4) 0.0557(15) Uani 1 1 d . . . C7 C 0.5010(7) 0.0433(3) 0.8049(5) 0.0736(19) Uani 1 1 d . . . H7 H 0.533(6) 0.087(3) 0.800(4) 0.088 Uiso 1 1 calc . . . C8 C 0.4860(8) 0.0128(5) 0.7026(5) 0.126(3) Uani 1 1 d . . . H8A H 0.4453 -0.0284 0.7024 0.188 Uiso 1 1 calc R . . H8B H 0.5677 0.0071 0.6864 0.188 Uiso 1 1 calc R . . H8C H 0.4356 0.0405 0.6547 0.188 Uiso 1 1 calc R . . C9 C 0.5996(7) 0.0072(3) 0.8785(6) 0.101(3) Uani 1 1 d . . . H9A H 0.6109 0.0281 0.9415 0.151 Uiso 1 1 calc R . . H9B H 0.6782 0.0070 0.8561 0.151 Uiso 1 1 calc R . . H9C H 0.5720 -0.0364 0.8844 0.151 Uiso 1 1 calc R . . C10 C 0.1636(7) 0.1617(3) 0.9552(5) 0.079(2) Uani 1 1 d . . . H10 H 0.223(7) 0.197(3) 0.957(5) 0.095 Uiso 1 1 calc . . . C11 C 0.0359(7) 0.1842(4) 0.8979(6) 0.124(3) Uani 1 1 d . . . H11A H 0.0381 0.1865 0.8290 0.186 Uiso 1 1 calc R . . H11B H 0.0173 0.2262 0.9209 0.186 Uiso 1 1 calc R . . H11C H -0.0283 0.1543 0.9078 0.186 Uiso 1 1 calc R . . C12 C 0.1525(8) 0.1479(4) 1.0610(5) 0.110(3) Uani 1 1 d . . . H12A H 0.0925 0.1138 1.0618 0.165 Uiso 1 1 calc R . . H12B H 0.1246 0.1861 1.0896 0.165 Uiso 1 1 calc R . . H12C H 0.2334 0.1350 1.0983 0.165 Uiso 1 1 calc R . . C13 C 0.3770(6) 0.2129(2) 0.8047(4) 0.0544(15) Uani 1 1 d . . . C14 C 0.2537(5) 0.2024(3) 0.7343(4) 0.0588(15) Uani 1 1 d . . . H14A H 0.1852 0.2129 0.7662 0.088 Uiso 1 1 calc R . . H14B H 0.2471 0.1580 0.7141 0.088 Uiso 1 1 calc R . . H14C H 0.2500 0.2294 0.6775 0.088 Uiso 1 1 calc R . . C15 C 0.4872(7) 0.2135(4) 0.7400(5) 0.097(2) Uani 1 1 d . . . H15A H 0.4903 0.2552 0.7105 0.146 Uiso 1 1 calc R . . H15B H 0.4692 0.1814 0.6893 0.146 Uiso 1 1 calc R . . H15C H 0.5672 0.2043 0.7821 0.146 Uiso 1 1 calc R . . C16 C 0.4009(5) 0.2783(2) 0.8479(4) 0.0491(14) Uani 1 1 d . . . C17 C 0.3445(7) 0.3353(3) 0.7927(4) 0.074(2) Uani 1 1 d . . . H17A H 0.2541 0.3326 0.7827 0.111 Uiso 1 1 calc R . . H17B H 0.3696 0.3367 0.7300 0.111 Uiso 1 1 calc R . . H17C H 0.3730 0.3736 0.8294 0.111 Uiso 1 1 calc R . . C18 C 0.4969(5) 0.3436(2) 0.9899(4) 0.0438(13) Uani 1 1 d . . . C19 C 0.6076(5) 0.3752(2) 0.9784(4) 0.0448(13) Uani 1 1 d . . . C20 C 0.6408(5) 0.4300(3) 1.0362(4) 0.0556(15) Uani 1 1 d . . . H20 H 0.7127 0.4529 1.0294 0.067 Uiso 1 1 calc R . . C21 C 0.5715(6) 0.4514(3) 1.1022(4) 0.0657(17) Uani 1 1 d . . . H21 H 0.5981 0.4871 1.1415 0.079 Uiso 1 1 calc R . . C22 C 0.4629(6) 0.4198(3) 1.1100(4) 0.0634(16) Uani 1 1 d . . . H22 H 0.4153 0.4351 1.1542 0.076 Uiso 1 1 calc R . . C23 C 0.4218(5) 0.3662(3) 1.0544(4) 0.0522(14) Uani 1 1 d . . . C24 C 0.6882(6) 0.3556(3) 0.9055(4) 0.0627(16) Uani 1 1 d . . . H24 H 0.656(6) 0.315(3) 0.875(4) 0.075 Uiso 1 1 calc . . . C25 C 0.6785(7) 0.4067(4) 0.8229(5) 0.102(3) Uani 1 1 d . . . H25A H 0.7106 0.4471 0.8510 0.153 Uiso 1 1 calc R . . H25B H 0.5918 0.4117 0.7908 0.153 Uiso 1 1 calc R . . H25C H 0.7272 0.3929 0.7757 0.153 Uiso 1 1 calc R . . C26 C 0.8257(6) 0.3459(4) 0.9539(5) 0.090(2) Uani 1 1 d . . . H26A H 0.8631 0.3869 0.9749 0.136 Uiso 1 1 calc R . . H26B H 0.8699 0.3267 0.9074 0.136 Uiso 1 1 calc R . . H26C H 0.8311 0.3180 1.0099 0.136 Uiso 1 1 calc R . . C27 C 0.2966(7) 0.3363(3) 1.0610(6) 0.085(2) Uani 1 1 d . . . H27 H 0.296(6) 0.293(3) 1.033(5) 0.102 Uiso 1 1 calc . . . C28 C 0.1885(7) 0.3729(5) 0.9995(7) 0.138(4) Uani 1 1 d . . . H28A H 0.1939 0.4175 1.0184 0.207 Uiso 1 1 calc R . . H28B H 0.1099 0.3553 1.0097 0.207 Uiso 1 1 calc R . . H28C H 0.1929 0.3692 0.9311 0.207 Uiso 1 1 calc R . . C29 C 0.2766(9) 0.3293(4) 1.1681(7) 0.134(4) Uani 1 1 d . . . H29A H 0.3439 0.3040 1.2055 0.201 Uiso 1 1 calc R . . H29B H 0.1973 0.3083 1.1678 0.201 Uiso 1 1 calc R . . H29C H 0.2761 0.3713 1.1973 0.201 Uiso 1 1 calc R . . N1 N 0.4085(6) 0.1621(2) 0.8827(3) 0.0535(12) Uani 1 1 d D . . N2 N 0.4626(4) 0.28228(19) 0.9389(3) 0.0497(11) Uani 1 1 d . . . Ni Ni 0.50003(6) 0.19986(3) 1.01359(4) 0.0441(2) Uani 1 1 d . . . H1A H 0.477(3) 0.156(4) 0.880(6) 0.10(3) Uiso 1 1 d 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 Br1 0.0485(4) 0.0713(4) 0.0703(4) -0.0030(3) 0.0000(3) 0.0123(3) Br2 0.0721(5) 0.1050(6) 0.0487(4) 0.0166(3) 0.0102(3) -0.0063(4) C1 0.050(4) 0.041(3) 0.045(3) 0.003(2) -0.009(3) -0.003(3) C2 0.063(4) 0.043(3) 0.050(3) 0.008(3) -0.005(3) -0.003(3) C3 0.095(6) 0.047(4) 0.067(4) -0.001(3) 0.002(4) -0.005(4) C4 0.094(6) 0.062(5) 0.070(5) 0.001(3) -0.004(4) -0.034(4) C5 0.064(4) 0.087(5) 0.062(4) 0.006(4) 0.004(3) -0.019(4) C6 0.059(4) 0.053(4) 0.050(3) 0.005(3) -0.002(3) 0.001(3) C7 0.077(5) 0.063(4) 0.075(5) 0.004(4) 0.002(4) 0.010(4) C8 0.117(7) 0.192(10) 0.066(5) -0.015(5) 0.015(5) 0.035(7) C9 0.087(6) 0.106(6) 0.100(6) -0.006(5) -0.006(5) 0.017(5) C10 0.077(5) 0.081(5) 0.083(5) 0.005(4) 0.022(4) 0.007(4) C11 0.091(6) 0.159(9) 0.133(8) 0.052(6) 0.053(6) 0.054(6) C12 0.132(7) 0.118(6) 0.086(6) -0.016(5) 0.036(5) 0.008(6) C13 0.070(4) 0.043(3) 0.043(3) -0.001(2) -0.007(3) 0.005(3) C14 0.065(4) 0.062(4) 0.043(3) 0.010(3) -0.007(3) -0.007(3) C15 0.101(6) 0.135(6) 0.067(4) 0.006(4) 0.044(4) 0.023(5) C16 0.040(3) 0.045(3) 0.057(4) 0.008(3) -0.006(3) -0.005(3) C17 0.101(6) 0.049(4) 0.058(4) 0.003(3) -0.020(4) 0.003(3) C18 0.049(4) 0.036(3) 0.038(3) 0.002(2) -0.010(3) 0.003(3) C19 0.049(4) 0.041(3) 0.041(3) 0.000(2) -0.001(3) 0.005(3) C20 0.054(4) 0.051(3) 0.056(3) -0.006(3) -0.005(3) -0.008(3) C21 0.080(5) 0.054(4) 0.058(4) -0.022(3) 0.000(4) 0.003(3) C22 0.065(4) 0.053(4) 0.076(4) -0.010(3) 0.021(4) 0.010(3) C23 0.048(4) 0.046(3) 0.062(4) 0.000(3) 0.009(3) 0.007(3) C24 0.066(5) 0.061(4) 0.062(4) -0.013(3) 0.014(3) 0.002(3) C25 0.126(7) 0.120(6) 0.065(4) 0.016(4) 0.033(5) 0.018(5) C26 0.062(5) 0.112(6) 0.102(6) -0.004(5) 0.027(4) 0.013(4) C27 0.065(5) 0.077(5) 0.118(6) -0.024(4) 0.032(5) -0.002(4) C28 0.055(5) 0.203(11) 0.149(8) -0.016(8) 0.005(5) 0.022(6) C29 0.116(8) 0.160(9) 0.146(8) 0.020(7) 0.076(7) -0.016(6) N1 0.065(4) 0.048(3) 0.039(3) 0.004(2) -0.010(3) -0.014(3) N2 0.056(3) 0.039(3) 0.046(3) 0.000(2) -0.009(2) -0.001(2) Ni 0.0465(4) 0.0443(4) 0.0371(4) 0.0027(3) -0.0020(3) -0.0001(3) _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 Ni 2.3942(10) . ? Br2 Ni 2.3164(10) . ? C1 C2 1.389(7) . ? C1 C6 1.391(8) . ? C1 N1 1.466(7) . ? C2 C3 1.381(8) . ? C2 C7 1.525(9) . ? C3 C4 1.375(9) . ? C3 H3 0.9300 . ? C4 C5 1.365(9) . ? C4 H4 0.9300 . ? C5 C6 1.395(8) . ? C5 H5 0.9300 . ? C6 C10 1.509(9) . ? C7 C9 1.517(9) . ? C7 C8 1.530(9) . ? C7 H7 0.98(6) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C12 1.520(10) . ? C10 C11 1.522(10) . ? C10 H10 0.98(6) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C16 1.484(7) . ? C13 N1 1.498(7) . ? C13 C14 1.502(8) . ? C13 C15 1.625(8) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N2 1.306(6) . ? C16 C17 1.470(7) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.400(7) . ? C18 C23 1.401(7) . ? C18 N2 1.465(6) . ? C19 C20 1.394(7) . ? C19 C24 1.514(7) . ? C20 C21 1.365(8) . ? C20 H20 0.9300 . ? C21 C22 1.366(8) . ? C21 H21 0.9300 . ? C22 C23 1.375(8) . ? C22 H22 0.9300 . ? C23 C27 1.507(9) . ? C24 C26 1.516(9) . ? C24 C25 1.546(9) . ? C24 H24 0.98(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.507(11) . ? C27 C29 1.546(11) . ? C27 H27 0.98(7) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? N1 Ni 2.040(5) . ? N1 H1A 0.764(11) . ? N2 Ni 1.996(4) . ? 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 C2 C1 C6 122.0(5) . . ? C2 C1 N1 117.0(5) . . ? C6 C1 N1 121.0(5) . . ? C3 C2 C1 118.3(6) . . ? C3 C2 C7 116.1(6) . . ? C1 C2 C7 125.6(5) . . ? C4 C3 C2 121.1(6) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 119.7(6) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.7(6) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C1 C6 C5 117.2(5) . . ? C1 C6 C10 124.9(5) . . ? C5 C6 C10 117.9(6) . . ? C9 C7 C2 111.5(6) . . ? C9 C7 C8 110.4(6) . . ? C2 C7 C8 112.9(6) . . ? C9 C7 H7 107(4) . . ? C2 C7 H7 107(4) . . ? C8 C7 H7 107(4) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 C10 C12 111.1(6) . . ? C6 C10 C11 113.9(6) . . ? C12 C10 C11 108.8(6) . . ? C6 C10 H10 107(4) . . ? C12 C10 H10 108(4) . . ? C11 C10 H10 108(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C16 C13 N1 110.8(4) . . ? C16 C13 C14 117.1(5) . . ? N1 C13 C14 114.2(5) . . ? C16 C13 C15 97.3(5) . . ? N1 C13 C15 108.5(5) . . ? C14 C13 C15 107.2(5) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 C17 122.1(5) . . ? N2 C16 C13 117.4(5) . . ? C17 C16 C13 120.2(5) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 122.2(5) . . ? C19 C18 N2 119.4(5) . . ? C23 C18 N2 118.3(5) . . ? C20 C19 C18 116.4(5) . . ? C20 C19 C24 119.0(5) . . ? C18 C19 C24 124.6(5) . . ? C21 C20 C19 122.4(5) . . ? C21 C20 H20 118.8 . . ? C19 C20 H20 118.8 . . ? C20 C21 C22 119.4(5) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C21 C22 C23 122.0(5) . . ? C21 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? C22 C23 C18 117.6(5) . . ? C22 C23 C27 119.5(5) . . ? C18 C23 C27 122.8(5) . . ? C19 C24 C26 112.6(5) . . ? C19 C24 C25 110.2(5) . . ? C26 C24 C25 109.5(6) . . ? C19 C24 H24 108(4) . . ? C26 C24 H24 108(4) . . ? C25 C24 H24 108(3) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C23 111.3(7) . . ? C28 C27 C29 110.4(7) . . ? C23 C27 C29 113.2(7) . . ? C28 C27 H27 107(4) . . ? C23 C27 H27 107(4) . . ? C29 C27 H27 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 . . ? 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 . . ? C1 N1 C13 119.7(4) . . ? C1 N1 Ni 122.3(4) . . ? C13 N1 Ni 111.8(3) . . ? C1 N1 H1A 114(6) . . ? C13 N1 H1A 100(6) . . ? Ni N1 H1A 79(6) . . ? C16 N2 C18 123.4(4) . . ? C16 N2 Ni 117.3(3) . . ? C18 N2 Ni 119.2(3) . . ? N2 Ni N1 81.72(18) . . ? N2 Ni Br2 127.01(13) . . ? N1 Ni Br2 132.49(15) . . ? N2 Ni Br1 102.95(13) . . ? N1 Ni Br1 97.63(19) . . ? Br2 Ni Br1 108.72(3) . . ? 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 C6 C1 C2 C3 -1.0(8) . . . . ? N1 C1 C2 C3 177.3(5) . . . . ? C6 C1 C2 C7 -178.5(5) . . . . ? N1 C1 C2 C7 -0.2(8) . . . . ? C1 C2 C3 C4 2.1(9) . . . . ? C7 C2 C3 C4 179.8(6) . . . . ? C2 C3 C4 C5 -1.4(10) . . . . ? C3 C4 C5 C6 -0.4(10) . . . . ? C2 C1 C6 C5 -0.7(8) . . . . ? N1 C1 C6 C5 -179.0(5) . . . . ? C2 C1 C6 C10 177.1(6) . . . . ? N1 C1 C6 C10 -1.2(8) . . . . ? C4 C5 C6 C1 1.4(9) . . . . ? C4 C5 C6 C10 -176.5(6) . . . . ? C3 C2 C7 C9 -72.0(7) . . . . ? C1 C2 C7 C9 105.6(6) . . . . ? C3 C2 C7 C8 53.0(8) . . . . ? C1 C2 C7 C8 -129.5(7) . . . . ? C1 C6 C10 C12 -117.4(7) . . . . ? C5 C6 C10 C12 60.4(8) . . . . ? C1 C6 C10 C11 119.3(7) . . . . ? C5 C6 C10 C11 -63.0(8) . . . . ? N1 C13 C16 N2 11.0(7) . . . . ? C14 C13 C16 N2 144.4(5) . . . . ? C15 C13 C16 N2 -102.0(6) . . . . ? N1 C13 C16 C17 -162.6(6) . . . . ? C14 C13 C16 C17 -29.2(8) . . . . ? C15 C13 C16 C17 84.4(6) . . . . ? C23 C18 C19 C20 1.1(7) . . . . ? N2 C18 C19 C20 -174.1(4) . . . . ? C23 C18 C19 C24 -176.1(5) . . . . ? N2 C18 C19 C24 8.7(7) . . . . ? C18 C19 C20 C21 1.5(8) . . . . ? C24 C19 C20 C21 178.8(5) . . . . ? C19 C20 C21 C22 -2.6(9) . . . . ? C20 C21 C22 C23 1.3(9) . . . . ? C21 C22 C23 C18 1.2(9) . . . . ? C21 C22 C23 C27 -175.7(6) . . . . ? C19 C18 C23 C22 -2.4(8) . . . . ? N2 C18 C23 C22 172.9(5) . . . . ? C19 C18 C23 C27 174.4(5) . . . . ? N2 C18 C23 C27 -10.4(8) . . . . ? C20 C19 C24 C26 56.2(7) . . . . ? C18 C19 C24 C26 -126.7(6) . . . . ? C20 C19 C24 C25 -66.3(7) . . . . ? C18 C19 C24 C25 110.8(6) . . . . ? C22 C23 C27 C28 79.9(8) . . . . ? C18 C23 C27 C28 -96.8(7) . . . . ? C22 C23 C27 C29 -45.2(9) . . . . ? C18 C23 C27 C29 138.1(6) . . . . ? C2 C1 N1 C13 100.2(7) . . . . ? C6 C1 N1 C13 -81.4(7) . . . . ? C2 C1 N1 Ni -109.8(5) . . . . ? C6 C1 N1 Ni 68.6(7) . . . . ? C16 C13 N1 C1 143.1(5) . . . . ? C14 C13 N1 C1 8.3(8) . . . . ? C15 C13 N1 C1 -111.2(7) . . . . ? C16 C13 N1 Ni -9.9(6) . . . . ? C14 C13 N1 Ni -144.7(4) . . . . ? C15 C13 N1 Ni 95.9(5) . . . . ? C17 C16 N2 C18 -8.8(9) . . . . ? C13 C16 N2 C18 177.7(5) . . . . ? C17 C16 N2 Ni 166.7(4) . . . . ? C13 C16 N2 Ni -6.8(7) . . . . ? C19 C18 N2 C16 -84.8(7) . . . . ? C23 C18 N2 C16 99.9(6) . . . . ? C19 C18 N2 Ni 99.9(5) . . . . ? C23 C18 N2 Ni -75.5(5) . . . . ? C16 N2 Ni N1 0.6(4) . . . . ? C18 N2 Ni N1 176.3(4) . . . . ? C16 N2 Ni Br2 -137.5(4) . . . . ? C18 N2 Ni Br2 38.1(4) . . . . ? C16 N2 Ni Br1 96.6(4) . . . . ? C18 N2 Ni Br1 -87.7(4) . . . . ? C1 N1 Ni N2 -146.7(5) . . . . ? C13 N1 Ni N2 5.4(4) . . . . ? C1 N1 Ni Br2 -13.0(6) . . . . ? C13 N1 Ni Br2 139.1(3) . . . . ? C1 N1 Ni Br1 111.2(5) . . . . ? C13 N1 Ni Br1 -96.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.749 _refine_diff_density_min -0.724 _refine_diff_density_rms 0.074