# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jwu-Ting Chen' _publ_contact_author_email jtchen@ntu.edu.tw _publ_author_name 'Jwu-Ting Chen' data_ic8185 _database_code_depnum_ccdc_archive 'CCDC 864436' #TrackingRef '- 1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18.50 H27 Br2 Cl N4 Ni' _chemical_formula_weight 559.42 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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)/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 10.9677(2) _cell_length_b 16.4392(3) _cell_length_c 13.4252(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.5146(7) _cell_angle_gamma 90.00 _cell_volume 2409.36(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1124 _exptl_absorpt_coefficient_mu 4.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.553 _exptl_absorpt_correction_T_max 0.668 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 39307 _diffrn_reflns_av_R_equivalents 0.0782 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5524 _reflns_number_gt 4268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _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^)+(0.0831P)^2^+9.3790P] 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 0.0054(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5524 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0860 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1846 _refine_ls_wR_factor_gt 0.1635 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.64710(8) 0.81323(6) 0.66866(7) 0.0648(3) Uani 1 1 d . . . Br1 Br 0.75526(13) 0.71004(9) 0.77436(12) 0.0662(4) Uani 0.67 1 d P A 1 Br1' Br 0.7105(3) 0.68473(19) 0.7456(3) 0.0791(9) Uani 0.33 1 d P A 2 Br2 Br 0.67247(4) 0.98190(3) 0.37422(4) 0.0398(2) Uani 1 1 d . . . N1 N 0.4735(6) 0.7609(3) 0.6608(4) 0.0633(16) Uani 1 1 d . A . N2 N 0.5978(6) 0.8220(3) 0.5162(4) 0.0601(15) Uani 1 1 d . A . N3 N 0.8102(5) 0.8778(5) 0.6636(5) 0.085(2) Uani 1 1 d . A . N4 N 0.5919(4) 0.9273(3) 0.7109(3) 0.0439(10) Uani 1 1 d . A . C1 C 0.4274(9) 0.7093(4) 0.7265(6) 0.077(2) Uani 1 1 d . . . H1A H 0.4773 0.6946 0.7855 0.093 Uiso 1 1 calc R A . C2 C 0.3131(10) 0.6780(5) 0.7113(7) 0.088(3) Uani 1 1 d . A . H2A H 0.2829 0.6425 0.7590 0.106 Uiso 1 1 calc R . . C3 C 0.2415(11) 0.6986(6) 0.6252(7) 0.104(4) Uani 1 1 d . . . H3A H 0.1614 0.6765 0.6127 0.125 Uiso 1 1 calc R A . C4 C 0.2859(9) 0.7517(6) 0.5563(6) 0.087(3) Uani 1 1 d . A . H4A H 0.2369 0.7676 0.4973 0.105 Uiso 1 1 calc R . . C5 C 0.4035(7) 0.7803(4) 0.5770(5) 0.0597(18) Uani 1 1 d . . . C6 C 0.4629(7) 0.8357(3) 0.5059(5) 0.0532(15) Uani 1 1 d . A . H6A H 0.4290 0.8245 0.4363 0.064 Uiso 1 1 calc R . . H6B H 0.4451 0.8932 0.5214 0.064 Uiso 1 1 calc R . . C7 C 0.6339(13) 0.7504(6) 0.4574(10) 0.115(4) Uani 1 1 d . . . H7A H 0.6069 0.7018 0.4943 0.138 Uiso 0.67 1 calc PR A 1 H7'A H 0.6162 0.7698 0.3869 0.138 Uiso 0.33 1 d PR A 2 C8 C 0.7794(12) 0.7470(9) 0.4699(10) 0.145(6) Uani 1 1 d . A . H8A H 0.8074 0.7009 0.4318 0.218 Uiso 0.67 1 calc PR B 1 H8B H 0.8082 0.7404 0.5408 0.218 Uiso 0.67 1 calc PR B 1 H8C H 0.8124 0.7976 0.4448 0.218 Uiso 0.67 1 calc PR B 1 H8'A H 0.8077 0.7009 0.4319 0.218 Uiso 0.33 1 d PR B 2 H8'B H 0.8125 0.7977 0.4451 0.218 Uiso 0.33 1 d PR B 2 H8'C H 0.8077 0.7403 0.5409 0.218 Uiso 0.33 1 d PR B 2 C9 C 0.5877(16) 0.7399(10) 0.3639(15) 0.116(6) Uani 0.67 1 d P A 1 H9A H 0.4980 0.7418 0.3604 0.175 Uiso 0.67 1 calc PR A 1 H9B H 0.6134 0.6869 0.3399 0.175 Uiso 0.67 1 calc PR A 1 H9C H 0.6172 0.7831 0.3220 0.175 Uiso 0.67 1 calc PR A 1 C9' C 0.560(4) 0.6763(10) 0.457(2) 0.122(15) Uani 0.33 1 d P A 2 H9'A H 0.4734 0.6904 0.4458 0.182 Uiso 0.33 1 calc PR A 2 H9'B H 0.5764 0.6486 0.5215 0.182 Uiso 0.33 1 calc PR A 2 H9'C H 0.5823 0.6403 0.4033 0.182 Uiso 0.33 1 calc PR A 2 C10 C 0.9252(7) 0.8503(8) 0.6628(9) 0.125(5) Uani 1 1 d . . . H10A H 0.9409 0.7939 0.6724 0.150 Uiso 1 1 calc R A . C11 C 1.0231(7) 0.9027(9) 0.6484(9) 0.121(5) Uani 1 1 d . A . H11A H 1.1040 0.8818 0.6496 0.145 Uiso 1 1 calc R . . C12 C 1.0020(7) 0.9837(8) 0.6326(7) 0.098(3) Uani 1 1 d . . . H12A H 1.0667 1.0197 0.6204 0.117 Uiso 1 1 calc R A . C13 C 0.8859(6) 1.0110(7) 0.6349(6) 0.077(2) Uani 1 1 d . A . H13A H 0.8686 1.0672 0.6253 0.092 Uiso 1 1 calc R . . C14 C 0.7914(5) 0.9573(5) 0.6513(5) 0.0610(18) Uani 1 1 d . . . C15 C 0.6626(5) 0.9853(4) 0.6545(4) 0.0440(12) Uani 1 1 d . A . H15A H 0.6624 1.0395 0.6867 0.053 Uiso 1 1 calc R . . H15B H 0.6230 0.9908 0.5854 0.053 Uiso 1 1 calc R . . C16 C 0.6072(6) 0.9435(6) 0.8212(5) 0.071(2) Uani 1 1 d . . . H16A H 0.6953 0.9338 0.8447 0.085 Uiso 0.67 1 calc PR A 1 H16B H 0.5731 0.9986 0.8339 0.085 Uiso 0.33 1 d PR A 2 C17 C 0.5314(9) 0.8793(7) 0.8719(6) 0.090(3) Uani 1 1 d . A . H17A H 0.5393 0.8884 0.9443 0.135 Uiso 0.67 1 calc PR C 1 H17B H 0.5617 0.8248 0.8577 0.135 Uiso 0.67 1 calc PR C 1 H17C H 0.4451 0.8838 0.8458 0.135 Uiso 0.67 1 calc PR C 1 H17D H 0.5392 0.8883 0.9444 0.135 Uiso 0.33 1 d PR C 2 H17E H 0.4451 0.8836 0.8457 0.135 Uiso 0.33 1 d PR C 2 H17F H 0.5620 0.8249 0.8576 0.135 Uiso 0.33 1 d PR C 2 C18 C 0.5757(16) 1.0278(9) 0.8542(8) 0.094(5) Uani 0.67 1 d P A 1 H18A H 0.6248 1.0677 0.8216 0.142 Uiso 0.67 1 calc PR A 1 H18B H 0.5931 1.0322 0.9270 0.142 Uiso 0.67 1 calc PR A 1 H18C H 0.4885 1.0383 0.8356 0.142 Uiso 0.67 1 calc PR A 1 C18' C 0.725(2) 0.941(3) 0.8662(17) 0.115(14) Uani 0.33 1 d P A 2 H18D H 0.7748 0.9816 0.8360 0.173 Uiso 0.33 1 calc PR A 2 H18E H 0.7593 0.8864 0.8568 0.173 Uiso 0.33 1 calc PR A 2 H18F H 0.7245 0.9517 0.9379 0.173 Uiso 0.33 1 calc PR A 2 C19 C 0.584(3) 1.5073(14) 0.401(3) 0.19(2) Uani 0.50 1 d P . . H19A H 0.5195 1.5014 0.3474 0.230 Uiso 0.50 1 d PR . . H19B H 0.6034 1.4536 0.4254 0.230 Uiso 0.50 1 d PR . . Cl1 Cl 0.5135(19) 1.5335(6) 0.5468(11) 0.299(11) Uani 0.50 1 d P . . Cl2 Cl 0.6991(9) 1.5116(5) 0.4144(9) 0.168(4) Uani 0.50 1 d P . . 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 0.0588(5) 0.0655(6) 0.0759(6) 0.0433(5) 0.0366(4) 0.0340(4) Br1 0.0585(8) 0.0600(8) 0.0783(9) 0.0353(7) -0.0033(6) 0.0146(6) Br1' 0.088(2) 0.0506(15) 0.092(2) 0.0253(14) -0.0256(16) 0.0145(14) Br2 0.0366(3) 0.0396(3) 0.0450(3) 0.0051(2) 0.0127(2) 0.0081(2) N1 0.089(4) 0.043(3) 0.065(3) 0.019(2) 0.043(3) 0.013(3) N2 0.081(4) 0.040(3) 0.067(3) 0.012(2) 0.046(3) 0.020(3) N3 0.039(3) 0.116(6) 0.104(5) 0.071(4) 0.031(3) 0.034(3) N4 0.030(2) 0.065(3) 0.037(2) 0.013(2) 0.0052(17) 0.003(2) C1 0.109(6) 0.053(4) 0.080(5) 0.019(4) 0.057(5) 0.002(4) C2 0.140(9) 0.064(5) 0.071(5) 0.000(4) 0.057(6) -0.026(5) C3 0.135(9) 0.110(7) 0.074(6) -0.022(5) 0.041(6) -0.080(7) C4 0.125(7) 0.090(6) 0.051(4) -0.015(4) 0.026(4) -0.062(6) C5 0.092(5) 0.038(3) 0.056(4) -0.009(3) 0.037(4) -0.011(3) C6 0.084(4) 0.034(3) 0.045(3) -0.002(2) 0.027(3) -0.007(3) C7 0.166(11) 0.065(5) 0.129(9) -0.014(6) 0.093(9) 0.027(6) C8 0.148(11) 0.160(12) 0.140(10) -0.002(9) 0.086(9) 0.088(10) C9 0.116(13) 0.085(11) 0.158(17) -0.048(11) 0.062(12) -0.022(9) C9' 0.28(4) 0.016(8) 0.092(17) -0.002(9) 0.12(2) 0.012(14) C10 0.051(4) 0.179(11) 0.151(9) 0.111(9) 0.044(5) 0.057(6) C11 0.034(4) 0.182(12) 0.152(10) 0.079(9) 0.036(5) 0.029(5) C12 0.040(4) 0.165(11) 0.092(6) 0.032(7) 0.019(4) -0.007(5) C13 0.044(4) 0.123(7) 0.066(4) 0.010(4) 0.014(3) -0.014(4) C14 0.034(3) 0.100(5) 0.050(3) 0.026(3) 0.006(2) 0.009(3) C15 0.032(2) 0.061(3) 0.039(3) 0.007(2) 0.001(2) -0.003(2) C16 0.051(4) 0.124(7) 0.037(3) 0.014(4) 0.007(3) -0.008(4) C17 0.110(7) 0.112(7) 0.054(4) 0.015(4) 0.035(4) -0.002(6) C18 0.138(12) 0.109(11) 0.039(5) -0.017(6) 0.025(6) -0.062(10) C18' 0.045(12) 0.25(4) 0.049(12) 0.030(18) -0.008(9) -0.041(19) C19 0.17(3) 0.065(13) 0.31(5) 0.04(2) -0.14(3) -0.038(16) Cl1 0.56(3) 0.094(5) 0.287(15) -0.048(7) 0.276(19) -0.061(10) Cl2 0.149(7) 0.117(6) 0.232(10) -0.059(6) -0.010(7) 0.027(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 Ni N4 2.067(5) . ? Ni N2 2.071(6) . ? Ni N1 2.082(7) . ? Ni N3 2.087(7) . ? Ni Br1' 2.424(3) . ? Ni Br1 2.4444(14) . ? N1 C5 1.339(10) . ? N1 C1 1.356(8) . ? N2 C6 1.490(9) . ? N2 C7 1.492(9) . ? N3 C14 1.331(11) . ? N3 C10 1.341(9) . ? N4 C15 1.483(7) . ? N4 C16 1.499(8) . ? C1 C2 1.352(13) . ? C2 C3 1.376(15) . ? C3 C4 1.393(11) . ? C4 C5 1.375(11) . ? C5 C6 1.511(8) . ? C7 C9 1.32(2) . ? C7 C9' 1.46(3) . ? C7 C8 1.590(18) . ? C10 C11 1.404(15) . ? C11 C12 1.364(16) . ? C12 C13 1.354(12) . ? C13 C14 1.395(11) . ? C14 C15 1.490(8) . ? C16 C18' 1.37(2) . ? C16 C18 1.504(17) . ? C16 C17 1.542(11) . ? C19 Cl2 1.26(3) . ? C19 Cl1 1.49(4) 3_686 ? C19 Cl1 2.22(5) . ? Cl1 C19 1.49(4) 3_686 ? Cl1 Cl1 1.68(3) 3_686 ? 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 N4 Ni N2 98.75(18) . . ? N4 Ni N1 95.62(19) . . ? N2 Ni N1 80.1(2) . . ? N4 Ni N3 79.7(2) . . ? N2 Ni N3 94.3(3) . . ? N1 Ni N3 172.2(2) . . ? N4 Ni Br1' 138.90(16) . . ? N2 Ni Br1' 121.26(17) . . ? N1 Ni Br1' 83.40(18) . . ? N3 Ni Br1' 104.23(18) . . ? N4 Ni Br1 127.53(14) . . ? N2 Ni Br1 133.49(14) . . ? N1 Ni Br1 97.65(16) . . ? N3 Ni Br1 90.13(16) . . ? Br1' Ni Br1 17.14(7) . . ? C5 N1 C1 118.4(7) . . ? C5 N1 Ni 113.1(4) . . ? C1 N1 Ni 128.4(6) . . ? C6 N2 C7 112.5(8) . . ? C6 N2 Ni 105.4(3) . . ? C7 N2 Ni 114.3(6) . . ? C14 N3 C10 117.7(8) . . ? C14 N3 Ni 112.4(4) . . ? C10 N3 Ni 129.7(8) . . ? C15 N4 C16 112.1(5) . . ? C15 N4 Ni 105.2(3) . . ? C16 N4 Ni 115.1(5) . . ? C2 C1 N1 122.5(9) . . ? C1 C2 C3 118.7(7) . . ? C2 C3 C4 120.2(9) . . ? C5 C4 C3 117.5(9) . . ? N1 C5 C4 122.6(6) . . ? N1 C5 C6 115.3(6) . . ? C4 C5 C6 122.1(7) . . ? N2 C6 C5 109.5(6) . . ? C9 C7 C9' 74.0(16) . . ? C9 C7 N2 120.7(12) . . ? C9' C7 N2 119.0(11) . . ? C9 C7 C8 112.7(10) . . ? C9' C7 C8 121.3(17) . . ? N2 C7 C8 106.7(10) . . ? N3 C10 C11 121.8(10) . . ? C12 C11 C10 120.0(8) . . ? C13 C12 C11 117.8(9) . . ? C12 C13 C14 120.6(10) . . ? N3 C14 C13 122.1(7) . . ? N3 C14 C15 115.8(6) . . ? C13 C14 C15 122.0(7) . . ? N4 C15 C14 111.1(5) . . ? C18' C16 N4 116.1(13) . . ? C18' C16 C18 98(2) . . ? N4 C16 C18 116.6(7) . . ? C18' C16 C17 107.8(15) . . ? N4 C16 C17 107.4(7) . . ? C18 C16 C17 110.6(8) . . ? Cl2 C19 Cl1 135(3) . 3_686 ? Cl2 C19 Cl1 107(2) . . ? Cl1 C19 Cl1 49.1(17) 3_686 . ? C19 Cl1 Cl1 88.6(18) 3_686 3_686 ? C19 Cl1 C19 130.9(17) 3_686 . ? Cl1 Cl1 C19 42.3(8) 3_686 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.879 _refine_diff_density_min -2.200 _refine_diff_density_rms 0.121 # Attachment '- 1b.cif' data_ic8184 _database_code_depnum_ccdc_archive 'CCDC 864437' #TrackingRef '- 1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 Br2 N4 Ni' _chemical_formula_weight 545.01 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)/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 11.1769(2) _cell_length_b 15.9132(2) _cell_length_c 13.9105(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.1397(7) _cell_angle_gamma 90.00 _cell_volume 2464.18(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour green _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 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 4.041 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.437 _exptl_absorpt_correction_T_max 0.572 _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 'NONIUS KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14272 _diffrn_reflns_av_R_equivalents 0.0796 _diffrn_reflns_av_sigmaI/netI 0.0875 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5649 _reflns_number_gt 3737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _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^)+(0.0457P)^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 0.0048(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5649 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Ni Ni -0.14876(4) -0.18646(3) 0.33062(4) 0.02104(14) Uani 1 1 d . . . Br1 Br -0.24510(4) -0.28683(3) 0.21633(4) 0.03591(15) Uani 1 1 d . . . Br2 Br 0.17884(3) 0.01128(3) 0.38666(3) 0.02942(13) Uani 1 1 d . . . N1 N -0.3067(3) -0.1209(2) 0.3434(2) 0.0252(8) Uani 1 1 d . . . N2 N -0.0935(3) -0.0661(2) 0.2906(2) 0.0235(7) Uani 1 1 d . . . N3 N 0.0211(3) -0.2431(2) 0.3331(2) 0.0260(8) Uani 1 1 d . . . N4 N -0.0998(3) -0.1854(2) 0.4799(3) 0.0260(8) Uani 1 1 d . . . C1 C -0.4192(4) -0.1519(3) 0.3454(3) 0.0343(11) Uani 1 1 d . . . H1A H -0.4327 -0.2103 0.3352 0.041 Uiso 1 1 calc R . . C2 C -0.5151(4) -0.1004(3) 0.3620(3) 0.0374(11) Uani 1 1 d . . . H2A H -0.5937 -0.1231 0.3628 0.045 Uiso 1 1 calc R . . C3 C -0.4949(4) -0.0151(3) 0.3776(4) 0.0370(11) Uani 1 1 d . . . H3A H -0.5590 0.0212 0.3904 0.044 Uiso 1 1 calc R . . C4 C -0.3813(4) 0.0158(3) 0.3742(3) 0.0324(10) Uani 1 1 d . . . H4A H -0.3658 0.0740 0.3845 0.039 Uiso 1 1 calc R . . C5 C -0.2884(4) -0.0384(3) 0.3554(3) 0.0252(9) Uani 1 1 d . . . C6 C -0.1621(3) -0.0090(2) 0.3496(3) 0.0235(9) Uani 1 1 d . . . H6A H -0.1633 0.0480 0.3211 0.028 Uiso 1 1 calc R . . H6B H -0.1210 -0.0054 0.4156 0.028 Uiso 1 1 calc R . . C7 C -0.1010(4) -0.0449(3) 0.1842(3) 0.0315(10) Uani 1 1 d . . . C8 C -0.2303(4) -0.0481(3) 0.1398(3) 0.0398(12) Uani 1 1 d . . . H8A H -0.2775 -0.0049 0.1697 0.060 Uiso 1 1 calc R . . H8B H -0.2642 -0.1036 0.1510 0.060 Uiso 1 1 calc R . . H8C H -0.2324 -0.0377 0.0703 0.060 Uiso 1 1 calc R . . C9 C -0.0469(4) 0.0419(3) 0.1687(4) 0.0430(12) Uani 1 1 d . . . H9A H -0.0951 0.0849 0.1977 0.064 Uiso 1 1 calc R . . H9B H -0.0466 0.0527 0.0993 0.064 Uiso 1 1 calc R . . H9C H 0.0356 0.0437 0.1990 0.064 Uiso 1 1 calc R . . C10 C -0.0260(4) -0.1113(3) 0.1381(3) 0.0440(13) Uani 1 1 d . . . H10A H -0.0606 -0.1670 0.1473 0.066 Uiso 1 1 calc R . . H10B H 0.0566 -0.1097 0.1684 0.066 Uiso 1 1 calc R . . H10C H -0.0258 -0.0998 0.0689 0.066 Uiso 1 1 calc R . . C11 C 0.0640(4) -0.2948(3) 0.2688(3) 0.0351(11) Uani 1 1 d . . . H11A H 0.0150 -0.3067 0.2110 0.042 Uiso 1 1 calc R . . C12 C 0.1754(4) -0.3315(3) 0.2821(4) 0.0409(12) Uani 1 1 d . . . H12A H 0.2023 -0.3693 0.2357 0.049 Uiso 1 1 calc R . . C13 C 0.2481(4) -0.3115(3) 0.3662(4) 0.0471(13) Uani 1 1 d . . . H13A H 0.3269 -0.3340 0.3767 0.057 Uiso 1 1 calc R . . C14 C 0.2049(4) -0.2593(3) 0.4330(4) 0.0366(11) Uani 1 1 d . . . H14A H 0.2530 -0.2454 0.4906 0.044 Uiso 1 1 calc R . . C15 C 0.0899(4) -0.2271(3) 0.4154(3) 0.0273(9) Uani 1 1 d . . . C16 C 0.0331(3) -0.1734(3) 0.4873(3) 0.0262(9) Uani 1 1 d . . . H16A H 0.0672 -0.1881 0.5533 0.031 Uiso 1 1 calc R . . H16B H 0.0515 -0.1136 0.4758 0.031 Uiso 1 1 calc R . . C17 C -0.1383(4) -0.2601(3) 0.5380(3) 0.0308(10) Uani 1 1 d . . . C18 C -0.2759(4) -0.2595(3) 0.5272(4) 0.0447(13) Uani 1 1 d . . . H18A H -0.3051 -0.2063 0.5519 0.067 Uiso 1 1 calc R . . H18B H -0.3060 -0.3064 0.5639 0.067 Uiso 1 1 calc R . . H18C H -0.3047 -0.2655 0.4589 0.067 Uiso 1 1 calc R . . C19 C -0.0944(4) -0.2518(3) 0.6437(3) 0.0441(13) Uani 1 1 d . . . H19A H -0.1220 -0.1982 0.6685 0.066 Uiso 1 1 calc R . . H19B H -0.0064 -0.2535 0.6509 0.066 Uiso 1 1 calc R . . H19C H -0.1263 -0.2982 0.6800 0.066 Uiso 1 1 calc R . . C20 C -0.0947(5) -0.3439(3) 0.4986(4) 0.0536(15) Uani 1 1 d . . . H20A H -0.0067 -0.3453 0.5054 0.080 Uiso 1 1 calc R . . H20B H -0.1236 -0.3492 0.4302 0.080 Uiso 1 1 calc R . . H20C H -0.1260 -0.3905 0.5349 0.080 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 0.0187(3) 0.0204(3) 0.0235(3) -0.0026(2) -0.0004(2) -0.0008(2) Br1 0.0321(3) 0.0304(3) 0.0435(3) -0.0137(2) -0.0068(2) -0.00168(18) Br2 0.0225(2) 0.0340(2) 0.0322(3) -0.00126(19) 0.00505(17) -0.00557(17) N1 0.0203(17) 0.0285(19) 0.027(2) -0.0007(15) 0.0009(14) -0.0016(14) N2 0.0247(17) 0.0247(18) 0.0216(19) 0.0001(14) 0.0046(14) -0.0004(14) N3 0.0262(18) 0.0246(19) 0.028(2) -0.0029(15) 0.0050(16) 0.0005(14) N4 0.0186(16) 0.0316(19) 0.028(2) 0.0043(16) 0.0021(15) -0.0039(14) C1 0.023(2) 0.041(3) 0.039(3) 0.000(2) 0.002(2) -0.0059(19) C2 0.023(2) 0.048(3) 0.041(3) 0.001(2) 0.002(2) -0.002(2) C3 0.026(2) 0.044(3) 0.043(3) 0.002(2) 0.010(2) 0.006(2) C4 0.030(2) 0.031(2) 0.036(3) 0.002(2) 0.003(2) 0.0038(19) C5 0.026(2) 0.026(2) 0.023(2) 0.0032(18) 0.0012(17) 0.0033(17) C6 0.023(2) 0.021(2) 0.027(2) -0.0016(17) 0.0035(17) -0.0003(16) C7 0.032(2) 0.034(2) 0.029(2) 0.009(2) 0.0068(19) 0.0034(19) C8 0.041(3) 0.054(3) 0.024(3) 0.006(2) 0.000(2) 0.003(2) C9 0.050(3) 0.042(3) 0.039(3) 0.010(2) 0.011(2) -0.004(2) C10 0.053(3) 0.050(3) 0.032(3) 0.003(2) 0.017(2) 0.010(2) C11 0.033(2) 0.039(3) 0.034(3) -0.008(2) 0.004(2) 0.001(2) C12 0.037(3) 0.044(3) 0.044(3) -0.008(2) 0.016(2) 0.013(2) C13 0.032(3) 0.056(3) 0.054(4) -0.001(3) 0.007(2) 0.017(2) C14 0.026(2) 0.047(3) 0.035(3) -0.002(2) -0.002(2) 0.010(2) C15 0.024(2) 0.027(2) 0.031(2) 0.0021(19) 0.0028(18) -0.0031(17) C16 0.021(2) 0.027(2) 0.029(2) 0.0028(18) -0.0020(18) -0.0029(17) C17 0.031(2) 0.029(2) 0.033(3) 0.010(2) 0.005(2) -0.0009(18) C18 0.035(3) 0.060(3) 0.039(3) 0.019(3) 0.002(2) -0.013(2) C19 0.032(3) 0.060(3) 0.041(3) 0.024(3) 0.002(2) -0.002(2) C20 0.071(4) 0.032(3) 0.060(4) 0.010(3) 0.018(3) -0.005(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 Ni N1 2.071(3) . ? Ni N3 2.099(3) . ? Ni N4 2.099(4) . ? Ni N2 2.102(3) . ? Ni Br1 2.4355(7) . ? N1 C5 1.337(5) . ? N1 C1 1.353(5) . ? N2 C6 1.482(5) . ? N2 C7 1.514(5) . ? N3 C11 1.336(5) . ? N3 C15 1.345(5) . ? N4 C16 1.492(5) . ? N4 C17 1.521(5) . ? C1 C2 1.386(6) . ? C2 C3 1.390(6) . ? C3 C4 1.366(6) . ? C4 C5 1.392(6) . ? C5 C6 1.497(5) . ? C7 C8 1.520(6) . ? C7 C10 1.526(6) . ? C7 C9 1.531(6) . ? C11 C12 1.374(6) . ? C12 C13 1.400(7) . ? C13 C14 1.366(7) . ? C14 C15 1.385(6) . ? C15 C16 1.500(6) . ? C17 C19 1.514(6) . ? C17 C18 1.532(6) . ? C17 C20 1.538(7) . ? 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 N3 172.37(14) . . ? N1 Ni N4 93.44(13) . . ? N3 Ni N4 80.31(13) . . ? N1 Ni N2 80.60(12) . . ? N3 Ni N2 96.26(13) . . ? N4 Ni N2 101.41(13) . . ? N1 Ni Br1 93.19(10) . . ? N3 Ni Br1 94.34(9) . . ? N4 Ni Br1 135.36(9) . . ? N2 Ni Br1 123.22(10) . . ? C5 N1 C1 119.1(4) . . ? C5 N1 Ni 112.5(3) . . ? C1 N1 Ni 128.3(3) . . ? C6 N2 C7 114.8(3) . . ? C6 N2 Ni 103.5(2) . . ? C7 N2 Ni 118.0(3) . . ? C11 N3 C15 118.4(4) . . ? C11 N3 Ni 129.1(3) . . ? C15 N3 Ni 112.4(3) . . ? C16 N4 C17 113.0(3) . . ? C16 N4 Ni 103.8(2) . . ? C17 N4 Ni 117.3(3) . . ? N1 C1 C2 121.5(4) . . ? C1 C2 C3 119.1(4) . . ? C4 C3 C2 119.0(4) . . ? C3 C4 C5 119.6(4) . . ? N1 C5 C4 121.6(4) . . ? N1 C5 C6 115.7(3) . . ? C4 C5 C6 122.6(4) . . ? N2 C6 C5 112.0(3) . . ? N2 C7 C8 110.9(3) . . ? N2 C7 C10 105.8(3) . . ? C8 C7 C10 110.1(4) . . ? N2 C7 C9 110.6(4) . . ? C8 C7 C9 110.2(4) . . ? C10 C7 C9 109.1(4) . . ? N3 C11 C12 123.2(5) . . ? C11 C12 C13 117.8(4) . . ? C14 C13 C12 119.5(4) . . ? C13 C14 C15 118.9(5) . . ? N3 C15 C14 122.1(4) . . ? N3 C15 C16 115.6(3) . . ? C14 C15 C16 122.3(4) . . ? N4 C16 C15 111.1(3) . . ? C19 C17 N4 111.4(4) . . ? C19 C17 C18 109.3(4) . . ? N4 C17 C18 105.8(3) . . ? C19 C17 C20 109.7(4) . . ? N4 C17 C20 112.0(4) . . ? C18 C17 C20 108.5(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.668 _refine_diff_density_min -0.881 _refine_diff_density_rms 0.146 # Attachment '- 1d.cif' data_ic8769 _database_code_depnum_ccdc_archive 'CCDC 864438' #TrackingRef '- 1d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 Br4 N4 Ni2' _chemical_formula_weight 861.64 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 10.4314(8) _cell_length_b 10.5173(8) _cell_length_c 16.3410(12) _cell_angle_alpha 99.6200(10) _cell_angle_beta 97.4620(10) _cell_angle_gamma 115.3910(10) _cell_volume 1555.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2759 _cell_measurement_theta_min 1.30 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.840 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 6.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4808 _exptl_absorpt_correction_T_max 0.6461 _exptl_absorpt_process_details ? _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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14418 _diffrn_reflns_av_R_equivalents 0.0672 _diffrn_reflns_av_sigmaI/netI 0.1082 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5482 _reflns_number_gt 2832 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.1055P)^2^+20.6978P] 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 0.0014(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5482 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1537 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2710 _refine_ls_wR_factor_gt 0.2482 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 1.0412(2) -0.3267(2) -0.02535(12) 0.0394(6) Uani 1 1 d . . . Br1 Br 1.1481(2) -0.4948(2) -0.03662(14) 0.0622(6) Uani 1 1 d . . . Br2 Br 1.1347(2) -0.1228(2) 0.09995(12) 0.0683(7) Uani 1 1 d . . . N1 N 1.1741(15) -0.2004(15) -0.0947(8) 0.047(3) Uani 1 1 d . . . N2 N 0.8949(14) -0.2727(14) -0.0905(8) 0.040(3) Uani 1 1 d . . . H2A H 0.8945 -0.2023 -0.0499 0.048 Uiso 1 1 calc R . . C1 C 1.3159(19) -0.164(2) -0.0884(12) 0.057(5) Uani 1 1 d . . . H1A H 1.3577 -0.2030 -0.0530 0.068 Uiso 1 1 calc R . . C2 C 1.397(2) -0.077(2) -0.1285(13) 0.072(6) Uani 1 1 d . . . H2B H 1.4970 -0.0465 -0.1175 0.086 Uiso 1 1 calc R . . C3 C 1.331(3) -0.030(3) -0.1897(13) 0.076(7) Uani 1 1 d . . . H3A H 1.3854 0.0266 -0.2225 0.092 Uiso 1 1 calc R . . C4 C 1.186(2) -0.069(2) -0.2001(12) 0.060(5) Uani 1 1 d . . . H4B H 1.1390 -0.0406 -0.2400 0.072 Uiso 1 1 calc R . . C5 C 1.1126(18) -0.1531(16) -0.1486(10) 0.040(4) Uani 1 1 d . . . C6 C 0.9500(18) -0.1963(19) -0.1532(11) 0.049(4) Uani 1 1 d . . . H6A H 0.9372 -0.1093 -0.1450 0.059 Uiso 1 1 calc R . . H6B H 0.8938 -0.2573 -0.2094 0.059 Uiso 1 1 calc R . . C7 C 0.7374(17) -0.3833(18) -0.1166(9) 0.041(4) Uani 1 1 d . . . C8 C 0.641(2) -0.353(2) -0.0772(12) 0.056(5) Uani 1 1 d . . . C9 C 0.499(2) -0.451(3) -0.0992(16) 0.078(7) Uani 1 1 d . . . H9A H 0.4334 -0.4367 -0.0708 0.094 Uiso 1 1 calc R . . C10 C 0.448(2) -0.586(3) -0.1705(14) 0.077(7) Uani 1 1 d . . . H10A H 0.3507 -0.6537 -0.1903 0.093 Uiso 1 1 calc R . . C11 C 0.551(3) -0.601(3) -0.2021(13) 0.082(7) Uani 1 1 d . . . H11A H 0.5228 -0.6838 -0.2451 0.098 Uiso 1 1 calc R . . C12 C 0.6977(19) -0.503(2) -0.1770(11) 0.053(5) Uani 1 1 d . . . C13 C 0.690(2) -0.219(2) -0.0027(13) 0.080(7) Uani 1 1 d . . . H13A H 0.7924 -0.1569 0.0052 0.120 Uiso 1 1 calc R . . H13B H 0.6711 -0.2495 0.0485 0.120 Uiso 1 1 calc R . . H13C H 0.6371 -0.1664 -0.0155 0.120 Uiso 1 1 calc R . . C14 C 0.806(2) -0.544(2) -0.2150(12) 0.066(5) Uani 1 1 d . . . H14A H 0.9029 -0.4669 -0.1919 0.098 Uiso 1 1 calc R . . H14B H 0.7830 -0.5596 -0.2758 0.098 Uiso 1 1 calc R . . H14C H 0.7991 -0.6316 -0.2011 0.098 Uiso 1 1 calc R . . Ni2 Ni 1.3200(3) -0.5498(2) -0.47845(14) 0.0481(6) Uani 1 1 d . . . Br3 Br 1.5092(2) -0.6271(2) -0.44965(14) 0.0664(7) Uani 1 1 d . . . Br4 Br 1.1207(2) -0.6708(3) -0.60417(13) 0.0814(8) Uani 1 1 d . . . N3 N 1.2044(15) -0.6661(15) -0.4024(9) 0.048(4) Uani 1 1 d . . . N4 N 1.286(2) -0.3945(17) -0.4039(11) 0.110(9) Uani 1 1 d . . . H4A H 1.2098 -0.4011 -0.4421 0.132 Uiso 1 1 calc R . . C15 C 1.150(2) -0.818(2) -0.4159(15) 0.080(7) Uani 1 1 d . . . H15A H 1.1691 -0.8687 -0.4611 0.096 Uiso 1 1 calc R . . C16 C 1.072(2) -0.891(2) -0.3652(13) 0.067(6) Uani 1 1 d . . . H16A H 1.0495 -0.9879 -0.3698 0.080 Uiso 1 1 calc R . . C17 C 1.0258(19) -0.824(2) -0.3077(13) 0.062(5) Uani 1 1 d . . . H17A H 0.9625 -0.8767 -0.2768 0.074 Uiso 1 1 calc R . . C18 C 1.071(2) -0.681(2) -0.2950(10) 0.062(5) Uani 1 1 d . . . H18A H 1.0445 -0.6322 -0.2528 0.074 Uiso 1 1 calc R . . C19 C 1.1608(16) -0.6032(17) -0.3473(11) 0.045(4) Uani 1 1 d . . . C20 C 1.206(2) -0.446(2) -0.3409(12) 0.063(5) Uani 1 1 d . . . H20A H 1.1197 -0.4310 -0.3482 0.075 Uiso 1 1 calc R . . H20B H 1.2659 -0.3893 -0.2846 0.075 Uiso 1 1 calc R . . C21 C 1.378(2) -0.2394(19) -0.3899(10) 0.050(5) Uani 1 1 d . . . C22 C 1.330(2) -0.166(3) -0.4339(12) 0.067(6) Uani 1 1 d . . . C23 C 1.408(3) -0.027(3) -0.4245(14) 0.077(6) Uani 1 1 d . . . H23A H 1.3761 0.0199 -0.4594 0.092 Uiso 1 1 calc R . . C24 C 1.535(3) 0.051(2) -0.3641(15) 0.087(8) Uani 1 1 d . . . H24A H 1.5842 0.1515 -0.3535 0.104 Uiso 1 1 calc R . . C25 C 1.591(2) -0.022(3) -0.3183(12) 0.077(7) Uani 1 1 d . . . H25A H 1.6804 0.0289 -0.2789 0.092 Uiso 1 1 calc R . . C26 C 1.510(2) -0.173(2) -0.3331(12) 0.060(5) Uani 1 1 d . . . C27 C 1.191(3) -0.242(4) -0.5060(16) 0.142(14) Uani 1 1 d . . . H27A H 1.1754 -0.1696 -0.5288 0.214 Uiso 1 1 calc R . . H27B H 1.1089 -0.2962 -0.4839 0.214 Uiso 1 1 calc R . . H27C H 1.2020 -0.3060 -0.5503 0.214 Uiso 1 1 calc R . . C28 C 1.578(4) -0.245(4) -0.2789(16) 0.130(12) Uani 1 1 d . . . H28A H 1.5152 -0.3481 -0.2930 0.195 Uiso 1 1 calc R . . H28B H 1.5905 -0.2051 -0.2196 0.195 Uiso 1 1 calc R . . H28C H 1.6715 -0.2279 -0.2907 0.195 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0422(12) 0.0420(13) 0.0380(11) 0.0162(9) 0.0162(10) 0.0190(10) Br1 0.0595(12) 0.0659(13) 0.0949(15) 0.0491(12) 0.0498(11) 0.0398(11) Br2 0.0799(15) 0.0683(14) 0.0397(10) 0.0062(9) 0.0098(10) 0.0224(12) N1 0.047(9) 0.061(10) 0.038(8) 0.013(7) 0.007(7) 0.030(8) N2 0.048(8) 0.044(8) 0.031(7) 0.016(6) 0.015(6) 0.020(7) C1 0.049(11) 0.067(13) 0.076(13) 0.039(11) 0.033(10) 0.033(10) C2 0.045(11) 0.081(15) 0.075(14) 0.008(12) 0.034(11) 0.013(11) C3 0.096(17) 0.105(18) 0.063(13) 0.057(13) 0.058(13) 0.054(15) C4 0.061(12) 0.054(12) 0.066(13) 0.033(10) 0.022(10) 0.018(10) C5 0.051(10) 0.022(8) 0.037(9) 0.004(7) 0.015(8) 0.009(8) C6 0.049(10) 0.051(11) 0.047(10) 0.025(9) 0.011(8) 0.018(9) C7 0.040(9) 0.056(11) 0.021(8) 0.011(8) 0.010(7) 0.016(9) C8 0.048(11) 0.075(14) 0.066(12) 0.042(11) 0.026(10) 0.033(11) C9 0.051(13) 0.109(19) 0.107(18) 0.083(17) 0.046(13) 0.039(13) C10 0.057(13) 0.089(17) 0.059(13) 0.036(13) 0.014(11) 0.003(12) C11 0.080(17) 0.105(19) 0.040(11) 0.015(11) 0.005(12) 0.028(15) C12 0.042(11) 0.068(13) 0.036(10) 0.008(9) -0.003(8) 0.019(10) C13 0.082(15) 0.094(17) 0.071(14) 0.002(12) 0.032(12) 0.049(14) C14 0.063(13) 0.051(12) 0.061(12) 0.010(10) 0.011(10) 0.009(10) Ni2 0.0594(15) 0.0507(14) 0.0455(13) 0.0244(11) 0.0258(11) 0.0272(12) Br3 0.0735(14) 0.0718(14) 0.0883(15) 0.0550(12) 0.0458(12) 0.0444(12) Br4 0.0688(14) 0.1061(19) 0.0508(12) 0.0339(12) 0.0119(10) 0.0191(13) N3 0.056(9) 0.039(9) 0.058(9) 0.027(7) 0.033(8) 0.019(7) N4 0.157(19) 0.041(11) 0.062(11) -0.007(8) 0.061(12) -0.020(12) C15 0.097(17) 0.083(17) 0.091(16) 0.058(13) 0.060(14) 0.046(14) C16 0.064(13) 0.055(13) 0.083(15) 0.045(12) 0.025(12) 0.017(11) C17 0.046(11) 0.065(14) 0.073(13) 0.038(11) 0.033(10) 0.011(10) C18 0.071(13) 0.087(16) 0.028(9) 0.025(10) 0.023(9) 0.031(12) C19 0.023(8) 0.035(10) 0.051(10) -0.007(8) -0.011(8) 0.002(8) C20 0.071(13) 0.062(13) 0.059(12) 0.024(10) 0.042(10) 0.023(11) C21 0.059(12) 0.043(11) 0.024(8) -0.002(8) 0.017(9) 0.004(9) C22 0.062(14) 0.099(19) 0.035(10) 0.005(12) 0.017(10) 0.036(14) C23 0.096(18) 0.10(2) 0.046(12) 0.005(13) 0.015(13) 0.059(17) C24 0.13(2) 0.050(14) 0.062(15) 0.018(12) 0.063(17) 0.019(15) C25 0.051(12) 0.098(19) 0.038(11) -0.009(12) 0.008(9) 0.005(13) C26 0.086(15) 0.074(15) 0.053(11) 0.032(11) 0.049(12) 0.051(13) C27 0.085(19) 0.28(4) 0.070(17) 0.04(2) 0.035(15) 0.08(2) C28 0.18(3) 0.21(4) 0.077(18) 0.05(2) 0.021(19) 0.15(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 Ni1 N1 2.075(13) . ? Ni1 N2 2.076(12) . ? Ni1 Br2 2.442(3) . ? Ni1 Br1 2.457(3) . ? Ni1 Br1 2.534(2) 2_745 ? Br1 Ni1 2.534(2) 2_745 ? N1 C5 1.31(2) . ? N1 C1 1.34(2) . ? N2 C6 1.433(18) . ? N2 C7 1.50(2) . ? C1 C2 1.29(2) . ? C2 C3 1.42(3) . ? C3 C4 1.36(3) . ? C4 C5 1.38(2) . ? C5 C6 1.54(2) . ? C7 C12 1.33(2) . ? C7 C8 1.38(2) . ? C8 C9 1.34(3) . ? C8 C13 1.55(3) . ? C9 C10 1.51(3) . ? C10 C11 1.30(3) . ? C11 C12 1.39(3) . ? C12 C14 1.53(3) . ? Ni2 N3 2.031(12) . ? Ni2 N4 2.058(19) . ? Ni2 Br4 2.431(3) . ? Ni2 Br3 2.457(3) . ? Ni2 Br3 2.539(3) 2_844 ? Br3 Ni2 2.539(3) 2_844 ? N3 C19 1.27(2) . ? N3 C15 1.41(2) . ? N4 C20 1.44(2) . ? N4 C21 1.45(2) . ? C15 C16 1.34(2) . ? C16 C17 1.34(3) . ? C17 C18 1.34(3) . ? C18 C19 1.43(2) . ? C19 C20 1.50(2) . ? C21 C22 1.34(3) . ? C21 C26 1.37(3) . ? C22 C23 1.30(3) . ? C22 C27 1.54(3) . ? C23 C24 1.37(3) . ? C24 C25 1.39(3) . ? C25 C26 1.40(3) . ? C26 C28 1.55(3) . ? 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 80.8(5) . . ? N1 Ni1 Br2 92.5(4) . . ? N2 Ni1 Br2 96.3(4) . . ? N1 Ni1 Br1 93.1(4) . . ? N2 Ni1 Br1 143.8(4) . . ? Br2 Ni1 Br1 119.65(11) . . ? N1 Ni1 Br1 170.9(4) . 2_745 ? N2 Ni1 Br1 94.2(3) . 2_745 ? Br2 Ni1 Br1 95.58(10) . 2_745 ? Br1 Ni1 Br1 86.51(8) . 2_745 ? Ni1 Br1 Ni1 93.49(8) . 2_745 ? C5 N1 C1 118.3(15) . . ? C5 N1 Ni1 116.1(11) . . ? C1 N1 Ni1 125.6(11) . . ? C6 N2 C7 115.3(12) . . ? C6 N2 Ni1 113.2(10) . . ? C7 N2 Ni1 118.0(9) . . ? C2 C1 N1 123.8(18) . . ? C1 C2 C3 118.3(18) . . ? C4 C3 C2 119.4(17) . . ? C3 C4 C5 116.8(17) . . ? N1 C5 C4 123.0(16) . . ? N1 C5 C6 116.7(13) . . ? C4 C5 C6 120.3(15) . . ? N2 C6 C5 112.7(13) . . ? C12 C7 C8 123.5(17) . . ? C12 C7 N2 118.7(14) . . ? C8 C7 N2 117.8(15) . . ? C9 C8 C7 119(2) . . ? C9 C8 C13 118.2(19) . . ? C7 C8 C13 122.8(17) . . ? C8 C9 C10 120(2) . . ? C11 C10 C9 115(2) . . ? C10 C11 C12 125(2) . . ? C7 C12 C11 117.4(18) . . ? C7 C12 C14 123.7(16) . . ? C11 C12 C14 118.7(18) . . ? N3 Ni2 N4 79.4(6) . . ? N3 Ni2 Br4 94.4(4) . . ? N4 Ni2 Br4 107.7(7) . . ? N3 Ni2 Br3 91.9(4) . . ? N4 Ni2 Br3 129.6(7) . . ? Br4 Ni2 Br3 122.50(13) . . ? N3 Ni2 Br3 170.4(4) . 2_844 ? N4 Ni2 Br3 94.3(4) . 2_844 ? Br4 Ni2 Br3 94.47(10) . 2_844 ? Br3 Ni2 Br3 86.47(9) . 2_844 ? Ni2 Br3 Ni2 93.53(9) . 2_844 ? C19 N3 C15 117.5(14) . . ? C19 N3 Ni2 118.3(11) . . ? C15 N3 Ni2 123.5(12) . . ? C20 N4 C21 118.8(15) . . ? C20 N4 Ni2 113.6(13) . . ? C21 N4 Ni2 123.1(13) . . ? C16 C15 N3 122(2) . . ? C15 C16 C17 120(2) . . ? C18 C17 C16 119.8(16) . . ? C17 C18 C19 119.1(17) . . ? N3 C19 C18 121.4(16) . . ? N3 C19 C20 116.7(15) . . ? C18 C19 C20 121.8(16) . . ? N4 C20 C19 111.9(16) . . ? C22 C21 C26 122.1(18) . . ? C22 C21 N4 118(2) . . ? C26 C21 N4 120(2) . . ? C23 C22 C21 121(2) . . ? C23 C22 C27 116(2) . . ? C21 C22 C27 123(3) . . ? C22 C23 C24 121(2) . . ? C23 C24 C25 120(2) . . ? C24 C25 C26 118(2) . . ? C21 C26 C25 117.6(18) . . ? C21 C26 C28 127(2) . . ? C25 C26 C28 115(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.366 _refine_diff_density_min -0.899 _refine_diff_density_rms 0.177 data_ic8600 _database_code_depnum_ccdc_archive 'CCDC 864439' #TrackingRef '- 1e (new).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H46 Br4 N4 Ni2' _chemical_formula_weight 971.83 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)/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 12.86520(10) _cell_length_b 10.15710(10) _cell_length_c 14.6983(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.6604(5) _cell_angle_gamma 90.00 _cell_volume 1858.14(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 1.88 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 5.345 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.319 _exptl_absorpt_correction_T_max 0.360 _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 'NONIUS KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15027 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4263 _reflns_number_gt 3585 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _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^)+(0.0493P)^2^+0.8624P] 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 0.0093(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4263 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.225 _refine_ls_restrained_S_all 1.225 _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 0.41575(3) 1.07451(4) 0.06998(3) 0.02477(13) Uani 1 1 d . . . Br1 Br 0.48216(3) 0.84948(3) 0.04845(3) 0.03203(13) Uani 1 1 d . . . Br2 Br 0.50127(3) 1.09157(4) 0.23653(3) 0.03813(13) Uani 1 1 d . . . N1 N 0.3549(2) 1.2595(3) 0.05873(19) 0.0274(6) Uani 1 1 d . . . N2 N 0.2632(2) 1.0355(3) -0.0224(2) 0.0266(6) Uani 1 1 d . . . C1 C 0.4161(3) 1.3657(3) 0.0884(3) 0.0339(8) Uani 1 1 d . . . H1 H 0.4856 1.3537 0.1291 0.041 Uiso 1 1 calc R . . C2 C 0.3814(3) 1.4916(3) 0.0618(3) 0.0334(8) Uani 1 1 d . . . H2 H 0.4264 1.5652 0.0837 0.040 Uiso 1 1 calc R . . C3 C 0.2806(3) 1.5088(3) 0.0031(2) 0.0312(7) Uani 1 1 d . . . H3 H 0.2550 1.5947 -0.0162 0.037 Uiso 1 1 calc R . . C4 C 0.2168(3) 1.4000(3) -0.0274(2) 0.0282(7) Uani 1 1 d . . . H4 H 0.1467 1.4101 -0.0675 0.034 Uiso 1 1 calc R . . C5 C 0.2565(2) 1.2759(3) 0.0014(2) 0.0233(6) Uani 1 1 d . . . C6 C 0.1929(3) 1.1521(3) -0.0277(2) 0.0265(7) Uani 1 1 d . . . H6A H 0.1439 1.1382 0.0136 0.032 Uiso 1 1 calc R . . H6B H 0.1485 1.1621 -0.0930 0.032 Uiso 1 1 calc R . . C7 C 0.2005(2) 0.9141(3) -0.0222(2) 0.0246(7) Uani 1 1 d . . . C8 C 0.1684(2) 0.8401(3) -0.1057(2) 0.0268(7) Uani 1 1 d . . . C9 C 0.0951(3) 0.7383(3) -0.1080(3) 0.0305(7) Uani 1 1 d . . . H9 H 0.0697 0.6897 -0.1645 0.037 Uiso 1 1 calc R . . C10 C 0.0586(3) 0.7064(3) -0.0306(3) 0.0319(8) Uani 1 1 d . . . H10 H 0.0066 0.6388 -0.0347 0.038 Uiso 1 1 calc R . . C11 C 0.0979(3) 0.7731(3) 0.0536(3) 0.0312(8) Uani 1 1 d . . . H11 H 0.0760 0.7469 0.1080 0.037 Uiso 1 1 calc R . . C12 C 0.1695(2) 0.8786(3) 0.0591(2) 0.0271(7) Uani 1 1 d . . . C13 C 0.2091(3) 0.8644(3) -0.1924(3) 0.0318(8) Uani 1 1 d . . . H13 H 0.2712 0.9268 -0.1753 0.038 Uiso 1 1 calc R . . C14 C 0.1218(3) 0.9268(4) -0.2700(3) 0.0428(9) Uani 1 1 d . . . H14A H 0.0589 0.8689 -0.2854 0.064 Uiso 1 1 calc R . . H14B H 0.1488 0.9396 -0.3260 0.064 Uiso 1 1 calc R . . H14C H 0.1015 1.0121 -0.2486 0.064 Uiso 1 1 calc R . . C15 C 0.2483(3) 0.7352(4) -0.2282(3) 0.0441(9) Uani 1 1 d . . . H15A H 0.2999 0.6917 -0.1764 0.066 Uiso 1 1 calc R . . H15B H 0.2830 0.7551 -0.2788 0.066 Uiso 1 1 calc R . . H15C H 0.1868 0.6769 -0.2522 0.066 Uiso 1 1 calc R . . C16 C 0.2094(3) 0.9475(4) 0.1533(2) 0.0325(7) Uani 1 1 d . . . H16 H 0.2578 1.0211 0.1449 0.039 Uiso 1 1 calc R . . C17 C 0.2753(3) 0.8521(4) 0.2272(3) 0.0463(10) Uani 1 1 d . . . H17A H 0.2279 0.7835 0.2409 0.069 Uiso 1 1 calc R . . H17B H 0.3081 0.9006 0.2849 0.069 Uiso 1 1 calc R . . H17C H 0.3317 0.8114 0.2027 0.069 Uiso 1 1 calc R . . C18 C 0.1166(3) 1.0064(4) 0.1867(3) 0.0458(10) Uani 1 1 d . . . H18A H 0.0729 1.0619 0.1369 0.069 Uiso 1 1 calc R . . H18B H 0.1451 1.0598 0.2430 0.069 Uiso 1 1 calc R . . H18C H 0.0720 0.9354 0.2016 0.069 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 0.0214(2) 0.0199(2) 0.0298(3) 0.00029(15) 0.00053(17) 0.00243(14) Br1 0.0316(2) 0.01984(19) 0.0457(2) 0.00427(13) 0.01179(15) 0.00425(12) Br2 0.0413(2) 0.0371(2) 0.0301(2) 0.00136(14) -0.00176(15) 0.00429(15) N1 0.0258(13) 0.0231(13) 0.0299(15) -0.0009(11) 0.0009(11) 0.0023(11) N2 0.0206(12) 0.0182(13) 0.0395(16) -0.0001(11) 0.0047(11) 0.0000(10) C1 0.0308(18) 0.0259(17) 0.039(2) -0.0032(15) -0.0020(15) 0.0046(13) C2 0.0345(18) 0.0249(17) 0.039(2) -0.0057(14) 0.0061(15) -0.0016(14) C3 0.0379(18) 0.0215(16) 0.0338(19) 0.0045(13) 0.0081(15) 0.0059(13) C4 0.0259(16) 0.0275(17) 0.0294(18) 0.0036(13) 0.0035(13) 0.0063(13) C5 0.0235(15) 0.0247(16) 0.0223(16) 0.0005(12) 0.0068(12) 0.0028(12) C6 0.0237(15) 0.0249(16) 0.0299(18) 0.0021(13) 0.0051(13) 0.0007(12) C7 0.0166(14) 0.0217(15) 0.0345(18) 0.0024(12) 0.0047(13) 0.0001(11) C8 0.0201(15) 0.0243(16) 0.0345(19) 0.0041(13) 0.0040(13) 0.0022(12) C9 0.0245(16) 0.0274(17) 0.037(2) -0.0007(14) 0.0029(14) -0.0006(13) C10 0.0243(16) 0.0248(17) 0.047(2) 0.0030(15) 0.0095(15) -0.0044(13) C11 0.0257(17) 0.0294(18) 0.040(2) 0.0052(14) 0.0120(15) 0.0016(13) C12 0.0225(15) 0.0251(16) 0.0339(18) 0.0027(13) 0.0076(13) 0.0047(12) C13 0.0298(17) 0.0315(18) 0.0341(19) -0.0017(14) 0.0080(15) -0.0014(14) C14 0.045(2) 0.047(2) 0.036(2) 0.0088(17) 0.0108(18) 0.0045(17) C15 0.048(2) 0.040(2) 0.049(2) -0.0035(18) 0.0207(19) 0.0070(18) C16 0.0330(17) 0.0357(19) 0.0303(19) 0.0000(14) 0.0106(14) -0.0016(15) C17 0.049(2) 0.048(2) 0.039(2) 0.0094(18) 0.0050(19) 0.0032(18) C18 0.054(2) 0.047(2) 0.043(2) 0.0005(18) 0.0237(19) 0.0048(19) _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 2.026(3) . ? Ni N2 2.122(3) . ? Ni Br2 2.4229(5) . ? Ni Br1 2.4882(5) . ? Ni Br1 2.5512(5) 3_675 ? Br1 Ni 2.5512(5) 3_675 ? N1 C5 1.341(4) . ? N1 C1 1.342(4) . ? N2 C7 1.474(4) . ? N2 C6 1.479(4) . ? C1 C2 1.377(5) . ? C2 C3 1.376(5) . ? C3 C4 1.382(5) . ? C4 C5 1.386(4) . ? C5 C6 1.502(4) . ? C7 C12 1.400(5) . ? C7 C8 1.409(5) . ? C8 C9 1.394(4) . ? C8 C13 1.515(5) . ? C9 C10 1.375(5) . ? C10 C11 1.389(5) . ? C11 C12 1.402(5) . ? C12 C16 1.520(5) . ? C13 C14 1.522(5) . ? C13 C15 1.545(5) . ? C16 C18 1.524(5) . ? C16 C17 1.539(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 81.08(10) . . ? N1 Ni Br2 94.78(8) . . ? N2 Ni Br2 140.32(8) . . ? N1 Ni Br1 168.39(8) . . ? N2 Ni Br1 92.24(7) . . ? Br2 Ni Br1 96.398(18) . . ? N1 Ni Br1 85.34(8) . 3_675 ? N2 Ni Br1 99.94(8) . 3_675 ? Br2 Ni Br1 119.160(19) . 3_675 ? Br1 Ni Br1 86.479(17) . 3_675 ? Ni Br1 Ni 93.520(17) . 3_675 ? C5 N1 C1 119.1(3) . . ? C5 N1 Ni 116.8(2) . . ? C1 N1 Ni 122.4(2) . . ? C7 N2 C6 110.0(2) . . ? C7 N2 Ni 125.0(2) . . ? C6 N2 Ni 109.79(19) . . ? N1 C1 C2 122.2(3) . . ? C3 C2 C1 118.8(3) . . ? C2 C3 C4 119.3(3) . . ? C3 C4 C5 119.0(3) . . ? N1 C5 C4 121.4(3) . . ? N1 C5 C6 115.7(3) . . ? C4 C5 C6 122.8(3) . . ? N2 C6 C5 111.9(2) . . ? C12 C7 C8 121.5(3) . . ? C12 C7 N2 119.4(3) . . ? C8 C7 N2 119.0(3) . . ? C9 C8 C7 117.6(3) . . ? C9 C8 C13 118.5(3) . . ? C7 C8 C13 123.9(3) . . ? C10 C9 C8 121.7(3) . . ? C9 C10 C11 119.9(3) . . ? C10 C11 C12 120.7(3) . . ? C7 C12 C11 118.1(3) . . ? C7 C12 C16 123.8(3) . . ? C11 C12 C16 118.1(3) . . ? C8 C13 C14 110.6(3) . . ? C8 C13 C15 111.1(3) . . ? C14 C13 C15 109.9(3) . . ? C12 C16 C18 111.2(3) . . ? C12 C16 C17 110.6(3) . . ? C18 C16 C17 110.9(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.836 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.207 # Attachment '- 1f.cif' data_ic8599 _database_code_depnum_ccdc_archive 'CCDC 864440' #TrackingRef '- 1f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 Br2 N2 Ni' _chemical_formula_weight 382.78 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 13.4202(2) _cell_length_b 7.5579(1) _cell_length_c 13.7783(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.6451(7) _cell_angle_gamma 90.00 _cell_volume 1368.75(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used all _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 27.50 _exptl_crystal_description rod _exptl_crystal_colour purple _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.858 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 7.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.108 _exptl_absorpt_correction_T_max 0.274 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10524 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3138 _reflns_number_gt 2566 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _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^)+(0.0619P)^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 0.0053(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3138 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.1061 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.73429(3) -0.12245(5) 0.11609(3) 0.02496(15) Uani 1 1 d . . . Br1 Br 0.70038(3) -0.02405(6) -0.04811(3) 0.03920(15) Uani 1 1 d . . . Br2 Br 0.78104(3) 0.03382(5) 0.26757(3) 0.03164(14) Uani 1 1 d . . . N1 N 0.6242(2) -0.2866(4) 0.1332(2) 0.0258(6) Uani 1 1 d . . . N2 N 0.8231(2) -0.3442(4) 0.13952(19) 0.0245(6) Uani 1 1 d . . . C1 C 0.5231(3) -0.2642(5) 0.1038(3) 0.0311(8) Uani 1 1 d . . . H1 H 0.4969 -0.1559 0.0721 0.037 Uiso 1 1 d R . . C2 C 0.4543(3) -0.3934(5) 0.1161(3) 0.0334(8) Uani 1 1 d . . . H2 H 0.3827 -0.3717 0.0958 0.040 Uiso 1 1 d R . . C3 C 0.4909(3) -0.5527(5) 0.1581(3) 0.0390(9) Uani 1 1 d . . . H3 H 0.4442 -0.6448 0.1667 0.047 Uiso 1 1 d R . . C4 C 0.5955(3) -0.5776(5) 0.1882(3) 0.0336(8) Uani 1 1 d . . . H4 H 0.6213 -0.6879 0.2176 0.040 Uiso 1 1 d R . . C5 C 0.6605(3) -0.4408(4) 0.1754(2) 0.0264(7) Uani 1 1 d . . . C6 C 0.7746(3) -0.4468(4) 0.2096(3) 0.0281(8) Uani 1 1 d . . . H6A H 0.7978 -0.5672 0.2120 0.034 Uiso 1 1 d R . . H6B H 0.7927 -0.3953 0.2745 0.034 Uiso 1 1 d R . . C7 C 0.9309(3) -0.3006(5) 0.1852(3) 0.0304(8) Uani 1 1 d . . . H7A H 0.9333 -0.2496 0.2494 0.036 Uiso 1 1 d R . . H7B H 0.9712 -0.4065 0.1919 0.036 Uiso 1 1 d R . . C8 C 0.9767(3) -0.1686(5) 0.1236(3) 0.0347(8) Uani 1 1 d . . . H8A H 1.0456 -0.1435 0.1556 0.042 Uiso 1 1 d R . . H8B H 0.9377 -0.0612 0.1168 0.042 Uiso 1 1 d R . . H8C H 0.9757 -0.2181 0.0593 0.042 Uiso 1 1 d R . . C9 C 0.8154(3) -0.4445(5) 0.0446(3) 0.0299(8) Uani 1 1 d . . . H9A H 0.7458 -0.4785 0.0208 0.036 Uiso 1 1 d R . . H9B H 0.8375 -0.3710 -0.0038 0.036 Uiso 1 1 d R . . C10 C 0.8771(4) -0.6134(5) 0.0512(3) 0.0438(10) Uani 1 1 d . . . H10A H 0.8670 -0.6689 -0.0128 0.053 Uiso 1 1 d R . . H10B H 0.8562 -0.6927 0.0976 0.053 Uiso 1 1 d R . . H10C H 0.9479 -0.5852 0.0731 0.053 Uiso 1 1 d 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 0.0264(3) 0.0236(2) 0.0242(2) 0.00124(16) 0.00337(18) 0.00253(18) Br1 0.0441(3) 0.0457(3) 0.0270(2) 0.01003(15) 0.00525(17) 0.01059(18) Br2 0.0376(2) 0.0281(2) 0.0294(2) -0.00611(13) 0.00736(16) 0.00071(15) N1 0.0264(16) 0.0231(14) 0.0270(14) -0.0005(11) 0.0031(12) 0.0029(12) N2 0.0252(15) 0.0244(14) 0.0230(13) -0.0023(11) 0.0028(11) 0.0001(12) C1 0.030(2) 0.0341(18) 0.0292(18) -0.0021(15) 0.0053(15) 0.0043(16) C2 0.0253(19) 0.041(2) 0.0334(19) -0.0051(16) 0.0038(15) -0.0017(16) C3 0.038(2) 0.042(2) 0.038(2) -0.0017(18) 0.0117(17) -0.0088(18) C4 0.038(2) 0.0274(18) 0.0354(19) 0.0035(16) 0.0077(17) 0.0002(17) C5 0.0299(19) 0.0279(17) 0.0213(16) -0.0003(13) 0.0047(13) 0.0015(15) C6 0.0289(19) 0.0285(18) 0.0261(17) 0.0032(14) 0.0041(14) 0.0047(15) C7 0.0250(19) 0.0326(19) 0.0305(18) -0.0051(15) -0.0014(14) 0.0039(15) C8 0.028(2) 0.040(2) 0.038(2) -0.0061(17) 0.0089(16) -0.0028(16) C9 0.034(2) 0.0285(18) 0.0265(17) -0.0088(14) 0.0044(15) -0.0023(15) C10 0.062(3) 0.032(2) 0.040(2) -0.0088(17) 0.016(2) 0.007(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 1.979(3) . ? Ni N2 2.044(3) . ? Ni Br1 2.3373(5) . ? Ni Br2 2.3698(5) . ? N1 C1 1.346(4) . ? N1 C5 1.348(4) . ? N2 C6 1.487(4) . ? N2 C7 1.493(4) . ? N2 C9 1.497(4) . ? C1 C2 1.378(5) . ? C2 C3 1.381(6) . ? C3 C4 1.394(6) . ? C4 C5 1.387(5) . ? C5 C6 1.510(5) . ? C7 C8 1.517(5) . ? C9 C10 1.515(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 83.82(11) . . ? N1 Ni Br1 108.09(8) . . ? N2 Ni Br1 114.02(8) . . ? N1 Ni Br2 106.20(8) . . ? N2 Ni Br2 103.14(8) . . ? Br1 Ni Br2 131.23(2) . . ? C1 N1 C5 119.5(3) . . ? C1 N1 Ni 128.0(2) . . ? C5 N1 Ni 112.3(2) . . ? C6 N2 C7 110.8(3) . . ? C6 N2 C9 109.9(3) . . ? C7 N2 C9 111.7(3) . . ? C6 N2 Ni 102.29(19) . . ? C7 N2 Ni 111.7(2) . . ? C9 N2 Ni 110.0(2) . . ? N1 C1 C2 122.2(3) . . ? C1 C2 C3 118.6(4) . . ? C2 C3 C4 119.6(4) . . ? C5 C4 C3 118.8(3) . . ? N1 C5 C4 121.2(3) . . ? N1 C5 C6 114.6(3) . . ? C4 C5 C6 124.2(3) . . ? N2 C6 C5 109.3(3) . . ? N2 C7 C8 112.1(3) . . ? N2 C9 C10 115.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.858 _refine_diff_density_min -0.808 _refine_diff_density_rms 0.155 # Attachment '- 2a.cif' data_ic8396 _database_code_depnum_ccdc_archive 'CCDC 864442' #TrackingRef '- 2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 Br2 N2 Ni' _chemical_formula_weight 382.78 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 6.7101(3) _cell_length_b 15.5170(7) _cell_length_c 12.6527(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.437(1) _cell_angle_gamma 90.00 _cell_volume 1313.46(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5043 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 27.50 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.936 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 7.533 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2292 _exptl_absorpt_correction_T_max 0.4915 _exptl_absorpt_process_details ? _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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11726 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3008 _reflns_number_gt 2373 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0220P)^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 0.00098(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3008 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0486 _refine_ls_wR_factor_gt 0.0463 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.26257(5) 0.452245(19) 0.05132(2) 0.02822(9) Uani 1 1 d . . . Br1 Br 0.44377(4) 0.600166(16) 0.05791(2) 0.03356(8) Uani 1 1 d . . . Br2 Br 0.05968(4) 0.487286(18) -0.127414(19) 0.03469(8) Uani 1 1 d . . . N1 N 0.1734(3) 0.32701(13) 0.06815(18) 0.0357(5) Uani 1 1 d . . . N2 N 0.4293(3) 0.42057(13) 0.19561(16) 0.0346(5) Uani 1 1 d . . . H2B H 0.5578 0.4321 0.1818 0.042 Uiso 1 1 calc R . . C1 C 0.0307(4) 0.28786(18) 0.0073(3) 0.0482(8) Uani 1 1 d . . . H1A H -0.0273 0.3169 -0.0516 0.058 Uiso 1 1 calc R . . C2 C -0.0346(5) 0.2057(2) 0.0282(3) 0.0666(10) Uani 1 1 d . . . H2A H -0.1331 0.1793 -0.0163 0.080 Uiso 1 1 calc R . . C3 C 0.0493(6) 0.1640(2) 0.1161(4) 0.0796(12) Uani 1 1 d . . . H3A H 0.0054 0.1092 0.1329 0.096 Uiso 1 1 calc R . . C4 C 0.1966(6) 0.2027(2) 0.1788(3) 0.0653(10) Uani 1 1 d . . . H4A H 0.2546 0.1750 0.2387 0.078 Uiso 1 1 calc R . . C5 C 0.2584(4) 0.28431(17) 0.1515(2) 0.0438(7) Uani 1 1 d . . . C6 C 0.4306(5) 0.32638(18) 0.2161(2) 0.0486(8) Uani 1 1 d . . . H6A H 0.4085 0.3180 0.2910 0.058 Uiso 1 1 calc R . . C7 C 0.6279(5) 0.2832(2) 0.1963(3) 0.0723(11) Uani 1 1 d . . . H7A H 0.6197 0.2228 0.2115 0.108 Uiso 1 1 calc R . . H7B H 0.7335 0.3086 0.2414 0.108 Uiso 1 1 calc R . . H7C H 0.6548 0.2910 0.1235 0.108 Uiso 1 1 calc R . . C8 C 0.4002(5) 0.4738(2) 0.2917(2) 0.0482(8) Uani 1 1 d . . . H8A H 0.3660 0.5323 0.2675 0.058 Uiso 1 1 calc R . . C9 C 0.2309(5) 0.4417(2) 0.3536(2) 0.0647(10) Uani 1 1 d . . . H9A H 0.1101 0.4392 0.3079 0.097 Uiso 1 1 calc R . . H9B H 0.2128 0.4804 0.4113 0.097 Uiso 1 1 calc R . . H9C H 0.2626 0.3853 0.3810 0.097 Uiso 1 1 calc R . . C10 C 0.5927(6) 0.4795(3) 0.3633(3) 0.0803(12) Uani 1 1 d . . . H10A H 0.6986 0.5002 0.3231 0.120 Uiso 1 1 calc R . . H10B H 0.6267 0.4234 0.3912 0.120 Uiso 1 1 calc R . . H10C H 0.5742 0.5185 0.4206 0.120 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 0.02577(18) 0.03233(18) 0.02635(17) 0.00229(14) 0.00067(13) -0.00165(13) Br1 0.02830(14) 0.03560(14) 0.03708(15) -0.00042(11) 0.00457(11) -0.00016(11) Br2 0.02736(14) 0.04926(16) 0.02731(13) 0.00030(11) 0.00125(10) 0.00352(12) N1 0.0318(12) 0.0347(12) 0.0414(13) 0.0001(10) 0.0072(11) -0.0022(10) N2 0.0366(13) 0.0395(12) 0.0275(11) 0.0041(9) 0.0004(10) -0.0001(10) C1 0.0409(18) 0.0428(17) 0.061(2) -0.0038(15) 0.0037(16) -0.0013(14) C2 0.051(2) 0.0430(19) 0.105(3) -0.014(2) 0.002(2) -0.0112(16) C3 0.082(3) 0.0373(18) 0.120(4) 0.013(2) 0.012(3) -0.0081(19) C4 0.076(3) 0.0414(18) 0.078(2) 0.0159(18) 0.005(2) -0.0017(18) C5 0.0485(18) 0.0345(15) 0.0500(18) 0.0058(13) 0.0128(15) 0.0033(13) C6 0.057(2) 0.0441(17) 0.0443(17) 0.0103(14) -0.0015(15) 0.0085(15) C7 0.056(2) 0.066(2) 0.095(3) 0.015(2) 0.002(2) 0.0182(18) C8 0.063(2) 0.0532(18) 0.0273(14) 0.0008(13) 0.0009(14) -0.0002(16) C9 0.054(2) 0.100(3) 0.0414(18) 0.0094(19) 0.0063(16) 0.018(2) C10 0.074(3) 0.123(3) 0.043(2) -0.012(2) 0.0016(19) -0.030(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 2.049(2) . ? Ni N2 2.124(2) . ? Ni Br1 2.5958(4) . ? Ni Br2 2.6052(4) . ? Ni Br2 2.6087(4) 3_565 ? Ni Br1 2.6221(4) 3_665 ? Br1 Ni 2.6221(4) 3_665 ? Br2 Ni 2.6087(4) 3_565 ? N1 C1 1.328(3) . ? N1 C5 1.335(3) . ? N2 C6 1.484(3) . ? N2 C8 1.495(3) . ? C1 C2 1.381(4) . ? C2 C3 1.370(5) . ? C3 C4 1.359(5) . ? C4 C5 1.385(4) . ? C5 C6 1.511(4) . ? C6 C7 1.521(4) . ? C8 C9 1.513(4) . ? C8 C10 1.522(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 N1 Ni N2 80.21(9) . . ? N1 Ni Br1 167.16(7) . . ? N2 Ni Br1 87.86(6) . . ? N1 Ni Br2 98.68(7) . . ? N2 Ni Br2 178.58(6) . . ? Br1 Ni Br2 93.172(13) . . ? N1 Ni Br2 92.62(6) . 3_565 ? N2 Ni Br2 99.36(6) . 3_565 ? Br1 Ni Br2 93.996(13) . 3_565 ? Br2 Ni Br2 81.540(12) . 3_565 ? N1 Ni Br1 89.89(6) . 3_665 ? N2 Ni Br1 90.80(6) . 3_665 ? Br1 Ni Br1 85.524(13) . 3_665 ? Br2 Ni Br1 88.323(12) . 3_665 ? Br2 Ni Br1 169.813(15) 3_565 3_665 ? Ni Br1 Ni 94.476(13) . 3_665 ? Ni Br2 Ni 98.460(12) . 3_565 ? C1 N1 C5 118.4(2) . . ? C1 N1 Ni 125.22(19) . . ? C5 N1 Ni 116.25(18) . . ? C6 N2 C8 113.7(2) . . ? C6 N2 Ni 111.92(17) . . ? C8 N2 Ni 118.54(17) . . ? N1 C1 C2 122.5(3) . . ? C3 C2 C1 118.4(3) . . ? C4 C3 C2 120.0(3) . . ? C3 C4 C5 118.5(3) . . ? N1 C5 C4 122.2(3) . . ? N1 C5 C6 118.3(2) . . ? C4 C5 C6 119.4(3) . . ? N2 C6 C5 109.7(2) . . ? N2 C6 C7 113.5(3) . . ? C5 C6 C7 111.1(3) . . ? N2 C8 C9 113.0(3) . . ? N2 C8 C10 111.0(3) . . ? C9 C8 C10 110.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.388 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.076 # Attachment '- 2d.CIF' data_ic8755 _database_code_depnum_ccdc_archive 'CCDC 864443' #TrackingRef '- 2d.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 Br4 N4 Ni2' _chemical_formula_weight 889.69 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)/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 11.7867(4) _cell_length_b 10.3876(4) _cell_length_c 14.1012(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.0572(8) _cell_angle_gamma 90.00 _cell_volume 1641.45(10) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5364 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 6.042 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3562 _exptl_absorpt_correction_T_max 0.4914 _exptl_absorpt_process_details ? _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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17090 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3775 _reflns_number_gt 2573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0485P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3775 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 -0.06453(4) 0.40926(4) 0.08404(3) 0.03436(13) Uani 1 1 d . . . Br1 Br -0.00972(4) 0.64169(3) 0.05850(3) 0.05132(14) Uani 1 1 d . . . Br2 Br -0.27983(4) 0.43866(5) 0.03932(4) 0.06784(17) Uani 1 1 d . . . N1 N -0.0683(3) 0.2200(2) 0.1245(2) 0.0350(7) Uani 1 1 d . . . N2 N -0.0300(3) 0.4291(3) 0.2378(2) 0.0415(8) Uani 1 1 d . . . H2A H -0.106(4) 0.448(4) 0.230(3) 0.058(14) Uiso 1 1 d . . . C1 C -0.0997(4) 0.1223(3) 0.0589(3) 0.0489(10) Uani 1 1 d . . . H1A H -0.1238 0.1406 -0.0090 0.059 Uiso 1 1 calc R . . C2 C -0.0972(4) -0.0039(4) 0.0892(3) 0.0560(12) Uani 1 1 d . . . H2B H -0.1197 -0.0696 0.0423 0.067 Uiso 1 1 calc R . . C3 C -0.0616(4) -0.0313(3) 0.1879(3) 0.0523(11) Uani 1 1 d . . . H3A H -0.0576 -0.1162 0.2098 0.063 Uiso 1 1 calc R . . C4 C -0.0313(4) 0.0684(4) 0.2556(3) 0.0509(10) Uani 1 1 d . . . H4A H -0.0071 0.0515 0.3237 0.061 Uiso 1 1 calc R . . C5 C -0.0370(3) 0.1925(3) 0.2218(3) 0.0362(8) Uani 1 1 d . . . C6 C -0.0047(4) 0.3054(4) 0.2934(3) 0.0543(11) Uani 1 1 d . . . H6A H 0.0821 0.3018 0.3240 0.065 Uiso 1 1 calc R . . C7 C -0.0564(8) 0.2950(5) 0.3767(4) 0.143(4) Uani 1 1 d . . . H7A H -0.0335 0.3687 0.4195 0.215 Uiso 1 1 calc R . . H7B H -0.0274 0.2182 0.4143 0.215 Uiso 1 1 calc R . . H7C H -0.1419 0.2914 0.3503 0.215 Uiso 1 1 calc R . . C8 C 0.0403(3) 0.5355(3) 0.2921(3) 0.0350(8) Uani 1 1 d . . . C9 C 0.1604(4) 0.5423(4) 0.3011(3) 0.0463(9) Uani 1 1 d . . . C10 C 0.2249(4) 0.6443(5) 0.3533(3) 0.0629(13) Uani 1 1 d . . . H10A H 0.3058 0.6501 0.3604 0.075 Uiso 1 1 calc R . . C11 C 0.1739(5) 0.7368(4) 0.3949(3) 0.0661(14) Uani 1 1 d . . . H11A H 0.2203 0.8030 0.4316 0.079 Uiso 1 1 calc R . . C12 C 0.0551(5) 0.7326(4) 0.3827(3) 0.0585(13) Uani 1 1 d . . . H12A H 0.0203 0.7979 0.4092 0.070 Uiso 1 1 calc R . . C13 C -0.0153(4) 0.6318(4) 0.3311(3) 0.0451(10) Uani 1 1 d . . . C14 C 0.2212(4) 0.4466(5) 0.2515(4) 0.0757(15) Uani 1 1 d . . . H14A H 0.2949 0.4824 0.2480 0.114 Uiso 1 1 calc R . . H14B H 0.1700 0.4283 0.1854 0.114 Uiso 1 1 calc R . . H14C H 0.2372 0.3685 0.2898 0.114 Uiso 1 1 calc R . . C15 C -0.1454(5) 0.6313(5) 0.3176(5) 0.0871(18) Uani 1 1 d . . . H15A H -0.1888 0.6239 0.2479 0.131 Uiso 1 1 calc R . . H15B H -0.1671 0.7100 0.3432 0.131 Uiso 1 1 calc R . . H15C H -0.1644 0.5596 0.3529 0.131 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 0.0470(3) 0.0256(2) 0.0312(3) 0.00362(18) 0.0130(2) -0.00121(19) Br1 0.0901(4) 0.02718(18) 0.0488(3) 0.00042(16) 0.0392(2) -0.00395(18) Br2 0.0464(3) 0.0686(3) 0.0821(4) 0.0316(3) 0.0106(2) 0.0033(2) N1 0.0461(19) 0.0267(14) 0.0344(17) -0.0008(12) 0.0155(14) -0.0002(12) N2 0.055(2) 0.0325(16) 0.0327(18) 0.0008(12) 0.0064(16) -0.0076(15) C1 0.072(3) 0.035(2) 0.039(2) -0.0045(16) 0.017(2) -0.0073(18) C2 0.082(3) 0.0296(19) 0.062(3) -0.0082(18) 0.029(3) -0.008(2) C3 0.069(3) 0.0277(19) 0.060(3) 0.0078(18) 0.020(2) 0.0022(18) C4 0.067(3) 0.038(2) 0.044(2) 0.0118(17) 0.011(2) -0.0024(18) C5 0.043(2) 0.0317(17) 0.033(2) 0.0031(15) 0.0100(16) -0.0042(15) C6 0.082(3) 0.037(2) 0.038(2) 0.0024(17) 0.009(2) -0.011(2) C7 0.337(12) 0.059(3) 0.065(4) -0.003(3) 0.109(6) -0.013(5) C8 0.046(2) 0.0297(17) 0.0294(19) -0.0021(14) 0.0113(16) -0.0053(15) C9 0.046(3) 0.055(2) 0.037(2) -0.0036(18) 0.0124(18) -0.0025(19) C10 0.056(3) 0.075(3) 0.056(3) -0.003(2) 0.015(2) -0.024(2) C11 0.100(4) 0.051(3) 0.042(3) -0.007(2) 0.014(3) -0.029(3) C12 0.102(4) 0.035(2) 0.042(2) -0.0045(18) 0.027(3) 0.002(2) C13 0.057(3) 0.046(2) 0.037(2) 0.0016(17) 0.0222(19) 0.0059(18) C14 0.055(3) 0.096(4) 0.076(4) -0.016(3) 0.021(3) 0.011(3) C15 0.078(4) 0.095(4) 0.100(5) -0.027(3) 0.045(3) 0.014(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 Ni N1 2.051(3) . ? Ni N2 2.089(3) . ? Ni Br2 2.4370(7) . ? Ni Br1 2.4852(6) 3_565 ? Ni Br1 2.5535(5) . ? Br1 Ni 2.4851(6) 3_565 ? N1 C5 1.336(4) . ? N1 C1 1.346(4) . ? N2 C8 1.449(4) . ? N2 C6 1.486(5) . ? C1 C2 1.376(5) . ? C2 C3 1.354(6) . ? C3 C4 1.378(6) . ? C4 C5 1.369(5) . ? C5 C6 1.517(5) . ? C6 C7 1.487(7) . ? C8 C9 1.384(5) . ? C8 C13 1.399(5) . ? C9 C10 1.377(6) . ? C9 C14 1.517(6) . ? C10 C11 1.358(7) . ? C11 C12 1.357(7) . ? C12 C13 1.393(6) . ? C13 C15 1.486(7) . ? 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 79.61(11) . . ? N1 Ni Br2 94.67(9) . . ? N2 Ni Br2 96.23(11) . . ? N1 Ni Br1 93.69(8) . 3_565 ? N2 Ni Br1 148.92(11) . 3_565 ? Br2 Ni Br1 114.64(3) . 3_565 ? N1 Ni Br1 166.81(9) . . ? N2 Ni Br1 94.41(8) . . ? Br2 Ni Br1 97.68(2) . . ? Br1 Ni Br1 85.373(18) 3_565 . ? Ni Br1 Ni 94.627(18) 3_565 . ? C5 N1 C1 118.3(3) . . ? C5 N1 Ni 117.9(2) . . ? C1 N1 Ni 123.8(3) . . ? C8 N2 C6 113.1(3) . . ? C8 N2 Ni 121.2(2) . . ? C6 N2 Ni 113.9(2) . . ? N1 C1 C2 122.0(4) . . ? C3 C2 C1 119.3(4) . . ? C2 C3 C4 119.0(3) . . ? C5 C4 C3 119.5(4) . . ? N1 C5 C4 121.8(3) . . ? N1 C5 C6 116.7(3) . . ? C4 C5 C6 121.4(3) . . ? N2 C6 C7 114.5(4) . . ? N2 C6 C5 110.5(3) . . ? C7 C6 C5 112.9(4) . . ? C9 C8 C13 121.1(3) . . ? C9 C8 N2 119.3(3) . . ? C13 C8 N2 119.5(4) . . ? C10 C9 C8 117.9(4) . . ? C10 C9 C14 119.3(4) . . ? C8 C9 C14 122.7(4) . . ? C11 C10 C9 122.0(5) . . ? C12 C11 C10 120.0(4) . . ? C11 C12 C13 121.0(4) . . ? C12 C13 C8 117.9(4) . . ? C12 C13 C15 119.6(4) . . ? C8 C13 C15 122.5(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.188 _refine_diff_density_min -0.985 _refine_diff_density_rms 0.084 # Attachment '- 3e.cif' data_ic8803 _database_code_depnum_ccdc_archive 'CCDC 864445' #TrackingRef '- 3e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 Br2 N2 Ni' _chemical_formula_weight 500.95 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)/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 10.2488(2) _cell_length_b 14.7285(3) _cell_length_c 13.6969(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.5792(9) _cell_angle_gamma 90.00 _cell_volume 2063.51(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 27.50 _exptl_crystal_description irregular _exptl_crystal_colour 'deep brown' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 4.816 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.606 _exptl_absorpt_correction_T_max 0.872 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14536 _diffrn_reflns_av_R_equivalents 0.0817 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4745 _reflns_number_gt 3030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _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^)+(0.0683P)^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 0.0137(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4745 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Ni1 Ni 0.39717(6) 0.50230(4) 0.38102(5) 0.0271(2) Uani 1 1 d . . . Br1 Br 0.63248(5) 0.52720(4) 0.43785(4) 0.03567(19) Uani 1 1 d . . . Br2 Br 0.40122(6) 0.61467(4) 0.25224(5) 0.0460(2) Uani 1 1 d . . . N1 N 0.2001(4) 0.4790(3) 0.3561(3) 0.0277(9) Uani 1 1 d . . . N2 N 0.4055(4) 0.3636(3) 0.3469(3) 0.0276(9) Uani 1 1 d . . . H2A H 0.3892 0.3381 0.4070 0.033 Uiso 1 1 calc R . . C1 C 0.1381(6) 0.6291(4) 0.4149(5) 0.0421(14) Uani 1 1 d . . . H1A H 0.2331 0.6372 0.4171 0.063 Uiso 1 1 calc R . . H1B H 0.1073 0.6374 0.4806 0.063 Uiso 1 1 calc R . . H1C H 0.0962 0.6741 0.3704 0.063 Uiso 1 1 calc R . . C2 C 0.1037(5) 0.5352(3) 0.3789(4) 0.0301(11) Uani 1 1 d . . . C3 C -0.0269(5) 0.5060(4) 0.3687(4) 0.0361(13) Uani 1 1 d . . . H3A H -0.0952 0.5464 0.3836 0.043 Uiso 1 1 calc R . . C4 C -0.0563(5) 0.4197(4) 0.3373(4) 0.0369(13) Uani 1 1 d . . . H4A H -0.1443 0.3993 0.3317 0.044 Uiso 1 1 calc R . . C5 C 0.0432(5) 0.3634(4) 0.3140(4) 0.0331(12) Uani 1 1 d . . . H5A H 0.0252 0.3031 0.2925 0.040 Uiso 1 1 calc R . . C6 C 0.1712(5) 0.3953(4) 0.3222(4) 0.0293(11) Uani 1 1 d . . . C7 C 0.2834(5) 0.3402(4) 0.2894(4) 0.0352(13) Uani 1 1 d . . . H7A H 0.2645 0.2748 0.2975 0.042 Uiso 1 1 calc R . . H7B H 0.2944 0.3518 0.2192 0.042 Uiso 1 1 calc R . . C8 C 0.5163(5) 0.3090(3) 0.3204(4) 0.0278(11) Uani 1 1 d . A . C9 C 0.5553(6) 0.2341(4) 0.3788(4) 0.0415(14) Uani 1 1 d . . . C10 C 0.6629(6) 0.1839(4) 0.3528(5) 0.0475(16) Uani 1 1 d . A . H10A H 0.6912 0.1340 0.3926 0.057 Uiso 1 1 calc R . . C11 C 0.7289(6) 0.2039(4) 0.2725(5) 0.0452(15) Uani 1 1 d . . . H11A H 0.8034 0.1694 0.2577 0.054 Uiso 1 1 calc R A . C12 C 0.6868(5) 0.2747(4) 0.2128(4) 0.0382(13) Uani 1 1 d . A . H12A H 0.7306 0.2868 0.1551 0.046 Uiso 1 1 calc R . . C13 C 0.5817(5) 0.3289(3) 0.2351(4) 0.0296(11) Uani 1 1 d . . . C14 C 0.4635(18) 0.1878(10) 0.4591(13) 0.042(4) Uani 0.60 1 d P A 1 H14A H 0.3863 0.2280 0.4674 0.050 Uiso 0.60 1 calc PR A 1 C15 C 0.549(4) 0.189(3) 0.552(3) 0.102(14) Uani 0.60 1 d P A 1 H15A H 0.5016 0.1631 0.6049 0.154 Uiso 0.60 1 calc PR A 1 H15B H 0.5735 0.2520 0.5679 0.154 Uiso 0.60 1 calc PR A 1 H15C H 0.6281 0.1534 0.5428 0.154 Uiso 0.60 1 calc PR A 1 C16 C 0.4146(15) 0.0944(9) 0.4275(10) 0.059(4) Uani 0.60 1 d P A 1 H16A H 0.3582 0.0701 0.4766 0.089 Uiso 0.60 1 calc PR A 1 H16B H 0.4893 0.0537 0.4214 0.089 Uiso 0.60 1 calc PR A 1 H16C H 0.3647 0.0990 0.3643 0.089 Uiso 0.60 1 calc PR A 1 C14' C 0.501(3) 0.2209(15) 0.472(2) 0.041(5) Uani 0.40 1 d P A 2 H14B H 0.4662 0.2804 0.4943 0.049 Uiso 0.40 1 calc PR A 2 C15' C 0.586(6) 0.178(3) 0.557(4) 0.072(15) Uani 0.40 1 d P A 2 H15D H 0.6602 0.2181 0.5743 0.109 Uiso 0.40 1 calc PR A 2 H15E H 0.6175 0.1189 0.5370 0.109 Uiso 0.40 1 calc PR A 2 H15F H 0.5330 0.1710 0.6139 0.109 Uiso 0.40 1 calc PR A 2 C16' C 0.386(2) 0.1553(19) 0.4530(14) 0.062(6) Uani 0.40 1 d P A 2 H16D H 0.3230 0.1814 0.4039 0.093 Uiso 0.40 1 calc PR A 2 H16E H 0.3425 0.1454 0.5140 0.093 Uiso 0.40 1 calc PR A 2 H16F H 0.4179 0.0973 0.4292 0.093 Uiso 0.40 1 calc PR A 2 C17 C 0.5423(6) 0.4078(4) 0.1679(4) 0.0378(13) Uani 1 1 d . A . H17A H 0.4702 0.4416 0.1978 0.045 Uiso 1 1 calc R . . C18 C 0.4900(8) 0.3732(5) 0.0676(5) 0.0598(19) Uani 1 1 d . . . H18A H 0.4166 0.3318 0.0758 0.090 Uiso 1 1 calc R A . H18B H 0.5596 0.3409 0.0361 0.090 Uiso 1 1 calc R . . H18C H 0.4603 0.4248 0.0268 0.090 Uiso 1 1 calc R . . C19 C 0.6549(6) 0.4734(4) 0.1577(4) 0.0448(15) Uani 1 1 d . . . H19A H 0.6856 0.4958 0.2224 0.067 Uiso 1 1 calc R A . H19B H 0.6253 0.5246 0.1163 0.067 Uiso 1 1 calc R . . H19C H 0.7266 0.4421 0.1276 0.067 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0174(3) 0.0268(4) 0.0369(4) -0.0044(3) 0.0001(3) 0.0003(3) Br1 0.0179(3) 0.0548(4) 0.0345(3) -0.0097(2) 0.00367(19) -0.0036(2) Br2 0.0322(3) 0.0347(3) 0.0715(5) 0.0179(3) 0.0057(3) 0.0028(2) N1 0.018(2) 0.026(2) 0.038(2) -0.0030(18) 0.0003(17) 0.0005(17) N2 0.018(2) 0.025(2) 0.039(2) -0.0013(19) 0.0030(17) 0.0016(17) C1 0.035(3) 0.034(3) 0.059(4) -0.009(3) 0.012(3) 0.002(3) C2 0.023(3) 0.025(3) 0.043(3) 0.002(2) 0.003(2) 0.006(2) C3 0.021(3) 0.039(3) 0.048(3) 0.001(3) 0.003(2) 0.005(2) C4 0.017(3) 0.048(3) 0.046(3) -0.004(3) -0.001(2) -0.002(2) C5 0.025(3) 0.035(3) 0.039(3) -0.004(2) -0.004(2) -0.004(2) C6 0.021(3) 0.036(3) 0.030(3) -0.003(2) -0.002(2) 0.003(2) C7 0.025(3) 0.035(3) 0.046(3) -0.012(3) -0.001(2) 0.000(2) C8 0.021(2) 0.024(3) 0.039(3) -0.005(2) 0.006(2) 0.002(2) C9 0.047(3) 0.043(3) 0.036(3) 0.011(3) 0.014(3) 0.019(3) C10 0.041(4) 0.045(4) 0.057(4) 0.011(3) 0.006(3) 0.018(3) C11 0.031(3) 0.039(3) 0.068(4) 0.000(3) 0.019(3) 0.005(3) C12 0.028(3) 0.038(3) 0.050(3) -0.003(3) 0.017(2) -0.003(2) C13 0.025(3) 0.024(3) 0.039(3) 0.001(2) 0.001(2) -0.006(2) C14 0.049(11) 0.022(9) 0.056(9) 0.013(7) 0.023(8) -0.001(7) C15 0.11(2) 0.15(3) 0.050(18) 0.00(2) 0.012(15) -0.05(2) C16 0.064(9) 0.058(8) 0.056(8) -0.003(7) 0.009(6) -0.023(7) C14' 0.055(15) 0.026(13) 0.044(12) 0.013(11) 0.024(10) 0.002(10) C15' 0.14(4) 0.035(13) 0.035(16) 0.007(11) -0.02(2) 0.004(17) C16' 0.054(13) 0.093(19) 0.041(11) 0.030(11) 0.010(9) -0.031(14) C17 0.043(3) 0.035(3) 0.035(3) 0.007(2) -0.002(2) -0.009(3) C18 0.078(5) 0.053(4) 0.046(4) 0.011(3) -0.012(3) -0.020(4) C19 0.050(4) 0.039(3) 0.045(3) 0.009(3) 0.006(3) -0.012(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 Ni1 N1 2.056(4) . ? Ni1 N2 2.098(4) . ? Ni1 Br2 2.4210(9) . ? Ni1 Br1 2.5143(8) . ? Ni1 Br1 2.5555(8) 3_666 ? Br1 Ni1 2.5555(8) 3_666 ? N1 C2 1.340(6) . ? N1 C6 1.344(6) . ? N2 C8 1.456(6) . ? N2 C7 1.477(6) . ? C1 C2 1.503(7) . ? C2 C3 1.405(7) . ? C3 C4 1.370(8) . ? C4 C5 1.368(7) . ? C5 C6 1.391(7) . ? C6 C7 1.499(7) . ? C8 C9 1.405(7) . ? C8 C13 1.413(7) . ? C9 C10 1.393(8) . ? C9 C14' 1.44(3) . ? C9 C14 1.640(17) . ? C10 C11 1.358(8) . ? C11 C12 1.378(8) . ? C12 C13 1.390(7) . ? C13 C17 1.522(7) . ? C14 C15 1.50(4) . ? C14 C16 1.518(17) . ? C14' C16' 1.54(3) . ? C14' C15' 1.54(6) . ? C17 C19 1.518(8) . ? C17 C18 1.530(8) . ? 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 81.61(15) . . ? N1 Ni1 Br2 93.11(12) . . ? N2 Ni1 Br2 120.03(12) . . ? N1 Ni1 Br1 171.50(12) . . ? N2 Ni1 Br1 99.16(11) . . ? Br2 Ni1 Br1 93.79(3) . . ? N1 Ni1 Br1 87.59(12) . 3_666 ? N2 Ni1 Br1 93.42(12) . 3_666 ? Br2 Ni1 Br1 146.31(3) . 3_666 ? Br1 Ni1 Br1 83.92(3) . 3_666 ? Ni1 Br1 Ni1 96.08(3) . 3_666 ? C2 N1 C6 119.8(4) . . ? C2 N1 Ni1 126.1(3) . . ? C6 N1 Ni1 113.8(3) . . ? C8 N2 C7 112.7(4) . . ? C8 N2 Ni1 129.6(3) . . ? C7 N2 Ni1 107.5(3) . . ? N1 C2 C3 120.0(5) . . ? N1 C2 C1 118.9(4) . . ? C3 C2 C1 121.1(5) . . ? C4 C3 C2 120.3(5) . . ? C5 C4 C3 119.0(5) . . ? C4 C5 C6 119.3(5) . . ? N1 C6 C5 121.6(5) . . ? N1 C6 C7 116.3(4) . . ? C5 C6 C7 122.0(5) . . ? N2 C7 C6 110.7(4) . . ? C9 C8 C13 120.1(5) . . ? C9 C8 N2 119.3(4) . . ? C13 C8 N2 120.6(4) . . ? C10 C9 C8 118.2(5) . . ? C10 C9 C14' 120.8(11) . . ? C8 C9 C14' 120.0(11) . . ? C10 C9 C14 116.6(7) . . ? C8 C9 C14 123.6(8) . . ? C14' C9 C14 22.8(10) . . ? C11 C10 C9 122.3(6) . . ? C10 C11 C12 119.4(5) . . ? C11 C12 C13 121.4(5) . . ? C12 C13 C8 118.5(5) . . ? C12 C13 C17 119.0(5) . . ? C8 C13 C17 122.5(5) . . ? C15 C14 C16 114.8(19) . . ? C15 C14 C9 103(2) . . ? C16 C14 C9 112.3(12) . . ? C9 C14' C16' 105.8(19) . . ? C9 C14' C15' 120(3) . . ? C16' C14' C15' 105(3) . . ? C19 C17 C13 111.6(5) . . ? C19 C17 C18 110.8(5) . . ? C13 C17 C18 110.7(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.848 _refine_diff_density_min -0.939 _refine_diff_density_rms 0.253 # Attachment '- 4a.cif' data_ic8329 _database_code_depnum_ccdc_archive 'CCDC 864446' #TrackingRef '- 4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H32 Br4 N4 Ni2' _chemical_formula_weight 765.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 8.0121(3) _cell_length_b 8.6141(3) _cell_length_c 10.4721(4) _cell_angle_alpha 76.293(1) _cell_angle_beta 89.199(1) _cell_angle_gamma 71.404(1) _cell_volume 664.02(4) _cell_formula_units_Z 1 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4488 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.914 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 7.450 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3627 _exptl_absorpt_correction_T_max 0.4915 _exptl_absorpt_process_details ? _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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9354 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0240 _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 -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3058 _reflns_number_gt 2412 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0259P)^2^+0.0724P] 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(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3058 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0529 _refine_ls_wR_factor_gt 0.0508 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.45492(4) 0.05344(4) 0.66875(3) 0.02902(9) Uani 1 1 d . . . Br1 Br 0.29322(3) -0.00254(3) 0.47711(2) 0.03422(8) Uani 1 1 d . . . Br2 Br 0.64575(4) 0.08313(5) 0.84052(3) 0.05744(11) Uani 1 1 d . . . N1 N 0.3021(3) 0.2979(2) 0.62151(19) 0.0325(4) Uani 1 1 d . . . N2 N 0.3049(3) -0.0380(3) 0.80839(19) 0.0354(5) Uani 1 1 d . . . H2 H 0.359(4) -0.044(3) 0.886(3) 0.052(8) Uiso 1 1 d . . . C1 C 0.3377(3) 0.3987(3) 0.5123(3) 0.0379(6) Uani 1 1 d . . . H1A H 0.4258 0.3504 0.4612 0.045 Uiso 1 1 calc R . . C2 C 0.2496(4) 0.5694(3) 0.4732(3) 0.0461(7) Uani 1 1 d . . . H2A H 0.2778 0.6354 0.3976 0.055 Uiso 1 1 calc R . . C3 C 0.1193(4) 0.6398(3) 0.5481(3) 0.0482(7) Uani 1 1 d . . . H3A H 0.0584 0.7552 0.5245 0.058 Uiso 1 1 calc R . . C4 C 0.0799(3) 0.5401(3) 0.6569(3) 0.0462(7) Uani 1 1 d . . . H4A H -0.0103 0.5870 0.7071 0.055 Uiso 1 1 calc R . . C5 C 0.1742(3) 0.3664(3) 0.6945(2) 0.0382(6) Uani 1 1 d . . . C6 C 0.1340(4) 0.2558(3) 0.8151(3) 0.0517(7) Uani 1 1 d . . . H6A H 0.0211 0.3169 0.8427 0.062 Uiso 1 1 calc R . . H6B H 0.2226 0.2358 0.8846 0.062 Uiso 1 1 calc R . . C7 C 0.1270(3) 0.0861(3) 0.8028(3) 0.0464(7) Uani 1 1 d . . . H7A H 0.0620 0.0428 0.8735 0.056 Uiso 1 1 calc R . . H7B H 0.0642 0.1009 0.7200 0.056 Uiso 1 1 calc R . . C8 C 0.3066(4) -0.2114(3) 0.8082(3) 0.0489(7) Uani 1 1 d . . . H8A H 0.2575 -0.2076 0.7219 0.059 Uiso 1 1 calc R . . C9 C 0.4954(5) -0.3252(4) 0.8252(3) 0.0723(10) Uani 1 1 d . . . H9A H 0.5614 -0.2797 0.7578 0.108 Uiso 1 1 calc R . . H9B H 0.5001 -0.4357 0.8185 0.108 Uiso 1 1 calc R . . H9C H 0.5453 -0.3328 0.9102 0.108 Uiso 1 1 calc R . . C10 C 0.1970(5) -0.2811(4) 0.9140(3) 0.0651(9) Uani 1 1 d . . . H10A H 0.0771 -0.2067 0.9015 0.098 Uiso 1 1 calc R . . H10B H 0.2452 -0.2892 0.9997 0.098 Uiso 1 1 calc R . . H10C H 0.2001 -0.3912 0.9071 0.098 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 0.02800(17) 0.03258(17) 0.02563(16) -0.00753(13) 0.00369(12) -0.00847(13) Br1 0.02924(14) 0.04297(15) 0.03323(14) -0.01474(11) 0.00692(10) -0.01179(11) Br2 0.04902(18) 0.1037(3) 0.03185(15) -0.01918(15) 0.00206(12) -0.03963(18) N1 0.0318(11) 0.0342(11) 0.0329(11) -0.0117(9) 0.0020(9) -0.0100(9) N2 0.0382(12) 0.0470(13) 0.0240(10) -0.0078(9) 0.0033(9) -0.0185(10) C1 0.0352(14) 0.0372(14) 0.0431(14) -0.0097(12) 0.0033(11) -0.0145(11) C2 0.0428(16) 0.0359(15) 0.0579(18) -0.0019(13) -0.0079(13) -0.0170(13) C3 0.0368(15) 0.0323(14) 0.074(2) -0.0141(14) -0.0116(14) -0.0078(12) C4 0.0354(15) 0.0451(16) 0.0629(19) -0.0294(15) 0.0019(13) -0.0078(13) C5 0.0332(13) 0.0428(15) 0.0427(14) -0.0204(12) 0.0027(11) -0.0108(12) C6 0.0517(18) 0.0537(17) 0.0452(16) -0.0190(14) 0.0176(13) -0.0065(14) C7 0.0361(15) 0.0615(18) 0.0399(15) -0.0058(13) 0.0130(12) -0.0188(14) C8 0.073(2) 0.0474(16) 0.0321(14) -0.0077(12) 0.0072(14) -0.0297(16) C9 0.098(3) 0.0449(18) 0.065(2) -0.0081(16) 0.021(2) -0.0161(19) C10 0.098(3) 0.070(2) 0.0439(17) -0.0052(15) 0.0115(17) -0.057(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 2.0142(19) . ? Ni N2 2.0525(19) . ? Ni Br2 2.4865(4) . ? Ni Br1 2.5029(4) 2_656 ? Ni Br1 2.6208(4) . ? Br1 Ni 2.5029(4) 2_656 ? N1 C5 1.337(3) . ? N1 C1 1.349(3) . ? N2 C7 1.476(3) . ? N2 C8 1.490(3) . ? C1 C2 1.375(4) . ? C2 C3 1.368(4) . ? C3 C4 1.355(4) . ? C4 C5 1.404(3) . ? C5 C6 1.490(4) . ? C6 C7 1.516(4) . ? C8 C9 1.503(4) . ? C8 C10 1.534(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 N1 Ni N2 98.41(8) . . ? N1 Ni Br2 95.39(5) . . ? N2 Ni Br2 91.54(6) . . ? N1 Ni Br1 111.05(6) . 2_656 ? N2 Ni Br1 150.08(6) . 2_656 ? Br2 Ni Br1 90.783(13) . 2_656 ? N1 Ni Br1 90.21(5) . . ? N2 Ni Br1 92.90(6) . . ? Br2 Ni Br1 172.274(15) . . ? Br1 Ni Br1 82.224(11) 2_656 . ? Ni Br1 Ni 97.776(11) 2_656 . ? C5 N1 C1 118.7(2) . . ? C5 N1 Ni 124.02(17) . . ? C1 N1 Ni 117.19(16) . . ? C7 N2 C8 114.5(2) . . ? C7 N2 Ni 111.04(15) . . ? C8 N2 Ni 113.32(15) . . ? N1 C1 C2 122.9(2) . . ? C3 C2 C1 118.4(3) . . ? C4 C3 C2 119.4(2) . . ? C3 C4 C5 120.5(3) . . ? N1 C5 C4 120.0(2) . . ? N1 C5 C6 119.0(2) . . ? C4 C5 C6 121.0(2) . . ? C5 C6 C7 116.5(2) . . ? N2 C7 C6 112.0(2) . . ? N2 C8 C9 108.1(2) . . ? N2 C8 C10 113.4(2) . . ? C9 C8 C10 110.8(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.816 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.063 # Attachment '- 4b.cif' data_ic8678 _database_code_depnum_ccdc_archive 'CCDC 864447' #TrackingRef '- 4b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 Br2 N2 Ni' _chemical_formula_weight 396.80 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 13.9446(5) _cell_length_b 8.1918(3) _cell_length_c 13.5562(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.2726(7) _cell_angle_gamma 90.00 _cell_volume 1470.46(9) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4525 _cell_measurement_theta_min 1.54 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 6.732 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3791 _exptl_absorpt_correction_T_max 0.4915 _exptl_absorpt_process_details ? _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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13160 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3374 _reflns_number_gt 2412 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0751P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3374 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Ni Ni 0.24769(4) 0.04443(6) 0.07640(4) 0.03149(16) Uani 1 1 d . . . Br1 Br 0.11995(4) -0.12714(7) 0.10093(5) 0.05708(19) Uani 1 1 d . . . Br2 Br 0.36880(4) 0.14769(8) 0.22531(4) 0.0634(2) Uani 1 1 d . . . N1 N 0.3239(3) -0.0892(4) 0.0034(3) 0.0335(7) Uani 1 1 d . . . N2 N 0.1603(2) 0.1730(4) -0.0480(3) 0.0297(7) Uani 1 1 d . . . H2B H 0.0960 0.1456 -0.0517 0.036 Uiso 1 1 calc R . . C1 C 0.4172(3) -0.1443(6) 0.0556(4) 0.0437(11) Uani 1 1 d . . . H1A H 0.4450 -0.1177 0.1255 0.052 Uiso 1 1 calc R . . C2 C 0.4722(4) -0.2376(7) 0.0096(4) 0.0562(13) Uani 1 1 d . . . H2A H 0.5357 -0.2758 0.0482 0.067 Uiso 1 1 calc R . . C3 C 0.4331(4) -0.2749(6) -0.0943(4) 0.0521(12) Uani 1 1 d . . . H3A H 0.4698 -0.3371 -0.1273 0.063 Uiso 1 1 calc R . . C4 C 0.3385(4) -0.2180(6) -0.1481(4) 0.0462(11) Uani 1 1 d . . . H4A H 0.3105 -0.2412 -0.2184 0.055 Uiso 1 1 calc R . . C5 C 0.2847(3) -0.1264(5) -0.0979(3) 0.0335(9) Uani 1 1 d . . . C6 C 0.1787(3) -0.0650(5) -0.1544(3) 0.0437(11) Uani 1 1 d . . . H6A H 0.1601 -0.0981 -0.2267 0.052 Uiso 1 1 calc R . . H6B H 0.1315 -0.1156 -0.1242 0.052 Uiso 1 1 calc R . . C7 C 0.1694(4) 0.1179(5) -0.1492(3) 0.0426(10) Uani 1 1 d . . . H7A H 0.2283 0.1685 -0.1597 0.051 Uiso 1 1 calc R . . H7B H 0.1105 0.1537 -0.2048 0.051 Uiso 1 1 calc R . . C8 C 0.1635(3) 0.3567(5) -0.0334(4) 0.0362(10) Uani 1 1 d . . . C9 C 0.2700(4) 0.4198(6) -0.0165(4) 0.0512(12) Uani 1 1 d . . . H9A H 0.3157 0.3669 0.0429 0.077 Uiso 1 1 calc R . . H9B H 0.2716 0.5355 -0.0050 0.077 Uiso 1 1 calc R . . H9C H 0.2898 0.3969 -0.0768 0.077 Uiso 1 1 calc R . . C10 C 0.0893(4) 0.4413(6) -0.1281(4) 0.0520(12) Uani 1 1 d . . . H10A H 0.1099 0.4223 -0.1883 0.078 Uiso 1 1 calc R . . H10B H 0.0888 0.5565 -0.1153 0.078 Uiso 1 1 calc R . . H10C H 0.0227 0.3978 -0.1397 0.078 Uiso 1 1 calc R . . C11 C 0.1310(4) 0.3877(6) 0.0628(4) 0.0470(11) Uani 1 1 d . . . H11A H 0.1847 0.3571 0.1239 0.070 Uiso 1 1 calc R . . H11B H 0.0720 0.3240 0.0583 0.070 Uiso 1 1 calc R . . H11C H 0.1159 0.5015 0.0664 0.070 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 0.0340(3) 0.0348(3) 0.0254(3) 0.0004(2) 0.0090(2) 0.0027(2) Br1 0.0511(3) 0.0561(3) 0.0627(4) 0.0173(2) 0.0159(3) -0.0061(2) Br2 0.0623(4) 0.0786(4) 0.0430(3) -0.0112(3) 0.0074(3) -0.0070(3) N1 0.0331(18) 0.0340(17) 0.0318(18) -0.0016(15) 0.0078(15) 0.0020(14) N2 0.0306(17) 0.0288(16) 0.0326(18) 0.0032(14) 0.0139(14) 0.0024(13) C1 0.037(2) 0.055(3) 0.038(2) -0.002(2) 0.009(2) 0.009(2) C2 0.036(3) 0.066(3) 0.065(4) -0.001(3) 0.014(2) 0.013(2) C3 0.049(3) 0.053(3) 0.064(3) -0.007(3) 0.031(3) 0.006(2) C4 0.055(3) 0.045(3) 0.042(3) -0.008(2) 0.021(2) -0.002(2) C5 0.039(2) 0.0286(19) 0.031(2) -0.0015(16) 0.0082(18) 0.0008(17) C6 0.046(3) 0.046(2) 0.032(2) -0.010(2) 0.0016(19) 0.006(2) C7 0.053(3) 0.044(2) 0.027(2) 0.0057(19) 0.007(2) 0.013(2) C8 0.040(2) 0.0267(19) 0.048(3) 0.0055(18) 0.022(2) 0.0061(17) C9 0.049(3) 0.041(2) 0.071(4) 0.006(2) 0.029(3) -0.006(2) C10 0.057(3) 0.042(3) 0.061(3) 0.018(2) 0.023(3) 0.017(2) C11 0.051(3) 0.044(3) 0.053(3) -0.002(2) 0.025(2) 0.007(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 2.037(3) . ? Ni Br2 2.3462(7) . ? Ni Br1 2.3728(7) . ? N1 C5 1.344(5) . ? N1 C1 1.349(6) . ? N2 C7 1.487(5) . ? N2 C8 1.516(5) . ? C1 C2 1.365(7) . ? C2 C3 1.375(7) . ? C3 C4 1.374(7) . ? C4 C5 1.381(6) . ? C5 C6 1.522(6) . ? C6 C7 1.508(6) . ? C8 C9 1.520(6) . ? C8 C11 1.530(6) . ? C8 C10 1.538(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 98.46(13) . . ? N1 Ni Br2 105.86(10) . . ? N2 Ni Br2 127.46(9) . . ? N1 Ni Br1 106.55(10) . . ? N2 Ni Br1 98.14(9) . . ? Br2 Ni Br1 117.55(3) . . ? C5 N1 C1 118.4(4) . . ? C5 N1 Ni 121.6(3) . . ? C1 N1 Ni 120.1(3) . . ? C7 N2 C8 114.4(3) . . ? C7 N2 Ni 113.9(2) . . ? C8 N2 Ni 114.8(3) . . ? N1 C1 C2 122.4(4) . . ? C1 C2 C3 119.6(5) . . ? C4 C3 C2 118.3(4) . . ? C3 C4 C5 120.1(4) . . ? N1 C5 C4 121.2(4) . . ? N1 C5 C6 117.3(4) . . ? C4 C5 C6 121.5(4) . . ? C7 C6 C5 112.9(4) . . ? N2 C7 C6 112.3(4) . . ? N2 C8 C9 110.2(3) . . ? N2 C8 C11 105.7(3) . . ? C9 C8 C11 110.6(4) . . ? N2 C8 C10 110.7(4) . . ? C9 C8 C10 110.0(4) . . ? C11 C8 C10 109.5(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.861 _refine_diff_density_min -1.059 _refine_diff_density_rms 0.101