# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Sun, Hong Mei' _publ_contact_author_email sunhm@suda.edu.cn _publ_section_title ; Controlled synthesis of nickel(II) dihalides bearing two different or identical N-heterocyclic carbene ligands and the influence of carbene ligands on their structures and catalysis ; loop_ _publ_author_name 'Zhi Hong Liu.' 'Yan Chao Xu.' 'Ling Zhi Xie.' 'Hong Mei Sun.' 'Qi Shen.' ; Yong Zhang ; # Attachment '- shelxl-5.cif' data_shelxl5 _database_code_depnum_ccdc_archive 'CCDC 636607' #TrackingRef '- shelxl-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H32 Br2 N4 Ni' _chemical_formula_sum 'C18 H32 Br2 N4 Ni' _chemical_formula_weight 523.01 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p 21/c' _symmetry_space_group_name_Hall '-p 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.474(4) _cell_length_b 8.907(2) _cell_length_c 16.744(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.525(5) _cell_angle_gamma 90.00 _cell_volume 2301.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 9267 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 4.324 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2464 _exptl_absorpt_correction_T_max 0.6717 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25167 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5273 _reflns_number_gt 4384 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+5.4539P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5273 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.1906 _refine_ls_wR_factor_gt 0.1804 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.41195(4) 0.64360(7) 0.38818(4) 0.0585(2) Uani 1 1 d . . . Br2 Br 1.07235(4) 1.14230(9) 0.43250(4) 0.0592(2) Uani 1 1 d . . . Ni1 Ni 0.5000 0.5000 0.5000 0.0296(2) Uani 1 2 d S . . Ni2 Ni 1.0000 1.0000 0.5000 0.0241(2) Uani 1 2 d S . . N1 N 0.4258(3) 0.2140(4) 0.4180(3) 0.0313(9) Uani 1 1 d . . . N2 N 0.3445(2) 0.3197(5) 0.4765(3) 0.0308(9) Uani 1 1 d . . . N3 N 0.9252(3) 0.8215(5) 0.3449(2) 0.0319(9) Uani 1 1 d . . . N4 N 0.8445(2) 1.0107(5) 0.3445(3) 0.0325(9) Uani 1 1 d . . . C1 C 0.4199(3) 0.3362(5) 0.4636(3) 0.0303(10) Uani 1 1 d . . . C2 C 0.3530(3) 0.1235(6) 0.4015(4) 0.0391(12) Uani 1 1 d . . . H2 H 0.3412 0.0325 0.3699 0.047 Uiso 1 1 calc R . . C3 C 0.3027(3) 0.1905(6) 0.4393(3) 0.0387(12) Uani 1 1 d . . . H3 H 0.2485 0.1552 0.4400 0.046 Uiso 1 1 calc R . . C4 C 0.4987(3) 0.1863(6) 0.3879(3) 0.0372(11) Uani 1 1 d . . . H4 H 0.5530 0.2187 0.4344 0.045 Uiso 1 1 calc R . . C5 C 0.4893(6) 0.2813(11) 0.3114(5) 0.078(2) Uani 1 1 d . . . H5A H 0.4371 0.2510 0.2642 0.117 Uiso 1 1 calc R . . H5B H 0.5402 0.2680 0.2947 0.117 Uiso 1 1 calc R . . H5C H 0.4844 0.3870 0.3252 0.117 Uiso 1 1 calc R . . C6 C 0.5074(6) 0.0226(8) 0.3731(7) 0.075(2) Uani 1 1 d . . . H6A H 0.5022 -0.0349 0.4210 0.113 Uiso 1 1 calc R . . H6B H 0.5641 0.0034 0.3684 0.113 Uiso 1 1 calc R . . H6C H 0.4615 -0.0080 0.3202 0.113 Uiso 1 1 calc R . . C7 C 0.3121(3) 0.4237(7) 0.5274(3) 0.0424(12) Uani 1 1 d . . . H7 H 0.3572 0.5021 0.5528 0.051 Uiso 1 1 calc R . . C8 C 0.2306(4) 0.4998(7) 0.4718(4) 0.0528(15) Uani 1 1 d . . . H8A H 0.2422 0.5546 0.4261 0.079 Uiso 1 1 calc R . . H8B H 0.2109 0.5703 0.5061 0.079 Uiso 1 1 calc R . . H8C H 0.1856 0.4243 0.4467 0.079 Uiso 1 1 calc R . . C9 C 0.2972(6) 0.3378(10) 0.5994(5) 0.080(3) Uani 1 1 d . . . H9A H 0.2481 0.2691 0.5756 0.121 Uiso 1 1 calc R . . H9B H 0.2845 0.4087 0.6382 0.121 Uiso 1 1 calc R . . H9C H 0.3493 0.2802 0.6307 0.121 Uiso 1 1 calc R . . C10 C 0.9187(3) 0.9437(5) 0.3915(3) 0.0301(10) Uani 1 1 d . . . C11 C 0.8538(4) 0.8154(6) 0.2694(3) 0.0420(12) Uani 1 1 d . . . H11 H 0.8425 0.7405 0.2264 0.050 Uiso 1 1 calc R . . C12 C 0.8043(4) 0.9344(7) 0.2686(3) 0.0415(12) Uani 1 1 d . . . H12 H 0.7517 0.9615 0.2246 0.050 Uiso 1 1 calc R . . C13 C 0.9969(4) 0.7141(6) 0.3712(3) 0.0406(12) Uani 1 1 d . . . H13 H 1.0349 0.7389 0.4309 0.049 Uiso 1 1 calc R . . C14 C 1.0496(5) 0.7296(11) 0.3150(5) 0.077(2) Uani 1 1 d . . . H14A H 1.0158 0.6936 0.2576 0.115 Uiso 1 1 calc R . . H14B H 1.1027 0.6700 0.3383 0.115 Uiso 1 1 calc R . . H14C H 1.0647 0.8354 0.3121 0.115 Uiso 1 1 calc R . . C15 C 0.9617(6) 0.5576(8) 0.3709(7) 0.086(3) Uani 1 1 d . . . H15A H 0.9204 0.5576 0.4012 0.129 Uiso 1 1 calc R . . H15B H 1.0095 0.4887 0.3994 0.129 Uiso 1 1 calc R . . H15C H 0.9322 0.5247 0.3119 0.129 Uiso 1 1 calc R . . C16 C 0.8110(3) 1.1486(6) 0.3705(4) 0.0410(12) Uani 1 1 d . . . H16 H 0.8553 1.1868 0.4243 0.049 Uiso 1 1 calc R . . C17 C 0.7951(5) 1.2664(7) 0.3034(5) 0.0636(18) Uani 1 1 d . . . H17A H 0.8463 1.2761 0.2869 0.095 Uiso 1 1 calc R . . H17B H 0.7835 1.3626 0.3258 0.095 Uiso 1 1 calc R . . H17C H 0.7450 1.2380 0.2535 0.095 Uiso 1 1 calc R . . C18 C 0.7298(5) 1.1140(9) 0.3874(7) 0.078(2) Uani 1 1 d . . . H18A H 0.6886 1.0635 0.3377 0.117 Uiso 1 1 calc R . . H18B H 0.7041 1.2076 0.3983 0.117 Uiso 1 1 calc R . . H18C H 0.7433 1.0484 0.4374 0.117 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0490(4) 0.0461(4) 0.0582(4) 0.0116(3) -0.0088(3) -0.0095(3) Br2 0.0462(4) 0.0799(5) 0.0491(4) 0.0074(3) 0.0138(3) -0.0220(3) Ni1 0.0225(4) 0.0255(4) 0.0327(5) -0.0027(3) -0.0005(3) -0.0040(3) Ni2 0.0169(4) 0.0312(4) 0.0217(4) -0.0048(3) 0.0035(3) -0.0028(3) N1 0.0260(19) 0.030(2) 0.034(2) -0.0075(17) 0.0056(16) -0.0083(16) N2 0.0207(19) 0.033(2) 0.033(2) -0.0054(16) 0.0019(16) -0.0033(15) N3 0.029(2) 0.034(2) 0.0251(19) -0.0076(16) 0.0000(16) 0.0042(16) N4 0.0195(18) 0.044(2) 0.0269(19) -0.0058(17) -0.0002(15) 0.0033(16) C1 0.026(2) 0.027(2) 0.029(2) -0.0010(18) -0.0009(18) 0.0031(17) C2 0.031(3) 0.038(3) 0.046(3) -0.010(2) 0.010(2) -0.013(2) C3 0.030(3) 0.038(3) 0.045(3) -0.002(2) 0.009(2) -0.011(2) C4 0.033(3) 0.039(3) 0.041(3) -0.006(2) 0.014(2) -0.006(2) C5 0.085(6) 0.103(6) 0.060(4) 0.017(4) 0.042(4) 0.022(5) C6 0.074(5) 0.047(4) 0.128(7) -0.019(4) 0.063(5) -0.004(3) C7 0.031(3) 0.050(3) 0.040(3) -0.013(2) 0.004(2) 0.006(2) C8 0.044(3) 0.053(4) 0.057(4) -0.002(3) 0.013(3) 0.012(3) C9 0.103(7) 0.096(6) 0.048(4) 0.011(4) 0.035(4) 0.042(5) C10 0.024(2) 0.032(2) 0.032(2) -0.0044(19) 0.0078(19) -0.0050(18) C11 0.038(3) 0.042(3) 0.031(3) -0.014(2) -0.007(2) -0.002(2) C12 0.032(3) 0.050(3) 0.032(3) -0.006(2) -0.001(2) -0.001(2) C13 0.041(3) 0.038(3) 0.034(3) -0.004(2) 0.002(2) 0.013(2) C14 0.071(5) 0.107(6) 0.056(4) 0.015(4) 0.027(4) 0.048(5) C15 0.073(5) 0.038(4) 0.127(8) 0.006(4) 0.010(5) 0.010(4) C16 0.029(3) 0.050(3) 0.042(3) -0.009(2) 0.010(2) 0.005(2) C17 0.081(5) 0.037(3) 0.075(5) -0.005(3) 0.030(4) -0.001(3) C18 0.069(5) 0.064(5) 0.124(7) 0.001(5) 0.064(5) 0.012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Ni1 2.3111(7) . ? Br2 Ni2 2.2911(7) . ? Ni1 C1 1.918(5) 3_666 ? Ni1 C1 1.918(5) . ? Ni1 Br1 2.3111(7) 3_666 ? Ni2 C10 1.908(5) 3_776 ? Ni2 C10 1.908(5) . ? Ni2 Br2 2.2911(7) 3_776 ? N1 C1 1.353(6) . ? N1 C2 1.390(6) . ? N1 C4 1.476(7) . ? N2 C1 1.341(7) . ? N2 C3 1.373(6) . ? N2 C7 1.480(7) . ? N3 C10 1.365(6) . ? N3 C11 1.394(6) . ? N3 C13 1.463(6) . ? N4 C10 1.341(6) . ? N4 C12 1.389(6) . ? N4 C16 1.473(7) . ? C2 C3 1.346(8) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C6 1.494(8) . ? C4 C5 1.497(9) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.501(8) . ? C7 C9 1.517(10) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C11 C12 1.335(8) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.494(9) . ? C13 C15 1.510(10) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.492(9) . ? C16 C18 1.493(9) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 C1 180.0 3_666 . ? C1 Ni1 Br1 89.82(14) 3_666 3_666 ? C1 Ni1 Br1 90.18(14) . 3_666 ? C1 Ni1 Br1 90.18(14) 3_666 . ? C1 Ni1 Br1 89.82(14) . . ? Br1 Ni1 Br1 180.0 3_666 . ? C10 Ni2 C10 180.000(1) 3_776 . ? C10 Ni2 Br2 90.67(14) 3_776 . ? C10 Ni2 Br2 89.33(14) . . ? C10 Ni2 Br2 89.33(14) 3_776 3_776 ? C10 Ni2 Br2 90.67(14) . 3_776 ? Br2 Ni2 Br2 180.0 . 3_776 ? C1 N1 C2 110.5(4) . . ? C1 N1 C4 123.7(4) . . ? C2 N1 C4 125.7(4) . . ? C1 N2 C3 111.4(4) . . ? C1 N2 C7 124.5(4) . . ? C3 N2 C7 124.1(4) . . ? C10 N3 C11 109.8(4) . . ? C10 N3 C13 124.4(4) . . ? C11 N3 C13 125.7(4) . . ? C10 N4 C12 111.3(4) . . ? C10 N4 C16 123.9(4) . . ? C12 N4 C16 124.8(4) . . ? N2 C1 N1 104.9(4) . . ? N2 C1 Ni1 127.2(4) . . ? N1 C1 Ni1 127.8(4) . . ? C3 C2 N1 106.3(4) . . ? C3 C2 H2 126.9 . . ? N1 C2 H2 126.9 . . ? C2 C3 N2 106.9(4) . . ? C2 C3 H3 126.5 . . ? N2 C3 H3 126.5 . . ? N1 C4 C6 110.9(5) . . ? N1 C4 C5 110.1(5) . . ? C6 C4 C5 113.4(6) . . ? N1 C4 H4 107.4 . . ? C6 C4 H4 107.4 . . ? C5 C4 H4 107.4 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 110.5(5) . . ? N2 C7 C9 109.5(5) . . ? C8 C7 C9 111.3(6) . . ? N2 C7 H7 108.5 . . ? C8 C7 H7 108.5 . . ? C9 C7 H7 108.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N4 C10 N3 105.0(4) . . ? N4 C10 Ni2 129.2(4) . . ? N3 C10 Ni2 125.8(4) . . ? C12 C11 N3 107.2(4) . . ? C12 C11 H11 126.4 . . ? N3 C11 H11 126.4 . . ? C11 C12 N4 106.7(4) . . ? C11 C12 H12 126.7 . . ? N4 C12 H12 126.7 . . ? N3 C13 C14 109.6(5) . . ? N3 C13 C15 109.5(5) . . ? C14 C13 C15 113.0(7) . . ? N3 C13 H13 108.2 . . ? C14 C13 H13 108.2 . . ? C15 C13 H13 108.2 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N4 C16 C17 110.4(5) . . ? N4 C16 C18 109.7(5) . . ? C17 C16 C18 110.8(6) . . ? N4 C16 H16 108.6 . . ? C17 C16 H16 108.6 . . ? C18 C16 H16 108.6 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N2 C1 N1 -0.6(5) . . . . ? C7 N2 C1 N1 177.0(4) . . . . ? C3 N2 C1 Ni1 178.2(4) . . . . ? C7 N2 C1 Ni1 -4.2(7) . . . . ? C2 N1 C1 N2 1.1(5) . . . . ? C4 N1 C1 N2 179.0(4) . . . . ? C2 N1 C1 Ni1 -177.7(4) . . . . ? C4 N1 C1 Ni1 0.2(7) . . . . ? C1 Ni1 C1 N2 171(100) 3_666 . . . ? Br1 Ni1 C1 N2 101.6(4) 3_666 . . . ? Br1 Ni1 C1 N2 -78.4(4) . . . . ? C1 Ni1 C1 N1 -11(100) 3_666 . . . ? Br1 Ni1 C1 N1 -79.9(4) 3_666 . . . ? Br1 Ni1 C1 N1 100.1(4) . . . . ? C1 N1 C2 C3 -1.2(6) . . . . ? C4 N1 C2 C3 -179.1(5) . . . . ? N1 C2 C3 N2 0.8(6) . . . . ? C1 N2 C3 C2 -0.1(6) . . . . ? C7 N2 C3 C2 -177.7(5) . . . . ? C1 N1 C4 C6 156.2(6) . . . . ? C2 N1 C4 C6 -26.2(8) . . . . ? C1 N1 C4 C5 -77.5(7) . . . . ? C2 N1 C4 C5 100.1(7) . . . . ? C1 N2 C7 C8 115.2(6) . . . . ? C3 N2 C7 C8 -67.5(7) . . . . ? C1 N2 C7 C9 -121.9(6) . . . . ? C3 N2 C7 C9 55.3(7) . . . . ? C12 N4 C10 N3 -0.7(6) . . . . ? C16 N4 C10 N3 179.9(5) . . . . ? C12 N4 C10 Ni2 179.6(4) . . . . ? C16 N4 C10 Ni2 0.2(7) . . . . ? C11 N3 C10 N4 -0.2(6) . . . . ? C13 N3 C10 N4 179.8(5) . . . . ? C11 N3 C10 Ni2 179.5(4) . . . . ? C13 N3 C10 Ni2 -0.5(7) . . . . ? C10 Ni2 C10 N4 38(67) 3_776 . . . ? Br2 Ni2 C10 N4 -89.8(4) . . . . ? Br2 Ni2 C10 N4 90.2(4) 3_776 . . . ? C10 Ni2 C10 N3 -141(67) 3_776 . . . ? Br2 Ni2 C10 N3 90.5(4) . . . . ? Br2 Ni2 C10 N3 -89.5(4) 3_776 . . . ? C10 N3 C11 C12 1.0(7) . . . . ? C13 N3 C11 C12 -178.9(5) . . . . ? N3 C11 C12 N4 -1.4(7) . . . . ? C10 N4 C12 C11 1.4(6) . . . . ? C16 N4 C12 C11 -179.2(5) . . . . ? C10 N3 C13 C14 -110.8(6) . . . . ? C11 N3 C13 C14 69.1(8) . . . . ? C10 N3 C13 C15 124.7(7) . . . . ? C11 N3 C13 C15 -55.3(8) . . . . ? C10 N4 C16 C17 124.7(6) . . . . ? C12 N4 C16 C17 -54.6(7) . . . . ? C10 N4 C16 C18 -112.8(6) . . . . ? C12 N4 C16 C18 67.9(8) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.738 _refine_diff_density_min -1.713 _refine_diff_density_rms 0.136 # Attachment '- shelxl-4.cif' data_shelxl4 _database_code_depnum_ccdc_archive 'CCDC 636608' #TrackingRef '- shelxl-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H32 Cl2 N4 Ni' _chemical_formula_sum 'C18 H32 Cl2 N4 Ni' _chemical_formula_weight 434.09 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.280(4) _cell_length_b 8.7682(16) _cell_length_c 16.734(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.472(4) _cell_angle_gamma 90.00 _cell_volume 2222.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 8015 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour orange-red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6323 _exptl_absorpt_correction_T_max 0.8152 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24040 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5082 _reflns_number_gt 4436 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+2.9022P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5082 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.5000 0.0000 0.02574(13) Uani 1 2 d S . . Ni2 Ni 1.0000 0.5000 0.5000 0.03203(14) Uani 1 2 d S . . Cl1 Cl 0.42761(6) 0.63438(13) 0.06213(5) 0.0605(3) Uani 1 1 d . . . Cl2 Cl 0.90857(5) 0.63938(9) 0.39720(6) 0.0521(2) Uani 1 1 d . . . N1 N 0.65902(15) 0.5145(3) 0.15896(15) 0.0356(6) Uani 1 1 d . . . N2 N 0.57843(15) 0.3213(3) 0.15755(15) 0.0352(6) Uani 1 1 d . . . N3 N 0.84300(15) 0.3139(3) 0.47869(15) 0.0352(5) Uani 1 1 d . . . N4 N 0.92477(15) 0.2050(3) 0.42059(14) 0.0314(5) Uani 1 1 d . . . C1 C 0.58334(16) 0.4435(3) 0.11080(17) 0.0293(6) Uani 1 1 d . . . C2 C 0.7013(2) 0.4374(4) 0.23497(19) 0.0426(7) Uani 1 1 d . . . H2 H 0.7555 0.4648 0.2790 0.051 Uiso 1 1 calc R . . C3 C 0.6511(2) 0.3168(4) 0.23427(19) 0.0449(8) Uani 1 1 d . . . H3 H 0.6627 0.2419 0.2780 0.054 Uiso 1 1 calc R . . C4 C 0.6914(2) 0.6554(4) 0.1328(2) 0.0430(7) Uani 1 1 d . . . H4 H 0.6433 0.6984 0.0815 0.052 Uiso 1 1 calc R . . C5 C 0.7155(3) 0.7713(4) 0.2038(3) 0.0722(12) Uani 1 1 d . . . H5A H 0.6648 0.7888 0.2209 0.108 Uiso 1 1 calc R . . H5B H 0.7321 0.8672 0.1836 0.108 Uiso 1 1 calc R . . H5C H 0.7654 0.7334 0.2531 0.108 Uiso 1 1 calc R . . C6 C 0.7692(4) 0.6195(6) 0.1086(5) 0.112(2) Uani 1 1 d . . . H6A H 0.8135 0.5639 0.1556 0.168 Uiso 1 1 calc R . . H6B H 0.7950 0.7146 0.0977 0.168 Uiso 1 1 calc R . . H6C H 0.7501 0.5564 0.0566 0.168 Uiso 1 1 calc R . . C7 C 0.5050(2) 0.2107(4) 0.1312(2) 0.0416(7) Uani 1 1 d . . . H7 H 0.4642 0.2393 0.0721 0.050 Uiso 1 1 calc R . . C8 C 0.4541(3) 0.2233(7) 0.1900(3) 0.0961(19) Uani 1 1 d . . . H8A H 0.4931 0.1992 0.2489 0.144 Uiso 1 1 calc R . . H8B H 0.4046 0.1515 0.1716 0.144 Uiso 1 1 calc R . . H8C H 0.4316 0.3275 0.1879 0.144 Uiso 1 1 calc R . . C9 C 0.5389(4) 0.0538(5) 0.1265(4) 0.110(2) Uani 1 1 d . . . H9A H 0.5658 0.0514 0.0828 0.164 Uiso 1 1 calc R . . H9B H 0.4899 -0.0191 0.1111 0.164 Uiso 1 1 calc R . . H9C H 0.5832 0.0263 0.1824 0.164 Uiso 1 1 calc R . . C10 C 0.91932(17) 0.3318(3) 0.46509(17) 0.0318(6) Uani 1 1 d . . . C11 C 0.80132(19) 0.1791(4) 0.44312(19) 0.0388(7) Uani 1 1 d . . . H11 H 0.7470 0.1420 0.4444 0.047 Uiso 1 1 calc R . . C12 C 0.8518(2) 0.1117(4) 0.4069(2) 0.0392(7) Uani 1 1 d . . . H12 H 0.8403 0.0172 0.3771 0.047 Uiso 1 1 calc R . . C13 C 0.8107(2) 0.4213(4) 0.5285(2) 0.0461(8) Uani 1 1 d . . . H13 H 0.8553 0.5042 0.5513 0.055 Uiso 1 1 calc R . . C14 C 0.7999(4) 0.3386(6) 0.6035(3) 0.100(2) Uani 1 1 d . . . H14A H 0.7517 0.2646 0.5820 0.150 Uiso 1 1 calc R . . H14B H 0.7863 0.4125 0.6408 0.150 Uiso 1 1 calc R . . H14C H 0.8549 0.2852 0.6362 0.150 Uiso 1 1 calc R . . C15 C 0.7247(2) 0.4918(5) 0.4722(3) 0.0589(10) Uani 1 1 d . . . H15A H 0.7337 0.5498 0.4260 0.088 Uiso 1 1 calc R . . H15B H 0.7034 0.5604 0.5067 0.088 Uiso 1 1 calc R . . H15C H 0.6810 0.4113 0.4474 0.088 Uiso 1 1 calc R . . C16 C 0.99801(19) 0.1770(3) 0.39011(19) 0.0360(6) Uani 1 1 d . . . H16 H 1.0546 0.2009 0.4383 0.043 Uiso 1 1 calc R . . C17 C 1.0003(3) 0.0115(4) 0.3663(3) 0.0570(10) Uani 1 1 d . . . H17A H 1.0020 -0.0530 0.4147 0.086 Uiso 1 1 calc R . . H17B H 1.0530 -0.0075 0.3526 0.086 Uiso 1 1 calc R . . H17C H 0.9474 -0.0125 0.3162 0.086 Uiso 1 1 calc R . . C18 C 0.9896(3) 0.2843(5) 0.3162(2) 0.0613(10) Uani 1 1 d . . . H18A H 0.9330 0.2665 0.2692 0.092 Uiso 1 1 calc R . . H18B H 1.0380 0.2654 0.2959 0.092 Uiso 1 1 calc R . . H18C H 0.9923 0.3901 0.3359 0.092 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 0.0182(2) 0.0347(3) 0.0216(2) 0.0051(2) 0.00409(17) 0.0030(2) Ni2 0.0245(2) 0.0243(2) 0.0358(3) -0.0023(2) -0.0026(2) -0.0027(2) Cl1 0.0469(5) 0.0914(7) 0.0397(4) -0.0080(5) 0.0119(4) 0.0314(5) Cl2 0.0411(4) 0.0342(4) 0.0549(5) 0.0083(4) -0.0135(3) -0.0051(3) N1 0.0223(11) 0.0487(15) 0.0284(11) 0.0074(11) 0.0007(9) -0.0032(10) N2 0.0306(12) 0.0391(13) 0.0264(11) 0.0085(10) -0.0009(10) -0.0016(10) N3 0.0264(12) 0.0379(13) 0.0353(13) -0.0049(11) 0.0040(10) -0.0029(10) N4 0.0293(12) 0.0281(12) 0.0317(12) -0.0022(10) 0.0053(10) -0.0070(10) C1 0.0203(12) 0.0388(15) 0.0257(13) 0.0044(12) 0.0048(10) 0.0034(11) C2 0.0302(15) 0.0535(19) 0.0308(15) 0.0073(14) -0.0044(12) -0.0016(14) C3 0.0410(17) 0.0502(19) 0.0288(15) 0.0133(14) -0.0047(13) -0.0014(15) C4 0.0304(15) 0.0521(19) 0.0432(17) 0.0094(15) 0.0095(13) -0.0094(14) C5 0.104(3) 0.039(2) 0.067(3) 0.0066(19) 0.025(2) -0.001(2) C6 0.128(5) 0.064(3) 0.207(7) -0.018(4) 0.136(5) -0.023(3) C7 0.0386(16) 0.0428(17) 0.0344(15) 0.0085(13) 0.0027(13) -0.0091(14) C8 0.088(3) 0.144(5) 0.064(3) -0.028(3) 0.037(3) -0.074(4) C9 0.084(4) 0.042(2) 0.166(6) -0.014(3) 0.002(4) -0.010(2) C10 0.0269(13) 0.0282(14) 0.0306(14) -0.0012(11) -0.0008(11) -0.0010(11) C11 0.0324(15) 0.0403(16) 0.0384(16) -0.0038(13) 0.0067(13) -0.0120(13) C12 0.0395(16) 0.0351(16) 0.0379(16) -0.0061(13) 0.0081(13) -0.0135(13) C13 0.0342(16) 0.0495(19) 0.0459(18) -0.0131(16) 0.0043(14) 0.0079(14) C14 0.155(5) 0.104(4) 0.049(2) 0.014(3) 0.046(3) 0.067(4) C15 0.047(2) 0.066(2) 0.058(2) -0.0033(19) 0.0115(17) 0.0169(18) C16 0.0353(15) 0.0364(15) 0.0365(15) -0.0033(13) 0.0134(12) -0.0065(12) C17 0.061(2) 0.0425(19) 0.077(3) -0.0129(19) 0.037(2) -0.0033(17) C18 0.076(3) 0.064(2) 0.052(2) 0.0117(19) 0.033(2) 0.005(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 Ni1 C1 1.919(3) 3_665 ? Ni1 C1 1.919(3) . ? Ni1 Cl1 2.1806(9) . ? Ni1 Cl1 2.1806(9) 3_665 ? Ni2 C10 1.918(3) . ? Ni2 C10 1.918(3) 3_766 ? Ni2 Cl2 2.1895(8) . ? Ni2 Cl2 2.1895(8) 3_766 ? N1 C1 1.352(3) . ? N1 C2 1.381(4) . ? N1 C4 1.471(4) . ? N2 C1 1.346(4) . ? N2 C3 1.391(3) . ? N2 C7 1.476(4) . ? N3 C10 1.352(4) . ? N3 C11 1.384(4) . ? N3 C13 1.476(4) . ? N4 C10 1.359(4) . ? N4 C12 1.390(4) . ? N4 C16 1.479(4) . ? C2 C3 1.335(5) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C6 1.498(5) . ? C4 C5 1.502(5) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C9 1.495(6) . ? C7 C8 1.505(5) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C11 C12 1.326(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C15 1.505(5) . ? C13 C14 1.514(6) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.509(4) . ? C16 C18 1.519(5) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 C1 180.0(2) 3_665 . ? C1 Ni1 Cl1 90.38(9) 3_665 . ? C1 Ni1 Cl1 89.62(9) . . ? C1 Ni1 Cl1 89.62(9) 3_665 3_665 ? C1 Ni1 Cl1 90.38(9) . 3_665 ? Cl1 Ni1 Cl1 180.00(4) . 3_665 ? C10 Ni2 C10 180.0 . 3_766 ? C10 Ni2 Cl2 89.83(8) . . ? C10 Ni2 Cl2 90.17(8) 3_766 . ? C10 Ni2 Cl2 90.17(8) . 3_766 ? C10 Ni2 Cl2 89.83(8) 3_766 3_766 ? Cl2 Ni2 Cl2 180.00(4) . 3_766 ? C1 N1 C2 111.2(2) . . ? C1 N1 C4 123.8(2) . . ? C2 N1 C4 124.9(2) . . ? C1 N2 C3 110.3(2) . . ? C1 N2 C7 124.3(2) . . ? C3 N2 C7 125.4(2) . . ? C10 N3 C11 111.3(2) . . ? C10 N3 C13 124.1(3) . . ? C11 N3 C13 124.6(3) . . ? C10 N4 C12 110.4(2) . . ? C10 N4 C16 123.2(2) . . ? C12 N4 C16 126.4(2) . . ? N2 C1 N1 104.8(2) . . ? N2 C1 Ni1 126.6(2) . . ? N1 C1 Ni1 128.7(2) . . ? C3 C2 N1 106.4(3) . . ? C3 C2 H2 126.8 . . ? N1 C2 H2 126.8 . . ? C2 C3 N2 107.3(3) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? N1 C4 C6 109.5(3) . . ? N1 C4 C5 110.6(3) . . ? C6 C4 C5 110.7(4) . . ? N1 C4 H4 108.7 . . ? C6 C4 H4 108.7 . . ? C5 C4 H4 108.7 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C9 110.2(3) . . ? N2 C7 C8 109.6(3) . . ? C9 C7 C8 113.8(4) . . ? N2 C7 H7 107.7 . . ? C9 C7 H7 107.7 . . ? C8 C7 H7 107.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 N4 104.2(2) . . ? N3 C10 Ni2 127.4(2) . . ? N4 C10 Ni2 128.4(2) . . ? C12 C11 N3 106.8(3) . . ? C12 C11 H11 126.6 . . ? N3 C11 H11 126.6 . . ? C11 C12 N4 107.3(3) . . ? C11 C12 H12 126.3 . . ? N4 C12 H12 126.3 . . ? N3 C13 C15 110.6(3) . . ? N3 C13 C14 109.6(3) . . ? C15 C13 C14 110.6(3) . . ? N3 C13 H13 108.7 . . ? C15 C13 H13 108.7 . . ? C14 C13 H13 108.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N4 C16 C17 110.6(3) . . ? N4 C16 C18 109.5(3) . . ? C17 C16 C18 112.6(3) . . ? N4 C16 H16 108.0 . . ? C17 C16 H16 108.0 . . ? C18 C16 H16 108.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N2 C1 N1 -0.1(3) . . . . ? C7 N2 C1 N1 178.6(3) . . . . ? C3 N2 C1 Ni1 179.6(2) . . . . ? C7 N2 C1 Ni1 -1.7(4) . . . . ? C2 N1 C1 N2 0.2(3) . . . . ? C4 N1 C1 N2 -179.9(3) . . . . ? C2 N1 C1 Ni1 -179.5(2) . . . . ? C4 N1 C1 Ni1 0.3(4) . . . . ? C1 Ni1 C1 N2 146(50) 3_665 . . . ? Cl1 Ni1 C1 N2 90.0(2) . . . . ? Cl1 Ni1 C1 N2 -90.0(2) 3_665 . . . ? C1 Ni1 C1 N1 -34(51) 3_665 . . . ? Cl1 Ni1 C1 N1 -90.3(3) . . . . ? Cl1 Ni1 C1 N1 89.7(3) 3_665 . . . ? C1 N1 C2 C3 -0.2(4) . . . . ? C4 N1 C2 C3 180.0(3) . . . . ? N1 C2 C3 N2 0.1(4) . . . . ? C1 N2 C3 C2 0.0(4) . . . . ? C7 N2 C3 C2 -178.7(3) . . . . ? C1 N1 C4 C6 -107.3(4) . . . . ? C2 N1 C4 C6 72.6(5) . . . . ? C1 N1 C4 C5 130.5(3) . . . . ? C2 N1 C4 C5 -49.7(4) . . . . ? C1 N2 C7 C9 121.5(4) . . . . ? C3 N2 C7 C9 -60.0(5) . . . . ? C1 N2 C7 C8 -112.4(4) . . . . ? C3 N2 C7 C8 66.1(5) . . . . ? C11 N3 C10 N4 -0.3(3) . . . . ? C13 N3 C10 N4 177.1(3) . . . . ? C11 N3 C10 Ni2 179.1(2) . . . . ? C13 N3 C10 Ni2 -3.5(4) . . . . ? C12 N4 C10 N3 0.4(3) . . . . ? C16 N4 C10 N3 178.8(2) . . . . ? C12 N4 C10 Ni2 -178.9(2) . . . . ? C16 N4 C10 Ni2 -0.5(4) . . . . ? C10 Ni2 C10 N3 -71(100) 3_766 . . . ? Cl2 Ni2 C10 N3 -75.1(2) . . . . ? Cl2 Ni2 C10 N3 104.9(2) 3_766 . . . ? C10 Ni2 C10 N4 108(100) 3_766 . . . ? Cl2 Ni2 C10 N4 104.0(2) . . . . ? Cl2 Ni2 C10 N4 -76.0(2) 3_766 . . . ? C10 N3 C11 C12 0.0(3) . . . . ? C13 N3 C11 C12 -177.4(3) . . . . ? N3 C11 C12 N4 0.2(3) . . . . ? C10 N4 C12 C11 -0.4(3) . . . . ? C16 N4 C12 C11 -178.8(3) . . . . ? C10 N3 C13 C15 117.0(3) . . . . ? C11 N3 C13 C15 -65.9(4) . . . . ? C10 N3 C13 C14 -120.8(4) . . . . ? C11 N3 C13 C14 56.3(4) . . . . ? C10 N4 C16 C17 163.7(3) . . . . ? C12 N4 C16 C17 -18.2(4) . . . . ? C10 N4 C16 C18 -71.7(3) . . . . ? C12 N4 C16 C18 106.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.660 _refine_diff_density_min -0.656 _refine_diff_density_rms 0.057 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 805189' #TrackingRef '- shelxl-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H52 Cl2 N4 Ni' _chemical_formula_sum 'C36 H52 Cl2 N4 Ni' _chemical_formula_weight 670.43 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 12.5520(11) _cell_length_b 13.6298(12) _cell_length_c 21.938(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.117(2) _cell_angle_gamma 90.00 _cell_volume 3655.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 11768 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.706 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.618 _exptl_absorpt_correction_T_max 0.759 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35003 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.35 _reflns_number_total 6688 _reflns_number_gt 6048 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+2.6280P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6688 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.61373(2) 0.36363(2) 0.856257(13) 0.02185(9) Uani 1 1 d . . . Cl1 Cl 0.61047(5) 0.29919(4) 0.94692(3) 0.03608(15) Uani 1 1 d . . . Cl2 Cl 0.63929(5) 0.43305(4) 0.77081(3) 0.03090(14) Uani 1 1 d . . . N1 N 0.68713(14) 0.17222(13) 0.81232(8) 0.0211(4) Uani 1 1 d . . . N2 N 0.51986(14) 0.20539(12) 0.77082(8) 0.0205(4) Uani 1 1 d . . . N3 N 0.51048(16) 0.53518(13) 0.89681(9) 0.0285(4) Uani 1 1 d . . . N4 N 0.68412(16) 0.55562(14) 0.91461(9) 0.0331(5) Uani 1 1 d . . . C1 C 0.60724(17) 0.23924(15) 0.81418(9) 0.0199(4) Uani 1 1 d . . . C2 C 0.65053(18) 0.10015(16) 0.76791(10) 0.0259(5) Uani 1 1 d . . . H2 H 0.6917 0.0466 0.7577 0.031 Uiso 1 1 calc R . . C3 C 0.54565(18) 0.12088(16) 0.74220(10) 0.0259(5) Uani 1 1 d . . . H3 H 0.4980 0.0845 0.7103 0.031 Uiso 1 1 calc R . . C4 C 0.78981(17) 0.16473(16) 0.85832(10) 0.0233(5) Uani 1 1 d . . . C5 C 0.88120(18) 0.21638(17) 0.84891(11) 0.0279(5) Uani 1 1 d . . . C6 C 0.97744(19) 0.20617(19) 0.89443(12) 0.0373(6) Uani 1 1 d . . . H6 H 1.0408 0.2412 0.8901 0.045 Uiso 1 1 calc R . . C7 C 0.9830(2) 0.1464(2) 0.94560(12) 0.0403(6) Uani 1 1 d . . . H7 H 1.0496 0.1413 0.9763 0.048 Uiso 1 1 calc R . . C8 C 0.8928(2) 0.09407(19) 0.95284(11) 0.0360(6) Uani 1 1 d . . . H8 H 0.8982 0.0523 0.9881 0.043 Uiso 1 1 calc R . . C9 C 0.79387(19) 0.10182(17) 0.90897(10) 0.0279(5) Uani 1 1 d . . . C10 C 0.87762(19) 0.27410(18) 0.78941(12) 0.0333(6) Uani 1 1 d . . . H10 H 0.7997 0.2926 0.7714 0.040 Uiso 1 1 calc R . . C11 C 0.9446(2) 0.36797(18) 0.80039(14) 0.0423(7) Uani 1 1 d . . . H11A H 0.9192 0.4090 0.8309 0.063 Uiso 1 1 calc R . . H11B H 0.9360 0.4038 0.7608 0.063 Uiso 1 1 calc R . . H11C H 1.0220 0.3517 0.8165 0.063 Uiso 1 1 calc R . . C12 C 0.9164(2) 0.2095(2) 0.74151(13) 0.0462(7) Uani 1 1 d . . . H12A H 0.9926 0.1900 0.7583 0.069 Uiso 1 1 calc R . . H12B H 0.9112 0.2464 0.7026 0.069 Uiso 1 1 calc R . . H12C H 0.8703 0.1508 0.7330 0.069 Uiso 1 1 calc R . . C13 C 0.6970(2) 0.03905(18) 0.91584(12) 0.0364(6) Uani 1 1 d . . . H13 H 0.6305 0.0657 0.8865 0.044 Uiso 1 1 calc R . . C14 C 0.6755(2) 0.0414(2) 0.98164(13) 0.0498(7) Uani 1 1 d . . . H14A H 0.7359 0.0090 1.0109 0.075 Uiso 1 1 calc R . . H14B H 0.6069 0.0071 0.9816 0.075 Uiso 1 1 calc R . . H14C H 0.6699 0.1097 0.9946 0.075 Uiso 1 1 calc R . . C15 C 0.7124(3) -0.0669(2) 0.89602(15) 0.0564(8) Uani 1 1 d . . . H15A H 0.7258 -0.0673 0.8537 0.085 Uiso 1 1 calc R . . H15B H 0.6463 -0.1049 0.8964 0.085 Uiso 1 1 calc R . . H15C H 0.7750 -0.0963 0.9253 0.085 Uiso 1 1 calc R . . C16 C 0.41021(17) 0.24617(15) 0.75817(10) 0.0218(5) Uani 1 1 d . . . C17 C 0.34628(18) 0.22963(16) 0.80220(10) 0.0253(5) Uani 1 1 d . . . C18 C 0.24032(19) 0.26614(18) 0.78772(12) 0.0336(6) Uani 1 1 d . . . H18 H 0.1953 0.2575 0.8167 0.040 Uiso 1 1 calc R . . C19 C 0.1988(2) 0.31466(19) 0.73225(13) 0.0382(6) Uani 1 1 d . . . H19 H 0.1260 0.3390 0.7236 0.046 Uiso 1 1 calc R . . C20 C 0.26222(19) 0.32796(18) 0.68958(12) 0.0333(6) Uani 1 1 d . . . H20 H 0.2321 0.3603 0.6512 0.040 Uiso 1 1 calc R . . C21 C 0.37021(18) 0.29485(16) 0.70147(11) 0.0257(5) Uani 1 1 d . . . C22 C 0.3872(2) 0.16922(17) 0.86105(11) 0.0299(5) Uani 1 1 d . . . H22 H 0.4682 0.1786 0.8743 0.036 Uiso 1 1 calc R . . C23 C 0.3379(2) 0.2000(2) 0.91581(12) 0.0471(7) Uani 1 1 d . . . H23A H 0.3476 0.2708 0.9227 0.071 Uiso 1 1 calc R . . H23B H 0.3748 0.1647 0.9537 0.071 Uiso 1 1 calc R . . H23C H 0.2597 0.1842 0.9061 0.071 Uiso 1 1 calc R . . C24 C 0.3658(2) 0.06042(19) 0.84687(13) 0.0442(7) Uani 1 1 d . . . H24A H 0.2868 0.0491 0.8335 0.066 Uiso 1 1 calc R . . H24B H 0.3955 0.0219 0.8846 0.066 Uiso 1 1 calc R . . H24C H 0.4012 0.0405 0.8134 0.066 Uiso 1 1 calc R . . C25 C 0.43559(19) 0.30889(17) 0.65198(11) 0.0305(5) Uani 1 1 d . . . H25 H 0.5124 0.2872 0.6698 0.037 Uiso 1 1 calc R . . C26 C 0.4381(2) 0.41698(19) 0.63281(12) 0.0407(6) Uani 1 1 d . . . H26A H 0.3645 0.4376 0.6111 0.061 Uiso 1 1 calc R . . H26B H 0.4884 0.4249 0.6049 0.061 Uiso 1 1 calc R . . H26C H 0.4631 0.4575 0.6702 0.061 Uiso 1 1 calc R . . C27 C 0.3883(2) 0.2450(2) 0.59509(12) 0.0423(6) Uani 1 1 d . . . H27A H 0.3897 0.1761 0.6079 0.063 Uiso 1 1 calc R . . H27B H 0.4321 0.2531 0.5637 0.063 Uiso 1 1 calc R . . H27C H 0.3126 0.2648 0.5771 0.063 Uiso 1 1 calc R . . C28 C 0.60408(18) 0.49071(16) 0.89101(10) 0.0266(5) Uani 1 1 d . . . C29 C 0.5322(2) 0.62701(18) 0.92376(12) 0.0400(6) Uani 1 1 d . . . H29 H 0.4804 0.6724 0.9327 0.048 Uiso 1 1 calc R . . C30 C 0.6404(2) 0.63918(19) 0.93472(12) 0.0427(7) Uani 1 1 d . . . H30 H 0.6801 0.6952 0.9530 0.051 Uiso 1 1 calc R . . C31 C 0.40089(19) 0.49358(18) 0.87192(11) 0.0319(5) Uani 1 1 d . . . H31 H 0.4103 0.4221 0.8643 0.038 Uiso 1 1 calc R . . C32 C 0.3309(2) 0.5024(3) 0.91906(15) 0.0571(8) Uani 1 1 d . . . H32A H 0.3698 0.4741 0.9590 0.086 Uiso 1 1 calc R . . H32B H 0.2620 0.4672 0.9038 0.086 Uiso 1 1 calc R . . H32C H 0.3156 0.5718 0.9251 0.086 Uiso 1 1 calc R . . C33 C 0.3497(3) 0.5400(3) 0.80983(14) 0.0617(9) Uani 1 1 d . . . H33A H 0.3395 0.6104 0.8157 0.093 Uiso 1 1 calc R . . H33B H 0.2786 0.5094 0.7926 0.093 Uiso 1 1 calc R . . H33C H 0.3977 0.5306 0.7808 0.093 Uiso 1 1 calc R . . C34 C 0.8002(2) 0.5349(2) 0.91657(14) 0.0475(7) Uani 1 1 d . . . H34 H 0.8025 0.4963 0.8781 0.057 Uiso 1 1 calc R . . C35 C 0.8485(3) 0.4713(3) 0.97189(19) 0.0761(11) Uani 1 1 d . . . H35A H 0.8560 0.5094 1.0105 0.114 Uiso 1 1 calc R . . H35B H 0.9207 0.4479 0.9683 0.114 Uiso 1 1 calc R . . H35C H 0.8004 0.4149 0.9729 0.114 Uiso 1 1 calc R . . C36 C 0.8636(3) 0.6274(3) 0.91394(19) 0.0813(12) Uani 1 1 d . . . H36A H 0.8266 0.6668 0.8780 0.122 Uiso 1 1 calc R . . H36B H 0.9375 0.6109 0.9096 0.122 Uiso 1 1 calc R . . H36C H 0.8680 0.6650 0.9525 0.122 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 0.02380(16) 0.01807(15) 0.02421(16) -0.00263(11) 0.00655(12) -0.00045(11) Cl1 0.0505(4) 0.0325(3) 0.0262(3) -0.0006(2) 0.0109(3) -0.0060(3) Cl2 0.0393(3) 0.0245(3) 0.0302(3) 0.0021(2) 0.0105(3) -0.0028(2) N1 0.0219(9) 0.0189(9) 0.0221(9) 0.0003(8) 0.0042(8) 0.0025(7) N2 0.0217(9) 0.0180(9) 0.0211(9) -0.0003(7) 0.0037(8) 0.0020(7) N3 0.0343(11) 0.0207(10) 0.0315(11) -0.0041(8) 0.0096(9) 0.0009(8) N4 0.0371(12) 0.0296(11) 0.0349(11) -0.0112(9) 0.0131(9) -0.0107(9) C1 0.0233(11) 0.0189(11) 0.0185(10) 0.0031(9) 0.0072(9) -0.0009(9) C2 0.0307(13) 0.0207(11) 0.0259(12) -0.0046(9) 0.0059(10) 0.0048(9) C3 0.0282(13) 0.0217(12) 0.0259(12) -0.0057(9) 0.0025(10) 0.0005(9) C4 0.0227(11) 0.0223(11) 0.0233(11) -0.0029(9) 0.0019(9) 0.0039(9) C5 0.0243(12) 0.0253(12) 0.0337(13) -0.0020(10) 0.0060(10) 0.0038(10) C6 0.0230(13) 0.0412(15) 0.0452(15) 0.0000(12) 0.0024(11) -0.0008(11) C7 0.0286(14) 0.0501(17) 0.0358(14) -0.0022(12) -0.0061(11) 0.0057(12) C8 0.0404(15) 0.0371(14) 0.0271(13) 0.0016(11) 0.0006(11) 0.0071(12) C9 0.0318(13) 0.0238(12) 0.0265(12) -0.0014(10) 0.0035(10) 0.0023(10) C10 0.0247(12) 0.0325(13) 0.0435(15) 0.0070(11) 0.0090(11) 0.0023(10) C11 0.0402(15) 0.0286(14) 0.0642(18) 0.0026(13) 0.0248(14) 0.0034(11) C12 0.0590(18) 0.0392(16) 0.0436(16) -0.0006(13) 0.0183(14) -0.0095(13) C13 0.0387(14) 0.0345(14) 0.0325(13) 0.0109(11) 0.0009(11) -0.0022(11) C14 0.0571(18) 0.0510(18) 0.0426(16) 0.0139(14) 0.0143(14) -0.0083(14) C15 0.073(2) 0.0366(16) 0.0536(19) 0.0031(14) 0.0016(16) -0.0112(15) C16 0.0203(11) 0.0162(10) 0.0280(12) -0.0026(9) 0.0039(9) 0.0004(8) C17 0.0263(12) 0.0199(11) 0.0309(12) -0.0032(9) 0.0091(10) -0.0045(9) C18 0.0260(13) 0.0355(14) 0.0432(15) 0.0028(12) 0.0163(11) 0.0005(10) C19 0.0248(13) 0.0361(14) 0.0545(17) 0.0046(13) 0.0110(12) 0.0085(11) C20 0.0286(13) 0.0308(13) 0.0390(14) 0.0079(11) 0.0044(11) 0.0061(10) C21 0.0259(12) 0.0199(11) 0.0306(12) 0.0014(9) 0.0051(10) 0.0011(9) C22 0.0327(13) 0.0282(12) 0.0299(13) 0.0030(10) 0.0096(10) -0.0041(10) C23 0.0580(18) 0.0515(18) 0.0375(15) 0.0055(13) 0.0229(14) -0.0005(14) C24 0.0560(18) 0.0312(14) 0.0427(16) 0.0069(12) 0.0057(13) -0.0068(13) C25 0.0262(12) 0.0366(14) 0.0281(12) 0.0081(11) 0.0051(10) 0.0065(10) C26 0.0419(16) 0.0432(16) 0.0355(14) 0.0129(12) 0.0057(12) -0.0036(12) C27 0.0437(16) 0.0474(16) 0.0357(14) 0.0009(12) 0.0086(12) 0.0095(13) C28 0.0296(13) 0.0238(12) 0.0272(12) -0.0027(10) 0.0083(10) -0.0025(10) C29 0.0568(18) 0.0232(13) 0.0437(15) -0.0095(11) 0.0194(13) 0.0024(12) C30 0.0598(19) 0.0293(14) 0.0431(16) -0.0157(12) 0.0201(14) -0.0153(13) C31 0.0314(13) 0.0269(13) 0.0380(14) -0.0035(11) 0.0088(11) 0.0023(10) C32 0.0435(17) 0.075(2) 0.0573(19) -0.0049(17) 0.0217(15) -0.0071(16) C33 0.059(2) 0.072(2) 0.0459(18) 0.0094(16) -0.0039(15) -0.0069(17) C34 0.0329(15) 0.0619(19) 0.0514(17) -0.0226(15) 0.0175(13) -0.0159(13) C35 0.0325(17) 0.085(3) 0.108(3) 0.010(2) 0.0102(18) -0.0054(17) C36 0.063(2) 0.096(3) 0.092(3) -0.006(2) 0.032(2) -0.043(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 Ni1 C28 1.907(2) . ? Ni1 C1 1.923(2) . ? Ni1 Cl1 2.1831(7) . ? Ni1 Cl2 2.1875(6) . ? N1 C1 1.364(3) . ? N1 C2 1.386(3) . ? N1 C4 1.449(3) . ? N2 C1 1.359(3) . ? N2 C3 1.385(3) . ? N2 C16 1.452(3) . ? N3 C28 1.353(3) . ? N3 C29 1.385(3) . ? N3 C31 1.473(3) . ? N4 C28 1.351(3) . ? N4 C30 1.379(3) . ? N4 C34 1.475(3) . ? C2 C3 1.339(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C9 1.395(3) . ? C4 C5 1.401(3) . ? C5 C6 1.389(3) . ? C5 C10 1.516(3) . ? C6 C7 1.376(4) . ? C6 H6 0.9500 . ? C7 C8 1.377(4) . ? C7 H7 0.9500 . ? C8 C9 1.392(3) . ? C8 H8 0.9500 . ? C9 C13 1.522(3) . ? C10 C11 1.520(3) . ? C10 C12 1.533(4) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.528(4) . ? C13 C15 1.533(4) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C21 1.399(3) . ? C16 C17 1.407(3) . ? C17 C18 1.388(3) . ? C17 C22 1.519(3) . ? C18 C19 1.379(3) . ? C18 H18 0.9500 . ? C19 C20 1.371(3) . ? C19 H19 0.9500 . ? C20 C21 1.396(3) . ? C20 H20 0.9500 . ? C21 C25 1.514(3) . ? C22 C24 1.526(3) . ? C22 C23 1.530(3) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C27 1.527(3) . ? C25 C26 1.534(3) . ? C25 H25 1.0000 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C29 C30 1.335(4) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.506(4) . ? C31 C33 1.507(4) . ? C31 H31 1.0000 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C36 1.498(4) . ? C34 C35 1.503(5) . ? C34 H34 1.0000 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C28 Ni1 C1 173.10(9) . . ? C28 Ni1 Cl1 89.15(7) . . ? C1 Ni1 Cl1 94.30(6) . . ? C28 Ni1 Cl2 89.12(7) . . ? C1 Ni1 Cl2 88.19(6) . . ? Cl1 Ni1 Cl2 172.51(3) . . ? C1 N1 C2 111.53(17) . . ? C1 N1 C4 124.76(17) . . ? C2 N1 C4 122.68(17) . . ? C1 N2 C3 111.42(17) . . ? C1 N2 C16 125.68(17) . . ? C3 N2 C16 122.74(17) . . ? C28 N3 C29 110.7(2) . . ? C28 N3 C31 123.38(18) . . ? C29 N3 C31 125.7(2) . . ? C28 N4 C30 110.4(2) . . ? C28 N4 C34 122.0(2) . . ? C30 N4 C34 127.6(2) . . ? N2 C1 N1 103.51(17) . . ? N2 C1 Ni1 125.08(15) . . ? N1 C1 Ni1 130.80(15) . . ? C3 C2 N1 106.48(19) . . ? C3 C2 H2 126.8 . . ? N1 C2 H2 126.8 . . ? C2 C3 N2 107.04(19) . . ? C2 C3 H3 126.5 . . ? N2 C3 H3 126.5 . . ? C9 C4 C5 122.9(2) . . ? C9 C4 N1 117.64(19) . . ? C5 C4 N1 119.39(19) . . ? C6 C5 C4 116.8(2) . . ? C6 C5 C10 121.5(2) . . ? C4 C5 C10 121.5(2) . . ? C7 C6 C5 121.4(2) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C6 C7 C8 120.7(2) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 117.6(2) . . ? C8 C9 C13 119.8(2) . . ? C4 C9 C13 122.6(2) . . ? C5 C10 C11 113.2(2) . . ? C5 C10 C12 109.9(2) . . ? C11 C10 C12 110.0(2) . . ? C5 C10 H10 107.9 . . ? C11 C10 H10 107.9 . . ? C12 C10 H10 107.9 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 C14 113.4(2) . . ? C9 C13 C15 110.3(2) . . ? C14 C13 C15 110.4(2) . . ? C9 C13 H13 107.5 . . ? C14 C13 H13 107.5 . . ? C15 C13 H13 107.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 122.8(2) . . ? C21 C16 N2 119.01(19) . . ? C17 C16 N2 118.11(19) . . ? C18 C17 C16 116.9(2) . . ? C18 C17 C22 120.7(2) . . ? C16 C17 C22 122.3(2) . . ? C19 C18 C17 121.6(2) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C20 C19 C18 120.3(2) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 121.3(2) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C16 117.2(2) . . ? C20 C21 C25 119.1(2) . . ? C16 C21 C25 123.7(2) . . ? C17 C22 C24 110.1(2) . . ? C17 C22 C23 113.6(2) . . ? C24 C22 C23 110.0(2) . . ? C17 C22 H22 107.6 . . ? C24 C22 H22 107.6 . . ? C23 C22 H22 107.6 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 C27 109.9(2) . . ? C21 C25 C26 111.5(2) . . ? C27 C25 C26 110.6(2) . . ? C21 C25 H25 108.2 . . ? C27 C25 H25 108.2 . . ? C26 C25 H25 108.2 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N4 C28 N3 104.87(19) . . ? N4 C28 Ni1 129.72(17) . . ? N3 C28 Ni1 125.41(16) . . ? C30 C29 N3 106.5(2) . . ? C30 C29 H29 126.8 . . ? N3 C29 H29 126.8 . . ? C29 C30 N4 107.6(2) . . ? C29 C30 H30 126.2 . . ? N4 C30 H30 126.2 . . ? N3 C31 C32 110.8(2) . . ? N3 C31 C33 110.1(2) . . ? C32 C31 C33 113.1(2) . . ? N3 C31 H31 107.5 . . ? C32 C31 H31 107.5 . . ? C33 C31 H31 107.5 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N4 C34 C36 111.6(3) . . ? N4 C34 C35 110.4(2) . . ? C36 C34 C35 113.4(3) . . ? N4 C34 H34 107.1 . . ? C36 C34 H34 107.1 . . ? C35 C34 H34 107.1 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N2 C1 N1 -1.1(2) . . . . ? C16 N2 C1 N1 174.51(18) . . . . ? C3 N2 C1 Ni1 170.83(15) . . . . ? C16 N2 C1 Ni1 -13.6(3) . . . . ? C2 N1 C1 N2 1.3(2) . . . . ? C4 N1 C1 N2 -167.31(18) . . . . ? C2 N1 C1 Ni1 -169.90(16) . . . . ? C4 N1 C1 Ni1 21.5(3) . . . . ? C28 Ni1 C1 N2 -9.9(9) . . . . ? Cl1 Ni1 C1 N2 110.00(17) . . . . ? Cl2 Ni1 C1 N2 -77.08(17) . . . . ? C28 Ni1 C1 N1 159.7(7) . . . . ? Cl1 Ni1 C1 N1 -80.45(19) . . . . ? Cl2 Ni1 C1 N1 92.48(19) . . . . ? C1 N1 C2 C3 -1.1(2) . . . . ? C4 N1 C2 C3 167.79(19) . . . . ? N1 C2 C3 N2 0.4(2) . . . . ? C1 N2 C3 C2 0.4(2) . . . . ? C16 N2 C3 C2 -175.30(19) . . . . ? C1 N1 C4 C9 91.4(3) . . . . ? C2 N1 C4 C9 -76.0(3) . . . . ? C1 N1 C4 C5 -91.6(3) . . . . ? C2 N1 C4 C5 101.0(2) . . . . ? C9 C4 C5 C6 -3.0(3) . . . . ? N1 C4 C5 C6 -179.8(2) . . . . ? C9 C4 C5 C10 172.3(2) . . . . ? N1 C4 C5 C10 -4.5(3) . . . . ? C4 C5 C6 C7 1.3(4) . . . . ? C10 C5 C6 C7 -173.9(2) . . . . ? C5 C6 C7 C8 0.6(4) . . . . ? C6 C7 C8 C9 -1.0(4) . . . . ? C7 C8 C9 C4 -0.5(4) . . . . ? C7 C8 C9 C13 176.6(2) . . . . ? C5 C4 C9 C8 2.6(3) . . . . ? N1 C4 C9 C8 179.5(2) . . . . ? C5 C4 C9 C13 -174.4(2) . . . . ? N1 C4 C9 C13 2.4(3) . . . . ? C6 C5 C10 C11 -40.7(3) . . . . ? C4 C5 C10 C11 144.3(2) . . . . ? C6 C5 C10 C12 82.7(3) . . . . ? C4 C5 C10 C12 -92.3(3) . . . . ? C8 C9 C13 C14 48.4(3) . . . . ? C4 C9 C13 C14 -134.6(2) . . . . ? C8 C9 C13 C15 -76.0(3) . . . . ? C4 C9 C13 C15 101.0(3) . . . . ? C1 N2 C16 C21 110.5(2) . . . . ? C3 N2 C16 C21 -74.4(3) . . . . ? C1 N2 C16 C17 -73.3(3) . . . . ? C3 N2 C16 C17 101.8(2) . . . . ? C21 C16 C17 C18 -1.5(3) . . . . ? N2 C16 C17 C18 -177.52(19) . . . . ? C21 C16 C17 C22 174.7(2) . . . . ? N2 C16 C17 C22 -1.4(3) . . . . ? C16 C17 C18 C19 1.2(3) . . . . ? C22 C17 C18 C19 -174.9(2) . . . . ? C17 C18 C19 C20 0.1(4) . . . . ? C18 C19 C20 C21 -1.3(4) . . . . ? C19 C20 C21 C16 1.1(3) . . . . ? C19 C20 C21 C25 178.3(2) . . . . ? C17 C16 C21 C20 0.3(3) . . . . ? N2 C16 C21 C20 176.37(19) . . . . ? C17 C16 C21 C25 -176.8(2) . . . . ? N2 C16 C21 C25 -0.7(3) . . . . ? C18 C17 C22 C24 90.8(3) . . . . ? C16 C17 C22 C24 -85.2(3) . . . . ? C18 C17 C22 C23 -33.1(3) . . . . ? C16 C17 C22 C23 150.9(2) . . . . ? C20 C21 C25 C27 -67.5(3) . . . . ? C16 C21 C25 C27 109.6(2) . . . . ? C20 C21 C25 C26 55.5(3) . . . . ? C16 C21 C25 C26 -127.4(2) . . . . ? C30 N4 C28 N3 0.0(3) . . . . ? C34 N4 C28 N3 -179.6(2) . . . . ? C30 N4 C28 Ni1 179.85(18) . . . . ? C34 N4 C28 Ni1 0.2(3) . . . . ? C29 N3 C28 N4 0.0(3) . . . . ? C31 N3 C28 N4 174.7(2) . . . . ? C29 N3 C28 Ni1 -179.83(17) . . . . ? C31 N3 C28 Ni1 -5.2(3) . . . . ? C1 Ni1 C28 N4 -143.1(7) . . . . ? Cl1 Ni1 C28 N4 96.7(2) . . . . ? Cl2 Ni1 C28 N4 -76.0(2) . . . . ? C1 Ni1 C28 N3 36.7(9) . . . . ? Cl1 Ni1 C28 N3 -83.45(19) . . . . ? Cl2 Ni1 C28 N3 103.84(19) . . . . ? C28 N3 C29 C30 -0.1(3) . . . . ? C31 N3 C29 C30 -174.6(2) . . . . ? N3 C29 C30 N4 0.0(3) . . . . ? C28 N4 C30 C29 0.0(3) . . . . ? C34 N4 C30 C29 179.6(2) . . . . ? C28 N3 C31 C32 135.7(2) . . . . ? C29 N3 C31 C32 -50.4(3) . . . . ? C28 N3 C31 C33 -98.4(3) . . . . ? C29 N3 C31 C33 75.4(3) . . . . ? C28 N4 C34 C36 152.0(3) . . . . ? C30 N4 C34 C36 -27.5(4) . . . . ? C28 N4 C34 C35 -81.0(3) . . . . ? C30 N4 C34 C35 99.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.341 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.048 # Attachment '- shelxl-2.cif' data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 805190' #TrackingRef '- shelxl-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H52 Br2 N4 Ni' _chemical_formula_sum 'C36 H52 Br2 N4 Ni' _chemical_formula_weight 759.35 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 12.663(2) _cell_length_b 13.596(2) _cell_length_c 22.415(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.855(2) _cell_angle_gamma 90.00 _cell_volume 3730.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 7480 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 2.691 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.235 _exptl_absorpt_correction_T_max 0.297 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16211 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.50 _reflns_number_total 6862 _reflns_number_gt 5826 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1879P)^2^+22.3926P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6862 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.2927 _refine_ls_wR_factor_gt 0.2804 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.85702(9) 0.44946(8) 0.22407(5) 0.0567(4) Uani 1 1 d . . . Br2 Br 0.85911(9) 0.30696(7) 0.04190(4) 0.0535(3) Uani 1 1 d . . . Ni1 Ni 0.87290(6) 0.37417(5) 0.13702(3) 0.0160(3) Uani 1 1 d . . . N1 N 0.9709(4) 0.2172(4) 0.2230(2) 0.0162(10) Uani 1 1 d . . . N2 N 0.8023(4) 0.1829(4) 0.1823(2) 0.0150(10) Uani 1 1 d . . . N3 N 0.8099(5) 0.5664(5) 0.0745(3) 0.0302(13) Uani 1 1 d . . . N4 N 0.9824(5) 0.5466(4) 0.1061(3) 0.0253(12) Uani 1 1 d . . . C1 C 0.8818(4) 0.2509(4) 0.1790(3) 0.0140(11) Uani 1 1 d . . . C2 C 0.9468(5) 0.1330(4) 0.2520(3) 0.0211(13) Uani 1 1 d . . . H2 H 0.9954 0.0967 0.2829 0.025 Uiso 1 1 calc R . . C3 C 0.8417(5) 0.1136(5) 0.2275(3) 0.0195(13) Uani 1 1 d . . . H3 H 0.8016 0.0620 0.2389 0.023 Uiso 1 1 calc R . . C4 C 1.0796(5) 0.2575(4) 0.2348(3) 0.0168(12) Uani 1 1 d . . . C5 C 1.1407(5) 0.2380(5) 0.1909(3) 0.0222(13) Uani 1 1 d . . . C6 C 1.2460(6) 0.2749(6) 0.2046(4) 0.0315(16) Uani 1 1 d . . . H6 H 1.2891 0.2650 0.1767 0.038 Uiso 1 1 calc R . . C7 C 1.2890(6) 0.3260(6) 0.2586(4) 0.0395(19) Uani 1 1 d . . . H7 H 1.3601 0.3516 0.2660 0.047 Uiso 1 1 calc R . . C8 C 1.2317(6) 0.3402(6) 0.3010(4) 0.0330(17) Uani 1 1 d . . . H8 H 1.2643 0.3726 0.3383 0.040 Uiso 1 1 calc R . . C9 C 1.1230(5) 0.3066(5) 0.2897(3) 0.0228(13) Uani 1 1 d . . . C10 C 1.0966(6) 0.1742(5) 0.1345(3) 0.0274(15) Uani 1 1 d . . . H10 H 1.0163 0.1828 0.1214 0.033 Uiso 1 1 calc R . . C11 C 1.1204(8) 0.0663(6) 0.1519(4) 0.043(2) Uani 1 1 d . . . H11A H 1.0867 0.0250 0.1169 0.064 Uiso 1 1 calc R . . H11B H 1.0909 0.0499 0.1865 0.064 Uiso 1 1 calc R . . H11C H 1.1987 0.0555 0.1632 0.064 Uiso 1 1 calc R . . C12 C 1.1423(9) 0.1989(8) 0.0802(4) 0.052(2) Uani 1 1 d . . . H12A H 1.1445 0.2698 0.0756 0.077 Uiso 1 1 calc R . . H12B H 1.0961 0.1703 0.0429 0.077 Uiso 1 1 calc R . . H12C H 1.2156 0.1725 0.0873 0.077 Uiso 1 1 calc R . . C13 C 1.0616(6) 0.3216(6) 0.3394(3) 0.0309(16) Uani 1 1 d . . . H13 H 0.9843 0.3028 0.3222 0.037 Uiso 1 1 calc R . . C14 C 1.0658(7) 0.4298(7) 0.3606(4) 0.046(2) Uani 1 1 d . . . H14A H 1.1396 0.4460 0.3838 0.069 Uiso 1 1 calc R . . H14B H 1.0160 0.4392 0.3866 0.069 Uiso 1 1 calc R . . H14C H 1.0446 0.4724 0.3248 0.069 Uiso 1 1 calc R . . C15 C 1.1108(8) 0.2550(7) 0.3943(4) 0.046(2) Uani 1 1 d . . . H15A H 1.1118 0.1876 0.3802 0.069 Uiso 1 1 calc R . . H15B H 1.0670 0.2589 0.4240 0.069 Uiso 1 1 calc R . . H15C H 1.1848 0.2761 0.4137 0.069 Uiso 1 1 calc R . . C16 C 0.6985(5) 0.1741(5) 0.1373(3) 0.0196(13) Uani 1 1 d . . . C17 C 0.6088(5) 0.2263(5) 0.1463(3) 0.0241(14) Uani 1 1 d . . . C18 C 0.5092(6) 0.2150(6) 0.1008(4) 0.0386(18) Uani 1 1 d . . . H18 H 0.4468 0.2491 0.1049 0.046 Uiso 1 1 calc R . . C19 C 0.5025(7) 0.1545(6) 0.0505(4) 0.042(2) Uani 1 1 d . . . H19 H 0.4364 0.1496 0.0197 0.050 Uiso 1 1 calc R . . C20 C 0.5917(7) 0.1017(6) 0.0451(3) 0.0346(17) Uani 1 1 d . . . H20 H 0.5852 0.0595 0.0111 0.042 Uiso 1 1 calc R . . C21 C 0.6911(6) 0.1089(5) 0.0886(3) 0.0236(14) Uani 1 1 d . . . C22 C 0.6146(6) 0.2866(6) 0.2028(4) 0.0300(15) Uani 1 1 d . . . H22 H 0.6924 0.3032 0.2207 0.036 Uiso 1 1 calc R . . C23 C 0.5508(7) 0.3840(6) 0.1907(5) 0.045(2) Uani 1 1 d . . . H23A H 0.5756 0.4221 0.1603 0.067 Uiso 1 1 calc R . . H23B H 0.5632 0.4211 0.2288 0.067 Uiso 1 1 calc R . . H23C H 0.4734 0.3702 0.1753 0.067 Uiso 1 1 calc R . . C24 C 0.5767(8) 0.2253(7) 0.2509(4) 0.045(2) Uani 1 1 d . . . H24A H 0.5006 0.2072 0.2347 0.068 Uiso 1 1 calc R . . H24B H 0.5847 0.2636 0.2883 0.068 Uiso 1 1 calc R . . H24C H 0.6208 0.1662 0.2602 0.068 Uiso 1 1 calc R . . C25 C 0.7878(6) 0.0443(6) 0.0836(3) 0.0325(16) Uani 1 1 d . . . H25 H 0.8551 0.0727 0.1108 0.039 Uiso 1 1 calc R . . C26 C 0.8021(9) 0.0403(7) 0.0174(4) 0.052(2) Uani 1 1 d . . . H26A H 0.7469 -0.0025 -0.0076 0.078 Uiso 1 1 calc R . . H26B H 0.8741 0.0149 0.0184 0.078 Uiso 1 1 calc R . . H26C H 0.7943 0.1059 -0.0001 0.078 Uiso 1 1 calc R . . C27 C 0.7748(9) -0.0591(7) 0.1058(5) 0.057(3) Uani 1 1 d . . . H27A H 0.7832 -0.0583 0.1500 0.085 Uiso 1 1 calc R . . H27B H 0.8301 -0.1013 0.0963 0.085 Uiso 1 1 calc R . . H27C H 0.7029 -0.0838 0.0852 0.085 Uiso 1 1 calc R . . C28 C 0.8850(5) 0.5008(5) 0.1038(3) 0.0239(13) Uani 1 1 d . . . C29 C 0.8581(7) 0.6499(6) 0.0598(4) 0.0375(18) Uani 1 1 d . . . H29 H 0.8217 0.7057 0.0398 0.045 Uiso 1 1 calc R . . C30 C 0.9651(7) 0.6383(5) 0.0789(4) 0.0387(19) Uani 1 1 d . . . H30 H 1.0189 0.6836 0.0748 0.046 Uiso 1 1 calc R . . C31 C 0.6898(8) 0.5487(9) 0.0619(5) 0.0607(17) Uani 1 1 d . . . H31 H 0.6776 0.4823 0.0770 0.073 Uiso 1 1 calc R . . C32 C 0.6397(8) 0.6227(9) 0.0948(5) 0.0607(17) Uani 1 1 d . . . H32A H 0.6824 0.6274 0.1374 0.091 Uiso 1 1 calc R . . H32B H 0.5657 0.6028 0.0938 0.091 Uiso 1 1 calc R . . H32C H 0.6383 0.6861 0.0749 0.091 Uiso 1 1 calc R . . C33 C 0.6429(8) 0.5522(9) -0.0054(5) 0.0607(17) Uani 1 1 d . . . H33A H 0.6788 0.6034 -0.0231 0.091 Uiso 1 1 calc R . . H33B H 0.5654 0.5661 -0.0140 0.091 Uiso 1 1 calc R . . H33C H 0.6537 0.4892 -0.0233 0.091 Uiso 1 1 calc R . . C34 C 1.0896(5) 0.5039(5) 0.1354(3) 0.0262(14) Uani 1 1 d . . . H34 H 1.0770 0.4366 0.1489 0.031 Uiso 1 1 calc R . . C35 C 1.1454(9) 0.5609(8) 0.1919(5) 0.061(3) Uani 1 1 d . . . H35A H 1.1535 0.6289 0.1808 0.091 Uiso 1 1 calc R . . H35B H 1.2169 0.5328 0.2098 0.091 Uiso 1 1 calc R . . H35C H 1.1019 0.5579 0.2218 0.091 Uiso 1 1 calc R . . C36 C 1.1598(8) 0.4951(8) 0.0893(5) 0.053(2) Uani 1 1 d . . . H36A H 1.1174 0.4645 0.0517 0.079 Uiso 1 1 calc R . . H36B H 1.2235 0.4550 0.1071 0.079 Uiso 1 1 calc R . . H36C H 1.1830 0.5600 0.0800 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0706(7) 0.0441(6) 0.0591(7) -0.0038(4) 0.0231(5) 0.0036(4) Br2 0.0816(8) 0.0423(6) 0.0375(5) 0.0014(4) 0.0169(5) 0.0031(4) Ni1 0.0208(4) 0.0103(4) 0.0179(4) 0.0025(3) 0.0065(3) -0.0001(3) N1 0.017(2) 0.016(3) 0.015(2) -0.001(2) 0.0030(19) -0.0046(19) N2 0.016(2) 0.011(2) 0.017(2) -0.0006(19) 0.0011(19) -0.0054(18) N3 0.036(3) 0.024(3) 0.033(3) 0.012(3) 0.014(3) 0.009(2) N4 0.034(3) 0.014(3) 0.031(3) 0.006(2) 0.012(2) -0.002(2) C1 0.014(3) 0.014(3) 0.015(3) -0.005(2) 0.005(2) 0.001(2) C2 0.028(3) 0.012(3) 0.021(3) 0.007(2) 0.004(2) -0.004(2) C3 0.028(3) 0.012(3) 0.015(3) 0.007(2) 0.000(2) -0.007(2) C4 0.013(3) 0.012(3) 0.024(3) 0.002(2) 0.002(2) -0.001(2) C5 0.023(3) 0.019(3) 0.026(3) 0.002(3) 0.007(3) 0.005(2) C6 0.024(3) 0.028(4) 0.047(4) 0.003(3) 0.018(3) -0.003(3) C7 0.021(3) 0.034(4) 0.065(5) 0.001(4) 0.013(4) -0.007(3) C8 0.022(3) 0.025(4) 0.047(4) -0.010(3) 0.000(3) -0.007(3) C9 0.022(3) 0.016(3) 0.030(3) 0.000(3) 0.004(3) -0.003(2) C10 0.031(4) 0.024(4) 0.029(3) -0.001(3) 0.012(3) 0.012(3) C11 0.063(5) 0.021(4) 0.040(4) -0.003(3) 0.005(4) 0.006(4) C12 0.072(6) 0.054(6) 0.037(5) -0.006(4) 0.029(4) -0.003(5) C13 0.029(3) 0.038(4) 0.025(3) -0.014(3) 0.006(3) -0.008(3) C14 0.049(5) 0.049(5) 0.038(4) -0.023(4) 0.007(4) -0.004(4) C15 0.052(5) 0.054(6) 0.028(4) 0.002(4) 0.004(4) -0.016(4) C16 0.017(3) 0.019(3) 0.019(3) 0.003(2) -0.002(2) -0.005(2) C17 0.016(3) 0.019(3) 0.033(4) 0.002(3) -0.001(3) -0.005(2) C18 0.024(4) 0.038(4) 0.049(5) 0.007(4) 0.001(3) 0.001(3) C19 0.033(4) 0.041(5) 0.038(4) 0.002(4) -0.014(3) -0.006(3) C20 0.044(4) 0.030(4) 0.024(3) -0.004(3) 0.000(3) -0.009(3) C21 0.031(3) 0.015(3) 0.023(3) 0.000(3) 0.003(3) -0.005(3) C22 0.021(3) 0.029(4) 0.041(4) -0.005(3) 0.011(3) -0.005(3) C23 0.046(5) 0.020(4) 0.071(6) -0.001(4) 0.019(4) 0.007(3) C24 0.049(5) 0.043(5) 0.048(5) 0.004(4) 0.019(4) 0.010(4) C25 0.040(4) 0.029(4) 0.025(3) -0.009(3) 0.001(3) 0.003(3) C26 0.077(7) 0.046(5) 0.034(4) -0.016(4) 0.017(4) 0.011(5) C27 0.082(7) 0.027(5) 0.054(6) -0.003(4) 0.007(5) 0.012(4) C28 0.029(3) 0.019(3) 0.026(3) 0.003(3) 0.010(3) 0.005(3) C29 0.052(5) 0.024(4) 0.042(4) 0.019(3) 0.021(4) 0.010(3) C30 0.059(5) 0.014(3) 0.049(5) 0.010(3) 0.025(4) 0.002(3) C31 0.045(3) 0.084(5) 0.060(4) 0.015(3) 0.025(3) 0.014(3) C32 0.045(3) 0.084(5) 0.060(4) 0.015(3) 0.025(3) 0.014(3) C33 0.045(3) 0.084(5) 0.060(4) 0.015(3) 0.025(3) 0.014(3) C34 0.027(3) 0.021(3) 0.031(4) 0.007(3) 0.008(3) -0.003(3) C35 0.063(6) 0.051(6) 0.058(6) -0.015(5) -0.004(5) 0.002(5) C36 0.053(5) 0.054(6) 0.060(6) 0.014(5) 0.028(5) 0.015(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Ni1 2.2577(13) . ? Br2 Ni1 2.2847(12) . ? Ni1 C28 1.897(7) . ? Ni1 C1 1.912(6) . ? N1 C1 1.373(8) . ? N1 C2 1.388(8) . ? N1 C4 1.441(7) . ? N2 C3 1.379(8) . ? N2 C1 1.383(7) . ? N2 C16 1.442(7) . ? N3 C28 1.346(9) . ? N3 C29 1.369(10) . ? N3 C31 1.493(12) . ? N4 C28 1.371(9) . ? N4 C30 1.380(9) . ? N4 C34 1.468(9) . ? C2 C3 1.329(9) . ? C2 H2 0.9400 . ? C3 H3 0.9400 . ? C4 C9 1.383(9) . ? C4 C5 1.425(9) . ? C5 C6 1.383(10) . ? C5 C10 1.517(10) . ? C6 C7 1.380(12) . ? C6 H6 0.9400 . ? C7 C8 1.350(12) . ? C7 H7 0.9400 . ? C8 C9 1.409(9) . ? C8 H8 0.9400 . ? C9 C13 1.527(10) . ? C10 C12 1.513(11) . ? C10 C11 1.528(10) . ? C10 H10 0.9900 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? C13 C15 1.527(12) . ? C13 C14 1.543(11) . ? C13 H13 0.9900 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? C16 C21 1.391(9) . ? C16 C17 1.397(9) . ? C17 C18 1.412(10) . ? C17 C22 1.494(10) . ? C18 C19 1.381(13) . ? C18 H18 0.9400 . ? C19 C20 1.370(12) . ? C19 H19 0.9400 . ? C20 C21 1.384(10) . ? C20 H20 0.9400 . ? C21 C25 1.533(10) . ? C22 C24 1.535(12) . ? C22 C23 1.539(11) . ? C22 H22 0.9900 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 H24C 0.9700 . ? C25 C27 1.513(12) . ? C25 C26 1.542(11) . ? C25 H25 0.9900 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 H26C 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C29 C30 1.321(12) . ? C29 H29 0.9400 . ? C30 H30 0.9400 . ? C31 C33 1.472(15) . ? C31 C32 1.484(15) . ? C31 H31 0.9900 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C34 C35 1.498(12) . ? C34 C36 1.531(11) . ? C34 H34 0.9900 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C35 H35C 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C36 H36C 0.9700 . ? 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 C28 Ni1 C1 171.2(3) . . ? C28 Ni1 Br1 87.8(2) . . ? C1 Ni1 Br1 88.79(17) . . ? C28 Ni1 Br2 89.5(2) . . ? C1 Ni1 Br2 95.15(17) . . ? Br1 Ni1 Br2 170.21(5) . . ? C1 N1 C2 111.8(5) . . ? C1 N1 C4 125.2(5) . . ? C2 N1 C4 122.8(5) . . ? C3 N2 C1 111.3(5) . . ? C3 N2 C16 123.5(5) . . ? C1 N2 C16 124.2(5) . . ? C28 N3 C29 111.3(6) . . ? C28 N3 C31 123.0(7) . . ? C29 N3 C31 125.7(7) . . ? C28 N4 C30 110.8(6) . . ? C28 N4 C34 123.8(5) . . ? C30 N4 C34 125.4(6) . . ? N1 C1 N2 102.4(5) . . ? N1 C1 Ni1 125.4(4) . . ? N2 C1 Ni1 131.4(4) . . ? C3 C2 N1 106.7(5) . . ? C3 C2 H2 126.7 . . ? N1 C2 H2 126.7 . . ? C2 C3 N2 107.7(5) . . ? C2 C3 H3 126.1 . . ? N2 C3 H3 126.1 . . ? C9 C4 C5 122.8(6) . . ? C9 C4 N1 119.3(6) . . ? C5 C4 N1 117.7(5) . . ? C6 C5 C4 116.2(6) . . ? C6 C5 C10 121.5(6) . . ? C4 C5 C10 122.2(6) . . ? C7 C6 C5 121.3(7) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C8 C7 C6 121.8(7) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 120.2(7) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 117.7(6) . . ? C4 C9 C13 123.5(6) . . ? C8 C9 C13 118.8(6) . . ? C12 C10 C5 114.0(7) . . ? C12 C10 C11 109.1(7) . . ? C5 C10 C11 109.3(6) . . ? C12 C10 H10 108.1 . . ? C5 C10 H10 108.1 . . ? C11 C10 H10 108.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 C15 109.3(7) . . ? C9 C13 C14 111.6(6) . . ? C15 C13 C14 110.0(6) . . ? C9 C13 H13 108.6 . . ? C15 C13 H13 108.6 . . ? C14 C13 H13 108.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 122.9(6) . . ? C21 C16 N2 117.9(6) . . ? C17 C16 N2 119.0(6) . . ? C16 C17 C18 116.7(7) . . ? C16 C17 C22 122.4(6) . . ? C18 C17 C22 120.8(7) . . ? C19 C18 C17 120.7(7) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C20 C19 C18 120.3(7) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 121.5(7) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C20 C21 C16 117.6(6) . . ? C20 C21 C25 120.5(6) . . ? C16 C21 C25 121.8(6) . . ? C17 C22 C24 110.0(6) . . ? C17 C22 C23 114.4(7) . . ? C24 C22 C23 110.3(6) . . ? C17 C22 H22 107.3 . . ? C24 C22 H22 107.3 . . ? C23 C22 H22 107.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C27 C25 C21 110.7(7) . . ? C27 C25 C26 109.4(7) . . ? C21 C25 C26 112.5(7) . . ? C27 C25 H25 108.0 . . ? C21 C25 H25 108.0 . . ? C26 C25 H25 108.0 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N3 C28 N4 103.5(6) . . ? N3 C28 Ni1 132.4(5) . . ? N4 C28 Ni1 124.1(5) . . ? C30 C29 N3 107.9(7) . . ? C30 C29 H29 126.1 . . ? N3 C29 H29 126.1 . . ? C29 C30 N4 106.5(7) . . ? C29 C30 H30 126.7 . . ? N4 C30 H30 126.7 . . ? C33 C31 C32 112.1(9) . . ? C33 C31 N3 108.3(8) . . ? C32 C31 N3 109.9(10) . . ? C33 C31 H31 108.8 . . ? C32 C31 H31 108.8 . . ? N3 C31 H31 108.8 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N4 C34 C35 110.9(7) . . ? N4 C34 C36 111.0(6) . . ? C35 C34 C36 112.4(8) . . ? N4 C34 H34 107.4 . . ? C35 C34 H34 107.4 . . ? C36 C34 H34 107.4 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N2 -0.3(6) . . . . ? C4 N1 C1 N2 174.4(5) . . . . ? C2 N1 C1 Ni1 170.4(4) . . . . ? C4 N1 C1 Ni1 -15.0(8) . . . . ? C3 N2 C1 N1 1.6(6) . . . . ? C16 N2 C1 N1 -167.5(5) . . . . ? C3 N2 C1 Ni1 -168.2(5) . . . . ? C16 N2 C1 Ni1 22.7(9) . . . . ? C28 Ni1 C1 N1 -7(2) . . . . ? Br1 Ni1 C1 N1 -74.4(5) . . . . ? Br2 Ni1 C1 N1 114.5(5) . . . . ? C28 Ni1 C1 N2 160.5(15) . . . . ? Br1 Ni1 C1 N2 93.3(5) . . . . ? Br2 Ni1 C1 N2 -77.7(5) . . . . ? C1 N1 C2 C3 -1.2(7) . . . . ? C4 N1 C2 C3 -176.0(6) . . . . ? N1 C2 C3 N2 2.1(7) . . . . ? C1 N2 C3 C2 -2.4(7) . . . . ? C16 N2 C3 C2 166.8(6) . . . . ? C1 N1 C4 C9 111.5(7) . . . . ? C2 N1 C4 C9 -74.4(8) . . . . ? C1 N1 C4 C5 -73.1(8) . . . . ? C2 N1 C4 C5 101.0(7) . . . . ? C9 C4 C5 C6 -2.7(10) . . . . ? N1 C4 C5 C6 -177.9(6) . . . . ? C9 C4 C5 C10 172.9(6) . . . . ? N1 C4 C5 C10 -2.3(9) . . . . ? C4 C5 C6 C7 1.1(11) . . . . ? C10 C5 C6 C7 -174.5(7) . . . . ? C5 C6 C7 C8 1.7(13) . . . . ? C6 C7 C8 C9 -3.0(13) . . . . ? C5 C4 C9 C8 1.4(10) . . . . ? N1 C4 C9 C8 176.6(6) . . . . ? C5 C4 C9 C13 -175.4(6) . . . . ? N1 C4 C9 C13 -0.2(10) . . . . ? C7 C8 C9 C4 1.4(11) . . . . ? C7 C8 C9 C13 178.4(7) . . . . ? C6 C5 C10 C12 -32.2(10) . . . . ? C4 C5 C10 C12 152.5(7) . . . . ? C6 C5 C10 C11 90.2(8) . . . . ? C4 C5 C10 C11 -85.2(8) . . . . ? C4 C9 C13 C15 107.3(7) . . . . ? C8 C9 C13 C15 -69.5(8) . . . . ? C4 C9 C13 C14 -130.8(7) . . . . ? C8 C9 C13 C14 52.4(9) . . . . ? C3 N2 C16 C21 -75.9(8) . . . . ? C1 N2 C16 C21 91.9(7) . . . . ? C3 N2 C16 C17 100.1(7) . . . . ? C1 N2 C16 C17 -92.0(7) . . . . ? C21 C16 C17 C18 -4.1(10) . . . . ? N2 C16 C17 C18 -179.9(6) . . . . ? C21 C16 C17 C22 172.3(6) . . . . ? N2 C16 C17 C22 -3.5(9) . . . . ? C16 C17 C18 C19 0.4(11) . . . . ? C22 C17 C18 C19 -176.0(7) . . . . ? C17 C18 C19 C20 2.4(13) . . . . ? C18 C19 C20 C21 -1.7(13) . . . . ? C19 C20 C21 C16 -1.8(11) . . . . ? C19 C20 C21 C25 176.3(7) . . . . ? C17 C16 C21 C20 4.8(10) . . . . ? N2 C16 C21 C20 -179.3(6) . . . . ? C17 C16 C21 C25 -173.2(6) . . . . ? N2 C16 C21 C25 2.6(9) . . . . ? C16 C17 C22 C24 -94.0(8) . . . . ? C18 C17 C22 C24 82.3(9) . . . . ? C16 C17 C22 C23 141.2(7) . . . . ? C18 C17 C22 C23 -42.5(9) . . . . ? C20 C21 C25 C27 -77.9(9) . . . . ? C16 C21 C25 C27 100.1(8) . . . . ? C20 C21 C25 C26 44.9(10) . . . . ? C16 C21 C25 C26 -137.1(7) . . . . ? C29 N3 C28 N4 -0.7(8) . . . . ? C31 N3 C28 N4 -179.3(7) . . . . ? C29 N3 C28 Ni1 178.8(6) . . . . ? C31 N3 C28 Ni1 0.3(12) . . . . ? C30 N4 C28 N3 0.4(8) . . . . ? C34 N4 C28 N3 178.6(6) . . . . ? C30 N4 C28 Ni1 -179.2(5) . . . . ? C34 N4 C28 Ni1 -1.0(10) . . . . ? C1 Ni1 C28 N3 -152.4(14) . . . . ? Br1 Ni1 C28 N3 -85.2(7) . . . . ? Br2 Ni1 C28 N3 85.4(7) . . . . ? C1 Ni1 C28 N4 27(2) . . . . ? Br1 Ni1 C28 N4 94.3(6) . . . . ? Br2 Ni1 C28 N4 -95.1(6) . . . . ? C28 N3 C29 C30 0.8(10) . . . . ? C31 N3 C29 C30 179.3(8) . . . . ? N3 C29 C30 N4 -0.5(9) . . . . ? C28 N4 C30 C29 0.0(9) . . . . ? C34 N4 C30 C29 -178.1(7) . . . . ? C28 N3 C31 C33 -120.1(10) . . . . ? C29 N3 C31 C33 61.5(13) . . . . ? C28 N3 C31 C32 117.1(9) . . . . ? C29 N3 C31 C32 -61.2(11) . . . . ? C28 N4 C34 C35 -112.2(8) . . . . ? C30 N4 C34 C35 65.7(10) . . . . ? C28 N4 C34 C36 122.1(8) . . . . ? C30 N4 C34 C36 -60.0(10) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 3.089 _refine_diff_density_min -2.708 _refine_diff_density_rms 0.200 # Attachment '- shelxl-3.cif' data_shelxl3 _database_code_depnum_ccdc_archive 'CCDC 805191' #TrackingRef '- shelxl-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H40 Br2 N4 Ni' _chemical_formula_sum 'C30 H40 Br2 N4 Ni' _chemical_formula_weight 675.19 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43 21 2' _symmetry_space_group_name_Hall 'P 4nw 2abw' _symmetry_Int_Tables_number 96 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' 'x+1/2, -y+1/2, -z+1/4' '-y, -x, -z+1/2' _cell_length_a 11.533(4) _cell_length_b 11.533(4) _cell_length_c 22.823(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3036.0(17) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5470 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 3.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.330 _exptl_absorpt_correction_T_max 0.500 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5587 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2807 _reflns_number_gt 2493 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1605P)^2^+8.9169P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.12(4) _refine_ls_number_reflns 2807 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0868 _refine_ls_wR_factor_ref 0.2654 _refine_ls_wR_factor_gt 0.2533 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.50162(13) 0.39332(14) 0.65815(5) 0.0582(5) Uani 1 1 d . . . Ni1 Ni 0.54790(8) 0.45210(8) 0.7500 0.0160(4) Uani 1 2 d S . . N1 N 0.3137(6) 0.5557(6) 0.7519(3) 0.0203(15) Uani 1 1 d . . . N2 N 0.7730(6) 0.3471(6) 0.7289(4) 0.0262(17) Uani 1 1 d . . . C1 C 0.4297(7) 0.5703(7) 0.7500 0.020(2) Uani 1 2 d S . . C2 C 0.2590(8) 0.6627(8) 0.7520(5) 0.031(2) Uani 1 1 d . . . H2 H 0.1787 0.6755 0.7545 0.037 Uiso 1 1 calc R . . C3 C 0.2583(7) 0.4423(7) 0.7520(4) 0.0214(10) Uani 1 1 d . . . C4 C 0.2557(7) 0.3814(8) 0.8066(4) 0.0214(10) Uani 1 1 d . . . C5 C 0.2136(7) 0.2676(8) 0.8037(4) 0.0214(10) Uani 1 1 d . . . H5 H 0.2129 0.2230 0.8381 0.026 Uiso 1 1 calc R . . C6 C 0.1730(7) 0.2176(7) 0.7525(5) 0.0257(19) Uani 1 1 d . . . C7 C 0.1719(7) 0.2853(8) 0.7010(4) 0.0237(19) Uani 1 1 d . . . H7 H 0.1429 0.2529 0.6662 0.028 Uiso 1 1 calc R . . C8 C 0.2126(7) 0.3984(8) 0.7005(4) 0.0203(18) Uani 1 1 d . . . C9 C 0.2972(10) 0.4295(9) 0.8607(4) 0.036(3) Uani 1 1 d . . . H9A H 0.3076 0.3678 0.8891 0.054 Uiso 1 1 calc R . . H9B H 0.2414 0.4851 0.8755 0.054 Uiso 1 1 calc R . . H9C H 0.3708 0.4680 0.8540 0.054 Uiso 1 1 calc R . . C10 C 0.1296(11) 0.0957(9) 0.7506(5) 0.044(3) Uani 1 1 d . . . H10A H 0.1950 0.0428 0.7489 0.066 Uiso 1 1 calc R . . H10B H 0.0815 0.0852 0.7161 0.066 Uiso 1 1 calc R . . H10C H 0.0843 0.0799 0.7855 0.066 Uiso 1 1 calc R . . C11 C 0.2080(9) 0.4705(8) 0.6459(4) 0.031(2) Uani 1 1 d . . . H11A H 0.1289 0.4731 0.6315 0.046 Uiso 1 1 calc R . . H11B H 0.2578 0.4364 0.6163 0.046 Uiso 1 1 calc R . . H11C H 0.2342 0.5485 0.6546 0.046 Uiso 1 1 calc R . . C12 C 0.6637(7) 0.3363(7) 0.7500 0.022(2) Uani 1 2 d S . . C13 C 0.8325(8) 0.2396(8) 0.7377(4) 0.029(2) Uani 1 1 d . . . H13 H 0.9099 0.2238 0.7275 0.035 Uiso 1 1 calc R . . C14 C 0.8200(8) 0.4519(9) 0.7041(4) 0.030(2) Uani 1 1 d . . . H14 H 0.7562 0.5092 0.7021 0.036 Uiso 1 1 calc R . . C15 C 0.9117(9) 0.5013(12) 0.7436(6) 0.048(3) Uani 1 1 d . . . H15A H 0.8789 0.5157 0.7820 0.071 Uiso 1 1 calc R . . H15B H 0.9401 0.5736 0.7272 0.071 Uiso 1 1 calc R . . H15C H 0.9752 0.4467 0.7469 0.071 Uiso 1 1 calc R . . C16 C 0.8637(12) 0.4340(12) 0.6430(5) 0.050(3) Uani 1 1 d . . . H16A H 0.9298 0.3820 0.6437 0.075 Uiso 1 1 calc R . . H16B H 0.8869 0.5079 0.6264 0.075 Uiso 1 1 calc R . . H16C H 0.8027 0.4004 0.6191 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0543(8) 0.0651(10) 0.0550(8) -0.0107(6) -0.0029(7) 0.0101(6) Ni1 0.0133(5) 0.0133(5) 0.0214(7) 0.0004(4) 0.0004(4) 0.0010(5) N1 0.014(3) 0.020(3) 0.026(3) -0.010(3) 0.004(3) 0.002(3) N2 0.013(3) 0.020(4) 0.046(4) 0.005(4) 0.006(3) 0.002(3) C1 0.020(4) 0.020(4) 0.021(5) 0.002(3) 0.002(3) -0.012(5) C2 0.020(4) 0.021(4) 0.052(6) -0.001(5) 0.000(5) 0.005(3) C3 0.013(2) 0.023(3) 0.029(2) 0.006(2) 0.002(2) -0.0002(19) C4 0.013(2) 0.023(3) 0.029(2) 0.006(2) 0.002(2) -0.0002(19) C5 0.013(2) 0.023(3) 0.029(2) 0.006(2) 0.002(2) -0.0002(19) C6 0.023(4) 0.015(4) 0.040(5) 0.007(4) 0.002(4) -0.006(3) C7 0.012(4) 0.030(5) 0.029(4) -0.007(4) -0.006(4) -0.006(3) C8 0.015(4) 0.021(4) 0.024(4) 0.006(4) -0.006(3) -0.003(3) C9 0.051(6) 0.031(6) 0.026(4) 0.006(4) 0.006(4) -0.016(5) C10 0.059(7) 0.027(5) 0.045(5) 0.008(5) -0.002(6) -0.015(5) C11 0.037(5) 0.026(5) 0.029(5) 0.011(4) -0.006(4) -0.005(4) C12 0.023(4) 0.023(4) 0.022(5) -0.001(4) -0.001(4) 0.003(5) C13 0.017(4) 0.031(5) 0.039(5) 0.001(4) 0.008(4) 0.019(3) C14 0.018(4) 0.033(5) 0.039(5) -0.004(5) 0.008(4) 0.000(4) C15 0.030(5) 0.062(7) 0.051(7) -0.016(7) 0.002(5) -0.010(6) C16 0.053(7) 0.057(8) 0.040(6) 0.000(6) 0.009(6) -0.014(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Ni1 2.2670(14) . ? Ni1 C12 1.888(12) . ? Ni1 C1 1.929(12) . ? Ni1 Br1 2.2670(14) 8_666 ? N1 C1 1.349(9) . ? N1 C2 1.386(11) . ? N1 C3 1.456(11) . ? N2 C12 1.356(10) . ? N2 C13 1.432(11) . ? N2 C14 1.440(12) . ? C1 N1 1.349(10) 8_666 ? C2 C2 1.280(19) 8_666 ? C2 H2 0.9400 . ? C3 C8 1.385(13) . ? C3 C4 1.431(12) . ? C4 C5 1.400(12) . ? C4 C9 1.436(13) . ? C5 C6 1.384(14) . ? C5 H5 0.9400 . ? C6 C7 1.411(13) . ? C6 C10 1.493(12) . ? C7 C8 1.386(13) . ? C7 H7 0.9400 . ? C8 C11 1.498(12) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 N2 1.356(10) 8_666 ? C13 C13 1.304(19) 8_666 ? C13 H13 0.9400 . ? C14 C16 1.498(14) . ? C14 C15 1.501(14) . ? C14 H14 0.9900 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 H16C 0.9700 . ? 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 C12 Ni1 C1 180.000(1) . . ? C12 Ni1 Br1 87.42(5) . 8_666 ? C1 Ni1 Br1 92.58(5) . 8_666 ? C12 Ni1 Br1 87.42(5) . . ? C1 Ni1 Br1 92.58(5) . . ? Br1 Ni1 Br1 174.85(10) 8_666 . ? C1 N1 C2 109.9(8) . . ? C1 N1 C3 123.2(7) . . ? C2 N1 C3 126.9(7) . . ? C12 N2 C13 108.5(7) . . ? C12 N2 C14 124.5(8) . . ? C13 N2 C14 127.0(7) . . ? N1 C1 N1 104.4(10) 8_666 . ? N1 C1 Ni1 127.8(5) 8_666 . ? N1 C1 Ni1 127.8(5) . . ? C2 C2 N1 107.9(5) 8_666 . ? C2 C2 H2 126.1 8_666 . ? N1 C2 H2 126.1 . . ? C8 C3 C4 123.5(8) . . ? C8 C3 N1 119.5(8) . . ? C4 C3 N1 116.9(8) . . ? C5 C4 C3 115.2(8) . . ? C5 C4 C9 121.3(8) . . ? C3 C4 C9 123.5(8) . . ? C6 C5 C4 123.3(8) . . ? C6 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C5 C6 C7 118.4(8) . . ? C5 C6 C10 122.1(9) . . ? C7 C6 C10 119.6(9) . . ? C8 C7 C6 121.7(8) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C3 C8 C7 117.7(8) . . ? C3 C8 C11 121.2(8) . . ? C7 C8 C11 121.1(8) . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 N2 107.3(10) . 8_666 ? N2 C12 Ni1 126.4(5) . . ? N2 C12 Ni1 126.4(5) 8_666 . ? C13 C13 N2 107.9(5) 8_666 . ? C13 C13 H13 126.1 8_666 . ? N2 C13 H13 126.1 . . ? N2 C14 C16 112.1(9) . . ? N2 C14 C15 110.4(9) . . ? C16 C14 C15 112.0(9) . . ? N2 C14 H14 107.4 . . ? C16 C14 H14 107.4 . . ? C15 C14 H14 107.4 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N1 -0.9(6) . . . 8_666 ? C3 N1 C1 N1 177.5(9) . . . 8_666 ? C2 N1 C1 Ni1 179.1(6) . . . . ? C3 N1 C1 Ni1 -2.5(9) . . . . ? C12 Ni1 C1 N1 -178(100) . . . 8_666 ? Br1 Ni1 C1 N1 70.1(4) 8_666 . . 8_666 ? Br1 Ni1 C1 N1 -109.9(4) . . . 8_666 ? C12 Ni1 C1 N1 2(100) . . . . ? Br1 Ni1 C1 N1 -109.9(4) 8_666 . . . ? Br1 Ni1 C1 N1 70.1(4) . . . . ? C1 N1 C2 C2 2.4(16) . . . 8_666 ? C3 N1 C2 C2 -175.9(12) . . . 8_666 ? C1 N1 C3 C8 -99.9(9) . . . . ? C2 N1 C3 C8 78.2(12) . . . . ? C1 N1 C3 C4 79.4(9) . . . . ? C2 N1 C3 C4 -102.5(11) . . . . ? C8 C3 C4 C5 6.2(12) . . . . ? N1 C3 C4 C5 -173.1(7) . . . . ? C8 C3 C4 C9 -176.4(9) . . . . ? N1 C3 C4 C9 4.3(13) . . . . ? C3 C4 C5 C6 -2.4(12) . . . . ? C9 C4 C5 C6 -179.8(9) . . . . ? C4 C5 C6 C7 -1.2(13) . . . . ? C4 C5 C6 C10 179.4(9) . . . . ? C5 C6 C7 C8 1.4(13) . . . . ? C10 C6 C7 C8 -179.2(9) . . . . ? C4 C3 C8 C7 -6.1(13) . . . . ? N1 C3 C8 C7 173.2(7) . . . . ? C4 C3 C8 C11 174.3(8) . . . . ? N1 C3 C8 C11 -6.4(12) . . . . ? C6 C7 C8 C3 2.1(13) . . . . ? C6 C7 C8 C11 -178.3(9) . . . . ? C13 N2 C12 N2 -0.3(5) . . . 8_666 ? C14 N2 C12 N2 -178.1(10) . . . 8_666 ? C13 N2 C12 Ni1 179.7(5) . . . . ? C14 N2 C12 Ni1 1.9(10) . . . . ? C1 Ni1 C12 N2 154(100) . . . . ? Br1 Ni1 C12 N2 -93.9(4) 8_666 . . . ? Br1 Ni1 C12 N2 86.1(4) . . . . ? C1 Ni1 C12 N2 -26(100) . . . 8_666 ? Br1 Ni1 C12 N2 86.1(4) 8_666 . . 8_666 ? Br1 Ni1 C12 N2 -93.9(4) . . . 8_666 ? C12 N2 C13 C13 0.9(13) . . . 8_666 ? C14 N2 C13 C13 178.6(11) . . . 8_666 ? C12 N2 C14 C16 -123.2(10) . . . . ? C13 N2 C14 C16 59.4(13) . . . . ? C12 N2 C14 C15 111.2(9) . . . . ? C13 N2 C14 C15 -66.2(13) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.944 _refine_diff_density_min -1.998 _refine_diff_density_rms 0.227