# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'XiaoMing Ren' _publ_contact_author_email xmren@njut.edu.cn _publ_author_name 'XiaoMing Ren' # Attachment '- 822589-808974.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 822589' #TrackingRef '- 822589-808974.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H6 Cl D5 N5 Ni S4' _chemical_formula_weight 548.77 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0783(13) _cell_length_b 26.163(3) _cell_length_c 7.3540(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.526(2) _cell_angle_gamma 90.00 _cell_volume 2268.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4823 _cell_measurement_theta_min 2.3254 _cell_measurement_theta_max 27.9369 _exptl_crystal_description club-shaped _exptl_crystal_colour dark _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1100 _exptl_absorpt_coefficient_mu 1.360 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7727 _exptl_absorpt_correction_T_max 0.9351 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12081 _diffrn_reflns_av_R_equivalents 0.1047 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4438 _reflns_number_gt 3744 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The crystal has low quality, 3 violations of systematic absences and 350 inconsistent equivalentRint reflections were observed, which lead to Rint value is higher (0.1047). ; _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^)+(0.0554P)^2^+0.4306P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0094(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4438 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.76817(3) 0.774959(15) 0.53965(6) 0.04560(17) Uani 1 1 d . . . Cl1 Cl 0.76119(12) 0.16770(4) 0.00007(15) 0.0925(4) Uani 1 1 d . . . S1 S 0.90950(7) 0.82328(3) 0.64732(12) 0.0544(2) Uani 1 1 d . . . S2 S 0.65975(7) 0.83888(3) 0.44276(12) 0.0524(2) Uani 1 1 d . . . S3 S 0.88209(7) 0.71278(3) 0.62513(12) 0.0531(2) Uani 1 1 d . . . S4 S 0.63039(7) 0.72449(3) 0.43116(13) 0.0526(2) Uani 1 1 d . . . N1 N 1.0105(3) 0.95399(13) 0.6615(6) 0.0913(11) Uani 1 1 d . . . N2 N 0.6679(3) 0.97837(12) 0.3824(5) 0.0833(10) Uani 1 1 d . . . N3 N 0.9038(3) 0.57368(13) 0.6124(6) 0.0810(10) Uani 1 1 d . . . N4 N 0.5609(3) 0.58802(13) 0.3609(6) 0.0860(11) Uani 1 1 d . . . N5 N 0.7209(2) 0.42266(9) 0.1178(4) 0.0514(6) Uani 1 1 d . . . C1 C 0.9410(3) 0.92349(14) 0.6254(5) 0.0638(9) Uani 1 1 d . . . C2 C 0.8600(3) 0.88350(12) 0.5843(5) 0.0493(7) Uani 1 1 d . . . C3 C 0.7052(3) 0.93989(14) 0.4347(5) 0.0612(9) Uani 1 1 d . . . C4 C 0.7501(3) 0.89019(13) 0.4954(4) 0.0497(7) Uani 1 1 d . . . C5 C 0.8565(3) 0.61172(14) 0.5849(5) 0.0563(8) Uani 1 1 d . . . C6 C 0.8009(3) 0.66018(12) 0.5545(4) 0.0453(7) Uani 1 1 d . . . C7 C 0.6196(3) 0.62173(13) 0.4104(5) 0.0569(8) Uani 1 1 d . . . C8 C 0.6900(3) 0.66506(12) 0.4692(4) 0.0474(7) Uani 1 1 d . . . C9 C 0.8169(3) 0.44018(13) 0.2226(6) 0.0625(9) Uani 1 1 d . . . C10 C 0.8185(4) 0.46430(15) 0.3849(6) 0.0779(12) Uani 1 1 d . . . C11 C 0.7204(5) 0.47116(16) 0.4421(6) 0.0849(14) Uani 1 1 d . . . C12 C 0.6216(4) 0.45358(16) 0.3322(8) 0.0880(14) Uani 1 1 d . . . C13 C 0.6236(3) 0.42925(15) 0.1715(6) 0.0707(10) Uani 1 1 d . . . C14 C 0.7222(3) 0.39545(14) -0.0587(5) 0.0623(9) Uani 1 1 d . . . H14A H 0.7861(3) 0.40738(14) -0.1072(5) 0.075 Uiso 1 1 d R . . H14B H 0.6534(3) 0.40359(14) -0.1495(5) 0.075 Uiso 1 1 d R . . C15 C 0.7305(3) 0.33811(13) -0.0332(4) 0.0499(8) Uani 1 1 d . . . C16 C 0.8331(3) 0.31517(14) 0.0314(5) 0.0624(9) Uani 1 1 d . . . H16 H 0.8977(3) 0.33529(14) 0.0671(5) 0.075 Uiso 1 1 d R . . C17 C 0.8431(3) 0.26326(15) 0.0441(6) 0.0673(10) Uani 1 1 d . . . H17 H 0.9133(3) 0.24807(15) 0.0894(6) 0.081 Uiso 1 1 d R . . C18 C 0.7479(3) 0.23373(14) -0.0095(5) 0.0570(9) Uani 1 1 d . . . C19 C 0.6439(3) 0.25533(15) -0.0719(6) 0.0689(10) Uani 1 1 d . . . H19 H 0.5796(3) 0.23497(15) -0.1056(6) 0.083 Uiso 1 1 d R . . C20 C 0.6360(3) 0.30803(15) -0.0844(5) 0.0665(10) Uani 1 1 d . . . H20 H 0.5656(3) 0.32321(15) -0.1278(5) 0.080 Uiso 1 1 d R . . D9 D 0.8845 0.4355 0.1829 0.080 Uiso 1 1 d R . . D10 D 0.8869 0.4760 0.4568 0.080 Uiso 1 1 d R . . D11 D 0.7205 0.4873 0.5542 0.080 Uiso 1 1 d R . . D12 D 0.5532 0.4582 0.3684 0.080 Uiso 1 1 d R . . D13 D 0.5567 0.4167 0.0969 0.080 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0428(2) 0.0432(3) 0.0461(3) -0.00449(17) -0.00062(18) 0.00215(16) Cl1 0.1548(12) 0.0531(6) 0.0684(7) -0.0076(5) 0.0218(7) -0.0009(6) S1 0.0461(4) 0.0499(5) 0.0602(5) -0.0023(4) -0.0040(4) 0.0005(3) S2 0.0453(4) 0.0480(5) 0.0588(5) -0.0041(4) 0.0004(4) 0.0037(3) S3 0.0425(4) 0.0495(5) 0.0592(5) -0.0046(4) -0.0068(4) 0.0012(3) S4 0.0416(4) 0.0493(5) 0.0600(5) -0.0021(4) -0.0043(4) 0.0027(3) N1 0.087(3) 0.068(2) 0.108(3) -0.001(2) -0.003(2) -0.024(2) N2 0.089(2) 0.0507(19) 0.098(3) 0.0013(19) -0.006(2) 0.0084(18) N3 0.071(2) 0.0557(19) 0.106(3) 0.0055(19) -0.0036(19) 0.0116(17) N4 0.072(2) 0.059(2) 0.117(3) 0.001(2) -0.003(2) -0.0137(17) N5 0.0484(15) 0.0408(14) 0.0598(17) 0.0047(13) 0.0002(12) 0.0008(11) C1 0.065(2) 0.056(2) 0.064(2) 0.0004(18) -0.0011(18) -0.0008(18) C2 0.0514(18) 0.0451(17) 0.0494(18) -0.0039(15) 0.0064(14) -0.0022(14) C3 0.059(2) 0.053(2) 0.066(2) -0.0078(18) 0.0016(17) -0.0004(17) C4 0.0530(18) 0.0449(17) 0.0500(18) -0.0051(15) 0.0089(14) 0.0031(14) C5 0.0519(19) 0.0511(19) 0.061(2) 0.0007(17) 0.0015(16) 0.0003(16) C6 0.0437(15) 0.0452(17) 0.0432(17) 0.0009(14) 0.0016(13) 0.0005(13) C7 0.0496(18) 0.0509(19) 0.064(2) 0.0032(17) -0.0005(15) -0.0037(16) C8 0.0486(17) 0.0480(17) 0.0430(17) 0.0015(14) 0.0041(13) 0.0013(14) C9 0.0502(19) 0.0482(19) 0.081(3) -0.0034(19) -0.0029(17) -0.0005(15) C10 0.082(3) 0.056(2) 0.080(3) -0.010(2) -0.015(2) 0.002(2) C11 0.135(4) 0.048(2) 0.070(3) -0.010(2) 0.019(3) 0.009(2) C12 0.088(3) 0.068(3) 0.118(4) -0.013(3) 0.044(3) 0.003(2) C13 0.052(2) 0.067(2) 0.090(3) -0.007(2) 0.0082(19) -0.0008(18) C14 0.066(2) 0.061(2) 0.055(2) 0.0038(18) 0.0012(17) 0.0003(17) C15 0.0483(18) 0.057(2) 0.0414(17) -0.0032(15) 0.0021(14) 0.0000(14) C16 0.0447(18) 0.061(2) 0.075(2) -0.0123(19) -0.0005(16) -0.0025(16) C17 0.054(2) 0.066(2) 0.072(2) -0.013(2) -0.0071(18) 0.0099(18) C18 0.081(3) 0.0480(18) 0.0408(17) -0.0053(15) 0.0104(17) 0.0021(17) C19 0.060(2) 0.073(3) 0.070(2) -0.009(2) 0.0068(19) -0.0192(19) C20 0.0432(18) 0.070(2) 0.077(3) 0.001(2) -0.0054(16) 0.0025(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S1 2.1338(9) . ? Ni1 S3 2.1353(9) . ? Ni1 S4 2.1386(9) . ? Ni1 S2 2.1481(9) . ? Cl1 C18 1.735(4) . ? S1 C2 1.713(3) . ? S2 C4 1.720(3) . ? S3 C6 1.705(3) . ? S4 C8 1.711(3) . ? N1 C1 1.147(5) . ? N2 C3 1.135(5) . ? N3 C5 1.143(4) . ? N4 C7 1.140(4) . ? N5 C9 1.327(4) . ? N5 C13 1.329(4) . ? N5 C14 1.483(4) . ? C1 C2 1.419(5) . ? C2 C4 1.358(4) . ? C3 C4 1.442(5) . ? C5 C6 1.430(4) . ? C6 C8 1.355(4) . ? C7 C8 1.427(5) . ? C9 C10 1.347(6) . ? C10 C11 1.353(6) . ? C11 C12 1.368(7) . ? C12 C13 1.347(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.512(5) . ? C15 C16 1.366(5) . ? C15 C20 1.370(5) . ? C16 H16 0.9300 . ? C16 C17 1.365(5) . ? C17 H17 0.9300 . ? C17 C18 1.370(5) . ? C18 C19 1.363(5) . ? C19 H19 0.9300 . ? C19 C20 1.384(5) . ? C20 H20 0.9300 . ? 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 S1 Ni1 S3 85.96(3) . . ? S1 Ni1 S4 178.08(4) . . ? S3 Ni1 S4 92.24(3) . . ? S1 Ni1 S2 92.46(3) . . ? S3 Ni1 S2 176.64(4) . . ? S4 Ni1 S2 89.31(3) . . ? C2 S1 Ni1 103.91(11) . . ? C4 S2 Ni1 102.80(12) . . ? C6 S3 Ni1 103.52(11) . . ? C8 S4 Ni1 103.54(11) . . ? C9 N5 C13 120.0(3) . . ? C9 N5 C14 120.0(3) . . ? C13 N5 C14 120.0(3) . . ? N1 C1 C2 176.6(4) . . ? C4 C2 C1 124.3(3) . . ? C4 C2 S1 119.8(3) . . ? C1 C2 S1 115.9(2) . . ? N2 C3 C4 178.0(4) . . ? C2 C4 C3 121.9(3) . . ? C2 C4 S2 120.9(3) . . ? C3 C4 S2 117.1(3) . . ? N3 C5 C6 177.9(4) . . ? C8 C6 C5 122.7(3) . . ? C8 C6 S3 120.7(2) . . ? C5 C6 S3 116.6(2) . . ? N4 C7 C8 178.1(4) . . ? C6 C8 C7 122.0(3) . . ? C6 C8 S4 120.0(2) . . ? C7 C8 S4 118.0(2) . . ? N5 C9 C10 121.3(4) . . ? C9 C10 C11 119.5(4) . . ? C10 C11 C12 118.9(4) . . ? C13 C12 C11 119.8(4) . . ? N5 C13 C12 120.5(4) . . ? H14A C14 H14B 107.9 . . ? H14A C14 N5 109.14(18) . . ? H14B C14 N5 109.11(17) . . ? H14A C14 C15 109.14(18) . . ? H14B C14 C15 109.09(19) . . ? N5 C14 C15 112.4(3) . . ? C16 C15 C20 118.8(3) . . ? C16 C15 C14 120.6(3) . . ? C20 C15 C14 120.4(3) . . ? H16 C16 C17 119.2(2) . . ? H16 C16 C15 119.4(2) . . ? C17 C16 C15 121.4(3) . . ? H17 C17 C16 120.6(2) . . ? H17 C17 C18 120.3(2) . . ? C16 C17 C18 119.0(3) . . ? C19 C18 C17 121.2(4) . . ? C19 C18 Cl1 119.8(3) . . ? C17 C18 Cl1 119.0(3) . . ? H19 C19 C18 120.5(2) . . ? H19 C19 C20 120.8(2) . . ? C18 C19 C20 118.7(3) . . ? H20 C20 C15 119.6(2) . . ? H20 C20 C19 119.5(2) . . ? C15 C20 C19 120.9(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.633 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.079 # Attachment '- 822590-808975.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 822590' #TrackingRef '- 822590-808975.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H6 Br D5 N5 Ni S4' _chemical_formula_weight 593.23 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' S S 0.1246 0.1234 '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' D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0244(17) _cell_length_b 26.253(4) _cell_length_c 7.4047(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.646(3) _cell_angle_gamma 90.00 _cell_volume 2280.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2885 _cell_measurement_theta_min 2.3282 _cell_measurement_theta_max 23.8059 _exptl_crystal_description club-shaped _exptl_crystal_colour dark _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 _exptl_absorpt_coefficient_mu 2.987 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5865 _exptl_absorpt_correction_T_max 0.8650 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12169 _diffrn_reflns_av_R_equivalents 0.1290 _diffrn_reflns_av_sigmaI/netI 0.1084 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4458 _reflns_number_gt 3069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The crystal has low quality, 3 violations of systematic absences and 163 inconsistent equivalentRint reflections were observed, which lead to Rint value is higher (0.1290). ; _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^)+(0.0884P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0044(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4458 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.1728 _refine_ls_wR_factor_gt 0.1631 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.73413(5) 0.22623(3) 0.45856(9) 0.0459(2) Uani 1 1 d . . . S1 S 0.87127(12) 0.27668(5) 0.5696(2) 0.0537(4) Uani 1 1 d . . . S2 S 0.61999(12) 0.28801(5) 0.3712(2) 0.0538(4) Uani 1 1 d . . . S3 S 0.84220(12) 0.16277(5) 0.5580(2) 0.0530(4) Uani 1 1 d . . . S4 S 0.59315(12) 0.17815(5) 0.3486(2) 0.0550(4) Uani 1 1 d . . . Br1 Br 0.26548(9) 0.16697(3) -0.00222(10) 0.0944(4) Uani 1 1 d . . . N1 N 0.9404(5) 0.4125(2) 0.6413(10) 0.0882(19) Uani 1 1 d . . . N2 N 0.5969(5) 0.4264(2) 0.3849(9) 0.0823(17) Uani 1 1 d . . . N3 N 0.8325(5) 0.0240(2) 0.6206(8) 0.0848(18) Uani 1 1 d . . . N4 N 0.4921(5) 0.0481(2) 0.3381(9) 0.0895(19) Uani 1 1 d . . . N5 N 0.2222(4) 0.42632(16) 0.1183(6) 0.0512(11) Uani 1 1 d . . . C1 C 0.8815(5) 0.3786(2) 0.5908(8) 0.0592(15) Uani 1 1 d . . . C2 C 0.8116(5) 0.33554(19) 0.5315(7) 0.0476(13) Uani 1 1 d . . . C3 C 0.7020(4) 0.3403(2) 0.4441(7) 0.0463(12) Uani 1 1 d . . . C4 C 0.6447(5) 0.3885(2) 0.4123(8) 0.0582(14) Uani 1 1 d . . . C5 C 0.7962(6) 0.0623(2) 0.5666(9) 0.0631(16) Uani 1 1 d . . . C6 C 0.7508(4) 0.1116(2) 0.5049(7) 0.0505(13) Uani 1 1 d . . . C7 C 0.6423(5) 0.1182(2) 0.4146(7) 0.0511(13) Uani 1 1 d . . . C8 C 0.5620(5) 0.0780(2) 0.3730(9) 0.0621(15) Uani 1 1 d . . . C9 C 0.3180(5) 0.4430(2) 0.2217(9) 0.0620(16) Uani 1 1 d . . . C10 C 0.3199(6) 0.4664(2) 0.3850(10) 0.078(2) Uani 1 1 d . . . C11 C 0.2200(8) 0.4734(2) 0.4396(10) 0.081(2) Uani 1 1 d . . . C12 C 0.1227(7) 0.4558(3) 0.3310(12) 0.087(2) Uani 1 1 d . . . C13 C 0.1243(5) 0.4324(3) 0.1691(10) 0.0722(18) Uani 1 1 d . . . C14 C 0.2234(5) 0.3993(2) -0.0573(8) 0.0628(16) Uani 1 1 d . . . H14A H 0.2873(5) 0.4115(2) -0.1056(8) 0.075 Uiso 1 1 d R . . H14B H 0.1541(5) 0.4074(2) -0.1474(8) 0.075 Uiso 1 1 d R . . C15 C 0.2325(4) 0.3422(2) -0.0337(7) 0.0485(13) Uani 1 1 d . . . C16 C 0.3360(5) 0.3195(2) 0.0262(9) 0.0620(16) Uani 1 1 d . . . H16 H 0.4010(5) 0.3396(2) 0.0595(9) 0.074 Uiso 1 1 d R . . C17 C 0.3457(5) 0.2674(2) 0.0385(9) 0.0641(16) Uani 1 1 d . . . H17 H 0.4164(5) 0.2520(2) 0.0798(9) 0.077 Uiso 1 1 d R . . C18 C 0.2493(5) 0.2388(2) -0.0114(7) 0.0547(15) Uani 1 1 d . . . C19 C 0.1448(6) 0.2600(3) -0.0679(9) 0.0699(18) Uani 1 1 d . . . H19 H 0.0801(6) 0.2397(3) -0.0982(9) 0.084 Uiso 1 1 d R . . C20 C 0.1361(5) 0.3128(2) -0.0799(9) 0.0649(16) Uani 1 1 d . . . H20 H 0.0651(5) 0.3280(2) -0.1190(9) 0.078 Uiso 1 1 d R . . D9 D 0.3859 0.4387 0.1826 0.078 Uiso 1 1 d R . . D10 D 0.3889 0.4776 0.4591 0.078 Uiso 1 1 d R . . D11 D 0.2194 0.4899 0.5505 0.078 Uiso 1 1 d R . . D12 D 0.0543 0.4598 0.3681 0.078 Uiso 1 1 d R . . D13 D 0.0572 0.4207 0.0934 0.078 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0491(4) 0.0397(4) 0.0478(4) -0.0043(3) 0.0084(3) 0.0009(3) S1 0.0507(8) 0.0457(8) 0.0611(9) -0.0023(7) 0.0047(7) 0.0028(6) S2 0.0495(8) 0.0472(8) 0.0599(9) -0.0033(7) 0.0017(7) -0.0002(6) S3 0.0512(8) 0.0449(8) 0.0616(9) -0.0044(7) 0.0093(7) 0.0018(6) S4 0.0538(8) 0.0464(8) 0.0615(9) -0.0018(7) 0.0052(7) -0.0013(6) Br1 0.1704(9) 0.0519(4) 0.0639(5) -0.0082(3) 0.0323(5) -0.0088(4) N1 0.072(4) 0.054(3) 0.129(5) 0.004(3) 0.002(4) -0.012(3) N2 0.082(4) 0.051(3) 0.105(5) 0.003(3) 0.000(3) 0.009(3) N3 0.094(4) 0.052(4) 0.099(4) 0.001(3) 0.000(4) 0.011(3) N4 0.083(4) 0.068(4) 0.110(5) -0.004(3) 0.006(4) -0.020(3) N5 0.056(3) 0.036(2) 0.059(3) 0.007(2) 0.009(2) 0.004(2) C1 0.056(3) 0.052(4) 0.067(4) 0.008(3) 0.005(3) 0.000(3) C2 0.057(3) 0.040(3) 0.047(3) 0.002(2) 0.013(3) 0.002(2) C3 0.046(3) 0.049(3) 0.043(3) 0.001(2) 0.008(2) 0.000(2) C4 0.059(3) 0.052(4) 0.061(3) 0.000(3) 0.008(3) -0.003(3) C5 0.070(4) 0.050(4) 0.068(4) -0.005(3) 0.013(3) 0.001(3) C6 0.054(3) 0.048(3) 0.052(3) -0.002(2) 0.016(3) 0.004(2) C7 0.060(3) 0.045(3) 0.049(3) -0.004(3) 0.016(3) 0.001(3) C8 0.063(4) 0.053(4) 0.070(4) -0.002(3) 0.012(3) -0.001(3) C9 0.056(4) 0.048(3) 0.079(4) -0.003(3) 0.008(3) -0.001(3) C10 0.087(5) 0.048(4) 0.087(5) -0.010(4) -0.006(4) 0.002(3) C11 0.129(7) 0.040(4) 0.076(5) -0.006(3) 0.026(5) 0.007(4) C12 0.096(6) 0.069(5) 0.110(6) -0.019(4) 0.053(5) -0.008(4) C13 0.059(4) 0.064(4) 0.092(5) -0.006(4) 0.014(4) 0.002(3) C14 0.070(4) 0.064(4) 0.055(3) 0.004(3) 0.014(3) 0.002(3) C15 0.051(3) 0.055(3) 0.038(3) -0.002(2) 0.006(2) 0.003(2) C16 0.051(3) 0.061(4) 0.071(4) -0.013(3) 0.008(3) -0.007(3) C17 0.061(4) 0.064(4) 0.062(4) -0.008(3) 0.002(3) 0.012(3) C18 0.081(4) 0.046(3) 0.038(3) -0.006(2) 0.015(3) -0.005(3) C19 0.071(4) 0.074(4) 0.063(4) -0.010(3) 0.012(3) -0.028(4) C20 0.051(3) 0.072(4) 0.067(4) 0.001(3) 0.005(3) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S4 2.1274(16) . ? Ni1 S2 2.1316(15) . ? Ni1 S1 2.1344(15) . ? Ni1 S3 2.1420(15) . ? S1 C2 1.701(5) . ? S2 C3 1.707(5) . ? S3 C6 1.726(6) . ? S4 C7 1.715(6) . ? Br1 C18 1.896(6) . ? N1 C1 1.147(7) . ? N2 C4 1.144(7) . ? N3 C5 1.133(8) . ? N4 C8 1.137(7) . ? N5 C9 1.312(7) . ? N5 C13 1.321(7) . ? N5 C14 1.484(7) . ? C1 C2 1.419(8) . ? C2 C3 1.341(8) . ? C3 C4 1.437(8) . ? C5 C6 1.440(8) . ? C6 C7 1.340(7) . ? C7 C8 1.419(8) . ? C9 C10 1.353(9) . ? C10 C11 1.362(10) . ? C11 C12 1.347(10) . ? C12 C13 1.351(10) . ? C14 H14B 0.9700 . ? C14 H14A 0.9700 . ? C14 C15 1.511(8) . ? C15 C16 1.363(8) . ? C15 C20 1.373(8) . ? C16 H16 0.9300 . ? C16 C17 1.374(8) . ? C17 H17 0.9300 . ? C17 C18 1.362(8) . ? C18 C19 1.354(9) . ? C19 H19 0.9300 . ? C19 C20 1.390(9) . ? C20 H20 0.9300 . ? 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 S4 Ni1 S2 85.94(6) . . ? S4 Ni1 S1 177.89(6) . . ? S2 Ni1 S1 92.09(6) . . ? S4 Ni1 S3 92.44(6) . . ? S2 Ni1 S3 176.39(7) . . ? S1 Ni1 S3 89.48(6) . . ? C2 S1 Ni1 103.8(2) . . ? C3 S2 Ni1 103.10(19) . . ? C6 S3 Ni1 102.65(19) . . ? C7 S4 Ni1 103.9(2) . . ? C9 N5 C13 121.1(5) . . ? C9 N5 C14 119.7(5) . . ? C13 N5 C14 119.2(5) . . ? N1 C1 C2 178.0(7) . . ? C3 C2 C1 121.9(5) . . ? C3 C2 S1 119.9(4) . . ? C1 C2 S1 118.2(4) . . ? C2 C3 C4 123.1(5) . . ? C2 C3 S2 121.1(4) . . ? C4 C3 S2 115.7(4) . . ? N2 C4 C3 178.5(7) . . ? N3 C5 C6 177.9(7) . . ? C7 C6 C5 122.3(5) . . ? C7 C6 S3 121.0(5) . . ? C5 C6 S3 116.7(4) . . ? C6 C7 C8 123.7(5) . . ? C6 C7 S4 119.9(4) . . ? C8 C7 S4 116.4(4) . . ? N4 C8 C7 175.5(7) . . ? N5 C9 C10 121.0(6) . . ? C9 C10 C11 118.9(6) . . ? C12 C11 C10 119.0(7) . . ? C11 C12 C13 120.4(7) . . ? N5 C13 C12 119.7(6) . . ? H14B C14 H14A 107.8 . . ? H14B C14 N5 109.0(3) . . ? H14A C14 N5 109.0(3) . . ? H14B C14 C15 109.0(3) . . ? H14A C14 C15 109.0(3) . . ? N5 C14 C15 112.8(5) . . ? C16 C15 C20 119.8(6) . . ? C16 C15 C14 120.6(5) . . ? C20 C15 C14 119.6(5) . . ? H16 C16 C15 119.6(4) . . ? H16 C16 C17 119.5(4) . . ? C15 C16 C17 121.0(6) . . ? H17 C17 C18 120.8(4) . . ? H17 C17 C16 120.8(4) . . ? C18 C17 C16 118.4(6) . . ? C19 C18 C17 122.3(7) . . ? C19 C18 Br1 120.1(5) . . ? C17 C18 Br1 117.6(5) . . ? H19 C19 C18 120.6(4) . . ? H19 C19 C20 120.6(4) . . ? C18 C19 C20 118.8(6) . . ? H20 C20 C15 120.2(4) . . ? H20 C20 C19 120.0(4) . . ? C15 C20 C19 119.8(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.343 _refine_diff_density_min -1.132 _refine_diff_density_rms 0.152 # Attachment '- 828237-Br-Py-d5-95K.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 828237' #TrackingRef '- 828237-Br-Py-d5-95K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H6 Br D5 N5 Ni S4' _chemical_formula_weight 593.23 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' S S 0.1246 0.1234 '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' D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2590(15) _cell_length_b 12.042(2) _cell_length_c 26.147(5) _cell_angle_alpha 88.54(3) _cell_angle_beta 86.73(3) _cell_angle_gamma 77.42(3) _cell_volume 2227.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 95(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 _exptl_absorpt_coefficient_mu 3.059 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 95(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22522 _diffrn_reflns_av_R_equivalents 0.1109 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.50 _reflns_number_total 8277 _reflns_number_gt 7527 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+711.8755P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0068(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8277 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2736 _refine_ls_R_factor_gt 0.2664 _refine_ls_wR_factor_ref 0.5639 _refine_ls_wR_factor_gt 0.5616 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _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 0.9350(6) 0.7604(3) 0.27068(15) 0.0144(9) Uiso 1 1 d . . . Ni2 Ni 0.4326(5) 0.7618(3) 0.23323(15) 0.0133(9) Uiso 1 1 d . . . S1 S 0.8341(12) 0.9039(7) 0.3189(3) 0.0234(18) Uiso 1 1 d . . . S2 S 1.0436(12) 0.6516(7) 0.3344(3) 0.0243(18) Uiso 1 1 d . . . S3 S 0.8516(11) 0.8775(6) 0.2088(3) 0.0156(15) Uiso 1 1 d . . . S4 S 1.0474(11) 0.6229(6) 0.2195(3) 0.0151(15) Uiso 1 1 d . . . S5 S 0.3463(11) 0.8788(7) 0.2951(3) 0.0189(16) Uiso 1 1 d . . . S6 S 0.5374(11) 0.6243(7) 0.2851(3) 0.0180(16) Uiso 1 1 d . . . S7 S 0.3241(12) 0.9048(7) 0.1846(3) 0.0214(17) Uiso 1 1 d . . . S8 S 0.5336(12) 0.6514(7) 0.1694(3) 0.0240(18) Uiso 1 1 d . . . Br1 Br 0.4743(6) 0.2265(3) 0.33388(15) 0.0340(10) Uiso 1 1 d . . . Br2 Br -0.0294(5) 0.2320(3) 0.16738(14) 0.0285(9) Uiso 1 1 d . . . N1 N 0.838(6) 1.006(4) 0.4506(16) 0.052(10) Uiso 1 1 d . . . N2 N 1.129(6) 0.665(3) 0.4726(15) 0.046(9) Uiso 1 1 d . . . N3 N 0.855(5) 0.902(3) 0.0702(13) 0.035(8) Uiso 1 1 d . . . N4 N 1.131(4) 0.554(3) 0.0805(12) 0.030(7) Uiso 1 1 d . . . N5 N 0.399(5) 0.910(3) 0.4326(14) 0.041(8) Uiso 1 1 d . . . N6 N 0.653(5) 0.558(3) 0.4198(13) 0.037(8) Uiso 1 1 d . . . N7 N 0.308(6) 1.007(3) 0.0510(15) 0.046(9) Uiso 1 1 d . . . N8 N 0.608(6) 0.658(3) 0.0297(15) 0.045(9) Uiso 1 1 d . . . N9 N 0.603(4) 0.279(3) 0.0712(12) 0.029(7) Uiso 1 1 d . . . N10 N 0.102(4) 0.279(2) 0.4279(10) 0.015(5) Uiso 1 1 d . . . C1 C 0.878(5) 0.938(3) 0.4190(13) 0.022(7) Uiso 1 1 d . . . C2 C 0.917(6) 0.859(3) 0.3802(15) 0.032(8) Uiso 1 1 d . . . C3 C 1.013(5) 0.743(3) 0.3843(13) 0.020(7) Uiso 1 1 d . . . C4 C 1.088(6) 0.701(3) 0.4336(15) 0.033(8) Uiso 1 1 d . . . C5 C 0.892(5) 0.856(3) 0.1064(13) 0.023(7) Uiso 1 1 d . . . C6 C 0.922(5) 0.800(3) 0.1579(13) 0.021(7) Uiso 1 1 d . . . C7 C 1.016(4) 0.689(2) 0.1602(11) 0.010(5) Uiso 1 1 d . . . C8 C 1.086(5) 0.616(3) 0.1181(13) 0.023(7) Uiso 1 1 d . . . C9 C 0.417(5) 0.861(3) 0.3966(13) 0.024(7) Uiso 1 1 d . . . C10 C 0.430(5) 0.803(3) 0.3494(14) 0.027(8) Uiso 1 1 d . . . C11 C 0.506(5) 0.686(3) 0.3448(13) 0.024(7) Uiso 1 1 d . . . C12 C 0.586(6) 0.621(3) 0.3863(15) 0.033(9) Uiso 1 1 d . . . C13 C 0.346(5) 0.936(3) 0.0829(13) 0.023(7) Uiso 1 1 d . . . C14 C 0.396(5) 0.854(3) 0.1257(14) 0.029(8) Uiso 1 1 d . . . C15 C 0.500(4) 0.751(2) 0.1150(11) 0.012(6) Uiso 1 1 d . . . C16 C 0.564(5) 0.694(3) 0.0689(12) 0.019(6) Uiso 1 1 d . . . C17 C 0.650(6) 0.379(3) 0.0642(15) 0.032(8) Uiso 1 1 d . . . D17 D 0.5657 0.4462 0.0733 0.038 Uiso 1 1 d R . . C18 C 0.828(6) 0.380(3) 0.0433(15) 0.033(9) Uiso 1 1 d . . . D18 D 0.8687 0.4487 0.0403 0.040 Uiso 1 1 d R . . C19 C 0.949(6) 0.278(4) 0.0261(16) 0.039(10) Uiso 1 1 d . . . D19 D 1.0676 0.2767 0.0103 0.047 Uiso 1 1 d R . . C20 C 0.878(5) 0.178(3) 0.0345(13) 0.024(7) Uiso 1 1 d . . . D20 D 0.9547 0.1084 0.0246 0.029 Uiso 1 1 d R . . C21 C 0.712(5) 0.178(3) 0.0552(12) 0.019(6) Uiso 1 1 d . . . D21 D 0.6687 0.1111 0.0591 0.022 Uiso 1 1 d R . . C22 C 0.414(8) 0.279(5) 0.096(2) 0.057(13) Uiso 1 1 d . . . H22A H 0.364(8) 0.216(5) 0.085(2) 0.068 Uiso 1 1 d R . . H22B H 0.325(8) 0.350(5) 0.089(2) 0.068 Uiso 1 1 d R . . C23 C 0.450(3) 0.2655(16) 0.1573(7) 0.017(6) Uiso 1 1 d G . . C24 C 0.398(3) 0.3596(16) 0.1873(7) 0.015(6) Uiso 1 1 d G . . H24 H 0.358(5) 0.431(2) 0.1722(10) 0.018 Uiso 1 1 d R . . C25 C 0.404(3) 0.3487(16) 0.2393(7) 0.030(8) Uiso 1 1 d G . . H25 H 0.368(5) 0.413(2) 0.2597(10) 0.035 Uiso 1 1 d R . . C26 C 0.462(3) 0.2438(16) 0.2614(7) 0.018(6) Uiso 1 1 d G . . C27 C 0.514(3) 0.1497(16) 0.2314(7) 0.017(6) Uiso 1 1 d G . . H27 H 0.554(5) 0.078(2) 0.2465(10) 0.020 Uiso 1 1 d R . . C28 C 0.508(3) 0.1605(16) 0.1794(7) 0.021(7) Uiso 1 1 d G . . H28 H 0.544(5) 0.096(2) 0.1589(10) 0.025 Uiso 1 1 d R . . C29 C 0.152(4) 0.377(3) 0.4345(12) 0.016(6) Uiso 1 1 d . . . D29 D 0.0713 0.4439 0.4238 0.019 Uiso 1 1 d R . . C30 C 0.324(6) 0.386(4) 0.4571(17) 0.042(10) Uiso 1 1 d . . . D30 D 0.3610 0.4545 0.4616 0.051 Uiso 1 1 d R . . C31 C 0.426(6) 0.280(3) 0.4711(14) 0.030(8) Uiso 1 1 d . . . D31 D 0.5421 0.2765 0.4852 0.036 Uiso 1 1 d R . . C32 C 0.369(5) 0.183(3) 0.4658(12) 0.018(6) Uiso 1 1 d . . . D32 D 0.4435 0.1161 0.4782 0.022 Uiso 1 1 d R . . C33 C 0.198(5) 0.176(3) 0.4422(14) 0.027(8) Uiso 1 1 d . . . D33 D 0.1596 0.1086 0.4374 0.032 Uiso 1 1 d R . . C34 C -0.091(5) 0.279(3) 0.4027(12) 0.020(7) Uiso 1 1 d . . . H34A H -0.144(5) 0.217(3) 0.4174(12) 0.024 Uiso 1 1 d R . . H34B H -0.180(5) 0.350(3) 0.4107(12) 0.024 Uiso 1 1 d R . . C35 C -0.066(4) 0.2661(19) 0.3439(8) 0.032(8) Uiso 1 1 d G . . C36 C -0.114(4) 0.3613(18) 0.3138(8) 0.024(7) Uiso 1 1 d G . . H36 H -0.157(5) 0.432(2) 0.3288(11) 0.029 Uiso 1 1 d R . . C37 C -0.098(3) 0.3526(17) 0.2617(8) 0.028(8) Uiso 1 1 d G . . H37 H -0.131(5) 0.417(2) 0.2412(11) 0.034 Uiso 1 1 d R . . C38 C -0.035(3) 0.2487(18) 0.2396(8) 0.019(7) Uiso 1 1 d G . . C39 C 0.013(4) 0.1535(18) 0.2697(8) 0.031(8) Uiso 1 1 d G . . H39 H 0.056(5) 0.083(3) 0.2547(11) 0.037 Uiso 1 1 d R . . C40 C -0.003(4) 0.1622(19) 0.3219(9) 0.033(9) Uiso 1 1 d G . . H40 H 0.030(6) 0.097(3) 0.3423(12) 0.040 Uiso 1 1 d R . . _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 S1 2.138(9) . ? Ni1 S3 2.143(8) . ? Ni1 S4 2.144(8) . ? Ni1 S2 2.169(10) . ? Ni2 S5 2.146(9) . ? Ni2 S6 2.148(9) . ? Ni2 S7 2.148(9) . ? Ni2 S8 2.154(10) . ? S1 C2 1.77(4) . ? S2 C3 1.70(3) . ? S3 C6 1.64(3) . ? S4 C7 1.73(3) . ? S5 C10 1.73(4) . ? S6 C11 1.73(4) . ? S7 C14 1.68(4) . ? S8 C15 1.83(3) . ? Br1 C26 1.906(19) . ? Br2 C38 1.90(2) . ? N1 C1 1.16(5) . ? N2 C4 1.13(5) . ? N3 C5 1.10(5) . ? N4 C8 1.23(5) . ? N5 C9 1.11(5) . ? N6 C12 1.19(5) . ? N7 C13 1.19(5) . ? N8 C16 1.13(5) . ? N9 C17 1.33(5) . ? N9 C21 1.36(4) . ? N9 C22 1.48(6) . ? N10 C29 1.33(4) . ? N10 C33 1.34(4) . ? N10 C34 1.58(4) . ? C1 C2 1.38(5) . ? C2 C3 1.43(5) . ? C3 C4 1.46(5) . ? C5 C6 1.49(5) . ? C6 C7 1.37(4) . ? C7 C8 1.43(4) . ? C9 C10 1.42(5) . ? C10 C11 1.41(5) . ? C11 C12 1.40(5) . ? C13 C14 1.48(5) . ? C14 C15 1.33(5) . ? C15 C16 1.41(4) . ? C17 C18 1.38(6) . ? C18 C19 1.41(6) . ? C19 C20 1.42(5) . ? C20 C21 1.29(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 C23 1.63(5) . ? C23 C28 1.367(13) . ? C23 C24 1.367(13) . ? C24 H24 0.930(9) . ? C24 C25 1.366(13) . ? C25 H25 0.930(9) . ? C25 C26 1.367(13) . ? C26 C27 1.367(13) . ? C27 H27 0.930(9) . ? C27 C28 1.367(13) . ? C28 H28 0.930(9) . ? C29 C30 1.44(5) . ? C30 C31 1.38(6) . ? C31 C32 1.34(5) . ? C32 C33 1.43(5) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 C35 1.55(4) . ? C35 C40 1.366(15) . ? C35 C36 1.366(15) . ? C36 H36 0.930(10) . ? C36 C37 1.366(15) . ? C37 H37 0.930(10) . ? C37 C38 1.366(15) . ? C38 C39 1.366(15) . ? C39 H39 0.930(10) . ? C39 C40 1.366(15) . ? C40 H40 0.930(10) . ? 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 S1 Ni1 S3 85.2(3) . . ? S1 Ni1 S4 176.2(4) . . ? S3 Ni1 S4 92.5(3) . . ? S1 Ni1 S2 92.6(4) . . ? S3 Ni1 S2 173.8(4) . . ? S4 Ni1 S2 89.3(3) . . ? S5 Ni2 S6 91.9(3) . . ? S5 Ni2 S7 85.2(3) . . ? S6 Ni2 S7 177.2(4) . . ? S5 Ni2 S8 175.9(4) . . ? S6 Ni2 S8 89.7(3) . . ? S7 Ni2 S8 93.1(3) . . ? C2 S1 Ni1 105.1(13) . . ? C3 S2 Ni1 103.4(12) . . ? C6 S3 Ni1 103.2(12) . . ? C7 S4 Ni1 102.1(10) . . ? C10 S5 Ni2 104.9(13) . . ? C11 S6 Ni2 104.6(12) . . ? C14 S7 Ni2 102.5(13) . . ? C15 S8 Ni2 102.0(10) . . ? C17 N9 C21 124(3) . . ? C17 N9 C22 117(4) . . ? C21 N9 C22 119(3) . . ? C29 N10 C33 126(3) . . ? C29 N10 C34 119(2) . . ? C33 N10 C34 115(3) . . ? N1 C1 C2 177(4) . . ? C1 C2 C3 127(3) . . ? C1 C2 S1 117(3) . . ? C3 C2 S1 116(3) . . ? C2 C3 C4 118(3) . . ? C2 C3 S2 123(3) . . ? C4 C3 S2 119(3) . . ? N2 C4 C3 173(4) . . ? N3 C5 C6 174(4) . . ? C7 C6 C5 118(3) . . ? C7 C6 S3 123(3) . . ? C5 C6 S3 118(2) . . ? C6 C7 C8 127(3) . . ? C6 C7 S4 119(2) . . ? C8 C7 S4 114(2) . . ? N4 C8 C7 175(4) . . ? N5 C9 C10 176(4) . . ? C11 C10 C9 123(3) . . ? C11 C10 S5 118(3) . . ? C9 C10 S5 119(3) . . ? C12 C11 C10 121(3) . . ? C12 C11 S6 118(3) . . ? C10 C11 S6 120(3) . . ? N6 C12 C11 175(4) . . ? N7 C13 C14 175(4) . . ? C15 C14 C13 118(3) . . ? C15 C14 S7 126(3) . . ? C13 C14 S7 116(3) . . ? C14 C15 C16 133(3) . . ? C14 C15 S8 115(2) . . ? C16 C15 S8 111(2) . . ? N8 C16 C15 174(4) . . ? N9 C17 C18 118(4) . . ? C17 C18 C19 120(4) . . ? C18 C19 C20 116(4) . . ? C21 C20 C19 123(4) . . ? C20 C21 N9 119(3) . . ? H22A C22 H22B 108.8 . . ? H22A C22 N9 111(2) . . ? H22B C22 N9 111(2) . . ? H22A C22 C23 111(2) . . ? H22B C22 C23 111(2) . . ? N9 C22 C23 105(3) . . ? C28 C23 C24 120.0 . . ? C28 C23 C22 121(2) . . ? C24 C23 C22 119(2) . . ? H24 C24 C25 120.0 . . ? H24 C24 C23 120.0 . . ? C25 C24 C23 120.0 . . ? H25 C25 C24 120.0 . . ? H25 C25 C26 120.0 . . ? C24 C25 C26 120.0 . . ? C27 C26 C25 120.0 . . ? C27 C26 Br1 119.2(11) . . ? C25 C26 Br1 120.8(11) . . ? H27 C27 C26 120.0 . . ? H27 C27 C28 120.0 . . ? C26 C27 C28 120.0 . . ? H28 C28 C23 120.0 . . ? H28 C28 C27 120.0 . . ? C23 C28 C27 120.0 . . ? N10 C29 C30 124(3) . . ? C31 C30 C29 111(4) . . ? C32 C31 C30 124(4) . . ? C31 C32 C33 124(3) . . ? N10 C33 C32 112(3) . . ? H34A C34 H34B 107.9 . . ? H34A C34 C35 109.1(15) . . ? H34B C34 C35 109.1(15) . . ? H34A C34 N10 109.2(15) . . ? H34B C34 N10 109.2(15) . . ? C35 C34 N10 112(2) . . ? C40 C35 C36 120.0 . . ? C40 C35 C34 121.6(18) . . ? C36 C35 C34 118.4(18) . . ? H36 C36 C37 120.0 . . ? H36 C36 C35 120.0 . . ? C37 C36 C35 120.0 . . ? H37 C37 C38 120.0 . . ? H37 C37 C36 120.0 . . ? C38 C37 C36 120.0 . . ? C37 C38 C39 120.0 . . ? C37 C38 Br2 121.0(12) . . ? C39 C38 Br2 118.8(12) . . ? H39 C39 C40 120.0 . . ? H39 C39 C38 120.0 . . ? C40 C39 C38 120.0 . . ? H40 C40 C35 120.0 . . ? H40 C40 C39 120.0 . . ? C35 C40 C39 120.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 4.961 _refine_diff_density_min -3.131 _refine_diff_density_rms 0.515 # Attachment '- 828238-Cl-Py-d5-95K.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 828238' #TrackingRef '- 828238-Cl-Py-d5-95K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H6 Cl D5 N5 Ni S4' _chemical_formula_weight 548.77 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' S S 0.1246 0.1234 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2039(14) _cell_length_b 12.095(2) _cell_length_c 26.005(5) _cell_angle_alpha 88.53(3) _cell_angle_beta 86.86(3) _cell_angle_gamma 77.42(3) _cell_volume 2208.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 95(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1100 _exptl_absorpt_coefficient_mu 1.397 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 95(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19323 _diffrn_reflns_av_R_equivalents 0.1086 _diffrn_reflns_av_sigmaI/netI 0.1067 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.50 _reflns_number_total 8204 _reflns_number_gt 6929 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0005P)^2^+644.1237P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8204 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2819 _refine_ls_R_factor_gt 0.2689 _refine_ls_wR_factor_ref 0.5820 _refine_ls_wR_factor_gt 0.5764 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 0.9332(5) 0.7646(3) 0.27162(14) 0.0139(8) Uiso 1 1 d . . . Ni2 Ni 0.4328(5) 0.7654(3) 0.23245(14) 0.0127(8) Uiso 1 1 d . . . S1 S 0.8336(11) 0.9084(6) 0.3197(3) 0.0215(16) Uiso 1 1 d . . . S2 S 1.0354(11) 0.6551(7) 0.3359(3) 0.0218(16) Uiso 1 1 d . . . S3 S 0.8541(10) 0.8808(6) 0.2092(3) 0.0141(14) Uiso 1 1 d . . . S4 S 1.0455(10) 0.6269(6) 0.2200(3) 0.0136(14) Uiso 1 1 d . . . S5 S 0.3464(10) 0.8812(6) 0.2945(3) 0.0177(15) Uiso 1 1 d . . . S6 S 0.5354(10) 0.6264(6) 0.2840(3) 0.0169(14) Uiso 1 1 d . . . S7 S 0.3285(11) 0.9091(6) 0.1834(3) 0.0196(15) Uiso 1 1 d . . . S8 S 0.5338(11) 0.6554(6) 0.1684(3) 0.0199(15) Uiso 1 1 d . . . Cl1 Cl 0.4709(12) 0.2325(7) 0.3333(3) 0.0322(18) Uiso 1 1 d . . . Cl2 Cl -0.0275(11) 0.2372(7) 0.1690(3) 0.0273(17) Uiso 1 1 d . . . N1 N 0.852(4) 1.014(3) 0.4497(12) 0.035(7) Uiso 1 1 d . . . N2 N 1.135(4) 0.667(3) 0.4745(12) 0.036(7) Uiso 1 1 d . . . N3 N 0.862(4) 0.904(3) 0.0678(12) 0.035(7) Uiso 1 1 d . . . N4 N 1.132(4) 0.557(2) 0.0814(11) 0.028(6) Uiso 1 1 d . . . N5 N 0.398(4) 0.912(3) 0.4328(12) 0.034(7) Uiso 1 1 d . . . N6 N 0.647(4) 0.560(3) 0.4197(12) 0.035(7) Uiso 1 1 d . . . N7 N 0.323(4) 1.011(3) 0.0502(11) 0.032(7) Uiso 1 1 d . . . N8 N 0.604(5) 0.660(3) 0.0274(13) 0.039(7) Uiso 1 1 d . . . N9 N 0.607(4) 0.278(2) 0.0747(10) 0.021(5) Uiso 1 1 d . . . N10 N 0.100(3) 0.282(2) 0.4255(9) 0.015(5) Uiso 1 1 d . . . C1 C 0.879(5) 0.941(3) 0.4204(13) 0.030(7) Uiso 1 1 d . . . C2 C 0.910(5) 0.859(3) 0.3804(14) 0.031(8) Uiso 1 1 d . . . C3 C 1.007(5) 0.744(3) 0.3868(14) 0.031(7) Uiso 1 1 d . . . C4 C 1.082(5) 0.704(3) 0.4355(13) 0.026(7) Uiso 1 1 d . . . C5 C 0.891(5) 0.858(3) 0.1073(12) 0.024(7) Uiso 1 1 d . . . C6 C 0.929(4) 0.800(2) 0.1580(11) 0.014(5) Uiso 1 1 d . . . C7 C 1.010(3) 0.691(2) 0.1605(9) 0.008(5) Uiso 1 1 d . . . C8 C 1.080(4) 0.619(3) 0.1174(12) 0.022(6) Uiso 1 1 d . . . C9 C 0.419(5) 0.863(3) 0.3967(13) 0.027(7) Uiso 1 1 d . . . C10 C 0.421(4) 0.803(3) 0.3471(12) 0.021(6) Uiso 1 1 d . . . C11 C 0.501(4) 0.685(3) 0.3443(12) 0.021(6) Uiso 1 1 d . . . C12 C 0.593(5) 0.619(3) 0.3859(13) 0.028(7) Uiso 1 1 d . . . C13 C 0.354(4) 0.939(3) 0.0812(12) 0.023(6) Uiso 1 1 d . . . C14 C 0.392(5) 0.857(3) 0.1233(12) 0.025(7) Uiso 1 1 d . . . C15 C 0.499(4) 0.756(2) 0.1180(10) 0.014(5) Uiso 1 1 d . . . C16 C 0.554(4) 0.700(3) 0.0670(12) 0.021(6) Uiso 1 1 d . . . C17 C 0.656(5) 0.380(3) 0.0695(14) 0.032(8) Uiso 1 1 d . . . D17 D 0.5766 0.4467 0.0813 0.039 Uiso 1 1 d R . . C18 C 0.825(5) 0.377(3) 0.0463(14) 0.032(8) Uiso 1 1 d . . . D18 D 0.8612 0.4461 0.0409 0.038 Uiso 1 1 d R . . C19 C 0.958(6) 0.277(3) 0.0289(15) 0.038(9) Uiso 1 1 d . . . D19 D 1.0798 0.2769 0.0151 0.046 Uiso 1 1 d R . . C20 C 0.878(5) 0.176(3) 0.0352(12) 0.025(7) Uiso 1 1 d . . . D20 D 0.9509 0.1078 0.0234 0.030 Uiso 1 1 d R . . C21 C 0.714(5) 0.177(3) 0.0559(13) 0.032(8) Uiso 1 1 d . . . D21 D 0.6676 0.1109 0.0584 0.038 Uiso 1 1 d R . . C22 C 0.417(5) 0.279(3) 0.1014(14) 0.037(8) Uiso 1 1 d . . . H22A H 0.368(5) 0.217(3) 0.0893(14) 0.045 Uiso 1 1 d R . . H22B H 0.329(5) 0.349(3) 0.0927(14) 0.045 Uiso 1 1 d R . . C23 C 0.431(4) 0.269(2) 0.1625(10) 0.013(5) Uiso 1 1 d . . . C24 C 0.394(4) 0.365(2) 0.1918(10) 0.014(5) Uiso 1 1 d . . . H24 H 0.362(4) 0.436(2) 0.1761(10) 0.017 Uiso 1 1 d R . . C25 C 0.405(4) 0.356(3) 0.2433(11) 0.020(6) Uiso 1 1 d . . . H25 H 0.376(4) 0.420(3) 0.2632(11) 0.024 Uiso 1 1 d R . . C26 C 0.459(4) 0.248(2) 0.2675(11) 0.018(6) Uiso 1 1 d . . . C27 C 0.518(4) 0.150(3) 0.2375(11) 0.020(6) Uiso 1 1 d . . . H27 H 0.555(4) 0.078(3) 0.2524(11) 0.024 Uiso 1 1 d R . . C28 C 0.519(5) 0.166(3) 0.1841(13) 0.028(7) Uiso 1 1 d . . . H28 H 0.579(5) 0.107(3) 0.1628(13) 0.033 Uiso 1 1 d R . . C29 C 0.153(5) 0.378(3) 0.4311(13) 0.029(7) Uiso 1 1 d . . . D29 D 0.0756 0.4443 0.4190 0.035 Uiso 1 1 d R . . C30 C 0.323(6) 0.385(3) 0.4548(15) 0.039(9) Uiso 1 1 d . . . D30 D 0.3545 0.4544 0.4595 0.047 Uiso 1 1 d R . . C31 C 0.438(6) 0.286(3) 0.4705(15) 0.037(8) Uiso 1 1 d . . . D31 D 0.5541 0.2844 0.4846 0.045 Uiso 1 1 calc R . . C32 C 0.370(4) 0.180(3) 0.4641(12) 0.023(7) Uiso 1 1 d . . . D32 D 0.4407 0.1124 0.4766 0.028 Uiso 1 1 d R . . C33 C 0.197(4) 0.181(3) 0.4391(12) 0.024(7) Uiso 1 1 d . . . D33 D 0.1569 0.1145 0.4329 0.028 Uiso 1 1 d R . . C34 C -0.093(4) 0.283(3) 0.4000(12) 0.021(6) Uiso 1 1 d . . . H34A H -0.148(4) 0.223(3) 0.4155(12) 0.025 Uiso 1 1 d R . . H34B H -0.181(4) 0.354(3) 0.4079(12) 0.025 Uiso 1 1 d R . . C35 C -0.077(5) 0.268(3) 0.3408(14) 0.031(8) Uiso 1 1 d . . . C36 C -0.118(4) 0.366(3) 0.3105(11) 0.018(6) Uiso 1 1 d . . . H36 H -0.153(4) 0.437(3) 0.3256(11) 0.022 Uiso 1 1 d R . . C37 C -0.106(4) 0.356(3) 0.2585(12) 0.024(7) Uiso 1 1 d . . . H37 H -0.144(4) 0.420(3) 0.2382(12) 0.029 Uiso 1 1 d R . . C38 C -0.037(4) 0.252(3) 0.2345(12) 0.021(6) Uiso 1 1 d . . . C39 C 0.019(5) 0.153(3) 0.2642(13) 0.028(7) Uiso 1 1 d . . . H39 H 0.060(5) 0.083(3) 0.2491(13) 0.033 Uiso 1 1 d R . . C40 C 0.009(5) 0.165(3) 0.3182(14) 0.032(8) Uiso 1 1 d . . . H40 H 0.061(5) 0.104(3) 0.3390(14) 0.038 Uiso 1 1 d R . . _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 S3 2.137(8) . ? Ni1 S1 2.138(9) . ? Ni1 S4 2.155(8) . ? Ni1 S2 2.165(9) . ? Ni2 S5 2.139(8) . ? Ni2 S6 2.151(8) . ? Ni2 S8 2.153(8) . ? Ni2 S7 2.153(8) . ? S1 C2 1.75(4) . ? S2 C3 1.70(4) . ? S3 C6 1.67(3) . ? S4 C7 1.72(2) . ? S5 C10 1.69(3) . ? S6 C11 1.72(3) . ? S7 C14 1.70(3) . ? S8 C15 1.76(3) . ? Cl1 C26 1.72(3) . ? Cl2 C38 1.71(3) . ? N1 C1 1.15(4) . ? N2 C4 1.15(4) . ? N3 C5 1.16(4) . ? N4 C8 1.21(4) . ? N5 C9 1.11(4) . ? N6 C12 1.15(4) . ? N7 C13 1.16(4) . ? N8 C16 1.15(4) . ? N9 C17 1.35(4) . ? N9 C21 1.39(4) . ? N9 C22 1.50(4) . ? N10 C29 1.32(4) . ? N10 C33 1.32(4) . ? N10 C34 1.58(4) . ? C1 C2 1.43(5) . ? C2 C3 1.43(5) . ? C3 C4 1.43(5) . ? C5 C6 1.49(4) . ? C6 C7 1.32(4) . ? C7 C8 1.44(4) . ? C9 C10 1.49(4) . ? C10 C11 1.42(4) . ? C11 C12 1.43(4) . ? C13 C14 1.46(4) . ? C14 C15 1.30(4) . ? C15 C16 1.50(4) . ? C17 C18 1.33(5) . ? C18 C19 1.43(5) . ? C19 C20 1.46(5) . ? C20 C21 1.27(5) . ? C22 H22B 0.9700 . ? C22 H22A 0.9700 . ? C22 C23 1.60(4) . ? C23 C24 1.37(4) . ? C23 C28 1.39(4) . ? C24 H24 0.9300 . ? C24 C25 1.35(4) . ? C25 H25 0.9300 . ? C25 C26 1.42(4) . ? C26 C27 1.41(4) . ? C27 H27 0.9300 . ? C27 C28 1.40(4) . ? C28 H28 0.9300 . ? C29 C30 1.42(5) . ? C30 C31 1.37(5) . ? C31 C32 1.47(5) . ? C32 C33 1.43(4) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 C35 1.55(4) . ? C35 C36 1.39(4) . ? C35 C40 1.39(5) . ? C36 H36 0.9300 . ? C36 C37 1.36(4) . ? C37 H37 0.9300 . ? C37 C38 1.40(4) . ? C38 C39 1.40(4) . ? C39 H39 0.9300 . ? C39 C40 1.41(5) . ? C40 H40 0.9300 . ? 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 S3 Ni1 S1 85.2(3) . . ? S3 Ni1 S4 92.2(3) . . ? S1 Ni1 S4 175.9(3) . . ? S3 Ni1 S2 174.5(3) . . ? S1 Ni1 S2 93.0(3) . . ? S4 Ni1 S2 89.4(3) . . ? S5 Ni2 S6 92.5(3) . . ? S5 Ni2 S8 176.1(3) . . ? S6 Ni2 S8 89.1(3) . . ? S5 Ni2 S7 85.2(3) . . ? S6 Ni2 S7 177.7(3) . . ? S8 Ni2 S7 93.1(3) . . ? C2 S1 Ni1 103.5(12) . . ? C3 S2 Ni1 104.3(13) . . ? C6 S3 Ni1 102.1(10) . . ? C7 S4 Ni1 102.5(9) . . ? C10 S5 Ni2 103.6(11) . . ? C11 S6 Ni2 104.6(11) . . ? C14 S7 Ni2 102.7(12) . . ? C15 S8 Ni2 99.3(9) . . ? C17 N9 C21 126(3) . . ? C17 N9 C22 116(3) . . ? C21 N9 C22 119(3) . . ? C29 N10 C33 126(3) . . ? C29 N10 C34 119(3) . . ? C33 N10 C34 115(2) . . ? N1 C1 C2 174(4) . . ? C3 C2 C1 124(3) . . ? C3 C2 S1 120(3) . . ? C1 C2 S1 116(3) . . ? C2 C3 C4 120(3) . . ? C2 C3 S2 119(3) . . ? C4 C3 S2 120(3) . . ? N2 C4 C3 176(4) . . ? N3 C5 C6 180(4) . . ? C7 C6 C5 121(3) . . ? C7 C6 S3 124(2) . . ? C5 C6 S3 115(2) . . ? C6 C7 C8 126(3) . . ? C6 C7 S4 119(2) . . ? C8 C7 S4 115(2) . . ? N4 C8 C7 177(3) . . ? N5 C9 C10 172(4) . . ? C11 C10 C9 119(3) . . ? C11 C10 S5 122(2) . . ? C9 C10 S5 118(2) . . ? C10 C11 C12 124(3) . . ? C10 C11 S6 117(2) . . ? C12 C11 S6 117(2) . . ? N6 C12 C11 171(4) . . ? N7 C13 C14 175(3) . . ? C15 C14 C13 124(3) . . ? C15 C14 S7 120(3) . . ? C13 C14 S7 115(2) . . ? C14 C15 C16 124(3) . . ? C14 C15 S8 123(2) . . ? C16 C15 S8 111(2) . . ? N8 C16 C15 176(3) . . ? C18 C17 N9 115(3) . . ? C17 C18 C19 126(4) . . ? C18 C19 C20 112(3) . . ? C21 C20 C19 124(3) . . ? C20 C21 N9 118(3) . . ? H22B C22 H22A 107.9 . . ? H22B C22 N9 109.3(18) . . ? H22A C22 N9 109.3(18) . . ? H22B C22 C23 109.3(17) . . ? H22A C22 C23 109.3(17) . . ? N9 C22 C23 112(3) . . ? C24 C23 C28 120(3) . . ? C24 C23 C22 120(3) . . ? C28 C23 C22 119(3) . . ? H24 C24 C25 120.1(18) . . ? H24 C24 C23 120.1(16) . . ? C25 C24 C23 120(3) . . ? H25 C25 C24 119.7(18) . . ? H25 C25 C26 119.7(17) . . ? C24 C25 C26 121(3) . . ? C27 C26 C25 120(3) . . ? C27 C26 Cl1 118(2) . . ? C25 C26 Cl1 122(2) . . ? H27 C27 C28 121.8(19) . . ? H27 C27 C26 121.8(17) . . ? C28 C27 C26 116(3) . . ? H28 C28 C23 119.5(18) . . ? H28 C28 C27 119.5(19) . . ? C23 C28 C27 121(3) . . ? N10 C29 C30 123(3) . . ? C31 C30 C29 117(4) . . ? C30 C31 C32 117(4) . . ? C33 C32 C31 122(3) . . ? N10 C33 C32 115(3) . . ? H34A C34 H34B 107.5 . . ? H34A C34 C35 108.6(17) . . ? H34B C34 C35 108.6(17) . . ? H34A C34 N10 108.6(14) . . ? H34B C34 N10 108.6(14) . . ? C35 C34 N10 115(2) . . ? C36 C35 C40 120(3) . . ? C36 C35 C34 117(3) . . ? C40 C35 C34 122(3) . . ? H36 C36 C37 120.8(19) . . ? H36 C36 C35 120.8(19) . . ? C37 C36 C35 118(3) . . ? H37 C37 C36 118.8(19) . . ? H37 C37 C38 118.8(18) . . ? C36 C37 C38 122(3) . . ? C39 C38 C37 120(3) . . ? C39 C38 Cl2 117(2) . . ? C37 C38 Cl2 123(2) . . ? H39 C39 C38 121.3(19) . . ? H39 C39 C40 121(2) . . ? C38 C39 C40 117(3) . . ? H40 C40 C35 120(2) . . ? H40 C40 C39 120(2) . . ? C35 C40 C39 121(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.952 _refine_diff_density_min -4.543 _refine_diff_density_rms 0.480