# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H5 D6 N6 Ni S4' _chemical_formula_weight 480.29 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' 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9131(8) _cell_length_b 17.7611(19) _cell_length_c 14.9879(18) _cell_angle_alpha 90.00 _cell_angle_beta 99.912(3) _cell_angle_gamma 90.00 _cell_volume 2075.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(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 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 1.351 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 28961 _diffrn_reflns_av_R_equivalents 0.0707 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4739 _reflns_number_gt 2300 _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^)+(0.0953P)^2^+1.0367P] 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 4739 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1512 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1955 _refine_ls_wR_factor_gt 0.1549 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.002 _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 0.75138(7) 0.03686(3) 0.51919(5) 0.0728(3) Uani 1 1 d . . . S1 S 0.70049(18) 0.07803(7) 0.64621(9) 0.0835(4) Uani 1 1 d . . . S2 S 0.68513(15) -0.07544(7) 0.54956(9) 0.0775(4) Uani 1 1 d . . . S3 S 0.83127(18) 0.14859(8) 0.49216(11) 0.0944(5) Uani 1 1 d . . . S4 S 0.79908(16) -0.00399(8) 0.39145(10) 0.0824(4) Uani 1 1 d . . . N1 N 0.5729(10) 0.0076(3) 0.8585(4) 0.140(2) Uani 1 1 d . . . N2 N 0.5543(8) -0.1861(3) 0.7357(5) 0.142(2) Uani 1 1 d . . . N3 N 1.0253(8) 0.2561(4) 0.3249(5) 0.149(2) Uani 1 1 d . . . N4 N 0.9811(7) 0.0575(4) 0.1924(4) 0.125(2) Uani 1 1 d . . . N5 N 0.5351(11) 0.6238(3) 0.5524(4) 0.131(2) Uani 1 1 d . . . N6 N 0.6872(11) 0.6291(6) 0.5084(6) 0.180(4) Uani 1 1 d . . . C1 C 0.6045(8) 0.0049(3) 0.7872(5) 0.0971(17) Uani 1 1 d . . . C2 C 0.6427(6) -0.0010(3) 0.6979(4) 0.0774(13) Uani 1 1 d . . . C3 C 0.6362(5) -0.0680(3) 0.6552(3) 0.0726(13) Uani 1 1 d . . . C4 C 0.5903(7) -0.1339(3) 0.6997(4) 0.0949(16) Uani 1 1 d . . . C5 C 0.9656(8) 0.2054(4) 0.3525(5) 0.1091(19) Uani 1 1 d . . . C6 C 0.8923(6) 0.1405(4) 0.3892(4) 0.0893(16) Uani 1 1 d . . . C7 C 0.8779(6) 0.0740(4) 0.3443(4) 0.0835(15) Uani 1 1 d . . . C8 C 0.9335(7) 0.0646(4) 0.2591(5) 0.0968(18) Uani 1 1 d . . . C9 C 0.3826(16) 0.5885(5) 0.5115(6) 0.154(3) Uani 1 1 d . . . H9A H 0.3716(16) 0.5702(5) 0.4526(6) 0.185 Uiso 1 1 d R . . C10 C 0.2596(15) 0.5816(5) 0.5554(7) 0.151(3) Uani 1 1 d . . . H10A H 0.1581(15) 0.5580(5) 0.5295(7) 0.182 Uiso 1 1 d R . . C11 C 0.2791(15) 0.6092(5) 0.6402(7) 0.175(4) Uani 1 1 d . . . H11A H 0.1929(15) 0.6019(5) 0.6744(7) 0.210 Uiso 1 1 d R . . C12 C 0.4274(15) 0.6488(4) 0.6778(6) 0.147(3) Uani 1 1 d . . . H12A H 0.4365(15) 0.6700(4) 0.7351(6) 0.176 Uiso 1 1 d R . . C13 C 0.5495(13) 0.6556(5) 0.6335(6) 0.139(3) Uani 1 1 d . . . H13A H 0.6476(13) 0.6825(5) 0.6575(6) 0.166 Uiso 1 1 d R . . C14 C 0.8306(12) 0.6840(8) 0.4124(8) 0.265(8) Uani 1 1 d . . . D14A D 0.8336 0.7246 0.3704 0.398 Uiso 1 1 d R . . D14B D 0.8326 0.6368 0.3814 0.398 Uiso 1 1 d R . . D14C D 0.9287 0.6872 0.4599 0.398 Uiso 1 1 d R . . C15 C 0.6809(11) 0.6889(8) 0.4496(7) 0.165(4) Uani 1 1 d . . . C16 C 0.5408(10) 0.7355(3) 0.4347(4) 0.118(2) Uani 1 1 d . . . D16A D 0.4622 0.7214 0.4739 0.177 Uiso 1 1 calc R . . D16B D 0.4852 0.7313 0.3727 0.177 Uiso 1 1 calc R . . D16C D 0.5771 0.7866 0.4470 0.177 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 0.0569(4) 0.0757(5) 0.0839(5) 0.0048(3) 0.0070(3) 0.0057(3) S1 0.0915(9) 0.0732(8) 0.0822(9) -0.0008(7) 0.0051(7) 0.0008(7) S2 0.0651(7) 0.0748(8) 0.0927(9) -0.0060(7) 0.0138(6) 0.0019(6) S3 0.0867(9) 0.0805(9) 0.1197(12) 0.0080(8) 0.0286(8) 0.0035(7) S4 0.0661(8) 0.0941(10) 0.0871(9) 0.0060(7) 0.0131(6) 0.0051(7) N1 0.224(7) 0.111(4) 0.089(4) 0.006(3) 0.039(4) 0.021(4) N2 0.181(6) 0.091(4) 0.177(6) 0.004(4) 0.094(5) -0.014(4) N3 0.145(5) 0.129(5) 0.179(6) 0.048(5) 0.049(4) -0.016(4) N4 0.113(4) 0.177(6) 0.085(4) 0.030(4) 0.017(3) -0.011(4) N5 0.181(6) 0.119(4) 0.091(4) -0.008(3) 0.020(4) 0.048(5) N6 0.160(7) 0.246(10) 0.120(6) -0.057(6) -0.019(5) 0.104(7) C1 0.122(5) 0.080(4) 0.085(4) 0.000(3) 0.004(4) 0.011(3) C2 0.066(3) 0.081(3) 0.082(4) 0.003(3) 0.003(2) 0.006(2) C3 0.055(3) 0.075(3) 0.087(3) 0.003(3) 0.010(2) 0.004(2) C4 0.089(4) 0.082(4) 0.119(5) -0.004(4) 0.033(3) -0.001(3) C5 0.085(4) 0.109(5) 0.134(5) 0.028(4) 0.023(4) 0.011(4) C6 0.058(3) 0.096(4) 0.114(4) 0.032(4) 0.015(3) 0.010(3) C7 0.050(3) 0.107(4) 0.091(4) 0.031(3) 0.005(2) 0.009(3) C8 0.065(3) 0.125(5) 0.095(5) 0.027(4) -0.001(3) 0.001(3) C9 0.202(10) 0.142(7) 0.107(6) -0.044(5) -0.005(6) -0.018(7) C10 0.221(10) 0.118(6) 0.120(7) -0.016(5) 0.041(7) -0.042(6) C11 0.288(13) 0.124(6) 0.117(7) -0.005(5) 0.048(7) -0.074(8) C12 0.233(11) 0.099(5) 0.105(6) -0.021(4) 0.020(7) -0.019(6) C13 0.171(8) 0.139(6) 0.106(6) -0.046(5) 0.025(5) 0.002(6) C14 0.120(7) 0.43(2) 0.261(13) -0.185(14) 0.068(8) -0.072(10) C15 0.101(6) 0.272(14) 0.118(7) -0.101(8) 0.004(5) -0.010(8) C16 0.161(7) 0.080(4) 0.121(5) -0.016(4) 0.046(5) 0.004(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 Ni1 S2 2.1312(15) . ? Ni1 S4 2.1408(16) . ? Ni1 S1 2.1413(16) . ? Ni1 S3 2.1425(16) . ? S1 C2 1.703(5) . ? S2 C3 1.699(5) . ? S3 C6 1.700(6) . ? S4 C7 1.719(6) . ? N1 C1 1.139(8) . ? N2 C4 1.134(7) . ? N3 C5 1.129(8) . ? N4 C8 1.134(8) . ? N5 C13 1.327(8) . ? N5 C9 1.404(10) . ? N5 N6 1.472(11) . ? N6 C15 1.375(14) . ? C1 C2 1.427(8) . ? C2 C3 1.348(7) . ? C3 C4 1.424(8) . ? C5 C6 1.441(9) . ? C6 C7 1.355(8) . ? C7 C8 1.430(8) . ? C9 H9A 0.9300 . ? C9 C10 1.271(11) . ? C10 H10A 0.9300 . ? C10 C11 1.346(11) . ? C11 H11A 0.9300 . ? C11 C12 1.400(12) . ? C12 H12A 0.9300 . ? C12 C13 1.268(11) . ? C13 H13A 0.9300 . ? C14 C15 1.396(11) . ? C14 D14A 0.9600 . ? C14 D14B 0.9600 . ? C14 D14C 0.9600 . ? C15 C16 1.371(12) . ? C16 D16A 0.9600 . ? C16 D16B 0.9600 . ? C16 D16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S2 Ni1 S4 87.80(6) . . ? S2 Ni1 S1 92.23(6) . . ? S4 Ni1 S1 179.30(5) . . ? S2 Ni1 S3 177.03(6) . . ? S4 Ni1 S3 92.38(6) . . ? S1 Ni1 S3 87.62(6) . . ? C2 S1 Ni1 103.2(2) . . ? C3 S2 Ni1 103.33(19) . . ? C6 S3 Ni1 103.4(2) . . ? C7 S4 Ni1 103.1(2) . . ? C13 N5 C9 121.5(8) . . ? C13 N5 N6 115.8(8) . . ? C9 N5 N6 122.8(7) . . ? C15 N6 N5 113.3(7) . . ? N1 C1 C2 178.2(7) . . ? C3 C2 C1 120.9(5) . . ? C3 C2 S1 120.3(4) . . ? C1 C2 S1 118.9(4) . . ? C2 C3 C4 119.7(5) . . ? C2 C3 S2 120.9(4) . . ? C4 C3 S2 119.3(4) . . ? N2 C4 C3 179.5(8) . . ? N3 C5 C6 178.8(8) . . ? C7 C6 C5 120.9(6) . . ? C7 C6 S3 120.8(4) . . ? C5 C6 S3 118.3(5) . . ? C6 C7 C8 122.1(5) . . ? C6 C7 S4 120.3(5) . . ? C8 C7 S4 117.5(5) . . ? N4 C8 C7 178.5(6) . . ? H9A C9 C10 120.2(6) . . ? H9A C9 N5 120.2(5) . . ? C10 C9 N5 119.6(9) . . ? H10A C10 C9 120.6(6) . . ? H10A C10 C11 120.6(7) . . ? C9 C10 C11 118.7(10) . . ? H11A C11 C10 119.5(7) . . ? H11A C11 C12 119.5(6) . . ? C10 C11 C12 120.9(10) . . ? H12A C12 C13 120.0(6) . . ? H12A C12 C11 120.0(6) . . ? C13 C12 C11 119.9(9) . . ? H13A C13 C12 120.5(6) . . ? H13A C13 N5 120.5(6) . . ? C12 C13 N5 119.0(9) . . ? C15 C14 D14A 109.5 . . ? C15 C14 D14B 109.5 . . ? D14A C14 D14B 109.5 . . ? C15 C14 D14C 109.5 . . ? D14A C14 D14C 109.5 . . ? D14B C14 D14C 109.5 . . ? C16 C15 N6 120.6(9) . . ? C16 C15 C14 133.7(15) . . ? N6 C15 C14 105.6(13) . . ? C15 C16 D16A 109.5 . . ? C15 C16 D16B 109.5 . . ? D16A C16 D16B 109.5 . . ? C15 C16 D16C 109.5 . . ? D16A C16 D16C 109.5 . . ? D16B C16 D16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.854 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.101 _database_code_depnum_ccdc_archive 'CCDC 948261' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H5 D6 N6 Ni S4' _chemical_formula_weight 480.29 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' 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.4940(12) _cell_length_b 17.3801(12) _cell_length_c 16.0217(14) _cell_angle_alpha 90.00 _cell_angle_beta 110.099(9) _cell_angle_gamma 90.00 _cell_volume 4051.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 200(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 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1928 _exptl_absorpt_coefficient_mu 1.383 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 29355 _diffrn_reflns_av_R_equivalents 0.0591 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7950 _reflns_number_gt 5263 _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^)+(0.0433P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7950 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.00893(3) 0.46113(3) 0.37873(3) 0.03386(14) Uani 1 1 d . . . Ni2 Ni 0.03883(3) 0.45375(3) 0.89749(3) 0.03805(15) Uani 1 1 d . . . S1 S 0.04781(6) 0.57389(5) 0.43320(6) 0.0380(2) Uani 1 1 d . . . S2 S 0.13702(6) 0.41163(5) 0.46119(7) 0.0420(2) Uani 1 1 d . . . S3 S -0.11770(6) 0.51113(5) 0.29274(6) 0.0376(2) Uani 1 1 d . . . S4 S -0.02593(6) 0.34911(5) 0.32073(7) 0.0411(2) Uani 1 1 d . . . S5 S 0.06918(7) 0.57000(6) 0.94426(7) 0.0444(3) Uani 1 1 d . . . S6 S 0.16202(6) 0.41005(6) 0.99543(7) 0.0450(3) Uani 1 1 d . . . S7 S -0.08941(7) 0.49523(6) 0.80545(7) 0.0418(2) Uani 1 1 d . . . S8 S 0.01728(7) 0.33998(6) 0.84076(7) 0.0468(3) Uani 1 1 d . . . N1 N 0.2478(2) 0.6778(2) 0.5908(3) 0.0662(11) Uani 1 1 d . . . N2 N 0.3640(2) 0.4692(2) 0.6209(3) 0.0645(11) Uani 1 1 d . . . N3 N -0.3143(2) 0.46196(18) 0.0880(2) 0.0481(9) Uani 1 1 d . . . N4 N -0.1954(2) 0.2518(2) 0.1295(2) 0.0567(9) Uani 1 1 d . . . N5 N 0.2558(3) 0.6820(3) 1.1095(3) 0.1078(17) Uani 1 1 d . . . N6 N 0.3682(3) 0.4834(2) 1.1810(3) 0.0654(11) Uani 1 1 d . . . N7 N -0.2923(2) 0.4275(2) 0.6182(2) 0.0586(10) Uani 1 1 d . . . N8 N -0.1427(2) 0.2320(2) 0.6513(3) 0.0681(11) Uani 1 1 d . . . N9 N 0.9966(2) 0.80969(19) 1.0036(2) 0.0443(8) Uani 1 1 d . . . N10 N 0.9300(2) 0.75842(18) 0.9454(2) 0.0488(8) Uani 1 1 d . . . N11 N 0.05711(19) 0.88156(16) 0.5248(2) 0.0390(7) Uani 1 1 d . . . N12 N 0.0151(2) 0.89176(19) 0.4309(2) 0.0482(8) Uani 1 1 d . . . C1 C 0.2066(3) 0.6259(2) 0.5539(3) 0.0451(10) Uani 1 1 d . . . C2 C 0.1569(2) 0.5600(2) 0.5068(2) 0.0381(9) Uani 1 1 d . . . C3 C 0.1962(2) 0.4894(2) 0.5184(2) 0.0383(9) Uani 1 1 d . . . C4 C 0.2894(3) 0.4784(2) 0.5754(3) 0.0466(10) Uani 1 1 d . . . C5 C -0.2502(3) 0.4509(2) 0.1482(3) 0.0361(9) Uani 1 1 d . . . C6 C -0.1681(2) 0.4360(2) 0.2233(2) 0.0355(9) Uani 1 1 d . . . C7 C -0.1279(2) 0.3657(2) 0.2359(2) 0.0360(9) Uani 1 1 d . . . C8 C -0.1663(2) 0.3025(2) 0.1767(3) 0.0409(9) Uani 1 1 d . . . C9 C 0.2178(3) 0.6290(3) 1.0724(3) 0.0674(13) Uani 1 1 d . . . C10 C 0.1733(3) 0.5610(2) 1.0280(2) 0.0432(10) Uani 1 1 d . . . C11 C 0.2134(3) 0.4916(2) 1.0513(3) 0.0426(10) Uani 1 1 d . . . C12 C 0.3003(3) 0.4856(2) 1.1232(3) 0.0492(11) Uani 1 1 d . . . C13 C -0.2217(3) 0.4227(2) 0.6728(3) 0.0433(10) Uani 1 1 d . . . C14 C -0.1338(2) 0.4153(2) 0.7414(2) 0.0404(9) Uani 1 1 d . . . C15 C -0.0861(2) 0.3481(2) 0.7559(3) 0.0417(9) Uani 1 1 d . . . C16 C -0.1182(3) 0.2828(2) 0.6989(3) 0.0495(11) Uani 1 1 d . . . C17 C 1.0857(3) 0.7998(3) 1.0173(3) 0.0580(12) Uani 1 1 d . . . H17A H 1.1050(3) 0.7629(3) 0.9836(3) 0.070 Uiso 1 1 d R . . C18 C 1.1490(3) 0.8432(3) 1.0801(3) 0.0677(14) Uani 1 1 d . . . H18A H 1.2125(3) 0.8370(3) 1.0894(3) 0.081 Uiso 1 1 d R . . C19 C 1.1216(3) 0.8961(3) 1.1301(3) 0.0665(13) Uani 1 1 d . . . H19A H 1.1653(3) 0.9259(3) 1.1747(3) 0.080 Uiso 1 1 d R . . C20 C 1.0292(3) 0.9042(3) 1.1135(3) 0.0737(14) Uani 1 1 d . . . H20A H 1.0082(3) 0.9414(3) 1.1456(3) 0.088 Uiso 1 1 d R . . C21 C 0.9668(3) 0.8593(3) 1.0512(3) 0.0646(13) Uani 1 1 d . . . H21A H 0.9030(3) 0.8635(3) 1.0419(3) 0.078 Uiso 1 1 d R . . C22 C 0.9525(3) 0.8295(2) 0.8202(3) 0.0572(12) Uani 1 1 d . . . D22A D 0.9948 0.8619 0.8663 0.086 Uiso 1 1 d R . . D22B D 0.9024 0.8611 0.7814 0.086 Uiso 1 1 d R . . D22C D 0.9858 0.8054 0.7849 0.086 Uiso 1 1 d R . . C23 C 0.9140(2) 0.7687(2) 0.8626(3) 0.0445(10) Uani 1 1 d . . . C24 C 0.8479(3) 0.7134(2) 0.8027(3) 0.0594(12) Uani 1 1 d . . . D24A D 0.8273 0.6767 0.8384 0.089 Uiso 1 1 d R . . D24B D 0.8780 0.6856 0.7671 0.089 Uiso 1 1 d R . . D24C D 0.7947 0.7416 0.7631 0.089 Uiso 1 1 d R . . C25 C 0.1394(3) 0.8460(2) 0.5560(3) 0.0473(10) Uani 1 1 d . . . H25A H 0.1657(3) 0.8238(2) 0.5161(3) 0.057 Uiso 1 1 d R . . C26 C 0.1842(3) 0.8425(2) 0.6454(3) 0.0521(11) Uani 1 1 d . . . H26A H 0.2417(3) 0.8169(2) 0.6683(3) 0.062 Uiso 1 1 d R . . C27 C 0.1461(3) 0.8763(2) 0.7031(3) 0.0513(11) Uani 1 1 d . . . H27A H 0.1771(3) 0.8741(2) 0.7656(3) 0.062 Uiso 1 1 d R . . C28 C 0.0629(3) 0.9127(2) 0.6685(3) 0.0473(10) Uani 1 1 d . . . H28A H 0.0360(3) 0.9361(2) 0.7072(3) 0.057 Uiso 1 1 d R . . C29 C 0.0187(3) 0.9156(2) 0.5788(3) 0.0435(10) Uani 1 1 d . . . H29A H -0.0386(3) 0.9415(2) 0.5547(3) 0.052 Uiso 1 1 d R . . C30 C -0.0823(3) 0.8459(3) 0.2940(3) 0.0761(15) Uani 1 1 d . . . D30A D -0.0617 0.8943 0.2756 0.114 Uiso 1 1 d R . . D30B D -0.1493 0.8467 0.2777 0.114 Uiso 1 1 d R . . D30C D -0.0644 0.8028 0.2640 0.114 Uiso 1 1 d R . . C31 C -0.0389(3) 0.8367(3) 0.3922(3) 0.0511(11) Uani 1 1 d . . . C32 C -0.0605(3) 0.7674(2) 0.4346(3) 0.0702(14) Uani 1 1 d . . . D32A D -0.0271 0.7693 0.4987 0.105 Uiso 1 1 d R . . D32B D -0.0420 0.7214 0.4095 0.105 Uiso 1 1 d R . . D32C D -0.1267 0.7655 0.4235 0.105 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 0.0314(3) 0.0353(3) 0.0356(3) 0.0031(2) 0.0124(2) 0.0024(2) Ni2 0.0446(3) 0.0326(3) 0.0415(3) 0.0030(2) 0.0207(3) 0.0006(2) S1 0.0396(5) 0.0365(5) 0.0381(6) 0.0014(4) 0.0137(5) 0.0047(4) S2 0.0352(5) 0.0365(6) 0.0495(6) 0.0047(5) 0.0085(5) 0.0033(4) S3 0.0351(5) 0.0360(5) 0.0400(6) 0.0004(4) 0.0107(5) 0.0046(4) S4 0.0389(5) 0.0365(6) 0.0446(6) 0.0026(5) 0.0099(5) 0.0041(4) S5 0.0623(6) 0.0349(6) 0.0390(6) 0.0012(5) 0.0212(5) 0.0041(5) S6 0.0454(6) 0.0346(6) 0.0546(7) 0.0043(5) 0.0168(5) 0.0003(4) S7 0.0508(6) 0.0376(6) 0.0405(6) 0.0031(5) 0.0202(5) 0.0058(4) S8 0.0495(6) 0.0355(6) 0.0525(7) 0.0011(5) 0.0138(5) 0.0053(4) N1 0.065(2) 0.051(3) 0.069(3) -0.013(2) 0.006(2) 0.0025(19) N2 0.055(2) 0.062(3) 0.061(3) 0.012(2) 0.001(2) -0.0003(19) N3 0.0372(19) 0.050(2) 0.054(2) 0.0072(18) 0.0110(18) 0.0009(16) N4 0.057(2) 0.047(2) 0.059(3) -0.0035(19) 0.011(2) -0.0007(18) N5 0.141(4) 0.054(3) 0.076(3) -0.017(3) -0.030(3) 0.004(3) N6 0.063(2) 0.064(3) 0.063(3) 0.002(2) 0.013(2) 0.003(2) N7 0.051(2) 0.065(3) 0.057(3) 0.000(2) 0.015(2) 0.0047(19) N8 0.060(2) 0.058(3) 0.086(3) -0.016(2) 0.024(2) -0.0013(19) N9 0.0428(19) 0.048(2) 0.043(2) 0.0109(17) 0.0152(17) 0.0059(16) N10 0.055(2) 0.044(2) 0.046(2) 0.0043(17) 0.0147(19) -0.0010(16) N11 0.0412(18) 0.0315(18) 0.044(2) 0.0037(15) 0.0137(17) -0.0014(14) N12 0.054(2) 0.051(2) 0.036(2) 0.0043(17) 0.0118(18) 0.0073(17) C1 0.045(2) 0.046(3) 0.043(3) -0.003(2) 0.012(2) 0.003(2) C2 0.035(2) 0.051(3) 0.027(2) -0.0030(18) 0.0091(18) -0.0045(18) C3 0.038(2) 0.044(2) 0.034(2) 0.0045(18) 0.0122(18) -0.0013(17) C4 0.048(2) 0.041(2) 0.044(3) 0.010(2) 0.008(2) 0.0045(19) C5 0.037(2) 0.035(2) 0.042(3) 0.0018(18) 0.021(2) -0.0001(17) C6 0.0311(19) 0.043(2) 0.036(2) 0.0045(18) 0.0166(18) -0.0008(16) C7 0.0318(19) 0.045(2) 0.033(2) 0.0020(18) 0.0133(17) -0.0073(17) C8 0.042(2) 0.037(2) 0.043(3) 0.007(2) 0.013(2) 0.0011(18) C9 0.095(4) 0.049(3) 0.047(3) -0.001(2) 0.010(3) 0.005(3) C10 0.057(2) 0.043(2) 0.034(2) 0.0027(19) 0.020(2) -0.0051(19) C11 0.050(2) 0.049(3) 0.038(2) 0.0019(19) 0.026(2) -0.0054(19) C12 0.052(3) 0.049(3) 0.049(3) 0.006(2) 0.020(2) 0.001(2) C13 0.051(2) 0.041(2) 0.045(3) 0.005(2) 0.025(2) 0.005(2) C14 0.050(2) 0.045(2) 0.035(2) 0.0029(18) 0.026(2) -0.0053(18) C15 0.048(2) 0.036(2) 0.048(3) 0.0045(19) 0.025(2) -0.0020(18) C16 0.049(2) 0.041(3) 0.060(3) -0.003(2) 0.019(2) 0.001(2) C17 0.050(3) 0.070(3) 0.058(3) 0.001(2) 0.023(2) 0.007(2) C18 0.053(3) 0.087(4) 0.065(3) 0.006(3) 0.021(3) -0.008(3) C19 0.064(3) 0.063(3) 0.065(3) 0.000(3) 0.013(3) -0.012(2) C20 0.079(3) 0.064(3) 0.069(4) -0.021(3) 0.014(3) 0.013(3) C21 0.051(3) 0.081(4) 0.060(3) -0.009(3) 0.016(3) 0.019(2) C22 0.054(2) 0.068(3) 0.052(3) 0.019(2) 0.022(2) 0.003(2) C23 0.039(2) 0.045(2) 0.052(3) 0.008(2) 0.020(2) 0.0081(18) C24 0.068(3) 0.058(3) 0.048(3) 0.003(2) 0.015(2) -0.003(2) C25 0.043(2) 0.036(2) 0.064(3) -0.006(2) 0.019(2) 0.0014(18) C26 0.045(2) 0.036(2) 0.062(3) -0.004(2) 0.001(2) 0.0064(18) C27 0.060(3) 0.039(2) 0.046(3) 0.003(2) 0.006(2) 0.001(2) C28 0.055(3) 0.041(2) 0.046(3) -0.001(2) 0.018(2) -0.004(2) C29 0.042(2) 0.035(2) 0.057(3) -0.001(2) 0.021(2) -0.0003(17) C30 0.080(3) 0.092(4) 0.047(3) -0.012(3) 0.010(3) 0.029(3) C31 0.046(2) 0.055(3) 0.051(3) -0.008(2) 0.014(2) 0.018(2) C32 0.064(3) 0.042(3) 0.090(4) -0.006(3) 0.007(3) -0.002(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 S4 2.1450(11) . ? Ni1 S1 2.1456(10) . ? Ni1 S2 2.1500(10) . ? Ni1 S3 2.1551(10) . ? Ni2 S5 2.1501(11) . ? Ni2 S6 2.1504(11) . ? Ni2 S7 2.1513(11) . ? Ni2 S8 2.1538(11) . ? S1 C2 1.714(4) . ? S2 C3 1.712(4) . ? S3 C6 1.719(4) . ? S4 C7 1.718(4) . ? S5 C10 1.715(4) . ? S6 C11 1.718(4) . ? S7 C14 1.724(4) . ? S8 C15 1.714(4) . ? N1 C1 1.146(5) . ? N2 C4 1.146(5) . ? N3 C5 1.138(4) . ? N4 C8 1.148(5) . ? N5 C9 1.143(6) . ? N6 C12 1.139(5) . ? N7 C13 1.145(5) . ? N8 C16 1.143(5) . ? N9 C17 1.332(4) . ? N9 C21 1.334(5) . ? N9 N10 1.438(4) . ? N10 C23 1.276(5) . ? N11 C29 1.345(4) . ? N11 C25 1.348(4) . ? N11 N12 1.429(4) . ? N12 C31 1.282(5) . ? C1 C2 1.441(5) . ? C2 C3 1.353(5) . ? C3 C4 1.432(5) . ? C5 C6 1.442(5) . ? C6 C7 1.355(5) . ? C7 C8 1.439(5) . ? C9 C10 1.429(6) . ? C10 C11 1.349(5) . ? C11 C12 1.444(6) . ? C13 C14 1.432(5) . ? C14 C15 1.359(5) . ? C15 C16 1.434(6) . ? C17 H17A 0.9500 . ? C17 C18 1.366(6) . ? C18 H18A 0.9500 . ? C18 C19 1.379(6) . ? C19 H19A 0.9500 . ? C19 C20 1.370(6) . ? C20 H20A 0.9500 . ? C20 C21 1.370(6) . ? C21 H21A 0.9500 . ? C22 C23 1.487(5) . ? C22 D22A 0.9800 . ? C22 D22B 0.9800 . ? C22 D22C 0.9800 . ? C23 C24 1.489(5) . ? C24 D24A 0.9800 . ? C24 D24B 0.9800 . ? C24 D24C 0.9800 . ? C25 H25A 0.9500 . ? C25 C26 1.362(5) . ? C26 H26A 0.9500 . ? C26 C27 1.386(5) . ? C27 H27A 0.9500 . ? C27 C28 1.371(5) . ? C28 H28A 0.9500 . ? C28 C29 1.365(5) . ? C29 H29A 0.9500 . ? C30 C31 1.493(6) . ? C30 D30A 0.9800 . ? C30 D30B 0.9800 . ? C30 D30C 0.9800 . ? C31 C32 1.476(6) . ? C32 D32A 0.9800 . ? C32 D32B 0.9800 . ? C32 D32C 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 S4 Ni1 S1 177.37(4) . . ? S4 Ni1 S2 86.84(4) . . ? S1 Ni1 S2 92.56(4) . . ? S4 Ni1 S3 92.90(4) . . ? S1 Ni1 S3 87.62(4) . . ? S2 Ni1 S3 178.19(4) . . ? S5 Ni2 S6 92.56(4) . . ? S5 Ni2 S7 87.93(4) . . ? S6 Ni2 S7 176.08(4) . . ? S5 Ni2 S8 173.43(4) . . ? S6 Ni2 S8 87.34(4) . . ? S7 Ni2 S8 92.62(4) . . ? C2 S1 Ni1 102.93(14) . . ? C3 S2 Ni1 102.96(13) . . ? C6 S3 Ni1 102.67(13) . . ? C7 S4 Ni1 102.50(13) . . ? C10 S5 Ni2 102.76(14) . . ? C11 S6 Ni2 103.00(14) . . ? C14 S7 Ni2 102.91(14) . . ? C15 S8 Ni2 103.09(14) . . ? C17 N9 C21 122.1(4) . . ? C17 N9 N10 119.9(3) . . ? C21 N9 N10 117.3(3) . . ? C23 N10 N9 115.3(3) . . ? C29 N11 C25 122.3(4) . . ? C29 N11 N12 118.7(3) . . ? C25 N11 N12 118.5(3) . . ? C31 N12 N11 113.7(3) . . ? N1 C1 C2 178.5(4) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 S1 120.9(3) . . ? C1 C2 S1 118.1(3) . . ? C2 C3 C4 121.0(4) . . ? C2 C3 S2 120.6(3) . . ? C4 C3 S2 118.3(3) . . ? N2 C4 C3 179.6(5) . . ? N3 C5 C6 178.7(4) . . ? C7 C6 C5 121.0(3) . . ? C7 C6 S3 120.3(3) . . ? C5 C6 S3 118.6(3) . . ? C6 C7 C8 121.7(3) . . ? C6 C7 S4 121.4(3) . . ? C8 C7 S4 116.9(3) . . ? N4 C8 C7 178.8(4) . . ? N5 C9 C10 177.7(6) . . ? C11 C10 C9 120.3(4) . . ? C11 C10 S5 121.2(3) . . ? C9 C10 S5 118.5(3) . . ? C10 C11 C12 119.9(4) . . ? C10 C11 S6 120.4(3) . . ? C12 C11 S6 119.6(3) . . ? N6 C12 C11 177.5(5) . . ? N7 C13 C14 179.0(4) . . ? C15 C14 C13 121.8(4) . . ? C15 C14 S7 120.6(3) . . ? C13 C14 S7 117.6(3) . . ? C14 C15 C16 121.4(4) . . ? C14 C15 S8 120.8(3) . . ? C16 C15 S8 117.8(3) . . ? N8 C16 C15 177.5(5) . . ? H17A C17 N9 120.3(3) . . ? H17A C17 C18 120.3(3) . . ? N9 C17 C18 119.4(4) . . ? H18A C18 C17 119.7(3) . . ? H18A C18 C19 119.7(3) . . ? C17 C18 C19 120.7(4) . . ? H19A C19 C20 121.2(3) . . ? H19A C19 C18 121.2(3) . . ? C20 C19 C18 117.7(5) . . ? H20A C20 C19 119.6(3) . . ? H20A C20 C21 119.6(3) . . ? C19 C20 C21 120.8(4) . . ? H21A C21 N9 120.4(2) . . ? H21A C21 C20 120.4(3) . . ? N9 C21 C20 119.2(4) . . ? C23 C22 D22A 109.5 . . ? C23 C22 D22B 109.5 . . ? D22A C22 D22B 109.5 . . ? C23 C22 D22C 109.5 . . ? D22A C22 D22C 109.5 . . ? D22B C22 D22C 109.5 . . ? N10 C23 C22 127.6(4) . . ? N10 C23 C24 115.1(4) . . ? C22 C23 C24 117.3(4) . . ? C23 C24 D24A 109.5 . . ? C23 C24 D24B 109.5 . . ? D24A C24 D24B 109.5 . . ? C23 C24 D24C 109.5 . . ? D24A C24 D24C 109.5 . . ? D24B C24 D24C 109.5 . . ? H25A C25 N11 120.5(2) . . ? H25A C25 C26 120.5(2) . . ? N11 C25 C26 119.1(4) . . ? H26A C26 C25 119.9(2) . . ? H26A C26 C27 119.9(2) . . ? C25 C26 C27 120.2(4) . . ? H27A C27 C28 120.6(3) . . ? H27A C27 C26 120.6(2) . . ? C28 C27 C26 118.8(4) . . ? H28A C28 C29 119.8(2) . . ? H28A C28 C27 119.8(3) . . ? C29 C28 C27 120.3(4) . . ? H29A C29 N11 120.4(2) . . ? H29A C29 C28 120.4(2) . . ? N11 C29 C28 119.3(4) . . ? C31 C30 D30A 109.5 . . ? C31 C30 D30B 109.5 . . ? D30A C30 D30B 109.5 . . ? C31 C30 D30C 109.5 . . ? D30A C30 D30C 109.5 . . ? D30B C30 D30C 109.5 . . ? N12 C31 C32 126.9(4) . . ? N12 C31 C30 114.4(4) . . ? C32 C31 C30 118.7(4) . . ? C31 C32 D32A 109.5 . . ? C31 C32 D32B 109.5 . . ? D32A C32 D32B 109.5 . . ? C31 C32 D32C 109.5 . . ? D32A C32 D32C 109.5 . . ? D32B C32 D32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.595 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 948262' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H5 D6 N6 Ni S4' _chemical_formula_weight 480.29 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' 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8725(9) _cell_length_b 17.8806(17) _cell_length_c 15.1206(16) _cell_angle_alpha 90.00 _cell_angle_beta 99.488(11) _cell_angle_gamma 90.00 _cell_volume 2099.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 353(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 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 1.335 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 353(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 13902 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4123 _reflns_number_gt 2070 _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^)+(0.0866P)^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 0.0055(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4123 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1275 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.2022 _refine_ls_wR_factor_gt 0.1672 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.75175(8) 0.03648(4) 0.51940(5) 0.0828(4) Uani 1 1 d . . . S1 S 0.7023(2) 0.07674(8) 0.64609(10) 0.0953(5) Uani 1 1 d . . . S2 S 0.68581(18) -0.07562(8) 0.54919(10) 0.0893(5) Uani 1 1 d . . . S3 S 0.8292(2) 0.14823(9) 0.49254(11) 0.1009(5) Uani 1 1 d . . . S4 S 0.79965(18) -0.00333(9) 0.39232(10) 0.0903(5) Uani 1 1 d . . . N1 N 0.5769(11) 0.0055(4) 0.8555(5) 0.152(3) Uani 1 1 d . . . N2 N 0.5584(10) -0.1873(4) 0.7323(5) 0.161(3) Uani 1 1 d . . . N3 N 1.0144(10) 0.2569(4) 0.3267(5) 0.153(3) Uani 1 1 d . . . N4 N 0.9753(8) 0.0599(4) 0.1941(4) 0.127(2) Uani 1 1 d . . . N5 N 0.5422(12) 0.6249(4) 0.5510(5) 0.140(2) Uani 1 1 d . . . N6 N 0.6924(12) 0.6314(6) 0.5044(6) 0.173(3) Uani 1 1 d . . . C1 C 0.6082(10) 0.0036(4) 0.7849(5) 0.112(2) Uani 1 1 d . . . C2 C 0.6461(7) -0.0024(3) 0.6960(4) 0.0920(16) Uani 1 1 d . . . C3 C 0.6383(6) -0.0687(3) 0.6543(4) 0.0829(15) Uani 1 1 d . . . C4 C 0.5929(9) -0.1335(4) 0.6966(5) 0.111(2) Uani 1 1 d . . . C5 C 0.9601(9) 0.2055(4) 0.3553(5) 0.116(2) Uani 1 1 d . . . C6 C 0.8879(7) 0.1395(4) 0.3891(4) 0.0920(16) Uani 1 1 d . . . C7 C 0.8758(6) 0.0744(3) 0.3449(4) 0.0856(16) Uani 1 1 d . . . C8 C 0.9296(8) 0.0669(4) 0.2606(5) 0.0972(18) Uani 1 1 d . . . C9 C 0.3963(16) 0.5901(5) 0.5107(7) 0.155(3) Uani 1 1 d . . . H9A H 0.3885(16) 0.5731(5) 0.4520(7) 0.186 Uiso 1 1 d R . . C10 C 0.2680(14) 0.5803(5) 0.5535(7) 0.148(3) Uani 1 1 d . . . H10A H 0.1681(14) 0.5559(5) 0.5269(7) 0.177 Uiso 1 1 d R . . C11 C 0.2845(15) 0.6068(5) 0.6377(7) 0.159(3) Uani 1 1 d . . . H11A H 0.1968(15) 0.5987(5) 0.6710(7) 0.191 Uiso 1 1 d R . . C12 C 0.4277(17) 0.6454(5) 0.6750(6) 0.156(3) Uani 1 1 d . . . H12A H 0.4351(17) 0.6646(5) 0.7327(6) 0.187 Uiso 1 1 d R . . C13 C 0.5537(14) 0.6556(6) 0.6310(7) 0.162(4) Uani 1 1 d . . . H13A H 0.6495(14) 0.6837(6) 0.6551(7) 0.194 Uiso 1 1 d R . . C14 C 0.8298(14) 0.6950(9) 0.4049(8) 0.302(9) Uani 1 1 d . . . D14A D 0.8199 0.7371 0.3649 0.453 Uiso 1 1 d R . . D14B D 0.8390 0.6499 0.3716 0.453 Uiso 1 1 d R . . D14C D 0.9307 0.7007 0.4497 0.453 Uiso 1 1 d R . . C15 C 0.6811(13) 0.6908(8) 0.4477(6) 0.151(3) Uani 1 1 d . . . C16 C 0.5374(12) 0.7363(4) 0.4336(5) 0.144(3) Uani 1 1 d . . . D16A D 0.4597 0.7216 0.4732 0.215 Uiso 1 1 d R . . D16B D 0.4809 0.7316 0.3726 0.215 Uiso 1 1 d R . . D16C D 0.5716 0.7873 0.4454 0.215 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 0.0672(5) 0.0834(6) 0.0941(6) -0.0048(4) 0.0022(4) 0.0056(3) S1 0.1042(11) 0.0835(10) 0.0952(10) -0.0115(8) 0.0079(9) 0.0052(8) S2 0.0733(9) 0.0826(9) 0.1099(11) -0.0122(8) 0.0089(8) 0.0040(7) S3 0.0974(11) 0.0867(10) 0.1202(13) -0.0079(9) 0.0232(9) 0.0037(8) S4 0.0747(9) 0.0948(10) 0.0984(10) -0.0075(8) 0.0054(8) 0.0043(7) N1 0.216(8) 0.134(5) 0.114(5) 0.005(4) 0.049(5) 0.025(5) N2 0.201(8) 0.116(5) 0.186(7) 0.008(5) 0.089(6) -0.004(5) N3 0.180(7) 0.116(5) 0.169(6) 0.029(5) 0.053(5) -0.006(4) N4 0.133(5) 0.152(5) 0.097(4) 0.010(4) 0.018(4) 0.002(4) N5 0.163(7) 0.140(5) 0.117(5) -0.024(4) 0.024(5) 0.017(5) N6 0.161(7) 0.225(9) 0.122(6) -0.029(6) -0.007(6) 0.063(7) C1 0.128(6) 0.106(5) 0.101(5) 0.005(5) 0.018(5) 0.016(4) C2 0.073(4) 0.097(4) 0.100(4) 0.001(4) -0.002(3) 0.013(3) C3 0.068(3) 0.089(4) 0.091(4) 0.008(3) 0.011(3) -0.001(3) C4 0.100(5) 0.109(5) 0.126(5) 0.000(5) 0.028(4) 0.009(4) C5 0.109(5) 0.106(5) 0.136(6) 0.013(5) 0.028(4) 0.020(4) C6 0.068(4) 0.097(4) 0.108(4) 0.020(4) 0.006(3) 0.010(3) C7 0.057(3) 0.093(4) 0.100(4) 0.017(3) -0.005(3) 0.008(3) C8 0.078(4) 0.113(5) 0.095(5) 0.011(4) -0.003(4) 0.001(3) C9 0.174(9) 0.136(7) 0.146(8) -0.041(6) 0.002(8) -0.030(7) C10 0.165(9) 0.130(7) 0.155(9) -0.024(6) 0.044(7) -0.037(6) C11 0.228(11) 0.120(6) 0.142(8) -0.015(6) 0.066(7) -0.033(7) C12 0.227(11) 0.110(6) 0.131(7) -0.013(5) 0.030(8) -0.019(7) C13 0.178(9) 0.174(8) 0.139(8) -0.066(7) 0.041(7) -0.034(7) C14 0.153(9) 0.53(3) 0.245(12) -0.199(14) 0.101(8) -0.156(12) C15 0.127(7) 0.216(11) 0.110(6) -0.060(7) 0.017(6) -0.047(8) C16 0.172(8) 0.095(5) 0.165(8) -0.025(5) 0.032(6) 0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S2 2.1371(16) . ? Ni1 S4 2.1401(17) . ? Ni1 S1 2.1412(17) . ? Ni1 S3 2.1473(17) . ? S1 C2 1.696(6) . ? S2 C3 1.696(6) . ? S3 C6 1.710(6) . ? S4 C7 1.716(6) . ? N1 C1 1.136(8) . ? N2 C4 1.157(8) . ? N3 C5 1.129(8) . ? N4 C8 1.129(8) . ? N5 C13 1.318(9) . ? N5 C9 1.359(10) . ? N5 N6 1.478(10) . ? N6 C15 1.358(12) . ? C1 C2 1.428(9) . ? C2 C3 1.340(7) . ? C3 C4 1.398(9) . ? C5 C6 1.440(10) . ? C6 C7 1.338(8) . ? C7 C8 1.415(8) . ? C9 H9A 0.9300 . ? C9 C10 1.298(11) . ? C10 H10A 0.9300 . ? C10 C11 1.346(11) . ? C11 H11A 0.9300 . ? C11 C12 1.362(11) . ? C12 H12A 0.9300 . ? C12 C13 1.295(11) . ? C13 H13A 0.9300 . ? C14 C15 1.430(12) . ? C14 D14A 0.9600 . ? C14 D14B 0.9600 . ? C14 D14C 0.9600 . ? C15 C16 1.382(12) . ? C16 D16A 0.9600 . ? C16 D16B 0.9600 . ? C16 D16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S2 Ni1 S4 87.83(6) . . ? S2 Ni1 S1 92.32(7) . . ? S4 Ni1 S1 179.61(7) . . ? S2 Ni1 S3 177.50(6) . . ? S4 Ni1 S3 92.42(7) . . ? S1 Ni1 S3 87.45(6) . . ? C2 S1 Ni1 102.5(2) . . ? C3 S2 Ni1 103.2(2) . . ? C6 S3 Ni1 102.5(2) . . ? C7 S4 Ni1 103.4(2) . . ? C13 N5 C9 121.8(9) . . ? C13 N5 N6 117.8(9) . . ? C9 N5 N6 120.4(8) . . ? C15 N6 N5 112.9(8) . . ? N1 C1 C2 177.4(9) . . ? C3 C2 C1 120.6(6) . . ? C3 C2 S1 121.6(5) . . ? C1 C2 S1 117.8(5) . . ? C2 C3 C4 120.9(6) . . ? C2 C3 S2 120.4(5) . . ? C4 C3 S2 118.7(5) . . ? N2 C4 C3 178.8(8) . . ? N3 C5 C6 178.2(9) . . ? C7 C6 C5 122.5(6) . . ? C7 C6 S3 121.9(5) . . ? C5 C6 S3 115.5(5) . . ? C6 C7 C8 121.7(6) . . ? C6 C7 S4 119.8(5) . . ? C8 C7 S4 118.5(5) . . ? N4 C8 C7 178.5(7) . . ? H9A C9 C10 119.8(6) . . ? H9A C9 N5 119.7(6) . . ? C10 C9 N5 120.5(9) . . ? H10A C10 C9 121.3(6) . . ? H10A C10 C11 121.2(7) . . ? C9 C10 C11 117.5(9) . . ? H11A C11 C10 119.5(7) . . ? H11A C11 C12 119.5(7) . . ? C10 C11 C12 121.0(10) . . ? H12A C12 C13 119.7(7) . . ? H12A C12 C11 119.7(7) . . ? C13 C12 C11 120.6(10) . . ? H13A C13 C12 121.0(7) . . ? H13A C13 N5 120.9(7) . . ? C12 C13 N5 118.1(10) . . ? C15 C14 D14A 109.8 . . ? C15 C14 D14B 109.3 . . ? D14A C14 D14B 109.5 . . ? C15 C14 D14C 109.3 . . ? D14A C14 D14C 109.5 . . ? D14B C14 D14C 109.5 . . ? N6 C15 C16 121.6(9) . . ? N6 C15 C14 110.7(14) . . ? C16 C15 C14 127.6(14) . . ? C15 C16 D16A 109.4 . . ? C15 C16 D16B 109.5 . . ? D16A C16 D16B 109.5 . . ? C15 C16 D16C 109.5 . . ? D16A C16 D16C 109.5 . . ? D16B C16 D16C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.547 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 948263'