# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 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_11 _database_code_depnum_ccdc_archive 'CCDC 891213' #TrackingRef '105K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H26 N4, C16 N8 Ni2 S8' _chemical_formula_sum 'C31 H26 N12 Ni2 S8' _chemical_formula_weight 940.58 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0535(2) _cell_length_b 10.0931(5) _cell_length_c 29.7271(16) _cell_angle_alpha 93.655(4) _cell_angle_beta 90.387(4) _cell_angle_gamma 110.399(4) _cell_volume 1978.62(16) _cell_formula_units_Z 2 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 4312 _cell_measurement_theta_min 2.9671 _cell_measurement_theta_max 29.1748 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960.0 _exptl_absorpt_coefficient_mu 1.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.719 _exptl_absorpt_correction_T_max 0.753 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 105(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 'Xcalibur, Sapphire3, Gemini ultra' _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 9325 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6955 _reflns_number_gt 4732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+5.8585P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6012 _refine_ls_number_parameters 478 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 0.751 _refine_ls_restrained_S_all 0.751 _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 0.87812(7) 0.67340(4) 0.274771(15) 0.02100(13) Uani 1 1 d . . . Ni2 Ni 0.39874(7) 0.77630(4) 0.221354(15) 0.02128(13) Uani 1 1 d . . . S1 S 0.98546(14) 0.84639(9) 0.32528(3) 0.0236(2) Uani 1 1 d . . . S2 S 0.82962(14) 0.51701(9) 0.32348(3) 0.0248(2) Uani 1 1 d . . . S3 S 0.92567(14) 0.82964(9) 0.22632(3) 0.0234(2) Uani 1 1 d . . . S4 S 0.76255(14) 0.50095(9) 0.22436(3) 0.0252(2) Uani 1 1 d . . . S5 S 0.52219(14) 0.94653(9) 0.27230(3) 0.0253(2) Uani 1 1 d . . . S6 S 0.34577(14) 0.61702(9) 0.26886(3) 0.0231(2) Uani 1 1 d . . . S7 S 0.43853(14) 0.93710(9) 0.17456(3) 0.0254(2) Uani 1 1 d . . . S8 S 0.29861(14) 0.60765(9) 0.16901(3) 0.0248(2) Uani 1 1 d . . . N1 N 1.0963(5) 0.9260(4) 0.44727(12) 0.0377(8) Uani 1 1 d . . . N2 N 0.8788(5) 0.4831(3) 0.44533(11) 0.0343(8) Uani 1 1 d . . . N3 N 0.6820(5) 0.4254(4) 0.10169(13) 0.0418(9) Uani 1 1 d . . . N4 N 0.8724(5) 0.8587(3) 0.10315(11) 0.0349(8) Uani 1 1 d . . . N5 N 0.4036(5) 0.5892(3) 0.39316(11) 0.0315(8) Uani 1 1 d . . . N6 N 0.6324(5) 1.0079(3) 0.39582(12) 0.0341(8) Uani 1 1 d . . . N7 N 0.2019(6) 0.5428(4) 0.04566(13) 0.0437(9) Uani 1 1 d . . . N8 N 0.3816(5) 0.9843(4) 0.05436(11) 0.0361(8) Uani 1 1 d . . . N9 N 0.4718(5) 0.2472(3) 0.47916(10) 0.0250(7) Uani 1 1 d . . . N10 N 0.2638(4) 0.2680(3) 0.42877(10) 0.0229(7) Uani 1 1 d . . . N11 N 0.0310(5) 0.2058(3) 0.09058(10) 0.0261(7) Uani 1 1 d . . . N12 N 0.2096(5) 0.2320(3) 0.03080(10) 0.0284(7) Uani 1 1 d . . . C1 C 0.8905(6) 0.5446(4) 0.41376(13) 0.0263(8) Uani 1 1 d . . . C2 C 0.9041(5) 0.6184(4) 0.37348(12) 0.0238(8) Uani 1 1 d . . . C3 C 0.9743(5) 0.7627(4) 0.37451(12) 0.0231(8) Uani 1 1 d . . . C4 C 1.0398(6) 0.8523(4) 0.41513(14) 0.0280(9) Uani 1 1 d . . . C5 C 0.7809(5) 0.5853(4) 0.17535(12) 0.0235(8) Uani 1 1 d . . . C6 C 0.7247(6) 0.4977(4) 0.13417(14) 0.0285(9) Uani 1 1 d . . . C7 C 0.8631(5) 0.8024(4) 0.13569(13) 0.0264(8) Uani 1 1 d . . . C8 C 0.8508(5) 0.7300(4) 0.17638(12) 0.0238(8) Uani 1 1 d . . . C9 C 0.4125(5) 0.6422(4) 0.35980(13) 0.0241(8) Uani 1 1 d . . . C10 C 0.4273(5) 0.7136(4) 0.31890(12) 0.0230(8) Uani 1 1 d . . . C11 C 0.5060(5) 0.8589(4) 0.32017(12) 0.0233(8) Uani 1 1 d . . . C12 C 0.5772(5) 0.9423(4) 0.36206(13) 0.0254(8) Uani 1 1 d . . . C13 C 0.3031(5) 0.6963(4) 0.12093(13) 0.0248(8) Uani 1 1 d . . . C14 C 0.2448(6) 0.6114(4) 0.07907(14) 0.0311(9) Uani 1 1 d . . . C15 C 0.3726(6) 0.9192(4) 0.08493(13) 0.0293(9) Uani 1 1 d . . . C16 C 0.3644(5) 0.8400(4) 0.12357(12) 0.0253(8) Uani 1 1 d . . . C17 C 0.6288(6) 0.2084(4) 0.50160(13) 0.0318(9) Uani 1 1 d . . . H17A H 0.6860 0.1592 0.4801 0.048 Uiso 1 1 calc R . . H17B H 0.5701 0.1480 0.5253 0.048 Uiso 1 1 calc R . . H17C H 0.7330 0.2926 0.5141 0.048 Uiso 1 1 calc R . . C18 C 0.3578(6) 0.3185(4) 0.49995(13) 0.0309(9) Uani 1 1 d . . . H18A H 0.3690 0.3520 0.5301 0.037 Uiso 1 1 calc R . . C19 C 0.2283(6) 0.3304(4) 0.46882(12) 0.0286(9) Uani 1 1 d . . . H19A H 0.1319 0.3731 0.4734 0.034 Uiso 1 1 calc R . . C20 C 0.4113(5) 0.2181(4) 0.43634(12) 0.0258(8) Uani 1 1 d . . . H20A H 0.4637 0.1703 0.4149 0.031 Uiso 1 1 calc R . . C21 C 0.1418(5) 0.2473(4) 0.38671(12) 0.0250(8) Uani 1 1 d . . . H21A H 0.0920 0.3254 0.3854 0.030 Uiso 1 1 calc R . . H21B H 0.0251 0.1610 0.3877 0.030 Uiso 1 1 calc R . . C22 C 0.2527(6) 0.2379(4) 0.34382(12) 0.0245(8) Uani 1 1 d . . . H22A H 0.2903 0.1540 0.3428 0.029 Uiso 1 1 calc R . . H22B H 0.3752 0.3203 0.3431 0.029 Uiso 1 1 calc R . . C23 C 0.1144(5) 0.2305(4) 0.30350(12) 0.0236(8) Uani 1 1 d . . . H23A H 0.0782 0.3150 0.3054 0.028 Uiso 1 1 calc R . . H23B H -0.0092 0.1498 0.3056 0.028 Uiso 1 1 calc R . . C24 C 0.2028(6) 0.2179(4) 0.25737(12) 0.0235(8) Uani 1 1 d . . . H24A H 0.3293 0.2961 0.2551 0.028 Uiso 1 1 calc R . . H24B H 0.2310 0.1304 0.2542 0.028 Uiso 1 1 calc R . . C25 C 0.0564(6) 0.2194(4) 0.21955(12) 0.0246(8) Uani 1 1 d . . . H25A H -0.0696 0.1411 0.2223 0.029 Uiso 1 1 calc R . . H25B H 0.0272 0.3064 0.2236 0.029 Uiso 1 1 calc R . . C26 C 0.1321(6) 0.2085(4) 0.17203(12) 0.0245(8) Uani 1 1 d . . . H26A H 0.2574 0.2867 0.1685 0.029 Uiso 1 1 calc R . . H26B H 0.1587 0.1207 0.1671 0.029 Uiso 1 1 calc R . . C27 C -0.0253(6) 0.2122(4) 0.13803(13) 0.0292(9) Uani 1 1 d . . . H27A H -0.1490 0.1331 0.1420 0.035 Uiso 1 1 calc R . . H27B H -0.0542 0.2986 0.1444 0.035 Uiso 1 1 calc R . . C28 C -0.0997(6) 0.1649(4) 0.05380(14) 0.0363(10) Uani 1 1 d . . . H28A H -0.2403 0.1312 0.0544 0.044 Uiso 1 1 calc R . . C29 C 0.0119(6) 0.1822(4) 0.01679(14) 0.0351(10) Uani 1 1 d . . . H29A H -0.0370 0.1635 -0.0129 0.042 Uiso 1 1 calc R . . C30 C 0.3836(7) 0.2706(5) 0.00156(13) 0.0408(10) Uani 1 1 d . . . H30A H 0.5063 0.3028 0.0197 0.061 Uiso 1 1 calc R . . H30B H 0.3795 0.3449 -0.0166 0.061 Uiso 1 1 calc R . . H30C H 0.3794 0.1894 -0.0177 0.061 Uiso 1 1 calc R . . C31 C 0.2178(6) 0.2458(4) 0.07537(13) 0.0283(9) Uani 1 1 d . . . H31A H 0.3358 0.2784 0.0933 0.034 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 0.0191(3) 0.0193(2) 0.0261(3) 0.00450(18) 0.00301(19) 0.0082(2) Ni2 0.0183(3) 0.0201(2) 0.0270(3) 0.00511(18) 0.0020(2) 0.0080(2) S1 0.0242(5) 0.0197(4) 0.0284(5) 0.0044(4) 0.0008(4) 0.0090(4) S2 0.0272(6) 0.0199(4) 0.0286(5) 0.0058(4) 0.0043(4) 0.0090(4) S3 0.0234(5) 0.0216(4) 0.0263(5) 0.0051(4) 0.0025(4) 0.0085(4) S4 0.0234(5) 0.0202(4) 0.0314(5) 0.0034(4) -0.0005(4) 0.0068(4) S5 0.0238(5) 0.0197(4) 0.0328(5) 0.0047(4) 0.0000(4) 0.0074(4) S6 0.0226(5) 0.0197(4) 0.0268(5) 0.0046(4) 0.0008(4) 0.0066(4) S7 0.0253(5) 0.0223(5) 0.0297(5) 0.0058(4) 0.0019(4) 0.0089(4) S8 0.0244(5) 0.0213(4) 0.0293(5) 0.0040(4) 0.0001(4) 0.0083(4) N1 0.046(2) 0.0333(19) 0.034(2) 0.0024(16) -0.0044(17) 0.0135(18) N2 0.040(2) 0.0330(18) 0.032(2) 0.0078(15) 0.0028(16) 0.0146(17) N3 0.033(2) 0.047(2) 0.042(2) -0.0080(18) -0.0045(17) 0.0116(19) N4 0.039(2) 0.0360(19) 0.030(2) 0.0086(15) 0.0002(16) 0.0126(17) N5 0.037(2) 0.0293(17) 0.0283(19) 0.0012(14) 0.0017(15) 0.0119(16) N6 0.035(2) 0.0330(18) 0.035(2) -0.0025(16) 0.0049(16) 0.0133(17) N7 0.045(2) 0.040(2) 0.040(2) -0.0002(17) -0.0002(18) 0.0072(19) N8 0.036(2) 0.0384(19) 0.031(2) 0.0093(16) 0.0016(16) 0.0089(17) N9 0.0267(18) 0.0235(16) 0.0256(17) 0.0033(12) -0.0013(13) 0.0095(15) N10 0.0234(18) 0.0221(15) 0.0232(17) 0.0035(12) 0.0023(13) 0.0075(14) N11 0.0246(19) 0.0246(16) 0.0274(18) 0.0059(13) 0.0006(14) 0.0059(15) N12 0.027(2) 0.0279(17) 0.0282(18) 0.0026(13) -0.0018(14) 0.0066(16) C1 0.026(2) 0.0237(19) 0.032(2) 0.0023(17) 0.0023(17) 0.0123(18) C2 0.018(2) 0.0265(19) 0.031(2) 0.0059(15) 0.0037(16) 0.0109(17) C3 0.018(2) 0.0277(19) 0.027(2) 0.0039(15) -0.0007(15) 0.0115(17) C4 0.029(2) 0.025(2) 0.034(2) 0.0058(17) 0.0015(18) 0.0130(19) C5 0.015(2) 0.029(2) 0.027(2) 0.0000(15) -0.0022(15) 0.0089(17) C6 0.017(2) 0.029(2) 0.038(2) 0.0032(18) -0.0018(18) 0.0063(18) C7 0.018(2) 0.030(2) 0.033(2) 0.0012(17) -0.0008(16) 0.0111(18) C8 0.015(2) 0.031(2) 0.028(2) 0.0030(15) 0.0008(15) 0.0102(17) C9 0.021(2) 0.0220(18) 0.028(2) 0.0008(16) 0.0014(16) 0.0069(17) C10 0.016(2) 0.029(2) 0.028(2) 0.0030(15) 0.0035(15) 0.0129(17) C11 0.0145(19) 0.0279(19) 0.030(2) 0.0049(15) 0.0022(15) 0.0095(17) C12 0.021(2) 0.0242(19) 0.034(2) 0.0026(17) 0.0054(17) 0.0118(18) C13 0.015(2) 0.031(2) 0.029(2) 0.0044(16) 0.0003(16) 0.0096(17) C14 0.026(2) 0.032(2) 0.035(2) 0.0096(18) 0.0037(19) 0.0094(19) C15 0.021(2) 0.031(2) 0.033(2) 0.0054(18) 0.0016(17) 0.0054(18) C16 0.017(2) 0.035(2) 0.026(2) 0.0080(16) 0.0034(16) 0.0103(18) C17 0.035(2) 0.037(2) 0.028(2) 0.0059(17) -0.0035(17) 0.018(2) C18 0.039(3) 0.033(2) 0.024(2) 0.0033(16) 0.0024(17) 0.016(2) C19 0.031(2) 0.035(2) 0.024(2) 0.0013(16) 0.0038(17) 0.0170(19) C20 0.025(2) 0.0248(19) 0.027(2) 0.0001(15) 0.0039(16) 0.0073(18) C21 0.022(2) 0.0267(19) 0.026(2) 0.0026(15) 0.0001(16) 0.0087(17) C22 0.024(2) 0.0196(18) 0.028(2) 0.0004(14) -0.0002(16) 0.0060(17) C23 0.022(2) 0.0196(17) 0.031(2) 0.0037(15) 0.0026(16) 0.0082(17) C24 0.025(2) 0.0167(17) 0.027(2) 0.0007(14) 0.0027(16) 0.0061(16) C25 0.027(2) 0.0230(18) 0.026(2) 0.0057(15) 0.0027(16) 0.0114(17) C26 0.027(2) 0.0213(18) 0.027(2) 0.0052(15) 0.0030(16) 0.0106(17) C27 0.025(2) 0.033(2) 0.030(2) 0.0067(16) 0.0038(17) 0.0099(19) C28 0.024(2) 0.040(2) 0.039(3) 0.0065(19) -0.0100(19) 0.003(2) C29 0.037(3) 0.033(2) 0.028(2) 0.0046(17) -0.0111(19) 0.004(2) C30 0.042(3) 0.054(3) 0.024(2) 0.0040(19) 0.0046(19) 0.014(2) C31 0.025(2) 0.030(2) 0.026(2) 0.0000(16) -0.0046(17) 0.0067(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S1 2.1461(10) . ? Ni1 S3 2.1451(9) . ? Ni1 S4 2.1450(10) . ? Ni1 S2 2.1509(9) . ? Ni2 S6 2.1439(9) . ? Ni2 S5 2.1473(11) . ? Ni2 S7 2.1502(10) . ? Ni2 S8 2.1511(10) . ? S1 C3 1.725(4) . ? S2 C2 1.719(4) . ? S3 C8 1.709(4) . ? S4 C5 1.717(4) . ? S5 C11 1.707(4) . ? S6 C10 1.705(4) . ? S7 C16 1.724(4) . ? S8 C13 1.729(4) . ? N1 C4 1.150(5) . ? N2 C1 1.146(5) . ? N3 C6 1.144(5) . ? N4 C7 1.144(5) . ? N5 C9 1.148(5) . ? N6 C12 1.152(5) . ? N7 C14 1.149(5) . ? N8 C15 1.145(5) . ? N9 C20 1.322(5) . ? N9 C18 1.378(5) . ? N9 C17 1.466(4) . ? N10 C20 1.328(4) . ? N10 C19 1.377(4) . ? N10 C21 1.475(5) . ? N11 C31 1.328(5) . ? N11 C28 1.371(5) . ? N11 C27 1.471(5) . ? N12 C31 1.322(5) . ? N12 C29 1.359(5) . ? N12 C30 1.462(5) . ? C1 C2 1.436(5) . ? C2 C3 1.364(5) . ? C3 C4 1.432(5) . ? C5 C8 1.368(5) . ? C5 C6 1.431(5) . ? C7 C8 1.440(5) . ? C9 C10 1.439(5) . ? C10 C11 1.373(5) . ? C11 C12 1.440(5) . ? C13 C16 1.358(5) . ? C13 C14 1.437(6) . ? C15 C16 1.430(5) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.336(5) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? C21 C22 1.515(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.522(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.526(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.526(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.525(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.509(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.342(6) . ? C28 H28A 0.9300 . ? C29 H29A 0.9300 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 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 87.04(4) . . ? S1 Ni1 S4 178.39(4) . . ? S3 Ni1 S4 92.76(4) . . ? S1 Ni1 S2 92.86(4) . . ? S3 Ni1 S2 179.78(4) . . ? S4 Ni1 S2 87.33(4) . . ? S6 Ni2 S5 93.00(4) . . ? S6 Ni2 S7 177.30(4) . . ? S5 Ni2 S7 86.69(4) . . ? S6 Ni2 S8 87.73(4) . . ? S5 Ni2 S8 175.59(4) . . ? S7 Ni2 S8 92.77(4) . . ? C3 S1 Ni1 103.20(13) . . ? C2 S2 Ni1 102.85(12) . . ? C8 S3 Ni1 103.23(13) . . ? C5 S4 Ni1 103.02(13) . . ? C11 S5 Ni2 102.53(13) . . ? C10 S6 Ni2 103.13(12) . . ? C16 S7 Ni2 102.96(12) . . ? C13 S8 Ni2 103.13(13) . . ? C20 N9 C18 108.1(3) . . ? C20 N9 C17 126.8(3) . . ? C18 N9 C17 125.1(3) . . ? C20 N10 C19 107.9(3) . . ? C20 N10 C21 126.8(3) . . ? C19 N10 C21 125.0(3) . . ? C31 N11 C28 107.4(3) . . ? C31 N11 C27 126.3(3) . . ? C28 N11 C27 126.2(3) . . ? C31 N12 C29 108.3(3) . . ? C31 N12 C30 125.8(3) . . ? C29 N12 C30 125.8(3) . . ? N2 C1 C2 178.5(4) . . ? C3 C2 C1 121.8(3) . . ? C3 C2 S2 121.0(3) . . ? C1 C2 S2 117.2(3) . . ? C2 C3 C4 123.4(3) . . ? C2 C3 S1 120.1(3) . . ? C4 C3 S1 116.6(3) . . ? N1 C4 C3 178.5(4) . . ? C8 C5 C6 122.5(3) . . ? C8 C5 S4 120.4(3) . . ? C6 C5 S4 117.1(3) . . ? N3 C6 C5 178.3(4) . . ? N4 C7 C8 179.4(4) . . ? C5 C8 C7 121.1(3) . . ? C5 C8 S3 120.5(3) . . ? C7 C8 S3 118.4(3) . . ? N5 C9 C10 177.9(4) . . ? C11 C10 C9 120.2(3) . . ? C11 C10 S6 120.1(3) . . ? C9 C10 S6 119.7(3) . . ? C10 C11 C12 121.0(3) . . ? C10 C11 S5 121.2(3) . . ? C12 C11 S5 117.9(3) . . ? N6 C12 C11 179.2(4) . . ? C16 C13 C14 122.8(3) . . ? C16 C13 S8 120.2(3) . . ? C14 C13 S8 117.0(3) . . ? N7 C14 C13 178.5(4) . . ? N8 C15 C16 178.9(5) . . ? C13 C16 C15 122.7(4) . . ? C13 C16 S7 120.9(3) . . ? C15 C16 S7 116.4(3) . . ? N9 C17 H17A 109.5 . . ? N9 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N9 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 N9 107.3(3) . . ? C19 C18 H18A 126.3 . . ? N9 C18 H18A 126.3 . . ? C18 C19 N10 107.5(3) . . ? C18 C19 H19A 126.3 . . ? N10 C19 H19A 126.3 . . ? N9 C20 N10 109.2(3) . . ? N9 C20 H20A 125.4 . . ? N10 C20 H20A 125.4 . . ? N10 C21 C22 115.0(3) . . ? N10 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? N10 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C21 C22 C23 108.8(3) . . ? C21 C22 H22A 109.9 . . ? C23 C22 H22A 109.9 . . ? C21 C22 H22B 109.9 . . ? C23 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? C22 C23 C24 115.4(3) . . ? C22 C23 H23A 108.4 . . ? C24 C23 H23A 108.4 . . ? C22 C23 H23B 108.4 . . ? C24 C23 H23B 108.4 . . ? H23A C23 H23B 107.5 . . ? C25 C24 C23 111.0(3) . . ? C25 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 . . ? C25 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C26 C25 C24 114.9(3) . . ? C26 C25 H25A 108.5 . . ? C24 C25 H25A 108.5 . . ? C26 C25 H25B 108.5 . . ? C24 C25 H25B 108.5 . . ? H25A C25 H25B 107.5 . . ? C27 C26 C25 109.6(3) . . ? C27 C26 H26A 109.8 . . ? C25 C26 H26A 109.8 . . ? C27 C26 H26B 109.8 . . ? C25 C26 H26B 109.8 . . ? H26A C26 H26B 108.2 . . ? N11 C27 C26 115.1(3) . . ? N11 C27 H27A 108.5 . . ? C26 C27 H27A 108.5 . . ? N11 C27 H27B 108.5 . . ? C26 C27 H27B 108.5 . . ? H27A C27 H27B 107.5 . . ? C29 C28 N11 107.6(4) . . ? C29 C28 H28A 126.2 . . ? N11 C28 H28A 126.2 . . ? C28 C29 N12 107.3(4) . . ? C28 C29 H29A 126.3 . . ? N12 C29 H29A 126.3 . . ? N12 C30 H30A 109.5 . . ? N12 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N12 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N12 C31 N11 109.3(3) . . ? N12 C31 H31A 125.3 . . ? N11 C31 H31A 125.3 . . ? _diffrn_measured_fraction_theta_max 0.864 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.864 _refine_diff_density_max 0.430 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.061 data_1 _database_code_depnum_ccdc_archive 'CCDC 891214' #TrackingRef '296K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H26 N4, C16 N8 Ni2 S8' _chemical_formula_sum 'C31 H26 N12 Ni2 S8' _chemical_formula_weight 940.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.080(3) _cell_length_b 7.1663(10) _cell_length_c 31.103(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.318(2) _cell_angle_gamma 90.00 _cell_volume 4120.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4756 _cell_measurement_theta_min 1.350 _cell_measurement_theta_max 27.530 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920.0 _exptl_absorpt_coefficient_mu 1.359 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_T_max 0.762 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _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 'Xcalibur, Sapphire3, Gemini ultra' _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 17371 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 27.53 _reflns_number_total 4719 _reflns_number_gt 2732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+1.4715P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00132(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4719 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.290456(18) 0.40567(5) 0.274329(12) 0.06065(16) Uani 1 1 d . . . S1 S 0.22984(4) 0.40885(10) 0.32407(3) 0.0677(2) Uani 1 1 d . . . S2 S 0.39242(4) 0.40034(12) 0.32320(3) 0.0738(2) Uani 1 1 d . . . S3 S 0.18886(4) 0.40564(11) 0.22551(3) 0.0674(2) Uani 1 1 d . . . S4 S 0.35118(4) 0.40848(11) 0.22474(3) 0.0723(2) Uani 1 1 d . . . N1 N 0.2544(2) 0.4173(6) 0.44550(13) 0.1254(13) Uani 1 1 d . . . N2 N 0.4695(2) 0.3928(5) 0.44382(11) 0.1125(12) Uani 1 1 d . . . N3 N 0.1146(2) 0.4112(4) 0.10342(11) 0.1028(10) Uani 1 1 d . . . N4 N 0.3264(2) 0.4221(5) 0.10339(12) 0.1188(13) Uani 1 1 d . . . N5 N 0.43242(15) 0.9021(4) 0.08187(9) 0.0770(7) Uani 1 1 d . . . N6 N 0.39263(16) 1.0888(4) 0.02695(9) 0.0835(8) Uani 1 1 d . . . C1 C 0.2733(2) 0.4119(5) 0.41341(14) 0.0875(10) Uani 1 1 d . . . C2 C 0.29604(19) 0.4056(4) 0.37302(11) 0.0707(8) Uani 1 1 d . . . C3 C 0.36699(18) 0.4020(4) 0.37249(11) 0.0706(8) Uani 1 1 d . . . C4 C 0.42378(19) 0.3968(5) 0.41238(13) 0.0839(10) Uani 1 1 d . . . C5 C 0.1584(2) 0.4103(4) 0.13570(12) 0.0767(9) Uani 1 1 d . . . C6 C 0.21391(18) 0.4096(3) 0.17630(10) 0.0646(8) Uani 1 1 d . . . C7 C 0.28500(18) 0.4112(4) 0.17609(11) 0.0686(8) Uani 1 1 d . . . C8 C 0.3077(2) 0.4170(4) 0.13552(13) 0.0841(10) Uani 1 1 d . . . C9 C 0.5000 0.9655(6) 0.2500 0.0719(11) Uani 1 2 d S . . H9A H 0.4588 1.0451 0.2499 0.086 Uiso 0.50 1 calc PR . . H9B H 0.5412 1.0451 0.2501 0.086 Uiso 0.50 1 calc PR . . C10 C 0.48359(16) 0.8470(5) 0.20853(10) 0.0731(8) Uani 1 1 d . . . H10A H 0.4429 0.7667 0.2092 0.088 Uiso 1 1 calc R . . H10B H 0.5249 0.7670 0.2094 0.088 Uiso 1 1 calc R . . C11 C 0.46606(17) 0.9524(4) 0.16455(10) 0.0733(9) Uani 1 1 d . . . H11A H 0.4243 1.0320 0.1628 0.088 Uiso 1 1 calc R . . H11B H 0.5067 1.0310 0.1628 0.088 Uiso 1 1 calc R . . C12 C 0.45046(19) 0.8167(5) 0.12628(11) 0.0852(10) Uani 1 1 d . . . H12A H 0.4925 0.7373 0.1288 0.102 Uiso 1 1 calc R . . H12B H 0.4105 0.7375 0.1289 0.102 Uiso 1 1 calc R . . C13 C 0.40656(19) 1.0685(5) 0.07057(12) 0.0823(10) Uani 1 1 d . . . H13 H 0.3990 1.1595 0.0903 0.099 Uiso 1 1 calc R . . C14 C 0.3619(2) 1.2553(6) 0.00179(12) 0.1100(13) Uani 1 1 d . . . H14A H 0.3487 1.3443 0.0215 0.165 Uiso 1 1 calc R . . H14B H 0.3197 1.2208 -0.0208 0.165 Uiso 1 1 calc R . . H14C H 0.3971 1.3096 -0.0118 0.165 Uiso 1 1 calc R . . C15 C 0.4110(2) 0.9291(6) 0.00988(13) 0.1081(14) Uani 1 1 d . . . H15 H 0.4072 0.9052 -0.0200 0.130 Uiso 1 1 calc R . . C16 C 0.4356(2) 0.8107(6) 0.04348(14) 0.1115(14) Uani 1 1 d . . . H16 H 0.4518 0.6894 0.0413 0.134 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 0.0533(2) 0.0447(2) 0.0827(3) 0.00243(18) 0.01449(18) -0.00030(16) S1 0.0558(4) 0.0582(5) 0.0887(5) 0.0007(4) 0.0171(4) -0.0014(3) S2 0.0537(4) 0.0714(5) 0.0937(6) 0.0026(4) 0.0132(4) -0.0012(4) S3 0.0548(4) 0.0622(5) 0.0839(5) 0.0019(4) 0.0147(4) 0.0002(3) S4 0.0594(5) 0.0619(5) 0.0978(6) 0.0017(4) 0.0235(4) 0.0012(4) N1 0.116(3) 0.159(4) 0.105(3) -0.008(3) 0.036(2) -0.016(2) N2 0.098(3) 0.123(3) 0.099(2) 0.002(2) -0.007(2) -0.014(2) N3 0.099(2) 0.116(3) 0.086(2) -0.0040(19) 0.0084(19) 0.001(2) N4 0.149(3) 0.112(3) 0.113(3) -0.014(2) 0.066(3) 0.006(2) N5 0.0731(17) 0.0737(19) 0.0810(18) -0.0094(16) 0.0127(14) 0.0018(14) N6 0.0814(19) 0.090(2) 0.0782(19) -0.0083(17) 0.0178(15) 0.0059(16) C1 0.077(2) 0.092(3) 0.094(3) -0.004(2) 0.023(2) -0.0094(19) C2 0.078(2) 0.0482(17) 0.083(2) -0.0025(15) 0.0154(17) -0.0050(15) C3 0.073(2) 0.0484(17) 0.085(2) 0.0024(15) 0.0106(17) -0.0041(15) C4 0.071(2) 0.077(2) 0.096(3) 0.002(2) 0.006(2) -0.0071(18) C5 0.079(2) 0.062(2) 0.089(2) -0.0031(18) 0.019(2) 0.0001(17) C6 0.075(2) 0.0367(14) 0.081(2) -0.0009(14) 0.0170(16) 0.0002(14) C7 0.080(2) 0.0411(16) 0.087(2) -0.0023(15) 0.0250(17) 0.0037(14) C8 0.095(3) 0.062(2) 0.103(3) -0.010(2) 0.038(2) 0.0030(18) C9 0.065(3) 0.067(3) 0.088(3) 0.000 0.026(2) 0.000 C10 0.0609(18) 0.069(2) 0.087(2) -0.0030(16) 0.0135(15) -0.0043(15) C11 0.066(2) 0.067(2) 0.090(2) -0.0005(17) 0.0256(17) -0.0080(15) C12 0.089(2) 0.065(2) 0.098(3) -0.0067(19) 0.0155(19) -0.0067(18) C13 0.089(2) 0.080(3) 0.080(2) -0.0073(19) 0.0233(18) 0.0039(19) C14 0.127(3) 0.111(3) 0.087(3) 0.011(2) 0.017(2) 0.020(3) C15 0.118(3) 0.112(3) 0.085(3) -0.020(3) 0.007(2) 0.021(3) C16 0.130(4) 0.091(3) 0.104(3) -0.029(3) 0.011(3) 0.021(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 2.1461(9) . ? Ni1 S3 2.1466(8) . ? Ni1 S1 2.1487(9) . ? Ni1 S2 2.1527(9) . ? S1 C2 1.721(3) . ? S2 C3 1.719(4) . ? S3 C6 1.713(3) . ? S4 C7 1.714(3) . ? N1 C1 1.142(5) . ? N2 C4 1.138(4) . ? N3 C5 1.136(4) . ? N4 C8 1.142(5) . ? N5 C13 1.305(4) . ? N5 C16 1.376(4) . ? N5 C12 1.472(4) . ? N6 C13 1.324(4) . ? N6 C15 1.344(4) . ? N6 C14 1.467(4) . ? C1 C2 1.428(5) . ? C2 C3 1.358(5) . ? C3 C4 1.432(5) . ? C5 C6 1.434(5) . ? C6 C7 1.358(4) . ? C7 C8 1.432(5) . ? C9 C10 1.511(4) . ? C9 C10 1.511(4) 2_655 ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.526(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.509(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.338(5) . ? C15 H15 0.9300 . ? C16 H16 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 S3 92.59(4) . . ? S4 Ni1 S1 178.85(3) . . ? S3 Ni1 S1 87.52(3) . . ? S4 Ni1 S2 87.33(4) . . ? S3 Ni1 S2 178.97(3) . . ? S1 Ni1 S2 92.59(4) . . ? C2 S1 Ni1 103.23(12) . . ? C3 S2 Ni1 102.97(12) . . ? C6 S3 Ni1 103.26(11) . . ? C7 S4 Ni1 102.93(12) . . ? C13 N5 C16 107.2(3) . . ? C13 N5 C12 128.1(3) . . ? C16 N5 C12 124.5(3) . . ? C13 N6 C15 107.8(3) . . ? C13 N6 C14 126.0(3) . . ? C15 N6 C14 126.2(3) . . ? N1 C1 C2 179.4(4) . . ? C3 C2 C1 122.2(3) . . ? C3 C2 S1 120.3(3) . . ? C1 C2 S1 117.5(3) . . ? C2 C3 C4 122.2(3) . . ? C2 C3 S2 120.9(3) . . ? C4 C3 S2 116.9(3) . . ? N2 C4 C3 179.2(4) . . ? N3 C5 C6 179.7(4) . . ? C7 C6 C5 121.2(3) . . ? C7 C6 S3 120.3(3) . . ? C5 C6 S3 118.6(3) . . ? C6 C7 C8 121.6(3) . . ? C6 C7 S4 120.9(3) . . ? C8 C7 S4 117.4(3) . . ? N4 C8 C7 179.3(5) . . ? C10 C9 C10 111.6(4) . 2_655 ? C10 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 2_655 . ? C10 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 2_655 . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 116.1(3) . . ? C9 C10 H10A 108.3 . . ? C11 C10 H10A 108.3 . . ? C9 C10 H10B 108.3 . . ? C11 C10 H10B 108.3 . . ? H10A C10 H10B 107.4 . . ? C12 C11 C10 110.2(3) . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N5 C12 C11 115.3(3) . . ? N5 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? N5 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? N5 C13 N6 110.1(3) . . ? N5 C13 H13 125.0 . . ? N6 C13 H13 125.0 . . ? N6 C14 H14A 109.5 . . ? N6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 N6 107.9(4) . . ? C16 C15 H15 126.1 . . ? N6 C15 H15 126.1 . . ? C15 C16 N5 107.1(4) . . ? C15 C16 H16 126.5 . . ? N5 C16 H16 126.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.302 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.106