# 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_EDT-TTF-CONH-Tpy.DMSO _database_code_depnum_ccdc_archive 'CCDC 917571' #TrackingRef 'sad-1-dmso-fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 N4 O S6, C2 H6 O S' _chemical_formula_sum 'C26 H22 N4 O2 S7' _chemical_formula_weight 646.90 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' O O 0.0106 0.0060 '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 20.167(3) _cell_length_b 19.979(5) _cell_length_c 15.367(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.935(13) _cell_angle_gamma 90.00 _cell_volume 5659(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2672 _exptl_absorpt_coefficient_mu 0.591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6943 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2008))' ; _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 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26564 _diffrn_reflns_av_R_equivalents 0.0775 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4935 _reflns_number_gt 2638 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0335P)^2^+37.7378P] 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 4935 _refine_ls_number_parameters 373 _refine_ls_number_restraints 61 _refine_ls_R_factor_all 0.1545 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.1680 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.074 _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 S1 S -0.05623(8) 0.39688(7) 0.61748(12) 0.0482(4) Uani 1 1 d . . . S2 S 0.09400(8) 0.43382(8) 0.64916(13) 0.0546(4) Uani 1 1 d . . . S3 S -0.09909(9) 0.55346(8) 0.60250(14) 0.0611(5) Uani 1 1 d . . . S4 S 0.04952(9) 0.59085(8) 0.62739(14) 0.0635(5) Uani 1 1 d . . . S5 S -0.15098(11) 0.69297(10) 0.58936(19) 0.0934(8) Uani 1 1 d . . . S6 S 0.02379(12) 0.73554(9) 0.61567(18) 0.0916(8) Uani 1 1 d . . . N1 N -0.0083(2) 0.0051(2) 0.6204(3) 0.0385(11) Uani 1 1 d . . . N2 N 0.1698(3) 0.0093(3) 0.8108(4) 0.0542(14) Uani 1 1 d . . . N3 N -0.1849(3) 0.0570(2) 0.4519(4) 0.0563(14) Uani 1 1 d . . . N4 N 0.0250(2) 0.2128(2) 0.6538(3) 0.0481(13) Uani 1 1 d . . . H4A H 0.0700 0.2240 0.6815 0.058 Uiso 1 1 calc R . . O1 O -0.0896(2) 0.2557(2) 0.5957(3) 0.0633(13) Uani 1 1 d . . . C1 C -0.0601(3) 0.0483(3) 0.5670(4) 0.0372(13) Uani 1 1 d . . . C2 C -0.0533(3) 0.1178(3) 0.5746(4) 0.0426(14) Uani 1 1 d . . . H2 H -0.0904 0.1456 0.5356 0.051 Uiso 1 1 calc R . . C3 C 0.0099(3) 0.1440(3) 0.6415(4) 0.0385(13) Uani 1 1 d . . . C4 C 0.0636(3) 0.1000(3) 0.6998(4) 0.0423(14) Uani 1 1 d . . . H4 H 0.1062 0.1165 0.7469 0.051 Uiso 1 1 calc R . . C5 C 0.0526(3) 0.0318(3) 0.6864(4) 0.0390(13) Uani 1 1 d . . . C6 C 0.1100(3) -0.0173(3) 0.7440(4) 0.0445(14) Uani 1 1 d . . . C7 C 0.2223(3) -0.0339(4) 0.8620(5) 0.068(2) Uani 1 1 d . . . H7 H 0.2641 -0.0165 0.9095 0.081 Uiso 1 1 calc R . . C8 C 0.2180(4) -0.1016(4) 0.8486(5) 0.071(2) Uani 1 1 d . . . H8 H 0.2559 -0.1292 0.8864 0.085 Uiso 1 1 calc R . . C9 C 0.1571(4) -0.1280(4) 0.7789(5) 0.073(2) Uani 1 1 d . . . H9 H 0.1527 -0.1738 0.7670 0.088 Uiso 1 1 calc R . . C10 C 0.1026(3) -0.0844(3) 0.7267(5) 0.0640(19) Uani 1 1 d . . . H10 H 0.0603 -0.1010 0.6793 0.077 Uiso 1 1 calc R . . C11 C -0.1272(3) 0.0171(3) 0.4938(4) 0.0395(13) Uani 1 1 d . . . C12 C -0.1277(3) -0.0496(3) 0.4699(4) 0.0471(15) Uani 1 1 d . . . H12 H -0.0868 -0.0761 0.5002 0.057 Uiso 1 1 calc R . . C13 C -0.1898(3) -0.0765(3) 0.4003(4) 0.0546(17) Uani 1 1 d . . . H13 H -0.1916 -0.1215 0.3840 0.066 Uiso 1 1 calc R . . C14 C -0.2480(3) -0.0362(3) 0.3561(5) 0.0565(17) Uani 1 1 d . . . H14 H -0.2899 -0.0527 0.3077 0.068 Uiso 1 1 calc R . . C15 C -0.2436(3) 0.0296(4) 0.3844(5) 0.0637(19) Uani 1 1 d . . . H15 H -0.2841 0.0566 0.3548 0.076 Uiso 1 1 calc R . . C16 C -0.0241(3) 0.2635(3) 0.6264(4) 0.0472(15) Uani 1 1 d . . . C17 C 0.0071(3) 0.3324(3) 0.6362(4) 0.0482(15) Uani 1 1 d . . . C18 C 0.0744(3) 0.3503(3) 0.6495(4) 0.0519(16) Uani 1 1 d . . . H18 H 0.1100 0.3181 0.6587 0.062 Uiso 1 1 calc R . . C19 C 0.0063(3) 0.4612(3) 0.6291(4) 0.0438(14) Uani 1 1 d . . . C20 C -0.0117(3) 0.5261(3) 0.6221(4) 0.0475(15) Uani 1 1 d . . . C21 C -0.0789(3) 0.6386(3) 0.6059(5) 0.0568(17) Uani 1 1 d . A . C22 C -0.0119(4) 0.6551(3) 0.6158(4) 0.0548(17) Uani 1 1 d . A . C23A C -0.1217(10) 0.7556(13) 0.5273(16) 0.096(7) Uani 0.55 1 d PDU A 1 H23A H -0.1082 0.7354 0.4795 0.115 Uiso 0.55 1 calc PR A 1 H23B H -0.1593 0.7887 0.4972 0.115 Uiso 0.55 1 calc PR A 1 C24A C -0.0545(9) 0.7874(9) 0.6094(12) 0.080(5) Uani 0.55 1 d PDU A 1 H24A H -0.0601 0.7858 0.6691 0.096 Uiso 0.55 1 calc PR A 1 H24B H -0.0482 0.8337 0.5950 0.096 Uiso 0.55 1 calc PR A 1 C23B C -0.1281(12) 0.7674(14) 0.555(2) 0.084(7) Uani 0.45 1 d PDU A 2 H23C H -0.1601 0.7730 0.4885 0.100 Uiso 0.45 1 calc PR A 2 H23D H -0.1414 0.8018 0.5897 0.100 Uiso 0.45 1 calc PR A 2 C24B C -0.0513(11) 0.7856(12) 0.5637(16) 0.080(6) Uani 0.45 1 d PDU A 2 H24C H -0.0392 0.8281 0.5970 0.096 Uiso 0.45 1 calc PR A 2 H24D H -0.0558 0.7943 0.4994 0.096 Uiso 0.45 1 calc PR A 2 S7 S 0.25648(10) 0.22150(11) 0.80399(15) 0.0768(6) Uani 1 1 d . . . O2 O 0.1829(2) 0.2246(2) 0.7225(3) 0.0643(13) Uani 1 1 d . . . C25 C 0.2593(6) 0.2884(4) 0.8790(6) 0.117(3) Uani 1 1 d . . . H25A H 0.2615 0.3298 0.8486 0.176 Uiso 1 1 calc R . . H25B H 0.3015 0.2843 0.9377 0.176 Uiso 1 1 calc R . . H25C H 0.2166 0.2877 0.8919 0.176 Uiso 1 1 calc R . . C26 C 0.2544(5) 0.1574(4) 0.8799(6) 0.127(4) Uani 1 1 d . . . H26A H 0.2147 0.1648 0.8982 0.191 Uiso 1 1 calc R . . H26B H 0.2992 0.1571 0.9357 0.191 Uiso 1 1 calc R . . H26C H 0.2481 0.1152 0.8477 0.191 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 S1 0.0405(8) 0.0415(8) 0.0600(10) 0.0008(7) 0.0176(7) -0.0010(7) S2 0.0434(9) 0.0477(9) 0.0704(11) -0.0006(8) 0.0207(8) -0.0036(7) S3 0.0507(10) 0.0468(10) 0.0859(13) 0.0040(9) 0.0280(9) 0.0011(8) S4 0.0544(10) 0.0470(10) 0.0889(14) 0.0080(9) 0.0287(9) -0.0031(8) S5 0.0723(13) 0.0539(11) 0.150(2) -0.0069(13) 0.0413(14) 0.0088(10) S6 0.0797(14) 0.0431(10) 0.1233(19) -0.0056(11) 0.0116(13) -0.0144(10) N1 0.033(2) 0.038(3) 0.041(3) 0.005(2) 0.012(2) 0.001(2) N2 0.043(3) 0.068(4) 0.045(3) 0.004(3) 0.012(3) 0.006(3) N3 0.041(3) 0.048(3) 0.064(4) -0.003(3) 0.005(3) 0.001(3) N4 0.040(3) 0.036(3) 0.058(3) -0.006(2) 0.010(2) -0.004(2) O1 0.041(3) 0.046(3) 0.096(4) -0.009(2) 0.021(2) -0.002(2) C1 0.031(3) 0.042(3) 0.034(3) -0.003(3) 0.008(2) -0.003(3) C2 0.036(3) 0.043(3) 0.043(3) 0.006(3) 0.010(3) 0.007(3) C3 0.037(3) 0.037(3) 0.044(3) -0.005(3) 0.019(3) -0.002(3) C4 0.033(3) 0.049(4) 0.041(3) -0.008(3) 0.012(3) -0.005(3) C5 0.033(3) 0.043(3) 0.039(3) 0.003(3) 0.013(3) 0.000(3) C6 0.039(3) 0.056(4) 0.038(3) 0.005(3) 0.016(3) 0.002(3) C7 0.038(4) 0.094(6) 0.055(4) 0.013(4) 0.002(3) 0.017(4) C8 0.062(5) 0.074(5) 0.074(5) 0.023(4) 0.026(4) 0.029(4) C9 0.063(5) 0.052(4) 0.092(6) 0.017(4) 0.019(4) 0.014(4) C10 0.048(4) 0.048(4) 0.076(5) 0.007(4) 0.005(3) 0.002(3) C11 0.041(3) 0.039(3) 0.042(3) -0.002(3) 0.020(3) -0.001(3) C12 0.044(3) 0.045(4) 0.047(4) 0.001(3) 0.013(3) 0.004(3) C13 0.055(4) 0.052(4) 0.051(4) -0.014(3) 0.016(3) -0.013(3) C14 0.043(4) 0.068(5) 0.051(4) -0.011(3) 0.011(3) -0.014(3) C15 0.042(4) 0.066(5) 0.063(5) -0.002(4) 0.000(3) 0.003(3) C16 0.045(4) 0.045(4) 0.049(4) -0.012(3) 0.016(3) -0.005(3) C17 0.045(4) 0.046(4) 0.049(4) -0.009(3) 0.015(3) -0.004(3) C18 0.043(4) 0.044(4) 0.063(4) -0.002(3) 0.016(3) 0.006(3) C19 0.047(3) 0.043(4) 0.041(3) -0.005(3) 0.017(3) -0.006(3) C20 0.045(3) 0.044(4) 0.048(4) 0.000(3) 0.014(3) -0.003(3) C21 0.050(4) 0.048(4) 0.064(4) -0.009(3) 0.014(3) -0.003(3) C22 0.064(4) 0.043(4) 0.048(4) 0.001(3) 0.014(3) -0.007(3) C23A 0.093(9) 0.098(11) 0.092(11) 0.021(9) 0.032(8) 0.036(8) C24A 0.104(9) 0.045(7) 0.087(10) 0.010(8) 0.034(8) 0.003(6) C23B 0.092(10) 0.064(10) 0.098(12) 0.003(9) 0.041(8) 0.011(8) C24B 0.100(9) 0.060(9) 0.090(11) 0.023(9) 0.047(9) 0.012(8) S7 0.0507(10) 0.0845(14) 0.0820(14) -0.0171(11) 0.0134(10) -0.0096(10) O2 0.046(2) 0.062(3) 0.068(3) -0.008(2) 0.005(2) -0.001(2) C25 0.151(9) 0.075(6) 0.101(7) -0.032(5) 0.025(6) -0.024(6) C26 0.129(8) 0.088(6) 0.088(7) 0.015(5) -0.034(6) -0.026(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S1 C17 1.754(6) . ? S1 C19 1.759(6) . ? S2 C18 1.714(6) . ? S2 C19 1.755(6) . ? S3 C21 1.744(6) . ? S3 C20 1.750(6) . ? S4 C22 1.742(7) . ? S4 C20 1.768(6) . ? S5 C23B 1.70(3) . ? S5 C21 1.748(7) . ? S5 C23A 1.81(3) . ? S6 C24B 1.72(2) . ? S6 C22 1.762(6) . ? S6 C24A 1.859(19) . ? N1 C5 1.345(7) . ? N1 C1 1.346(6) . ? N2 C6 1.337(7) . ? N2 C7 1.343(8) . ? N3 C15 1.335(7) . ? N3 C11 1.340(7) . ? N4 C16 1.360(7) . ? N4 C3 1.404(7) . ? N4 H4A 0.8600 . ? O1 C16 1.219(7) . ? C1 C2 1.396(7) . ? C1 C11 1.501(7) . ? C2 C3 1.375(7) . ? C2 H2 0.9300 . ? C3 C4 1.400(7) . ? C4 C5 1.384(7) . ? C4 H4 0.9300 . ? C5 C6 1.501(8) . ? C6 C10 1.364(8) . ? C7 C8 1.366(10) . ? C7 H7 0.9300 . ? C8 C9 1.367(10) . ? C8 H8 0.9300 . ? C9 C10 1.376(8) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.380(7) . ? C12 C13 1.384(8) . ? C12 H12 0.9300 . ? C13 C14 1.356(8) . ? C13 H13 0.9300 . ? C14 C15 1.377(9) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.495(8) . ? C17 C18 1.338(8) . ? C18 H18 0.9300 . ? C19 C20 1.338(8) . ? C21 C22 1.338(8) . ? C23A C24A 1.563(17) . ? C23A H23A 0.9700 . ? C23A H23B 0.9700 . ? C24A H24A 0.9700 . ? C24A H24B 0.9700 . ? C23B C24B 1.543(19) . ? C23B H23C 0.9700 . ? C23B H23D 0.9700 . ? C24B H24C 0.9700 . ? C24B H24D 0.9700 . ? S7 O2 1.506(4) . ? S7 C26 1.744(9) . ? S7 C25 1.750(8) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 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 C17 S1 C19 94.4(3) . . ? C18 S2 C19 95.0(3) . . ? C21 S3 C20 95.3(3) . . ? C22 S4 C20 94.6(3) . . ? C23B S5 C21 105.9(9) . . ? C21 S5 C23A 94.4(8) . . ? C24B S6 C22 104.4(8) . . ? C22 S6 C24A 99.8(6) . . ? C5 N1 C1 116.9(4) . . ? C6 N2 C7 116.4(6) . . ? C15 N3 C11 116.9(5) . . ? C16 N4 C3 126.7(5) . . ? C16 N4 H4A 116.7 . . ? C3 N4 H4A 116.7 . . ? N1 C1 C2 124.1(5) . . ? N1 C1 C11 115.6(5) . . ? C2 C1 C11 120.3(5) . . ? C3 C2 C1 118.1(5) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 118.7(5) . . ? C2 C3 N4 123.9(5) . . ? C4 C3 N4 117.3(5) . . ? C5 C4 C3 119.2(5) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 123.0(5) . . ? N1 C5 C6 115.9(5) . . ? C4 C5 C6 121.1(5) . . ? N2 C6 C10 122.3(6) . . ? N2 C6 C5 115.7(5) . . ? C10 C6 C5 122.0(5) . . ? N2 C7 C8 124.1(7) . . ? N2 C7 H7 117.9 . . ? C8 C7 H7 117.9 . . ? C7 C8 C9 118.8(6) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C8 C9 C10 117.6(7) . . ? C8 C9 H9 121.2 . . ? C10 C9 H9 121.2 . . ? C6 C10 C9 120.7(6) . . ? C6 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? N3 C11 C12 122.4(5) . . ? N3 C11 C1 117.1(5) . . ? C12 C11 C1 120.5(5) . . ? C11 C12 C13 119.1(6) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C14 C13 C12 119.1(6) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 118.4(6) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? N3 C15 C14 124.1(6) . . ? N3 C15 H15 117.9 . . ? C14 C15 H15 117.9 . . ? O1 C16 N4 124.2(5) . . ? O1 C16 C17 120.3(5) . . ? N4 C16 C17 115.5(5) . . ? C18 C17 C16 128.5(6) . . ? C18 C17 S1 117.1(5) . . ? C16 C17 S1 114.2(4) . . ? C17 C18 S2 118.7(5) . . ? C17 C18 H18 120.6 . . ? S2 C18 H18 120.6 . . ? C20 C19 S2 122.5(4) . . ? C20 C19 S1 122.7(5) . . ? S2 C19 S1 114.8(3) . . ? C19 C20 S3 122.5(5) . . ? C19 C20 S4 122.9(5) . . ? S3 C20 S4 114.5(3) . . ? C22 C21 S3 117.1(5) . . ? C22 C21 S5 127.2(5) . . ? S3 C21 S5 115.6(4) . . ? C21 C22 S4 118.3(5) . . ? C21 C22 S6 128.3(5) . . ? S4 C22 S6 113.4(4) . . ? C24A C23A S5 102.6(15) . . ? C24A C23A H23A 111.3 . . ? S5 C23A H23A 111.3 . . ? C24A C23A H23B 111.3 . . ? S5 C23A H23B 111.3 . . ? H23A C23A H23B 109.2 . . ? C23A C24A S6 104.8(14) . . ? C23A C24A H24A 110.8 . . ? S6 C24A H24A 110.8 . . ? C23A C24A H24B 110.8 . . ? S6 C24A H24B 110.8 . . ? H24A C24A H24B 108.9 . . ? C24B C23B S5 125(2) . . ? C24B C23B H23C 106.2 . . ? S5 C23B H23C 106.2 . . ? C24B C23B H23D 106.2 . . ? S5 C23B H23D 106.2 . . ? H23C C23B H23D 106.4 . . ? C23B C24B S6 124.5(19) . . ? C23B C24B H24C 106.2 . . ? S6 C24B H24C 106.2 . . ? C23B C24B H24D 106.2 . . ? S6 C24B H24D 106.2 . . ? H24C C24B H24D 106.4 . . ? O2 S7 C26 107.6(4) . . ? O2 S7 C25 105.9(4) . . ? C26 S7 C25 97.1(5) . . ? S7 C25 H25A 109.5 . . ? S7 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S7 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? S7 C26 H26A 109.5 . . ? S7 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? S7 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A O2 0.86 2.10 2.929(6) 161.1 . C13 H13 O2 0.93 2.68 3.542(8) 154.4 5_556 C18 H18 O2 0.93 2.33 3.219(7) 158.9 . C25 H25A N3 0.96 2.72 3.322(9) 121.2 8_556 C25 H25B O1 0.96 2.65 3.593(10) 167.2 8_556 C26 H26C N2 0.96 2.56 3.366(10) 141.3 . C24B H24D N4 0.97 2.67 3.59(2) 158.2 5_566 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.911 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.077 data_EDT-TTF-CONH-Tpy.MeOH _database_code_depnum_ccdc_archive 'CCDC 917572' #TrackingRef 'sad-1-MeOH-fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 N4 O S6, C H4 O' _chemical_formula_sum 'C25 H20 N4 O2 S6' _chemical_formula_weight 600.81 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' O O 0.0106 0.0060 '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 1 2/c 1' _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 25.001(2) _cell_length_b 11.856(1) _cell_length_c 20.044(1) _cell_angle_alpha 90.00 _cell_angle_beta 117.164(7) _cell_angle_gamma 90.00 _cell_volume 5286.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 11011 _cell_measurement_theta_min 3.82 _cell_measurement_theta_max 27.53 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2480 _exptl_absorpt_coefficient_mu 0.550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.686 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2008))' ; _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 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49500 _diffrn_reflns_av_R_equivalents 0.1001 _diffrn_reflns_av_sigmaI/netI 0.0860 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6039 _reflns_number_gt 3510 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0062P)^2^+26.6576P] 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 6039 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1375 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 C1 C 0.83609(16) 1.1594(3) 0.40957(19) 0.0215(8) Uani 1 1 d . . . C2 C 0.83373(17) 1.0666(3) 0.4500(2) 0.0237(9) Uani 1 1 d . . . H2 H 0.8641 1.0127 0.4668 0.028 Uiso 1 1 calc R . . C3 C 0.78476(16) 1.0558(3) 0.46510(19) 0.0219(8) Uani 1 1 d . . . C4 C 0.73898(16) 1.1353(3) 0.43517(19) 0.0217(8) Uani 1 1 d . . . H4 H 0.7053 1.1290 0.4431 0.026 Uiso 1 1 calc R . . C5 C 0.74397(16) 1.2241(3) 0.39331(19) 0.0216(8) Uani 1 1 d . . . C6 C 0.88958(16) 1.1744(3) 0.39486(19) 0.0229(8) Uani 1 1 d . . . C7 C 0.89394(19) 1.2647(4) 0.3542(2) 0.0409(12) Uani 1 1 d . . . H7 H 0.8634 1.3181 0.3344 0.049 Uiso 1 1 calc R . . C8 C 0.9449(2) 1.2742(4) 0.3434(3) 0.0534(14) Uani 1 1 d . . . H8 H 0.9488 1.3342 0.3161 0.064 Uiso 1 1 calc R . . C9 C 0.98939(19) 1.1946(4) 0.3734(3) 0.0453(12) Uani 1 1 d . . . H9 H 1.0240 1.1997 0.3672 0.054 Uiso 1 1 calc R . . C10 C 0.98128(18) 1.1069(4) 0.4127(2) 0.0323(10) Uani 1 1 d . . . H10 H 1.0113 1.0525 0.4328 0.039 Uiso 1 1 calc R . . C11 C 0.69506(16) 1.3098(3) 0.3580(2) 0.0232(8) Uani 1 1 d . . . C12 C 0.69627(18) 1.3885(3) 0.3076(2) 0.0310(10) Uani 1 1 d . . . H12 H 0.7272 1.3876 0.2939 0.037 Uiso 1 1 calc R . . C13 C 0.65137(19) 1.4680(4) 0.2779(2) 0.0387(11) Uani 1 1 d . . . H13 H 0.6519 1.5224 0.2447 0.046 Uiso 1 1 calc R . . C14 C 0.6057(2) 1.4655(4) 0.2983(2) 0.0423(11) Uani 1 1 d . . . H14 H 0.5745 1.5179 0.2791 0.051 Uiso 1 1 calc R . . C15 C 0.60724(19) 1.3836(4) 0.3477(2) 0.0380(11) Uani 1 1 d . . . H15 H 0.5761 1.3821 0.3609 0.046 Uiso 1 1 calc R . . C16 C 0.81861(17) 0.8801(3) 0.5405(2) 0.0230(8) Uani 1 1 d . . . C17 C 0.80427(16) 0.7995(3) 0.58615(19) 0.0212(8) Uani 1 1 d . . . C18 C 0.76046(16) 0.8006(3) 0.60644(19) 0.0238(9) Uani 1 1 d . . . H18 H 0.7331 0.8599 0.5923 0.029 Uiso 1 1 calc R . . C19 C 0.82152(16) 0.6229(3) 0.66948(19) 0.0228(8) Uani 1 1 d . . . C20 C 0.84405(16) 0.5307(3) 0.71158(19) 0.0213(8) Uani 1 1 d . . . C21 C 0.92217(17) 0.3893(3) 0.8011(2) 0.0267(9) Uani 1 1 d . . . C22 C 0.87875(17) 0.3930(3) 0.8228(2) 0.0247(9) Uani 1 1 d . . . C23 C 0.9224(2) 0.1992(4) 0.8979(3) 0.0418(11) Uani 1 1 d . . . H23A H 0.9245 0.1456 0.9356 0.050 Uiso 1 1 calc R . . H23B H 0.9022 0.1629 0.8493 0.050 Uiso 1 1 calc R . . C24 C 0.9853(2) 0.2321(5) 0.9129(3) 0.0620(16) Uani 1 1 d . . . H24A H 1.0080 0.1636 0.9177 0.074 Uiso 1 1 calc R . . H24B H 1.0043 0.2709 0.9607 0.074 Uiso 1 1 calc R . . C25 C 0.61946(18) 1.0584(4) 0.4943(2) 0.0409(11) Uani 1 1 d . . . H25A H 0.5939 1.0649 0.5181 0.061 Uiso 1 1 calc R . . H25B H 0.6047 0.9995 0.4574 0.061 Uiso 1 1 calc R . . H25C H 0.6196 1.1285 0.4704 0.061 Uiso 1 1 calc R . . N1 N 0.79311(13) 1.2388(3) 0.38171(16) 0.0233(7) Uani 1 1 d . . . N2 N 0.93252(14) 1.0956(3) 0.42365(18) 0.0283(8) Uani 1 1 d . . . N3 N 0.65070(14) 1.3059(3) 0.37826(18) 0.0301(8) Uani 1 1 d . . . N4 N 0.77988(13) 0.9686(3) 0.50947(16) 0.0241(7) Uani 1 1 d . . . H4B H 0.7492 0.9711 0.5181 0.029 Uiso 1 1 calc R . . O1 O 0.86326(12) 0.8625(2) 0.53128(15) 0.0340(7) Uani 1 1 d . . . O2 O 0.67886(12) 1.0322(2) 0.54892(15) 0.0329(7) Uani 1 1 d . . . H2B H 0.6907 1.0806 0.5818 0.049 Uiso 1 1 calc R . . S1 S 0.85455(4) 0.68402(9) 0.61704(5) 0.0279(2) Uani 1 1 d . . . S2 S 0.75527(4) 0.68998(9) 0.65961(5) 0.0268(2) Uani 1 1 d . . . S3 S 0.90802(4) 0.45966(9) 0.71717(5) 0.0271(2) Uani 1 1 d . . . S4 S 0.81189(4) 0.46402(9) 0.76335(5) 0.0256(2) Uani 1 1 d . . . S5 S 0.99129(5) 0.31981(11) 0.84383(7) 0.0447(3) Uani 1 1 d . . . S6 S 0.87987(5) 0.32052(10) 0.89967(6) 0.0342(3) Uani 1 1 d . . . 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 C1 0.023(2) 0.019(2) 0.0219(19) -0.0021(15) 0.0096(16) -0.0012(17) C2 0.027(2) 0.019(2) 0.026(2) 0.0007(16) 0.0130(18) 0.0037(17) C3 0.026(2) 0.018(2) 0.0207(18) 0.0008(16) 0.0101(17) -0.0020(17) C4 0.020(2) 0.022(2) 0.0230(19) 0.0002(16) 0.0101(16) 0.0006(16) C5 0.023(2) 0.020(2) 0.0185(18) -0.0025(15) 0.0072(17) -0.0032(16) C6 0.023(2) 0.022(2) 0.0223(19) -0.0034(17) 0.0097(16) -0.0042(18) C7 0.031(3) 0.046(3) 0.050(3) 0.026(2) 0.023(2) 0.013(2) C8 0.039(3) 0.059(3) 0.074(4) 0.039(3) 0.037(3) 0.009(3) C9 0.029(2) 0.060(3) 0.055(3) 0.018(3) 0.026(2) 0.009(2) C10 0.027(2) 0.029(2) 0.041(2) 0.003(2) 0.016(2) 0.0063(19) C11 0.0197(19) 0.020(2) 0.0254(19) -0.0014(17) 0.0061(16) -0.0040(17) C12 0.030(2) 0.033(3) 0.030(2) 0.0086(19) 0.0131(19) 0.004(2) C13 0.043(3) 0.033(3) 0.033(2) 0.015(2) 0.011(2) 0.006(2) C14 0.035(3) 0.031(3) 0.050(3) 0.003(2) 0.010(2) 0.012(2) C15 0.027(2) 0.033(3) 0.056(3) 0.002(2) 0.020(2) -0.001(2) C16 0.020(2) 0.025(2) 0.024(2) 0.0026(16) 0.0099(17) -0.0016(17) C17 0.021(2) 0.017(2) 0.0232(19) 0.0048(15) 0.0082(16) 0.0034(16) C18 0.025(2) 0.019(2) 0.026(2) 0.0045(16) 0.0109(17) 0.0057(17) C19 0.024(2) 0.023(2) 0.0219(19) 0.0013(16) 0.0113(17) -0.0033(17) C20 0.024(2) 0.020(2) 0.0219(18) -0.0026(16) 0.0119(16) -0.0020(17) C21 0.026(2) 0.023(2) 0.031(2) 0.0069(17) 0.0137(18) 0.0025(18) C22 0.024(2) 0.024(2) 0.026(2) 0.0051(17) 0.0112(18) 0.0010(17) C23 0.051(3) 0.029(3) 0.051(3) 0.012(2) 0.027(2) 0.009(2) C24 0.052(3) 0.065(4) 0.084(4) 0.049(3) 0.044(3) 0.032(3) C25 0.032(3) 0.045(3) 0.040(3) 0.003(2) 0.012(2) 0.008(2) N1 0.0214(17) 0.0239(18) 0.0234(16) 0.0023(14) 0.0090(14) 0.0008(14) N2 0.0264(19) 0.0243(19) 0.0364(19) 0.0003(15) 0.0162(16) -0.0003(15) N3 0.0244(18) 0.0265(19) 0.042(2) 0.0023(16) 0.0168(16) 0.0011(16) N4 0.0238(17) 0.0222(18) 0.0315(17) 0.0075(15) 0.0172(15) 0.0039(15) O1 0.0323(17) 0.0326(17) 0.0441(17) 0.0154(13) 0.0235(14) 0.0120(13) O2 0.0323(16) 0.0294(17) 0.0346(16) -0.0031(13) 0.0131(13) 0.0026(14) S1 0.0285(6) 0.0263(6) 0.0349(5) 0.0108(5) 0.0197(5) 0.0078(5) S2 0.0278(5) 0.0250(5) 0.0335(5) 0.0097(4) 0.0191(5) 0.0056(5) S3 0.0302(6) 0.0272(6) 0.0293(5) 0.0065(4) 0.0181(5) 0.0073(5) S4 0.0238(5) 0.0247(5) 0.0312(5) 0.0066(4) 0.0150(4) 0.0029(5) S5 0.0264(6) 0.0583(8) 0.0516(7) 0.0297(6) 0.0197(5) 0.0150(6) S6 0.0382(6) 0.0338(6) 0.0393(6) 0.0137(5) 0.0253(5) 0.0075(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 C1 N1 1.343(5) . ? C1 C2 1.384(5) . ? C1 C6 1.505(5) . ? C2 C3 1.394(5) . ? C2 H2 0.9300 . ? C3 C4 1.389(5) . ? C3 N4 1.405(4) . ? C4 C5 1.387(5) . ? C4 H4 0.9300 . ? C5 N1 1.362(5) . ? C5 C11 1.496(5) . ? C6 N2 1.338(5) . ? C6 C7 1.379(5) . ? C7 C8 1.392(6) . ? C7 H7 0.9300 . ? C8 C9 1.370(6) . ? C8 H8 0.9300 . ? C9 C10 1.375(6) . ? C9 H9 0.9300 . ? C10 N2 1.340(5) . ? C10 H10 0.9300 . ? C11 N3 1.345(5) . ? C11 C12 1.386(5) . ? C12 C13 1.376(6) . ? C12 H12 0.9300 . ? C13 C14 1.378(6) . ? C13 H13 0.9300 . ? C14 C15 1.376(6) . ? C14 H14 0.9300 . ? C15 N3 1.341(5) . ? C15 H15 0.9300 . ? C16 O1 1.229(4) . ? C16 N4 1.369(5) . ? C16 C17 1.477(5) . ? C17 C18 1.331(5) . ? C17 S1 1.768(4) . ? C18 S2 1.732(4) . ? C18 H18 0.9300 . ? C19 C20 1.338(5) . ? C19 S1 1.762(3) . ? C19 S2 1.765(4) . ? C20 S4 1.764(4) . ? C20 S3 1.765(4) . ? C21 C22 1.342(5) . ? C21 S5 1.746(4) . ? C21 S3 1.763(4) . ? C22 S6 1.753(4) . ? C22 S4 1.762(4) . ? C23 C24 1.511(6) . ? C23 S6 1.798(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 S5 1.791(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 O2 1.420(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? N4 H4B 0.8600 . ? O2 H2B 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 124.1(3) . . ? N1 C1 C6 116.7(3) . . ? C2 C1 C6 119.2(3) . . ? C1 C2 C3 118.4(3) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 118.4(3) . . ? C4 C3 N4 118.7(3) . . ? C2 C3 N4 122.9(3) . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N1 C5 C4 122.5(3) . . ? N1 C5 C11 116.0(3) . . ? C4 C5 C11 121.5(3) . . ? N2 C6 C7 122.1(3) . . ? N2 C6 C1 116.3(3) . . ? C7 C6 C1 121.6(4) . . ? C6 C7 C8 118.7(4) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? C9 C8 C7 119.6(4) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 118.0(4) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? N2 C10 C9 123.6(4) . . ? N2 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? N3 C11 C12 122.6(4) . . ? N3 C11 C5 116.2(3) . . ? C12 C11 C5 121.2(3) . . ? C13 C12 C11 119.5(4) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 118.7(4) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 118.3(4) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? N3 C15 C14 124.4(4) . . ? N3 C15 H15 117.8 . . ? C14 C15 H15 117.8 . . ? O1 C16 N4 124.4(3) . . ? O1 C16 C17 118.5(3) . . ? N4 C16 C17 117.1(3) . . ? C18 C17 C16 130.5(3) . . ? C18 C17 S1 117.0(3) . . ? C16 C17 S1 112.5(3) . . ? C17 C18 S2 118.9(3) . . ? C17 C18 H18 120.5 . . ? S2 C18 H18 120.5 . . ? C20 C19 S1 122.4(3) . . ? C20 C19 S2 122.8(3) . . ? S1 C19 S2 114.8(2) . . ? C19 C20 S4 124.3(3) . . ? C19 C20 S3 122.6(3) . . ? S4 C20 S3 113.1(2) . . ? C22 C21 S5 128.5(3) . . ? C22 C21 S3 117.0(3) . . ? S5 C21 S3 114.4(2) . . ? C21 C22 S6 125.3(3) . . ? C21 C22 S4 117.0(3) . . ? S6 C22 S4 117.3(2) . . ? C24 C23 S6 111.2(3) . . ? C24 C23 H23A 109.4 . . ? S6 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? S6 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 C24 S5 116.3(3) . . ? C23 C24 H24A 108.2 . . ? S5 C24 H24A 108.2 . . ? C23 C24 H24B 108.2 . . ? S5 C24 H24B 108.2 . . ? H24A C24 H24B 107.4 . . ? O2 C25 H25A 109.5 . . ? O2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C1 N1 C5 116.9(3) . . ? C6 N2 C10 118.1(3) . . ? C15 N3 C11 116.6(3) . . ? C16 N4 C3 127.1(3) . . ? C16 N4 H4B 116.4 . . ? C3 N4 H4B 116.4 . . ? C25 O2 H2B 109.5 . . ? C19 S1 C17 94.32(17) . . ? C18 S2 C19 94.60(17) . . ? C21 S3 C20 93.87(17) . . ? C22 S4 C20 93.76(17) . . ? C21 S5 C24 103.9(2) . . ? C22 S6 C23 98.46(19) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4B O2 0.86 2.23 3.065(4) 162.4 . C18 H18 O2 0.93 2.39 3.299(5) 167.0 . O2 H2B N1 0.82 2.24 2.984(4) 151.2 7_676 C9 H9 O1 0.93 2.72 3.355(5) 126.4 5_776 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.478 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.096 data_[{(MeS)3-TTF-SCH2CONH-Tpy}2Ni]*(ClO4)2*0.5(H2O) _database_code_depnum_ccdc_archive 'CCDC 917573' #TrackingRef 'sad-2-Ni-180K-fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H44 N8 Ni O2 S16, 2(Cl O4), 0.5(H2 O)' _chemical_formula_sum 'C52 H45 Cl2 N8 Ni O10.5 S16' _chemical_formula_weight 1592.53 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.967(9) _cell_length_b 17.79(1) _cell_length_c 21.38(2) _cell_angle_alpha 83.0(1) _cell_angle_beta 88.3(1) _cell_angle_gamma 77.74(9) _cell_volume 3308(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5180 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 27.06 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1630 _exptl_absorpt_coefficient_mu 0.941 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.700 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2008))' ; _exptl_special_details ; MOLTECH ANJOU UMR CNRS 6200 2, bd Lavoisier 49045 Angers cedex France ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49431 _diffrn_reflns_av_R_equivalents 0.2350 _diffrn_reflns_av_sigmaI/netI 0.3547 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.06 _reflns_number_total 14074 _reflns_number_gt 4340 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.2i (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1129P)^2^+12.0684P] 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 14074 _refine_ls_number_parameters 817 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3442 _refine_ls_R_factor_gt 0.1152 _refine_ls_wR_factor_ref 0.3306 _refine_ls_wR_factor_gt 0.2286 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C1 C 0.7214(16) -0.3921(8) -0.2111(6) 0.053(4) Uani 1 1 d . . . C2 C 0.7350(15) -0.3815(8) -0.2729(6) 0.048(4) Uani 1 1 d . . . C3 C 0.8161(19) -0.3920(10) -0.3892(7) 0.067(4) Uani 1 1 d . . . C4 C 0.6953(19) -0.3322(10) -0.3936(6) 0.064(4) Uani 1 1 d . . . C5 C 1.1018(16) -0.4119(10) -0.4469(9) 0.086(5) Uani 1 1 d . . . H5A H 1.0933 -0.3588 -0.4398 0.129 Uiso 1 1 calc R . . H5B H 1.1608 -0.4216 -0.4843 0.129 Uiso 1 1 calc R . . H5C H 1.1512 -0.4454 -0.4115 0.129 Uiso 1 1 calc R . . C6 C 0.446(2) -0.2989(11) -0.4651(10) 0.123(8) Uani 1 1 d . . . H6A H 0.4589 -0.3539 -0.4550 0.185 Uiso 1 1 calc R . . H6B H 0.4053 -0.2838 -0.5069 0.185 Uiso 1 1 calc R . . H6C H 0.3768 -0.2732 -0.4355 0.185 Uiso 1 1 calc R . . C7 C 0.7318(19) -0.4453(10) -0.0912(6) 0.059(4) Uani 1 1 d . . . C8 C 0.6211(17) -0.3799(9) -0.0963(6) 0.058(4) Uani 1 1 d . . . C9 C 0.878(3) -0.5955(12) -0.0427(11) 0.165(12) Uani 1 1 d . . . H9A H 0.8173 -0.6086 -0.0743 0.248 Uiso 1 1 calc R . . H9B H 0.8848 -0.6334 -0.0063 0.248 Uiso 1 1 calc R . . H9C H 0.9786 -0.5947 -0.0591 0.248 Uiso 1 1 calc R . . C10 C 0.5738(16) -0.2552(8) -0.0308(6) 0.055(4) Uani 1 1 d . . . H10A H 0.6795 -0.2666 -0.0175 0.066 Uiso 1 1 calc R . . H10B H 0.5662 -0.2257 -0.0722 0.066 Uiso 1 1 calc R . . C11 C 0.4727(16) -0.2093(9) 0.0161(6) 0.054(4) Uani 1 1 d . . . C12 C 0.4529(14) -0.0895(7) 0.0666(5) 0.036(3) Uani 1 1 d . . . C13 C 0.5371(12) -0.0372(7) 0.0810(5) 0.030(3) Uani 1 1 d . . . H13 H 0.6269 -0.0335 0.0591 0.036 Uiso 1 1 calc R . . C14 C 0.4883(13) 0.0095(7) 0.1279(5) 0.033(3) Uani 1 1 d . . . C15 C 0.3113(13) -0.0909(7) 0.0958(5) 0.037(3) Uani 1 1 d . . . H15 H 0.2492 -0.1230 0.0850 0.045 Uiso 1 1 calc R . . C16 C 0.2687(12) -0.0411(7) 0.1422(5) 0.030(3) Uani 1 1 d . . . C17 C 0.5683(12) 0.0633(7) 0.1523(5) 0.032(3) Uani 1 1 d . . . C18 C 0.6929(13) 0.0887(8) 0.1211(5) 0.042(3) Uani 1 1 d . . . H18 H 0.7280 0.0724 0.0826 0.051 Uiso 1 1 calc R . . C19 C 0.7595(14) 0.1373(8) 0.1486(6) 0.052(4) Uani 1 1 d . . . H19 H 0.8392 0.1559 0.1277 0.062 Uiso 1 1 calc R . . C20 C 0.7142(14) 0.1605(8) 0.2067(5) 0.045(3) Uani 1 1 d . . . H20 H 0.7654 0.1912 0.2266 0.054 Uiso 1 1 calc R . . C21 C 0.5839(12) 0.1348(7) 0.2347(5) 0.036(3) Uani 1 1 d . . . H21 H 0.5453 0.1522 0.2724 0.044 Uiso 1 1 calc R . . C22 C 0.1278(13) -0.0417(7) 0.1818(5) 0.035(3) Uani 1 1 d . . . C23 C 0.0154(13) -0.0776(8) 0.1698(6) 0.046(3) Uani 1 1 d . . . H23 H 0.0201 -0.1030 0.1340 0.055 Uiso 1 1 calc R . . C24 C -0.1077(14) -0.0767(8) 0.2111(6) 0.052(4) Uani 1 1 d . . . H24 H -0.1843 -0.1027 0.2044 0.063 Uiso 1 1 calc R . . C25 C -0.1126(13) -0.0360(8) 0.2620(5) 0.041(3) Uani 1 1 d . . . H25 H -0.1932 -0.0345 0.2906 0.049 Uiso 1 1 calc R . . C26 C 0.0014(13) 0.0023(7) 0.2707(5) 0.041(3) Uani 1 1 d . . . H26 H -0.0059 0.0313 0.3045 0.049 Uiso 1 1 calc R . . C27 C 0.0539(14) 0.3440(8) 0.6947(7) 0.053(4) Uani 1 1 d . . . C28 C 0.1665(16) 0.3817(7) 0.6970(7) 0.056(4) Uani 1 1 d . . . C29 C 0.3855(18) 0.4544(9) 0.6749(8) 0.068(4) Uani 1 1 d . . . C30 C 0.3365(18) 0.4681(9) 0.7339(8) 0.074(5) Uani 1 1 d . . . C31 C 0.631(2) 0.4355(11) 0.6067(12) 0.135(10) Uani 1 1 d . . . H31A H 0.6242 0.3876 0.6315 0.202 Uiso 1 1 calc R . . H31B H 0.7317 0.4449 0.6101 0.202 Uiso 1 1 calc R . . H31C H 0.6100 0.4325 0.5634 0.202 Uiso 1 1 calc R . . C32 C 0.356(3) 0.4997(14) 0.8557(9) 0.124(8) Uani 1 1 d . . . H32A H 0.2554 0.4886 0.8563 0.186 Uiso 1 1 calc R . . H32B H 0.3565 0.5403 0.8813 0.186 Uiso 1 1 calc R . . H32C H 0.4277 0.4539 0.8720 0.186 Uiso 1 1 calc R . . C33 C -0.1275(15) 0.2593(8) 0.6636(7) 0.057(4) Uani 1 1 d . . . C34 C -0.1703(15) 0.2733(8) 0.7238(7) 0.058(4) Uani 1 1 d . . . C35 C -0.377(3) 0.3104(14) 0.8148(12) 0.173(12) Uani 1 1 d . . . H35A H -0.4132 0.3585 0.7890 0.260 Uiso 1 1 calc R . . H35B H -0.2955 0.3154 0.8410 0.260 Uiso 1 1 calc R . . H35C H -0.4592 0.2973 0.8409 0.260 Uiso 1 1 calc R . . C36 C -0.0684(15) 0.1391(8) 0.5910(6) 0.054(4) Uani 1 1 d . . . H36A H 0.0118 0.1259 0.6224 0.065 Uiso 1 1 calc R . . H36B H -0.1032 0.0921 0.5862 0.065 Uiso 1 1 calc R . . C37 C 0.0000(15) 0.1666(9) 0.5285(6) 0.040(3) Uani 1 1 d . . . C38 C 0.1715(13) 0.1056(7) 0.4476(5) 0.030(3) Uani 1 1 d . . . C39 C 0.2774(13) 0.0395(8) 0.4382(5) 0.038(3) Uani 1 1 d . . . H39 H 0.3162 0.0036 0.4723 0.046 Uiso 1 1 calc R . . C40 C 0.3256(12) 0.0271(7) 0.3774(5) 0.030(3) Uani 1 1 d . . . C41 C 0.1202(13) 0.1605(7) 0.3975(5) 0.034(3) Uani 1 1 d . . . H41 H 0.0527 0.2065 0.4037 0.041 Uiso 1 1 calc R . . C42 C 0.1723(12) 0.1451(7) 0.3371(5) 0.026(3) Uani 1 1 d . . . C43 C 0.4317(12) -0.0450(7) 0.3595(5) 0.029(3) Uani 1 1 d . . . C44 C 0.5170(14) -0.0998(7) 0.4029(6) 0.041(3) Uani 1 1 d . . . H44 H 0.5119 -0.0940 0.4456 0.049 Uiso 1 1 calc R . . C45 C 0.6100(14) -0.1633(8) 0.3811(6) 0.045(3) Uani 1 1 d . . . H45 H 0.6680 -0.2017 0.4092 0.054 Uiso 1 1 calc R . . C46 C 0.6167(15) -0.1696(8) 0.3171(6) 0.045(3) Uani 1 1 d . . . H46 H 0.6782 -0.2123 0.3016 0.054 Uiso 1 1 calc R . . C47 C 0.5301(13) -0.1113(7) 0.2770(6) 0.038(3) Uani 1 1 d . . . H47 H 0.5343 -0.1158 0.2341 0.046 Uiso 1 1 calc R . . C48 C 0.1169(12) 0.1936(7) 0.2778(5) 0.031(3) Uani 1 1 d . . . C49 C 0.0164(14) 0.2635(8) 0.2750(6) 0.041(3) Uani 1 1 d . . . H49 H -0.0222 0.2824 0.3122 0.049 Uiso 1 1 calc R . . C50 C -0.0287(15) 0.3064(7) 0.2180(6) 0.047(3) Uani 1 1 d . . . H50 H -0.0935 0.3549 0.2168 0.056 Uiso 1 1 calc R . . C51 C 0.0239(16) 0.2763(8) 0.1622(6) 0.052(4) Uani 1 1 d . . . H51 H -0.0073 0.3027 0.1229 0.063 Uiso 1 1 calc R . . C52 C 0.1258(14) 0.2044(8) 0.1682(5) 0.045(4) Uani 1 1 d . . . H52 H 0.1625 0.1838 0.1314 0.054 Uiso 1 1 calc R . . N1 N 0.5123(12) -0.1392(6) 0.0222(4) 0.047(3) Uani 1 1 d . . . H1 H 0.5794 -0.1252 -0.0037 0.057 Uiso 1 1 calc R . . N2 N 0.3522(10) 0.0064(5) 0.1578(4) 0.030(2) Uani 1 1 d . . . N3 N 0.5174(10) 0.0875(6) 0.2086(4) 0.033(2) Uani 1 1 d . . . N4 N 0.1218(10) -0.0005(5) 0.2328(4) 0.028(2) Uani 1 1 d . . . N5 N 0.1132(11) 0.1104(6) 0.5086(4) 0.040(3) Uani 1 1 d . . . H5 H 0.1534 0.0737 0.5369 0.048 Uiso 1 1 calc R . . N6 N 0.2736(10) 0.0796(6) 0.3277(4) 0.029(2) Uani 1 1 d . . . N7 N 0.4404(9) -0.0485(5) 0.2966(4) 0.025(2) Uani 1 1 d . . . N8 N 0.1748(10) 0.1627(5) 0.2238(4) 0.029(2) Uani 1 1 d . . . O1 O 0.3702(13) -0.2329(6) 0.0447(5) 0.078(3) Uani 1 1 d . . . O2 O -0.0397(11) 0.2304(6) 0.5018(4) 0.059(3) Uani 1 1 d . . . O3 O 0.2587(16) -0.1212(7) -0.4694(5) 0.102(4) Uani 1 1 d . . . O4 O 0.3851(19) -0.0739(12) -0.3958(8) 0.184(9) Uani 1 1 d . . . O5 O 0.1272(16) -0.0360(8) -0.4111(6) 0.120(5) Uani 1 1 d . . . O6 O 0.2242(10) -0.1558(6) -0.3607(4) 0.059(3) Uani 1 1 d . . . O7 O -0.0179(15) -0.2266(7) -0.0231(5) 0.105(4) Uani 1 1 d . . . O8 O 0.0448(13) -0.1114(8) -0.0060(6) 0.106(4) Uani 1 1 d . . . O9 O -0.2063(9) -0.1118(6) -0.0352(4) 0.053(2) Uani 1 1 d . . . O10 O -0.1136(13) -0.1667(7) 0.0653(4) 0.092(4) Uani 1 1 d . . . O11 O 0.699(3) -0.2230(14) 0.1613(11) 0.094(7) Uani 0.50 1 d P . . S1 S 0.8277(5) -0.4693(2) -0.16145(18) 0.0653(11) Uani 1 1 d . . . S2 S 0.5789(5) -0.3295(2) -0.17125(18) 0.0649(11) Uani 1 1 d . . . S3 S 0.8766(4) -0.4403(2) -0.31553(18) 0.0620(11) Uani 1 1 d . . . S4 S 0.6142(5) -0.3072(2) -0.32146(17) 0.0605(11) Uani 1 1 d . . . S5 S 0.9152(5) -0.4300(4) -0.4562(2) 0.0960(17) Uani 1 1 d . . . S6 S 0.6221(6) -0.2728(4) -0.4614(2) 0.1040(18) Uani 1 1 d . . . S7 S 0.7901(8) -0.5005(4) -0.0206(2) 0.125(2) Uani 1 1 d . . . S8 S 0.5069(5) -0.3447(2) -0.0330(2) 0.0722(13) Uani 1 1 d . . . S9 S 0.0112(4) 0.3051(2) 0.62573(17) 0.0586(11) Uani 1 1 d . . . S10 S -0.0693(6) 0.3318(3) 0.7584(2) 0.0961(18) Uani 1 1 d . . . S11 S 0.2912(5) 0.3965(2) 0.63522(19) 0.0671(12) Uani 1 1 d . . . S12 S 0.1939(5) 0.4204(3) 0.7665(2) 0.0729(13) Uani 1 1 d . . . S13 S 0.5071(7) 0.5058(4) 0.6323(3) 0.132(3) Uani 1 1 d . . . S14 S 0.4060(6) 0.5292(3) 0.7777(3) 0.0968(17) Uani 1 1 d . . . S15 S -0.3119(6) 0.2380(3) 0.7672(3) 0.114(2) Uani 1 1 d . . . S16 S -0.2265(4) 0.2079(2) 0.62075(17) 0.0566(11) Uani 1 1 d . . . Cl1 Cl 0.2555(4) -0.0972(2) -0.40750(14) 0.0469(9) Uani 1 1 d . . . Cl2 Cl -0.0720(4) -0.1532(2) 0.00009(15) 0.0572(10) Uani 1 1 d . . . Ni1 Ni 0.31279(16) 0.05059(9) 0.24024(6) 0.0287(4) Uani 1 1 d . . . 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 C1 0.060(9) 0.062(10) 0.039(8) -0.021(7) 0.007(7) -0.012(8) C2 0.053(8) 0.056(10) 0.046(8) -0.025(7) -0.004(7) -0.022(7) C3 0.076(11) 0.085(13) 0.044(9) -0.010(9) 0.014(8) -0.024(10) C4 0.079(11) 0.077(12) 0.043(8) -0.015(8) -0.007(8) -0.029(10) C5 0.053(10) 0.073(13) 0.126(16) -0.006(11) 0.016(10) -0.006(9) C6 0.147(19) 0.094(15) 0.129(17) -0.019(13) -0.093(16) -0.011(14) C7 0.085(11) 0.074(12) 0.023(7) -0.016(7) 0.003(7) -0.020(10) C8 0.068(10) 0.067(11) 0.049(9) -0.037(8) 0.007(8) -0.018(9) C9 0.25(3) 0.079(16) 0.116(18) 0.014(14) 0.065(19) 0.060(18) C10 0.059(9) 0.057(10) 0.054(9) -0.031(7) 0.010(7) -0.012(7) C11 0.055(9) 0.066(11) 0.048(8) -0.041(8) 0.020(7) -0.015(8) C12 0.056(8) 0.035(8) 0.021(6) -0.016(5) 0.010(6) -0.007(6) C13 0.023(6) 0.047(8) 0.021(6) -0.012(5) 0.014(5) -0.010(6) C14 0.042(7) 0.040(8) 0.019(6) -0.001(5) 0.009(5) -0.017(6) C15 0.046(8) 0.054(9) 0.019(6) -0.022(6) 0.001(6) -0.017(6) C16 0.030(6) 0.039(8) 0.022(6) 0.002(5) 0.010(5) -0.009(6) C17 0.024(6) 0.053(8) 0.017(6) -0.011(5) -0.001(5) -0.004(6) C18 0.032(7) 0.080(10) 0.028(6) -0.026(6) 0.017(5) -0.035(7) C19 0.042(8) 0.073(11) 0.050(8) -0.013(7) 0.014(7) -0.034(8) C20 0.045(8) 0.069(10) 0.027(7) -0.015(6) -0.007(6) -0.016(7) C21 0.033(7) 0.059(9) 0.028(6) -0.028(6) 0.006(5) -0.022(6) C22 0.030(7) 0.048(8) 0.030(7) -0.020(6) -0.001(5) -0.003(6) C23 0.040(8) 0.059(10) 0.046(8) -0.026(7) 0.015(6) -0.018(7) C24 0.027(7) 0.077(11) 0.063(9) -0.023(8) 0.015(7) -0.027(7) C25 0.028(7) 0.069(10) 0.025(6) 0.005(6) 0.003(5) -0.014(7) C26 0.037(7) 0.063(10) 0.032(7) -0.015(6) 0.015(6) -0.028(7) C27 0.041(8) 0.057(10) 0.068(9) -0.029(8) 0.024(7) -0.018(7) C28 0.056(9) 0.032(8) 0.082(10) -0.014(7) 0.024(8) -0.017(7) C29 0.079(11) 0.068(11) 0.066(10) -0.021(9) 0.011(9) -0.026(9) C30 0.066(11) 0.074(12) 0.086(12) -0.007(10) 0.012(9) -0.030(9) C31 0.090(14) 0.071(14) 0.25(3) -0.048(16) 0.102(17) -0.023(12) C32 0.142(19) 0.16(2) 0.094(15) -0.054(15) -0.007(14) -0.066(17) C33 0.044(8) 0.069(10) 0.070(10) -0.042(8) 0.031(7) -0.025(7) C34 0.053(9) 0.063(10) 0.063(9) -0.044(8) 0.030(7) -0.009(7) C35 0.18(2) 0.14(2) 0.19(3) -0.014(19) 0.15(2) -0.023(18) C36 0.061(9) 0.071(11) 0.038(8) -0.028(7) 0.025(7) -0.023(8) C37 0.046(8) 0.041(9) 0.036(7) -0.009(7) 0.004(6) -0.012(7) C38 0.040(7) 0.036(8) 0.016(6) -0.010(5) 0.003(5) -0.009(6) C39 0.032(7) 0.064(10) 0.023(6) -0.008(6) -0.001(5) -0.020(7) C40 0.033(7) 0.049(8) 0.014(6) -0.011(6) 0.001(5) -0.017(6) C41 0.042(7) 0.056(9) 0.017(6) -0.021(6) 0.020(5) -0.031(6) C42 0.022(6) 0.033(7) 0.026(6) -0.005(5) -0.005(5) -0.010(6) C43 0.024(6) 0.041(8) 0.029(6) -0.016(6) 0.016(5) -0.016(6) C44 0.047(8) 0.048(9) 0.027(7) -0.006(6) 0.000(6) -0.007(7) C45 0.038(7) 0.057(10) 0.041(8) -0.006(7) 0.010(6) -0.010(7) C46 0.050(8) 0.037(9) 0.055(9) -0.024(7) 0.022(7) -0.015(7) C47 0.028(7) 0.026(8) 0.060(8) -0.016(7) 0.010(6) 0.000(6) C48 0.024(6) 0.046(8) 0.025(6) -0.010(6) -0.005(5) -0.007(6) C49 0.048(8) 0.047(9) 0.030(7) -0.010(6) 0.002(6) -0.011(7) C50 0.063(9) 0.030(8) 0.050(8) -0.013(7) 0.003(7) -0.010(7) C51 0.065(10) 0.047(10) 0.039(8) 0.006(7) 0.009(7) -0.007(8) C52 0.042(8) 0.075(11) 0.021(7) -0.018(7) 0.005(6) -0.012(8) N1 0.062(7) 0.054(8) 0.034(6) -0.019(5) 0.016(5) -0.023(6) N2 0.025(5) 0.044(6) 0.028(5) -0.018(5) 0.007(4) -0.014(5) N3 0.035(6) 0.050(7) 0.015(5) -0.008(4) 0.006(4) -0.012(5) N4 0.027(5) 0.038(6) 0.021(5) -0.004(4) 0.011(4) -0.016(4) N5 0.052(7) 0.055(7) 0.010(5) -0.004(5) 0.010(4) -0.005(6) N6 0.023(5) 0.039(6) 0.028(5) -0.018(5) 0.008(4) -0.011(5) N7 0.017(5) 0.031(6) 0.025(5) -0.009(4) 0.008(4) 0.000(4) N8 0.029(5) 0.047(7) 0.012(5) -0.005(4) 0.002(4) -0.009(5) O1 0.090(8) 0.066(7) 0.094(8) -0.047(6) 0.056(7) -0.043(6) O2 0.088(7) 0.052(7) 0.041(5) -0.017(5) 0.030(5) -0.022(6) O3 0.176(13) 0.105(10) 0.038(6) -0.018(6) 0.014(7) -0.055(9) O4 0.156(14) 0.31(2) 0.134(13) 0.055(14) -0.065(11) -0.184(16) O5 0.131(11) 0.091(10) 0.104(10) 0.027(8) 0.055(9) 0.024(9) O6 0.067(6) 0.073(7) 0.042(5) 0.013(5) -0.001(5) -0.034(5) O7 0.138(11) 0.078(9) 0.092(9) -0.053(7) -0.036(8) 0.021(8) O8 0.062(7) 0.148(12) 0.119(11) 0.002(9) 0.007(7) -0.055(8) O9 0.042(5) 0.085(7) 0.030(5) -0.006(5) 0.002(4) -0.007(5) O10 0.099(9) 0.133(11) 0.037(6) -0.006(6) 0.002(6) -0.012(8) O11 0.096(17) 0.095(19) 0.094(17) -0.022(14) 0.005(14) -0.023(14) S1 0.075(3) 0.063(3) 0.051(2) -0.017(2) 0.004(2) 0.005(2) S2 0.077(3) 0.059(3) 0.057(2) -0.027(2) 0.006(2) -0.001(2) S3 0.069(3) 0.064(3) 0.056(2) -0.026(2) 0.012(2) -0.012(2) S4 0.074(3) 0.059(3) 0.049(2) -0.0132(19) -0.006(2) -0.013(2) S5 0.081(3) 0.164(5) 0.062(3) -0.052(3) 0.027(2) -0.049(3) S6 0.101(4) 0.142(5) 0.063(3) 0.026(3) -0.013(3) -0.034(4) S7 0.183(6) 0.120(5) 0.049(3) -0.015(3) 0.001(3) 0.025(4) S8 0.096(3) 0.054(3) 0.076(3) -0.032(2) 0.045(2) -0.030(2) S9 0.047(2) 0.085(3) 0.055(2) -0.032(2) 0.0180(18) -0.026(2) S10 0.099(3) 0.144(5) 0.082(3) -0.075(3) 0.046(3) -0.079(3) S11 0.076(3) 0.070(3) 0.065(3) -0.012(2) 0.016(2) -0.037(2) S12 0.070(3) 0.093(3) 0.071(3) -0.029(2) 0.011(2) -0.041(3) S13 0.125(5) 0.131(5) 0.171(6) -0.058(5) 0.076(4) -0.084(4) S14 0.085(3) 0.110(4) 0.120(4) -0.060(3) 0.022(3) -0.053(3) S15 0.120(4) 0.138(5) 0.126(4) -0.092(4) 0.091(4) -0.088(4) S16 0.047(2) 0.081(3) 0.053(2) -0.036(2) 0.0142(17) -0.026(2) Cl1 0.044(2) 0.059(2) 0.0398(19) -0.0140(17) 0.0111(15) -0.0137(19) Cl2 0.058(2) 0.078(3) 0.0386(19) -0.0188(19) 0.0057(17) -0.017(2) Ni1 0.0268(8) 0.0434(10) 0.0207(8) -0.0140(7) 0.0072(6) -0.0134(7) _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 C1 C2 1.316(17) . ? C1 S1 1.752(15) . ? C1 S2 1.778(14) . ? C2 S4 1.767(15) . ? C2 S3 1.772(14) . ? C3 C4 1.34(2) . ? C3 S3 1.743(16) . ? C3 S5 1.789(15) . ? C4 S6 1.744(16) . ? C4 S4 1.752(15) . ? C5 S5 1.791(15) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 S6 1.74(2) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.35(2) . ? C7 S7 1.727(15) . ? C7 S1 1.761(14) . ? C8 S2 1.749(16) . ? C8 S8 1.768(14) . ? C9 S7 1.82(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.524(17) . ? C10 S8 1.824(13) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O1 1.209(15) . ? C11 N1 1.389(16) . ? C12 C13 1.382(15) . ? C12 N1 1.394(14) . ? C12 C15 1.402(16) . ? C13 C14 1.383(14) . ? C13 H13 0.9300 . ? C14 N2 1.369(13) . ? C14 C17 1.462(15) . ? C15 C16 1.401(15) . ? C15 H15 0.9300 . ? C16 N2 1.318(13) . ? C16 C22 1.501(15) . ? C17 N3 1.364(13) . ? C17 C18 1.412(15) . ? C18 C19 1.347(15) . ? C18 H18 0.9300 . ? C19 C20 1.379(16) . ? C19 H19 0.9300 . ? C20 C21 1.432(16) . ? C20 H20 0.9300 . ? C21 N3 1.311(13) . ? C21 H21 0.9300 . ? C22 C23 1.349(15) . ? C22 N4 1.380(13) . ? C23 C24 1.392(16) . ? C23 H23 0.9300 . ? C24 C25 1.373(17) . ? C24 H24 0.9300 . ? C25 C26 1.373(15) . ? C25 H25 0.9300 . ? C26 N4 1.326(13) . ? C26 H26 0.9300 . ? C27 C28 1.330(17) . ? C27 S10 1.752(13) . ? C27 S9 1.787(13) . ? C28 S11 1.737(14) . ? C28 S12 1.757(15) . ? C29 C30 1.36(2) . ? C29 S13 1.736(16) . ? C29 S11 1.767(15) . ? C30 S14 1.738(17) . ? C30 S12 1.763(15) . ? C31 S13 1.623(17) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 S14 1.76(2) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.368(17) . ? C33 S16 1.749(13) . ? C33 S9 1.754(13) . ? C34 S15 1.731(14) . ? C34 S10 1.755(14) . ? C35 S15 1.73(2) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 C37 1.522(17) . ? C36 S16 1.821(13) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 O2 1.193(14) . ? C37 N5 1.363(16) . ? C38 C41 1.376(16) . ? C38 C39 1.377(16) . ? C38 N5 1.397(13) . ? C39 C40 1.386(14) . ? C39 H39 0.9300 . ? C40 N6 1.350(14) . ? C40 C43 1.509(16) . ? C41 C42 1.399(14) . ? C41 H41 0.9300 . ? C42 N6 1.348(14) . ? C42 C48 1.480(15) . ? C43 N7 1.352(13) . ? C43 C44 1.378(16) . ? C44 C45 1.376(17) . ? C44 H44 0.9300 . ? C45 C46 1.385(17) . ? C45 H45 0.9300 . ? C46 C47 1.377(17) . ? C46 H46 0.9300 . ? C47 N7 1.336(13) . ? C47 H47 0.9300 . ? C48 C49 1.368(16) . ? C48 N8 1.378(13) . ? C49 C50 1.380(17) . ? C49 H49 0.9300 . ? C50 C51 1.396(17) . ? C50 H50 0.9300 . ? C51 C52 1.399(18) . ? C51 H51 0.9300 . ? C52 N8 1.355(15) . ? C52 H52 0.9300 . ? N1 H1 0.8600 . ? N2 Ni1 2.008(8) . ? N3 Ni1 2.141(9) . ? N4 Ni1 2.120(8) . ? N5 H5 0.8600 . ? N6 Ni1 2.002(9) . ? N7 Ni1 2.139(9) . ? N8 Ni1 2.107(10) . ? O3 Cl1 1.437(10) . ? O4 Cl1 1.352(12) . ? O5 Cl1 1.403(13) . ? O6 Cl1 1.422(9) . ? O7 Cl2 1.435(11) . ? O8 Cl2 1.403(11) . ? O9 Cl2 1.451(9) . ? O10 Cl2 1.438(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 C2 C1 S1 125.3(11) . . ? C2 C1 S2 120.8(12) . . ? S1 C1 S2 113.8(7) . . ? C1 C2 S4 123.5(11) . . ? C1 C2 S3 123.2(12) . . ? S4 C2 S3 113.3(7) . . ? C4 C3 S3 119.8(11) . . ? C4 C3 S5 123.5(12) . . ? S3 C3 S5 116.5(11) . . ? C3 C4 S6 127.5(12) . . ? C3 C4 S4 115.1(11) . . ? S6 C4 S4 117.1(11) . . ? S5 C5 H5A 109.5 . . ? S5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? S5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? S6 C6 H6A 109.5 . . ? S6 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? S6 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 S7 124.0(11) . . ? C8 C7 S1 116.1(11) . . ? S7 C7 S1 119.7(10) . . ? C7 C8 S2 118.2(10) . . ? C7 C8 S8 124.6(12) . . ? S2 C8 S8 117.1(10) . . ? S7 C9 H9A 109.5 . . ? S7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? S7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 S8 107.1(9) . . ? C11 C10 H10A 110.3 . . ? S8 C10 H10A 110.3 . . ? C11 C10 H10B 110.3 . . ? S8 C10 H10B 110.3 . . ? H10A C10 H10B 108.5 . . ? O1 C11 N1 124.7(11) . . ? O1 C11 C10 122.5(12) . . ? N1 C11 C10 112.8(12) . . ? C13 C12 N1 118.1(10) . . ? C13 C12 C15 120.1(9) . . ? N1 C12 C15 121.8(10) . . ? C12 C13 C14 120.2(10) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? N2 C14 C13 119.5(10) . . ? N2 C14 C17 113.2(9) . . ? C13 C14 C17 127.3(10) . . ? C16 C15 C12 116.2(10) . . ? C16 C15 H15 121.9 . . ? C12 C15 H15 121.9 . . ? N2 C16 C15 123.6(10) . . ? N2 C16 C22 114.1(9) . . ? C15 C16 C22 122.2(10) . . ? N3 C17 C18 120.6(10) . . ? N3 C17 C14 115.9(9) . . ? C18 C17 C14 123.4(9) . . ? C19 C18 C17 118.2(10) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C18 C19 C20 122.5(11) . . ? C18 C19 H19 118.7 . . ? C20 C19 H19 118.7 . . ? C19 C20 C21 116.4(11) . . ? C19 C20 H20 121.8 . . ? C21 C20 H20 121.8 . . ? N3 C21 C20 121.9(10) . . ? N3 C21 H21 119.0 . . ? C20 C21 H21 119.0 . . ? C23 C22 N4 121.9(10) . . ? C23 C22 C16 124.8(10) . . ? N4 C22 C16 113.3(9) . . ? C22 C23 C24 119.8(11) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C25 C24 C23 118.0(11) . . ? C25 C24 H24 121.0 . . ? C23 C24 H24 121.0 . . ? C26 C25 C24 119.9(11) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? N4 C26 C25 122.5(11) . . ? N4 C26 H26 118.7 . . ? C25 C26 H26 118.7 . . ? C28 C27 S10 122.4(11) . . ? C28 C27 S9 123.1(11) . . ? S10 C27 S9 114.5(7) . . ? C27 C28 S11 124.6(11) . . ? C27 C28 S12 119.1(11) . . ? S11 C28 S12 116.4(7) . . ? C30 C29 S13 122.6(12) . . ? C30 C29 S11 117.3(12) . . ? S13 C29 S11 118.8(9) . . ? C29 C30 S14 123.7(12) . . ? C29 C30 S12 117.0(12) . . ? S14 C30 S12 119.3(10) . . ? S13 C31 H31A 109.5 . . ? S13 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? S13 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? S14 C32 H32A 109.5 . . ? S14 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? S14 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 S16 121.0(10) . . ? C34 C33 S9 118.8(10) . . ? S16 C33 S9 119.6(8) . . ? C33 C34 S15 125.7(10) . . ? C33 C34 S10 115.7(10) . . ? S15 C34 S10 118.6(7) . . ? S15 C35 H35A 109.5 . . ? S15 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? S15 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C37 C36 S16 115.7(10) . . ? C37 C36 H36A 108.4 . . ? S16 C36 H36A 108.4 . . ? C37 C36 H36B 108.4 . . ? S16 C36 H36B 108.4 . . ? H36A C36 H36B 107.4 . . ? O2 C37 N5 125.1(12) . . ? O2 C37 C36 123.2(12) . . ? N5 C37 C36 111.7(12) . . ? C41 C38 C39 120.3(10) . . ? C41 C38 N5 122.9(11) . . ? C39 C38 N5 116.6(11) . . ? C38 C39 C40 119.2(12) . . ? C38 C39 H39 120.4 . . ? C40 C39 H39 120.4 . . ? N6 C40 C39 121.1(11) . . ? N6 C40 C43 113.8(9) . . ? C39 C40 C43 125.1(11) . . ? C38 C41 C42 118.1(11) . . ? C38 C41 H41 120.9 . . ? C42 C41 H41 120.9 . . ? N6 C42 C41 121.5(11) . . ? N6 C42 C48 113.1(9) . . ? C41 C42 C48 125.2(11) . . ? N7 C43 C44 123.5(10) . . ? N7 C43 C40 113.3(10) . . ? C44 C43 C40 123.1(10) . . ? C45 C44 C43 118.1(11) . . ? C45 C44 H44 121.0 . . ? C43 C44 H44 121.0 . . ? C44 C45 C46 119.5(13) . . ? C44 C45 H45 120.2 . . ? C46 C45 H45 120.2 . . ? C47 C46 C45 118.5(12) . . ? C47 C46 H46 120.7 . . ? C45 C46 H46 120.7 . . ? N7 C47 C46 123.3(12) . . ? N7 C47 H47 118.4 . . ? C46 C47 H47 118.4 . . ? C49 C48 N8 121.4(10) . . ? C49 C48 C42 124.1(10) . . ? N8 C48 C42 114.5(10) . . ? C48 C49 C50 121.1(11) . . ? C48 C49 H49 119.4 . . ? C50 C49 H49 119.4 . . ? C49 C50 C51 119.3(13) . . ? C49 C50 H50 120.3 . . ? C51 C50 H50 120.3 . . ? C50 C51 C52 116.7(12) . . ? C50 C51 H51 121.6 . . ? C52 C51 H51 121.6 . . ? N8 C52 C51 124.6(11) . . ? N8 C52 H52 117.7 . . ? C51 C52 H52 117.7 . . ? C11 N1 C12 125.7(10) . . ? C11 N1 H1 117.2 . . ? C12 N1 H1 117.2 . . ? C16 N2 C14 120.3(9) . . ? C16 N2 Ni1 119.4(7) . . ? C14 N2 Ni1 118.0(7) . . ? C21 N3 C17 120.3(9) . . ? C21 N3 Ni1 126.6(7) . . ? C17 N3 Ni1 112.7(7) . . ? C26 N4 C22 117.7(9) . . ? C26 N4 Ni1 128.2(7) . . ? C22 N4 Ni1 114.1(7) . . ? C37 N5 C38 127.6(11) . . ? C37 N5 H5 116.2 . . ? C38 N5 H5 116.2 . . ? C42 N6 C40 119.7(9) . . ? C42 N6 Ni1 119.7(7) . . ? C40 N6 Ni1 119.4(7) . . ? C47 N7 C43 117.0(10) . . ? C47 N7 Ni1 127.8(8) . . ? C43 N7 Ni1 115.2(7) . . ? C52 N8 C48 116.8(10) . . ? C52 N8 Ni1 128.8(8) . . ? C48 N8 Ni1 114.2(7) . . ? C1 S1 C7 96.4(7) . . ? C8 S2 C1 95.4(7) . . ? C3 S3 C2 94.9(7) . . ? C4 S4 C2 96.8(7) . . ? C3 S5 C5 102.0(8) . . ? C4 S6 C6 99.7(9) . . ? C7 S7 C9 104.4(9) . . ? C8 S8 C10 98.4(6) . . ? C33 S9 C27 94.0(6) . . ? C27 S10 C34 96.3(6) . . ? C28 S11 C29 94.6(7) . . ? C28 S12 C30 94.4(7) . . ? C31 S13 C29 100.7(9) . . ? C30 S14 C32 103.5(9) . . ? C34 S15 C35 102.1(9) . . ? C33 S16 C36 100.6(6) . . ? O4 Cl1 O5 112.3(12) . . ? O4 Cl1 O6 112.6(8) . . ? O5 Cl1 O6 107.2(7) . . ? O4 Cl1 O3 111.2(10) . . ? O5 Cl1 O3 101.7(9) . . ? O6 Cl1 O3 111.2(6) . . ? O8 Cl2 O7 109.0(9) . . ? O8 Cl2 O10 109.9(8) . . ? O7 Cl2 O10 108.8(8) . . ? O8 Cl2 O9 111.3(7) . . ? O7 Cl2 O9 109.1(6) . . ? O10 Cl2 O9 108.8(6) . . ? N6 Ni1 N2 172.0(4) . . ? N6 Ni1 N8 77.8(4) . . ? N2 Ni1 N8 108.8(4) . . ? N6 Ni1 N4 98.1(3) . . ? N2 Ni1 N4 77.7(3) . . ? N8 Ni1 N4 91.3(3) . . ? N6 Ni1 N7 77.5(4) . . ? N2 Ni1 N7 95.9(4) . . ? N8 Ni1 N7 155.3(3) . . ? N4 Ni1 N7 93.7(3) . . ? N6 Ni1 N3 106.3(3) . . ? N2 Ni1 N3 78.1(3) . . ? N8 Ni1 N3 93.9(4) . . ? N4 Ni1 N3 155.7(3) . . ? N7 Ni1 N3 91.5(3) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.086 _refine_diff_density_min -0.856 _refine_diff_density_rms 0.136 data_(MeS)3-TTF-SCH2CONH-Terpy-ZnCl2.MeOH _database_code_depnum_ccdc_archive 'CCDC 917574' #TrackingRef 'sad-2-Zn-squeezed.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H22 Cl2 N4 O S8 Zn, C1 H4 O' _chemical_formula_sum 'C27 H26 Cl2 N4 O2 S8 Zn' _chemical_formula_weight 831.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' Zn Zn 0.2839 1.4301 '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 '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1990(8) _cell_length_b 11.455(1) _cell_length_c 19.958(2) _cell_angle_alpha 96.439(7) _cell_angle_beta 90.342(7) _cell_angle_gamma 110.707(8) _cell_volume 1740.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 26098 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 29.01 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.682 _exptl_absorpt_correction_T_max 0.803 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2008))' ; _exptl_special_details ; MOLTECH ANJOU UMR CNRS 6200 2, bd Lavoisier 49045 Angers cedex France ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53602 _diffrn_reflns_av_R_equivalents 0.0744 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 29.01 _reflns_number_total 9212 _reflns_number_gt 6830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.2g (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0680P)^2^+3.4935P] 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 9212 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1553 _refine_ls_wR_factor_gt 0.1440 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 C1 C 1.3603(7) 0.8406(5) 0.4778(2) 0.0500(12) Uani 1 1 d . . . C2 C 1.3986(7) 0.7979(4) 0.5339(2) 0.0518(12) Uani 1 1 d . . . C3 C 1.4121(7) 0.7327(4) 0.6536(2) 0.0517(13) Uani 1 1 d . . . C4 C 1.5466(8) 0.7110(5) 0.6231(2) 0.0579(14) Uani 1 1 d . . . C5 C 1.1534(14) 0.6963(14) 0.7430(4) 0.165(6) Uani 1 1 d . . . H5A H 1.1440 0.7765 0.7392 0.247 Uiso 1 1 calc R . . H5B H 1.1111 0.6693 0.7855 0.247 Uiso 1 1 calc R . . H5C H 1.0852 0.6358 0.7069 0.247 Uiso 1 1 calc R . . C6 C 1.609(2) 0.4979(9) 0.6387(6) 0.175(6) Uani 1 1 d . . . H6A H 1.4887 0.4684 0.6504 0.263 Uiso 1 1 calc R . . H6B H 1.6716 0.4579 0.6628 0.263 Uiso 1 1 calc R . . H6C H 1.6155 0.4780 0.5911 0.263 Uiso 1 1 calc R . . C7 C 1.2295(6) 0.9278(5) 0.3845(2) 0.0466(11) Uani 1 1 d . . . C8 C 1.3656(6) 0.9060(4) 0.35744(18) 0.0411(10) Uani 1 1 d . . . C9 C 0.8894(10) 0.8551(12) 0.3298(6) 0.156(5) Uani 1 1 d . . . H9A H 0.9110 0.7881 0.3025 0.234 Uiso 1 1 calc R . . H9B H 0.8047 0.8785 0.3067 0.234 Uiso 1 1 calc R . . H9C H 0.8458 0.8276 0.3721 0.234 Uiso 1 1 calc R . . C10 C 1.3872(5) 0.7747(4) 0.23473(18) 0.0334(8) Uani 1 1 d . . . H10A H 1.4624 0.7742 0.1975 0.040 Uiso 1 1 calc R . . H10B H 1.4060 0.7220 0.2665 0.040 Uiso 1 1 calc R . . C11 C 1.2001(5) 0.7231(3) 0.20893(17) 0.0277(7) Uani 1 1 d . . . C12 C 1.0218(4) 0.7398(3) 0.11068(15) 0.0190(6) Uani 1 1 d . . . C13 C 1.0364(4) 0.7970(3) 0.05159(15) 0.0203(6) Uani 1 1 d . . . H13 H 1.1454 0.8434 0.0372 0.024 Uiso 1 1 calc R . . C14 C 0.8865(4) 0.7835(3) 0.01500(15) 0.0184(6) Uani 1 1 d . . . C15 C 0.8808(4) 0.8414(3) -0.04769(15) 0.0194(6) Uani 1 1 d . . . C16 C 1.0269(4) 0.8931(3) -0.08445(17) 0.0242(7) Uani 1 1 d . . . H16 H 1.1366 0.8973 -0.0693 0.029 Uiso 1 1 calc R . . C17 C 1.0050(5) 0.9382(3) -0.14437(18) 0.0308(8) Uani 1 1 d . . . H17 H 1.1005 0.9731 -0.1701 0.037 Uiso 1 1 calc R . . C18 C 0.8396(5) 0.9309(4) -0.16570(17) 0.0310(8) Uani 1 1 d . . . H18 H 0.8225 0.9592 -0.2061 0.037 Uiso 1 1 calc R . . C19 C 0.7006(5) 0.8805(3) -0.12557(17) 0.0259(7) Uani 1 1 d . . . H19 H 0.5902 0.8773 -0.1391 0.031 Uiso 1 1 calc R . . C20 C 0.8570(4) 0.6652(3) 0.12982(16) 0.0219(6) Uani 1 1 d . . . H20 H 0.8446 0.6239 0.1681 0.026 Uiso 1 1 calc R . . C21 C 0.7133(4) 0.6552(3) 0.08940(16) 0.0207(6) Uani 1 1 d . . . C22 C 0.5294(4) 0.5795(3) 0.10295(16) 0.0210(6) Uani 1 1 d . . . C23 C 0.4846(4) 0.5008(3) 0.15326(18) 0.0278(7) Uani 1 1 d . . . H23 H 0.5700 0.4920 0.1810 0.033 Uiso 1 1 calc R . . C24 C 0.3069(5) 0.4351(3) 0.16117(19) 0.0305(8) Uani 1 1 d . . . H24 H 0.2725 0.3828 0.1949 0.037 Uiso 1 1 calc R . . C25 C 0.1834(5) 0.4487(3) 0.11844(19) 0.0302(8) Uani 1 1 d . . . H25 H 0.0651 0.4051 0.1226 0.036 Uiso 1 1 calc R . . C26 C 0.2388(4) 0.5280(3) 0.06965(18) 0.0264(7) Uani 1 1 d . . . H26 H 0.1552 0.5362 0.0408 0.032 Uiso 1 1 calc R . . Cl1 Cl 0.52213(10) 0.91185(8) 0.07731(4) 0.02705(18) Uani 1 1 d . . . Cl2 Cl 0.28168(11) 0.68116(9) -0.07829(4) 0.0315(2) Uani 1 1 d . . . N1 N 1.1759(4) 0.7628(3) 0.14820(14) 0.0235(6) Uani 1 1 d . . . H1 H 1.2696 0.8084 0.1310 0.028 Uiso 1 1 calc R . . N2 N 0.7276(3) 0.7144(2) 0.03420(13) 0.0196(5) Uani 1 1 d . . . N3 N 0.7206(4) 0.8362(3) -0.06776(13) 0.0214(5) Uani 1 1 d . . . N4 N 0.4070(3) 0.5938(3) 0.06167(14) 0.0227(6) Uani 1 1 d . . . O1 O 1.0836(4) 0.6564(3) 0.23964(14) 0.0432(7) Uani 1 1 d . . . S1 S 1.19262(18) 0.89944(15) 0.46915(6) 0.0591(4) Uani 1 1 d . . . S2 S 1.49218(19) 0.85166(13) 0.40769(5) 0.0533(3) Uani 1 1 d . . . S3 S 1.28044(18) 0.79064(14) 0.60746(6) 0.0576(4) Uani 1 1 d . . . S4 S 1.5766(2) 0.74570(15) 0.53947(6) 0.0636(4) Uani 1 1 d . . . S5 S 1.3683(2) 0.70917(14) 0.73846(6) 0.0615(4) Uani 1 1 d . . . S6 S 1.7006(3) 0.66148(17) 0.66062(8) 0.0817(5) Uani 1 1 d . . . S7 S 1.0896(2) 0.9886(2) 0.34514(8) 0.0835(6) Uani 1 1 d . . . S8 S 1.44276(14) 0.93547(10) 0.27630(5) 0.0392(3) Uani 1 1 d . . . Zn1 Zn 0.51150(5) 0.74719(4) -0.003284(18) 0.02112(11) Uani 1 1 d . . . 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 C1 0.067(3) 0.050(3) 0.0186(18) 0.0098(17) -0.0125(18) 0.002(2) C2 0.071(3) 0.044(3) 0.026(2) 0.0099(18) -0.013(2) 0.001(2) C3 0.080(3) 0.033(2) 0.026(2) 0.0110(17) -0.016(2) -0.001(2) C4 0.092(4) 0.050(3) 0.027(2) 0.013(2) -0.007(2) 0.018(3) C5 0.171(10) 0.345(18) 0.059(4) 0.093(8) 0.047(5) 0.170(12) C6 0.326(19) 0.091(7) 0.126(9) 0.015(6) -0.026(10) 0.097(10) C7 0.047(2) 0.054(3) 0.0254(19) 0.0146(18) -0.0104(18) -0.001(2) C8 0.056(3) 0.036(2) 0.0173(16) 0.0072(15) -0.0113(17) -0.0020(19) C9 0.059(5) 0.227(13) 0.184(11) 0.023(10) -0.015(6) 0.055(7) C10 0.040(2) 0.039(2) 0.0224(17) 0.0050(15) -0.0095(15) 0.0153(17) C11 0.0335(18) 0.0294(18) 0.0194(15) 0.0027(13) -0.0049(13) 0.0105(15) C12 0.0195(14) 0.0185(15) 0.0192(14) 0.0010(12) -0.0014(11) 0.0075(12) C13 0.0199(15) 0.0213(15) 0.0190(14) 0.0037(12) 0.0022(11) 0.0063(12) C14 0.0182(14) 0.0189(15) 0.0163(14) 0.0005(11) 0.0002(11) 0.0049(12) C15 0.0203(15) 0.0193(15) 0.0182(14) 0.0023(12) -0.0004(11) 0.0066(12) C16 0.0235(16) 0.0254(17) 0.0237(16) 0.0056(13) 0.0026(13) 0.0081(13) C17 0.0333(19) 0.0292(19) 0.0294(18) 0.0123(15) 0.0058(15) 0.0077(15) C18 0.042(2) 0.0317(19) 0.0193(16) 0.0059(14) -0.0027(14) 0.0115(16) C19 0.0285(17) 0.0292(18) 0.0224(16) 0.0035(13) -0.0048(13) 0.0131(14) C20 0.0210(15) 0.0230(16) 0.0207(15) 0.0051(12) 0.0017(12) 0.0059(12) C21 0.0190(15) 0.0199(15) 0.0228(15) 0.0015(12) 0.0028(12) 0.0069(12) C22 0.0179(14) 0.0194(15) 0.0242(15) 0.0030(12) 0.0006(12) 0.0045(12) C23 0.0233(16) 0.0275(18) 0.0312(18) 0.0058(14) 0.0037(14) 0.0066(14) C24 0.0345(19) 0.0208(17) 0.0329(19) 0.0089(14) 0.0113(15) 0.0040(14) C25 0.0204(16) 0.0220(17) 0.040(2) -0.0007(15) 0.0058(14) -0.0008(13) C26 0.0167(15) 0.0240(17) 0.0343(18) -0.0010(14) -0.0019(13) 0.0036(13) Cl1 0.0223(4) 0.0243(4) 0.0307(4) 0.0000(3) 0.0037(3) 0.0045(3) Cl2 0.0227(4) 0.0398(5) 0.0301(4) -0.0001(4) -0.0089(3) 0.0100(4) N1 0.0194(13) 0.0281(15) 0.0214(13) 0.0065(11) -0.0015(10) 0.0053(11) N2 0.0181(12) 0.0201(13) 0.0204(12) 0.0028(10) -0.0007(10) 0.0064(10) N3 0.0234(13) 0.0235(14) 0.0177(12) 0.0009(10) -0.0018(10) 0.0096(11) N4 0.0176(13) 0.0213(14) 0.0274(14) 0.0018(11) 0.0015(11) 0.0053(11) O1 0.0404(16) 0.0539(19) 0.0289(14) 0.0193(13) 0.0004(12) 0.0047(14) S1 0.0586(7) 0.0841(10) 0.0261(5) 0.0215(6) -0.0024(5) 0.0106(7) S2 0.0768(9) 0.0630(8) 0.0214(5) 0.0123(5) -0.0077(5) 0.0244(7) S3 0.0632(8) 0.0711(9) 0.0276(5) 0.0234(5) -0.0068(5) 0.0057(6) S4 0.0947(11) 0.0680(9) 0.0319(6) 0.0192(6) -0.0021(6) 0.0297(8) S5 0.0840(10) 0.0624(8) 0.0268(5) 0.0203(5) -0.0087(6) 0.0079(7) S6 0.1334(16) 0.0815(11) 0.0501(8) 0.0234(8) -0.0061(9) 0.0584(11) S7 0.0626(9) 0.1308(16) 0.0574(9) 0.0495(10) -0.0102(7) 0.0238(9) S8 0.0497(6) 0.0356(5) 0.0189(4) 0.0082(4) -0.0076(4) -0.0024(4) Zn1 0.01556(18) 0.0254(2) 0.02228(19) 0.00196(15) -0.00151(13) 0.00742(15) _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 C1 C2 1.348(6) . ? C1 S1 1.747(6) . ? C1 S2 1.762(5) . ? C2 S3 1.758(5) . ? C2 S4 1.769(6) . ? C3 C4 1.348(8) . ? C3 S3 1.757(5) . ? C3 S5 1.763(5) . ? C4 S6 1.751(6) . ? C4 S4 1.758(5) . ? C5 S5 1.719(9) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 S6 1.756(10) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.331(7) . ? C7 S7 1.759(5) . ? C7 S1 1.764(4) . ? C8 S2 1.748(4) . ? C8 S8 1.766(4) . ? C9 S7 1.800(10) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.500(5) . ? C10 S8 1.829(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O1 1.211(4) . ? C11 N1 1.379(4) . ? C12 N1 1.391(4) . ? C12 C13 1.398(4) . ? C12 C20 1.402(4) . ? C13 C14 1.377(4) . ? C13 H13 0.9300 . ? C14 N2 1.347(4) . ? C14 C15 1.488(4) . ? C15 N3 1.349(4) . ? C15 C16 1.390(4) . ? C16 C17 1.390(5) . ? C16 H16 0.9300 . ? C17 C18 1.391(5) . ? C17 H17 0.9300 . ? C18 C19 1.387(5) . ? C18 H18 0.9300 . ? C19 N3 1.343(4) . ? C19 H19 0.9300 . ? C20 C21 1.388(4) . ? C20 H20 0.9300 . ? C21 N2 1.342(4) . ? C21 C22 1.494(4) . ? C22 N4 1.360(4) . ? C22 C23 1.388(5) . ? C23 C24 1.403(5) . ? C23 H23 0.9300 . ? C24 C25 1.381(5) . ? C24 H24 0.9300 . ? C25 C26 1.375(5) . ? C25 H25 0.9300 . ? C26 N4 1.337(4) . ? C26 H26 0.9300 . ? Cl1 Zn1 2.3139(9) . ? Cl2 Zn1 2.2513(9) . ? N1 H1 0.8600 . ? N2 Zn1 2.088(3) . ? N3 Zn1 2.173(3) . ? N4 Zn1 2.228(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 S1 125.0(4) . . ? C2 C1 S2 120.7(5) . . ? S1 C1 S2 114.1(2) . . ? C1 C2 S3 123.7(5) . . ? C1 C2 S4 122.0(4) . . ? S3 C2 S4 114.2(2) . . ? C4 C3 S3 118.4(3) . . ? C4 C3 S5 122.3(4) . . ? S3 C3 S5 119.3(4) . . ? C3 C4 S6 126.1(3) . . ? C3 C4 S4 116.2(4) . . ? S6 C4 S4 117.5(4) . . ? S5 C5 H5A 109.5 . . ? S5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? S5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? S6 C6 H6A 109.5 . . ? S6 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? S6 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 S7 126.3(3) . . ? C8 C7 S1 116.6(3) . . ? S7 C7 S1 117.1(3) . . ? C7 C8 S2 118.1(3) . . ? C7 C8 S8 126.7(3) . . ? S2 C8 S8 115.0(3) . . ? S7 C9 H9A 109.5 . . ? S7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? S7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 S8 110.3(3) . . ? C11 C10 H10A 109.6 . . ? S8 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? S8 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O1 C11 N1 124.3(3) . . ? O1 C11 C10 122.9(3) . . ? N1 C11 C10 112.7(3) . . ? N1 C12 C13 116.8(3) . . ? N1 C12 C20 123.5(3) . . ? C13 C12 C20 119.8(3) . . ? C14 C13 C12 118.9(3) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? N2 C14 C13 121.4(3) . . ? N2 C14 C15 113.5(3) . . ? C13 C14 C15 125.1(3) . . ? N3 C15 C16 122.1(3) . . ? N3 C15 C14 114.8(3) . . ? C16 C15 C14 123.1(3) . . ? C15 C16 C17 118.3(3) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C16 C17 C18 119.6(3) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C19 C18 C17 118.7(3) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? N3 C19 C18 122.0(3) . . ? N3 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C21 C20 C12 117.4(3) . . ? C21 C20 H20 121.3 . . ? C12 C20 H20 121.3 . . ? N2 C21 C20 122.5(3) . . ? N2 C21 C22 113.6(3) . . ? C20 C21 C22 123.9(3) . . ? N4 C22 C23 122.0(3) . . ? N4 C22 C21 114.3(3) . . ? C23 C22 C21 123.6(3) . . ? C22 C23 C24 118.2(3) . . ? C22 C23 H23 120.9 . . ? C24 C23 H23 120.9 . . ? C25 C24 C23 119.4(3) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C26 C25 C24 118.7(3) . . ? C26 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? N4 C26 C25 123.3(3) . . ? N4 C26 H26 118.4 . . ? C25 C26 H26 118.4 . . ? C11 N1 C12 129.3(3) . . ? C11 N1 H1 115.3 . . ? C12 N1 H1 115.3 . . ? C21 N2 C14 120.0(3) . . ? C21 N2 Zn1 119.3(2) . . ? C14 N2 Zn1 117.9(2) . . ? C19 N3 C15 119.2(3) . . ? C19 N3 Zn1 125.3(2) . . ? C15 N3 Zn1 115.4(2) . . ? C26 N4 C22 118.3(3) . . ? C26 N4 Zn1 126.7(2) . . ? C22 N4 Zn1 114.4(2) . . ? C1 S1 C7 95.6(2) . . ? C8 S2 C1 95.2(2) . . ? C3 S3 C2 95.2(3) . . ? C4 S4 C2 95.9(3) . . ? C5 S5 C3 103.1(3) . . ? C4 S6 C6 101.4(5) . . ? C7 S7 C9 103.2(4) . . ? C8 S8 C10 100.63(19) . . ? N2 Zn1 N3 75.36(10) . . ? N2 Zn1 N4 73.88(10) . . ? N3 Zn1 N4 145.27(10) . . ? N2 Zn1 Cl2 146.66(8) . . ? N3 Zn1 Cl2 100.30(7) . . ? N4 Zn1 Cl2 96.58(8) . . ? N2 Zn1 Cl1 97.48(8) . . ? N3 Zn1 Cl1 102.63(8) . . ? N4 Zn1 Cl1 97.00(8) . . ? Cl2 Zn1 Cl1 115.55(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.207 _refine_diff_density_min -1.109 _refine_diff_density_rms 0.114 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.500 0.500 156.3 35.4 _platon_squeeze_details ; The unit cell contains disordered methanol molecules which could not be reliably modelled during refinement but the corresponding scattering contribution were taken into account using SQUEEZE/PLATON procedure. The solvent region contains about 35 e/cell in a void of 156 A3, which corresponds to 2 molecules of methanol per cell , i.e 1 molecule of methanol per formula unit and empirical formula, F(000), M, mu, D have been calculated on this assumption. ;