# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_date 2013-11-14 _audit_creation_method ; Olex2 1.2 (compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C26 H26 Ga N16 S2' _chemical_formula_sum 'C26 H26 Ga N16 S2' _chemical_formula_weight 696.47 _chemical_melting_point ? 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' Ga Ga 0.2307 1.6083 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 70 _space_group_name_H-M_alt 'F d d d' _space_group_name_Hall '-F 2uv 2vw' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+3/4, -y+3/4, z' 3 '-x+3/4, y, -z+3/4' 4 'x, -y+3/4, -z+3/4' 5 'x, y+1/2, z+1/2' 6 '-x+3/4, -y+5/4, z+1/2' 7 '-x+3/4, y+1/2, -z+5/4' 8 'x, -y+5/4, -z+5/4' 9 'x+1/2, y, z+1/2' 10 '-x+5/4, -y+3/4, z+1/2' 11 '-x+5/4, y, -z+5/4' 12 'x+1/2, -y+3/4, -z+5/4' 13 'x+1/2, y+1/2, z' 14 '-x+5/4, -y+5/4, z' 15 '-x+5/4, y+1/2, -z+3/4' 16 'x+1/2, -y+5/4, -z+3/4' 17 '-x, -y, -z' 18 'x-3/4, y-3/4, -z' 19 'x-3/4, -y, z-3/4' 20 '-x, y-3/4, z-3/4' 21 '-x, -y+1/2, -z+1/2' 22 'x-3/4, y-1/4, -z+1/2' 23 'x-3/4, -y+1/2, z-1/4' 24 '-x, y-1/4, z-1/4' 25 '-x+1/2, -y, -z+1/2' 26 'x-1/4, y-3/4, -z+1/2' 27 'x-1/4, -y, z-1/4' 28 '-x+1/2, y-3/4, z-1/4' 29 '-x+1/2, -y+1/2, -z' 30 'x-1/4, y-1/4, -z' 31 'x-1/4, -y+1/2, z-3/4' 32 '-x+1/2, y-1/4, z-3/4' _cell_length_a 13.4347(9) _cell_length_b 31.954(2) _cell_length_c 33.272(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 14283.1(16) _cell_formula_units_Z 16 _cell_measurement_reflns_used 3209 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 21.180 _cell_measurement_theta_min 2.449 _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6097 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0687 before and 0.0515 after correction. The Ratio of minimum to maximum transmission is 0.8176. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 5712 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0620 _diffrn_reflns_av_unetI/netI 0.0529 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_number 22702 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_min 1.22 _diffrn_ambient_temperature 153(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker Apex2' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _reflns_number_gt 2300 _reflns_number_total 3116 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)' _refine_diff_density_max 0.328 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 204 _refine_ls_number_reflns 3116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0373 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0905 _refine_ls_wR_factor_ref 0.0956 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Me refined with riding coordinates: C6(H6A,H6B,H6C), C9(H9A,H9B,H9C) 2.b Aromatic/amide H refined with riding coordinates: N5(H5), C1(H1), C2(H2), C3(H3), C11(H11), C12(H12), C13(H13) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 0.57369(5) 0.57327(2) 0.57769(2) 0.0551(2) Uani 1 1 d . . . Ga1 Ga 0.6250 0.6250 0.533116(12) 0.03966(15) Uani 1 2 d S . . N1 N 0.61415(16) 0.66971(6) 0.48523(7) 0.0463(5) Uani 1 1 d . . . N2 N 0.5751(3) 0.72988(11) 0.42770(10) 0.0956(11) Uani 1 1 d . . . N3 N 0.47440(15) 0.63503(6) 0.52737(6) 0.0402(5) Uani 1 1 d . . . N4 N 0.40882(15) 0.61621(7) 0.55295(6) 0.0423(5) Uani 1 1 d . . . N5 N 0.38912(16) 0.57155(7) 0.60478(6) 0.0457(5) Uani 1 1 d . . . H5 H 0.3253 0.5777 0.6048 0.055 Uiso 1 1 calc R . . N6 N 0.42710(16) 0.54426(7) 0.63206(6) 0.0440(5) Uani 1 1 d . . . N7 N 0.36470(19) 0.48149(9) 0.71484(8) 0.0726(8) Uani 1 1 d . . . N8 N 0.5649(2) 0.46230(10) 0.70670(11) 0.0875(10) Uani 1 1 d . . . C1 C 0.6876(2) 0.68922(10) 0.46647(10) 0.0652(9) Uani 1 1 d . . . H1 H 0.7548 0.6824 0.4725 0.078 Uiso 1 1 calc R . . C2 C 0.6664(3) 0.71981(12) 0.43795(12) 0.0860(12) Uani 1 1 d . . . H2 H 0.7202 0.7340 0.4254 0.103 Uiso 1 1 calc R . . C3 C 0.5027(3) 0.71007(11) 0.44695(11) 0.0775(10) Uani 1 1 d . . . H3 H 0.4358 0.7168 0.4404 0.093 Uiso 1 1 calc R . . C4 C 0.5197(2) 0.68017(8) 0.47610(8) 0.0497(7) Uani 1 1 d . . . C5 C 0.4412(2) 0.65967(8) 0.49961(8) 0.0471(7) Uani 1 1 d . . . C6 C 0.3343(2) 0.66792(11) 0.49153(10) 0.0699(9) Uani 1 1 d . . . H6A H 0.3281 0.6875 0.4690 0.105 Uiso 1 1 calc R . . H6B H 0.3033 0.6800 0.5155 0.105 Uiso 1 1 calc R . . H6C H 0.3008 0.6416 0.4847 0.105 Uiso 1 1 calc R . . C7 C 0.45168(19) 0.58911(8) 0.57737(8) 0.0415(6) Uani 1 1 d . . . C8 C 0.36716(19) 0.52559(8) 0.65628(8) 0.0461(7) Uani 1 1 d . . . C9 C 0.2574(2) 0.53061(11) 0.65787(11) 0.0707(9) Uani 1 1 d . . . H9A H 0.2302 0.5127 0.6791 0.106 Uiso 1 1 calc R . . H9B H 0.2285 0.5225 0.6320 0.106 Uiso 1 1 calc R . . H9C H 0.2410 0.5599 0.6635 0.106 Uiso 1 1 calc R . . C10 C 0.4183(2) 0.49707(8) 0.68462(8) 0.0460(7) Uani 1 1 d . . . C11 C 0.5169(2) 0.48655(10) 0.68089(11) 0.0678(9) Uani 1 1 d . . . H11 H 0.5527 0.4973 0.6585 0.081 Uiso 1 1 calc R . . C12 C 0.5107(3) 0.44799(11) 0.73719(11) 0.0752(10) Uani 1 1 d . . . H12 H 0.5418 0.4311 0.7570 0.090 Uiso 1 1 calc R . . C13 C 0.4132(3) 0.45675(13) 0.74074(11) 0.0832(11) Uani 1 1 d . . . H13 H 0.3772 0.4449 0.7625 0.100 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 0.0393(4) 0.0654(5) 0.0605(5) 0.0223(4) 0.0034(3) 0.0049(3) Ga1 0.0342(2) 0.0442(3) 0.0406(2) 0.000 0.000 -0.00029(17) N1 0.0458(14) 0.0457(14) 0.0474(13) 0.0065(10) -0.0011(11) -0.0009(10) N2 0.076(2) 0.103(2) 0.108(3) 0.061(2) -0.005(2) -0.0034(18) N3 0.0372(12) 0.0399(13) 0.0434(13) -0.0040(10) 0.0006(10) 0.0007(9) N4 0.0354(12) 0.0440(13) 0.0475(13) 0.0028(10) 0.0010(10) 0.0006(9) N5 0.0395(13) 0.0500(14) 0.0475(13) 0.0020(11) 0.0071(11) 0.0023(10) N6 0.0420(12) 0.0436(13) 0.0464(13) -0.0020(10) 0.0059(11) -0.0053(10) N7 0.0568(17) 0.090(2) 0.0712(18) 0.0236(16) 0.0163(14) 0.0038(14) N8 0.0524(18) 0.099(2) 0.111(3) 0.037(2) -0.0033(17) 0.0022(16) C1 0.0525(19) 0.070(2) 0.073(2) 0.0264(17) -0.0052(16) -0.0072(15) C2 0.074(2) 0.096(3) 0.089(3) 0.044(2) 0.002(2) -0.016(2) C3 0.061(2) 0.085(3) 0.086(3) 0.034(2) -0.008(2) 0.0068(18) C4 0.0512(17) 0.0470(17) 0.0509(17) 0.0083(13) -0.0058(14) 0.0047(13) C5 0.0465(16) 0.0445(16) 0.0504(16) 0.0019(13) -0.0067(13) 0.0047(12) C6 0.0447(17) 0.077(2) 0.088(2) 0.0233(18) -0.0090(17) 0.0120(15) C7 0.0407(15) 0.0429(15) 0.0408(15) -0.0068(12) 0.0031(12) -0.0035(11) C8 0.0416(15) 0.0471(16) 0.0496(16) -0.0053(13) 0.0105(13) -0.0031(12) C9 0.0475(18) 0.086(2) 0.078(2) 0.0167(18) 0.0216(17) 0.0097(16) C10 0.0445(16) 0.0442(16) 0.0493(16) -0.0007(13) 0.0087(13) -0.0082(12) C11 0.0439(18) 0.080(2) 0.079(2) 0.0222(19) 0.0105(17) -0.0062(16) C12 0.068(2) 0.073(2) 0.085(3) 0.0258(19) -0.005(2) -0.0021(18) C13 0.075(2) 0.103(3) 0.072(2) 0.032(2) 0.015(2) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Highly disordered solvent was located in the structures. Reflection contributions from this solvent were removed using program OLEX2, function MSAKS, which determined there to be 913 electrons in 3226.7 \%A^3^ removed per unit cell. One set of residual peaks did appear to one acetate ion. However, this did not define the entire solvent area. Thus, the total number of electrons [913] in the void per unit cell, equivalent to about 913/16 = 57 per molecule unit, which is attributed to one disordered acetate ion and one alcohol molecule. All these reported items that derive from the molecular formula (e.g., F(000), density, molecular weight, etc.) are known to be incorrect. ; 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 Ga1 2.3252(8) . ? S1 C7 1.716(3) . ? Ga1 S1 2.3252(8) 14 ? Ga1 N1 2.145(2) 14 ? Ga1 N1 2.145(2) . ? Ga1 N3 2.057(2) . ? Ga1 N3 2.057(2) 14 ? N1 C1 1.324(4) . ? N1 C4 1.347(3) . ? N2 C2 1.313(5) . ? N2 C3 1.326(4) . ? N3 N4 1.365(3) . ? N3 C5 1.293(3) . ? N4 C7 1.320(3) . ? N5 H5 0.8800 . ? N5 N6 1.358(3) . ? N5 C7 1.361(3) . ? N6 C8 1.286(3) . ? N7 C10 1.333(3) . ? N7 C13 1.339(4) . ? N8 C11 1.324(4) . ? N8 C12 1.330(4) . ? C1 H1 0.9500 . ? C1 C2 1.392(4) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C3 C4 1.380(4) . ? C4 C5 1.467(4) . ? C5 C6 1.486(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 C9 1.485(4) . ? C8 C10 1.481(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.372(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C12 C13 1.345(5) . ? C13 H13 0.9500 . ? 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 C7 S1 Ga1 93.99(9) . . ? S1 Ga1 S1 100.74(4) 14 . ? N1 Ga1 S1 91.17(6) 14 . ? N1 Ga1 S1 157.99(6) . . ? N1 Ga1 S1 157.99(6) 14 14 ? N1 Ga1 S1 91.17(6) . 14 ? N1 Ga1 N1 84.07(12) 14 . ? N3 Ga1 S1 83.02(6) 14 14 ? N3 Ga1 S1 103.89(6) . 14 ? N3 Ga1 S1 83.02(6) . . ? N3 Ga1 S1 103.89(6) 14 . ? N3 Ga1 N1 76.14(8) . . ? N3 Ga1 N1 95.83(8) 14 . ? N3 Ga1 N1 95.83(8) . 14 ? N3 Ga1 N1 76.14(8) 14 14 ? N3 Ga1 N3 169.34(12) 14 . ? C1 N1 Ga1 127.8(2) . . ? C1 N1 C4 118.6(2) . . ? C4 N1 Ga1 113.39(17) . . ? C2 N2 C3 116.3(3) . . ? N4 N3 Ga1 120.56(16) . . ? C5 N3 Ga1 120.01(18) . . ? C5 N3 N4 119.4(2) . . ? C7 N4 N3 113.0(2) . . ? N6 N5 H5 120.6 . . ? N6 N5 C7 118.7(2) . . ? C7 N5 H5 120.6 . . ? C8 N6 N5 118.8(2) . . ? C10 N7 C13 116.3(3) . . ? C11 N8 C12 115.4(3) . . ? N1 C1 H1 120.0 . . ? N1 C1 C2 120.0(3) . . ? C2 C1 H1 120.0 . . ? N2 C2 C1 122.7(3) . . ? N2 C2 H2 118.6 . . ? C1 C2 H2 118.6 . . ? N2 C3 H3 118.4 . . ? N2 C3 C4 123.3(3) . . ? C4 C3 H3 118.4 . . ? N1 C4 C3 119.1(3) . . ? N1 C4 C5 116.5(2) . . ? C3 C4 C5 124.4(3) . . ? N3 C5 C4 113.9(2) . . ? N3 C5 C6 124.8(3) . . ? C4 C5 C6 121.3(2) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 S1 127.9(2) . . ? N4 C7 N5 114.4(2) . . ? N5 C7 S1 117.7(2) . . ? N6 C8 C9 126.5(3) . . ? N6 C8 C10 113.2(2) . . ? C10 C8 C9 120.3(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N7 C10 C8 117.3(2) . . ? N7 C10 C11 119.9(3) . . ? C11 C10 C8 122.8(3) . . ? N8 C11 C10 123.7(3) . . ? N8 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? N8 C12 H12 119.0 . . ? N8 C12 C13 121.9(3) . . ? C13 C12 H12 119.0 . . ? N7 C13 C12 122.7(3) . . ? N7 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 Ga1 N1 C1 70.2(3) 14 . . . ? S1 Ga1 N1 C1 -166.6(2) . . . . ? S1 Ga1 N1 C4 -105.08(18) 14 . . . ? S1 Ga1 N1 C4 18.1(3) . . . . ? S1 Ga1 N3 N4 10.41(16) . . . . ? S1 Ga1 N3 N4 -88.98(17) 14 . . . ? S1 Ga1 N3 C5 -170.3(2) . . . . ? S1 Ga1 N3 C5 90.3(2) 14 . . . ? Ga1 S1 C7 N4 11.1(2) . . . . ? Ga1 S1 C7 N5 -170.35(18) . . . . ? Ga1 N1 C1 C2 -175.1(3) . . . . ? Ga1 N1 C4 C3 177.2(2) . . . . ? Ga1 N1 C4 C5 -0.3(3) . . . . ? Ga1 N3 N4 C7 -6.4(3) . . . . ? Ga1 N3 C5 C4 -3.5(3) . . . . ? Ga1 N3 C5 C6 177.4(2) . . . . ? N1 Ga1 N1 C1 -88.3(3) 14 . . . ? N1 Ga1 N1 C4 96.5(2) 14 . . . ? N1 Ga1 N3 N4 -176.72(18) . . . . ? N1 Ga1 N3 N4 100.88(18) 14 . . . ? N1 Ga1 N3 C5 2.60(19) . . . . ? N1 Ga1 N3 C5 -79.8(2) 14 . . . ? N1 C1 C2 N2 -1.7(6) . . . . ? N1 C4 C5 N3 2.4(4) . . . . ? N1 C4 C5 C6 -178.4(3) . . . . ? N2 C3 C4 N1 -1.3(5) . . . . ? N2 C3 C4 C5 176.0(3) . . . . ? N3 Ga1 N1 C1 174.2(3) . . . . ? N3 Ga1 N1 C1 -12.9(3) 14 . . . ? N3 Ga1 N1 C4 171.82(18) 14 . . . ? N3 Ga1 N1 C4 -1.06(18) . . . . ? N3 Ga1 N3 N4 141.47(17) 14 . . . ? N3 Ga1 N3 C5 -39.21(19) 14 . . . ? N3 N4 C7 S1 -4.9(3) . . . . ? N3 N4 C7 N5 176.5(2) . . . . ? N4 N3 C5 C4 175.8(2) . . . . ? N4 N3 C5 C6 -3.3(4) . . . . ? N5 N6 C8 C9 0.0(4) . . . . ? N5 N6 C8 C10 -179.5(2) . . . . ? N6 N5 C7 S1 3.3(3) . . . . ? N6 N5 C7 N4 -177.9(2) . . . . ? N6 C8 C10 N7 169.6(3) . . . . ? N6 C8 C10 C11 -10.2(4) . . . . ? N7 C10 C11 N8 -2.3(5) . . . . ? N8 C12 C13 N7 -2.4(6) . . . . ? C1 N1 C4 C3 1.5(4) . . . . ? C1 N1 C4 C5 -176.1(3) . . . . ? C2 N2 C3 C4 -0.4(6) . . . . ? C3 N2 C2 C1 1.9(6) . . . . ? C3 C4 C5 N3 -175.0(3) . . . . ? C3 C4 C5 C6 4.2(5) . . . . ? C4 N1 C1 C2 -0.1(5) . . . . ? C5 N3 N4 C7 174.3(2) . . . . ? C7 S1 Ga1 S1 93.78(9) . . . 14 ? C7 S1 Ga1 N1 -27.87(19) . . . . ? C7 S1 Ga1 N1 -104.84(10) . . . 14 ? C7 S1 Ga1 N3 179.16(10) . . . 14 ? C7 S1 Ga1 N3 -9.10(10) . . . . ? C7 N5 N6 C8 -175.6(2) . . . . ? C8 C10 C11 N8 177.5(3) . . . . ? C9 C8 C10 N7 -9.9(4) . . . . ? C9 C8 C10 C11 170.3(3) . . . . ? C10 N7 C13 C12 0.5(6) . . . . ? C11 N8 C12 C13 1.7(6) . . . . ? C12 N8 C11 C10 0.5(5) . . . . ? C13 N7 C10 C8 -178.1(3) . . . . ? C13 N7 C10 C11 1.7(5) . . . . ? loop_ _smtbx_masks_void_nr _smtbx_masks_void_average_x _smtbx_masks_void_average_y _smtbx_masks_void_average_z _smtbx_masks_void_volume _smtbx_masks_void_count_electrons _smtbx_masks_void_content 1 -0.767 0.125 0.875 308.4 73.4 'acetate ion and alcohol' 2 -0.206 0.125 0.375 308.4 73.4 'acetate ion and alcohol' 3 0.125 0.125 0.125 94.9 40.8 'acetate ion and alcohol' 4 -0.282 0.375 0.125 308.4 72.9 'acetate ion and alcohol' 5 -0.854 0.375 0.625 308.4 72.9 'acetate ion and alcohol' 6 -0.125 0.375 0.375 94.9 41.2 'acetate ion and alcohol' 7 -0.767 0.625 0.375 308.4 73.4 'acetate ion and alcohol' 8 -0.206 0.625 0.875 308.4 73.4 'acetate ion and alcohol' 9 0.125 0.625 0.625 94.9 40.8 'acetate ion and alcohol' 10 -0.282 0.875 0.625 308.4 72.9 'acetate ion and alcohol' 11 -0.854 0.875 0.125 308.4 72.9 'acetate ion and alcohol' 12 -0.125 0.875 0.875 94.9 41.2 'acetate ion and alcohol' 13 0.375 0.375 0.875 94.9 41.2 'acetate ion and alcohol' 14 0.375 0.875 0.375 94.9 41.2 'acetate ion and alcohol' 15 0.625 0.125 0.625 94.9 40.8 'acetate ion and alcohol' 16 0.625 0.625 0.125 94.9 40.8 'acetate ion and alcohol' _smtbx_masks_special_details ; Highly disordered solvent was located in the structures. Reflection contributions from this solvent were removed using program OLEX2, function MSAKS, which determined there to be 913 electrons in 3226.7 \%A^3^ removed per unit cell. One set of residual peaks did appear to one acetate ion. However, this did not define the entire solvent area. Thus, the total number of electrons [913] in the void per unit cell, equivalent to about 913/16 = 57 per molecule unit, which is attributed to one disordered acetate ion and one alcohol molecule. All these reported items that derive from the molecular formula (e.g., F(000), density, molecular weight, etc.) are known to be incorrect. ; _database_code_depnum_ccdc_archive 'CCDC 934513' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H26 N8 O2 S Sn, C3 H7 N O' _chemical_formula_sum 'C30 H33 N9 O3 S Sn' _chemical_formula_weight 718.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Sn Sn -0.6537 1.4246 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.916(2) _cell_length_b 11.8640(18) _cell_length_c 14.183(2) _cell_angle_alpha 86.149(3) _cell_angle_beta 69.356(2) _cell_angle_gamma 67.672(3) _cell_volume 1585.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 141 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 13.03 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.919 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7962 _exptl_absorpt_correction_T_max 0.8978 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8169 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0782 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5549 _reflns_number_gt 4255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The DELU instruction was used for the two couples of N7, C13 and N8, C11 atoms in order to solve the large Hirshfeld Test Diff. ; _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^)+(0.0568P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5549 _refine_ls_number_parameters 397 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.057 _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 Sn1 Sn 0.32161(4) 0.20281(3) 0.78640(3) 0.03256(14) Uani 1 1 d . . . S1 S 0.57995(14) 0.04974(12) 0.71762(10) 0.0390(3) Uani 1 1 d . . . N1 N 0.1279(4) 0.3358(4) 0.7264(3) 0.0338(10) Uani 1 1 d . . . N2 N -0.0784(5) 0.4647(4) 0.6435(4) 0.0538(13) Uani 1 1 d . . . N3 N 0.3939(4) 0.2034(3) 0.6064(3) 0.0285(9) Uani 1 1 d . . . N4 N 0.5301(4) 0.1374(4) 0.5435(3) 0.0349(10) Uani 1 1 d . . . N5 N 0.7424(4) 0.0016(4) 0.5261(3) 0.0428(11) Uani 1 1 d . . . H5A H 0.7623 0.0139 0.4630 0.051 Uiso 1 1 calc RD . . N6 N 0.8449(4) -0.0847(4) 0.5559(3) 0.0364(10) Uani 1 1 d . . . N7 N 1.0149(6) -0.2758(5) 0.6275(4) 0.0644(15) Uani 1 1 d U . . N8 N 1.2899(6) -0.3607(5) 0.5211(5) 0.0749(18) Uani 1 1 d U . . C1 C -0.0065(6) 0.3987(5) 0.7840(5) 0.0449(14) Uani 1 1 d . . . H1A H -0.0328 0.3995 0.8540 0.054 Uiso 1 1 calc R . . C2 C -0.1079(6) 0.4632(5) 0.7419(5) 0.0525(16) Uani 1 1 d . . . H2B H -0.2001 0.5068 0.7847 0.063 Uiso 1 1 calc R . . C3 C 0.0566(6) 0.4024(5) 0.5863(5) 0.0454(14) Uani 1 1 d . . . H3A H 0.0821 0.4023 0.5165 0.054 Uiso 1 1 calc R . . C4 C 0.1610(5) 0.3376(4) 0.6265(4) 0.0321(12) Uani 1 1 d . . . C5 C 0.3092(5) 0.2694(4) 0.5613(4) 0.0330(12) Uani 1 1 d . . . C6 C 0.3534(6) 0.2782(5) 0.4498(4) 0.0476(15) Uani 1 1 d . . . H6B H 0.4523 0.2290 0.4186 0.071 Uiso 1 1 calc R . . H6C H 0.3369 0.3618 0.4352 0.071 Uiso 1 1 calc R . . H6D H 0.2994 0.2496 0.4237 0.071 Uiso 1 1 calc R . . C7 C 0.6132(5) 0.0675(4) 0.5906(4) 0.0331(12) Uani 1 1 d . . . C8 C 0.9687(5) -0.1410(5) 0.4903(4) 0.0350(12) Uani 1 1 d . . . C9 C 1.0278(4) -0.1245(5) 0.3772(4) 0.0524(16) Uani 1 1 d . . . H9A H 0.9552 -0.0627 0.3582 0.079 Uiso 1 1 calc RD . . H9B H 1.0587 -0.2003 0.3390 0.079 Uiso 1 1 calc R . . H9C H 1.1065 -0.1003 0.3636 0.079 Uiso 1 1 calc R . . C10 C 1.0665(6) -0.2346(5) 0.5339(4) 0.0352(12) Uani 1 1 d . . . C11 C 1.2049(5) -0.2789(4) 0.4803(4) 0.0353(12) Uani 1 1 d U . . H11A H 1.2405 -0.2533 0.4166 0.042 Uiso 1 1 calc R . . C12 C 1.2376(7) -0.4009(5) 0.6139(5) 0.0461(15) Uani 1 1 d . . . H12A H 1.3003 -0.4588 0.6400 0.055 Uiso 1 1 calc R . . C13 C 1.1004(6) -0.3598(5) 0.6674(4) 0.0383(12) Uani 1 1 d U . . H13A H 1.0653 -0.3882 0.7299 0.046 Uiso 1 1 calc R . . C14 C 0.2300(5) 0.0714(4) 0.7848(4) 0.0337(12) Uani 1 1 d . . . C15 C 0.1053(6) 0.0726(5) 0.8601(4) 0.0406(13) Uani 1 1 d . . . H15A H 0.0547 0.1357 0.9110 0.049 Uiso 1 1 calc R . . C16 C 0.0563(6) -0.0188(5) 0.8599(5) 0.0479(15) Uani 1 1 d . . . H16A H -0.0266 -0.0169 0.9107 0.058 Uiso 1 1 calc R . . C17 C 0.1287(7) -0.1121(5) 0.7856(5) 0.0499(15) Uani 1 1 d . . . H17A H 0.0953 -0.1735 0.7857 0.060 Uiso 1 1 calc R . . C18 C 0.2510(6) -0.1148(5) 0.7108(4) 0.0432(14) Uani 1 1 d . . . H18A H 0.3004 -0.1786 0.6605 0.052 Uiso 1 1 calc R . . C19 C 0.3019(6) -0.0244(4) 0.7093(4) 0.0385(13) Uani 1 1 d . . . H19A H 0.3845 -0.0272 0.6576 0.046 Uiso 1 1 calc R . . C20 C 0.3603(6) 0.3664(4) 0.7902(4) 0.0367(13) Uani 1 1 d . . . C21 C 0.4894(6) 0.3705(5) 0.7336(4) 0.0451(14) Uani 1 1 d . . . H21A H 0.5585 0.3021 0.6917 0.054 Uiso 1 1 calc R . . C22 C 0.5207(8) 0.4734(6) 0.7367(5) 0.0577(17) Uani 1 1 d . . . H22A H 0.6102 0.4728 0.6993 0.069 Uiso 1 1 calc R . . C23 C 0.4170(9) 0.5756(6) 0.7962(5) 0.0619(19) Uani 1 1 d . . . H23A H 0.4354 0.6457 0.7973 0.074 Uiso 1 1 calc R . . C24 C 0.2848(8) 0.5756(5) 0.8549(5) 0.0592(18) Uani 1 1 d . . . H24A H 0.2156 0.6448 0.8958 0.071 Uiso 1 1 calc R . . C25 C 0.2566(6) 0.4707(5) 0.8519(4) 0.0460(14) Uani 1 1 d . . . H25A H 0.1684 0.4701 0.8913 0.055 Uiso 1 1 calc R . . C26 C 0.1820(8) 0.2209(7) 1.1008(5) 0.078(2) Uani 1 1 d . . . H26A H 0.0855 0.2762 1.1322 0.117 Uiso 1 1 calc R . . H26B H 0.2428 0.2471 1.1210 0.117 Uiso 1 1 calc R . . H26C H 0.1915 0.1402 1.1215 0.117 Uiso 1 1 calc R . . C27 C 0.2223(7) 0.2196(6) 0.9893(4) 0.0468(15) Uani 1 1 d . . . O1 O 0.1369(4) 0.2819(4) 0.9480(3) 0.0517(10) Uani 1 1 d . . . O2 O 0.3480(4) 0.1506(3) 0.9348(3) 0.0471(10) Uani 1 1 d . . . N9 N 0.5867(7) 0.2493(5) -0.0138(5) 0.0763(19) Uani 1 1 d . . . C28 C 0.4795(8) 0.3545(6) 0.0057(5) 0.0612(18) Uani 1 1 d . . . H28A H 0.4849 0.4101 -0.0436 0.073 Uiso 1 1 calc R . . C29 C 0.5858(12) 0.1564(8) 0.0524(9) 0.130(4) Uani 1 1 d . . . H29A H 0.5020 0.1860 0.1118 0.195 Uiso 1 1 calc R . . H29B H 0.6680 0.1318 0.0713 0.195 Uiso 1 1 calc R . . H29C H 0.5868 0.0877 0.0196 0.195 Uiso 1 1 calc R . . C30 C 0.7079(10) 0.2227(10) -0.1099(8) 0.140(5) Uani 1 1 d . . . H30A H 0.6946 0.2935 -0.1481 0.210 Uiso 1 1 calc R . . H30B H 0.7142 0.1556 -0.1482 0.210 Uiso 1 1 calc R . . H30C H 0.7936 0.2016 -0.0961 0.210 Uiso 1 1 calc R . . O3 O 0.3758(6) 0.3868(6) 0.0799(5) 0.105(2) 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 Sn1 0.0312(2) 0.0315(2) 0.0298(2) 0.00218(14) -0.00676(15) -0.01018(15) S1 0.0311(8) 0.0407(8) 0.0336(8) 0.0054(6) -0.0098(6) -0.0035(6) N1 0.031(2) 0.029(2) 0.035(3) 0.0035(19) -0.010(2) -0.0063(18) N2 0.031(3) 0.057(3) 0.060(4) -0.004(3) -0.018(3) 0.002(2) N3 0.022(2) 0.026(2) 0.028(2) 0.0009(17) -0.0059(18) -0.0025(17) N4 0.028(2) 0.037(2) 0.032(2) 0.001(2) -0.008(2) -0.0070(19) N5 0.035(3) 0.043(3) 0.034(3) 0.010(2) -0.010(2) -0.001(2) N6 0.027(2) 0.034(2) 0.036(3) -0.001(2) -0.009(2) -0.0017(19) N7 0.055(4) 0.065(3) 0.062(4) 0.014(3) -0.026(3) -0.008(3) N8 0.055(4) 0.078(4) 0.082(5) 0.015(3) -0.038(3) -0.003(3) C1 0.037(3) 0.048(3) 0.042(3) 0.003(3) -0.010(3) -0.011(3) C2 0.034(4) 0.051(4) 0.054(4) -0.003(3) -0.007(3) -0.004(3) C3 0.038(3) 0.039(3) 0.051(4) -0.001(3) -0.021(3) -0.002(3) C4 0.030(3) 0.027(3) 0.033(3) 0.002(2) -0.007(2) -0.008(2) C5 0.030(3) 0.036(3) 0.027(3) 0.007(2) -0.008(2) -0.009(2) C6 0.041(4) 0.053(4) 0.034(3) 0.008(3) -0.011(3) -0.005(3) C7 0.025(3) 0.029(3) 0.036(3) 0.001(2) -0.008(2) -0.003(2) C8 0.028(3) 0.037(3) 0.033(3) 0.000(2) -0.008(2) -0.006(2) C9 0.047(4) 0.052(4) 0.046(4) 0.012(3) -0.016(3) -0.008(3) C10 0.040(3) 0.033(3) 0.033(3) 0.005(2) -0.015(3) -0.014(2) C11 0.018(3) 0.040(3) 0.027(3) 0.006(2) 0.003(2) -0.001(2) C12 0.058(4) 0.040(3) 0.046(4) 0.011(3) -0.032(3) -0.013(3) C13 0.036(3) 0.043(3) 0.032(3) 0.013(2) -0.010(2) -0.014(2) C14 0.034(3) 0.032(3) 0.032(3) 0.005(2) -0.011(2) -0.009(2) C15 0.036(3) 0.039(3) 0.040(3) -0.003(3) -0.006(3) -0.013(3) C16 0.041(4) 0.053(4) 0.047(4) 0.007(3) -0.007(3) -0.024(3) C17 0.054(4) 0.040(3) 0.065(4) 0.013(3) -0.023(3) -0.027(3) C18 0.047(4) 0.037(3) 0.039(3) -0.004(3) -0.010(3) -0.013(3) C19 0.038(3) 0.035(3) 0.037(3) 0.003(2) -0.006(3) -0.015(3) C20 0.047(4) 0.031(3) 0.033(3) 0.008(2) -0.019(3) -0.013(3) C21 0.048(4) 0.049(3) 0.043(3) 0.010(3) -0.021(3) -0.019(3) C22 0.069(5) 0.060(4) 0.064(4) 0.021(4) -0.037(4) -0.036(4) C23 0.101(6) 0.041(4) 0.069(5) 0.016(3) -0.050(5) -0.037(4) C24 0.082(5) 0.032(3) 0.058(4) 0.000(3) -0.032(4) -0.010(3) C25 0.048(4) 0.039(3) 0.045(4) 0.003(3) -0.019(3) -0.009(3) C26 0.090(6) 0.116(6) 0.038(4) -0.002(4) -0.003(4) -0.065(5) C27 0.068(5) 0.057(4) 0.029(3) 0.001(3) -0.009(3) -0.046(4) O1 0.050(3) 0.056(3) 0.044(2) -0.004(2) -0.007(2) -0.022(2) O2 0.056(3) 0.050(2) 0.037(2) 0.0074(19) -0.016(2) -0.023(2) N9 0.075(5) 0.061(4) 0.088(5) 0.000(3) -0.047(4) -0.003(3) C28 0.058(5) 0.065(4) 0.058(5) -0.001(4) -0.018(4) -0.022(4) C29 0.177(11) 0.086(7) 0.186(12) 0.064(7) -0.118(10) -0.072(7) C30 0.064(6) 0.182(11) 0.096(8) -0.006(7) -0.009(6) 0.021(6) O3 0.069(4) 0.123(5) 0.085(4) -0.024(4) 0.005(3) -0.020(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sn1 C20 2.145(5) . ? Sn1 C14 2.153(5) . ? Sn1 O2 2.240(4) . ? Sn1 N3 2.392(4) . ? Sn1 O1 2.407(4) . ? Sn1 N1 2.498(4) . ? Sn1 S1 2.5708(14) . ? Sn1 C27 2.685(6) . ? S1 C7 1.722(5) . ? N1 C1 1.335(7) . ? N1 C4 1.335(6) . ? N2 C2 1.317(8) . ? N2 C3 1.336(7) . ? N3 C5 1.295(6) . ? N3 N4 1.376(5) . ? N4 C7 1.318(6) . ? N5 C7 1.336(6) . ? N5 N6 1.373(5) . ? N5 H5A 0.8600 . ? N6 C8 1.285(6) . ? N7 C13 1.333(7) . ? N7 C10 1.384(7) . ? N8 C11 1.326(7) . ? N8 C12 1.371(8) . ? C1 C2 1.390(8) . ? C1 H1A 0.9300 . ? C2 H2B 0.9300 . ? C3 C4 1.396(7) . ? C3 H3A 0.9300 . ? C4 C5 1.475(7) . ? C5 C6 1.492(7) . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C6 H6D 0.9600 . ? C8 C10 1.492(7) . ? C8 C9 1.533(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.332(7) . ? C11 H11A 0.9300 . ? C12 C13 1.323(8) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C19 1.395(7) . ? C14 C15 1.399(7) . ? C15 C16 1.380(7) . ? C15 H15A 0.9300 . ? C16 C17 1.365(8) . ? C16 H16A 0.9300 . ? C17 C18 1.372(8) . ? C17 H17A 0.9300 . ? C18 C19 1.379(7) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C21 1.371(8) . ? C20 C25 1.401(7) . ? C21 C22 1.395(8) . ? C21 H21A 0.9300 . ? C22 C23 1.373(9) . ? C22 H22A 0.9300 . ? C23 C24 1.389(9) . ? C23 H23A 0.9300 . ? C24 C25 1.396(8) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 C27 1.484(8) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 O1 1.249(7) . ? C27 O2 1.278(7) . ? N9 C28 1.308(8) . ? N9 C29 1.400(10) . ? N9 C30 1.476(11) . ? C28 O3 1.192(8) . ? C28 H28A 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 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 C20 Sn1 C14 165.31(19) . . ? C20 Sn1 O2 93.16(16) . . ? C14 Sn1 O2 93.20(16) . . ? C20 Sn1 N3 88.92(16) . . ? C14 Sn1 N3 90.57(16) . . ? O2 Sn1 N3 156.25(14) . . ? C20 Sn1 O1 85.97(17) . . ? C14 Sn1 O1 86.64(16) . . ? O2 Sn1 O1 55.99(15) . . ? N3 Sn1 O1 147.73(14) . . ? C20 Sn1 N1 84.13(16) . . ? C14 Sn1 N1 82.20(16) . . ? O2 Sn1 N1 137.20(15) . . ? N3 Sn1 N1 66.55(13) . . ? O1 Sn1 N1 81.23(15) . . ? C20 Sn1 S1 98.59(15) . . ? C14 Sn1 S1 95.40(14) . . ? O2 Sn1 S1 82.03(11) . . ? N3 Sn1 S1 74.27(9) . . ? O1 Sn1 S1 138.00(11) . . ? N1 Sn1 S1 140.69(10) . . ? C20 Sn1 C27 89.01(18) . . ? C14 Sn1 C27 90.34(17) . . ? O2 Sn1 C27 28.27(17) . . ? N3 Sn1 C27 175.23(18) . . ? O1 Sn1 C27 27.72(17) . . ? N1 Sn1 C27 108.95(18) . . ? S1 Sn1 C27 110.30(16) . . ? C7 S1 Sn1 98.61(17) . . ? C1 N1 C4 117.2(4) . . ? C1 N1 Sn1 126.4(4) . . ? C4 N1 Sn1 116.2(3) . . ? C2 N2 C3 115.8(5) . . ? C5 N3 N4 115.2(4) . . ? C5 N3 Sn1 122.4(3) . . ? N4 N3 Sn1 122.4(3) . . ? C7 N4 N3 114.2(4) . . ? C7 N5 N6 123.1(4) . . ? C7 N5 H5A 118.5 . . ? N6 N5 H5A 118.5 . . ? C8 N6 N5 119.6(4) . . ? C13 N7 C10 121.7(5) . . ? C11 N8 C12 121.4(6) . . ? N1 C1 C2 121.5(6) . . ? N1 C1 H1A 119.3 . . ? C2 C1 H1A 119.3 . . ? N2 C2 C1 122.4(6) . . ? N2 C2 H2B 118.8 . . ? C1 C2 H2B 118.8 . . ? N2 C3 C4 123.1(6) . . ? N2 C3 H3A 118.4 . . ? C4 C3 H3A 118.4 . . ? N1 C4 C3 120.0(5) . . ? N1 C4 C5 118.2(4) . . ? C3 C4 C5 121.9(5) . . ? N3 C5 C4 116.4(4) . . ? N3 C5 C6 123.8(5) . . ? C4 C5 C6 119.8(4) . . ? C5 C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C6 H6D 109.5 . . ? H6B C6 H6D 109.5 . . ? H6C C6 H6D 109.5 . . ? N4 C7 N5 111.9(5) . . ? N4 C7 S1 130.4(4) . . ? N5 C7 S1 117.7(4) . . ? N6 C8 C10 113.1(5) . . ? N6 C8 C9 129.6(5) . . ? C10 C8 C9 117.3(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N7 120.5(5) . . ? C11 C10 C8 118.7(5) . . ? N7 C10 C8 120.8(5) . . ? N8 C11 C10 117.6(5) . . ? N8 C11 H11A 121.2 . . ? C10 C11 H11A 121.2 . . ? C13 C12 N8 121.9(5) . . ? C13 C12 H12A 119.0 . . ? N8 C12 H12A 119.0 . . ? C12 C13 N7 116.8(5) . . ? C12 C13 H13A 121.6 . . ? N7 C13 H13A 121.6 . . ? C19 C14 C15 117.8(5) . . ? C19 C14 Sn1 119.1(4) . . ? C15 C14 Sn1 123.0(4) . . ? C16 C15 C14 120.9(5) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C17 C16 C15 120.4(5) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 119.7(5) . . ? C16 C17 H17A 120.1 . . ? C18 C17 H17A 120.1 . . ? C17 C18 C19 120.9(5) . . ? C17 C18 H18A 119.5 . . ? C19 C18 H18A 119.5 . . ? C18 C19 C14 120.3(5) . . ? C18 C19 H19A 119.9 . . ? C14 C19 H19A 119.9 . . ? C21 C20 C25 118.1(5) . . ? C21 C20 Sn1 120.6(4) . . ? C25 C20 Sn1 121.3(4) . . ? C20 C21 C22 122.4(6) . . ? C20 C21 H21A 118.8 . . ? C22 C21 H21A 118.8 . . ? C23 C22 C21 118.6(7) . . ? C23 C22 H22A 120.7 . . ? C21 C22 H22A 120.7 . . ? C22 C23 C24 120.9(6) . . ? C22 C23 H23A 119.6 . . ? C24 C23 H23A 119.6 . . ? C23 C24 C25 119.4(6) . . ? C23 C24 H24A 120.3 . . ? C25 C24 H24A 120.3 . . ? C24 C25 C20 120.5(6) . . ? C24 C25 H25A 119.8 . . ? C20 C25 H25A 119.8 . . ? C27 C26 H26A 109.5 . . ? C27 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C27 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O1 C27 O2 119.7(5) . . ? O1 C27 C26 122.1(6) . . ? O2 C27 C26 118.2(6) . . ? O1 C27 Sn1 63.6(3) . . ? O2 C27 Sn1 56.1(3) . . ? C26 C27 Sn1 174.3(6) . . ? C27 O1 Sn1 88.6(4) . . ? C27 O2 Sn1 95.6(3) . . ? C28 N9 C29 121.2(8) . . ? C28 N9 C30 120.5(7) . . ? C29 N9 C30 118.1(7) . . ? O3 C28 N9 126.9(8) . . ? O3 C28 H28A 116.5 . . ? N9 C28 H28A 116.5 . . ? N9 C29 H29A 109.5 . . ? N9 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N9 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N9 C30 H30A 109.5 . . ? N9 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N9 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C20 Sn1 S1 C7 -84.3(2) . . . . ? C14 Sn1 S1 C7 91.1(2) . . . . ? O2 Sn1 S1 C7 -176.4(2) . . . . ? N3 Sn1 S1 C7 2.1(2) . . . . ? O1 Sn1 S1 C7 -177.9(2) . . . . ? N1 Sn1 S1 C7 6.9(2) . . . . ? C27 Sn1 S1 C7 -176.5(2) . . . . ? C20 Sn1 N1 C1 -91.5(4) . . . . ? C14 Sn1 N1 C1 83.1(4) . . . . ? O2 Sn1 N1 C1 -3.2(5) . . . . ? N3 Sn1 N1 C1 177.1(4) . . . . ? O1 Sn1 N1 C1 -4.7(4) . . . . ? S1 Sn1 N1 C1 172.1(4) . . . . ? C27 Sn1 N1 C1 -4.6(4) . . . . ? C20 Sn1 N1 C4 93.0(4) . . . . ? C14 Sn1 N1 C4 -92.4(4) . . . . ? O2 Sn1 N1 C4 -178.7(3) . . . . ? N3 Sn1 N1 C4 1.6(3) . . . . ? O1 Sn1 N1 C4 179.8(4) . . . . ? S1 Sn1 N1 C4 -3.4(4) . . . . ? C27 Sn1 N1 C4 179.9(3) . . . . ? C20 Sn1 N3 C5 -82.2(4) . . . . ? C14 Sn1 N3 C5 83.1(4) . . . . ? O2 Sn1 N3 C5 -177.7(4) . . . . ? O1 Sn1 N3 C5 -1.5(5) . . . . ? N1 Sn1 N3 C5 1.8(4) . . . . ? S1 Sn1 N3 C5 178.5(4) . . . . ? C27 Sn1 N3 C5 -18(2) . . . . ? C20 Sn1 N3 N4 95.1(4) . . . . ? C14 Sn1 N3 N4 -99.6(3) . . . . ? O2 Sn1 N3 N4 -0.3(6) . . . . ? O1 Sn1 N3 N4 175.8(3) . . . . ? N1 Sn1 N3 N4 179.2(4) . . . . ? S1 Sn1 N3 N4 -4.1(3) . . . . ? C27 Sn1 N3 N4 159.4(16) . . . . ? C5 N3 N4 C7 -177.6(4) . . . . ? Sn1 N3 N4 C7 4.8(5) . . . . ? C7 N5 N6 C8 -177.1(5) . . . . ? C4 N1 C1 C2 0.1(8) . . . . ? Sn1 N1 C1 C2 -175.4(4) . . . . ? C3 N2 C2 C1 -1.5(9) . . . . ? N1 C1 C2 N2 0.9(9) . . . . ? C2 N2 C3 C4 1.0(8) . . . . ? C1 N1 C4 C3 -0.6(7) . . . . ? Sn1 N1 C4 C3 175.4(4) . . . . ? C1 N1 C4 C5 179.6(4) . . . . ? Sn1 N1 C4 C5 -4.4(6) . . . . ? N2 C3 C4 N1 0.0(8) . . . . ? N2 C3 C4 C5 179.8(5) . . . . ? N4 N3 C5 C4 177.8(4) . . . . ? Sn1 N3 C5 C4 -4.7(6) . . . . ? N4 N3 C5 C6 -1.7(7) . . . . ? Sn1 N3 C5 C6 175.8(4) . . . . ? N1 C4 C5 N3 6.1(7) . . . . ? C3 C4 C5 N3 -173.8(5) . . . . ? N1 C4 C5 C6 -174.4(5) . . . . ? C3 C4 C5 C6 5.8(8) . . . . ? N3 N4 C7 N5 177.4(4) . . . . ? N3 N4 C7 S1 -2.4(7) . . . . ? N6 N5 C7 N4 -175.1(4) . . . . ? N6 N5 C7 S1 4.8(7) . . . . ? Sn1 S1 C7 N4 -0.8(5) . . . . ? Sn1 S1 C7 N5 179.4(4) . . . . ? N5 N6 C8 C10 -178.2(4) . . . . ? N5 N6 C8 C9 2.5(8) . . . . ? C13 N7 C10 C11 0.4(9) . . . . ? C13 N7 C10 C8 179.6(5) . . . . ? N6 C8 C10 C11 -164.9(5) . . . . ? C9 C8 C10 C11 14.5(7) . . . . ? N6 C8 C10 N7 16.0(7) . . . . ? C9 C8 C10 N7 -164.6(5) . . . . ? C12 N8 C11 C10 1.7(9) . . . . ? N7 C10 C11 N8 -1.7(8) . . . . ? C8 C10 C11 N8 179.1(5) . . . . ? C11 N8 C12 C13 -0.5(10) . . . . ? N8 C12 C13 N7 -0.8(9) . . . . ? C10 N7 C13 C12 0.8(9) . . . . ? C20 Sn1 C14 C19 128.5(7) . . . . ? O2 Sn1 C14 C19 -115.9(4) . . . . ? N3 Sn1 C14 C19 40.6(4) . . . . ? O1 Sn1 C14 C19 -171.6(4) . . . . ? N1 Sn1 C14 C19 106.8(4) . . . . ? S1 Sn1 C14 C19 -33.6(4) . . . . ? C27 Sn1 C14 C19 -144.1(4) . . . . ? C20 Sn1 C14 C15 -55.8(9) . . . . ? O2 Sn1 C14 C15 59.8(4) . . . . ? N3 Sn1 C14 C15 -143.7(4) . . . . ? O1 Sn1 C14 C15 4.1(4) . . . . ? N1 Sn1 C14 C15 -77.5(4) . . . . ? S1 Sn1 C14 C15 142.0(4) . . . . ? C27 Sn1 C14 C15 31.6(4) . . . . ? C19 C14 C15 C16 0.6(8) . . . . ? Sn1 C14 C15 C16 -175.1(4) . . . . ? C14 C15 C16 C17 -0.3(9) . . . . ? C15 C16 C17 C18 0.0(9) . . . . ? C16 C17 C18 C19 -0.2(9) . . . . ? C17 C18 C19 C14 0.6(8) . . . . ? C15 C14 C19 C18 -0.8(8) . . . . ? Sn1 C14 C19 C18 175.1(4) . . . . ? C14 Sn1 C20 C21 -142.5(7) . . . . ? O2 Sn1 C20 C21 102.0(4) . . . . ? N3 Sn1 C20 C21 -54.3(4) . . . . ? O1 Sn1 C20 C21 157.5(4) . . . . ? N1 Sn1 C20 C21 -120.9(4) . . . . ? S1 Sn1 C20 C21 19.6(4) . . . . ? C27 Sn1 C20 C21 130.0(4) . . . . ? C14 Sn1 C20 C25 39.2(10) . . . . ? O2 Sn1 C20 C25 -76.4(4) . . . . ? N3 Sn1 C20 C25 127.3(4) . . . . ? O1 Sn1 C20 C25 -20.8(4) . . . . ? N1 Sn1 C20 C25 60.8(4) . . . . ? S1 Sn1 C20 C25 -158.8(4) . . . . ? C27 Sn1 C20 C25 -48.4(4) . . . . ? C25 C20 C21 C22 0.9(8) . . . . ? Sn1 C20 C21 C22 -177.5(4) . . . . ? C20 C21 C22 C23 -2.1(9) . . . . ? C21 C22 C23 C24 2.1(9) . . . . ? C22 C23 C24 C25 -1.0(10) . . . . ? C23 C24 C25 C20 -0.2(9) . . . . ? C21 C20 C25 C24 0.3(8) . . . . ? Sn1 C20 C25 C24 178.7(4) . . . . ? C20 Sn1 C27 O1 83.2(3) . . . . ? C14 Sn1 C27 O1 -82.1(3) . . . . ? O2 Sn1 C27 O1 -178.2(5) . . . . ? N3 Sn1 C27 O1 18.9(19) . . . . ? N1 Sn1 C27 O1 -0.2(3) . . . . ? S1 Sn1 C27 O1 -178.0(3) . . . . ? C20 Sn1 C27 O2 -98.5(3) . . . . ? C14 Sn1 C27 O2 96.1(3) . . . . ? N3 Sn1 C27 O2 -162.9(16) . . . . ? O1 Sn1 C27 O2 178.2(5) . . . . ? N1 Sn1 C27 O2 178.0(3) . . . . ? S1 Sn1 C27 O2 0.3(3) . . . . ? C20 Sn1 C27 C26 -93(4) . . . . ? C14 Sn1 C27 C26 102(4) . . . . ? O2 Sn1 C27 C26 6(4) . . . . ? N3 Sn1 C27 C26 -157(4) . . . . ? O1 Sn1 C27 C26 -176(4) . . . . ? N1 Sn1 C27 C26 -176(4) . . . . ? S1 Sn1 C27 C26 6(4) . . . . ? O2 C27 O1 Sn1 -1.7(5) . . . . ? C26 C27 O1 Sn1 179.6(5) . . . . ? C20 Sn1 O1 C27 -95.6(3) . . . . ? C14 Sn1 O1 C27 97.2(3) . . . . ? O2 Sn1 O1 C27 1.0(3) . . . . ? N3 Sn1 O1 C27 -177.1(3) . . . . ? N1 Sn1 O1 C27 179.8(3) . . . . ? S1 Sn1 O1 C27 2.8(4) . . . . ? O1 C27 O2 Sn1 1.8(5) . . . . ? C26 C27 O2 Sn1 -179.4(4) . . . . ? C20 Sn1 O2 C27 82.0(3) . . . . ? C14 Sn1 O2 C27 -84.8(3) . . . . ? N3 Sn1 O2 C27 176.5(3) . . . . ? O1 Sn1 O2 C27 -1.0(3) . . . . ? N1 Sn1 O2 C27 -2.8(4) . . . . ? S1 Sn1 O2 C27 -179.8(3) . . . . ? C29 N9 C28 O3 3.8(12) . . . . ? C30 N9 C28 O3 179.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.751 _refine_diff_density_min -0.719 _refine_diff_density_rms 0.103 _database_code_depnum_ccdc_archive 'CCDC 934514'