# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1997 data_global # version 16-12-1999 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Dr. Jose S. Casas Fernandez' _publ_contact_author_address ; Departamento de Qu\'imica Inorg\'anica Facultade de Farmacia Universidade de Santiago de Compostela 15706 Santiago de Compostela Galicia, Spain ; _publ_contact_author_email qiscasas@usc.es _publ_contact_author_fax '0034 981 594636' _publ_contact_author_phone '0034 981 594912' _publ_contact_letter ; Dear Editor, Please consider this CIF submission as suplementary material of the paper recently submitted by air mail. Yours sincerely, J.S. Casas ; _publ_requested_journal 'J. Chem. Soc., Dalton Trans.' # 3. TITLE AND AUTHOR LIST _publ_section_title ; Diorganotin(IV) complexes of 2-formylimidazole thiosemicarbazone (H2ImTSC). Crystal and molecular structure of the free ligand and [SnMe2(ImTSC)] ; data_imh _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-forylimidazole thiosemicarbazone ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 N5 O0.50 S' _chemical_formula_weight 178.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 '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 7.7676(9) _cell_length_b 7.8401(9) _cell_length_c 15.873(2) _cell_angle_alpha 81.828(9) _cell_angle_beta 89.140(10) _cell_angle_gamma 61.146(9) _cell_volume 836.44(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 35 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 3.081 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.2594 _exptl_absorpt_correction_T_max 0.8612 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD4 Enraf-Nonius ' _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3637 _diffrn_reflns_av_R_equivalents 0.0798 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 5.64 _diffrn_reflns_theta_max 67.51 _reflns_number_total 2968 _reflns_number_gt 2870 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4-Express (Enraf-Nonius, 1995)' _computing_cell_refinement 'CAD4-Express (Enraf-Nonius, 1995)' _computing_data_reduction 'HELENA (Spek, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+0.2192P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens direct _refine_ls_hydrogen_treatment isotropic _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0190(19) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2968 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1365 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.32883(7) 0.35254(7) 0.63959(3) 0.0420(2) Uani 1 d . . . N1 N 0.0086(3) 0.5958(3) 0.71119(14) 0.0437(4) Uani 1 d . . . H1N1 H -0.017(5) 0.696(6) 0.668(2) 0.072(9) Uiso 1 d . . . H2N1 H -0.058(4) 0.614(4) 0.7518(19) 0.047(7) Uiso 1 d . . . N2 N 0.1929(3) 0.2848(3) 0.78607(12) 0.0408(4) Uani 1 d . . . H2 H 0.301(4) 0.172(5) 0.7945(19) 0.057(7) Uiso 1 d . . . N3 N 0.0649(2) 0.3373(2) 0.84950(11) 0.0386(4) Uani 1 d . . . N5 N 0.0114(3) 0.1517(3) 1.06326(12) 0.0457(4) Uani 1 d . . . N4 N -0.1894(3) 0.4356(3) 0.98311(13) 0.0401(4) Uani 1 d . . . H4 H -0.227(4) 0.512(4) 0.9435(18) 0.036(7) Uiso 1 d . . . C1 C 0.1641(3) 0.4193(3) 0.71625(13) 0.0343(4) Uani 1 d . . . C2 C 0.1102(3) 0.2130(3) 0.91873(14) 0.0397(5) Uani 1 d . . . H2 H 0.227(4) 0.093(5) 0.9267(19) 0.054(7) Uiso 1 d . . . C3 C -0.0186(3) 0.2631(3) 0.98779(13) 0.0368(4) Uani 1 d . . . C5 C -0.1463(4) 0.2567(4) 1.10768(15) 0.0491(5) Uani 1 d . . . H5 H -0.162(5) 0.211(5) 1.168(2) 0.064(8) Uiso 1 d . . . C4 C -0.2719(3) 0.4335(4) 1.05877(15) 0.0466(5) Uani 1 d . . . H4 H -0.391(4) 0.539(5) 1.0709(18) 0.052(7) Uiso 1 d . . . S11 S 0.59345(7) -0.17363(7) 0.82173(3) 0.0402(2) Uani 1 d . . . N11 N 0.5417(3) -0.4265(3) 0.74570(14) 0.0459(5) Uani 1 d . . . H1N2 H 0.584(4) -0.505(4) 0.7888(18) 0.039(6) Uiso 1 d . . . H2N2 H 0.507(4) -0.461(5) 0.701(2) 0.057(8) Uiso 1 d . . . N12 N 0.4426(3) -0.1218(3) 0.66699(12) 0.0420(4) Uani 1 d . . . H12 H 0.430(4) -0.012(4) 0.6622(17) 0.044(7) Uiso 1 d . . . N13 N 0.3819(2) -0.1801(3) 0.60149(11) 0.0382(4) Uani 1 d . . . N15 N 0.1490(3) 0.0054(3) 0.39029(12) 0.0456(4) Uani 1 d . . . N14 N 0.2303(3) -0.2822(3) 0.47099(13) 0.0410(4) Uani 1 d . . . H14 H 0.261(4) -0.369(4) 0.5156(18) 0.043(6) Uiso 1 d . . . C11 C 0.5229(3) -0.2491(3) 0.74063(13) 0.0352(4) Uani 1 d . . . C12 C 0.2987(3) -0.0524(3) 0.53434(14) 0.0387(5) Uani 1 d . . . H12 H 0.278(4) 0.083(4) 0.5273(18) 0.050(7) Uiso 1 d . . . C13 C 0.2262(3) -0.1062(3) 0.46540(13) 0.0361(4) Uani 1 d . . . C15 C 0.1036(4) -0.1065(4) 0.34611(15) 0.0520(6) Uani 1 d . . . H15 H 0.056(4) -0.058(5) 0.286(2) 0.067(9) Uiso 1 d . . . C14 C 0.1511(3) -0.2825(4) 0.39510(16) 0.0501(6) Uani 1 d . . . H14 H 0.137(4) -0.399(4) 0.3882(18) 0.052(7) Uiso 1 d . . . O1W O 0.3369(3) 0.7930(3) 0.14163(15) 0.0591(5) Uani 1 d . . . H1W H 0.364(6) 0.840(7) 0.182(3) 0.104(14) Uiso 1 d . . . H2W H 0.240(7) 0.897(7) 0.113(3) 0.098(13) Uiso 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 S1 0.0465(3) 0.0303(3) 0.0470(4) -0.0060(2) 0.0111(2) -0.0171(2) N1 0.0407(9) 0.0302(9) 0.0444(11) 0.0015(8) 0.0039(8) -0.0067(7) N2 0.0357(9) 0.0281(9) 0.0454(10) -0.0001(7) 0.0042(7) -0.0066(7) N3 0.0361(8) 0.0329(9) 0.0411(10) -0.0034(7) 0.0017(7) -0.0129(7) N5 0.0491(10) 0.0381(10) 0.0396(10) 0.0026(8) -0.0045(7) -0.0150(8) N4 0.0387(9) 0.0338(10) 0.0375(10) -0.0013(8) -0.0056(7) -0.0105(7) C1 0.0328(9) 0.0279(9) 0.0406(10) -0.0046(8) -0.0022(7) -0.0137(7) C2 0.0388(10) 0.0306(10) 0.0419(11) 0.0001(9) -0.0024(8) -0.0121(9) C3 0.0380(10) 0.0295(9) 0.0390(11) -0.0017(8) -0.0058(8) -0.0141(8) C5 0.0555(13) 0.0541(14) 0.0345(11) -0.0029(10) 0.0008(9) -0.0251(11) C4 0.0427(11) 0.0457(13) 0.0452(12) -0.0115(10) 0.0016(9) -0.0155(10) S11 0.0408(3) 0.0291(3) 0.0398(4) -0.0045(2) -0.0073(2) -0.0082(2) N11 0.0600(12) 0.0288(9) 0.0421(11) 0.0005(9) -0.0078(9) -0.0175(8) N12 0.0542(10) 0.0287(9) 0.0417(10) -0.0029(7) -0.0088(8) -0.0193(8) N13 0.0415(9) 0.0317(9) 0.0379(9) -0.0048(7) -0.0026(7) -0.0149(7) N15 0.0476(10) 0.0401(10) 0.0378(10) 0.0011(8) -0.0023(7) -0.0140(8) N14 0.0451(9) 0.0346(9) 0.0398(10) -0.0032(8) -0.0014(7) -0.0170(8) C11 0.0292(9) 0.0271(9) 0.0405(10) -0.0061(8) 0.0017(7) -0.0064(7) C12 0.0411(10) 0.0298(10) 0.0405(11) -0.0028(8) 0.0012(8) -0.0141(8) C13 0.0334(9) 0.0325(10) 0.0352(10) -0.0039(8) 0.0030(7) -0.0107(8) C15 0.0511(12) 0.0566(15) 0.0367(12) -0.0067(11) -0.0053(10) -0.0169(11) C14 0.0486(12) 0.0525(14) 0.0496(13) -0.0171(11) 0.0009(10) -0.0225(11) O1W 0.0606(11) 0.0318(9) 0.0713(12) 0.0007(8) -0.0181(9) -0.0135(8) _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 S1 C1 1.697(2) . ? N1 C1 1.318(3) . ? N2 C1 1.356(3) . ? N2 N3 1.365(3) . ? N3 C2 1.287(3) . ? N5 C3 1.329(3) . ? N5 C5 1.357(3) . ? N4 C4 1.355(3) . ? N4 C3 1.355(3) . ? C2 C3 1.438(3) . ? C5 C4 1.374(4) . ? S11 C11 1.691(2) . ? N11 C11 1.317(3) . ? N12 C11 1.357(3) . ? N12 N13 1.368(2) . ? N13 C12 1.284(3) . ? N15 C13 1.329(3) . ? N15 C15 1.366(3) . ? N14 C13 1.354(3) . ? N14 C14 1.362(3) . ? C12 C13 1.439(3) . ? C15 C14 1.363(4) . ? 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 C1 N2 N3 119.48(17) . . ? C2 N3 N2 117.34(17) . . ? C3 N5 C5 105.51(19) . . ? C4 N4 C3 107.1(2) . . ? N1 C1 N2 118.20(19) . . ? N1 C1 S1 123.20(17) . . ? N2 C1 S1 118.60(15) . . ? N3 C2 C3 119.31(18) . . ? N5 C3 N4 111.24(19) . . ? N5 C3 C2 125.87(19) . . ? N4 C3 C2 122.89(19) . . ? N5 C5 C4 109.9(2) . . ? N4 C4 C5 106.3(2) . . ? C11 N12 N13 119.38(17) . . ? C12 N13 N12 117.42(17) . . ? C13 N15 C15 104.64(19) . . ? C13 N14 C14 106.4(2) . . ? N11 C11 N12 118.23(19) . . ? N11 C11 S11 122.92(17) . . ? N12 C11 S11 118.86(15) . . ? N13 C12 C13 118.94(18) . . ? N15 C13 N14 112.07(19) . . ? N15 C13 C12 125.57(19) . . ? N14 C13 C12 122.37(19) . . ? C14 C15 N15 110.3(2) . . ? N14 C14 C15 106.6(2) . . ? 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 N1 H1N1 N15 0.91(4) 2.12(4) 2.967(3) 155(3) 2_566 N1 H2N1 S11 0.81(3) 2.72(3) 3.443(2) 150(3) 1_465 N2 H2 S11 0.87(3) 2.54(3) 3.4060(19) 174(3) . N4 H4 S11 0.75(3) 2.68(3) 3.421(2) 170(2) 1_465 N11 H1N2 O1W 0.80(3) 2.16(3) 2.884(3) 150(2) 2_656 N11 H2N2 S1 0.89(3) 2.72(3) 3.500(2) 148(3) 1_545 N12 H12 S1 0.81(3) 2.54(3) 3.3439(19) 170(2) . N14 H14 S1 0.86(3) 2.57(3) 3.423(2) 173(2) 1_545 O1W H1W S11 0.85(5) 2.78(5) 3.406(2) 131(4) 2_666 O1W H2W N5 0.87(5) 1.98(5) 2.844(3) 171(4) 1_564 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 67.51 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.487 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.080 #===END data_c2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-forylimidazole thiosemicarbazonato)dimethyltin(IV) ethanol solvate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H17 N5 O S Sn' _chemical_formula_weight 362.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sn' 'Sn' -0.6537 1.4246 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 22.920(8) _cell_length_b 6.3651(7) _cell_length_c 10.488(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.655(16) _cell_angle_gamma 90.00 _cell_volume 1498.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 14 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 1.838 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Enraf Nonius CAD4' _diffrn_measurement_method 'omegha/2theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2465 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 29.95 _reflns_number_total 2350 _reflns_number_gt 2213 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4-Software (Enraf Nonius, 1989)' _computing_cell_refinement 'CAD4-Software (Enraf Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.9831P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(13) _refine_ls_number_reflns 2350 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn Sn 0.808397(12) 0.75758(19) 0.73165(3) 0.03599(12) Uani 1 d . . . S S 0.83477(10) 0.8556(5) 0.50342(15) 0.0653(6) Uani 1 d . . . C1 C 0.8911(3) 0.9708(12) 0.6122(5) 0.0428(12) Uani 1 d . . . N1 N 0.9345(3) 1.0834(13) 0.5784(5) 0.0533(14) Uani 1 d . . . H1A H 0.9608 1.1432 0.6373 0.064 Uiso 1 calc R . . H1B H 0.9362 1.0964 0.4976 0.064 Uiso 1 calc R . . N2 N 0.8859(2) 0.9442(10) 0.7363(4) 0.0387(10) Uani 1 d . . . N3 N 0.9295(2) 1.0422(12) 0.8299(5) 0.0486(13) Uani 1 d . . . N4 N 0.8283(2) 0.8318(11) 0.9383(4) 0.0428(11) Uani 1 d . . . N5 N 0.8713(3) 0.9815(12) 1.1269(4) 0.0500(13) Uani 1 d . . . C2 C 0.9221(3) 1.0399(15) 0.9474(6) 0.0513(17) Uani 1 d . . . H2 H 0.9522 1.1038 1.0077 0.05(2) Uiso 1 calc R . . C3 C 0.8736(3) 0.9523(12) 1.0005(5) 0.0418(12) Uani 1 d . . . C4 C 0.8239(3) 0.8741(14) 1.1442(6) 0.0503(15) Uani 1 d . . . H4 H 0.8113 0.8631 1.2229 0.05(3) Uiso 1 calc R . . C5 C 0.7959(3) 0.782(2) 1.0301(6) 0.0514(18) Uani 1 d . . . H5 H 0.7615 0.7002 1.0175 0.09(4) Uiso 1 calc R . . C6 C 0.8268(4) 0.4303(13) 0.7382(9) 0.0574(17) Uani 1 d . . . H6A H 0.7921 0.3552 0.6948 0.086 Uiso 1 calc R . . H6B H 0.8373 0.3854 0.8273 0.086 Uiso 1 calc R . . H6C H 0.8593 0.4025 0.6956 0.086 Uiso 1 calc R . . C7 C 0.7200(3) 0.8773(14) 0.6942(8) 0.0547(16) Uani 1 d . . . H7A H 0.6992 0.8293 0.6106 0.082 Uiso 1 calc R . . H7B H 0.7212 1.0281 0.6949 0.082 Uiso 1 calc R . . H7C H 0.6998 0.8288 0.7603 0.082 Uiso 1 calc R . . O O 0.0549(2) 0.2257(14) 0.6866(5) 0.0570(19) Uani 1 d . . . H10 H 0.077(5) 0.11(2) 0.721(11) 0.068 Uiso 1 d . . . C21 C 0.0623(6) 0.440(3) 0.720(2) 0.143(6) Uani 1 d . . . H21A H 0.0864 0.4447 0.8076 0.171 Uiso 1 calc R . . H21B H 0.0863 0.5004 0.6632 0.171 Uiso 1 calc R . . C22 C 0.0165(6) 0.571(3) 0.719(2) 0.143(6) Uani 1 d . . . H22A H 0.0314 0.7086 0.7458 0.214 Uiso 1 calc R . . H22B H -0.0076 0.5207 0.7773 0.214 Uiso 1 calc R . . H22C H -0.0072 0.5789 0.6322 0.214 Uiso 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 Sn 0.03704(17) 0.03525(17) 0.03560(16) -0.00206(19) 0.00719(11) -0.0004(2) S 0.0752(11) 0.0870(14) 0.0338(6) -0.0083(8) 0.0115(7) -0.0338(11) C1 0.045(3) 0.047(3) 0.039(2) -0.001(2) 0.016(2) -0.001(3) N1 0.050(3) 0.071(4) 0.043(2) -0.003(3) 0.018(2) -0.016(3) N2 0.033(2) 0.048(3) 0.0360(19) -0.0043(19) 0.0096(16) -0.005(2) N3 0.034(2) 0.069(4) 0.043(2) -0.008(3) 0.0091(18) -0.012(3) N4 0.046(2) 0.050(3) 0.0330(18) -0.0004(18) 0.0098(17) -0.003(2) N5 0.056(3) 0.060(3) 0.032(2) -0.004(2) 0.0055(19) -0.001(3) C2 0.036(3) 0.078(5) 0.040(2) -0.009(3) 0.007(2) -0.012(3) C3 0.038(2) 0.050(3) 0.037(2) 0.002(2) 0.0063(19) 0.001(3) C4 0.054(3) 0.060(4) 0.040(2) 0.004(3) 0.018(2) -0.003(3) C5 0.058(3) 0.056(5) 0.044(2) 0.005(3) 0.020(2) -0.001(4) C6 0.053(3) 0.039(4) 0.082(5) -0.005(3) 0.020(3) 0.005(3) C7 0.041(3) 0.055(4) 0.065(4) 0.001(3) 0.001(3) 0.015(3) O 0.044(2) 0.075(6) 0.051(2) 0.004(3) 0.0094(17) 0.000(3) C21 0.074(5) 0.087(7) 0.251(17) -0.036(10) -0.006(8) 0.007(5) C22 0.074(5) 0.087(7) 0.251(17) -0.036(10) -0.006(8) 0.007(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 Sn C6 2.123(8) . ? Sn C7 2.125(7) . ? Sn N2 2.129(5) . ? Sn N4 2.174(5) . ? Sn S 2.659(2) . ? S C1 1.707(7) . ? C1 N1 1.329(8) . ? C1 N2 1.342(7) . ? N2 N3 1.398(7) . ? N3 C2 1.277(8) . ? N4 C3 1.349(8) . ? N4 C5 1.367(8) . ? N5 C4 1.328(9) . ? N5 C3 1.351(7) . ? C2 C3 1.451(8) . ? C4 C5 1.372(11) . ? O C21 1.41(2) . ? C21 C22 1.341(19) . ? 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 C6 Sn C7 122.2(4) . . ? C6 Sn N2 112.8(3) . . ? C7 Sn N2 124.3(3) . . ? C6 Sn N4 100.4(3) . . ? C7 Sn N4 96.1(3) . . ? N2 Sn N4 81.37(19) . . ? C6 Sn S 100.4(2) . . ? C7 Sn S 97.5(2) . . ? N2 Sn S 63.22(13) . . ? N4 Sn S 143.74(19) . . ? C1 S Sn 77.2(2) . . ? N1 C1 N2 123.0(6) . . ? N1 C1 S 123.9(4) . . ? N2 C1 S 113.0(5) . . ? C1 N2 N3 115.7(5) . . ? C1 N2 Sn 106.6(4) . . ? N3 N2 Sn 137.7(4) . . ? C2 N3 N2 117.2(5) . . ? C3 N4 C5 105.5(5) . . ? C3 N4 Sn 126.2(4) . . ? C5 N4 Sn 128.1(5) . . ? C4 N5 C3 105.0(5) . . ? N3 C2 C3 129.5(6) . . ? N4 C3 N5 111.9(5) . . ? N4 C3 C2 127.4(5) . . ? N5 C3 C2 120.6(6) . . ? N5 C4 C5 110.7(5) . . ? N4 C5 C4 106.8(7) . . ? C22 C21 O 123.1(14) . . ? 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 N1 H1A O 0.86 2.18 2.909(8) 142.5 1_665 N1 H1B O 0.86 2.15 2.980(8) 162.7 2_666 O H10 N5 0.94(14) 1.95(13) 2.787(9) 147(11) 2_647 _diffrn_measured_fraction_theta_max 0.499 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.499 _refine_diff_density_max 0.909 _refine_diff_density_min -1.010 _refine_diff_density_rms 0.154