#Copyright The Royal Society of Chemistry, 1998 data_95js01 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 N O2 S Sn' _chemical_formula_weight 356.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Sn' 'Sn' -0.6537 1.4246 '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' 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21/b 21/c 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 23.455(4) _cell_length_b 11.1793(14) _cell_length_c 10.3097(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2703.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.7 _cell_measurement_theta_max 12.1 _exptl_crystal_description prism _exptl_crystal_colour 'amber' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.749 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 2.034 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.5805 _exptl_absorpt_correction_T_max 0.7501 _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 'CAD4 Enraf Nonius' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3919 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0931 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 29.94 _reflns_number_total 3919 _reflns_number_gt 2173 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4/SDP Software (Enraf Nonius, 1989)' _computing_cell_refinement 'CAD4/SDP Software (Enraf Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1997)' _computing_publication_material 'SHELXL-97 (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^)+(0.0249P)^2^+1.8627P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment isotropically _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00012(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3919 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1268 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn Sn 0.462523(16) 0.66796(4) 0.18835(3) 0.02996(12) Uani 1 d . . . S S 0.39957(7) 0.83321(16) 0.23999(13) 0.0398(4) Uani 1 d . . . O1 O 0.46682(17) 0.7702(4) 0.0033(4) 0.0383(10) Uani 1 d . . . O2 O 0.43188(18) 0.9098(4) -0.1263(4) 0.0380(10) Uani 1 d . . . N1 N 0.3051(2) 1.0119(5) 0.2578(5) 0.0494(15) Uani 1 d . . . C1 C 0.4336(2) 0.8564(5) -0.0176(5) 0.0286(13) Uani 1 d . . . C2 C 0.3949(2) 0.9008(5) 0.0882(5) 0.0259(12) Uani 1 d . . . C3 C 0.3598(3) 0.9931(6) 0.0592(6) 0.0343(14) Uani 1 d . . . C4 C 0.3181(2) 1.0559(5) 0.1390(6) 0.0314(13) Uani 1 d . . . C5 C 0.2937(3) 1.1579(7) 0.0928(7) 0.0449(16) Uani 1 d . . . C6 C 0.2565(3) 1.2212(8) 0.1696(9) 0.062(2) Uani 1 d . . . C7 C 0.2423(3) 1.1790(8) 0.2884(8) 0.062(2) Uani 1 d . . . C8 C 0.2674(3) 1.0744(8) 0.3283(7) 0.059(2) Uani 1 d . . . C11 C 0.5507(3) 0.6827(8) 0.2370(7) 0.0422(17) Uani 1 d . . . C12 C 0.5856(4) 0.7600(10) 0.1497(8) 0.063(2) Uani 1 d . . . C21 C 0.4286(3) 0.5171(7) 0.0888(6) 0.0457(17) Uani 1 d . . . C22 C 0.3648(4) 0.5051(12) 0.0985(12) 0.079(3) Uani 1 d . . . H3 H 0.361(2) 1.017(5) -0.028(5) 0.033(16) Uiso 1 d . . . H5 H 0.304(2) 1.190(5) 0.019(5) 0.024(15) Uiso 1 d . . . H6 H 0.235(3) 1.292(6) 0.137(6) 0.07(2) Uiso 1 d . . . H7 H 0.219(3) 1.228(6) 0.354(6) 0.06(2) Uiso 1 d . . . H8 H 0.260(2) 1.044(5) 0.405(5) 0.040(19) Uiso 1 d . . . H11A H 0.552(3) 0.731(8) 0.306(8) 0.10(3) Uiso 1 d . . . H11B H 0.560(3) 0.612(7) 0.250(8) 0.08(3) Uiso 1 d . . . H12A H 0.584(3) 0.742(7) 0.063(7) 0.07(2) Uiso 1 d . . . H12B H 0.628(3) 0.765(8) 0.182(8) 0.10(3) Uiso 1 d . . . H12C H 0.569(3) 0.841(6) 0.117(7) 0.06(2) Uiso 1 d . . . H21A H 0.436(3) 0.525(6) -0.006(7) 0.08(2) Uiso 1 d . . . H21B H 0.451(2) 0.456(5) 0.128(5) 0.032(17) Uiso 1 d . . . H22A H 0.347(4) 0.507(9) 0.182(9) 0.13(4) Uiso 1 d . . . H22B H 0.357(3) 0.438(7) 0.049(8) 0.08(3) Uiso 1 d . . . H22C H 0.344(3) 0.582(7) 0.048(7) 0.07(3) 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 Sn 0.0301(2) 0.02969(19) 0.03012(17) 0.0008(2) 0.0023(2) 0.0005(2) S 0.0476(9) 0.0413(9) 0.0304(6) 0.0034(8) 0.0095(7) 0.0145(9) O1 0.039(2) 0.040(2) 0.0358(19) 0.0055(19) 0.009(2) 0.015(2) O2 0.050(3) 0.033(2) 0.0304(19) 0.0022(19) 0.006(2) 0.008(2) N1 0.043(3) 0.053(4) 0.052(3) 0.002(3) 0.011(3) 0.007(3) C1 0.032(3) 0.029(3) 0.026(2) 0.000(2) 0.001(2) -0.002(3) C2 0.023(3) 0.024(3) 0.031(3) -0.003(2) 0.001(2) -0.002(2) C3 0.035(3) 0.034(3) 0.034(3) 0.000(3) -0.002(3) 0.000(3) C4 0.022(3) 0.033(3) 0.039(3) -0.001(3) -0.003(3) -0.002(3) C5 0.038(4) 0.047(4) 0.050(4) 0.006(4) 0.008(3) 0.009(4) C6 0.040(4) 0.061(5) 0.084(6) -0.003(5) -0.001(4) 0.023(4) C7 0.028(4) 0.082(6) 0.075(5) -0.027(5) 0.000(4) 0.019(4) C8 0.039(4) 0.092(7) 0.046(4) 0.006(5) 0.008(3) 0.012(4) C11 0.031(4) 0.052(5) 0.044(3) 0.009(4) -0.005(3) -0.006(4) C12 0.036(4) 0.093(7) 0.061(5) 0.017(5) -0.004(4) -0.021(5) C21 0.054(5) 0.046(5) 0.037(3) -0.009(3) -0.001(3) -0.001(4) C22 0.055(6) 0.086(8) 0.098(8) -0.037(8) -0.006(6) -0.009(6) _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 C21 2.128(7) . y Sn C11 2.134(6) . y Sn O2 2.219(4) 8_576 y Sn O1 2.226(4) . y Sn S 2.4242(16) . y S C2 1.742(5) . y O1 C1 1.258(6) . y O2 C1 1.271(6) . y O2 Sn 2.219(4) 8_575 y N1 C8 1.341(9) . ? N1 C4 1.354(7) . ? C1 C2 1.503(7) . y C2 C3 1.354(8) . y C3 C4 1.459(8) . y C3 H3 0.94(5) . ? C4 C5 1.362(8) . ? C5 C6 1.374(9) . ? C5 H5 0.88(5) . ? C6 C7 1.355(11) . ? C6 H6 1.00(7) . ? C7 C8 1.372(11) . ? C7 H7 1.03(6) . ? C8 H8 0.87(5) . ? C11 C12 1.493(10) . y C11 H11A 0.89(8) . ? C11 H11B 0.83(8) . ? C12 H12A 0.91(7) . ? C12 H12B 1.04(8) . ? C12 H12C 1.05(7) . ? C21 C22 1.506(11) . y C21 H21A 1.00(7) . ? C21 H21B 0.95(5) . ? C22 H22A 0.96(9) . ? C22 H22B 0.92(8) . ? C22 H22C 1.11(7) . ? 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 C21 Sn C11 122.5(3) . . y C21 Sn O2 89.1(2) . 8_576 y C11 Sn O2 98.2(2) . 8_576 y C21 Sn O1 90.6(2) . . y C11 Sn O1 96.8(2) . . y O2 Sn O1 162.51(15) 8_576 . y C21 Sn S 118.8(2) . . y C11 Sn S 118.7(3) . . y O2 Sn S 84.96(12) 8_576 . y O1 Sn S 79.89(10) . . y C2 S Sn 99.89(18) . . ? C1 O1 Sn 120.8(3) . . ? C1 O2 Sn 124.4(4) . 8_575 ? C8 N1 C4 116.7(6) . . ? O1 C1 O2 122.0(5) . . y O1 C1 C2 120.2(5) . . y O2 C1 C2 117.8(5) . . y C3 C2 C1 117.3(5) . . y C3 C2 S 124.6(4) . . y C1 C2 S 118.1(4) . . y C2 C3 C4 130.6(6) . . y C2 C3 H3 114(3) . . ? C4 C3 H3 115(3) . . ? N1 C4 C5 121.7(6) . . y N1 C4 C3 119.1(6) . . y C5 C4 C3 119.1(6) . . y C4 C5 C6 119.7(7) . . ? C4 C5 H5 122(4) . . ? C6 C5 H5 118(4) . . ? C7 C6 C5 119.8(8) . . ? C7 C6 H6 117(4) . . ? C5 C6 H6 123(4) . . ? C6 C7 C8 117.6(7) . . ? C6 C7 H7 123(4) . . ? C8 C7 H7 119(4) . . ? N1 C8 C7 124.3(7) . . ? N1 C8 H8 114(4) . . ? C7 C8 H8 121(4) . . ? C12 C11 Sn 115.8(5) . . ? C12 C11 H11A 96(5) . . ? Sn C11 H11A 106(5) . . ? C12 C11 H11B 120(5) . . ? Sn C11 H11B 102(5) . . ? H11A C11 H11B 116(7) . . ? C11 C12 H12A 116(5) . . ? C11 C12 H12B 111(5) . . ? H12A C12 H12B 111(6) . . ? C11 C12 H12C 119(4) . . ? H12A C12 H12C 82(5) . . ? H12B C12 H12C 114(6) . . ? C22 C21 Sn 114.2(6) . . ? C22 C21 H21A 104(4) . . ? Sn C21 H21A 110(4) . . ? C22 C21 H21B 117(3) . . ? Sn C21 H21B 99(3) . . ? H21A C21 H21B 113(5) . . ? C21 C22 H22A 120(6) . . ? C21 C22 H22B 103(5) . . ? H22A C22 H22B 115(8) . . ? C21 C22 H22C 110(4) . . ? H22A C22 H22C 102(7) . . ? H22B C22 H22C 106(6) . . ? 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 C21 Sn S C2 -76.9(3) . . . . ? C11 Sn S C2 100.4(3) . . . . ? O2 Sn S C2 -163.0(2) 8_576 . . . ? O1 Sn S C2 8.2(2) . . . . ? C21 Sn O1 C1 109.5(5) . . . . ? C11 Sn O1 C1 -127.7(5) . . . . ? O2 Sn O1 C1 20.7(8) 8_576 . . . ? S Sn O1 C1 -9.7(4) . . . . ? Sn O1 C1 O2 -174.0(4) . . . . ? Sn O1 C1 C2 7.0(7) . . . . ? Sn O2 C1 O1 20.9(8) 8_575 . . . ? Sn O2 C1 C2 -160.1(3) 8_575 . . . ? O1 C1 C2 C3 -179.5(5) . . . . ? O2 C1 C2 C3 1.5(8) . . . . ? O1 C1 C2 S 2.3(7) . . . . ? O2 C1 C2 S -176.7(4) . . . . ? Sn S C2 C3 173.4(5) . . . . ? Sn S C2 C1 -8.5(4) . . . . ? C1 C2 C3 C4 -179.8(6) . . . . ? S C2 C3 C4 -1.7(10) . . . . ? C8 N1 C4 C5 -0.6(9) . . . . ? C8 N1 C4 C3 178.6(6) . . . . ? C2 C3 C4 N1 -8.7(10) . . . . ? C2 C3 C4 C5 170.5(6) . . . . ? N1 C4 C5 C6 2.5(10) . . . . ? C3 C4 C5 C6 -176.7(6) . . . . ? C4 C5 C6 C7 -3.0(11) . . . . ? C5 C6 C7 C8 1.7(12) . . . . ? C4 N1 C8 C7 -0.8(11) . . . . ? C6 C7 C8 N1 0.3(13) . . . . ? C21 Sn C11 C12 100.6(7) . . . . ? O2 Sn C11 C12 -165.3(7) 8_576 . . . ? O1 Sn C11 C12 5.5(7) . . . . ? S Sn C11 C12 -76.6(7) . . . . ? C11 Sn C21 C22 162.5(7) . . . . ? O2 Sn C21 C22 63.5(7) 8_576 . . . ? O1 Sn C21 C22 -99.1(7) . . . . ? S Sn C21 C22 -20.3(8) . . . . ? _diffrn_reflns_theta_full 29.94 _refine_diff_density_max 0.789 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.142