Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name 'Sarah L. Hinchley' 'Peter Trickey' 'Heather E. Robertson' 'Bruce A. Smart' 'David W. H. Rankin' 'Dirk Leusser' 'Bernhard Walfort' 'Dietmar Stalke' 'Michael Buhl' 'Stephen J. Obrey' _publ_contact_author_name 'Prof David Rankin' _publ_contact_author_address ; Chemistry Department University of Edinburgh West Mains Road Edinburgh EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email 'D.W.H.RANKIN@ED.AC.UK' _journal_name_full 'J. Chem. Soc., Dalton Trans.' _publ_section_title ; Bis(tert-butyl)sulfurdiimide, S(NBut)2 and Tris(tert-butyl)sulfurtriimide, S(NBut)3: Molecular Structures by Gas-Phase Electron Diffraction, X-ray Crystallography and Ab Initio Calculations. ; data_diimid _database_code_CSD 191359 _ccdc_compound_id 'diimid' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H18 N2 S' _chemical_formula_weight 175.31 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' _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 5.9699(3) _cell_length_b 9.2877(4) _cell_length_c 9.9338(4) _cell_angle_alpha 72.5050(10) _cell_angle_beta 88.3380(10) _cell_angle_gamma 84.6610(10) _cell_volume 523.04(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8646 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 26.5 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 194 _exptl_absorpt_coefficient_mu 0.258 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'MULABS implemented in PLATON' _exptl_special_details ; Data collection was performed within two steps. A low angle batch (2 theta position -31 degrees)and a high angle batch (2 theta -80 degrees) with a detector/sample distance of 5 cm were collected.This strategy leads to a high redundancy at more than 97% completeness in average up to 2 theta104 degrees but to a relatively low degree of overlap for the two batches. Due to that the two batches were treated separately during all subsequent steps of data processing (absorption correction, merging) and were included in the refinements with two scaling factors. ; _diffrn_ambient_temperature 100(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 'Bruker Smart Apex with D8-Goniometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number '12299 (low angle batch), 25532 (high angle batch)' _diffrn_reflns_av_R_equivalents '0.0546 (low angle batch), 0.0666 (high angle batch)' _diffrn_reflns_av_sigmaI/netI '0.0135 (low angle batch), 0.0760 (high angle batch)' _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 52.41 _reflns_number_total 11808 _reflns_number_gt 8183 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.6' _computing_cell_refinement 'SAINT-NT V5/6.0' _computing_data_reduction 'SAINT-NT V5/6.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT V5.1' _computing_publication_material 'SHELXTL-NT V5.1' _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^)+(0.0490P)^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 11808 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_restrained_S_all 0.885 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.715985(17) 0.503895(11) 0.618879(10) 0.01672(3) Uani 1 1 d . . . N1 N 0.60238(5) 0.52422(3) 0.75439(3) 0.01597(5) Uani 1 1 d . . . N2 N 0.83880(6) 0.34924(4) 0.62851(3) 0.01854(5) Uani 1 1 d . . . C1 C 0.47917(6) 0.67352(4) 0.74662(4) 0.01535(5) Uani 1 1 d . . . C2 C 0.86979(6) 0.21474(4) 0.75400(4) 0.01633(5) Uani 1 1 d . . . C11 C 0.51656(9) 0.80082(5) 0.61105(4) 0.02350(7) Uani 1 1 d . . . H11 H 0.4637(15) 0.7799(11) 0.5243(10) 0.035 Uiso 1 1 d . . . H12 H 0.4442(15) 0.8947(11) 0.6158(10) 0.035 Uiso 1 1 d . . . H13 H 0.6705(16) 0.8194(11) 0.5968(10) 0.035 Uiso 1 1 d . . . C12 C 0.22957(7) 0.64762(5) 0.76201(6) 0.02402(7) Uani 1 1 d . . . H14 H 0.1768(16) 0.6178(11) 0.6836(10) 0.036 Uiso 1 1 d . . . H15 H 0.2053(15) 0.5671(10) 0.8496(10) 0.036 Uiso 1 1 d . . . H16 H 0.1443(16) 0.7378(11) 0.7677(10) 0.036 Uiso 1 1 d . . . C13 C 0.55936(8) 0.71647(5) 0.87290(4) 0.02164(7) Uani 1 1 d . . . H17 H 0.5305(15) 0.6418(10) 0.9568(10) 0.032 Uiso 1 1 d . . . H18 H 0.7180(15) 0.7279(10) 0.8701(10) 0.032 Uiso 1 1 d . . . H19 H 0.4834(16) 0.8094(10) 0.8776(10) 0.032 Uiso 1 1 d . . . C21 C 1.01145(9) 0.09519(5) 0.70331(6) 0.02567(8) Uani 1 1 d . . . H21 H 0.9385(16) 0.0717(11) 0.6249(10) 0.039 Uiso 1 1 d . . . H22 H 1.0404(16) -0.0006(11) 0.7834(10) 0.039 Uiso 1 1 d . . . H23 H 1.1622(16) 0.1341(11) 0.6617(10) 0.039 Uiso 1 1 d . . . C22 C 0.64298(7) 0.15702(5) 0.80907(5) 0.02121(6) Uani 1 1 d . . . H24 H 0.6674(15) 0.0650(10) 0.8862(9) 0.032 Uiso 1 1 d . . . H25 H 0.5666(16) 0.1286(10) 0.7358(9) 0.032 Uiso 1 1 d . . . H26 H 0.5523(15) 0.2328(11) 0.8430(10) 0.032 Uiso 1 1 d . . . C23 C 0.99610(8) 0.25225(5) 0.86943(5) 0.02231(7) Uani 1 1 d . . . H27 H 1.0282(15) 0.1629(10) 0.9445(10) 0.033 Uiso 1 1 d . . . H28 H 1.1331(15) 0.2942(10) 0.8362(10) 0.033 Uiso 1 1 d . . . H29 H 0.9120(15) 0.3208(10) 0.9088(10) 0.033 Uiso 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 S1 0.01929(4) 0.01593(4) 0.01469(4) -0.00504(2) 0.00199(2) 0.00068(3) N1 0.01864(11) 0.01362(10) 0.01545(9) -0.00490(7) 0.00150(8) 0.00089(8) N2 0.02015(12) 0.01799(12) 0.01804(11) -0.00745(9) 0.00316(9) 0.00130(9) C1 0.01848(12) 0.01186(10) 0.01574(10) -0.00454(8) 0.00117(9) -0.00056(9) C2 0.01506(11) 0.01549(11) 0.01963(12) -0.00765(9) 0.00072(9) 0.00046(9) C11 0.0343(2) 0.01534(13) 0.01806(13) -0.00178(10) 0.00256(13) 0.00023(13) C12 0.01764(14) 0.01990(15) 0.0361(2) -0.01134(14) 0.00187(13) -0.00014(11) C13 0.02983(18) 0.01819(13) 0.01913(13) -0.00866(11) -0.00001(12) -0.00313(12) C21 0.02562(17) 0.02123(16) 0.03210(19) -0.01322(14) 0.00341(14) 0.00464(13) C22 0.01926(14) 0.02094(15) 0.02506(15) -0.00876(12) 0.00326(11) -0.00476(11) C23 0.02061(15) 0.02133(15) 0.02631(16) -0.00957(12) -0.00681(12) 0.00173(12) _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 N2 1.5282(3) . ? S1 N1 1.5439(3) . ? N1 C1 1.4896(4) . ? N2 C2 1.4774(5) . ? C1 C12 1.5274(6) . ? C1 C13 1.5275(5) . ? C1 C11 1.5284(5) . ? C2 C22 1.5283(6) . ? C2 C21 1.5293(5) . ? C2 C23 1.5310(5) . ? 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 N2 S1 N1 117.382(18) . . ? C1 N1 S1 118.17(2) . . ? C2 N2 S1 128.06(2) . . ? N1 C1 C12 106.45(3) . . ? N1 C1 C13 105.93(3) . . ? C12 C1 C13 110.26(3) . . ? N1 C1 C11 115.12(3) . . ? C12 C1 C11 109.54(4) . . ? C13 C1 C11 109.42(3) . . ? N2 C2 C22 110.67(3) . . ? N2 C2 C21 105.38(3) . . ? C22 C2 C21 109.91(3) . . ? N2 C2 C23 110.32(3) . . ? C22 C2 C23 110.58(3) . . ? C21 C2 C23 109.86(3) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 52.41 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.028 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.070 data_stern _database_code_CSD 191360 _ccdc_compound_id 'stern' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H27 N3 S' _chemical_formula_weight 245.43 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' 'S' 'S' 0.1246 0.1234 '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 9.3228(3) _cell_length_b 9.3455(3) _cell_length_c 10.6675(3) _cell_angle_alpha 70.5150(10) _cell_angle_beta 77.5710(10) _cell_angle_gamma 60.5540(10) _cell_volume 761.52(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7829 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.4 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'MULABS implemented in PLATON' _exptl_special_details ; Data collection was performed within two steps. A low angle batch (2 theta position -31 degrees) and a high angle batch (2 theta -80 degrees) with a detector/sample distance of 5 cm were collected. This strategy lead to a high redundancy at more than 96% completeness in average up to 2 theta 104 degrees but to a relatively low degree of overlap for the two batches. Due to that the two batches were treated separately during all subsequent steps of data processing (absorption correction, merging) and were included in the refinements with two scaling factors. ; _diffrn_ambient_temperature 100(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 'Bruker Smart Apex with D8-Goniometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number '17996 (low angle batch), 44864 (high angle batch)' _diffrn_reflns_av_R_equivalents '0.0287 (low angle batch), 0.0307 (high angle batch)' _diffrn_reflns_av_sigmaI/netI '0.0101 (low angle batch), 0.0284 (high angle batch)' _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 54.19 _reflns_number_total 18250 _reflns_number_gt 14949 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.6' _computing_cell_refinement 'SAINT-NT V5/6.0' _computing_data_reduction 'SAINT-NT V5/6.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT V5.1' _computing_publication_material 'SHELXTL-NT V5.1' _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^)+(0.0500P)^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 18250 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0750 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 S1 S 0.025609(6) 0.413798(7) 0.242600(6) 0.01501(2) Uani 1 1 d . . . N1 N -0.15845(2) 0.47419(3) 0.26522(3) 0.01834(3) Uani 1 1 d . . . N2 N 0.14009(2) 0.23274(2) 0.23543(3) 0.01776(3) Uani 1 1 d . . . N3 N 0.09534(2) 0.53507(3) 0.22601(3) 0.01811(3) Uani 1 1 d . . . C1 C -0.24452(3) 0.36889(3) 0.28888(2) 0.01584(3) Uani 1 1 d . . . C11 C -0.42748(3) 0.49513(4) 0.29882(4) 0.02565(5) Uani 1 1 d . . . H11 H -0.4491(10) 0.5435(10) 0.3713(8) 0.038 Uiso 1 1 d . . . H12 H -0.4950(10) 0.4362(10) 0.3189(8) 0.038 Uiso 1 1 d . . . H13 H -0.4605(10) 0.5850(10) 0.2198(8) 0.038 Uiso 1 1 d . . . C12 C -0.21136(4) 0.29342(4) 0.17287(3) 0.02090(4) Uani 1 1 d . . . H14 H -0.2309(9) 0.3774(9) 0.0844(7) 0.031 Uiso 1 1 d . . . H15 H -0.0948(9) 0.2090(9) 0.1691(7) 0.031 Uiso 1 1 d . . . H16 H -0.2837(9) 0.2405(9) 0.1845(7) 0.031 Uiso 1 1 d . . . C13 C -0.19582(5) 0.22800(5) 0.41865(3) 0.02618(5) Uani 1 1 d . . . H17 H -0.0797(10) 0.1505(10) 0.4119(8) 0.039 Uiso 1 1 d . . . H18 H -0.2636(10) 0.1621(10) 0.4364(8) 0.039 Uiso 1 1 d . . . H19 H -0.2179(10) 0.2746(10) 0.4935(8) 0.039 Uiso 1 1 d . . . C2 C 0.32305(2) 0.15558(3) 0.21936(2) 0.01473(3) Uani 1 1 d . . . C21 C 0.37562(3) -0.02319(3) 0.20940(3) 0.02193(4) Uani 1 1 d . . . H21 H 0.3360(10) -0.0867(10) 0.2921(7) 0.033 Uiso 1 1 d . . . H22 H 0.3300(9) -0.0119(9) 0.1290(7) 0.033 Uiso 1 1 d . . . H23 H 0.4952(9) -0.0837(9) 0.2006(7) 0.033 Uiso 1 1 d . . . C22 C 0.38366(3) 0.25341(3) 0.09277(3) 0.01955(4) Uani 1 1 d . . . H24 H 0.5026(9) 0.1850(9) 0.0805(7) 0.029 Uiso 1 1 d . . . H25 H 0.3319(9) 0.2750(9) 0.0149(7) 0.029 Uiso 1 1 d . . . H26 H 0.3585(9) 0.3652(9) 0.0987(7) 0.029 Uiso 1 1 d . . . C23 C 0.39266(4) 0.14321(4) 0.34175(3) 0.02172(4) Uani 1 1 d . . . H27 H 0.5157(9) 0.0889(9) 0.3280(7) 0.033 Uiso 1 1 d . . . H28 H 0.3505(9) 0.0824(9) 0.4201(7) 0.033 Uiso 1 1 d . . . H29 H 0.3589(9) 0.2586(9) 0.3499(7) 0.033 Uiso 1 1 d . . . C3 C -0.00108(3) 0.71516(3) 0.23173(2) 0.01528(3) Uani 1 1 d . . . C31 C 0.12851(3) 0.77876(3) 0.20333(4) 0.02217(4) Uani 1 1 d . . . H31 H 0.2052(9) 0.7146(10) 0.2690(8) 0.033 Uiso 1 1 d . . . H32 H 0.1852(9) 0.7704(10) 0.1171(8) 0.033 Uiso 1 1 d . . . H33 H 0.0873(9) 0.8896(9) 0.2061(7) 0.033 Uiso 1 1 d . . . C32 C -0.12688(3) 0.82110(4) 0.12520(3) 0.02120(4) Uani 1 1 d . . . H34 H -0.0774(9) 0.8124(9) 0.0363(7) 0.032 Uiso 1 1 d . . . H35 H -0.1769(9) 0.9405(9) 0.1242(7) 0.032 Uiso 1 1 d . . . H36 H -0.2125(9) 0.7871(9) 0.1422(7) 0.032 Uiso 1 1 d . . . C33 C -0.08625(4) 0.72663(4) 0.36990(3) 0.02427(5) Uani 1 1 d . . . H37 H -0.1393(9) 0.8493(10) 0.3737(8) 0.036 Uiso 1 1 d . . . H38 H -0.1719(10) 0.6868(10) 0.3907(8) 0.036 Uiso 1 1 d . . . H39 H -0.0173(9) 0.6665(10) 0.4369(7) 0.036 Uiso 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 S1 0.01097(2) 0.01196(2) 0.02330(3) -0.00659(2) 0.00018(1) -0.00543(1) N1 0.01165(5) 0.01447(6) 0.03054(9) -0.00899(6) 0.00190(5) -0.00657(4) N2 0.01160(5) 0.01273(5) 0.02979(9) -0.00816(5) -0.00016(5) -0.00507(4) N3 0.01274(5) 0.01328(6) 0.03050(9) -0.00845(6) -0.00014(5) -0.00641(4) C1 0.01332(6) 0.01425(6) 0.02103(8) -0.00524(5) 0.00064(5) -0.00742(5) C11 0.01328(7) 0.02123(9) 0.04274(16) -0.01194(10) 0.00426(8) -0.00833(7) C12 0.02162(9) 0.01982(8) 0.02415(10) -0.00793(7) -0.00254(7) -0.00988(7) C13 0.03038(13) 0.02701(12) 0.02139(10) 0.00024(8) -0.00241(8) -0.01717(10) C2 0.01178(5) 0.01305(6) 0.01925(7) -0.00453(5) -0.00108(5) -0.00541(5) C21 0.01570(7) 0.01450(7) 0.03514(13) -0.00986(7) 0.00057(7) -0.00538(6) C22 0.01850(8) 0.02018(8) 0.01966(9) -0.00409(6) 0.00053(6) -0.01004(7) C23 0.02103(9) 0.02449(10) 0.02044(9) -0.00392(7) -0.00485(7) -0.01090(8) C3 0.01363(6) 0.01267(6) 0.02053(8) -0.00572(5) -0.00084(5) -0.00602(5) C31 0.01776(8) 0.01662(8) 0.03564(13) -0.00757(8) -0.00217(7) -0.00988(6) C32 0.01717(8) 0.01865(8) 0.02521(10) -0.00384(7) -0.00465(7) -0.00624(6) C33 0.02887(12) 0.02538(11) 0.02268(10) -0.01133(8) 0.00358(8) -0.01439(9) _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 N3 1.5098(2) . ? S1 N1 1.5105(2) . ? S1 N2 1.5112(2) . ? N1 C1 1.4831(3) . ? N2 C2 1.4853(3) . ? N3 C3 1.4838(3) . ? C1 C13 1.5242(4) . ? C1 C12 1.5257(4) . ? C1 C11 1.5296(3) . ? C11 H11 0.958(8) . ? C11 H12 0.974(8) . ? C11 H13 0.947(8) . ? C12 H14 0.989(7) . ? C12 H15 0.982(7) . ? C12 H16 0.983(8) . ? C13 H17 0.965(8) . ? C13 H18 1.033(8) . ? C13 H19 0.971(8) . ? C2 C23 1.5263(4) . ? C2 C21 1.5276(3) . ? C2 C22 1.5279(3) . ? C21 H21 0.996(7) . ? C21 H22 0.990(8) . ? C21 H23 0.970(7) . ? C22 H24 0.976(7) . ? C22 H25 0.964(7) . ? C22 H26 0.974(7) . ? C23 H27 1.000(7) . ? C23 H28 0.968(7) . ? C23 H29 0.993(7) . ? C3 C32 1.5260(4) . ? C3 C33 1.5272(4) . ? C3 C31 1.5274(3) . ? C31 H31 0.935(8) . ? C31 H32 0.964(8) . ? C31 H33 0.920(7) . ? C32 H34 0.973(7) . ? C32 H35 0.972(7) . ? C32 H36 0.959(7) . ? C33 H37 1.013(8) . ? C33 H38 0.993(8) . ? C33 H39 0.902(8) . ? 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 N3 S1 N1 119.909(11) . . ? N3 S1 N2 119.885(11) . . ? N1 S1 N2 120.204(11) . . ? C1 N1 S1 126.204(16) . . ? C2 N2 S1 125.528(15) . . ? C3 N3 S1 125.969(16) . . ? N1 C1 C13 110.75(2) . . ? N1 C1 C12 111.79(2) . . ? C13 C1 C12 110.46(2) . . ? N1 C1 C11 103.973(19) . . ? C13 C1 C11 110.41(2) . . ? C12 C1 C11 109.28(2) . . ? C1 C11 H11 109.7(5) . . ? C1 C11 H12 110.2(5) . . ? H11 C11 H12 106.5(6) . . ? C1 C11 H13 112.1(5) . . ? H11 C11 H13 108.4(6) . . ? H12 C11 H13 109.7(7) . . ? C1 C12 H14 114.4(4) . . ? C1 C12 H15 109.0(4) . . ? H14 C12 H15 106.2(6) . . ? C1 C12 H16 109.8(4) . . ? H14 C12 H16 106.6(6) . . ? H15 C12 H16 110.7(6) . . ? C1 C13 H17 109.7(5) . . ? C1 C13 H18 109.3(4) . . ? H17 C13 H18 109.4(6) . . ? C1 C13 H19 111.3(5) . . ? H17 C13 H19 108.9(6) . . ? H18 C13 H19 108.2(6) . . ? N2 C2 C23 110.33(2) . . ? N2 C2 C21 103.984(17) . . ? C23 C2 C21 109.78(2) . . ? N2 C2 C22 112.222(19) . . ? C23 C2 C22 110.64(2) . . ? C21 C2 C22 109.68(2) . . ? C2 C21 H21 109.5(4) . . ? C2 C21 H22 108.3(4) . . ? H21 C21 H22 112.0(6) . . ? C2 C21 H23 109.2(4) . . ? H21 C21 H23 108.7(6) . . ? H22 C21 H23 109.2(6) . . ? C2 C22 H24 107.6(4) . . ? C2 C22 H25 112.7(4) . . ? H24 C22 H25 109.2(6) . . ? C2 C22 H26 111.6(4) . . ? H24 C22 H26 110.3(6) . . ? H25 C22 H26 105.4(6) . . ? C2 C23 H27 108.0(4) . . ? C2 C23 H28 108.5(4) . . ? H27 C23 H28 114.6(6) . . ? C2 C23 H29 110.7(4) . . ? H27 C23 H29 105.8(6) . . ? H28 C23 H29 109.2(6) . . ? N3 C3 C32 111.50(2) . . ? N3 C3 C33 111.04(2) . . ? C32 C3 C33 110.54(2) . . ? N3 C3 C31 104.026(18) . . ? C32 C3 C31 109.64(2) . . ? C33 C3 C31 109.90(2) . . ? C3 C31 H31 109.8(4) . . ? C3 C31 H32 111.1(5) . . ? H31 C31 H32 109.4(7) . . ? C3 C31 H33 114.4(4) . . ? H31 C31 H33 104.4(7) . . ? H32 C31 H33 107.5(6) . . ? C3 C32 H34 112.7(4) . . ? C3 C32 H35 109.0(4) . . ? H34 C32 H35 107.4(6) . . ? C3 C32 H36 111.7(4) . . ? H34 C32 H36 107.3(6) . . ? H35 C32 H36 108.6(6) . . ? C3 C33 H37 109.0(4) . . ? C3 C33 H38 111.6(4) . . ? H37 C33 H38 109.3(6) . . ? C3 C33 H39 114.3(5) . . ? H37 C33 H39 105.1(7) . . ? H38 C33 H39 107.2(6) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 54.19 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.607 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.067