# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Francisco Foubelo' _publ_contact_author_email foubelo@ua.es loop_ _publ_author_name 'Miguel Yus' 'Francisco Foubelo' 'Juan Sirvent' data_p31b _database_code_depnum_ccdc_archive 'CCDC 855612' #TrackingRef 'p31b_final.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H23 N O S' _chemical_formula_sum 'C13 H23 N O S' _chemical_formula_weight 241.38 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 3(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' _cell_length_a 10.109(12) _cell_length_b 10.109(12) _cell_length_c 12.65(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1119(3) _cell_formula_units_Z 3 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 1642 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 18.1 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.074 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4220 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details 'Bruker/Siemens SADABS V2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(1) _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7422 _diffrn_reflns_av_R_equivalents 0.1177 _diffrn_reflns_av_sigmaI/netI 0.1296 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2364 _reflns_number_gt 1191 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART V5.625' _computing_cell_refinement 'Bruker SMART V5.625' _computing_data_reduction 'Bruker SAINT V6.28A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL Rel. 6.12/V (Siemens, 1996)' _computing_publication_material 'SHELX-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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.093(5) _refine_ls_number_reflns 2364 _refine_ls_number_parameters 149 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1527 _refine_ls_goodness_of_fit_ref 0.849 _refine_ls_restrained_S_all 0.849 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0258(8) 0.5716(8) 0.8674(7) 0.097(2) Uani 1 1 d . . . C2 C 0.0789(8) 0.6902(8) 0.9430(6) 0.0874(18) Uani 1 1 d . . . H2 H 0.0362 0.7225 0.9949 0.105 Uiso 1 1 calc R . . C3 C 0.2293(9) 0.7529(9) 0.9412(6) 0.100(2) Uani 1 1 d . . . H3 H 0.2820 0.8306 0.9901 0.120 Uiso 1 1 calc R . . C4 C 0.3210(12) 0.7183(11) 0.8755(8) 0.123(3) Uani 1 1 d . . . H4A H 0.4030 0.7202 0.9165 0.147 Uiso 1 1 calc R . . H4B H 0.3660 0.7939 0.8197 0.147 Uiso 1 1 calc R . . C5 C 0.2278(13) 0.5694(15) 0.8303(9) 0.143(4) Uani 1 1 d . . . H5A H 0.1962 0.4926 0.8853 0.172 Uiso 1 1 calc R . . H5B H 0.2867 0.5498 0.7786 0.172 Uiso 1 1 calc R . . C6 C 0.0847(13) 0.5584(10) 0.7765(7) 0.119(3) Uani 1 1 d . . . H6A H 0.0287 0.4618 0.7395 0.143 Uiso 1 1 calc R . . H6B H 0.1158 0.6402 0.7254 0.143 Uiso 1 1 calc R . . C7 C -0.1257(12) 0.6152(10) 0.8090(10) 0.133(3) Uani 1 1 d . . . H7A H -0.0623 0.7108 0.7723 0.159 Uiso 1 1 calc R . . H7B H -0.1831 0.5378 0.7562 0.159 Uiso 1 1 calc R . . C8 C -0.2309(15) 0.6322(17) 0.8767(12) 0.155(4) Uani 1 1 d . . . H8 H -0.2867 0.5611 0.9289 0.186 Uiso 1 1 calc R . . C9 C -0.245(2) 0.7681(18) 0.8586(13) 0.190(6) Uani 1 1 d . . . H9A H -0.1876 0.8373 0.8058 0.229 Uiso 1 1 calc R . . H9B H -0.3110 0.7851 0.9000 0.229 Uiso 1 1 calc R . . N1 N -0.1138(5) 0.4173(5) 0.9198(4) 0.0717(13) Uani 1 1 d . . . H1 H -0.1621 0.3376 0.8805 0.086 Uiso 1 1 calc R . . S1 S -0.12078(15) 0.39572(18) 1.04631(12) 0.0764(5) Uani 1 1 d . . . O1 O -0.2568(6) 0.4011(7) 1.0893(5) 0.1144(17) Uani 1 1 d . . . C10 C -0.1751(7) 0.1907(8) 1.0504(6) 0.0866(19) Uani 1 1 d . . . C11 C -0.1917(12) 0.1567(13) 1.1722(7) 0.134(4) Uani 1 1 d . . . H11A H -0.2281 0.0501 1.1837 0.200 Uiso 1 1 calc R . . H11B H -0.2631 0.1829 1.2017 0.200 Uiso 1 1 calc R . . H11C H -0.0942 0.2162 1.2058 0.200 Uiso 1 1 calc R . . C12 C -0.0529(9) 0.1719(10) 1.0015(11) 0.130(4) Uani 1 1 d . . . H12A H 0.0429 0.2402 1.0346 0.195 Uiso 1 1 calc R . . H12B H -0.0470 0.1947 0.9274 0.195 Uiso 1 1 calc R . . H12C H -0.0752 0.0685 1.0108 0.195 Uiso 1 1 calc R . . C13 C -0.3271(9) 0.0882(8) 0.9960(8) 0.104(2) Uani 1 1 d . . . H13A H -0.3203 0.1169 0.9230 0.156 Uiso 1 1 calc R . . H13B H -0.4060 0.0993 1.0300 0.156 Uiso 1 1 calc R . . H13C H -0.3510 -0.0162 1.0009 0.156 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 C1 0.085(4) 0.073(4) 0.136(7) -0.006(4) -0.030(5) 0.042(4) C2 0.073(4) 0.089(4) 0.088(5) -0.020(3) -0.004(3) 0.031(3) C3 0.088(5) 0.099(5) 0.084(5) 0.010(4) -0.015(4) 0.026(4) C4 0.116(6) 0.106(7) 0.117(8) 0.019(5) 0.012(6) 0.033(6) C5 0.128(8) 0.189(12) 0.124(8) 0.029(8) 0.047(7) 0.089(8) C6 0.165(9) 0.091(5) 0.063(5) -0.010(4) 0.009(5) 0.036(5) C7 0.134(8) 0.091(5) 0.140(9) -0.008(6) -0.023(6) 0.031(5) C8 0.152(10) 0.174(11) 0.159(10) -0.004(8) 0.022(7) 0.096(8) C9 0.249(19) 0.211(14) 0.170(15) -0.020(10) 0.011(11) 0.159(15) N1 0.064(3) 0.070(3) 0.072(3) -0.018(2) -0.004(2) 0.027(2) S1 0.0679(9) 0.0913(11) 0.0637(8) -0.0165(8) -0.0025(8) 0.0351(8) O1 0.093(3) 0.160(5) 0.096(4) -0.022(3) 0.022(3) 0.068(3) C10 0.063(4) 0.086(4) 0.093(5) 0.000(4) -0.003(3) 0.024(3) C11 0.154(8) 0.136(7) 0.072(6) 0.024(5) -0.010(5) 0.044(6) C12 0.095(5) 0.094(5) 0.216(12) 0.023(6) 0.014(6) 0.059(5) C13 0.088(5) 0.076(4) 0.123(7) 0.003(4) -0.009(4) 0.022(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 C1 C2 1.484(10) . ? C1 C7 1.485(12) . ? C1 N1 1.509(9) . ? C1 C6 1.654(14) . ? C2 C3 1.322(10) . ? C3 C4 1.413(13) . ? C4 C5 1.436(15) . ? C5 C6 1.552(15) . ? C7 C8 1.441(16) . ? C8 C9 1.469(18) . ? N1 S1 1.612(6) . ? S1 O1 1.505(5) . ? S1 C10 1.861(8) . ? C10 C12 1.476(12) . ? C10 C13 1.522(11) . ? C10 C11 1.570(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C7 113.4(6) . . ? C2 C1 N1 111.5(7) . . ? C7 C1 N1 112.9(6) . . ? C2 C1 C6 106.0(6) . . ? C7 C1 C6 105.3(8) . . ? N1 C1 C6 107.1(6) . . ? C3 C2 C1 124.1(7) . . ? C2 C3 C4 129.1(8) . . ? C3 C4 C5 109.0(8) . . ? C4 C5 C6 110.4(9) . . ? C5 C6 C1 109.4(7) . . ? C8 C7 C1 113.0(10) . . ? C7 C8 C9 116.2(12) . . ? C1 N1 S1 122.6(4) . . ? O1 S1 N1 109.5(3) . . ? O1 S1 C10 105.3(3) . . ? N1 S1 C10 98.4(3) . . ? C12 C10 C13 110.4(8) . . ? C12 C10 C11 112.8(8) . . ? C13 C10 C11 109.5(7) . . ? C12 C10 S1 109.4(5) . . ? C13 C10 S1 112.4(5) . . ? C11 C10 S1 102.2(6) . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.912 _refine_diff_density_max 0.281 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.059 data_p31 _database_code_depnum_ccdc_archive 'CCDC 855613' #TrackingRef 'A201_final.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H25 N O S' _chemical_formula_sum 'C14 H25 N O S' _chemical_formula_weight 255.41 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 3(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' _cell_length_a 10.2768(10) _cell_length_b 10.2768(10) _cell_length_c 12.750(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1166.1(3) _cell_formula_units_Z 3 _cell_measurement_temperature 297(1) _cell_measurement_reflns_used 2014 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 19.15 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.091 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7521 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details 'Bruker/Siemens SADABS V2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(1) _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9839 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.08 _reflns_number_total 2749 _reflns_number_gt 2099 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART V5.625' _computing_cell_refinement 'Bruker SMART V5.625' _computing_data_reduction 'Bruker SAINT V6.28A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL Rel. 6.12/V (Siemens, 1996)' _computing_publication_material 'SHELX-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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+0.0497P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _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 0.075(3) _refine_ls_number_reflns 2749 _refine_ls_number_parameters 160 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6193(4) 0.5634(4) 0.4944(3) 0.0742(9) Uani 1 1 d . . . C2 C 0.6028(4) 0.6742(4) 0.4276(3) 0.0886(10) Uani 1 1 d . . . H2 H 0.6569 0.7000 0.3652 0.106 Uiso 1 1 calc R . . C3 C 0.5237(5) 0.7401(4) 0.4438(3) 0.0929(11) Uani 1 1 d . . . H3 H 0.5412 0.8164 0.3969 0.111 Uiso 1 1 calc R . . C4 C 0.4111(5) 0.7109(5) 0.5257(4) 0.1041(12) Uani 1 1 d . . . H4A H 0.3427 0.7434 0.5006 0.125 Uiso 1 1 calc R . . H4B H 0.4615 0.7699 0.5874 0.125 Uiso 1 1 calc R . . C5 C 0.3238(5) 0.5509(5) 0.5552(4) 0.1123(15) Uani 1 1 d . . . H5A H 0.2956 0.4909 0.4916 0.135 Uiso 1 1 calc R . . H5B H 0.2319 0.5329 0.5893 0.135 Uiso 1 1 calc R . . C6 C 0.4064(6) 0.4958(5) 0.6288(3) 0.1103(15) Uani 1 1 d . . . H6A H 0.3926 0.5177 0.7006 0.132 Uiso 1 1 calc R . . H6B H 0.3593 0.3875 0.6222 0.132 Uiso 1 1 calc R . . C7 C 0.5727(5) 0.5640(4) 0.6085(3) 0.0946(12) Uani 1 1 d . . . H7A H 0.6093 0.5104 0.6506 0.113 Uiso 1 1 calc R . . H7B H 0.6230 0.6672 0.6328 0.113 Uiso 1 1 calc R . . C8 C 0.7873(4) 0.6029(5) 0.4879(4) 0.1181(16) Uani 1 1 d . . . H8A H 0.7999 0.5309 0.5294 0.142 Uiso 1 1 calc R . . H8B H 0.8108 0.5932 0.4156 0.142 Uiso 1 1 calc R . . C9 C 0.8952(6) 0.7566(7) 0.5253(7) 0.171(3) Uani 1 1 d . . . H9 H 0.8593 0.8227 0.5151 0.205 Uiso 1 1 calc R . . C10 C 1.0058(9) 0.8115(9) 0.5616(9) 0.218(4) Uani 1 1 d . . . H10A H 1.0536 0.7569 0.5758 0.261 Uiso 1 1 calc R . . H10B H 1.0525 0.9131 0.5785 0.261 Uiso 1 1 calc R . . N1 N 0.5264(3) 0.4077(3) 0.4560(2) 0.0656(7) Uani 1 1 d . . . H1N H 0.546(4) 0.351(4) 0.483(3) 0.079 Uiso 1 1 d . . . S1 S 0.50492(9) 0.37977(9) 0.32860(5) 0.0736(3) Uani 1 1 d . . . O1 O 0.6363(3) 0.3803(4) 0.2793(2) 0.1079(9) Uani 1 1 d . . . C11 C 0.3576(4) 0.1819(4) 0.3299(3) 0.0852(10) Uani 1 1 d . . . C12 C 0.3251(8) 0.1381(7) 0.2147(4) 0.143(2) Uani 1 1 d . . . H12A H 0.4148 0.1522 0.1811 0.214 Uiso 1 1 calc R . . H12B H 0.2920 0.2000 0.1810 0.214 Uiso 1 1 calc R . . H12C H 0.2480 0.0346 0.2093 0.214 Uiso 1 1 calc R . . C13 C 0.4096(6) 0.0850(4) 0.3856(4) 0.1100(15) Uani 1 1 d . . . H13A H 0.3332 -0.0188 0.3801 0.165 Uiso 1 1 calc R . . H13B H 0.4280 0.1131 0.4582 0.165 Uiso 1 1 calc R . . H13C H 0.5005 0.0995 0.3537 0.165 Uiso 1 1 calc R . . C14 C 0.2199(5) 0.1736(5) 0.3818(6) 0.1263(18) Uani 1 1 d . . . H14A H 0.2038 0.2513 0.3540 0.189 Uiso 1 1 calc R . . H14B H 0.2358 0.1871 0.4562 0.189 Uiso 1 1 calc R . . H14C H 0.1333 0.0773 0.3680 0.189 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 C1 0.0609(18) 0.064(2) 0.091(2) -0.0075(17) -0.0036(16) 0.0266(16) C2 0.091(2) 0.066(2) 0.098(3) 0.0099(18) 0.0155(19) 0.032(2) C3 0.110(3) 0.068(2) 0.104(3) 0.0058(18) -0.006(2) 0.047(2) C4 0.103(3) 0.097(3) 0.127(3) -0.012(2) -0.002(2) 0.061(2) C5 0.084(3) 0.094(3) 0.150(4) -0.016(3) 0.027(3) 0.038(2) C6 0.149(4) 0.099(3) 0.081(3) 0.003(2) 0.031(3) 0.060(3) C7 0.125(3) 0.082(2) 0.079(2) -0.0189(19) -0.025(2) 0.053(2) C8 0.076(3) 0.098(3) 0.173(5) -0.028(3) -0.012(3) 0.037(2) C9 0.078(3) 0.133(5) 0.290(9) -0.070(5) -0.047(4) 0.044(3) C10 0.115(5) 0.172(7) 0.338(13) -0.070(7) -0.093(7) 0.050(5) N1 0.0706(15) 0.0620(15) 0.0672(15) 0.0075(12) 0.0087(12) 0.0354(13) S1 0.0841(6) 0.0813(6) 0.0644(4) 0.0076(4) 0.0035(4) 0.0480(5) O1 0.109(2) 0.145(2) 0.0815(16) 0.0113(16) 0.0297(14) 0.071(2) C11 0.093(3) 0.077(2) 0.090(2) -0.0151(18) -0.0177(18) 0.0457(19) C12 0.194(6) 0.137(5) 0.105(3) -0.041(3) -0.053(4) 0.088(4) C13 0.143(4) 0.069(2) 0.125(3) -0.013(2) -0.036(3) 0.058(3) C14 0.083(3) 0.088(3) 0.188(6) -0.024(3) -0.011(3) 0.027(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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.477(4) . ? C1 C2 1.498(5) . ? C1 C7 1.532(5) . ? C1 C8 1.565(5) . ? C2 C3 1.309(5) . ? C2 H2 0.9300 . ? C3 C4 1.474(6) . ? C3 H3 0.9300 . ? C4 C5 1.475(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.550(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.511(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.483(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.087(7) . ? C9 H9 0.9300 . ? C10 H10A 0.9300 . ? C10 H10B 0.9300 . ? N1 S1 1.645(3) . ? N1 H1N 0.79(4) . ? S1 O1 1.487(3) . ? S1 C11 1.830(4) . ? C11 C13 1.521(5) . ? C11 C12 1.524(6) . ? C11 C14 1.525(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 N1 C1 C2 112.1(3) . . ? N1 C1 C7 106.5(3) . . ? C2 C1 C7 112.5(3) . . ? N1 C1 C8 107.2(3) . . ? C2 C1 C8 107.5(3) . . ? C7 C1 C8 110.9(3) . . ? C3 C2 C1 129.7(4) . . ? C3 C2 H2 115.1 . . ? C1 C2 H2 115.1 . . ? C2 C3 C4 129.4(4) . . ? C2 C3 H3 115.3 . . ? C4 C3 H3 115.3 . . ? C3 C4 C5 112.6(3) . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C6 115.0(4) . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C7 C6 C5 115.2(3) . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6A 108.5 . . ? C7 C6 H6B 108.5 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C1 116.4(3) . . ? C6 C7 H7A 108.2 . . ? C1 C7 H7A 108.2 . . ? C6 C7 H7B 108.2 . . ? C1 C7 H7B 108.2 . . ? H7A C7 H7B 107.3 . . ? C9 C8 C1 113.6(4) . . ? C9 C8 H8A 108.8 . . ? C1 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C1 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 136.1(8) . . ? C10 C9 H9 111.9 . . ? C8 C9 H9 111.9 . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? C1 N1 S1 118.3(2) . . ? C1 N1 H1N 113(3) . . ? S1 N1 H1N 111(3) . . ? O1 S1 N1 111.99(16) . . ? O1 S1 C11 104.67(18) . . ? N1 S1 C11 98.57(15) . . ? C13 C11 C12 110.7(3) . . ? C13 C11 C14 112.4(4) . . ? C12 C11 C14 110.0(4) . . ? C13 C11 S1 111.4(3) . . ? C12 C11 S1 104.8(3) . . ? C14 C11 S1 107.2(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.149 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.029