Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Stuart Warren' _publ_contact_author_address ; University Chemical Laboratories University of Cambridge Lensfield Road Cambridge Cambridgeshire CB2 1EW UNITED KINGDOM ; _publ_contact_author_email SW134@CAM.AC.UK _publ_section_title ; Selective five- and six-membered cyclic amine syntheses via capture of episulfonium ions ; loop_ _publ_author_name 'Stuart Warren' 'David J. Fox' 'Thomas J. Morley' 'Sarah Taylor' data_sw0402 _database_code_depnum_ccdc_archive 'CCDC 261090' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N3 O5 S' _chemical_formula_sum 'C20 H21 N3 O5 S' _chemical_formula_weight 415.46 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 6.04760(10) _cell_length_b 10.1799(3) _cell_length_c 32.0263(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1971.67(9) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 48285 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The absolute structure was determined reliably (Flack parameter -0.08(8)). ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7221 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3248 _reflns_number_gt 3055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0219P)^2^+0.6647P] 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 -0.08(8) _refine_ls_number_reflns 3248 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.003 _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 0.67097(10) 0.15552(5) 0.039770(17) 0.03623(15) Uani 1 1 d . . . N1 N 0.9716(3) 0.17747(16) 0.15290(5) 0.0256(4) Uani 1 1 d . . . C1 C 0.8394(3) 0.21187(19) 0.11537(6) 0.0274(4) Uani 1 1 d . . . H1 H 0.6884 0.2406 0.1243 0.033 Uiso 1 1 calc R . . N2 N 1.0909(4) 0.1834(2) 0.33836(6) 0.0400(5) Uani 1 1 d . . . O2 O 0.9393(3) 0.26213(19) 0.34247(5) 0.0553(5) Uani 1 1 d . . . O3 O 1.2159(3) 0.15140(18) 0.36651(5) 0.0569(5) Uani 1 1 d . . . C2 C 0.9635(4) 0.3299(2) 0.09632(7) 0.0372(5) Uani 1 1 d . . . H2A H 1.0281 0.3060 0.0689 0.045 Uiso 1 1 calc R . . H2B H 0.8618 0.4051 0.0923 0.045 Uiso 1 1 calc R . . N3 N 1.5309(3) -0.0900(2) 0.24352(7) 0.0401(5) Uani 1 1 d . . . O4 O 1.6784(3) -0.09090(17) 0.26983(6) 0.0499(4) Uani 1 1 d . . . O5 O 1.5319(3) -0.15290(18) 0.21093(6) 0.0566(5) Uani 1 1 d . . . C3 C 1.1459(4) 0.3651(2) 0.12749(8) 0.0455(6) Uani 1 1 d . . . H3A H 1.2789 0.3983 0.1129 0.055 Uiso 1 1 calc R . . H3B H 1.0943 0.4325 0.1475 0.055 Uiso 1 1 calc R . . C4 C 1.1941(3) 0.2362(2) 0.14953(7) 0.0301(5) Uani 1 1 d . . . H4A H 1.2943 0.1801 0.1328 0.036 Uiso 1 1 calc R . . H4B H 1.2602 0.2511 0.1774 0.036 Uiso 1 1 calc R . . C5 C 0.8185(3) 0.0899(2) 0.08647(6) 0.0279(4) Uani 1 1 d . . . C6 C 0.6794(4) -0.0172(2) 0.10682(7) 0.0362(5) Uani 1 1 d . . . H6A H 0.7523 -0.0474 0.1324 0.054 Uiso 1 1 calc R . . H6B H 0.6633 -0.0911 0.0874 0.054 Uiso 1 1 calc R . . H6C H 0.5330 0.0180 0.1137 0.054 Uiso 1 1 calc R . . C7 C 1.0432(4) 0.0334(2) 0.07457(7) 0.0347(5) Uani 1 1 d . . . H7A H 1.1168 -0.0005 0.0996 0.052 Uiso 1 1 calc R . . H7B H 1.1344 0.1024 0.0620 0.052 Uiso 1 1 calc R . . H7C H 1.0229 -0.0382 0.0545 0.052 Uiso 1 1 calc R . . C8 C 0.6933(4) 0.0245(2) 0.00318(6) 0.0309(5) Uani 1 1 d . . . C9 C 0.5220(4) -0.0646(2) -0.00153(7) 0.0369(5) Uani 1 1 d . . . H9 H 0.3951 -0.0587 0.0159 0.044 Uiso 1 1 calc R . . C10 C 0.5355(4) -0.1623(2) -0.03154(7) 0.0424(6) Uani 1 1 d . . . H10 H 0.4166 -0.2224 -0.0349 0.051 Uiso 1 1 calc R . . C11 C 0.7199(4) -0.1731(2) -0.05652(7) 0.0427(6) Uani 1 1 d . . . H11 H 0.7287 -0.2406 -0.0769 0.051 Uiso 1 1 calc R . . C12 C 0.8919(4) -0.0852(2) -0.05175(7) 0.0407(6) Uani 1 1 d . . . H12 H 1.0200 -0.0929 -0.0687 0.049 Uiso 1 1 calc R . . C13 C 0.8786(4) 0.0143(2) -0.02230(7) 0.0367(5) Uani 1 1 d . . . H13 H 0.9963 0.0756 -0.0195 0.044 Uiso 1 1 calc R . . C14 C 0.8725(3) 0.1492(2) 0.18975(6) 0.0274(4) Uani 1 1 d . . . O1 O 0.6723(2) 0.14872(17) 0.19549(5) 0.0402(4) Uani 1 1 d . . . C15 C 1.0259(3) 0.1104(2) 0.22483(6) 0.0267(4) Uani 1 1 d . . . C16 C 0.9838(3) 0.1589(2) 0.26468(6) 0.0286(4) Uani 1 1 d . . . H16 H 0.8599 0.2139 0.2698 0.034 Uiso 1 1 calc R . . C17 C 1.1265(3) 0.1252(2) 0.29657(6) 0.0306(5) Uani 1 1 d . . . C18 C 1.3072(4) 0.0436(2) 0.29113(7) 0.0328(5) Uani 1 1 d . . . H18 H 1.4044 0.0223 0.3134 0.039 Uiso 1 1 calc R . . C19 C 1.3373(4) -0.00466(19) 0.25147(7) 0.0302(5) Uani 1 1 d . . . C20 C 1.2031(3) 0.02691(19) 0.21815(6) 0.0277(5) Uani 1 1 d . . . H20 H 1.2316 -0.0079 0.1912 0.033 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 0.0453(3) 0.0309(3) 0.0325(3) -0.0031(2) -0.0117(2) 0.0098(3) N1 0.0224(8) 0.0287(9) 0.0258(9) 0.0010(7) -0.0006(7) 0.0011(7) C1 0.0265(10) 0.0285(10) 0.0273(10) 0.0013(9) -0.0024(9) 0.0056(9) N2 0.0536(12) 0.0371(11) 0.0292(10) 0.0001(9) -0.0023(9) -0.0089(10) O2 0.0703(13) 0.0576(12) 0.0379(11) -0.0086(9) 0.0036(9) 0.0115(10) O3 0.0803(13) 0.0594(11) 0.0310(9) 0.0027(9) -0.0181(9) -0.0042(11) C2 0.0488(14) 0.0282(11) 0.0347(12) 0.0037(10) -0.0042(10) 0.0004(11) N3 0.0327(11) 0.0347(11) 0.0528(13) 0.0118(10) -0.0027(9) 0.0060(9) O4 0.0326(9) 0.0547(10) 0.0622(11) 0.0207(9) -0.0131(9) 0.0061(8) O5 0.0528(11) 0.0499(11) 0.0670(12) -0.0106(10) -0.0038(9) 0.0239(9) C3 0.0559(15) 0.0368(13) 0.0438(14) 0.0080(11) -0.0079(11) -0.0116(12) C4 0.0261(11) 0.0337(11) 0.0306(11) -0.0012(9) 0.0013(9) -0.0040(9) C5 0.0282(10) 0.0287(10) 0.0268(10) -0.0007(9) -0.0033(9) 0.0057(9) C6 0.0327(12) 0.0336(12) 0.0422(13) 0.0019(10) -0.0060(10) -0.0010(10) C7 0.0327(12) 0.0370(12) 0.0343(12) -0.0064(10) -0.0023(9) 0.0095(10) C8 0.0393(12) 0.0291(10) 0.0243(10) 0.0001(9) -0.0081(9) 0.0039(10) C9 0.0346(12) 0.0404(13) 0.0357(12) -0.0018(10) -0.0034(10) -0.0012(10) C10 0.0455(14) 0.0375(13) 0.0443(14) -0.0064(12) -0.0081(11) -0.0050(11) C11 0.0642(16) 0.0324(12) 0.0314(11) -0.0054(10) -0.0103(11) 0.0035(12) C12 0.0497(14) 0.0454(14) 0.0269(12) 0.0033(11) 0.0036(10) 0.0034(11) C13 0.0430(14) 0.0350(12) 0.0321(12) 0.0044(10) -0.0015(10) -0.0056(10) C14 0.0226(10) 0.0311(11) 0.0284(10) 0.0001(9) -0.0001(8) 0.0008(9) O1 0.0221(7) 0.0653(10) 0.0333(8) 0.0044(8) 0.0025(6) 0.0030(8) C15 0.0239(10) 0.0312(11) 0.0250(10) 0.0023(8) 0.0014(8) -0.0040(9) C16 0.0276(10) 0.0272(11) 0.0310(11) 0.0043(10) 0.0023(8) -0.0024(10) C17 0.0366(12) 0.0297(11) 0.0254(10) 0.0027(9) 0.0001(8) -0.0077(9) C18 0.0330(12) 0.0313(11) 0.0341(12) 0.0088(9) -0.0080(10) -0.0056(10) C19 0.0272(11) 0.0237(10) 0.0396(12) 0.0068(9) -0.0010(9) 0.0016(9) C20 0.0264(11) 0.0283(10) 0.0285(11) 0.0014(9) 0.0000(8) -0.0014(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 C8 1.780(2) . ? S1 C5 1.865(2) . ? N1 C14 1.355(2) . ? N1 C4 1.476(3) . ? N1 C1 1.485(2) . ? C1 C2 1.543(3) . ? C1 C5 1.554(3) . ? C1 H1 1.0000 . ? N2 O3 1.221(3) . ? N2 O2 1.225(3) . ? N2 C17 1.480(3) . ? C2 C3 1.530(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? N3 O5 1.224(3) . ? N3 O4 1.227(3) . ? N3 C19 1.480(3) . ? C3 C4 1.519(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.524(3) . ? C5 C7 1.524(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.385(3) . ? C8 C13 1.390(3) . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.377(3) . ? C10 H10 0.9500 . ? C11 C12 1.381(3) . ? C11 H11 0.9500 . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O1 1.225(2) . ? C14 C15 1.510(3) . ? C15 C20 1.384(3) . ? C15 C16 1.392(3) . ? C16 C17 1.380(3) . ? C16 H16 0.9500 . ? C17 C18 1.384(3) . ? C18 C19 1.374(3) . ? C18 H18 0.9500 . ? C19 C20 1.379(3) . ? C20 H20 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 C8 S1 C5 102.91(9) . . ? C14 N1 C4 123.57(16) . . ? C14 N1 C1 121.12(16) . . ? C4 N1 C1 109.64(15) . . ? N1 C1 C2 103.99(17) . . ? N1 C1 C5 109.71(15) . . ? C2 C1 C5 115.23(17) . . ? N1 C1 H1 109.2 . . ? C2 C1 H1 109.2 . . ? C5 C1 H1 109.2 . . ? O3 N2 O2 124.0(2) . . ? O3 N2 C17 118.1(2) . . ? O2 N2 C17 117.92(19) . . ? C3 C2 C1 105.97(17) . . ? C3 C2 H2A 110.5 . . ? C1 C2 H2A 110.5 . . ? C3 C2 H2B 110.5 . . ? C1 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? O5 N3 O4 125.3(2) . . ? O5 N3 C19 117.21(19) . . ? O4 N3 C19 117.4(2) . . ? C4 C3 C2 103.83(18) . . ? C4 C3 H3A 111.0 . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3B 111.0 . . ? C2 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? N1 C4 C3 102.05(17) . . ? N1 C4 H4A 111.4 . . ? C3 C4 H4A 111.4 . . ? N1 C4 H4B 111.4 . . ? C3 C4 H4B 111.4 . . ? H4A C4 H4B 109.2 . . ? C6 C5 C7 109.21(17) . . ? C6 C5 C1 111.22(17) . . ? C7 C5 C1 112.24(17) . . ? C6 C5 S1 109.56(15) . . ? C7 C5 S1 111.18(15) . . ? C1 C5 S1 103.32(13) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 119.3(2) . . ? C9 C8 S1 120.37(18) . . ? C13 C8 S1 120.22(17) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 119.6(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 120.0(2) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? O1 C14 N1 124.69(18) . . ? O1 C14 C15 119.66(18) . . ? N1 C14 C15 115.59(16) . . ? C20 C15 C16 120.06(18) . . ? C20 C15 C14 121.42(18) . . ? C16 C15 C14 118.51(18) . . ? C17 C16 C15 118.44(19) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C16 C17 C18 123.3(2) . . ? C16 C17 N2 118.61(19) . . ? C18 C17 N2 118.00(19) . . ? C19 C18 C17 115.84(19) . . ? C19 C18 H18 122.1 . . ? C17 C18 H18 122.1 . . ? C18 C19 C20 123.6(2) . . ? C18 C19 N3 118.29(19) . . ? C20 C19 N3 118.00(19) . . ? C19 C20 C15 118.64(19) . . ? C19 C20 H20 120.7 . . ? C15 C20 H20 120.7 . . ? 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 C14 N1 C1 C2 136.3(2) . . . . ? C4 N1 C1 C2 -18.0(2) . . . . ? C14 N1 C1 C5 -99.9(2) . . . . ? C4 N1 C1 C5 105.73(19) . . . . ? N1 C1 C2 C3 -6.4(2) . . . . ? C5 C1 C2 C3 -126.5(2) . . . . ? C1 C2 C3 C4 27.3(2) . . . . ? C14 N1 C4 C3 -118.5(2) . . . . ? C1 N1 C4 C3 35.1(2) . . . . ? C2 C3 C4 N1 -37.4(2) . . . . ? N1 C1 C5 C6 67.2(2) . . . . ? C2 C1 C5 C6 -175.84(17) . . . . ? N1 C1 C5 C7 -55.4(2) . . . . ? C2 C1 C5 C7 61.5(2) . . . . ? N1 C1 C5 S1 -175.30(13) . . . . ? C2 C1 C5 S1 -58.4(2) . . . . ? C8 S1 C5 C6 -71.76(16) . . . . ? C8 S1 C5 C7 49.04(17) . . . . ? C8 S1 C5 C1 169.63(13) . . . . ? C5 S1 C8 C9 96.66(18) . . . . ? C5 S1 C8 C13 -86.31(19) . . . . ? C13 C8 C9 C10 -0.4(3) . . . . ? S1 C8 C9 C10 176.69(17) . . . . ? C8 C9 C10 C11 0.9(3) . . . . ? C9 C10 C11 C12 -0.4(4) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C11 C12 C13 C8 1.2(3) . . . . ? C9 C8 C13 C12 -0.7(3) . . . . ? S1 C8 C13 C12 -177.75(17) . . . . ? C4 N1 C14 O1 151.0(2) . . . . ? C1 N1 C14 O1 0.3(3) . . . . ? C4 N1 C14 C15 -31.7(3) . . . . ? C1 N1 C14 C15 177.56(17) . . . . ? O1 C14 C15 C20 135.4(2) . . . . ? N1 C14 C15 C20 -42.0(3) . . . . ? O1 C14 C15 C16 -43.5(3) . . . . ? N1 C14 C15 C16 139.02(19) . . . . ? C20 C15 C16 C17 2.1(3) . . . . ? C14 C15 C16 C17 -178.90(18) . . . . ? C15 C16 C17 C18 -1.2(3) . . . . ? C15 C16 C17 N2 176.04(18) . . . . ? O3 N2 C17 C16 178.90(19) . . . . ? O2 N2 C17 C16 -2.0(3) . . . . ? O3 N2 C17 C18 -3.7(3) . . . . ? O2 N2 C17 C18 175.42(19) . . . . ? C16 C17 C18 C19 -0.7(3) . . . . ? N2 C17 C18 C19 -177.96(18) . . . . ? C17 C18 C19 C20 1.8(3) . . . . ? C17 C18 C19 N3 178.62(18) . . . . ? O5 N3 C19 C18 165.7(2) . . . . ? O4 N3 C19 C18 -15.1(3) . . . . ? O5 N3 C19 C20 -17.2(3) . . . . ? O4 N3 C19 C20 161.89(19) . . . . ? C18 C19 C20 C15 -0.9(3) . . . . ? N3 C19 C20 C15 -177.75(17) . . . . ? C16 C15 C20 C19 -1.1(3) . . . . ? C14 C15 C20 C19 179.93(19) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.149 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.038 data_sw0404 _database_code_depnum_ccdc_archive 'CCDC 261091' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H25 N O2 S2' _chemical_formula_sum 'C20 H25 N O2 S2' _chemical_formula_weight 375.53 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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 15.717(3) _cell_length_b 6.1884(12) _cell_length_c 39.420(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3834.1(13) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 31876 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 11360 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5387 _reflns_number_gt 4382 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+1.2490P] 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 0.44(8) _refine_ls_number_reflns 5387 _refine_ls_number_parameters 457 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.008 _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 S1_1 S 0.30160(6) 0.56479(18) 0.60460(3) 0.0288(3) Uani 1 1 d . . . S2_1 S 0.41063(7) 0.80217(18) 0.71032(3) 0.0422(3) Uani 1 1 d . . . O1_1 O 0.36926(16) 0.6606(5) 0.58570(8) 0.0367(7) Uani 1 1 d . . . O2_1 O 0.29415(18) 0.3337(4) 0.60641(9) 0.0376(8) Uani 1 1 d . . . N1_1 N 0.3117(2) 0.6506(5) 0.64389(9) 0.0285(8) Uani 1 1 d . . . C1_1 C 0.3315(2) 0.8838(6) 0.64924(11) 0.0290(9) Uani 1 1 d . . . H1_1 H 0.3338 0.9553 0.6265 0.035 Uiso 1 1 calc R . . C2_1 C 0.2542(3) 0.9767(6) 0.66875(17) 0.0327(13) Uani 1 1 d . . . H2A_1 H 0.2722 1.0316 0.6912 0.039 Uiso 1 1 calc R . . H2B_1 H 0.2282 1.0972 0.6559 0.039 Uiso 1 1 calc R . . C3_1 C 0.1914(3) 0.7943(7) 0.67282(14) 0.0496(13) Uani 1 1 d . . . H3A_1 H 0.1457 0.8048 0.6556 0.059 Uiso 1 1 calc R . . H3B_1 H 0.1652 0.7977 0.6957 0.059 Uiso 1 1 calc R . . C4_1 C 0.2427(3) 0.5884(6) 0.66795(12) 0.0356(10) Uani 1 1 d . . . H4A_1 H 0.2667 0.5381 0.6898 0.043 Uiso 1 1 calc R . . H4B_1 H 0.2068 0.4722 0.6583 0.043 Uiso 1 1 calc R . . C5_1 C 0.4196(3) 0.9175(7) 0.66696(12) 0.0310(10) Uani 1 1 d . . . C6_1 C 0.4369(3) 1.1612(7) 0.66848(14) 0.0382(12) Uani 1 1 d . . . H6A_1 H 0.4362 1.2210 0.6455 0.057 Uiso 1 1 calc R . . H6B_1 H 0.4927 1.1867 0.6788 0.057 Uiso 1 1 calc R . . H6C_1 H 0.3928 1.2315 0.6821 0.057 Uiso 1 1 calc R . . C7_1 C 0.4898(3) 0.8049(7) 0.64730(12) 0.0363(10) Uani 1 1 d . . . H7A_1 H 0.4940 0.8681 0.6246 0.054 Uiso 1 1 calc R . . H7B_1 H 0.4766 0.6506 0.6454 0.054 Uiso 1 1 calc R . . H7C_1 H 0.5440 0.8234 0.6592 0.054 Uiso 1 1 calc R . . C8_1 C 0.5107(3) 0.8667(7) 0.72886(12) 0.0362(10) Uani 1 1 d . . . C9_1 C 0.5219(4) 1.0588(9) 0.74628(14) 0.0441(14) Uani 1 1 d . . . H9_1 H 0.4764 1.1596 0.7474 0.053 Uiso 1 1 calc R . . C10_1 C 0.5979(4) 1.1064(8) 0.76198(13) 0.0523(13) Uani 1 1 d . . . H10_1 H 0.6041 1.2387 0.7739 0.063 Uiso 1 1 calc R . . C11_1 C 0.6658(4) 0.9620(9) 0.76045(15) 0.0526(14) Uani 1 1 d . . . H11_1 H 0.7185 0.9942 0.7711 0.063 Uiso 1 1 calc R . . C12_1 C 0.6540(3) 0.7700(8) 0.74300(13) 0.0526(13) Uani 1 1 d . . . H12_1 H 0.6996 0.6694 0.7417 0.063 Uiso 1 1 calc R . . C13_1 C 0.5772(3) 0.7210(8) 0.72729(12) 0.0457(12) Uani 1 1 d . . . H13_1 H 0.5705 0.5880 0.7155 0.055 Uiso 1 1 calc R . . C14_1 C 0.2047(2) 0.6650(6) 0.58843(11) 0.0275(9) Uani 1 1 d . . . C15_1 C 0.2008(3) 0.8697(6) 0.57417(11) 0.0313(10) Uani 1 1 d . . . H15_1 H 0.2507 0.9556 0.5724 0.038 Uiso 1 1 calc R . . C16_1 C 0.1235(3) 0.9471(7) 0.56262(13) 0.0353(12) Uani 1 1 d . . . H16_1 H 0.1209 1.0868 0.5527 0.042 Uiso 1 1 calc R . . C17_1 C 0.0495(3) 0.8253(6) 0.56522(11) 0.0311(9) Uani 1 1 d . . . C18_1 C 0.0546(2) 0.6222(7) 0.57960(11) 0.0343(10) Uani 1 1 d . . . H18_1 H 0.0045 0.5375 0.5817 0.041 Uiso 1 1 calc R . . C19_1 C 0.1320(3) 0.5391(7) 0.59109(14) 0.0319(12) Uani 1 1 d . . . H19_1 H 0.1348 0.3982 0.6006 0.038 Uiso 1 1 calc R . . C20_1 C -0.0336(3) 0.9080(8) 0.55126(14) 0.0458(12) Uani 1 1 d . . . H20A_1 H -0.0275 1.0604 0.5450 0.069 Uiso 1 1 calc R . . H20B_1 H -0.0781 0.8936 0.5686 0.069 Uiso 1 1 calc R . . H20C_1 H -0.0494 0.8237 0.5312 0.069 Uiso 1 1 calc R . . S1_2 S 0.04801(6) 0.93932(18) 0.95444(3) 0.0290(3) Uani 1 1 d . . . S2_2 S 0.15910(7) 0.72543(18) 0.84936(3) 0.0418(3) Uani 1 1 d . . . O1_2 O 0.11676(16) 0.8435(4) 0.97332(8) 0.0342(7) Uani 1 1 d . . . O2_2 O 0.04029(18) 1.1701(4) 0.95306(8) 0.0364(7) Uani 1 1 d . . . N1_2 N 0.05775(19) 0.8550(5) 0.91519(9) 0.0255(7) Uani 1 1 d . . . C1_2 C 0.0802(2) 0.6238(6) 0.90925(10) 0.0274(9) Uani 1 1 d . . . H1_2 H 0.0829 0.5505 0.9318 0.033 Uiso 1 1 calc R . . C2_2 C 0.0024(4) 0.5317(7) 0.88992(18) 0.0430(16) Uani 1 1 d . . . H2A_2 H 0.0202 0.4753 0.8675 0.052 Uiso 1 1 calc R . . H2B_2 H -0.0237 0.4121 0.9030 0.052 Uiso 1 1 calc R . . C3_2 C -0.0603(3) 0.7119(7) 0.88552(16) 0.0574(15) Uani 1 1 d . . . H3A_2 H -0.1075 0.6979 0.9020 0.069 Uiso 1 1 calc R . . H3B_2 H -0.0844 0.7101 0.8623 0.069 Uiso 1 1 calc R . . C4_2 C -0.0113(3) 0.9189(7) 0.89161(12) 0.0372(10) Uani 1 1 d . . . H4A_2 H 0.0124 0.9759 0.8701 0.045 Uiso 1 1 calc R . . H4B_2 H -0.0482 1.0305 0.9020 0.045 Uiso 1 1 calc R . . C5_2 C 0.1672(3) 0.5946(6) 0.89182(11) 0.0272(10) Uani 1 1 d . . . C6_2 C 0.1848(3) 0.3538(7) 0.88864(14) 0.0415(13) Uani 1 1 d . . . H6A_2 H 0.1833 0.2871 0.9112 0.062 Uiso 1 1 calc R . . H6B_2 H 0.2410 0.3317 0.8785 0.062 Uiso 1 1 calc R . . H6C_2 H 0.1413 0.2873 0.8742 0.062 Uiso 1 1 calc R . . C7_2 C 0.2387(3) 0.7031(6) 0.91199(12) 0.0351(10) Uani 1 1 d . . . H7A_2 H 0.2397 0.6451 0.9351 0.053 Uiso 1 1 calc R . . H7B_2 H 0.2288 0.8594 0.9128 0.053 Uiso 1 1 calc R . . H7C_2 H 0.2934 0.6743 0.9010 0.053 Uiso 1 1 calc R . . C8_2 C 0.2593(3) 0.6670(7) 0.83035(11) 0.0368(10) Uani 1 1 d . . . C9_2 C 0.2707(5) 0.4766(8) 0.81237(17) 0.0477(16) Uani 1 1 d . . . H9_2 H 0.2255 0.3750 0.8110 0.057 Uiso 1 1 calc R . . C10_2 C 0.3477(4) 0.4326(10) 0.79621(14) 0.0579(14) Uani 1 1 d . . . H10_2 H 0.3560 0.2999 0.7846 0.069 Uiso 1 1 calc R . . C11_2 C 0.4103(4) 0.5819(10) 0.79742(15) 0.0598(15) Uani 1 1 d . . . H11_2 H 0.4623 0.5535 0.7860 0.072 Uiso 1 1 calc R . . C12_2 C 0.4012(4) 0.7732(9) 0.81462(14) 0.0593(15) Uani 1 1 d . . . H12_2 H 0.4463 0.8754 0.8151 0.071 Uiso 1 1 calc R . . C13_2 C 0.3244(3) 0.8156(8) 0.83141(12) 0.0486(12) Uani 1 1 d . . . H13_2 H 0.3172 0.9470 0.8435 0.058 Uiso 1 1 calc R . . C14_2 C -0.0479(2) 0.8371(6) 0.97060(10) 0.0267(9) Uani 1 1 d . . . C15_2 C -0.0508(3) 0.6320(6) 0.98501(11) 0.0326(10) Uani 1 1 d . . . H15_2 H -0.0003 0.5490 0.9872 0.039 Uiso 1 1 calc R . . C16_2 C -0.1284(3) 0.5486(7) 0.99631(12) 0.0290(10) Uani 1 1 d . . . H16_2 H -0.1306 0.4070 1.0055 0.035 Uiso 1 1 calc R . . C17_2 C -0.2026(3) 0.6716(7) 0.99415(10) 0.0314(10) Uani 1 1 d . . . C18_2 C -0.1984(3) 0.8788(7) 0.97973(11) 0.0364(10) Uani 1 1 d . . . H18_2 H -0.2487 0.9631 0.9779 0.044 Uiso 1 1 calc R . . C19_2 C -0.1226(3) 0.9616(7) 0.96816(14) 0.0323(12) Uani 1 1 d . . . H19_2 H -0.1207 1.1023 0.9586 0.039 Uiso 1 1 calc R . . C20_2 C -0.2862(3) 0.5848(8) 1.00689(13) 0.0434(12) Uani 1 1 d . . . H20A_2 H -0.2880 0.4280 1.0035 0.065 Uiso 1 1 calc R . . H20B_2 H -0.3329 0.6528 0.9944 0.065 Uiso 1 1 calc R . . H20C_2 H -0.2919 0.6170 1.0311 0.065 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_1 0.0243(5) 0.0270(5) 0.0350(7) -0.0003(6) -0.0014(5) 0.0027(5) S2_1 0.0379(7) 0.0554(7) 0.0333(7) 0.0083(5) -0.0022(5) -0.0100(5) O1_1 0.0295(17) 0.0429(17) 0.038(2) -0.0004(14) 0.0048(13) -0.0003(13) O2_1 0.0404(18) 0.0221(15) 0.050(2) -0.0020(16) -0.0029(15) 0.0079(12) N1_1 0.0263(18) 0.0259(18) 0.033(2) 0.0002(15) 0.0006(15) 0.0018(14) C1_1 0.024(2) 0.025(2) 0.039(3) 0.0021(17) -0.0018(18) 0.0004(16) C2_1 0.024(3) 0.030(2) 0.043(4) -0.004(2) 0.001(2) 0.0059(17) C3_1 0.042(3) 0.047(3) 0.059(4) -0.012(2) 0.019(2) -0.005(2) C4_1 0.037(3) 0.035(2) 0.034(3) 0.001(2) 0.0049(19) -0.009(2) C5_1 0.029(3) 0.035(3) 0.030(3) 0.0017(19) -0.001(2) -0.004(2) C6_1 0.032(3) 0.029(2) 0.053(3) -0.001(2) -0.006(2) -0.0062(19) C7_1 0.030(2) 0.041(2) 0.038(3) 0.0033(19) -0.0025(19) 0.0010(19) C8_1 0.033(3) 0.047(3) 0.029(3) 0.007(2) -0.0026(19) -0.002(2) C9_1 0.046(3) 0.052(3) 0.034(4) -0.009(3) 0.003(3) 0.004(3) C10_1 0.061(4) 0.061(3) 0.034(3) -0.004(3) -0.010(3) -0.006(3) C11_1 0.043(3) 0.080(4) 0.035(3) 0.004(3) -0.014(3) -0.005(3) C12_1 0.052(3) 0.066(3) 0.040(3) 0.002(2) -0.010(2) 0.016(3) C13_1 0.053(3) 0.047(3) 0.036(3) 0.002(2) -0.004(2) 0.006(2) C14_1 0.029(2) 0.025(2) 0.029(2) 0.0003(17) 0.0014(17) 0.0027(17) C15_1 0.029(2) 0.030(2) 0.034(3) 0.0004(17) -0.0005(18) -0.0052(18) C16_1 0.043(3) 0.029(2) 0.033(3) 0.002(2) -0.004(2) 0.005(2) C17_1 0.029(2) 0.038(2) 0.026(2) -0.0042(18) -0.0009(17) 0.0023(19) C18_1 0.020(2) 0.042(2) 0.041(3) -0.0004(19) 0.0002(18) -0.0059(18) C19_1 0.031(3) 0.029(2) 0.035(3) 0.004(2) 0.002(2) -0.0072(19) C20_1 0.035(3) 0.060(3) 0.042(3) -0.002(3) -0.003(2) 0.012(2) S1_2 0.0285(6) 0.0268(5) 0.0318(7) -0.0009(6) 0.0007(5) -0.0014(5) S2_2 0.0425(6) 0.0526(7) 0.0304(6) 0.0067(5) 0.0023(5) 0.0103(5) O1_2 0.0250(15) 0.0403(16) 0.0373(19) 0.0006(13) -0.0051(12) 0.0002(12) O2_2 0.0427(18) 0.0270(15) 0.040(2) -0.0030(16) 0.0049(14) -0.0020(13) N1_2 0.0274(18) 0.0204(16) 0.029(2) -0.0006(14) 0.0024(14) 0.0012(13) C1_2 0.028(2) 0.0205(19) 0.034(3) 0.0008(17) -0.0009(18) -0.0005(16) C2_2 0.038(3) 0.028(2) 0.063(5) -0.007(2) -0.002(3) -0.007(2) C3_2 0.048(3) 0.044(3) 0.080(4) -0.012(3) -0.026(3) 0.003(2) C4_2 0.032(2) 0.042(3) 0.037(3) 0.007(2) -0.0009(19) 0.007(2) C5_2 0.028(2) 0.026(2) 0.028(3) 0.0010(19) 0.0014(19) -0.0015(19) C6_2 0.040(3) 0.037(2) 0.048(3) 0.000(2) 0.006(2) 0.001(2) C7_2 0.025(2) 0.045(2) 0.035(3) 0.002(2) -0.0015(18) -0.0030(18) C8_2 0.042(3) 0.044(3) 0.025(3) 0.000(2) 0.0019(19) 0.003(2) C9_2 0.052(4) 0.057(3) 0.034(4) -0.005(2) 0.008(3) -0.004(2) C10_2 0.068(4) 0.067(4) 0.038(3) -0.010(3) 0.012(3) 0.007(3) C11_2 0.048(4) 0.088(4) 0.043(4) 0.008(3) 0.012(3) 0.014(3) C12_2 0.046(3) 0.085(4) 0.046(3) 0.015(3) 0.004(2) -0.021(3) C13_2 0.063(3) 0.056(3) 0.027(3) 0.004(2) 0.003(2) -0.012(2) C14_2 0.025(2) 0.026(2) 0.029(2) -0.0002(16) 0.0032(17) 0.0029(16) C15_2 0.034(2) 0.028(2) 0.036(3) -0.0002(17) -0.0012(19) 0.0041(19) C16_2 0.030(3) 0.026(2) 0.031(3) 0.000(2) -0.0002(19) -0.002(2) C17_2 0.029(2) 0.040(2) 0.025(3) -0.0037(18) 0.0009(17) -0.0070(19) C18_2 0.033(2) 0.044(3) 0.032(3) 0.0034(19) -0.0032(19) 0.009(2) C19_2 0.031(3) 0.031(2) 0.035(3) 0.003(2) 0.000(2) 0.0041(19) C20_2 0.031(2) 0.060(3) 0.039(3) 0.002(2) 0.006(2) -0.006(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 S1_1 O1_1 1.427(3) . ? S1_1 O2_1 1.437(3) . ? S1_1 N1_1 1.645(4) . ? S1_1 C14_1 1.764(4) . ? S2_1 C8_1 1.780(4) . ? S2_1 C5_1 1.858(5) . ? N1_1 C1_1 1.492(5) . ? N1_1 C4_1 1.492(5) . ? C1_1 C2_1 1.548(7) . ? C1_1 C5_1 1.565(6) . ? C1_1 H1_1 1.0000 . ? C2_1 C3_1 1.508(6) . ? C2_1 H2A_1 0.9900 . ? C2_1 H2B_1 0.9900 . ? C3_1 C4_1 1.520(6) . ? C3_1 H3A_1 0.9900 . ? C3_1 H3B_1 0.9900 . ? C4_1 H4A_1 0.9900 . ? C4_1 H4B_1 0.9900 . ? C5_1 C7_1 1.516(6) . ? C5_1 C6_1 1.533(6) . ? C6_1 H6A_1 0.9800 . ? C6_1 H6B_1 0.9800 . ? C6_1 H6C_1 0.9800 . ? C7_1 H7A_1 0.9800 . ? C7_1 H7B_1 0.9800 . ? C7_1 H7C_1 0.9800 . ? C8_1 C13_1 1.381(6) . ? C8_1 C9_1 1.384(7) . ? C9_1 C10_1 1.377(8) . ? C9_1 H9_1 0.9500 . ? C10_1 C11_1 1.393(8) . ? C10_1 H10_1 0.9500 . ? C11_1 C12_1 1.385(7) . ? C11_1 H11_1 0.9500 . ? C12_1 C13_1 1.390(7) . ? C12_1 H12_1 0.9500 . ? C13_1 H13_1 0.9500 . ? C14_1 C15_1 1.387(6) . ? C14_1 C19_1 1.387(6) . ? C15_1 C16_1 1.384(6) . ? C15_1 H15_1 0.9500 . ? C16_1 C17_1 1.389(6) . ? C16_1 H16_1 0.9500 . ? C17_1 C18_1 1.381(6) . ? C17_1 C20_1 1.507(6) . ? C18_1 C19_1 1.396(6) . ? C18_1 H18_1 0.9500 . ? C19_1 H19_1 0.9500 . ? C20_1 H20A_1 0.9800 . ? C20_1 H20B_1 0.9800 . ? C20_1 H20C_1 0.9800 . ? S1_2 O2_2 1.434(3) . ? S1_2 O1_2 1.440(3) . ? S1_2 N1_2 1.640(4) . ? S1_2 C14_2 1.754(4) . ? S2_2 C8_2 1.781(4) . ? S2_2 C5_2 1.864(5) . ? N1_2 C4_2 1.482(5) . ? N1_2 C1_2 1.492(5) . ? C1_2 C5_2 1.542(6) . ? C1_2 C2_2 1.549(7) . ? C1_2 H1_2 1.0000 . ? C2_2 C3_2 1.498(7) . ? C2_2 H2A_2 0.9900 . ? C2_2 H2B_2 0.9900 . ? C3_2 C4_2 1.515(6) . ? C3_2 H3A_2 0.9900 . ? C3_2 H3B_2 0.9900 . ? C4_2 H4A_2 0.9900 . ? C4_2 H4B_2 0.9900 . ? C5_2 C6_2 1.521(6) . ? C5_2 C7_2 1.532(6) . ? C6_2 H6A_2 0.9800 . ? C6_2 H6B_2 0.9800 . ? C6_2 H6C_2 0.9800 . ? C7_2 H7A_2 0.9800 . ? C7_2 H7B_2 0.9800 . ? C7_2 H7C_2 0.9800 . ? C8_2 C13_2 1.375(6) . ? C8_2 C9_2 1.387(7) . ? C9_2 C10_2 1.395(8) . ? C9_2 H9_2 0.9500 . ? C10_2 C11_2 1.351(9) . ? C10_2 H10_2 0.9500 . ? C11_2 C12_2 1.372(8) . ? C11_2 H11_2 0.9500 . ? C12_2 C13_2 1.402(7) . ? C12_2 H12_2 0.9500 . ? C13_2 H13_2 0.9500 . ? C14_2 C15_2 1.391(5) . ? C14_2 C19_2 1.408(6) . ? C15_2 C16_2 1.396(6) . ? C15_2 H15_2 0.9500 . ? C16_2 C17_2 1.396(6) . ? C16_2 H16_2 0.9500 . ? C17_2 C18_2 1.404(6) . ? C17_2 C20_2 1.505(6) . ? C18_2 C19_2 1.375(7) . ? C18_2 H18_2 0.9500 . ? C19_2 H19_2 0.9500 . ? C20_2 H20A_2 0.9800 . ? C20_2 H20B_2 0.9800 . ? C20_2 H20C_2 0.9800 . ? 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 O1_1 S1_1 O2_1 120.00(18) . . ? O1_1 S1_1 N1_1 106.60(18) . . ? O2_1 S1_1 N1_1 106.40(19) . . ? O1_1 S1_1 C14_1 107.98(19) . . ? O2_1 S1_1 C14_1 107.30(18) . . ? N1_1 S1_1 C14_1 108.08(18) . . ? C8_1 S2_1 C5_1 103.0(2) . . ? C1_1 N1_1 C4_1 108.1(3) . . ? C1_1 N1_1 S1_1 117.7(3) . . ? C4_1 N1_1 S1_1 116.4(3) . . ? N1_1 C1_1 C2_1 105.4(3) . . ? N1_1 C1_1 C5_1 112.1(3) . . ? C2_1 C1_1 C5_1 115.1(4) . . ? N1_1 C1_1 H1_1 108.0 . . ? C2_1 C1_1 H1_1 108.0 . . ? C5_1 C1_1 H1_1 108.0 . . ? C3_1 C2_1 C1_1 106.8(3) . . ? C3_1 C2_1 H2A_1 110.4 . . ? C1_1 C2_1 H2A_1 110.4 . . ? C3_1 C2_1 H2B_1 110.4 . . ? C1_1 C2_1 H2B_1 110.4 . . ? H2A_1 C2_1 H2B_1 108.6 . . ? C2_1 C3_1 C4_1 105.5(4) . . ? C2_1 C3_1 H3A_1 110.6 . . ? C4_1 C3_1 H3A_1 110.6 . . ? C2_1 C3_1 H3B_1 110.6 . . ? C4_1 C3_1 H3B_1 110.6 . . ? H3A_1 C3_1 H3B_1 108.8 . . ? N1_1 C4_1 C3_1 104.5(3) . . ? N1_1 C4_1 H4A_1 110.9 . . ? C3_1 C4_1 H4A_1 110.9 . . ? N1_1 C4_1 H4B_1 110.9 . . ? C3_1 C4_1 H4B_1 110.9 . . ? H4A_1 C4_1 H4B_1 108.9 . . ? C7_1 C5_1 C6_1 110.1(3) . . ? C7_1 C5_1 C1_1 110.8(4) . . ? C6_1 C5_1 C1_1 107.7(3) . . ? C7_1 C5_1 S2_1 110.4(3) . . ? C6_1 C5_1 S2_1 110.8(3) . . ? C1_1 C5_1 S2_1 107.0(3) . . ? C5_1 C6_1 H6A_1 109.5 . . ? C5_1 C6_1 H6B_1 109.5 . . ? H6A_1 C6_1 H6B_1 109.5 . . ? C5_1 C6_1 H6C_1 109.5 . . ? H6A_1 C6_1 H6C_1 109.5 . . ? H6B_1 C6_1 H6C_1 109.5 . . ? C5_1 C7_1 H7A_1 109.5 . . ? C5_1 C7_1 H7B_1 109.5 . . ? H7A_1 C7_1 H7B_1 109.5 . . ? C5_1 C7_1 H7C_1 109.5 . . ? H7A_1 C7_1 H7C_1 109.5 . . ? H7B_1 C7_1 H7C_1 109.5 . . ? C13_1 C8_1 C9_1 119.1(5) . . ? C13_1 C8_1 S2_1 120.2(4) . . ? C9_1 C8_1 S2_1 120.6(4) . . ? C10_1 C9_1 C8_1 121.1(5) . . ? C10_1 C9_1 H9_1 119.4 . . ? C8_1 C9_1 H9_1 119.4 . . ? C9_1 C10_1 C11_1 120.5(5) . . ? C9_1 C10_1 H10_1 119.8 . . ? C11_1 C10_1 H10_1 119.8 . . ? C12_1 C11_1 C10_1 118.0(5) . . ? C12_1 C11_1 H11_1 121.0 . . ? C10_1 C11_1 H11_1 121.0 . . ? C11_1 C12_1 C13_1 121.6(5) . . ? C11_1 C12_1 H12_1 119.2 . . ? C13_1 C12_1 H12_1 119.2 . . ? C8_1 C13_1 C12_1 119.6(5) . . ? C8_1 C13_1 H13_1 120.2 . . ? C12_1 C13_1 H13_1 120.2 . . ? C15_1 C14_1 C19_1 120.5(4) . . ? C15_1 C14_1 S1_1 120.3(3) . . ? C19_1 C14_1 S1_1 119.1(3) . . ? C16_1 C15_1 C14_1 119.2(4) . . ? C16_1 C15_1 H15_1 120.4 . . ? C14_1 C15_1 H15_1 120.4 . . ? C15_1 C16_1 C17_1 121.5(4) . . ? C15_1 C16_1 H16_1 119.2 . . ? C17_1 C16_1 H16_1 119.2 . . ? C18_1 C17_1 C16_1 118.4(4) . . ? C18_1 C17_1 C20_1 120.6(4) . . ? C16_1 C17_1 C20_1 120.9(4) . . ? C17_1 C18_1 C19_1 121.3(4) . . ? C17_1 C18_1 H18_1 119.4 . . ? C19_1 C18_1 H18_1 119.4 . . ? C14_1 C19_1 C18_1 119.1(4) . . ? C14_1 C19_1 H19_1 120.5 . . ? C18_1 C19_1 H19_1 120.5 . . ? C17_1 C20_1 H20A_1 109.5 . . ? C17_1 C20_1 H20B_1 109.5 . . ? H20A_1 C20_1 H20B_1 109.5 . . ? C17_1 C20_1 H20C_1 109.5 . . ? H20A_1 C20_1 H20C_1 109.5 . . ? H20B_1 C20_1 H20C_1 109.5 . . ? O2_2 S1_2 O1_2 119.55(18) . . ? O2_2 S1_2 N1_2 106.79(18) . . ? O1_2 S1_2 N1_2 106.66(18) . . ? O2_2 S1_2 C14_2 107.47(18) . . ? O1_2 S1_2 C14_2 107.98(19) . . ? N1_2 S1_2 C14_2 107.94(18) . . ? C8_2 S2_2 C5_2 103.2(2) . . ? C4_2 N1_2 C1_2 109.3(3) . . ? C4_2 N1_2 S1_2 116.0(3) . . ? C1_2 N1_2 S1_2 118.4(3) . . ? N1_2 C1_2 C5_2 113.1(3) . . ? N1_2 C1_2 C2_2 104.1(3) . . ? C5_2 C1_2 C2_2 116.0(4) . . ? N1_2 C1_2 H1_2 107.8 . . ? C5_2 C1_2 H1_2 107.8 . . ? C2_2 C1_2 H1_2 107.8 . . ? C3_2 C2_2 C1_2 107.6(4) . . ? C3_2 C2_2 H2A_2 110.2 . . ? C1_2 C2_2 H2A_2 110.2 . . ? C3_2 C2_2 H2B_2 110.2 . . ? C1_2 C2_2 H2B_2 110.2 . . ? H2A_2 C2_2 H2B_2 108.5 . . ? C2_2 C3_2 C4_2 106.0(4) . . ? C2_2 C3_2 H3A_2 110.5 . . ? C4_2 C3_2 H3A_2 110.5 . . ? C2_2 C3_2 H3B_2 110.5 . . ? C4_2 C3_2 H3B_2 110.5 . . ? H3A_2 C3_2 H3B_2 108.7 . . ? N1_2 C4_2 C3_2 104.3(3) . . ? N1_2 C4_2 H4A_2 110.9 . . ? C3_2 C4_2 H4A_2 110.9 . . ? N1_2 C4_2 H4B_2 110.9 . . ? C3_2 C4_2 H4B_2 110.9 . . ? H4A_2 C4_2 H4B_2 108.9 . . ? C6_2 C5_2 C7_2 109.9(3) . . ? C6_2 C5_2 C1_2 108.2(3) . . ? C7_2 C5_2 C1_2 111.6(4) . . ? C6_2 C5_2 S2_2 111.3(3) . . ? C7_2 C5_2 S2_2 109.0(3) . . ? C1_2 C5_2 S2_2 106.8(3) . . ? C5_2 C6_2 H6A_2 109.5 . . ? C5_2 C6_2 H6B_2 109.5 . . ? H6A_2 C6_2 H6B_2 109.5 . . ? C5_2 C6_2 H6C_2 109.5 . . ? H6A_2 C6_2 H6C_2 109.5 . . ? H6B_2 C6_2 H6C_2 109.5 . . ? C5_2 C7_2 H7A_2 109.5 . . ? C5_2 C7_2 H7B_2 109.5 . . ? H7A_2 C7_2 H7B_2 109.5 . . ? C5_2 C7_2 H7C_2 109.5 . . ? H7A_2 C7_2 H7C_2 109.5 . . ? H7B_2 C7_2 H7C_2 109.5 . . ? C13_2 C8_2 C9_2 119.2(5) . . ? C13_2 C8_2 S2_2 120.6(4) . . ? C9_2 C8_2 S2_2 120.1(4) . . ? C8_2 C9_2 C10_2 120.7(6) . . ? C8_2 C9_2 H9_2 119.6 . . ? C10_2 C9_2 H9_2 119.6 . . ? C11_2 C10_2 C9_2 118.9(5) . . ? C11_2 C10_2 H10_2 120.6 . . ? C9_2 C10_2 H10_2 120.6 . . ? C10_2 C11_2 C12_2 122.1(6) . . ? C10_2 C11_2 H11_2 118.9 . . ? C12_2 C11_2 H11_2 118.9 . . ? C11_2 C12_2 C13_2 119.0(5) . . ? C11_2 C12_2 H12_2 120.5 . . ? C13_2 C12_2 H12_2 120.5 . . ? C8_2 C13_2 C12_2 120.0(5) . . ? C8_2 C13_2 H13_2 120.0 . . ? C12_2 C13_2 H13_2 120.0 . . ? C15_2 C14_2 C19_2 120.0(4) . . ? C15_2 C14_2 S1_2 120.4(3) . . ? C19_2 C14_2 S1_2 119.6(3) . . ? C14_2 C15_2 C16_2 119.7(4) . . ? C14_2 C15_2 H15_2 120.1 . . ? C16_2 C15_2 H15_2 120.1 . . ? C17_2 C16_2 C15_2 120.6(4) . . ? C17_2 C16_2 H16_2 119.7 . . ? C15_2 C16_2 H16_2 119.7 . . ? C16_2 C17_2 C18_2 118.9(4) . . ? C16_2 C17_2 C20_2 121.0(4) . . ? C18_2 C17_2 C20_2 120.2(4) . . ? C19_2 C18_2 C17_2 121.1(4) . . ? C19_2 C18_2 H18_2 119.5 . . ? C17_2 C18_2 H18_2 119.5 . . ? C18_2 C19_2 C14_2 119.8(4) . . ? C18_2 C19_2 H19_2 120.1 . . ? C14_2 C19_2 H19_2 120.1 . . ? C17_2 C20_2 H20A_2 109.5 . . ? C17_2 C20_2 H20B_2 109.5 . . ? H20A_2 C20_2 H20B_2 109.5 . . ? C17_2 C20_2 H20C_2 109.5 . . ? H20A_2 C20_2 H20C_2 109.5 . . ? H20B_2 C20_2 H20C_2 109.5 . . ? 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 O1_1 S1_1 N1_1 C1_1 43.4(3) . . . . ? O2_1 S1_1 N1_1 C1_1 172.6(3) . . . . ? C14_1 S1_1 N1_1 C1_1 -72.5(3) . . . . ? O1_1 S1_1 N1_1 C4_1 174.3(3) . . . . ? O2_1 S1_1 N1_1 C4_1 -56.6(3) . . . . ? C14_1 S1_1 N1_1 C4_1 58.4(3) . . . . ? C4_1 N1_1 C1_1 C2_1 -17.5(4) . . . . ? S1_1 N1_1 C1_1 C2_1 117.0(4) . . . . ? C4_1 N1_1 C1_1 C5_1 108.4(4) . . . . ? S1_1 N1_1 C1_1 C5_1 -117.1(3) . . . . ? N1_1 C1_1 C2_1 C3_1 -1.9(5) . . . . ? C5_1 C1_1 C2_1 C3_1 -126.0(4) . . . . ? C1_1 C2_1 C3_1 C4_1 20.0(6) . . . . ? C1_1 N1_1 C4_1 C3_1 30.0(4) . . . . ? S1_1 N1_1 C4_1 C3_1 -105.2(4) . . . . ? C2_1 C3_1 C4_1 N1_1 -30.5(5) . . . . ? N1_1 C1_1 C5_1 C7_1 54.9(5) . . . . ? C2_1 C1_1 C5_1 C7_1 175.3(3) . . . . ? N1_1 C1_1 C5_1 C6_1 175.3(3) . . . . ? C2_1 C1_1 C5_1 C6_1 -64.2(5) . . . . ? N1_1 C1_1 C5_1 S2_1 -65.5(4) . . . . ? C2_1 C1_1 C5_1 S2_1 54.9(4) . . . . ? C8_1 S2_1 C5_1 C7_1 63.5(3) . . . . ? C8_1 S2_1 C5_1 C6_1 -58.7(3) . . . . ? C8_1 S2_1 C5_1 C1_1 -175.9(3) . . . . ? C5_1 S2_1 C8_1 C13_1 -92.6(4) . . . . ? C5_1 S2_1 C8_1 C9_1 90.2(5) . . . . ? C13_1 C8_1 C9_1 C10_1 0.0(8) . . . . ? S2_1 C8_1 C9_1 C10_1 177.2(4) . . . . ? C8_1 C9_1 C10_1 C11_1 0.5(9) . . . . ? C9_1 C10_1 C11_1 C12_1 -0.5(9) . . . . ? C10_1 C11_1 C12_1 C13_1 0.2(8) . . . . ? C9_1 C8_1 C13_1 C12_1 -0.3(7) . . . . ? S2_1 C8_1 C13_1 C12_1 -177.5(4) . . . . ? C11_1 C12_1 C13_1 C8_1 0.3(8) . . . . ? O1_1 S1_1 C14_1 C15_1 -29.6(4) . . . . ? O2_1 S1_1 C14_1 C15_1 -160.2(3) . . . . ? N1_1 S1_1 C14_1 C15_1 85.4(4) . . . . ? O1_1 S1_1 C14_1 C19_1 152.4(4) . . . . ? O2_1 S1_1 C14_1 C19_1 21.7(4) . . . . ? N1_1 S1_1 C14_1 C19_1 -92.7(4) . . . . ? C19_1 C14_1 C15_1 C16_1 0.0(7) . . . . ? S1_1 C14_1 C15_1 C16_1 -178.0(4) . . . . ? C14_1 C15_1 C16_1 C17_1 0.5(7) . . . . ? C15_1 C16_1 C17_1 C18_1 -0.3(7) . . . . ? C15_1 C16_1 C17_1 C20_1 -177.5(4) . . . . ? C16_1 C17_1 C18_1 C19_1 -0.5(7) . . . . ? C20_1 C17_1 C18_1 C19_1 176.7(5) . . . . ? C15_1 C14_1 C19_1 C18_1 -0.8(7) . . . . ? S1_1 C14_1 C19_1 C18_1 177.3(4) . . . . ? C17_1 C18_1 C19_1 C14_1 1.0(7) . . . . ? O2_2 S1_2 N1_2 C4_2 -56.2(3) . . . . ? O1_2 S1_2 N1_2 C4_2 174.9(3) . . . . ? C14_2 S1_2 N1_2 C4_2 59.0(3) . . . . ? O2_2 S1_2 N1_2 C1_2 170.8(3) . . . . ? O1_2 S1_2 N1_2 C1_2 41.9(3) . . . . ? C14_2 S1_2 N1_2 C1_2 -73.9(3) . . . . ? C4_2 N1_2 C1_2 C5_2 108.3(4) . . . . ? S1_2 N1_2 C1_2 C5_2 -116.0(3) . . . . ? C4_2 N1_2 C1_2 C2_2 -18.5(4) . . . . ? S1_2 N1_2 C1_2 C2_2 117.3(4) . . . . ? N1_2 C1_2 C2_2 C3_2 0.3(6) . . . . ? C5_2 C1_2 C2_2 C3_2 -124.6(5) . . . . ? C1_2 C2_2 C3_2 C4_2 17.3(7) . . . . ? C1_2 N1_2 C4_2 C3_2 29.4(5) . . . . ? S1_2 N1_2 C4_2 C3_2 -107.6(4) . . . . ? C2_2 C3_2 C4_2 N1_2 -28.2(6) . . . . ? N1_2 C1_2 C5_2 C6_2 177.4(3) . . . . ? C2_2 C1_2 C5_2 C6_2 -62.4(5) . . . . ? N1_2 C1_2 C5_2 C7_2 56.4(4) . . . . ? C2_2 C1_2 C5_2 C7_2 176.6(3) . . . . ? N1_2 C1_2 C5_2 S2_2 -62.6(4) . . . . ? C2_2 C1_2 C5_2 S2_2 57.5(4) . . . . ? C8_2 S2_2 C5_2 C6_2 -58.3(3) . . . . ? C8_2 S2_2 C5_2 C7_2 63.1(3) . . . . ? C8_2 S2_2 C5_2 C1_2 -176.2(3) . . . . ? C5_2 S2_2 C8_2 C13_2 -96.6(4) . . . . ? C5_2 S2_2 C8_2 C9_2 87.7(5) . . . . ? C13_2 C8_2 C9_2 C10_2 1.6(9) . . . . ? S2_2 C8_2 C9_2 C10_2 177.4(5) . . . . ? C8_2 C9_2 C10_2 C11_2 -2.2(9) . . . . ? C9_2 C10_2 C11_2 C12_2 1.4(9) . . . . ? C10_2 C11_2 C12_2 C13_2 -0.2(9) . . . . ? C9_2 C8_2 C13_2 C12_2 -0.4(7) . . . . ? S2_2 C8_2 C13_2 C12_2 -176.2(4) . . . . ? C11_2 C12_2 C13_2 C8_2 -0.3(8) . . . . ? O2_2 S1_2 C14_2 C15_2 -159.2(3) . . . . ? O1_2 S1_2 C14_2 C15_2 -29.0(4) . . . . ? N1_2 S1_2 C14_2 C15_2 86.0(4) . . . . ? O2_2 S1_2 C14_2 C19_2 22.4(4) . . . . ? O1_2 S1_2 C14_2 C19_2 152.6(4) . . . . ? N1_2 S1_2 C14_2 C19_2 -92.4(4) . . . . ? C19_2 C14_2 C15_2 C16_2 1.4(7) . . . . ? S1_2 C14_2 C15_2 C16_2 -177.0(3) . . . . ? C14_2 C15_2 C16_2 C17_2 -1.8(7) . . . . ? C15_2 C16_2 C17_2 C18_2 1.4(7) . . . . ? C15_2 C16_2 C17_2 C20_2 -178.8(4) . . . . ? C16_2 C17_2 C18_2 C19_2 -0.6(7) . . . . ? C20_2 C17_2 C18_2 C19_2 179.6(5) . . . . ? C17_2 C18_2 C19_2 C14_2 0.3(8) . . . . ? C15_2 C14_2 C19_2 C18_2 -0.7(7) . . . . ? S1_2 C14_2 C19_2 C18_2 177.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.288 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.045 data_sw0406 _database_code_depnum_ccdc_archive 'CCDC 261092' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H20 Cl N S' _chemical_formula_weight 257.81 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 8.5638(3) _cell_length_b 14.0302(5) _cell_length_c 23.1201(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2777.92(18) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 108549 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.818 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 13217 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3144 _reflns_number_gt 2519 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1130P)^2^+1.3114P] 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_number_reflns 3144 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.2037 _refine_ls_wR_factor_gt 0.1926 _refine_ls_goodness_of_fit_ref 1.189 _refine_ls_restrained_S_all 1.189 _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 Cl1 Cl 0.21399(8) 0.33116(5) 0.46733(3) 0.0386(3) Uani 1 1 d . . . S1 S 0.04001(11) 0.19749(5) 0.68592(3) 0.0452(3) Uani 1 1 d . . . N1 N 0.3594(3) 0.18526(15) 0.55286(10) 0.0329(5) Uani 1 1 d . . . H1A H 0.3144 0.2282 0.5279 0.040 Uiso 1 1 calc R . . H1B H 0.4655 0.1956 0.5521 0.040 Uiso 1 1 calc R . . C1 C 0.3010(3) 0.20649(19) 0.61346(12) 0.0337(6) Uani 1 1 d . . . C2 C 0.1250(3) 0.18342(17) 0.61377(11) 0.0315(6) Uani 1 1 d . . . H2 H 0.0719 0.2296 0.5874 0.038 Uiso 1 1 calc R . . C3 C 0.0877(3) 0.08269(19) 0.59229(13) 0.0387(6) Uani 1 1 d . . . H3A H 0.1320 0.0353 0.6194 0.046 Uiso 1 1 calc R . . H3B H -0.0269 0.0736 0.5911 0.046 Uiso 1 1 calc R . . C4 C 0.1555(4) 0.0670(2) 0.53229(13) 0.0415(7) Uani 1 1 d . . . H4A H 0.1364 0.0002 0.5203 0.050 Uiso 1 1 calc R . . H4B H 0.1016 0.1093 0.5044 0.050 Uiso 1 1 calc R . . C5 C 0.3285(3) 0.0869(2) 0.53049(13) 0.0390(7) Uani 1 1 d . . . H5A H 0.3847 0.0396 0.5545 0.047 Uiso 1 1 calc R . . H5B H 0.3669 0.0813 0.4902 0.047 Uiso 1 1 calc R . . C6 C 0.3296(4) 0.3130(2) 0.62258(15) 0.0455(7) Uani 1 1 d . . . H6A H 0.4403 0.3272 0.6162 0.068 Uiso 1 1 calc R . . H6B H 0.3009 0.3304 0.6622 0.068 Uiso 1 1 calc R . . H6C H 0.2661 0.3495 0.5952 0.068 Uiso 1 1 calc R . . C7 C 0.3958(4) 0.1483(3) 0.65623(14) 0.0499(8) Uani 1 1 d . . . H7A H 0.5071 0.1618 0.6508 0.075 Uiso 1 1 calc R . . H7B H 0.3764 0.0803 0.6497 0.075 Uiso 1 1 calc R . . H7C H 0.3651 0.1652 0.6957 0.075 Uiso 1 1 calc R . . C8 C -0.0458(3) 0.3129(2) 0.68481(12) 0.0351(6) Uani 1 1 d . . . C9 C -0.1516(4) 0.3398(2) 0.64249(14) 0.0436(7) Uani 1 1 d . . . H9 H -0.1767 0.2972 0.6119 0.052 Uiso 1 1 calc R . . C10 C -0.2206(4) 0.4291(3) 0.64498(18) 0.0539(9) Uani 1 1 d . . . H10 H -0.2901 0.4486 0.6152 0.065 Uiso 1 1 calc R . . C11 C -0.1888(4) 0.4896(2) 0.69034(19) 0.0574(10) Uani 1 1 d . . . H11 H -0.2384 0.5501 0.6923 0.069 Uiso 1 1 calc R . . C12 C -0.0855(5) 0.4626(2) 0.73277(16) 0.0570(10) Uani 1 1 d . . . H12 H -0.0646 0.5044 0.7642 0.068 Uiso 1 1 calc R . . C13 C -0.0114(4) 0.3745(2) 0.73012(13) 0.0449(7) Uani 1 1 d . . . H13 H 0.0621 0.3567 0.7590 0.054 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 Cl1 0.0329(4) 0.0351(4) 0.0477(4) 0.0008(3) -0.0033(3) 0.0009(3) S1 0.0639(6) 0.0298(4) 0.0420(4) 0.0083(3) 0.0146(3) 0.0085(3) N1 0.0287(12) 0.0278(11) 0.0423(12) -0.0004(9) -0.0009(9) -0.0007(9) C1 0.0371(15) 0.0284(13) 0.0356(14) 0.0002(10) -0.0029(11) -0.0011(10) C2 0.0362(14) 0.0225(12) 0.0359(13) 0.0021(10) 0.0020(11) 0.0018(10) C3 0.0337(15) 0.0252(13) 0.0571(17) -0.0012(12) 0.0028(13) -0.0027(11) C4 0.0430(17) 0.0272(13) 0.0543(17) -0.0117(12) -0.0032(13) 0.0000(12) C5 0.0365(16) 0.0299(14) 0.0506(17) -0.0088(12) 0.0018(12) 0.0044(11) C6 0.056(2) 0.0329(15) 0.0477(17) -0.0065(13) -0.0006(14) -0.0139(13) C7 0.0459(19) 0.056(2) 0.0481(18) 0.0076(14) -0.0105(14) 0.0060(15) C8 0.0404(16) 0.0244(13) 0.0405(15) -0.0016(10) 0.0110(11) -0.0045(11) C9 0.0427(18) 0.0386(16) 0.0495(17) -0.0080(13) 0.0002(13) 0.0042(13) C10 0.046(2) 0.0470(19) 0.069(2) 0.0013(16) 0.0056(15) 0.0119(15) C11 0.057(2) 0.0266(15) 0.088(3) -0.0036(16) 0.031(2) 0.0018(14) C12 0.075(2) 0.0328(16) 0.063(2) -0.0175(15) 0.0240(19) -0.0135(16) C13 0.0540(19) 0.0399(17) 0.0407(16) -0.0055(13) 0.0055(14) -0.0094(14) _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 C8 1.778(3) . ? S1 C2 1.831(3) . ? N1 C5 1.498(3) . ? N1 C1 1.517(4) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? C1 C7 1.518(4) . ? C1 C6 1.528(4) . ? C1 C2 1.541(4) . ? C2 C3 1.532(4) . ? C2 H2 1.0000 . ? C3 C4 1.520(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.508(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.385(4) . ? C8 C13 1.390(4) . ? C9 C10 1.387(4) . ? C9 H9 0.9500 . ? C10 C11 1.377(6) . ? C10 H10 0.9500 . ? C11 C12 1.374(6) . ? C11 H11 0.9500 . ? C12 C13 1.390(5) . ? C12 H12 0.9500 . ? 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 C8 S1 C2 104.44(12) . . ? C5 N1 C1 116.2(2) . . ? C5 N1 H1A 108.2 . . ? C1 N1 H1A 108.2 . . ? C5 N1 H1B 108.2 . . ? C1 N1 H1B 108.2 . . ? H1A N1 H1B 107.4 . . ? N1 C1 C7 108.6(2) . . ? N1 C1 C6 105.4(2) . . ? C7 C1 C6 110.5(3) . . ? N1 C1 C2 106.6(2) . . ? C7 C1 C2 114.0(2) . . ? C6 C1 C2 111.2(2) . . ? C3 C2 C1 113.3(2) . . ? C3 C2 S1 108.18(18) . . ? C1 C2 S1 111.74(19) . . ? C3 C2 H2 107.8 . . ? C1 C2 H2 107.8 . . ? S1 C2 H2 107.8 . . ? C4 C3 C2 110.5(2) . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 111.9(2) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N1 C5 C4 109.6(2) . . ? N1 C5 H5A 109.8 . . ? C4 C5 H5A 109.8 . . ? N1 C5 H5B 109.8 . . ? C4 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 120.1(3) . . ? C9 C8 S1 121.9(2) . . ? C13 C8 S1 117.9(2) . . ? C8 C9 C10 119.7(3) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.5(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 119.3(3) . . ? C12 C13 H13 120.4 . . ? C8 C13 H13 120.4 . . ? 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 C5 N1 C1 C7 68.1(3) . . . . ? C5 N1 C1 C6 -173.5(2) . . . . ? C5 N1 C1 C2 -55.2(3) . . . . ? N1 C1 C2 C3 53.4(3) . . . . ? C7 C1 C2 C3 -66.5(3) . . . . ? C6 C1 C2 C3 167.8(2) . . . . ? N1 C1 C2 S1 175.92(16) . . . . ? C7 C1 C2 S1 56.1(3) . . . . ? C6 C1 C2 S1 -69.6(3) . . . . ? C8 S1 C2 C3 -136.9(2) . . . . ? C8 S1 C2 C1 97.7(2) . . . . ? C1 C2 C3 C4 -55.6(3) . . . . ? S1 C2 C3 C4 179.9(2) . . . . ? C2 C3 C4 C5 55.1(3) . . . . ? C1 N1 C5 C4 57.0(3) . . . . ? C3 C4 C5 N1 -54.6(3) . . . . ? C2 S1 C8 C9 53.8(3) . . . . ? C2 S1 C8 C13 -130.2(2) . . . . ? C13 C8 C9 C10 1.2(5) . . . . ? S1 C8 C9 C10 177.1(3) . . . . ? C8 C9 C10 C11 -2.4(5) . . . . ? C9 C10 C11 C12 1.5(5) . . . . ? C10 C11 C12 C13 0.5(5) . . . . ? C11 C12 C13 C8 -1.6(5) . . . . ? C9 C8 C13 C12 0.8(5) . . . . ? S1 C8 C13 C12 -175.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.713 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.097