data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ;Stereoselective synthesis of 3,4-disubstituted and 3,4,5-trisubstituted piperidines by Lewis acid-catalysed ene cyclisation of 4-aza-1,7-dienes ; _publ_contact_author_name J.Snaith _publ_contact_author_email J.S.SNAITH@BHAM.AC.UK loop_ _publ_author_name J.Snaith B.M.Kariuki A.G.Russell S.M.Walker J.T.Williams data_global _journal_coden_Cambridge 24 _journal_volume 46 _journal_page_first 6611 _journal_year 2005 loop_ _publ_author_name S.M.Walker J.T.Williams A.G.Russell J.S.Snaith _publ_contact_author_name 'John S. Snaith' _publ_contact_author_email j.s.snaith@bham.ac.uk # Attachment 'jtw55.cif' data_jtw55 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H31 N O6 S' _chemical_formula_weight 437.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.2895(6) _cell_length_b 10.2232(5) _cell_length_c 22.4956(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.284(2) _cell_angle_gamma 90.00 _cell_volume 2359.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.520 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6261 _exptl_absorpt_correction_T_max 0.9702 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8325 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 4.75 _diffrn_reflns_theta_max 70.14 _reflns_number_total 3020 _reflns_number_gt 2180 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0810P)^2^+0.4298P] 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 3020 _refine_ls_number_parameters 304 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1469 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.028 _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 N1 N 0.5028(2) 0.19802(19) 0.79103(9) 0.0607(6) Uani 1 1 d . A 1 O1 O 0.6863(2) 0.1422(2) 0.86298(10) 0.0878(6) Uani 1 1 d . A 1 O2 O 0.5590(2) -0.03294(19) 0.81043(10) 0.0942(7) Uani 1 1 d . A 1 O3 O 0.5339(2) 0.4432(2) 0.61266(10) 0.0897(7) Uani 1 1 d . A 1 O4 O 0.3503(3) 0.3685(3) 0.56690(11) 0.1177(9) Uani 1 1 d . A 1 O5 O 0.1154(3) 0.4240(3) 0.65161(12) 0.1183(9) Uani 1 1 d . A 1 O6 O 0.1878(5) 0.5935(6) 0.6004(4) 0.090(2) Uani 0.543(10) 1 d PD A 1 O6A O 0.1718(7) 0.6300(9) 0.6341(4) 0.104(3) Uani 0.457(10) 1 d PD A 1 S1 S 0.56358(7) 0.09169(7) 0.83937(3) 0.0711(3) Uani 1 1 d . A 1 C1 C 0.5083(3) 0.3371(2) 0.80898(11) 0.0609(7) Uani 1 1 d . A 1 H1A H 0.5901 0.3549 0.8318 0.073 Uiso 1 1 calc R A 1 H1B H 0.4378 0.3564 0.8339 0.073 Uiso 1 1 calc R A 1 C2 C 0.4964(3) 0.4234(2) 0.75323(11) 0.0588(7) Uani 1 1 d . A 1 H2 H 0.5670 0.3995 0.7284 0.071 Uiso 1 1 calc R A 1 C3 C 0.3664(3) 0.3939(2) 0.71746(12) 0.0615(7) Uani 1 1 d . A 1 H3 H 0.2965 0.4139 0.7434 0.074 Uiso 1 1 calc R A 1 C4 C 0.3580(3) 0.2481(2) 0.70318(12) 0.0678(8) Uani 1 1 d . A 1 H4A H 0.2732 0.2292 0.6832 0.081 Uiso 1 1 calc R A 1 H4B H 0.4236 0.2262 0.6761 0.081 Uiso 1 1 calc R A 1 C5 C 0.3777(3) 0.1639(3) 0.75838(12) 0.0682(8) Uani 1 1 d . A 1 H5A H 0.3068 0.1780 0.7838 0.082 Uiso 1 1 calc R A 1 H5B H 0.3779 0.0723 0.7471 0.082 Uiso 1 1 calc R A 1 C6 C 0.4587(3) 0.0855(3) 0.89722(13) 0.0683(8) Uani 1 1 d . A 1 C7 C 0.4824(4) 0.1632(3) 0.94650(16) 0.0887(10) Uani 1 1 d . A 1 H7 H 0.5556 0.2168 0.9498 0.106 Uiso 1 1 calc R A 1 C8 C 0.3979(5) 0.1618(4) 0.99105(17) 0.1082(12) Uani 1 1 d . A 1 H8 H 0.4158 0.2142 1.0245 0.130 Uiso 1 1 calc R A 1 C9 C 0.2885(5) 0.0857(5) 0.9876(2) 0.1083(13) Uani 1 1 d . A 1 C10 C 0.2649(4) 0.0082(4) 0.9378(2) 0.1112(13) Uani 1 1 d . A 1 H10 H 0.1910 -0.0444 0.9345 0.133 Uiso 1 1 calc R A 1 C11 C 0.3492(3) 0.0068(3) 0.89242(15) 0.0877(10) Uani 1 1 d . A 1 H11 H 0.3323 -0.0464 0.8592 0.105 Uiso 1 1 calc R A 1 C12 C 0.1954(5) 0.0845(5) 1.0370(2) 0.167(2) Uani 1 1 d . A 1 H12A H 0.1107 0.0566 1.0210 0.200 Uiso 1 1 calc R A 1 H12B H 0.1894 0.1708 1.0533 0.200 Uiso 1 1 calc R A 1 H12C H 0.2272 0.0251 1.0678 0.200 Uiso 1 1 calc R A 1 C13 C 0.5144(3) 0.5658(3) 0.77082(13) 0.0718(8) Uani 1 1 d . A 1 C14 C 0.6173(3) 0.6327(3) 0.75441(16) 0.0972(11) Uani 1 1 d . A 1 H14A H 0.6283 0.7199 0.7655 0.117 Uiso 1 1 calc R A 1 H14B H 0.6779 0.5922 0.7319 0.117 Uiso 1 1 calc R A 1 C15 C 0.4170(4) 0.6275(3) 0.8064(2) 0.1207(14) Uani 1 1 d . A 1 H15A H 0.4418 0.7165 0.8149 0.145 Uiso 1 1 calc R A 1 H15B H 0.4124 0.5804 0.8431 0.145 Uiso 1 1 calc R A 1 H15C H 0.3333 0.6258 0.7845 0.145 Uiso 1 1 calc R A 1 C16 C 0.3435(3) 0.4797(3) 0.66110(14) 0.0723(8) Uani 1 1 d . A 1 H16 H 0.3816 0.5659 0.6701 0.087 Uiso 1 1 calc R A 1 C17 C 0.4070(3) 0.4246(3) 0.60813(15) 0.0795(9) Uani 1 1 d . A 1 C18 C 0.6084(4) 0.3886(4) 0.56570(16) 0.1107(12) Uani 1 1 d . A 1 H18A H 0.5604 0.3986 0.5272 0.133 Uiso 1 1 calc R A 1 H18B H 0.6243 0.2962 0.5727 0.133 Uiso 1 1 calc R A 1 C19 C 0.7336(5) 0.4606(5) 0.5667(2) 0.1370(16) Uani 1 1 d . A 1 H19A H 0.7169 0.5510 0.5574 0.164 Uiso 1 1 calc R A 1 H19B H 0.7868 0.4236 0.5377 0.164 Uiso 1 1 calc R A 1 H19C H 0.7782 0.4538 0.6056 0.164 Uiso 1 1 calc R A 1 C20 C 0.1998(4) 0.4984(4) 0.64346(17) 0.0956(11) Uani 1 1 d . A 1 C21 C 0.0585(6) 0.6171(9) 0.5700(3) 0.115(4) Uani 0.543(10) 1 d PD A 1 H21A H 0.0099 0.5360 0.5652 0.138 Uiso 0.543(10) 1 calc PR A 1 H21B H 0.0665 0.6554 0.5310 0.138 Uiso 0.543(10) 1 calc PR A 1 C22 C -0.0085(8) 0.7106(10) 0.6097(5) 0.144(5) Uani 0.543(10) 1 d PD A 1 H22A H -0.0325 0.6651 0.6445 0.173 Uiso 0.543(10) 1 calc PR A 1 H22B H -0.0852 0.7452 0.5884 0.173 Uiso 0.543(10) 1 calc PR A 1 H22C H 0.0498 0.7810 0.6213 0.173 Uiso 0.543(10) 1 calc PR A 1 C21A C 0.0312(7) 0.6531(14) 0.6224(4) 0.162(7) Uani 0.457(10) 1 d PD A 1 H21C H 0.0024 0.7227 0.6476 0.195 Uiso 0.457(10) 1 calc PR A 1 H21D H -0.0178 0.5745 0.6298 0.195 Uiso 0.457(10) 1 calc PR A 1 C22A C 0.0129(11) 0.6915(17) 0.5575(4) 0.168(7) Uani 0.457(10) 1 d PD A 1 H22D H 0.0853 0.7439 0.5473 0.201 Uiso 0.457(10) 1 calc PR A 1 H22E H -0.0663 0.7407 0.5507 0.201 Uiso 0.457(10) 1 calc PR A 1 H22F H 0.0079 0.6141 0.5332 0.201 Uiso 0.457(10) 1 calc PR A 1 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 N1 0.0608(15) 0.0537(13) 0.0679(14) 0.0043(10) 0.0066(10) -0.0007(9) O1 0.0555(14) 0.0972(15) 0.1097(16) 0.0224(12) 0.0001(11) 0.0041(10) O2 0.1161(19) 0.0584(13) 0.1101(16) 0.0003(12) 0.0214(13) 0.0193(11) O3 0.0662(17) 0.1157(17) 0.0880(15) 0.0083(12) 0.0099(12) -0.0076(12) O4 0.097(2) 0.178(2) 0.0767(16) 0.0040(16) -0.0059(14) -0.0276(17) O5 0.0634(18) 0.131(2) 0.158(2) 0.0400(17) -0.0050(15) -0.0129(14) O6 0.071(3) 0.082(4) 0.115(5) 0.013(3) -0.010(3) 0.019(2) O6A 0.080(4) 0.095(5) 0.138(7) 0.013(5) 0.004(4) 0.029(3) S1 0.0671(6) 0.0636(5) 0.0836(5) 0.0104(4) 0.0120(4) 0.0077(3) C1 0.0566(18) 0.0584(17) 0.0680(17) -0.0041(13) 0.0059(13) -0.0025(11) C2 0.0520(18) 0.0542(16) 0.0708(17) 0.0008(12) 0.0091(13) -0.0016(11) C3 0.0501(18) 0.0631(17) 0.0721(17) 0.0052(13) 0.0098(13) -0.0026(11) C4 0.066(2) 0.0667(18) 0.0695(18) 0.0003(14) -0.0002(14) -0.0081(13) C5 0.072(2) 0.0582(16) 0.0745(19) 0.0000(13) 0.0063(14) -0.0121(13) C6 0.064(2) 0.0680(18) 0.0734(19) 0.0160(15) 0.0052(14) 0.0033(13) C7 0.089(3) 0.095(2) 0.083(2) 0.0065(19) 0.012(2) 0.0038(18) C8 0.119(4) 0.127(3) 0.081(3) 0.011(2) 0.018(3) 0.029(3) C9 0.094(3) 0.141(4) 0.094(3) 0.056(3) 0.029(3) 0.041(3) C10 0.076(3) 0.133(3) 0.126(3) 0.059(3) 0.017(3) -0.003(2) C11 0.082(3) 0.092(2) 0.089(2) 0.0262(18) 0.0074(19) -0.0098(18) C12 0.139(4) 0.235(6) 0.136(4) 0.097(4) 0.068(3) 0.075(4) C13 0.069(2) 0.0577(17) 0.088(2) 0.0007(14) 0.0023(16) -0.0026(14) C14 0.079(3) 0.068(2) 0.145(3) 0.000(2) 0.008(2) -0.0171(16) C15 0.132(4) 0.073(2) 0.163(4) -0.027(2) 0.048(3) -0.001(2) C16 0.055(2) 0.0711(18) 0.089(2) 0.0171(16) -0.0011(15) -0.0036(13) C17 0.068(3) 0.095(2) 0.075(2) 0.0266(17) -0.0021(18) -0.0118(16) C18 0.092(3) 0.154(4) 0.087(3) 0.009(2) 0.019(2) 0.009(2) C19 0.092(4) 0.185(4) 0.138(4) 0.053(3) 0.034(3) 0.012(3) C20 0.064(3) 0.093(3) 0.127(3) 0.026(2) -0.010(2) -0.0013(18) C21 0.086(7) 0.106(6) 0.146(10) -0.006(5) -0.027(6) 0.032(4) C22 0.143(10) 0.112(8) 0.173(14) -0.031(8) -0.012(8) 0.043(6) C21A 0.112(11) 0.139(12) 0.226(16) 0.025(12) -0.048(11) 0.057(9) C22A 0.099(10) 0.254(18) 0.150(11) 0.047(13) 0.009(9) 0.038(10) _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 N1 C5 1.476(3) . ? N1 C1 1.478(3) . ? N1 S1 1.629(2) . ? O1 S1 1.429(2) . ? O2 S1 1.430(2) . ? O3 C17 1.315(4) . ? O3 C18 1.461(4) . ? O4 C17 1.204(4) . ? O5 C20 1.178(4) . ? O6 C20 1.372(7) . ? O6 C21 1.4699(11) . ? O6A C20 1.388(9) . ? O6A C21A 1.4700(11) . ? S1 C6 1.753(3) . ? C1 C2 1.531(3) . ? C2 C13 1.516(4) . ? C2 C3 1.538(3) . ? C3 C4 1.525(3) . ? C3 C16 1.545(4) . ? C4 C5 1.512(3) . ? C6 C7 1.371(4) . ? C6 C11 1.381(4) . ? C7 C8 1.375(5) . ? C8 C9 1.366(6) . ? C9 C10 1.380(6) . ? C9 C12 1.520(6) . ? C10 C11 1.388(5) . ? C13 C14 1.336(4) . ? C13 C15 1.471(5) . ? C16 C17 1.510(5) . ? C16 C20 1.514(4) . ? C18 C19 1.483(6) . ? C21 C22 1.5086(11) . ? C21A C22A 1.5090(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 C5 N1 C1 112.16(19) . . ? C5 N1 S1 116.86(16) . . ? C1 N1 S1 117.04(16) . . ? C17 O3 C18 117.4(3) . . ? C20 O6 C21 118.4(6) . . ? C20 O6A C21A 111.9(7) . . ? O1 S1 O2 119.29(13) . . ? O1 S1 N1 106.93(11) . . ? O2 S1 N1 107.02(12) . . ? O1 S1 C6 108.25(14) . . ? O2 S1 C6 107.74(14) . . ? N1 S1 C6 107.03(12) . . ? N1 C1 C2 109.4(2) . . ? C13 C2 C1 109.8(2) . . ? C13 C2 C3 114.2(2) . . ? C1 C2 C3 109.2(2) . . ? C4 C3 C2 109.6(2) . . ? C4 C3 C16 112.3(2) . . ? C2 C3 C16 113.0(2) . . ? C5 C4 C3 112.4(2) . . ? N1 C5 C4 109.4(2) . . ? C7 C6 C11 119.7(3) . . ? C7 C6 S1 119.8(3) . . ? C11 C6 S1 120.4(3) . . ? C6 C7 C8 120.0(4) . . ? C9 C8 C7 121.9(4) . . ? C8 C9 C10 117.9(4) . . ? C8 C9 C12 121.7(5) . . ? C10 C9 C12 120.4(5) . . ? C9 C10 C11 121.4(4) . . ? C6 C11 C10 119.2(3) . . ? C14 C13 C15 121.1(3) . . ? C14 C13 C2 120.2(3) . . ? C15 C13 C2 118.6(3) . . ? C17 C16 C20 108.2(3) . . ? C17 C16 C3 112.8(2) . . ? C20 C16 C3 111.9(3) . . ? O4 C17 O3 123.4(4) . . ? O4 C17 C16 124.9(3) . . ? O3 C17 C16 111.7(3) . . ? O3 C18 C19 107.6(3) . . ? O5 C20 O6 122.6(4) . . ? O5 C20 O6A 120.1(4) . . ? O6 C20 O6A 36.9(3) . . ? O5 C20 C16 126.4(3) . . ? O6 C20 C16 108.0(4) . . ? O6A C20 C16 110.5(4) . . ? O6 C21 C22 105.46(10) . . ? O6A C21A C22A 105.44(10) . . ? _diffrn_measured_fraction_theta_max 0.671 _diffrn_reflns_theta_full 70.14 _diffrn_measured_fraction_theta_full 0.671 _refine_diff_density_max 0.219 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.034 # Attachment 'jtw54.cif' data_jtw54 _database_code_depnum_ccdc_archive 'CCDC 649646' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H35 N O10 S' _chemical_formula_sum 'C27 H35 N O10 S' _chemical_formula_weight 565.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0618(2) _cell_length_b 17.0577(2) _cell_length_c 16.0387(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.5090(10) _cell_angle_gamma 90.00 _cell_volume 2916.13(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3116 _cell_measurement_theta_min 3.86 _cell_measurement_theta_max 71.86 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.459 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7591 _exptl_absorpt_correction_T_max 0.8679 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16860 _diffrn_reflns_av_R_equivalents 0.0827 _diffrn_reflns_av_sigmaI/netI 0.0809 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 71.24 _reflns_number_total 5381 _reflns_number_gt 3116 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution SHELXL _computing_structure_refinement SHELXL _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1860P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5381 _refine_ls_number_parameters 358 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1213 _refine_ls_R_factor_gt 0.0885 _refine_ls_wR_factor_ref 0.2724 _refine_ls_wR_factor_gt 0.2425 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.954 _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 C1 C 0.7397(3) 0.01592(19) 0.9094(2) 0.0598(8) Uani 1 1 d . . . H1A H 0.6704 0.0492 0.8798 0.072 Uiso 1 1 calc R . . H1B H 0.7063 -0.0276 0.9352 0.072 Uiso 1 1 calc R . . C2 C 0.8082(3) -0.01426(17) 0.8461(2) 0.0530(8) Uani 1 1 d . . . H2 H 0.8802 -0.0447 0.8791 0.064 Uiso 1 1 calc R . . C3 C 0.8593(3) 0.05317(18) 0.8026(2) 0.0555(8) Uani 1 1 d . . . H3 H 0.7883 0.0853 0.7709 0.067 Uiso 1 1 calc R . . C4 C 0.9454(3) 0.10440(19) 0.8729(2) 0.0594(9) Uani 1 1 d . . . H4 H 1.0176 0.0721 0.9021 0.071 Uiso 1 1 calc R . . C5 C 0.8796(4) 0.12929(19) 0.9413(2) 0.0679(10) Uani 1 1 d . . . H5A H 0.9387 0.1568 0.9877 0.081 Uiso 1 1 calc R . . H5B H 0.8117 0.1650 0.9156 0.081 Uiso 1 1 calc R . . C6 C 0.6698(3) 0.1479(2) 1.0430(2) 0.0604(8) Uani 1 1 d . . . C7 C 0.7016(3) 0.2271(2) 1.0554(3) 0.0688(10) Uani 1 1 d . . . H7 H 0.7849 0.2420 1.0777 0.083 Uiso 1 1 calc R . . C8 C 0.6085(4) 0.2829(2) 1.0343(3) 0.0750(11) Uani 1 1 d . . . H8 H 0.6296 0.3356 1.0425 0.090 Uiso 1 1 calc R . . C9 C 0.4831(4) 0.2617(3) 1.0006(3) 0.0755(11) Uani 1 1 d . . . C10 C 0.4552(4) 0.1828(3) 0.9889(3) 0.0830(12) Uani 1 1 d . . . H10 H 0.3721 0.1677 0.9662 0.100 Uiso 1 1 calc R . . C11 C 0.5463(4) 0.1261(2) 1.0097(3) 0.0753(10) Uani 1 1 d . . . H11 H 0.5250 0.0734 1.0014 0.090 Uiso 1 1 calc R . . C12 C 0.3835(5) 0.3246(3) 0.9784(4) 0.1145(18) Uani 1 1 d . . . H12A H 0.3755 0.3430 0.9206 0.172 Uiso 1 1 calc R . . H12B H 0.4070 0.3675 1.0183 0.172 Uiso 1 1 calc R . . H12C H 0.3048 0.3034 0.9821 0.172 Uiso 1 1 calc R . . C13 C 0.7274(3) -0.06888(19) 0.7775(2) 0.0597(9) Uani 1 1 d . . . C14 C 0.6053(4) -0.0274(2) 0.7242(3) 0.0732(11) Uani 1 1 d D . . C15 C 0.3918(5) 0.0007(3) 0.7221(5) 0.137(2) Uani 1 1 d D . . H15A H 0.3588 0.0284 0.7640 0.165 Uiso 1 1 calc R . . H15B H 0.3975 0.0373 0.6770 0.165 Uiso 1 1 calc R . . C16 C 0.3088(6) -0.0638(4) 0.6849(8) 0.204(5) Uani 1 1 d D . . H16A H 0.3176 -0.0756 0.6282 0.306 Uiso 1 1 calc R . . H16B H 0.2235 -0.0493 0.6806 0.306 Uiso 1 1 calc R . . H16C H 0.3305 -0.1092 0.7212 0.306 Uiso 1 1 calc R . . C17 C 0.6945(4) -0.1449(2) 0.8162(3) 0.0688(10) Uani 1 1 d D . . C18 C 0.5810(5) -0.2636(3) 0.7798(4) 0.126(2) Uani 1 1 d D . . H18A H 0.6399 -0.3027 0.7708 0.151 Uiso 1 1 calc R . . H18B H 0.5835 -0.2635 0.8407 0.151 Uiso 1 1 calc R . . C19 C 0.4562(5) -0.2830(4) 0.7288(5) 0.149(3) Uani 1 1 d D . . H19A H 0.3986 -0.2433 0.7364 0.224 Uiso 1 1 calc R . . H19B H 0.4319 -0.3327 0.7471 0.224 Uiso 1 1 calc R . . H19C H 0.4552 -0.2858 0.6688 0.224 Uiso 1 1 calc R . . C20 C 0.9273(3) 0.0224(2) 0.7384(2) 0.0619(9) Uani 1 1 d . . . H20 H 1.0146 0.0132 0.7709 0.074 Uiso 1 1 calc R . . C21 C 0.8783(5) -0.0544(3) 0.6932(3) 0.0810(11) Uani 1 1 d . . . C22 C 0.9301(4) 0.0779(3) 0.6658(3) 0.0888(13) Uani 1 1 d D . . C23 C 1.0282(9) 0.1079(4) 0.5537(4) 0.190(4) Uani 1 1 d D . . H23A H 1.0812 0.0803 0.5241 0.228 Uiso 1 1 calc R . . H23B H 0.9432 0.1107 0.5166 0.228 Uiso 1 1 calc R . . C24 C 1.0772(7) 0.1843(5) 0.5829(7) 0.171(3) Uani 1 1 d D . . H24A H 1.0198 0.2110 0.6087 0.256 Uiso 1 1 calc R . . H24B H 1.0876 0.2142 0.5346 0.256 Uiso 1 1 calc R . . H24C H 1.1568 0.1788 0.6249 0.256 Uiso 1 1 calc R . . C25 C 0.9960(4) 0.1761(2) 0.8373(3) 0.0745(11) Uani 1 1 d . . . C26 C 1.1170(4) 0.1787(3) 0.8385(4) 0.1123(19) Uani 1 1 d . . . H26A H 1.1486 0.2220 0.8161 0.135 Uiso 1 1 calc R . . H26B H 1.1698 0.1372 0.8619 0.135 Uiso 1 1 calc R . . C27 C 0.9101(5) 0.2405(2) 0.8009(4) 0.0972(15) Uani 1 1 d . . . H27A H 0.8837 0.2660 0.8465 0.146 Uiso 1 1 calc R . . H27B H 0.8382 0.2201 0.7589 0.146 Uiso 1 1 calc R . . H27C H 0.9525 0.2777 0.7737 0.146 Uiso 1 1 calc R . . O1 O 0.7377(3) 0.00495(15) 1.08755(18) 0.0882(9) Uani 1 1 d . . . O2 O 0.8971(3) 0.10964(17) 1.12747(17) 0.0868(9) Uani 1 1 d . . . O3 O 0.5999(3) 0.0039(2) 0.6573(2) 0.1124(12) Uani 1 1 d . . . O4 O 0.5175(3) -0.03127(19) 0.7646(2) 0.0952(10) Uani 1 1 d D . . O5 O 0.7337(3) -0.16416(15) 0.8893(2) 0.0889(9) Uani 1 1 d . . . O6 O 0.6168(3) -0.18718(15) 0.75527(19) 0.0942(10) Uani 1 1 d D . . O7 O 0.7945(3) -0.09686(14) 0.71894(17) 0.0750(8) Uani 1 1 d . . . O8 O 0.9173(5) -0.0800(2) 0.6361(3) 0.1374(17) Uani 1 1 d . . . O9 O 0.8467(3) 0.1225(2) 0.6355(2) 0.1165(13) Uani 1 1 d . . . O10 O 1.0328(4) 0.0722(3) 0.6389(3) 0.1421(18) Uani 1 1 d D . . S1 S 0.78867(10) 0.07700(5) 1.06671(6) 0.0690(4) Uani 1 1 d . . . N1 N 0.8294(3) 0.06096(16) 0.97701(19) 0.0617(8) Uani 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 C1 0.059(2) 0.0567(16) 0.059(2) -0.0034(14) 0.0083(17) -0.0042(14) C2 0.0512(17) 0.0526(15) 0.0504(18) 0.0006(13) 0.0050(15) -0.0022(13) C3 0.0516(18) 0.0551(16) 0.054(2) 0.0061(14) 0.0033(16) -0.0002(13) C4 0.0518(18) 0.0583(17) 0.059(2) 0.0049(15) -0.0008(17) -0.0038(14) C5 0.069(2) 0.0573(17) 0.066(2) -0.0011(15) -0.0012(19) -0.0049(16) C6 0.058(2) 0.0679(19) 0.0513(19) -0.0041(15) 0.0074(16) -0.0012(16) C7 0.056(2) 0.072(2) 0.070(2) -0.0089(17) 0.0021(18) 0.0045(16) C8 0.076(3) 0.067(2) 0.076(3) 0.0003(18) 0.012(2) 0.0101(18) C9 0.063(2) 0.104(3) 0.057(2) 0.006(2) 0.0115(19) 0.020(2) C10 0.056(2) 0.113(3) 0.074(3) -0.003(2) 0.007(2) -0.007(2) C11 0.064(2) 0.080(2) 0.078(3) -0.0044(19) 0.012(2) -0.0089(19) C12 0.092(3) 0.145(4) 0.098(4) 0.024(3) 0.011(3) 0.053(3) C13 0.059(2) 0.0617(18) 0.054(2) -0.0044(14) 0.0082(17) -0.0073(15) C14 0.067(2) 0.069(2) 0.069(3) 0.0005(18) -0.007(2) -0.0114(18) C15 0.076(3) 0.127(5) 0.176(7) -0.014(4) -0.023(4) 0.022(3) C16 0.081(4) 0.172(7) 0.310(13) -0.063(7) -0.032(6) -0.005(4) C17 0.074(2) 0.0619(19) 0.067(3) -0.0062(17) 0.012(2) -0.0068(17) C18 0.149(5) 0.079(3) 0.129(5) 0.011(3) 0.002(4) -0.050(3) C19 0.127(5) 0.132(5) 0.160(6) 0.035(4) -0.012(5) -0.062(4) C20 0.0552(19) 0.0667(19) 0.061(2) 0.0129(16) 0.0097(17) 0.0038(15) C21 0.092(3) 0.084(3) 0.071(3) -0.003(2) 0.029(3) 0.001(2) C22 0.080(3) 0.092(3) 0.092(3) 0.031(2) 0.018(3) 0.011(2) C23 0.249(11) 0.174(7) 0.196(9) 0.045(7) 0.144(9) 0.001(8) C24 0.121(5) 0.150(6) 0.236(10) 0.000(6) 0.040(6) -0.013(5) C25 0.067(2) 0.069(2) 0.076(3) 0.0066(18) -0.002(2) -0.0143(17) C26 0.067(3) 0.108(3) 0.146(5) 0.041(3) 0.003(3) -0.021(2) C27 0.099(3) 0.065(2) 0.118(4) 0.024(2) 0.011(3) -0.004(2) O1 0.127(3) 0.0710(16) 0.0698(18) 0.0118(13) 0.0318(18) 0.0129(15) O2 0.0779(18) 0.1031(19) 0.0576(16) -0.0109(14) -0.0196(14) 0.0259(15) O3 0.103(3) 0.123(2) 0.085(2) 0.0343(19) -0.0205(19) -0.008(2) O4 0.0587(17) 0.110(2) 0.106(2) 0.0016(18) 0.0036(18) 0.0084(15) O5 0.112(2) 0.0725(16) 0.0700(19) 0.0080(13) 0.0039(17) -0.0157(15) O6 0.112(2) 0.0743(16) 0.0784(19) -0.0016(13) -0.0058(17) -0.0335(15) O7 0.0898(19) 0.0731(15) 0.0656(17) -0.0134(12) 0.0269(15) -0.0120(13) O8 0.189(4) 0.136(3) 0.120(3) -0.037(2) 0.098(4) -0.030(3) O9 0.102(2) 0.123(3) 0.117(3) 0.060(2) 0.016(2) 0.030(2) O10 0.125(3) 0.158(4) 0.171(4) 0.087(3) 0.087(3) 0.039(3) S1 0.0796(7) 0.0686(5) 0.0510(6) 0.0008(4) 0.0037(5) 0.0138(4) N1 0.0638(17) 0.0637(15) 0.0520(17) -0.0016(12) 0.0059(14) 0.0004(13) _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 1.475(4) . ? C1 C2 1.510(5) . ? C2 C3 1.530(4) . ? C2 C13 1.533(4) . ? C3 C20 1.521(5) . ? C3 C4 1.539(4) . ? C4 C25 1.518(5) . ? C4 C5 1.529(5) . ? C5 N1 1.472(4) . ? C6 C11 1.378(5) . ? C6 C7 1.397(5) . ? C6 S1 1.752(4) . ? C7 C8 1.376(5) . ? C8 C9 1.396(6) . ? C9 C10 1.381(6) . ? C9 C12 1.511(6) . ? C10 C11 1.372(6) . ? C13 O7 1.426(4) . ? C13 C17 1.524(5) . ? C13 C14 1.561(5) . ? C14 O3 1.185(5) . ? C14 O4 1.307(5) . ? C15 C16 1.455(3) . ? C15 O4 1.480(5) . ? C17 O5 1.183(5) . ? C17 O6 1.328(4) . ? C18 C19 1.442(3) . ? C18 O6 1.447(4) . ? C20 C22 1.508(5) . ? C20 C21 1.524(6) . ? C21 O8 1.195(5) . ? C21 O7 1.327(5) . ? C22 O9 1.194(5) . ? C22 O10 1.322(5) . ? C23 C24 1.441(3) . ? C23 O10 1.484(5) . ? C25 C26 1.335(6) . ? C25 C27 1.468(6) . ? O1 S1 1.428(3) . ? O2 S1 1.440(3) . ? S1 N1 1.641(3) . ? 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 108.2(3) . . ? C1 C2 C3 111.3(3) . . ? C1 C2 C13 112.9(3) . . ? C3 C2 C13 110.2(3) . . ? C20 C3 C2 111.0(3) . . ? C20 C3 C4 111.8(3) . . ? C2 C3 C4 108.9(3) . . ? C25 C4 C5 109.9(3) . . ? C25 C4 C3 113.5(3) . . ? C5 C4 C3 111.3(3) . . ? N1 C5 C4 111.1(3) . . ? C11 C6 C7 120.2(3) . . ? C11 C6 S1 120.4(3) . . ? C7 C6 S1 119.4(3) . . ? C8 C7 C6 119.3(3) . . ? C7 C8 C9 121.2(4) . . ? C10 C9 C8 117.9(4) . . ? C10 C9 C12 122.6(4) . . ? C8 C9 C12 119.6(4) . . ? C11 C10 C9 122.0(4) . . ? C10 C11 C6 119.5(4) . . ? O7 C13 C17 101.9(3) . . ? O7 C13 C2 111.7(3) . . ? C17 C13 C2 112.5(3) . . ? O7 C13 C14 108.5(3) . . ? C17 C13 C14 110.0(3) . . ? C2 C13 C14 111.7(3) . . ? O3 C14 O4 127.4(4) . . ? O3 C14 C13 121.8(4) . . ? O4 C14 C13 110.7(3) . . ? C16 C15 O4 108.8(5) . . ? O5 C17 O6 124.9(4) . . ? O5 C17 C13 125.2(3) . . ? O6 C17 C13 109.9(3) . . ? C19 C18 O6 110.0(4) . . ? C22 C20 C3 114.9(3) . . ? C22 C20 C21 104.5(4) . . ? C3 C20 C21 116.2(3) . . ? O8 C21 O7 117.7(4) . . ? O8 C21 C20 121.6(4) . . ? O7 C21 C20 120.7(4) . . ? O9 C22 O10 123.5(4) . . ? O9 C22 C20 122.8(4) . . ? O10 C22 C20 113.7(4) . . ? C24 C23 O10 99.0(6) . . ? C26 C25 C27 121.4(4) . . ? C26 C25 C4 119.4(4) . . ? C27 C25 C4 119.2(3) . . ? C14 O4 C15 119.0(4) . . ? C17 O6 C18 117.3(3) . . ? C21 O7 C13 123.5(3) . . ? C22 O10 C23 116.6(5) . . ? O1 S1 O2 118.93(18) . . ? O1 S1 N1 106.23(16) . . ? O2 S1 N1 106.47(17) . . ? O1 S1 C6 108.95(18) . . ? O2 S1 C6 108.73(16) . . ? N1 S1 C6 106.89(16) . . ? C5 N1 C1 112.1(3) . . ? C5 N1 S1 115.4(2) . . ? C1 N1 S1 116.3(2) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 71.24 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.496 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.074 # Attachment 'swm118.cif' data_swm118 _database_code_depnum_ccdc_archive 'CCDC 649647' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H23 N O4 S' _chemical_formula_sum 'C17 H23 N O4 S' _chemical_formula_weight 337.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 6.1394(8) _cell_length_b 21.563(3) _cell_length_c 13.0265(14) _cell_angle_alpha 90.00 _cell_angle_beta 102.480(8) _cell_angle_gamma 90.00 _cell_volume 1683.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 726 _cell_measurement_theta_min 3.47 _cell_measurement_theta_max 41.59 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 1.877 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.5678 _exptl_absorpt_correction_T_max 0.9634 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4093 _diffrn_reflns_av_R_equivalents 0.0841 _diffrn_reflns_av_sigmaI/netI 0.0940 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 41.59 _reflns_number_total 1101 _reflns_number_gt 726 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1061P)^2^+10.0728P] 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 SHELXL _refine_ls_extinction_coef 0.0033(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1101 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1303 _refine_ls_R_factor_gt 0.0894 _refine_ls_wR_factor_ref 0.2425 _refine_ls_wR_factor_gt 0.2196 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.003 _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 0.851(3) 0.1532(7) 0.5674(11) 0.044(4) Uani 1 1 d . . . C2 C 0.653(3) 0.1839(7) 0.5724(15) 0.054(4) Uani 1 1 d . . . H2 H 0.5630 0.1985 0.5103 0.064 Uiso 1 1 calc R . . C3 C 0.586(3) 0.1933(6) 0.6634(17) 0.052(5) Uani 1 1 d . . . H3 H 0.4527 0.2139 0.6624 0.063 Uiso 1 1 calc R . . C4 C 0.714(4) 0.1729(7) 0.7578(15) 0.056(5) Uani 1 1 d . . . C5 C 0.911(4) 0.1430(8) 0.7546(14) 0.069(5) Uani 1 1 d . . . H5 H 1.0018 0.1303 0.8178 0.083 Uiso 1 1 calc R . . C6 C 0.981(3) 0.1306(7) 0.6615(16) 0.061(5) Uani 1 1 d . . . H6 H 1.1105 0.1082 0.6621 0.073 Uiso 1 1 calc R . . C7 C 0.641(3) 0.1829(7) 0.8581(12) 0.090(6) Uani 1 1 d . . . H7A H 0.7488 0.1654 0.9152 0.135 Uiso 1 1 calc R . . H7B H 0.4989 0.1633 0.8543 0.135 Uiso 1 1 calc R . . H7C H 0.6273 0.2266 0.8697 0.135 Uiso 1 1 calc R . . C8 C 0.549(3) 0.1359(7) 0.3084(11) 0.062(5) Uani 1 1 d . . . H8A H 0.5991 0.1765 0.2912 0.074 Uiso 1 1 calc R . . H8B H 0.4307 0.1416 0.3465 0.074 Uiso 1 1 calc R . . C9 C 0.462(2) 0.0993(7) 0.2085(12) 0.058(4) Uani 1 1 d . . . H9 H 0.5899 0.0943 0.1755 0.069 Uiso 1 1 calc R . . C10 C 0.395(2) 0.0336(6) 0.2332(11) 0.041(4) Uani 1 1 d . . . H10 H 0.2675 0.0374 0.2668 0.049 Uiso 1 1 calc R . . C11 C 0.583(3) 0.0022(6) 0.3127(12) 0.061(5) Uani 1 1 d . . . H11A H 0.5282 -0.0362 0.3361 0.073 Uiso 1 1 calc R . . H11B H 0.7039 -0.0079 0.2782 0.073 Uiso 1 1 calc R . . C12 C 0.674(3) 0.0423(8) 0.4072(12) 0.070(5) Uani 1 1 d . . . H12A H 0.5614 0.0472 0.4489 0.084 Uiso 1 1 calc R . . H12B H 0.8035 0.0228 0.4508 0.084 Uiso 1 1 calc R . . C13 C 0.284(3) 0.1294(7) 0.1271(12) 0.046(4) Uani 1 1 d . . . C14 C 0.259(2) 0.0313(11) 0.0300(16) 0.063(5) Uani 1 1 d . . . C15 C 0.317(3) -0.0041(8) 0.1325(13) 0.077(5) Uani 1 1 d . . . H15A H 0.4337 -0.0336 0.1274 0.092 Uiso 1 1 calc R . . H15B H 0.1871 -0.0278 0.1397 0.092 Uiso 1 1 calc R . . C16 C 0.355(3) 0.1916(7) 0.0929(11) 0.074(5) Uani 1 1 d . . . H16A H 0.2349 0.2096 0.0421 0.111 Uiso 1 1 calc R . . H16B H 0.4825 0.1864 0.0620 0.111 Uiso 1 1 calc R . . H16C H 0.3935 0.2185 0.1528 0.111 Uiso 1 1 calc R . . C17 C 0.059(2) 0.1323(8) 0.1591(11) 0.087(6) Uani 1 1 d . . . H17A H 0.0218 0.0918 0.1809 0.130 Uiso 1 1 calc R . . H17B H -0.0535 0.1458 0.1004 0.130 Uiso 1 1 calc R . . H17C H 0.0684 0.1609 0.2163 0.130 Uiso 1 1 calc R . . N1 N 0.733(2) 0.1018(6) 0.3732(9) 0.053(3) Uani 1 1 d . . . O1 O 0.9538(16) 0.1979(5) 0.4000(7) 0.069(3) Uani 1 1 d . . . O2 O 1.1223(17) 0.0998(5) 0.4712(7) 0.083(4) Uani 1 1 d . . . O3 O 0.2457(16) 0.0933(7) 0.0293(7) 0.064(3) Uani 1 1 d . . . O4 O 0.2149(17) 0.0041(6) -0.0551(9) 0.082(4) Uani 1 1 d . . . S1 S 0.9346(7) 0.1390(2) 0.4486(3) 0.0585(17) Uani 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 C1 0.060(12) 0.057(11) 0.012(11) -0.011(9) 0.002(9) -0.002(10) C2 0.058(13) 0.032(10) 0.067(17) -0.019(9) 0.004(10) 0.003(9) C3 0.076(13) 0.042(10) 0.043(11) -0.026(11) 0.020(14) 0.014(9) C4 0.074(14) 0.044(11) 0.046(16) -0.007(10) 0.007(13) 0.024(10) C5 0.091(17) 0.066(13) 0.036(15) 0.008(10) -0.015(11) -0.003(12) C6 0.072(12) 0.072(13) 0.040(12) -0.007(11) 0.012(13) 0.001(9) C7 0.148(17) 0.081(13) 0.052(12) -0.008(10) 0.044(12) 0.010(12) C8 0.085(13) 0.057(11) 0.037(10) -0.014(10) 0.002(10) 0.001(11) C9 0.057(11) 0.066(13) 0.058(12) -0.004(11) 0.028(10) 0.017(10) C10 0.056(10) 0.023(9) 0.046(11) 0.004(9) 0.011(9) 0.001(8) C11 0.070(12) 0.041(10) 0.072(11) 0.013(11) 0.016(10) -0.005(10) C12 0.079(12) 0.044(12) 0.075(13) 0.011(11) -0.011(10) -0.006(9) C13 0.066(12) 0.032(11) 0.033(10) 0.000(10) -0.001(10) 0.025(9) C14 0.045(11) 0.083(18) 0.059(17) -0.008(16) 0.010(10) -0.011(11) C15 0.073(12) 0.079(13) 0.076(14) -0.012(14) 0.011(11) -0.007(10) C16 0.104(13) 0.065(13) 0.053(11) 0.022(10) 0.016(10) 0.014(10) C17 0.054(12) 0.142(17) 0.057(11) -0.009(11) -0.005(9) 0.044(11) N1 0.056(9) 0.046(9) 0.047(8) 0.011(8) -0.006(8) -0.001(8) O1 0.091(8) 0.068(8) 0.045(6) -0.006(6) 0.009(6) -0.018(6) O2 0.053(7) 0.119(10) 0.071(8) -0.019(7) 0.002(6) 0.026(8) O3 0.086(8) 0.060(9) 0.042(8) 0.003(8) 0.004(6) -0.004(6) O4 0.079(8) 0.106(10) 0.061(8) -0.042(8) 0.014(7) -0.007(7) S1 0.057(3) 0.071(4) 0.044(3) -0.010(3) 0.004(2) 0.001(3) _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 C6 1.398(18) . ? C1 C2 1.397(18) . ? C1 S1 1.761(14) . ? C2 C3 1.349(17) . ? C3 C4 1.381(18) . ? C4 C5 1.38(2) . ? C4 C7 1.487(19) . ? C5 C6 1.40(2) . ? C8 N1 1.458(16) . ? C8 C9 1.517(17) . ? C9 C13 1.496(17) . ? C9 C10 1.528(17) . ? C10 C15 1.529(17) . ? C10 C11 1.533(17) . ? C11 C12 1.508(17) . ? C12 N1 1.431(15) . ? C13 O3 1.468(15) . ? C13 C16 1.507(17) . ? C13 C17 1.527(18) . ? C14 O4 1.231(17) . ? C14 O3 1.338(19) . ? C14 C15 1.51(2) . ? N1 S1 1.614(12) . ? O1 S1 1.436(10) . ? O2 S1 1.408(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 117.6(13) . . ? C6 C1 S1 119.3(15) . . ? C2 C1 S1 123.1(16) . . ? C3 C2 C1 122.9(14) . . ? C2 C3 C4 120.8(14) . . ? C3 C4 C5 117.1(14) . . ? C3 C4 C7 121.0(19) . . ? C5 C4 C7 121.9(19) . . ? C4 C5 C6 123.5(14) . . ? C1 C6 C5 118.0(14) . . ? N1 C8 C9 108.6(12) . . ? C13 C9 C8 116.7(13) . . ? C13 C9 C10 111.3(13) . . ? C8 C9 C10 111.2(12) . . ? C9 C10 C15 111.1(12) . . ? C9 C10 C11 110.7(12) . . ? C15 C10 C11 113.3(12) . . ? C12 C11 C10 112.9(11) . . ? N1 C12 C11 109.5(12) . . ? O3 C13 C9 109.9(11) . . ? O3 C13 C16 102.6(12) . . ? C9 C13 C16 112.5(13) . . ? O3 C13 C17 105.9(12) . . ? C9 C13 C17 112.8(12) . . ? C16 C13 C17 112.4(12) . . ? O4 C14 O3 118.0(17) . . ? O4 C14 C15 121.2(19) . . ? O3 C14 C15 120.8(17) . . ? C14 C15 C10 117.4(14) . . ? C12 N1 C8 114.3(11) . . ? C12 N1 S1 118.0(11) . . ? C8 N1 S1 119.9(10) . . ? C14 O3 C13 121.7(13) . . ? O2 S1 O1 118.8(7) . . ? O2 S1 N1 108.3(7) . . ? O1 S1 N1 107.2(6) . . ? O2 S1 C1 107.6(8) . . ? O1 S1 C1 107.5(7) . . ? N1 S1 C1 106.9(7) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 41.59 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.418 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.073 # Attachment 'smw137.cif' data_smw137 _database_code_depnum_ccdc_archive 'CCDC 649648' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H21 N O4 S' _chemical_formula_sum 'C16 H21 N O4 S' _chemical_formula_weight 323.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6072(3) _cell_length_b 12.0948(4) _cell_length_c 17.8368(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.330(2) _cell_angle_gamma 90.00 _cell_volume 1631.11(10) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2513 _cell_measurement_theta_min 4.43 _cell_measurement_theta_max 70.38 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.916 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5537 _exptl_absorpt_correction_T_max 0.7006 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10303 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.43 _diffrn_reflns_theta_max 70.38 _reflns_number_total 3014 _reflns_number_gt 2513 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0617P)^2^+0.3571P] 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 3014 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C1 C 0.1515(2) 0.24524(14) 0.12282(10) 0.0369(4) Uani 1 1 d . . . C2 C 0.0977(2) 0.27922(15) 0.04984(10) 0.0429(4) Uani 1 1 d . . . H2 H 0.0255 0.2341 0.0174 0.051 Uiso 1 1 calc R . . C3 C 0.1523(3) 0.38127(15) 0.02544(11) 0.0463(4) Uani 1 1 d . . . H3 H 0.1170 0.4039 -0.0238 0.056 Uiso 1 1 calc R . . C4 C 0.2591(2) 0.45029(15) 0.07339(12) 0.0455(4) Uani 1 1 d . . . C5 C 0.3145(2) 0.41336(16) 0.14576(11) 0.0460(4) Uani 1 1 d . . . H5 H 0.3879 0.4582 0.1780 0.055 Uiso 1 1 calc R . . C6 C 0.2634(2) 0.31160(16) 0.17120(10) 0.0420(4) Uani 1 1 d . . . H6 H 0.3028 0.2877 0.2197 0.050 Uiso 1 1 calc R . . C7 C 0.3112(3) 0.56415(18) 0.04850(15) 0.0683(7) Uani 1 1 d . . . H7A H 0.2562 0.5782 -0.0016 0.102 Uiso 1 1 calc R . . H7B H 0.4374 0.5678 0.0490 0.102 Uiso 1 1 calc R . . H7C H 0.2731 0.6186 0.0823 0.102 Uiso 1 1 calc R . . C8 C 0.4042(2) 0.04451(16) 0.19417(10) 0.0424(4) Uani 1 1 d . . . H8A H 0.3821 0.0642 0.2450 0.051 Uiso 1 1 calc R . . H8B H 0.4672 0.1051 0.1736 0.051 Uiso 1 1 calc R . . C9 C 0.5163(2) -0.06009(15) 0.19604(10) 0.0391(4) Uani 1 1 d . . . H9 H 0.4546 -0.1190 0.2204 0.047 Uiso 1 1 calc R . . C10 C 0.5423(3) -0.09693(16) 0.11625(11) 0.0438(4) Uani 1 1 d . . . H10 H 0.6077 -0.0392 0.0925 0.053 Uiso 1 1 calc R . . C11 C 0.3633(3) -0.11193(18) 0.07017(12) 0.0532(5) Uani 1 1 d . . . H11A H 0.3806 -0.1325 0.0189 0.064 Uiso 1 1 calc R . . H11B H 0.2993 -0.1713 0.0917 0.064 Uiso 1 1 calc R . . C12 C 0.2552(3) -0.00679(18) 0.06897(11) 0.0516(5) Uani 1 1 d . . . H12A H 0.3142 0.0516 0.0441 0.062 Uiso 1 1 calc R . . H12B H 0.1399 -0.0189 0.0412 0.062 Uiso 1 1 calc R . . C13 C 0.6941(2) -0.04002(17) 0.24189(11) 0.0447(4) Uani 1 1 d . . . H13 H 0.7410 0.0301 0.2250 0.054 Uiso 1 1 calc R . . C14 C 0.8215(3) -0.19287(18) 0.17272(12) 0.0553(5) Uani 1 1 d . . . C15 C 0.6525(3) -0.20169(19) 0.12143(13) 0.0578(6) Uani 1 1 d . . . H15A H 0.5823 -0.2613 0.1391 0.069 Uiso 1 1 calc R . . H15B H 0.6802 -0.2211 0.0713 0.069 Uiso 1 1 calc R . . C16 C 0.6847(3) -0.0316(2) 0.32564(12) 0.0651(6) Uani 1 1 d . . . H16A H 0.6437 -0.1005 0.3440 0.098 Uiso 1 1 calc R . . H16B H 0.6042 0.0263 0.3356 0.098 Uiso 1 1 calc R . . H16C H 0.8000 -0.0153 0.3506 0.098 Uiso 1 1 calc R . . N1 N 0.23445(19) 0.02615(12) 0.14719(8) 0.0402(4) Uani 1 1 d . . . O1 O -0.07333(17) 0.08324(12) 0.10722(8) 0.0536(4) Uani 1 1 d . . . O2 O 0.06593(18) 0.12995(12) 0.23537(8) 0.0515(4) Uani 1 1 d . . . O3 O 0.8248(2) -0.12616(13) 0.23233(9) 0.0617(4) Uani 1 1 d . . . O4 O 0.9509(2) -0.24756(17) 0.16513(11) 0.0846(6) Uani 1 1 d . . . S1 S 0.07882(6) 0.11769(4) 0.15629(3) 0.04089(16) Uani 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 C1 0.0329(9) 0.0378(9) 0.0401(10) -0.0011(7) 0.0045(7) 0.0030(7) C2 0.0434(10) 0.0422(10) 0.0414(10) -0.0049(8) -0.0028(7) -0.0003(8) C3 0.0510(11) 0.0452(10) 0.0416(11) 0.0037(8) 0.0006(8) 0.0040(8) C4 0.0404(10) 0.0389(9) 0.0574(12) -0.0010(8) 0.0064(8) 0.0008(8) C5 0.0380(10) 0.0449(10) 0.0537(12) -0.0117(9) -0.0011(8) -0.0023(8) C6 0.0378(9) 0.0480(10) 0.0394(10) -0.0026(8) 0.0003(7) 0.0032(8) C7 0.0666(15) 0.0482(12) 0.0880(18) 0.0080(12) -0.0001(12) -0.0088(11) C8 0.0392(10) 0.0469(10) 0.0398(10) -0.0042(8) -0.0014(7) -0.0005(8) C9 0.0366(9) 0.0419(9) 0.0381(10) 0.0002(7) 0.0015(7) -0.0037(7) C10 0.0440(10) 0.0463(10) 0.0403(10) -0.0040(8) 0.0007(8) 0.0019(8) C11 0.0546(12) 0.0541(12) 0.0475(12) -0.0142(9) -0.0085(9) 0.0054(9) C12 0.0520(11) 0.0584(12) 0.0416(11) -0.0063(9) -0.0071(8) 0.0091(9) C13 0.0361(10) 0.0534(11) 0.0441(11) -0.0031(9) 0.0027(7) -0.0010(8) C14 0.0492(12) 0.0576(12) 0.0574(13) -0.0031(10) -0.0014(9) 0.0122(10) C15 0.0558(13) 0.0566(12) 0.0583(13) -0.0151(10) -0.0061(10) 0.0115(10) C16 0.0453(12) 0.1048(19) 0.0431(12) -0.0085(12) -0.0041(9) -0.0014(12) N1 0.0379(8) 0.0410(8) 0.0404(8) -0.0007(6) -0.0019(6) 0.0012(6) O1 0.0354(7) 0.0593(8) 0.0639(9) 0.0060(7) -0.0045(6) -0.0077(6) O2 0.0494(8) 0.0597(9) 0.0472(8) 0.0076(6) 0.0136(6) 0.0039(6) O3 0.0480(8) 0.0738(10) 0.0595(9) -0.0141(8) -0.0113(7) 0.0179(7) O4 0.0628(11) 0.0924(13) 0.0945(14) -0.0234(11) -0.0095(9) 0.0353(10) S1 0.0333(2) 0.0443(3) 0.0450(3) 0.00401(19) 0.00379(17) -0.00068(18) _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 1.383(3) . ? C1 C6 1.397(2) . ? C1 S1 1.7648(18) . ? C2 C3 1.388(3) . ? C3 C4 1.391(3) . ? C4 C5 1.387(3) . ? C4 C7 1.513(3) . ? C5 C6 1.382(3) . ? C8 N1 1.476(2) . ? C8 C9 1.524(3) . ? C9 C13 1.521(2) . ? C9 C10 1.525(3) . ? C10 C15 1.516(3) . ? C10 C11 1.522(3) . ? C11 C12 1.513(3) . ? C12 N1 1.476(2) . ? C13 O3 1.463(2) . ? C13 C16 1.507(3) . ? C14 O4 1.206(3) . ? C14 O3 1.333(3) . ? C14 C15 1.498(3) . ? N1 S1 1.6420(15) . ? O1 S1 1.4339(14) . ? O2 S1 1.4323(14) . ? 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 C6 120.50(17) . . ? C2 C1 S1 120.46(14) . . ? C6 C1 S1 119.04(14) . . ? C1 C2 C3 119.46(17) . . ? C2 C3 C4 121.05(18) . . ? C5 C4 C3 118.42(18) . . ? C5 C4 C7 120.23(18) . . ? C3 C4 C7 121.33(19) . . ? C6 C5 C4 121.63(17) . . ? C5 C6 C1 118.90(17) . . ? N1 C8 C9 109.85(15) . . ? C13 C9 C8 109.97(15) . . ? C13 C9 C10 110.43(15) . . ? C8 C9 C10 110.62(15) . . ? C15 C10 C11 112.89(16) . . ? C15 C10 C9 108.37(16) . . ? C11 C10 C9 109.77(16) . . ? C12 C11 C10 111.10(16) . . ? N1 C12 C11 109.15(16) . . ? O3 C13 C16 105.72(16) . . ? O3 C13 C9 113.53(15) . . ? C16 C13 C9 114.00(16) . . ? O4 C14 O3 118.6(2) . . ? O4 C14 C15 123.3(2) . . ? O3 C14 C15 118.02(18) . . ? C14 C15 C10 114.16(17) . . ? C12 N1 C8 113.53(15) . . ? C12 N1 S1 115.39(12) . . ? C8 N1 S1 115.94(12) . . ? C14 O3 C13 124.81(15) . . ? O2 S1 O1 119.53(9) . . ? O2 S1 N1 107.19(8) . . ? O1 S1 N1 106.62(8) . . ? O2 S1 C1 107.50(8) . . ? O1 S1 C1 108.01(8) . . ? N1 S1 C1 107.45(8) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 70.38 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.270 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.041 # Attachment 'sw1.cif' data_sw1 _database_code_depnum_ccdc_archive 'CCDC 649649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H26 N2 O5 S, C H CL3' _chemical_formula_sum 'C21 H27 Cl3 N2 O5 S' _chemical_formula_weight 525.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 6.0833(5) _cell_length_b 9.5865(7) _cell_length_c 22.1903(17) _cell_angle_alpha 81.993(5) _cell_angle_beta 86.709(5) _cell_angle_gamma 78.059(4) _cell_volume 1253.19(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2208 _cell_measurement_theta_min 4.03 _cell_measurement_theta_max 70.42 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 4.383 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4744 _exptl_absorpt_correction_T_max 0.8442 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8035 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0988 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 70.42 _reflns_number_total 4167 _reflns_number_gt 2208 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0691P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4167 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1168 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1692 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _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 1.2986(7) -0.0951(4) 0.18230(18) 0.0602(11) Uani 1 1 d . . . C2 C 1.2170(8) 0.0026(5) 0.1324(2) 0.0731(13) Uani 1 1 d . . . H2 H 1.2638 0.0898 0.1237 0.088 Uiso 1 1 calc R . . C3 C 1.0662(9) -0.0321(5) 0.0964(2) 0.0789(14) Uani 1 1 d . . . H3 H 1.0145 0.0324 0.0625 0.095 Uiso 1 1 calc R . . C4 C 0.9873(8) -0.1596(6) 0.1083(2) 0.0780(14) Uani 1 1 d . . . C5 C 1.0746(9) -0.2543(5) 0.1581(3) 0.0842(15) Uani 1 1 d . . . H5 H 1.0276 -0.3414 0.1671 0.101 Uiso 1 1 calc R . . C6 C 1.2280(9) -0.2239(5) 0.1946(2) 0.0776(13) Uani 1 1 d . . . H6 H 1.2843 -0.2901 0.2275 0.093 Uiso 1 1 calc R . . C7 C 0.8146(9) -0.1924(6) 0.0694(2) 0.1049(18) Uani 1 1 d . . . H7A H 0.8887 -0.2367 0.0354 0.157 Uiso 1 1 calc R . . H7B H 0.7136 -0.1048 0.0548 0.157 Uiso 1 1 calc R . . H7C H 0.7315 -0.2568 0.0931 0.157 Uiso 1 1 calc R . . C8 C 1.1671(7) 0.1765(4) 0.26489(17) 0.0594(11) Uani 1 1 d . . . H8A H 1.0402 0.1711 0.2414 0.071 Uiso 1 1 calc R . . H8B H 1.2622 0.2314 0.2392 0.071 Uiso 1 1 calc R . . C9 C 1.0836(6) 0.2512(4) 0.32082(16) 0.0548(10) Uani 1 1 d . . . H9 H 1.2155 0.2542 0.3436 0.066 Uiso 1 1 calc R . . C10 C 0.9369(6) 0.1631(4) 0.36261(17) 0.0561(10) Uani 1 1 d . . . H10 H 0.8034 0.1600 0.3405 0.067 Uiso 1 1 calc R . . C11 C 1.0683(7) 0.0106(4) 0.37797(17) 0.0624(11) Uani 1 1 d . . . H11A H 0.9723 -0.0467 0.4019 0.075 Uiso 1 1 calc R . . H11B H 1.1943 0.0118 0.4026 0.075 Uiso 1 1 calc R . . C12 C 1.1561(7) -0.0596(4) 0.32142(17) 0.0626(11) Uani 1 1 d . . . H12A H 1.2446 -0.1550 0.3332 0.075 Uiso 1 1 calc R . . H12B H 1.0311 -0.0687 0.2980 0.075 Uiso 1 1 calc R . . C13 C 0.9662(8) 0.4060(5) 0.30079(19) 0.0675(12) Uani 1 1 d . . . C14 C 0.7493(10) 0.4311(6) 0.2714(3) 0.121(2) Uani 1 1 d . . . H14A H 0.6925 0.5326 0.2625 0.182 Uiso 1 1 calc R . . H14B H 0.6447 0.3884 0.2981 0.182 Uiso 1 1 calc R . . H14C H 0.7687 0.3886 0.2342 0.182 Uiso 1 1 calc R . . C15 C 1.0598(9) 0.5138(5) 0.3116(2) 0.0924(16) Uani 1 1 d . . . H15A H 0.9873 0.6085 0.3003 0.111 Uiso 1 1 calc R . . H15B H 1.1977 0.4942 0.3303 0.111 Uiso 1 1 calc R . . C16 C 0.8603(7) 0.2350(5) 0.41982(18) 0.0665(12) Uani 1 1 d . . . H16A H 0.9776 0.2046 0.4495 0.080 Uiso 1 1 calc R . . H16B H 0.8414 0.3384 0.4093 0.080 Uiso 1 1 calc R . . C17 C 0.6470(6) 0.2016(4) 0.44836(17) 0.0540(10) Uani 1 1 d . . . C18 C 0.6582(7) 0.3423(4) 0.53390(16) 0.0518(10) Uani 1 1 d . . . C19 C 0.3276(8) 0.3124(6) 0.5825(2) 0.0785(14) Uani 1 1 d . . . H19A H 0.1906 0.3854 0.5809 0.094 Uiso 1 1 calc R . . H19B H 0.3226 0.2455 0.6193 0.094 Uiso 1 1 calc R . . C20 C 0.3523(8) 0.2360(6) 0.5281(2) 0.0914(17) Uani 1 1 d . . . H20A H 0.3505 0.1348 0.5395 0.110 Uiso 1 1 calc R . . H20B H 0.2332 0.2780 0.4999 0.110 Uiso 1 1 calc R . . N1 N 1.2956(5) 0.0301(3) 0.28441(13) 0.0552(8) Uani 1 1 d . . . N2 N 0.5672(5) 0.2556(3) 0.50205(13) 0.0505(8) Uani 1 1 d . . . O1 O 1.5959(5) -0.1748(3) 0.26517(14) 0.0843(10) Uani 1 1 d . . . O2 O 1.5832(5) 0.0609(3) 0.20310(13) 0.0768(9) Uani 1 1 d . . . O3 O 0.5380(5) 0.1300(4) 0.42689(15) 0.0968(12) Uani 1 1 d . . . O4 O 0.8312(5) 0.3819(4) 0.52440(13) 0.0804(9) Uani 1 1 d . . . O5 O 0.5207(5) 0.3770(3) 0.58115(12) 0.0710(8) Uani 1 1 d . . . S1 S 1.46899(18) -0.04621(12) 0.23398(5) 0.0661(4) Uani 1 1 d . . . C21 C 0.6544(8) 0.3159(5) 0.0954(2) 0.0836(14) Uani 1 1 d . . . H21 H 0.6760 0.2307 0.1262 0.100 Uiso 1 1 calc R . . Cl1 Cl 0.4457(3) 0.44773(19) 0.12259(8) 0.1281(6) Uani 1 1 d . . . Cl2 Cl 0.5760(3) 0.2674(2) 0.02907(8) 0.1304(6) Uani 1 1 d . . . Cl3 Cl 0.9076(2) 0.37600(16) 0.08482(8) 0.1181(6) Uani 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 C1 0.076(3) 0.040(2) 0.057(3) -0.007(2) 0.020(2) -0.002(2) C2 0.097(4) 0.056(3) 0.061(3) -0.006(3) 0.017(3) -0.011(3) C3 0.102(4) 0.070(4) 0.058(3) -0.010(3) 0.009(3) -0.005(3) C4 0.088(4) 0.075(4) 0.073(3) -0.033(3) 0.023(3) -0.012(3) C5 0.110(4) 0.060(3) 0.083(4) -0.021(3) 0.023(3) -0.018(3) C6 0.099(4) 0.052(3) 0.075(3) -0.008(3) 0.017(3) -0.006(3) C7 0.118(5) 0.109(4) 0.097(4) -0.039(4) 0.010(3) -0.031(4) C8 0.070(3) 0.052(2) 0.049(2) -0.004(2) 0.0086(19) 0.001(2) C9 0.060(2) 0.058(3) 0.044(2) -0.012(2) 0.0042(18) -0.0062(19) C10 0.056(2) 0.066(3) 0.049(2) -0.016(2) 0.0077(18) -0.015(2) C11 0.068(3) 0.070(3) 0.048(2) -0.001(2) 0.0119(19) -0.018(2) C12 0.069(3) 0.058(3) 0.057(3) -0.004(2) 0.011(2) -0.010(2) C13 0.080(3) 0.059(3) 0.056(3) -0.014(2) 0.017(2) 0.001(2) C14 0.117(5) 0.093(4) 0.135(5) -0.022(4) -0.036(4) 0.036(4) C15 0.115(4) 0.061(3) 0.098(4) -0.012(3) 0.033(3) -0.019(3) C16 0.069(3) 0.085(3) 0.052(2) -0.022(2) 0.015(2) -0.024(2) C17 0.051(2) 0.062(3) 0.051(2) -0.018(2) 0.0001(18) -0.0093(19) C18 0.049(2) 0.066(3) 0.041(2) -0.013(2) 0.0023(18) -0.008(2) C19 0.065(3) 0.112(4) 0.062(3) -0.023(3) 0.018(2) -0.022(3) C20 0.071(3) 0.113(4) 0.107(4) -0.061(3) 0.039(3) -0.039(3) N1 0.057(2) 0.050(2) 0.0508(19) -0.0027(16) 0.0121(15) -0.0003(15) N2 0.0466(18) 0.058(2) 0.0500(19) -0.0166(16) 0.0081(14) -0.0130(15) O1 0.073(2) 0.065(2) 0.094(2) 0.0029(17) 0.0056(17) 0.0214(16) O2 0.0664(19) 0.074(2) 0.083(2) -0.0049(17) 0.0292(16) -0.0102(15) O3 0.075(2) 0.140(3) 0.104(2) -0.080(2) 0.0285(18) -0.053(2) O4 0.066(2) 0.112(3) 0.080(2) -0.0460(19) 0.0151(16) -0.0406(18) O5 0.0607(18) 0.100(2) 0.0590(18) -0.0357(17) 0.0112(14) -0.0193(16) S1 0.0632(7) 0.0591(7) 0.0658(7) -0.0049(6) 0.0142(5) 0.0043(5) C21 0.080(3) 0.080(3) 0.091(4) -0.005(3) -0.007(3) -0.017(3) Cl1 0.0930(11) 0.1440(14) 0.1377(14) -0.0363(11) 0.0102(9) 0.0065(10) Cl2 0.1541(15) 0.1413(15) 0.1036(12) -0.0265(10) -0.0294(10) -0.0337(12) Cl3 0.0859(10) 0.0967(11) 0.1762(16) -0.0265(10) 0.0110(9) -0.0266(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.377(6) . ? C1 C2 1.389(6) . ? C1 S1 1.760(5) . ? C2 C3 1.370(7) . ? C3 C4 1.390(6) . ? C4 C5 1.384(7) . ? C4 C7 1.505(7) . ? C5 C6 1.369(7) . ? C8 N1 1.477(4) . ? C8 C9 1.529(5) . ? C9 C13 1.524(6) . ? C9 C10 1.539(5) . ? C10 C11 1.517(5) . ? C10 C16 1.532(5) . ? C11 C12 1.524(5) . ? C12 N1 1.470(5) . ? C13 C15 1.333(6) . ? C13 C14 1.466(7) . ? C16 C17 1.486(5) . ? C17 O3 1.206(4) . ? C17 N2 1.387(5) . ? C18 O4 1.189(4) . ? C18 O5 1.338(4) . ? C18 N2 1.377(5) . ? C19 O5 1.434(5) . ? C19 C20 1.481(6) . ? C20 N2 1.436(5) . ? N1 S1 1.635(3) . ? O1 S1 1.423(3) . ? O2 S1 1.432(3) . ? C21 Cl2 1.725(5) . ? C21 Cl1 1.741(5) . ? C21 Cl3 1.746(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 C6 C1 C2 119.9(5) . . ? C6 C1 S1 120.0(4) . . ? C2 C1 S1 119.8(4) . . ? C3 C2 C1 118.7(4) . . ? C2 C3 C4 122.8(5) . . ? C5 C4 C3 116.5(5) . . ? C5 C4 C7 121.7(5) . . ? C3 C4 C7 121.7(5) . . ? C6 C5 C4 122.1(5) . . ? C5 C6 C1 119.9(5) . . ? N1 C8 C9 109.6(3) . . ? C13 C9 C8 109.7(3) . . ? C13 C9 C10 113.9(3) . . ? C8 C9 C10 110.2(3) . . ? C11 C10 C16 112.0(3) . . ? C11 C10 C9 109.1(3) . . ? C16 C10 C9 110.2(3) . . ? C10 C11 C12 112.5(3) . . ? N1 C12 C11 108.8(3) . . ? C15 C13 C14 122.1(5) . . ? C15 C13 C9 119.6(5) . . ? C14 C13 C9 118.3(5) . . ? C17 C16 C10 114.0(3) . . ? O3 C17 N2 117.9(4) . . ? O3 C17 C16 123.1(4) . . ? N2 C17 C16 119.0(3) . . ? O4 C18 O5 122.2(4) . . ? O4 C18 N2 128.7(3) . . ? O5 C18 N2 109.1(3) . . ? O5 C19 C20 105.9(3) . . ? N2 C20 C19 103.5(4) . . ? C12 N1 C8 111.9(3) . . ? C12 N1 S1 116.9(2) . . ? C8 N1 S1 116.9(2) . . ? C18 N2 C17 128.4(3) . . ? C18 N2 C20 110.8(3) . . ? C17 N2 C20 120.5(3) . . ? C18 O5 C19 110.5(3) . . ? O1 S1 O2 119.46(19) . . ? O1 S1 N1 106.74(17) . . ? O2 S1 N1 107.15(17) . . ? O1 S1 C1 107.9(2) . . ? O2 S1 C1 109.2(2) . . ? N1 S1 C1 105.62(17) . . ? Cl2 C21 Cl1 111.1(3) . . ? Cl2 C21 Cl3 111.1(3) . . ? Cl1 C21 Cl3 110.0(3) . . ? _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 70.42 _diffrn_measured_fraction_theta_full 0.867 _refine_diff_density_max 0.282 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.059