# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Alajos Kalman' _publ_contact_author_email AKALMAN@CHEMRES.HU _publ_section_title ; Annular desmotropy of three pairs of seven-membered heterocycles confirmed by X-ray crystallography ; loop_ _publ_author_name 'Alajos Kalman' 'Peter Csomos' 'Laszlo Fabian' 'Lajos Fodor' 'Tamas Holczbauer' # Attachment 'cs164a.cif' data_cs164a _database_code_depnum_ccdc_archive 'CCDC 756120' #TrackingRef 'cs164a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Ethoxycarbonyl-2-phenyl-1,5-dihydro-4,1-benzothiazepine ; _chemical_name_common 3-Ethoxycarbonyl-2-phenyl-1,5-dihydro-4,1-benzothiazepine _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O2 S' _chemical_formula_sum 'C18 H17 N O2 S' _chemical_formula_weight 311.39 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 monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.905(2) _cell_length_b 7.947(4) _cell_length_c 16.797(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.611(15) _cell_angle_gamma 90.00 _cell_volume 781.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 10889 _cell_measurement_theta_min 3.48 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9485 _exptl_absorpt_correction_T_max 0.9790 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12443 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 26.36 _reflns_number_total 3040 _reflns_number_gt 2443 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0224P)^2^+0.2426P] 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 0.10(9) _refine_ls_number_reflns 3040 _refine_ls_number_parameters 200 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 C5 C 0.4261(5) 0.0697(4) 0.37562(16) 0.0466(7) Uani 1 1 d . . . H5A H 0.3716 0.1750 0.3509 0.056 Uiso 1 1 calc R . . H5B H 0.2967 0.0128 0.3936 0.056 Uiso 1 1 calc R . . S4 S 0.53941(13) -0.06081(10) 0.30067(4) 0.0495(2) Uani 1 1 d . . . C3 C 0.6677(4) 0.0960(4) 0.24682(15) 0.0374(6) Uani 1 1 d . . . C2 C 0.7991(4) 0.2231(4) 0.28212(14) 0.0364(6) Uani 1 1 d . . . N1 N 0.8553(4) 0.2572(3) 0.36331(12) 0.0403(6) Uani 1 1 d . . . H1 H 0.9549 0.3561 0.3721 0.048 Uiso 1 1 d R . . C9A C 0.8004(4) 0.1931(3) 0.43695(14) 0.0365(6) Uani 1 1 d . . . C9 C 0.9547(5) 0.2316(4) 0.50444(16) 0.0434(7) Uani 1 1 d . . . H9 H 1.0884 0.2890 0.4981 0.052 Uiso 1 1 calc R . . C8 C 0.9140(5) 0.1869(4) 0.58002(17) 0.0493(8) Uani 1 1 d . . . H8 H 1.0181 0.2158 0.6244 0.059 Uiso 1 1 calc R . . C7 C 0.7170(5) 0.0984(4) 0.59036(16) 0.0494(7) Uani 1 1 d . . . H7 H 0.6891 0.0655 0.6413 0.059 Uiso 1 1 calc R . . C6 C 0.5636(5) 0.0604(4) 0.52341(16) 0.0456(7) Uani 1 1 d . . . H6 H 0.4315 0.0013 0.5303 0.055 Uiso 1 1 calc R . . C5A C 0.5985(4) 0.1066(3) 0.44658(15) 0.0370(6) Uani 1 1 d . . . C10 C 0.6217(5) 0.0869(4) 0.15776(16) 0.0412(6) Uani 1 1 d . . . O1 O 0.5228(4) -0.0582(3) 0.13400(10) 0.0617(6) Uani 1 1 d . . . O2 O 0.6621(4) 0.1945(3) 0.11168(12) 0.0664(7) Uani 1 1 d . . . C11 C 0.4574(6) -0.0785(6) 0.04782(16) 0.0676(10) Uani 1 1 d . . . H11A H 0.4610 -0.1968 0.0339 0.081 Uiso 1 1 calc R . . H11B H 0.5656 -0.0196 0.0191 0.081 Uiso 1 1 calc R . . C12 C 0.2252(8) -0.0109(6) 0.0235(2) 0.0988(16) Uani 1 1 d . . . H12A H 0.1194 -0.0658 0.0537 0.148 Uiso 1 1 calc R . . H12B H 0.1810 -0.0309 -0.0328 0.148 Uiso 1 1 calc R . . H12C H 0.2246 0.1079 0.0338 0.148 Uiso 1 1 calc R . . C13 C 0.9144(5) 0.3525(4) 0.23629(16) 0.0351(7) Uani 1 1 d . . . C14 C 1.1102(5) 0.3104(4) 0.20259(16) 0.0432(7) Uani 1 1 d . . . H14 H 1.1583 0.1989 0.2025 0.052 Uiso 1 1 calc R . . C15 C 1.2326(5) 0.4337(6) 0.16945(16) 0.0547(7) Uani 1 1 d . . . H15 H 1.3629 0.4050 0.1469 0.066 Uiso 1 1 calc R . . C16 C 1.1631(6) 0.6001(5) 0.16954(18) 0.0593(9) Uani 1 1 d . . . H16 H 1.2481 0.6833 0.1482 0.071 Uiso 1 1 calc R . . C17 C 0.9677(6) 0.6414(4) 0.20129(17) 0.0543(8) Uani 1 1 d . . . H17 H 0.9187 0.7526 0.2004 0.065 Uiso 1 1 calc R . . C18 C 0.8441(5) 0.5192(4) 0.23442(17) 0.0446(8) Uani 1 1 d . . . H18 H 0.7121 0.5486 0.2558 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 C5 0.0449(16) 0.053(2) 0.0420(16) 0.0072(14) 0.0070(12) -0.0043(15) S4 0.0722(5) 0.0391(4) 0.0379(4) -0.0010(4) 0.0093(3) -0.0149(5) C3 0.0446(15) 0.0347(17) 0.0320(13) 0.0006(12) 0.0025(11) -0.0015(14) C2 0.0373(14) 0.0419(17) 0.0299(14) 0.0023(12) 0.0041(10) 0.0026(13) N1 0.0452(13) 0.0448(16) 0.0300(12) 0.0003(10) 0.0025(9) -0.0128(11) C9A 0.0441(16) 0.0372(16) 0.0283(14) 0.0009(12) 0.0056(11) 0.0047(13) C9 0.0486(17) 0.043(2) 0.0371(15) 0.0005(13) 0.0003(12) -0.0009(14) C8 0.0612(19) 0.0483(19) 0.0365(16) -0.0027(14) -0.0001(14) 0.0061(16) C7 0.072(2) 0.0472(19) 0.0297(15) 0.0077(13) 0.0102(14) 0.0083(17) C6 0.0511(17) 0.0432(19) 0.0445(17) 0.0041(14) 0.0133(13) 0.0016(14) C5A 0.0418(15) 0.0323(16) 0.0376(15) 0.0031(12) 0.0084(11) 0.0041(13) C10 0.0456(15) 0.0426(18) 0.0351(15) 0.0006(14) 0.0046(12) 0.0020(15) O1 0.0990(16) 0.0483(12) 0.0352(10) -0.0047(12) -0.0001(10) -0.0246(15) O2 0.0944(17) 0.0655(16) 0.0364(12) 0.0066(11) -0.0024(11) -0.0288(14) C11 0.102(3) 0.063(2) 0.0353(16) -0.0135(18) 0.0030(16) -0.022(2) C12 0.123(4) 0.106(4) 0.058(2) -0.004(2) -0.020(2) -0.006(3) C13 0.0388(15) 0.0376(18) 0.0275(14) 0.0018(12) -0.0008(11) -0.0038(13) C14 0.0446(17) 0.0469(19) 0.0374(16) 0.0052(14) 0.0032(13) 0.0065(14) C15 0.0482(16) 0.069(2) 0.0485(16) 0.006(2) 0.0131(13) -0.005(2) C16 0.070(2) 0.059(2) 0.050(2) 0.0124(17) 0.0103(16) -0.019(2) C17 0.071(2) 0.0420(19) 0.0490(19) 0.0068(14) 0.0031(16) -0.0064(17) C18 0.0499(18) 0.0453(18) 0.0380(17) 0.0024(14) 0.0034(13) 0.0002(16) _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 C5 C5A 1.491(4) . ? C5 S4 1.825(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? S4 C3 1.768(3) . ? C3 C2 1.361(4) . ? C3 C10 1.486(4) . ? C2 N1 1.387(3) . ? C2 C13 1.501(4) . ? N1 C9A 1.414(3) . ? N1 H1 0.9814 . ? C9A C9 1.391(4) . ? C9A C5A 1.404(4) . ? C9 C8 1.370(4) . ? C9 H9 0.9300 . ? C8 C7 1.389(4) . ? C8 H8 0.9300 . ? C7 C6 1.381(4) . ? C7 H7 0.9300 . ? C6 C5A 1.383(4) . ? C6 H6 0.9300 . ? C10 O2 1.199(3) . ? C10 O1 1.330(4) . ? O1 C11 1.457(3) . ? C11 C12 1.479(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C18 1.387(4) . ? C13 C14 1.394(4) . ? C14 C15 1.379(4) . ? C14 H14 0.9300 . ? C15 C16 1.384(6) . ? C15 H15 0.9300 . ? C16 C17 1.373(4) . ? C16 H16 0.9300 . ? C17 C18 1.376(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? 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 C5A C5 S4 112.91(19) . . ? C5A C5 H5A 109.0 . . ? S4 C5 H5A 109.0 . . ? C5A C5 H5B 109.0 . . ? S4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C3 S4 C5 99.99(14) . . ? C2 C3 C10 119.5(2) . . ? C2 C3 S4 123.9(2) . . ? C10 C3 S4 116.5(2) . . ? C3 C2 N1 128.4(2) . . ? C3 C2 C13 123.8(2) . . ? N1 C2 C13 107.7(2) . . ? C2 N1 C9A 137.5(2) . . ? C2 N1 H1 111.4 . . ? C9A N1 H1 111.0 . . ? C9 C9A C5A 119.2(2) . . ? C9 C9A N1 115.6(2) . . ? C5A C9A N1 125.0(2) . . ? C8 C9 C9A 121.5(3) . . ? C8 C9 H9 119.3 . . ? C9A C9 H9 119.3 . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C6 C7 C8 118.6(3) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? C7 C6 C5A 122.6(3) . . ? C7 C6 H6 118.7 . . ? C5A C6 H6 118.7 . . ? C6 C5A C9A 118.1(2) . . ? C6 C5A C5 121.6(2) . . ? C9A C5A C5 120.3(2) . . ? O2 C10 O1 122.8(2) . . ? O2 C10 C3 126.1(3) . . ? O1 C10 C3 111.0(2) . . ? C10 O1 C11 116.2(3) . . ? O1 C11 C12 110.4(3) . . ? O1 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? O1 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 118.8(3) . . ? C18 C13 C2 120.7(3) . . ? C14 C13 C2 120.0(3) . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 119.6(3) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.4(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C13 120.7(3) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? 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 C5A C5 S4 C3 -84.3(2) . . . . ? C5 S4 C3 C2 44.8(3) . . . . ? C5 S4 C3 C10 -133.8(2) . . . . ? C10 C3 C2 N1 177.6(2) . . . . ? S4 C3 C2 N1 -1.0(4) . . . . ? C10 C3 C2 C13 -3.6(4) . . . . ? S4 C3 C2 C13 177.8(2) . . . . ? C3 C2 N1 C9A -4.4(5) . . . . ? C13 C2 N1 C9A 176.6(3) . . . . ? C2 N1 C9A C9 159.6(3) . . . . ? C2 N1 C9A C5A -25.2(5) . . . . ? C5A C9A C9 C8 0.0(4) . . . . ? N1 C9A C9 C8 175.6(3) . . . . ? C9A C9 C8 C7 1.2(4) . . . . ? C9 C8 C7 C6 -1.3(5) . . . . ? C8 C7 C6 C5A 0.1(5) . . . . ? C7 C6 C5A C9A 1.1(4) . . . . ? C7 C6 C5A C5 -177.6(3) . . . . ? C9 C9A C5A C6 -1.2(4) . . . . ? N1 C9A C5A C6 -176.2(3) . . . . ? C9 C9A C5A C5 177.6(3) . . . . ? N1 C9A C5A C5 2.5(4) . . . . ? S4 C5 C5A C6 -120.8(3) . . . . ? S4 C5 C5A C9A 60.5(3) . . . . ? C2 C3 C10 O2 -11.2(4) . . . . ? S4 C3 C10 O2 167.4(3) . . . . ? C2 C3 C10 O1 170.0(3) . . . . ? S4 C3 C10 O1 -11.3(3) . . . . ? O2 C10 O1 C11 -2.1(4) . . . . ? C3 C10 O1 C11 176.7(2) . . . . ? C10 O1 C11 C12 -87.8(4) . . . . ? C3 C2 C13 C18 111.6(3) . . . . ? N1 C2 C13 C18 -69.4(3) . . . . ? C3 C2 C13 C14 -75.6(3) . . . . ? N1 C2 C13 C14 103.4(3) . . . . ? C18 C13 C14 C15 1.1(4) . . . . ? C2 C13 C14 C15 -171.7(2) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C14 C15 C16 C17 -1.5(4) . . . . ? C15 C16 C17 C18 1.4(4) . . . . ? C16 C17 C18 C13 0.0(5) . . . . ? C14 C13 C18 C17 -1.2(4) . . . . ? C2 C13 C18 C17 171.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.197 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.039 # Attachment 'cs164f.cif' data_cs164f _database_code_depnum_ccdc_archive 'CCDC 756121' #TrackingRef 'cs164f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R*)-3-Ethoxycarbonyl-2-phenyl-3,5-dihydro-4,1-benzothiazepine ; _chemical_name_common (R*)-3-Ethoxycarbonyl-2-phenyl-3,5-dihydro-4,1-benzothiazepine _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O2 S' _chemical_formula_sum 'C18 H17 N O2 S' _chemical_formula_weight 311.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.0826 0.0763 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5761(11) _cell_length_b 9.7540(11) _cell_length_c 10.7880(14) _cell_angle_alpha 65.345(3) _cell_angle_beta 73.471(3) _cell_angle_gamma 72.509(3) _cell_volume 768.95(16) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 31090 _cell_measurement_theta_min 2.425 _cell_measurement_theta_max 24.745 _exptl_crystal_description chunk _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9210 _exptl_absorpt_correction_T_max 0.9537 _exptl_absorpt_process_details 'CrystalClear v1.4.0 (Rigaku, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.56089 _diffrn_radiation_type AgK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis RAPID' _diffrn_measurement_method '\w -scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24226 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 19.50 _reflns_number_total 2710 _reflns_number_gt 2577 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)' _computing_cell_refinement 'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)' _computing_data_reduction 'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; ; _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^)+(0.0323P)^2^+0.3161P] 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 2710 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0751 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 N1 N -0.01892(13) 0.29373(12) 0.70175(11) 0.0219(2) Uani 1 1 d . . . C2 C 0.08384(16) 0.27436(14) 0.77657(12) 0.0203(3) Uani 1 1 d . . . C3 C 0.04158(16) 0.34949(15) 0.88433(13) 0.0213(3) Uani 1 1 d . . . H3 H 0.1498 0.3409 0.9076 0.026 Uiso 1 1 calc R . . S4 S -0.07839(4) 0.23834(4) 1.04313(3) 0.02671(11) Uani 1 1 d . . . C5 C -0.21928(17) 0.19673(16) 0.97063(14) 0.0275(3) Uani 1 1 d . . . H5A H -0.1592 0.1121 0.9359 0.033 Uiso 1 1 calc R . . H5B H -0.3130 0.1610 1.0451 0.033 Uiso 1 1 calc R . . C5A C -0.28689(16) 0.33415(15) 0.85460(13) 0.0229(3) Uani 1 1 d . . . C6 C -0.44969(17) 0.41642(16) 0.87180(14) 0.0263(3) Uani 1 1 d . . . H6 H -0.5200 0.3876 0.9601 0.032 Uiso 1 1 calc R . . C7 C -0.51055(18) 0.54006(17) 0.76158(15) 0.0301(3) Uani 1 1 d . . . H7 H -0.6217 0.5962 0.7746 0.036 Uiso 1 1 calc R . . C8 C -0.40872(18) 0.58173(16) 0.63212(15) 0.0298(3) Uani 1 1 d . . . H8 H -0.4509 0.6658 0.5563 0.036 Uiso 1 1 calc R . . C9 C -0.24590(17) 0.50154(15) 0.61267(14) 0.0255(3) Uani 1 1 d . . . H9 H -0.1771 0.5298 0.5235 0.031 Uiso 1 1 calc R . . C9A C -0.18330(16) 0.37945(14) 0.72405(13) 0.0214(3) Uani 1 1 d . . . C10 C -0.03490(15) 0.52200(15) 0.82786(13) 0.0209(3) Uani 1 1 d . . . O1 O 0.05888(11) 0.58535(10) 0.70469(9) 0.0235(2) Uani 1 1 d . . . O2 O -0.15098(11) 0.59198(11) 0.88576(10) 0.0271(2) Uani 1 1 d . . . C11 C 0.00735(17) 0.74985(15) 0.63080(15) 0.0266(3) Uani 1 1 d . . . H11B H -0.0338 0.8049 0.6967 0.032 Uiso 1 1 calc R . . H11A H -0.0832 0.7695 0.5818 0.032 Uiso 1 1 calc R . . C12 C 0.15596(18) 0.80527(16) 0.52872(16) 0.0315(3) Uani 1 1 d . . . H12C H 0.2397 0.7964 0.5788 0.047 Uiso 1 1 calc R . . H12B H 0.1222 0.9133 0.4699 0.047 Uiso 1 1 calc R . . H12A H 0.2030 0.7423 0.4707 0.047 Uiso 1 1 calc R . . C13 C 0.24847(16) 0.16929(14) 0.75992(13) 0.0223(3) Uani 1 1 d . . . C14 C 0.38095(18) 0.16107(18) 0.81393(18) 0.0358(4) Uani 1 1 d . . . H14 H 0.3694 0.2272 0.8617 0.043 Uiso 1 1 calc R . . C15 C 0.53029(19) 0.0575(2) 0.7992(2) 0.0448(4) Uani 1 1 d . . . H15 H 0.6200 0.0537 0.8365 0.054 Uiso 1 1 calc R . . C16 C 0.54937(18) -0.03996(18) 0.73065(17) 0.0368(4) Uani 1 1 d . . . H16 H 0.6509 -0.1122 0.7222 0.044 Uiso 1 1 calc R . . C17 C 0.41923(18) -0.03126(16) 0.67443(14) 0.0308(3) Uani 1 1 d . . . H17 H 0.4322 -0.0967 0.6256 0.037 Uiso 1 1 calc R . . C18 C 0.27048(18) 0.07156(15) 0.68849(13) 0.0268(3) Uani 1 1 d . . . H18 H 0.1821 0.0761 0.6493 0.032 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 N1 0.0267(6) 0.0200(5) 0.0181(5) -0.0065(4) -0.0022(4) -0.0059(4) C2 0.0258(6) 0.0167(6) 0.0158(6) -0.0034(5) -0.0002(5) -0.0079(5) C3 0.0228(6) 0.0233(6) 0.0176(6) -0.0076(5) -0.0014(5) -0.0066(5) S4 0.0317(2) 0.0307(2) 0.01540(17) -0.00476(14) -0.00250(13) -0.01031(15) C5 0.0321(7) 0.0270(7) 0.0220(7) -0.0046(6) -0.0018(6) -0.0136(6) C5A 0.0284(7) 0.0233(6) 0.0213(6) -0.0091(5) -0.0034(5) -0.0113(5) C6 0.0270(7) 0.0312(7) 0.0259(7) -0.0145(6) 0.0015(5) -0.0128(6) C7 0.0246(7) 0.0307(7) 0.0363(8) -0.0160(6) -0.0038(6) -0.0039(6) C8 0.0310(7) 0.0267(7) 0.0290(7) -0.0078(6) -0.0087(6) -0.0026(6) C9 0.0295(7) 0.0270(7) 0.0198(6) -0.0082(5) -0.0031(5) -0.0074(6) C9A 0.0250(7) 0.0209(6) 0.0217(6) -0.0105(5) -0.0035(5) -0.0062(5) C10 0.0217(6) 0.0244(6) 0.0210(6) -0.0113(5) -0.0037(5) -0.0067(5) O1 0.0254(5) 0.0183(4) 0.0226(5) -0.0070(4) -0.0002(4) -0.0034(4) O2 0.0255(5) 0.0287(5) 0.0294(5) -0.0169(4) 0.0007(4) -0.0051(4) C11 0.0275(7) 0.0186(6) 0.0292(7) -0.0052(5) -0.0072(6) -0.0018(5) C12 0.0327(8) 0.0220(7) 0.0348(8) -0.0070(6) -0.0023(6) -0.0072(6) C13 0.0258(7) 0.0180(6) 0.0183(6) -0.0035(5) 0.0014(5) -0.0077(5) C14 0.0271(7) 0.0353(8) 0.0548(10) -0.0266(7) -0.0049(7) -0.0075(6) C15 0.0221(7) 0.0485(10) 0.0728(12) -0.0319(9) -0.0082(7) -0.0060(7) C16 0.0241(7) 0.0321(8) 0.0455(9) -0.0155(7) 0.0068(6) -0.0041(6) C17 0.0379(8) 0.0249(7) 0.0229(7) -0.0097(6) 0.0024(6) -0.0031(6) C18 0.0347(8) 0.0242(7) 0.0180(6) -0.0067(5) -0.0038(5) -0.0038(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.2812(17) . ? N1 C9A 1.4179(17) . ? C2 C13 1.4885(18) . ? C2 C3 1.5267(17) . ? C3 C10 1.5302(18) . ? C3 S4 1.8130(13) . ? C3 H3 1.0000 . ? S4 C5 1.8258(14) . ? C5 C5A 1.4986(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5A C6 1.390(2) . ? C5A C9A 1.4046(18) . ? C6 C7 1.385(2) . ? C6 H6 0.9500 . ? C7 C8 1.387(2) . ? C7 H7 0.9500 . ? C8 C9 1.385(2) . ? C8 H8 0.9500 . ? C9 C9A 1.3926(19) . ? C9 H9 0.9500 . ? C10 O2 1.2002(16) . ? C10 O1 1.3416(16) . ? O1 C11 1.4535(15) . ? C11 C12 1.4994(19) . ? C11 H11B 0.9900 . ? C11 H11A 0.9900 . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C12 H12A 0.9800 . ? C13 C14 1.386(2) . ? C13 C18 1.4001(19) . ? C14 C15 1.388(2) . ? C14 H14 0.9500 . ? C15 C16 1.378(2) . ? C15 H15 0.9500 . ? C16 C17 1.381(2) . ? C16 H16 0.9500 . ? C17 C18 1.380(2) . ? C17 H17 0.9500 . ? C18 H18 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 C2 N1 C9A 119.90(11) . . ? N1 C2 C13 117.80(11) . . ? N1 C2 C3 122.76(11) . . ? C13 C2 C3 119.40(11) . . ? C2 C3 C10 112.94(10) . . ? C2 C3 S4 109.91(9) . . ? C10 C3 S4 114.78(9) . . ? C2 C3 H3 106.2 . . ? C10 C3 H3 106.2 . . ? S4 C3 H3 106.2 . . ? C3 S4 C5 99.85(6) . . ? C5A C5 S4 112.65(9) . . ? C5A C5 H5A 109.1 . . ? S4 C5 H5A 109.1 . . ? C5A C5 H5B 109.1 . . ? S4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C6 C5A C9A 119.10(12) . . ? C6 C5A C5 121.95(12) . . ? C9A C5A C5 118.94(12) . . ? C7 C6 C5A 120.73(13) . . ? C7 C6 H6 119.6 . . ? C5A C6 H6 119.6 . . ? C6 C7 C8 119.82(13) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 120.42(13) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C9A 119.86(12) . . ? C8 C9 H9 120.1 . . ? C9A C9 H9 120.1 . . ? C9 C9A C5A 120.01(12) . . ? C9 C9A N1 119.41(11) . . ? C5A C9A N1 120.38(11) . . ? O2 C10 O1 125.14(12) . . ? O2 C10 C3 126.95(12) . . ? O1 C10 C3 107.73(10) . . ? C10 O1 C11 117.18(10) . . ? O1 C11 C12 107.55(11) . . ? O1 C11 H11B 110.2 . . ? C12 C11 H11B 110.2 . . ? O1 C11 H11A 110.2 . . ? C12 C11 H11A 110.2 . . ? H11B C11 H11A 108.5 . . ? C11 C12 H12C 109.5 . . ? C11 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? C11 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? H12B C12 H12A 109.5 . . ? C14 C13 C18 118.04(13) . . ? C14 C13 C2 123.24(12) . . ? C18 C13 C2 118.71(12) . . ? C13 C14 C15 120.90(14) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 120.47(15) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.21(14) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C18 C17 C16 120.67(14) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C13 120.69(13) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? 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 C9A N1 C2 C13 173.34(10) . . . . ? C9A N1 C2 C3 -4.38(17) . . . . ? N1 C2 C3 C10 -48.45(16) . . . . ? C13 C2 C3 C10 133.86(11) . . . . ? N1 C2 C3 S4 81.15(13) . . . . ? C13 C2 C3 S4 -96.54(11) . . . . ? C2 C3 S4 C5 -42.37(10) . . . . ? C10 C3 S4 C5 86.22(10) . . . . ? C3 S4 C5 C5A -43.31(11) . . . . ? S4 C5 C5A C6 -105.52(13) . . . . ? S4 C5 C5A C9A 75.53(14) . . . . ? C9A C5A C6 C7 1.00(19) . . . . ? C5 C5A C6 C7 -177.94(12) . . . . ? C5A C6 C7 C8 0.6(2) . . . . ? C6 C7 C8 C9 -0.7(2) . . . . ? C7 C8 C9 C9A -0.7(2) . . . . ? C8 C9 C9A C5A 2.34(19) . . . . ? C8 C9 C9A N1 177.19(12) . . . . ? C6 C5A C9A C9 -2.46(18) . . . . ? C5 C5A C9A C9 176.52(12) . . . . ? C6 C5A C9A N1 -177.25(11) . . . . ? C5 C5A C9A N1 1.72(18) . . . . ? C2 N1 C9A C9 127.19(13) . . . . ? C2 N1 C9A C5A -57.99(16) . . . . ? C2 C3 C10 O2 137.38(13) . . . . ? S4 C3 C10 O2 10.32(17) . . . . ? C2 C3 C10 O1 -47.22(13) . . . . ? S4 C3 C10 O1 -174.28(8) . . . . ? O2 C10 O1 C11 -5.25(18) . . . . ? C3 C10 O1 C11 179.25(10) . . . . ? C10 O1 C11 C12 159.23(11) . . . . ? N1 C2 C13 C14 167.32(13) . . . . ? C3 C2 C13 C14 -14.88(18) . . . . ? N1 C2 C13 C18 -13.91(17) . . . . ? C3 C2 C13 C18 163.90(11) . . . . ? C18 C13 C14 C15 -0.8(2) . . . . ? C2 C13 C14 C15 177.94(14) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 1.3(3) . . . . ? C15 C16 C17 C18 -1.2(2) . . . . ? C16 C17 C18 C13 0.1(2) . . . . ? C14 C13 C18 C17 0.94(19) . . . . ? C2 C13 C18 C17 -177.90(12) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 19.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.260 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.039 # Attachment 'cs170a.cif' data_cs170a _database_code_depnum_ccdc_archive 'CCDC 756122' #TrackingRef 'cs170a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Ethoxycarbonyl-2-(4-chlorophenyl)-1,5-dihydro-4,1-benzothiazepine ; _chemical_name_common ;3-Ethoxycarbonyl-2-(4-chlorophenyl)-1,5-dihydro-4,1- benzothiazepine ; _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N O2 S' _chemical_formula_sum 'C19 H19 N O2 S' _chemical_formula_weight 325.41 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 7.75740(10) _cell_length_b 11.3316(2) _cell_length_c 17.9221(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1575.42(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 11841 _cell_measurement_theta_min 6.9 _cell_measurement_theta_max 71.63 _exptl_crystal_description Chunk _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.71 _exptl_crystal_size_mid 0.65 _exptl_crystal_size_min 0.54 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.897 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.42 _exptl_absorpt_correction_T_max 0.60 _exptl_absorpt_process_details 'CrystalClear v1.4.0 (Rigaku, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis RAPID' _diffrn_measurement_method '\w -scan' _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12715 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 6.92 _diffrn_reflns_theta_max 66.55 _reflns_number_total 2748 _reflns_number_gt 2707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear v1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear v1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear v1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; ; _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^)+(0.0414P)^2^+0.3484P] 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 0.105(15) _refine_ls_number_reflns 2748 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0699 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 N1 N 0.7163(2) 0.20653(12) 0.09325(7) 0.0156(3) Uani 1 1 d . . . H1 H 0.6671 0.2678 0.0766 0.019 Uiso 1 1 d R . . C2 C 0.7974(2) 0.13980(13) 0.04006(8) 0.0142(3) Uani 1 1 d . . . C3 C 0.8852(2) 0.03548(13) 0.04787(8) 0.0152(3) Uani 1 1 d . . . S4 S 0.88353(5) -0.05616(3) 0.12842(2) 0.01634(11) Uani 1 1 d . . . C5 C 0.6715(2) -0.02049(14) 0.16614(9) 0.0178(4) Uani 1 1 d . . . H5A H 0.5893 -0.0138 0.1256 0.021 Uiso 1 1 calc R . . H5B H 0.6336 -0.0838 0.1987 0.021 Uiso 1 1 calc R . . C5A C 0.6755(2) 0.09254(15) 0.20895(9) 0.0172(3) Uani 1 1 d . . . C6 C 0.6572(2) 0.09302(15) 0.28642(9) 0.0204(4) Uani 1 1 d . . . H6 H 0.6338 0.0228 0.3113 0.024 Uiso 1 1 calc R . . C7 C 0.6735(2) 0.19687(16) 0.32686(9) 0.0220(4) Uani 1 1 d . . . H7 H 0.6645 0.1959 0.3786 0.026 Uiso 1 1 calc R . . C8 C 0.7032(2) 0.30209(15) 0.28957(9) 0.0211(4) Uani 1 1 d . . . H8 H 0.7141 0.3719 0.3165 0.025 Uiso 1 1 calc R . . C9 C 0.7168(2) 0.30406(14) 0.21224(9) 0.0181(4) Uani 1 1 d . . . H9 H 0.7325 0.3753 0.1874 0.022 Uiso 1 1 calc R . . C9A C 0.7069(2) 0.19903(15) 0.17213(9) 0.0156(3) Uani 1 1 d . . . C10 C 1.0037(2) -0.00455(14) -0.01082(9) 0.0158(3) Uani 1 1 d . . . O1 O 1.06370(16) -0.11449(10) 0.00374(6) 0.0220(3) Uani 1 1 d . . . O2 O 1.05346(15) 0.05141(10) -0.06474(6) 0.0189(3) Uani 1 1 d . . . C11 C 1.1902(2) -0.16360(15) -0.04742(10) 0.0217(4) Uani 1 1 d . . . H11A H 1.1576 -0.1439 -0.0982 0.026 Uiso 1 1 calc R . . H11B H 1.1899 -0.2489 -0.0429 0.026 Uiso 1 1 calc R . . C12 C 1.3678(3) -0.11875(16) -0.03280(11) 0.0297(4) Uani 1 1 d . . . H12A H 1.3740 -0.0367 -0.0459 0.045 Uiso 1 1 calc R . . H12B H 1.4490 -0.1625 -0.0623 0.045 Uiso 1 1 calc R . . H12C H 1.3947 -0.1282 0.0191 0.045 Uiso 1 1 calc R . . C13 C 0.7671(2) 0.19167(14) -0.03581(9) 0.0156(3) Uani 1 1 d . . . C14 C 0.6841(2) 0.12612(14) -0.09079(9) 0.0167(4) Uani 1 1 d . . . H14 H 0.6535 0.0482 -0.0812 0.020 Uiso 1 1 calc R . . C15 C 0.6465(2) 0.17536(15) -0.15967(9) 0.0180(4) Uani 1 1 d . . . H15 H 0.5907 0.1301 -0.1956 0.022 Uiso 1 1 calc R . . C16 C 0.6914(2) 0.29200(15) -0.17593(9) 0.0180(4) Uani 1 1 d . . . C17 C 0.7730(2) 0.35680(14) -0.12034(9) 0.0179(4) Uani 1 1 d . . . H17 H 0.8034 0.4348 -0.1298 0.021 Uiso 1 1 calc R . . C18 C 0.8104(2) 0.30863(14) -0.05133(9) 0.0165(3) Uani 1 1 d . . . H18 H 0.8645 0.3543 -0.0151 0.020 Uiso 1 1 calc R . . C19 C 0.6525(2) 0.34596(15) -0.25102(9) 0.0223(4) Uani 1 1 d . . . H19A H 0.6114 0.2859 -0.2843 0.033 Uiso 1 1 calc R . . H19B H 0.7555 0.3805 -0.2711 0.033 Uiso 1 1 calc R . . H19C H 0.5659 0.4058 -0.2454 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 N1 0.0182(8) 0.0156(7) 0.0131(6) 0.0007(5) 0.0003(6) 0.0028(6) C2 0.0132(8) 0.0169(7) 0.0125(7) -0.0001(6) -0.0007(7) -0.0033(7) C3 0.0169(8) 0.0172(7) 0.0116(7) 0.0001(6) -0.0012(7) -0.0026(7) S4 0.0184(2) 0.01678(18) 0.01379(18) 0.00223(14) 0.00188(16) 0.00186(16) C5 0.0172(9) 0.0203(8) 0.0161(8) 0.0021(6) 0.0026(7) -0.0011(7) C5A 0.0133(9) 0.0217(8) 0.0167(8) -0.0005(6) 0.0004(7) 0.0025(7) C6 0.0195(10) 0.0238(8) 0.0178(8) 0.0049(6) 0.0025(7) 0.0039(7) C7 0.0205(10) 0.0319(9) 0.0137(8) -0.0026(7) 0.0019(7) 0.0049(8) C8 0.0204(10) 0.0237(9) 0.0193(8) -0.0071(7) 0.0004(8) 0.0017(7) C9 0.0174(9) 0.0184(8) 0.0184(8) 0.0000(6) 0.0016(7) 0.0022(7) C9A 0.0114(8) 0.0219(8) 0.0134(8) 0.0000(6) -0.0003(7) 0.0011(7) C10 0.0140(9) 0.0185(8) 0.0147(8) -0.0014(6) -0.0024(7) -0.0018(7) O1 0.0265(7) 0.0177(6) 0.0219(6) 0.0015(5) 0.0093(5) 0.0052(5) O2 0.0187(6) 0.0212(6) 0.0166(6) 0.0017(5) 0.0026(5) 0.0006(5) C11 0.0230(9) 0.0193(8) 0.0227(9) -0.0033(7) 0.0071(8) 0.0014(7) C12 0.0246(10) 0.0267(10) 0.0378(10) -0.0088(8) 0.0000(9) 0.0063(9) C13 0.0133(9) 0.0195(8) 0.0140(8) 0.0013(6) 0.0023(7) 0.0040(7) C14 0.0145(8) 0.0171(8) 0.0185(8) -0.0007(6) 0.0010(7) -0.0015(7) C15 0.0160(9) 0.0221(8) 0.0158(7) -0.0032(6) -0.0012(7) 0.0009(7) C16 0.0155(9) 0.0238(8) 0.0146(8) 0.0013(6) 0.0017(7) 0.0058(8) C17 0.0168(9) 0.0167(7) 0.0201(8) 0.0023(6) 0.0043(7) 0.0017(7) C18 0.0152(9) 0.0184(8) 0.0158(7) -0.0025(6) -0.0008(7) -0.0004(7) C19 0.0239(11) 0.0275(9) 0.0156(8) 0.0020(7) 0.0005(7) 0.0031(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 N1 C2 1.370(2) . ? N1 C9A 1.418(2) . ? N1 H1 0.8467 . ? C2 C3 1.371(2) . ? C2 C13 1.500(2) . ? C3 C10 1.469(2) . ? C3 S4 1.7784(15) . ? S4 C5 1.8236(18) . ? C5 C5A 1.493(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5A C6 1.396(2) . ? C5A C9A 1.397(2) . ? C6 C7 1.388(2) . ? C6 H6 0.9300 . ? C7 C8 1.386(3) . ? C7 H7 0.9300 . ? C8 C9 1.390(2) . ? C8 H8 0.9300 . ? C9 C9A 1.393(2) . ? C9 H9 0.9300 . ? C10 O2 1.218(2) . ? C10 O1 1.3551(19) . ? O1 C11 1.4536(19) . ? C11 C12 1.492(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.392(2) . ? C13 C18 1.395(2) . ? C14 C15 1.386(2) . ? C14 H14 0.9300 . ? C15 C16 1.397(2) . ? C15 H15 0.9300 . ? C16 C17 1.390(2) . ? C16 C19 1.509(2) . ? C17 C18 1.383(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C9A 133.18(15) . . ? C2 N1 H1 114.5 . . ? C9A N1 H1 112.1 . . ? N1 C2 C3 129.26(14) . . ? N1 C2 C13 110.04(13) . . ? C3 C2 C13 120.54(14) . . ? C2 C3 C10 120.26(13) . . ? C2 C3 S4 125.64(12) . . ? C10 C3 S4 113.91(11) . . ? C3 S4 C5 100.25(8) . . ? C5A C5 S4 111.22(12) . . ? C5A C5 H5A 109.4 . . ? S4 C5 H5A 109.4 . . ? C5A C5 H5B 109.4 . . ? S4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C6 C5A C9A 118.98(15) . . ? C6 C5A C5 120.82(15) . . ? C9A C5A C5 120.12(14) . . ? C7 C6 C5A 120.90(16) . . ? C7 C6 H6 119.5 . . ? C5A C6 H6 119.5 . . ? C8 C7 C6 119.51(15) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 120.48(16) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C9A 119.78(16) . . ? C8 C9 H9 120.1 . . ? C9A C9 H9 120.1 . . ? C9 C9A C5A 120.27(14) . . ? C9 C9A N1 117.43(15) . . ? C5A C9A N1 122.12(15) . . ? O2 C10 O1 121.51(15) . . ? O2 C10 C3 127.25(15) . . ? O1 C10 C3 111.15(13) . . ? C10 O1 C11 117.52(13) . . ? O1 C11 C12 112.47(14) . . ? O1 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? O1 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 118.50(15) . . ? C14 C13 C2 120.34(14) . . ? C18 C13 C2 121.02(14) . . ? C15 C14 C13 120.87(15) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 120.94(15) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 117.62(14) . . ? C17 C16 C19 121.08(15) . . ? C15 C16 C19 121.30(15) . . ? C18 C17 C16 121.87(15) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C13 120.19(15) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C9A N1 C2 C3 6.5(3) . . . . ? C9A N1 C2 C13 -178.15(18) . . . . ? N1 C2 C3 C10 -162.38(17) . . . . ? C13 C2 C3 C10 22.7(2) . . . . ? N1 C2 C3 S4 12.4(3) . . . . ? C13 C2 C3 S4 -162.50(13) . . . . ? C2 C3 S4 C5 28.21(16) . . . . ? C10 C3 S4 C5 -156.74(12) . . . . ? C3 S4 C5 C5A -80.70(12) . . . . ? S4 C5 C5A C6 -110.15(16) . . . . ? S4 C5 C5A C9A 66.42(19) . . . . ? C9A C5A C6 C7 -1.4(3) . . . . ? C5 C5A C6 C7 175.23(17) . . . . ? C5A C6 C7 C8 1.9(3) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C7 C8 C9 C9A -2.4(3) . . . . ? C8 C9 C9A C5A 2.9(3) . . . . ? C8 C9 C9A N1 178.11(16) . . . . ? C6 C5A C9A C9 -1.1(3) . . . . ? C5 C5A C9A C9 -177.70(17) . . . . ? C6 C5A C9A N1 -176.02(16) . . . . ? C5 C5A C9A N1 7.4(3) . . . . ? C2 N1 C9A C9 139.27(19) . . . . ? C2 N1 C9A C5A -45.6(3) . . . . ? C2 C3 C10 O2 9.8(3) . . . . ? S4 C3 C10 O2 -165.53(14) . . . . ? C2 C3 C10 O1 -173.69(14) . . . . ? S4 C3 C10 O1 10.97(18) . . . . ? O2 C10 O1 C11 0.1(2) . . . . ? C3 C10 O1 C11 -176.67(14) . . . . ? C10 O1 C11 C12 80.23(19) . . . . ? N1 C2 C13 C14 -119.70(16) . . . . ? C3 C2 C13 C14 56.1(2) . . . . ? N1 C2 C13 C18 55.9(2) . . . . ? C3 C2 C13 C18 -128.34(17) . . . . ? C18 C13 C14 C15 0.6(2) . . . . ? C2 C13 C14 C15 176.25(15) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C14 C15 C16 C17 -0.7(2) . . . . ? C14 C15 C16 C19 179.40(16) . . . . ? C15 C16 C17 C18 0.4(2) . . . . ? C19 C16 C17 C18 -179.69(16) . . . . ? C16 C17 C18 C13 0.4(3) . . . . ? C14 C13 C18 C17 -0.9(2) . . . . ? C2 C13 C18 C17 -176.51(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.85 2.24 3.0627(18) 164.0 3_455 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 66.55 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.201 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.063 # Attachment 'cs170f.cif' data_cs170f _database_code_depnum_ccdc_archive 'CCDC 756123' #TrackingRef 'cs170f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R*)-3-Ethoxycarbonyl-2-(4-chlorophenyl)-3,5-dihydro-4,1-benzothiazepine ; _chemical_name_common ;(R*)-3-Ethoxycarbonyl-2-(4-chlorophenyl)-3,5-dihydro-4,1- benzothiazepine ; _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N O2 S' _chemical_formula_sum 'C19 H19 N O2 S' _chemical_formula_weight 325.41 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.9550(4) _cell_length_b 7.1696(2) _cell_length_c 18.6157(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.082(2) _cell_angle_gamma 90.00 _cell_volume 1634.06(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 26.35 _exptl_crystal_description block _exptl_crystal_colour clolorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32297 _diffrn_reflns_av_R_equivalents 0.0795 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.35 _reflns_number_total 3324 _reflns_number_gt 2637 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0142P)^2^+1.8579P] 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 3324 _refine_ls_number_parameters 222 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.058 _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 C5 C 1.08928(18) 0.2471(3) 0.29580(12) 0.0300(5) Uani 1 1 d . . . H5A H 1.1114 0.3480 0.2676 0.036 Uiso 1 1 calc R . . H5B H 1.1432 0.2436 0.3477 0.036 Uiso 1 1 calc R . . S4 S 0.95534(5) 0.30435(8) 0.30272(3) 0.03021(15) Uani 1 1 d . . . C3 C 0.87358(16) 0.2264(3) 0.20792(11) 0.0225(4) Uani 1 1 d . . . H3 H 0.8774 0.0871 0.2080 0.027 Uiso 1 1 calc R . . C2 C 0.92018(15) 0.2955(3) 0.14710(11) 0.0203(4) Uani 1 1 d . . . N1 N 0.99837(13) 0.2094(2) 0.13311(9) 0.0223(4) Uani 1 1 d . . . C9A C 1.04849(15) 0.0527(3) 0.17750(11) 0.0210(4) Uani 1 1 d . . . C9 C 1.06150(16) -0.1109(3) 0.14037(12) 0.0248(5) Uani 1 1 d . . . H9 H 1.0330 -0.1177 0.0865 0.030 Uiso 1 1 calc R . . C8 C 1.11560(16) -0.2628(3) 0.18157(13) 0.0284(5) Uani 1 1 d . . . H8 H 1.1229 -0.3741 0.1560 0.034 Uiso 1 1 calc R . . C7 C 1.15926(17) -0.2527(3) 0.26026(13) 0.0302(5) Uani 1 1 d . . . H7 H 1.1969 -0.3566 0.2886 0.036 Uiso 1 1 calc R . . C6 C 1.14766(17) -0.0896(3) 0.29750(13) 0.0283(5) Uani 1 1 d . . . H6 H 1.1772 -0.0835 0.3514 0.034 Uiso 1 1 calc R . . C5A C 1.09355(16) 0.0644(3) 0.25713(12) 0.0237(4) Uani 1 1 d . . . C10 C 0.75555(17) 0.2783(3) 0.19574(12) 0.0262(5) Uani 1 1 d D A . O1 O 0.69211(11) 0.2275(2) 0.12624(9) 0.0297(4) Uani 1 1 d D . . O2 O 0.72317(13) 0.3530(2) 0.24246(9) 0.0357(4) Uani 1 1 d . . . C11 C 0.5771(2) 0.2827(6) 0.1017(3) 0.0333(10) Uani 0.833(12) 1 d PD A 1 H11A H 0.5702 0.4124 0.1178 0.040 Uiso 0.833(12) 1 calc PR A 1 H11B H 0.5357 0.1998 0.1249 0.040 Uiso 0.833(12) 1 calc PR A 1 C12 C 0.5322(3) 0.2685(6) 0.0166(3) 0.0465(13) Uani 0.833(12) 1 d PD A 1 H12A H 0.5723 0.3536 -0.0060 0.070 Uiso 0.833(12) 1 calc PR A 1 H12B H 0.4547 0.3023 -0.0008 0.070 Uiso 0.833(12) 1 calc PR A 1 H12C H 0.5405 0.1403 0.0010 0.070 Uiso 0.833(12) 1 calc PR A 1 C11B C 0.5781(11) 0.297(4) 0.1257(11) 0.040(7) Uiso 0.167(12) 1 d PD A 2 H11C H 0.5561 0.2444 0.1676 0.048 Uiso 0.167(12) 1 calc PR A 2 H11D H 0.5726 0.4351 0.1255 0.048 Uiso 0.167(12) 1 calc PR A 2 C12B C 0.5193(14) 0.214(3) 0.0520(12) 0.040(5) Uiso 0.167(12) 1 d PD A 2 H12D H 0.5218 0.0782 0.0565 0.060 Uiso 0.167(12) 1 calc PR A 2 H12E H 0.5536 0.2532 0.0146 0.060 Uiso 0.167(12) 1 calc PR A 2 H12F H 0.4431 0.2563 0.0355 0.060 Uiso 0.167(12) 1 calc PR A 2 C13 C 0.87522(15) 0.4660(3) 0.10224(11) 0.0203(4) Uani 1 1 d . . . C14 C 0.82570(16) 0.6084(3) 0.13036(11) 0.0221(4) Uani 1 1 d . . . H14 H 0.8197 0.5971 0.1797 0.026 Uiso 1 1 calc R . . C15 C 0.78503(16) 0.7662(3) 0.08730(11) 0.0229(4) Uani 1 1 d . . . H15 H 0.7500 0.8599 0.1070 0.027 Uiso 1 1 calc R . . C16 C 0.79488(15) 0.7892(3) 0.01537(11) 0.0228(4) Uani 1 1 d . . . C17 C 0.84663(16) 0.6483(3) -0.01208(11) 0.0232(4) Uani 1 1 d . . . H17 H 0.8555 0.6626 -0.0605 0.028 Uiso 1 1 calc R . . C18 C 0.88524(15) 0.4887(3) 0.02980(11) 0.0217(4) Uani 1 1 d . . . H18 H 0.9187 0.3937 0.0095 0.026 Uiso 1 1 calc R . . C19 C 0.75163(18) 0.9613(3) -0.03119(13) 0.0313(5) Uani 1 1 d . . . H19A H 0.6750 0.9418 -0.0619 0.047 Uiso 1 1 calc R . . H19B H 0.7947 0.9862 -0.0647 0.047 Uiso 1 1 calc R . . H19C H 0.7571 1.0680 0.0028 0.047 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 C5 0.0325(12) 0.0244(11) 0.0285(11) -0.0022(9) 0.0034(9) -0.0024(9) S4 0.0414(3) 0.0280(3) 0.0222(3) -0.0018(2) 0.0117(2) 0.0030(2) C3 0.0274(11) 0.0215(10) 0.0217(10) 0.0008(8) 0.0122(8) 0.0014(9) C2 0.0201(10) 0.0225(10) 0.0186(9) -0.0017(8) 0.0067(7) -0.0018(8) N1 0.0198(8) 0.0237(9) 0.0239(9) 0.0010(7) 0.0079(7) 0.0008(7) C9A 0.0152(9) 0.0224(10) 0.0263(11) 0.0030(9) 0.0080(8) -0.0010(8) C9 0.0179(10) 0.0292(11) 0.0279(11) -0.0033(9) 0.0082(8) -0.0002(9) C8 0.0219(10) 0.0231(11) 0.0406(13) -0.0041(10) 0.0109(9) -0.0001(9) C7 0.0234(11) 0.0229(11) 0.0428(13) 0.0077(10) 0.0086(9) 0.0016(9) C6 0.0232(11) 0.0302(12) 0.0279(11) 0.0050(10) 0.0034(9) -0.0031(9) C5A 0.0202(10) 0.0224(10) 0.0271(11) 0.0004(9) 0.0056(8) -0.0026(8) C10 0.0318(11) 0.0198(10) 0.0340(12) 0.0097(9) 0.0203(10) 0.0032(9) O1 0.0205(7) 0.0298(8) 0.0409(9) 0.0040(7) 0.0129(6) 0.0031(6) O2 0.0470(10) 0.0328(9) 0.0411(9) 0.0085(7) 0.0332(8) 0.0113(8) C11 0.0189(16) 0.038(2) 0.048(3) 0.008(2) 0.0179(15) 0.0061(12) C12 0.0304(17) 0.051(2) 0.049(3) -0.0005(19) 0.0003(15) 0.0035(15) C13 0.0175(9) 0.0228(11) 0.0214(10) 0.0005(8) 0.0074(8) -0.0009(8) C14 0.0219(10) 0.0244(11) 0.0220(10) 0.0004(9) 0.0101(8) -0.0004(8) C15 0.0219(10) 0.0218(10) 0.0266(10) 0.0006(9) 0.0100(8) 0.0009(8) C16 0.0182(10) 0.0259(11) 0.0228(10) 0.0026(9) 0.0046(8) -0.0028(8) C17 0.0201(10) 0.0311(12) 0.0187(10) 0.0012(9) 0.0066(8) -0.0032(9) C18 0.0189(10) 0.0253(11) 0.0223(10) -0.0024(9) 0.0085(8) -0.0012(8) C19 0.0301(12) 0.0327(13) 0.0320(12) 0.0087(10) 0.0112(10) 0.0045(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 C5 C5A 1.505(3) . ? C5 S4 1.828(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? S4 C3 1.824(2) . ? C3 C10 1.517(3) . ? C3 C2 1.529(3) . ? C3 H3 1.0000 . ? C2 N1 1.284(2) . ? C2 C13 1.488(3) . ? N1 C9A 1.420(3) . ? C9A C9 1.399(3) . ? C9A C5A 1.407(3) . ? C9 C8 1.383(3) . ? C9 H9 0.9500 . ? C8 C7 1.389(3) . ? C8 H8 0.9500 . ? C7 C6 1.392(3) . ? C7 H7 0.9500 . ? C6 C5A 1.390(3) . ? C6 H6 0.9500 . ? C10 O2 1.207(2) . ? C10 O1 1.337(3) . ? O1 C11 1.463(3) . ? O1 C11B 1.557(14) . ? C11 C12 1.502(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C11B C12B 1.460(16) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13 C14 1.395(3) . ? C13 C18 1.406(3) . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 C16 1.396(3) . ? C15 H15 0.9500 . ? C16 C17 1.398(3) . ? C16 C19 1.507(3) . ? C17 C18 1.383(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C5A C5 S4 114.41(15) . . ? C5A C5 H5A 108.7 . . ? S4 C5 H5A 108.7 . . ? C5A C5 H5B 108.7 . . ? S4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C3 S4 C5 97.33(9) . . ? C10 C3 C2 115.63(16) . . ? C10 C3 S4 107.93(14) . . ? C2 C3 S4 111.86(14) . . ? C10 C3 H3 107.0 . . ? C2 C3 H3 107.0 . . ? S4 C3 H3 107.0 . . ? N1 C2 C13 118.13(17) . . ? N1 C2 C3 121.55(18) . . ? C13 C2 C3 120.32(16) . . ? C2 N1 C9A 120.24(17) . . ? C9 C9A C5A 119.66(19) . . ? C9 C9A N1 118.80(18) . . ? C5A C9A N1 121.29(18) . . ? C8 C9 C9A 120.5(2) . . ? C8 C9 H9 119.8 . . ? C9A C9 H9 119.8 . . ? C9 C8 C7 120.1(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C7 C6 119.7(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C5A C6 C7 121.0(2) . . ? C5A C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C5A C9A 118.98(19) . . ? C6 C5A C5 121.61(19) . . ? C9A C5A C5 119.25(18) . . ? O2 C10 O1 124.7(2) . . ? O2 C10 C3 124.9(2) . . ? O1 C10 C3 110.41(17) . . ? C10 O1 C11 118.0(2) . . ? C10 O1 C11B 101.6(7) . . ? C11 O1 C11B 17.0(7) . . ? O1 C11 C12 108.3(3) . . ? O1 C11 H11A 110.0 . . ? C12 C11 H11A 110.0 . . ? O1 C11 H11B 110.0 . . ? C12 C11 H11B 110.0 . . ? H11A C11 H11B 108.4 . . ? C12B C11B O1 94.4(12) . . ? C12B C11B H11C 112.8 . . ? O1 C11B H11C 112.8 . . ? C12B C11B H11D 112.8 . . ? O1 C11B H11D 112.8 . . ? H11C C11B H11D 110.3 . . ? C11B C12B H12D 109.5 . . ? C11B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C11B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C14 C13 C18 118.25(18) . . ? C14 C13 C2 122.29(17) . . ? C18 C13 C2 119.43(17) . . ? C15 C14 C13 120.94(19) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 120.95(19) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C17 118.06(19) . . ? C15 C16 C19 121.01(19) . . ? C17 C16 C19 120.93(18) . . ? C18 C17 C16 121.33(18) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C13 120.43(19) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C5A C5 S4 C3 -40.98(17) . . . . ? C5 S4 C3 C10 -174.20(14) . . . . ? C5 S4 C3 C2 -45.91(16) . . . . ? C10 C3 C2 N1 -153.06(19) . . . . ? S4 C3 C2 N1 82.9(2) . . . . ? C10 C3 C2 C13 26.9(3) . . . . ? S4 C3 C2 C13 -97.20(18) . . . . ? C13 C2 N1 C9A 176.14(17) . . . . ? C3 C2 N1 C9A -3.9(3) . . . . ? C2 N1 C9A C9 130.5(2) . . . . ? C2 N1 C9A C5A -55.2(3) . . . . ? C5A C9A C9 C8 1.8(3) . . . . ? N1 C9A C9 C8 176.24(17) . . . . ? C9A C9 C8 C7 -1.2(3) . . . . ? C9 C8 C7 C6 0.5(3) . . . . ? C8 C7 C6 C5A -0.4(3) . . . . ? C7 C6 C5A C9A 1.1(3) . . . . ? C7 C6 C5A C5 -174.30(19) . . . . ? C9 C9A C5A C6 -1.8(3) . . . . ? N1 C9A C5A C6 -176.03(18) . . . . ? C9 C9A C5A C5 173.72(18) . . . . ? N1 C9A C5A C5 -0.5(3) . . . . ? S4 C5 C5A C6 -108.5(2) . . . . ? S4 C5 C5A C9A 76.1(2) . . . . ? C2 C3 C10 O2 -128.1(2) . . . . ? S4 C3 C10 O2 -2.0(3) . . . . ? C2 C3 C10 O1 52.6(2) . . . . ? S4 C3 C10 O1 178.75(13) . . . . ? O2 C10 O1 C11 6.6(3) . . . . ? C3 C10 O1 C11 -174.1(2) . . . . ? O2 C10 O1 C11B 2.2(12) . . . . ? C3 C10 O1 C11B -178.6(11) . . . . ? C10 O1 C11 C12 161.6(3) . . . . ? C11B O1 C11 C12 177(4) . . . . ? C10 O1 C11B C12B -174.1(13) . . . . ? C11 O1 C11B C12B 20(3) . . . . ? N1 C2 C13 C14 -153.34(19) . . . . ? C3 C2 C13 C14 26.7(3) . . . . ? N1 C2 C13 C18 24.8(3) . . . . ? C3 C2 C13 C18 -155.15(18) . . . . ? C18 C13 C14 C15 1.5(3) . . . . ? C2 C13 C14 C15 179.68(18) . . . . ? C13 C14 C15 C16 -1.6(3) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C14 C15 C16 C19 -179.44(19) . . . . ? C15 C16 C17 C18 1.3(3) . . . . ? C19 C16 C17 C18 -179.10(19) . . . . ? C16 C17 C18 C13 -1.3(3) . . . . ? C14 C13 C18 C17 -0.1(3) . . . . ? C2 C13 C18 C17 -178.28(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.273 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.050 # Attachment 'cs173a.cif' data_cs173a _database_code_depnum_ccdc_archive 'CCDC 756124' #TrackingRef 'cs173a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Ethoxycarbonyl-2-(4-methylphenyl)-1,5-dihydro-4,1-benzothiazepine ; _chemical_name_common ;3-Ethoxycarbonyl-2-(4-methylphenyl)-1,5-dihydro-4,1- benzothiazepine ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Cl N O2 S' _chemical_formula_sum 'C18 H16 Cl N O2 S' _chemical_formula_weight 345.83 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' 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 P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' _chemical_absolute_configuration ad 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 8.005(4) _cell_length_b 10.923(3) _cell_length_c 18.797(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1643.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 99(2) _cell_measurement_reflns_used 12727 _cell_measurement_theta_min 3.16 _cell_measurement_theta_max 27.51 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.368 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8519 _exptl_absorpt_correction_T_max 0.8976 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 99(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-Axis Rapid' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13178 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3758 _reflns_number_gt 3543 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ; _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^)+(0.0699P)^2^+0.0484P] 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 0.095(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(7) _refine_ls_number_reflns 3758 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.257 _refine_ls_restrained_S_all 1.257 _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 C5 C 0.2259(3) 0.1353(2) 0.93428(12) 0.0231(5) Uani 1 1 d . . . H5A H 0.1692 0.0907 0.9732 0.028 Uiso 1 1 calc R . . H5B H 0.3331 0.0934 0.9246 0.028 Uiso 1 1 calc R . . S4 S 0.09590(7) 0.12939(5) 0.85474(3) 0.02231(16) Uani 1 1 d . . . C3 C 0.2530(3) 0.1521(2) 0.79018(12) 0.0189(4) Uani 1 1 d . . . C2 C 0.3733(3) 0.23983(19) 0.79251(11) 0.0174(4) Uani 1 1 d . . . N1 N 0.4026(2) 0.32638(16) 0.84489(9) 0.0192(4) Uani 1 1 d . . . H1 H 0.4719 0.3792 0.8312 0.025 Uiso 1 1 d R . . C9A C 0.3381(3) 0.35028(19) 0.91367(11) 0.0179(4) Uani 1 1 d . . . C9 C 0.3642(3) 0.4694(2) 0.93875(12) 0.0207(5) Uani 1 1 d . . . H9 H 0.4174 0.5280 0.9091 0.025 Uiso 1 1 calc R . . C8 C 0.3131(3) 0.5026(2) 1.00651(13) 0.0230(5) Uani 1 1 d . . . H8 H 0.3312 0.5838 1.0228 0.028 Uiso 1 1 calc R . . C7 C 0.2357(3) 0.4183(2) 1.05056(12) 0.0246(5) Uani 1 1 d . . . H7 H 0.2006 0.4411 1.0970 0.030 Uiso 1 1 calc R . . C6 C 0.2103(3) 0.3000(2) 1.02589(12) 0.0231(5) Uani 1 1 d . . . H6 H 0.1572 0.2420 1.0560 0.028 Uiso 1 1 calc R . . C5A C 0.2607(3) 0.2641(2) 0.95792(13) 0.0199(5) Uani 1 1 d . . . C10 C 0.2485(3) 0.0645(2) 0.73013(13) 0.0209(5) Uani 1 1 d . . . O1 O 0.0901(2) 0.03575(16) 0.71480(10) 0.0287(4) Uani 1 1 d . . . O2 O 0.3679(2) 0.02171(15) 0.69895(9) 0.0254(4) Uani 1 1 d . . . C11 C 0.0636(4) -0.0550(2) 0.65946(15) 0.0345(6) Uani 1 1 d . . . H11A H 0.1459 -0.1220 0.6651 0.041 Uiso 1 1 calc R . . H11B H -0.0495 -0.0905 0.6647 0.041 Uiso 1 1 calc R . . C12 C 0.0803(4) -0.0019(3) 0.58899(16) 0.0402(7) Uani 1 1 d . . . H12A H 0.0018 0.0664 0.5839 0.060 Uiso 1 1 calc R . . H12B H 0.0556 -0.0643 0.5530 0.060 Uiso 1 1 calc R . . H12C H 0.1947 0.0280 0.5825 0.060 Uiso 1 1 calc R . . C13 C 0.4914(3) 0.2569(2) 0.73155(12) 0.0186(4) Uani 1 1 d . . . C14 C 0.4340(3) 0.3055(2) 0.66785(12) 0.0222(5) Uani 1 1 d . . . H14 H 0.3195 0.3268 0.6630 0.027 Uiso 1 1 calc R . . C15 C 0.5427(3) 0.3232(2) 0.61097(12) 0.0233(5) Uani 1 1 d . . . H15 H 0.5033 0.3559 0.5672 0.028 Uiso 1 1 calc R . . C16 C 0.7089(3) 0.2923(2) 0.61927(12) 0.0218(5) Uani 1 1 d . . . C17 C 0.7705(3) 0.2447(2) 0.68246(13) 0.0248(5) Uani 1 1 d . . . H17 H 0.8854 0.2244 0.6872 0.030 Uiso 1 1 calc R . . C18 C 0.6603(3) 0.2274(2) 0.73846(12) 0.0224(5) Uani 1 1 d . . . H18 H 0.7003 0.1951 0.7822 0.027 Uiso 1 1 calc R . . Cl1 Cl 0.84374(8) 0.31128(5) 0.54735(3) 0.03097(19) 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 C5 0.0238(11) 0.0183(10) 0.0272(11) 0.0046(9) 0.0036(9) -0.0007(9) S4 0.0168(3) 0.0212(3) 0.0290(3) -0.0017(2) 0.0040(2) -0.0052(2) C3 0.0151(10) 0.0178(10) 0.0237(10) -0.0010(9) 0.0009(8) 0.0006(8) C2 0.0143(10) 0.0168(9) 0.0210(9) 0.0024(8) -0.0012(8) 0.0014(7) N1 0.0187(9) 0.0165(8) 0.0226(8) 0.0012(7) 0.0027(8) -0.0059(7) C9A 0.0153(10) 0.0171(9) 0.0215(10) 0.0014(8) -0.0015(8) 0.0007(8) C9 0.0157(11) 0.0195(10) 0.0268(11) 0.0029(9) -0.0020(9) -0.0013(8) C8 0.0205(11) 0.0218(10) 0.0267(11) -0.0050(9) -0.0049(9) 0.0004(8) C7 0.0194(11) 0.0317(12) 0.0228(11) -0.0024(10) -0.0028(9) 0.0049(9) C6 0.0169(10) 0.0266(11) 0.0257(11) 0.0058(10) 0.0006(9) 0.0009(9) C5A 0.0140(10) 0.0194(10) 0.0262(11) 0.0036(9) 0.0000(8) 0.0007(8) C10 0.0191(11) 0.0135(9) 0.0300(11) 0.0006(9) -0.0017(9) -0.0006(8) O1 0.0180(8) 0.0300(9) 0.0379(9) -0.0139(8) -0.0033(8) -0.0019(7) O2 0.0202(9) 0.0195(7) 0.0364(9) -0.0057(7) 0.0013(7) 0.0030(6) C11 0.0283(14) 0.0294(12) 0.0458(16) -0.0157(12) -0.0096(12) -0.0023(10) C12 0.0386(16) 0.0395(14) 0.0423(15) -0.0107(13) -0.0074(13) 0.0028(13) C13 0.0179(10) 0.0148(9) 0.0232(11) -0.0002(9) 0.0011(8) -0.0030(8) C14 0.0183(11) 0.0198(10) 0.0285(11) -0.0013(9) -0.0013(9) 0.0002(9) C15 0.0279(12) 0.0200(10) 0.0221(10) 0.0012(9) 0.0000(9) 0.0004(9) C16 0.0247(11) 0.0152(10) 0.0255(10) -0.0017(9) 0.0082(9) -0.0033(8) C17 0.0185(11) 0.0255(11) 0.0305(12) -0.0028(10) 0.0017(9) 0.0006(9) C18 0.0182(11) 0.0231(10) 0.0258(11) 0.0041(9) -0.0008(9) 0.0002(9) Cl1 0.0361(3) 0.0229(3) 0.0340(3) -0.0010(2) 0.0176(3) -0.0020(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 C5 C5A 1.501(3) . ? C5 S4 1.823(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? S4 C3 1.765(2) . ? C3 C2 1.359(3) . ? C3 C10 1.480(3) . ? C2 N1 1.385(3) . ? C2 C13 1.497(3) . ? N1 C9A 1.416(3) . ? N1 H1 0.8406 . ? C9A C9 1.400(3) . ? C9A C5A 1.401(3) . ? C9 C8 1.386(3) . ? C9 H9 0.9500 . ? C8 C7 1.384(4) . ? C8 H8 0.9500 . ? C7 C6 1.388(3) . ? C7 H7 0.9500 . ? C6 C5A 1.396(3) . ? C6 H6 0.9500 . ? C10 O2 1.215(3) . ? C10 O1 1.338(3) . ? O1 C11 1.452(3) . ? C11 C12 1.452(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.388(3) . ? C13 C18 1.395(3) . ? C14 C15 1.392(3) . ? C14 H14 0.9500 . ? C15 C16 1.381(4) . ? C15 H15 0.9500 . ? C16 C17 1.387(4) . ? C16 Cl1 1.742(2) . ? C17 C18 1.387(3) . ? C17 H17 0.9500 . ? C18 H18 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 C5A C5 S4 112.46(16) . . ? C5A C5 H5A 109.1 . . ? S4 C5 H5A 109.1 . . ? C5A C5 H5B 109.1 . . ? S4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C3 S4 C5 98.75(11) . . ? C2 C3 C10 119.8(2) . . ? C2 C3 S4 125.58(17) . . ? C10 C3 S4 114.58(16) . . ? C3 C2 N1 128.6(2) . . ? C3 C2 C13 120.69(19) . . ? N1 C2 C13 110.63(18) . . ? C2 N1 C9A 135.48(19) . . ? C2 N1 H1 111.2 . . ? C9A N1 H1 113.2 . . ? C9 C9A C5A 119.4(2) . . ? C9 C9A N1 115.1(2) . . ? C5A C9A N1 125.4(2) . . ? C8 C9 C9A 120.6(2) . . ? C8 C9 H9 119.7 . . ? C9A C9 H9 119.7 . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C7 C6 119.0(2) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C6 C5A 121.7(2) . . ? C7 C6 H6 119.2 . . ? C5A C6 H6 119.2 . . ? C6 C5A C9A 118.8(2) . . ? C6 C5A C5 118.7(2) . . ? C9A C5A C5 122.4(2) . . ? O2 C10 O1 123.5(2) . . ? O2 C10 C3 126.7(2) . . ? O1 C10 C3 109.8(2) . . ? C10 O1 C11 116.9(2) . . ? C12 C11 O1 111.6(2) . . ? C12 C11 H11A 109.3 . . ? O1 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? O1 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 119.3(2) . . ? C14 C13 C2 119.9(2) . . ? C18 C13 C2 120.8(2) . . ? C13 C14 C15 120.6(2) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 118.8(2) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 122.1(2) . . ? C15 C16 Cl1 118.69(19) . . ? C17 C16 Cl1 119.24(19) . . ? C18 C17 C16 118.3(2) . . ? C18 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? C17 C18 C13 121.0(2) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? 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 C5A C5 S4 C3 82.54(18) . . . . ? C5 S4 C3 C2 -47.3(2) . . . . ? C5 S4 C3 C10 131.77(17) . . . . ? C10 C3 C2 N1 -177.2(2) . . . . ? S4 C3 C2 N1 1.9(3) . . . . ? C10 C3 C2 C13 6.0(3) . . . . ? S4 C3 C2 C13 -174.88(16) . . . . ? C3 C2 N1 C9A 6.9(4) . . . . ? C13 C2 N1 C9A -176.1(2) . . . . ? C2 N1 C9A C9 -160.0(2) . . . . ? C2 N1 C9A C5A 23.4(4) . . . . ? C5A C9A C9 C8 -0.5(3) . . . . ? N1 C9A C9 C8 -177.3(2) . . . . ? C9A C9 C8 C7 0.2(3) . . . . ? C9 C8 C7 C6 0.1(3) . . . . ? C8 C7 C6 C5A 0.0(3) . . . . ? C7 C6 C5A C9A -0.3(3) . . . . ? C7 C6 C5A C5 -178.8(2) . . . . ? C9 C9A C5A C6 0.6(3) . . . . ? N1 C9A C5A C6 177.0(2) . . . . ? C9 C9A C5A C5 178.9(2) . . . . ? N1 C9A C5A C5 -4.6(3) . . . . ? S4 C5 C5A C6 120.5(2) . . . . ? S4 C5 C5A C9A -57.8(3) . . . . ? C2 C3 C10 O2 35.2(3) . . . . ? S4 C3 C10 O2 -144.0(2) . . . . ? C2 C3 C10 O1 -145.9(2) . . . . ? S4 C3 C10 O1 35.0(2) . . . . ? O2 C10 O1 C11 2.3(3) . . . . ? C3 C10 O1 C11 -176.7(2) . . . . ? C10 O1 C11 C12 -79.5(3) . . . . ? C3 C2 C13 C14 70.6(3) . . . . ? N1 C2 C13 C14 -106.7(2) . . . . ? C3 C2 C13 C18 -111.1(3) . . . . ? N1 C2 C13 C18 71.6(3) . . . . ? C18 C13 C14 C15 0.9(3) . . . . ? C2 C13 C14 C15 179.3(2) . . . . ? C13 C14 C15 C16 -0.5(3) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C14 C15 C16 Cl1 178.55(17) . . . . ? C15 C16 C17 C18 0.3(4) . . . . ? Cl1 C16 C17 C18 -178.39(18) . . . . ? C16 C17 C18 C13 0.1(4) . . . . ? C14 C13 C18 C17 -0.8(3) . . . . ? C2 C13 C18 C17 -179.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.84 2.09 2.933(3) 175.3 4_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.503 _refine_diff_density_min -0.795 _refine_diff_density_rms 0.191 # Attachment 'cs173f.cif' data_cs173f _database_code_depnum_ccdc_archive 'CCDC 756125' #TrackingRef 'cs173f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R*)-3-Ethoxycarbonyl-2-(4-methylphenyl)-3,5-dihydro-4,1-benzothiazepine ; _chemical_name_common ;(R*)-3-Ethoxycarbonyl-2-(4-methylphenyl)-3,5-dihydro-4,1- benzothiazepine ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Cl N O2 S' _chemical_formula_sum 'C18 H16 Cl N O2 S' _chemical_formula_weight 345.83 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' Cl Cl 0.1484 0.1585 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 12.699(2) _cell_length_b 7.2028(9) _cell_length_c 18.542(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.578(6) _cell_angle_gamma 90.00 _cell_volume 1607.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 49989 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8955 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-Axis Rapid' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 59115 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3690 _reflns_number_gt 3325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ; _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^)+(0.0320P)^2^+0.9814P] 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 3690 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0769 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 C5 C 0.41471(12) 0.7337(2) 0.20056(8) 0.0216(3) Uani 1 1 d . . . H5A H 0.3895 0.8334 0.2262 0.026 Uiso 1 1 calc R . . H5B H 0.3642 0.7271 0.1489 0.026 Uiso 1 1 calc R . . S4 S 0.55336(3) 0.79104(5) 0.197437(18) 0.01958(9) Uani 1 1 d . . . C3 C 0.63054(10) 0.71405(18) 0.29324(7) 0.0147(2) Uani 1 1 d . . . H3 H 0.6258 0.5783 0.2935 0.018 Uiso 1 1 calc R . . C2 C 0.57893(11) 0.78617(18) 0.35184(7) 0.0149(2) Uani 1 1 d . . . N1 N 0.49654(9) 0.70416(16) 0.36403(6) 0.0168(2) Uani 1 1 d . . . C9A C 0.44767(10) 0.54659(18) 0.32018(8) 0.0163(3) Uani 1 1 d . . . C9 C 0.43166(11) 0.3865(2) 0.35790(8) 0.0198(3) Uani 1 1 d . . . H9 H 0.4557 0.3832 0.4108 0.024 Uiso 1 1 calc R . . C8 C 0.38012(12) 0.2328(2) 0.31677(9) 0.0240(3) Uani 1 1 d . . . H8 H 0.3704 0.1261 0.3422 0.029 Uiso 1 1 calc R . . C7 C 0.34291(12) 0.2374(2) 0.23773(9) 0.0243(3) Uani 1 1 d . . . H7 H 0.3086 0.1340 0.2102 0.029 Uiso 1 1 calc R . . C6 C 0.35733(11) 0.3975(2) 0.20014(8) 0.0221(3) Uani 1 1 d . . . H6 H 0.3325 0.4000 0.1472 0.027 Uiso 1 1 calc R . . C5A C 0.40836(11) 0.55421(19) 0.24020(8) 0.0178(3) Uani 1 1 d . . . C10 C 0.75180(11) 0.76376(18) 0.30865(7) 0.0157(3) Uani 1 1 d . . . O1 O 0.81134(8) 0.71233(14) 0.37887(5) 0.0180(2) Uani 1 1 d . . . O2 O 0.78863(8) 0.83721(14) 0.26336(5) 0.0212(2) Uani 1 1 d . . . C11 C 0.92836(11) 0.7660(2) 0.40410(8) 0.0229(3) Uani 1 1 d . . . H11A H 0.9371 0.8897 0.3861 0.027 Uiso 1 1 calc R . . H11B H 0.9715 0.6799 0.3846 0.027 Uiso 1 1 calc R . . C12 C 0.96651(13) 0.7615(2) 0.48974(9) 0.0307(3) Uani 1 1 d . . . H12A H 0.9257 0.8517 0.5082 0.046 Uiso 1 1 calc R . . H12B H 1.0444 0.7899 0.5089 0.046 Uiso 1 1 calc R . . H12C H 0.9538 0.6401 0.5067 0.046 Uiso 1 1 calc R . . C13 C 0.62365(10) 0.95598(18) 0.39682(7) 0.0148(2) Uani 1 1 d . . . C14 C 0.67296(11) 1.09823(18) 0.36797(7) 0.0162(3) Uani 1 1 d . . . H14 H 0.6792 1.0867 0.3195 0.019 Uiso 1 1 calc R . . C15 C 0.71294(11) 1.25725(19) 0.41047(8) 0.0171(3) Uani 1 1 d . . . H15 H 0.7469 1.3510 0.3914 0.021 Uiso 1 1 calc R . . C16 C 0.70089(11) 1.27269(18) 0.48202(7) 0.0168(3) Uani 1 1 d . . . C17 C 0.65096(11) 1.1350(2) 0.51192(7) 0.0175(3) Uani 1 1 d . . . H17 H 0.6426 1.1493 0.5596 0.021 Uiso 1 1 calc R . . C18 C 0.61366(11) 0.97538(19) 0.46960(7) 0.0163(3) Uani 1 1 d . . . H18 H 0.5818 0.8805 0.4897 0.020 Uiso 1 1 calc R . . Cl1 Cl 0.74885(3) 1.47246(5) 0.53564(2) 0.02643(10) 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 C5 0.0196(6) 0.0218(7) 0.0199(7) 0.0030(5) 0.0014(5) 0.0020(5) S4 0.02431(17) 0.02034(17) 0.01358(15) 0.00210(12) 0.00531(12) -0.00076(13) C3 0.0176(6) 0.0151(6) 0.0120(6) -0.0001(5) 0.0059(5) -0.0004(5) C2 0.0165(6) 0.0159(6) 0.0123(6) 0.0010(5) 0.0047(5) 0.0012(5) N1 0.0168(5) 0.0175(5) 0.0169(5) -0.0013(4) 0.0066(4) -0.0007(4) C9A 0.0122(6) 0.0169(6) 0.0204(6) -0.0022(5) 0.0059(5) 0.0004(5) C9 0.0144(6) 0.0226(7) 0.0230(7) 0.0020(5) 0.0067(5) -0.0003(5) C8 0.0181(6) 0.0181(7) 0.0365(8) 0.0035(6) 0.0097(6) -0.0001(5) C7 0.0176(6) 0.0183(7) 0.0351(8) -0.0077(6) 0.0056(6) -0.0018(5) C6 0.0169(6) 0.0235(7) 0.0232(7) -0.0047(6) 0.0026(5) 0.0007(5) C5A 0.0145(6) 0.0179(6) 0.0202(6) -0.0008(5) 0.0042(5) 0.0024(5) C10 0.0201(6) 0.0128(6) 0.0164(6) -0.0038(5) 0.0090(5) -0.0010(5) O1 0.0150(4) 0.0210(5) 0.0183(5) 0.0002(4) 0.0057(4) -0.0027(4) O2 0.0261(5) 0.0218(5) 0.0206(5) -0.0022(4) 0.0142(4) -0.0042(4) C11 0.0151(6) 0.0253(7) 0.0285(7) -0.0031(6) 0.0075(5) -0.0038(5) C12 0.0251(7) 0.0325(8) 0.0290(8) 0.0021(7) 0.0007(6) -0.0066(6) C13 0.0140(6) 0.0162(6) 0.0148(6) -0.0014(5) 0.0052(5) 0.0014(5) C14 0.0196(6) 0.0168(6) 0.0143(6) -0.0001(5) 0.0082(5) 0.0009(5) C15 0.0182(6) 0.0160(6) 0.0186(6) 0.0007(5) 0.0079(5) -0.0005(5) C16 0.0166(6) 0.0159(6) 0.0167(6) -0.0051(5) 0.0037(5) -0.0014(5) C17 0.0160(6) 0.0232(7) 0.0137(6) -0.0022(5) 0.0055(5) -0.0009(5) C18 0.0154(6) 0.0197(6) 0.0147(6) 0.0004(5) 0.0060(5) -0.0016(5) Cl1 0.0343(2) 0.02251(18) 0.02468(18) -0.01064(13) 0.01253(15) -0.00976(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 C5 C5A 1.5018(19) . ? C5 S4 1.8274(15) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? S4 C3 1.8206(13) . ? C3 C10 1.5168(18) . ? C3 C2 1.5277(17) . ? C3 H3 0.9800 . ? C2 N1 1.2827(17) . ? C2 C13 1.4874(18) . ? N1 C9A 1.4187(17) . ? C9A C9 1.3965(19) . ? C9A C5A 1.4070(18) . ? C9 C8 1.385(2) . ? C9 H9 0.9300 . ? C8 C7 1.390(2) . ? C8 H8 0.9300 . ? C7 C6 1.389(2) . ? C7 H7 0.9300 . ? C6 C5A 1.3927(19) . ? C6 H6 0.9300 . ? C10 O2 1.2060(16) . ? C10 O1 1.3329(16) . ? O1 C11 1.4607(16) . ? C11 C12 1.506(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.3935(18) . ? C13 C18 1.4020(17) . ? C14 C15 1.3914(18) . ? C14 H14 0.9300 . ? C15 C16 1.3876(18) . ? C15 H15 0.9300 . ? C16 C17 1.3847(19) . ? C16 Cl1 1.7447(13) . ? C17 C18 1.3874(19) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? 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 C5A C5 S4 114.37(10) . . ? C5A C5 H5A 108.7 . . ? S4 C5 H5A 108.7 . . ? C5A C5 H5B 108.7 . . ? S4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C3 S4 C5 97.17(6) . . ? C10 C3 C2 115.19(10) . . ? C10 C3 S4 108.09(9) . . ? C2 C3 S4 111.77(9) . . ? C10 C3 H3 107.1 . . ? C2 C3 H3 107.1 . . ? S4 C3 H3 107.1 . . ? N1 C2 C13 117.84(11) . . ? N1 C2 C3 121.84(12) . . ? C13 C2 C3 120.32(11) . . ? C2 N1 C9A 119.99(11) . . ? C9 C9A C5A 120.05(12) . . ? C9 C9A N1 118.70(12) . . ? C5A C9A N1 121.09(12) . . ? C8 C9 C9A 120.19(13) . . ? C8 C9 H9 119.9 . . ? C9A C9 H9 119.9 . . ? C9 C8 C7 120.27(14) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C6 C7 C8 119.61(13) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C6 C5A 121.23(13) . . ? C7 C6 H6 119.4 . . ? C5A C6 H6 119.4 . . ? C6 C5A C9A 118.63(13) . . ? C6 C5A C5 121.68(12) . . ? C9A C5A C5 119.54(12) . . ? O2 C10 O1 125.24(12) . . ? O2 C10 C3 124.62(12) . . ? O1 C10 C3 110.14(10) . . ? C10 O1 C11 116.23(10) . . ? O1 C11 C12 106.55(12) . . ? O1 C11 H11A 110.4 . . ? C12 C11 H11A 110.4 . . ? O1 C11 H11B 110.4 . . ? C12 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 119.07(12) . . ? C14 C13 C2 121.82(11) . . ? C18 C13 C2 119.09(12) . . ? C15 C14 C13 121.02(12) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C16 C15 C14 118.43(12) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C17 C16 C15 121.97(12) . . ? C17 C16 Cl1 118.94(10) . . ? C15 C16 Cl1 119.09(10) . . ? C16 C17 C18 118.97(12) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C17 C18 C13 120.51(12) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? 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 C5A C5 S4 C3 -39.73(11) . . . . ? C5 S4 C3 C10 -174.81(9) . . . . ? C5 S4 C3 C2 -47.03(10) . . . . ? C10 C3 C2 N1 -153.35(12) . . . . ? S4 C3 C2 N1 82.78(14) . . . . ? C10 C3 C2 C13 26.70(17) . . . . ? S4 C3 C2 C13 -97.18(12) . . . . ? C13 C2 N1 C9A 177.14(11) . . . . ? C3 C2 N1 C9A -2.81(19) . . . . ? C2 N1 C9A C9 129.72(14) . . . . ? C2 N1 C9A C5A -54.91(17) . . . . ? C5A C9A C9 C8 2.0(2) . . . . ? N1 C9A C9 C8 177.39(12) . . . . ? C9A C9 C8 C7 -0.7(2) . . . . ? C9 C8 C7 C6 -0.2(2) . . . . ? C8 C7 C6 C5A -0.1(2) . . . . ? C7 C6 C5A C9A 1.4(2) . . . . ? C7 C6 C5A C5 -174.08(13) . . . . ? C9 C9A C5A C6 -2.29(19) . . . . ? N1 C9A C5A C6 -177.59(12) . . . . ? C9 C9A C5A C5 173.26(12) . . . . ? N1 C9A C5A C5 -2.04(19) . . . . ? S4 C5 C5A C6 -107.95(13) . . . . ? S4 C5 C5A C9A 76.64(14) . . . . ? C2 C3 C10 O2 -127.55(14) . . . . ? S4 C3 C10 O2 -1.76(16) . . . . ? C2 C3 C10 O1 53.24(15) . . . . ? S4 C3 C10 O1 179.03(9) . . . . ? O2 C10 O1 C11 5.94(19) . . . . ? C3 C10 O1 C11 -174.86(11) . . . . ? C10 O1 C11 C12 158.85(12) . . . . ? N1 C2 C13 C14 -150.14(13) . . . . ? C3 C2 C13 C14 29.82(18) . . . . ? N1 C2 C13 C18 28.39(18) . . . . ? C3 C2 C13 C18 -151.66(12) . . . . ? C18 C13 C14 C15 0.57(19) . . . . ? C2 C13 C14 C15 179.09(12) . . . . ? C13 C14 C15 C16 -1.1(2) . . . . ? C14 C15 C16 C17 0.2(2) . . . . ? C14 C15 C16 Cl1 -179.15(10) . . . . ? C15 C16 C17 C18 1.2(2) . . . . ? Cl1 C16 C17 C18 -179.45(10) . . . . ? C16 C17 C18 C13 -1.7(2) . . . . ? C14 C13 C18 C17 0.86(19) . . . . ? C2 C13 C18 C17 -177.71(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.373 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.050 # Attachment 'Fo1835.cif' data_alap19 _database_code_depnum_ccdc_archive 'CCDC 756126' #TrackingRef 'Fo1835.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Ethoxycarbonyl-3-(4-chlorophenyl)- 4,5-dihydro-7,8-dimethoxy-1,4-benzothiazepine ; _chemical_name_common ; 2-Ethoxycarbonyl-3-(4-chlorophenyl)-4,5-dihydro-7,8-dimethoxy- 1,4-benzothiazepine ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 Cl N O4 S' _chemical_formula_sum 'C20 H20 Cl N O4 S' _chemical_formula_weight 405.88 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' Cl Cl 0.3639 0.7018 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 15.2508(4) _cell_length_b 9.1719(3) _cell_length_c 14.8923(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.920(2) _cell_angle_gamma 90.00 _cell_volume 1873.57(10) _cell_formula_units_Z 4 _cell_measurement_temperature 98(2) _cell_measurement_reflns_used 7880 _cell_measurement_theta_min 6.60 _cell_measurement_theta_max 71.75 _exptl_crystal_description chunk _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 3.077 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4588 _exptl_absorpt_correction_T_max 0.8369 _exptl_absorpt_process_details 'CrystalClear v1.4.0 (Rigaku, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 98(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis RAPID' _diffrn_measurement_method '\w -scan' _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12566 _diffrn_reflns_av_R_equivalents 0.0746 _diffrn_reflns_av_sigmaI/netI 0.0819 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 6.61 _diffrn_reflns_theta_max 66.59 _reflns_number_total 3194 _reflns_number_gt 1795 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear v1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear v1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear v1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; ; _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^)+(0.0752P)^2^+7.6759P] 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 3194 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1311 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.2473 _refine_ls_wR_factor_gt 0.1690 _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_restrained_S_all 1.193 _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 -0.30921(12) 0.7749(2) 0.28772(12) 0.0413(5) Uani 1 1 d . . . S1 S 0.27463(11) 0.73921(19) 0.32810(11) 0.0337(5) Uani 1 1 d . . . O1 O -0.0023(3) 0.8153(5) 0.1608(3) 0.0336(11) Uani 1 1 d . . . O2 O 0.1261(3) 0.7633(5) 0.1318(3) 0.0367(11) Uani 1 1 d . . . O4 O 0.4561(3) 0.3095(5) 0.5608(3) 0.0366(11) Uani 1 1 d . . . O3 O 0.4730(3) 0.4444(5) 0.7183(3) 0.0353(11) Uani 1 1 d . . . C2 C 0.1495(4) 0.7719(7) 0.2997(4) 0.0286(14) Uani 1 1 d . . . N4 N 0.1652(4) 0.8334(6) 0.4665(4) 0.0306(12) Uani 1 1 d . . . H4N H 0.1328 0.8413 0.5028 0.043 Uiso 1 1 calc R . . C3 C 0.1127(4) 0.8008(7) 0.3680(4) 0.0286(14) Uani 1 1 d . . . C9 C 0.3654(4) 0.5098(7) 0.4522(4) 0.0296(14) Uani 1 1 d . . . H9 H 0.3608 0.4614 0.3939 0.038 Uiso 1 1 calc R . . C10 C 0.0918(5) 0.7795(7) 0.1921(5) 0.0344(15) Uani 1 1 d . . . C14 C -0.0482(5) 0.6651(8) 0.3066(5) 0.0339(15) Uani 1 1 d . . . H14 H -0.0179 0.5812 0.2951 0.044 Uiso 1 1 calc R . . C18 C -0.0386(4) 0.9173(7) 0.3592(4) 0.0310(14) Uani 1 1 d . . . H18 H -0.0019 1.0037 0.3856 0.040 Uiso 1 1 calc R . . C16 C -0.1885(4) 0.7844(7) 0.3051(4) 0.0292(14) Uani 1 1 d . . . C15 C -0.1454(5) 0.6599(8) 0.2888(5) 0.0372(16) Uani 1 1 d . . . H15 H -0.1820 0.5726 0.2659 0.048 Uiso 1 1 calc R . . C13 C 0.0058(5) 0.7949(7) 0.3417(4) 0.0315(15) Uani 1 1 d . . . C5A C 0.3250(4) 0.7155(7) 0.5297(5) 0.0308(14) Uani 1 1 d . . . C7 C 0.4194(4) 0.5163(8) 0.6304(5) 0.0342(15) Uani 1 1 d . . . C8 C 0.4130(5) 0.4454(7) 0.5440(5) 0.0300(14) Uani 1 1 d . . . C5 C 0.2695(4) 0.8564(7) 0.5168(5) 0.0314(14) Uani 1 1 d . . . H5B H 0.2869 0.9003 0.5832 0.041 Uiso 1 1 calc R . . H5A H 0.2888 0.9256 0.4776 0.041 Uiso 1 1 calc R . . C6 C 0.3736(5) 0.6497(7) 0.6223(5) 0.0335(15) Uani 1 1 d . . . H6 H 0.3756 0.6960 0.6803 0.044 Uiso 1 1 calc R . . C19 C 0.4843(5) 0.5155(8) 0.8080(4) 0.0409(17) Uani 1 1 d . . . H19C H 0.5140 0.6116 0.8121 0.057 Uiso 1 1 calc R . . H19B H 0.5265 0.4566 0.8657 0.057 Uiso 1 1 calc R . . H19A H 0.4204 0.5272 0.8078 0.057 Uiso 1 1 calc R . . C17 C -0.1376(5) 0.9123(7) 0.3375(5) 0.0353(15) Uani 1 1 d . . . H17 H -0.1695 0.9971 0.3452 0.046 Uiso 1 1 calc R . . C9A C 0.3235(5) 0.6479(8) 0.4453(4) 0.0346(15) Uani 1 1 d . . . C20 C 0.4410(5) 0.2267(7) 0.4739(5) 0.0383(16) Uani 1 1 d . . . H20C H 0.3710 0.2146 0.4322 0.054 Uiso 1 1 calc R . . H20B H 0.4716 0.1307 0.4940 0.054 Uiso 1 1 calc R . . H20A H 0.4702 0.2781 0.4359 0.054 Uiso 1 1 calc R . . C11 C -0.0606(5) 0.8375(8) 0.0550(4) 0.0381(16) Uani 1 1 d . . . H11B H -0.0629 0.7473 0.0176 0.050 Uiso 1 1 calc R . . H11A H -0.0328 0.9168 0.0303 0.050 Uiso 1 1 calc R . . C12 C -0.1586(5) 0.8767(11) 0.0422(5) 0.061(2) Uani 1 1 d . . . H12A H -0.1885 0.7926 0.0587 0.080 Uiso 1 1 calc R . . H12B H -0.1987 0.9055 -0.0273 0.080 Uiso 1 1 calc R . . H12C H -0.1542 0.9582 0.0865 0.080 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 0.0321(9) 0.0600(11) 0.0358(9) 0.0013(8) 0.0187(7) -0.0008(8) S1 0.0323(9) 0.0499(10) 0.0248(8) 0.0018(7) 0.0179(7) 0.0012(7) O1 0.038(3) 0.046(3) 0.020(2) -0.001(2) 0.016(2) 0.002(2) O2 0.041(3) 0.053(3) 0.022(2) 0.001(2) 0.019(2) 0.003(2) O4 0.048(3) 0.044(3) 0.023(2) 0.001(2) 0.020(2) 0.006(2) O3 0.042(3) 0.047(3) 0.025(2) -0.005(2) 0.022(2) -0.003(2) C2 0.028(3) 0.042(4) 0.015(3) 0.001(3) 0.009(3) -0.004(3) N4 0.036(3) 0.040(3) 0.025(3) -0.010(2) 0.023(2) -0.004(2) C3 0.024(3) 0.032(3) 0.028(3) 0.002(3) 0.010(3) 0.001(3) C9 0.038(4) 0.031(3) 0.024(3) -0.006(3) 0.018(3) 0.001(3) C10 0.041(4) 0.038(4) 0.031(4) -0.003(3) 0.022(3) 0.004(3) C14 0.034(4) 0.043(4) 0.029(3) -0.005(3) 0.017(3) -0.004(3) C18 0.034(3) 0.036(3) 0.028(3) -0.010(3) 0.018(3) -0.005(3) C16 0.021(3) 0.045(4) 0.022(3) 0.002(3) 0.010(3) -0.006(3) C15 0.039(4) 0.047(4) 0.027(3) -0.003(3) 0.016(3) -0.009(3) C13 0.040(4) 0.047(4) 0.011(3) 0.001(3) 0.015(3) -0.003(3) C5A 0.027(3) 0.042(4) 0.028(3) -0.008(3) 0.017(3) -0.009(3) C7 0.030(3) 0.052(4) 0.026(3) -0.006(3) 0.016(3) -0.014(3) C8 0.036(4) 0.033(3) 0.032(3) 0.001(3) 0.025(3) 0.002(3) C5 0.023(3) 0.040(4) 0.031(3) -0.002(3) 0.013(3) 0.006(3) C6 0.033(4) 0.047(4) 0.026(3) -0.005(3) 0.018(3) 0.003(3) C19 0.048(4) 0.058(5) 0.022(3) -0.004(3) 0.020(3) 0.002(4) C17 0.032(4) 0.037(4) 0.044(4) 0.004(3) 0.023(3) 0.005(3) C9A 0.034(4) 0.050(4) 0.022(3) 0.000(3) 0.014(3) 0.000(3) C20 0.057(4) 0.036(4) 0.031(4) -0.007(3) 0.027(3) 0.001(3) C11 0.043(4) 0.049(4) 0.019(3) 0.006(3) 0.011(3) 0.009(3) C12 0.041(4) 0.109(7) 0.033(4) -0.001(5) 0.016(4) 0.011(5) _geom_special_details ; ; 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 Cl1 C16 1.745(6) . ? S1 C9A 1.779(6) . ? S1 C2 1.790(6) . ? O1 C10 1.342(7) . ? O1 C11 1.446(7) . ? O2 C10 1.229(7) . ? O4 C8 1.380(7) . ? O4 C20 1.430(7) . ? O3 C7 1.371(7) . ? O3 C19 1.428(7) . ? C2 C3 1.386(8) . ? C2 C10 1.454(8) . ? N4 C3 1.363(7) . ? N4 C5 1.448(7) . ? N4 H4N 0.8800 . ? C3 C13 1.501(8) . ? C9 C8 1.370(8) . ? C9 C9A 1.402(9) . ? C9 H9 0.9500 . ? C14 C15 1.389(9) . ? C14 C13 1.411(9) . ? C14 H14 0.9500 . ? C18 C13 1.393(9) . ? C18 C17 1.401(8) . ? C18 H18 0.9500 . ? C16 C17 1.372(9) . ? C16 C15 1.391(9) . ? C15 H15 0.9500 . ? C5A C6 1.386(9) . ? C5A C9A 1.394(8) . ? C5A C5 1.510(9) . ? C7 C6 1.388(9) . ? C7 C8 1.406(8) . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? C6 H6 0.9500 . ? C19 H19C 0.9800 . ? C19 H19B 0.9800 . ? C19 H19A 0.9800 . ? C17 H17 0.9500 . ? C20 H20C 0.9800 . ? C20 H20B 0.9800 . ? C20 H20A 0.9800 . ? C11 C12 1.466(9) . ? C11 H11B 0.9900 . ? C11 H11A 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 C9A S1 C2 104.9(3) . . ? C10 O1 C11 117.9(5) . . ? C8 O4 C20 116.2(5) . . ? C7 O3 C19 116.8(5) . . ? C3 C2 C10 123.7(6) . . ? C3 C2 S1 126.2(5) . . ? C10 C2 S1 109.7(4) . . ? C3 N4 C5 125.8(5) . . ? C3 N4 H4N 117.1 . . ? C5 N4 H4N 117.1 . . ? N4 C3 C2 126.6(5) . . ? N4 C3 C13 110.4(5) . . ? C2 C3 C13 123.0(5) . . ? C8 C9 C9A 119.3(6) . . ? C8 C9 H9 120.4 . . ? C9A C9 H9 120.4 . . ? O2 C10 O1 120.6(6) . . ? O2 C10 C2 123.6(6) . . ? O1 C10 C2 115.7(5) . . ? C15 C14 C13 120.1(6) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C13 C18 C17 119.6(6) . . ? C13 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C17 C16 C15 121.7(6) . . ? C17 C16 Cl1 119.5(5) . . ? C15 C16 Cl1 118.8(5) . . ? C14 C15 C16 119.0(6) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C18 C13 C14 119.7(6) . . ? C18 C13 C3 118.9(6) . . ? C14 C13 C3 121.2(6) . . ? C6 C5A C9A 119.6(6) . . ? C6 C5A C5 121.7(5) . . ? C9A C5A C5 118.6(6) . . ? O3 C7 C6 125.0(6) . . ? O3 C7 C8 115.1(6) . . ? C6 C7 C8 119.8(6) . . ? C9 C8 O4 124.9(5) . . ? C9 C8 C7 120.5(6) . . ? O4 C8 C7 114.6(6) . . ? N4 C5 C5A 111.7(5) . . ? N4 C5 H5B 109.3 . . ? C5A C5 H5B 109.3 . . ? N4 C5 H5A 109.3 . . ? C5A C5 H5A 109.3 . . ? H5B C5 H5A 107.9 . . ? C5A C6 C7 120.0(6) . . ? C5A C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? O3 C19 H19C 109.5 . . ? O3 C19 H19B 109.5 . . ? H19C C19 H19B 109.5 . . ? O3 C19 H19A 109.5 . . ? H19C C19 H19A 109.5 . . ? H19B C19 H19A 109.5 . . ? C16 C17 C18 119.7(6) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C5A C9A C9 120.6(6) . . ? C5A C9A S1 120.7(5) . . ? C9 C9A S1 118.7(5) . . ? O4 C20 H20C 109.5 . . ? O4 C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? O4 C20 H20A 109.5 . . ? H20C C20 H20A 109.5 . . ? H20B C20 H20A 109.5 . . ? O1 C11 C12 106.4(5) . . ? O1 C11 H11B 110.4 . . ? C12 C11 H11B 110.4 . . ? O1 C11 H11A 110.4 . . ? C12 C11 H11A 110.4 . . ? H11B C11 H11A 108.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 C9A S1 C2 C3 33.3(7) . . . . ? C9A S1 C2 C10 -152.8(5) . . . . ? C5 N4 C3 C2 5.6(10) . . . . ? C5 N4 C3 C13 -176.2(6) . . . . ? C10 C2 C3 N4 -161.4(6) . . . . ? S1 C2 C3 N4 11.7(10) . . . . ? C10 C2 C3 C13 20.7(10) . . . . ? S1 C2 C3 C13 -166.3(5) . . . . ? C11 O1 C10 O2 -1.6(9) . . . . ? C11 O1 C10 C2 174.4(6) . . . . ? C3 C2 C10 O2 175.0(6) . . . . ? S1 C2 C10 O2 1.0(8) . . . . ? C3 C2 C10 O1 -0.9(9) . . . . ? S1 C2 C10 O1 -174.9(5) . . . . ? C13 C14 C15 C16 0.7(9) . . . . ? C17 C16 C15 C14 0.5(9) . . . . ? Cl1 C16 C15 C14 -177.3(5) . . . . ? C17 C18 C13 C14 -2.8(9) . . . . ? C17 C18 C13 C3 -178.3(5) . . . . ? C15 C14 C13 C18 0.5(9) . . . . ? C15 C14 C13 C3 175.9(5) . . . . ? N4 C3 C13 C18 57.4(7) . . . . ? C2 C3 C13 C18 -124.4(7) . . . . ? N4 C3 C13 C14 -118.0(6) . . . . ? C2 C3 C13 C14 60.2(8) . . . . ? C19 O3 C7 C6 -2.0(8) . . . . ? C19 O3 C7 C8 177.7(5) . . . . ? C9A C9 C8 O4 179.2(6) . . . . ? C9A C9 C8 C7 0.4(9) . . . . ? C20 O4 C8 C9 -6.1(9) . . . . ? C20 O4 C8 C7 172.7(5) . . . . ? O3 C7 C8 C9 -176.9(5) . . . . ? C6 C7 C8 C9 2.8(9) . . . . ? O3 C7 C8 O4 4.2(8) . . . . ? C6 C7 C8 O4 -176.1(5) . . . . ? C3 N4 C5 C5A -71.9(8) . . . . ? C6 C5A C5 N4 -108.2(6) . . . . ? C9A C5A C5 N4 69.3(7) . . . . ? C9A C5A C6 C7 -0.9(9) . . . . ? C5 C5A C6 C7 176.6(6) . . . . ? O3 C7 C6 C5A 177.1(6) . . . . ? C8 C7 C6 C5A -2.5(9) . . . . ? C15 C16 C17 C18 -2.8(10) . . . . ? Cl1 C16 C17 C18 175.0(5) . . . . ? C13 C18 C17 C16 4.0(9) . . . . ? C6 C5A C9A C9 4.2(9) . . . . ? C5 C5A C9A C9 -173.4(6) . . . . ? C6 C5A C9A S1 -172.4(5) . . . . ? C5 C5A C9A S1 10.1(8) . . . . ? C8 C9 C9A C5A -3.9(9) . . . . ? C8 C9 C9A S1 172.7(5) . . . . ? C2 S1 C9A C5A -61.4(6) . . . . ? C2 S1 C9A C9 122.0(5) . . . . ? C10 O1 C11 C12 -179.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.717 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.139