data_b733 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 Cl N2 O7 S' _chemical_formula_weight 446.89 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.128(4) _cell_length_b 11.5838(13) _cell_length_c 10.9008(12) _cell_angle_alpha 90.00 _cell_angle_beta 106.391(2) _cell_angle_gamma 90.00 _cell_volume 4013.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3629 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.52 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 0.338 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8994 _exptl_absorpt_correction_T_max 0.9354 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13786 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4603 _reflns_number_gt 3900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0663P)^2^+2.0092P] 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 4603 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _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 Cl1 Cl 0.400047(18) 0.09672(5) 0.08264(5) 0.02955(17) Uani 1 1 d . . . S1 S 0.302955(14) 0.57157(4) 0.17613(4) 0.01196(13) Uani 1 1 d . . . O1 O 0.40788(4) 0.33416(12) 0.19382(12) 0.0153(3) Uani 1 1 d . . . O2 O 0.31241(4) 0.63601(12) 0.29298(12) 0.0171(3) Uani 1 1 d . . . O3 O 0.26516(4) 0.50531(12) 0.13620(13) 0.0163(3) Uani 1 1 d . . . O4 O 0.49318(4) 0.17665(12) 0.55030(14) 0.0194(3) Uani 1 1 d . . . O5 O 0.55101(5) 0.27319(14) 0.65922(17) 0.0363(4) Uani 1 1 d . . . O6 O 0.32149(6) 1.00056(15) -0.20669(18) 0.0383(4) Uani 1 1 d . . . O7 O 0.28407(6) 0.88386(15) -0.34787(15) 0.0338(4) Uani 1 1 d . . . N1 N 0.34168(5) 0.48199(14) 0.18820(14) 0.0125(3) Uani 1 1 d . . . N2 N 0.30290(6) 0.90949(16) -0.23755(18) 0.0249(4) Uani 1 1 d . . . C1 C 0.41165(6) 0.41359(16) 0.29850(17) 0.0128(4) Uani 1 1 d . . . C2 C 0.38521(6) 0.52006(16) 0.24704(17) 0.0126(4) Uani 1 1 d . . . H2A H 0.3862 0.5749 0.3175 0.015 Uiso 1 1 calc R . . H2B H 0.3963 0.5595 0.1828 0.015 Uiso 1 1 calc R . . C3 C 0.33812(6) 0.40139(16) 0.08112(18) 0.0148(4) Uani 1 1 d . . . H3A H 0.3470 0.4399 0.0119 0.018 Uiso 1 1 calc R . . H3B H 0.3086 0.3757 0.0463 0.018 Uiso 1 1 calc R . . C4 C 0.36634(6) 0.29859(16) 0.13140(18) 0.0151(4) Uani 1 1 d . . . H4 H 0.3548 0.2550 0.1933 0.018 Uiso 1 1 calc R . . C5 C 0.36817(6) 0.21951(17) 0.02357(19) 0.0185(4) Uani 1 1 d . . . H5A H 0.3799 0.2618 -0.0375 0.022 Uiso 1 1 calc R . . H5B H 0.3394 0.1940 -0.0226 0.022 Uiso 1 1 calc R . . C6 C 0.39891(6) 0.36134(17) 0.41067(18) 0.0149(4) Uani 1 1 d . . . H6A H 0.3688 0.3400 0.3818 0.018 Uiso 1 1 calc R . . H6B H 0.4025 0.4202 0.4788 0.018 Uiso 1 1 calc R . . C7 C 0.42478(6) 0.25464(18) 0.46592(19) 0.0174(4) Uani 1 1 d . . . H7A H 0.4163 0.2262 0.5407 0.021 Uiso 1 1 calc R . . H7B H 0.4193 0.1926 0.4009 0.021 Uiso 1 1 calc R . . C8 C 0.47128(6) 0.28434(16) 0.50620(18) 0.0154(4) Uani 1 1 d . . . H8 H 0.4773 0.3413 0.5780 0.018 Uiso 1 1 calc R . . C9 C 0.48474(6) 0.33393(17) 0.39484(19) 0.0170(4) Uani 1 1 d . . . H9A H 0.4809 0.2751 0.3267 0.020 Uiso 1 1 calc R . . H9B H 0.5149 0.3547 0.4238 0.020 Uiso 1 1 calc R . . C10 C 0.45851(6) 0.44170(17) 0.34130(18) 0.0156(4) Uani 1 1 d . . . H10A H 0.4639 0.5024 0.4079 0.019 Uiso 1 1 calc R . . H10B H 0.4672 0.4720 0.2677 0.019 Uiso 1 1 calc R . . C11 C 0.53261(6) 0.18349(19) 0.6275(2) 0.0227(5) Uani 1 1 d . . . C12 C 0.54973(7) 0.0666(2) 0.6718(3) 0.0312(6) Uani 1 1 d . . . H12A H 0.5805 0.0688 0.6949 0.047 Uiso 1 1 calc R . . H12B H 0.5392 0.0105 0.6029 0.047 Uiso 1 1 calc R . . H12C H 0.5407 0.0441 0.7465 0.047 Uiso 1 1 calc R . . C13 C 0.30291(6) 0.67072(16) 0.05226(17) 0.0120(4) Uani 1 1 d . . . C14 C 0.32407(6) 0.77502(17) 0.08399(19) 0.0163(4) Uani 1 1 d . . . H14 H 0.3385 0.7922 0.1705 0.020 Uiso 1 1 calc R . . C15 C 0.32394(6) 0.85339(18) -0.0118(2) 0.0192(4) Uani 1 1 d . . . H15 H 0.3381 0.9254 0.0076 0.023 Uiso 1 1 calc R . . C16 C 0.30283(6) 0.82467(17) -0.13619(19) 0.0177(4) Uani 1 1 d . . . C17 C 0.28142(6) 0.72173(17) -0.16965(18) 0.0170(4) Uani 1 1 d . . . H17 H 0.2671 0.7051 -0.2564 0.020 Uiso 1 1 calc R . . C18 C 0.28139(6) 0.64344(17) -0.07358(18) 0.0143(4) Uani 1 1 d . . . H18 H 0.2669 0.5721 -0.0933 0.017 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 0.0346(3) 0.0170(3) 0.0291(3) -0.0026(2) -0.0039(2) 0.0103(2) S1 0.0120(2) 0.0145(2) 0.0090(2) 0.00140(17) 0.00228(16) 0.00304(17) O1 0.0146(7) 0.0174(7) 0.0123(6) -0.0027(5) 0.0011(5) 0.0023(5) O2 0.0196(7) 0.0209(7) 0.0101(6) -0.0008(5) 0.0033(5) 0.0050(6) O3 0.0132(6) 0.0180(7) 0.0174(7) 0.0042(5) 0.0036(5) 0.0019(5) O4 0.0156(7) 0.0153(7) 0.0230(7) 0.0049(6) -0.0016(6) 0.0019(6) O5 0.0240(8) 0.0243(9) 0.0461(11) 0.0052(8) -0.0135(7) -0.0019(7) O6 0.0457(11) 0.0267(9) 0.0463(11) 0.0159(8) 0.0191(9) -0.0032(8) O7 0.0421(10) 0.0381(10) 0.0233(9) 0.0141(7) 0.0128(7) 0.0128(8) N1 0.0120(8) 0.0137(8) 0.0104(7) -0.0008(6) 0.0009(6) 0.0027(6) N2 0.0265(10) 0.0260(10) 0.0266(10) 0.0118(8) 0.0143(8) 0.0092(8) C1 0.0137(9) 0.0136(9) 0.0101(8) -0.0017(7) 0.0017(7) 0.0018(7) C2 0.0120(8) 0.0142(9) 0.0107(8) 0.0005(7) 0.0017(7) -0.0001(7) C3 0.0166(9) 0.0158(10) 0.0107(9) -0.0017(7) 0.0016(7) 0.0021(7) C4 0.0150(9) 0.0151(9) 0.0129(9) 0.0009(7) 0.0000(7) 0.0005(7) C5 0.0228(10) 0.0149(10) 0.0137(9) -0.0006(7) -0.0014(7) 0.0065(8) C6 0.0113(9) 0.0203(10) 0.0129(9) 0.0033(8) 0.0032(7) 0.0021(8) C7 0.0140(9) 0.0187(10) 0.0186(10) 0.0056(8) 0.0031(7) 0.0001(8) C8 0.0147(9) 0.0130(9) 0.0165(9) 0.0025(7) 0.0012(7) 0.0041(7) C9 0.0132(9) 0.0205(10) 0.0167(9) 0.0026(8) 0.0030(7) 0.0038(8) C10 0.0111(9) 0.0200(10) 0.0155(9) 0.0038(8) 0.0036(7) 0.0016(7) C11 0.0170(10) 0.0223(11) 0.0244(11) 0.0062(9) -0.0012(8) 0.0025(9) C12 0.0227(11) 0.0237(12) 0.0414(14) 0.0125(10) -0.0004(10) 0.0074(9) C13 0.0114(9) 0.0128(9) 0.0122(9) 0.0026(7) 0.0039(7) 0.0045(7) C14 0.0149(9) 0.0173(10) 0.0155(9) -0.0009(7) 0.0022(7) 0.0017(8) C15 0.0190(10) 0.0146(10) 0.0255(11) 0.0014(8) 0.0085(8) 0.0008(8) C16 0.0183(10) 0.0165(10) 0.0212(10) 0.0072(8) 0.0104(8) 0.0083(8) C17 0.0161(9) 0.0220(11) 0.0125(9) 0.0016(8) 0.0035(7) 0.0076(8) C18 0.0131(9) 0.0149(9) 0.0142(9) -0.0002(7) 0.0025(7) 0.0041(7) _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 Cl1 C5 1.7802(19) . ? S1 O3 1.4279(14) . ? S1 O2 1.4327(14) . ? S1 N1 1.6263(16) . ? S1 C13 1.7724(19) . ? O1 C4 1.414(2) . ? O1 C1 1.444(2) . ? O4 C11 1.342(2) . ? O4 C8 1.455(2) . ? O5 C11 1.205(3) . ? O6 N2 1.220(2) . ? O7 N2 1.225(3) . ? N1 C2 1.471(2) . ? N1 C3 1.473(2) . ? N2 C16 1.479(3) . ? C1 C10 1.525(3) . ? C1 C2 1.525(2) . ? C1 C6 1.527(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.518(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.505(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.528(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.517(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.519(3) . ? C8 H8 1.0000 . ? C9 C10 1.539(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.494(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.391(3) . ? C13 C18 1.392(3) . ? C14 C15 1.383(3) . ? C14 H14 0.9500 . ? C15 C16 1.380(3) . ? C15 H15 0.9500 . ? C16 C17 1.383(3) . ? C17 C18 1.386(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 O3 S1 O2 120.27(8) . . ? O3 S1 N1 106.60(8) . . ? O2 S1 N1 106.92(8) . . ? O3 S1 C13 107.70(8) . . ? O2 S1 C13 107.01(9) . . ? N1 S1 C13 107.82(8) . . ? C4 O1 C1 114.93(14) . . ? C11 O4 C8 117.58(15) . . ? C2 N1 C3 112.66(14) . . ? C2 N1 S1 119.86(13) . . ? C3 N1 S1 117.08(12) . . ? O6 N2 O7 123.91(19) . . ? O6 N2 C16 118.39(19) . . ? O7 N2 C16 117.70(19) . . ? O1 C1 C10 103.38(14) . . ? O1 C1 C2 108.19(14) . . ? C10 C1 C2 111.67(15) . . ? O1 C1 C6 113.49(15) . . ? C10 C1 C6 109.10(15) . . ? C2 C1 C6 110.82(15) . . ? N1 C2 C1 107.97(15) . . ? N1 C2 H2A 110.1 . . ? C1 C2 H2A 110.1 . . ? N1 C2 H2B 110.1 . . ? C1 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? N1 C3 C4 107.92(15) . . ? N1 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? N1 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? O1 C4 C5 107.76(15) . . ? O1 C4 C3 111.22(15) . . ? C5 C4 C3 110.62(15) . . ? O1 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? C4 C5 Cl1 110.76(13) . . ? C4 C5 H5A 109.5 . . ? Cl1 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? Cl1 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C1 C6 C7 112.68(15) . . ? C1 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C1 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 109.97(16) . . ? C8 C7 H7A 109.7 . . ? C6 C7 H7A 109.7 . . ? C8 C7 H7B 109.7 . . ? C6 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O4 C8 C7 105.79(15) . . ? O4 C8 C9 110.91(15) . . ? C7 C8 C9 110.94(15) . . ? O4 C8 H8 109.7 . . ? C7 C8 H8 109.7 . . ? C9 C8 H8 109.7 . . ? C8 C9 C10 110.39(16) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C1 C10 C9 111.10(16) . . ? C1 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C1 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O5 C11 O4 123.71(19) . . ? O5 C11 C12 124.99(19) . . ? O4 C11 C12 111.27(18) . . ? 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 121.62(17) . . ? C14 C13 S1 118.79(14) . . ? C18 C13 S1 119.58(14) . . ? C15 C14 C13 119.26(18) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C16 C15 C14 118.47(19) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C15 C16 C17 123.18(18) . . ? C15 C16 N2 117.84(18) . . ? C17 C16 N2 118.98(18) . . ? C16 C17 C18 118.35(18) . . ? C16 C17 H17 120.8 . . ? C18 C17 H17 120.8 . . ? C17 C18 C13 119.13(18) . . ? C17 C18 H18 120.4 . . ? C13 C18 H18 120.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.695 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.088