data_pb29(R11) _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 O3 S' _chemical_formula_weight 240.31 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' '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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.8940(9) _cell_length_b 5.7394(6) _cell_length_c 13.2234(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.583(2) _cell_angle_gamma 90.00 _cell_volume 590.75(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5446 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.26 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9089 _exptl_absorpt_correction_T_max 0.9641 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6641 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2579 _reflns_number_gt 2552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0391P)^2^+0.0627P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration 'ad' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(5) _refine_ls_number_reflns 2579 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0234 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.0615 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 S1 S 0.26879(3) 0.82388(6) 0.25668(2) 0.02728(9) Uani 1 1 d . . . O1 O 0.41023(11) 0.63038(18) 0.59246(7) 0.0301(2) Uani 1 1 d . . . O2 O 0.11889(12) 0.58319(19) 0.56587(8) 0.0326(2) Uani 1 1 d . . . O3 O 0.42850(12) 0.69971(19) 0.23956(7) 0.0342(2) Uani 1 1 d . . . C1 C 0.24420(16) 0.7768(2) 0.38876(9) 0.0258(3) Uani 1 1 d . . . C2 C 0.27511(17) 0.5256(2) 0.42350(10) 0.0279(3) Uani 1 1 d . . . C3 C 0.27445(17) 0.4983(2) 0.53723(10) 0.0276(3) Uani 1 1 d . . . C4 C 0.34901(18) 0.7111(3) 0.68241(10) 0.0307(3) Uani 1 1 d . . . C5 C 0.16388(19) 0.7645(2) 0.64001(10) 0.0305(3) Uani 1 1 d . . . C6 C 0.09124(15) 0.6524(2) 0.19530(9) 0.0245(2) Uani 1 1 d . . . C7 C -0.07565(18) 0.7341(2) 0.19295(10) 0.0291(3) Uani 1 1 d . . . C8 C -0.21356(16) 0.6070(2) 0.14241(10) 0.0295(3) Uani 1 1 d . . . C9 C -0.18729(17) 0.3990(2) 0.09279(10) 0.0280(3) Uani 1 1 d . . . C10 C -0.01928(16) 0.3199(3) 0.09534(9) 0.0288(2) Uani 1 1 d . . . C11 C 0.11999(17) 0.4463(2) 0.14643(10) 0.0274(3) Uani 1 1 d . . . C12 C -0.3380(2) 0.2613(3) 0.03854(12) 0.0381(3) Uani 1 1 d . . . H1A H 0.1286(19) 0.826(4) 0.3960(11) 0.029(3) Uiso 1 1 d . . . H1B H 0.325(2) 0.874(3) 0.4247(12) 0.031(4) Uiso 1 1 d . . . H2A H 0.194(2) 0.433(4) 0.3861(14) 0.039(5) Uiso 1 1 d . . . H2B H 0.381(2) 0.474(3) 0.4103(12) 0.028(4) Uiso 1 1 d . . . H3 H 0.2837(18) 0.331(4) 0.5581(11) 0.031(4) Uiso 1 1 d . . . H4A H 0.425(2) 0.840(4) 0.7096(13) 0.042(4) Uiso 1 1 d . . . H4B H 0.3592(19) 0.585(3) 0.7290(11) 0.024(4) Uiso 1 1 d . . . H5A H 0.1533(18) 0.913(3) 0.6082(11) 0.017(3) Uiso 1 1 d . . . H5B H 0.095(2) 0.751(3) 0.6919(12) 0.032(4) Uiso 1 1 d . . . H7 H -0.088(2) 0.880(3) 0.2232(12) 0.029(4) Uiso 1 1 d . . . H8 H -0.322(2) 0.663(4) 0.1435(14) 0.043(5) Uiso 1 1 d . . . H10 H -0.0007(19) 0.177(3) 0.0628(11) 0.022(3) Uiso 1 1 d . . . H11 H 0.238(2) 0.396(3) 0.1495(13) 0.038(5) Uiso 1 1 d . . . H12A H -0.315(3) 0.102(6) 0.038(2) 0.096(10) Uiso 1 1 d . . . H12B H -0.435(2) 0.284(4) 0.0653(15) 0.050(5) Uiso 1 1 d . . . H12C H -0.365(3) 0.305(5) -0.0346(17) 0.065(6) Uiso 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 S1 0.02422(14) 0.02943(15) 0.02924(15) 0.00148(13) 0.00751(10) -0.00090(14) O1 0.0230(4) 0.0391(5) 0.0288(4) -0.0033(4) 0.0061(3) -0.0023(4) O2 0.0228(4) 0.0435(6) 0.0330(5) -0.0065(4) 0.0093(4) -0.0063(4) O3 0.0228(4) 0.0465(6) 0.0353(5) -0.0014(5) 0.0108(4) 0.0004(4) C1 0.0239(6) 0.0278(7) 0.0262(5) -0.0036(5) 0.0053(5) -0.0001(4) C2 0.0274(6) 0.0283(6) 0.0290(6) -0.0034(5) 0.0075(5) 0.0001(5) C3 0.0261(6) 0.0283(6) 0.0290(6) -0.0012(5) 0.0066(5) -0.0015(5) C4 0.0297(7) 0.0366(7) 0.0266(6) -0.0018(6) 0.0067(5) -0.0027(6) C5 0.0320(7) 0.0328(8) 0.0285(6) -0.0001(5) 0.0106(5) 0.0013(5) C6 0.0235(6) 0.0280(6) 0.0224(5) 0.0013(4) 0.0049(4) 0.0002(5) C7 0.0275(6) 0.0278(6) 0.0329(7) -0.0003(6) 0.0078(5) 0.0043(5) C8 0.0231(6) 0.0351(7) 0.0306(6) 0.0034(6) 0.0052(5) 0.0052(5) C9 0.0291(6) 0.0334(6) 0.0219(5) 0.0040(5) 0.0052(5) -0.0001(5) C10 0.0331(6) 0.0302(6) 0.0239(5) -0.0009(6) 0.0072(4) 0.0030(7) C11 0.0258(6) 0.0309(6) 0.0263(6) 0.0022(5) 0.0071(5) 0.0068(5) C12 0.0332(8) 0.0467(10) 0.0334(7) -0.0027(6) 0.0022(6) -0.0040(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 S1 O3 1.4979(10) . ? S1 C6 1.7926(13) . ? S1 C1 1.8094(13) . ? O1 C3 1.4129(16) . ? O1 C4 1.4334(16) . ? O2 C3 1.4297(16) . ? O2 C5 1.4330(17) . ? C1 C2 1.5204(18) . ? C1 H1A 0.975(15) . ? C1 H1B 0.916(18) . ? C2 C3 1.5130(18) . ? C2 H2A 0.91(2) . ? C2 H2B 0.929(16) . ? C3 H3 1.00(2) . ? C4 C5 1.507(2) . ? C4 H4A 0.98(2) . ? C4 H4B 0.945(17) . ? C5 H5A 0.947(16) . ? C5 H5B 0.945(15) . ? C6 C11 1.3844(18) . ? C6 C7 1.3940(18) . ? C7 C8 1.386(2) . ? C7 H7 0.939(18) . ? C8 C9 1.394(2) . ? C8 H8 0.918(18) . ? C9 C10 1.3969(18) . ? C9 C12 1.507(2) . ? C10 C11 1.3943(19) . ? C10 H10 0.950(16) . ? C11 H11 0.972(17) . ? C12 H12A 0.93(4) . ? C12 H12B 0.904(19) . ? C12 H12C 0.99(2) . ? 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 C6 106.54(6) . . ? O3 S1 C1 107.64(6) . . ? C6 S1 C1 98.83(6) . . ? C3 O1 C4 105.72(9) . . ? C3 O2 C5 107.62(10) . . ? C2 C1 S1 113.31(9) . . ? C2 C1 H1A 110.6(12) . . ? S1 C1 H1A 107.7(9) . . ? C2 C1 H1B 111.0(10) . . ? S1 C1 H1B 103.5(10) . . ? H1A C1 H1B 110.5(15) . . ? C3 C2 C1 111.82(10) . . ? C3 C2 H2A 111.0(11) . . ? C1 C2 H2A 109.1(12) . . ? C3 C2 H2B 107.8(10) . . ? C1 C2 H2B 110.3(10) . . ? H2A C2 H2B 106.7(15) . . ? O1 C3 O2 106.93(10) . . ? O1 C3 C2 109.29(10) . . ? O2 C3 C2 111.91(11) . . ? O1 C3 H3 111.1(8) . . ? O2 C3 H3 106.3(8) . . ? C2 C3 H3 111.2(9) . . ? O1 C4 C5 101.36(10) . . ? O1 C4 H4A 106.2(10) . . ? C5 C4 H4A 118.5(11) . . ? O1 C4 H4B 106.8(9) . . ? C5 C4 H4B 111.7(9) . . ? H4A C4 H4B 110.9(14) . . ? O2 C5 C4 102.81(11) . . ? O2 C5 H5A 110.8(9) . . ? C4 C5 H5A 110.9(9) . . ? O2 C5 H5B 109.2(10) . . ? C4 C5 H5B 110.4(10) . . ? H5A C5 H5B 112.3(13) . . ? C11 C6 C7 120.33(12) . . ? C11 C6 S1 120.26(10) . . ? C7 C6 S1 119.34(11) . . ? C8 C7 C6 119.79(13) . . ? C8 C7 H7 123.1(10) . . ? C6 C7 H7 117.1(10) . . ? C7 C8 C9 120.75(12) . . ? C7 C8 H8 118.0(13) . . ? C9 C8 H8 121.2(13) . . ? C8 C9 C10 118.81(13) . . ? C8 C9 C12 120.36(12) . . ? C10 C9 C12 120.83(13) . . ? C11 C10 C9 120.77(13) . . ? C11 C10 H10 120.0(9) . . ? C9 C10 H10 119.2(9) . . ? C6 C11 C10 119.56(12) . . ? C6 C11 H11 117.6(10) . . ? C10 C11 H11 122.9(10) . . ? C9 C12 H12A 112.4(17) . . ? C9 C12 H12B 112.9(13) . . ? H12A C12 H12B 109(2) . . ? C9 C12 H12C 111.1(15) . . ? H12A C12 H12C 104(2) . . ? H12B C12 H12C 106.6(17) . . ? 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 O3 S1 C1 C2 -44.70(11) . . . . ? C6 S1 C1 C2 65.90(10) . . . . ? S1 C1 C2 C3 173.19(9) . . . . ? C4 O1 C3 O2 25.36(13) . . . . ? C4 O1 C3 C2 146.69(11) . . . . ? C5 O2 C3 O1 -0.97(13) . . . . ? C5 O2 C3 C2 -120.61(11) . . . . ? C1 C2 C3 O1 -62.42(14) . . . . ? C1 C2 C3 O2 55.83(14) . . . . ? C3 O1 C4 C5 -38.17(13) . . . . ? C3 O2 C5 C4 -22.22(13) . . . . ? O1 C4 C5 O2 36.68(13) . . . . ? O3 S1 C6 C11 1.04(12) . . . . ? C1 S1 C6 C11 -110.43(11) . . . . ? O3 S1 C6 C7 -175.84(10) . . . . ? C1 S1 C6 C7 72.69(11) . . . . ? C11 C6 C7 C8 0.75(19) . . . . ? S1 C6 C7 C8 177.63(10) . . . . ? C6 C7 C8 C9 -0.7(2) . . . . ? C7 C8 C9 C10 0.37(19) . . . . ? C7 C8 C9 C12 179.66(13) . . . . ? C8 C9 C10 C11 -0.06(19) . . . . ? C12 C9 C10 C11 -179.36(12) . . . . ? C7 C6 C11 C10 -0.45(19) . . . . ? S1 C6 C11 C10 -177.30(10) . . . . ? C9 C10 C11 C6 0.11(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.203 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.035 #===END data_pb26(SsynH12) _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H15 Cl O3 S' _chemical_formula_sum 'C12 H15 Cl O3 S' _chemical_formula_weight 274.75 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' '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 P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8959(12) _cell_length_b 9.5822(16) _cell_length_c 10.2161(17) _cell_angle_alpha 90.00 _cell_angle_beta 107.309(2) _cell_angle_gamma 90.00 _cell_volume 644.49(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5324 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 28.26 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.451 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8400 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7197 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2804 _reflns_number_gt 2764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0511P)^2^+0.0328P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration 'ad' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_number_reflns 2804 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0256 _refine_ls_R_factor_gt 0.0252 _refine_ls_wR_factor_ref 0.0695 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.80170(7) 0.93223(4) 0.73895(4) 0.03594(11) Uani 1 1 d . . . S1 S 0.91776(6) 0.84286(4) 0.49225(4) 0.02686(10) Uani 1 1 d . . . O1 O 0.91895(19) 0.69719(12) 0.54421(13) 0.0354(3) Uani 1 1 d . . . O2 O 1.4755(2) 1.01028(15) 0.90795(15) 0.0477(4) Uani 1 1 d . . . O3 O 1.23009(19) 1.16587(13) 0.80943(13) 0.0355(3) Uani 1 1 d . . . C1 C 0.9742(2) 0.95818(16) 0.64116(16) 0.0260(3) Uani 1 1 d . . . C2 C 1.1931(3) 0.9320(2) 0.72480(17) 0.0318(3) Uani 1 1 d . . . C3 C 1.2632(3) 1.02523(19) 0.84871(18) 0.0327(3) Uani 1 1 d . . . C4 C 1.5525(3) 1.1438(2) 0.9626(2) 0.0414(4) Uani 1 1 d . . . C5 C 1.3718(3) 1.2411(2) 0.9175(2) 0.0387(4) Uani 1 1 d . . . C6 C 0.6602(2) 0.89274(16) 0.41270(15) 0.0240(3) Uani 1 1 d . . . C7 C 0.6201(2) 1.02754(17) 0.36182(17) 0.0281(3) Uani 1 1 d . . . C8 C 0.4213(3) 1.06262(18) 0.28893(17) 0.0300(3) Uani 1 1 d . . . C9 C 0.2656(3) 0.96382(18) 0.26489(17) 0.0300(3) Uani 1 1 d . . . C10 C 0.3113(2) 0.8304(2) 0.31651(18) 0.0330(3) Uani 1 1 d . . . C11 C 0.5081(3) 0.79300(18) 0.39107(18) 0.0308(3) Uani 1 1 d . . . C12 C 0.0523(3) 1.0040(2) 0.1834(2) 0.0411(4) Uani 1 1 d . . . H12A H -0.0377 0.9233 0.1758 0.062 Uiso 1 1 calc R . . H12B H 0.0510 1.0344 0.0916 0.062 Uiso 1 1 calc R . . H12C H 0.0050 1.0804 0.2300 0.062 Uiso 1 1 calc R . . H1 H 0.964(3) 1.046(2) 0.610(2) 0.031(5) Uiso 1 1 d . . . H2A H 1.288(3) 0.945(2) 0.673(2) 0.030(5) Uiso 1 1 d . . . H2B H 1.208(3) 0.831(3) 0.755(2) 0.050(7) Uiso 1 1 d . . . H3 H 1.208(3) 1.004(2) 0.912(2) 0.038(6) Uiso 1 1 d . . . H4A H 1.674(3) 1.170(2) 0.929(2) 0.035(5) Uiso 1 1 d . . . H4B H 1.596(3) 1.134(3) 1.059(2) 0.040(6) Uiso 1 1 d . . . H5A H 1.414(3) 1.318(3) 0.883(2) 0.038(6) Uiso 1 1 d . . . H5B H 1.320(3) 1.260(2) 0.984(2) 0.032(5) Uiso 1 1 d . . . H7 H 0.737(4) 1.103(3) 0.371(2) 0.044(6) Uiso 1 1 d . . . H8 H 0.388(3) 1.153(2) 0.2641(19) 0.024(4) Uiso 1 1 d . . . H10 H 0.206(3) 0.754(3) 0.303(2) 0.042(6) Uiso 1 1 d . . . H11 H 0.542(3) 0.699(2) 0.428(2) 0.029(5) Uiso 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 Cl1 0.0401(2) 0.0361(2) 0.0389(2) -0.00785(17) 0.02277(17) -0.00844(17) S1 0.02640(18) 0.02772(18) 0.02756(17) -0.00061(15) 0.00973(13) 0.00627(14) O1 0.0415(7) 0.0242(5) 0.0373(6) -0.0010(5) 0.0070(5) 0.0092(5) O2 0.0365(7) 0.0462(8) 0.0471(8) -0.0001(6) -0.0079(6) 0.0088(6) O3 0.0344(6) 0.0307(6) 0.0341(6) -0.0009(5) -0.0013(5) 0.0019(5) C1 0.0288(7) 0.0217(7) 0.0301(7) 0.0005(6) 0.0126(6) 0.0003(6) C2 0.0303(8) 0.0290(7) 0.0343(8) -0.0001(7) 0.0068(6) 0.0037(7) C3 0.0328(8) 0.0342(8) 0.0294(8) 0.0045(7) 0.0070(7) 0.0011(7) C4 0.0339(9) 0.0531(11) 0.0317(9) 0.0009(8) 0.0015(7) -0.0048(8) C5 0.0408(10) 0.0398(10) 0.0315(9) -0.0046(8) 0.0048(7) -0.0049(8) C6 0.0230(7) 0.0237(7) 0.0265(7) -0.0004(5) 0.0093(6) 0.0043(5) C7 0.0280(8) 0.0233(7) 0.0329(8) 0.0003(6) 0.0088(6) -0.0008(6) C8 0.0288(8) 0.0266(8) 0.0328(8) 0.0000(6) 0.0063(6) 0.0046(6) C9 0.0264(8) 0.0380(9) 0.0279(7) -0.0054(6) 0.0115(6) 0.0020(6) C10 0.0294(8) 0.0347(9) 0.0387(8) -0.0041(7) 0.0158(6) -0.0079(7) C11 0.0349(8) 0.0249(7) 0.0360(9) -0.0001(7) 0.0158(7) -0.0003(6) C12 0.0256(8) 0.0573(12) 0.0386(9) -0.0061(9) 0.0068(7) 0.0036(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 Cl1 C1 1.7841(16) . ? S1 O1 1.4925(13) . ? S1 C6 1.7843(16) . ? S1 C1 1.8260(16) . ? O2 C3 1.415(2) . ? O2 C4 1.433(3) . ? O3 C3 1.405(2) . ? O3 C5 1.432(2) . ? C1 C2 1.518(2) . ? C1 H1 0.90(2) . ? C2 C3 1.507(3) . ? C2 H2A 0.96(2) . ? C2 H2B 1.01(3) . ? C3 H3 0.87(2) . ? C4 C5 1.515(3) . ? C4 H4A 1.02(2) . ? C4 H4B 0.95(2) . ? C5 H5A 0.90(3) . ? C5 H5B 0.87(2) . ? C6 C11 1.387(2) . ? C6 C7 1.389(2) . ? C7 C8 1.393(2) . ? C7 H7 1.06(3) . ? C8 C9 1.397(2) . ? C8 H8 0.91(2) . ? C9 C10 1.383(3) . ? C9 C12 1.509(2) . ? C10 C11 1.391(2) . ? C10 H10 1.01(2) . ? C11 H11 0.98(2) . ? 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 O1 S1 C6 108.17(8) . . ? O1 S1 C1 107.00(7) . . ? C6 S1 C1 98.86(7) . . ? C3 O2 C4 107.02(14) . . ? C3 O3 C5 104.29(13) . . ? C2 C1 Cl1 112.26(11) . . ? C2 C1 S1 107.38(11) . . ? Cl1 C1 S1 111.70(8) . . ? C2 C1 H1 108.4(13) . . ? Cl1 C1 H1 109.7(13) . . ? S1 C1 H1 107.2(13) . . ? C3 C2 C1 113.04(14) . . ? C3 C2 H2A 106.6(13) . . ? C1 C2 H2A 113.1(12) . . ? C3 C2 H2B 109.5(14) . . ? C1 C2 H2B 108.9(13) . . ? H2A C2 H2B 105.4(18) . . ? O3 C3 O2 106.18(14) . . ? O3 C3 C2 110.16(14) . . ? O2 C3 C2 109.36(15) . . ? O3 C3 H3 111.8(15) . . ? O2 C3 H3 106.5(15) . . ? C2 C3 H3 112.5(16) . . ? O2 C4 C5 104.77(15) . . ? O2 C4 H4A 109.7(13) . . ? C5 C4 H4A 115.1(13) . . ? O2 C4 H4B 106.6(15) . . ? C5 C4 H4B 110.8(14) . . ? H4A C4 H4B 109.5(18) . . ? O3 C5 C4 103.62(16) . . ? O3 C5 H5A 109.9(15) . . ? C4 C5 H5A 106.7(15) . . ? O3 C5 H5B 111.1(15) . . ? C4 C5 H5B 112.3(14) . . ? H5A C5 H5B 113(2) . . ? C11 C6 C7 121.59(15) . . ? C11 C6 S1 119.40(12) . . ? C7 C6 S1 118.69(12) . . ? C6 C7 C8 118.65(15) . . ? C6 C7 H7 122.4(14) . . ? C8 C7 H7 118.8(13) . . ? C7 C8 C9 120.87(16) . . ? C7 C8 H8 120.1(12) . . ? C9 C8 H8 118.7(12) . . ? C10 C9 C8 118.91(15) . . ? C10 C9 C12 121.34(16) . . ? C8 C9 C12 119.75(16) . . ? C9 C10 C11 121.41(16) . . ? C9 C10 H10 122.9(14) . . ? C11 C10 H10 115.7(14) . . ? C6 C11 C10 118.56(16) . . ? C6 C11 H11 119.5(12) . . ? C10 C11 H11 122.0(12) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 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 O1 S1 C1 C2 68.01(12) . . . . ? C6 S1 C1 C2 -179.79(11) . . . . ? O1 S1 C1 Cl1 -55.47(10) . . . . ? C6 S1 C1 Cl1 56.72(10) . . . . ? Cl1 C1 C2 C3 -59.25(17) . . . . ? S1 C1 C2 C3 177.61(13) . . . . ? C5 O3 C3 O2 -38.41(19) . . . . ? C5 O3 C3 C2 -156.73(16) . . . . ? C4 O2 C3 O3 27.25(19) . . . . ? C4 O2 C3 C2 146.09(16) . . . . ? C1 C2 C3 O3 -54.3(2) . . . . ? C1 C2 C3 O2 -170.63(14) . . . . ? C3 O2 C4 C5 -5.7(2) . . . . ? C3 O3 C5 C4 33.58(19) . . . . ? O2 C4 C5 O3 -17.1(2) . . . . ? O1 S1 C6 C11 -9.30(15) . . . . ? C1 S1 C6 C11 -120.56(13) . . . . ? O1 S1 C6 C7 177.04(12) . . . . ? C1 S1 C6 C7 65.78(14) . . . . ? C11 C6 C7 C8 0.8(2) . . . . ? S1 C6 C7 C8 174.30(12) . . . . ? C6 C7 C8 C9 -1.2(2) . . . . ? C7 C8 C9 C10 0.9(2) . . . . ? C7 C8 C9 C12 -178.91(16) . . . . ? C8 C9 C10 C11 -0.2(2) . . . . ? C12 C9 C10 C11 179.68(15) . . . . ? C7 C6 C11 C10 0.0(2) . . . . ? S1 C6 C11 C10 -173.51(12) . . . . ? C9 C10 C11 C6 -0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.292 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.044 #===END data_pbr27(SantiD12) _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 Cl O3 S' _chemical_formula_weight 274.75 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' '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 15.176(2) _cell_length_b 9.6244(15) _cell_length_c 8.8976(14) _cell_angle_alpha 90.00 _cell_angle_beta 94.396(2) _cell_angle_gamma 90.00 _cell_volume 1295.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4957 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 28.19 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.449 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8338 _exptl_absorpt_correction_T_max 0.9077 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7327 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2834 _reflns_number_gt 2790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0751P)^2^+0.2741P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration 'ad' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(7) _refine_ls_number_reflns 2834 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.39366(4) 0.52084(7) 0.49453(7) 0.0498(2) Uani 1 1 d . . . S1 S 0.20858(3) 0.55011(6) 0.52162(5) 0.03667(15) Uani 1 1 d . . . O1 O 0.34718(19) 0.6783(3) 0.0271(3) 0.0707(6) Uani 1 1 d . . . O2 O 0.33512(19) 0.4524(3) 0.0825(3) 0.0671(6) Uani 1 1 d . . . O3 O 0.22212(12) 0.6963(2) 0.5713(2) 0.0502(5) Uani 1 1 d . . . C1 C 0.28966(13) 0.5165(3) 0.3838(2) 0.0368(5) Uani 1 1 d . . . C2 C 0.28950(17) 0.6196(3) 0.2577(3) 0.0394(5) Uani 1 1 d . . . C3 C 0.35595(17) 0.5816(3) 0.1446(3) 0.0507(7) Uani 1 1 d . . . H3A H 0.4175 0.5822 0.1936 0.061 Uiso 1 1 calc R . . C4 C 0.3707(2) 0.6060(5) -0.1024(4) 0.0652(9) Uani 1 1 d . . . H4A H 0.4322 0.6281 -0.1238 0.078 Uiso 1 1 calc R . . H4B H 0.3308 0.6316 -0.1914 0.078 Uiso 1 1 calc R . . C5 C 0.3618(3) 0.4563(4) -0.0669(4) 0.0720(10) Uani 1 1 d . . . H5A H 0.3168 0.4119 -0.1378 0.086 Uiso 1 1 calc R . . H5B H 0.4188 0.4076 -0.0732 0.086 Uiso 1 1 calc R . . C6 C 0.11199(13) 0.5465(3) 0.3929(2) 0.0343(4) Uani 1 1 d . . . C7 C 0.07765(18) 0.4214(3) 0.3403(4) 0.0449(6) Uani 1 1 d . . . C8 C 0.00122(19) 0.4224(3) 0.2434(4) 0.0513(7) Uani 1 1 d . . . C9 C -0.04131(13) 0.5439(3) 0.2009(2) 0.0418(5) Uani 1 1 d . . . C10 C -0.00663(17) 0.6692(3) 0.2592(3) 0.0455(6) Uani 1 1 d . . . C11 C 0.06994(17) 0.6704(3) 0.3546(3) 0.0429(6) Uani 1 1 d . . . C12 C -0.12318(16) 0.5449(4) 0.0941(3) 0.0563(7) Uani 1 1 d . . . H12A H -0.1385 0.4494 0.0641 0.084 Uiso 1 1 calc R . . H12B H -0.1122 0.5995 0.0044 0.084 Uiso 1 1 calc R . . H12C H -0.1721 0.5864 0.1441 0.084 Uiso 1 1 calc R . . D1 H 0.2784(17) 0.413(3) 0.350(3) 0.026(6) Uiso 1 1 d . . . H2A H 0.2279(19) 0.613(3) 0.206(3) 0.044(7) Uiso 1 1 d . . . H2B H 0.300(2) 0.716(4) 0.298(4) 0.057(9) Uiso 1 1 d . . . H7 H 0.104(3) 0.351(4) 0.365(5) 0.064(11) Uiso 1 1 d . . . H8 H -0.025(3) 0.343(4) 0.216(5) 0.065(11) Uiso 1 1 d . . . H10 H -0.043(3) 0.754(5) 0.238(5) 0.074(11) Uiso 1 1 d . . . H11 H 0.089(2) 0.761(3) 0.392(4) 0.044(8) Uiso 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 Cl1 0.0340(3) 0.0648(4) 0.0487(3) 0.0034(3) -0.0101(2) 0.0017(3) S1 0.0342(3) 0.0463(3) 0.0289(2) -0.0020(2) -0.00144(17) -0.0005(2) O1 0.0995(18) 0.0680(14) 0.0462(12) 0.0012(10) 0.0158(12) -0.0158(13) O2 0.0854(17) 0.0597(12) 0.0589(13) -0.0040(10) 0.0223(12) 0.0072(11) O3 0.0434(9) 0.0568(11) 0.0486(10) -0.0205(9) -0.0072(8) 0.0035(8) C1 0.0274(9) 0.0489(13) 0.0333(10) -0.0009(9) -0.0034(7) 0.0026(9) C2 0.0428(12) 0.0397(12) 0.0350(12) -0.0002(9) -0.0011(9) 0.0003(10) C3 0.0397(13) 0.074(2) 0.0383(12) 0.0014(12) 0.0027(9) -0.0104(12) C4 0.0438(15) 0.111(3) 0.0404(14) 0.0054(15) 0.0024(11) -0.0124(16) C5 0.0531(18) 0.095(3) 0.068(2) -0.030(2) 0.0025(15) 0.0098(17) C6 0.0302(9) 0.0423(11) 0.0303(9) 0.0001(10) 0.0026(7) 0.0001(10) C7 0.0404(13) 0.0385(13) 0.0549(16) 0.0011(11) -0.0032(12) -0.0014(11) C8 0.0431(14) 0.0519(16) 0.0578(17) -0.0086(12) -0.0039(12) -0.0096(12) C9 0.0286(9) 0.0632(15) 0.0339(9) -0.0005(12) 0.0050(7) 0.0003(11) C10 0.0361(12) 0.0522(14) 0.0479(15) -0.0017(11) 0.0005(10) 0.0065(11) C11 0.0372(12) 0.0412(12) 0.0496(14) -0.0096(11) -0.0021(10) 0.0033(10) C12 0.0333(11) 0.089(2) 0.0457(12) -0.0078(16) -0.0009(9) -0.0019(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 Cl1 C1 1.796(2) . ? S1 O3 1.484(2) . ? S1 C6 1.790(2) . ? S1 C1 1.831(2) . ? O1 C3 1.398(4) . ? O1 C4 1.415(4) . ? O2 C3 1.388(4) . ? O2 C5 1.420(5) . ? C1 C2 1.498(3) . ? C1 D1 1.05(3) . ? C2 C3 1.523(3) . ? C2 H2A 1.01(3) . ? C2 H2B 1.01(4) . ? C3 H3A 1.0000 . ? C4 C5 1.484(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.380(4) . ? C6 C11 1.383(4) . ? C7 C8 1.391(4) . ? C7 H7 0.81(4) . ? C8 C9 1.375(4) . ? C8 H8 0.89(4) . ? C9 C10 1.399(4) . ? C9 C12 1.505(3) . ? C10 C11 1.386(4) . ? C10 H10 1.00(4) . ? C11 H11 0.97(3) . ? 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 O3 S1 C6 107.26(11) . . ? O3 S1 C1 106.38(12) . . ? C6 S1 C1 97.33(9) . . ? C3 O1 C4 105.5(3) . . ? C3 O2 C5 106.1(3) . . ? C2 C1 Cl1 110.29(17) . . ? C2 C1 S1 114.97(17) . . ? Cl1 C1 S1 103.64(11) . . ? C2 C1 D1 114.9(15) . . ? Cl1 C1 D1 107.2(15) . . ? S1 C1 D1 104.9(13) . . ? C1 C2 C3 111.9(2) . . ? C1 C2 H2A 104.1(17) . . ? C3 C2 H2A 108.6(16) . . ? C1 C2 H2B 111(2) . . ? C3 C2 H2B 111(2) . . ? H2A C2 H2B 110(3) . . ? O2 C3 O1 107.0(2) . . ? O2 C3 C2 109.6(2) . . ? O1 C3 C2 107.7(2) . . ? O2 C3 H3A 110.8 . . ? O1 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? O1 C4 C5 105.7(3) . . ? O1 C4 H4A 110.6 . . ? C5 C4 H4A 110.6 . . ? O1 C4 H4B 110.6 . . ? C5 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? O2 C5 C4 105.2(3) . . ? O2 C5 H5A 110.7 . . ? C4 C5 H5A 110.7 . . ? O2 C5 H5B 110.7 . . ? C4 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? C7 C6 C11 120.9(2) . . ? C7 C6 S1 120.2(2) . . ? C11 C6 S1 118.77(19) . . ? C6 C7 C8 118.6(3) . . ? C6 C7 H7 118(3) . . ? C8 C7 H7 123(3) . . ? C9 C8 C7 121.9(3) . . ? C9 C8 H8 118(3) . . ? C7 C8 H8 120(3) . . ? C8 C9 C10 118.4(2) . . ? C8 C9 C12 121.8(3) . . ? C10 C9 C12 119.8(3) . . ? C11 C10 C9 120.6(2) . . ? C11 C10 H10 122(3) . . ? C9 C10 H10 117(3) . . ? C6 C11 C10 119.6(2) . . ? C6 C11 H11 124.7(19) . . ? C10 C11 H11 115.8(19) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 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 O3 S1 C1 C2 -52.3(2) . . . . ? C6 S1 C1 C2 58.1(2) . . . . ? O3 S1 C1 Cl1 68.11(14) . . . . ? C6 S1 C1 Cl1 178.57(12) . . . . ? Cl1 C1 C2 C3 65.6(2) . . . . ? S1 C1 C2 C3 -177.71(17) . . . . ? C5 O2 C3 O1 31.7(3) . . . . ? C5 O2 C3 C2 148.3(3) . . . . ? C4 O1 C3 O2 -32.3(3) . . . . ? C4 O1 C3 C2 -150.2(2) . . . . ? C1 C2 C3 O2 60.2(3) . . . . ? C1 C2 C3 O1 176.4(2) . . . . ? C3 O1 C4 C5 19.8(4) . . . . ? C3 O2 C5 C4 -18.4(4) . . . . ? O1 C4 C5 O2 -1.0(4) . . . . ? O3 S1 C6 C7 -173.1(2) . . . . ? C1 S1 C6 C7 77.2(2) . . . . ? O3 S1 C6 C11 3.3(2) . . . . ? C1 S1 C6 C11 -106.5(2) . . . . ? C11 C6 C7 C8 2.1(4) . . . . ? S1 C6 C7 C8 178.4(2) . . . . ? C6 C7 C8 C9 -0.9(4) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? C7 C8 C9 C12 179.0(3) . . . . ? C8 C9 C10 C11 1.5(4) . . . . ? C12 C9 C10 C11 -178.3(2) . . . . ? C7 C6 C11 C10 -1.5(3) . . . . ? S1 C6 C11 C10 -177.80(19) . . . . ? C9 C10 C11 C6 -0.3(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.733 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.061 #===END data_pb28(RRDD17) _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H20 Cl N O5' _chemical_formula_sum 'C15 H20 Cl N O5' _chemical_formula_weight 329.77 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' '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 P2(1)2(1)2(1) _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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.0356(7) _cell_length_b 11.0921(10) _cell_length_c 17.5466(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1564.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9194 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 28.12 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9029 _exptl_absorpt_correction_T_max 0.9635 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17516 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.98 _reflns_number_total 3419 _reflns_number_gt 3324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0575P)^2^+0.1147P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration 'ad' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 3419 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0300 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.67634(4) 0.28942(3) 0.84934(2) 0.03296(10) Uani 1 1 d . . . O1 O -0.20465(13) 0.63303(11) 0.83822(6) 0.0352(2) Uani 1 1 d . . . O2 O 0.05023(16) 0.70878(11) 1.04174(6) 0.0381(2) Uani 1 1 d . . . O3 O -0.02361(16) 0.51622(10) 1.01891(6) 0.0390(3) Uani 1 1 d . . . O4 O -0.08393(15) 0.45212(10) 0.58318(6) 0.0363(3) Uani 1 1 d . . . O5 O 0.04547(18) 0.62367(11) 0.61518(6) 0.0454(3) Uani 1 1 d . . . N1 N 0.50418(14) 0.47792(11) 0.80721(7) 0.0278(2) Uani 1 1 d . . . C1 C 0.49112(17) 0.36330(13) 0.82812(7) 0.0259(3) Uani 1 1 d . . . C2 C 0.34316(18) 0.30088(13) 0.83407(10) 0.0342(3) Uani 1 1 d . . . C3 C 0.19827(19) 0.36194(13) 0.81680(9) 0.0327(3) Uani 1 1 d . . . C4 C 0.20479(17) 0.48268(12) 0.79447(7) 0.0248(3) Uani 1 1 d . . . C5 C 0.36130(17) 0.53516(13) 0.79082(8) 0.0271(3) Uani 1 1 d . . . C6 C 0.04830(17) 0.55488(12) 0.77882(8) 0.0250(3) Uani 1 1 d . . . C7 C -0.05377(17) 0.56963(12) 0.85325(8) 0.0266(3) Uani 1 1 d . . . C8 C 0.04164(19) 0.64264(13) 0.91231(8) 0.0299(3) Uani 1 1 d . . . C9 C -0.03801(19) 0.63515(13) 0.98986(8) 0.0295(3) Uani 1 1 d . . . C10 C 0.0088(2) 0.66049(16) 1.11442(9) 0.0377(3) Uani 1 1 d . . . C11 C -0.0072(2) 0.52645(15) 1.09974(8) 0.0348(3) Uani 1 1 d . . . C12 C -0.05830(17) 0.49783(13) 0.71565(8) 0.0277(3) Uani 1 1 d . . . C13 C 0.02117(18) 0.50324(14) 0.63839(8) 0.0304(3) Uani 1 1 d . . . C14 C -0.0331(3) 0.5037(2) 0.51236(10) 0.0482(4) Uani 1 1 d . . . C15 C 0.0523(4) 0.6191(2) 0.53341(10) 0.0637(7) Uani 1 1 d . . . H1O H -0.274(3) 0.579(2) 0.8297(14) 0.061(7) Uiso 1 1 d . . . H2 H 0.342(2) 0.2147(18) 0.8511(10) 0.040(5) Uiso 1 1 d . . . H3 H 0.091(2) 0.3201(16) 0.8236(11) 0.038(5) Uiso 1 1 d . . . H5 H 0.373(2) 0.6203(16) 0.7760(9) 0.026(4) Uiso 1 1 d . . . D6 H 0.0767(19) 0.6345(14) 0.7629(8) 0.015(3) Uiso 1 1 d . . . D7 H -0.0787(18) 0.4874(13) 0.8750(8) 0.014(3) Uiso 1 1 d . . . H8A H 0.152(3) 0.6122(18) 0.9158(11) 0.044(5) Uiso 1 1 d . . . H8B H 0.046(2) 0.7215(17) 0.8961(10) 0.030(4) Uiso 1 1 d . . . H9 H -0.154(2) 0.6549(15) 0.9901(9) 0.024(4) Uiso 1 1 d . . . H10A H -0.099(3) 0.696(2) 1.1339(14) 0.060(7) Uiso 1 1 d . . . H10B H 0.099(3) 0.6828(17) 1.1460(12) 0.041(5) Uiso 1 1 d . . . H11A H -0.106(3) 0.4900(18) 1.1234(12) 0.047(6) Uiso 1 1 d . . . H11B H 0.092(3) 0.4848(18) 1.1173(12) 0.043(5) Uiso 1 1 d . . . H12A H -0.088(2) 0.4131(17) 0.7280(11) 0.036(5) Uiso 1 1 d . . . H12B H -0.168(2) 0.5420(15) 0.7106(10) 0.031(4) Uiso 1 1 d . . . H13 H 0.123(3) 0.4574(18) 0.6379(11) 0.040(5) Uiso 1 1 d . . . H14A H 0.036(3) 0.450(3) 0.4918(17) 0.080(9) Uiso 1 1 d . . . H14B H -0.140(4) 0.522(3) 0.4861(15) 0.074(8) Uiso 1 1 d . . . H15A H 0.185(6) 0.621(4) 0.518(2) 0.154(16) Uiso 1 1 d . . . H15B H -0.025(3) 0.687(2) 0.5158(17) 0.082(9) Uiso 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 Cl1 0.02717(16) 0.03235(16) 0.03935(18) -0.00219(14) -0.00435(14) 0.00804(13) O1 0.0258(5) 0.0394(6) 0.0404(6) -0.0070(5) -0.0027(4) 0.0050(5) O2 0.0546(6) 0.0333(5) 0.0263(5) -0.0013(4) -0.0049(5) -0.0119(5) O3 0.0574(7) 0.0289(5) 0.0307(5) -0.0008(4) 0.0030(5) -0.0055(5) O4 0.0457(6) 0.0384(6) 0.0246(5) -0.0023(4) -0.0043(5) -0.0116(5) O5 0.0656(8) 0.0447(6) 0.0261(5) 0.0014(5) -0.0032(5) -0.0271(6) N1 0.0241(6) 0.0298(6) 0.0296(6) -0.0001(5) -0.0013(4) -0.0002(5) C1 0.0242(6) 0.0275(6) 0.0258(6) -0.0029(5) -0.0034(5) 0.0049(5) C2 0.0308(7) 0.0247(6) 0.0469(8) 0.0014(6) -0.0053(6) 0.0004(6) C3 0.0263(7) 0.0290(7) 0.0427(8) 0.0019(6) -0.0052(6) -0.0039(6) C4 0.0247(6) 0.0276(6) 0.0220(6) -0.0016(5) -0.0019(5) 0.0010(5) C5 0.0252(6) 0.0289(7) 0.0273(6) 0.0025(5) -0.0009(5) 0.0009(5) C6 0.0229(6) 0.0268(6) 0.0253(6) 0.0005(5) -0.0017(5) -0.0014(5) C7 0.0246(6) 0.0289(6) 0.0261(6) -0.0006(5) -0.0016(5) -0.0010(5) C8 0.0311(7) 0.0300(7) 0.0287(7) -0.0002(5) -0.0008(6) -0.0058(6) C9 0.0301(7) 0.0299(7) 0.0285(7) -0.0036(5) -0.0011(5) -0.0018(6) C10 0.0460(9) 0.0408(8) 0.0265(6) -0.0009(6) -0.0006(7) -0.0019(7) C11 0.0337(8) 0.0404(8) 0.0304(7) 0.0042(6) 0.0010(6) -0.0010(7) C12 0.0238(6) 0.0347(7) 0.0245(6) 0.0014(6) -0.0035(5) -0.0022(6) C13 0.0263(6) 0.0376(7) 0.0273(7) -0.0016(6) -0.0018(5) -0.0005(6) C14 0.0598(11) 0.0584(11) 0.0264(7) -0.0030(7) 0.0006(8) -0.0182(10) C15 0.0993(18) 0.0650(13) 0.0266(8) 0.0087(8) -0.0086(10) -0.0373(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 Cl1 C1 1.7393(14) . ? O1 C7 1.4263(17) . ? O1 H1O 0.84(3) . ? O2 C9 1.4137(18) . ? O2 C10 1.4226(19) . ? O3 C9 1.4189(18) . ? O3 C11 1.4289(18) . ? O4 C13 1.4047(18) . ? O4 C14 1.428(2) . ? O5 C13 1.4101(19) . ? O5 C15 1.437(2) . ? N1 C1 1.3274(19) . ? N1 C5 1.3432(18) . ? C1 C2 1.380(2) . ? C2 C3 1.381(2) . ? C2 H2 1.001(19) . ? C3 C4 1.396(2) . ? C3 H3 0.98(2) . ? C4 C5 1.3873(19) . ? C4 C6 1.5160(19) . ? C5 H5 0.984(17) . ? C6 C12 1.5372(19) . ? C6 C7 1.5508(19) . ? C6 D6 0.954(15) . ? C7 C8 1.522(2) . ? C7 D7 1.009(15) . ? C8 C9 1.506(2) . ? C8 H8A 0.95(2) . ? C8 H8B 0.920(18) . ? C9 H9 0.959(18) . ? C10 C11 1.514(2) . ? C10 H10A 1.01(2) . ? C10 H10B 0.94(2) . ? C11 H11A 0.98(2) . ? C11 H11B 0.97(2) . ? C12 C13 1.4997(19) . ? C12 H12A 0.994(19) . ? C12 H12B 1.011(19) . ? C13 H13 0.97(2) . ? C14 C15 1.499(3) . ? C14 H14A 0.89(3) . ? C14 H14B 1.00(3) . ? C15 H15A 1.10(4) . ? C15 H15B 1.02(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1O 104.3(17) . . ? C9 O2 C10 104.03(12) . . ? C9 O3 C11 106.88(11) . . ? C13 O4 C14 105.47(12) . . ? C13 O5 C15 105.09(13) . . ? C1 N1 C5 116.38(12) . . ? N1 C1 C2 124.72(13) . . ? N1 C1 Cl1 116.28(11) . . ? C2 C1 Cl1 119.00(11) . . ? C3 C2 C1 117.64(13) . . ? C3 C2 H2 121.6(11) . . ? C1 C2 H2 120.8(11) . . ? C2 C3 C4 120.02(14) . . ? C2 C3 H3 118.7(11) . . ? C4 C3 H3 121.2(11) . . ? C5 C4 C3 116.71(13) . . ? C5 C4 C6 121.46(12) . . ? C3 C4 C6 121.76(12) . . ? N1 C5 C4 124.52(13) . . ? N1 C5 H5 115.5(10) . . ? C4 C5 H5 120.0(10) . . ? C4 C6 C12 112.05(11) . . ? C4 C6 C7 109.99(11) . . ? C12 C6 C7 110.85(11) . . ? C4 C6 D6 110.1(9) . . ? C12 C6 D6 107.6(9) . . ? C7 C6 D6 106.0(9) . . ? O1 C7 C8 106.96(11) . . ? O1 C7 C6 110.24(12) . . ? C8 C7 C6 111.29(12) . . ? O1 C7 D7 110.3(8) . . ? C8 C7 D7 108.8(8) . . ? C6 C7 D7 109.2(8) . . ? C9 C8 C7 111.82(12) . . ? C9 C8 H8A 108.6(12) . . ? C7 C8 H8A 108.9(12) . . ? C9 C8 H8B 110.3(11) . . ? C7 C8 H8B 108.3(11) . . ? H8A C8 H8B 108.9(17) . . ? O2 C9 O3 105.36(12) . . ? O2 C9 C8 109.68(12) . . ? O3 C9 C8 109.95(12) . . ? O2 C9 H9 110.7(10) . . ? O3 C9 H9 106.9(10) . . ? C8 C9 H9 113.9(10) . . ? O2 C10 C11 103.71(12) . . ? O2 C10 H10A 110.9(14) . . ? C11 C10 H10A 111.4(13) . . ? O2 C10 H10B 104.4(13) . . ? C11 C10 H10B 115.0(12) . . ? H10A C10 H10B 110.9(18) . . ? O3 C11 C10 104.75(12) . . ? O3 C11 H11A 108.3(13) . . ? C10 C11 H11A 113.7(12) . . ? O3 C11 H11B 110.6(12) . . ? C10 C11 H11B 110.0(12) . . ? H11A C11 H11B 109.4(17) . . ? C13 C12 C6 113.45(11) . . ? C13 C12 H12A 109.8(11) . . ? C6 C12 H12A 111.5(11) . . ? C13 C12 H12B 105.8(10) . . ? C6 C12 H12B 110.4(10) . . ? H12A C12 H12B 105.4(15) . . ? O4 C13 O5 105.46(12) . . ? O4 C13 C12 110.56(12) . . ? O5 C13 C12 110.97(12) . . ? O4 C13 H13 107.0(11) . . ? O5 C13 H13 112.3(12) . . ? C12 C13 H13 110.4(12) . . ? O4 C14 C15 104.98(14) . . ? O4 C14 H14A 105.4(19) . . ? C15 C14 H14A 112.6(19) . . ? O4 C14 H14B 103.8(16) . . ? C15 C14 H14B 109.6(17) . . ? H14A C14 H14B 119(2) . . ? O5 C15 C14 104.99(15) . . ? O5 C15 H15A 107(2) . . ? C14 C15 H15A 114(2) . . ? O5 C15 H15B 104.7(17) . . ? C14 C15 H15B 105.8(16) . . ? H15A C15 H15B 120(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -0.1(2) . . . . ? C5 N1 C1 Cl1 -179.98(10) . . . . ? N1 C1 C2 C3 0.2(2) . . . . ? Cl1 C1 C2 C3 -179.96(13) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C2 C3 C4 C6 -176.89(14) . . . . ? C1 N1 C5 C4 0.0(2) . . . . ? C3 C4 C5 N1 0.0(2) . . . . ? C6 C4 C5 N1 176.96(13) . . . . ? C5 C4 C6 C12 124.58(13) . . . . ? C3 C4 C6 C12 -58.57(18) . . . . ? C5 C4 C6 C7 -111.64(14) . . . . ? C3 C4 C6 C7 65.21(17) . . . . ? C4 C6 C7 O1 -177.51(11) . . . . ? C12 C6 C7 O1 -53.04(14) . . . . ? C4 C6 C7 C8 63.98(14) . . . . ? C12 C6 C7 C8 -171.54(11) . . . . ? O1 C7 C8 C9 71.93(15) . . . . ? C6 C7 C8 C9 -167.61(12) . . . . ? C10 O2 C9 O3 -39.95(16) . . . . ? C10 O2 C9 C8 -158.24(13) . . . . ? C11 O3 C9 O2 28.85(16) . . . . ? C11 O3 C9 C8 146.97(12) . . . . ? C7 C8 C9 O2 -177.22(12) . . . . ? C7 C8 C9 O3 67.37(16) . . . . ? C9 O2 C10 C11 34.49(16) . . . . ? C9 O3 C11 C10 -6.96(17) . . . . ? O2 C10 C11 O3 -16.96(17) . . . . ? C4 C6 C12 C13 -68.05(15) . . . . ? C7 C6 C12 C13 168.65(12) . . . . ? C14 O4 C13 O5 37.04(17) . . . . ? C14 O4 C13 C12 157.06(15) . . . . ? C15 O5 C13 O4 -36.4(2) . . . . ? C15 O5 C13 C12 -156.12(17) . . . . ? C6 C12 C13 O4 -178.71(12) . . . . ? C6 C12 C13 O5 -62.06(16) . . . . ? C13 O4 C14 C15 -22.7(2) . . . . ? C13 O5 C15 C14 21.3(3) . . . . ? O4 C14 C15 O5 0.7(3) . . . . ? 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 O1 H1O N1 0.84(3) 2.14(3) 2.9547(16) 165(2) 1_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.271 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.042 #===END