data_ic15591 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 O5 S' _chemical_formula_weight 346.38 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5480(4) _cell_length_b 8.7031(5) _cell_length_c 21.6417(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1610.01(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3105 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 22.75 _chemical_absolute_configuration 'ad' _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9689 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14591 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3697 _reflns_number_gt 3449 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0425P)^2^+0.3750P] 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 0.00(10) _refine_ls_number_reflns 3697 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _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 S1 S 0.66225(8) 1.11550(9) 1.13195(3) 0.03506(17) Uani 1 1 d . . . O1 O 0.56563(19) 0.8984(2) 0.79587(7) 0.0304(4) Uani 1 1 d . . . O2 O 0.6431(2) 1.1392(2) 0.79130(8) 0.0357(4) Uani 1 1 d . . . O3 O 0.3440(2) 1.1340(2) 1.07984(8) 0.0384(5) Uani 1 1 d . . . O4 O 1.0041(2) 0.8681(3) 0.89219(8) 0.0507(6) Uani 1 1 d . . . O5 O 0.92943(18) 0.8959(2) 0.79366(7) 0.0283(4) Uani 1 1 d . . . C1 C 0.6528(3) 1.0163(3) 0.81590(10) 0.0250(5) Uani 1 1 d . . . C2 C 0.7572(3) 0.9860(3) 0.87167(10) 0.0207(4) Uani 1 1 d . . . H2 H 0.7832 1.0881 0.8902 0.025 Uiso 1 1 calc R . . C3 C 0.6727(3) 0.8904(3) 0.92240(9) 0.0194(4) Uani 1 1 d . . . H3 H 0.7518 0.8471 0.9517 0.023 Uiso 1 1 calc R . . C4 C 0.5536(3) 0.9807(2) 0.95768(10) 0.0185(4) Uani 1 1 d . . . C5 C 0.5534(3) 1.0491(2) 1.01374(10) 0.0189(4) Uani 1 1 d . . . C6 C 0.3875(3) 1.0756(3) 1.03181(11) 0.0252(5) Uani 1 1 d . . . C7 C 0.2825(3) 1.0118(3) 0.98154(11) 0.0269(5) Uani 1 1 d . . . H7A H 0.2111 1.0923 0.9658 0.032 Uiso 1 1 calc R . . H7B H 0.2192 0.9252 0.9975 0.032 Uiso 1 1 calc R . . C8 C 0.3934(3) 0.9572(3) 0.93058(10) 0.0210(5) Uani 1 1 d . . . H8 H 0.3800 1.0209 0.8925 0.025 Uiso 1 1 calc R . . C9 C 0.4013(3) 0.7870(3) 0.91417(12) 0.0283(5) Uani 1 1 d . . . H9A H 0.3281 0.7629 0.8801 0.034 Uiso 1 1 calc R . . H9B H 0.3738 0.7230 0.9504 0.034 Uiso 1 1 calc R . . C10 C 0.5736(3) 0.7566(3) 0.89388(10) 0.0226(5) Uani 1 1 d . . . H10 H 0.6094 0.6569 0.9120 0.027 Uiso 1 1 calc R . . C11 C 0.5926(3) 0.7503(3) 0.82449(11) 0.0297(6) Uani 1 1 d . . . H11A H 0.6997 0.7150 0.8144 0.036 Uiso 1 1 calc R . . H11B H 0.5179 0.6746 0.8073 0.036 Uiso 1 1 calc R . . C12 C 0.6863(3) 1.0830(3) 1.05352(9) 0.0205(5) Uani 1 1 d . . . C13 C 0.8431(3) 1.0937(2) 1.03756(10) 0.0202(4) Uani 1 1 d . . . H13 H 0.8816 1.0793 0.9968 0.024 Uiso 1 1 calc R . . C14 C 0.9394(3) 1.1288(3) 1.08907(11) 0.0255(5) Uani 1 1 d . . . H14 H 1.0495 1.1419 1.0863 0.031 Uiso 1 1 calc R . . C15 C 0.8586(3) 1.1416(3) 1.14247(11) 0.0314(5) Uani 1 1 d . . . H15 H 0.9055 1.1628 1.1813 0.038 Uiso 1 1 calc R . . C16 C 0.9118(3) 0.9092(3) 0.85447(10) 0.0255(5) Uani 1 1 d . . . C17 C 1.0777(3) 0.8340(3) 0.77050(12) 0.0298(6) Uani 1 1 d . . . H17A H 1.0578 0.7665 0.7345 0.036 Uiso 1 1 calc R . . H17B H 1.1289 0.7721 0.8031 0.036 Uiso 1 1 calc R . . C18 C 1.1813(3) 0.9627(3) 0.75202(16) 0.0441(7) Uani 1 1 d . . . H18A H 1.1284 1.0260 0.7210 0.066 Uiso 1 1 calc R . . H18B H 1.2785 0.9215 0.7346 0.066 Uiso 1 1 calc R . . H18C H 1.2057 1.0257 0.7883 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0331(3) 0.0535(4) 0.0186(3) -0.0080(3) 0.0022(3) -0.0039(3) O1 0.0266(9) 0.0463(11) 0.0183(8) -0.0005(8) -0.0055(7) -0.0017(9) O2 0.0355(10) 0.0410(11) 0.0307(9) 0.0133(8) 0.0023(8) 0.0074(9) O3 0.0290(9) 0.0560(12) 0.0302(9) -0.0114(9) 0.0050(8) 0.0056(10) O4 0.0302(10) 0.0977(18) 0.0241(9) 0.0019(12) -0.0045(8) 0.0207(12) O5 0.0220(8) 0.0433(10) 0.0196(7) 0.0000(8) 0.0017(7) 0.0100(8) C1 0.0186(11) 0.0382(13) 0.0180(10) 0.0016(9) 0.0033(10) 0.0034(10) C2 0.0204(11) 0.0233(11) 0.0185(10) -0.0010(9) -0.0016(9) -0.0013(9) C3 0.0221(10) 0.0216(11) 0.0144(9) 0.0008(8) -0.0027(8) 0.0022(10) C4 0.0224(11) 0.0155(10) 0.0177(10) 0.0049(9) -0.0006(9) -0.0034(8) C5 0.0209(11) 0.0179(10) 0.0178(10) 0.0007(8) 0.0019(9) -0.0006(9) C6 0.0242(12) 0.0286(12) 0.0227(11) 0.0015(9) 0.0026(9) 0.0003(10) C7 0.0203(12) 0.0307(13) 0.0297(12) 0.0023(10) 0.0014(10) -0.0019(10) C8 0.0181(11) 0.0250(11) 0.0199(10) 0.0031(9) -0.0012(9) -0.0028(9) C9 0.0267(13) 0.0284(13) 0.0297(13) -0.0037(10) 0.0037(11) -0.0087(10) C10 0.0270(12) 0.0193(11) 0.0214(11) -0.0029(9) -0.0036(10) -0.0017(10) C11 0.0293(13) 0.0346(14) 0.0254(13) -0.0085(10) -0.0021(11) -0.0003(11) C12 0.0267(12) 0.0201(11) 0.0148(10) -0.0002(8) 0.0011(8) 0.0017(9) C13 0.0252(11) 0.0166(10) 0.0189(9) 0.0002(8) -0.0021(9) 0.0000(9) C14 0.0265(12) 0.0229(12) 0.0272(11) -0.0002(10) -0.0031(10) -0.0004(10) C15 0.0342(13) 0.0350(13) 0.0250(12) -0.0053(11) -0.0093(10) -0.0024(11) C16 0.0191(11) 0.0369(13) 0.0204(11) -0.0009(10) 0.0005(9) -0.0010(10) C17 0.0217(13) 0.0390(14) 0.0286(12) -0.0025(11) 0.0022(10) 0.0068(11) C18 0.0249(14) 0.0382(15) 0.069(2) -0.0036(14) 0.0074(14) 0.0002(12) _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 C15 1.709(3) . ? S1 C12 1.733(2) . ? O1 C1 1.341(3) . ? O1 C11 1.448(3) . ? O2 C1 1.197(3) . ? O3 C6 1.215(3) . ? O4 C16 1.190(3) . ? O5 C16 1.330(3) . ? O5 C17 1.465(3) . ? C1 C2 1.524(3) . ? C2 C16 1.527(3) . ? C2 C3 1.556(3) . ? C3 C4 1.496(3) . ? C3 C10 1.566(3) . ? C4 C5 1.352(3) . ? C4 C8 1.504(3) . ? C5 C12 1.456(3) . ? C5 C6 1.489(3) . ? C6 C7 1.516(3) . ? C7 C8 1.530(3) . ? C8 C9 1.525(3) . ? C9 C10 1.560(3) . ? C10 C11 1.511(3) . ? C12 C13 1.387(3) . ? C13 C14 1.419(3) . ? C14 C15 1.351(3) . ? C17 C18 1.483(4) . ? 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 C15 S1 C12 92.03(12) . . ? C1 O1 C11 117.07(18) . . ? C16 O5 C17 117.94(18) . . ? O2 C1 O1 120.1(2) . . ? O2 C1 C2 123.2(2) . . ? O1 C1 C2 116.7(2) . . ? C1 C2 C16 112.94(19) . . ? C1 C2 C3 112.31(19) . . ? C16 C2 C3 109.85(18) . . ? C4 C3 C2 113.28(18) . . ? C4 C3 C10 102.91(17) . . ? C2 C3 C10 111.75(17) . . ? C5 C4 C3 133.7(2) . . ? C5 C4 C8 114.1(2) . . ? C3 C4 C8 110.47(18) . . ? C4 C5 C12 128.2(2) . . ? C4 C5 C6 107.76(19) . . ? C12 C5 C6 123.84(19) . . ? O3 C6 C5 125.5(2) . . ? O3 C6 C7 125.9(2) . . ? C5 C6 C7 108.59(19) . . ? C6 C7 C8 105.33(19) . . ? C4 C8 C9 100.51(19) . . ? C4 C8 C7 103.94(19) . . ? C9 C8 C7 119.8(2) . . ? C8 C9 C10 105.79(19) . . ? C11 C10 C9 112.8(2) . . ? C11 C10 C3 111.2(2) . . ? C9 C10 C3 105.88(18) . . ? O1 C11 C10 112.1(2) . . ? C13 C12 C5 128.4(2) . . ? C13 C12 S1 110.34(17) . . ? C5 C12 S1 121.30(17) . . ? C12 C13 C14 112.3(2) . . ? C15 C14 C13 113.2(2) . . ? C14 C15 S1 112.14(18) . . ? O4 C16 O5 125.3(2) . . ? O4 C16 C2 122.5(2) . . ? O5 C16 C2 112.17(19) . . ? O5 C17 C18 109.3(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.300 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.049