# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Muraleedharan Kannoth' _publ_contact_author_email MKM@IITM.AC.IN _publ_section_title ; As many as six tandem reactions in one step! - Unprecedented formation of highly functionalized benzothiophenes ; loop_ _publ_author_name 'Muraleedharan Kannoth' 'Gopinath Pushparathinam' 'Nilaya Surapaneni' 'Debiranjan Tripathy' ; R.Venkatachalam ; #===END data_155B _database_code_depnum_ccdc_archive 'CCDC 720185' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 O4 S' _chemical_formula_weight 264.29 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4664(3) _cell_length_b 8.7330(4) _cell_length_c 9.3615(4) _cell_angle_alpha 90.151(2) _cell_angle_beta 106.357(2) _cell_angle_gamma 105.808(2) _cell_volume 636.66(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5452 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.25 _exptl_crystal_description Rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8930 _exptl_absorpt_correction_T_max 0.9086 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ApexII 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 8096 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2929 _reflns_number_gt 2554 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction 'SAINT PLUS ,Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0496P)^2^+0.1375P] 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 2929 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.37594(18) 0.60169(17) 0.54592(16) 0.0419(3) Uani 1 1 d . . . H1 H 0.3791 0.6192 0.4487 0.050 Uiso 1 1 calc R . . C2 C 0.4977(2) 0.69608(18) 0.66547(18) 0.0494(4) Uani 1 1 d . . . H2 H 0.5859 0.7776 0.6489 0.059 Uiso 1 1 calc R . . C3 C 0.4923(2) 0.67244(19) 0.81206(18) 0.0501(4) Uani 1 1 d . . . H3 H 0.5769 0.7383 0.8910 0.060 Uiso 1 1 calc R . . C4 C 0.36421(18) 0.55383(18) 0.84122(15) 0.0425(3) Uani 1 1 d . . . H4 H 0.3603 0.5400 0.9388 0.051 Uiso 1 1 calc R . . C5 C 0.23946(16) 0.45382(15) 0.72149(14) 0.0340(3) Uani 1 1 d . . . C6 C 0.09706(17) 0.32218(16) 0.72208(13) 0.0346(3) Uani 1 1 d . . . C7 C 0.00178(16) 0.24948(16) 0.58436(14) 0.0353(3) Uani 1 1 d . . . C8 C 0.24659(16) 0.47798(15) 0.57460(14) 0.0341(3) Uani 1 1 d . . . C9 C -0.0586(2) 0.29809(19) 0.89841(16) 0.0465(3) Uani 1 1 d . . . C10 C -0.0748(3) 0.2146(3) 1.0345(2) 0.0738(6) Uani 1 1 d . . . H10A H -0.1458 0.2556 1.0790 0.111 Uiso 1 1 calc R . . H10B H 0.0370 0.2322 1.1048 0.111 Uiso 1 1 calc R . . H10C H -0.1259 0.1021 1.0073 0.111 Uiso 1 1 calc R . . C11 C -0.15110(18) 0.11031(16) 0.55064(15) 0.0384(3) Uani 1 1 d . . . C12 C -0.36249(19) -0.07114(18) 0.35764(16) 0.0443(3) Uani 1 1 d . . . H12A H -0.4542 -0.0480 0.3888 0.053 Uiso 1 1 calc R . . H12B H -0.3411 -0.1666 0.4017 0.053 Uiso 1 1 calc R . . C13 C -0.4113(2) -0.0951(2) 0.19086(18) 0.0588(4) Uani 1 1 d . . . H13A H -0.4388 -0.0022 0.1485 0.088 Uiso 1 1 calc R . . H13B H -0.5095 -0.1867 0.1558 0.088 Uiso 1 1 calc R . . H13C H -0.3171 -0.1117 0.1613 0.088 Uiso 1 1 calc R . . O1 O 0.07342(13) 0.26864(12) 0.85545(10) 0.0426(2) Uani 1 1 d . . . O2 O -0.14236(18) 0.37896(18) 0.83372(14) 0.0670(4) Uani 1 1 d . . . O3 O -0.21736(15) 0.04832(14) 0.64191(12) 0.0565(3) Uani 1 1 d . . . O4 O -0.20758(13) 0.06270(12) 0.40476(11) 0.0438(2) Uani 1 1 d . . . S1 S 0.08131(4) 0.34074(4) 0.44460(3) 0.03783(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0441(7) 0.0408(7) 0.0436(7) 0.0088(6) 0.0195(6) 0.0094(6) C2 0.0472(8) 0.0407(8) 0.0570(9) 0.0037(7) 0.0194(7) 0.0027(6) C3 0.0458(8) 0.0468(8) 0.0462(8) -0.0050(6) 0.0054(6) 0.0030(6) C4 0.0434(7) 0.0465(8) 0.0328(6) 0.0022(6) 0.0066(6) 0.0101(6) C5 0.0348(6) 0.0360(6) 0.0316(6) 0.0045(5) 0.0088(5) 0.0120(5) C6 0.0369(6) 0.0403(7) 0.0288(6) 0.0081(5) 0.0118(5) 0.0124(5) C7 0.0353(6) 0.0389(7) 0.0318(6) 0.0054(5) 0.0117(5) 0.0087(5) C8 0.0348(6) 0.0359(6) 0.0328(6) 0.0045(5) 0.0108(5) 0.0111(5) C9 0.0505(8) 0.0530(9) 0.0344(7) -0.0003(6) 0.0178(6) 0.0066(7) C10 0.0888(15) 0.0964(15) 0.0504(10) 0.0233(10) 0.0423(10) 0.0268(12) C11 0.0391(7) 0.0382(7) 0.0364(7) 0.0013(5) 0.0122(5) 0.0073(5) C12 0.0397(7) 0.0434(8) 0.0431(7) -0.0035(6) 0.0104(6) 0.0028(6) C13 0.0586(10) 0.0614(11) 0.0435(8) -0.0060(7) 0.0041(7) 0.0076(8) O1 0.0449(5) 0.0537(6) 0.0302(5) 0.0111(4) 0.0138(4) 0.0125(4) O2 0.0741(8) 0.0880(9) 0.0571(7) 0.0156(7) 0.0300(6) 0.0415(8) O3 0.0598(7) 0.0553(7) 0.0429(6) -0.0016(5) 0.0225(5) -0.0101(5) O4 0.0417(5) 0.0467(6) 0.0355(5) -0.0020(4) 0.0115(4) 0.0003(4) S1 0.04021(19) 0.0436(2) 0.02737(17) 0.00256(13) 0.01118(13) 0.00684(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 C1 C2 1.370(2) . ? C1 C8 1.4004(18) . ? C1 H1 0.9300 . ? C2 C3 1.400(2) . ? C2 H2 0.9300 . ? C3 C4 1.371(2) . ? C3 H3 0.9300 . ? C4 C5 1.4001(19) . ? C4 H4 0.9300 . ? C5 C8 1.4072(17) . ? C5 C6 1.4226(18) . ? C6 C7 1.3590(18) . ? C6 O1 1.3822(14) . ? C7 C11 1.4707(19) . ? C7 S1 1.7348(13) . ? C8 S1 1.7306(13) . ? C9 O2 1.1837(19) . ? C9 O1 1.3738(18) . ? C9 C10 1.491(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 O3 1.2020(16) . ? C11 O4 1.3369(16) . ? C12 O4 1.4551(17) . ? C12 C13 1.497(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 C1 C8 117.97(13) . . ? C2 C1 H1 121.0 . . ? C8 C1 H1 121.0 . . ? C1 C2 C3 121.43(14) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 121.08(14) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 118.79(13) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C4 C5 C8 119.69(12) . . ? C4 C5 C6 129.67(12) . . ? C8 C5 C6 110.64(11) . . ? C7 C6 O1 124.99(12) . . ? C7 C6 C5 114.24(11) . . ? O1 C6 C5 120.48(11) . . ? C6 C7 C11 126.38(12) . . ? C6 C7 S1 111.84(10) . . ? C11 C7 S1 121.78(10) . . ? C1 C8 C5 121.01(12) . . ? C1 C8 S1 127.01(10) . . ? C5 C8 S1 111.98(10) . . ? O2 C9 O1 122.96(13) . . ? O2 C9 C10 127.61(16) . . ? O1 C9 C10 109.43(14) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 O4 124.46(13) . . ? O3 C11 C7 124.51(13) . . ? O4 C11 C7 111.02(11) . . ? O4 C12 C13 106.98(13) . . ? O4 C12 H12A 110.3 . . ? C13 C12 H12A 110.3 . . ? O4 C12 H12B 110.3 . . ? C13 C12 H12B 110.3 . . ? H12A C12 H12B 108.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 O1 C6 118.04(11) . . ? C11 O4 C12 115.78(11) . . ? C8 S1 C7 91.29(6) . . ? 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 C8 C1 C2 C3 -1.2(2) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 1.2(2) . . . . ? C3 C4 C5 C8 -0.8(2) . . . . ? C3 C4 C5 C6 178.83(14) . . . . ? C4 C5 C6 C7 -179.27(13) . . . . ? C8 C5 C6 C7 0.37(16) . . . . ? C4 C5 C6 O1 -5.0(2) . . . . ? C8 C5 C6 O1 174.61(11) . . . . ? O1 C6 C7 C11 5.5(2) . . . . ? C5 C6 C7 C11 179.43(13) . . . . ? O1 C6 C7 S1 -174.49(10) . . . . ? C5 C6 C7 S1 -0.56(15) . . . . ? C2 C1 C8 C5 1.5(2) . . . . ? C2 C1 C8 S1 -178.74(11) . . . . ? C4 C5 C8 C1 -0.6(2) . . . . ? C6 C5 C8 C1 179.74(12) . . . . ? C4 C5 C8 S1 179.67(10) . . . . ? C6 C5 C8 S1 -0.02(14) . . . . ? C6 C7 C11 O3 4.5(2) . . . . ? S1 C7 C11 O3 -175.49(12) . . . . ? C6 C7 C11 O4 -176.03(12) . . . . ? S1 C7 C11 O4 3.96(17) . . . . ? O2 C9 O1 C6 -7.0(2) . . . . ? C10 C9 O1 C6 173.33(14) . . . . ? C7 C6 O1 C9 -78.31(17) . . . . ? C5 C6 O1 C9 108.11(15) . . . . ? O3 C11 O4 C12 1.6(2) . . . . ? C7 C11 O4 C12 -177.89(11) . . . . ? C13 C12 O4 C11 175.10(13) . . . . ? C1 C8 S1 C7 -179.98(13) . . . . ? C5 C8 S1 C7 -0.24(10) . . . . ? C6 C7 S1 C8 0.46(11) . . . . ? C11 C7 S1 C8 -179.53(12) . . . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.293 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.039 _vrf_PLAT029_155B ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.93 RESPONSE: The crytal size was small even after several attempts of recrystallisation.Even though the data was collected up to 0.75 \%A resolution, the crystal (the largest available) still diffracted quite weakly at high angle ; # Attachment 'CIF_for_compounds_6a,_7a,7b,_8b,_9b,_11d_and_12b' data_157B _database_code_depnum_ccdc_archive 'CCDC 720186' #==================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 O5 S' _chemical_formula_sum 'C12 H10 O5 S' _chemical_formula_weight 266.26 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.8201(6) _cell_length_b 7.8657(4) _cell_length_c 14.7561(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.514(2) _cell_angle_gamma 90.00 _cell_volume 1210.10(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2126 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 24.43 _exptl_crystal_description rectangular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9415 _exptl_absorpt_correction_T_max 0.9701 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ApexII 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 8429 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2802 _reflns_number_gt 1788 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction 'SAINT PLUS ,Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0872P)^2^+0.7614P] 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 2802 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1835 _refine_ls_wR_factor_gt 0.1607 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3803(3) 0.3905(4) 0.1735(2) 0.0497(8) Uani 1 1 d . . . H1 H 0.3944 0.3896 0.1140 0.060 Uiso 1 1 calc R . . C2 C 0.2689(3) 0.4543(5) 0.1869(3) 0.0592(10) Uani 1 1 d . . . H2 H 0.2065 0.4961 0.1355 0.071 Uiso 1 1 calc R . . C3 C 0.2466(3) 0.4581(5) 0.2751(3) 0.0592(10) Uani 1 1 d . . . H3 H 0.1705 0.5038 0.2823 0.071 Uiso 1 1 calc R . . C4 C 0.3362(3) 0.3949(4) 0.3516(3) 0.0498(8) Uani 1 1 d . . . H4 H 0.3216 0.3965 0.4109 0.060 Uiso 1 1 calc R . . C5 C 0.4499(3) 0.3280(4) 0.3390(2) 0.0377(7) Uani 1 1 d . . . C6 C 0.4720(3) 0.3268(4) 0.2512(2) 0.0388(7) Uani 1 1 d . . . C7 C 0.5540(3) 0.2492(4) 0.4141(3) 0.0479(8) Uani 1 1 d . . . C8 C 0.6649(3) 0.1872(4) 0.36933(19) 0.0360(6) Uani 1 1 d . . . C9 C 0.6795(3) -0.0033(4) 0.38848(19) 0.0387(7) Uani 1 1 d . . . C10 C 0.5843(4) -0.2706(4) 0.3439(3) 0.0552(9) Uani 1 1 d . . . H10A H 0.6642 -0.3214 0.3417 0.083 Uiso 1 1 calc R . . H10B H 0.5157 -0.3196 0.2958 0.083 Uiso 1 1 calc R . . H10C H 0.5698 -0.2911 0.4044 0.083 Uiso 1 1 calc R . . C11 C 0.7891(3) 0.2820(4) 0.4147(2) 0.0391(7) Uani 1 1 d . . . C12 C 1.0068(3) 0.3052(5) 0.4184(3) 0.0627(10) Uani 1 1 d . . . H12A H 0.9997 0.4215 0.3979 0.094 Uiso 1 1 calc R . . H12B H 1.0695 0.2481 0.3940 0.094 Uiso 1 1 calc R . . H12C H 1.0329 0.3014 0.4859 0.094 Uiso 1 1 calc R . . O1 O 0.5569(2) 0.2273(4) 0.4847(2) 0.0678(8) Uani 1 1 d . . . O2 O 0.58931(19) -0.0897(3) 0.32857(14) 0.0461(6) Uani 1 1 d . . . O3 O 0.7582(2) -0.0619(3) 0.45306(17) 0.0671(8) Uani 1 1 d . . . O4 O 0.8843(2) 0.2222(3) 0.38448(17) 0.0531(6) Uani 1 1 d . . . O5 O 0.7963(2) 0.3984(3) 0.46755(18) 0.0654(7) Uani 1 1 d . . . S1 S 0.62009(8) 0.24171(12) 0.24227(6) 0.0505(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0540(19) 0.0402(19) 0.0461(17) -0.0021(13) -0.0021(15) 0.0018(15) C2 0.0474(19) 0.050(2) 0.064(2) 0.0058(17) -0.0123(17) 0.0089(17) C3 0.0375(17) 0.049(2) 0.084(3) -0.0005(18) 0.0050(17) 0.0119(16) C4 0.0445(18) 0.043(2) 0.061(2) -0.0016(15) 0.0135(15) 0.0014(15) C5 0.0336(14) 0.0296(16) 0.0442(16) -0.0006(12) 0.0004(12) -0.0024(12) C6 0.0350(14) 0.0278(16) 0.0475(17) -0.0047(12) 0.0003(12) -0.0032(12) C7 0.0265(15) 0.0369(19) 0.074(2) 0.0093(16) 0.0027(15) -0.0001(13) C8 0.0295(14) 0.0380(17) 0.0356(14) 0.0001(12) 0.0001(11) 0.0023(12) C9 0.0335(14) 0.0416(18) 0.0388(15) -0.0015(12) 0.0058(12) 0.0023(13) C10 0.071(2) 0.040(2) 0.061(2) -0.0052(15) 0.0268(18) -0.0123(17) C11 0.0320(14) 0.0378(18) 0.0439(16) -0.0007(13) 0.0041(12) 0.0011(12) C12 0.0309(16) 0.070(3) 0.083(3) -0.011(2) 0.0078(17) -0.0085(16) O1 0.0485(15) 0.098(2) 0.0621(17) -0.0122(15) 0.0240(13) 0.0168(14) O2 0.0440(12) 0.0414(14) 0.0474(12) 0.0006(9) 0.0025(10) -0.0113(10) O3 0.0674(16) 0.0502(16) 0.0628(15) 0.0073(12) -0.0187(13) 0.0060(13) O4 0.0301(11) 0.0577(15) 0.0690(15) -0.0220(11) 0.0086(10) -0.0047(10) O5 0.0526(15) 0.0617(17) 0.0802(17) -0.0344(14) 0.0152(13) -0.0093(12) S1 0.0479(5) 0.0594(6) 0.0418(4) 0.0039(4) 0.0078(3) 0.0022(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.368(5) . ? C1 C6 1.393(4) . ? C1 H1 0.9300 . ? C2 C3 1.385(5) . ? C2 H2 0.9300 . ? C3 C4 1.370(5) . ? C3 H3 0.9300 . ? C4 C5 1.395(4) . ? C4 H4 0.9300 . ? C5 C6 1.380(4) . ? C5 C7 1.488(4) . ? C6 S1 1.774(3) . ? C7 O1 1.047(4) . ? C7 C8 1.594(5) . ? C8 C9 1.525(5) . ? C8 C11 1.526(4) . ? C8 S1 1.857(3) . ? C9 O3 1.188(3) . ? C9 O2 1.317(3) . ? C10 O2 1.444(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 O5 1.191(4) . ? C11 O4 1.314(4) . ? C12 O4 1.442(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C1 C6 118.3(3) . . ? C2 C1 H1 120.9 . . ? C6 C1 H1 120.9 . . ? C1 C2 C3 121.7(3) . . ? C1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? C4 C3 C2 120.2(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 120.5(3) . . ? C6 C5 C7 114.2(3) . . ? C4 C5 C7 125.2(3) . . ? C5 C6 C1 120.4(3) . . ? C5 C6 S1 117.3(2) . . ? C1 C6 S1 122.2(2) . . ? O1 C7 C5 128.6(3) . . ? O1 C7 C8 122.4(3) . . ? C5 C7 C8 108.8(3) . . ? C9 C8 C11 111.3(2) . . ? C9 C8 C7 106.0(2) . . ? C11 C8 C7 109.9(2) . . ? C9 C8 S1 113.60(19) . . ? C11 C8 S1 107.0(2) . . ? C7 C8 S1 109.01(19) . . ? O3 C9 O2 125.6(3) . . ? O3 C9 C8 123.1(3) . . ? O2 C9 C8 111.2(2) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O5 C11 O4 125.2(3) . . ? O5 C11 C8 124.0(3) . . ? O4 C11 C8 110.7(2) . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 O2 C10 117.1(2) . . ? C11 O4 C12 116.8(3) . . ? C6 S1 C8 90.56(13) . . ? 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 C6 C1 C2 C3 0.6(5) . . . . ? C1 C2 C3 C4 -1.0(6) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C3 C4 C5 C7 -177.7(3) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? C7 C5 C6 C1 177.5(3) . . . . ? C4 C5 C6 S1 179.2(2) . . . . ? C7 C5 C6 S1 -2.4(3) . . . . ? C2 C1 C6 C5 0.3(5) . . . . ? C2 C1 C6 S1 -179.8(3) . . . . ? C6 C5 C7 O1 -175.3(4) . . . . ? C4 C5 C7 O1 3.0(6) . . . . ? C6 C5 C7 C8 0.8(3) . . . . ? C4 C5 C7 C8 179.1(3) . . . . ? O1 C7 C8 C9 54.7(4) . . . . ? C5 C7 C8 C9 -121.7(2) . . . . ? O1 C7 C8 C11 -65.7(4) . . . . ? C5 C7 C8 C11 117.9(3) . . . . ? O1 C7 C8 S1 177.4(3) . . . . ? C5 C7 C8 S1 0.9(3) . . . . ? C11 C8 C9 O3 22.8(4) . . . . ? C7 C8 C9 O3 -96.6(3) . . . . ? S1 C8 C9 O3 143.7(3) . . . . ? C11 C8 C9 O2 -161.3(2) . . . . ? C7 C8 C9 O2 79.2(3) . . . . ? S1 C8 C9 O2 -40.5(3) . . . . ? C9 C8 C11 O5 -125.2(3) . . . . ? C7 C8 C11 O5 -8.0(4) . . . . ? S1 C8 C11 O5 110.2(3) . . . . ? C9 C8 C11 O4 57.5(3) . . . . ? C7 C8 C11 O4 174.6(3) . . . . ? S1 C8 C11 O4 -67.2(3) . . . . ? O3 C9 O2 C10 1.3(4) . . . . ? C8 C9 O2 C10 -174.4(2) . . . . ? O5 C11 O4 C12 0.0(5) . . . . ? C8 C11 O4 C12 177.3(3) . . . . ? C5 C6 S1 C8 2.5(2) . . . . ? C1 C6 S1 C8 -177.4(3) . . . . ? C9 C8 S1 C6 116.1(2) . . . . ? C11 C8 S1 C6 -120.6(2) . . . . ? C7 C8 S1 C6 -1.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.610 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.064 #===END data_173B _database_code_depnum_ccdc_archive 'CCDC 720188' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 O4 S' _chemical_formula_weight 288.31 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 Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 8.8103(3) _cell_length_b 7.9336(2) _cell_length_c 38.3842(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2682.96(14) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2787 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 21.92 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9106 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ApexII 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 20215 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -51 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 1.06 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3257 _reflns_number_gt 1883 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction 'SAINT PLUS ,Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0334P)^2^+1.5680P] 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 3257 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1004 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3274(3) 1.0830(3) 0.44832(6) 0.0479(6) Uani 1 1 d . . . C2 C 0.2414(4) 1.1362(4) 0.47678(6) 0.0606(8) Uani 1 1 d . . . H2 H 0.2880 1.1689 0.4974 0.073 Uiso 1 1 calc R . . C3 C 0.0869(4) 1.1389(4) 0.47352(7) 0.0660(8) Uani 1 1 d . . . H3 H 0.0287 1.1755 0.4923 0.079 Uiso 1 1 calc R . . C4 C 0.0141(3) 1.0890(4) 0.44317(7) 0.0625(8) Uani 1 1 d . . . H4 H -0.0913 1.0917 0.4420 0.075 Uiso 1 1 calc R . . C5 C 0.0962(3) 1.0356(3) 0.41482(6) 0.0490(6) Uani 1 1 d . . . H5 H 0.0477 1.0018 0.3945 0.059 Uiso 1 1 calc R . . C6 C 0.2539(3) 1.0333(3) 0.41733(5) 0.0412(6) Uani 1 1 d . . . C7 C 0.3664(3) 0.9827(3) 0.39297(5) 0.0387(5) Uani 1 1 d . . . C8 C 0.4967(2) 0.8940(3) 0.34648(5) 0.0371(5) Uani 1 1 d . . . C9 C 0.6075(3) 0.9198(3) 0.37772(6) 0.0458(6) Uani 1 1 d . . . C10 C 0.5120(3) 0.9924(3) 0.40388(6) 0.0446(6) Uani 1 1 d . . . C11 C 0.4516(2) 0.7250(3) 0.30006(6) 0.0416(6) Uani 1 1 d . . . C12 C 0.4278(3) 0.9012(3) 0.28805(6) 0.0413(6) Uani 1 1 d . . . H12A H 0.3210 0.9311 0.2887 0.050 Uiso 1 1 calc R . . H12B H 0.4656 0.9167 0.2645 0.050 Uiso 1 1 calc R . . C13 C 0.5188(2) 1.0064(3) 0.31407(6) 0.0379(5) Uani 1 1 d . . . C14 C 0.6861(3) 1.0092(3) 0.30316(6) 0.0509(6) Uani 1 1 d . . . H14A H 0.6962 1.0686 0.2815 0.076 Uiso 1 1 calc R . . H14B H 0.7219 0.8957 0.3004 0.076 Uiso 1 1 calc R . . H14C H 0.7449 1.0650 0.3208 0.076 Uiso 1 1 calc R . . C15 C 0.4606(3) 1.1853(3) 0.31912(7) 0.0551(7) Uani 1 1 d . . . H15A H 0.5211 1.2413 0.3364 0.083 Uiso 1 1 calc R . . H15B H 0.3568 1.1820 0.3267 0.083 Uiso 1 1 calc R . . H15C H 0.4674 1.2455 0.2975 0.083 Uiso 1 1 calc R . . O1 O 0.34491(16) 0.9208(2) 0.36053(4) 0.0413(4) Uani 1 1 d . . . O2 O 0.49932(18) 0.7270(2) 0.33427(4) 0.0424(4) Uani 1 1 d . . . O3 O 0.7401(2) 0.8813(3) 0.37744(4) 0.0687(6) Uani 1 1 d . . . O4 O 0.4364(2) 0.5943(2) 0.28513(5) 0.0600(5) Uani 1 1 d . . . S1 S 0.52525(8) 1.06639(10) 0.446427(17) 0.0584(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0598(16) 0.0413(15) 0.0427(13) -0.0020(11) 0.0005(12) 0.0008(12) C2 0.082(2) 0.0555(18) 0.0441(14) -0.0076(12) 0.0031(15) -0.0003(16) C3 0.081(2) 0.062(2) 0.0553(17) -0.0052(14) 0.0219(16) 0.0061(17) C4 0.0515(17) 0.071(2) 0.0647(18) 0.0035(15) 0.0169(14) 0.0093(15) C5 0.0458(15) 0.0535(17) 0.0477(14) 0.0013(12) 0.0048(12) 0.0035(12) C6 0.0464(14) 0.0382(14) 0.0389(12) 0.0016(10) 0.0015(11) 0.0021(11) C7 0.0388(13) 0.0390(14) 0.0383(12) -0.0040(10) -0.0015(10) 0.0004(11) C8 0.0309(12) 0.0386(13) 0.0417(12) -0.0065(10) -0.0007(10) 0.0027(10) C9 0.0374(14) 0.0513(16) 0.0487(14) 0.0012(12) -0.0060(11) 0.0044(12) C10 0.0418(14) 0.0501(15) 0.0420(12) -0.0065(11) -0.0076(11) -0.0013(12) C11 0.0338(13) 0.0430(15) 0.0479(14) -0.0081(11) 0.0058(11) 0.0004(11) C12 0.0383(13) 0.0451(14) 0.0404(12) 0.0011(10) -0.0001(10) -0.0020(11) C13 0.0326(12) 0.0351(13) 0.0459(12) 0.0005(10) -0.0008(10) -0.0004(10) C14 0.0382(13) 0.0491(16) 0.0653(16) 0.0044(13) 0.0040(12) -0.0062(12) C15 0.0513(16) 0.0377(14) 0.0764(18) -0.0002(13) -0.0035(14) 0.0036(12) O1 0.0299(8) 0.0553(11) 0.0387(8) -0.0095(7) -0.0009(6) 0.0008(7) O2 0.0478(10) 0.0346(9) 0.0448(9) -0.0008(7) 0.0012(7) 0.0030(7) O3 0.0391(11) 0.0988(17) 0.0680(12) -0.0064(11) -0.0117(9) 0.0191(10) O4 0.0619(12) 0.0480(12) 0.0700(12) -0.0224(9) 0.0040(9) -0.0032(9) S1 0.0589(4) 0.0692(5) 0.0471(4) -0.0139(3) -0.0126(3) -0.0012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.395(3) . ? C1 C6 1.410(3) . ? C1 S1 1.749(3) . ? C2 C3 1.367(4) . ? C2 H2 0.9300 . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.374(3) . ? C4 H4 0.9300 . ? C5 C6 1.393(3) . ? C5 H5 0.9300 . ? C6 C7 1.420(3) . ? C7 C10 1.352(3) . ? C7 O1 1.352(2) . ? C8 O2 1.406(3) . ? C8 O1 1.457(2) . ? C8 C13 1.543(3) . ? C8 C9 1.560(3) . ? C9 O3 1.207(3) . ? C9 C10 1.432(3) . ? C10 S1 1.739(2) . ? C11 O4 1.193(3) . ? C11 O2 1.379(3) . ? C11 C12 1.487(3) . ? C12 C13 1.529(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C15 1.521(3) . ? C13 C14 1.533(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 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 C1 C6 119.7(2) . . ? C2 C1 S1 126.6(2) . . ? C6 C1 S1 113.66(18) . . ? C3 C2 C1 118.3(3) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 122.2(3) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C5 C4 C3 120.6(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 118.3(2) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C5 C6 C1 120.8(2) . . ? C5 C6 C7 130.8(2) . . ? C1 C6 C7 108.3(2) . . ? C10 C7 O1 116.06(19) . . ? C10 C7 C6 116.2(2) . . ? O1 C7 C6 127.7(2) . . ? O2 C8 O1 106.03(17) . . ? O2 C8 C13 105.91(17) . . ? O1 C8 C13 109.24(17) . . ? O2 C8 C9 111.68(18) . . ? O1 C8 C9 105.72(16) . . ? C13 C8 C9 117.71(19) . . ? O3 C9 C10 132.6(2) . . ? O3 C9 C8 124.5(2) . . ? C10 C9 C8 102.94(19) . . ? C7 C10 C9 108.5(2) . . ? C7 C10 S1 111.97(17) . . ? C9 C10 S1 139.04(18) . . ? O4 C11 O2 120.1(2) . . ? O4 C11 C12 130.8(2) . . ? O2 C11 C12 109.14(18) . . ? C11 C12 C13 103.69(18) . . ? C11 C12 H12A 111.0 . . ? C13 C12 H12A 111.0 . . ? C11 C12 H12B 111.0 . . ? C13 C12 H12B 111.0 . . ? H12A C12 H12B 109.0 . . ? C15 C13 C12 114.59(19) . . ? C15 C13 C14 110.19(19) . . ? C12 C13 C14 109.49(18) . . ? C15 C13 C8 113.22(19) . . ? C12 C13 C8 98.34(17) . . ? C14 C13 C8 110.48(18) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 O1 C8 105.38(16) . . ? C11 O2 C8 108.83(17) . . ? C10 S1 C1 89.86(11) . . ? 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 C6 C1 C2 C3 -0.3(4) . . . . ? S1 C1 C2 C3 -179.1(2) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C1 0.6(4) . . . . ? C4 C5 C6 C7 178.9(3) . . . . ? C2 C1 C6 C5 -0.4(4) . . . . ? S1 C1 C6 C5 178.61(19) . . . . ? C2 C1 C6 C7 -179.0(2) . . . . ? S1 C1 C6 C7 0.0(3) . . . . ? C5 C6 C7 C10 -178.5(3) . . . . ? C1 C6 C7 C10 -0.1(3) . . . . ? C5 C6 C7 O1 -0.9(4) . . . . ? C1 C6 C7 O1 177.6(2) . . . . ? O2 C8 C9 O3 52.5(3) . . . . ? O1 C8 C9 O3 167.4(2) . . . . ? C13 C8 C9 O3 -70.3(3) . . . . ? O2 C8 C9 C10 -126.6(2) . . . . ? O1 C8 C9 C10 -11.8(2) . . . . ? C13 C8 C9 C10 110.5(2) . . . . ? O1 C7 C10 C9 -4.2(3) . . . . ? C6 C7 C10 C9 173.7(2) . . . . ? O1 C7 C10 S1 -177.79(17) . . . . ? C6 C7 C10 S1 0.1(3) . . . . ? O3 C9 C10 C7 -169.4(3) . . . . ? C8 C9 C10 C7 9.7(3) . . . . ? O3 C9 C10 S1 1.5(5) . . . . ? C8 C9 C10 S1 -179.5(3) . . . . ? O4 C11 C12 C13 -160.4(2) . . . . ? O2 C11 C12 C13 19.4(2) . . . . ? C11 C12 C13 C15 -152.9(2) . . . . ? C11 C12 C13 C14 82.7(2) . . . . ? C11 C12 C13 C8 -32.6(2) . . . . ? O2 C8 C13 C15 158.00(19) . . . . ? O1 C8 C13 C15 44.2(2) . . . . ? C9 C8 C13 C15 -76.3(2) . . . . ? O2 C8 C13 C12 36.6(2) . . . . ? O1 C8 C13 C12 -77.2(2) . . . . ? C9 C8 C13 C12 162.34(19) . . . . ? O2 C8 C13 C14 -77.9(2) . . . . ? O1 C8 C13 C14 168.33(17) . . . . ? C9 C8 C13 C14 47.8(3) . . . . ? C10 C7 O1 C8 -3.9(3) . . . . ? C6 C7 O1 C8 178.5(2) . . . . ? O2 C8 O1 C7 128.27(18) . . . . ? C13 C8 O1 C7 -118.00(19) . . . . ? C9 C8 O1 C7 9.6(2) . . . . ? O4 C11 O2 C8 -175.5(2) . . . . ? C12 C11 O2 C8 4.7(2) . . . . ? O1 C8 O2 C11 89.07(19) . . . . ? C13 C8 O2 C11 -26.9(2) . . . . ? C9 C8 O2 C11 -156.26(18) . . . . ? C7 C10 S1 C1 -0.1(2) . . . . ? C9 C10 S1 C1 -170.8(3) . . . . ? C2 C1 S1 C10 179.0(3) . . . . ? C6 C1 S1 C10 0.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.224 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.043 #===END data_175a _database_code_depnum_ccdc_archive 'CCDC 720189' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 O4 S' _chemical_formula_weight 292.34 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.0834(10) _cell_length_b 5.9233(3) _cell_length_c 12.5540(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.986(2) _cell_angle_gamma 90.00 _cell_volume 1455.23(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5159 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 28.13 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9088 _exptl_absorpt_correction_T_max 0.9660 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ApexII 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 9564 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.04 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2981 _reflns_number_gt 2410 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction 'SAINT PLUS ,Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0706P)^2^+0.2449P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2981 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.35217(8) 0.5852(3) 0.72221(14) 0.0374(4) Uani 1 1 d . . . C2 C 0.36822(10) 0.7655(3) 0.66141(16) 0.0473(4) Uani 1 1 d . . . H2 H 0.3445 0.7890 0.5897 0.057 Uiso 1 1 calc R . . C3 C 0.42020(10) 0.9077(3) 0.71047(18) 0.0526(5) Uani 1 1 d . . . H3 H 0.4315 1.0294 0.6712 0.063 Uiso 1 1 calc R . . C4 C 0.45635(10) 0.8734(4) 0.81805(18) 0.0538(5) Uani 1 1 d . . . H4 H 0.4915 0.9717 0.8489 0.065 Uiso 1 1 calc R . . C5 C 0.44073(9) 0.6969(3) 0.87872(16) 0.0476(5) Uani 1 1 d . . . H5 H 0.4647 0.6756 0.9505 0.057 Uiso 1 1 calc R . . C6 C 0.38807(8) 0.5495(3) 0.83053(14) 0.0387(4) Uani 1 1 d . . . C7 C 0.36262(8) 0.3570(3) 0.87681(13) 0.0387(4) Uani 1 1 d . . . C8 C 0.30815(8) 0.2530(3) 0.80738(13) 0.0370(4) Uani 1 1 d . . . C9 C 0.27515(8) 0.0561(3) 0.83806(14) 0.0379(4) Uani 1 1 d . . . C10 C 0.21326(9) -0.0447(3) 0.76322(14) 0.0389(4) Uani 1 1 d . . . H10A H 0.2186 -0.2074 0.7630 0.047 Uiso 1 1 calc R . . H10B H 0.2112 0.0087 0.6895 0.047 Uiso 1 1 calc R . . C11 C 0.14455(8) 0.0119(3) 0.79446(13) 0.0368(4) Uani 1 1 d . . . C12 C 0.14461(9) -0.0999(3) 0.90576(15) 0.0453(4) Uani 1 1 d . . . H12A H 0.1498 -0.2617 0.8990 0.054 Uiso 1 1 calc R . . H12B H 0.1838 -0.0453 0.9596 0.054 Uiso 1 1 calc R . . C13 C 0.08118(9) -0.0549(3) 0.94618(15) 0.0475(5) Uani 1 1 d . . . C14 C 0.13619(11) 0.2671(3) 0.80003(19) 0.0551(5) Uani 1 1 d . . . H14A H 0.1405 0.3335 0.7321 0.083 Uiso 1 1 calc R . . H14B H 0.1709 0.3270 0.8586 0.083 Uiso 1 1 calc R . . H14C H 0.0919 0.3014 0.8129 0.083 Uiso 1 1 calc R . . C15 C 0.08739(11) -0.0870(4) 0.70504(17) 0.0551(5) Uani 1 1 d . . . H15A H 0.0439 -0.0510 0.7205 0.083 Uiso 1 1 calc R . . H15B H 0.0925 -0.2480 0.7030 0.083 Uiso 1 1 calc R . . H15C H 0.0899 -0.0241 0.6356 0.083 Uiso 1 1 calc R . . O1 O 0.39004(7) 0.2866(3) 0.97806(10) 0.0550(4) Uani 1 1 d . . . O2 O 0.29776(7) -0.0288(2) 0.92983(10) 0.0515(3) Uani 1 1 d . . . O3 O 0.07848(8) 0.1101(3) 1.00573(14) 0.0774(5) Uani 1 1 d . . . O4 O 0.03266(9) -0.1949(3) 0.92026(15) 0.0800(6) Uani 1 1 d . . . S1 S 0.28775(2) 0.38678(8) 0.67970(3) 0.04082(17) Uani 1 1 d . . . H1A H 0.3654(15) 0.165(4) 0.984(2) 0.079(8) Uiso 1 1 d . . . H2A H -0.006(3) -0.156(8) 0.953(4) 0.20(2) 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 C1 0.0330(8) 0.0393(10) 0.0418(9) -0.0050(7) 0.0122(7) 0.0020(7) C2 0.0481(10) 0.0452(11) 0.0501(10) 0.0012(8) 0.0144(8) 0.0007(8) C3 0.0464(11) 0.0452(12) 0.0696(13) 0.0039(9) 0.0199(10) -0.0029(8) C4 0.0388(10) 0.0482(12) 0.0750(14) -0.0101(10) 0.0138(10) -0.0066(8) C5 0.0353(9) 0.0531(12) 0.0525(10) -0.0087(9) 0.0058(8) -0.0019(8) C6 0.0302(8) 0.0430(10) 0.0439(9) -0.0059(7) 0.0106(7) 0.0033(7) C7 0.0327(8) 0.0479(11) 0.0352(8) -0.0030(7) 0.0070(7) 0.0029(7) C8 0.0338(8) 0.0421(10) 0.0355(8) -0.0017(7) 0.0087(7) 0.0025(7) C9 0.0341(9) 0.0414(10) 0.0403(9) 0.0001(7) 0.0129(7) 0.0063(7) C10 0.0427(9) 0.0347(9) 0.0416(9) -0.0043(7) 0.0139(7) 0.0001(7) C11 0.0344(9) 0.0332(9) 0.0429(9) 0.0004(7) 0.0086(7) -0.0003(7) C12 0.0395(9) 0.0504(11) 0.0467(10) 0.0020(8) 0.0113(8) 0.0015(8) C13 0.0414(10) 0.0579(13) 0.0449(10) -0.0049(9) 0.0133(8) -0.0064(8) C14 0.0493(11) 0.0384(11) 0.0809(14) 0.0009(10) 0.0217(10) 0.0072(8) C15 0.0466(11) 0.0584(13) 0.0544(11) 0.0012(9) -0.0009(9) -0.0066(9) O1 0.0461(8) 0.0722(10) 0.0414(7) 0.0079(6) -0.0016(6) -0.0091(7) O2 0.0428(7) 0.0606(9) 0.0498(7) 0.0139(6) 0.0073(6) 0.0012(6) O3 0.0653(10) 0.0875(12) 0.0911(12) -0.0441(10) 0.0423(9) -0.0266(8) O4 0.0635(10) 0.0887(13) 0.0992(12) -0.0398(10) 0.0425(9) -0.0340(9) S1 0.0415(3) 0.0450(3) 0.0343(2) -0.00033(16) 0.00502(18) -0.00429(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.392(3) . ? C1 C6 1.405(2) . ? C1 S1 1.7408(17) . ? C2 C3 1.375(3) . ? C2 H2 0.9300 . ? C3 C4 1.397(3) . ? C3 H3 0.9300 . ? C4 C5 1.371(3) . ? C4 H4 0.9300 . ? C5 C6 1.400(3) . ? C5 H5 0.9300 . ? C6 C7 1.426(3) . ? C7 O1 1.334(2) . ? C7 C8 1.381(2) . ? C8 C9 1.436(2) . ? C8 S1 1.7522(16) . ? C9 O2 1.245(2) . ? C9 C10 1.503(2) . ? C10 C11 1.554(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C14 1.524(2) . ? C11 C15 1.530(3) . ? C11 C12 1.546(2) . ? C12 C13 1.497(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O3 1.239(2) . ? C13 O4 1.265(2) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? O1 H1A 0.89(3) . ? O4 H2A 0.99(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.00(16) . . ? C2 C1 S1 126.70(14) . . ? C6 C1 S1 112.29(13) . . ? C3 C2 C1 118.07(18) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 121.42(18) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 120.93(18) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 118.74(18) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C1 119.85(17) . . ? C5 C6 C7 128.92(16) . . ? C1 C6 C7 111.23(15) . . ? O1 C7 C8 124.12(17) . . ? O1 C7 C6 121.97(15) . . ? C8 C7 C6 113.91(15) . . ? C7 C8 C9 122.74(15) . . ? C7 C8 S1 111.39(13) . . ? C9 C8 S1 125.84(13) . . ? O2 C9 C8 118.77(16) . . ? O2 C9 C10 119.78(16) . . ? C8 C9 C10 121.42(15) . . ? C9 C10 C11 114.42(13) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C14 C11 C15 109.93(16) . . ? C14 C11 C12 111.17(15) . . ? C15 C11 C12 110.32(15) . . ? C14 C11 C10 109.79(14) . . ? C15 C11 C10 107.15(14) . . ? C12 C11 C10 108.39(14) . . ? C13 C12 C11 113.70(15) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? O3 C13 O4 122.45(18) . . ? O3 C13 C12 120.07(17) . . ? O4 C13 C12 117.43(18) . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 O1 H1A 102.7(18) . . ? C13 O4 H2A 112(3) . . ? C1 S1 C8 91.15(8) . . ? 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 C6 C1 C2 C3 -0.1(3) . . . . ? S1 C1 C2 C3 178.51(14) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? C4 C5 C6 C7 -179.65(17) . . . . ? C2 C1 C6 C5 0.2(2) . . . . ? S1 C1 C6 C5 -178.60(13) . . . . ? C2 C1 C6 C7 179.52(15) . . . . ? S1 C1 C6 C7 0.75(18) . . . . ? C5 C6 C7 O1 -2.5(3) . . . . ? C1 C6 C7 O1 178.20(15) . . . . ? C5 C6 C7 C8 177.76(17) . . . . ? C1 C6 C7 C8 -1.5(2) . . . . ? O1 C7 C8 C9 0.1(3) . . . . ? C6 C7 C8 C9 179.85(15) . . . . ? O1 C7 C8 S1 -178.12(14) . . . . ? C6 C7 C8 S1 1.59(19) . . . . ? C7 C8 C9 O2 -2.2(3) . . . . ? S1 C8 C9 O2 175.79(13) . . . . ? C7 C8 C9 C10 176.15(15) . . . . ? S1 C8 C9 C10 -5.8(2) . . . . ? O2 C9 C10 C11 75.9(2) . . . . ? C8 C9 C10 C11 -102.40(18) . . . . ? C9 C10 C11 C14 56.1(2) . . . . ? C9 C10 C11 C15 175.43(15) . . . . ? C9 C10 C11 C12 -65.52(19) . . . . ? C14 C11 C12 C13 58.3(2) . . . . ? C15 C11 C12 C13 -63.9(2) . . . . ? C10 C11 C12 C13 179.08(15) . . . . ? C11 C12 C13 O3 -91.1(2) . . . . ? C11 C12 C13 O4 91.3(2) . . . . ? C2 C1 S1 C8 -178.58(16) . . . . ? C6 C1 S1 C8 0.10(13) . . . . ? C7 C8 S1 C1 -0.96(13) . . . . ? C9 C8 S1 C1 -179.15(15) . . . . ? 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 H1A O2 0.89(3) 1.79(3) 2.605(2) 151(3) . O4 H2A O3 0.99(6) 1.67(6) 2.651(2) 172(4) 3_557 _diffrn_measured_fraction_theta_max 0.827 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.296 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.048 # end Validation Reply Form #===END data_272c _database_code_depnum_ccdc_archive 'CCDC 735538' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 O4 S' _chemical_formula_sum 'C14 H14 O4 S' _chemical_formula_weight 278.31 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)/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 18.9046(9) _cell_length_b 5.6296(3) _cell_length_c 13.0661(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.761(3) _cell_angle_gamma 90.00 _cell_volume 1350.65(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1959 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 22.85 _exptl_crystal_description Rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9187 _exptl_absorpt_correction_T_max 0.9663 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ApexII 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 9308 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.11 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3206 _reflns_number_gt 1890 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction 'SAINT PLUS ,Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0622P)^2^+0.4183P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3206 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1060 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.36295(15) 0.7647(5) 0.1775(2) 0.0513(7) Uani 1 1 d . . . H1 H 0.3389 0.7823 0.1071 0.062 Uiso 1 1 calc R . . C2 C 0.41913(14) 0.9134(5) 0.2239(3) 0.0566(8) Uani 1 1 d . . . H2 H 0.4333 1.0328 0.1837 0.068 Uiso 1 1 calc R . . C3 C 0.45529(14) 0.8896(5) 0.3291(3) 0.0563(8) Uani 1 1 d . . . H3 H 0.4929 0.9936 0.3582 0.068 Uiso 1 1 calc R . . C4 C 0.43635(14) 0.7155(5) 0.3907(2) 0.0520(7) Uani 1 1 d . . . H4 H 0.4608 0.7002 0.4611 0.062 Uiso 1 1 calc R . . C5 C 0.37941(12) 0.5609(4) 0.3456(2) 0.0405(6) Uani 1 1 d . . . C6 C 0.34933(13) 0.3703(5) 0.3933(2) 0.0417(6) Uani 1 1 d . . . C7 C 0.29166(13) 0.2600(4) 0.32630(19) 0.0399(6) Uani 1 1 d . . . C8 C 0.34318(13) 0.5867(4) 0.2396(2) 0.0408(6) Uani 1 1 d . . . C9 C 0.25247(13) 0.0665(5) 0.3594(2) 0.0433(6) Uani 1 1 d . . . C10 C 0.18764(13) -0.0380(5) 0.2826(2) 0.0474(7) Uani 1 1 d . . . H10A H 0.2045 -0.1120 0.2257 0.057 Uiso 1 1 calc R . . H10B H 0.1552 0.0907 0.2524 0.057 Uiso 1 1 calc R . . C11 C 0.14412(14) -0.2202(5) 0.3278(2) 0.0507(7) Uani 1 1 d . . . H11 H 0.1781 -0.3386 0.3668 0.061 Uiso 1 1 calc R . . C12 C 0.10506(16) -0.1044(5) 0.4040(3) 0.0601(8) Uani 1 1 d . . . H12A H 0.1407 -0.0361 0.4624 0.072 Uiso 1 1 calc R . . H12B H 0.0745 0.0234 0.3683 0.072 Uiso 1 1 calc R . . C13 C 0.05900(17) -0.2794(6) 0.4456(2) 0.0600(8) Uani 1 1 d . . . C14 C 0.09023(16) -0.3475(6) 0.2386(3) 0.0696(9) Uani 1 1 d . . . H14A H 0.0543 -0.2364 0.2026 0.104 Uiso 1 1 calc R . . H14B H 0.0667 -0.4733 0.2674 0.104 Uiso 1 1 calc R . . H14C H 0.1159 -0.4125 0.1899 0.104 Uiso 1 1 calc R . . O1 O 0.37578(11) 0.3098(4) 0.49320(15) 0.0635(6) Uani 1 1 d . . . O2 O 0.27262(10) -0.0109(4) 0.44999(15) 0.0604(6) Uani 1 1 d . . . O3 O 0.09286(12) -0.4558(5) 0.4969(2) 0.0845(8) Uani 1 1 d . . . O4 O -0.00737(12) -0.2569(5) 0.4294(2) 0.0871(8) Uani 1 1 d . . . S1 S 0.27332(3) 0.38181(12) 0.19999(5) 0.0457(2) Uani 1 1 d . . . H3X H 0.062(2) -0.554(9) 0.516(4) 0.15(2) Uiso 1 1 d . . . H1X H 0.348(2) 0.191(7) 0.499(3) 0.111(15) 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 C1 0.0506(15) 0.0526(17) 0.0515(17) 0.0044(13) 0.0138(13) -0.0019(13) C2 0.0524(17) 0.0482(17) 0.073(2) 0.0038(14) 0.0225(15) -0.0059(13) C3 0.0441(15) 0.0477(16) 0.077(2) -0.0093(15) 0.0146(15) -0.0099(13) C4 0.0420(14) 0.0513(16) 0.0600(18) -0.0084(14) 0.0069(13) -0.0025(13) C5 0.0328(12) 0.0427(14) 0.0459(16) -0.0064(11) 0.0091(11) 0.0016(11) C6 0.0367(13) 0.0508(15) 0.0371(15) -0.0017(12) 0.0078(11) 0.0007(12) C7 0.0384(13) 0.0470(15) 0.0348(14) -0.0013(11) 0.0097(11) -0.0038(11) C8 0.0372(13) 0.0425(14) 0.0446(15) -0.0037(11) 0.0132(11) -0.0003(11) C9 0.0412(14) 0.0482(15) 0.0420(16) -0.0002(12) 0.0128(12) -0.0012(12) C10 0.0448(14) 0.0521(16) 0.0465(16) 0.0007(12) 0.0129(12) -0.0083(13) C11 0.0460(14) 0.0507(16) 0.0555(18) 0.0051(13) 0.0125(13) -0.0044(13) C12 0.0603(17) 0.0567(18) 0.068(2) 0.0031(15) 0.0258(15) -0.0046(15) C13 0.0562(19) 0.066(2) 0.062(2) 0.0126(16) 0.0218(15) 0.0010(16) C14 0.0597(18) 0.075(2) 0.075(2) -0.0080(17) 0.0178(16) -0.0239(17) O1 0.0641(13) 0.0777(15) 0.0418(12) 0.0034(10) -0.0010(10) -0.0191(12) O2 0.0631(12) 0.0697(14) 0.0449(12) 0.0138(10) 0.0056(9) -0.0122(11) O3 0.0601(13) 0.0940(19) 0.104(2) 0.0464(16) 0.0295(13) 0.0063(13) O4 0.0538(13) 0.0984(19) 0.115(2) 0.0510(16) 0.0325(13) 0.0065(12) S1 0.0454(4) 0.0516(4) 0.0385(4) 0.0011(3) 0.0065(3) -0.0093(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.374(4) . ? C1 C8 1.395(4) . ? C1 H1 0.9300 . ? C2 C3 1.389(4) . ? C2 H2 0.9300 . ? C3 C4 1.369(4) . ? C3 H3 0.9300 . ? C4 C5 1.401(4) . ? C4 H4 0.9300 . ? C5 C8 1.399(3) . ? C5 C6 1.425(4) . ? C6 O1 1.326(3) . ? C6 C7 1.374(3) . ? C7 C9 1.441(4) . ? C7 S1 1.744(3) . ? C8 S1 1.737(2) . ? C9 O2 1.233(3) . ? C9 C10 1.507(3) . ? C10 C11 1.520(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.520(4) . ? C11 C14 1.532(4) . ? C11 H11 0.9800 . ? C12 C13 1.500(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O4 1.228(3) . ? C13 O3 1.281(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O1 H1X 0.86(4) . ? O3 H3X 0.88(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C8 117.9(3) . . ? C2 C1 H1 121.1 . . ? C8 C1 H1 121.1 . . ? C1 C2 C3 121.6(3) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C8 C5 C4 119.9(2) . . ? C8 C5 C6 111.0(2) . . ? C4 C5 C6 129.1(2) . . ? O1 C6 C7 124.6(2) . . ? O1 C6 C5 121.8(2) . . ? C7 C6 C5 113.6(2) . . ? C6 C7 C9 122.5(2) . . ? C6 C7 S1 112.01(19) . . ? C9 C7 S1 125.50(18) . . ? C1 C8 C5 121.0(2) . . ? C1 C8 S1 126.4(2) . . ? C5 C8 S1 112.60(19) . . ? O2 C9 C7 119.5(2) . . ? O2 C9 C10 121.2(2) . . ? C7 C9 C10 119.3(2) . . ? C9 C10 C11 115.7(2) . . ? C9 C10 H10A 108.3 . . ? C11 C10 H10A 108.3 . . ? C9 C10 H10B 108.3 . . ? C11 C10 H10B 108.3 . . ? H10A C10 H10B 107.4 . . ? C10 C11 C12 110.9(2) . . ? C10 C11 C14 110.1(2) . . ? C12 C11 C14 111.1(2) . . ? C10 C11 H11 108.2 . . ? C12 C11 H11 108.2 . . ? C14 C11 H11 108.2 . . ? C13 C12 C11 111.7(2) . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? O4 C13 O3 122.2(3) . . ? O4 C13 C12 121.8(3) . . ? O3 C13 C12 116.0(3) . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C6 O1 H1X 101(3) . . ? C13 O3 H3X 111(3) . . ? C8 S1 C7 90.76(12) . . ? 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 C8 C1 C2 C3 -0.3(4) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C8 -0.1(4) . . . . ? C3 C4 C5 C6 -179.0(2) . . . . ? C8 C5 C6 O1 178.8(2) . . . . ? C4 C5 C6 O1 -2.2(4) . . . . ? C8 C5 C6 C7 -1.2(3) . . . . ? C4 C5 C6 C7 177.8(2) . . . . ? O1 C6 C7 C9 1.3(4) . . . . ? C5 C6 C7 C9 -178.6(2) . . . . ? O1 C6 C7 S1 -178.5(2) . . . . ? C5 C6 C7 S1 1.5(3) . . . . ? C2 C1 C8 C5 0.1(4) . . . . ? C2 C1 C8 S1 178.7(2) . . . . ? C4 C5 C8 C1 0.1(4) . . . . ? C6 C5 C8 C1 179.2(2) . . . . ? C4 C5 C8 S1 -178.75(19) . . . . ? C6 C5 C8 S1 0.4(3) . . . . ? C6 C7 C9 O2 -2.9(4) . . . . ? S1 C7 C9 O2 176.9(2) . . . . ? C6 C7 C9 C10 177.2(2) . . . . ? S1 C7 C9 C10 -3.0(4) . . . . ? O2 C9 C10 C11 7.3(4) . . . . ? C7 C9 C10 C11 -172.8(2) . . . . ? C9 C10 C11 C12 68.1(3) . . . . ? C9 C10 C11 C14 -168.5(2) . . . . ? C10 C11 C12 C13 177.3(2) . . . . ? C14 C11 C12 C13 54.5(3) . . . . ? C11 C12 C13 O4 -118.1(3) . . . . ? C11 C12 C13 O3 60.5(4) . . . . ? C1 C8 S1 C7 -178.3(2) . . . . ? C5 C8 S1 C7 0.42(19) . . . . ? C6 C7 S1 C8 -1.1(2) . . . . ? C9 C7 S1 C8 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 O1 H1X O2 0.86(4) 1.82(4) 2.619(3) 153(4) . O3 H3X O4 0.88(5) 1.75(5) 2.626(3) 173(5) 3_546 _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.344 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.050 #===END data_272b _database_code_depnum_ccdc_archive 'CCDC 735540' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 O4 S' _chemical_formula_sum 'C14 H12 O4 S' _chemical_formula_weight 276.30 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)/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 7.2014(9) _cell_length_b 9.5258(12) _cell_length_c 18.552(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.133(4) _cell_angle_gamma 90.00 _cell_volume 1271.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1217 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 19.98 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9376 _exptl_absorpt_correction_T_max 0.9496 _exptl_absorpt_process_details 'SADABS (BRUKER,1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ApexII 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 7891 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_sigmaI/netI 0.0966 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.98 _reflns_number_total 2682 _reflns_number_gt 1200 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction 'SAINT PLUS ,Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0445P)^2^+1.0318P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2682 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1552 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1460 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3044(5) -0.1633(4) 0.9453(2) 0.0442(10) Uani 1 1 d . . . C2 C 0.3176(6) -0.3094(4) 0.9518(3) 0.0609(12) Uani 1 1 d . . . H2 H 0.3487 -0.3651 0.9129 0.073 Uiso 1 1 calc R . . C3 C 0.2831(6) -0.3675(5) 1.0175(3) 0.0732(14) Uani 1 1 d . . . H3 H 0.2910 -0.4644 1.0228 0.088 Uiso 1 1 calc R . . C4 C 0.2366(6) -0.2862(5) 1.0765(3) 0.0681(13) Uani 1 1 d . . . H4 H 0.2176 -0.3290 1.1207 0.082 Uiso 1 1 calc R . . C5 C 0.2187(5) -0.1433(5) 1.0699(2) 0.0542(11) Uani 1 1 d . . . H5 H 0.1847 -0.0890 1.1089 0.065 Uiso 1 1 calc R . . C6 C 0.2525(5) -0.0806(4) 1.0033(2) 0.0412(9) Uani 1 1 d . . . C7 C 0.2448(5) 0.0630(4) 0.9848(2) 0.0430(10) Uani 1 1 d . . . C8 C 0.2906(5) 0.0900(4) 0.9145(2) 0.0405(10) Uani 1 1 d . . . C9 C 0.2939(5) 0.2279(4) 0.8842(2) 0.0448(10) Uani 1 1 d . . . C10 C 0.3469(5) 0.2457(4) 0.8067(2) 0.0427(10) Uani 1 1 d . . . H10 H 0.4498 0.1827 0.7958 0.051 Uiso 1 1 calc R . . C11 C 0.2527(5) 0.4617(4) 0.7643(2) 0.0493(11) Uani 1 1 d . . . C12 C 0.0968(5) 0.3645(4) 0.7473(3) 0.0631(13) Uani 1 1 d . . . H12A H 0.0481 0.3793 0.6984 0.076 Uiso 1 1 calc R . . H12B H -0.0027 0.3782 0.7804 0.076 Uiso 1 1 calc R . . C13 C 0.1791(5) 0.2172(4) 0.7555(2) 0.0485(11) Uani 1 1 d . . . H13 H 0.0908 0.1552 0.7788 0.058 Uiso 1 1 calc R . . C14 C 0.2367(6) 0.1536(5) 0.6852(2) 0.0702(13) Uani 1 1 d . . . H14A H 0.3192 0.2167 0.6619 0.105 Uiso 1 1 calc R . . H14B H 0.1285 0.1377 0.6545 0.105 Uiso 1 1 calc R . . H14C H 0.2989 0.0660 0.6946 0.105 Uiso 1 1 calc R . . O1 O 0.1963(4) 0.1612(4) 1.03162(17) 0.0585(9) Uani 1 1 d . . . O2 O 0.2484(4) 0.3314(3) 0.92040(16) 0.0634(8) Uani 1 1 d . . . O3 O 0.3981(3) 0.3896(3) 0.79390(15) 0.0547(8) Uani 1 1 d . . . O4 O 0.2641(4) 0.5849(3) 0.75365(17) 0.0686(9) Uani 1 1 d . . . S1 S 0.34601(14) -0.06404(11) 0.86916(6) 0.0484(3) Uani 1 1 d . . . H1X H 0.203(7) 0.237(6) 1.006(3) 0.11(2) 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 C1 0.038(2) 0.053(3) 0.042(3) 0.003(2) -0.0014(18) -0.0024(19) C2 0.066(3) 0.050(3) 0.066(3) 0.003(2) 0.003(2) -0.001(2) C3 0.075(3) 0.056(3) 0.088(4) 0.021(3) 0.005(3) -0.003(2) C4 0.068(3) 0.078(4) 0.059(3) 0.026(3) 0.005(2) -0.001(3) C5 0.041(2) 0.075(3) 0.046(3) 0.002(3) 0.0022(19) -0.004(2) C6 0.032(2) 0.054(3) 0.037(3) 0.003(2) -0.0026(17) -0.0021(18) C7 0.035(2) 0.054(3) 0.040(3) -0.006(2) -0.0046(18) 0.000(2) C8 0.037(2) 0.044(2) 0.040(3) -0.0015(19) 0.0014(18) 0.0025(17) C9 0.036(2) 0.047(2) 0.051(3) -0.003(2) -0.0030(19) -0.0003(18) C10 0.040(2) 0.044(2) 0.045(3) 0.0081(19) 0.0013(19) -0.0024(17) C11 0.047(2) 0.050(3) 0.051(3) 0.007(2) 0.007(2) 0.004(2) C12 0.043(2) 0.061(3) 0.085(4) 0.017(3) -0.007(2) -0.002(2) C13 0.043(2) 0.051(2) 0.051(3) 0.011(2) -0.007(2) -0.0069(19) C14 0.085(3) 0.075(3) 0.050(3) -0.004(3) 0.002(2) -0.006(3) O1 0.0637(19) 0.065(2) 0.047(2) -0.0135(19) 0.0037(15) 0.0060(17) O2 0.071(2) 0.0503(18) 0.070(2) -0.0060(17) 0.0071(15) -0.0001(15) O3 0.0392(15) 0.0534(17) 0.071(2) 0.0136(15) -0.0037(14) -0.0094(13) O4 0.078(2) 0.0478(19) 0.081(2) 0.0132(17) 0.0085(17) -0.0025(16) S1 0.0563(6) 0.0495(6) 0.0394(7) -0.0007(5) 0.0030(5) 0.0049(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.397(5) . ? C1 C2 1.400(5) . ? C1 S1 1.735(4) . ? C2 C3 1.369(6) . ? C2 H2 0.9300 . ? C3 C4 1.393(6) . ? C3 H3 0.9300 . ? C4 C5 1.373(6) . ? C4 H4 0.9300 . ? C5 C6 1.401(5) . ? C5 H5 0.9300 . ? C6 C7 1.411(5) . ? C7 O1 1.332(5) . ? C7 C8 1.381(5) . ? C8 C9 1.430(5) . ? C8 S1 1.745(4) . ? C9 O2 1.244(4) . ? C9 C10 1.510(5) . ? C10 O3 1.442(4) . ? C10 C13 1.534(5) . ? C10 H10 0.9800 . ? C11 O4 1.193(4) . ? C11 O3 1.352(4) . ? C11 C12 1.480(5) . ? C12 C13 1.528(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.510(5) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O1 H1X 0.86(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.9(4) . . ? C6 C1 S1 112.3(3) . . ? C2 C1 S1 126.8(3) . . ? C3 C2 C1 117.7(4) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 122.2(4) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C5 C4 C3 120.3(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 118.9(4) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C1 C6 C5 120.0(4) . . ? C1 C6 C7 111.6(4) . . ? C5 C6 C7 128.4(4) . . ? O1 C7 C8 124.2(4) . . ? O1 C7 C6 122.0(4) . . ? C8 C7 C6 113.7(4) . . ? C7 C8 C9 123.4(4) . . ? C7 C8 S1 111.4(3) . . ? C9 C8 S1 125.1(3) . . ? O2 C9 C8 120.5(4) . . ? O2 C9 C10 120.4(4) . . ? C8 C9 C10 119.1(4) . . ? O3 C10 C9 109.8(3) . . ? O3 C10 C13 105.4(3) . . ? C9 C10 C13 110.4(3) . . ? O3 C10 H10 110.4 . . ? C9 C10 H10 110.4 . . ? C13 C10 H10 110.4 . . ? O4 C11 O3 120.7(4) . . ? O4 C11 C12 129.5(4) . . ? O3 C11 C12 109.8(3) . . ? C11 C12 C13 105.4(3) . . ? C11 C12 H12A 110.7 . . ? C13 C12 H12A 110.7 . . ? C11 C12 H12B 110.7 . . ? C13 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C14 C13 C12 113.6(4) . . ? C14 C13 C10 111.7(3) . . ? C12 C13 C10 101.2(3) . . ? C14 C13 H13 110.0 . . ? C12 C13 H13 110.0 . . ? C10 C13 H13 110.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 O1 H1X 102(4) . . ? C11 O3 C10 110.6(3) . . ? C1 S1 C8 90.93(19) . . ? 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 C6 C1 C2 C3 -1.8(6) . . . . ? S1 C1 C2 C3 178.5(3) . . . . ? C1 C2 C3 C4 -0.1(7) . . . . ? C2 C3 C4 C5 1.8(7) . . . . ? C3 C4 C5 C6 -1.6(6) . . . . ? C2 C1 C6 C5 2.1(5) . . . . ? S1 C1 C6 C5 -178.2(3) . . . . ? C2 C1 C6 C7 -179.0(3) . . . . ? S1 C1 C6 C7 0.8(4) . . . . ? C4 C5 C6 C1 -0.3(6) . . . . ? C4 C5 C6 C7 -179.1(4) . . . . ? C1 C6 C7 O1 179.3(3) . . . . ? C5 C6 C7 O1 -1.9(6) . . . . ? C1 C6 C7 C8 -0.3(4) . . . . ? C5 C6 C7 C8 178.5(3) . . . . ? O1 C7 C8 C9 1.0(6) . . . . ? C6 C7 C8 C9 -179.4(3) . . . . ? O1 C7 C8 S1 -179.8(3) . . . . ? C6 C7 C8 S1 -0.3(4) . . . . ? C7 C8 C9 O2 -2.4(6) . . . . ? S1 C8 C9 O2 178.6(3) . . . . ? C7 C8 C9 C10 179.7(3) . . . . ? S1 C8 C9 C10 0.7(5) . . . . ? O2 C9 C10 O3 20.1(5) . . . . ? C8 C9 C10 O3 -162.0(3) . . . . ? O2 C9 C10 C13 -95.7(4) . . . . ? C8 C9 C10 C13 82.1(4) . . . . ? O4 C11 C12 C13 166.1(4) . . . . ? O3 C11 C12 C13 -11.8(5) . . . . ? C11 C12 C13 C14 -96.4(4) . . . . ? C11 C12 C13 C10 23.5(4) . . . . ? O3 C10 C13 C14 93.9(4) . . . . ? C9 C10 C13 C14 -147.6(3) . . . . ? O3 C10 C13 C12 -27.3(4) . . . . ? C9 C10 C13 C12 91.2(4) . . . . ? O4 C11 O3 C10 175.4(4) . . . . ? C12 C11 O3 C10 -6.5(4) . . . . ? C9 C10 O3 C11 -96.9(3) . . . . ? C13 C10 O3 C11 22.1(4) . . . . ? C6 C1 S1 C8 -0.8(3) . . . . ? C2 C1 S1 C8 179.0(4) . . . . ? C7 C8 S1 C1 0.6(3) . . . . ? C9 C8 S1 C1 179.7(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 H1X O2 0.86(5) 1.87(5) 2.662(5) 152(5) . _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.915 _refine_diff_density_max 0.217 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.057 _vrf_PLAT029_272b ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: The crytal size was small even after several attempts of recrystallisation.Even though the data was collected up to 0.75 \%A resolution, the crystal (the largest available) still diffracted quite weakly at high angle ; # end Validation Reply Form #===END data_new _database_code_depnum_ccdc_archive 'CCDC 738524' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 O4 S' _chemical_formula_sum 'C14 H12 O4 S' _chemical_formula_weight 276.30 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)/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 10.3417(4) _cell_length_b 9.8285(4) _cell_length_c 12.6105(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.270(2) _cell_angle_gamma 90.00 _cell_volume 1281.46(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3412 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 28.23 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9079 _exptl_absorpt_correction_T_max 0.9380 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 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 9635 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 29.88 _reflns_number_total 3643 _reflns_number_gt 2348 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II,Bruker,2004' _computing_cell_refinement 'APEX II,Bruker,2004' _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1000P)^2^+1.0192P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3643 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1470 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 0.691 _refine_ls_restrained_S_all 0.691 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.01906(18) 0.15706(19) 0.59490(15) 0.0497(4) Uani 1 1 d . . . C2 C 1.1387(2) 0.1742(2) 0.64705(19) 0.0631(6) Uani 1 1 d . . . H2 H 1.1988 0.2367 0.6227 0.076 Uiso 1 1 calc R . . C3 C 1.1650(2) 0.0964(3) 0.7351(2) 0.0721(7) Uani 1 1 d . . . H3 H 1.2436 0.1076 0.7713 0.086 Uiso 1 1 calc R . . C4 C 1.0776(2) 0.0016(3) 0.77166(18) 0.0707(7) Uani 1 1 d . . . H4 H 1.0984 -0.0496 0.8316 0.085 Uiso 1 1 calc R . . C5 C 0.9612(2) -0.0174(2) 0.72057(16) 0.0605(5) Uani 1 1 d . . . H5 H 0.9033 -0.0821 0.7449 0.073 Uiso 1 1 calc R . . C6 C 0.93002(18) 0.06158(19) 0.63113(14) 0.0489(4) Uani 1 1 d . . . C7 C 0.81551(18) 0.06072(19) 0.56572(15) 0.0473(4) Uani 1 1 d . . . C8 C 0.81817(18) 0.15275(19) 0.48370(15) 0.0469(4) Uani 1 1 d . . . C9 C 0.71339(19) 0.16743(19) 0.40740(15) 0.0490(4) Uani 1 1 d . . . C10 C 0.72415(19) 0.2726(2) 0.31994(14) 0.0490(4) Uani 1 1 d . . . H10 H 0.8152 0.2879 0.3035 0.059 Uiso 1 1 calc R . . C11 C 0.5349(2) 0.2784(2) 0.22247(18) 0.0624(6) Uani 1 1 d . . . C12 C 0.5207(2) 0.3807(2) 0.30953(18) 0.0596(5) Uani 1 1 d . . . H12A H 0.4700 0.3438 0.3666 0.071 Uiso 1 1 calc R . . H12B H 0.4794 0.4629 0.2831 0.071 Uiso 1 1 calc R . . C13 C 0.65804(18) 0.40897(19) 0.34687(14) 0.0481(4) Uani 1 1 d . . . H13 H 0.6933 0.4785 0.3000 0.058 Uiso 1 1 calc R . . C14 C 0.6755(2) 0.4595(2) 0.45960(16) 0.0580(5) Uani 1 1 d . . . H14A H 0.6329 0.5456 0.4669 0.087 Uiso 1 1 calc R . . H14B H 0.7661 0.4699 0.4760 0.087 Uiso 1 1 calc R . . H14C H 0.6387 0.3949 0.5075 0.087 Uiso 1 1 calc R . . O1 O 0.71812(16) -0.02423(17) 0.58522(14) 0.0657(4) Uani 1 1 d . . . O2 O 0.61510(14) 0.09773(16) 0.41438(12) 0.0635(4) Uani 1 1 d . . . O3 O 0.65474(15) 0.22351(15) 0.22764(11) 0.0611(4) Uani 1 1 d . . . O4 O 0.4590(2) 0.24326(19) 0.15512(17) 0.0945(7) Uani 1 1 d . . . S1 S 0.96328(5) 0.24399(5) 0.48352(4) 0.05439(17) Uani 1 1 d . . . H1X H 0.662(3) -0.016(3) 0.537(2) 0.086(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 C1 0.0517(10) 0.0450(9) 0.0522(10) -0.0061(8) -0.0032(8) 0.0123(8) C2 0.0555(11) 0.0611(13) 0.0722(14) -0.0121(11) -0.0096(10) 0.0090(10) C3 0.0630(13) 0.0794(16) 0.0727(15) -0.0172(13) -0.0213(11) 0.0219(12) C4 0.0785(15) 0.0780(16) 0.0548(12) 0.0001(11) -0.0153(10) 0.0317(13) C5 0.0669(12) 0.0619(12) 0.0526(11) 0.0071(9) 0.0006(9) 0.0198(10) C6 0.0532(10) 0.0482(10) 0.0451(9) -0.0012(8) -0.0016(7) 0.0143(8) C7 0.0501(10) 0.0440(9) 0.0478(9) 0.0006(8) 0.0002(7) 0.0087(7) C8 0.0495(9) 0.0444(9) 0.0468(9) 0.0004(7) -0.0027(7) 0.0095(7) C9 0.0542(10) 0.0447(10) 0.0480(10) -0.0044(8) -0.0038(8) 0.0126(8) C10 0.0536(10) 0.0512(10) 0.0418(9) -0.0011(8) -0.0048(7) 0.0128(8) C11 0.0716(14) 0.0520(11) 0.0629(13) -0.0087(10) -0.0183(10) 0.0101(10) C12 0.0536(11) 0.0529(11) 0.0716(13) -0.0141(10) -0.0122(9) 0.0139(9) C13 0.0544(10) 0.0420(9) 0.0476(10) 0.0003(7) -0.0041(8) 0.0082(7) C14 0.0694(13) 0.0518(11) 0.0525(11) -0.0097(9) -0.0054(9) 0.0101(9) O1 0.0596(9) 0.0675(10) 0.0698(10) 0.0172(8) -0.0068(7) -0.0060(7) O2 0.0591(9) 0.0597(9) 0.0711(10) 0.0045(7) -0.0106(7) 0.0007(7) O3 0.0778(10) 0.0606(9) 0.0442(7) -0.0103(6) -0.0112(6) 0.0221(7) O4 0.0980(14) 0.0821(13) 0.1012(14) -0.0319(10) -0.0506(12) 0.0166(10) S1 0.0562(3) 0.0489(3) 0.0579(3) 0.0050(2) -0.0019(2) 0.0037(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 C1 C6 1.399(3) . ? C1 C2 1.399(3) . ? C1 S1 1.732(2) . ? C2 C3 1.371(3) . ? C2 H2 0.9300 . ? C3 C4 1.384(4) . ? C3 H3 0.9300 . ? C4 C5 1.366(3) . ? C4 H4 0.9300 . ? C5 C6 1.401(3) . ? C5 H5 0.9300 . ? C6 C7 1.428(3) . ? C7 O1 1.335(2) . ? C7 C8 1.375(3) . ? C8 C9 1.440(3) . ? C8 S1 1.748(2) . ? C9 O2 1.230(2) . ? C9 C10 1.517(3) . ? C10 O3 1.437(2) . ? C10 C13 1.546(2) . ? C10 H10 0.9800 . ? C11 O4 1.194(3) . ? C11 O3 1.352(3) . ? C11 C12 1.498(3) . ? C12 C13 1.512(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.513(3) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O1 H1X 0.84(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 C6 C1 C2 120.63(19) . . ? C6 C1 S1 112.71(14) . . ? C2 C1 S1 126.66(17) . . ? C3 C2 C1 118.1(2) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 121.8(2) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 120.7(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C1 C6 C5 119.57(19) . . ? C1 C6 C7 111.03(16) . . ? C5 C6 C7 129.4(2) . . ? O1 C7 C8 125.29(17) . . ? O1 C7 C6 121.10(17) . . ? C8 C7 C6 113.61(17) . . ? C7 C8 C9 122.76(18) . . ? C7 C8 S1 111.71(14) . . ? C9 C8 S1 125.52(15) . . ? O2 C9 C8 120.46(18) . . ? O2 C9 C10 120.34(17) . . ? C8 C9 C10 119.18(18) . . ? O3 C10 C9 108.47(16) . . ? O3 C10 C13 104.68(14) . . ? C9 C10 C13 113.02(15) . . ? O3 C10 H10 110.2 . . ? C9 C10 H10 110.2 . . ? C13 C10 H10 110.2 . . ? O4 C11 O3 120.4(2) . . ? O4 C11 C12 129.9(2) . . ? O3 C11 C12 109.70(17) . . ? C11 C12 C13 104.19(17) . . ? C11 C12 H12A 110.9 . . ? C13 C12 H12A 110.9 . . ? C11 C12 H12B 110.9 . . ? C13 C12 H12B 110.9 . . ? H12A C12 H12B 108.9 . . ? C12 C13 C14 116.42(17) . . ? C12 C13 C10 100.89(15) . . ? C14 C13 C10 116.53(15) . . ? C12 C13 H13 107.5 . . ? C14 C13 H13 107.5 . . ? C10 C13 H13 107.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 O1 H1X 109(2) . . ? C11 O3 C10 110.24(15) . . ? C1 S1 C8 90.94(9) . . ? 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 C6 C1 C2 C3 -0.9(3) . . . . ? S1 C1 C2 C3 179.36(16) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 0.0(4) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? S1 C1 C6 C5 179.78(15) . . . . ? C2 C1 C6 C7 -179.56(17) . . . . ? S1 C1 C6 C7 0.2(2) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? C4 C5 C6 C7 -179.6(2) . . . . ? C1 C6 C7 O1 179.16(17) . . . . ? C5 C6 C7 O1 -0.4(3) . . . . ? C1 C6 C7 C8 -0.3(2) . . . . ? C5 C6 C7 C8 -179.87(19) . . . . ? O1 C7 C8 C9 -0.3(3) . . . . ? C6 C7 C8 C9 179.15(16) . . . . ? O1 C7 C8 S1 -179.15(16) . . . . ? C6 C7 C8 S1 0.3(2) . . . . ? C7 C8 C9 O2 1.1(3) . . . . ? S1 C8 C9 O2 179.75(15) . . . . ? C7 C8 C9 C10 179.48(17) . . . . ? S1 C8 C9 C10 -1.9(2) . . . . ? O2 C9 C10 O3 -32.9(2) . . . . ? C8 C9 C10 O3 148.73(16) . . . . ? O2 C9 C10 C13 82.7(2) . . . . ? C8 C9 C10 C13 -95.7(2) . . . . ? O4 C11 C12 C13 -164.1(3) . . . . ? O3 C11 C12 C13 15.9(3) . . . . ? C11 C12 C13 C14 -155.19(18) . . . . ? C11 C12 C13 C10 -28.1(2) . . . . ? O3 C10 C13 C12 31.4(2) . . . . ? C9 C10 C13 C12 -86.42(19) . . . . ? O3 C10 C13 C14 158.46(17) . . . . ? C9 C10 C13 C14 40.6(2) . . . . ? O4 C11 O3 C10 -175.0(2) . . . . ? C12 C11 O3 C10 5.0(3) . . . . ? C9 C10 O3 C11 97.45(19) . . . . ? C13 C10 O3 C11 -23.5(2) . . . . ? C6 C1 S1 C8 -0.02(14) . . . . ? C2 C1 S1 C8 179.72(18) . . . . ? C7 C8 S1 C1 -0.17(14) . . . . ? C9 C8 S1 C1 -178.96(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 O1 H1X O2 0.84(3) 1.96(3) 2.667(2) 142(3) . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.205 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.040