data_ypj3006 _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_absolute_configuration ad _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 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6054(14) _cell_length_b 8.8177(14) _cell_length_c 21.769(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1651.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 999 _cell_measurement_theta_min -23.529 _cell_measurement_theta_max 23.529 _exptl_crystal_description 'rod' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type 'Empirical' _exptl_absorpt_correction_T_min 0.9590 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 Apex' _diffrn_measurement_method 'phi-omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 19380 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0310 _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 -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4007 _reflns_number_gt 3067 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3' _computing_publication_material 'Wingx publication routines (Farrugia, 1999)' _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^)+(0.1154P)^2^+0.1166P] 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 -0.03(14) _refine_ls_number_reflns 4007 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1854 _refine_ls_wR_factor_gt 0.1663 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.002 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 0.16921(13) 1.11097(16) 1.13075(4) 0.0797(4) Uani 1 1 d . . . O1 O -0.1497(3) 1.1308(4) 1.07934(12) 0.0800(8) Uani 1 1 d . . . O2 O 0.1426(4) 1.1389(4) 0.79292(12) 0.0775(8) Uani 1 1 d . . . O3 O 0.0705(3) 0.8999(4) 0.79684(9) 0.0691(7) Uani 1 1 d . . . O4 O 0.5004(4) 0.8669(6) 0.89159(13) 0.1075(14) Uani 1 1 d . . . O5 O 0.4336(3) 0.9077(4) 0.79507(10) 0.0736(8) Uani 1 1 d . . . C1 C -0.1057(4) 1.0737(4) 1.03172(14) 0.0538(7) Uani 1 1 d . . . C2 C 0.0585(3) 1.0468(3) 1.01372(12) 0.0413(6) Uani 1 1 d . . . C3 C 0.0593(3) 0.9811(3) 0.95784(12) 0.0379(5) Uani 1 1 d . . . C4 C 0.1751(3) 0.8930(3) 0.92245(11) 0.0396(6) Uani 1 1 d . . . H4 H 0.2527 0.8506 0.9506 0.048 Uiso 1 1 calc R . . C5 C 0.2584(3) 0.9886(3) 0.87189(12) 0.0437(6) Uani 1 1 d . . . H5 H 0.2830 1.0875 0.8901 0.052 Uiso 1 1 calc R . . C6 C 0.1551(4) 1.0180(4) 0.81629(13) 0.0524(7) Uani 1 1 d . . . C7 C 0.0957(5) 0.7552(5) 0.82556(15) 0.0671(10) Uani 1 1 d . . . H7A H 0.1996 0.7200 0.8158 0.081 Uiso 1 1 calc R . . H7B H 0.0224 0.6823 0.8090 0.081 Uiso 1 1 calc R . . C8 C 0.0772(4) 0.7619(3) 0.89396(14) 0.0502(7) Uani 1 1 d . . . H8 H 0.1118 0.6654 0.9116 0.060 Uiso 1 1 calc R . . C9 C -0.0938(4) 0.7915(4) 0.91384(18) 0.0600(8) Uani 1 1 d . . . H9A H -0.1646 0.7703 0.8802 0.072 Uiso 1 1 calc R . . H9B H -0.1215 0.7280 0.9485 0.072 Uiso 1 1 calc R . . C10 C -0.1009(3) 0.9576(3) 0.93142(14) 0.0449(6) Uani 1 1 d . . . H10 H -0.1146 1.0203 0.8947 0.054 Uiso 1 1 calc R . . C11 C -0.2096(4) 1.0106(4) 0.98203(17) 0.0568(8) Uani 1 1 d . . . H11A H -0.2796 1.0882 0.9668 0.068 Uiso 1 1 calc R . . H11B H -0.2707 0.9265 0.9976 0.068 Uiso 1 1 calc R . . C12 C 0.4124(4) 0.9137(5) 0.85480(14) 0.0581(8) Uani 1 1 d . . . C13 C 0.5795(4) 0.8435(5) 0.77114(19) 0.0730(10) Uani 1 1 d . . . H13A H 0.6292 0.7820 0.8024 0.088 Uiso 1 1 calc R . . H13B H 0.5583 0.7798 0.7358 0.088 Uiso 1 1 calc R . . C14 C 0.6793(6) 0.9661(7) 0.7539(4) 0.112(2) Uani 1 1 d . . . H14A H 0.6349 1.0190 0.7195 0.167 Uiso 1 1 calc R . . H14B H 0.7794 0.9269 0.7426 0.167 Uiso 1 1 calc R . . H14C H 0.6905 1.0347 0.7878 0.167 Uiso 1 1 calc R . . C15 C 0.1909(3) 1.0811(3) 1.05318(11) 0.0425(6) Uani 1 1 d . . . C16 C 0.3524(3) 1.0927(3) 1.03545(11) 0.0383(5) Uani 1 1 d U . . H16 H 0.3914 1.0799 0.9959 0.046 Uiso 1 1 calc R . . C17 C 0.4425(4) 1.1274(4) 1.08927(15) 0.0561(8) Uani 1 1 d U . . H17 H 0.5495 1.1413 1.0878 0.067 Uiso 1 1 calc R . . C18 C 0.3620(5) 1.1384(5) 1.14154(16) 0.0686(10) Uani 1 1 d . . . H18 H 0.4068 1.1587 1.1795 0.082 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 0.0773(6) 0.1213(9) 0.0406(4) -0.0174(5) 0.0063(4) -0.0077(6) O1 0.0580(14) 0.122(2) 0.0602(14) -0.0233(16) 0.0138(12) 0.0141(15) O2 0.0785(17) 0.0956(19) 0.0585(14) 0.0306(14) 0.0024(13) 0.0187(15) O3 0.0634(14) 0.107(2) 0.0366(10) -0.0006(12) -0.0163(10) -0.0031(15) O4 0.0618(16) 0.206(4) 0.0544(15) 0.010(2) -0.0051(13) 0.049(2) O5 0.0588(14) 0.115(2) 0.0470(12) 0.0011(13) 0.0077(11) 0.0299(15) C1 0.0499(17) 0.0670(19) 0.0446(15) 0.0004(14) 0.0097(12) -0.0002(15) C2 0.0457(14) 0.0421(13) 0.0361(12) 0.0036(10) 0.0053(11) -0.0017(11) C3 0.0447(14) 0.0343(11) 0.0346(12) 0.0069(10) -0.0027(11) -0.0046(10) C4 0.0462(14) 0.0442(13) 0.0285(11) 0.0006(10) -0.0064(10) 0.0034(11) C5 0.0438(14) 0.0542(15) 0.0330(12) -0.0039(12) -0.0017(11) 0.0030(12) C6 0.0466(15) 0.080(2) 0.0303(12) 0.0050(14) 0.0017(13) 0.0134(15) C7 0.068(2) 0.079(2) 0.054(2) -0.0255(17) -0.0105(16) -0.003(2) C8 0.0635(19) 0.0421(14) 0.0449(15) -0.0021(12) -0.0092(14) -0.0015(14) C9 0.0597(19) 0.0570(18) 0.063(2) -0.0024(15) -0.0032(16) -0.0193(15) C10 0.0445(15) 0.0482(14) 0.0420(14) 0.0046(11) -0.0025(12) -0.0056(12) C11 0.0406(16) 0.0674(19) 0.0625(19) 0.0047(16) 0.0057(14) -0.0058(14) C12 0.0438(15) 0.089(2) 0.0416(15) -0.0017(15) 0.0012(12) 0.0082(16) C13 0.055(2) 0.095(3) 0.069(2) 0.004(2) 0.0111(18) 0.019(2) C14 0.061(3) 0.092(3) 0.181(7) 0.020(4) 0.016(3) 0.002(2) C15 0.0533(16) 0.0452(13) 0.0288(11) -0.0022(11) 0.0024(10) 0.0025(12) C16 0.0492(14) 0.0300(11) 0.0355(11) -0.0009(10) -0.0091(10) 0.0000(10) C17 0.0599(19) 0.0574(17) 0.0509(16) -0.0039(14) -0.0178(13) -0.0021(15) C18 0.084(3) 0.079(2) 0.0422(16) -0.0111(16) -0.0163(16) 0.000(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 S1 C18 1.693(4) . ? S1 C15 1.719(3) . ? O1 C1 1.213(4) . ? O2 C6 1.186(4) . ? O3 C6 1.339(5) . ? O3 C7 1.437(5) . ? O4 C12 1.177(4) . ? O5 C12 1.314(4) . ? O5 C13 1.472(4) . ? C1 C2 1.485(4) . ? C1 C11 1.510(5) . ? C2 C3 1.347(4) . ? C2 C15 1.459(4) . ? C3 C4 1.480(4) . ? C3 C10 1.508(4) . ? C4 C8 1.559(4) . ? C4 C5 1.561(4) . ? C4 H4 0.9800 . ? C5 C6 1.524(4) . ? C5 C12 1.527(4) . ? C5 H5 0.9800 . ? C7 C8 1.499(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.556(5) . ? C8 H8 0.9800 . ? C9 C10 1.515(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.519(5) . ? C10 H10 0.9800 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 C14 1.431(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.446(4) . ? C16 C17 1.438(4) . ? C16 H16 0.9300 . ? C17 C18 1.335(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 S1 C15 92.96(16) . . ? C6 O3 C7 118.1(2) . . ? C12 O5 C13 118.9(3) . . ? O1 C1 C2 126.1(3) . . ? O1 C1 C11 125.5(3) . . ? C2 C1 C11 108.4(3) . . ? C3 C2 C15 128.1(3) . . ? C3 C2 C1 108.2(3) . . ? C15 C2 C1 123.7(2) . . ? C2 C3 C4 134.4(3) . . ? C2 C3 C10 113.5(2) . . ? C4 C3 C10 110.2(2) . . ? C3 C4 C8 103.4(2) . . ? C3 C4 C5 113.1(2) . . ? C8 C4 C5 111.6(2) . . ? C3 C4 H4 109.5 . . ? C8 C4 H4 109.5 . . ? C5 C4 H4 109.5 . . ? C6 C5 C12 112.7(2) . . ? C6 C5 C4 112.6(3) . . ? C12 C5 C4 109.6(3) . . ? C6 C5 H5 107.2 . . ? C12 C5 H5 107.2 . . ? C4 C5 H5 107.2 . . ? O2 C6 O3 121.0(3) . . ? O2 C6 C5 123.1(3) . . ? O3 C6 C5 115.8(3) . . ? O3 C7 C8 112.4(3) . . ? O3 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? O3 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C7 C8 C9 112.5(3) . . ? C7 C8 C4 111.6(3) . . ? C9 C8 C4 106.0(2) . . ? C7 C8 H8 108.9 . . ? C9 C8 H8 108.9 . . ? C4 C8 H8 108.9 . . ? C10 C9 C8 105.7(3) . . ? C10 C9 H9A 110.6 . . ? C8 C9 H9A 110.6 . . ? C10 C9 H9B 110.6 . . ? C8 C9 H9B 110.6 . . ? H9A C9 H9B 108.7 . . ? C3 C10 C9 101.1(2) . . ? C3 C10 C11 104.1(2) . . ? C9 C10 C11 120.4(3) . . ? C3 C10 H10 110.1 . . ? C9 C10 H10 110.1 . . ? C11 C10 H10 110.1 . . ? C1 C11 C10 105.6(2) . . ? C1 C11 H11A 110.6 . . ? C10 C11 H11A 110.6 . . ? C1 C11 H11B 110.6 . . ? C10 C11 H11B 110.6 . . ? H11A C11 H11B 108.8 . . ? O4 C12 O5 124.7(3) . . ? O4 C12 C5 123.0(3) . . ? O5 C12 C5 112.3(3) . . ? C14 C13 O5 108.3(4) . . ? C14 C13 H13A 110.0 . . ? O5 C13 H13A 110.0 . . ? C14 C13 H13B 110.0 . . ? O5 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? 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 . . ? C16 C15 C2 127.5(2) . . ? C16 C15 S1 110.8(2) . . ? C2 C15 S1 121.7(2) . . ? C17 C16 C15 108.4(3) . . ? C17 C16 H16 125.8 . . ? C15 C16 H16 125.8 . . ? C18 C17 C16 115.5(3) . . ? C18 C17 H17 122.2 . . ? C16 C17 H17 122.2 . . ? C17 C18 S1 112.3(3) . . ? C17 C18 H18 123.9 . . ? S1 C18 H18 123.9 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.515 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.083