data_dmmdb _audit_creation_method SHELXL-97 _publ_contact_author_name 'Tanmaya Pathak' _publ_contact_author_address 'Department of Chemistry, IIT, Kharagpur 721 302, India' _publ_contact_author_email tpathak@chem.iitkgp.ernet.in loop_ _publ_author_name 'Indrajit Das' 'Tarun K. Pal' 'Cheravakkattu G. Suresh' 'Tanmaya Pathak' _publ_requested_journal 'Journal of Organic Chemistry' _compound_number '17c' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H34 O10 S' _chemical_formula_sum 'C28 H34 O10 S' _chemical_formula_weight 562.61 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.926 _cell_length_b 13.267 _cell_length_c 14.196 _cell_angle_alpha 90.00 _cell_angle_beta 90.08 _cell_angle_gamma 90.00 _cell_volume 1492.6 _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2923 _cell_measurement_theta_min 1.43 _cell_measurement_theta_max 26.38 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CAD4' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 25 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '60 sec' _diffrn_standards_decay_% ? _diffrn_reflns_number 2923 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 26.38 _reflns_number_total 2731 _reflns_number_gt 2129 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXL-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _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^)+(0.1541P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(16) _refine_ls_number_reflns 2731 _refine_ls_number_parameters 352 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1689 _refine_ls_wR_factor_gt 0.1432 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.863 _refine_ls_shift/su_max 0.774 _refine_ls_shift/su_mean 0.105 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 0.65659(15) 0.37943(10) 0.36511(10) 0.0524(4) Uani 1 1 d . . . O1 O 0.3075(5) 0.1678(3) 0.4478(2) 0.0499(9) Uani 1 1 d . . . O8 O 0.0481(5) 0.2480(4) 0.6065(3) 0.0688(11) Uani 1 1 d . . . O4 O 0.1650(5) 0.2655(3) 0.2167(3) 0.0512(9) Uani 1 1 d . . . O5 O 0.7957(5) 0.4252(3) 0.4141(4) 0.0703(12) Uani 1 1 d . . . O10 O 0.2353(5) 0.5174(3) 0.4732(3) 0.0659(11) Uani 1 1 d . . . O3 O 0.2677(6) 0.0797(3) 0.2233(3) 0.0649(11) Uani 1 1 d . . . O2 O 0.4018(5) 0.0334(3) 0.3661(3) 0.0646(11) Uani 1 1 d . . . O7 O 0.3175(5) 0.2805(3) 0.6425(3) 0.0626(11) Uani 1 1 d . . . O6 O 0.6893(5) 0.2927(3) 0.3127(3) 0.0705(12) Uani 1 1 d . . . O9 O 0.1345(7) 0.4732(4) 0.6227(4) 0.0809(14) Uani 1 1 d . . . C16 C 0.1850(6) 0.3545(4) 0.4985(4) 0.0450(11) Uani 1 1 d . . . H16 H 0.0738 0.3423 0.4705 0.054 Uiso 1 1 calc R . . C3 C 0.1539(6) 0.2185(4) 0.3081(3) 0.0416(11) Uani 1 1 d . . . H3 H 0.0507 0.2397 0.3405 0.050 Uiso 1 1 calc R . . C21 C 0.5011(6) 0.3589(4) 0.4595(4) 0.0466(12) Uani 1 1 d . . . H21A H 0.5369 0.3026 0.4982 0.056 Uiso 1 1 calc R . . H21B H 0.4961 0.4183 0.4993 0.056 Uiso 1 1 calc R . . C1 C 0.2588(7) 0.0830(4) 0.3991(4) 0.0525(12) Uani 1 1 d . . . H1 H 0.1908 0.0384 0.4389 0.063 Uiso 1 1 calc R . . C5 C 0.3214(6) 0.3367(4) 0.4185(4) 0.0420(11) Uani 1 1 d . . . H5 H 0.3005 0.3880 0.3702 0.050 Uiso 1 1 calc R . . C4 C 0.3114(6) 0.2393(4) 0.3711(4) 0.0417(11) Uani 1 1 d . . . H4 H 0.4140 0.2287 0.3340 0.050 Uiso 1 1 calc R . . C2 C 0.1625(7) 0.1085(4) 0.3028(4) 0.0480(12) Uani 1 1 d . . . H2 H 0.0504 0.0775 0.2999 0.058 Uiso 1 1 calc R . . C22 C 0.5619(7) 0.4582(4) 0.2777(4) 0.0540(13) Uani 1 1 d . . . C27 C 0.4907(9) 0.4257(5) 0.1903(5) 0.0683(17) Uani 1 1 d . . . H27 H 0.4952 0.3572 0.1766 0.082 Uiso 1 1 calc R . . C17 C 0.1966(7) 0.2893(4) 0.5903(4) 0.0489(12) Uani 1 1 d . . . C19 C 0.1817(7) 0.4551(4) 0.5399(4) 0.0524(14) Uani 1 1 d . . . C10 C 0.0378(8) 0.3143(5) 0.0639(4) 0.0648(16) Uani 1 1 d . . . C9 C 0.0244(8) 0.2484(5) 0.1510(4) 0.0655(16) Uani 1 1 d . . . H9A H -0.0813 0.2626 0.1828 0.079 Uiso 1 1 calc R . . H9B H 0.0234 0.1782 0.1321 0.079 Uiso 1 1 calc R . . C23 C 0.5549(9) 0.5548(4) 0.3016(5) 0.0667(17) Uani 1 1 d . . . H23 H 0.5979 0.5799 0.3579 0.080 Uiso 1 1 calc R . . C6 C 0.3850(9) 0.0131(5) 0.2616(5) 0.0710(18) Uani 1 1 d . . . C26 C 0.4156(11) 0.4882(6) 0.1248(5) 0.084(2) Uani 1 1 d . . . H26 H 0.3719 0.4634 0.0686 0.101 Uiso 1 1 calc R . . C20 C 0.2444(10) 0.6160(5) 0.5071(7) 0.087(2) Uani 1 1 d . . . H20A H 0.2844 0.6597 0.4580 0.130 Uiso 1 1 calc R . . H20B H 0.3208 0.6186 0.5596 0.130 Uiso 1 1 calc R . . H20C H 0.1345 0.6375 0.5269 0.130 Uiso 1 1 calc R . . C25 C 0.4090(10) 0.5847(6) 0.1460(6) 0.0803(19) Uani 1 1 d . . . C24 C 0.4775(11) 0.6142(6) 0.2347(6) 0.084(2) Uani 1 1 d . . . H24 H 0.4688 0.6823 0.2493 0.101 Uiso 1 1 calc R . . C18 C 0.0399(11) 0.1841(7) 0.6924(6) 0.096(3) Uani 1 1 d . . . H18A H -0.0721 0.1575 0.6992 0.143 Uiso 1 1 calc R . . H18B H 0.0675 0.2240 0.7467 0.143 Uiso 1 1 calc R . . H18C H 0.1188 0.1296 0.6869 0.143 Uiso 1 1 calc R . . C15 C 0.1436(12) 0.2917(8) -0.0144(6) 0.104(3) Uani 1 1 d . . . H15 H 0.2075 0.2330 -0.0121 0.125 Uiso 1 1 calc R . . C11 C -0.0538(12) 0.3951(8) 0.0578(9) 0.118(3) Uani 1 1 d . . . H11 H -0.1278 0.4117 0.1061 0.142 Uiso 1 1 calc R . . C13 C 0.0599(19) 0.4363(16) -0.0939(12) 0.151(7) Uani 1 1 d . . . H13 H 0.0631 0.4803 -0.1449 0.181 Uiso 1 1 calc R . . C28 C 0.3247(17) 0.6534(9) 0.0721(7) 0.132(4) Uani 1 1 d . . . H28A H 0.3285 0.7220 0.0933 0.197 Uiso 1 1 calc R . . H28B H 0.2093 0.6332 0.0635 0.197 Uiso 1 1 calc R . . H28C H 0.3837 0.6477 0.0133 0.197 Uiso 1 1 calc R . . C8 C 0.3176(17) -0.0873(6) 0.2504(9) 0.141(5) Uani 1 1 d . . . H8A H 0.3954 -0.1353 0.2763 0.211 Uiso 1 1 calc R . . H8B H 0.3009 -0.1010 0.1846 0.211 Uiso 1 1 calc R . . H8C H 0.2116 -0.0921 0.2828 0.211 Uiso 1 1 calc R . . C7 C 0.5495(13) 0.0296(11) 0.2115(7) 0.126(4) Uani 1 1 d . . . H7A H 0.5864 0.0978 0.2212 0.189 Uiso 1 1 calc R . . H7B H 0.5346 0.0176 0.1453 0.189 Uiso 1 1 calc R . . H7C H 0.6327 -0.0160 0.2360 0.189 Uiso 1 1 calc R . . C14 C 0.1574(19) 0.3541(12) -0.0965(7) 0.136(5) Uani 1 1 d . . . H14 H 0.2278 0.3388 -0.1469 0.163 Uiso 1 1 calc R . . C12 C -0.0412(19) 0.4583(12) -0.0225(16) 0.179(8) Uani 1 1 d . . . H12 H -0.1057 0.5168 -0.0251 0.215 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 0.0426(6) 0.0378(6) 0.0770(9) -0.0085(7) 0.0058(5) -0.0002(6) O1 0.068(2) 0.0291(17) 0.052(2) -0.0002(16) -0.0098(17) 0.0037(16) O8 0.066(3) 0.060(3) 0.080(3) 0.009(2) 0.007(2) -0.015(2) O4 0.059(2) 0.0371(19) 0.057(2) 0.0106(17) -0.0087(16) -0.0079(16) O5 0.0408(19) 0.062(3) 0.108(3) -0.009(3) -0.003(2) -0.0034(19) O10 0.071(2) 0.0323(19) 0.094(3) -0.009(2) -0.002(2) 0.0126(19) O3 0.088(3) 0.045(2) 0.062(2) -0.003(2) -0.011(2) 0.012(2) O2 0.079(3) 0.038(2) 0.077(3) -0.008(2) -0.015(2) 0.011(2) O7 0.067(3) 0.049(2) 0.071(3) 0.005(2) -0.010(2) -0.0017(19) O6 0.062(2) 0.046(2) 0.104(3) -0.020(2) 0.023(2) 0.0069(19) O9 0.102(4) 0.050(3) 0.090(3) -0.016(2) 0.024(3) 0.018(2) C16 0.040(2) 0.036(3) 0.059(3) -0.004(2) 0.000(2) 0.0057(19) C3 0.046(3) 0.030(2) 0.048(3) 0.000(2) 0.000(2) -0.0010(19) C21 0.044(2) 0.034(3) 0.061(3) -0.009(2) 0.001(2) 0.005(2) C1 0.064(3) 0.032(2) 0.062(3) 0.003(3) -0.002(2) -0.004(2) C5 0.040(2) 0.030(2) 0.056(3) 0.002(2) -0.001(2) 0.0043(19) C4 0.045(3) 0.031(2) 0.049(3) -0.004(2) 0.001(2) 0.000(2) C2 0.052(3) 0.032(2) 0.060(3) 0.003(2) -0.006(2) -0.003(2) C22 0.057(3) 0.037(3) 0.068(3) -0.002(3) 0.006(3) -0.007(2) C27 0.086(4) 0.046(3) 0.073(4) -0.007(3) -0.001(3) -0.013(3) C17 0.054(3) 0.040(3) 0.052(3) -0.005(2) 0.001(3) -0.002(2) C19 0.047(3) 0.037(3) 0.072(4) -0.006(3) -0.003(3) 0.009(2) C10 0.063(3) 0.067(4) 0.064(4) 0.012(3) -0.014(3) -0.004(3) C9 0.065(3) 0.064(4) 0.068(4) 0.017(3) -0.016(3) -0.011(3) C23 0.077(4) 0.043(3) 0.080(4) -0.015(3) -0.010(3) -0.009(3) C6 0.089(4) 0.048(3) 0.077(4) -0.018(3) -0.022(4) 0.018(3) C26 0.114(6) 0.064(4) 0.073(4) 0.001(4) -0.021(4) -0.015(4) C20 0.095(5) 0.027(3) 0.138(7) -0.014(4) -0.011(5) 0.013(3) C25 0.099(5) 0.047(3) 0.096(5) 0.007(4) -0.009(4) -0.004(4) C24 0.105(5) 0.044(3) 0.102(5) 0.003(4) -0.019(5) 0.000(4) C18 0.099(5) 0.084(6) 0.105(5) 0.025(5) 0.018(4) -0.024(5) C15 0.110(6) 0.104(7) 0.098(6) -0.013(6) 0.029(5) -0.040(6) C11 0.093(5) 0.096(7) 0.166(9) 0.052(7) 0.005(6) 0.019(5) C13 0.112(10) 0.190(17) 0.149(11) 0.087(12) -0.057(9) -0.040(10) C28 0.173(11) 0.092(7) 0.130(7) 0.018(7) -0.046(8) 0.014(7) C8 0.199(11) 0.033(3) 0.190(11) -0.041(5) -0.101(10) 0.033(5) C7 0.101(6) 0.167(11) 0.110(6) -0.030(8) 0.010(5) 0.044(7) C14 0.158(11) 0.169(13) 0.081(6) -0.013(7) 0.027(6) -0.091(11) C12 0.116(10) 0.129(11) 0.29(2) 0.119(15) -0.041(12) 0.003(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O6 1.395(4) . ? S1 O5 1.437(4) . ? S1 C22 1.787(6) . ? S1 C21 1.842(5) . ? O1 C1 1.375(7) . ? O1 C4 1.444(6) . ? O8 C17 1.319(7) . ? O8 C18 1.487(9) . ? O4 C3 1.442(6) . ? O4 C9 1.470(7) . ? O10 C19 1.328(7) . ? O10 C20 1.395(7) . ? O3 C6 1.392(7) . ? O3 C2 1.454(7) . ? O2 C1 1.392(7) . ? O2 C6 1.514(8) . ? O7 C17 1.216(7) . ? O9 C19 1.257(7) . ? C16 C19 1.459(8) . ? C16 C17 1.566(8) . ? C16 C5 1.586(7) . ? C3 C2 1.464(7) . ? C3 C4 1.559(7) . ? C21 C5 1.565(7) . ? C1 C2 1.601(8) . ? C5 C4 1.459(7) . ? C22 C23 1.328(8) . ? C22 C27 1.428(9) . ? C27 C26 1.381(10) . ? C10 C11 1.298(12) . ? C10 C15 1.425(11) . ? C10 C9 1.517(8) . ? C23 C24 1.376(10) . ? C6 C8 1.444(12) . ? C6 C7 1.502(13) . ? C26 C25 1.316(11) . ? C25 C24 1.426(11) . ? C25 C28 1.541(12) . ? C15 C14 1.434(16) . ? C11 C12 1.418(18) . ? C13 C14 1.34(2) . ? C13 C12 1.33(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 S1 O5 117.6(3) . . ? O6 S1 C22 101.0(3) . . ? O5 S1 C22 114.2(3) . . ? O6 S1 C21 113.0(3) . . ? O5 S1 C21 103.0(2) . . ? C22 S1 C21 108.1(2) . . ? C1 O1 C4 99.5(3) . . ? C17 O8 C18 114.8(5) . . ? C3 O4 C9 117.2(4) . . ? C19 O10 C20 110.8(6) . . ? C6 O3 C2 104.3(4) . . ? C1 O2 C6 110.0(4) . . ? C19 C16 C17 99.8(4) . . ? C19 C16 C5 115.9(4) . . ? C17 C16 C5 118.3(4) . . ? O4 C3 C2 112.4(4) . . ? O4 C3 C4 113.0(4) . . ? C2 C3 C4 99.7(4) . . ? C5 C21 S1 111.5(3) . . ? O1 C1 O2 109.1(4) . . ? O1 C1 C2 112.9(4) . . ? O2 C1 C2 101.6(4) . . ? C4 C5 C21 112.7(4) . . ? C4 C5 C16 115.1(4) . . ? C21 C5 C16 109.1(4) . . ? O1 C4 C5 103.6(4) . . ? O1 C4 C3 107.3(4) . . ? C5 C4 C3 117.6(4) . . ? O3 C2 C3 109.2(4) . . ? O3 C2 C1 109.5(4) . . ? C3 C2 C1 100.8(4) . . ? C23 C22 C27 119.8(6) . . ? C23 C22 S1 113.9(5) . . ? C27 C22 S1 126.3(5) . . ? C26 C27 C22 125.0(6) . . ? O7 C17 O8 123.8(5) . . ? O7 C17 C16 127.3(5) . . ? O8 C17 C16 108.8(5) . . ? O9 C19 O10 130.0(5) . . ? O9 C19 C16 123.9(6) . . ? O10 C19 C16 106.1(5) . . ? C11 C10 C15 116.8(8) . . ? C11 C10 C9 119.4(8) . . ? C15 C10 C9 123.8(7) . . ? O4 C9 C10 112.0(5) . . ? C22 C23 C24 113.2(6) . . ? O3 C6 C8 107.2(6) . . ? O3 C6 O2 109.1(5) . . ? C8 C6 O2 107.7(8) . . ? O3 C6 C7 107.6(7) . . ? C8 C6 C7 113.8(9) . . ? O2 C6 C7 111.3(6) . . ? C25 C26 C27 116.6(7) . . ? C26 C25 C24 116.9(7) . . ? C26 C25 C28 115.9(8) . . ? C24 C25 C28 127.1(7) . . ? C23 C24 C25 128.4(7) . . ? C10 C15 C14 123.9(12) . . ? C10 C11 C12 120.2(12) . . ? C14 C13 C12 123.4(13) . . ? C13 C14 C15 113.8(12) . . ? C13 C12 C11 121.9(14) . . ? _diffrn_measured_fraction_theta_max 0.854 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.854 _refine_diff_density_max 0.223 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.057