# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Mysore Shashidhar' 'Mohan M. Bhadbhade' 'Rajesh G. Gonnade' 'Manoj K.' _publ_contact_author_name 'Mysore Shashidhar' _publ_contact_author_email MS.SHASHIDHAR@NCL.RES.IN _publ_section_title ; Isostructural Molecular Strings Linked via Conserved Dipolar (ether) O...C=O Short Contacts in Conformational Polymorphs of Racemic 2,4-Di-O-Acetyl-6-O-Tosyl-myo-Inositol 1,3,5-Orthoesters ; # Attachment 'CIF_KM.cif' data_1_FormI _database_code_depnum_ccdc_archive 'CCDC 706839' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4-O-TOSYL 2,6-O-DIACETYL MYO-INOSITOL 1,3,5 ORTHOFORMATE' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 O10 S' _chemical_formula_sum 'C18 H20 O10 S' _chemical_formula_weight 428.40 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 16.4270(17) _cell_length_b 6.1377(6) _cell_length_c 19.2741(19) _cell_angle_alpha 90.00 _cell_angle_beta 91.317(2) _cell_angle_gamma 90.00 _cell_volume 1942.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5893 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.18 _exptl_crystal_description REGULAR _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8748 _exptl_absorpt_correction_T_max 0.9654 _exptl_absorpt_process_details 'BRUKER SADABS' _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 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _chemical_absolute_configuration SYN _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13355 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3422 _reflns_number_gt 3062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, ORTEP3,MERCURY1.2.1' _computing_publication_material 'SHELXTL, PLATON' _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^)+(0.0525P)^2^+0.6931P] 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 3422 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.32160(3) 0.46572(10) 0.25064(2) 0.05520(17) Uani 1 1 d . . . O1 O 0.15957(9) 0.4631(2) 0.45791(7) 0.0522(3) Uani 1 1 d . . . O2 O 0.16123(8) 0.9251(2) 0.46739(6) 0.0483(3) Uani 1 1 d . . . O3 O 0.03758(8) 0.6280(2) 0.42648(7) 0.0513(3) Uani 1 1 d . . . O4 O 0.10920(7) 0.8063(2) 0.25940(6) 0.0446(3) Uani 1 1 d . . . O5 O 0.07984(8) 0.3189(2) 0.36867(7) 0.0551(4) Uani 1 1 d . . . O6 O 0.25584(7) 0.5926(2) 0.29425(6) 0.0488(3) Uani 1 1 d . . . O7 O 0.28854(10) 1.0407(3) 0.45188(8) 0.0665(4) Uani 1 1 d . . . O8 O 0.08296(9) 0.5708(3) 0.17283(7) 0.0653(4) Uani 1 1 d . . . O9 O 0.29071(10) 0.2552(3) 0.23496(9) 0.0774(5) Uani 1 1 d . . . O10 O 0.34052(10) 0.6134(3) 0.19679(7) 0.0805(5) Uani 1 1 d . . . C1 C 0.20568(11) 0.5946(3) 0.41127(9) 0.0438(4) Uani 1 1 d . . . H1 H 0.2611 0.6161 0.4300 0.053 Uiso 1 1 calc R . . C2 C 0.16330(11) 0.8138(3) 0.40178(8) 0.0400(4) Uani 1 1 d . . . H2 H 0.1915 0.9024 0.3675 0.048 Uiso 1 1 calc R . . C3 C 0.07626(10) 0.7713(3) 0.37808(9) 0.0418(4) Uani 1 1 d . . . H3 H 0.0463 0.9090 0.3747 0.050 Uiso 1 1 calc R . . C4 C 0.07485(10) 0.6567(3) 0.30781(9) 0.0426(4) Uani 1 1 d . . . H4 H 0.0183 0.6259 0.2938 0.051 Uiso 1 1 calc R . . C5 C 0.12136(11) 0.4409(3) 0.31628(9) 0.0442(4) Uani 1 1 d . . . H5 H 0.1207 0.3604 0.2724 0.053 Uiso 1 1 calc R . . C6 C 0.20813(11) 0.4701(3) 0.34333(9) 0.0429(4) Uani 1 1 d . . . H6 H 0.2332 0.3271 0.3513 0.052 Uiso 1 1 calc R . . C7 C 0.07994(13) 0.4307(3) 0.43223(11) 0.0539(5) Uani 1 1 d . . . H7 H 0.0515 0.3395 0.4657 0.065 Uiso 1 1 calc R . . C8 C 0.23062(14) 1.0275(3) 0.48764(10) 0.0510(5) Uani 1 1 d . . . C9 C 0.22417(17) 1.1149(4) 0.55958(10) 0.0688(6) Uani 1 1 d . . . H9A H 0.2507 1.0170 0.5917 0.103 Uiso 1 1 calc R . . H9B H 0.1678 1.1286 0.5710 0.103 Uiso 1 1 calc R . . H9C H 0.2498 1.2552 0.5623 0.103 Uiso 1 1 calc R . . C10 C 0.10991(11) 0.7424(4) 0.19203(9) 0.0491(5) Uani 1 1 d . . . C11 C 0.14887(15) 0.9109(4) 0.14844(11) 0.0647(6) Uani 1 1 d . . . H11A H 0.1433 0.8707 0.1004 0.097 Uiso 1 1 calc R . . H11B H 0.2056 0.9220 0.1611 0.097 Uiso 1 1 calc R . . H11C H 0.1229 1.0489 0.1556 0.097 Uiso 1 1 calc R . . C12 C 0.40489(11) 0.4439(3) 0.30851(10) 0.0501(5) Uani 1 1 d . . . C13 C 0.45915(14) 0.6144(4) 0.31503(12) 0.0662(6) Uani 1 1 d . . . H13 H 0.4522 0.7398 0.2885 0.079 Uiso 1 1 calc R . . C14 C 0.52389(15) 0.5963(5) 0.36151(14) 0.0771(7) Uani 1 1 d . . . H14 H 0.5608 0.7108 0.3658 0.092 Uiso 1 1 calc R . . C15 C 0.53530(14) 0.4132(5) 0.40175(13) 0.0708(7) Uani 1 1 d . . . C16 C 0.48071(15) 0.2461(5) 0.39434(14) 0.0754(7) Uani 1 1 d . . . H16 H 0.4876 0.1215 0.4213 0.090 Uiso 1 1 calc R . . C17 C 0.41540(13) 0.2578(4) 0.34760(12) 0.0637(6) Uani 1 1 d . . . H17 H 0.3793 0.1419 0.3427 0.076 Uiso 1 1 calc R . . C18 C 0.60708(17) 0.3961(7) 0.45208(16) 0.1050(11) Uani 1 1 d . . . H18A H 0.6559 0.3715 0.4268 0.157 Uiso 1 1 calc R . . H18B H 0.5986 0.2768 0.4833 0.157 Uiso 1 1 calc R . . H18C H 0.6122 0.5290 0.4781 0.157 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 0.0470(3) 0.0774(4) 0.0416(3) -0.0079(2) 0.0093(2) 0.0019(2) O1 0.0654(9) 0.0479(7) 0.0436(7) 0.0128(6) 0.0107(6) 0.0092(6) O2 0.0616(8) 0.0468(7) 0.0368(6) -0.0026(5) 0.0069(6) -0.0035(6) O3 0.0514(7) 0.0460(7) 0.0575(8) 0.0070(6) 0.0211(6) 0.0023(6) O4 0.0481(7) 0.0457(7) 0.0400(6) 0.0051(5) -0.0012(5) -0.0019(6) O5 0.0638(8) 0.0380(7) 0.0642(8) 0.0031(6) 0.0179(7) -0.0090(6) O6 0.0442(7) 0.0533(8) 0.0495(7) 0.0075(6) 0.0122(6) 0.0041(6) O7 0.0619(9) 0.0812(11) 0.0564(9) -0.0034(8) 0.0016(7) -0.0148(8) O8 0.0687(10) 0.0741(11) 0.0528(8) -0.0093(8) -0.0063(7) -0.0109(8) O9 0.0671(10) 0.0881(12) 0.0772(10) -0.0389(9) 0.0060(8) -0.0051(9) O10 0.0692(10) 0.1292(15) 0.0437(8) 0.0151(9) 0.0142(7) -0.0008(10) C1 0.0449(10) 0.0476(10) 0.0389(9) 0.0055(8) 0.0025(7) 0.0037(8) C2 0.0476(10) 0.0395(9) 0.0332(8) 0.0013(7) 0.0052(7) 0.0002(7) C3 0.0418(9) 0.0382(9) 0.0458(9) 0.0051(8) 0.0083(7) 0.0029(7) C4 0.0381(9) 0.0430(10) 0.0467(10) 0.0028(8) 0.0014(7) -0.0047(8) C5 0.0499(10) 0.0369(9) 0.0463(10) -0.0016(8) 0.0087(8) -0.0035(8) C6 0.0460(10) 0.0395(9) 0.0437(9) 0.0055(8) 0.0091(8) 0.0065(8) C7 0.0633(13) 0.0416(11) 0.0578(12) 0.0086(9) 0.0214(10) -0.0009(9) C8 0.0704(13) 0.0422(10) 0.0400(10) 0.0061(8) -0.0065(9) -0.0042(9) C9 0.1062(18) 0.0593(13) 0.0406(11) -0.0011(10) -0.0062(11) -0.0061(13) C10 0.0418(10) 0.0618(13) 0.0432(10) 0.0011(9) -0.0051(8) 0.0053(9) C11 0.0685(14) 0.0752(15) 0.0506(12) 0.0112(11) 0.0078(10) 0.0016(12) C12 0.0400(10) 0.0603(12) 0.0506(11) -0.0033(9) 0.0122(8) 0.0042(9) C13 0.0581(13) 0.0695(14) 0.0713(14) 0.0077(12) 0.0034(11) -0.0062(11) C14 0.0543(13) 0.0908(19) 0.0861(17) -0.0034(15) -0.0001(12) -0.0148(13) C15 0.0470(12) 0.0979(19) 0.0676(14) -0.0034(13) 0.0046(10) 0.0125(12) C16 0.0680(15) 0.0801(17) 0.0783(16) 0.0179(13) 0.0051(12) 0.0204(13) C17 0.0541(12) 0.0612(13) 0.0761(14) 0.0031(11) 0.0089(11) 0.0019(10) C18 0.0676(16) 0.156(3) 0.090(2) -0.006(2) -0.0164(14) 0.0240(19) _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 O10 1.4179(17) . ? S1 O9 1.4180(18) . ? S1 O6 1.5881(13) . ? S1 C12 1.750(2) . ? O1 C7 1.402(3) . ? O1 C1 1.437(2) . ? O2 C8 1.352(2) . ? O2 C2 1.438(2) . ? O3 C7 1.400(2) . ? O3 C3 1.440(2) . ? O4 C10 1.357(2) . ? O4 C4 1.434(2) . ? O5 C7 1.404(2) . ? O5 C5 1.441(2) . ? O6 C6 1.452(2) . ? O7 C8 1.190(3) . ? O8 C10 1.198(2) . ? C1 C6 1.517(2) . ? C1 C2 1.524(2) . ? C1 H1 0.9800 . ? C2 C3 1.514(2) . ? C2 H2 0.9800 . ? C3 C4 1.526(2) . ? C3 H3 0.9800 . ? C4 C5 1.536(2) . ? C4 H4 0.9800 . ? C5 C6 1.517(3) . ? C5 H5 0.9800 . ? C6 H6 0.9800 . ? C7 H7 0.9800 . ? C8 C9 1.493(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.487(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C17 1.377(3) . ? C12 C13 1.378(3) . ? C13 C14 1.379(3) . ? C13 H13 0.9300 . ? C14 C15 1.376(4) . ? C14 H14 0.9300 . ? C15 C16 1.368(4) . ? C15 C18 1.513(3) . ? C16 C17 1.387(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 O10 S1 O9 120.66(11) . . ? O10 S1 O6 103.71(10) . . ? O9 S1 O6 108.37(9) . . ? O10 S1 C12 109.52(10) . . ? O9 S1 C12 109.69(11) . . ? O6 S1 C12 103.38(8) . . ? C7 O1 C1 111.10(13) . . ? C8 O2 C2 115.98(14) . . ? C7 O3 C3 110.71(13) . . ? C10 O4 C4 116.74(14) . . ? C7 O5 C5 111.49(13) . . ? C6 O6 S1 118.34(11) . . ? O1 C1 C6 106.37(15) . . ? O1 C1 C2 108.95(14) . . ? C6 C1 C2 111.23(14) . . ? O1 C1 H1 110.1 . . ? C6 C1 H1 110.1 . . ? C2 C1 H1 110.1 . . ? O2 C2 C3 107.82(14) . . ? O2 C2 C1 109.50(13) . . ? C3 C2 C1 108.06(14) . . ? O2 C2 H2 110.5 . . ? C3 C2 H2 110.5 . . ? C1 C2 H2 110.5 . . ? O3 C3 C2 109.72(14) . . ? O3 C3 C4 107.21(14) . . ? C2 C3 C4 110.02(14) . . ? O3 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? C4 C3 H3 110.0 . . ? O4 C4 C3 106.54(14) . . ? O4 C4 C5 114.77(14) . . ? C3 C4 C5 107.80(14) . . ? O4 C4 H4 109.2 . . ? C3 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? O5 C5 C6 106.06(14) . . ? O5 C5 C4 106.28(14) . . ? C6 C5 C4 113.31(14) . . ? O5 C5 H5 110.3 . . ? C6 C5 H5 110.3 . . ? C4 C5 H5 110.3 . . ? O6 C6 C5 110.75(14) . . ? O6 C6 C1 109.07(15) . . ? C5 C6 C1 108.22(14) . . ? O6 C6 H6 109.6 . . ? C5 C6 H6 109.6 . . ? C1 C6 H6 109.6 . . ? O3 C7 O1 111.30(16) . . ? O3 C7 O5 111.29(17) . . ? O1 C7 O5 111.08(15) . . ? O3 C7 H7 107.7 . . ? O1 C7 H7 107.7 . . ? O5 C7 H7 107.7 . . ? O7 C8 O2 122.99(18) . . ? O7 C8 C9 126.0(2) . . ? O2 C8 C9 110.97(19) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O8 C10 O4 122.59(18) . . ? O8 C10 C11 126.74(18) . . ? O4 C10 C11 110.67(18) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 120.5(2) . . ? C17 C12 S1 119.89(16) . . ? C13 C12 S1 119.64(17) . . ? C12 C13 C14 119.1(2) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 121.6(2) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C16 C15 C14 118.2(2) . . ? C16 C15 C18 120.9(3) . . ? C14 C15 C18 120.8(3) . . ? C15 C16 C17 121.6(2) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C12 C17 C16 118.9(2) . . ? C12 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C9 H9B O8 0.96 2.72 3.417(3) 129.6 4_576 C9 H9A O10 0.96 2.60 3.518(3) 159.2 4_576 C7 H7 O3 0.98 2.58 3.393(2) 140.7 3_566 C3 H3 O5 0.98 2.58 3.367(2) 137.5 1_565 C3 H3 O8 0.98 2.50 3.326(2) 142.1 2 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.230 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.038 #===END data_1_Form-II _database_code_depnum_ccdc_archive 'CCDC 706840' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '6-O-TOSYL 2,4-O-DIACETYL MYO-INOSITOL 1,3,5 ORTHOFORMATE' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 O10 S' _chemical_formula_sum 'C18 H20 O10 S' _chemical_formula_weight 428.40 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' 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' H H 0.0000 0.0000 '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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 6.206(2) _cell_length_b 14.602(5) _cell_length_c 42.099(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3815(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 514 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 15.44 _exptl_crystal_description 'THIN NEEDLE' _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9395 _exptl_absorpt_correction_T_max 0.9955 _exptl_absorpt_process_details 'BRUKER SADABS' _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 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _chemical_absolute_configuration SYN _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17512 _diffrn_reflns_av_R_equivalents 0.1925 _diffrn_reflns_av_sigmaI/netI 0.1706 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3352 _reflns_number_gt 1379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, ORTEP3,MERCURY1.2.1' _computing_publication_material 'SHELXTL, PLATON' _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^)+(0.0665P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3352 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2079 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.1852 _refine_ls_wR_factor_gt 0.1408 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.7635(3) 0.36738(12) 0.08624(4) 0.0575(5) Uani 1 1 d . . . O1 O 0.6551(7) 0.2962(3) 0.20063(9) 0.0514(11) Uani 1 1 d . . . O2 O 1.1121(6) 0.2821(2) 0.20994(8) 0.0408(10) Uani 1 1 d . . . O3 O 0.8167(6) 0.4246(3) 0.22279(8) 0.0470(11) Uani 1 1 d . . . O4 O 1.0435(6) 0.5022(3) 0.14828(8) 0.0467(11) Uani 1 1 d . . . O5 O 0.5327(6) 0.4416(3) 0.18756(9) 0.0548(12) Uani 1 1 d . . . O6 O 0.8455(6) 0.3448(3) 0.12089(8) 0.0508(11) Uani 1 1 d . . . O7 O 1.2210(8) 0.1788(3) 0.17445(11) 0.0809(16) Uani 1 1 d . . . O8 O 0.8748(9) 0.6291(3) 0.13097(9) 0.0650(14) Uani 1 1 d . . . O9 O 0.5368(8) 0.3515(4) 0.08520(10) 0.0860(17) Uani 1 1 d . . . O10 O 0.8415(9) 0.4555(3) 0.07787(9) 0.0829(16) Uani 1 1 d . . . C1 C 0.8025(9) 0.2944(4) 0.17445(12) 0.0439(16) Uani 1 1 d . . . H1 H 0.8239 0.2311 0.1674 0.053 Uiso 1 1 calc R . . C2 C 1.0173(9) 0.3354(3) 0.18456(12) 0.0349(14) Uani 1 1 d . . . H2 H 1.1159 0.3388 0.1664 0.042 Uiso 1 1 calc R . . C3 C 0.9740(9) 0.4294(4) 0.19748(11) 0.0348(14) Uani 1 1 d . . . H3 H 1.1083 0.4556 0.2057 0.042 Uiso 1 1 calc R . . C4 C 0.8824(10) 0.4915(4) 0.17225(12) 0.0400(15) Uani 1 1 d . . . H4 H 0.8505 0.5514 0.1817 0.048 Uiso 1 1 calc R . . C5 C 0.6716(9) 0.4481(4) 0.16024(13) 0.0453(16) Uani 1 1 d . . . H5 H 0.6057 0.4867 0.1439 0.054 Uiso 1 1 calc R . . C6 C 0.7019(10) 0.3499(4) 0.14789(12) 0.0484(17) Uani 1 1 d . . . H6 H 0.5616 0.3238 0.1422 0.058 Uiso 1 1 calc R . . C7 C 0.6245(10) 0.3862(5) 0.21140(14) 0.0536(18) Uani 1 1 d . . . H7 H 0.5225 0.3839 0.2292 0.064 Uiso 1 1 calc R . . C8 C 1.2103(10) 0.2027(4) 0.20128(15) 0.0477(17) Uani 1 1 d . . . C9 C 1.2994(10) 0.1551(4) 0.22904(14) 0.0606(19) Uani 1 1 d . . . H9A H 1.4457 0.1376 0.2248 0.091 Uiso 1 1 calc R . . H9B H 1.2153 0.1013 0.2334 0.091 Uiso 1 1 calc R . . H9C H 1.2955 0.1951 0.2471 0.091 Uiso 1 1 calc R . . C10 C 1.0250(13) 0.5780(5) 0.12964(14) 0.0520(18) Uani 1 1 d . . . C11 C 1.2188(11) 0.5866(5) 0.10782(14) 0.068(2) Uani 1 1 d . . . H11A H 1.2005 0.6387 0.0942 0.101 Uiso 1 1 calc R . . H11B H 1.2316 0.5322 0.0951 0.101 Uiso 1 1 calc R . . H11C H 1.3469 0.5943 0.1203 0.101 Uiso 1 1 calc R . . C12 C 0.9029(11) 0.2845(4) 0.06469(12) 0.0465(16) Uani 1 1 d . . . C13 C 1.0978(12) 0.3061(4) 0.05042(15) 0.0591(19) Uani 1 1 d . . . H13 H 1.1546 0.3648 0.0523 0.071 Uiso 1 1 calc R . . C14 C 1.2080(11) 0.2393(5) 0.03322(15) 0.063(2) Uani 1 1 d . . . H14 H 1.3388 0.2536 0.0236 0.075 Uiso 1 1 calc R . . C15 C 1.1253(12) 0.1527(4) 0.03032(13) 0.0529(18) Uani 1 1 d . . . C16 C 0.9308(12) 0.1330(5) 0.04449(14) 0.064(2) Uani 1 1 d . . . H16 H 0.8742 0.0743 0.0425 0.077 Uiso 1 1 calc R . . C17 C 0.8174(11) 0.1977(5) 0.06158(13) 0.0576(19) Uani 1 1 d . . . H17 H 0.6858 0.1831 0.0708 0.069 Uiso 1 1 calc R . . C18 C 1.2521(12) 0.0794(5) 0.01287(16) 0.084(2) Uani 1 1 d . . . H18A H 1.2199 0.0823 -0.0094 0.127 Uiso 1 1 calc R . . H18B H 1.2132 0.0202 0.0209 0.127 Uiso 1 1 calc R . . H18C H 1.4035 0.0893 0.0160 0.127 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 0.0593(14) 0.0696(13) 0.0436(9) -0.0105(9) -0.0154(9) 0.0136(11) O1 0.038(3) 0.061(3) 0.055(3) 0.003(2) 0.001(2) -0.005(2) O2 0.038(3) 0.039(2) 0.045(2) 0.0013(19) -0.004(2) 0.009(2) O3 0.039(3) 0.063(3) 0.039(2) -0.0053(19) 0.000(2) 0.009(2) O4 0.038(3) 0.047(2) 0.055(3) 0.005(2) 0.004(2) 0.001(2) O5 0.026(3) 0.088(3) 0.050(3) -0.006(2) 0.002(2) 0.014(2) O6 0.043(3) 0.073(3) 0.035(2) -0.012(2) -0.005(2) 0.000(2) O7 0.093(4) 0.078(3) 0.071(3) -0.030(3) -0.013(3) 0.035(3) O8 0.074(4) 0.061(3) 0.060(3) 0.004(2) 0.003(3) 0.024(3) O9 0.038(3) 0.146(5) 0.074(3) -0.032(3) -0.023(2) 0.027(3) O10 0.127(5) 0.055(3) 0.066(3) 0.000(2) -0.012(3) 0.020(3) C1 0.043(5) 0.049(4) 0.040(3) -0.003(3) 0.007(3) -0.005(3) C2 0.027(4) 0.049(4) 0.028(3) 0.002(3) -0.003(3) -0.007(3) C3 0.026(4) 0.042(4) 0.036(3) -0.007(3) -0.008(3) -0.001(3) C4 0.032(4) 0.047(3) 0.041(4) -0.001(3) 0.007(3) 0.004(3) C5 0.034(4) 0.061(4) 0.041(4) 0.000(3) -0.005(3) 0.006(3) C6 0.034(4) 0.072(5) 0.040(4) -0.008(3) -0.006(3) -0.003(3) C7 0.022(4) 0.099(6) 0.040(4) 0.008(4) 0.005(3) 0.010(4) C8 0.037(4) 0.047(4) 0.059(4) -0.008(4) 0.001(3) 0.001(3) C9 0.050(5) 0.052(4) 0.079(5) 0.015(3) -0.002(4) 0.020(4) C10 0.057(5) 0.052(5) 0.047(4) 0.002(4) -0.003(4) -0.011(4) C11 0.069(6) 0.079(5) 0.055(4) 0.017(3) 0.011(4) -0.001(4) C12 0.046(5) 0.061(4) 0.033(3) -0.008(3) -0.008(3) 0.002(4) C13 0.056(5) 0.051(4) 0.071(5) 0.000(4) -0.006(4) -0.013(4) C14 0.052(5) 0.075(5) 0.061(5) 0.008(4) 0.011(4) -0.005(4) C15 0.064(5) 0.056(5) 0.039(4) -0.003(3) 0.001(4) 0.001(4) C16 0.075(6) 0.074(5) 0.044(4) -0.011(4) 0.004(4) -0.024(5) C17 0.050(5) 0.077(5) 0.045(4) -0.008(4) 0.011(3) -0.017(4) C18 0.081(6) 0.093(5) 0.079(5) -0.016(4) 0.022(4) 0.015(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 S1 O10 1.419(5) . ? S1 O9 1.426(5) . ? S1 O6 1.580(4) . ? S1 C12 1.742(6) . ? O1 C7 1.403(7) . ? O1 C1 1.432(6) . ? O2 C8 1.360(6) . ? O2 C2 1.447(6) . ? O3 C7 1.403(7) . ? O3 C3 1.447(6) . ? O4 C10 1.362(7) . ? O4 C4 1.429(6) . ? O5 C7 1.409(6) . ? O5 C5 1.440(6) . ? O6 C6 1.446(6) . ? O7 C8 1.184(6) . ? O8 C10 1.195(7) . ? C1 C6 1.515(7) . ? C1 C2 1.522(7) . ? C1 H1 0.9800 . ? C2 C3 1.500(7) . ? C2 H2 0.9800 . ? C3 C4 1.508(7) . ? C3 H3 0.9800 . ? C4 C5 1.538(7) . ? C4 H4 0.9800 . ? C5 C6 1.538(8) . ? C5 H5 0.9800 . ? C6 H6 0.9800 . ? C7 H7 0.9800 . ? C8 C9 1.468(8) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.519(9) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C17 1.380(8) . ? C12 C13 1.387(8) . ? C13 C14 1.394(8) . ? C13 H13 0.9300 . ? C14 C15 1.369(8) . ? C14 H14 0.9300 . ? C15 C16 1.377(9) . ? C15 C18 1.519(9) . ? C16 C17 1.381(8) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 O10 S1 O9 118.4(3) . . ? O10 S1 O6 108.0(2) . . ? O9 S1 O6 108.2(3) . . ? O10 S1 C12 109.3(3) . . ? O9 S1 C12 111.2(3) . . ? O6 S1 C12 100.1(2) . . ? C7 O1 C1 110.6(4) . . ? C8 O2 C2 116.3(4) . . ? C7 O3 C3 109.9(4) . . ? C10 O4 C4 115.9(5) . . ? C7 O5 C5 111.4(4) . . ? C6 O6 S1 121.1(4) . . ? O1 C1 C6 107.2(5) . . ? O1 C1 C2 109.7(4) . . ? C6 C1 C2 110.9(5) . . ? O1 C1 H1 109.7 . . ? C6 C1 H1 109.7 . . ? C2 C1 H1 109.7 . . ? O2 C2 C3 107.3(4) . . ? O2 C2 C1 110.6(4) . . ? C3 C2 C1 107.7(5) . . ? O2 C2 H2 110.4 . . ? C3 C2 H2 110.4 . . ? C1 C2 H2 110.4 . . ? O3 C3 C2 110.1(4) . . ? O3 C3 C4 107.0(4) . . ? C2 C3 C4 111.3(4) . . ? O3 C3 H3 109.5 . . ? C2 C3 H3 109.5 . . ? C4 C3 H3 109.5 . . ? O4 C4 C3 107.4(5) . . ? O4 C4 C5 114.1(4) . . ? C3 C4 C5 107.7(4) . . ? O4 C4 H4 109.2 . . ? C3 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? O5 C5 C6 106.3(5) . . ? O5 C5 C4 105.9(4) . . ? C6 C5 C4 113.0(5) . . ? O5 C5 H5 110.5 . . ? C6 C5 H5 110.5 . . ? C4 C5 H5 110.5 . . ? O6 C6 C1 107.4(5) . . ? O6 C6 C5 112.9(5) . . ? C1 C6 C5 107.4(4) . . ? O6 C6 H6 109.7 . . ? C1 C6 H6 109.7 . . ? C5 C6 H6 109.7 . . ? O1 C7 O3 111.7(5) . . ? O1 C7 O5 111.3(5) . . ? O3 C7 O5 110.9(5) . . ? O1 C7 H7 107.6 . . ? O3 C7 H7 107.6 . . ? O5 C7 H7 107.6 . . ? O7 C8 O2 122.1(6) . . ? O7 C8 C9 126.8(6) . . ? O2 C8 C9 111.1(5) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O8 C10 O4 123.1(6) . . ? O8 C10 C11 126.5(6) . . ? O4 C10 C11 110.4(7) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 120.2(6) . . ? C17 C12 S1 119.8(5) . . ? C13 C12 S1 120.1(5) . . ? C12 C13 C14 119.6(6) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.5(6) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 118.9(6) . . ? C14 C15 C18 120.0(7) . . ? C16 C15 C18 121.1(7) . . ? C15 C16 C17 122.0(6) . . ? C15 C16 H16 119.0 . . ? C17 C16 H16 119.0 . . ? C12 C17 C16 118.8(6) . . ? C12 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C13 H13 O9 0.93 2.75 3.164(8) 107.8 1_655 C17 H17 O8 0.93 2.68 3.311(7) 125.9 7_755 C1 H1 O8 0.98 2.47 3.224(7) 133.6 7_755 C11 H11C O7 0.96 2.62 3.134(8) 113.5 7_865 C3 H3 O5 0.98 2.75 3.497(7) 133.5 1_655 C7 H7 O3 0.98 2.47 3.412(7) 162.2 6_556 C16 H16 O10 0.93 2.65 3.398(8) 138.0 7_755 C9 H9C O1 0.96 2.79 3.717(7) 162.9 6_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.298 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.062 #===END data_2_FormI _database_code_depnum_ccdc_archive 'CCDC 706841' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '6-O-TOSYL 4,2-DI-O-ACETYL MYO-INOSITOL ORTHOACETATE' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 O10 S' _chemical_formula_sum 'C19 H22 O10 S' _chemical_formula_weight 442.43 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 6.2596(8) _cell_length_b 9.8947(12) _cell_length_c 17.022(2) _cell_angle_alpha 87.723(2) _cell_angle_beta 89.460(2) _cell_angle_gamma 76.195(2) _cell_volume 1023.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3704 _cell_measurement_theta_min 2.395 _cell_measurement_theta_max 27.93 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8919 _exptl_absorpt_correction_T_max 0.9728 _exptl_absorpt_process_details 'BRUKER SADABS' _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 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _chemical_absolute_configuration SYN _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9894 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3610 _reflns_number_gt 3110 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, ORTEP3,MERCURY1.2.1' _computing_publication_material SHELXTL,PLATON,PARST,CSU _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^)+(0.0592P)^2^+0.3158P] 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 3610 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.88669(10) -0.03838(6) 0.66871(3) 0.0591(2) Uani 1 1 d . . . O1 O 0.7404(2) 0.34914(13) 0.83676(8) 0.0450(3) Uani 1 1 d . . . O2 O 0.2799(2) 0.37739(14) 0.81561(9) 0.0526(4) Uani 1 1 d . . . O3 O 0.5582(2) 0.29042(14) 0.94714(8) 0.0438(3) Uani 1 1 d . . . O4 O 0.5087(2) -0.03743(13) 0.87429(8) 0.0456(3) Uani 1 1 d . . . O5 O 0.9129(2) 0.16663(13) 0.92093(8) 0.0440(3) Uani 1 1 d . . . O6 O 0.7516(2) 0.01972(15) 0.74450(8) 0.0517(4) Uani 1 1 d . . . O7 O 0.1676(3) 0.3324(2) 0.69827(11) 0.0863(6) Uani 1 1 d . . . O8 O 0.7752(3) -0.22384(16) 0.90656(11) 0.0703(5) Uani 1 1 d . . . O9 O 1.1137(3) -0.0504(2) 0.68246(10) 0.0848(6) Uani 1 1 d . . . O10 O 0.8066(4) -0.15677(16) 0.65246(10) 0.0825(6) Uani 1 1 d . . . C1 C 0.6563(3) 0.2590(2) 0.78781(11) 0.0432(4) Uani 1 1 d . . . H1 H 0.6406 0.2972 0.7336 0.052 Uiso 1 1 calc R . . C2 C 0.4347(3) 0.24399(19) 0.81933(12) 0.0418(4) Uani 1 1 d . . . H2 H 0.3806 0.1764 0.7894 0.050 Uiso 1 1 calc R . . C3 C 0.4641(3) 0.1967(2) 0.90499(11) 0.0409(4) Uani 1 1 d . . . H3 H 0.3215 0.1929 0.9280 0.049 Uiso 1 1 calc R . . C4 C 0.6213(3) 0.05306(19) 0.91188(11) 0.0400(4) Uani 1 1 d . . . H4 H 0.6427 0.0243 0.9676 0.048 Uiso 1 1 calc R . . C5 C 0.8417(3) 0.06504(19) 0.87631(11) 0.0404(4) Uani 1 1 d . . . H5 H 0.9491 -0.0249 0.8809 0.048 Uiso 1 1 calc R . . C6 C 0.8236(3) 0.1194(2) 0.79138(11) 0.0431(4) Uani 1 1 d . . . H6 H 0.9669 0.1310 0.7727 0.052 Uiso 1 1 calc R . . C7 C 0.7632(3) 0.2998(2) 0.91587(12) 0.0424(4) Uani 1 1 d . . . C8 C 0.8510(4) 0.3989(2) 0.96273(14) 0.0554(5) Uani 1 1 d . . . H8A H 0.7463 0.4873 0.9624 0.083 Uiso 1 1 calc R . . H8B H 0.9869 0.4103 0.9400 0.083 Uiso 1 1 calc R . . H8C H 0.8764 0.3627 1.0159 0.083 Uiso 1 1 calc R . . C9 C 0.1582(4) 0.4099(2) 0.74983(15) 0.0549(6) Uani 1 1 d . . . C10 C 0.0143(4) 0.5532(3) 0.75255(18) 0.0736(7) Uani 1 1 d . . . H10A H 0.0987 0.6200 0.7388 0.110 Uiso 1 1 calc R . . H10B H -0.0439 0.5691 0.8046 0.110 Uiso 1 1 calc R . . H10C H -0.1046 0.5631 0.7159 0.110 Uiso 1 1 calc R . . C11 C 0.6021(4) -0.1756(2) 0.87621(12) 0.0483(5) Uani 1 1 d . . . C12 C 0.4600(4) -0.2524(2) 0.83673(17) 0.0681(7) Uani 1 1 d . . . H12A H 0.5210 -0.3507 0.8439 0.102 Uiso 1 1 calc R . . H12B H 0.4519 -0.2273 0.7816 0.102 Uiso 1 1 calc R . . H12C H 0.3151 -0.2289 0.8591 0.102 Uiso 1 1 calc R . . C13 C 0.7936(4) 0.0922(2) 0.59608(12) 0.0518(5) Uani 1 1 d . . . C14 C 0.5852(5) 0.1095(3) 0.56719(18) 0.0792(8) Uani 1 1 d . . . H14 H 0.4933 0.0556 0.5877 0.095 Uiso 1 1 calc R . . C15 C 0.5126(5) 0.2069(3) 0.50771(19) 0.0876(9) Uani 1 1 d . . . H15 H 0.3706 0.2182 0.4885 0.105 Uiso 1 1 calc R . . C16 C 0.6412(5) 0.2870(3) 0.47619(14) 0.0684(7) Uani 1 1 d . . . C17 C 0.8465(5) 0.2697(3) 0.50670(18) 0.0874(9) Uani 1 1 d . . . H17 H 0.9368 0.3248 0.4865 0.105 Uiso 1 1 calc R . . C18 C 0.9255(5) 0.1728(3) 0.56683(17) 0.0800(8) Uani 1 1 d . . . H18 H 1.0663 0.1632 0.5868 0.096 Uiso 1 1 calc R . . C19 C 0.5601(7) 0.3896(4) 0.40845(18) 0.1067(11) Uani 1 1 d . . . H19A H 0.6453 0.4585 0.4056 0.160 Uiso 1 1 calc R . . H19B H 0.4081 0.4344 0.4166 0.160 Uiso 1 1 calc R . . H19C H 0.5753 0.3412 0.3602 0.160 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 0.0681(4) 0.0539(3) 0.0440(3) -0.0115(2) -0.0060(3) 0.0098(3) O1 0.0484(8) 0.0411(7) 0.0485(8) -0.0012(6) -0.0018(6) -0.0165(6) O2 0.0464(8) 0.0390(7) 0.0675(9) -0.0037(7) -0.0160(7) 0.0003(6) O3 0.0414(7) 0.0444(7) 0.0464(8) -0.0097(6) 0.0020(6) -0.0105(6) O4 0.0427(7) 0.0384(7) 0.0560(8) 0.0003(6) -0.0077(6) -0.0104(6) O5 0.0368(7) 0.0438(7) 0.0509(8) -0.0070(6) -0.0088(6) -0.0075(6) O6 0.0605(9) 0.0525(8) 0.0432(8) -0.0110(6) -0.0001(6) -0.0145(7) O7 0.1042(15) 0.0752(12) 0.0683(12) -0.0033(10) -0.0384(11) 0.0023(10) O8 0.0707(11) 0.0446(9) 0.0901(12) 0.0011(8) -0.0320(9) -0.0026(8) O9 0.0619(11) 0.1094(15) 0.0613(10) -0.0177(10) -0.0063(8) 0.0249(10) O10 0.1349(17) 0.0433(9) 0.0606(11) -0.0127(8) -0.0170(10) -0.0018(10) C1 0.0510(11) 0.0415(10) 0.0373(10) 0.0012(8) -0.0033(8) -0.0118(9) C2 0.0391(10) 0.0335(9) 0.0511(11) -0.0032(8) -0.0088(8) -0.0049(8) C3 0.0343(9) 0.0416(10) 0.0474(11) -0.0036(8) 0.0001(8) -0.0099(8) C4 0.0427(10) 0.0387(10) 0.0387(10) -0.0008(8) -0.0037(8) -0.0101(8) C5 0.0366(10) 0.0380(10) 0.0449(10) -0.0054(8) -0.0036(8) -0.0050(8) C6 0.0423(10) 0.0452(11) 0.0435(11) -0.0070(8) 0.0035(8) -0.0126(9) C7 0.0374(10) 0.0425(10) 0.0473(11) -0.0050(8) -0.0020(8) -0.0086(8) C8 0.0538(12) 0.0508(12) 0.0640(14) -0.0139(10) -0.0074(10) -0.0147(10) C9 0.0477(12) 0.0491(12) 0.0668(15) 0.0143(11) -0.0136(10) -0.0114(10) C10 0.0582(14) 0.0545(14) 0.099(2) 0.0227(13) -0.0085(13) 0.0004(11) C11 0.0564(13) 0.0392(11) 0.0478(11) 0.0006(9) -0.0048(10) -0.0085(9) C12 0.0720(16) 0.0476(13) 0.0864(18) -0.0101(12) -0.0164(13) -0.0161(11) C13 0.0546(12) 0.0553(12) 0.0415(11) -0.0093(9) 0.0008(9) -0.0043(10) C14 0.0691(16) 0.0810(19) 0.091(2) 0.0267(16) -0.0212(15) -0.0276(14) C15 0.0778(18) 0.093(2) 0.092(2) 0.0265(17) -0.0295(16) -0.0250(16) C16 0.0855(19) 0.0665(16) 0.0487(13) -0.0031(11) 0.0030(12) -0.0088(14) C17 0.087(2) 0.095(2) 0.082(2) 0.0165(17) 0.0211(16) -0.0288(17) C18 0.0587(15) 0.103(2) 0.0784(18) 0.0065(16) 0.0007(13) -0.0222(15) C19 0.146(3) 0.096(2) 0.0657(19) 0.0195(17) 0.0013(19) -0.010(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 O10 1.4173(19) . ? S1 O9 1.4182(19) . ? S1 O6 1.5862(15) . ? S1 C13 1.750(2) . ? O1 C7 1.411(2) . ? O1 C1 1.435(2) . ? O2 C9 1.345(3) . ? O2 C2 1.439(2) . ? O3 C7 1.407(2) . ? O3 C3 1.429(2) . ? O4 C11 1.352(2) . ? O4 C4 1.436(2) . ? O5 C7 1.423(2) . ? O5 C5 1.438(2) . ? O6 C6 1.447(2) . ? O7 C9 1.180(3) . ? O8 C11 1.188(2) . ? C1 C2 1.521(3) . ? C1 C6 1.521(3) . ? C1 H1 0.9800 . ? C2 C3 1.513(3) . ? C2 H2 0.9800 . ? C3 C4 1.525(3) . ? C3 H3 0.9800 . ? C4 C5 1.530(3) . ? C4 H4 0.9800 . ? C5 C6 1.518(3) . ? C5 H5 0.9800 . ? C6 H6 0.9800 . ? C7 C8 1.492(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.489(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.481(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C18 1.357(4) . ? C13 C14 1.368(3) . ? C14 C15 1.372(4) . ? C14 H14 0.9300 . ? C15 C16 1.351(4) . ? C15 H15 0.9300 . ? C16 C17 1.361(4) . ? C16 C19 1.514(4) . ? C17 C18 1.384(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 O10 S1 O9 121.01(12) . . ? O10 S1 O6 103.08(11) . . ? O9 S1 O6 109.05(9) . . ? O10 S1 C13 109.30(11) . . ? O9 S1 C13 109.20(12) . . ? O6 S1 C13 103.73(9) . . ? C7 O1 C1 112.37(14) . . ? C9 O2 C2 116.77(17) . . ? C7 O3 C3 111.76(14) . . ? C11 O4 C4 118.49(15) . . ? C7 O5 C5 112.60(13) . . ? C6 O6 S1 119.94(12) . . ? O1 C1 C2 109.39(15) . . ? O1 C1 C6 106.38(15) . . ? C2 C1 C6 110.76(15) . . ? O1 C1 H1 110.1 . . ? C2 C1 H1 110.1 . . ? C6 C1 H1 110.1 . . ? O2 C2 C3 107.60(16) . . ? O2 C2 C1 109.65(15) . . ? C3 C2 C1 107.92(15) . . ? O2 C2 H2 110.5 . . ? C3 C2 H2 110.5 . . ? C1 C2 H2 110.5 . . ? O3 C3 C2 110.19(15) . . ? O3 C3 C4 107.77(14) . . ? C2 C3 C4 109.61(15) . . ? O3 C3 H3 109.7 . . ? C2 C3 H3 109.7 . . ? C4 C3 H3 109.7 . . ? O4 C4 C3 104.77(14) . . ? O4 C4 C5 116.82(15) . . ? C3 C4 C5 107.69(15) . . ? O4 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? O5 C5 C6 106.69(15) . . ? O5 C5 C4 105.94(14) . . ? C6 C5 C4 113.30(15) . . ? O5 C5 H5 110.2 . . ? C6 C5 H5 110.2 . . ? C4 C5 H5 110.2 . . ? O6 C6 C5 108.32(15) . . ? O6 C6 C1 110.67(15) . . ? C5 C6 C1 107.94(15) . . ? O6 C6 H6 110.0 . . ? C5 C6 H6 110.0 . . ? C1 C6 H6 110.0 . . ? O3 C7 O1 110.48(15) . . ? O3 C7 O5 109.74(15) . . ? O1 C7 O5 109.77(15) . . ? O3 C7 C8 108.70(16) . . ? O1 C7 C8 109.08(16) . . ? O5 C7 C8 109.04(15) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O7 C9 O2 122.9(2) . . ? O7 C9 C10 126.3(2) . . ? O2 C9 C10 110.8(2) . . ? 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 . . ? O8 C11 O4 122.24(19) . . ? O8 C11 C12 126.9(2) . . ? O4 C11 C12 110.85(18) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 119.9(2) . . ? C18 C13 S1 121.38(19) . . ? C14 C13 S1 118.65(19) . . ? C13 C14 C15 119.5(3) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 122.0(3) . . ? C16 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C15 C16 C17 117.5(3) . . ? C15 C16 C19 120.9(3) . . ? C17 C16 C19 121.7(3) . . ? C16 C17 C18 122.3(3) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C13 C18 C17 118.8(3) . . ? C13 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 C3 H3 O5 0.98 2.64 3.540(2) 153.5 1_455 C8 H8C O8 0.96 2.62 3.359(3) 134.0 2_757 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.351 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.040 #===END data_2_FormII _database_code_depnum_ccdc_archive 'CCDC 706842' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '6-O-TOSYL 4,2-DI-O-ACETYL MYO-INOSITOL ORTHOACETATE' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 O10 S' _chemical_formula_sum 'C19 H22 O10 S' _chemical_formula_weight 442.43 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 9.2713(11) _cell_length_b 35.728(4) _cell_length_c 6.1772(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.872(2) _cell_angle_gamma 90.00 _cell_volume 2045.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2624 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 27.95 _exptl_crystal_description 'THIN PLATE' _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8955 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details 'BRUKER SADABS' _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 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _chemical_absolute_configuration SYN _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19352 _diffrn_reflns_av_R_equivalents 0.0846 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3621 _reflns_number_gt 2319 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, ORTEP3,MERCURY1.2.1' _computing_publication_material SHELXTL,PLATON,PARST,CSU _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^)+(0.0497P)^2^+0.4009P] 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 3621 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1404 _refine_ls_R_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1332 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_restrained_S_all 1.203 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.04873(12) 0.89632(3) 0.28993(19) 0.0595(4) Uani 1 1 d . . . O5 O 0.3951(2) 0.79594(7) 0.1852(4) 0.0403(6) Uani 1 1 d . . . O3 O 0.5295(2) 0.79288(7) 0.5030(4) 0.0381(6) Uani 1 1 d . . . O1 O 0.5273(2) 0.84737(7) 0.2992(4) 0.0395(6) Uani 1 1 d . . . O4 O 0.1567(3) 0.80275(7) 0.6568(4) 0.0423(7) Uani 1 1 d . . . O6 O 0.1455(3) 0.86509(7) 0.4000(4) 0.0498(7) Uani 1 1 d . . . O2 O 0.5446(2) 0.85776(7) 0.7528(4) 0.0452(7) Uani 1 1 d . . . C4 C 0.2737(4) 0.79143(10) 0.5187(5) 0.0362(9) Uani 1 1 d . . . H4 H 0.2756 0.7641 0.5067 0.043 Uiso 1 1 calc R . . C3 C 0.4105(4) 0.80503(10) 0.6303(6) 0.0381(9) Uani 1 1 d . . . H3 H 0.4181 0.7940 0.7754 0.046 Uiso 1 1 calc R . . C5 C 0.2677(4) 0.80893(10) 0.2926(6) 0.0370(9) Uani 1 1 d . . . H5 H 0.1812 0.8004 0.2140 0.044 Uiso 1 1 calc R . . C7 C 0.5237(4) 0.80795(10) 0.2923(6) 0.0362(9) Uani 1 1 d . . . C1 C 0.4091(4) 0.86287(10) 0.4173(6) 0.0383(9) Uani 1 1 d . . . H1 H 0.4162 0.8902 0.4211 0.046 Uiso 1 1 calc R . . O7 O 0.4462(3) 0.91028(9) 0.8773(5) 0.0757(10) Uani 1 1 d . . . O10 O -0.0839(3) 0.89348(9) 0.4013(6) 0.0836(10) Uani 1 1 d . . . C6 C 0.2733(4) 0.85104(10) 0.2942(6) 0.0410(10) Uani 1 1 d . . . H6 H 0.2763 0.8605 0.1454 0.049 Uiso 1 1 calc R . . O9 O 0.0540(3) 0.89203(9) 0.0606(5) 0.0751(10) Uani 1 1 d . . . C8 C 0.6510(4) 0.79418(12) 0.1709(6) 0.0515(11) Uani 1 1 d . . . H8A H 0.7380 0.8015 0.2458 0.077 Uiso 1 1 calc R . . H8B H 0.6498 0.8048 0.0282 0.077 Uiso 1 1 calc R . . H8C H 0.6470 0.7674 0.1604 0.077 Uiso 1 1 calc R . . O8 O 0.0010(3) 0.77101(10) 0.4503(5) 0.0787(11) Uani 1 1 d . . . C2 C 0.4115(4) 0.84717(10) 0.6471(5) 0.0379(9) Uani 1 1 d . . . H2 H 0.3285 0.8561 0.7286 0.046 Uiso 1 1 calc R . . C13 C 0.1349(4) 0.93792(12) 0.3630(7) 0.0539(11) Uani 1 1 d . . . C10 C 0.6972(4) 0.89831(12) 0.9409(7) 0.0654(13) Uani 1 1 d . . . H10A H 0.7065 0.9245 0.9732 0.098 Uiso 1 1 calc R . . H10B H 0.7663 0.8915 0.8337 0.098 Uiso 1 1 calc R . . H10C H 0.7143 0.8840 1.0701 0.098 Uiso 1 1 calc R . . C12 C -0.0879(4) 0.80776(13) 0.7430(7) 0.0672(13) Uani 1 1 d . . . H12A H -0.1819 0.7990 0.6999 0.101 Uiso 1 1 calc R . . H12B H -0.0847 0.8345 0.7317 0.101 Uiso 1 1 calc R . . H12C H -0.0682 0.8005 0.8901 0.101 Uiso 1 1 calc R . . C18 C 0.2227(5) 0.95602(14) 0.2197(8) 0.0666(13) Uani 1 1 d . . . H18 H 0.2361 0.9463 0.0819 0.080 Uiso 1 1 calc R . . C9 C 0.5493(5) 0.89062(12) 0.8566(6) 0.0462(10) Uani 1 1 d . . . C15 C 0.1843(6) 0.98517(16) 0.6217(8) 0.0798(16) Uani 1 1 d . . . H15 H 0.1704 0.9950 0.7593 0.096 Uiso 1 1 calc R . . C17 C 0.2910(6) 0.98875(14) 0.2808(9) 0.0755(14) Uani 1 1 d . . . H17 H 0.3503 1.0008 0.1827 0.091 Uiso 1 1 calc R . . C16 C 0.2738(5) 1.00400(13) 0.4822(9) 0.0688(14) Uani 1 1 d . . . C14 C 0.1153(6) 0.95272(15) 0.5661(8) 0.0747(14) Uani 1 1 d . . . H14 H 0.0558 0.9408 0.6643 0.090 Uiso 1 1 calc R . . C19 C 0.3498(6) 1.03959(14) 0.5482(9) 0.0954(18) Uani 1 1 d . . . H19A H 0.2857 1.0604 0.5279 0.143 Uiso 1 1 calc R . . H19B H 0.4336 1.0430 0.4609 0.143 Uiso 1 1 calc R . . H19C H 0.3786 1.0380 0.6979 0.143 Uiso 1 1 calc R . . C11 C 0.0225(4) 0.79106(12) 0.5991(7) 0.0496(11) 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 S1 0.0435(7) 0.0714(8) 0.0632(8) 0.0026(6) -0.0139(5) 0.0171(6) O5 0.0327(14) 0.0594(17) 0.0289(14) -0.0090(12) 0.0007(11) 0.0027(12) O3 0.0318(14) 0.0509(16) 0.0314(14) 0.0040(12) 0.0012(11) 0.0050(12) O1 0.0329(14) 0.0486(17) 0.0372(15) 0.0037(12) 0.0040(11) -0.0020(12) O4 0.0363(15) 0.0542(17) 0.0367(15) -0.0050(12) 0.0077(12) -0.0064(13) O6 0.0397(15) 0.0596(18) 0.0501(17) 0.0019(14) 0.0032(13) 0.0132(13) O2 0.0343(14) 0.0583(18) 0.0426(16) -0.0144(13) -0.0092(12) -0.0013(13) C4 0.033(2) 0.042(2) 0.034(2) -0.0040(17) 0.0075(17) 0.0036(17) C3 0.036(2) 0.051(3) 0.026(2) 0.0003(17) 0.0005(17) 0.0020(19) C5 0.026(2) 0.053(3) 0.032(2) -0.0066(18) -0.0008(16) 0.0043(18) C7 0.032(2) 0.048(3) 0.029(2) -0.0041(18) -0.0001(17) 0.0004(18) C1 0.036(2) 0.038(2) 0.041(2) -0.0018(18) 0.0039(18) 0.0035(18) O7 0.059(2) 0.069(2) 0.099(3) -0.0348(18) -0.0061(18) 0.0119(17) O10 0.0345(17) 0.106(3) 0.110(3) 0.005(2) 0.0042(17) 0.0187(18) C6 0.036(2) 0.056(3) 0.031(2) 0.0049(18) 0.0021(17) 0.0052(19) O9 0.075(2) 0.091(2) 0.058(2) -0.0010(17) -0.0313(16) 0.0193(18) C8 0.039(2) 0.069(3) 0.046(3) -0.006(2) 0.0105(19) 0.011(2) O8 0.0468(18) 0.111(3) 0.078(2) -0.040(2) 0.0084(16) -0.0257(18) C2 0.030(2) 0.056(3) 0.028(2) -0.0083(18) -0.0027(16) 0.0012(18) C13 0.056(3) 0.060(3) 0.046(3) 0.003(2) -0.005(2) 0.025(2) C10 0.062(3) 0.071(3) 0.064(3) -0.012(2) -0.010(2) -0.018(3) C12 0.046(3) 0.084(3) 0.072(3) -0.003(3) 0.023(2) -0.001(2) C18 0.085(4) 0.067(3) 0.048(3) 0.001(3) 0.008(3) 0.022(3) C9 0.049(3) 0.052(3) 0.037(2) -0.011(2) -0.002(2) -0.004(2) C15 0.108(4) 0.083(4) 0.049(3) -0.011(3) -0.001(3) 0.023(3) C17 0.094(4) 0.057(3) 0.076(4) 0.005(3) 0.012(3) 0.011(3) C16 0.076(4) 0.055(3) 0.075(4) -0.003(3) -0.010(3) 0.027(3) C14 0.090(4) 0.077(4) 0.057(3) 0.003(3) 0.008(3) 0.011(3) C19 0.115(5) 0.065(4) 0.105(5) -0.012(3) -0.017(4) 0.016(3) C11 0.038(3) 0.057(3) 0.054(3) -0.002(2) 0.007(2) -0.008(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 O10 1.421(3) . ? S1 O9 1.426(3) . ? S1 O6 1.579(3) . ? S1 C13 1.743(5) . ? O5 C7 1.421(4) . ? O5 C5 1.440(4) . ? O3 C7 1.409(4) . ? O3 C3 1.432(4) . ? O1 C7 1.410(4) . ? O1 C1 1.437(4) . ? O4 C11 1.355(4) . ? O4 C4 1.447(4) . ? O6 C6 1.452(4) . ? O2 C9 1.338(4) . ? O2 C2 1.437(4) . ? C4 C3 1.514(5) . ? C4 C5 1.531(5) . ? C4 H4 0.9800 . ? C3 C2 1.509(5) . ? C3 H3 0.9800 . ? C5 C6 1.506(5) . ? C5 H5 0.9800 . ? C7 C8 1.491(5) . ? C1 C6 1.521(5) . ? C1 C2 1.526(5) . ? C1 H1 0.9800 . ? O7 C9 1.194(4) . ? C6 H6 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? O8 C11 1.180(4) . ? C2 H2 0.9800 . ? C13 C18 1.374(6) . ? C13 C14 1.376(6) . ? C10 C9 1.485(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C12 C11 1.491(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C18 C17 1.379(6) . ? C18 H18 0.9300 . ? C15 C14 1.365(6) . ? C15 C16 1.381(7) . ? C15 H15 0.9300 . ? C17 C16 1.370(6) . ? C17 H17 0.9300 . ? C16 C19 1.507(6) . ? C14 H14 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 O10 S1 O9 121.0(2) . . ? O10 S1 O6 103.33(18) . . ? O9 S1 O6 108.91(17) . . ? O10 S1 C13 109.4(2) . . ? O9 S1 C13 109.1(2) . . ? O6 S1 C13 103.64(16) . . ? C7 O5 C5 112.1(3) . . ? C7 O3 C3 111.9(3) . . ? C7 O1 C1 112.5(3) . . ? C11 O4 C4 116.9(3) . . ? C6 O6 S1 120.8(2) . . ? C9 O2 C2 118.0(3) . . ? O4 C4 C3 105.8(3) . . ? O4 C4 C5 114.0(3) . . ? C3 C4 C5 107.6(3) . . ? O4 C4 H4 109.8 . . ? C3 C4 H4 109.8 . . ? C5 C4 H4 109.8 . . ? O3 C3 C2 109.6(3) . . ? O3 C3 C4 107.5(3) . . ? C2 C3 C4 110.9(3) . . ? O3 C3 H3 109.6 . . ? C2 C3 H3 109.6 . . ? C4 C3 H3 109.6 . . ? O5 C5 C6 107.3(3) . . ? O5 C5 C4 105.7(3) . . ? C6 C5 C4 113.7(3) . . ? O5 C5 H5 110.0 . . ? C6 C5 H5 110.0 . . ? C4 C5 H5 110.0 . . ? O3 C7 O1 110.7(3) . . ? O3 C7 O5 109.6(3) . . ? O1 C7 O5 109.6(3) . . ? O3 C7 C8 108.6(3) . . ? O1 C7 C8 109.0(3) . . ? O5 C7 C8 109.3(3) . . ? O1 C1 C6 105.7(3) . . ? O1 C1 C2 109.3(3) . . ? C6 C1 C2 111.3(3) . . ? O1 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? O6 C6 C5 108.7(3) . . ? O6 C6 C1 110.7(3) . . ? C5 C6 C1 108.0(3) . . ? O6 C6 H6 109.8 . . ? C5 C6 H6 109.8 . . ? C1 C6 H6 109.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C2 C3 107.4(3) . . ? O2 C2 C1 109.0(3) . . ? C3 C2 C1 107.6(3) . . ? O2 C2 H2 110.9 . . ? C3 C2 H2 110.9 . . ? C1 C2 H2 110.9 . . ? C18 C13 C14 119.6(5) . . ? C18 C13 S1 120.6(4) . . ? C14 C13 S1 119.8(4) . . ? 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 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C13 C18 C17 119.8(4) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? O7 C9 O2 123.2(4) . . ? O7 C9 C10 126.1(4) . . ? O2 C9 C10 110.7(4) . . ? C14 C15 C16 122.7(5) . . ? C14 C15 H15 118.6 . . ? C16 C15 H15 118.6 . . ? C16 C17 C18 121.8(5) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C17 C16 C15 116.9(5) . . ? C17 C16 C19 121.4(5) . . ? C15 C16 C19 121.7(5) . . ? C15 C14 C13 119.2(5) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 C11 O4 122.4(4) . . ? O8 C11 C12 126.7(4) . . ? O4 C11 C12 110.9(4) . . ? 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 C10 H10C O1 0.96 2.61 3.286(5) 128.0 1_556 C10 H10C O10 0.96 2.77 3.473(5) 130.5 1_656 C12 H12C O8 0.96 2.66 3.195(6) 115.8 4_576 C18 H18 O7 0.93 2.67 3.402(6) 136.3 1_554 C19 H19A O10 0.96 2.54 3.452(6) 159.8 3_576 C3 H3 O5 0.98 2.54 3.448(4) 153.3 1_556 C4 H4 O5 0.98 2.65 3.469(4) 141.6 4_576 C8 H8B O2 0.96 2.71 3.567(5) 148.2 1_554 C8 H8C O3 0.96 2.60 3.462(5) 150.2 4_575 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.268 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.044 #===END