# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Rajesh Gonnade' _publ_contact_author_email rg.gonnade@ncl.res.in _publ_section_title ; Concomitant Dimorphs of tri-O-[p-halobenzoyl]-myo-inositol 1,3,5-orthoformates with different halogen bonding contacts: first order crystal-to-crystal thermal phase transition of Kinetic form to the thermodynamic form ; loop_ _publ_author_name M.Bhadbhade R.G.Gonnade A.K.Sanki M.S.Shashidhar data_Form(I)_1 _database_code_depnum_ccdc_archive 'CCDC 281351' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tri-O-p-bromo-benzoyl-myo-inositol 1,3,5-orthoformate ; _chemical_name_common 'Tri-O-p-bromo-benzoyl-myo-inositol 1,3,5-orthoformate' _chemical_melting_point ? _chemical_formula_moiety 'C28 H19 Br3 O9' _chemical_formula_sum 'C28 H19 Br3 O9' _chemical_formula_weight 739.16 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 57.945(13) _cell_length_b 6.0511(13) _cell_length_c 15.465(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.469(4) _cell_angle_gamma 90.00 _cell_volume 5273(2) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1842 _cell_measurement_theta_min 2.628 _cell_measurement_theta_max 20.776 _exptl_crystal_description 'thin needle' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.862 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2912 _exptl_absorpt_coefficient_mu 4.646 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2360 _exptl_absorpt_correction_T_max 0.9087 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18012 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0669 _diffrn_reflns_limit_h_min -68 _diffrn_reflns_limit_h_max 68 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4623 _reflns_number_gt 3261 _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, Ortep32, mercury 1.2.1' _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^)+(0.0507P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4623 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 Br1 Br 0.237518(9) 0.03743(9) 0.30921(3) 0.03310(17) Uani 1 1 d . . . Br2 Br 0.495877(10) 0.37806(11) 0.87665(4) 0.0487(2) Uani 1 1 d . . . Br3 Br 0.466515(10) 0.03917(11) 1.14558(4) 0.0456(2) Uani 1 1 d . . . O1 O 0.30884(5) 0.6866(5) 0.7771(2) 0.0195(7) Uani 1 1 d . . . O2 O 0.32125(5) 0.4179(5) 0.6504(2) 0.0203(7) Uani 1 1 d . . . O3 O 0.32148(5) 0.8727(5) 0.6663(2) 0.0223(8) Uani 1 1 d . . . O4 O 0.38383(5) 0.7734(5) 0.7634(2) 0.0206(7) Uani 1 1 d . . . O5 O 0.32981(6) 1.0145(5) 0.8088(2) 0.0233(8) Uani 1 1 d . . . O6 O 0.36945(5) 0.5675(5) 0.9049(2) 0.0200(7) Uani 1 1 d . . . O7 O 0.34731(6) 0.2440(5) 0.5868(2) 0.0206(7) Uani 1 1 d . . . O8 O 0.40148(6) 1.0895(6) 0.8184(2) 0.0339(9) Uani 1 1 d . . . O9 O 0.35050(6) 0.3282(5) 0.9755(2) 0.0227(8) Uani 1 1 d . . . C1 C 0.32973(8) 0.5504(8) 0.7975(3) 0.0195(11) Uani 1 1 d . . . H1 H 0.3261 0.4054 0.8191 0.023 Uiso 1 1 calc R . . C2 C 0.33954(8) 0.5252(8) 0.7161(3) 0.0205(11) Uani 1 1 d . . . H2 H 0.3542 0.4387 0.7290 0.025 Uiso 1 1 calc R . . C3 C 0.34342(8) 0.7528(7) 0.6814(3) 0.0197(11) Uani 1 1 d . . . H3 H 0.3487 0.7404 0.6258 0.024 Uiso 1 1 calc R . . C4 C 0.36131(8) 0.8850(8) 0.7494(3) 0.0202(11) Uani 1 1 d . . . H4 H 0.3628 1.0338 0.7262 0.024 Uiso 1 1 calc R . . C5 C 0.35212(8) 0.9004(7) 0.8332(3) 0.0204(11) Uani 1 1 d . . . H5 H 0.3633 0.9847 0.8786 0.024 Uiso 1 1 calc R . . C6 C 0.34705(8) 0.6761(7) 0.8710(3) 0.0198(11) Uani 1 1 d . . . H6 H 0.3394 0.7015 0.9204 0.024 Uiso 1 1 calc R . . C7 C 0.31341(8) 0.8911(8) 0.7446(3) 0.0206(11) Uani 1 1 d . . . H7 H 0.2985 0.9736 0.7304 0.025 Uiso 1 1 calc R . . C8 C 0.32719(8) 0.2952(7) 0.5861(3) 0.0177(11) Uani 1 1 d . . . C9 C 0.30576(8) 0.2370(8) 0.5173(3) 0.0194(11) Uani 1 1 d . . . C10 C 0.30454(9) 0.0356(8) 0.4738(3) 0.0225(11) Uani 1 1 d . . . H10 H 0.3173 -0.0613 0.4873 0.027 Uiso 1 1 calc R . . C11 C 0.28461(8) -0.0215(8) 0.4109(3) 0.0227(11) Uani 1 1 d . . . H11 H 0.2838 -0.1570 0.3819 0.027 Uiso 1 1 calc R . . C12 C 0.26568(8) 0.1241(9) 0.3908(3) 0.0236(12) Uani 1 1 d . . . C13 C 0.26683(9) 0.3290(9) 0.4311(3) 0.0267(12) Uani 1 1 d . . . H13 H 0.2543 0.4288 0.4154 0.032 Uiso 1 1 calc R . . C14 C 0.28684(8) 0.3819(8) 0.4949(3) 0.0225(11) Uani 1 1 d . . . H14 H 0.2877 0.5177 0.5236 0.027 Uiso 1 1 calc R . . C15 C 0.40297(8) 0.8975(9) 0.8000(3) 0.0245(12) Uani 1 1 d . . . C16 C 0.42525(8) 0.7699(8) 0.8166(3) 0.0226(12) Uani 1 1 d . . . C17 C 0.44558(9) 0.8599(9) 0.8706(3) 0.0281(12) Uani 1 1 d . . . H17 H 0.4450 0.9997 0.8949 0.034 Uiso 1 1 calc R . . C18 C 0.46633(9) 0.7467(9) 0.8884(4) 0.0331(14) Uani 1 1 d . . . H18 H 0.4799 0.8071 0.9253 0.040 Uiso 1 1 calc R . . C19 C 0.46708(9) 0.5421(9) 0.8513(3) 0.0323(13) Uani 1 1 d . . . C20 C 0.44757(9) 0.4477(9) 0.7979(3) 0.0316(13) Uani 1 1 d . . . H20 H 0.4485 0.3083 0.7737 0.038 Uiso 1 1 calc R . . C21 C 0.42625(9) 0.5631(8) 0.7803(3) 0.0286(12) Uani 1 1 d . . . H21 H 0.4127 0.5010 0.7441 0.034 Uiso 1 1 calc R . . C22 C 0.36882(9) 0.4009(7) 0.9624(3) 0.0205(11) Uani 1 1 d . . . C23 C 0.39272(8) 0.3170(8) 1.0050(3) 0.0212(11) Uani 1 1 d . . . C24 C 0.39447(9) 0.1193(8) 1.0514(3) 0.0246(12) Uani 1 1 d . . . H24 H 0.3808 0.0431 1.0548 0.030 Uiso 1 1 calc R . . C25 C 0.41618(9) 0.0356(8) 1.0921(3) 0.0269(12) Uani 1 1 d . . . H25 H 0.4174 -0.0984 1.1223 0.032 Uiso 1 1 calc R . . C26 C 0.43623(9) 0.1525(9) 1.0878(3) 0.0300(13) Uani 1 1 d . . . C27 C 0.43517(9) 0.3517(9) 1.0428(3) 0.0300(13) Uani 1 1 d . . . H27 H 0.4489 0.4290 1.0406 0.036 Uiso 1 1 calc R . . C28 C 0.41313(9) 0.4311(9) 1.0016(3) 0.0294(13) Uani 1 1 d . . . H28 H 0.4119 0.5643 0.9708 0.035 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 Br1 0.0253(3) 0.0436(4) 0.0266(3) -0.0067(3) -0.0016(2) -0.0056(2) Br2 0.0316(4) 0.0533(4) 0.0559(4) -0.0047(3) -0.0006(3) 0.0154(3) Br3 0.0334(3) 0.0541(4) 0.0459(4) 0.0107(3) 0.0023(3) 0.0170(3) O1 0.0186(18) 0.0176(18) 0.0230(19) 0.0019(15) 0.0061(14) 0.0005(14) O2 0.0209(18) 0.0216(19) 0.0173(18) -0.0056(14) 0.0023(14) -0.0023(14) O3 0.0252(19) 0.0228(18) 0.0183(18) 0.0038(15) 0.0040(15) 0.0032(15) O4 0.0183(18) 0.0226(19) 0.0201(18) 0.0002(15) 0.0031(14) -0.0019(14) O5 0.0264(19) 0.0184(19) 0.0240(19) -0.0021(15) 0.0037(15) 0.0030(15) O6 0.0196(18) 0.0193(18) 0.0208(18) 0.0054(15) 0.0040(14) 0.0019(14) O7 0.027(2) 0.0184(18) 0.0160(18) -0.0002(14) 0.0031(15) -0.0009(15) O8 0.030(2) 0.023(2) 0.047(2) -0.0053(18) 0.0061(18) -0.0019(16) O9 0.025(2) 0.025(2) 0.0172(18) 0.0019(15) 0.0030(15) -0.0011(15) C1 0.025(3) 0.017(3) 0.016(3) 0.001(2) 0.004(2) 0.003(2) C2 0.016(2) 0.023(3) 0.021(3) -0.003(2) 0.001(2) -0.002(2) C3 0.022(3) 0.022(3) 0.015(3) 0.001(2) 0.006(2) 0.006(2) C4 0.023(3) 0.017(3) 0.020(3) 0.002(2) 0.004(2) 0.000(2) C5 0.026(3) 0.012(3) 0.022(3) -0.001(2) 0.003(2) 0.004(2) C6 0.022(3) 0.021(3) 0.016(3) -0.003(2) 0.003(2) 0.002(2) C7 0.022(3) 0.021(3) 0.019(3) -0.001(2) 0.004(2) 0.007(2) C8 0.024(3) 0.013(3) 0.019(3) 0.003(2) 0.011(2) 0.001(2) C9 0.020(3) 0.022(3) 0.016(3) 0.005(2) 0.003(2) -0.003(2) C10 0.031(3) 0.025(3) 0.011(2) 0.001(2) 0.004(2) 0.004(2) C11 0.027(3) 0.022(3) 0.019(3) -0.004(2) 0.008(2) 0.001(2) C12 0.028(3) 0.034(3) 0.008(2) 0.000(2) 0.003(2) -0.007(2) C13 0.025(3) 0.033(3) 0.021(3) 0.004(2) 0.003(2) 0.006(2) C14 0.028(3) 0.018(3) 0.023(3) -0.003(2) 0.010(2) -0.002(2) C15 0.023(3) 0.026(3) 0.022(3) 0.003(2) 0.001(2) -0.004(2) C16 0.023(3) 0.026(3) 0.022(3) 0.004(2) 0.010(2) -0.002(2) C17 0.027(3) 0.029(3) 0.028(3) 0.001(2) 0.004(2) -0.001(2) C18 0.024(3) 0.039(4) 0.033(3) -0.003(3) 0.001(2) -0.004(3) C19 0.021(3) 0.049(4) 0.028(3) 0.002(3) 0.005(2) 0.008(3) C20 0.031(3) 0.032(3) 0.031(3) -0.003(3) 0.007(2) 0.005(3) C21 0.029(3) 0.026(3) 0.028(3) -0.006(2) 0.002(2) -0.002(2) C22 0.031(3) 0.015(3) 0.016(3) -0.004(2) 0.007(2) -0.002(2) C23 0.028(3) 0.024(3) 0.010(3) -0.004(2) 0.003(2) 0.003(2) C24 0.032(3) 0.020(3) 0.022(3) -0.001(2) 0.007(2) 0.001(2) C25 0.031(3) 0.027(3) 0.020(3) 0.002(2) 0.000(2) 0.007(2) C26 0.021(3) 0.042(3) 0.021(3) 0.002(3) -0.005(2) 0.014(3) C27 0.025(3) 0.037(3) 0.028(3) 0.002(3) 0.007(2) 0.002(2) C28 0.035(3) 0.028(3) 0.025(3) 0.004(2) 0.008(2) -0.001(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 Br1 C12 1.889(5) . ? Br2 C19 1.902(5) . ? Br3 C26 1.902(5) . ? O1 C7 1.385(5) . ? O1 C1 1.437(5) . ? O2 C8 1.348(5) . ? O2 C2 1.441(5) . ? O3 C7 1.401(5) . ? O3 C3 1.435(5) . ? O4 C15 1.350(6) . ? O4 C4 1.440(5) . ? O5 C7 1.416(5) . ? O5 C5 1.436(5) . ? O6 C22 1.351(5) . ? O6 C6 1.440(5) . ? O7 C8 1.204(5) . ? O8 C15 1.204(6) . ? O9 C22 1.209(5) . ? C1 C2 1.505(6) . ? C1 C6 1.531(6) . ? C2 C3 1.514(6) . ? C3 C4 1.521(6) . ? C4 C5 1.515(6) . ? C5 C6 1.533(6) . ? C8 C9 1.477(6) . ? C9 C14 1.383(7) . ? C9 C10 1.386(6) . ? C10 C11 1.370(7) . ? C11 C12 1.385(7) . ? C12 C13 1.383(7) . ? C13 C14 1.374(7) . ? C15 C16 1.475(7) . ? C16 C21 1.379(7) . ? C16 C17 1.386(7) . ? C17 C18 1.355(7) . ? C18 C19 1.370(7) . ? C19 C20 1.360(7) . ? C20 C21 1.389(7) . ? C22 C23 1.478(7) . ? C23 C28 1.381(7) . ? C23 C24 1.387(7) . ? C24 C25 1.366(7) . ? C25 C26 1.375(7) . ? C26 C27 1.386(7) . ? C27 C28 1.375(7) . ? 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 C7 O1 C1 111.7(3) . . ? C8 O2 C2 119.7(4) . . ? C7 O3 C3 111.2(3) . . ? C15 O4 C4 115.4(4) . . ? C7 O5 C5 110.3(3) . . ? C22 O6 C6 114.9(4) . . ? O1 C1 C2 109.7(4) . . ? O1 C1 C6 104.6(4) . . ? C2 C1 C6 111.1(4) . . ? O2 C2 C1 106.0(4) . . ? O2 C2 C3 107.8(4) . . ? C1 C2 C3 108.7(4) . . ? O3 C3 C2 108.5(4) . . ? O3 C3 C4 106.4(4) . . ? C2 C3 C4 111.5(4) . . ? O4 C4 C5 112.8(4) . . ? O4 C4 C3 107.8(4) . . ? C5 C4 C3 107.8(4) . . ? O5 C5 C4 106.2(4) . . ? O5 C5 C6 106.6(4) . . ? C4 C5 C6 114.1(4) . . ? O6 C6 C1 115.0(4) . . ? O6 C6 C5 107.9(4) . . ? C1 C6 C5 107.9(4) . . ? O1 C7 O3 111.9(4) . . ? O1 C7 O5 111.8(4) . . ? O3 C7 O5 110.1(4) . . ? O7 C8 O2 123.2(4) . . ? O7 C8 C9 126.5(4) . . ? O2 C8 C9 110.2(4) . . ? C14 C9 C10 119.2(4) . . ? C14 C9 C8 120.9(4) . . ? C10 C9 C8 119.9(4) . . ? C11 C10 C9 120.4(5) . . ? C10 C11 C12 119.5(5) . . ? C13 C12 C11 121.1(4) . . ? C13 C12 Br1 119.6(4) . . ? C11 C12 Br1 119.3(4) . . ? C14 C13 C12 118.5(5) . . ? C13 C14 C9 121.3(5) . . ? O8 C15 O4 122.6(4) . . ? O8 C15 C16 124.9(4) . . ? O4 C15 C16 112.5(4) . . ? C21 C16 C17 119.4(5) . . ? C21 C16 C15 121.5(4) . . ? C17 C16 C15 119.1(5) . . ? C18 C17 C16 120.9(5) . . ? C17 C18 C19 119.0(5) . . ? C20 C19 C18 122.1(5) . . ? C20 C19 Br2 118.1(4) . . ? C18 C19 Br2 119.8(4) . . ? C19 C20 C21 118.9(5) . . ? C16 C21 C20 119.7(5) . . ? O9 C22 O6 122.8(4) . . ? O9 C22 C23 124.7(4) . . ? O6 C22 C23 112.5(4) . . ? C28 C23 C24 119.4(5) . . ? C28 C23 C22 122.2(5) . . ? C24 C23 C22 118.3(4) . . ? C25 C24 C23 120.4(5) . . ? C24 C25 C26 119.0(5) . . ? C25 C26 C27 122.2(5) . . ? C25 C26 Br3 119.3(4) . . ? C27 C26 Br3 118.5(4) . . ? C28 C27 C26 117.7(5) . . ? C27 C28 C23 121.3(5) . . ? 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 C7 O1 C1 C2 -56.8(5) . . . . ? C7 O1 C1 C6 62.5(4) . . . . ? C8 O2 C2 C1 -153.5(4) . . . . ? C8 O2 C2 C3 90.2(4) . . . . ? O1 C1 C2 O2 -61.4(5) . . . . ? C6 C1 C2 O2 -176.5(4) . . . . ? O1 C1 C2 C3 54.3(5) . . . . ? C6 C1 C2 C3 -60.9(5) . . . . ? C7 O3 C3 C2 58.9(5) . . . . ? C7 O3 C3 C4 -61.2(4) . . . . ? O2 C2 C3 O3 59.2(4) . . . . ? C1 C2 C3 O3 -55.3(5) . . . . ? O2 C2 C3 C4 176.1(4) . . . . ? C1 C2 C3 C4 61.5(5) . . . . ? C15 O4 C4 C5 -80.3(5) . . . . ? C15 O4 C4 C3 160.9(4) . . . . ? O3 C3 C4 O4 -177.8(3) . . . . ? C2 C3 C4 O4 64.1(5) . . . . ? O3 C3 C4 C5 60.3(4) . . . . ? C2 C3 C4 C5 -57.9(5) . . . . ? C7 O5 C5 C4 62.4(4) . . . . ? C7 O5 C5 C6 -59.6(4) . . . . ? O4 C4 C5 O5 180.0(3) . . . . ? C3 C4 C5 O5 -61.2(4) . . . . ? O4 C4 C5 C6 -62.9(5) . . . . ? C3 C4 C5 C6 55.9(5) . . . . ? C22 O6 C6 C1 -77.8(5) . . . . ? C22 O6 C6 C5 161.7(4) . . . . ? O1 C1 C6 O6 178.2(3) . . . . ? C2 C1 C6 O6 -63.4(5) . . . . ? O1 C1 C6 C5 -61.3(4) . . . . ? C2 C1 C6 C5 57.0(5) . . . . ? O5 C5 C6 O6 -173.8(3) . . . . ? C4 C5 C6 O6 69.2(5) . . . . ? O5 C5 C6 C1 61.3(4) . . . . ? C4 C5 C6 C1 -55.6(5) . . . . ? C1 O1 C7 O3 60.3(5) . . . . ? C1 O1 C7 O5 -63.7(4) . . . . ? C3 O3 C7 O1 -61.9(5) . . . . ? C3 O3 C7 O5 63.1(4) . . . . ? C5 O5 C7 O1 61.5(5) . . . . ? C5 O5 C7 O3 -63.6(4) . . . . ? C2 O2 C8 O7 10.5(6) . . . . ? C2 O2 C8 C9 -169.3(4) . . . . ? O7 C8 C9 C14 -145.6(5) . . . . ? O2 C8 C9 C14 34.2(6) . . . . ? O7 C8 C9 C10 33.8(7) . . . . ? O2 C8 C9 C10 -146.3(4) . . . . ? C14 C9 C10 C11 -1.6(7) . . . . ? C8 C9 C10 C11 179.0(4) . . . . ? C9 C10 C11 C12 0.3(7) . . . . ? C10 C11 C12 C13 2.0(7) . . . . ? C10 C11 C12 Br1 -176.3(4) . . . . ? C11 C12 C13 C14 -2.9(7) . . . . ? Br1 C12 C13 C14 175.3(4) . . . . ? C12 C13 C14 C9 1.6(7) . . . . ? C10 C9 C14 C13 0.6(7) . . . . ? C8 C9 C14 C13 -179.9(4) . . . . ? C4 O4 C15 O8 -1.3(7) . . . . ? C4 O4 C15 C16 177.1(4) . . . . ? O8 C15 C16 C21 -168.6(5) . . . . ? O4 C15 C16 C21 13.1(7) . . . . ? O8 C15 C16 C17 11.9(8) . . . . ? O4 C15 C16 C17 -166.4(4) . . . . ? C21 C16 C17 C18 -0.4(8) . . . . ? C15 C16 C17 C18 179.2(5) . . . . ? C16 C17 C18 C19 0.9(8) . . . . ? C17 C18 C19 C20 -0.8(8) . . . . ? C17 C18 C19 Br2 -179.1(4) . . . . ? C18 C19 C20 C21 0.3(8) . . . . ? Br2 C19 C20 C21 178.6(4) . . . . ? C17 C16 C21 C20 -0.1(7) . . . . ? C15 C16 C21 C20 -179.7(5) . . . . ? C19 C20 C21 C16 0.2(8) . . . . ? C6 O6 C22 O9 9.5(6) . . . . ? C6 O6 C22 C23 -171.7(4) . . . . ? O9 C22 C23 C28 -167.1(5) . . . . ? O6 C22 C23 C28 14.2(6) . . . . ? O9 C22 C23 C24 11.5(7) . . . . ? O6 C22 C23 C24 -167.3(4) . . . . ? C28 C23 C24 C25 -1.2(7) . . . . ? C22 C23 C24 C25 -179.8(4) . . . . ? C23 C24 C25 C26 1.2(7) . . . . ? C24 C25 C26 C27 -0.6(8) . . . . ? C24 C25 C26 Br3 179.2(4) . . . . ? C25 C26 C27 C28 -0.1(8) . . . . ? Br3 C26 C27 C28 -179.9(4) . . . . ? C26 C27 C28 C23 0.2(8) . . . . ? C24 C23 C28 C27 0.5(7) . . . . ? C22 C23 C28 C27 179.0(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 C21 H21 O8 0.93 2.88 3.318(6) 110.3 1_545 C24 H24 O7 0.93 2.73 3.646(6) 167.5 6_556 C10 H10 O9 0.93 2.55 3.450(6) 163.3 6 C4 H4 O7 0.98 2.48 3.278(6) 138.0 1_565 C5 H5 O9 0.98 2.76 3.413(6) 124.4 1_565 C6 H6 O7 0.98 2.53 3.370(6) 143.8 6_566 C1 H1 O5 0.98 2.38 3.248(6) 146.7 1_545 C3 H3 O9 0.98 2.39 3.339(6) 163.7 6_565 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.846 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.106 data_Form(II)_1 _database_code_depnum_ccdc_archive 'CCDC 281352' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tri-O-p-bromo-benzoyl-myo-inositol 1,3,5-orthoformate ; _chemical_name_common 'Tri-O-p-bromo-benzoyl-myo-inositol 1,3,5-orthoformate' _chemical_melting_point 469-470 _chemical_formula_moiety 'C28 H19 Br3 O9' _chemical_formula_sum 'C28 H19 Br3 O9' _chemical_formula_weight 739.16 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' Br Br -0.2901 2.4595 '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' _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 10.002(2) _cell_length_b 12.126(2) _cell_length_c 13.146(3) _cell_angle_alpha 70.536(3) _cell_angle_beta 80.100(3) _cell_angle_gamma 68.503(3) _cell_volume 1396.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6378 _cell_measurement_theta_min 2.472 _cell_measurement_theta_max 26.468 _exptl_crystal_description octahedral _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.57 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 4.386 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1657 _exptl_absorpt_correction_T_max 0.3528 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13350 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4893 _reflns_number_gt 4105 _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, Ortep32, mercury 1.2.1' _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^)+(0.0481P)^2^+1.7004P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4893 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Br1 Br 1.16982(5) 0.71462(5) 0.19422(5) 0.07868(18) Uani 1 1 d . . . Br2 Br 0.79717(4) -0.06217(4) 1.25785(3) 0.05726(14) Uani 1 1 d . . . Br3 Br 1.32951(9) -0.46950(6) 0.96408(8) 0.1420(4) Uani 1 1 d . . . O1 O 0.6773(3) 0.1904(2) 0.3903(2) 0.0543(6) Uani 1 1 d . . . O2 O 0.7991(3) 0.3228(2) 0.4801(2) 0.0489(6) Uani 1 1 d . . . O3 O 0.5082(3) 0.3368(2) 0.4655(2) 0.0505(6) Uani 1 1 d . . . O4 O 0.5763(3) 0.1385(2) 0.74493(19) 0.0488(6) Uani 1 1 d . . . O5 O 0.4737(3) 0.1502(2) 0.4870(2) 0.0554(7) Uani 1 1 d . . . O6 O 0.7960(3) -0.0356(2) 0.6482(2) 0.0488(6) Uani 1 1 d . . . O7 O 1.0210(3) 0.1965(2) 0.5332(2) 0.0599(7) Uani 1 1 d . . . O8 O 0.3894(3) 0.2729(3) 0.8118(3) 0.0741(9) Uani 1 1 d . . . O9 O 0.6953(3) -0.1863(2) 0.7060(2) 0.0577(7) Uani 1 1 d . . . C1 C 0.7611(4) 0.1311(3) 0.4856(3) 0.0473(8) Uani 1 1 d . . . H1 H 0.8630 0.0954 0.4649 0.046(10) Uiso 1 1 d R . . C2 C 0.7418(4) 0.2256(3) 0.5449(3) 0.0433(8) Uani 1 1 d . . . H2 H 0.7887 0.1839 0.6137 0.036(8) Uiso 1 1 d R . . C3 C 0.5810(4) 0.2877(3) 0.5655(3) 0.0458(8) Uani 1 1 d . . . H3 H 0.5648 0.3544 0.5973 0.055(11) Uiso 1 1 d R . . C4 C 0.5148(4) 0.1914(3) 0.6411(3) 0.0464(8) Uani 1 1 d . . . H4 H 0.4106 0.2310 0.6507 0.039(9) Uiso 1 1 d R . . C5 C 0.5440(4) 0.0885(4) 0.5892(3) 0.0496(9) Uani 1 1 d . . . H5 H 0.5027 0.0254 0.6354 0.060(11) Uiso 1 1 d R . . C6 C 0.7032(4) 0.0281(3) 0.5590(3) 0.0472(8) Uani 1 1 d . . . H6 H 0.7115 -0.0297 0.5191 0.055(11) Uiso 1 1 d R . . C7 C 0.5308(4) 0.2411(4) 0.4192(3) 0.0547(9) Uani 1 1 d . . . H7 H 0.4791 0.2785 0.3525 0.042(9) Uiso 1 1 d R . . C8 C 0.9428(4) 0.2962(3) 0.4826(3) 0.0448(8) Uani 1 1 d . . . C9 C 0.9909(4) 0.4018(3) 0.4161(3) 0.0447(8) Uani 1 1 d . . . C10 C 1.1325(4) 0.3932(3) 0.4210(3) 0.0492(8) Uani 1 1 d . . . H10 H 1.1931 0.3235 0.4676 0.052(10) Uiso 1 1 d R . . C11 C 1.1844(4) 0.4872(4) 0.3568(3) 0.0550(10) Uani 1 1 d . . . H11 H 1.2783 0.4821 0.3615 0.061(12) Uiso 1 1 d R . . C12 C 1.0935(4) 0.5895(4) 0.2864(3) 0.0548(9) Uani 1 1 d . . . C13 C 0.9523(4) 0.6014(4) 0.2809(3) 0.0567(10) Uani 1 1 d . . . H13 H 0.8927 0.6716 0.2340 0.057(11) Uiso 1 1 d R . . C14 C 0.8998(4) 0.5084(3) 0.3461(3) 0.0513(9) Uani 1 1 d . . . H14 H 0.8041 0.5168 0.3438 0.061(12) Uiso 1 1 d R . . C15 C 0.5015(4) 0.1885(3) 0.8248(3) 0.0480(8) Uani 1 1 d . . . C16 C 0.5766(4) 0.1260(3) 0.9279(3) 0.0438(8) Uani 1 1 d . . . C17 C 0.5131(4) 0.1666(4) 1.0176(3) 0.0536(9) Uani 1 1 d . . . H17 H 0.4259 0.2314 1.0119 0.062(12) Uiso 1 1 d R . . C18 C 0.5784(4) 0.1113(4) 1.1152(3) 0.0538(9) Uani 1 1 d . . . H18 H 0.5357 0.1391 1.1748 0.053(11) Uiso 1 1 d R . . C19 C 0.7072(4) 0.0148(3) 1.1230(3) 0.0469(8) Uani 1 1 d . . . C20 C 0.7729(4) -0.0271(4) 1.0352(3) 0.0549(9) Uani 1 1 d . . . H20 H 0.8603 -0.0916 1.0413 0.067(13) Uiso 1 1 d R . . C21 C 0.7068(4) 0.0290(4) 0.9377(3) 0.0540(9) Uani 1 1 d . . . H21 H 0.7492 0.0010 0.8784 0.061(12) Uiso 1 1 d R . . C22 C 0.7900(4) -0.1489(3) 0.7096(3) 0.0451(8) Uani 1 1 d . . . C23 C 0.9161(4) -0.2207(3) 0.7779(3) 0.0462(8) Uani 1 1 d . . . C24 C 0.9391(5) -0.3452(4) 0.8282(4) 0.0666(12) Uani 1 1 d . . . H24 H 0.8705 -0.3788 0.8253 0.077(14) Uiso 1 1 d R . . C25 C 1.0628(6) -0.4199(4) 0.8823(4) 0.0818(15) Uani 1 1 d . . . H25 H 1.0797 -0.5043 0.9132 0.15(3) Uiso 1 1 d R . . C26 C 1.1591(5) -0.3680(4) 0.8907(4) 0.0763(14) Uani 1 1 d . . . C27 C 1.1375(5) -0.2423(4) 0.8424(4) 0.0763(14) Uani 1 1 d . . . H27 H 1.2040 -0.2077 0.8478 0.105(19) Uiso 1 1 d R . . C28 C 1.0163(4) -0.1699(4) 0.7851(4) 0.0603(10) Uani 1 1 d . . . H28 H 1.0008 -0.0859 0.7516 0.065(12) Uiso 1 1 d 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 Br1 0.0696(3) 0.0632(3) 0.0988(4) -0.0118(3) 0.0078(3) -0.0335(2) Br2 0.0613(3) 0.0556(2) 0.0535(2) -0.01151(18) -0.01223(18) -0.01801(19) Br3 0.1208(6) 0.0765(4) 0.2125(9) -0.0238(5) -0.1134(6) 0.0145(4) O1 0.0538(15) 0.0570(16) 0.0457(14) -0.0169(12) -0.0103(12) -0.0064(13) O2 0.0390(13) 0.0414(13) 0.0596(15) -0.0046(11) -0.0096(11) -0.0121(11) O3 0.0468(14) 0.0438(14) 0.0519(14) -0.0098(11) -0.0147(11) -0.0034(11) O4 0.0409(13) 0.0546(15) 0.0455(13) -0.0126(11) -0.0066(11) -0.0098(12) O5 0.0503(15) 0.0558(16) 0.0613(16) -0.0132(13) -0.0226(12) -0.0139(13) O6 0.0448(13) 0.0386(13) 0.0609(15) -0.0106(11) -0.0173(11) -0.0087(11) O7 0.0446(14) 0.0469(15) 0.0730(18) -0.0019(13) -0.0162(13) -0.0066(12) O8 0.0627(19) 0.072(2) 0.0713(19) -0.0324(16) -0.0214(15) 0.0142(16) O9 0.0528(16) 0.0519(15) 0.0730(18) -0.0153(13) -0.0118(13) -0.0218(13) C1 0.0411(19) 0.046(2) 0.049(2) -0.0133(16) -0.0075(15) -0.0065(16) C2 0.0401(18) 0.0403(18) 0.0466(19) -0.0076(15) -0.0099(15) -0.0115(15) C3 0.0416(19) 0.0424(19) 0.051(2) -0.0144(16) -0.0107(15) -0.0072(15) C4 0.0353(18) 0.053(2) 0.0482(19) -0.0134(16) -0.0061(15) -0.0116(16) C5 0.0436(19) 0.050(2) 0.055(2) -0.0112(17) -0.0143(17) -0.0153(17) C6 0.048(2) 0.0410(19) 0.053(2) -0.0142(16) -0.0140(16) -0.0095(16) C7 0.051(2) 0.056(2) 0.052(2) -0.0132(18) -0.0185(18) -0.0074(19) C8 0.0395(18) 0.045(2) 0.0475(19) -0.0134(16) -0.0078(15) -0.0097(16) C9 0.0397(18) 0.0404(19) 0.053(2) -0.0162(16) -0.0050(15) -0.0088(15) C10 0.0420(19) 0.044(2) 0.058(2) -0.0147(17) -0.0096(17) -0.0078(16) C11 0.0385(19) 0.053(2) 0.075(3) -0.023(2) -0.0046(18) -0.0135(17) C12 0.050(2) 0.046(2) 0.068(3) -0.0162(19) 0.0034(18) -0.0180(18) C13 0.050(2) 0.041(2) 0.070(3) -0.0072(18) -0.0117(19) -0.0082(18) C14 0.0393(19) 0.042(2) 0.067(2) -0.0115(17) -0.0092(17) -0.0084(16) C15 0.045(2) 0.046(2) 0.054(2) -0.0153(17) -0.0018(16) -0.0163(18) C16 0.0416(18) 0.0401(18) 0.050(2) -0.0125(15) -0.0017(15) -0.0152(15) C17 0.046(2) 0.046(2) 0.062(2) -0.0179(18) -0.0038(18) -0.0048(17) C18 0.056(2) 0.054(2) 0.050(2) -0.0212(18) -0.0003(18) -0.0138(19) C19 0.049(2) 0.044(2) 0.048(2) -0.0104(16) -0.0071(16) -0.0174(17) C20 0.049(2) 0.048(2) 0.058(2) -0.0165(18) -0.0096(18) -0.0009(18) C21 0.053(2) 0.053(2) 0.053(2) -0.0211(18) -0.0019(18) -0.0105(18) C22 0.0441(19) 0.0374(18) 0.052(2) -0.0159(16) -0.0030(16) -0.0095(16) C23 0.047(2) 0.0398(19) 0.049(2) -0.0129(16) -0.0072(16) -0.0106(16) C24 0.082(3) 0.047(2) 0.072(3) -0.007(2) -0.027(2) -0.023(2) C25 0.104(4) 0.042(2) 0.095(4) -0.007(2) -0.048(3) -0.013(2) C26 0.070(3) 0.052(3) 0.096(4) -0.018(2) -0.043(3) 0.006(2) C27 0.061(3) 0.060(3) 0.107(4) -0.013(3) -0.034(3) -0.016(2) C28 0.051(2) 0.046(2) 0.076(3) -0.006(2) -0.018(2) -0.0118(18) _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 Br1 C12 1.913(4) . ? Br2 C19 1.912(4) . ? Br3 C26 1.894(4) . ? O1 C7 1.404(5) . ? O1 C1 1.452(4) . ? O2 C8 1.356(4) . ? O2 C2 1.449(4) . ? O3 C7 1.414(5) . ? O3 C3 1.450(4) . ? O4 C15 1.361(5) . ? O4 C4 1.439(4) . ? O5 C7 1.403(5) . ? O5 C5 1.458(4) . ? O6 C22 1.360(4) . ? O6 C6 1.441(4) . ? O7 C8 1.210(4) . ? O8 C15 1.201(5) . ? O9 C22 1.203(4) . ? C1 C2 1.530(5) . ? C1 C6 1.536(5) . ? C2 C3 1.525(5) . ? C3 C4 1.535(5) . ? C4 C5 1.529(5) . ? C5 C6 1.534(5) . ? C8 C9 1.483(5) . ? C9 C10 1.393(5) . ? C9 C14 1.407(5) . ? C10 C11 1.387(5) . ? C11 C12 1.385(6) . ? C12 C13 1.378(6) . ? C13 C14 1.385(5) . ? C15 C16 1.491(5) . ? C16 C21 1.390(5) . ? C16 C17 1.391(5) . ? C17 C18 1.385(6) . ? C18 C19 1.379(5) . ? C19 C20 1.381(5) . ? C20 C21 1.387(6) . ? C22 C23 1.490(5) . ? C23 C24 1.380(5) . ? C23 C28 1.384(5) . ? C24 C25 1.381(6) . ? C25 C26 1.365(7) . ? C26 C27 1.391(7) . ? C27 C28 1.379(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 C7 O1 C1 110.5(3) . . ? C8 O2 C2 116.1(3) . . ? C7 O3 C3 110.5(3) . . ? C15 O4 C4 116.8(3) . . ? C7 O5 C5 111.6(3) . . ? C22 O6 C6 116.5(3) . . ? O1 C1 C2 109.9(3) . . ? O1 C1 C6 107.0(3) . . ? C2 C1 C6 109.6(3) . . ? O2 C2 C3 107.0(3) . . ? O2 C2 C1 111.7(3) . . ? C3 C2 C1 108.2(3) . . ? O3 C3 C2 110.2(3) . . ? O3 C3 C4 106.2(3) . . ? C2 C3 C4 109.9(3) . . ? O4 C4 C5 109.3(3) . . ? O4 C4 C3 111.2(3) . . ? C5 C4 C3 108.5(3) . . ? O5 C5 C4 105.2(3) . . ? O5 C5 C6 105.5(3) . . ? C4 C5 C6 114.4(3) . . ? O6 C6 C5 115.5(3) . . ? O6 C6 C1 105.7(3) . . ? C5 C6 C1 108.1(3) . . ? O5 C7 O1 112.1(3) . . ? O5 C7 O3 111.7(3) . . ? O1 C7 O3 110.8(3) . . ? O7 C8 O2 122.9(3) . . ? O7 C8 C9 124.9(3) . . ? O2 C8 C9 112.2(3) . . ? C10 C9 C14 119.1(3) . . ? C10 C9 C8 118.6(3) . . ? C14 C9 C8 122.3(3) . . ? C11 C10 C9 120.7(4) . . ? C12 C11 C10 118.9(3) . . ? C13 C12 C11 121.7(4) . . ? C13 C12 Br1 120.2(3) . . ? C11 C12 Br1 118.1(3) . . ? C12 C13 C14 119.5(4) . . ? C13 C14 C9 120.1(3) . . ? O8 C15 O4 123.2(3) . . ? O8 C15 C16 125.3(4) . . ? O4 C15 C16 111.6(3) . . ? C21 C16 C17 119.0(3) . . ? C21 C16 C15 122.5(3) . . ? C17 C16 C15 118.5(3) . . ? C18 C17 C16 120.7(4) . . ? C19 C18 C17 119.2(4) . . ? C18 C19 C20 121.4(3) . . ? C18 C19 Br2 119.3(3) . . ? C20 C19 Br2 119.3(3) . . ? C19 C20 C21 119.0(4) . . ? C20 C21 C16 120.8(4) . . ? O9 C22 O6 123.3(3) . . ? O9 C22 C23 125.0(3) . . ? O6 C22 C23 111.7(3) . . ? C24 C23 C28 119.3(4) . . ? C24 C23 C22 117.9(3) . . ? C28 C23 C22 122.6(3) . . ? C23 C24 C25 120.7(4) . . ? C26 C25 C24 119.3(4) . . ? C25 C26 C27 121.2(4) . . ? C25 C26 Br3 119.7(4) . . ? C27 C26 Br3 119.1(4) . . ? C28 C27 C26 118.8(4) . . ? C27 C28 C23 120.6(4) . . ? 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 C7 O1 C1 C2 -58.9(4) . . . . ? C7 O1 C1 C6 60.0(4) . . . . ? C8 O2 C2 C3 158.7(3) . . . . ? C8 O2 C2 C1 -83.0(4) . . . . ? O1 C1 C2 O2 -64.5(4) . . . . ? C6 C1 C2 O2 178.2(3) . . . . ? O1 C1 C2 C3 53.0(4) . . . . ? C6 C1 C2 C3 -64.3(4) . . . . ? C7 O3 C3 C2 58.4(4) . . . . ? C7 O3 C3 C4 -60.6(4) . . . . ? O2 C2 C3 O3 67.5(3) . . . . ? C1 C2 C3 O3 -53.0(4) . . . . ? O2 C2 C3 C4 -175.8(3) . . . . ? C1 C2 C3 C4 63.7(4) . . . . ? C15 O4 C4 C5 -143.5(3) . . . . ? C15 O4 C4 C3 96.8(4) . . . . ? O3 C3 C4 O4 -178.3(3) . . . . ? C2 C3 C4 O4 62.5(4) . . . . ? O3 C3 C4 C5 61.5(3) . . . . ? C2 C3 C4 C5 -57.7(4) . . . . ? C7 O5 C5 C4 60.7(4) . . . . ? C7 O5 C5 C6 -60.6(4) . . . . ? O4 C4 C5 O5 178.0(3) . . . . ? C3 C4 C5 O5 -60.6(3) . . . . ? O4 C4 C5 C6 -66.7(4) . . . . ? C3 C4 C5 C6 54.7(4) . . . . ? C22 O6 C6 C5 76.7(4) . . . . ? C22 O6 C6 C1 -163.9(3) . . . . ? O5 C5 C6 O6 178.0(3) . . . . ? C4 C5 C6 O6 62.9(4) . . . . ? O5 C5 C6 C1 59.9(3) . . . . ? C4 C5 C6 C1 -55.2(4) . . . . ? O1 C1 C6 O6 175.3(3) . . . . ? C2 C1 C6 O6 -65.6(3) . . . . ? O1 C1 C6 C5 -60.5(4) . . . . ? C2 C1 C6 C5 58.6(4) . . . . ? C5 O5 C7 O1 62.5(4) . . . . ? C5 O5 C7 O3 -62.5(4) . . . . ? C1 O1 C7 O5 -61.5(4) . . . . ? C1 O1 C7 O3 64.0(4) . . . . ? C3 O3 C7 O5 62.0(4) . . . . ? C3 O3 C7 O1 -63.7(4) . . . . ? C2 O2 C8 O7 2.0(5) . . . . ? C2 O2 C8 C9 -178.7(3) . . . . ? O7 C8 C9 C10 -8.0(6) . . . . ? O2 C8 C9 C10 172.6(3) . . . . ? O7 C8 C9 C14 170.0(4) . . . . ? O2 C8 C9 C14 -9.3(5) . . . . ? C14 C9 C10 C11 -0.9(6) . . . . ? C8 C9 C10 C11 177.2(3) . . . . ? C9 C10 C11 C12 -0.9(6) . . . . ? C10 C11 C12 C13 1.9(6) . . . . ? C10 C11 C12 Br1 -177.4(3) . . . . ? C11 C12 C13 C14 -0.9(6) . . . . ? Br1 C12 C13 C14 178.3(3) . . . . ? C12 C13 C14 C9 -0.9(6) . . . . ? C10 C9 C14 C13 1.9(6) . . . . ? C8 C9 C14 C13 -176.2(4) . . . . ? C4 O4 C15 O8 -0.1(5) . . . . ? C4 O4 C15 C16 -179.8(3) . . . . ? O8 C15 C16 C21 -179.6(4) . . . . ? O4 C15 C16 C21 0.1(5) . . . . ? O8 C15 C16 C17 0.5(6) . . . . ? O4 C15 C16 C17 -179.8(3) . . . . ? C21 C16 C17 C18 0.0(6) . . . . ? C15 C16 C17 C18 179.8(4) . . . . ? C16 C17 C18 C19 -0.4(6) . . . . ? C17 C18 C19 C20 0.6(6) . . . . ? C17 C18 C19 Br2 -179.7(3) . . . . ? C18 C19 C20 C21 -0.5(6) . . . . ? Br2 C19 C20 C21 179.8(3) . . . . ? C19 C20 C21 C16 0.1(6) . . . . ? C17 C16 C21 C20 0.1(6) . . . . ? C15 C16 C21 C20 -179.7(4) . . . . ? C6 O6 C22 O9 -14.4(5) . . . . ? C6 O6 C22 C23 163.9(3) . . . . ? O9 C22 C23 C24 10.6(6) . . . . ? O6 C22 C23 C24 -167.6(4) . . . . ? O9 C22 C23 C28 -174.9(4) . . . . ? O6 C22 C23 C28 6.8(5) . . . . ? C28 C23 C24 C25 -2.2(7) . . . . ? C22 C23 C24 C25 172.5(4) . . . . ? C23 C24 C25 C26 3.5(8) . . . . ? C24 C25 C26 C27 -2.5(9) . . . . ? C24 C25 C26 Br3 -179.7(4) . . . . ? C25 C26 C27 C28 0.0(9) . . . . ? Br3 C26 C27 C28 177.2(4) . . . . ? C26 C27 C28 C23 1.4(8) . . . . ? C24 C23 C28 C27 -0.4(7) . . . . ? C22 C23 C28 C27 -174.7(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 C7 H7 O9 0.98 2.71 3.373(5) 125.2 2_656 C11 H11 O3 0.93 2.60 3.374(5) 140.9 1_655 C18 H18 O9 0.93 2.55 3.351(5) 144.5 2_657 C6 H6 O5 0.98 2.77 3.495(4) 131.1 2_656 C10 H10 O5 0.93 2.82 3.610(4) 144.1 1_655 C13 H13 O8 0.93 2.78 3.445(5) 129.8 2_666 C13 H13 Br2 0.93 3.12 3.720(4) 123.8 1_564 C5 H5 Br2 0.98 3.03 3.715(4) 128.4 2_657 C27 H27 Br2 0.93 3.10 3.745(5) 128.4 2_757 C28 H28 Br2 0.93 3.12 3.761(4) 127.5 2_757 C14 H14 O8 0.93 2.95 3.533(5) 122.2 2_666 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.211 _refine_diff_density_min -1.053 _refine_diff_density_rms 0.069 data_Form(II)_2 _database_code_depnum_ccdc_archive 'CCDC 281353' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tri-O-p-chloro-benzoyl-myo-inositol 1,3,5-orthoformate ; _chemical_name_common 'Tri-O-p-chloro-benzoyl-myo-inositol 1,3,5-orthoformate' _chemical_melting_point 468-469 _chemical_formula_moiety 'C28 H19 Cl3 O9' _chemical_formula_sum 'C28 H19 Cl3 O9' _chemical_formula_weight 605.78 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' Cl Cl 0.1484 0.1585 '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 10.2740(17) _cell_length_b 11.2899(18) _cell_length_c 12.717(2) _cell_angle_alpha 75.582(3) _cell_angle_beta 86.976(3) _cell_angle_gamma 68.503(3) _cell_volume 1328.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2508 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 22.086 _exptl_crystal_description octahedral _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8316 _exptl_absorpt_correction_T_max 0.9531 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9709 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4648 _reflns_number_gt 3362 _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, Ortep32, mercury 1.2.1' _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^)+(0.0820P)^2^+0.3543P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4648 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 Cl2 Cl 0.20102(10) 1.07005(9) 0.23697(7) 0.0826(3) Uani 1 1 d . . . Cl1 Cl -0.13867(10) 0.30419(10) 1.28650(8) 0.0867(3) Uani 1 1 d . . . Cl3 Cl -0.32083(11) 1.44051(12) 0.50773(11) 0.1138(4) Uani 1 1 d . . . O2 O 0.20582(18) 0.67748(17) 1.02828(14) 0.0498(5) Uani 1 1 d . . . O1 O 0.34728(19) 0.82016(17) 1.10895(14) 0.0531(5) Uani 1 1 d . . . O3 O 0.49350(19) 0.64800(17) 1.04190(14) 0.0517(5) Uani 1 1 d . . . O5 O 0.53749(19) 0.84029(18) 1.01213(15) 0.0550(5) Uani 1 1 d . . . O6 O 0.20969(18) 1.02979(17) 0.84477(14) 0.0516(5) Uani 1 1 d . . . O4 O 0.40637(18) 0.82764(19) 0.75722(14) 0.0560(5) Uani 1 1 d . . . O9 O 0.3078(2) 1.17539(19) 0.76565(16) 0.0610(5) Uani 1 1 d . . . O7 O -0.0115(2) 0.81857(19) 0.97359(17) 0.0643(6) Uani 1 1 d . . . C2 C 0.2603(3) 0.7689(2) 0.9599(2) 0.0458(6) Uani 1 1 d . . . H2 H 0.2067 0.8082 0.8903 0.055 Uiso 1 1 calc R . . C3 C 0.4110(3) 0.6930(3) 0.9412(2) 0.0471(6) Uani 1 1 d . . . H3 H 0.4173 0.6179 0.9130 0.057 Uiso 1 1 calc R . . C6 C 0.3102(3) 0.9725(3) 0.9352(2) 0.0479(6) Uani 1 1 d . . . H6 H 0.3101 1.0410 0.9699 0.058 Uiso 1 1 calc R . . C22 C 0.2125(3) 1.1382(3) 0.7716(2) 0.0477(6) Uani 1 1 d . . . C1 C 0.2568(3) 0.8762(2) 1.0133(2) 0.0464(6) Uani 1 1 d . . . H1 H 0.1609 0.9221 1.0322 0.056 Uiso 1 1 calc R . . C9 C 0.0193(3) 0.6102(2) 1.0932(2) 0.0456(6) Uani 1 1 d . . . C5 C 0.4602(3) 0.8959(3) 0.9093(2) 0.0515(7) Uani 1 1 d . . . H5 H 0.4996 0.9552 0.8607 0.062 Uiso 1 1 calc R . . C14 C 0.1055(3) 0.5073(3) 1.1725(2) 0.0515(7) Uani 1 1 d . . . H14 H 0.1964 0.5011 1.1851 0.062 Uiso 1 1 calc R . . C23 C 0.0818(3) 1.2035(2) 0.7027(2) 0.0470(6) Uani 1 1 d . . . C7 C 0.4846(3) 0.7538(3) 1.0835(2) 0.0517(7) Uani 1 1 d . . . H7 H 0.5425 0.7186 1.1511 0.062 Uiso 1 1 calc R . . C8 C 0.0652(3) 0.7141(3) 1.0257(2) 0.0485(6) Uani 1 1 d . . . C10 C -0.1150(3) 0.6176(3) 1.0745(2) 0.0548(7) Uani 1 1 d . . . H10 H -0.1736 0.6873 1.0217 0.066 Uiso 1 1 calc R . . C16 C 0.4072(3) 0.8601(3) 0.5680(2) 0.0509(7) Uani 1 1 d . . . C15 C 0.4824(3) 0.7925(3) 0.6739(2) 0.0568(7) Uani 1 1 d . . . C4 C 0.4751(3) 0.7807(3) 0.8626(2) 0.0507(7) Uani 1 1 d . . . H4 H 0.5746 0.7309 0.8565 0.061 Uiso 1 1 calc R . . C28 C -0.0397(3) 1.1829(3) 0.7348(2) 0.0585(7) Uani 1 1 d . . . H28 H -0.0381 1.1190 0.7976 0.070 Uiso 1 1 calc R . . C19 C 0.2800(3) 0.9888(3) 0.3654(2) 0.0596(7) Uani 1 1 d . . . C13 C 0.0568(3) 0.4136(3) 1.2332(2) 0.0574(7) Uani 1 1 d . . . H13 H 0.1139 0.3451 1.2876 0.069 Uiso 1 1 calc R . . C21 C 0.2711(3) 0.9469(3) 0.5577(2) 0.0622(8) Uani 1 1 d . . . H21 H 0.2220 0.9618 0.6196 0.075 Uiso 1 1 calc R . . C12 C -0.0760(3) 0.4224(3) 1.2125(2) 0.0560(7) Uani 1 1 d . . . C17 C 0.4772(3) 0.8372(3) 0.4753(2) 0.0663(8) Uani 1 1 d . . . H17 H 0.5688 0.7772 0.4815 0.080 Uiso 1 1 calc R . . C11 C -0.1627(3) 0.5235(3) 1.1329(3) 0.0597(8) Uani 1 1 d . . . H11 H -0.2524 0.5277 1.1190 0.072 Uiso 1 1 calc R . . O8 O 0.6006(3) 0.7167(3) 0.6862(2) 0.1068(10) Uani 1 1 d . . . C26 C -0.1642(3) 1.3455(3) 0.5811(3) 0.0662(8) Uani 1 1 d . . . C20 C 0.2062(3) 1.0123(3) 0.4562(2) 0.0685(9) Uani 1 1 d . . . H20 H 0.1140 1.0712 0.4494 0.082 Uiso 1 1 calc R . . C25 C -0.0433(3) 1.3629(3) 0.5437(3) 0.0743(9) Uani 1 1 d . . . H25 H -0.0440 1.4204 0.4770 0.089 Uiso 1 1 calc R . . C24 C 0.0790(3) 1.2945(3) 0.6060(3) 0.0643(8) Uani 1 1 d . . . H24 H 0.1604 1.3094 0.5831 0.077 Uiso 1 1 calc R . . C18 C 0.4142(3) 0.9010(3) 0.3744(2) 0.0689(9) Uani 1 1 d . . . H18 H 0.4626 0.8846 0.3125 0.083 Uiso 1 1 calc R . . C27 C -0.1632(3) 1.2552(3) 0.6755(3) 0.0671(8) Uani 1 1 d . . . H27 H -0.2455 1.2429 0.6993 0.081 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 Cl2 0.1027(7) 0.0710(6) 0.0558(5) -0.0088(4) -0.0125(4) -0.0131(5) Cl1 0.0842(6) 0.0898(7) 0.1008(7) -0.0177(5) 0.0192(5) -0.0544(5) Cl3 0.0698(6) 0.1129(9) 0.1270(9) -0.0129(7) -0.0351(6) -0.0028(6) O2 0.0436(10) 0.0431(10) 0.0577(11) -0.0026(8) -0.0047(8) -0.0158(8) O1 0.0600(12) 0.0506(11) 0.0432(10) -0.0089(8) -0.0044(8) -0.0149(9) O3 0.0528(11) 0.0422(10) 0.0514(10) -0.0060(8) -0.0102(8) -0.0095(8) O5 0.0541(11) 0.0559(11) 0.0549(11) -0.0039(9) -0.0138(9) -0.0240(9) O6 0.0531(11) 0.0434(10) 0.0535(11) 0.0015(8) -0.0102(8) -0.0192(9) O4 0.0447(10) 0.0724(13) 0.0418(10) -0.0100(9) -0.0017(8) -0.0131(9) O9 0.0530(12) 0.0592(12) 0.0671(13) 0.0015(10) -0.0041(9) -0.0266(10) O7 0.0507(11) 0.0484(12) 0.0770(14) 0.0020(10) -0.0123(10) -0.0082(10) C2 0.0478(15) 0.0407(14) 0.0447(14) -0.0023(11) -0.0043(11) -0.0159(12) C3 0.0463(15) 0.0443(15) 0.0481(15) -0.0111(12) -0.0083(11) -0.0123(12) C6 0.0516(15) 0.0416(14) 0.0483(15) -0.0072(12) -0.0076(12) -0.0157(12) C22 0.0485(15) 0.0449(15) 0.0479(15) -0.0094(12) 0.0029(12) -0.0165(13) C1 0.0452(15) 0.0433(15) 0.0453(14) -0.0077(12) -0.0032(11) -0.0113(12) C9 0.0388(14) 0.0423(14) 0.0536(15) -0.0141(12) -0.0031(11) -0.0103(11) C5 0.0509(16) 0.0536(16) 0.0478(15) -0.0007(13) -0.0091(12) -0.0228(13) C14 0.0392(14) 0.0520(16) 0.0609(17) -0.0104(13) -0.0034(12) -0.0156(12) C23 0.0458(15) 0.0391(14) 0.0523(15) -0.0082(12) -0.0009(12) -0.0127(11) C7 0.0537(17) 0.0495(16) 0.0485(15) -0.0069(13) -0.0104(12) -0.0168(13) C8 0.0416(15) 0.0447(16) 0.0552(16) -0.0126(13) -0.0070(12) -0.0101(12) C10 0.0423(15) 0.0503(16) 0.0674(18) -0.0168(14) -0.0061(13) -0.0091(13) C16 0.0475(15) 0.0517(16) 0.0520(16) -0.0148(13) 0.0014(12) -0.0150(13) C15 0.0473(17) 0.0597(18) 0.0553(17) -0.0154(14) 0.0003(13) -0.0094(14) C4 0.0401(14) 0.0592(17) 0.0461(15) -0.0082(13) -0.0030(11) -0.0130(12) C28 0.0563(18) 0.0648(19) 0.0547(17) -0.0072(14) 0.0016(14) -0.0272(15) C19 0.070(2) 0.0545(17) 0.0493(16) -0.0098(13) -0.0016(14) -0.0190(15) C13 0.0520(17) 0.0535(17) 0.0620(17) -0.0044(14) -0.0027(13) -0.0195(14) C21 0.0577(18) 0.072(2) 0.0499(16) -0.0210(15) 0.0033(13) -0.0122(15) C12 0.0521(17) 0.0540(17) 0.0665(18) -0.0193(15) 0.0078(14) -0.0223(14) C17 0.0530(17) 0.075(2) 0.0565(18) -0.0170(16) 0.0047(14) -0.0074(15) C11 0.0390(15) 0.0623(19) 0.086(2) -0.0305(17) 0.0049(14) -0.0198(14) O8 0.0691(16) 0.133(2) 0.0662(15) -0.0293(15) -0.0092(12) 0.0264(16) C26 0.0563(19) 0.0571(19) 0.076(2) -0.0140(16) -0.0103(15) -0.0102(15) C20 0.0627(19) 0.067(2) 0.0599(19) -0.0210(16) -0.0075(15) 0.0000(16) C25 0.070(2) 0.062(2) 0.075(2) 0.0111(17) -0.0125(17) -0.0219(17) C24 0.0503(17) 0.0572(18) 0.072(2) 0.0085(15) -0.0038(14) -0.0196(14) C18 0.069(2) 0.080(2) 0.0487(17) -0.0174(16) 0.0109(15) -0.0175(18) C27 0.0482(17) 0.083(2) 0.072(2) -0.0150(18) -0.0007(15) -0.0275(16) _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 Cl2 C19 1.737(3) . ? Cl1 C12 1.739(3) . ? Cl3 C26 1.734(3) . ? O2 C8 1.349(3) . ? O2 C2 1.436(3) . ? O1 C7 1.398(3) . ? O1 C1 1.432(3) . ? O3 C7 1.395(3) . ? O3 C3 1.446(3) . ? O5 C7 1.403(3) . ? O5 C5 1.438(3) . ? O6 C22 1.349(3) . ? O6 C6 1.440(3) . ? O4 C15 1.337(3) . ? O4 C4 1.431(3) . ? O9 C22 1.191(3) . ? O7 C8 1.198(3) . ? C2 C3 1.509(4) . ? C2 C1 1.517(4) . ? C3 C4 1.526(4) . ? C6 C1 1.521(4) . ? C6 C5 1.531(4) . ? C22 C23 1.480(4) . ? C9 C14 1.381(4) . ? C9 C10 1.382(4) . ? C9 C8 1.482(4) . ? C5 C4 1.515(4) . ? C14 C13 1.379(4) . ? C23 C28 1.375(4) . ? C23 C24 1.386(4) . ? C10 C11 1.368(4) . ? C16 C21 1.372(4) . ? C16 C17 1.379(4) . ? C16 C15 1.469(4) . ? C15 O8 1.193(3) . ? C28 C27 1.371(4) . ? C19 C18 1.362(4) . ? C19 C20 1.375(4) . ? C13 C12 1.366(4) . ? C21 C20 1.383(4) . ? C12 C11 1.376(4) . ? C17 C18 1.367(4) . ? C26 C27 1.365(5) . ? C26 C25 1.370(5) . ? C25 C24 1.376(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O2 C2 115.96(19) . . ? C7 O1 C1 110.73(19) . . ? C7 O3 C3 110.70(19) . . ? C7 O5 C5 111.83(19) . . ? C22 O6 C6 118.4(2) . . ? C15 O4 C4 117.7(2) . . ? O2 C2 C3 107.3(2) . . ? O2 C2 C1 111.8(2) . . ? C3 C2 C1 108.3(2) . . ? O3 C3 C2 109.8(2) . . ? O3 C3 C4 105.7(2) . . ? C2 C3 C4 111.1(2) . . ? O6 C6 C1 104.42(19) . . ? O6 C6 C5 115.8(2) . . ? C1 C6 C5 107.7(2) . . ? O9 C22 O6 123.6(2) . . ? O9 C22 C23 125.6(2) . . ? O6 C22 C23 110.9(2) . . ? O1 C1 C2 109.85(19) . . ? O1 C1 C6 107.9(2) . . ? C2 C1 C6 109.2(2) . . ? C14 C9 C10 119.4(3) . . ? C14 C9 C8 122.7(2) . . ? C10 C9 C8 117.9(2) . . ? O5 C5 C4 105.9(2) . . ? O5 C5 C6 105.6(2) . . ? C4 C5 C6 114.4(2) . . ? C13 C14 C9 120.1(2) . . ? C28 C23 C24 118.7(3) . . ? C28 C23 C22 122.0(2) . . ? C24 C23 C22 119.1(2) . . ? O3 C7 O1 111.2(2) . . ? O3 C7 O5 111.6(2) . . ? O1 C7 O5 110.9(2) . . ? O7 C8 O2 122.9(2) . . ? O7 C8 C9 125.0(2) . . ? O2 C8 C9 112.1(2) . . ? C11 C10 C9 120.6(3) . . ? C21 C16 C17 118.8(3) . . ? C21 C16 C15 122.7(2) . . ? C17 C16 C15 118.5(3) . . ? O8 C15 O4 122.2(3) . . ? O8 C15 C16 124.7(3) . . ? O4 C15 C16 113.1(2) . . ? O4 C4 C5 109.7(2) . . ? O4 C4 C3 111.5(2) . . ? C5 C4 C3 107.7(2) . . ? C27 C28 C23 121.0(3) . . ? C18 C19 C20 121.0(3) . . ? C18 C19 Cl2 119.1(2) . . ? C20 C19 Cl2 119.9(2) . . ? C12 C13 C14 119.4(3) . . ? C16 C21 C20 120.7(3) . . ? C13 C12 C11 121.3(3) . . ? C13 C12 Cl1 120.2(2) . . ? C11 C12 Cl1 118.5(2) . . ? C18 C17 C16 121.1(3) . . ? C10 C11 C12 119.1(3) . . ? C27 C26 C25 121.0(3) . . ? C27 C26 Cl3 119.6(3) . . ? C25 C26 Cl3 119.4(3) . . ? C19 C20 C21 119.0(3) . . ? C26 C25 C24 119.3(3) . . ? C25 C24 C23 120.4(3) . . ? C19 C18 C17 119.4(3) . . ? C26 C27 C28 119.4(3) . . ? 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 O2 C2 C3 -159.0(2) . . . . ? C8 O2 C2 C1 82.4(3) . . . . ? C7 O3 C3 C2 -58.2(3) . . . . ? C7 O3 C3 C4 61.7(3) . . . . ? O2 C2 C3 O3 -67.3(2) . . . . ? C1 C2 C3 O3 53.5(3) . . . . ? O2 C2 C3 C4 176.1(2) . . . . ? C1 C2 C3 C4 -63.1(3) . . . . ? C22 O6 C6 C1 166.9(2) . . . . ? C22 O6 C6 C5 -74.9(3) . . . . ? C6 O6 C22 O9 14.4(4) . . . . ? C6 O6 C22 C23 -164.7(2) . . . . ? C7 O1 C1 C2 58.7(3) . . . . ? C7 O1 C1 C6 -60.3(3) . . . . ? O2 C2 C1 O1 64.1(3) . . . . ? C3 C2 C1 O1 -53.9(3) . . . . ? O2 C2 C1 C6 -177.76(19) . . . . ? C3 C2 C1 C6 64.2(3) . . . . ? O6 C6 C1 O1 -176.71(18) . . . . ? C5 C6 C1 O1 59.7(3) . . . . ? O6 C6 C1 C2 63.9(2) . . . . ? C5 C6 C1 C2 -59.7(3) . . . . ? C7 O5 C5 C4 -60.2(3) . . . . ? C7 O5 C5 C6 61.5(3) . . . . ? O6 C6 C5 O5 -175.63(19) . . . . ? C1 C6 C5 O5 -59.2(3) . . . . ? O6 C6 C5 C4 -59.6(3) . . . . ? C1 C6 C5 C4 56.8(3) . . . . ? C10 C9 C14 C13 -0.7(4) . . . . ? C8 C9 C14 C13 179.8(2) . . . . ? O9 C22 C23 C28 -158.2(3) . . . . ? O6 C22 C23 C28 21.0(4) . . . . ? O9 C22 C23 C24 17.7(4) . . . . ? O6 C22 C23 C24 -163.2(2) . . . . ? C3 O3 C7 O1 62.7(3) . . . . ? C3 O3 C7 O5 -61.7(3) . . . . ? C1 O1 C7 O3 -63.2(3) . . . . ? C1 O1 C7 O5 61.6(3) . . . . ? C5 O5 C7 O3 61.2(3) . . . . ? C5 O5 C7 O1 -63.4(3) . . . . ? C2 O2 C8 O7 -3.1(4) . . . . ? C2 O2 C8 C9 176.4(2) . . . . ? C14 C9 C8 O7 -162.9(3) . . . . ? C10 C9 C8 O7 17.6(4) . . . . ? C14 C9 C8 O2 17.7(4) . . . . ? C10 C9 C8 O2 -161.8(2) . . . . ? C14 C9 C10 C11 -0.6(4) . . . . ? C8 C9 C10 C11 178.9(2) . . . . ? C4 O4 C15 O8 5.6(4) . . . . ? C4 O4 C15 C16 -172.2(2) . . . . ? C21 C16 C15 O8 -179.9(3) . . . . ? C17 C16 C15 O8 -1.0(5) . . . . ? C21 C16 C15 O4 -2.1(4) . . . . ? C17 C16 C15 O4 176.7(3) . . . . ? C15 O4 C4 C5 123.1(3) . . . . ? C15 O4 C4 C3 -117.7(3) . . . . ? O5 C5 C4 O4 -177.29(18) . . . . ? C6 C5 C4 O4 66.9(3) . . . . ? O5 C5 C4 C3 61.2(3) . . . . ? C6 C5 C4 C3 -54.7(3) . . . . ? O3 C3 C4 O4 177.41(19) . . . . ? C2 C3 C4 O4 -63.5(3) . . . . ? O3 C3 C4 C5 -62.1(2) . . . . ? C2 C3 C4 C5 56.9(3) . . . . ? C24 C23 C28 C27 -3.2(4) . . . . ? C22 C23 C28 C27 172.7(3) . . . . ? C9 C14 C13 C12 1.3(4) . . . . ? C17 C16 C21 C20 -1.4(5) . . . . ? C15 C16 C21 C20 177.4(3) . . . . ? C14 C13 C12 C11 -0.5(4) . . . . ? C14 C13 C12 Cl1 179.1(2) . . . . ? C21 C16 C17 C18 1.3(5) . . . . ? C15 C16 C17 C18 -177.6(3) . . . . ? C9 C10 C11 C12 1.4(4) . . . . ? C13 C12 C11 C10 -0.9(4) . . . . ? Cl1 C12 C11 C10 179.6(2) . . . . ? C18 C19 C20 C21 1.2(5) . . . . ? Cl2 C19 C20 C21 -179.8(2) . . . . ? C16 C21 C20 C19 0.2(5) . . . . ? C27 C26 C25 C24 -4.3(5) . . . . ? Cl3 C26 C25 C24 175.2(3) . . . . ? C26 C25 C24 C23 3.5(5) . . . . ? C28 C23 C24 C25 0.2(5) . . . . ? C22 C23 C24 C25 -175.8(3) . . . . ? C20 C19 C18 C17 -1.2(5) . . . . ? Cl2 C19 C18 C17 179.7(3) . . . . ? C16 C17 C18 C19 0.0(5) . . . . ? C25 C26 C27 C28 1.4(5) . . . . ? Cl3 C26 C27 C28 -178.2(2) . . . . ? C23 C28 C27 C26 2.5(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 C10 H10 O5 0.93 2.83 3.525(3) 132.8 1_455 C5 H5 Cl2 0.98 3.20 3.958(3) 135.8 2_676 C13 H13 Cl2 0.93 3.12 3.598(3) 113.6 1_546 C27 H27 O1 0.93 2.64 3.360(4) 134.9 2_577 C18 H18 O9 0.93 2.43 3.240(4) 144.8 2_676 C14 H14 O8 0.93 2.77 3.384(4) 124.5 2_667 C13 H13 O8 0.93 2.77 3.381(4) 124.0 2_667 C11 H11 O3 0.93 2.57 3.432(3) 153.4 1_455 C7 H7 O9 0.98 2.66 3.363(3) 129.0 2_677 C6 H6 O5 0.98 2.46 3.256(3) 138.6 2_677 C3 H3 O3 0.98 2.71 3.560(3) 144.8 2_667 C1 H1 O7 0.98 2.75 3.483(3) 132.4 2_577 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.487 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.060