# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_section_title ;Creating helical self-assembly of molecules in crystals for intermolecular acyl transfer reaction: Structures of solvatomorphs of racemic 2,6-di-O-(4-halobenzoyl)-myo-inositol 1,3,5-orthoformates ; _publ_contact_author_name 'Mysore Shashidhar' _publ_contact_author_email MS.SHASHIDHAR@NCL.RES.IN loop_ _publ_author_name S.Krishnaswamy R.G.Gonnade M.M.Bhadbhade M.S.Shashidhar # Attachment '2.cif' data_2A _database_code_depnum_ccdc_archive 'CCDC 752175' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate chloroform solvate ; _chemical_name_common ;2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate chloroform solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8, C H Cl3' _chemical_formula_sum 'C22 H17 Br2 Cl3 O8' _chemical_formula_weight 675.53 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8141(17) _cell_length_b 10.2601(14) _cell_length_c 18.756(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.832(2) _cell_angle_gamma 90.00 _cell_volume 2404.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 6308 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 28.04 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.866 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 3.753 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3653 _exptl_absorpt_correction_T_max 0.7584 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11791 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4223 _reflns_number_gt 3873 _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 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^)+(0.0303P)^2^+2.5064P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4223 _refine_ls_number_parameters 328 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0664 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.003 _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 0.95099(2) 1.19546(2) 1.203191(13) 0.02528(9) Uani 1 1 d . . . Br2 Br 1.11765(3) 0.72966(5) 0.50685(2) 0.02689(9) Uani 0.95 1 d P A 1 Br2' Br 1.1046(9) 0.6894(11) 0.4921(6) 0.051(4) Uiso 0.05 1 d PD A 2 O1 O 0.85930(13) 0.44584(17) 0.95966(9) 0.0199(4) Uani 1 1 d . . . O2 O 0.86256(13) 0.72276(15) 0.94323(9) 0.0185(4) Uani 1 1 d . . . O3 O 0.68957(13) 0.53490(16) 0.92208(9) 0.0206(4) Uani 1 1 d . . . O4 O 0.71260(15) 0.58704(17) 0.73492(9) 0.0222(4) Uani 1 1 d D . . O5 O 0.72838(14) 0.33334(16) 0.87702(9) 0.0215(4) Uani 1 1 d . . . O6 O 0.91905(14) 0.47719(16) 0.77967(9) 0.0211(4) Uani 1 1 d . . . O7 O 0.79992(15) 0.89097(17) 0.86912(9) 0.0245(4) Uani 1 1 d . . . O8 O 0.98421(16) 0.28568(18) 0.74889(11) 0.0311(5) Uani 1 1 d . . . C1 C 0.89826(19) 0.5106(2) 0.90202(13) 0.0187(5) Uani 1 1 d . . . H1 H 0.9764 0.5298 0.9186 0.022 Uiso 1 1 calc R . . C2 C 0.83615(19) 0.6359(2) 0.88054(12) 0.0172(5) Uani 1 1 d . . . H2 H 0.8576 0.6763 0.8374 0.021 Uiso 1 1 calc R . . C3 C 0.71686(19) 0.6043(2) 0.86176(12) 0.0182(5) Uani 1 1 d . . . H3 H 0.6742 0.6865 0.8520 0.022 Uiso 1 1 calc R . . C4 C 0.6910(2) 0.5158(2) 0.79475(13) 0.0197(5) Uani 1 1 d . . . H4 H 0.6134 0.4924 0.7843 0.024 Uiso 1 1 calc R . . C5 C 0.7584(2) 0.3913(2) 0.81378(13) 0.0193(5) Uani 1 1 d . . . H5 H 0.7431 0.3292 0.7716 0.023 Uiso 1 1 calc R . . C6 C 0.8790(2) 0.4162(2) 0.83738(12) 0.0185(5) Uani 1 1 d . . . H6 H 0.9178 0.3325 0.8521 0.022 Uiso 1 1 calc R . . C7 C 0.74862(19) 0.4196(2) 0.93684(13) 0.0205(5) Uani 1 1 d . . . H7 H 0.7257 0.3752 0.9783 0.025 Uiso 1 1 calc R . . C8 C 0.83989(19) 0.8496(2) 0.92976(13) 0.0184(5) Uani 1 1 d . . . C9 C 0.86825(18) 0.9309(2) 0.99676(13) 0.0172(5) Uani 1 1 d . . . C10 C 0.8539(2) 1.0659(2) 0.99018(13) 0.0202(5) Uani 1 1 d . . . H10 H 0.8266 1.1037 0.9435 0.024 Uiso 1 1 calc R . . C11 C 0.8794(2) 1.1444(2) 1.05172(13) 0.0215(5) Uani 1 1 d . . . H11 H 0.8702 1.2362 1.0477 0.026 Uiso 1 1 calc R . . C12 C 0.91866(19) 1.0869(2) 1.11895(13) 0.0192(5) Uani 1 1 d . . . C13 C 0.9342(2) 0.9530(2) 1.12718(13) 0.0205(5) Uani 1 1 d . . . H13 H 0.9615 0.9156 1.1739 0.025 Uiso 1 1 calc R . . C14 C 0.90849(19) 0.8757(2) 1.06496(13) 0.0197(5) Uani 1 1 d . . . H14 H 0.9185 0.7840 1.0691 0.024 Uiso 1 1 calc R . . C15 C 0.96793(19) 0.4001(2) 0.73844(13) 0.0191(5) Uani 1 1 d . . . C16 C 0.99836(19) 0.4778(2) 0.67898(13) 0.0196(5) Uani 1 1 d . A . C17 C 1.0751(2) 0.4271(3) 0.64457(14) 0.0251(6) Uani 1 1 d . . . H17 H 1.1037 0.3427 0.6571 0.030 Uiso 1 1 calc R . . C18 C 1.1097(2) 0.4999(3) 0.59189(14) 0.0251(6) Uani 1 1 d . A . H18 H 1.1624 0.4662 0.5683 0.030 Uiso 1 1 calc R . . C19 C 1.0665(2) 0.6218(3) 0.57434(13) 0.0212(5) Uani 1 1 d D . . C20 C 0.9873(2) 0.6724(3) 0.60583(14) 0.0231(5) Uani 1 1 d . A . H20 H 0.9569 0.7555 0.5916 0.028 Uiso 1 1 calc R . . C21 C 0.9534(2) 0.5993(2) 0.65858(13) 0.0211(5) Uani 1 1 d . . . H21 H 0.8991 0.6323 0.6809 0.025 Uiso 1 1 calc R A . H4A H 0.701(3) 0.539(3) 0.7001(14) 0.047(10) Uiso 1 1 d D . . C22 C 0.3096(2) 0.4942(3) 0.83869(18) 0.0419(8) Uani 1 1 d D . . H22 H 0.3307 0.4057 0.8244 0.050 Uiso 1 1 calc R B 1 Cl1 Cl 0.19621(6) 0.47913(9) 0.87604(5) 0.0478(2) Uani 1 1 d . C . Cl2 Cl 0.28310(7) 0.59466(11) 0.76097(4) 0.0549(2) Uani 1 1 d . C . Cl3 Cl 0.41619(8) 0.55983(12) 0.90577(7) 0.0585(3) Uani 0.90 1 d P C 1 Cl3' Cl 0.4329(6) 0.5285(8) 0.8754(4) 0.0271(18) Uiso 0.10 1 d PD C 2 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 0.03104(16) 0.02196(14) 0.02161(14) -0.00670(10) 0.00323(11) -0.00038(10) Br2 0.02437(18) 0.0338(2) 0.02581(18) 0.00820(18) 0.01278(14) 0.00184(16) O1 0.0202(9) 0.0226(9) 0.0171(8) 0.0039(7) 0.0048(7) 0.0001(7) O2 0.0227(9) 0.0154(8) 0.0168(8) -0.0017(6) 0.0030(7) -0.0013(7) O3 0.0193(9) 0.0241(9) 0.0202(9) 0.0009(7) 0.0081(7) 0.0001(7) O4 0.0338(10) 0.0180(9) 0.0140(9) -0.0001(7) 0.0037(8) -0.0005(8) O5 0.0264(10) 0.0185(9) 0.0210(9) 0.0008(7) 0.0088(7) -0.0057(7) O6 0.0287(10) 0.0175(9) 0.0210(9) 0.0014(7) 0.0136(7) 0.0023(7) O7 0.0363(11) 0.0204(9) 0.0156(9) 0.0017(7) 0.0030(8) -0.0013(8) O8 0.0411(12) 0.0199(10) 0.0391(11) 0.0033(8) 0.0234(10) 0.0057(8) C1 0.0183(12) 0.0206(13) 0.0182(12) 0.0017(10) 0.0065(10) -0.0007(10) C2 0.0201(12) 0.0171(12) 0.0147(11) -0.0026(9) 0.0043(9) -0.0031(10) C3 0.0212(13) 0.0177(12) 0.0159(12) 0.0004(9) 0.0049(10) 0.0015(10) C4 0.0207(12) 0.0194(12) 0.0186(12) -0.0002(10) 0.0037(10) -0.0020(10) C5 0.0251(13) 0.0175(12) 0.0159(12) -0.0005(9) 0.0056(10) -0.0031(10) C6 0.0227(13) 0.0173(12) 0.0172(12) 0.0025(9) 0.0080(10) 0.0003(10) C7 0.0215(13) 0.0220(13) 0.0193(12) 0.0005(10) 0.0075(10) -0.0026(10) C8 0.0166(12) 0.0187(12) 0.0216(13) -0.0001(10) 0.0078(10) -0.0040(10) C9 0.0146(12) 0.0179(12) 0.0191(12) -0.0013(9) 0.0038(9) -0.0038(9) C10 0.0203(12) 0.0207(13) 0.0192(12) 0.0031(10) 0.0037(10) -0.0003(10) C11 0.0222(13) 0.0165(12) 0.0255(13) 0.0002(10) 0.0043(11) 0.0007(10) C12 0.0184(12) 0.0205(13) 0.0192(12) -0.0063(10) 0.0052(10) -0.0032(10) C13 0.0217(13) 0.0213(13) 0.0177(12) 0.0010(10) 0.0028(10) -0.0006(10) C14 0.0220(13) 0.0150(12) 0.0223(13) 0.0002(10) 0.0052(10) 0.0003(10) C15 0.0168(12) 0.0191(13) 0.0219(12) -0.0026(10) 0.0056(10) 0.0003(10) C16 0.0179(12) 0.0199(13) 0.0215(12) -0.0039(10) 0.0054(10) -0.0031(10) C17 0.0270(14) 0.0218(13) 0.0286(14) -0.0016(11) 0.0105(11) 0.0038(11) C18 0.0237(13) 0.0299(14) 0.0256(13) -0.0017(11) 0.0139(11) 0.0015(11) C19 0.0202(13) 0.0283(14) 0.0164(12) 0.0009(10) 0.0067(10) -0.0032(11) C20 0.0220(13) 0.0242(13) 0.0237(13) 0.0044(10) 0.0066(11) 0.0046(11) C21 0.0184(12) 0.0254(13) 0.0209(12) -0.0018(10) 0.0071(10) 0.0020(10) C22 0.0286(16) 0.0404(18) 0.057(2) -0.0098(15) 0.0107(15) -0.0039(14) Cl1 0.0325(4) 0.0618(5) 0.0504(5) 0.0077(4) 0.0117(4) -0.0014(4) Cl2 0.0465(5) 0.0851(7) 0.0351(4) -0.0050(4) 0.0132(4) -0.0122(5) Cl3 0.0384(5) 0.0694(7) 0.0575(7) 0.0171(6) -0.0113(5) -0.0241(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 Br1 C12 1.902(2) . ? Br2 C19 1.904(2) . ? Br2' C19 1.853(10) . ? O1 C7 1.413(3) . ? O1 C1 1.449(3) . ? O2 C8 1.345(3) . ? O2 C2 1.454(3) . ? O3 C7 1.399(3) . ? O3 C3 1.444(3) . ? O4 C4 1.417(3) . ? O4 H4A 0.804(18) . ? O5 C7 1.407(3) . ? O5 C5 1.453(3) . ? O6 C15 1.353(3) . ? O6 C6 1.440(3) . ? O7 C8 1.215(3) . ? O8 C15 1.201(3) . ? C1 C2 1.518(3) . ? C1 C6 1.528(3) . ? C1 H1 1.0000 . ? C2 C3 1.525(3) . ? C2 H2 1.0000 . ? C3 C4 1.526(3) . ? C3 H3 1.0000 . ? C4 C5 1.539(3) . ? C4 H4 1.0000 . ? C5 C6 1.532(3) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.485(3) . ? C9 C14 1.389(3) . ? C9 C10 1.399(3) . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 C13 1.392(3) . ? C13 C14 1.389(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.492(3) . ? C16 C21 1.391(4) . ? C16 C17 1.391(3) . ? C17 C18 1.388(4) . ? C17 H17 0.9500 . ? C18 C19 1.379(4) . ? C18 H18 0.9500 . ? C19 C20 1.383(4) . ? C20 C21 1.387(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 Cl3' 1.616(8) . ? C22 Cl1 1.755(3) . ? C22 Cl2 1.756(4) . ? C22 Cl3 1.771(3) . ? C22 H22 1.0000 . ? 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 110.51(17) . . ? C8 O2 C2 116.05(18) . . ? C7 O3 C3 110.96(17) . . ? C4 O4 H4A 107(3) . . ? C7 O5 C5 111.01(18) . . ? C15 O6 C6 117.59(18) . . ? O1 C1 C2 109.83(19) . . ? O1 C1 C6 106.23(19) . . ? C2 C1 C6 110.09(19) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C1 106.86(18) . . ? O2 C2 C3 111.00(19) . . ? C1 C2 C3 108.69(19) . . ? O2 C2 H2 110.1 . . ? C1 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? O3 C3 C2 109.19(18) . . ? O3 C3 C4 107.83(19) . . ? C2 C3 C4 109.85(19) . . ? O3 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? C4 C3 H3 110.0 . . ? O4 C4 C3 107.49(19) . . ? O4 C4 C5 114.5(2) . . ? C3 C4 C5 107.16(19) . . ? O4 C4 H4 109.2 . . ? C3 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? O5 C5 C6 105.41(18) . . ? O5 C5 C4 107.00(19) . . ? C6 C5 C4 114.0(2) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C1 107.43(19) . . ? O6 C6 C5 111.12(19) . . ? C1 C6 C5 108.04(19) . . ? O6 C6 H6 110.1 . . ? C1 C6 H6 110.1 . . ? C5 C6 H6 110.1 . . ? O3 C7 O5 112.23(19) . . ? O3 C7 O1 111.14(19) . . ? O5 C7 O1 110.87(19) . . ? O3 C7 H7 107.4 . . ? O5 C7 H7 107.4 . . ? O1 C7 H7 107.4 . . ? O7 C8 O2 122.8(2) . . ? O7 C8 C9 124.7(2) . . ? O2 C8 C9 112.5(2) . . ? C14 C9 C10 120.0(2) . . ? C14 C9 C8 121.4(2) . . ? C10 C9 C8 118.6(2) . . ? C11 C10 C9 120.0(2) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 118.9(2) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C13 122.4(2) . . ? C11 C12 Br1 118.45(18) . . ? C13 C12 Br1 119.11(18) . . ? C14 C13 C12 118.0(2) . . ? C14 C13 H13 121.0 . . ? C12 C13 H13 121.0 . . ? C13 C14 C9 120.8(2) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O8 C15 O6 124.3(2) . . ? O8 C15 C16 125.4(2) . . ? O6 C15 C16 110.2(2) . . ? C21 C16 C17 120.0(2) . . ? C21 C16 C15 121.6(2) . . ? C17 C16 C15 118.4(2) . . ? C18 C17 C16 120.0(2) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 118.9(2) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C18 C19 C20 122.2(2) . . ? C18 C19 Br2' 111.8(4) . . ? C20 C19 Br2' 124.7(4) . . ? C18 C19 Br2 120.44(18) . . ? C20 C19 Br2 117.34(19) . . ? C19 C20 C21 118.5(2) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C20 C21 C16 120.3(2) . . ? C20 C21 H21 119.8 . . ? C16 C21 H21 119.8 . . ? Cl3' C22 Cl1 131.8(4) . . ? Cl3' C22 Cl2 102.5(3) . . ? Cl1 C22 Cl2 110.99(18) . . ? Cl1 C22 Cl3 109.03(18) . . ? Cl2 C22 Cl3 110.05(18) . . ? Cl3' C22 H22 90.9 . . ? Cl1 C22 H22 108.9 . . ? Cl2 C22 H22 108.9 . . ? Cl3 C22 H22 108.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C2 57.8(2) . . . . ? C7 O1 C1 C6 -61.2(2) . . . . ? C8 O2 C2 C1 162.53(19) . . . . ? C8 O2 C2 C3 -79.1(2) . . . . ? O1 C1 C2 O2 66.2(2) . . . . ? C6 C1 C2 O2 -177.20(18) . . . . ? O1 C1 C2 C3 -53.7(2) . . . . ? C6 C1 C2 C3 62.9(2) . . . . ? C7 O3 C3 C2 -59.1(2) . . . . ? C7 O3 C3 C4 60.3(2) . . . . ? O2 C2 C3 O3 -63.3(2) . . . . ? C1 C2 C3 O3 53.9(2) . . . . ? O2 C2 C3 C4 178.64(18) . . . . ? C1 C2 C3 C4 -64.1(2) . . . . ? O3 C3 C4 O4 176.92(18) . . . . ? C2 C3 C4 O4 -64.2(2) . . . . ? O3 C3 C4 C5 -59.6(2) . . . . ? C2 C3 C4 C5 59.3(2) . . . . ? C7 O5 C5 C6 61.7(2) . . . . ? C7 O5 C5 C4 -59.9(2) . . . . ? O4 C4 C5 O5 178.35(18) . . . . ? C3 C4 C5 O5 59.3(2) . . . . ? O4 C4 C5 C6 62.2(3) . . . . ? C3 C4 C5 C6 -56.8(2) . . . . ? C15 O6 C6 C1 142.6(2) . . . . ? C15 O6 C6 C5 -99.4(2) . . . . ? O1 C1 C6 O6 -178.88(17) . . . . ? C2 C1 C6 O6 62.3(2) . . . . ? O1 C1 C6 C5 61.2(2) . . . . ? C2 C1 C6 C5 -57.7(2) . . . . ? O5 C5 C6 O6 -178.55(17) . . . . ? C4 C5 C6 O6 -61.5(3) . . . . ? O5 C5 C6 C1 -60.9(2) . . . . ? C4 C5 C6 C1 56.1(2) . . . . ? C3 O3 C7 O5 -61.2(2) . . . . ? C3 O3 C7 O1 63.6(2) . . . . ? C5 O5 C7 O3 61.4(2) . . . . ? C5 O5 C7 O1 -63.5(2) . . . . ? C1 O1 C7 O3 -62.6(2) . . . . ? C1 O1 C7 O5 62.9(2) . . . . ? C2 O2 C8 O7 -0.2(3) . . . . ? C2 O2 C8 C9 179.37(19) . . . . ? O7 C8 C9 C14 176.5(2) . . . . ? O2 C8 C9 C14 -3.0(3) . . . . ? O7 C8 C9 C10 -3.6(4) . . . . ? O2 C8 C9 C10 176.9(2) . . . . ? C14 C9 C10 C11 -0.2(4) . . . . ? C8 C9 C10 C11 179.9(2) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C10 C11 C12 Br1 -178.88(19) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? Br1 C12 C13 C14 179.07(18) . . . . ? C12 C13 C14 C9 -0.2(4) . . . . ? C10 C9 C14 C13 0.4(4) . . . . ? C8 C9 C14 C13 -179.7(2) . . . . ? C6 O6 C15 O8 -3.4(4) . . . . ? C6 O6 C15 C16 176.72(19) . . . . ? O8 C15 C16 C21 163.0(3) . . . . ? O6 C15 C16 C21 -17.1(3) . . . . ? O8 C15 C16 C17 -18.1(4) . . . . ? O6 C15 C16 C17 161.7(2) . . . . ? C21 C16 C17 C18 2.5(4) . . . . ? C15 C16 C17 C18 -176.4(2) . . . . ? C16 C17 C18 C19 -0.4(4) . . . . ? C17 C18 C19 C20 -2.1(4) . . . . ? C17 C18 C19 Br2' -169.7(4) . . . . ? C17 C18 C19 Br2 176.14(19) . . . . ? C18 C19 C20 C21 2.2(4) . . . . ? Br2' C19 C20 C21 168.2(4) . . . . ? Br2 C19 C20 C21 -176.00(19) . . . . ? C19 C20 C21 C16 0.0(4) . . . . ? C17 C16 C21 C20 -2.3(4) . . . . ? C15 C16 C21 C20 176.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A O7 0.804(18) 2.00(2) 2.782(2) 165(4) 2_646 C5 H5 O4 1.00 2.56 3.296(3) 130.5 2_646 C13 H13 O8 0.95 2.53 3.378(3) 148.9 3_767 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.552 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.067 #===END data_2B _database_code_depnum_ccdc_archive 'CCDC 752176' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate acetone solvate ; _chemical_name_common ;2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate acetone solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8 , C3 H6 O' _chemical_formula_sum 'C24 H22 Br2 O9' _chemical_formula_weight 614.24 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 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8133(15) _cell_length_b 10.2045(12) _cell_length_c 18.814(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.599(2) _cell_angle_gamma 90.00 _cell_volume 2391.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 4283 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 27.87 _exptl_crystal_description 'square plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 3.443 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4248 _exptl_absorpt_correction_T_max 0.8123 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11778 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4208 _reflns_number_gt 3597 _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 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^)+(0.0503P)^2^+1.2000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4208 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.05149(3) 1.19994(3) -0.202224(16) 0.02696(11) Uani 1 1 d . . . Br2 Br -0.10818(3) 0.73375(4) 0.49954(2) 0.04357(13) Uani 1 1 d . . . C1 C 0.0983(2) 0.5097(3) 0.09935(15) 0.0200(6) Uani 1 1 d . . . H1 H 0.0202 0.5305 0.0824 0.024 Uiso 1 1 calc R . . C2 C 0.1627(2) 0.6353(3) 0.12033(15) 0.0177(6) Uani 1 1 d . . . H2 H 0.1425 0.6781 0.1630 0.021 Uiso 1 1 calc R . . C3 C 0.2817(2) 0.6005(3) 0.13908(15) 0.0203(6) Uani 1 1 d . . . H3 H 0.3259 0.6822 0.1482 0.024 Uiso 1 1 calc R . . C4 C 0.3070(2) 0.5133(3) 0.20698(16) 0.0213(6) Uani 1 1 d . . . H4 H 0.3844 0.4874 0.2175 0.026 Uiso 1 1 calc R . . C5 C 0.2372(2) 0.3896(3) 0.18919(16) 0.0219(6) Uani 1 1 d . . . H5 H 0.2523 0.3284 0.2319 0.026 Uiso 1 1 calc R . . C6 C 0.1171(2) 0.4169(3) 0.16514(15) 0.0210(6) Uani 1 1 d . . . H6 H 0.0773 0.3331 0.1509 0.025 Uiso 1 1 calc R . . C7 C 0.2453(2) 0.4125(3) 0.06558(16) 0.0233(6) Uani 1 1 d . . . H7 H 0.2666 0.3654 0.0246 0.028 Uiso 1 1 calc R . . C8 C 0.1603(2) 0.8478(3) 0.06986(16) 0.0201(6) Uani 1 1 d . . . C9 C 0.1323(2) 0.9296(3) 0.00233(15) 0.0183(6) Uani 1 1 d . . . C10 C 0.1439(2) 1.0650(3) 0.01038(16) 0.0211(6) Uani 1 1 d . . . H10 H 0.1689 1.1023 0.0576 0.025 Uiso 1 1 calc R . . C11 C 0.1187(2) 1.1449(3) -0.05092(16) 0.0223(6) Uani 1 1 d . . . H11 H 0.1257 1.2374 -0.0461 0.027 Uiso 1 1 calc R . . C12 C 0.0834(2) 1.0888(3) -0.11888(16) 0.0200(6) Uani 1 1 d . . . C13 C 0.0710(2) 0.9540(3) -0.12813(16) 0.0235(7) Uani 1 1 d . . . H13 H 0.0463 0.9171 -0.1755 0.028 Uiso 1 1 calc R . . C14 C 0.0954(2) 0.8747(3) -0.06648(16) 0.0221(6) Uani 1 1 d . . . H14 H 0.0869 0.7825 -0.0714 0.027 Uiso 1 1 calc R . . C15 C 0.0245(2) 0.4065(3) 0.26185(17) 0.0235(7) Uani 1 1 d . . . C16 C -0.0042(2) 0.4838(3) 0.32118(16) 0.0231(6) Uani 1 1 d . . . C17 C -0.0857(3) 0.4399(3) 0.35195(18) 0.0317(8) Uani 1 1 d . . . H17 H -0.1210 0.3597 0.3357 0.038 Uiso 1 1 calc R . . C18 C -0.1164(3) 0.5116(3) 0.40624(19) 0.0360(8) Uani 1 1 d . . . H18 H -0.1725 0.4814 0.4273 0.043 Uiso 1 1 calc R . . C19 C -0.0639(3) 0.6275(3) 0.42904(17) 0.0294(7) Uani 1 1 d . . . C20 C 0.0200(2) 0.6710(3) 0.40110(17) 0.0283(7) Uani 1 1 d . . . H20 H 0.0571 0.7493 0.4191 0.034 Uiso 1 1 calc R . . C21 C 0.0499(2) 0.5996(3) 0.34651(16) 0.0241(7) Uani 1 1 d . . . H21 H 0.1070 0.6294 0.3263 0.029 Uiso 1 1 calc R . . C24 C 0.5927(4) 0.5411(5) 0.1483(3) 0.0894(19) Uani 1 1 d . . . H24A H 0.5384 0.6087 0.1309 0.134 Uiso 1 1 calc R . . H24B H 0.6116 0.5405 0.2019 0.134 Uiso 1 1 calc R . . H24C H 0.5639 0.4553 0.1303 0.134 Uiso 1 1 calc R . . C23 C 0.6895(3) 0.5696(4) 0.1211(2) 0.0404(9) Uani 1 1 d . . . C22 C 0.7793(4) 0.4739(5) 0.1347(3) 0.0770(16) Uani 1 1 d . . . H22A H 0.7602 0.3993 0.1014 0.115 Uiso 1 1 calc R . . H22B H 0.7928 0.4429 0.1854 0.115 Uiso 1 1 calc R . . H22C H 0.8440 0.5162 0.1265 0.115 Uiso 1 1 calc R . . O1 O 0.13493(15) 0.44201(18) 0.04281(11) 0.0221(4) Uani 1 1 d . . . O2 O 0.13706(16) 0.72054(17) 0.05676(10) 0.0199(4) Uani 1 1 d . . . O3 O 0.30706(15) 0.52761(18) 0.07970(10) 0.0227(4) Uani 1 1 d . . . O4 O 0.28884(17) 0.5876(2) 0.26636(11) 0.0243(5) Uani 1 1 d . . . O5 O 0.26559(16) 0.32829(18) 0.12662(11) 0.0235(5) Uani 1 1 d . . . O6 O 0.07898(16) 0.47946(18) 0.22302(11) 0.0227(4) Uani 1 1 d . . . O7 O 0.20009(17) 0.88974(19) 0.13053(11) 0.0265(5) Uani 1 1 d . . . O8 O 0.0018(2) 0.2927(2) 0.24863(14) 0.0401(6) Uani 1 1 d . . . O9 O 0.6934(2) 0.6664(3) 0.08545(15) 0.0502(7) Uani 1 1 d . . . H4A H 0.295(3) 0.536(3) 0.2999(18) 0.027(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03511(19) 0.02146(17) 0.02104(18) 0.00579(12) 0.00004(13) -0.00037(12) Br2 0.0352(2) 0.0621(3) 0.0383(2) -0.02120(18) 0.01842(17) -0.00463(17) C1 0.0198(14) 0.0207(14) 0.0198(15) -0.0001(12) 0.0052(12) 0.0004(11) C2 0.0237(15) 0.0157(13) 0.0135(14) 0.0017(11) 0.0039(12) 0.0016(11) C3 0.0258(16) 0.0163(13) 0.0185(15) 0.0004(12) 0.0047(12) -0.0013(11) C4 0.0212(15) 0.0201(14) 0.0195(15) 0.0013(12) -0.0012(12) 0.0035(11) C5 0.0307(17) 0.0169(13) 0.0179(15) 0.0006(12) 0.0051(13) 0.0049(12) C6 0.0282(16) 0.0161(13) 0.0202(15) -0.0040(12) 0.0088(12) -0.0017(12) C7 0.0283(16) 0.0216(14) 0.0212(16) -0.0009(12) 0.0081(13) 0.0025(12) C8 0.0195(15) 0.0180(13) 0.0233(16) 0.0014(12) 0.0058(12) 0.0033(11) C9 0.0170(14) 0.0183(13) 0.0190(15) 0.0030(11) 0.0027(12) 0.0021(11) C10 0.0241(15) 0.0196(14) 0.0187(15) -0.0031(12) 0.0034(12) 0.0008(11) C11 0.0248(16) 0.0162(13) 0.0251(16) 0.0008(12) 0.0042(13) -0.0001(12) C12 0.0183(14) 0.0206(14) 0.0204(15) 0.0037(12) 0.0032(12) 0.0036(11) C13 0.0276(16) 0.0214(14) 0.0191(16) -0.0031(12) 0.0008(13) -0.0003(12) C14 0.0264(16) 0.0156(13) 0.0226(16) -0.0004(12) 0.0019(13) 0.0000(11) C15 0.0224(15) 0.0234(16) 0.0255(17) 0.0008(13) 0.0074(13) -0.0022(12) C16 0.0255(16) 0.0205(14) 0.0235(16) 0.0035(12) 0.0061(13) 0.0022(12) C17 0.0343(18) 0.0282(16) 0.038(2) -0.0032(15) 0.0186(16) -0.0073(14) C18 0.0368(19) 0.0376(19) 0.040(2) -0.0006(16) 0.0215(16) -0.0060(15) C19 0.0278(17) 0.0364(18) 0.0252(17) -0.0049(14) 0.0089(14) 0.0035(14) C20 0.0275(17) 0.0293(16) 0.0289(18) -0.0042(14) 0.0084(14) -0.0053(13) C21 0.0221(15) 0.0267(15) 0.0228(16) 0.0001(13) 0.0041(13) -0.0024(12) C24 0.104(4) 0.058(3) 0.133(5) 0.025(3) 0.081(4) 0.007(3) C23 0.049(2) 0.038(2) 0.035(2) -0.0046(17) 0.0103(17) -0.0022(17) C22 0.059(3) 0.057(3) 0.098(4) -0.004(3) -0.015(3) 0.004(2) O1 0.0256(11) 0.0216(10) 0.0183(10) -0.0021(8) 0.0032(9) 0.0007(8) O2 0.0264(11) 0.0153(9) 0.0164(11) 0.0013(8) 0.0019(9) 0.0001(8) O3 0.0241(11) 0.0230(10) 0.0220(11) 0.0006(8) 0.0074(9) 0.0002(8) O4 0.0377(13) 0.0189(10) 0.0147(11) 0.0014(9) 0.0030(9) 0.0017(9) O5 0.0312(12) 0.0175(10) 0.0222(11) -0.0006(8) 0.0073(9) 0.0054(8) O6 0.0307(11) 0.0177(10) 0.0235(11) 0.0001(8) 0.0139(9) -0.0019(8) O7 0.0413(13) 0.0212(10) 0.0142(11) -0.0015(9) 0.0009(9) -0.0005(9) O8 0.0554(16) 0.0232(12) 0.0526(16) -0.0077(11) 0.0350(13) -0.0118(10) O9 0.0609(18) 0.0449(15) 0.0518(17) 0.0018(14) 0.0270(14) -0.0024(13) _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 1.900(3) . ? Br2 C19 1.900(3) . ? C1 O1 1.436(3) . ? C1 C2 1.525(4) . ? C1 C6 1.532(4) . ? C1 H1 1.0000 . ? C2 O2 1.453(3) . ? C2 C3 1.524(4) . ? C2 H2 1.0000 . ? C3 O3 1.442(3) . ? C3 C4 1.528(4) . ? C3 H3 1.0000 . ? C4 O4 1.414(3) . ? C4 C5 1.538(4) . ? C4 H4 1.0000 . ? C5 O5 1.453(3) . ? C5 C6 1.524(4) . ? C5 H5 1.0000 . ? C6 O6 1.443(3) . ? C6 H6 1.0000 . ? C7 O3 1.406(3) . ? C7 O5 1.409(3) . ? C7 O1 1.411(3) . ? C7 H7 1.0000 . ? C8 O7 1.213(3) . ? C8 O2 1.342(3) . ? C8 C9 1.492(4) . ? C9 C14 1.387(4) . ? C9 C10 1.395(4) . ? C10 C11 1.387(4) . ? C10 H10 0.9500 . ? C11 C12 1.377(4) . ? C11 H11 0.9500 . ? C12 C13 1.391(4) . ? C13 C14 1.388(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 O8 1.209(3) . ? C15 O6 1.348(3) . ? C15 C16 1.482(4) . ? C16 C17 1.382(4) . ? C16 C21 1.396(4) . ? C17 C18 1.387(4) . ? C17 H17 0.9500 . ? C18 C19 1.378(5) . ? C18 H18 0.9500 . ? C19 C20 1.377(5) . ? C20 C21 1.385(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C24 C23 1.478(6) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C23 O9 1.202(4) . ? C23 C22 1.485(6) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? O4 H4A 0.81(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 110.2(2) . . ? O1 C1 C6 106.6(2) . . ? C2 C1 C6 109.7(2) . . ? O1 C1 H1 110.1 . . ? C2 C1 H1 110.1 . . ? C6 C1 H1 110.1 . . ? O2 C2 C3 110.5(2) . . ? O2 C2 C1 106.7(2) . . ? C3 C2 C1 108.3(2) . . ? O2 C2 H2 110.4 . . ? C3 C2 H2 110.4 . . ? C1 C2 H2 110.4 . . ? O3 C3 C2 109.7(2) . . ? O3 C3 C4 107.8(2) . . ? C2 C3 C4 109.5(2) . . ? O3 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? C4 C3 H3 110.0 . . ? O4 C4 C3 107.9(2) . . ? O4 C4 C5 114.6(2) . . ? C3 C4 C5 107.3(2) . . ? O4 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? O5 C5 C6 105.4(2) . . ? O5 C5 C4 106.6(2) . . ? C6 C5 C4 114.2(2) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 110.7(2) . . ? O6 C6 C1 108.7(2) . . ? C5 C6 C1 108.0(2) . . ? O6 C6 H6 109.8 . . ? C5 C6 H6 109.8 . . ? C1 C6 H6 109.8 . . ? O3 C7 O5 111.6(2) . . ? O3 C7 O1 111.0(2) . . ? O5 C7 O1 110.9(2) . . ? O3 C7 H7 107.7 . . ? O5 C7 H7 107.7 . . ? O1 C7 H7 107.7 . . ? O7 C8 O2 122.7(3) . . ? O7 C8 C9 124.6(3) . . ? O2 C8 C9 112.7(2) . . ? C14 C9 C10 120.3(3) . . ? C14 C9 C8 122.0(2) . . ? C10 C9 C8 117.6(3) . . ? C11 C10 C9 119.6(3) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 119.3(3) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 122.0(3) . . ? C11 C12 Br1 118.6(2) . . ? C13 C12 Br1 119.4(2) . . ? C14 C13 C12 118.4(3) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C9 C14 C13 120.3(3) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? O8 C15 O6 123.3(3) . . ? O8 C15 C16 125.2(3) . . ? O6 C15 C16 111.4(2) . . ? C17 C16 C21 119.7(3) . . ? C17 C16 C15 119.2(3) . . ? C21 C16 C15 121.1(3) . . ? C16 C17 C18 120.7(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 118.7(3) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C20 C19 C18 121.7(3) . . ? C20 C19 Br2 118.1(2) . . ? C18 C19 Br2 120.2(3) . . ? C19 C20 C21 119.3(3) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C20 C21 C16 119.8(3) . . ? C20 C21 H21 120.1 . . ? C16 C21 H21 120.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O9 C23 C24 120.3(4) . . ? O9 C23 C22 120.3(4) . . ? C24 C23 C22 119.3(4) . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C7 O1 C1 110.9(2) . . ? C8 O2 C2 115.5(2) . . ? C7 O3 C3 111.0(2) . . ? C4 O4 H4A 106(2) . . ? C7 O5 C5 111.4(2) . . ? C15 O6 C6 118.4(2) . . ? 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 O1 C1 C2 O2 65.6(3) . . . . ? C6 C1 C2 O2 -177.3(2) . . . . ? O1 C1 C2 C3 -53.3(3) . . . . ? C6 C1 C2 C3 63.7(3) . . . . ? O2 C2 C3 O3 -63.2(3) . . . . ? C1 C2 C3 O3 53.3(3) . . . . ? O2 C2 C3 C4 178.8(2) . . . . ? C1 C2 C3 C4 -64.7(3) . . . . ? O3 C3 C4 O4 176.2(2) . . . . ? C2 C3 C4 O4 -64.6(3) . . . . ? O3 C3 C4 C5 -59.8(3) . . . . ? C2 C3 C4 C5 59.4(3) . . . . ? O4 C4 C5 O5 179.0(2) . . . . ? C3 C4 C5 O5 59.3(3) . . . . ? O4 C4 C5 C6 63.0(3) . . . . ? C3 C4 C5 C6 -56.7(3) . . . . ? O5 C5 C6 O6 -179.5(2) . . . . ? C4 C5 C6 O6 -62.8(3) . . . . ? O5 C5 C6 C1 -60.7(3) . . . . ? C4 C5 C6 C1 56.0(3) . . . . ? O1 C1 C6 O6 -178.6(2) . . . . ? C2 C1 C6 O6 62.1(3) . . . . ? O1 C1 C6 C5 61.3(3) . . . . ? C2 C1 C6 C5 -58.1(3) . . . . ? O7 C8 C9 C14 174.4(3) . . . . ? O2 C8 C9 C14 -5.4(4) . . . . ? O7 C8 C9 C10 -5.9(4) . . . . ? O2 C8 C9 C10 174.3(2) . . . . ? C14 C9 C10 C11 -0.2(4) . . . . ? C8 C9 C10 C11 -179.9(3) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 C13 0.7(4) . . . . ? C10 C11 C12 Br1 -179.0(2) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? Br1 C12 C13 C14 179.6(2) . . . . ? C10 C9 C14 C13 0.8(4) . . . . ? C8 C9 C14 C13 -179.5(3) . . . . ? C12 C13 C14 C9 -0.6(4) . . . . ? O8 C15 C16 C17 -18.7(5) . . . . ? O6 C15 C16 C17 160.7(3) . . . . ? O8 C15 C16 C21 161.1(3) . . . . ? O6 C15 C16 C21 -19.6(4) . . . . ? C21 C16 C17 C18 1.9(5) . . . . ? C15 C16 C17 C18 -178.3(3) . . . . ? C16 C17 C18 C19 -0.1(5) . . . . ? C17 C18 C19 C20 -2.2(5) . . . . ? C17 C18 C19 Br2 176.7(3) . . . . ? C18 C19 C20 C21 2.7(5) . . . . ? Br2 C19 C20 C21 -176.2(2) . . . . ? C19 C20 C21 C16 -0.9(5) . . . . ? C17 C16 C21 C20 -1.4(4) . . . . ? C15 C16 C21 C20 178.8(3) . . . . ? O3 C7 O1 C1 -62.6(3) . . . . ? O5 C7 O1 C1 62.1(3) . . . . ? C2 C1 O1 C7 58.0(3) . . . . ? C6 C1 O1 C7 -61.0(3) . . . . ? O7 C8 O2 C2 0.1(4) . . . . ? C9 C8 O2 C2 179.8(2) . . . . ? C3 C2 O2 C8 -80.8(3) . . . . ? C1 C2 O2 C8 161.6(2) . . . . ? O5 C7 O3 C3 -61.3(3) . . . . ? O1 C7 O3 C3 63.0(3) . . . . ? C2 C3 O3 C7 -58.6(3) . . . . ? C4 C3 O3 C7 60.5(3) . . . . ? O3 C7 O5 C5 61.8(3) . . . . ? O1 C7 O5 C5 -62.6(3) . . . . ? C6 C5 O5 C7 61.3(3) . . . . ? C4 C5 O5 C7 -60.4(3) . . . . ? O8 C15 O6 C6 -3.3(4) . . . . ? C16 C15 O6 C6 177.3(2) . . . . ? C5 C6 O6 C15 -103.0(3) . . . . ? C1 C6 O6 C15 138.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C7 H7 O9 1.00 2.27 3.223(4) 159.0 3_665 C5 H5 O4 1.00 2.52 3.231(3) 128.2 2_545 C13 H13 O8 0.95 2.54 3.369(4) 145.7 3_565 C5 H5 O7 1.00 2.59 3.297(3) 127.4 2_545 O4 H4A O7 0.81(3) 1.98(4) 2.780(3) 171(3) 2_545 C22 H22A Br2 0.98 2.92 3.819(5) 153.4 2_545 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.822 _refine_diff_density_min -0.592 _refine_diff_density_rms 0.082 #===END data_2C _database_code_depnum_ccdc_archive 'CCDC 752177' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate dichloromethane solvate ; _chemical_name_common ;2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate dichloromethane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8 , C H2 Cl2' _chemical_formula_sum 'C22 H18 Br2 Cl2 O8' _chemical_formula_weight 641.08 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8524(11) _cell_length_b 10.2018(8) _cell_length_c 18.5250(15) _cell_angle_alpha 90.00 _cell_angle_beta 102.8700(10) _cell_angle_gamma 90.00 _cell_volume 2367.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 6186 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 28.08 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 3.696 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2397 _exptl_absorpt_correction_T_max 0.5773 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11686 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4166 _reflns_number_gt 3739 _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 1.4.1' _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^)+(0.0447P)^2^+3.2689P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4166 _refine_ls_number_parameters 359 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.049 _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 0.54873(3) 1.20226(3) -0.208304(16) 0.03096(11) Uani 1 1 d . . . Br2 Br 0.40413(9) 0.69429(9) 0.51163(5) 0.0368(2) Uani 0.80 1 d P A 1 Br2' Br 0.3853(3) 0.7322(3) 0.49255(19) 0.0316(7) Uani 0.20 1 d PD A 2 C1 C 0.6043(2) 0.5086(3) 0.09489(14) 0.0196(6) Uani 1 1 d . . . H1 H 0.5261 0.5271 0.0792 0.023 Uiso 1 1 calc R . . C2 C 0.6660(2) 0.6356(3) 0.11639(14) 0.0192(6) Uani 1 1 d . . . H2 H 0.6457 0.6757 0.1605 0.023 Uiso 1 1 calc R . . C3 C 0.7851(2) 0.6044(3) 0.13372(14) 0.0204(6) Uani 1 1 d . . . H3 H 0.8274 0.6874 0.1433 0.025 Uiso 1 1 calc R . . C4 C 0.8134(2) 0.5150(3) 0.20114(15) 0.0220(6) Uani 1 1 d . . . H4 H 0.8908 0.4917 0.2099 0.026 Uiso 1 1 calc R . . C5 C 0.7468(2) 0.3895(3) 0.18269(15) 0.0223(6) Uani 1 1 d . . . H5 H 0.7639 0.3267 0.2251 0.027 Uiso 1 1 calc R . . C6 C 0.6264(2) 0.4132(3) 0.16043(14) 0.0210(6) Uani 1 1 d . . . H6 H 0.5883 0.3285 0.1458 0.025 Uiso 1 1 calc R . . C7 C 0.7523(2) 0.4197(3) 0.05722(15) 0.0237(6) Uani 1 1 d . . . H7 H 0.7741 0.3758 0.0146 0.028 Uiso 1 1 calc R . . C8 C 0.6581(2) 0.8507(3) 0.06744(15) 0.0192(5) Uani 1 1 d . . . C9 C 0.6307(2) 0.9329(3) -0.00034(15) 0.0195(6) Uani 1 1 d . . . C10 C 0.6395(2) 1.0689(3) 0.00764(15) 0.0223(6) Uani 1 1 d . . . H10 H 0.6627 1.1065 0.0554 0.027 Uiso 1 1 calc R . . C11 C 0.6141(2) 1.1486(3) -0.05439(16) 0.0241(6) Uani 1 1 d . . . H11 H 0.6192 1.2412 -0.0495 0.029 Uiso 1 1 calc R . . C12 C 0.5813(2) 1.0919(3) -0.12339(15) 0.0228(6) Uani 1 1 d . . . C13 C 0.5726(2) 0.9571(3) -0.13294(15) 0.0247(6) Uani 1 1 d . . . H13 H 0.5502 0.9201 -0.1809 0.030 Uiso 1 1 calc R . . C14 C 0.5975(2) 0.8776(3) -0.07034(15) 0.0222(6) Uani 1 1 d . . . H14 H 0.5918 0.7851 -0.0755 0.027 Uiso 1 1 calc R . . C15 C 0.5110(2) 0.4128(3) 0.24479(17) 0.0311(7) Uani 1 1 d . . . C16 C 0.4865(2) 0.4828(3) 0.30958(16) 0.0254(6) Uani 1 1 d . A . C17 C 0.3951(3) 0.4493(4) 0.3334(2) 0.0439(9) Uani 1 1 d . . . H17 H 0.3497 0.3821 0.3084 0.053 Uiso 1 1 calc R . . C18 C 0.3693(3) 0.5123(4) 0.39289(19) 0.0401(8) Uani 1 1 d . A . H18 H 0.3069 0.4889 0.4093 0.048 Uiso 1 1 calc R . . C19 C 0.4358(2) 0.6098(3) 0.42807(16) 0.0301(7) Uani 1 1 d D . . C20 C 0.5269(2) 0.6448(3) 0.40531(16) 0.0296(7) Uani 1 1 d . A . H20 H 0.5717 0.7122 0.4304 0.036 Uiso 1 1 calc R . . C21 C 0.5526(2) 0.5814(3) 0.34583(16) 0.0247(6) Uani 1 1 d . . . H21 H 0.6153 0.6051 0.3297 0.030 Uiso 1 1 calc R A . O1 O 0.64160(15) 0.44520(18) 0.03563(10) 0.0216(4) Uani 1 1 d . . . O2 O 0.63822(15) 0.72274(18) 0.05335(10) 0.0208(4) Uani 1 1 d . . . O3 O 0.81037(15) 0.53622(19) 0.07167(10) 0.0236(4) Uani 1 1 d . . . O4 O 0.79570(17) 0.58614(19) 0.26294(11) 0.0264(4) Uani 1 1 d D . . O5 O 0.77506(16) 0.33293(19) 0.11760(11) 0.0250(4) Uani 1 1 d . . . O6 O 0.59069(16) 0.47042(18) 0.22151(10) 0.0247(4) Uani 1 1 d . . . O7 O 0.69444(16) 0.89230(19) 0.12919(10) 0.0256(4) Uani 1 1 d . . . O8 O 0.4647(3) 0.3199(3) 0.2150(2) 0.0850(13) Uani 1 1 d . . . C22 C 0.1813(9) 0.4427(10) 0.1197(7) 0.047(3) Uani 0.40 1 d PD B 1 H22A H 0.1987 0.4010 0.0756 0.056 Uiso 0.40 1 calc PR B 1 H22B H 0.1937 0.3773 0.1602 0.056 Uiso 0.40 1 calc PR B 1 Cl1 Cl 0.0491(2) 0.4880(3) 0.09949(16) 0.0459(6) Uani 0.40 1 d PD B 1 Cl2 Cl 0.2669(2) 0.5792(3) 0.14662(13) 0.0522(6) Uani 0.40 1 d PD B 1 C23 C 0.1059(10) 0.4886(14) 0.1174(6) 0.077(6) Uani 0.40 1 d PD C 2 H23A H 0.0782 0.5111 0.0647 0.092 Uiso 0.40 1 calc PR C 2 H23B H 0.0649 0.4126 0.1294 0.092 Uiso 0.40 1 calc PR C 2 Cl3 Cl 0.0882(2) 0.6212(3) 0.17237(16) 0.0588(6) Uani 0.40 1 d PD C 2 Cl4 Cl 0.2417(4) 0.4460(7) 0.1318(2) 0.120(2) Uani 0.40 1 d PD C 2 C24 C 0.200(2) 0.477(3) 0.1715(19) 0.094(9) Uiso 0.20 1 d PD D 3 H24A H 0.2263 0.5091 0.2227 0.113 Uiso 0.20 1 calc PR D 3 H24B H 0.1737 0.3858 0.1741 0.113 Uiso 0.20 1 calc PR D 3 Cl5 Cl 0.3014(5) 0.4795(5) 0.1241(3) 0.0525(13) Uiso 0.20 1 d PD D 3 Cl6 Cl 0.0963(11) 0.5762(14) 0.1250(8) 0.129(4) Uiso 0.20 1 d P D 3 H4A H 0.798(3) 0.535(3) 0.2962(15) 0.034(10) Uiso 1 1 d 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 Br1 0.0422(2) 0.02478(17) 0.02324(17) 0.00830(12) 0.00153(13) 0.00369(12) Br2 0.0440(4) 0.0423(5) 0.0300(5) -0.0127(3) 0.0208(4) -0.0032(3) Br2' 0.0387(15) 0.0340(18) 0.0257(16) -0.0104(11) 0.0148(12) -0.0024(12) C1 0.0245(14) 0.0187(13) 0.0158(13) -0.0035(11) 0.0049(11) 0.0012(11) C2 0.0261(14) 0.0176(14) 0.0132(12) 0.0014(10) 0.0032(11) 0.0009(11) C3 0.0236(14) 0.0193(13) 0.0173(13) 0.0021(11) 0.0023(11) -0.0020(11) C4 0.0248(14) 0.0202(14) 0.0192(13) 0.0024(11) 0.0012(11) 0.0022(11) C5 0.0332(15) 0.0173(13) 0.0171(13) 0.0010(11) 0.0070(11) 0.0026(12) C6 0.0290(15) 0.0180(13) 0.0179(13) -0.0045(11) 0.0094(11) -0.0030(11) C7 0.0294(15) 0.0239(15) 0.0194(14) -0.0011(11) 0.0088(11) 0.0032(12) C8 0.0217(13) 0.0160(13) 0.0197(14) -0.0036(11) 0.0036(11) 0.0018(11) C9 0.0211(13) 0.0176(13) 0.0192(13) -0.0010(11) 0.0030(10) 0.0013(11) C10 0.0255(14) 0.0196(14) 0.0200(14) -0.0040(11) 0.0016(11) 0.0009(11) C11 0.0300(15) 0.0145(13) 0.0271(15) -0.0007(11) 0.0048(12) 0.0025(11) C12 0.0256(14) 0.0204(14) 0.0208(14) 0.0044(11) 0.0021(11) 0.0043(11) C13 0.0308(15) 0.0222(14) 0.0183(13) 0.0008(11) -0.0004(11) 0.0013(12) C14 0.0271(14) 0.0161(13) 0.0218(14) 0.0002(11) 0.0021(11) 0.0025(11) C15 0.0324(16) 0.0326(17) 0.0324(16) -0.0118(14) 0.0157(13) -0.0085(14) C16 0.0288(15) 0.0246(15) 0.0251(15) -0.0048(12) 0.0110(12) -0.0045(12) C17 0.0385(18) 0.054(2) 0.044(2) -0.0268(18) 0.0208(16) -0.0240(17) C18 0.0325(17) 0.052(2) 0.0413(19) -0.0205(16) 0.0211(15) -0.0164(16) C19 0.0347(16) 0.0354(17) 0.0237(15) -0.0109(13) 0.0141(13) -0.0009(14) C20 0.0331(16) 0.0311(16) 0.0270(15) -0.0112(13) 0.0115(13) -0.0091(13) C21 0.0275(15) 0.0263(15) 0.0230(14) -0.0009(12) 0.0112(12) -0.0035(12) O1 0.0266(10) 0.0231(10) 0.0153(9) -0.0039(8) 0.0050(8) 0.0009(8) O2 0.0296(10) 0.0166(9) 0.0144(9) 0.0011(7) 0.0008(8) 0.0015(8) O3 0.0265(10) 0.0248(10) 0.0211(10) 0.0009(8) 0.0086(8) -0.0006(8) O4 0.0415(12) 0.0200(10) 0.0148(10) 0.0012(8) 0.0005(9) -0.0013(9) O5 0.0348(11) 0.0200(10) 0.0217(10) 0.0013(8) 0.0092(8) 0.0066(9) O6 0.0380(11) 0.0193(10) 0.0213(10) -0.0051(8) 0.0161(9) -0.0078(9) O7 0.0389(11) 0.0205(10) 0.0158(10) -0.0023(8) 0.0026(8) 0.0005(9) O8 0.100(2) 0.081(2) 0.101(3) -0.074(2) 0.080(2) -0.070(2) C22 0.029(6) 0.043(6) 0.057(7) 0.001(5) -0.013(6) -0.025(5) Cl1 0.0350(14) 0.0506(14) 0.0504(16) -0.0032(12) 0.0056(12) 0.0011(13) Cl2 0.0526(13) 0.0620(16) 0.0382(12) -0.0004(11) 0.0019(10) -0.0257(12) C23 0.058(10) 0.112(14) 0.041(6) 0.022(7) -0.029(7) -0.069(11) Cl3 0.0692(17) 0.0451(14) 0.0590(16) 0.0007(12) 0.0077(13) -0.0087(12) Cl4 0.065(3) 0.217(6) 0.069(2) -0.077(3) -0.001(2) 0.021(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C12 1.904(3) . ? Br2 C19 1.894(3) . ? Br2' C19 1.937(5) . ? C1 O1 1.445(3) . ? C1 C2 1.525(4) . ? C1 C6 1.533(4) . ? C1 H1 1.0000 . ? C2 O2 1.448(3) . ? C2 C3 1.526(4) . ? C2 H2 1.0000 . ? C3 O3 1.441(3) . ? C3 C4 1.524(4) . ? C3 H3 1.0000 . ? C4 O4 1.416(3) . ? C4 C5 1.536(4) . ? C4 H4 1.0000 . ? C5 O5 1.454(3) . ? C5 C6 1.530(4) . ? C5 H5 1.0000 . ? C6 O6 1.436(3) . ? C6 H6 1.0000 . ? C7 O3 1.397(3) . ? C7 O5 1.405(3) . ? C7 O1 1.414(3) . ? C7 H7 1.0000 . ? C8 O7 1.212(3) . ? C8 O2 1.345(3) . ? C8 C9 1.485(4) . ? C9 C14 1.391(4) . ? C9 C10 1.397(4) . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 C12 1.381(4) . ? C11 H11 0.9500 . ? C12 C13 1.388(4) . ? C13 C14 1.393(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 O8 1.187(4) . ? C15 O6 1.333(3) . ? C15 C16 1.489(4) . ? C16 C17 1.387(4) . ? C16 C21 1.389(4) . ? C17 C18 1.379(4) . ? C17 H17 0.9500 . ? C18 C19 1.377(5) . ? C18 H18 0.9500 . ? C19 C20 1.377(4) . ? C20 C21 1.380(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? O4 H4A 0.805(18) . ? C22 Cl1 1.720(12) . ? C22 Cl2 1.776(9) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 Cl3 1.738(13) . ? C23 Cl4 1.760(14) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 Cl5 1.731(18) . ? C24 Cl6 1.74(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? 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 O1 C1 C2 109.7(2) . . ? O1 C1 C6 106.5(2) . . ? C2 C1 C6 109.8(2) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C1 106.9(2) . . ? O2 C2 C3 110.7(2) . . ? C1 C2 C3 108.5(2) . . ? O2 C2 H2 110.2 . . ? C1 C2 H2 110.2 . . ? C3 C2 H2 110.2 . . ? O3 C3 C4 108.0(2) . . ? O3 C3 C2 109.1(2) . . ? C4 C3 C2 110.0(2) . . ? O3 C3 H3 109.9 . . ? C4 C3 H3 109.9 . . ? C2 C3 H3 109.9 . . ? O4 C4 C3 107.7(2) . . ? O4 C4 C5 115.2(2) . . ? C3 C4 C5 107.3(2) . . ? O4 C4 H4 108.8 . . ? C3 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? O5 C5 C6 105.3(2) . . ? O5 C5 C4 106.6(2) . . ? C6 C5 C4 114.1(2) . . ? O5 C5 H5 110.2 . . ? C6 C5 H5 110.2 . . ? C4 C5 H5 110.2 . . ? O6 C6 C5 109.5(2) . . ? O6 C6 C1 109.3(2) . . ? C5 C6 C1 108.1(2) . . ? O6 C6 H6 110.0 . . ? C5 C6 H6 110.0 . . ? C1 C6 H6 110.0 . . ? O3 C7 O5 112.1(2) . . ? O3 C7 O1 111.0(2) . . ? O5 C7 O1 111.0(2) . . ? O3 C7 H7 107.5 . . ? O5 C7 H7 107.5 . . ? O1 C7 H7 107.5 . . ? O7 C8 O2 122.7(2) . . ? O7 C8 C9 124.7(2) . . ? O2 C8 C9 112.6(2) . . ? C14 C9 C10 120.1(2) . . ? C14 C9 C8 121.7(2) . . ? C10 C9 C8 118.2(2) . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 119.2(3) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 122.2(3) . . ? C11 C12 Br1 118.9(2) . . ? C13 C12 Br1 118.9(2) . . ? C12 C13 C14 118.3(3) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? C9 C14 C13 120.4(3) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? O8 C15 O6 122.9(3) . . ? O8 C15 C16 125.7(3) . . ? O6 C15 C16 111.4(2) . . ? C17 C16 C21 119.7(3) . . ? C17 C16 C15 118.9(3) . . ? C21 C16 C15 121.4(3) . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C19 C18 C17 118.8(3) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C20 C19 C18 121.5(3) . . ? C20 C19 Br2 119.0(2) . . ? C18 C19 Br2 119.5(2) . . ? C20 C19 Br2' 116.5(3) . . ? C18 C19 Br2' 120.0(3) . . ? C19 C20 C21 119.6(3) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C20 C21 C16 119.7(3) . . ? C20 C21 H21 120.2 . . ? C16 C21 H21 120.2 . . ? C7 O1 C1 110.5(2) . . ? C8 O2 C2 115.95(19) . . ? C7 O3 C3 111.0(2) . . ? C4 O4 H4A 108(3) . . ? C7 O5 C5 111.3(2) . . ? C15 O6 C6 118.6(2) . . ? Cl1 C22 Cl2 111.8(6) . . ? Cl1 C22 H22A 109.3 . . ? Cl2 C22 H22A 109.3 . . ? Cl1 C22 H22B 109.3 . . ? Cl2 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? Cl3 C23 Cl4 111.0(6) . . ? Cl3 C23 H23A 109.4 . . ? Cl4 C23 H23A 109.4 . . ? Cl3 C23 H23B 109.4 . . ? Cl4 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? Cl5 C24 Cl6 108.6(17) . . ? Cl5 C24 H24A 110.0 . . ? Cl6 C24 H24A 110.0 . . ? Cl5 C24 H24B 110.0 . . ? Cl6 C24 H24B 110.0 . . ? H24A C24 H24B 108.4 . . ? 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 O1 C1 C2 O2 65.6(3) . . . . ? C6 C1 C2 O2 -177.7(2) . . . . ? O1 C1 C2 C3 -53.8(3) . . . . ? C6 C1 C2 C3 62.9(3) . . . . ? O2 C2 C3 O3 -62.9(3) . . . . ? C1 C2 C3 O3 54.1(3) . . . . ? O2 C2 C3 C4 178.8(2) . . . . ? C1 C2 C3 C4 -64.2(3) . . . . ? O3 C3 C4 O4 175.8(2) . . . . ? C2 C3 C4 O4 -65.2(3) . . . . ? O3 C3 C4 C5 -59.6(3) . . . . ? C2 C3 C4 C5 59.3(3) . . . . ? O4 C4 C5 O5 179.1(2) . . . . ? C3 C4 C5 O5 59.2(3) . . . . ? O4 C4 C5 C6 63.3(3) . . . . ? C3 C4 C5 C6 -56.6(3) . . . . ? O5 C5 C6 O6 -179.56(19) . . . . ? C4 C5 C6 O6 -63.0(3) . . . . ? O5 C5 C6 C1 -60.6(3) . . . . ? C4 C5 C6 C1 56.0(3) . . . . ? O1 C1 C6 O6 -179.8(2) . . . . ? C2 C1 C6 O6 61.4(3) . . . . ? O1 C1 C6 C5 61.1(3) . . . . ? C2 C1 C6 C5 -57.7(3) . . . . ? O7 C8 C9 C14 174.6(3) . . . . ? O2 C8 C9 C14 -5.3(4) . . . . ? O7 C8 C9 C10 -5.2(4) . . . . ? O2 C8 C9 C10 174.9(2) . . . . ? C14 C9 C10 C11 0.5(4) . . . . ? C8 C9 C10 C11 -179.7(2) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 C13 0.1(4) . . . . ? C10 C11 C12 Br1 -179.1(2) . . . . ? C11 C12 C13 C14 0.3(4) . . . . ? Br1 C12 C13 C14 179.5(2) . . . . ? C10 C9 C14 C13 -0.1(4) . . . . ? C8 C9 C14 C13 -179.9(3) . . . . ? C12 C13 C14 C9 -0.3(4) . . . . ? O8 C15 C16 C17 -8.1(6) . . . . ? O6 C15 C16 C17 169.7(3) . . . . ? O8 C15 C16 C21 172.7(4) . . . . ? O6 C15 C16 C21 -9.6(4) . . . . ? C21 C16 C17 C18 -0.3(6) . . . . ? C15 C16 C17 C18 -179.6(3) . . . . ? C16 C17 C18 C19 0.3(6) . . . . ? C17 C18 C19 C20 -0.2(6) . . . . ? C17 C18 C19 Br2 -178.2(3) . . . . ? C17 C18 C19 Br2' 163.1(3) . . . . ? C18 C19 C20 C21 0.1(5) . . . . ? Br2 C19 C20 C21 178.1(2) . . . . ? Br2' C19 C20 C21 -163.7(3) . . . . ? C19 C20 C21 C16 -0.1(5) . . . . ? C17 C16 C21 C20 0.2(5) . . . . ? C15 C16 C21 C20 179.5(3) . . . . ? O3 C7 O1 C1 -62.9(3) . . . . ? O5 C7 O1 C1 62.5(3) . . . . ? C2 C1 O1 C7 57.9(3) . . . . ? C6 C1 O1 C7 -60.9(3) . . . . ? O7 C8 O2 C2 -1.8(4) . . . . ? C9 C8 O2 C2 178.1(2) . . . . ? C1 C2 O2 C8 161.0(2) . . . . ? C3 C2 O2 C8 -81.0(3) . . . . ? O5 C7 O3 C3 -60.9(3) . . . . ? O1 C7 O3 C3 63.9(3) . . . . ? C4 C3 O3 C7 60.0(3) . . . . ? C2 C3 O3 C7 -59.5(3) . . . . ? O3 C7 O5 C5 61.5(3) . . . . ? O1 C7 O5 C5 -63.3(3) . . . . ? C6 C5 O5 C7 61.5(3) . . . . ? C4 C5 O5 C7 -60.1(3) . . . . ? O8 C15 O6 C6 -3.8(5) . . . . ? C16 C15 O6 C6 178.4(2) . . . . ? C5 C6 O6 C15 -126.1(3) . . . . ? C1 C6 O6 C15 115.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A O7 0.805(18) 1.992(19) 2.794(3) 174(4) 2_645 C13 H13 O8 0.95 2.53 3.195(4) 127.6 3_665 C11 H11 O1 0.95 2.59 3.435(3) 148.7 1_565 C5 H5 O4 1.00 2.60 3.337(3) 131.0 2_645 C22 H22A Br2 0.99 2.80 3.515(11) 129.4 2_545 C17 H17 Cl3 0.95 2.78 3.357(5) 120.1 2_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.776 _refine_diff_density_min -0.624 _refine_diff_density_rms 0.074 #===END data_2D _database_code_depnum_ccdc_archive 'CCDC 752178' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate nitromethane solvate ; _chemical_name_common ;2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate nitromethane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8 , C H3 N O2' _chemical_formula_sum 'C22 H19 Br2 N O10' _chemical_formula_weight 617.20 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.1747(15) _cell_length_b 10.1533(12) _cell_length_c 19.261(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.231(2) _cell_angle_gamma 90.00 _cell_volume 2317.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 5669 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 28.27 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 3.557 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5499 _exptl_absorpt_correction_T_max 0.8070 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11343 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4067 _reflns_number_gt 3666 _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 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^)+(0.0392P)^2^+1.6418P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4067 _refine_ls_number_parameters 338 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.002 _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 C22' C 0.343(3) 0.013(4) 0.8279(19) 0.065(10) Uiso 0.20 1 d PD A 2 H22D H 0.3889 -0.0674 0.8312 0.097 Uiso 0.20 1 calc PR A 2 H22E H 0.3901 0.0858 0.8508 0.097 Uiso 0.20 1 calc PR A 2 H22F H 0.3116 0.0339 0.7777 0.097 Uiso 0.20 1 calc PR A 2 Br1 Br 0.92967(3) 0.68214(3) 1.197383(14) 0.02576(11) Uani 1 1 d . . . Br2 Br 1.10479(3) 0.27633(3) 0.503093(16) 0.03270(11) Uani 1 1 d . . . O1 O 0.87786(16) -0.06640(18) 0.95088(9) 0.0204(4) Uani 1 1 d . . . O2 O 0.86710(16) 0.21324(17) 0.93921(9) 0.0190(4) Uani 1 1 d . . . O3 O 0.69456(16) 0.01197(18) 0.91367(9) 0.0210(4) Uani 1 1 d . . . O4 O 0.71823(18) 0.08050(18) 0.73287(10) 0.0227(4) Uani 1 1 d D . . O5 O 0.74698(17) -0.18401(17) 0.86743(10) 0.0215(4) Uani 1 1 d . . . O6 O 0.94224(16) -0.01641(17) 0.77683(9) 0.0211(4) Uani 1 1 d . . . O7 O 0.79748(18) 0.38420(18) 0.86859(9) 0.0265(5) Uani 1 1 d . . . O8 O 1.0009(2) -0.20552(18) 0.73472(11) 0.0314(5) Uani 1 1 d . . . C1 C 0.9170(2) 0.0068(3) 0.89641(13) 0.0193(6) Uani 1 1 d . . . H1 H 0.9982 0.0314 0.9138 0.023 Uiso 1 1 calc R . . C2 C 0.8454(2) 0.1288(2) 0.87673(12) 0.0171(5) Uani 1 1 d . . . H2 H 0.8668 0.1751 0.8359 0.021 Uiso 1 1 calc R . . C3 C 0.7213(2) 0.0893(3) 0.85652(13) 0.0183(5) Uani 1 1 d . . . H3 H 0.6725 0.1696 0.8476 0.022 Uiso 1 1 calc R . . C4 C 0.6998(2) 0.0024(3) 0.78991(13) 0.0193(6) Uani 1 1 d . . . H4 H 0.6194 -0.0276 0.7788 0.023 Uiso 1 1 calc R . . C5 C 0.7772(2) -0.1182(2) 0.80745(13) 0.0192(6) Uani 1 1 d . . . H5 H 0.7646 -0.1788 0.7654 0.023 Uiso 1 1 calc R . . C6 C 0.9022(2) -0.0854(2) 0.83169(13) 0.0187(5) Uani 1 1 d . . . H6 H 0.9469 -0.1678 0.8452 0.022 Uiso 1 1 calc R . . C7 C 0.7639(2) -0.0998(3) 0.92733(14) 0.0217(6) Uani 1 1 d . . . H7 H 0.7417 -0.1498 0.9667 0.026 Uiso 1 1 calc R . . C8 C 0.8387(2) 0.3400(2) 0.92763(14) 0.0186(6) Uani 1 1 d . . . C9 C 0.8621(2) 0.4193(3) 0.99389(13) 0.0176(5) Uani 1 1 d . . . C10 C 0.8535(2) 0.5566(3) 0.98808(14) 0.0198(6) Uani 1 1 d . . . H10 H 0.8321 0.5966 0.9424 0.024 Uiso 1 1 calc R . . C11 C 0.8761(2) 0.6343(3) 1.04884(14) 0.0211(6) Uani 1 1 d . . . H11 H 0.8718 0.7276 1.0453 0.025 Uiso 1 1 calc R . . C12 C 0.9050(2) 0.5732(3) 1.11486(13) 0.0195(6) Uani 1 1 d . . . C13 C 0.9146(2) 0.4377(3) 1.12215(14) 0.0230(6) Uani 1 1 d . . . H13 H 0.9351 0.3983 1.1680 0.028 Uiso 1 1 calc R . . C14 C 0.8935(2) 0.3609(3) 1.06117(14) 0.0217(6) Uani 1 1 d . . . H14 H 0.9005 0.2678 1.0651 0.026 Uiso 1 1 calc R . . C15 C 0.9858(2) -0.0882(3) 0.73028(13) 0.0204(6) Uani 1 1 d . . . C16 C 1.0119(2) -0.0016(3) 0.67370(14) 0.0201(6) Uani 1 1 d . . . C17 C 1.0841(3) -0.0463(3) 0.63219(15) 0.0269(6) Uani 1 1 d . . . H17 H 1.1153 -0.1323 0.6395 0.032 Uiso 1 1 calc R . . C18 C 1.1104(3) 0.0343(3) 0.58030(15) 0.0277(6) Uani 1 1 d . . . H18 H 1.1595 0.0040 0.5518 0.033 Uiso 1 1 calc R . . C19 C 1.0643(2) 0.1597(3) 0.57050(14) 0.0249(6) Uani 1 1 d . . . C20 C 0.9898(2) 0.2043(3) 0.60956(15) 0.0241(6) Uani 1 1 d . . . H20 H 0.9571 0.2894 0.6011 0.029 Uiso 1 1 calc R . . C21 C 0.9632(2) 0.1230(3) 0.66137(14) 0.0214(6) Uani 1 1 d . . . H21 H 0.9118 0.1523 0.6885 0.026 Uiso 1 1 calc R . . C22 C 0.3465(11) 0.0469(10) 0.8302(7) 0.119(5) Uani 0.80 1 d P B 1 H22A H 0.3344 -0.0374 0.8049 0.178 Uiso 0.80 1 calc PR B 1 H22B H 0.4239 0.0507 0.8592 0.178 Uiso 0.80 1 calc PR B 1 H22C H 0.3345 0.1192 0.7955 0.178 Uiso 0.80 1 calc PR B 1 N1 N 0.2713(4) 0.0587(6) 0.8740(3) 0.0519(11) Uani 0.80 1 d P B 1 O9 O 0.3008(4) 0.1507(4) 0.91720(19) 0.0690(11) Uani 0.80 1 d P B 1 O10 O 0.1888(4) -0.0051(6) 0.8748(4) 0.0991(19) Uani 0.80 1 d P B 1 N1' N 0.2496(15) -0.0091(15) 0.8645(7) 0.030(4) Uiso 0.20 1 d PD A 2 O9' O 0.2231(15) 0.0566(15) 0.9101(7) 0.047(3) Uiso 0.20 1 d PD A 2 O10' O 0.2136(11) -0.1035(12) 0.8313(6) 0.043(3) Uiso 0.20 1 d PD A 2 H4A H 0.714(3) 0.032(3) 0.6988(15) 0.054(12) Uiso 1 1 d 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 Br1 0.03644(19) 0.02181(17) 0.01696(16) -0.00608(10) 0.00185(12) 0.00197(12) Br2 0.0350(2) 0.0374(2) 0.03074(19) 0.01256(13) 0.01798(14) 0.00437(13) O1 0.0253(11) 0.0217(10) 0.0141(9) 0.0032(7) 0.0043(7) -0.0006(8) O2 0.0283(11) 0.0135(9) 0.0147(9) -0.0030(7) 0.0043(7) -0.0015(8) O3 0.0264(11) 0.0213(10) 0.0172(9) 0.0013(7) 0.0087(8) -0.0006(8) O4 0.0402(12) 0.0142(9) 0.0134(9) 0.0016(8) 0.0052(8) -0.0001(8) O5 0.0323(11) 0.0164(9) 0.0165(9) 0.0013(7) 0.0074(8) -0.0044(8) O6 0.0305(11) 0.0173(9) 0.0189(10) 0.0008(7) 0.0128(8) 0.0003(8) O7 0.0462(13) 0.0176(10) 0.0136(10) 0.0011(7) 0.0024(8) 0.0002(9) O8 0.0497(14) 0.0174(10) 0.0341(12) 0.0014(8) 0.0243(10) 0.0058(9) C1 0.0241(15) 0.0210(14) 0.0137(13) 0.0005(10) 0.0061(10) -0.0013(11) C2 0.0258(15) 0.0153(12) 0.0103(12) -0.0021(10) 0.0043(10) -0.0024(11) C3 0.0274(15) 0.0151(13) 0.0133(12) 0.0009(10) 0.0067(10) 0.0001(11) C4 0.0262(15) 0.0169(13) 0.0139(13) -0.0003(10) 0.0027(10) -0.0033(11) C5 0.0319(16) 0.0138(12) 0.0125(13) 0.0010(10) 0.0064(11) -0.0034(11) C6 0.0263(15) 0.0142(12) 0.0172(13) 0.0017(10) 0.0082(10) 0.0010(11) C7 0.0305(16) 0.0195(14) 0.0166(13) 0.0027(11) 0.0083(11) -0.0009(12) C8 0.0220(15) 0.0161(13) 0.0187(14) 0.0002(10) 0.0067(11) -0.0034(11) C9 0.0187(14) 0.0181(13) 0.0155(13) -0.0015(10) 0.0033(10) -0.0002(11) C10 0.0247(15) 0.0180(13) 0.0166(13) 0.0006(10) 0.0046(10) -0.0016(11) C11 0.0259(15) 0.0151(13) 0.0219(14) -0.0020(11) 0.0047(11) -0.0020(11) C12 0.0209(14) 0.0204(13) 0.0162(13) -0.0057(10) 0.0020(10) -0.0002(11) C13 0.0317(16) 0.0200(14) 0.0160(13) -0.0004(11) 0.0031(11) 0.0027(12) C14 0.0277(16) 0.0147(13) 0.0218(14) -0.0014(11) 0.0040(11) 0.0010(11) C15 0.0233(15) 0.0198(14) 0.0180(13) -0.0024(11) 0.0050(11) 0.0003(11) C16 0.0217(15) 0.0199(14) 0.0191(14) -0.0024(11) 0.0057(11) -0.0033(11) C17 0.0315(17) 0.0245(15) 0.0270(15) 0.0011(12) 0.0113(12) 0.0028(13) C18 0.0297(17) 0.0297(16) 0.0282(16) 0.0004(12) 0.0157(12) 0.0035(13) C19 0.0254(16) 0.0307(16) 0.0201(14) 0.0035(12) 0.0082(11) -0.0016(12) C20 0.0256(16) 0.0225(14) 0.0248(15) 0.0033(11) 0.0073(12) 0.0018(12) C21 0.0229(15) 0.0228(14) 0.0201(14) -0.0014(11) 0.0081(11) 0.0017(12) C22 0.171(11) 0.061(6) 0.172(11) -0.042(6) 0.138(9) -0.020(6) N1 0.049(3) 0.056(3) 0.054(3) 0.018(2) 0.020(2) 0.011(2) O9 0.094(3) 0.071(3) 0.045(2) 0.001(2) 0.022(2) 0.026(2) O10 0.038(3) 0.096(4) 0.154(5) 0.059(4) 0.003(3) -0.011(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C22' N1' 1.485(19) . ? C22' H22D 0.9800 . ? C22' H22E 0.9800 . ? C22' H22F 0.9800 . ? Br1 C12 1.903(2) . ? Br2 C19 1.904(3) . ? O1 C7 1.399(3) . ? O1 C1 1.452(3) . ? O2 C8 1.338(3) . ? O2 C2 1.452(3) . ? O3 C7 1.403(3) . ? O3 C3 1.449(3) . ? O4 C4 1.414(3) . ? O4 H4A 0.812(19) . ? O5 C7 1.413(3) . ? O5 C5 1.453(3) . ? O6 C15 1.354(3) . ? O6 C6 1.442(3) . ? O7 C8 1.219(3) . ? O8 C15 1.206(3) . ? C1 C2 1.512(4) . ? C1 C6 1.536(3) . ? C1 H1 1.0000 . ? C2 C3 1.525(4) . ? C2 H2 1.0000 . ? C3 C4 1.529(3) . ? C3 H3 1.0000 . ? C4 C5 1.534(4) . ? C4 H4 1.0000 . ? C5 C6 1.523(4) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.480(3) . ? C9 C14 1.397(4) . ? C9 C10 1.401(4) . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 C12 1.386(4) . ? C11 H11 0.9500 . ? C12 C13 1.385(4) . ? C13 C14 1.384(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.490(4) . ? C16 C17 1.392(4) . ? C16 C21 1.394(4) . ? C17 C18 1.385(4) . ? C17 H17 0.9500 . ? C18 C19 1.387(4) . ? C18 H18 0.9500 . ? C19 C20 1.381(4) . ? C20 C21 1.389(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 N1 1.385(8) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 O10 1.199(6) . ? N1 O9 1.248(7) . ? N1' O10' 1.179(16) . ? N1' O9' 1.204(15) . ? 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 N1' C22' H22D 109.5 . . ? N1' C22' H22E 109.5 . . ? H22D C22' H22E 109.5 . . ? N1' C22' H22F 109.5 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 109.5 . . ? C7 O1 C1 110.79(19) . . ? C8 O2 C2 116.04(19) . . ? C7 O3 C3 110.51(19) . . ? C4 O4 H4A 107(3) . . ? C7 O5 C5 110.77(19) . . ? C15 O6 C6 118.2(2) . . ? O1 C1 C2 109.5(2) . . ? O1 C1 C6 106.1(2) . . ? C2 C1 C6 110.0(2) . . ? O1 C1 H1 110.4 . . ? C2 C1 H1 110.4 . . ? C6 C1 H1 110.4 . . ? O2 C2 C1 106.91(19) . . ? O2 C2 C3 110.4(2) . . ? C1 C2 C3 109.2(2) . . ? O2 C2 H2 110.1 . . ? C1 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? O3 C3 C2 109.3(2) . . ? O3 C3 C4 107.4(2) . . ? C2 C3 C4 109.6(2) . . ? O3 C3 H3 110.1 . . ? C2 C3 H3 110.1 . . ? C4 C3 H3 110.1 . . ? O4 C4 C3 107.5(2) . . ? O4 C4 C5 114.8(2) . . ? C3 C4 C5 107.3(2) . . ? O4 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? O5 C5 C6 105.9(2) . . ? O5 C5 C4 106.7(2) . . ? C6 C5 C4 114.4(2) . . ? O5 C5 H5 109.9 . . ? C6 C5 H5 109.9 . . ? C4 C5 H5 109.9 . . ? O6 C6 C5 111.3(2) . . ? O6 C6 C1 107.6(2) . . ? C5 C6 C1 107.8(2) . . ? O6 C6 H6 110.0 . . ? C5 C6 H6 110.0 . . ? C1 C6 H6 110.0 . . ? O1 C7 O3 112.0(2) . . ? O1 C7 O5 111.1(2) . . ? O3 C7 O5 111.5(2) . . ? O1 C7 H7 107.3 . . ? O3 C7 H7 107.3 . . ? O5 C7 H7 107.3 . . ? O7 C8 O2 123.0(2) . . ? O7 C8 C9 124.1(2) . . ? O2 C8 C9 112.8(2) . . ? C14 C9 C10 119.8(2) . . ? C14 C9 C8 121.8(2) . . ? C10 C9 C8 118.4(2) . . ? C11 C10 C9 120.2(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 118.6(2) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 122.4(2) . . ? C13 C12 Br1 119.95(19) . . ? C11 C12 Br1 117.65(19) . . ? C14 C13 C12 118.6(2) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C9 120.4(2) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? O8 C15 O6 124.1(2) . . ? O8 C15 C16 125.5(2) . . ? O6 C15 C16 110.4(2) . . ? C17 C16 C21 119.8(2) . . ? C17 C16 C15 119.7(2) . . ? C21 C16 C15 120.4(2) . . ? C18 C17 C16 120.2(3) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 119.1(3) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C20 C19 C18 121.6(3) . . ? C20 C19 Br2 118.2(2) . . ? C18 C19 Br2 120.3(2) . . ? C19 C20 C21 119.1(3) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C16 120.1(2) . . ? C20 C21 H21 119.9 . . ? C16 C21 H21 119.9 . . ? O10 N1 O9 120.7(6) . . ? O10 N1 C22 129.4(9) . . ? O9 N1 C22 109.9(6) . . ? O10' N1' O9' 136(2) . . ? O10' N1' C22' 95.4(18) . . ? O9' N1' C22' 129(2) . . ? 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 57.5(3) . . . . ? C7 O1 C1 C6 -61.2(3) . . . . ? C8 O2 C2 C1 161.2(2) . . . . ? C8 O2 C2 C3 -80.1(3) . . . . ? O1 C1 C2 O2 66.0(3) . . . . ? C6 C1 C2 O2 -177.7(2) . . . . ? O1 C1 C2 C3 -53.4(3) . . . . ? C6 C1 C2 C3 62.8(3) . . . . ? C7 O3 C3 C2 -57.9(3) . . . . ? C7 O3 C3 C4 61.0(3) . . . . ? O2 C2 C3 O3 -63.5(2) . . . . ? C1 C2 C3 O3 53.8(3) . . . . ? O2 C2 C3 C4 179.05(19) . . . . ? C1 C2 C3 C4 -63.7(3) . . . . ? O3 C3 C4 O4 176.0(2) . . . . ? C2 C3 C4 O4 -65.4(3) . . . . ? O3 C3 C4 C5 -60.1(3) . . . . ? C2 C3 C4 C5 58.6(3) . . . . ? C7 O5 C5 C6 61.5(3) . . . . ? C7 O5 C5 C4 -60.8(3) . . . . ? O4 C4 C5 O5 179.1(2) . . . . ? C3 C4 C5 O5 59.8(3) . . . . ? O4 C4 C5 C6 62.4(3) . . . . ? C3 C4 C5 C6 -57.0(3) . . . . ? C15 O6 C6 C5 -91.6(3) . . . . ? C15 O6 C6 C1 150.5(2) . . . . ? O5 C5 C6 O6 -178.70(18) . . . . ? C4 C5 C6 O6 -61.5(3) . . . . ? O5 C5 C6 C1 -61.0(2) . . . . ? C4 C5 C6 C1 56.3(3) . . . . ? O1 C1 C6 O6 -179.0(2) . . . . ? C2 C1 C6 O6 62.6(3) . . . . ? O1 C1 C6 C5 60.9(3) . . . . ? C2 C1 C6 C5 -57.5(3) . . . . ? C1 O1 C7 O3 -62.6(3) . . . . ? C1 O1 C7 O5 62.9(3) . . . . ? C3 O3 C7 O1 62.9(2) . . . . ? C3 O3 C7 O5 -62.3(3) . . . . ? C5 O5 C7 O1 -63.1(3) . . . . ? C5 O5 C7 O3 62.6(3) . . . . ? C2 O2 C8 O7 -0.3(4) . . . . ? C2 O2 C8 C9 179.3(2) . . . . ? O7 C8 C9 C14 170.2(3) . . . . ? O2 C8 C9 C14 -9.3(4) . . . . ? O7 C8 C9 C10 -10.6(4) . . . . ? O2 C8 C9 C10 169.9(2) . . . . ? C14 C9 C10 C11 0.0(4) . . . . ? C8 C9 C10 C11 -179.2(2) . . . . ? C9 C10 C11 C12 -1.2(4) . . . . ? C10 C11 C12 C13 1.5(4) . . . . ? C10 C11 C12 Br1 -177.5(2) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? Br1 C12 C13 C14 178.5(2) . . . . ? C12 C13 C14 C9 -0.7(4) . . . . ? C10 C9 C14 C13 0.9(4) . . . . ? C8 C9 C14 C13 -179.9(3) . . . . ? C6 O6 C15 O8 -5.6(4) . . . . ? C6 O6 C15 C16 174.5(2) . . . . ? O8 C15 C16 C17 -17.2(4) . . . . ? O6 C15 C16 C17 162.7(3) . . . . ? O8 C15 C16 C21 161.8(3) . . . . ? O6 C15 C16 C21 -18.3(4) . . . . ? C21 C16 C17 C18 2.1(4) . . . . ? C15 C16 C17 C18 -178.9(3) . . . . ? C16 C17 C18 C19 0.1(5) . . . . ? C17 C18 C19 C20 -2.2(5) . . . . ? C17 C18 C19 Br2 176.7(2) . . . . ? C18 C19 C20 C21 2.0(4) . . . . ? Br2 C19 C20 C21 -177.0(2) . . . . ? C19 C20 C21 C16 0.3(4) . . . . ? C17 C16 C21 C20 -2.4(4) . . . . ? C15 C16 C21 C20 178.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A O7 0.812(19) 1.97(2) 2.767(3) 167(4) 2_646 C7 H7 O9 1.00 2.41 3.307(4) 149.2 3_657 C5 H5 O4 1.00 2.45 3.160(3) 127.3 2_646 C7 H7 O9' 1.00 2.50 3.130(13) 120.7 3_657 C21 H21 O5 0.95 2.59 3.170(3) 119.7 2_656 C5 H5 O7 1.00 2.60 3.303(3) 127.5 2_646 C4 H4 Br1 1.00 2.93 3.849(3) 152.8 4_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.737 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.089 #===END data_2E _database_code_depnum_ccdc_archive 'CCDC 752179' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate tetrahydrofuran solvate ; _chemical_name_common ;2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate tetrahydrofuran solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8 , C4 H8 O' _chemical_formula_sum 'C25 H24 Br2 O9' _chemical_formula_weight 628.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.181(4) _cell_length_b 10.046(3) _cell_length_c 18.813(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.436(4) _cell_angle_gamma 90.00 _cell_volume 2432.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 6686 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 27.45 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 3.386 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2593 _exptl_absorpt_correction_T_max 0.5762 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 15536 _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_sigmaI/netI 0.1035 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4268 _reflns_number_gt 3714 _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 1.4.1' _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^)+(0.1216P)^2^+0.4397P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4268 _refine_ls_number_parameters 374 _refine_ls_number_restraints 150 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.1914 _refine_ls_wR_factor_gt 0.1833 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.069 _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 Br1 Br 0.03896(4) 1.20508(4) -0.20300(2) 0.0319(2) Uani 1 1 d . . . Br2 Br -0.12721(12) 0.71945(15) 0.48614(8) 0.0401(4) Uani 0.50 1 d P A 1 Br2' Br -0.10965(13) 0.6630(2) 0.50752(9) 0.0540(5) Uani 0.50 1 d P A 2 O1 O 0.1479(2) 0.4440(3) 0.04181(15) 0.0297(7) Uani 1 1 d . . . O2 O 0.1408(2) 0.7256(3) 0.05685(14) 0.0243(6) Uani 1 1 d . . . O3 O 0.3107(2) 0.5407(3) 0.07461(15) 0.0289(7) Uani 1 1 d . . . O4 O 0.2953(3) 0.5932(3) 0.26268(15) 0.0305(7) Uani 1 1 d . . . O5 O 0.2791(3) 0.3352(3) 0.12156(16) 0.0328(7) Uani 1 1 d . . . O6 O 0.0981(3) 0.4682(3) 0.22534(15) 0.0328(7) Uani 1 1 d . . . O7 O 0.1954(2) 0.8996(3) 0.12901(14) 0.0294(7) Uani 1 1 d . . . O8 O -0.0207(4) 0.3089(4) 0.2180(3) 0.0727(15) Uani 1 1 d . . . C1 C 0.1119(3) 0.5087(4) 0.0999(2) 0.0251(9) Uani 1 1 d . . . H1 H 0.0355 0.5257 0.0851 0.030 Uiso 1 1 calc R . . C2 C 0.1698(3) 0.6394(4) 0.1196(2) 0.0217(8) Uani 1 1 d . . . H2 H 0.1500 0.6806 0.1630 0.026 Uiso 1 1 calc R . . C3 C 0.2860(3) 0.6106(4) 0.1352(2) 0.0245(8) Uani 1 1 d . . . H3 H 0.3261 0.6957 0.1436 0.029 Uiso 1 1 calc R . . C4 C 0.3148(3) 0.5210(4) 0.2027(2) 0.0270(9) Uani 1 1 d . . . H4 H 0.3905 0.4991 0.2116 0.032 Uiso 1 1 calc R . . C5 C 0.2518(4) 0.3925(4) 0.1857(2) 0.0290(9) Uani 1 1 d . . . H5 H 0.2699 0.3293 0.2276 0.035 Uiso 1 1 calc R . . C6 C 0.1348(3) 0.4130(4) 0.1649(2) 0.0257(9) Uani 1 1 d . . . H6 H 0.0997 0.3258 0.1507 0.031 Uiso 1 1 calc R . . C7 C 0.2553(4) 0.4216(4) 0.0616(2) 0.0301(9) Uani 1 1 d . . . H7 H 0.2766 0.3765 0.0197 0.036 Uiso 1 1 calc R . . C8 C 0.1596(3) 0.8561(4) 0.0695(2) 0.0215(8) Uani 1 1 d . . . C9 C 0.1291(3) 0.9377(4) 0.0025(2) 0.0205(8) Uani 1 1 d . . . C10 C 0.1407(3) 1.0746(4) 0.0084(2) 0.0255(9) Uani 1 1 d . . . H10 H 0.1670 1.1138 0.0546 0.031 Uiso 1 1 calc R . . C11 C 0.1141(3) 1.1545(4) -0.0527(2) 0.0258(9) Uani 1 1 d . . . H11 H 0.1213 1.2485 -0.0488 0.031 Uiso 1 1 calc R . . C12 C 0.0770(3) 1.0949(4) -0.1193(2) 0.0237(8) Uani 1 1 d . . . C13 C 0.0649(3) 0.9593(4) -0.1268(2) 0.0286(9) Uani 1 1 d . . . H13 H 0.0393 0.9207 -0.1733 0.034 Uiso 1 1 calc R . . C14 C 0.0909(3) 0.8799(4) -0.0652(2) 0.0263(9) Uani 1 1 d . . . H14 H 0.0827 0.7860 -0.0693 0.032 Uiso 1 1 calc R . . C15 C 0.0206(3) 0.4049(4) 0.2471(2) 0.0300(9) Uani 1 1 d . . . C16 C -0.0081(3) 0.4721(4) 0.3103(2) 0.0283(9) Uani 1 1 d . A . C17 C -0.0953(4) 0.4297(5) 0.3328(3) 0.0411(11) Uani 1 1 d . . . H17 H -0.1333 0.3559 0.3093 0.049 Uiso 1 1 calc R . . C18 C -0.1286(4) 0.4926(7) 0.3892(3) 0.0534(15) Uani 1 1 d . A . H18 H -0.1893 0.4640 0.4043 0.064 Uiso 1 1 calc R . . C19 C -0.0706(4) 0.5982(6) 0.4226(3) 0.0510(14) Uani 1 1 d . . . C20 C 0.0173(4) 0.6417(6) 0.4021(3) 0.0486(14) Uani 1 1 d . A . H20 H 0.0558 0.7142 0.4267 0.058 Uiso 1 1 calc R . . C21 C 0.0496(4) 0.5789(4) 0.3452(2) 0.0328(10) Uani 1 1 d . . . H21 H 0.1103 0.6083 0.3301 0.039 Uiso 1 1 calc R A . H4A H 0.303(5) 0.545(8) 0.298(4) 0.08(2) Uiso 1 1 d . . . O9 O 0.7116(4) 0.6307(4) 0.1030(2) 0.0624(11) Uani 1 1 d . C . C22 C 0.7649(5) 0.5212(7) 0.1379(4) 0.0659(16) Uani 1 1 d U . . H22A H 0.8344 0.5455 0.1669 0.079 Uiso 1 1 calc R B 1 H22B H 0.7717 0.4490 0.1034 0.079 Uiso 1 1 calc R B 1 C23 C 0.6874(16) 0.484(2) 0.1871(11) 0.066(3) Uani 0.40 1 d PU C 1 H23A H 0.6801 0.3866 0.1909 0.079 Uiso 0.40 1 calc PR C 1 H23B H 0.7098 0.5224 0.2365 0.079 Uiso 0.40 1 calc PR C 1 C24 C 0.586(2) 0.549(2) 0.1457(16) 0.066(3) Uani 0.40 1 d PU C 1 H24A H 0.5299 0.4809 0.1336 0.079 Uiso 0.40 1 calc PR C 1 H24B H 0.5627 0.6189 0.1756 0.079 Uiso 0.40 1 calc PR C 1 C23' C 0.6970(16) 0.434(2) 0.1718(13) 0.063(3) Uani 0.40 1 d PU C 2 H23C H 0.7190 0.4339 0.2256 0.076 Uiso 0.40 1 calc PR C 2 H23D H 0.6958 0.3416 0.1536 0.076 Uiso 0.40 1 calc PR C 2 C24' C 0.5901(19) 0.504(2) 0.1459(16) 0.061(3) Uani 0.40 1 d PU C 2 H24C H 0.5353 0.4379 0.1264 0.073 Uiso 0.40 1 calc PR C 2 H24D H 0.5701 0.5525 0.1865 0.073 Uiso 0.40 1 calc PR C 2 C23" C 0.702(3) 0.401(4) 0.132(2) 0.064(3) Uani 0.20 1 d PU C 3 H23E H 0.7210 0.3397 0.0956 0.077 Uiso 0.20 1 calc PR C 3 H23F H 0.7125 0.3552 0.1792 0.077 Uiso 0.20 1 calc PR C 3 C24" C 0.597(2) 0.443(3) 0.109(2) 0.061(3) Uani 0.20 1 d PU C 3 H24E H 0.5592 0.4339 0.1486 0.073 Uiso 0.20 1 calc PR C 3 H24F H 0.5606 0.3908 0.0663 0.073 Uiso 0.20 1 calc PR C 3 C25 C 0.6059(6) 0.5989(8) 0.0870(4) 0.0758(18) Uani 1 1 d U . . H25A H 0.5636 0.6797 0.0724 0.091 Uiso 1 1 calc R C 1 H25B H 0.5904 0.5336 0.0466 0.091 Uiso 1 1 calc R C 1 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 0.0441(4) 0.0272(3) 0.0216(3) 0.00714(15) 0.0011(2) -0.00019(16) Br2 0.0423(8) 0.0484(8) 0.0351(8) -0.0128(6) 0.0204(6) -0.0048(6) Br2' 0.0474(8) 0.0807(13) 0.0407(9) -0.0167(8) 0.0244(6) -0.0032(8) O1 0.0430(18) 0.0263(15) 0.0202(14) -0.0049(11) 0.0076(12) -0.0018(13) O2 0.0366(17) 0.0201(14) 0.0152(13) -0.0015(10) 0.0034(12) -0.0009(11) O3 0.0358(16) 0.0315(15) 0.0215(14) 0.0025(12) 0.0106(12) 0.0022(12) O4 0.0504(19) 0.0230(15) 0.0165(14) 0.0034(12) 0.0036(13) 0.0008(13) O5 0.052(2) 0.0210(14) 0.0264(15) 0.0022(12) 0.0119(13) 0.0096(14) O6 0.0523(19) 0.0250(15) 0.0255(15) -0.0043(12) 0.0184(13) -0.0093(13) O7 0.0467(18) 0.0227(14) 0.0170(14) -0.0005(11) 0.0025(12) -0.0018(12) O8 0.075(3) 0.066(3) 0.093(3) -0.056(3) 0.054(3) -0.042(2) C1 0.034(2) 0.024(2) 0.0180(19) -0.0040(16) 0.0081(16) -0.0031(17) C2 0.032(2) 0.020(2) 0.0136(17) 0.0026(15) 0.0055(14) 0.0034(16) C3 0.031(2) 0.0225(19) 0.0206(19) 0.0011(16) 0.0059(16) 0.0005(16) C4 0.034(2) 0.025(2) 0.0199(19) 0.0029(16) 0.0018(16) 0.0043(17) C5 0.052(3) 0.0197(19) 0.0173(18) 0.0038(16) 0.0109(17) 0.0050(18) C6 0.045(2) 0.0143(18) 0.0211(19) -0.0018(15) 0.0132(17) -0.0036(16) C7 0.047(3) 0.023(2) 0.022(2) -0.0047(16) 0.0116(18) 0.0059(18) C8 0.027(2) 0.020(2) 0.0178(19) -0.0018(15) 0.0056(15) 0.0020(15) C9 0.026(2) 0.0187(18) 0.0167(19) 0.0019(14) 0.0045(15) 0.0030(15) C10 0.031(2) 0.027(2) 0.0167(19) -0.0046(16) 0.0012(16) 0.0002(17) C11 0.034(2) 0.018(2) 0.024(2) 0.0003(16) 0.0049(16) 0.0012(16) C12 0.028(2) 0.025(2) 0.0179(19) 0.0040(15) 0.0039(15) 0.0016(16) C13 0.038(2) 0.025(2) 0.0199(19) -0.0023(16) -0.0010(17) 0.0004(17) C14 0.035(2) 0.0165(18) 0.025(2) -0.0007(16) 0.0000(17) -0.0007(16) C15 0.032(2) 0.028(2) 0.030(2) -0.0020(18) 0.0065(18) -0.0029(18) C16 0.034(2) 0.028(2) 0.022(2) -0.0028(17) 0.0052(17) -0.0022(17) C17 0.038(3) 0.046(3) 0.041(3) -0.012(2) 0.012(2) -0.013(2) C18 0.034(3) 0.086(4) 0.045(3) -0.015(3) 0.019(2) -0.017(3) C19 0.041(3) 0.082(4) 0.036(3) -0.031(3) 0.020(2) -0.018(3) C20 0.036(3) 0.067(4) 0.046(3) -0.030(3) 0.018(2) -0.019(2) C21 0.035(2) 0.038(2) 0.028(2) -0.0079(19) 0.0140(18) -0.0088(19) O9 0.072(3) 0.062(3) 0.050(2) 0.0087(19) 0.0063(19) -0.015(2) C22 0.046(3) 0.068(3) 0.081(4) 0.012(3) 0.009(3) -0.008(3) C23 0.059(5) 0.071(6) 0.068(5) 0.017(5) 0.015(4) 0.000(5) C24 0.060(5) 0.073(6) 0.066(5) 0.004(6) 0.014(4) 0.004(6) C23' 0.059(5) 0.065(5) 0.065(5) 0.016(5) 0.014(5) 0.000(5) C24' 0.058(4) 0.065(6) 0.062(5) 0.015(5) 0.017(4) 0.000(5) C23" 0.057(5) 0.065(6) 0.070(6) 0.007(6) 0.013(5) 0.003(5) C24" 0.055(5) 0.064(6) 0.065(5) 0.006(5) 0.015(5) 0.004(5) C25 0.065(4) 0.074(4) 0.084(4) 0.002(3) 0.005(3) 0.009(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C12 1.901(4) . ? Br2 C19 1.962(5) . ? Br2' C19 1.896(5) . ? O1 C7 1.403(5) . ? O1 C1 1.437(5) . ? O2 C8 1.346(5) . ? O2 C2 1.447(5) . ? O3 C7 1.396(5) . ? O3 C3 1.434(5) . ? O4 C4 1.410(5) . ? O4 H4A 0.82(7) . ? O5 C7 1.404(5) . ? O5 C5 1.450(5) . ? O6 C15 1.339(5) . ? O6 C6 1.438(5) . ? O7 C8 1.199(5) . ? O8 C15 1.182(6) . ? C1 C2 1.524(5) . ? C1 C6 1.534(5) . ? C1 H1 1.0000 . ? C2 C3 1.525(6) . ? C2 H2 1.0000 . ? C3 C4 1.536(5) . ? C3 H3 1.0000 . ? C4 C5 1.531(6) . ? C4 H4 1.0000 . ? C5 C6 1.522(6) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.485(5) . ? C9 C10 1.385(6) . ? C9 C14 1.392(5) . ? C10 C11 1.383(6) . ? C10 H10 0.9500 . ? C11 C12 1.381(6) . ? C11 H11 0.9500 . ? C12 C13 1.375(6) . ? C13 C14 1.388(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.486(6) . ? C16 C17 1.375(7) . ? C16 C21 1.395(6) . ? C17 C18 1.384(7) . ? C17 H17 0.9500 . ? C18 C19 1.377(8) . ? C18 H18 0.9500 . ? C19 C20 1.369(7) . ? C20 C21 1.387(7) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? O9 C22 1.392(7) . ? O9 C25 1.398(8) . ? C22 C23" 1.45(4) . ? C22 C23' 1.49(2) . ? C22 C23 1.56(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.54(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.29(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C23' C24' 1.55(3) . ? C23' H23C 0.9900 . ? C23' H23D 0.9900 . ? C24' C25 1.51(2) . ? C24' H24C 0.9900 . ? C24' H24D 0.9900 . ? C23" C24" 1.42(4) . ? C23" H23E 0.9900 . ? C23" H23F 0.9900 . ? C24" C25 1.63(3) . ? C24" H24E 0.9900 . ? C24" H24F 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? 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 115.6(3) . . ? C7 O3 C3 111.1(3) . . ? C4 O4 H4A 110(5) . . ? C7 O5 C5 111.8(3) . . ? C15 O6 C6 117.8(3) . . ? O1 C1 C2 110.2(3) . . ? O1 C1 C6 106.4(3) . . ? C2 C1 C6 110.1(3) . . ? O1 C1 H1 110.0 . . ? C2 C1 H1 110.0 . . ? C6 C1 H1 110.0 . . ? O2 C2 C1 106.7(3) . . ? O2 C2 C3 110.4(3) . . ? C1 C2 C3 108.2(3) . . ? O2 C2 H2 110.5 . . ? C1 C2 H2 110.5 . . ? C3 C2 H2 110.5 . . ? O3 C3 C2 109.3(3) . . ? O3 C3 C4 108.2(3) . . ? C2 C3 C4 109.3(3) . . ? O3 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? C4 C3 H3 110.0 . . ? O4 C4 C5 114.6(4) . . ? O4 C4 C3 107.8(3) . . ? C5 C4 C3 107.1(3) . . ? O4 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? O5 C5 C6 105.0(3) . . ? O5 C5 C4 106.8(3) . . ? C6 C5 C4 114.4(3) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 110.1(3) . . ? O6 C6 C1 110.3(3) . . ? C5 C6 C1 107.7(3) . . ? O6 C6 H6 109.6 . . ? C5 C6 H6 109.6 . . ? C1 C6 H6 109.6 . . ? O3 C7 O1 111.6(3) . . ? O3 C7 O5 111.8(3) . . ? O1 C7 O5 110.5(4) . . ? O3 C7 H7 107.6 . . ? O1 C7 H7 107.6 . . ? O5 C7 H7 107.6 . . ? O7 C8 O2 122.8(3) . . ? O7 C8 C9 124.8(3) . . ? O2 C8 C9 112.4(3) . . ? C10 C9 C14 119.9(3) . . ? C10 C9 C8 118.4(3) . . ? C14 C9 C8 121.7(3) . . ? C11 C10 C9 120.4(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 118.6(4) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C13 C12 C11 122.2(4) . . ? C13 C12 Br1 119.2(3) . . ? C11 C12 Br1 118.6(3) . . ? C12 C13 C14 118.8(4) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C13 C14 C9 120.0(4) . . ? C13 C14 H14 120.0 . . ? C9 C14 H14 120.0 . . ? O8 C15 O6 123.5(4) . . ? O8 C15 C16 124.7(4) . . ? O6 C15 C16 111.8(3) . . ? C17 C16 C21 120.0(4) . . ? C17 C16 C15 118.7(4) . . ? C21 C16 C15 121.2(4) . . ? C16 C17 C18 121.3(4) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 117.7(5) . . ? C19 C18 H18 121.2 . . ? C17 C18 H18 121.2 . . ? C20 C19 C18 122.5(5) . . ? C20 C19 Br2' 121.9(4) . . ? C18 C19 Br2' 115.1(4) . . ? C20 C19 Br2 115.4(4) . . ? C18 C19 Br2 120.6(4) . . ? C19 C20 C21 119.5(4) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C20 C21 C16 119.0(4) . . ? C20 C21 H21 120.5 . . ? C16 C21 H21 120.5 . . ? C22 O9 C25 107.4(5) . . ? O9 C22 C23" 113.4(14) . . ? O9 C22 C23' 112.2(9) . . ? O9 C22 C23 98.0(9) . . ? C23" C22 C23 54.3(17) . . ? O9 C22 H22A 112.2 . . ? C23" C22 H22A 133.9 . . ? C23' C22 H22A 118.6 . . ? C23 C22 H22A 112.2 . . ? O9 C22 H22B 112.2 . . ? C23" C22 H22B 58.0 . . ? C23' C22 H22B 89.9 . . ? C23 C22 H22B 112.2 . . ? H22A C22 H22B 109.8 . . ? C24 C23 C22 102.2(15) . . ? C24 C23 H23A 111.3 . . ? C22 C23 H23A 111.3 . . ? C24 C23 H23B 111.3 . . ? C22 C23 H23B 111.3 . . ? H23A C23 H23B 109.2 . . ? C25 C24 C23 106.1(19) . . ? C25 C24 H24A 110.5 . . ? C23 C24 H24A 110.5 . . ? C25 C24 H24B 110.5 . . ? C23 C24 H24B 110.5 . . ? H24A C24 H24B 108.7 . . ? C22 C23' C24' 100.9(13) . . ? C22 C23' H23C 111.6 . . ? C24' C23' H23C 111.6 . . ? C22 C23' H23D 111.6 . . ? C24' C23' H23D 111.6 . . ? H23C C23' H23D 109.4 . . ? C25 C24' C23' 104.8(17) . . ? C25 C24' H24C 110.8 . . ? C23' C24' H24C 110.8 . . ? C25 C24' H24D 110.8 . . ? C23' C24' H24D 110.8 . . ? H24C C24' H24D 108.9 . . ? C24" C23" C22 106(3) . . ? C24" C23" H23E 110.5 . . ? C22 C23" H23E 110.5 . . ? C24" C23" H23F 110.5 . . ? C22 C23" H23F 110.5 . . ? H23E C23" H23F 108.7 . . ? C23" C24" C25 104(2) . . ? C23" C24" H24E 110.9 . . ? C25 C24" H24E 110.9 . . ? C23" C24" H24F 110.9 . . ? C25 C24" H24F 110.9 . . ? H24E C24" H24F 109.0 . . ? C24 C25 O9 106.6(13) . . ? O9 C25 C24' 105.9(11) . . ? C24 C25 C24" 51.0(17) . . ? O9 C25 C24" 106.7(12) . . ? C24 C25 H25A 110.4 . . ? O9 C25 H25A 110.4 . . ? C24' C25 H25A 124.3 . . ? C24" C25 H25A 142.3 . . ? C24 C25 H25B 110.4 . . ? O9 C25 H25B 110.4 . . ? C24' C25 H25B 96.0 . . ? C24" C25 H25B 62.8 . . ? H25A C25 H25B 108.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C2 57.6(4) . . . . ? C7 O1 C1 C6 -61.7(4) . . . . ? C8 O2 C2 C1 162.0(3) . . . . ? C8 O2 C2 C3 -80.6(4) . . . . ? O1 C1 C2 O2 65.3(4) . . . . ? C6 C1 C2 O2 -177.7(3) . . . . ? O1 C1 C2 C3 -53.5(4) . . . . ? C6 C1 C2 C3 63.5(4) . . . . ? C7 O3 C3 C2 -58.9(4) . . . . ? C7 O3 C3 C4 60.0(4) . . . . ? O2 C2 C3 O3 -62.7(4) . . . . ? C1 C2 C3 O3 53.7(4) . . . . ? O2 C2 C3 C4 179.0(3) . . . . ? C1 C2 C3 C4 -64.6(4) . . . . ? O3 C3 C4 O4 177.0(3) . . . . ? C2 C3 C4 O4 -64.1(4) . . . . ? O3 C3 C4 C5 -59.2(4) . . . . ? C2 C3 C4 C5 59.8(4) . . . . ? C7 O5 C5 C6 61.8(4) . . . . ? C7 O5 C5 C4 -60.1(4) . . . . ? O4 C4 C5 O5 177.9(3) . . . . ? C3 C4 C5 O5 58.4(4) . . . . ? O4 C4 C5 C6 62.2(4) . . . . ? C3 C4 C5 C6 -57.3(4) . . . . ? C15 O6 C6 C5 -126.5(4) . . . . ? C15 O6 C6 C1 114.7(4) . . . . ? O5 C5 C6 O6 179.1(3) . . . . ? C4 C5 C6 O6 -64.1(4) . . . . ? O5 C5 C6 C1 -60.6(4) . . . . ? C4 C5 C6 C1 56.2(4) . . . . ? O1 C1 C6 O6 -178.2(3) . . . . ? C2 C1 C6 O6 62.5(4) . . . . ? O1 C1 C6 C5 61.6(4) . . . . ? C2 C1 C6 C5 -57.8(4) . . . . ? C3 O3 C7 O1 63.4(4) . . . . ? C3 O3 C7 O5 -61.0(4) . . . . ? C1 O1 C7 O3 -62.3(4) . . . . ? C1 O1 C7 O5 62.8(4) . . . . ? C5 O5 C7 O3 61.6(5) . . . . ? C5 O5 C7 O1 -63.4(4) . . . . ? C2 O2 C8 O7 -1.9(6) . . . . ? C2 O2 C8 C9 179.3(3) . . . . ? O7 C8 C9 C10 -1.2(6) . . . . ? O2 C8 C9 C10 177.7(4) . . . . ? O7 C8 C9 C14 177.9(4) . . . . ? O2 C8 C9 C14 -3.2(5) . . . . ? C14 C9 C10 C11 0.3(6) . . . . ? C8 C9 C10 C11 179.4(4) . . . . ? C9 C10 C11 C12 -0.6(6) . . . . ? C10 C11 C12 C13 0.5(7) . . . . ? C10 C11 C12 Br1 179.2(3) . . . . ? C11 C12 C13 C14 0.0(7) . . . . ? Br1 C12 C13 C14 -178.7(3) . . . . ? C12 C13 C14 C9 -0.4(7) . . . . ? C10 C9 C14 C13 0.3(6) . . . . ? C8 C9 C14 C13 -178.9(4) . . . . ? C6 O6 C15 O8 -2.2(7) . . . . ? C6 O6 C15 C16 179.3(3) . . . . ? O8 C15 C16 C17 -7.1(8) . . . . ? O6 C15 C16 C17 171.4(4) . . . . ? O8 C15 C16 C21 174.9(5) . . . . ? O6 C15 C16 C21 -6.5(6) . . . . ? C21 C16 C17 C18 1.1(8) . . . . ? C15 C16 C17 C18 -176.9(5) . . . . ? C16 C17 C18 C19 -0.8(9) . . . . ? C17 C18 C19 C20 -0.1(10) . . . . ? C17 C18 C19 Br2' -171.6(5) . . . . ? C17 C18 C19 Br2 165.5(5) . . . . ? C18 C19 C20 C21 0.7(10) . . . . ? Br2' C19 C20 C21 171.6(4) . . . . ? Br2 C19 C20 C21 -165.6(4) . . . . ? C19 C20 C21 C16 -0.4(8) . . . . ? C17 C16 C21 C20 -0.5(7) . . . . ? C15 C16 C21 C20 177.5(5) . . . . ? C25 O9 C22 C23" 14(2) . . . . ? C25 O9 C22 C23' -22.3(13) . . . . ? C25 O9 C22 C23 -40.7(10) . . . . ? O9 C22 C23 C24 22.4(15) . . . . ? C23" C22 C23 C24 -91(2) . . . . ? C23' C22 C23 C24 -108(4) . . . . ? C22 C23 C24 C25 3(2) . . . . ? O9 C22 C23' C24' 4.5(19) . . . . ? C23" C22 C23' C24' -95(3) . . . . ? C23 C22 C23' C24' 59(3) . . . . ? C22 C23' C24' C25 13(2) . . . . ? O9 C22 C23" C24" -16(3) . . . . ? C23' C22 C23" C24" 79(4) . . . . ? C23 C22 C23" C24" 67(3) . . . . ? C22 C23" C24" C25 11(4) . . . . ? C23 C24 C25 O9 -28.2(18) . . . . ? C23 C24 C25 C24' 62(6) . . . . ? C23 C24 C25 C24" 70(2) . . . . ? C22 O9 C25 C24 47.3(13) . . . . ? C22 O9 C25 C24' 30.2(13) . . . . ? C22 O9 C25 C24" -6.1(16) . . . . ? C23' C24' C25 C24 -121(8) . . . . ? C23' C24' C25 O9 -26.9(19) . . . . ? C23' C24' C25 C24" 70(3) . . . . ? C23" C24" C25 C24 -101(3) . . . . ? C23" C24" C25 O9 -3(3) . . . . ? C23" C24" C25 C24' -97(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 C23' H23D Br2 0.99 2.86 3.63(2) 134.4 2_545 C23' H23D Br2 0.99 2.86 3.63(2) 134.4 2_545 C24" H24F Br2 0.99 2.25 2.95(4) 126.4 2_545 C24" H24F Br2' 0.99 2.82 3.59(4) 134.9 2_545 C25 H25A Br2 0.99 2.87 3.723(7) 145.1 4_675 C25 H25A Br2' 0.99 2.83 3.769(7) 158.8 4_675 C11 H11 O1 0.95 2.57 3.387(5) 143.7 1_565 C5 H5 O4 1.00 2.54 3.261(5) 128.5 2_545 C13 H13 O8 0.95 2.45 3.180(5) 133.6 3_565 C7 H7 O9 1.00 2.35 3.261(6) 151.4 3_665 O4 H4A O7 0.82(7) 2.00(8) 2.800(4) 168(7) 2_545 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.989 _refine_diff_density_min -1.045 _refine_diff_density_rms 0.171 #===END data_2F _database_code_depnum_ccdc_archive 'CCDC 752180' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate dioxane solvate ; _chemical_name_common ;2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate dioxane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8 , C4 H8 O2' _chemical_formula_sum 'C25 H24 Br2 O10' _chemical_formula_weight 644.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.1856(16) _cell_length_b 10.2483(13) _cell_length_c 18.966(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.704(2) _cell_angle_gamma 90.00 _cell_volume 2478.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 3449 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.29 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 3.328 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5704 _exptl_absorpt_correction_T_max 0.8177 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 12106 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4352 _reflns_number_gt 3577 _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 1.4.1' _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^)+(0.0422P)^2^+2.0418P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4352 _refine_ls_number_parameters 356 _refine_ls_number_restraints 276 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.002 _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 0.96207(2) 0.70561(3) 1.199587(16) 0.03217(11) Uani 1 1 d . . . Br2 Br 1.10766(4) 0.19168(5) 0.50394(3) 0.07914(19) Uani 1 1 d . . . O1 O 0.85505(16) -0.0514(2) 0.95814(11) 0.0305(5) Uani 1 1 d . . . O2 O 0.85947(15) 0.22614(19) 0.94283(10) 0.0251(5) Uani 1 1 d . . . O3 O 0.68956(16) 0.0418(2) 0.92277(11) 0.0308(5) Uani 1 1 d . . . O4 O 0.69553(17) 0.0945(2) 0.73491(12) 0.0308(5) Uani 1 1 d . . . O5 O 0.72084(17) -0.1598(2) 0.87610(11) 0.0326(5) Uani 1 1 d . . . O6 O 0.89617(16) -0.0249(2) 0.77402(11) 0.0279(5) Uani 1 1 d . . . O7 O 0.80314(16) 0.3959(2) 0.86853(11) 0.0302(5) Uani 1 1 d . . . O8 O 1.05594(19) -0.1137(3) 0.81481(14) 0.0523(7) Uani 1 1 d . . . C1 C 0.8894(2) 0.0127(3) 0.90051(16) 0.0265(7) Uani 1 1 d . . . H1 H 0.9665 0.0300 0.9163 0.032 Uiso 1 1 calc R . . C2 C 0.8299(2) 0.1398(3) 0.88066(15) 0.0225(6) Uani 1 1 d . . . H2 H 0.8483 0.1803 0.8375 0.027 Uiso 1 1 calc R . . C3 C 0.7126(2) 0.1105(3) 0.86274(15) 0.0253(6) Uani 1 1 d . . . H3 H 0.6719 0.1938 0.8539 0.030 Uiso 1 1 calc R . . C4 C 0.6812(2) 0.0234(3) 0.79562(16) 0.0265(7) Uani 1 1 d . . . H4 H 0.6052 0.0007 0.7870 0.032 Uiso 1 1 calc R . . C5 C 0.7463(2) -0.1022(3) 0.81306(16) 0.0271(7) Uani 1 1 d . . . H5 H 0.7276 -0.1636 0.7708 0.032 Uiso 1 1 calc R . . C6 C 0.8645(2) -0.0798(3) 0.83537(16) 0.0268(7) Uani 1 1 d . . . H6 H 0.9013 -0.1648 0.8495 0.032 Uiso 1 1 calc R . . C7 C 0.7466(3) -0.0760(3) 0.93646(17) 0.0326(7) Uani 1 1 d . . . H7 H 0.7267 -0.1208 0.9779 0.039 Uiso 1 1 calc R . . C8 C 0.8403(2) 0.3540(3) 0.92918(16) 0.0243(6) Uani 1 1 d . . . C9 C 0.8698(2) 0.4342(3) 0.99624(15) 0.0230(6) Uani 1 1 d . . . C10 C 0.8593(2) 0.5698(3) 0.98874(16) 0.0276(7) Uani 1 1 d . . . H10 H 0.8330 0.6071 0.9418 0.033 Uiso 1 1 calc R . . C11 C 0.8868(2) 0.6493(3) 1.04896(16) 0.0286(7) Uani 1 1 d . . . H11 H 0.8803 0.7413 1.0438 0.034 Uiso 1 1 calc R . . C12 C 0.9239(2) 0.5939(3) 1.11695(16) 0.0254(6) Uani 1 1 d . . . C13 C 0.9345(2) 0.4599(3) 1.12651(16) 0.0268(7) Uani 1 1 d . . . H13 H 0.9595 0.4234 1.1738 0.032 Uiso 1 1 calc R . . C14 C 0.9076(2) 0.3807(3) 1.06531(15) 0.0256(6) Uani 1 1 d . . . H14 H 0.9151 0.2888 1.0706 0.031 Uiso 1 1 calc R . . C15 C 0.9950(3) -0.0501(3) 0.77018(18) 0.0329(7) Uani 1 1 d . . . C16 C 1.0185(2) 0.0112(3) 0.70506(17) 0.0320(7) Uani 1 1 d . . . C17 C 1.1211(3) 0.0100(4) 0.6992(2) 0.0481(9) Uani 1 1 d . . . H17 H 1.1742 -0.0285 0.7368 0.058 Uiso 1 1 calc R . . C18 C 1.1471(3) 0.0639(4) 0.6395(2) 0.0527(10) Uani 1 1 d . . . H18 H 1.2175 0.0623 0.6358 0.063 Uiso 1 1 calc R . . C19 C 1.0706(3) 0.1193(4) 0.5862(2) 0.0437(9) Uani 1 1 d . . . C20 C 0.9693(3) 0.1281(4) 0.5915(2) 0.0501(10) Uani 1 1 d . . . H20 H 0.9176 0.1706 0.5546 0.060 Uiso 1 1 calc R . . C21 C 0.9433(3) 0.0739(3) 0.65178(18) 0.0384(8) Uani 1 1 d . . . H21 H 0.8733 0.0799 0.6564 0.046 Uiso 1 1 calc R . . H4A H 0.701(3) 0.044(4) 0.700(2) 0.066(14) Uiso 1 1 d . . . O9 O 0.3784(8) 0.0356(6) 0.7964(4) 0.0571(13) Uani 0.70 1 d PDU A 1 O10 O 0.3430(7) 0.1262(7) 0.9289(4) 0.0663(14) Uani 0.70 1 d PDU A 1 C22 C 0.3810(7) -0.0485(7) 0.8563(4) 0.0707(15) Uani 0.70 1 d PDU A 1 H22A H 0.4541 -0.0561 0.8863 0.085 Uiso 0.70 1 calc PR A 1 H22B H 0.3571 -0.1365 0.8379 0.085 Uiso 0.70 1 calc PR A 1 C23 C 0.3147(6) -0.0004(6) 0.9017(4) 0.0758(14) Uani 0.70 1 d PDU A 1 H23A H 0.2409 0.0004 0.8726 0.091 Uiso 0.70 1 calc PR A 1 H23B H 0.3198 -0.0610 0.9431 0.091 Uiso 0.70 1 calc PR A 1 C24 C 0.3378(8) 0.2086(7) 0.8698(5) 0.0654(15) Uani 0.70 1 d PDU A 1 H24A H 0.3583 0.2980 0.8877 0.078 Uiso 0.70 1 calc PR A 1 H24B H 0.2647 0.2120 0.8394 0.078 Uiso 0.70 1 calc PR A 1 C25 C 0.4092(6) 0.1628(6) 0.8235(3) 0.0599(12) Uani 0.70 1 d PDU A 1 H25A H 0.4046 0.2237 0.7824 0.072 Uiso 0.70 1 calc PR A 1 H25B H 0.4827 0.1611 0.8532 0.072 Uiso 0.70 1 calc PR A 1 O9' O 0.388(2) 0.0657(17) 0.8002(10) 0.0571(13) Uani 0.30 1 d PDU B 2 O10' O 0.3617(18) 0.1499(18) 0.9344(10) 0.0663(14) Uani 0.30 1 d PDU B 2 C22' C 0.4113(18) -0.0171(15) 0.8608(10) 0.0707(15) Uani 0.30 1 d PDU B 2 H22C H 0.4750 -0.0677 0.8601 0.085 Uiso 0.30 1 calc PR B 2 H22D H 0.3529 -0.0800 0.8556 0.085 Uiso 0.30 1 calc PR B 2 C23' C 0.4280(14) 0.0456(14) 0.9312(7) 0.0758(14) Uani 0.30 1 d PDU B 2 H23C H 0.4197 -0.0207 0.9673 0.091 Uiso 0.30 1 calc PR B 2 H23D H 0.5013 0.0772 0.9460 0.091 Uiso 0.30 1 calc PR B 2 C24' C 0.361(2) 0.2392(15) 0.8791(10) 0.0654(15) Uani 0.30 1 d PDU B 2 H24C H 0.4321 0.2763 0.8855 0.078 Uiso 0.30 1 calc PR B 2 H24D H 0.3123 0.3115 0.8815 0.078 Uiso 0.30 1 calc PR B 2 C25' C 0.3276(13) 0.1731(13) 0.8072(7) 0.0599(12) Uani 0.30 1 d PDU B 2 H25C H 0.2538 0.1447 0.7994 0.072 Uiso 0.30 1 calc PR B 2 H25D H 0.3303 0.2369 0.7685 0.072 Uiso 0.30 1 calc PR B 2 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 0.03896(19) 0.02938(18) 0.02757(18) -0.00873(13) 0.00734(13) -0.00204(15) Br2 0.0898(4) 0.0877(4) 0.0842(4) 0.0341(3) 0.0667(3) 0.0194(3) O1 0.0365(12) 0.0307(12) 0.0243(11) 0.0068(9) 0.0079(9) 0.0010(10) O2 0.0327(11) 0.0208(11) 0.0199(10) -0.0019(8) 0.0034(9) -0.0010(9) O3 0.0330(12) 0.0345(12) 0.0290(11) -0.0018(10) 0.0151(9) -0.0022(10) O4 0.0412(13) 0.0276(12) 0.0228(11) -0.0024(10) 0.0069(10) -0.0015(10) O5 0.0437(13) 0.0256(11) 0.0316(12) -0.0006(10) 0.0151(10) -0.0087(10) O6 0.0311(11) 0.0285(11) 0.0281(11) 0.0001(9) 0.0147(9) 0.0022(9) O7 0.0424(13) 0.0266(11) 0.0195(11) 0.0025(9) 0.0038(9) 0.0012(10) O8 0.0419(14) 0.0640(18) 0.0541(16) 0.0233(14) 0.0179(13) 0.0157(14) C1 0.0277(16) 0.0268(16) 0.0255(16) 0.0019(13) 0.0076(13) 0.0005(13) C2 0.0280(15) 0.0225(15) 0.0172(14) -0.0042(12) 0.0065(12) -0.0029(13) C3 0.0296(16) 0.0267(16) 0.0203(15) 0.0016(13) 0.0077(12) 0.0013(13) C4 0.0267(16) 0.0267(16) 0.0256(16) -0.0004(13) 0.0054(13) -0.0025(13) C5 0.0360(17) 0.0228(15) 0.0243(15) -0.0020(13) 0.0111(13) -0.0053(14) C6 0.0314(16) 0.0229(15) 0.0284(16) 0.0027(13) 0.0118(13) 0.0017(13) C7 0.0410(19) 0.0305(17) 0.0306(17) 0.0047(14) 0.0170(15) -0.0023(15) C8 0.0222(15) 0.0255(16) 0.0260(16) 0.0000(13) 0.0079(12) -0.0017(13) C9 0.0220(15) 0.0236(15) 0.0226(15) -0.0008(12) 0.0044(12) -0.0035(12) C10 0.0308(16) 0.0259(16) 0.0243(16) 0.0035(13) 0.0039(13) -0.0002(13) C11 0.0331(17) 0.0210(15) 0.0302(17) -0.0013(13) 0.0050(14) -0.0008(13) C12 0.0263(15) 0.0246(15) 0.0260(15) -0.0070(13) 0.0080(12) -0.0016(13) C13 0.0298(16) 0.0290(16) 0.0207(15) 0.0019(13) 0.0045(13) -0.0014(13) C14 0.0292(16) 0.0201(14) 0.0268(16) -0.0001(12) 0.0057(13) 0.0002(13) C15 0.0342(18) 0.0312(17) 0.0347(18) -0.0011(15) 0.0117(15) 0.0026(15) C16 0.0334(17) 0.0285(17) 0.0380(18) -0.0037(14) 0.0163(15) 0.0009(14) C17 0.039(2) 0.055(2) 0.054(2) 0.0066(19) 0.0182(18) 0.0042(19) C18 0.042(2) 0.058(2) 0.071(3) 0.009(2) 0.037(2) 0.0010(19) C19 0.052(2) 0.041(2) 0.049(2) 0.0069(17) 0.0313(19) 0.0034(18) C20 0.050(2) 0.058(2) 0.051(2) 0.016(2) 0.0275(19) 0.013(2) C21 0.0376(19) 0.043(2) 0.0392(19) 0.0030(16) 0.0187(16) 0.0037(16) O9 0.084(2) 0.051(3) 0.0447(16) 0.003(2) 0.0318(16) 0.005(3) O10 0.099(3) 0.058(3) 0.0587(19) 0.0035(19) 0.051(2) 0.004(2) C22 0.110(3) 0.058(3) 0.053(2) 0.003(2) 0.038(3) -0.005(3) C23 0.119(3) 0.063(3) 0.060(3) 0.002(2) 0.049(3) -0.012(3) C24 0.090(3) 0.058(3) 0.062(2) 0.006(2) 0.044(2) 0.015(3) C25 0.082(3) 0.051(2) 0.058(2) 0.003(2) 0.039(2) 0.004(3) O9' 0.084(2) 0.051(3) 0.0447(16) 0.003(2) 0.0318(16) 0.005(3) O10' 0.099(3) 0.058(3) 0.0587(19) 0.0035(19) 0.051(2) 0.004(2) C22' 0.110(3) 0.058(3) 0.053(2) 0.003(2) 0.038(3) -0.005(3) C23' 0.119(3) 0.063(3) 0.060(3) 0.002(2) 0.049(3) -0.012(3) C24' 0.090(3) 0.058(3) 0.062(2) 0.006(2) 0.044(2) 0.015(3) C25' 0.082(3) 0.051(2) 0.058(2) 0.003(2) 0.039(2) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C12 1.902(3) . ? Br2 C19 1.899(3) . ? O1 C7 1.407(4) . ? O1 C1 1.443(3) . ? O2 C8 1.347(4) . ? O2 C2 1.446(3) . ? O3 C7 1.411(4) . ? O3 C3 1.435(3) . ? O4 C4 1.416(4) . ? O4 H4A 0.86(4) . ? O5 C7 1.402(4) . ? O5 C5 1.447(3) . ? O6 C15 1.349(4) . ? O6 C6 1.446(3) . ? O7 C8 1.209(3) . ? O8 C15 1.201(4) . ? C1 C2 1.518(4) . ? C1 C6 1.526(4) . ? C1 H1 1.0000 . ? C2 C3 1.527(4) . ? C2 H2 1.0000 . ? C3 C4 1.523(4) . ? C3 H3 1.0000 . ? C4 C5 1.536(4) . ? C4 H4 1.0000 . ? C5 C6 1.525(4) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.481(4) . ? C9 C14 1.390(4) . ? C9 C10 1.401(4) . ? C10 C11 1.374(4) . ? C10 H10 0.9500 . ? C11 C12 1.380(4) . ? C11 H11 0.9500 . ? C12 C13 1.388(4) . ? C13 C14 1.386(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.487(4) . ? C16 C21 1.381(5) . ? C16 C17 1.385(5) . ? C17 C18 1.378(5) . ? C17 H17 0.9500 . ? C18 C19 1.358(5) . ? C18 H18 0.9500 . ? C19 C20 1.367(5) . ? C20 C21 1.391(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? O9 C22 1.420(8) . ? O9 C25 1.421(9) . ? O10 C24 1.392(8) . ? O10 C23 1.412(9) . ? C22 C23 1.459(9) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.515(10) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? O9' C25' 1.389(16) . ? O9' C22' 1.399(16) . ? O10' C24' 1.389(16) . ? O10' C23' 1.393(16) . ? C22' C23' 1.448(15) . ? C22' H22C 0.9900 . ? C22' H22D 0.9900 . ? C23' H23C 0.9900 . ? C23' H23D 0.9900 . ? C24' C25' 1.487(16) . ? C24' H24C 0.9900 . ? C24' H24D 0.9900 . ? C25' H25C 0.9900 . ? C25' H25D 0.9900 . ? 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 110.6(2) . . ? C8 O2 C2 116.1(2) . . ? C7 O3 C3 110.8(2) . . ? C4 O4 H4A 112(3) . . ? C7 O5 C5 111.4(2) . . ? C15 O6 C6 116.7(2) . . ? O1 C1 C2 109.7(2) . . ? O1 C1 C6 106.6(2) . . ? C2 C1 C6 109.9(2) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C1 107.9(2) . . ? O2 C2 C3 110.5(2) . . ? C1 C2 C3 108.5(2) . . ? O2 C2 H2 110.0 . . ? C1 C2 H2 110.0 . . ? C3 C2 H2 110.0 . . ? O3 C3 C4 108.0(2) . . ? O3 C3 C2 109.0(2) . . ? C4 C3 C2 110.3(2) . . ? O3 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? O4 C4 C3 108.3(2) . . ? O4 C4 C5 115.1(2) . . ? C3 C4 C5 107.0(2) . . ? O4 C4 H4 108.8 . . ? C3 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? O5 C5 C6 105.5(2) . . ? O5 C5 C4 106.6(2) . . ? C6 C5 C4 114.2(2) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 108.6(2) . . ? O6 C6 C1 111.3(2) . . ? C5 C6 C1 108.2(2) . . ? O6 C6 H6 109.6 . . ? C5 C6 H6 109.6 . . ? C1 C6 H6 109.6 . . ? O5 C7 O1 111.5(2) . . ? O5 C7 O3 111.5(2) . . ? O1 C7 O3 110.8(2) . . ? O5 C7 H7 107.6 . . ? O1 C7 H7 107.6 . . ? O3 C7 H7 107.6 . . ? O7 C8 O2 122.6(3) . . ? O7 C8 C9 125.1(3) . . ? O2 C8 C9 112.3(2) . . ? C14 C9 C10 119.3(3) . . ? C14 C9 C8 123.0(3) . . ? C10 C9 C8 117.7(3) . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.3(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C11 C12 C13 121.9(3) . . ? C11 C12 Br1 118.6(2) . . ? C13 C12 Br1 119.4(2) . . ? C14 C13 C12 118.3(3) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C13 C14 C9 120.8(3) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O8 C15 O6 123.3(3) . . ? O8 C15 C16 124.9(3) . . ? O6 C15 C16 111.8(3) . . ? C21 C16 C17 118.7(3) . . ? C21 C16 C15 122.8(3) . . ? C17 C16 C15 118.5(3) . . ? C18 C17 C16 120.9(4) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 119.1(3) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 121.8(3) . . ? C18 C19 Br2 118.5(3) . . ? C20 C19 Br2 119.6(3) . . ? C19 C20 C21 118.9(4) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C16 C21 C20 120.4(3) . . ? C16 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C22 O9 C25 108.7(6) . . ? C24 O10 C23 108.0(6) . . ? O9 C22 C23 111.7(7) . . ? O9 C22 H22A 109.3 . . ? C23 C22 H22A 109.3 . . ? O9 C22 H22B 109.3 . . ? C23 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? O10 C23 C22 112.6(6) . . ? O10 C23 H23A 109.1 . . ? C22 C23 H23A 109.1 . . ? O10 C23 H23B 109.1 . . ? C22 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? O10 C24 C25 111.6(6) . . ? O10 C24 H24A 109.3 . . ? C25 C24 H24A 109.3 . . ? O10 C24 H24B 109.3 . . ? C25 C24 H24B 109.3 . . ? H24A C24 H24B 108.0 . . ? O9 C25 C24 109.4(6) . . ? O9 C25 H25A 109.8 . . ? C24 C25 H25A 109.8 . . ? O9 C25 H25B 109.8 . . ? C24 C25 H25B 109.8 . . ? H25A C25 H25B 108.3 . . ? C25' O9' C22' 114.3(14) . . ? C24' O10' C23' 110.9(14) . . ? O9' C22' C23' 116.1(12) . . ? O9' C22' H22C 108.3 . . ? C23' C22' H22C 108.3 . . ? O9' C22' H22D 108.3 . . ? C23' C22' H22D 108.3 . . ? H22C C22' H22D 107.4 . . ? O10' C23' C22' 115.5(13) . . ? O10' C23' H23C 108.4 . . ? C22' C23' H23C 108.4 . . ? O10' C23' H23D 108.4 . . ? C22' C23' H23D 108.4 . . ? H23C C23' H23D 107.5 . . ? O10' C24' C25' 109.7(13) . . ? O10' C24' H24C 109.7 . . ? C25' C24' H24C 109.7 . . ? O10' C24' H24D 109.7 . . ? C25' C24' H24D 109.7 . . ? H24C C24' H24D 108.2 . . ? O9' C25' C24' 113.9(13) . . ? O9' C25' H25C 108.8 . . ? C24' C25' H25C 108.8 . . ? O9' C25' H25D 108.8 . . ? C24' C25' H25D 108.8 . . ? H25C C25' H25D 107.7 . . ? 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 58.5(3) . . . . ? C7 O1 C1 C6 -60.4(3) . . . . ? C8 O2 C2 C1 160.8(2) . . . . ? C8 O2 C2 C3 -80.8(3) . . . . ? O1 C1 C2 O2 65.6(3) . . . . ? C6 C1 C2 O2 -177.5(2) . . . . ? O1 C1 C2 C3 -54.2(3) . . . . ? C6 C1 C2 C3 62.7(3) . . . . ? C7 O3 C3 C4 60.5(3) . . . . ? C7 O3 C3 C2 -59.3(3) . . . . ? O2 C2 C3 O3 -63.6(3) . . . . ? C1 C2 C3 O3 54.5(3) . . . . ? O2 C2 C3 C4 178.0(2) . . . . ? C1 C2 C3 C4 -63.9(3) . . . . ? O3 C3 C4 O4 175.3(2) . . . . ? C2 C3 C4 O4 -65.7(3) . . . . ? O3 C3 C4 C5 -60.2(3) . . . . ? C2 C3 C4 C5 58.9(3) . . . . ? C7 O5 C5 C6 61.0(3) . . . . ? C7 O5 C5 C4 -60.8(3) . . . . ? O4 C4 C5 O5 180.0(2) . . . . ? C3 C4 C5 O5 59.6(3) . . . . ? O4 C4 C5 C6 63.9(3) . . . . ? C3 C4 C5 C6 -56.5(3) . . . . ? C15 O6 C6 C5 -151.8(3) . . . . ? C15 O6 C6 C1 89.1(3) . . . . ? O5 C5 C6 O6 178.6(2) . . . . ? C4 C5 C6 O6 -64.7(3) . . . . ? O5 C5 C6 C1 -60.5(3) . . . . ? C4 C5 C6 C1 56.3(3) . . . . ? O1 C1 C6 O6 -179.9(2) . . . . ? C2 C1 C6 O6 61.3(3) . . . . ? O1 C1 C6 C5 60.9(3) . . . . ? C2 C1 C6 C5 -57.9(3) . . . . ? C5 O5 C7 O1 -62.7(3) . . . . ? C5 O5 C7 O3 61.7(3) . . . . ? C1 O1 C7 O5 61.9(3) . . . . ? C1 O1 C7 O3 -62.9(3) . . . . ? C3 O3 C7 O5 -61.0(3) . . . . ? C3 O3 C7 O1 63.8(3) . . . . ? C2 O2 C8 O7 -1.8(4) . . . . ? C2 O2 C8 C9 178.1(2) . . . . ? O7 C8 C9 C14 176.8(3) . . . . ? O2 C8 C9 C14 -3.2(4) . . . . ? O7 C8 C9 C10 -3.6(4) . . . . ? O2 C8 C9 C10 176.4(3) . . . . ? C14 C9 C10 C11 0.5(5) . . . . ? C8 C9 C10 C11 -179.1(3) . . . . ? C9 C10 C11 C12 -0.7(5) . . . . ? C10 C11 C12 C13 0.1(5) . . . . ? C10 C11 C12 Br1 179.8(2) . . . . ? C11 C12 C13 C14 0.6(5) . . . . ? Br1 C12 C13 C14 -179.1(2) . . . . ? C12 C13 C14 C9 -0.8(4) . . . . ? C10 C9 C14 C13 0.2(4) . . . . ? C8 C9 C14 C13 179.8(3) . . . . ? C6 O6 C15 O8 -0.6(4) . . . . ? C6 O6 C15 C16 -180.0(2) . . . . ? O8 C15 C16 C21 174.1(3) . . . . ? O6 C15 C16 C21 -6.5(4) . . . . ? O8 C15 C16 C17 -8.6(5) . . . . ? O6 C15 C16 C17 170.8(3) . . . . ? C21 C16 C17 C18 -3.4(6) . . . . ? C15 C16 C17 C18 179.1(4) . . . . ? C16 C17 C18 C19 0.3(6) . . . . ? C17 C18 C19 C20 2.9(6) . . . . ? C17 C18 C19 Br2 -179.4(3) . . . . ? C18 C19 C20 C21 -2.7(6) . . . . ? Br2 C19 C20 C21 179.6(3) . . . . ? C17 C16 C21 C20 3.5(5) . . . . ? C15 C16 C21 C20 -179.2(3) . . . . ? C19 C20 C21 C16 -0.5(6) . . . . ? C25 O9 C22 C23 56.8(10) . . . . ? C24 O10 C23 C22 57.3(10) . . . . ? O9 C22 C23 O10 -57.8(10) . . . . ? C23 O10 C24 C25 -58.2(9) . . . . ? C22 O9 C25 C24 -56.9(9) . . . . ? O10 C24 C25 O9 60.3(9) . . . . ? C25' O9' C22' C23' -36(3) . . . . ? C24' O10' C23' C22' -51(2) . . . . ? O9' C22' C23' O10' 39(3) . . . . ? C23' O10' C24' C25' 58(2) . . . . ? C22' O9' C25' C24' 44(3) . . . . ? O10' C24' C25' O9' -56(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C23' H23D Br2 0.99 2.83 3.620(17) 137.4 4_566 C23 H23B Br2 0.99 2.80 3.644(7) 143.0 2_646 O4 H4A O7 0.86(4) 1.99(5) 2.830(3) 166(4) 2_646 C7 H7 O10 1.00 2.19 3.116(8) 153.2 3_657 C7 H7 O10' 1.00 2.28 3.22(2) 156.6 3_657 C23 H23B O3 0.99 2.59 3.371(6) 136.3 3_657 C24' H24C Br2 0.99 2.81 3.57(2) 134.8 4_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.666 _refine_diff_density_min -0.742 _refine_diff_density_rms 0.071 #===END data_2G _database_code_depnum_ccdc_archive 'CCDC 752181' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate dimethyl sulphoxide solvate ; _chemical_name_common ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate dimethyl sulphoxide solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8 , C2 H6 O S' _chemical_formula_sum 'C23 H22 Br2 O9 S' _chemical_formula_weight 634.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.0322(15) _cell_length_b 10.2499(11) _cell_length_c 18.415(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.579(2) _cell_angle_gamma 90.00 _cell_volume 2391.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 4273 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 28.24 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 3.530 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4547 _exptl_absorpt_correction_T_max 0.8924 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11699 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4201 _reflns_number_gt 3768 _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 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^)+(0.0320P)^2^+5.1307P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4201 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.002 _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 0.04605(3) 0.70586(4) 0.29373(2) 0.02608(13) Uani 1 1 d . . . Br2 Br -0.10755(4) 0.21418(5) 1.00515(3) 0.03210(14) Uani 1 1 d . . . O1 O 0.1392(2) -0.0573(3) 0.53722(15) 0.0196(6) Uani 1 1 d . . . O2 O 0.1383(2) 0.2200(2) 0.55269(14) 0.0176(6) Uani 1 1 d . . . O3 O 0.3070(2) 0.0292(3) 0.57545(15) 0.0210(6) Uani 1 1 d . . . O4 O 0.2883(2) 0.0854(3) 0.76623(16) 0.0231(7) Uani 1 1 d . . . O5 O 0.2682(2) -0.1703(3) 0.62239(15) 0.0211(6) Uani 1 1 d . . . O6 O 0.0829(2) -0.0236(3) 0.72079(15) 0.0222(6) Uani 1 1 d . . . O7 O 0.1971(2) 0.3866(3) 0.62945(15) 0.0248(7) Uani 1 1 d . . . O8 O 0.0031(3) -0.2080(3) 0.74363(19) 0.0383(8) Uani 1 1 d . . . C1 C 0.1019(3) 0.0075(4) 0.5952(2) 0.0179(8) Uani 1 1 d . . . H1 H 0.0248 0.0268 0.5780 0.021 Uiso 1 1 calc R . . C2 C 0.1637(3) 0.1330(4) 0.6171(2) 0.0172(8) Uani 1 1 d . . . H2 H 0.1435 0.1741 0.6610 0.021 Uiso 1 1 calc R . . C3 C 0.2812(3) 0.0997(4) 0.6364(2) 0.0185(9) Uani 1 1 d . . . H3 H 0.3239 0.1817 0.6461 0.022 Uiso 1 1 calc R . . C4 C 0.3070(3) 0.0127(4) 0.7055(2) 0.0209(9) Uani 1 1 d . . . H4 H 0.3833 -0.0120 0.7161 0.025 Uiso 1 1 calc R . . C5 C 0.2396(3) -0.1109(4) 0.6863(2) 0.0226(9) Uani 1 1 d . . . H5 H 0.2549 -0.1724 0.7296 0.027 Uiso 1 1 calc R . . C6 C 0.1220(3) -0.0853(4) 0.6622(2) 0.0204(9) Uani 1 1 d . . . H6 H 0.0836 -0.1693 0.6476 0.024 Uiso 1 1 calc R . . C7 C 0.2481(3) -0.0856(4) 0.5607(2) 0.0204(9) Uani 1 1 d . . . H7 H 0.2697 -0.1313 0.5187 0.024 Uiso 1 1 calc R . . C8 C 0.1592(3) 0.3467(4) 0.5673(2) 0.0178(9) Uani 1 1 d . . . C9 C 0.1308(3) 0.4297(4) 0.4998(2) 0.0187(9) Uani 1 1 d . . . C10 C 0.1396(3) 0.5647(4) 0.5092(2) 0.0193(9) Uani 1 1 d . . . H10 H 0.1633 0.6007 0.5578 0.023 Uiso 1 1 calc R . . C11 C 0.1136(3) 0.6462(4) 0.4477(2) 0.0209(9) Uani 1 1 d . . . H11 H 0.1191 0.7382 0.4536 0.025 Uiso 1 1 calc R . . C12 C 0.0794(3) 0.5917(4) 0.3773(2) 0.0200(9) Uani 1 1 d . . . C13 C 0.0703(3) 0.4581(4) 0.3667(2) 0.0229(9) Uani 1 1 d . . . H13 H 0.0469 0.4226 0.3180 0.027 Uiso 1 1 calc R . . C14 C 0.0958(3) 0.3776(4) 0.4283(2) 0.0200(9) Uani 1 1 d . . . H14 H 0.0895 0.2857 0.4220 0.024 Uiso 1 1 calc R . . C15 C 0.0269(3) -0.0958(4) 0.7586(2) 0.0220(9) Uani 1 1 d . . . C16 C -0.0036(3) -0.0198(4) 0.8187(2) 0.0186(9) Uani 1 1 d . . . C17 C -0.0896(3) -0.0610(4) 0.8450(2) 0.0247(10) Uani 1 1 d . . . H17 H -0.1276 -0.1365 0.8241 0.030 Uiso 1 1 calc R . . C18 C -0.1207(3) 0.0059(4) 0.9011(2) 0.0259(10) Uani 1 1 d . . . H18 H -0.1794 -0.0227 0.9193 0.031 Uiso 1 1 calc R . . C19 C -0.0638(3) 0.1164(4) 0.9303(2) 0.0215(9) Uani 1 1 d . . . C20 C 0.0232(3) 0.1575(4) 0.9064(2) 0.0242(9) Uani 1 1 d . . . H20 H 0.0619 0.2320 0.9282 0.029 Uiso 1 1 calc R . . C21 C 0.0536(3) 0.0888(4) 0.8501(2) 0.0208(9) Uani 1 1 d . . . H21 H 0.1135 0.1161 0.8329 0.025 Uiso 1 1 calc R . . H4A H 0.296(5) 0.034(7) 0.802(4) 0.08(2) Uiso 1 1 d . . . S1 S 0.69934(11) 0.09370(14) 0.65112(7) 0.0400(3) Uani 1 1 d . . . O9 O 0.7021(3) 0.1907(3) 0.5909(2) 0.0404(8) Uani 1 1 d . . . C22 C 0.7783(4) -0.0409(5) 0.6347(3) 0.0477(14) Uani 1 1 d . . . H22A H 0.7534 -0.0708 0.5830 0.072 Uiso 1 1 calc R . . H22B H 0.7725 -0.1123 0.6690 0.072 Uiso 1 1 calc R . . H22C H 0.8521 -0.0133 0.6432 0.072 Uiso 1 1 calc R . . C23 C 0.5743(4) 0.0177(7) 0.6240(4) 0.0635(19) Uani 1 1 d . . . H23A H 0.5190 0.0810 0.6268 0.095 Uiso 1 1 calc R . . H23B H 0.5710 -0.0556 0.6575 0.095 Uiso 1 1 calc R . . H23C H 0.5636 -0.0144 0.5726 0.095 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 0.0334(3) 0.0195(2) 0.0215(2) 0.00619(17) -0.00127(18) -0.00082(18) Br2 0.0306(3) 0.0409(3) 0.0282(3) -0.0104(2) 0.0137(2) 0.0008(2) O1 0.0227(14) 0.0201(15) 0.0152(14) -0.0041(11) 0.0033(12) 0.0005(12) O2 0.0251(15) 0.0107(13) 0.0158(14) 0.0034(11) 0.0026(12) 0.0012(11) O3 0.0204(14) 0.0236(15) 0.0201(15) -0.0005(12) 0.0068(12) -0.0004(12) O4 0.0360(17) 0.0173(15) 0.0152(15) 0.0009(12) 0.0041(13) 0.0007(13) O5 0.0322(16) 0.0136(14) 0.0190(15) 0.0007(11) 0.0088(13) 0.0068(12) O6 0.0324(16) 0.0166(15) 0.0226(15) -0.0009(12) 0.0164(13) -0.0022(13) O7 0.0403(18) 0.0171(15) 0.0154(15) 0.0010(12) 0.0032(13) 0.0014(13) O8 0.056(2) 0.0215(18) 0.049(2) -0.0109(15) 0.0350(18) -0.0141(16) C1 0.018(2) 0.019(2) 0.016(2) -0.0024(16) 0.0038(16) 0.0012(17) C2 0.021(2) 0.015(2) 0.015(2) 0.0035(16) 0.0038(16) 0.0034(16) C3 0.021(2) 0.017(2) 0.017(2) 0.0018(16) 0.0029(16) -0.0010(17) C4 0.023(2) 0.018(2) 0.020(2) -0.0009(17) 0.0026(18) 0.0051(17) C5 0.034(2) 0.017(2) 0.017(2) 0.0009(17) 0.0045(18) 0.0036(18) C6 0.024(2) 0.016(2) 0.022(2) -0.0013(17) 0.0084(18) -0.0015(17) C7 0.020(2) 0.021(2) 0.020(2) -0.0009(17) 0.0060(17) 0.0011(17) C8 0.020(2) 0.016(2) 0.018(2) -0.0006(17) 0.0067(17) 0.0045(17) C9 0.019(2) 0.018(2) 0.018(2) -0.0001(16) 0.0023(17) 0.0008(17) C10 0.023(2) 0.019(2) 0.016(2) -0.0040(16) 0.0050(17) -0.0014(17) C11 0.021(2) 0.015(2) 0.025(2) -0.0004(17) 0.0024(18) -0.0018(17) C12 0.020(2) 0.019(2) 0.019(2) 0.0064(17) 0.0008(17) 0.0009(17) C13 0.028(2) 0.021(2) 0.017(2) -0.0033(17) -0.0001(18) -0.0003(18) C14 0.025(2) 0.0115(19) 0.021(2) -0.0005(16) 0.0020(18) 0.0003(17) C15 0.024(2) 0.020(2) 0.022(2) 0.0030(17) 0.0052(18) -0.0023(18) C16 0.023(2) 0.013(2) 0.020(2) 0.0048(16) 0.0053(17) 0.0003(16) C17 0.027(2) 0.023(2) 0.026(2) 0.0022(18) 0.0078(19) -0.0046(19) C18 0.024(2) 0.032(2) 0.025(2) 0.0036(19) 0.0110(19) 0.0002(19) C19 0.025(2) 0.024(2) 0.017(2) 0.0016(17) 0.0100(17) 0.0065(18) C20 0.027(2) 0.022(2) 0.025(2) -0.0043(18) 0.0083(19) -0.0031(19) C21 0.019(2) 0.024(2) 0.021(2) 0.0055(17) 0.0064(17) -0.0005(17) S1 0.0413(7) 0.0475(8) 0.0342(7) -0.0015(6) 0.0148(6) 0.0018(6) O9 0.049(2) 0.035(2) 0.045(2) -0.0008(16) 0.0257(18) 0.0001(17) C22 0.047(3) 0.046(3) 0.047(3) 0.007(3) 0.005(3) 0.014(3) C23 0.041(3) 0.068(4) 0.084(5) 0.032(4) 0.019(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C12 1.901(4) . ? Br2 C19 1.897(4) . ? O1 C7 1.414(5) . ? O1 C1 1.436(5) . ? O2 C8 1.341(5) . ? O2 C2 1.459(4) . ? O3 C7 1.395(5) . ? O3 C3 1.440(5) . ? O4 C4 1.413(5) . ? O4 H4A 0.83(7) . ? O5 C7 1.404(5) . ? O5 C5 1.449(5) . ? O6 C15 1.343(5) . ? O6 C6 1.443(5) . ? O7 C8 1.207(5) . ? O8 C15 1.206(5) . ? C1 C2 1.521(5) . ? C1 C6 1.531(5) . ? C1 H1 1.0000 . ? C2 C3 1.527(5) . ? C2 H2 1.0000 . ? C3 C4 1.525(5) . ? C3 H3 1.0000 . ? C4 C5 1.534(6) . ? C4 H4 1.0000 . ? C5 C6 1.515(6) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.479(5) . ? C9 C14 1.394(5) . ? C9 C10 1.396(6) . ? C10 C11 1.384(6) . ? C10 H10 0.9500 . ? C11 C12 1.384(6) . ? C11 H11 0.9500 . ? C12 C13 1.384(6) . ? C13 C14 1.379(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.482(6) . ? C16 C17 1.388(6) . ? C16 C21 1.388(6) . ? C17 C18 1.377(6) . ? C17 H17 0.9500 . ? C18 C19 1.391(6) . ? C18 H18 0.9500 . ? C19 C20 1.375(6) . ? C20 C21 1.387(6) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? S1 O9 1.496(4) . ? S1 C23 1.769(6) . ? S1 C22 1.788(5) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? 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 111.0(3) . . ? C8 O2 C2 115.6(3) . . ? C7 O3 C3 110.9(3) . . ? C4 O4 H4A 106(5) . . ? C7 O5 C5 111.2(3) . . ? C15 O6 C6 118.4(3) . . ? O1 C1 C2 109.7(3) . . ? O1 C1 C6 106.8(3) . . ? C2 C1 C6 109.4(3) . . ? O1 C1 H1 110.3 . . ? C2 C1 H1 110.3 . . ? C6 C1 H1 110.3 . . ? O2 C2 C1 107.3(3) . . ? O2 C2 C3 110.5(3) . . ? C1 C2 C3 108.2(3) . . ? O2 C2 H2 110.3 . . ? C1 C2 H2 110.3 . . ? C3 C2 H2 110.3 . . ? O3 C3 C4 108.1(3) . . ? O3 C3 C2 109.6(3) . . ? C4 C3 C2 109.7(3) . . ? O3 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? O4 C4 C3 107.8(3) . . ? O4 C4 C5 115.0(3) . . ? C3 C4 C5 106.8(3) . . ? O4 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? O5 C5 C6 105.7(3) . . ? O5 C5 C4 106.9(3) . . ? C6 C5 C4 114.2(3) . . ? O5 C5 H5 109.9 . . ? C6 C5 H5 109.9 . . ? C4 C5 H5 109.9 . . ? O6 C6 C5 111.6(3) . . ? O6 C6 C1 107.9(3) . . ? C5 C6 C1 108.2(3) . . ? O6 C6 H6 109.7 . . ? C5 C6 H6 109.7 . . ? C1 C6 H6 109.7 . . ? O3 C7 O5 112.0(3) . . ? O3 C7 O1 110.7(3) . . ? O5 C7 O1 111.0(3) . . ? O3 C7 H7 107.7 . . ? O5 C7 H7 107.7 . . ? O1 C7 H7 107.7 . . ? O7 C8 O2 122.5(4) . . ? O7 C8 C9 124.6(4) . . ? O2 C8 C9 113.0(3) . . ? C14 C9 C10 119.7(4) . . ? C14 C9 C8 122.3(4) . . ? C10 C9 C8 118.0(4) . . ? C11 C10 C9 120.0(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 119.0(4) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C13 C12 C11 122.0(4) . . ? C13 C12 Br1 119.9(3) . . ? C11 C12 Br1 118.1(3) . . ? C14 C13 C12 118.7(4) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C9 120.6(4) . . ? C13 C14 H14 119.7 . . ? C9 C14 H14 119.7 . . ? O8 C15 O6 123.3(4) . . ? O8 C15 C16 124.9(4) . . ? O6 C15 C16 111.8(3) . . ? C17 C16 C21 119.9(4) . . ? C17 C16 C15 118.7(4) . . ? C21 C16 C15 121.4(4) . . ? C18 C17 C16 121.0(4) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 118.1(4) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? C20 C19 C18 122.1(4) . . ? C20 C19 Br2 118.8(3) . . ? C18 C19 Br2 119.2(3) . . ? C19 C20 C21 119.1(4) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C16 119.9(4) . . ? C20 C21 H21 120.1 . . ? C16 C21 H21 120.1 . . ? O9 S1 C23 105.3(3) . . ? O9 S1 C22 105.9(2) . . ? C23 S1 C22 98.1(3) . . ? S1 C22 H22A 109.5 . . ? S1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? S1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? S1 C23 H23A 109.5 . . ? S1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? S1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 58.5(4) . . . . ? C7 O1 C1 C6 -60.0(4) . . . . ? C8 O2 C2 C1 160.9(3) . . . . ? C8 O2 C2 C3 -81.3(4) . . . . ? O1 C1 C2 O2 65.7(4) . . . . ? C6 C1 C2 O2 -177.5(3) . . . . ? O1 C1 C2 C3 -53.5(4) . . . . ? C6 C1 C2 C3 63.3(4) . . . . ? C7 O3 C3 C4 60.4(4) . . . . ? C7 O3 C3 C2 -59.1(4) . . . . ? O2 C2 C3 O3 -63.5(4) . . . . ? C1 C2 C3 O3 53.7(4) . . . . ? O2 C2 C3 C4 178.0(3) . . . . ? C1 C2 C3 C4 -64.8(4) . . . . ? O3 C3 C4 O4 176.1(3) . . . . ? C2 C3 C4 O4 -64.4(4) . . . . ? O3 C3 C4 C5 -59.8(4) . . . . ? C2 C3 C4 C5 59.6(4) . . . . ? C7 O5 C5 C6 61.7(4) . . . . ? C7 O5 C5 C4 -60.3(4) . . . . ? O4 C4 C5 O5 178.9(3) . . . . ? C3 C4 C5 O5 59.4(4) . . . . ? O4 C4 C5 C6 62.4(4) . . . . ? C3 C4 C5 C6 -57.2(4) . . . . ? C15 O6 C6 C5 -105.1(4) . . . . ? C15 O6 C6 C1 136.1(3) . . . . ? O5 C5 C6 O6 -179.0(3) . . . . ? C4 C5 C6 O6 -61.8(4) . . . . ? O5 C5 C6 C1 -60.5(4) . . . . ? C4 C5 C6 C1 56.7(4) . . . . ? O1 C1 C6 O6 -178.7(3) . . . . ? C2 C1 C6 O6 62.7(4) . . . . ? O1 C1 C6 C5 60.4(4) . . . . ? C2 C1 C6 C5 -58.2(4) . . . . ? C3 O3 C7 O5 -61.0(4) . . . . ? C3 O3 C7 O1 63.4(4) . . . . ? C5 O5 C7 O3 61.5(4) . . . . ? C5 O5 C7 O1 -62.8(4) . . . . ? C1 O1 C7 O3 -63.2(4) . . . . ? C1 O1 C7 O5 61.8(4) . . . . ? C2 O2 C8 O7 0.4(5) . . . . ? C2 O2 C8 C9 -179.5(3) . . . . ? O7 C8 C9 C14 174.3(4) . . . . ? O2 C8 C9 C14 -5.8(6) . . . . ? O7 C8 C9 C10 -6.0(6) . . . . ? O2 C8 C9 C10 174.0(3) . . . . ? C14 C9 C10 C11 0.0(6) . . . . ? C8 C9 C10 C11 -179.8(4) . . . . ? C9 C10 C11 C12 -0.2(6) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? C10 C11 C12 Br1 -179.2(3) . . . . ? C11 C12 C13 C14 0.2(6) . . . . ? Br1 C12 C13 C14 179.5(3) . . . . ? C12 C13 C14 C9 -0.4(6) . . . . ? C10 C9 C14 C13 0.4(6) . . . . ? C8 C9 C14 C13 -179.9(4) . . . . ? C6 O6 C15 O8 -3.8(6) . . . . ? C6 O6 C15 C16 177.6(3) . . . . ? O8 C15 C16 C17 -21.0(6) . . . . ? O6 C15 C16 C17 157.5(4) . . . . ? O8 C15 C16 C21 157.3(4) . . . . ? O6 C15 C16 C21 -24.1(5) . . . . ? C21 C16 C17 C18 1.3(6) . . . . ? C15 C16 C17 C18 179.7(4) . . . . ? C16 C17 C18 C19 0.3(6) . . . . ? C17 C18 C19 C20 -1.8(6) . . . . ? C17 C18 C19 Br2 177.8(3) . . . . ? C18 C19 C20 C21 1.7(6) . . . . ? Br2 C19 C20 C21 -178.0(3) . . . . ? C19 C20 C21 C16 0.0(6) . . . . ? C17 C16 C21 C20 -1.5(6) . . . . ? C15 C16 C21 C20 -179.8(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 C13 H13 O8 0.95 2.49 3.271(5) 139.5 3_556 C7 H7 O9 1.00 2.22 3.199(5) 165.7 3_656 C5 H5 O4 1.00 2.55 3.277(5) 129.4 2_546 C11 H11 O1 0.95 2.58 3.437(5) 150.5 1_565 C5 H5 O7 1.00 2.59 3.299(5) 127.4 2_546 O4 H4A O7 0.83(7) 1.96(7) 2.776(4) 169(6) 2_546 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.033 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.086 #===END data_2H _database_code_depnum_ccdc_archive 'CCDC 752182' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate 1,2-dichloroethane solvate ; _chemical_name_common ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate 1,2- dichloroethane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8 , C2 H4 Cl2' _chemical_formula_sum 'C23 H20 Br2 Cl2 O8' _chemical_formula_weight 655.11 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1687(8) _cell_length_b 10.0099(7) _cell_length_c 20.3518(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.6770(10) _cell_angle_gamma 90.00 _cell_volume 2476.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 4224 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.43 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 3.536 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3569 _exptl_absorpt_correction_T_max 0.8862 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 12144 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4335 _reflns_number_gt 3763 _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 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^)+(0.0560P)^2^+4.9543P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4335 _refine_ls_number_parameters 347 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.002 _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 0.26653(3) 1.20838(4) 1.130101(18) 0.02589(14) Uani 1 1 d . . . Br2 Br 1.09647(4) 0.63643(5) 0.67896(3) 0.05114(18) Uani 1 1 d . . . O1 O 0.3932(2) 0.4408(3) 0.92776(12) 0.0225(6) Uani 1 1 d . . . O2 O 0.4144(2) 0.7242(2) 0.91765(12) 0.0202(5) Uani 1 1 d . . . O3 O 0.2640(2) 0.5352(3) 0.85473(13) 0.0241(6) Uani 1 1 d . . . O4 O 0.4545(2) 0.5891(3) 0.72528(12) 0.0218(6) Uani 1 1 d D . . O5 O 0.3412(2) 0.3288(3) 0.83130(13) 0.0247(6) Uani 1 1 d . . . O6 O 0.6152(2) 0.4641(2) 0.81198(12) 0.0206(5) Uani 1 1 d . . . O7 O 0.4353(2) 0.8991(3) 0.85017(12) 0.0236(6) Uani 1 1 d . . . O8 O 0.7305(2) 0.3750(3) 0.89008(15) 0.0358(7) Uani 1 1 d . . . C1 C 0.4839(3) 0.5063(4) 0.89787(17) 0.0193(7) Uani 1 1 d . . . H1 H 0.5446 0.5245 0.9315 0.023 Uiso 1 1 calc R . . C2 C 0.4447(3) 0.6362(3) 0.86536(17) 0.0184(7) Uani 1 1 d . . . H2 H 0.5052 0.6769 0.8404 0.022 Uiso 1 1 calc R . . C3 C 0.3461(3) 0.6057(4) 0.81915(18) 0.0193(7) Uani 1 1 d . . . H3 H 0.3144 0.6909 0.8009 0.023 Uiso 1 1 calc R . . C4 C 0.3802(3) 0.5164(4) 0.76332(18) 0.0204(8) Uani 1 1 d . . . H4 H 0.3136 0.4930 0.7350 0.024 Uiso 1 1 calc R . . C5 C 0.4283(3) 0.3881(4) 0.79471(19) 0.0218(8) Uani 1 1 d . . . H5 H 0.4511 0.3252 0.7597 0.026 Uiso 1 1 calc R . . C6 C 0.5235(3) 0.4105(4) 0.84495(17) 0.0186(7) Uani 1 1 d . . . H6 H 0.5450 0.3233 0.8658 0.022 Uiso 1 1 calc R . . C7 C 0.3074(3) 0.4156(4) 0.8811(2) 0.0250(8) Uani 1 1 d . . . H7 H 0.2473 0.3698 0.9043 0.030 Uiso 1 1 calc R . . C8 C 0.4115(3) 0.8552(3) 0.90353(17) 0.0183(7) Uani 1 1 d . . . C9 C 0.3769(3) 0.9375(4) 0.95901(17) 0.0190(7) Uani 1 1 d . . . C14 C 0.3513(3) 0.8800(4) 1.01910(18) 0.0216(8) Uani 1 1 d . . . H14 H 0.3561 0.7859 1.0247 0.026 Uiso 1 1 calc R . . C13 C 0.3191(3) 0.9596(4) 1.07054(18) 0.0219(8) Uani 1 1 d . . . H13 H 0.3019 0.9211 1.1115 0.026 Uiso 1 1 calc R . . C12 C 0.3126(3) 1.0964(4) 1.06092(18) 0.0205(8) Uani 1 1 d . . . C11 C 0.3390(3) 1.1555(4) 1.00236(18) 0.0218(8) Uani 1 1 d . . . H11 H 0.3353 1.2498 0.9973 0.026 Uiso 1 1 calc R . . C10 C 0.3706(3) 1.0759(4) 0.95134(18) 0.0224(8) Uani 1 1 d . . . H10 H 0.3883 1.1155 0.9107 0.027 Uiso 1 1 calc R . . C15 C 0.7164(3) 0.4377(4) 0.83981(19) 0.0231(8) Uani 1 1 d . . . C16 C 0.8048(3) 0.4951(4) 0.80091(19) 0.0224(8) Uani 1 1 d . . . C21 C 0.7846(3) 0.5602(4) 0.7416(2) 0.0284(9) Uani 1 1 d . . . H21 H 0.7109 0.5737 0.7254 0.034 Uiso 1 1 calc R . . C20 C 0.8710(4) 0.6058(5) 0.7058(2) 0.0361(10) Uani 1 1 d . . . H20 H 0.8573 0.6516 0.6653 0.043 Uiso 1 1 calc R . . C19 C 0.9773(3) 0.5834(4) 0.7297(2) 0.0320(10) Uani 1 1 d . . . C18 C 0.9997(3) 0.5229(5) 0.7897(2) 0.0359(10) Uani 1 1 d . . . H18 H 1.0735 0.5116 0.8062 0.043 Uiso 1 1 calc R . . C17 C 0.9133(3) 0.4794(4) 0.8251(2) 0.0322(9) Uani 1 1 d . . . H17 H 0.9276 0.4380 0.8667 0.039 Uiso 1 1 calc R . . H4A H 0.482(3) 0.542(4) 0.6980(17) 0.029(12) Uiso 1 1 d D . . Cl1 Cl 0.12359(17) 0.8339(2) 0.88152(10) 0.0852(5) Uani 1 1 d D . . Cl2 Cl -0.06632(18) 0.6683(4) 1.02638(13) 0.1017(11) Uani 0.75 1 d PDU A 1 C22 C 0.0867(7) 0.7216(8) 0.9405(4) 0.0620(19) Uani 0.75 1 d PDU A 1 H22A H 0.0550 0.6400 0.9197 0.074 Uiso 0.75 1 calc PR A 1 H22B H 0.1516 0.6959 0.9689 0.074 Uiso 0.75 1 calc PR A 1 C23 C 0.0013(8) 0.7917(10) 0.9810(5) 0.085(2) Uani 0.75 1 d PDU A 1 H23A H -0.0524 0.8397 0.9516 0.102 Uiso 0.75 1 calc PR A 1 H23B H 0.0377 0.8573 1.0112 0.102 Uiso 0.75 1 calc PR A 1 Cl2' Cl -0.0683(5) 0.7913(11) 1.0185(3) 0.080(2) Uani 0.25 1 d PDU A 2 C22' C 0.068(2) 0.907(2) 0.9541(9) 0.074(4) Uani 0.25 1 d PDU A 2 H22C H 0.1140 0.9825 0.9708 0.089 Uiso 0.25 1 calc PR A 2 H22D H -0.0083 0.9375 0.9456 0.089 Uiso 0.25 1 calc PR A 2 C23' C 0.0744(15) 0.781(3) 1.0051(14) 0.073(4) Uani 0.25 1 d PDU A 2 H23C H 0.1214 0.7981 1.0453 0.088 Uiso 0.25 1 calc PR A 2 H23D H 0.0957 0.6958 0.9843 0.088 Uiso 0.25 1 calc PR A 2 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 0.0337(2) 0.0231(2) 0.0212(2) -0.00525(15) 0.00391(15) 0.00365(16) Br2 0.0258(3) 0.0551(3) 0.0742(4) 0.0218(3) 0.0203(2) 0.0022(2) O1 0.0233(14) 0.0246(13) 0.0200(13) 0.0048(11) 0.0062(10) -0.0013(11) O2 0.0281(14) 0.0176(13) 0.0155(12) -0.0010(10) 0.0055(10) -0.0007(10) O3 0.0186(13) 0.0257(14) 0.0283(15) 0.0030(11) 0.0034(11) 0.0000(11) O4 0.0277(14) 0.0209(13) 0.0173(13) -0.0016(11) 0.0047(11) 0.0033(11) O5 0.0232(14) 0.0204(13) 0.0308(15) -0.0010(11) 0.0046(11) -0.0058(11) O6 0.0171(12) 0.0221(13) 0.0228(13) 0.0036(11) 0.0025(10) 0.0026(10) O7 0.0308(15) 0.0228(13) 0.0178(13) 0.0013(11) 0.0062(11) -0.0009(11) O8 0.0286(16) 0.0451(18) 0.0334(16) 0.0164(14) -0.0021(12) 0.0008(13) C1 0.0187(18) 0.0201(18) 0.0191(18) 0.0017(15) 0.0007(14) -0.0015(15) C2 0.0219(18) 0.0187(18) 0.0148(17) -0.0019(14) 0.0033(14) 0.0001(14) C3 0.0193(18) 0.0177(17) 0.0210(18) -0.0002(14) 0.0031(14) 0.0011(14) C4 0.0211(18) 0.0205(18) 0.0193(18) -0.0004(15) -0.0022(14) -0.0019(15) C5 0.0244(19) 0.0183(18) 0.0231(19) -0.0004(15) 0.0040(15) -0.0020(15) C6 0.0173(17) 0.0185(18) 0.0204(18) 0.0019(14) 0.0040(14) 0.0009(14) C7 0.0215(19) 0.0224(19) 0.031(2) 0.0023(16) 0.0049(16) -0.0024(15) C8 0.0170(18) 0.0191(18) 0.0189(18) 0.0010(15) 0.0001(14) -0.0016(14) C9 0.0212(18) 0.0191(18) 0.0167(18) 0.0000(14) -0.0001(14) -0.0010(14) C14 0.0256(19) 0.0181(18) 0.0210(19) 0.0026(15) 0.0010(15) -0.0003(15) C13 0.028(2) 0.0212(18) 0.0164(18) 0.0021(15) 0.0045(15) 0.0000(15) C12 0.0203(18) 0.0235(19) 0.0175(18) -0.0046(15) 0.0000(14) 0.0031(15) C11 0.026(2) 0.0165(17) 0.0231(19) 0.0009(15) -0.0004(15) 0.0013(15) C10 0.0244(19) 0.0243(19) 0.0186(19) 0.0019(15) 0.0016(15) -0.0011(15) C15 0.0211(19) 0.0203(18) 0.028(2) -0.0013(16) -0.0013(15) 0.0034(15) C16 0.0197(18) 0.0209(18) 0.027(2) -0.0012(16) 0.0013(15) 0.0021(15) C21 0.0184(19) 0.034(2) 0.033(2) 0.0051(18) 0.0030(16) 0.0045(17) C20 0.029(2) 0.041(2) 0.039(3) 0.012(2) 0.0087(19) 0.0034(19) C19 0.019(2) 0.029(2) 0.048(3) 0.0030(19) 0.0105(18) 0.0006(16) C18 0.0137(19) 0.042(2) 0.052(3) 0.005(2) -0.0030(18) -0.0007(17) C17 0.023(2) 0.039(2) 0.034(2) 0.0065(19) -0.0037(17) -0.0011(18) Cl1 0.0878(13) 0.0767(11) 0.0908(13) 0.0171(10) 0.0024(10) -0.0023(10) Cl2 0.0379(11) 0.183(3) 0.0848(18) 0.066(2) 0.0088(10) 0.0049(16) C22 0.060(4) 0.062(4) 0.066(4) -0.016(4) 0.019(3) -0.007(3) C23 0.068(5) 0.104(5) 0.081(5) 0.008(4) -0.001(4) -0.002(4) Cl2' 0.025(3) 0.156(7) 0.059(4) -0.021(4) 0.005(2) 0.013(4) C22' 0.056(7) 0.086(8) 0.079(8) 0.007(7) -0.010(7) -0.006(7) C23' 0.057(6) 0.088(7) 0.075(7) -0.001(6) 0.000(6) -0.003(6) _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 1.904(4) . ? Br2 C19 1.895(4) . ? O1 C7 1.401(5) . ? O1 C1 1.443(4) . ? O2 C8 1.342(4) . ? O2 C2 1.443(4) . ? O3 C7 1.405(5) . ? O3 C3 1.445(4) . ? O4 C4 1.418(4) . ? O4 H4A 0.81(4) . ? O5 C7 1.411(5) . ? O5 C5 1.450(5) . ? O6 C15 1.357(4) . ? O6 C6 1.433(4) . ? O7 C8 1.219(4) . ? O8 C15 1.205(5) . ? C1 C2 1.525(5) . ? C1 C6 1.536(5) . ? C1 H1 1.0000 . ? C2 C3 1.521(5) . ? C2 H2 1.0000 . ? C3 C4 1.519(5) . ? C3 H3 1.0000 . ? C4 C5 1.538(5) . ? C4 H4 1.0000 . ? C5 C6 1.525(5) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.475(5) . ? C9 C10 1.396(5) . ? C9 C14 1.400(5) . ? C14 C13 1.386(5) . ? C14 H14 0.9500 . ? C13 C12 1.386(5) . ? C13 H13 0.9500 . ? C12 C11 1.382(5) . ? C11 C10 1.378(5) . ? C11 H11 0.9500 . ? C10 H10 0.9500 . ? C15 C16 1.481(5) . ? C16 C21 1.383(6) . ? C16 C17 1.397(5) . ? C21 C20 1.386(6) . ? C21 H21 0.9500 . ? C20 C19 1.379(6) . ? C20 H20 0.9500 . ? C19 C18 1.378(6) . ? C18 C17 1.374(6) . ? C18 H18 0.9500 . ? C17 H17 0.9500 . ? Cl1 C22 1.720(8) . ? Cl1 C22' 1.806(17) . ? Cl2 C23 1.769(10) . ? C22 C23 1.526(11) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? Cl2' C23' 1.773(17) . ? C22' C23' 1.633(19) . ? C22' H22C 0.9900 . ? C22' H22D 0.9900 . ? C23' H23C 0.9900 . ? C23' H23D 0.9900 . ? 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 110.9(3) . . ? C8 O2 C2 116.3(3) . . ? C7 O3 C3 110.6(3) . . ? C4 O4 H4A 112(3) . . ? C7 O5 C5 111.2(3) . . ? C15 O6 C6 116.3(3) . . ? O1 C1 C2 109.9(3) . . ? O1 C1 C6 106.4(3) . . ? C2 C1 C6 109.3(3) . . ? O1 C1 H1 110.4 . . ? C2 C1 H1 110.4 . . ? C6 C1 H1 110.4 . . ? O2 C2 C3 110.9(3) . . ? O2 C2 C1 106.6(3) . . ? C3 C2 C1 108.6(3) . . ? O2 C2 H2 110.2 . . ? C3 C2 H2 110.2 . . ? C1 C2 H2 110.2 . . ? O3 C3 C4 107.9(3) . . ? O3 C3 C2 109.4(3) . . ? C4 C3 C2 110.2(3) . . ? O3 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? O4 C4 C3 108.0(3) . . ? O4 C4 C5 114.6(3) . . ? C3 C4 C5 107.0(3) . . ? O4 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? O5 C5 C6 105.4(3) . . ? O5 C5 C4 106.4(3) . . ? C6 C5 C4 114.7(3) . . ? O5 C5 H5 110.0 . . ? C6 C5 H5 110.0 . . ? C4 C5 H5 110.0 . . ? O6 C6 C5 109.0(3) . . ? O6 C6 C1 111.8(3) . . ? C5 C6 C1 108.0(3) . . ? O6 C6 H6 109.4 . . ? C5 C6 H6 109.4 . . ? C1 C6 H6 109.4 . . ? O1 C7 O3 111.2(3) . . ? O1 C7 O5 111.4(3) . . ? O3 C7 O5 111.5(3) . . ? O1 C7 H7 107.5 . . ? O3 C7 H7 107.5 . . ? O5 C7 H7 107.5 . . ? O7 C8 O2 122.6(3) . . ? O7 C8 C9 124.6(3) . . ? O2 C8 C9 112.8(3) . . ? C10 C9 C14 119.5(3) . . ? C10 C9 C8 119.0(3) . . ? C14 C9 C8 121.5(3) . . ? C13 C14 C9 120.4(3) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? C12 C13 C14 118.5(3) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C11 C12 C13 122.1(3) . . ? C11 C12 Br1 118.3(3) . . ? C13 C12 Br1 119.6(3) . . ? C10 C11 C12 119.2(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? O8 C15 O6 123.1(4) . . ? O8 C15 C16 125.3(3) . . ? O6 C15 C16 111.7(3) . . ? C21 C16 C17 119.2(4) . . ? C21 C16 C15 123.0(3) . . ? C17 C16 C15 117.8(3) . . ? C16 C21 C20 120.4(4) . . ? C16 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C19 C20 C21 118.9(4) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C18 C19 C20 121.9(4) . . ? C18 C19 Br2 118.7(3) . . ? C20 C19 Br2 119.4(3) . . ? C17 C18 C19 118.7(4) . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? C18 C17 C16 120.9(4) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C22 Cl1 C22' 64.7(8) . . ? C23 C22 Cl1 106.4(6) . . ? C23 C22 H22A 110.4 . . ? Cl1 C22 H22A 110.4 . . ? C23 C22 H22B 110.4 . . ? Cl1 C22 H22B 110.4 . . ? H22A C22 H22B 108.6 . . ? C22 C23 Cl2 107.8(7) . . ? C22 C23 H23A 110.1 . . ? Cl2 C23 H23A 110.1 . . ? C22 C23 H23B 110.1 . . ? Cl2 C23 H23B 110.1 . . ? H23A C23 H23B 108.5 . . ? C23' C22' Cl1 101.6(15) . . ? C23' C22' H22C 111.5 . . ? Cl1 C22' H22C 111.5 . . ? C23' C22' H22D 111.5 . . ? Cl1 C22' H22D 111.5 . . ? H22C C22' H22D 109.3 . . ? C22' C23' Cl2' 92.1(14) . . ? C22' C23' H23C 113.3 . . ? Cl2' C23' H23C 113.3 . . ? C22' C23' H23D 113.3 . . ? Cl2' C23' H23D 113.3 . . ? H23C C23' H23D 110.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C2 57.6(4) . . . . ? C7 O1 C1 C6 -60.6(3) . . . . ? C8 O2 C2 C3 -82.7(4) . . . . ? C8 O2 C2 C1 159.2(3) . . . . ? O1 C1 C2 O2 66.6(3) . . . . ? C6 C1 C2 O2 -177.0(3) . . . . ? O1 C1 C2 C3 -53.0(4) . . . . ? C6 C1 C2 C3 63.4(4) . . . . ? C7 O3 C3 C4 60.8(4) . . . . ? C7 O3 C3 C2 -59.0(4) . . . . ? O2 C2 C3 O3 -63.3(4) . . . . ? C1 C2 C3 O3 53.6(4) . . . . ? O2 C2 C3 C4 178.3(3) . . . . ? C1 C2 C3 C4 -64.8(4) . . . . ? O3 C3 C4 O4 175.6(3) . . . . ? C2 C3 C4 O4 -65.0(4) . . . . ? O3 C3 C4 C5 -60.6(3) . . . . ? C2 C3 C4 C5 58.8(4) . . . . ? C7 O5 C5 C6 61.3(4) . . . . ? C7 O5 C5 C4 -60.9(4) . . . . ? O4 C4 C5 O5 179.8(3) . . . . ? C3 C4 C5 O5 60.1(4) . . . . ? O4 C4 C5 C6 63.7(4) . . . . ? C3 C4 C5 C6 -56.1(4) . . . . ? C15 O6 C6 C5 -152.6(3) . . . . ? C15 O6 C6 C1 88.1(4) . . . . ? O5 C5 C6 O6 177.6(3) . . . . ? C4 C5 C6 O6 -65.7(4) . . . . ? O5 C5 C6 C1 -60.8(3) . . . . ? C4 C5 C6 C1 55.9(4) . . . . ? O1 C1 C6 O6 -179.3(3) . . . . ? C2 C1 C6 O6 62.1(4) . . . . ? O1 C1 C6 C5 60.9(3) . . . . ? C2 C1 C6 C5 -57.7(4) . . . . ? C1 O1 C7 O3 -63.0(4) . . . . ? C1 O1 C7 O5 62.1(4) . . . . ? C3 O3 C7 O1 63.8(4) . . . . ? C3 O3 C7 O5 -61.2(4) . . . . ? C5 O5 C7 O1 -62.8(4) . . . . ? C5 O5 C7 O3 62.1(4) . . . . ? C2 O2 C8 O7 -1.5(5) . . . . ? C2 O2 C8 C9 178.5(3) . . . . ? O7 C8 C9 C10 -0.3(5) . . . . ? O2 C8 C9 C10 179.8(3) . . . . ? O7 C8 C9 C14 -179.7(3) . . . . ? O2 C8 C9 C14 0.4(5) . . . . ? C10 C9 C14 C13 0.5(6) . . . . ? C8 C9 C14 C13 179.9(3) . . . . ? C9 C14 C13 C12 0.2(6) . . . . ? C14 C13 C12 C11 -1.1(6) . . . . ? C14 C13 C12 Br1 179.1(3) . . . . ? C13 C12 C11 C10 1.3(6) . . . . ? Br1 C12 C11 C10 -178.9(3) . . . . ? C12 C11 C10 C9 -0.6(6) . . . . ? C14 C9 C10 C11 -0.3(6) . . . . ? C8 C9 C10 C11 -179.7(3) . . . . ? C6 O6 C15 O8 -1.4(5) . . . . ? C6 O6 C15 C16 178.7(3) . . . . ? O8 C15 C16 C21 176.4(4) . . . . ? O6 C15 C16 C21 -3.6(5) . . . . ? O8 C15 C16 C17 -2.1(6) . . . . ? O6 C15 C16 C17 177.9(3) . . . . ? C17 C16 C21 C20 1.9(6) . . . . ? C15 C16 C21 C20 -176.7(4) . . . . ? C16 C21 C20 C19 0.9(7) . . . . ? C21 C20 C19 C18 -3.2(7) . . . . ? C21 C20 C19 Br2 176.6(3) . . . . ? C20 C19 C18 C17 2.5(7) . . . . ? Br2 C19 C18 C17 -177.2(3) . . . . ? C19 C18 C17 C16 0.4(7) . . . . ? C21 C16 C17 C18 -2.6(6) . . . . ? C15 C16 C17 C18 176.1(4) . . . . ? C22' Cl1 C22 C23 23.6(10) . . . . ? Cl1 C22 C23 Cl2 164.0(5) . . . . ? C22 Cl1 C22' C23' 14.5(12) . . . . ? Cl1 C22' C23' Cl2' -124.0(14) . . . . ? 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 C23' H23C Br2 0.99 2.83 3.63(3) 138.6 4_476 C22' H22C Cl2' 0.99 2.34 3.07(3) 129.8 3_577 O4 H4A O7 0.81(4) 2.03(2) 2.822(4) 166(4) 2_646 C7 H7 Cl2 1.00 2.70 3.657(4) 160.8 3_567 C11 H11 O1 0.95 2.50 3.315(4) 143.9 1_565 C18 H18 O3 0.95 2.49 3.422(5) 167.4 1_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.785 _refine_diff_density_min -0.939 _refine_diff_density_rms 0.097 #===END # Attachment '3.cif' data_3A _database_code_depnum_ccdc_archive 'CCDC 752183' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate chloroform solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate chloroform solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, C H Cl3' _chemical_formula_sum 'C22 H17 Cl5 O8' _chemical_formula_weight 586.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9486(9) _cell_length_b 10.2705(7) _cell_length_c 18.0529(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.3980(10) _cell_angle_gamma 90.00 _cell_volume 2353.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 8263 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.28 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.665 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9238 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 16706 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4146 _reflns_number_gt 3906 _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 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^)+(0.0332P)^2^+3.1901P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4146 _refine_ls_number_parameters 320 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 O4 O 0.71033(13) 0.07540(16) 0.73735(9) 0.0234(4) Uani 1 1 d D . . O1 O 0.85960(12) -0.06207(15) 0.96768(8) 0.0202(3) Uani 1 1 d . . . O2 O 0.85445(12) 0.21539(14) 0.95036(8) 0.0182(3) Uani 1 1 d . . . O3 O 0.68986(12) 0.01810(15) 0.93230(8) 0.0209(3) Uani 1 1 d . . . O5 O 0.73450(13) -0.17941(15) 0.88374(9) 0.0219(4) Uani 1 1 d . . . O6 O 0.91852(13) -0.02610(15) 0.77978(9) 0.0221(4) Uani 1 1 d . . . O7 O 0.79544(13) 0.38121(15) 0.87247(8) 0.0229(4) Uani 1 1 d . . . O8 O 0.99331(16) -0.21260(17) 0.75179(11) 0.0377(5) Uani 1 1 d . . . Cl1 Cl 0.97424(4) 0.69368(5) 1.19991(3) 0.02327(14) Uani 1 1 d . . . Cl2 Cl 1.10715(5) 0.20623(6) 0.49289(3) 0.02915(16) Uani 1 1 d . . . C1 C 0.89558(17) 0.0056(2) 0.90722(12) 0.0179(5) Uani 1 1 d . . . H1 H 0.9718 0.0286 0.9230 0.021 Uiso 1 1 calc R . . C2 C 0.83031(17) 0.1278(2) 0.88613(12) 0.0172(5) Uani 1 1 d . . . H2 H 0.8498 0.1695 0.8407 0.021 Uiso 1 1 calc R . . C3 C 0.71452(17) 0.0905(2) 0.86914(12) 0.0183(5) Uani 1 1 d . . . H3 H 0.6698 0.1706 0.8600 0.022 Uiso 1 1 calc R . . C4 C 0.69203(18) 0.0024(2) 0.79986(12) 0.0202(5) Uani 1 1 d . . . H4 H 0.6164 -0.0250 0.7905 0.024 Uiso 1 1 calc R . . C5 C 0.76222(18) -0.1187(2) 0.81784(12) 0.0197(5) Uani 1 1 d . . . H5 H 0.7489 -0.1803 0.7741 0.024 Uiso 1 1 calc R . . C6 C 0.87977(18) -0.0884(2) 0.84010(12) 0.0190(5) Uani 1 1 d . . . H6 H 0.9200 -0.1706 0.8550 0.023 Uiso 1 1 calc R . . C7 C 0.75198(18) -0.0945(2) 0.94579(13) 0.0212(5) Uani 1 1 d . . . H7 H 0.7311 -0.1414 0.9891 0.025 Uiso 1 1 calc R . . C8 C 0.83408(17) 0.3422(2) 0.93506(12) 0.0176(5) Uani 1 1 d . . . C9 C 0.86614(17) 0.4264(2) 1.00250(12) 0.0174(5) Uani 1 1 d . . . C10 C 0.86420(17) 0.5608(2) 0.99193(12) 0.0184(5) Uani 1 1 d . . . H10 H 0.8401 0.5961 0.9429 0.022 Uiso 1 1 calc R . . C11 C 0.89744(17) 0.6434(2) 1.05284(13) 0.0198(5) Uani 1 1 d . . . H11 H 0.8972 0.7351 1.0460 0.024 Uiso 1 1 calc R . . C12 C 0.93101(17) 0.5895(2) 1.12391(12) 0.0185(5) Uani 1 1 d . . . C13 C 0.93153(18) 0.4562(2) 1.13605(13) 0.0212(5) Uani 1 1 d . . . H13 H 0.9535 0.4214 1.1854 0.025 Uiso 1 1 calc R . . C14 C 0.89939(17) 0.3749(2) 1.07482(12) 0.0197(5) Uani 1 1 d . . . H14 H 0.8999 0.2832 1.0820 0.024 Uiso 1 1 calc R . . C15 C 0.97352(18) -0.0997(2) 0.73889(13) 0.0207(5) Uani 1 1 d . . . C16 C 1.00435(18) -0.0230(2) 0.67735(12) 0.0192(5) Uani 1 1 d . . . C17 C 1.08703(18) -0.0681(2) 0.64553(13) 0.0232(5) Uani 1 1 d . . . H17 H 1.1216 -0.1471 0.6630 0.028 Uiso 1 1 calc R . . C18 C 1.11919(18) 0.0018(2) 0.58851(13) 0.0239(5) Uani 1 1 d . . . H18 H 1.1762 -0.0279 0.5670 0.029 Uiso 1 1 calc R . . C19 C 1.06673(18) 0.1155(2) 0.56355(12) 0.0217(5) Uani 1 1 d . . . C20 C 0.98298(18) 0.1609(2) 0.59320(13) 0.0234(5) Uani 1 1 d . . . H20 H 0.9472 0.2384 0.5743 0.028 Uiso 1 1 calc R . . C21 C 0.95221(18) 0.0917(2) 0.65089(13) 0.0202(5) Uani 1 1 d . . . H21 H 0.8955 0.1223 0.6725 0.024 Uiso 1 1 calc R . . C22 C 0.2972(2) 0.9550(3) 0.87817(15) 0.0340(6) Uani 1 1 d . . . H22 H 0.2864 0.9252 0.9288 0.041 Uiso 1 1 calc R . . Cl3 Cl 0.27380(6) 0.82223(7) 0.81603(4) 0.04118(19) Uani 1 1 d . . . Cl4 Cl 0.20522(7) 1.08057(8) 0.84683(4) 0.0508(2) Uani 1 1 d . . . Cl5 Cl 0.42633(7) 1.01215(9) 0.88857(6) 0.0613(3) Uani 1 1 d . . . H4A H 0.706(2) 0.025(3) 0.7026(14) 0.041(9) Uiso 1 1 d 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 O4 0.0358(10) 0.0190(8) 0.0142(8) -0.0008(7) 0.0016(7) 0.0010(7) O1 0.0242(8) 0.0200(8) 0.0160(8) 0.0032(6) 0.0030(6) -0.0024(7) O2 0.0241(8) 0.0139(8) 0.0158(7) -0.0009(6) 0.0018(6) -0.0013(6) O3 0.0219(8) 0.0230(8) 0.0190(8) -0.0005(6) 0.0071(6) -0.0011(7) O5 0.0304(9) 0.0176(8) 0.0188(8) -0.0004(6) 0.0075(7) -0.0056(7) O6 0.0307(9) 0.0167(8) 0.0225(8) 0.0022(6) 0.0139(7) 0.0032(7) O7 0.0323(9) 0.0203(8) 0.0152(8) 0.0016(6) 0.0028(7) 0.0006(7) O8 0.0551(12) 0.0220(10) 0.0447(11) 0.0099(8) 0.0309(10) 0.0128(9) Cl1 0.0277(3) 0.0196(3) 0.0204(3) -0.0052(2) -0.0005(2) 0.0008(2) Cl2 0.0291(3) 0.0370(4) 0.0234(3) 0.0063(3) 0.0103(2) -0.0040(3) C1 0.0193(11) 0.0183(11) 0.0165(11) 0.0021(9) 0.0048(9) -0.0008(9) C2 0.0225(11) 0.0159(11) 0.0131(10) -0.0032(8) 0.0033(9) -0.0020(9) C3 0.0210(11) 0.0177(11) 0.0165(11) -0.0003(9) 0.0048(9) -0.0005(9) C4 0.0204(11) 0.0207(12) 0.0181(11) -0.0017(9) 0.0008(9) -0.0036(9) C5 0.0272(12) 0.0160(11) 0.0164(11) -0.0011(9) 0.0055(9) -0.0029(9) C6 0.0260(12) 0.0147(11) 0.0179(11) 0.0039(9) 0.0085(9) 0.0016(9) C7 0.0260(12) 0.0190(11) 0.0194(11) 0.0003(9) 0.0069(9) -0.0034(9) C8 0.0173(11) 0.0173(11) 0.0195(12) 0.0012(9) 0.0064(9) -0.0015(9) C9 0.0157(10) 0.0179(11) 0.0189(11) -0.0003(9) 0.0043(9) -0.0008(9) C10 0.0201(11) 0.0203(12) 0.0150(11) 0.0030(9) 0.0041(9) 0.0004(9) C11 0.0205(11) 0.0153(11) 0.0237(12) -0.0002(9) 0.0046(9) 0.0002(9) C12 0.0180(11) 0.0185(11) 0.0189(11) -0.0045(9) 0.0030(9) -0.0001(9) C13 0.0254(12) 0.0194(12) 0.0180(11) 0.0024(9) 0.0024(9) 0.0013(9) C14 0.0228(11) 0.0143(11) 0.0220(12) 0.0011(9) 0.0043(9) -0.0001(9) C15 0.0197(11) 0.0197(12) 0.0235(12) -0.0015(9) 0.0060(9) 0.0010(9) C16 0.0215(11) 0.0198(11) 0.0167(11) -0.0022(9) 0.0050(9) -0.0027(9) C17 0.0245(12) 0.0220(12) 0.0236(12) -0.0004(10) 0.0061(10) 0.0030(10) C18 0.0211(12) 0.0290(13) 0.0235(12) -0.0037(10) 0.0088(10) -0.0003(10) C19 0.0219(11) 0.0279(13) 0.0157(11) -0.0001(9) 0.0047(9) -0.0055(10) C20 0.0239(12) 0.0231(12) 0.0227(12) 0.0029(10) 0.0035(9) 0.0009(10) C21 0.0193(11) 0.0211(12) 0.0211(11) -0.0008(9) 0.0063(9) 0.0009(9) C22 0.0333(14) 0.0397(16) 0.0279(14) 0.0010(12) 0.0034(11) 0.0092(12) Cl3 0.0442(4) 0.0431(4) 0.0336(4) -0.0039(3) 0.0011(3) 0.0095(3) Cl4 0.0614(5) 0.0547(5) 0.0330(4) -0.0018(3) 0.0011(3) 0.0321(4) Cl5 0.0430(5) 0.0573(5) 0.0810(6) -0.0008(5) 0.0058(4) -0.0093(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O4 C4 1.414(3) . ? O4 H4A 0.804(18) . ? O1 C7 1.411(3) . ? O1 C1 1.446(3) . ? O2 C8 1.346(3) . ? O2 C2 1.452(2) . ? O3 C7 1.402(3) . ? O3 C3 1.449(3) . ? O5 C7 1.402(3) . ? O5 C5 1.450(3) . ? O6 C15 1.353(3) . ? O6 C6 1.436(3) . ? O7 C8 1.210(3) . ? O8 C15 1.200(3) . ? Cl1 C12 1.743(2) . ? Cl2 C19 1.742(2) . ? C1 C2 1.520(3) . ? C1 C6 1.531(3) . ? C1 H1 1.0000 . ? C2 C3 1.519(3) . ? C2 H2 1.0000 . ? C3 C4 1.525(3) . ? C3 H3 1.0000 . ? C4 C5 1.536(3) . ? C4 H4 1.0000 . ? C5 C6 1.527(3) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.485(3) . ? C9 C10 1.393(3) . ? C9 C14 1.396(3) . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 C13 1.386(3) . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.480(3) . ? C16 C17 1.391(3) . ? C16 C21 1.394(3) . ? C17 C18 1.385(3) . ? C17 H17 0.9500 . ? C18 C19 1.381(3) . ? C18 H18 0.9500 . ? C19 C20 1.382(3) . ? C20 C21 1.383(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 Cl5 1.747(3) . ? C22 Cl3 1.754(3) . ? C22 Cl4 1.770(3) . ? C22 H22 1.0000 . ? 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 C4 O4 H4A 107(2) . . ? C7 O1 C1 110.45(16) . . ? C8 O2 C2 115.64(16) . . ? C7 O3 C3 110.61(16) . . ? C7 O5 C5 111.15(16) . . ? C15 O6 C6 117.71(17) . . ? O1 C1 C2 109.87(17) . . ? O1 C1 C6 106.37(17) . . ? C2 C1 C6 110.00(17) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C3 111.45(17) . . ? O2 C2 C1 106.89(16) . . ? C3 C2 C1 108.66(18) . . ? O2 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? C1 C2 H2 109.9 . . ? O3 C3 C2 109.45(17) . . ? O3 C3 C4 107.73(17) . . ? C2 C3 C4 109.65(18) . . ? O3 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? C4 C3 H3 110.0 . . ? O4 C4 C3 107.74(18) . . ? O4 C4 C5 114.38(19) . . ? C3 C4 C5 107.34(18) . . ? O4 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? O5 C5 C6 105.49(17) . . ? O5 C5 C4 106.83(17) . . ? C6 C5 C4 114.09(18) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 111.74(18) . . ? O6 C6 C1 107.88(17) . . ? C5 C6 C1 107.88(18) . . ? O6 C6 H6 109.8 . . ? C5 C6 H6 109.8 . . ? C1 C6 H6 109.8 . . ? O5 C7 O3 112.19(18) . . ? O5 C7 O1 111.42(18) . . ? O3 C7 O1 110.78(18) . . ? O5 C7 H7 107.4 . . ? O3 C7 H7 107.4 . . ? O1 C7 H7 107.4 . . ? O7 C8 O2 122.7(2) . . ? O7 C8 C9 124.7(2) . . ? O2 C8 C9 112.59(18) . . ? C10 C9 C14 119.9(2) . . ? C10 C9 C8 118.1(2) . . ? C14 C9 C8 122.0(2) . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 118.8(2) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C13 122.1(2) . . ? C11 C12 Cl1 118.46(17) . . ? C13 C12 Cl1 119.43(17) . . ? C14 C13 C12 118.6(2) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C9 120.5(2) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? O8 C15 O6 123.3(2) . . ? O8 C15 C16 125.5(2) . . ? O6 C15 C16 111.15(19) . . ? C17 C16 C21 120.0(2) . . ? C17 C16 C15 118.4(2) . . ? C21 C16 C15 121.5(2) . . ? C18 C17 C16 120.2(2) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 118.7(2) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C18 C19 C20 122.1(2) . . ? C18 C19 Cl2 119.46(18) . . ? C20 C19 Cl2 118.39(18) . . ? C19 C20 C21 118.9(2) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C20 C21 C16 120.0(2) . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? Cl5 C22 Cl3 111.73(15) . . ? Cl5 C22 Cl4 111.04(16) . . ? Cl3 C22 Cl4 109.99(14) . . ? Cl5 C22 H22 108.0 . . ? Cl3 C22 H22 108.0 . . ? Cl4 C22 H22 108.0 . . ? 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 58.3(2) . . . . ? C7 O1 C1 C6 -60.7(2) . . . . ? C8 O2 C2 C3 -83.1(2) . . . . ? C8 O2 C2 C1 158.34(18) . . . . ? O1 C1 C2 O2 66.9(2) . . . . ? C6 C1 C2 O2 -176.35(17) . . . . ? O1 C1 C2 C3 -53.5(2) . . . . ? C6 C1 C2 C3 63.3(2) . . . . ? C7 O3 C3 C2 -59.1(2) . . . . ? C7 O3 C3 C4 60.1(2) . . . . ? O2 C2 C3 O3 -63.9(2) . . . . ? C1 C2 C3 O3 53.6(2) . . . . ? O2 C2 C3 C4 178.13(17) . . . . ? C1 C2 C3 C4 -64.3(2) . . . . ? O3 C3 C4 O4 176.72(16) . . . . ? C2 C3 C4 O4 -64.2(2) . . . . ? O3 C3 C4 C5 -59.7(2) . . . . ? C2 C3 C4 C5 59.4(2) . . . . ? C7 O5 C5 C6 61.5(2) . . . . ? C7 O5 C5 C4 -60.2(2) . . . . ? O4 C4 C5 O5 178.82(17) . . . . ? C3 C4 C5 O5 59.4(2) . . . . ? O4 C4 C5 C6 62.7(2) . . . . ? C3 C4 C5 C6 -56.8(2) . . . . ? C15 O6 C6 C5 -102.3(2) . . . . ? C15 O6 C6 C1 139.29(19) . . . . ? O5 C5 C6 O6 -179.46(16) . . . . ? C4 C5 C6 O6 -62.5(2) . . . . ? O5 C5 C6 C1 -61.0(2) . . . . ? C4 C5 C6 C1 55.9(2) . . . . ? O1 C1 C6 O6 -177.83(16) . . . . ? C2 C1 C6 O6 63.2(2) . . . . ? O1 C1 C6 C5 61.3(2) . . . . ? C2 C1 C6 C5 -57.6(2) . . . . ? C5 O5 C7 O3 61.9(2) . . . . ? C5 O5 C7 O1 -63.0(2) . . . . ? C3 O3 C7 O5 -61.3(2) . . . . ? C3 O3 C7 O1 63.9(2) . . . . ? C1 O1 C7 O5 62.2(2) . . . . ? C1 O1 C7 O3 -63.4(2) . . . . ? C2 O2 C8 O7 2.0(3) . . . . ? C2 O2 C8 C9 -176.84(17) . . . . ? O7 C8 C9 C10 -8.4(3) . . . . ? O2 C8 C9 C10 170.40(19) . . . . ? O7 C8 C9 C14 172.7(2) . . . . ? O2 C8 C9 C14 -8.5(3) . . . . ? C14 C9 C10 C11 1.4(3) . . . . ? C8 C9 C10 C11 -177.46(19) . . . . ? C9 C10 C11 C12 -0.8(3) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? C10 C11 C12 Cl1 179.18(17) . . . . ? C11 C12 C13 C14 1.3(4) . . . . ? Cl1 C12 C13 C14 -178.46(17) . . . . ? C12 C13 C14 C9 -0.6(3) . . . . ? C10 C9 C14 C13 -0.7(3) . . . . ? C8 C9 C14 C13 178.1(2) . . . . ? C6 O6 C15 O8 -1.8(3) . . . . ? C6 O6 C15 C16 177.84(18) . . . . ? O8 C15 C16 C17 -20.3(4) . . . . ? O6 C15 C16 C17 160.0(2) . . . . ? O8 C15 C16 C21 159.3(2) . . . . ? O6 C15 C16 C21 -20.4(3) . . . . ? C21 C16 C17 C18 1.2(3) . . . . ? C15 C16 C17 C18 -179.1(2) . . . . ? C16 C17 C18 C19 -0.8(3) . . . . ? C17 C18 C19 C20 -0.5(4) . . . . ? C17 C18 C19 Cl2 179.03(18) . . . . ? C18 C19 C20 C21 1.4(4) . . . . ? Cl2 C19 C20 C21 -178.10(17) . . . . ? C19 C20 C21 C16 -1.0(3) . . . . ? C17 C16 C21 C20 -0.3(3) . . . . ? C15 C16 C21 C20 -179.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C4 H4 Cl1 1.00 2.81 3.640(2) 141.2 4_565 C5 H5 O4 1.00 2.58 3.336(3) 132.3 2_646 C22 H22 O3 1.00 2.53 3.403(3) 145.4 3_667 C11 H11 O1 0.95 2.51 3.385(3) 153.1 1_565 C13 H13 O8 0.95 2.46 3.244(3) 139.9 3_757 O4 H4A O7 0.804(18) 2.004(18) 2.803(2) 172(3) 2_646 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.745 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.057 #===END data_3B _database_code_depnum_ccdc_archive 'CCDC 752184' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate acetone solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate acetone solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, C3 H6 O' _chemical_formula_sum 'C24 H22 Cl2 O9' _chemical_formula_weight 525.32 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 monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.751(2) _cell_length_b 10.2210(18) _cell_length_c 18.520(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.209(3) _cell_angle_gamma 90.00 _cell_volume 2349.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 5299 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.96 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9133 _exptl_absorpt_correction_T_max 0.9693 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11485 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4136 _reflns_number_gt 3812 _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 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^)+(0.0460P)^2^+1.6755P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4136 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 Cl1 Cl 0.04351(4) 1.19425(5) -0.19913(3) 0.02934(15) Uani 1 1 d . . . Cl2 Cl -0.10584(5) 0.72166(7) 0.50210(3) 0.04553(19) Uani 1 1 d . . . O1 O 0.13440(10) 0.44182(13) 0.04011(7) 0.0213(3) Uani 1 1 d . . . O2 O 0.14079(10) 0.72097(12) 0.05419(7) 0.0194(3) Uani 1 1 d . . . O3 O 0.30845(10) 0.52277(13) 0.07657(7) 0.0225(3) Uani 1 1 d . . . O4 O 0.29025(12) 0.58656(14) 0.26608(8) 0.0244(3) Uani 1 1 d . . . O5 O 0.26344(11) 0.32555(13) 0.12489(7) 0.0230(3) Uani 1 1 d . . . O6 O 0.07734(11) 0.48305(13) 0.22285(7) 0.0231(3) Uani 1 1 d . . . O7 O 0.20444(12) 0.88986(13) 0.12898(7) 0.0264(3) Uani 1 1 d . . . O8 O 0.00183(14) 0.29584(15) 0.25074(9) 0.0380(4) Uani 1 1 d . . . C1 C 0.09861(15) 0.51174(18) 0.09778(10) 0.0195(4) Uani 1 1 d . . . H1 H 0.0206 0.5346 0.0809 0.023 Uiso 1 1 calc R . . C2 C 0.16536(15) 0.63534(18) 0.11823(10) 0.0188(4) Uani 1 1 d . . . H2 H 0.1461 0.6789 0.1618 0.023 Uiso 1 1 calc R . . C3 C 0.28432(15) 0.59755(19) 0.13692(10) 0.0192(4) Uani 1 1 d . . . H3 H 0.3302 0.6779 0.1459 0.023 Uiso 1 1 calc R . . C4 C 0.30784(16) 0.51055(19) 0.20570(10) 0.0208(4) Uani 1 1 d . . . H4 H 0.3851 0.4828 0.2163 0.025 Uiso 1 1 calc R . . C5 C 0.23588(16) 0.38885(19) 0.18834(10) 0.0208(4) Uani 1 1 d . . . H5 H 0.2501 0.3282 0.2319 0.025 Uiso 1 1 calc R . . C6 C 0.11566(15) 0.41895(18) 0.16442(10) 0.0200(4) Uani 1 1 d . . . H6 H 0.0745 0.3361 0.1499 0.024 Uiso 1 1 calc R . . C7 C 0.24489(16) 0.40960(19) 0.06298(11) 0.0220(4) Uani 1 1 d . . . H7 H 0.2655 0.3614 0.0213 0.026 Uiso 1 1 calc R . . C8 C 0.16377(15) 0.84837(18) 0.06752(10) 0.0192(4) Uani 1 1 d . . . C9 C 0.13358(15) 0.93060(18) 0.00012(10) 0.0190(4) Uani 1 1 d . . . C10 C 0.14215(15) 1.06640(19) 0.00822(10) 0.0206(4) Uani 1 1 d . . . H10 H 0.1678 1.1034 0.0561 0.025 Uiso 1 1 calc R . . C11 C 0.11349(15) 1.14737(19) -0.05316(11) 0.0221(4) Uani 1 1 d . . . H11 H 0.1186 1.2398 -0.0479 0.027 Uiso 1 1 calc R . . C12 C 0.07732(15) 1.09095(19) -0.12240(11) 0.0215(4) Uani 1 1 d . . . C13 C 0.06802(16) 0.95634(19) -0.13202(11) 0.0236(4) Uani 1 1 d . . . H13 H 0.0429 0.9198 -0.1800 0.028 Uiso 1 1 calc R . . C14 C 0.09619(15) 0.87622(19) -0.06991(11) 0.0218(4) Uani 1 1 d . . . H14 H 0.0899 0.7839 -0.0753 0.026 Uiso 1 1 calc R . . C15 C 0.02338(15) 0.40928(19) 0.26314(11) 0.0221(4) Uani 1 1 d . . . C16 C -0.00593(16) 0.48815(19) 0.32330(11) 0.0225(4) Uani 1 1 d . . . C17 C -0.08729(18) 0.4412(2) 0.35553(12) 0.0312(5) Uani 1 1 d . . . H17 H -0.1214 0.3603 0.3396 0.037 Uiso 1 1 calc R . . C18 C -0.11843(18) 0.5124(2) 0.41082(13) 0.0332(5) Uani 1 1 d . . . H18 H -0.1744 0.4817 0.4326 0.040 Uiso 1 1 calc R . . C19 C -0.06644(17) 0.6290(2) 0.43370(11) 0.0289(5) Uani 1 1 d . . . C20 C 0.01629(17) 0.6755(2) 0.40373(12) 0.0292(5) Uani 1 1 d . . . H20 H 0.0521 0.7548 0.4212 0.035 Uiso 1 1 calc R . . C21 C 0.04609(16) 0.6047(2) 0.34780(11) 0.0240(4) Uani 1 1 d . . . H21 H 0.1021 0.6360 0.3262 0.029 Uiso 1 1 calc R . . C22 C 0.7762(3) 0.4626(4) 0.1315(2) 0.0710(9) Uani 1 1 d . . . H22A H 0.8448 0.5025 0.1283 0.107 Uiso 1 1 calc R . . H22B H 0.7545 0.3984 0.0916 0.107 Uiso 1 1 calc R . . H22C H 0.7845 0.4189 0.1796 0.107 Uiso 1 1 calc R . . C23 C 0.6923(2) 0.5658(3) 0.12417(13) 0.0415(6) Uani 1 1 d . . . O9 O 0.70155(17) 0.66782(19) 0.09459(11) 0.0569(5) Uani 1 1 d . . . C24 C 0.5908(4) 0.5360(4) 0.1472(3) 0.1087(18) Uani 1 1 d . . . H24A H 0.5513 0.4676 0.1150 0.163 Uiso 1 1 calc R . . H24B H 0.5465 0.6151 0.1430 0.163 Uiso 1 1 calc R . . H24C H 0.6077 0.5055 0.1987 0.163 Uiso 1 1 calc R . . H4A H 0.297(2) 0.538(3) 0.3031(15) 0.045(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0386(3) 0.0237(3) 0.0223(3) 0.00688(19) -0.0001(2) -0.0003(2) Cl2 0.0378(3) 0.0658(4) 0.0389(3) -0.0225(3) 0.0210(3) -0.0040(3) O1 0.0236(7) 0.0235(7) 0.0165(7) -0.0029(5) 0.0044(5) 0.0003(6) O2 0.0261(7) 0.0160(7) 0.0155(7) 0.0015(5) 0.0031(5) 0.0012(5) O3 0.0231(7) 0.0260(7) 0.0197(7) -0.0003(6) 0.0080(6) -0.0001(6) O4 0.0363(8) 0.0192(7) 0.0163(7) 0.0002(6) 0.0031(6) -0.0002(6) O5 0.0298(7) 0.0207(7) 0.0191(7) -0.0007(5) 0.0071(6) 0.0051(6) O6 0.0315(8) 0.0190(7) 0.0227(7) -0.0022(5) 0.0143(6) -0.0040(6) O7 0.0399(8) 0.0215(7) 0.0165(7) -0.0008(6) 0.0039(6) -0.0007(6) O8 0.0537(10) 0.0222(8) 0.0480(10) -0.0065(7) 0.0323(8) -0.0097(7) C1 0.0199(9) 0.0207(10) 0.0182(10) -0.0011(8) 0.0051(7) -0.0002(8) C2 0.0235(10) 0.0182(9) 0.0144(9) 0.0028(7) 0.0038(7) 0.0015(8) C3 0.0208(10) 0.0195(10) 0.0175(9) -0.0007(7) 0.0049(7) -0.0009(8) C4 0.0220(10) 0.0214(10) 0.0179(10) 0.0007(8) 0.0026(8) 0.0031(8) C5 0.0282(10) 0.0182(10) 0.0164(9) -0.0009(7) 0.0059(8) 0.0036(8) C6 0.0255(10) 0.0174(9) 0.0187(10) -0.0016(7) 0.0087(8) -0.0021(8) C7 0.0252(10) 0.0226(10) 0.0187(10) -0.0012(8) 0.0058(8) 0.0021(8) C8 0.0189(9) 0.0197(10) 0.0196(10) -0.0008(8) 0.0060(8) 0.0023(8) C9 0.0169(9) 0.0201(10) 0.0202(10) 0.0014(8) 0.0044(7) 0.0014(7) C10 0.0224(10) 0.0208(10) 0.0182(10) -0.0027(8) 0.0041(8) -0.0001(8) C11 0.0244(10) 0.0163(9) 0.0253(10) 0.0001(8) 0.0051(8) -0.0004(8) C12 0.0212(10) 0.0220(10) 0.0209(10) 0.0051(8) 0.0037(8) 0.0010(8) C13 0.0286(11) 0.0233(10) 0.0172(10) -0.0014(8) 0.0017(8) -0.0007(8) C14 0.0257(10) 0.0163(9) 0.0226(10) -0.0011(8) 0.0038(8) 0.0003(8) C15 0.0215(10) 0.0223(11) 0.0242(10) 0.0020(8) 0.0084(8) -0.0017(8) C16 0.0242(10) 0.0221(10) 0.0223(10) 0.0034(8) 0.0078(8) 0.0019(8) C17 0.0332(12) 0.0285(11) 0.0359(12) -0.0014(9) 0.0163(10) -0.0058(9) C18 0.0310(12) 0.0394(13) 0.0351(13) -0.0008(10) 0.0196(10) -0.0036(10) C19 0.0270(11) 0.0384(12) 0.0235(11) -0.0042(9) 0.0106(9) 0.0035(9) C20 0.0268(11) 0.0329(12) 0.0285(11) -0.0071(9) 0.0073(9) -0.0036(9) C21 0.0210(10) 0.0284(11) 0.0243(10) 0.0006(8) 0.0087(8) -0.0018(8) C22 0.058(2) 0.075(2) 0.074(2) 0.0037(18) 0.0018(16) 0.0150(17) C23 0.0508(15) 0.0428(15) 0.0356(13) -0.0038(11) 0.0196(11) -0.0051(12) O9 0.0743(14) 0.0449(11) 0.0658(13) -0.0009(10) 0.0457(11) -0.0043(10) C24 0.111(3) 0.062(2) 0.189(5) 0.015(3) 0.110(4) -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 Cl1 C12 1.7436(19) . ? Cl2 C19 1.745(2) . ? O1 C7 1.414(2) . ? O1 C1 1.443(2) . ? O2 C8 1.345(2) . ? O2 C2 1.449(2) . ? O3 C7 1.402(2) . ? O3 C3 1.444(2) . ? O4 C4 1.421(2) . ? O4 H4A 0.84(3) . ? O5 C7 1.409(2) . ? O5 C5 1.453(2) . ? O6 C15 1.354(2) . ? O6 C6 1.442(2) . ? O7 C8 1.214(2) . ? O8 C15 1.201(2) . ? C1 C2 1.522(3) . ? C1 C6 1.532(3) . ? C1 H1 1.0000 . ? C2 C3 1.526(3) . ? C2 H2 1.0000 . ? C3 C4 1.526(3) . ? C3 H3 1.0000 . ? C4 C5 1.535(3) . ? C4 H4 1.0000 . ? C5 C6 1.526(3) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.481(3) . ? C9 C14 1.391(3) . ? C9 C10 1.398(3) . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.385(3) . ? C11 H11 0.9500 . ? C12 C13 1.389(3) . ? C13 C14 1.391(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.490(3) . ? C16 C21 1.389(3) . ? C16 C17 1.395(3) . ? C17 C18 1.386(3) . ? C17 H17 0.9500 . ? C18 C19 1.382(3) . ? C18 H18 0.9500 . ? C19 C20 1.384(3) . ? C20 C21 1.386(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.486(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 O9 1.197(3) . ? C23 C24 1.483(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 110.82(14) . . ? C8 O2 C2 115.92(14) . . ? C7 O3 C3 111.04(14) . . ? C4 O4 H4A 108.2(19) . . ? C7 O5 C5 111.09(14) . . ? C15 O6 C6 117.54(15) . . ? O1 C1 C2 109.99(15) . . ? O1 C1 C6 106.20(15) . . ? C2 C1 C6 110.18(15) . . ? O1 C1 H1 110.1 . . ? C2 C1 H1 110.1 . . ? C6 C1 H1 110.1 . . ? O2 C2 C1 107.07(14) . . ? O2 C2 C3 110.87(15) . . ? C1 C2 C3 108.45(15) . . ? O2 C2 H2 110.1 . . ? C1 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? O3 C3 C4 107.56(15) . . ? O3 C3 C2 109.56(14) . . ? C4 C3 C2 109.41(15) . . ? O3 C3 H3 110.1 . . ? C4 C3 H3 110.1 . . ? C2 C3 H3 110.1 . . ? O4 C4 C3 107.58(15) . . ? O4 C4 C5 114.43(15) . . ? C3 C4 C5 107.65(15) . . ? O4 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? O5 C5 C6 105.52(14) . . ? O5 C5 C4 106.66(15) . . ? C6 C5 C4 114.20(16) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 111.33(15) . . ? O6 C6 C1 108.25(15) . . ? C5 C6 C1 107.86(15) . . ? O6 C6 H6 109.8 . . ? C5 C6 H6 109.8 . . ? C1 C6 H6 109.8 . . ? O3 C7 O5 112.00(15) . . ? O3 C7 O1 110.93(15) . . ? O5 C7 O1 110.87(15) . . ? O3 C7 H7 107.6 . . ? O5 C7 H7 107.6 . . ? O1 C7 H7 107.6 . . ? O7 C8 O2 122.58(17) . . ? O7 C8 C9 124.40(17) . . ? O2 C8 C9 113.02(16) . . ? C14 C9 C10 119.90(17) . . ? C14 C9 C8 121.78(17) . . ? C10 C9 C8 118.31(17) . . ? C11 C10 C9 120.37(17) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 118.70(18) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 122.12(18) . . ? C11 C12 Cl1 118.06(15) . . ? C13 C12 Cl1 119.82(15) . . ? C12 C13 C14 118.61(18) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C13 C14 C9 120.30(18) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? O8 C15 O6 123.70(18) . . ? O8 C15 C16 125.41(18) . . ? O6 C15 C16 110.89(16) . . ? C21 C16 C17 120.11(19) . . ? C21 C16 C15 121.72(18) . . ? C17 C16 C15 118.16(18) . . ? C18 C17 C16 120.1(2) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 118.7(2) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C18 C19 C20 122.0(2) . . ? C18 C19 Cl2 119.54(16) . . ? C20 C19 Cl2 118.45(17) . . ? C19 C20 C21 119.0(2) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C16 120.02(19) . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O9 C23 C24 119.6(3) . . ? O9 C23 C22 121.1(3) . . ? C24 C23 C22 119.0(3) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 58.04(19) . . . . ? C7 O1 C1 C6 -61.17(18) . . . . ? C8 O2 C2 C1 159.79(15) . . . . ? C8 O2 C2 C3 -82.08(19) . . . . ? O1 C1 C2 O2 66.30(18) . . . . ? C6 C1 C2 O2 -176.96(14) . . . . ? O1 C1 C2 C3 -53.39(19) . . . . ? C6 C1 C2 C3 63.35(19) . . . . ? C7 O3 C3 C4 60.06(18) . . . . ? C7 O3 C3 C2 -58.78(19) . . . . ? O2 C2 C3 O3 -63.81(19) . . . . ? C1 C2 C3 O3 53.47(19) . . . . ? O2 C2 C3 C4 178.50(14) . . . . ? C1 C2 C3 C4 -64.22(19) . . . . ? O3 C3 C4 O4 176.60(14) . . . . ? C2 C3 C4 O4 -64.46(19) . . . . ? O3 C3 C4 C5 -59.61(18) . . . . ? C2 C3 C4 C5 59.32(19) . . . . ? C7 O5 C5 C6 61.71(18) . . . . ? C7 O5 C5 C4 -60.10(18) . . . . ? O4 C4 C5 O5 178.92(14) . . . . ? C3 C4 C5 O5 59.40(18) . . . . ? O4 C4 C5 C6 62.8(2) . . . . ? C3 C4 C5 C6 -56.7(2) . . . . ? C15 O6 C6 C5 -101.36(19) . . . . ? C15 O6 C6 C1 140.25(16) . . . . ? O5 C5 C6 O6 -179.82(14) . . . . ? C4 C5 C6 O6 -63.0(2) . . . . ? O5 C5 C6 C1 -61.20(18) . . . . ? C4 C5 C6 C1 55.6(2) . . . . ? O1 C1 C6 O6 -177.99(14) . . . . ? C2 C1 C6 O6 62.93(19) . . . . ? O1 C1 C6 C5 61.44(18) . . . . ? C2 C1 C6 C5 -57.65(19) . . . . ? C3 O3 C7 O5 -61.28(19) . . . . ? C3 O3 C7 O1 63.18(18) . . . . ? C5 O5 C7 O3 61.66(19) . . . . ? C5 O5 C7 O1 -62.83(19) . . . . ? C1 O1 C7 O3 -62.67(18) . . . . ? C1 O1 C7 O5 62.43(19) . . . . ? C2 O2 C8 O7 1.3(3) . . . . ? C2 O2 C8 C9 -178.24(14) . . . . ? O7 C8 C9 C14 174.12(19) . . . . ? O2 C8 C9 C14 -6.4(3) . . . . ? O7 C8 C9 C10 -6.7(3) . . . . ? O2 C8 C9 C10 172.87(16) . . . . ? C14 C9 C10 C11 0.1(3) . . . . ? C8 C9 C10 C11 -179.17(17) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C10 C11 C12 Cl1 -179.07(15) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? Cl1 C12 C13 C14 179.59(15) . . . . ? C12 C13 C14 C9 -0.5(3) . . . . ? C10 C9 C14 C13 0.5(3) . . . . ? C8 C9 C14 C13 179.68(18) . . . . ? C6 O6 C15 O8 -3.4(3) . . . . ? C6 O6 C15 C16 177.25(15) . . . . ? O8 C15 C16 C21 161.4(2) . . . . ? O6 C15 C16 C21 -19.3(3) . . . . ? O8 C15 C16 C17 -18.0(3) . . . . ? O6 C15 C16 C17 161.33(18) . . . . ? C21 C16 C17 C18 1.7(3) . . . . ? C15 C16 C17 C18 -178.9(2) . . . . ? C16 C17 C18 C19 -0.9(3) . . . . ? C17 C18 C19 C20 -0.8(3) . . . . ? C17 C18 C19 Cl2 178.91(18) . . . . ? C18 C19 C20 C21 1.6(3) . . . . ? Cl2 C19 C20 C21 -178.08(16) . . . . ? C19 C20 C21 C16 -0.8(3) . . . . ? C17 C16 C21 C20 -0.8(3) . . . . ? C15 C16 C21 C20 179.79(19) . . . . ? 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 C5 H5 O7 1.00 2.59 3.294(2) 127.6 2_545 C13 H13 O8 0.95 2.56 3.373(3) 143.6 3_565 C5 H5 O4 1.00 2.53 3.240(2) 128.2 2_545 C7 H7 O9 1.00 2.30 3.243(3) 157.0 3_665 O4 H4A O7 0.84(3) 1.97(3) 2.786(2) 165(3) 2_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.425 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.050 #===END data_3CF _database_code_depnum_ccdc_archive 'CCDC 752185' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate dichloromethane solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate dichloromethane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, C H2 Cl2' _chemical_formula_sum 'C22 H18 Cl4 O8' _chemical_formula_weight 552.16 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8921(11) _cell_length_b 10.1356(9) _cell_length_c 18.0788(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.5840(10) _cell_angle_gamma 90.00 _cell_volume 2314.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 9387 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.28 _exptl_crystal_description 'thick plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.559 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7731 _exptl_absorpt_correction_T_max 0.9462 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 16329 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4073 _reflns_number_gt 3780 _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 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^)+(0.0483P)^2^+3.3756P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4073 _refine_ls_number_parameters 338 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.030 _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 Cl1 Cl 0.95985(5) 0.69575(6) 1.20902(3) 0.03203(17) Uani 1 1 d . . . Cl2 Cl 1.10628(5) 0.18701(7) 0.48992(3) 0.03550(18) Uani 1 1 d . . . O1 O 0.85750(12) -0.05676(15) 0.96780(8) 0.0224(3) Uani 1 1 d . . . O2 O 0.86069(12) 0.22331(14) 0.95008(8) 0.0204(3) Uani 1 1 d . . . O3 O 0.69007(12) 0.03517(15) 0.93473(9) 0.0233(3) Uani 1 1 d . . . O4 O 0.70332(13) 0.08750(16) 0.73851(9) 0.0253(4) Uani 1 1 d . . . O5 O 0.72440(13) -0.16905(15) 0.88601(9) 0.0248(4) Uani 1 1 d . . . O6 O 0.90669(13) -0.03075(15) 0.77617(9) 0.0248(4) Uani 1 1 d . . . O7 O 0.80621(13) 0.39427(16) 0.87317(8) 0.0257(4) Uani 1 1 d . . . O8 O 1.03548(19) -0.1803(2) 0.78451(14) 0.0648(8) Uani 1 1 d . . . C1 C 0.89362(17) 0.0075(2) 0.90632(12) 0.0202(4) Uani 1 1 d . . . H1 H 0.9713 0.0258 0.9207 0.024 Uiso 1 1 calc R . . C2 C 0.83265(17) 0.1357(2) 0.88598(11) 0.0189(4) Uani 1 1 d . . . H2 H 0.8523 0.1763 0.8403 0.023 Uiso 1 1 calc R . . C3 C 0.71488(17) 0.1046(2) 0.87077(12) 0.0205(4) Uani 1 1 d . . . H3 H 0.6731 0.1883 0.8622 0.025 Uiso 1 1 calc R . . C4 C 0.68557(18) 0.0153(2) 0.80184(12) 0.0217(5) Uani 1 1 d . . . H4 H 0.6088 -0.0080 0.7943 0.026 Uiso 1 1 calc R . . C5 C 0.75195(18) -0.1110(2) 0.81913(12) 0.0224(5) Uani 1 1 d . . . H5 H 0.7347 -0.1737 0.7757 0.027 Uiso 1 1 calc R . . C6 C 0.87095(18) -0.0873(2) 0.83933(12) 0.0216(5) Uani 1 1 d . . . H6 H 0.9084 -0.1728 0.8535 0.026 Uiso 1 1 calc R . . C7 C 0.74791(18) -0.0822(2) 0.94782(12) 0.0229(5) Uani 1 1 d . . . H7 H 0.7267 -0.1270 0.9918 0.027 Uiso 1 1 calc R . . C8 C 0.84207(17) 0.3525(2) 0.93588(12) 0.0196(5) Uani 1 1 d . . . C9 C 0.87035(16) 0.4350(2) 1.00471(12) 0.0191(4) Uani 1 1 d . . . C10 C 0.86522(17) 0.5719(2) 0.99676(12) 0.0215(5) Uani 1 1 d . . . H10 H 0.8424 0.6100 0.9482 0.026 Uiso 1 1 calc R . . C11 C 0.89339(17) 0.6523(2) 1.05965(13) 0.0229(5) Uani 1 1 d . . . H11 H 0.8914 0.7456 1.0545 0.027 Uiso 1 1 calc R . . C12 C 0.92446(17) 0.5945(2) 1.13002(12) 0.0227(5) Uani 1 1 d . . . C13 C 0.92865(18) 0.4588(2) 1.13938(13) 0.0244(5) Uani 1 1 d . . . H13 H 0.9496 0.4212 1.1882 0.029 Uiso 1 1 calc R . . C14 C 0.90174(17) 0.3791(2) 1.07626(12) 0.0221(5) Uani 1 1 d . . . H14 H 0.9046 0.2859 1.0817 0.026 Uiso 1 1 calc R . . C15 C 0.98841(19) -0.0879(2) 0.75316(14) 0.0273(5) Uani 1 1 d . . . C16 C 1.01446(18) -0.0191(2) 0.68671(13) 0.0234(5) Uani 1 1 d . . . C17 C 1.1033(2) -0.0603(3) 0.66037(14) 0.0317(6) Uani 1 1 d . . . H17 H 1.1445 -0.1318 0.6843 0.038 Uiso 1 1 calc R . . C18 C 1.13190(19) 0.0022(3) 0.59953(14) 0.0306(5) Uani 1 1 d . . . H18 H 1.1925 -0.0256 0.5813 0.037 Uiso 1 1 calc R . . C19 C 1.07065(18) 0.1059(2) 0.56572(13) 0.0253(5) Uani 1 1 d . . . C20 C 0.98164(19) 0.1477(2) 0.59066(13) 0.0270(5) Uani 1 1 d . . . H20 H 0.9405 0.2191 0.5664 0.032 Uiso 1 1 calc R . . C21 C 0.95309(18) 0.0843(2) 0.65140(12) 0.0233(5) Uani 1 1 d . . . H21 H 0.8917 0.1115 0.6689 0.028 Uiso 1 1 calc R . . H4A H 0.699(3) 0.037(3) 0.7036(19) 0.047(9) Uiso 1 1 d . . . C22 C 0.6862(4) 0.0512(5) 0.1277(3) 0.0465(10) Uani 0.75 1 d PD A 1 H22A H 0.6909 0.1154 0.1695 0.056 Uiso 0.75 1 calc PR A 1 H22B H 0.7067 0.0972 0.0845 0.056 Uiso 0.75 1 calc PR A 1 Cl3 Cl 0.77524(9) -0.08058(12) 0.15687(6) 0.0586(3) Uani 0.75 1 d PD A 1 Cl4 Cl 0.55690(10) -0.00439(14) 0.10139(7) 0.0576(3) Uani 0.75 1 d PD A 1 C22' C 0.6152(12) 0.0462(12) 0.1109(8) 0.053(4) Uani 0.25 1 d PD B 2 H22C H 0.5993 0.0553 0.0552 0.063 Uiso 0.25 1 calc PR B 2 H22D H 0.5638 0.1014 0.1310 0.063 Uiso 0.25 1 calc PR B 2 Cl3' Cl 0.7396(4) 0.1036(5) 0.1451(3) 0.0878(15) Uani 0.25 1 d PD B 2 Cl4' Cl 0.5981(4) -0.1167(4) 0.1340(3) 0.0964(16) Uani 0.25 1 d PD B 2 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 Cl1 0.0431(4) 0.0247(3) 0.0246(3) -0.0071(2) -0.0020(2) -0.0013(2) Cl2 0.0369(3) 0.0420(4) 0.0318(3) 0.0127(3) 0.0168(3) 0.0007(3) O1 0.0265(8) 0.0240(8) 0.0172(8) 0.0044(6) 0.0056(6) -0.0004(6) O2 0.0271(8) 0.0164(7) 0.0167(7) -0.0008(6) 0.0015(6) -0.0021(6) O3 0.0258(8) 0.0249(8) 0.0211(8) -0.0006(6) 0.0095(6) -0.0001(6) O4 0.0376(9) 0.0205(8) 0.0161(8) -0.0006(7) 0.0016(7) 0.0003(7) O5 0.0338(9) 0.0195(8) 0.0226(8) -0.0004(6) 0.0095(7) -0.0062(7) O6 0.0349(9) 0.0210(8) 0.0223(8) 0.0049(6) 0.0146(7) 0.0066(7) O7 0.0366(9) 0.0219(8) 0.0173(8) 0.0023(6) 0.0026(7) 0.0003(7) O8 0.0737(16) 0.0620(15) 0.0748(16) 0.0486(13) 0.0537(13) 0.0453(13) C1 0.0227(11) 0.0208(11) 0.0180(10) 0.0030(9) 0.0060(8) 0.0002(9) C2 0.0237(11) 0.0181(11) 0.0145(10) -0.0012(8) 0.0028(8) -0.0022(8) C3 0.0234(11) 0.0194(11) 0.0185(10) 0.0002(9) 0.0041(9) 0.0008(9) C4 0.0239(11) 0.0211(11) 0.0194(11) -0.0013(9) 0.0024(9) -0.0030(9) C5 0.0325(12) 0.0175(11) 0.0182(10) -0.0014(9) 0.0076(9) -0.0035(9) C6 0.0297(12) 0.0174(11) 0.0198(11) 0.0037(9) 0.0099(9) 0.0028(9) C7 0.0264(11) 0.0237(12) 0.0202(11) 0.0018(9) 0.0085(9) -0.0034(9) C8 0.0195(10) 0.0188(11) 0.0210(11) 0.0022(9) 0.0050(9) -0.0014(8) C9 0.0178(10) 0.0186(11) 0.0208(11) 0.0002(9) 0.0033(8) -0.0018(8) C10 0.0233(11) 0.0207(11) 0.0204(11) 0.0029(9) 0.0038(9) -0.0008(9) C11 0.0259(11) 0.0158(10) 0.0268(12) 0.0008(9) 0.0049(9) -0.0011(9) C12 0.0226(11) 0.0218(11) 0.0225(11) -0.0048(9) 0.0019(9) -0.0019(9) C13 0.0281(12) 0.0227(11) 0.0203(11) 0.0010(9) -0.0003(9) 0.0008(9) C14 0.0250(11) 0.0163(10) 0.0238(11) 0.0007(9) 0.0022(9) -0.0007(9) C15 0.0302(12) 0.0251(12) 0.0290(12) 0.0050(10) 0.0118(10) 0.0065(10) C16 0.0273(12) 0.0223(11) 0.0220(11) -0.0001(9) 0.0081(9) 0.0002(9) C17 0.0302(13) 0.0344(14) 0.0327(13) 0.0096(11) 0.0111(11) 0.0102(11) C18 0.0264(12) 0.0373(14) 0.0315(13) 0.0049(11) 0.0143(10) 0.0053(10) C19 0.0276(12) 0.0287(12) 0.0212(11) 0.0019(10) 0.0083(9) -0.0050(10) C20 0.0296(12) 0.0253(12) 0.0268(12) 0.0054(10) 0.0077(10) 0.0041(10) C21 0.0249(11) 0.0239(12) 0.0228(11) -0.0009(9) 0.0087(9) 0.0024(9) C22 0.036(3) 0.042(2) 0.059(3) -0.010(2) 0.003(2) -0.001(2) Cl3 0.0556(6) 0.0696(7) 0.0455(6) -0.0053(5) -0.0019(5) 0.0256(5) Cl4 0.0394(6) 0.0695(8) 0.0631(7) 0.0024(6) 0.0084(5) -0.0023(6) C22' 0.041(9) 0.053(8) 0.059(9) -0.002(6) 0.000(7) -0.032(7) Cl3' 0.087(3) 0.106(4) 0.063(2) 0.027(2) -0.004(2) -0.043(3) Cl4' 0.078(3) 0.051(2) 0.147(5) 0.017(3) -0.009(3) -0.016(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 Cl1 C12 1.744(2) . ? Cl2 C19 1.737(2) . ? O1 C7 1.410(3) . ? O1 C1 1.444(3) . ? O2 C8 1.347(3) . ? O2 C2 1.447(2) . ? O3 C7 1.399(3) . ? O3 C3 1.443(3) . ? O4 C4 1.416(3) . ? O4 H4A 0.81(3) . ? O5 C7 1.407(3) . ? O5 C5 1.451(3) . ? O6 C15 1.340(3) . ? O6 C6 1.434(3) . ? O7 C8 1.211(3) . ? O8 C15 1.195(3) . ? C1 C2 1.526(3) . ? C1 C6 1.527(3) . ? C1 H1 1.0000 . ? C2 C3 1.521(3) . ? C2 H2 1.0000 . ? C3 C4 1.525(3) . ? C3 H3 1.0000 . ? C4 C5 1.536(3) . ? C4 H4 1.0000 . ? C5 C6 1.523(3) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.483(3) . ? C9 C10 1.395(3) . ? C9 C14 1.396(3) . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.385(3) . ? C11 H11 0.9500 . ? C12 C13 1.385(3) . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.485(3) . ? C16 C21 1.389(3) . ? C16 C17 1.390(3) . ? C17 C18 1.382(3) . ? C17 H17 0.9500 . ? C18 C19 1.381(3) . ? C18 H18 0.9500 . ? C19 C20 1.381(3) . ? C20 C21 1.385(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 Cl4 1.733(6) . ? C22 Cl3 1.771(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22' Cl3' 1.702(14) . ? C22' Cl4' 1.728(11) . ? C22' H22C 0.9900 . ? C22' H22D 0.9900 . ? 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 110.29(16) . . ? C8 O2 C2 115.94(16) . . ? C7 O3 C3 110.72(16) . . ? C4 O4 H4A 108(2) . . ? C7 O5 C5 111.01(16) . . ? C15 O6 C6 118.22(17) . . ? O1 C1 C2 109.86(17) . . ? O1 C1 C6 106.68(17) . . ? C2 C1 C6 109.73(17) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C3 110.61(17) . . ? O2 C2 C1 107.22(16) . . ? C3 C2 C1 108.30(18) . . ? O2 C2 H2 110.2 . . ? C3 C2 H2 110.2 . . ? C1 C2 H2 110.2 . . ? O3 C3 C2 109.28(17) . . ? O3 C3 C4 107.87(17) . . ? C2 C3 C4 110.22(17) . . ? O3 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? O4 C4 C3 107.46(18) . . ? O4 C4 C5 114.92(18) . . ? C3 C4 C5 106.96(17) . . ? O4 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? O5 C5 C6 105.51(17) . . ? O5 C5 C4 106.71(17) . . ? C6 C5 C4 114.24(18) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 109.96(18) . . ? O6 C6 C1 109.82(17) . . ? C5 C6 C1 108.21(17) . . ? O6 C6 H6 109.6 . . ? C5 C6 H6 109.6 . . ? C1 C6 H6 109.6 . . ? O3 C7 O5 112.03(18) . . ? O3 C7 O1 111.11(18) . . ? O5 C7 O1 111.29(17) . . ? O3 C7 H7 107.4 . . ? O5 C7 H7 107.4 . . ? O1 C7 H7 107.4 . . ? O7 C8 O2 122.6(2) . . ? O7 C8 C9 124.9(2) . . ? O2 C8 C9 112.57(18) . . ? C10 C9 C14 119.9(2) . . ? C10 C9 C8 118.41(19) . . ? C14 C9 C8 121.73(19) . . ? C11 C10 C9 120.1(2) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 119.0(2) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 121.9(2) . . ? C11 C12 Cl1 118.91(17) . . ? C13 C12 Cl1 119.15(18) . . ? C14 C13 C12 118.8(2) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C9 120.4(2) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? O8 C15 O6 123.2(2) . . ? O8 C15 C16 125.2(2) . . ? O6 C15 C16 111.59(19) . . ? C21 C16 C17 120.1(2) . . ? C21 C16 C15 121.7(2) . . ? C17 C16 C15 118.2(2) . . ? C18 C17 C16 120.3(2) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 118.7(2) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C20 C19 C18 121.8(2) . . ? C20 C19 Cl2 118.76(18) . . ? C18 C19 Cl2 119.40(18) . . ? C19 C20 C21 119.2(2) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C20 C21 C16 119.8(2) . . ? C20 C21 H21 120.1 . . ? C16 C21 H21 120.1 . . ? Cl4 C22 Cl3 111.5(3) . . ? Cl4 C22 H22A 109.3 . . ? Cl3 C22 H22A 109.3 . . ? Cl4 C22 H22B 109.3 . . ? Cl3 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? Cl3' C22' Cl4' 113.3(9) . . ? Cl3' C22' H22C 108.9 . . ? Cl4' C22' H22C 108.9 . . ? Cl3' C22' H22D 108.9 . . ? Cl4' C22' H22D 108.9 . . ? H22C C22' H22D 107.7 . . ? 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 58.2(2) . . . . ? C7 O1 C1 C6 -60.7(2) . . . . ? C8 O2 C2 C3 -81.8(2) . . . . ? C8 O2 C2 C1 160.30(17) . . . . ? O1 C1 C2 O2 65.4(2) . . . . ? C6 C1 C2 O2 -177.57(16) . . . . ? O1 C1 C2 C3 -53.9(2) . . . . ? C6 C1 C2 C3 63.0(2) . . . . ? C7 O3 C3 C2 -59.4(2) . . . . ? C7 O3 C3 C4 60.4(2) . . . . ? O2 C2 C3 O3 -63.2(2) . . . . ? C1 C2 C3 O3 54.1(2) . . . . ? O2 C2 C3 C4 178.47(16) . . . . ? C1 C2 C3 C4 -64.3(2) . . . . ? O3 C3 C4 O4 176.06(16) . . . . ? C2 C3 C4 O4 -64.7(2) . . . . ? O3 C3 C4 C5 -60.0(2) . . . . ? C2 C3 C4 C5 59.2(2) . . . . ? C7 O5 C5 C6 61.4(2) . . . . ? C7 O5 C5 C4 -60.5(2) . . . . ? O4 C4 C5 O5 178.90(17) . . . . ? C3 C4 C5 O5 59.7(2) . . . . ? O4 C4 C5 C6 62.7(2) . . . . ? C3 C4 C5 C6 -56.5(2) . . . . ? C15 O6 C6 C5 -128.3(2) . . . . ? C15 O6 C6 C1 112.8(2) . . . . ? O5 C5 C6 O6 179.45(16) . . . . ? C4 C5 C6 O6 -63.7(2) . . . . ? O5 C5 C6 C1 -60.6(2) . . . . ? C4 C5 C6 C1 56.3(2) . . . . ? O1 C1 C6 O6 -178.97(16) . . . . ? C2 C1 C6 O6 62.1(2) . . . . ? O1 C1 C6 C5 61.0(2) . . . . ? C2 C1 C6 C5 -58.0(2) . . . . ? C3 O3 C7 O5 -61.2(2) . . . . ? C3 O3 C7 O1 63.9(2) . . . . ? C5 O5 C7 O3 61.8(2) . . . . ? C5 O5 C7 O1 -63.3(2) . . . . ? C1 O1 C7 O3 -63.1(2) . . . . ? C1 O1 C7 O5 62.4(2) . . . . ? C2 O2 C8 O7 -1.6(3) . . . . ? C2 O2 C8 C9 178.53(16) . . . . ? O7 C8 C9 C10 -6.4(3) . . . . ? O2 C8 C9 C10 173.54(19) . . . . ? O7 C8 C9 C14 173.7(2) . . . . ? O2 C8 C9 C14 -6.3(3) . . . . ? C14 C9 C10 C11 1.4(3) . . . . ? C8 C9 C10 C11 -178.54(19) . . . . ? C9 C10 C11 C12 -1.2(3) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? C10 C11 C12 Cl1 179.99(17) . . . . ? C11 C12 C13 C14 0.5(4) . . . . ? Cl1 C12 C13 C14 -179.18(17) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? C10 C9 C14 C13 -0.5(3) . . . . ? C8 C9 C14 C13 179.4(2) . . . . ? C6 O6 C15 O8 -3.1(4) . . . . ? C6 O6 C15 C16 179.07(19) . . . . ? O8 C15 C16 C21 177.2(3) . . . . ? O6 C15 C16 C21 -5.0(3) . . . . ? O8 C15 C16 C17 -3.2(4) . . . . ? O6 C15 C16 C17 174.6(2) . . . . ? C21 C16 C17 C18 0.8(4) . . . . ? C15 C16 C17 C18 -178.8(2) . . . . ? C16 C17 C18 C19 0.0(4) . . . . ? C17 C18 C19 C20 -0.5(4) . . . . ? C17 C18 C19 Cl2 179.2(2) . . . . ? C18 C19 C20 C21 0.2(4) . . . . ? Cl2 C19 C20 C21 -179.53(18) . . . . ? C19 C20 C21 C16 0.6(4) . . . . ? C17 C16 C21 C20 -1.1(4) . . . . ? C15 C16 C21 C20 178.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H13 O8 0.95 2.49 3.133(3) 125.0 3_757 C11 H11 O1 0.95 2.53 3.371(3) 147.9 1_565 C5 H5 O4 1.00 2.58 3.316(3) 130.6 2_646 C17 H17 Cl4' 0.95 2.73 3.307(5) 119.6 4_656 O4 H4A O7 0.81(3) 1.99(4) 2.798(2) 173(3) 2_646 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.075 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.061 #===END data_3D _database_code_depnum_ccdc_archive 'CCDC 752186' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate nitromethane solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate nitromethane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, C H3 N O2' _chemical_formula_sum 'C22 H19 Cl2 N O10' _chemical_formula_weight 528.28 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6835(7) _cell_length_b 10.0712(5) _cell_length_c 18.2980(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.1000(10) _cell_angle_gamma 90.00 _cell_volume 2276.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 8905 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.22 _exptl_crystal_description 'thick square plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.345 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8742 _exptl_absorpt_correction_T_max 0.9373 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11138 _diffrn_reflns_av_R_equivalents 0.0122 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3999 _reflns_number_gt 3767 _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 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^)+(0.0442P)^2^+1.1303P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3999 _refine_ls_number_parameters 358 _refine_ls_number_restraints 149 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.044 _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 Cl1 Cl 0.45285(3) 0.69768(4) 1.20921(2) 0.02975(12) Uani 1 1 d . . . Cl2 Cl 0.59188(3) 0.18752(4) 0.48572(2) 0.03152(12) Uani 1 1 d . . . O1 O 0.36156(8) -0.05638(10) 0.96434(5) 0.0212(2) Uani 1 1 d . . . O2 O 0.36181(8) 0.22531(9) 0.94891(5) 0.0199(2) Uani 1 1 d . . . O3 O 0.18895(8) 0.03446(10) 0.93172(5) 0.0223(2) Uani 1 1 d . . . O4 O 0.19541(8) 0.09208(10) 0.73720(6) 0.0226(2) Uani 1 1 d D . . O5 O 0.22429(8) -0.16905(10) 0.88220(5) 0.0225(2) Uani 1 1 d . . . O6 O 0.40297(8) -0.02852(10) 0.77261(5) 0.0211(2) Uani 1 1 d . . . O7 O 0.30614(8) 0.39905(10) 0.87313(5) 0.0248(2) Uani 1 1 d . . . O8 O 0.56838(10) -0.12105(14) 0.80802(7) 0.0424(3) Uani 1 1 d . . . C1 C 0.39612(11) 0.01052(14) 0.90380(7) 0.0192(3) Uani 1 1 d . . . H1 H 0.4754 0.0299 0.9185 0.023 Uiso 1 1 calc R . . C2 C 0.33231(11) 0.13871(14) 0.88440(7) 0.0185(3) Uani 1 1 d . . . H2 H 0.3505 0.1814 0.8395 0.022 Uiso 1 1 calc R . . C3 C 0.21185(11) 0.10638(14) 0.86882(7) 0.0194(3) Uani 1 1 d . . . H3 H 0.1686 0.1902 0.8606 0.023 Uiso 1 1 calc R . . C4 C 0.18078(11) 0.01766(14) 0.79977(8) 0.0198(3) Uani 1 1 d . . . H4 H 0.1026 -0.0069 0.7920 0.024 Uiso 1 1 calc R . . C5 C 0.24955(12) -0.10889(14) 0.81605(8) 0.0199(3) Uani 1 1 d . . . H5 H 0.2307 -0.1712 0.7725 0.024 Uiso 1 1 calc R . . C6 C 0.37167(11) -0.08445(13) 0.83664(8) 0.0193(3) Uani 1 1 d . . . H6 H 0.4105 -0.1704 0.8506 0.023 Uiso 1 1 calc R . . C7 C 0.24974(12) -0.08312(14) 0.94429(8) 0.0223(3) Uani 1 1 d . . . H7 H 0.2302 -0.1297 0.9876 0.027 Uiso 1 1 calc R . . C8 C 0.34232(11) 0.35532(14) 0.93547(8) 0.0188(3) Uani 1 1 d . . . C9 C 0.37018(11) 0.43666(14) 1.00478(8) 0.0183(3) Uani 1 1 d . . . C10 C 0.36256(11) 0.57456(14) 0.99746(8) 0.0207(3) Uani 1 1 d . . . H10 H 0.3392 0.6136 0.9492 0.025 Uiso 1 1 calc R . . C11 C 0.38915(11) 0.65437(14) 1.06063(8) 0.0222(3) Uani 1 1 d . . . H11 H 0.3853 0.7483 1.0561 0.027 Uiso 1 1 calc R . . C12 C 0.42150(11) 0.59505(14) 1.13053(8) 0.0214(3) Uani 1 1 d . . . C13 C 0.42887(11) 0.45827(15) 1.13925(8) 0.0222(3) Uani 1 1 d . . . H13 H 0.4509 0.4197 1.1877 0.027 Uiso 1 1 calc R . . C14 C 0.40318(11) 0.37894(14) 1.07540(8) 0.0203(3) Uani 1 1 d . . . H14 H 0.4082 0.2851 1.0800 0.024 Uiso 1 1 calc R . . C15 C 0.50306(12) -0.05747(15) 0.76340(8) 0.0249(3) Uani 1 1 d . . . C16 C 0.52169(12) 0.00179(14) 0.69298(8) 0.0222(3) Uani 1 1 d . . . C17 C 0.61612(13) -0.03120(17) 0.67030(9) 0.0299(4) Uani 1 1 d . . . H17 H 0.6662 -0.0917 0.6993 0.036 Uiso 1 1 calc R . . C18 C 0.63732(13) 0.02362(17) 0.60590(9) 0.0292(3) Uani 1 1 d . . . H18 H 0.7009 0.0001 0.5898 0.035 Uiso 1 1 calc R . . C19 C 0.56425(12) 0.11338(15) 0.56532(8) 0.0238(3) Uani 1 1 d . . . C20 C 0.46971(12) 0.14660(15) 0.58635(8) 0.0252(3) Uani 1 1 d . . . H20 H 0.4202 0.2077 0.5573 0.030 Uiso 1 1 calc R . . C21 C 0.44793(12) 0.08974(14) 0.65032(8) 0.0230(3) Uani 1 1 d . . . H21 H 0.3827 0.1108 0.6650 0.028 Uiso 1 1 calc R . . C22 C 0.6055(11) 0.4656(14) 0.6045(8) 0.059(3) Uani 0.25 1 d PDU A 1 H22A H 0.5357 0.4570 0.6187 0.089 Uiso 0.25 1 calc PR A 1 H22B H 0.6489 0.3858 0.6200 0.089 Uiso 0.25 1 calc PR A 1 H22C H 0.5931 0.4762 0.5500 0.089 Uiso 0.25 1 calc PR A 1 N1 N 0.6654(13) 0.5867(19) 0.6432(13) 0.062(3) Uani 0.25 1 d PDU A 1 O9 O 0.7121(17) 0.661(2) 0.6169(14) 0.060(4) Uani 0.25 1 d PDU A 1 O10 O 0.6498(9) 0.6120(9) 0.7063(5) 0.086(2) Uani 0.25 1 d PDU A 1 C22' C 0.6591(4) 0.4507(5) 0.6221(3) 0.0610(11) Uani 0.75 1 d PDU B 2 H22D H 0.7359 0.4327 0.6434 0.091 Uiso 0.75 1 calc PR B 2 H22E H 0.6425 0.4328 0.5680 0.091 Uiso 0.75 1 calc PR B 2 H22F H 0.6146 0.3934 0.6463 0.091 Uiso 0.75 1 calc PR B 2 N1' N 0.6343(4) 0.5984(5) 0.6356(4) 0.0496(10) Uani 0.75 1 d PDU B 2 O9' O 0.6834(5) 0.6783(8) 0.6043(4) 0.0555(14) Uani 0.75 1 d PDU B 2 O10' O 0.5754(2) 0.6299(3) 0.67652(13) 0.0599(6) Uani 0.75 1 d PDU B 2 H4A H 0.1934(15) 0.0419(18) 0.7036(9) 0.034(5) Uiso 1 1 d 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 Cl1 0.0383(2) 0.0244(2) 0.0231(2) -0.00794(14) -0.00034(16) 0.00018(15) Cl2 0.0382(2) 0.0322(2) 0.0289(2) 0.00584(15) 0.01755(17) -0.00255(16) O1 0.0244(5) 0.0230(5) 0.0163(5) 0.0033(4) 0.0046(4) -0.0010(4) O2 0.0268(5) 0.0163(5) 0.0154(5) -0.0012(4) 0.0019(4) -0.0018(4) O3 0.0250(5) 0.0240(5) 0.0200(5) -0.0002(4) 0.0093(4) 0.0000(4) O4 0.0311(6) 0.0198(5) 0.0157(5) -0.0015(4) 0.0028(4) 0.0002(4) O5 0.0290(5) 0.0194(5) 0.0204(5) 0.0001(4) 0.0082(4) -0.0054(4) O6 0.0242(5) 0.0222(5) 0.0189(5) 0.0031(4) 0.0092(4) 0.0035(4) O7 0.0345(6) 0.0220(5) 0.0164(5) 0.0022(4) 0.0028(4) 0.0002(4) O8 0.0356(7) 0.0578(8) 0.0370(7) 0.0222(6) 0.0149(5) 0.0184(6) C1 0.0213(7) 0.0207(7) 0.0159(7) 0.0018(5) 0.0052(5) -0.0011(5) C2 0.0231(7) 0.0178(7) 0.0143(6) -0.0019(5) 0.0038(5) -0.0025(5) C3 0.0227(7) 0.0189(7) 0.0170(7) 0.0003(5) 0.0050(5) 0.0016(5) C4 0.0204(7) 0.0206(7) 0.0180(7) -0.0014(5) 0.0032(5) -0.0025(5) C5 0.0261(7) 0.0182(7) 0.0160(7) -0.0005(5) 0.0062(5) -0.0030(6) C6 0.0250(7) 0.0170(7) 0.0174(7) 0.0027(5) 0.0075(5) 0.0016(6) C7 0.0269(7) 0.0215(7) 0.0196(7) 0.0011(6) 0.0077(6) -0.0023(6) C8 0.0177(7) 0.0185(7) 0.0206(7) 0.0011(6) 0.0052(5) -0.0014(5) C9 0.0158(6) 0.0195(7) 0.0198(7) -0.0002(5) 0.0043(5) -0.0018(5) C10 0.0213(7) 0.0205(7) 0.0196(7) 0.0026(5) 0.0033(5) -0.0004(6) C11 0.0231(7) 0.0168(7) 0.0263(7) -0.0006(6) 0.0045(6) -0.0005(6) C12 0.0196(7) 0.0226(7) 0.0207(7) -0.0060(6) 0.0019(6) -0.0010(6) C13 0.0233(7) 0.0237(7) 0.0182(7) 0.0004(6) 0.0019(6) 0.0003(6) C14 0.0211(7) 0.0173(7) 0.0216(7) 0.0001(5) 0.0033(5) -0.0004(5) C15 0.0269(8) 0.0244(7) 0.0246(7) 0.0017(6) 0.0083(6) 0.0051(6) C16 0.0247(7) 0.0218(7) 0.0215(7) -0.0009(6) 0.0078(6) 0.0003(6) C17 0.0257(8) 0.0351(9) 0.0300(8) 0.0066(7) 0.0086(6) 0.0088(7) C18 0.0240(8) 0.0367(9) 0.0300(8) 0.0024(7) 0.0126(6) 0.0041(7) C19 0.0286(8) 0.0229(7) 0.0219(7) -0.0003(6) 0.0099(6) -0.0053(6) C20 0.0290(8) 0.0225(7) 0.0253(8) 0.0035(6) 0.0087(6) 0.0048(6) C21 0.0241(7) 0.0226(7) 0.0243(7) -0.0009(6) 0.0096(6) 0.0027(6) C22 0.086(7) 0.046(5) 0.052(6) -0.022(4) 0.028(6) -0.027(6) N1 0.089(6) 0.065(5) 0.045(5) -0.012(4) 0.045(5) -0.011(5) O9 0.072(8) 0.056(8) 0.055(6) -0.006(5) 0.022(6) -0.029(6) O10 0.138(7) 0.081(5) 0.055(4) -0.007(4) 0.056(5) -0.008(5) C22' 0.085(3) 0.049(2) 0.056(3) -0.0120(17) 0.029(2) -0.027(2) N1' 0.072(3) 0.0468(18) 0.0380(18) -0.0105(14) 0.029(2) -0.0214(18) O9' 0.083(4) 0.0421(17) 0.056(3) -0.0051(18) 0.045(3) -0.011(2) O10' 0.0737(15) 0.0688(15) 0.0491(13) -0.0041(11) 0.0387(12) -0.0127(13) _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 Cl1 C12 1.7435(14) . ? Cl2 C19 1.7417(14) . ? O1 C7 1.4082(18) . ? O1 C1 1.4468(16) . ? O2 C8 1.3448(17) . ? O2 C2 1.4470(16) . ? O3 C7 1.4033(18) . ? O3 C3 1.4440(16) . ? O4 C4 1.4153(17) . ? O4 H4A 0.791(15) . ? O5 C7 1.4063(17) . ? O5 C5 1.4528(16) . ? O6 C15 1.3499(18) . ? O6 C6 1.4347(16) . ? O7 C8 1.2119(17) . ? O8 C15 1.2069(19) . ? C1 C2 1.5223(19) . ? C1 C6 1.5325(19) . ? C1 H1 1.0000 . ? C2 C3 1.5245(19) . ? C2 H2 1.0000 . ? C3 C4 1.5245(19) . ? C3 H3 1.0000 . ? C4 C5 1.535(2) . ? C4 H4 1.0000 . ? C5 C6 1.529(2) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.4835(19) . ? C9 C14 1.392(2) . ? C9 C10 1.396(2) . ? C10 C11 1.385(2) . ? C10 H10 0.9500 . ? C11 C12 1.387(2) . ? C11 H11 0.9500 . ? C12 C13 1.388(2) . ? C13 C14 1.392(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.487(2) . ? C16 C21 1.392(2) . ? C16 C17 1.394(2) . ? C17 C18 1.382(2) . ? C17 H17 0.9500 . ? C18 C19 1.384(2) . ? C18 H18 0.9500 . ? C19 C20 1.381(2) . ? C20 C21 1.386(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 N1 1.524(17) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 O9 1.13(3) . ? N1 O10 1.24(3) . ? C22' N1' 1.552(6) . ? C22' H22D 0.9800 . ? C22' H22E 0.9800 . ? C22' H22F 0.9800 . ? N1' O10' 1.212(7) . ? N1' O9' 1.236(10) . ? 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 110.59(10) . . ? C8 O2 C2 115.78(10) . . ? C7 O3 C3 110.59(10) . . ? C4 O4 H4A 107.6(14) . . ? C7 O5 C5 111.28(10) . . ? C15 O6 C6 117.34(11) . . ? O1 C1 C2 109.64(11) . . ? O1 C1 C6 106.38(11) . . ? C2 C1 C6 110.00(11) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C1 107.18(10) . . ? O2 C2 C3 110.13(11) . . ? C1 C2 C3 108.65(11) . . ? O2 C2 H2 110.3 . . ? C1 C2 H2 110.3 . . ? C3 C2 H2 110.3 . . ? O3 C3 C2 109.41(11) . . ? O3 C3 C4 107.80(11) . . ? C2 C3 C4 109.87(11) . . ? O3 C3 H3 109.9 . . ? C2 C3 H3 109.9 . . ? C4 C3 H3 109.9 . . ? O4 C4 C3 107.66(11) . . ? O4 C4 C5 115.07(11) . . ? C3 C4 C5 107.28(11) . . ? O4 C4 H4 108.9 . . ? C3 C4 H4 108.9 . . ? C5 C4 H4 108.9 . . ? O5 C5 C6 105.32(11) . . ? O5 C5 C4 106.56(11) . . ? C6 C5 C4 114.42(11) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 108.32(11) . . ? O6 C6 C1 111.51(11) . . ? C5 C6 C1 107.92(11) . . ? O6 C6 H6 109.7 . . ? C5 C6 H6 109.7 . . ? C1 C6 H6 109.7 . . ? O3 C7 O5 111.71(11) . . ? O3 C7 O1 111.40(11) . . ? O5 C7 O1 111.18(11) . . ? O3 C7 H7 107.4 . . ? O5 C7 H7 107.4 . . ? O1 C7 H7 107.4 . . ? O7 C8 O2 122.73(13) . . ? O7 C8 C9 124.75(13) . . ? O2 C8 C9 112.53(11) . . ? C14 C9 C10 120.26(13) . . ? C14 C9 C8 121.74(12) . . ? C10 C9 C8 117.99(12) . . ? C11 C10 C9 119.91(13) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.00(13) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 C13 122.13(13) . . ? C11 C12 Cl1 118.08(11) . . ? C13 C12 Cl1 119.78(11) . . ? C12 C13 C14 118.46(13) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C13 C14 C9 120.23(13) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? O8 C15 O6 123.43(14) . . ? O8 C15 C16 125.44(14) . . ? O6 C15 C16 111.11(12) . . ? C21 C16 C17 119.89(14) . . ? C21 C16 C15 121.52(13) . . ? C17 C16 C15 118.58(13) . . ? C18 C17 C16 120.34(14) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 118.84(14) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 121.79(14) . . ? C20 C19 Cl2 118.77(12) . . ? C18 C19 Cl2 119.44(12) . . ? C19 C20 C21 119.15(14) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C20 C21 C16 119.94(14) . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? O9 N1 O10 118(2) . . ? O9 N1 C22 126(2) . . ? O10 N1 C22 115.3(19) . . ? N1' C22' H22D 109.5 . . ? N1' C22' H22E 109.5 . . ? H22D C22' H22E 109.5 . . ? N1' C22' H22F 109.5 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 109.5 . . ? O10' N1' O9' 124.2(5) . . ? O10' N1' C22' 121.6(5) . . ? O9' N1' C22' 114.0(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C2 57.97(14) . . . . ? C7 O1 C1 C6 -60.94(13) . . . . ? C8 O2 C2 C1 159.51(11) . . . . ? C8 O2 C2 C3 -82.47(14) . . . . ? O1 C1 C2 O2 65.30(13) . . . . ? C6 C1 C2 O2 -178.05(10) . . . . ? O1 C1 C2 C3 -53.68(14) . . . . ? C6 C1 C2 C3 62.97(14) . . . . ? C7 O3 C3 C2 -58.80(14) . . . . ? C7 O3 C3 C4 60.65(14) . . . . ? O2 C2 C3 O3 -63.10(14) . . . . ? C1 C2 C3 O3 54.01(14) . . . . ? O2 C2 C3 C4 178.74(11) . . . . ? C1 C2 C3 C4 -64.15(14) . . . . ? O3 C3 C4 O4 175.56(10) . . . . ? C2 C3 C4 O4 -65.29(14) . . . . ? O3 C3 C4 C5 -60.06(13) . . . . ? C2 C3 C4 C5 59.10(14) . . . . ? C7 O5 C5 C6 61.54(13) . . . . ? C7 O5 C5 C4 -60.38(14) . . . . ? O4 C4 C5 O5 179.12(10) . . . . ? C3 C4 C5 O5 59.36(13) . . . . ? O4 C4 C5 C6 63.16(15) . . . . ? C3 C4 C5 C6 -56.60(15) . . . . ? C15 O6 C6 C5 -148.51(12) . . . . ? C15 O6 C6 C1 92.87(14) . . . . ? O5 C5 C6 O6 178.24(10) . . . . ? C4 C5 C6 O6 -65.08(14) . . . . ? O5 C5 C6 C1 -60.89(13) . . . . ? C4 C5 C6 C1 55.79(14) . . . . ? O1 C1 C6 O6 -179.88(10) . . . . ? C2 C1 C6 O6 61.45(14) . . . . ? O1 C1 C6 C5 61.26(13) . . . . ? C2 C1 C6 C5 -57.41(14) . . . . ? C3 O3 C7 O5 -61.54(14) . . . . ? C3 O3 C7 O1 63.47(14) . . . . ? C5 O5 C7 O3 62.03(14) . . . . ? C5 O5 C7 O1 -63.10(14) . . . . ? C1 O1 C7 O3 -62.96(14) . . . . ? C1 O1 C7 O5 62.34(14) . . . . ? C2 O2 C8 O7 -2.66(19) . . . . ? C2 O2 C8 C9 177.46(11) . . . . ? O7 C8 C9 C14 174.69(13) . . . . ? O2 C8 C9 C14 -5.44(18) . . . . ? O7 C8 C9 C10 -5.4(2) . . . . ? O2 C8 C9 C10 174.50(12) . . . . ? C14 C9 C10 C11 0.8(2) . . . . ? C8 C9 C10 C11 -179.17(12) . . . . ? C9 C10 C11 C12 -1.0(2) . . . . ? C10 C11 C12 C13 0.5(2) . . . . ? C10 C11 C12 Cl1 -179.20(11) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? Cl1 C12 C13 C14 179.92(11) . . . . ? C12 C13 C14 C9 -0.5(2) . . . . ? C10 C9 C14 C13 0.0(2) . . . . ? C8 C9 C14 C13 179.90(13) . . . . ? C6 O6 C15 O8 -4.2(2) . . . . ? C6 O6 C15 C16 177.20(11) . . . . ? O8 C15 C16 C21 -170.42(16) . . . . ? O6 C15 C16 C21 8.1(2) . . . . ? O8 C15 C16 C17 8.8(2) . . . . ? O6 C15 C16 C17 -172.60(14) . . . . ? C21 C16 C17 C18 0.4(2) . . . . ? C15 C16 C17 C18 -178.85(15) . . . . ? C16 C17 C18 C19 1.2(2) . . . . ? C17 C18 C19 C20 -1.8(2) . . . . ? C17 C18 C19 Cl2 177.91(13) . . . . ? C18 C19 C20 C21 0.8(2) . . . . ? Cl2 C19 C20 C21 -178.94(11) . . . . ? C19 C20 C21 C16 0.9(2) . . . . ? C17 C16 C21 C20 -1.5(2) . . . . ? C15 C16 C21 C20 177.78(14) . . . . ? 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' 1.00 2.39 3.363(7) 163.8 4_566 C22' H22D O8 0.98 2.50 3.479(5) 177.0 2_656 C7 H7 O9 1.00 2.45 3.39(3) 157.0 4_566 C13 H13 O10 0.95 2.57 3.281(8) 131.5 3_667 C11 H11 O1 0.95 2.56 3.3814(17) 144.9 1_565 C5 H5 O4 1.00 2.58 3.2886(17) 127.5 2_546 C14 H14 O8 0.95 2.60 3.3282(19) 134.2 3_657 O4 H4A O7 0.791(15) 2.012(15) 2.7995(14) 174(2) 2_546 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.373 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.049 #===END data_3E _database_code_depnum_ccdc_archive 'CCDC 752187' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate tetrahydrofuran solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate tetrahydrofuran solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, C4 H8 O' _chemical_formula_sum 'C25 H24 Cl2 O9' _chemical_formula_weight 539.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.908(3) _cell_length_b 10.135(2) _cell_length_c 18.299(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.682(4) _cell_angle_gamma 90.00 _cell_volume 2344.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 5048 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 28.04 _exptl_crystal_description 'square plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.333 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9304 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11470 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4120 _reflns_number_gt 3351 _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 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^)+(0.0515P)^2^+2.0023P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4120 _refine_ls_number_parameters 356 _refine_ls_number_restraints 53 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1313 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.112 _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 Cl1 Cl 0.03642(7) 1.20046(8) -0.20248(4) 0.0299(2) Uani 1 1 d . . . Cl2 Cl -0.11063(12) 0.66805(15) 0.50714(8) 0.0348(3) Uani 0.85 1 d P A 1 Cl2' Cl -0.1280(8) 0.7243(9) 0.4830(5) 0.046(2) Uani 0.15 1 d PD A 2 O1 O 0.15020(17) 0.4497(2) 0.03497(11) 0.0235(5) Uani 1 1 d . . . O2 O 0.14395(16) 0.72811(19) 0.05257(11) 0.0201(5) Uani 1 1 d . . . O3 O 0.31684(17) 0.5428(2) 0.06965(12) 0.0250(5) Uani 1 1 d . . . O4 O 0.29809(19) 0.5930(2) 0.26242(12) 0.0264(5) Uani 1 1 d D . . O5 O 0.28291(19) 0.3380(2) 0.11659(12) 0.0289(6) Uani 1 1 d . . . O6 O 0.09651(18) 0.4713(2) 0.22301(12) 0.0280(5) Uani 1 1 d . . . O7 O 0.19838(18) 0.8995(2) 0.12828(11) 0.0245(5) Uani 1 1 d . . . O8 O -0.0267(2) 0.3143(3) 0.21579(15) 0.0494(8) Uani 1 1 d . . . C1 C 0.1123(3) 0.5122(3) 0.09507(17) 0.0218(7) Uani 1 1 d . . . H1 H 0.0347 0.5298 0.0800 0.026 Uiso 1 1 calc R . . C2 C 0.1720(2) 0.6404(3) 0.11577(16) 0.0194(7) Uani 1 1 d . . . H2 H 0.1511 0.6803 0.1606 0.023 Uiso 1 1 calc R . . C3 C 0.2899(2) 0.6110(3) 0.13217(16) 0.0210(7) Uani 1 1 d . . . H3 H 0.3308 0.6952 0.1413 0.025 Uiso 1 1 calc R . . C4 C 0.3181(3) 0.5220(3) 0.20000(17) 0.0239(7) Uani 1 1 d . . . H4 H 0.3950 0.4996 0.2085 0.029 Uiso 1 1 calc R . . C5 C 0.2531(3) 0.3954(3) 0.18178(17) 0.0243(7) Uani 1 1 d . . . H5 H 0.2702 0.3326 0.2247 0.029 Uiso 1 1 calc R . . C6 C 0.1343(3) 0.4165(3) 0.16098(17) 0.0253(8) Uani 1 1 d . . . H6 H 0.0982 0.3305 0.1462 0.030 Uiso 1 1 calc R . . C7 C 0.2604(3) 0.4256(3) 0.05528(18) 0.0263(8) Uani 1 1 d . . . H7 H 0.2828 0.3818 0.0120 0.032 Uiso 1 1 calc R . . C8 C 0.1613(2) 0.8579(3) 0.06647(17) 0.0200(7) Uani 1 1 d . . . C9 C 0.1310(2) 0.9396(3) -0.00118(16) 0.0182(7) Uani 1 1 d . . . C10 C 0.1398(2) 1.0763(3) 0.00583(17) 0.0217(7) Uani 1 1 d . . . H10 H 0.1658 1.1146 0.0534 0.026 Uiso 1 1 calc R . . C11 C 0.1110(2) 1.1557(3) -0.05563(17) 0.0213(7) Uani 1 1 d . . . H11 H 0.1164 1.2489 -0.0507 0.026 Uiso 1 1 calc R . . C12 C 0.0741(2) 1.0991(3) -0.12493(17) 0.0211(7) Uani 1 1 d . . . C13 C 0.0655(2) 0.9633(3) -0.13320(17) 0.0225(7) Uani 1 1 d . . . H13 H 0.0399 0.9253 -0.1809 0.027 Uiso 1 1 calc R . . C14 C 0.0944(2) 0.8845(3) -0.07148(17) 0.0214(7) Uani 1 1 d . . . H14 H 0.0894 0.7914 -0.0767 0.026 Uiso 1 1 calc R . . C15 C 0.0166(3) 0.4102(3) 0.24601(18) 0.0252(7) Uani 1 1 d . . . C16 C -0.0116(3) 0.4757(3) 0.31128(17) 0.0238(7) Uani 1 1 d . A . C17 C -0.1006(3) 0.4314(3) 0.33654(18) 0.0294(8) Uani 1 1 d . . . H17 H -0.1403 0.3592 0.3122 0.035 Uiso 1 1 calc R . . C18 C -0.1317(3) 0.4910(4) 0.39622(19) 0.0324(8) Uani 1 1 d . A . H18 H -0.1924 0.4609 0.4132 0.039 Uiso 1 1 calc R . . C19 C -0.0730(3) 0.5953(4) 0.43076(19) 0.0341(9) Uani 1 1 d D . . C20 C 0.0174(3) 0.6400(4) 0.40773(19) 0.0329(8) Uani 1 1 d . A . H20 H 0.0577 0.7107 0.4331 0.040 Uiso 1 1 calc R . . C21 C 0.0476(3) 0.5803(3) 0.34773(18) 0.0263(7) Uani 1 1 d . . . H21 H 0.1086 0.6104 0.3312 0.032 Uiso 1 1 calc R A . H4A H 0.300(3) 0.542(3) 0.2983(16) 0.049(13) Uiso 1 1 d D . . O9 O 0.6993(2) 0.6413(3) 0.11318(14) 0.0443(7) Uani 1 1 d . C . C22 C 0.7667(4) 0.5394(4) 0.1487(3) 0.0559(12) Uani 1 1 d D . . H22A H 0.7930 0.5612 0.2019 0.067 Uiso 1 1 calc R B 1 H22B H 0.8283 0.5293 0.1245 0.067 Uiso 1 1 calc R B 1 C23 C 0.7050(5) 0.4158(6) 0.1419(4) 0.0620(16) Uani 0.80 1 d PU C 1 H23B H 0.7100 0.3740 0.1914 0.074 Uiso 0.80 1 calc PR C 1 H23A H 0.7314 0.3528 0.1085 0.074 Uiso 0.80 1 calc PR C 1 C23' C 0.6946(13) 0.464(2) 0.1859(13) 0.054(4) Uani 0.20 1 d PDU C 2 H23C H 0.7002 0.3691 0.1750 0.065 Uiso 0.20 1 calc PR C 2 H23D H 0.7157 0.4765 0.2406 0.065 Uiso 0.20 1 calc PR C 2 C24 C 0.5925(4) 0.4552(5) 0.1095(3) 0.0422(12) Uani 0.80 1 d PU C 1 H24A H 0.5710 0.4251 0.0571 0.051 Uiso 0.80 1 calc PR C 1 H24B H 0.5432 0.4177 0.1390 0.051 Uiso 0.80 1 calc PR C 1 C24' C 0.5862(14) 0.5067(19) 0.1610(11) 0.047(4) Uani 0.20 1 d PDU C 2 H24C H 0.5411 0.4336 0.1368 0.056 Uiso 0.20 1 calc PR C 2 H24D H 0.5565 0.5410 0.2031 0.056 Uiso 0.20 1 calc PR C 2 C25 C 0.5939(4) 0.5992(5) 0.1137(3) 0.0708(15) Uani 1 1 d D . . H25A H 0.5440 0.6371 0.0706 0.085 Uiso 1 1 calc R C 1 H25B H 0.5726 0.6288 0.1601 0.085 Uiso 1 1 calc R C 1 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 Cl1 0.0378(5) 0.0221(4) 0.0263(4) 0.0080(3) -0.0018(4) -0.0005(4) Cl2 0.0314(7) 0.0455(9) 0.0306(8) -0.0128(6) 0.0139(6) -0.0037(7) Cl2' 0.051(5) 0.055(6) 0.036(5) -0.003(4) 0.014(4) 0.003(5) O1 0.0298(13) 0.0224(11) 0.0176(11) -0.0049(9) 0.0034(9) 0.0004(10) O2 0.0267(12) 0.0133(10) 0.0184(11) -0.0001(8) -0.0001(9) 0.0005(9) O3 0.0268(13) 0.0237(12) 0.0255(12) 0.0005(9) 0.0075(10) 0.0031(10) O4 0.0414(15) 0.0183(12) 0.0180(12) 0.0012(10) 0.0023(11) 0.0014(11) O5 0.0445(15) 0.0189(11) 0.0240(12) 0.0001(9) 0.0084(11) 0.0103(11) O6 0.0404(14) 0.0206(11) 0.0266(12) -0.0055(10) 0.0149(11) -0.0092(11) O7 0.0358(14) 0.0189(11) 0.0162(11) -0.0020(9) -0.0005(10) -0.0011(10) O8 0.0565(19) 0.0402(16) 0.0595(18) -0.0288(14) 0.0309(15) -0.0254(14) C1 0.0244(18) 0.0199(16) 0.0218(16) -0.0027(13) 0.0059(14) -0.0006(14) C2 0.0279(18) 0.0149(15) 0.0161(15) 0.0027(12) 0.0058(13) 0.0005(13) C3 0.0243(18) 0.0190(16) 0.0200(16) -0.0003(13) 0.0051(13) -0.0004(14) C4 0.0265(18) 0.0204(16) 0.0237(17) 0.0014(13) 0.0027(14) 0.0052(14) C5 0.038(2) 0.0158(15) 0.0190(16) 0.0015(13) 0.0040(15) 0.0058(15) C6 0.042(2) 0.0150(15) 0.0210(16) -0.0039(13) 0.0116(15) -0.0053(15) C7 0.034(2) 0.0226(17) 0.0229(17) -0.0019(14) 0.0061(15) 0.0061(15) C8 0.0164(16) 0.0203(16) 0.0239(17) -0.0018(13) 0.0049(13) -0.0009(13) C9 0.0147(16) 0.0180(15) 0.0215(16) -0.0004(12) 0.0024(13) 0.0028(13) C10 0.0252(18) 0.0199(16) 0.0199(16) -0.0017(13) 0.0042(13) 0.0011(14) C11 0.0234(17) 0.0139(15) 0.0268(17) -0.0007(13) 0.0054(14) -0.0011(13) C12 0.0199(17) 0.0204(16) 0.0220(16) 0.0052(13) 0.0014(13) 0.0029(14) C13 0.0251(18) 0.0194(16) 0.0205(16) -0.0021(13) -0.0013(14) -0.0007(14) C14 0.0219(18) 0.0141(15) 0.0261(17) -0.0029(13) -0.0002(14) 0.0002(13) C15 0.0276(19) 0.0186(17) 0.0283(18) 0.0008(14) 0.0033(15) 0.0007(15) C16 0.0259(18) 0.0226(17) 0.0216(16) 0.0007(13) 0.0023(14) -0.0007(14) C17 0.0287(19) 0.0300(19) 0.0293(18) -0.0031(15) 0.0053(15) -0.0085(16) C18 0.0245(19) 0.042(2) 0.0318(19) -0.0023(16) 0.0080(15) -0.0061(17) C19 0.029(2) 0.042(2) 0.0320(19) -0.0108(17) 0.0080(16) -0.0024(17) C20 0.030(2) 0.036(2) 0.035(2) -0.0127(16) 0.0097(16) -0.0095(17) C21 0.0237(18) 0.0280(18) 0.0282(18) -0.0021(15) 0.0075(15) -0.0039(15) O9 0.0461(17) 0.0363(15) 0.0489(16) 0.0062(13) 0.0058(13) -0.0044(13) C22 0.045(3) 0.053(3) 0.064(3) 0.017(2) -0.002(2) -0.004(2) C23 0.053(3) 0.038(3) 0.086(4) 0.005(3) -0.008(3) 0.004(3) C23' 0.046(7) 0.046(7) 0.065(8) 0.011(7) -0.003(7) 0.001(6) C24 0.041(3) 0.035(3) 0.051(3) -0.001(2) 0.009(2) -0.001(2) C24' 0.045(7) 0.041(7) 0.055(7) 0.005(6) 0.009(6) -0.003(6) C25 0.037(3) 0.047(3) 0.123(5) -0.001(3) 0.004(3) 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 Cl1 C12 1.740(3) . ? Cl2 C19 1.735(4) . ? Cl2' C19 1.845(9) . ? O1 C7 1.417(4) . ? O1 C1 1.438(4) . ? O2 C8 1.350(4) . ? O2 C2 1.445(3) . ? O3 C7 1.391(4) . ? O3 C3 1.438(4) . ? O4 C4 1.417(4) . ? O4 H4A 0.834(19) . ? O5 C7 1.414(4) . ? O5 C5 1.448(4) . ? O6 C15 1.341(4) . ? O6 C6 1.435(4) . ? O7 C8 1.211(3) . ? O8 C15 1.200(4) . ? C1 C2 1.519(4) . ? C1 C6 1.529(4) . ? C1 H1 1.0000 . ? C2 C3 1.520(4) . ? C2 H2 1.0000 . ? C3 C4 1.518(4) . ? C3 H3 1.0000 . ? C4 C5 1.532(4) . ? C4 H4 1.0000 . ? C5 C6 1.518(5) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.475(4) . ? C9 C10 1.394(4) . ? C9 C14 1.394(4) . ? C10 C11 1.371(4) . ? C10 H10 0.9500 . ? C11 C12 1.386(4) . ? C11 H11 0.9500 . ? C12 C13 1.387(4) . ? C13 C14 1.372(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.475(4) . ? C16 C21 1.395(4) . ? C16 C17 1.397(5) . ? C17 C18 1.377(5) . ? C17 H17 0.9500 . ? C18 C19 1.377(5) . ? C18 H18 0.9500 . ? C19 C20 1.394(5) . ? C20 C21 1.377(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? O9 C22 1.421(5) . ? O9 C25 1.427(5) . ? C22 C23' 1.472(16) . ? C22 C23 1.476(7) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.508(7) . ? C23 H23B 0.9900 . ? C23 H23A 0.9900 . ? C23' C24' 1.447(17) . ? C23' H23C 0.9900 . ? C23' H23D 0.9900 . ? C24 C25 1.461(6) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C24' C25 1.293(15) . ? C24' H24C 0.9900 . ? C24' H24D 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? 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 110.7(2) . . ? C8 O2 C2 116.3(2) . . ? C7 O3 C3 111.0(2) . . ? C4 O4 H4A 110(3) . . ? C7 O5 C5 110.8(2) . . ? C15 O6 C6 118.4(2) . . ? O1 C1 C2 109.5(2) . . ? O1 C1 C6 106.6(2) . . ? C2 C1 C6 110.0(2) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C1 107.1(2) . . ? O2 C2 C3 110.9(2) . . ? C1 C2 C3 108.5(3) . . ? O2 C2 H2 110.1 . . ? C1 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? O3 C3 C4 108.0(2) . . ? O3 C3 C2 109.3(2) . . ? C4 C3 C2 110.0(3) . . ? O3 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? O4 C4 C3 107.7(2) . . ? O4 C4 C5 114.8(3) . . ? C3 C4 C5 106.9(2) . . ? O4 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? O5 C5 C6 105.9(2) . . ? O5 C5 C4 106.9(3) . . ? C6 C5 C4 114.7(3) . . ? O5 C5 H5 109.7 . . ? C6 C5 H5 109.7 . . ? C4 C5 H5 109.7 . . ? O6 C6 C5 110.1(2) . . ? O6 C6 C1 109.9(2) . . ? C5 C6 C1 107.7(3) . . ? O6 C6 H6 109.7 . . ? C5 C6 H6 109.7 . . ? C1 C6 H6 109.7 . . ? O3 C7 O5 111.8(3) . . ? O3 C7 O1 111.2(2) . . ? O5 C7 O1 110.5(3) . . ? O3 C7 H7 107.7 . . ? O5 C7 H7 107.7 . . ? O1 C7 H7 107.7 . . ? O7 C8 O2 122.3(3) . . ? O7 C8 C9 125.2(3) . . ? O2 C8 C9 112.5(2) . . ? C10 C9 C14 119.3(3) . . ? C10 C9 C8 118.6(3) . . ? C14 C9 C8 122.2(3) . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.6(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 121.1(3) . . ? C11 C12 Cl1 119.3(2) . . ? C13 C12 Cl1 119.6(2) . . ? C14 C13 C12 119.0(3) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C9 120.8(3) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O8 C15 O6 123.1(3) . . ? O8 C15 C16 124.7(3) . . ? O6 C15 C16 112.2(3) . . ? C21 C16 C17 119.6(3) . . ? C21 C16 C15 121.9(3) . . ? C17 C16 C15 118.5(3) . . ? C18 C17 C16 120.8(3) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C19 C18 C17 118.6(3) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C18 C19 C20 121.8(3) . . ? C18 C19 Cl2 118.6(3) . . ? C20 C19 Cl2 119.6(3) . . ? C18 C19 Cl2' 123.2(4) . . ? C20 C19 Cl2' 111.1(4) . . ? C21 C20 C19 119.2(3) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C20 C21 C16 120.0(3) . . ? C20 C21 H21 120.0 . . ? C16 C21 H21 120.0 . . ? C22 O9 C25 106.0(3) . . ? O9 C22 C23' 101.6(8) . . ? O9 C22 C23 108.0(4) . . ? O9 C22 H22A 110.1 . . ? C23' C22 H22A 77.5 . . ? C23 C22 H22A 110.1 . . ? O9 C22 H22B 110.1 . . ? C23' C22 H22B 142.5 . . ? C23 C22 H22B 110.1 . . ? H22A C22 H22B 108.4 . . ? C22 C23 C24 105.6(4) . . ? C22 C23 H23B 110.6 . . ? C24 C23 H23B 110.6 . . ? C22 C23 H23A 110.6 . . ? C24 C23 H23A 110.6 . . ? H23B C23 H23A 108.8 . . ? C24' C23' C22 111.3(14) . . ? C24' C23' H23C 109.4 . . ? C22 C23' H23C 109.4 . . ? C24' C23' H23D 109.4 . . ? C22 C23' H23D 109.4 . . ? H23C C23' H23D 108.0 . . ? C25 C24 C23 104.0(4) . . ? C25 C24 H24A 110.9 . . ? C23 C24 H24A 110.9 . . ? C25 C24 H24B 110.9 . . ? C23 C24 H24B 110.9 . . ? H24A C24 H24B 109.0 . . ? C25 C24' C23' 103.0(14) . . ? C25 C24' H24C 111.2 . . ? C23' C24' H24C 111.2 . . ? C25 C24' H24D 111.2 . . ? C23' C24' H24D 111.2 . . ? H24C C24' H24D 109.1 . . ? C24' C25 O9 115.1(9) . . ? C24' C25 C24 46.4(10) . . ? O9 C25 C24 107.5(4) . . ? C24' C25 H25A 133.5 . . ? O9 C25 H25A 110.2 . . ? C24 C25 H25A 110.2 . . ? C24' C25 H25B 64.7 . . ? O9 C25 H25B 110.2 . . ? C24 C25 H25B 110.2 . . ? H25A C25 H25B 108.5 . . ? 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 57.9(3) . . . . ? C7 O1 C1 C6 -61.1(3) . . . . ? C8 O2 C2 C1 160.3(2) . . . . ? C8 O2 C2 C3 -81.4(3) . . . . ? O1 C1 C2 O2 65.7(3) . . . . ? C6 C1 C2 O2 -177.4(2) . . . . ? O1 C1 C2 C3 -54.1(3) . . . . ? C6 C1 C2 C3 62.8(3) . . . . ? C7 O3 C3 C4 60.7(3) . . . . ? C7 O3 C3 C2 -59.0(3) . . . . ? O2 C2 C3 O3 -63.2(3) . . . . ? C1 C2 C3 O3 54.3(3) . . . . ? O2 C2 C3 C4 178.4(2) . . . . ? C1 C2 C3 C4 -64.2(3) . . . . ? O3 C3 C4 O4 176.1(2) . . . . ? C2 C3 C4 O4 -64.7(3) . . . . ? O3 C3 C4 C5 -60.0(3) . . . . ? C2 C3 C4 C5 59.2(3) . . . . ? C7 O5 C5 C6 62.2(3) . . . . ? C7 O5 C5 C4 -60.5(3) . . . . ? O4 C4 C5 O5 179.3(2) . . . . ? C3 C4 C5 O5 59.9(3) . . . . ? O4 C4 C5 C6 62.3(3) . . . . ? C3 C4 C5 C6 -57.1(3) . . . . ? C15 O6 C6 C5 -126.7(3) . . . . ? C15 O6 C6 C1 114.8(3) . . . . ? O5 C5 C6 O6 178.9(2) . . . . ? C4 C5 C6 O6 -63.5(3) . . . . ? O5 C5 C6 C1 -61.3(3) . . . . ? C4 C5 C6 C1 56.3(3) . . . . ? O1 C1 C6 O6 -178.8(2) . . . . ? C2 C1 C6 O6 62.5(3) . . . . ? O1 C1 C6 C5 61.2(3) . . . . ? C2 C1 C6 C5 -57.5(3) . . . . ? C3 O3 C7 O5 -61.1(3) . . . . ? C3 O3 C7 O1 62.9(3) . . . . ? C5 O5 C7 O3 61.5(3) . . . . ? C5 O5 C7 O1 -63.0(3) . . . . ? C1 O1 C7 O3 -62.4(3) . . . . ? C1 O1 C7 O5 62.3(3) . . . . ? C2 O2 C8 O7 0.1(4) . . . . ? C2 O2 C8 C9 179.6(2) . . . . ? O7 C8 C9 C10 -3.7(5) . . . . ? O2 C8 C9 C10 176.8(3) . . . . ? O7 C8 C9 C14 176.2(3) . . . . ? O2 C8 C9 C14 -3.3(4) . . . . ? C14 C9 C10 C11 1.0(5) . . . . ? C8 C9 C10 C11 -179.1(3) . . . . ? C9 C10 C11 C12 -0.6(5) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C10 C11 C12 Cl1 179.3(2) . . . . ? C11 C12 C13 C14 -0.2(5) . . . . ? Cl1 C12 C13 C14 -179.3(2) . . . . ? C12 C13 C14 C9 0.6(5) . . . . ? C10 C9 C14 C13 -1.1(5) . . . . ? C8 C9 C14 C13 179.1(3) . . . . ? C6 O6 C15 O8 -2.3(5) . . . . ? C6 O6 C15 C16 178.5(3) . . . . ? O8 C15 C16 C21 174.5(3) . . . . ? O6 C15 C16 C21 -6.3(4) . . . . ? O8 C15 C16 C17 -5.9(5) . . . . ? O6 C15 C16 C17 173.3(3) . . . . ? C21 C16 C17 C18 1.0(5) . . . . ? C15 C16 C17 C18 -178.6(3) . . . . ? C16 C17 C18 C19 -0.2(5) . . . . ? C17 C18 C19 C20 -1.1(6) . . . . ? C17 C18 C19 Cl2 -178.7(3) . . . . ? C17 C18 C19 Cl2' 154.7(4) . . . . ? C18 C19 C20 C21 1.5(6) . . . . ? Cl2 C19 C20 C21 179.1(3) . . . . ? Cl2' C19 C20 C21 -156.9(4) . . . . ? C19 C20 C21 C16 -0.6(5) . . . . ? C17 C16 C21 C20 -0.6(5) . . . . ? C15 C16 C21 C20 179.0(3) . . . . ? C25 O9 C22 C23' -15.8(12) . . . . ? C25 O9 C22 C23 23.7(6) . . . . ? O9 C22 C23 C24 -7.7(7) . . . . ? C23' C22 C23 C24 78.5(13) . . . . ? O9 C22 C23' C24' 11(2) . . . . ? C23 C22 C23' C24' -94(2) . . . . ? C22 C23 C24 C25 -10.7(7) . . . . ? C22 C23' C24' C25 0(2) . . . . ? C23' C24' C25 O9 -11(2) . . . . ? C23' C24' C25 C24 79.9(17) . . . . ? C22 O9 C25 C24' 18.2(13) . . . . ? C22 O9 C25 C24 -31.1(5) . . . . ? C23 C24 C25 C24' -82.7(12) . . . . ? C23 C24 C25 O9 25.6(6) . . . . ? 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 C23 H23A Cl2' 0.99 2.32 3.009(11) 126.1 2_545 C24 H24A Cl2' 0.99 2.33 2.977(11) 121.9 2_545 C7 H7 O9 1.00 2.36 3.299(4) 156.0 3_665 C13 H13 O8 0.95 2.51 3.184(4) 128.2 3_565 C11 H11 O1 0.95 2.55 3.397(4) 148.3 1_565 O4 H4A O7 0.834(19) 1.97(2) 2.795(3) 171(4) 2_545 C25 H25A Cl2' 0.99 2.83 3.789(11) 162.2 4_675 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.362 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.064 #===END data_3F _database_code_depnum_ccdc_archive 'CCDC 752188' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate dioxane solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate dioxane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, C4 H8 O2' _chemical_formula_sum 'C25 H24 Cl2 O10' _chemical_formula_weight 555.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.047(3) _cell_length_b 10.141(3) _cell_length_c 18.678(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.518(4) _cell_angle_gamma 90.00 _cell_volume 2402.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 3018 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 26.90 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9309 _exptl_absorpt_correction_T_max 0.9811 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11795 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4212 _reflns_number_gt 3490 _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 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^)+(0.0472P)^2^+3.5764P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4212 _refine_ls_number_parameters 392 _refine_ls_number_restraints 283 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.077 _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 Cl1 Cl 0.02977(6) 1.19724(7) -0.19967(4) 0.0292(2) Uani 1 1 d . . . Cl2 Cl -0.09649(9) 0.68865(11) 0.50680(6) 0.0629(3) Uani 1 1 d . . . O1 O 0.14011(16) 0.4494(2) 0.04208(11) 0.0262(5) Uani 1 1 d . . . O2 O 0.14093(15) 0.72993(18) 0.05568(10) 0.0213(4) Uani 1 1 d . . . O3 O 0.30810(16) 0.5384(2) 0.07440(11) 0.0263(5) Uani 1 1 d . . . O4 O 0.30518(16) 0.5991(2) 0.26490(11) 0.0253(5) Uani 1 1 d D . . O5 O 0.27301(16) 0.3376(2) 0.12387(11) 0.0280(5) Uani 1 1 d . . . O6 O 0.10105(15) 0.48382(19) 0.22961(11) 0.0248(5) Uani 1 1 d . . . O7 O 0.20075(16) 0.90278(19) 0.12857(10) 0.0258(5) Uani 1 1 d . . . O8 O -0.06283(18) 0.4037(3) 0.18905(14) 0.0454(6) Uani 1 1 d . . . C1 C 0.1076(2) 0.5176(3) 0.10062(15) 0.0215(6) Uani 1 1 d . . . H1 H 0.0304 0.5375 0.0859 0.026 Uiso 1 1 calc R . . C2 C 0.1702(2) 0.6445(3) 0.11948(15) 0.0200(6) Uani 1 1 d . . . H2 H 0.1529 0.6875 0.1634 0.024 Uiso 1 1 calc R . . C3 C 0.2869(2) 0.6108(3) 0.13523(15) 0.0216(6) Uani 1 1 d . . . H3 H 0.3296 0.6937 0.1428 0.026 Uiso 1 1 calc R . . C4 C 0.3177(2) 0.5242(3) 0.20342(15) 0.0225(6) Uani 1 1 d . . . H4 H 0.3935 0.4988 0.2108 0.027 Uiso 1 1 calc R . . C5 C 0.2496(2) 0.3993(3) 0.18790(16) 0.0235(6) Uani 1 1 d . . . H5 H 0.2676 0.3381 0.2310 0.028 Uiso 1 1 calc R . . C6 C 0.1310(2) 0.4251(3) 0.16725(15) 0.0226(6) Uani 1 1 d . . . H6 H 0.0924 0.3401 0.1542 0.027 Uiso 1 1 calc R . . C7 C 0.2488(2) 0.4220(3) 0.06231(17) 0.0280(7) Uani 1 1 d . . . H7 H 0.2678 0.3748 0.0202 0.034 Uiso 1 1 calc R . . C8 C 0.1618(2) 0.8585(3) 0.06809(15) 0.0192(6) Uani 1 1 d . . . C9 C 0.1305(2) 0.9388(3) -0.00005(15) 0.0187(6) Uani 1 1 d . . . C10 C 0.1408(2) 1.0751(3) 0.00629(16) 0.0237(6) Uani 1 1 d . . . H10 H 0.1691 1.1138 0.0531 0.028 Uiso 1 1 calc R . . C11 C 0.1103(2) 1.1542(3) -0.05496(16) 0.0245(7) Uani 1 1 d . . . H11 H 0.1170 1.2474 -0.0507 0.029 Uiso 1 1 calc R . . C12 C 0.0698(2) 1.0961(3) -0.12277(15) 0.0223(6) Uani 1 1 d . . . C13 C 0.0599(2) 0.9604(3) -0.13062(16) 0.0235(6) Uani 1 1 d . . . H13 H 0.0328 0.9220 -0.1777 0.028 Uiso 1 1 calc R . . C14 C 0.0902(2) 0.8819(3) -0.06871(15) 0.0210(6) Uani 1 1 d . . . H14 H 0.0834 0.7888 -0.0731 0.025 Uiso 1 1 calc R . . C15 C 0.0009(2) 0.4634(3) 0.23452(18) 0.0291(7) Uani 1 1 d . . . C16 C -0.0200(2) 0.5238(3) 0.30217(17) 0.0276(7) Uani 1 1 d . . . C17 C -0.1223(3) 0.5194(4) 0.3115(2) 0.0456(9) Uani 1 1 d . . . H17 H -0.1766 0.4810 0.2746 0.055 Uiso 1 1 calc R . . C18 C -0.1454(3) 0.5708(4) 0.3744(2) 0.0482(10) Uani 1 1 d . . . H18 H -0.2155 0.5677 0.3808 0.058 Uiso 1 1 calc R . . C19 C -0.0668(3) 0.6264(3) 0.4274(2) 0.0396(9) Uani 1 1 d . . . C20 C 0.0348(3) 0.6362(4) 0.4184(2) 0.0407(9) Uani 1 1 d . . . H20 H 0.0883 0.6776 0.4548 0.049 Uiso 1 1 calc R . . C21 C 0.0574(3) 0.5847(3) 0.35524(18) 0.0322(7) Uani 1 1 d . . . H21 H 0.1270 0.5912 0.3482 0.039 Uiso 1 1 calc R . . H4A H 0.300(3) 0.548(4) 0.2977(18) 0.067(14) Uiso 1 1 d D . . C22 C 0.6239(10) 0.4576(12) 0.1470(7) 0.064(2) Uani 0.50 1 d PDU A 1 H22A H 0.5748 0.3842 0.1496 0.077 Uiso 0.50 1 calc PR A 1 H22B H 0.6949 0.4194 0.1512 0.077 Uiso 0.50 1 calc PR A 1 C23 C 0.5911(10) 0.5211(11) 0.0771(5) 0.084(2) Uani 0.50 1 d PDU A 1 H23A H 0.5999 0.4578 0.0386 0.101 Uiso 0.50 1 calc PR A 1 H23B H 0.5149 0.5407 0.0687 0.101 Uiso 0.50 1 calc PR A 1 C24 C 0.6516(10) 0.7227(10) 0.1259(5) 0.062(2) Uani 0.50 1 d PDU A 1 H24A H 0.5904 0.7833 0.1141 0.075 Uiso 0.50 1 calc PR A 1 H24B H 0.7155 0.7768 0.1283 0.075 Uiso 0.50 1 calc PR A 1 C25 C 0.6575(10) 0.6712(11) 0.1977(5) 0.073(2) Uani 0.50 1 d PDU A 1 H25A H 0.7316 0.6802 0.2258 0.088 Uiso 0.50 1 calc PR A 1 H25B H 0.6147 0.7295 0.2218 0.088 Uiso 0.50 1 calc PR A 1 O9 O 0.627(2) 0.5434(16) 0.2067(8) 0.055(2) Uani 0.50 1 d PDU A 1 O10 O 0.6426(9) 0.6361(11) 0.0675(6) 0.058(2) Uani 0.50 1 d PDU A 1 C22' C 0.5848(8) 0.4639(11) 0.1406(6) 0.048(2) Uani 0.50 1 d PDU B 2 H22C H 0.5153 0.4936 0.1114 0.058 Uiso 0.50 1 calc PR B 2 H22D H 0.5801 0.3690 0.1519 0.058 Uiso 0.50 1 calc PR B 2 C23' C 0.6714(6) 0.4874(7) 0.0971(4) 0.0382(15) Uani 0.50 1 d PDU B 2 H23C H 0.7412 0.4608 0.1272 0.046 Uiso 0.50 1 calc PR B 2 H23D H 0.6561 0.4346 0.0512 0.046 Uiso 0.50 1 calc PR B 2 C24' C 0.6979(8) 0.6928(9) 0.1468(5) 0.056(2) Uani 0.50 1 d PDU B 2 H24C H 0.7076 0.7876 0.1376 0.067 Uiso 0.50 1 calc PR B 2 H24D H 0.7636 0.6580 0.1791 0.067 Uiso 0.50 1 calc PR B 2 C25' C 0.6003(7) 0.6706(8) 0.1826(5) 0.0456(17) Uani 0.50 1 d PDU B 2 H25C H 0.6022 0.7324 0.2239 0.055 Uiso 0.50 1 calc PR B 2 H25D H 0.5327 0.6814 0.1457 0.055 Uiso 0.50 1 calc PR B 2 O9' O 0.615(2) 0.5390(15) 0.2077(8) 0.050(2) Uani 0.50 1 d PDU B 2 O10' O 0.6714(9) 0.6222(12) 0.0803(6) 0.062(2) Uani 0.50 1 d PDU B 2 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 Cl1 0.0359(4) 0.0259(4) 0.0240(4) 0.0085(3) 0.0033(3) 0.0031(3) Cl2 0.0810(8) 0.0556(6) 0.0705(7) -0.0194(5) 0.0547(6) -0.0081(6) O1 0.0317(12) 0.0264(11) 0.0193(11) -0.0043(9) 0.0036(9) -0.0006(9) O2 0.0289(11) 0.0166(10) 0.0168(10) 0.0023(8) 0.0025(8) 0.0005(8) O3 0.0284(11) 0.0281(11) 0.0246(11) -0.0007(9) 0.0110(9) 0.0005(9) O4 0.0322(12) 0.0239(11) 0.0182(11) 0.0000(9) 0.0030(9) 0.0003(9) O5 0.0380(12) 0.0208(11) 0.0265(11) -0.0015(9) 0.0101(10) 0.0067(9) O6 0.0279(11) 0.0259(11) 0.0224(11) 0.0011(9) 0.0096(9) -0.0016(9) O7 0.0356(12) 0.0239(11) 0.0154(10) -0.0009(9) 0.0010(9) 0.0001(9) O8 0.0321(13) 0.0593(17) 0.0449(15) -0.0135(13) 0.0093(11) -0.0118(12) C1 0.0221(15) 0.0219(15) 0.0201(15) 0.0000(12) 0.0041(12) -0.0002(12) C2 0.0255(15) 0.0202(15) 0.0136(13) 0.0036(11) 0.0029(12) 0.0015(12) C3 0.0228(15) 0.0228(15) 0.0193(14) -0.0011(12) 0.0054(12) -0.0026(12) C4 0.0223(15) 0.0236(15) 0.0206(15) 0.0008(12) 0.0032(12) 0.0046(12) C5 0.0311(16) 0.0211(15) 0.0185(14) 0.0009(12) 0.0066(12) 0.0061(13) C6 0.0300(16) 0.0184(15) 0.0199(15) -0.0016(12) 0.0068(12) -0.0030(12) C7 0.0343(17) 0.0278(16) 0.0242(16) -0.0025(13) 0.0114(14) 0.0010(14) C8 0.0167(14) 0.0214(15) 0.0196(15) 0.0016(12) 0.0044(12) 0.0028(12) C9 0.0184(14) 0.0195(14) 0.0191(14) 0.0005(11) 0.0063(11) 0.0023(11) C10 0.0260(16) 0.0239(16) 0.0198(15) -0.0010(12) 0.0025(12) -0.0007(13) C11 0.0291(16) 0.0179(15) 0.0256(16) 0.0030(12) 0.0047(13) -0.0002(12) C12 0.0206(14) 0.0262(16) 0.0203(15) 0.0072(12) 0.0056(12) 0.0027(12) C13 0.0267(16) 0.0250(16) 0.0171(15) -0.0016(12) 0.0019(12) -0.0023(13) C14 0.0242(15) 0.0175(14) 0.0213(15) 0.0008(12) 0.0054(12) -0.0001(12) C15 0.0292(17) 0.0280(17) 0.0306(18) 0.0054(14) 0.0080(14) -0.0026(14) C16 0.0284(16) 0.0245(16) 0.0321(17) 0.0054(13) 0.0116(14) 0.0019(13) C17 0.037(2) 0.052(2) 0.053(2) -0.0074(19) 0.0187(18) -0.0080(17) C18 0.037(2) 0.050(2) 0.067(3) -0.011(2) 0.032(2) -0.0044(18) C19 0.052(2) 0.0273(18) 0.048(2) -0.0032(16) 0.0291(18) 0.0010(16) C20 0.044(2) 0.043(2) 0.040(2) -0.0053(17) 0.0190(17) -0.0064(17) C21 0.0317(17) 0.0343(18) 0.0345(18) 0.0013(15) 0.0154(15) 0.0002(15) C22 0.084(5) 0.061(4) 0.047(4) -0.011(3) 0.016(4) -0.005(4) C23 0.103(5) 0.085(4) 0.066(4) -0.010(4) 0.024(4) -0.013(4) C24 0.084(5) 0.062(4) 0.046(4) -0.005(3) 0.027(4) -0.012(4) C25 0.102(5) 0.062(4) 0.053(4) -0.006(3) 0.012(4) -0.008(4) O9 0.075(5) 0.054(3) 0.037(3) -0.006(3) 0.019(3) -0.011(3) O10 0.082(5) 0.061(4) 0.040(4) 0.001(3) 0.033(3) -0.004(3) C22' 0.062(5) 0.056(4) 0.034(3) -0.008(3) 0.024(3) -0.013(4) C23' 0.057(4) 0.041(3) 0.026(3) -0.002(3) 0.028(3) 0.007(3) C24' 0.079(5) 0.049(4) 0.047(4) 0.006(3) 0.030(4) -0.010(4) C25' 0.056(4) 0.048(3) 0.041(3) -0.006(3) 0.028(3) -0.004(4) O9' 0.069(5) 0.054(3) 0.035(3) -0.007(3) 0.027(3) -0.012(3) O10' 0.085(5) 0.066(4) 0.047(4) -0.001(3) 0.041(3) -0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C12 1.743(3) . ? Cl2 C19 1.736(3) . ? O1 C7 1.408(4) . ? O1 C1 1.439(3) . ? O2 C8 1.341(3) . ? O2 C2 1.451(3) . ? O3 C7 1.400(4) . ? O3 C3 1.433(3) . ? O4 C4 1.417(3) . ? O4 H4A 0.82(4) . ? O5 C7 1.409(4) . ? O5 C5 1.444(3) . ? O6 C15 1.347(4) . ? O6 C6 1.441(3) . ? O7 C8 1.212(3) . ? O8 C15 1.204(4) . ? C1 C2 1.520(4) . ? C1 C6 1.531(4) . ? C1 H1 1.0000 . ? C2 C3 1.520(4) . ? C2 H2 1.0000 . ? C3 C4 1.521(4) . ? C3 H3 1.0000 . ? C4 C5 1.535(4) . ? C4 H4 1.0000 . ? C5 C6 1.527(4) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.486(4) . ? C9 C10 1.392(4) . ? C9 C14 1.393(4) . ? C10 C11 1.378(4) . ? C10 H10 0.9500 . ? C11 C12 1.385(4) . ? C11 H11 0.9500 . ? C12 C13 1.387(4) . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.486(4) . ? C16 C21 1.384(5) . ? C16 C17 1.387(4) . ? C17 C18 1.381(5) . ? C17 H17 0.9500 . ? C18 C19 1.369(5) . ? C18 H18 0.9500 . ? C19 C20 1.379(5) . ? C20 C21 1.383(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 O9 1.409(14) . ? C22 C23 1.428(13) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O10 1.379(13) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 O10 1.384(12) . ? C24 C25 1.425(12) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 O9 1.378(14) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C22' O9' 1.439(14) . ? C22' C23' 1.558(10) . ? C22' H22C 0.9900 . ? C22' H22D 0.9900 . ? C23' O10' 1.402(12) . ? C23' H23C 0.9900 . ? C23' H23D 0.9900 . ? C24' O10' 1.405(12) . ? C24' C25' 1.588(10) . ? C24' H24C 0.9900 . ? C24' H24D 0.9900 . ? C25' O9' 1.413(15) . ? C25' H25C 0.9900 . ? C25' H25D 0.9900 . ? 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 110.4(2) . . ? C8 O2 C2 115.8(2) . . ? C7 O3 C3 111.0(2) . . ? C4 O4 H4A 108(3) . . ? C7 O5 C5 111.3(2) . . ? C15 O6 C6 116.2(2) . . ? O1 C1 C2 110.2(2) . . ? O1 C1 C6 106.5(2) . . ? C2 C1 C6 109.6(2) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C1 106.9(2) . . ? O2 C2 C3 110.6(2) . . ? C1 C2 C3 108.3(2) . . ? O2 C2 H2 110.3 . . ? C1 C2 H2 110.3 . . ? C3 C2 H2 110.3 . . ? O3 C3 C2 109.4(2) . . ? O3 C3 C4 107.8(2) . . ? C2 C3 C4 110.4(2) . . ? O3 C3 H3 109.7 . . ? C2 C3 H3 109.7 . . ? C4 C3 H3 109.7 . . ? O4 C4 C3 108.1(2) . . ? O4 C4 C5 115.1(2) . . ? C3 C4 C5 106.9(2) . . ? O4 C4 H4 108.9 . . ? C3 C4 H4 108.9 . . ? C5 C4 H4 108.9 . . ? O5 C5 C6 105.3(2) . . ? O5 C5 C4 106.8(2) . . ? C6 C5 C4 114.4(2) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 108.5(2) . . ? O6 C6 C1 111.3(2) . . ? C5 C6 C1 108.0(2) . . ? O6 C6 H6 109.7 . . ? C5 C6 H6 109.7 . . ? C1 C6 H6 109.7 . . ? O3 C7 O1 111.2(2) . . ? O3 C7 O5 111.8(2) . . ? O1 C7 O5 111.0(2) . . ? O3 C7 H7 107.6 . . ? O1 C7 H7 107.6 . . ? O5 C7 H7 107.6 . . ? O7 C8 O2 123.1(3) . . ? O7 C8 C9 124.5(3) . . ? O2 C8 C9 112.4(2) . . ? C10 C9 C14 119.9(3) . . ? C10 C9 C8 118.0(3) . . ? C14 C9 C8 122.0(3) . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.1(3) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 C13 121.7(3) . . ? C11 C12 Cl1 118.7(2) . . ? C13 C12 Cl1 119.6(2) . . ? C14 C13 C12 118.8(3) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C9 120.3(3) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? O8 C15 O6 123.4(3) . . ? O8 C15 C16 125.0(3) . . ? O6 C15 C16 111.6(3) . . ? C21 C16 C17 119.1(3) . . ? C21 C16 C15 123.1(3) . . ? C17 C16 C15 117.8(3) . . ? C18 C17 C16 120.2(4) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 119.7(3) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C20 121.3(3) . . ? C18 C19 Cl2 119.2(3) . . ? C20 C19 Cl2 119.4(3) . . ? C19 C20 C21 118.7(3) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C20 C21 C16 121.0(3) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? O9 C22 C23 113.1(11) . . ? O9 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? O9 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? O10 C23 C22 116.7(10) . . ? O10 C23 H23A 108.1 . . ? C22 C23 H23A 108.1 . . ? O10 C23 H23B 108.1 . . ? C22 C23 H23B 108.1 . . ? H23A C23 H23B 107.3 . . ? O10 C24 C25 119.1(9) . . ? O10 C24 H24A 107.5 . . ? C25 C24 H24A 107.5 . . ? O10 C24 H24B 107.5 . . ? C25 C24 H24B 107.5 . . ? H24A C24 H24B 107.0 . . ? O9 C25 C24 120.4(10) . . ? O9 C25 H25A 107.2 . . ? C24 C25 H25A 107.2 . . ? O9 C25 H25B 107.2 . . ? C24 C25 H25B 107.2 . . ? H25A C25 H25B 106.9 . . ? C25 O9 C22 116.1(11) . . ? C23 O10 C24 112.8(9) . . ? O9' C22' C23' 106.9(9) . . ? O9' C22' H22C 110.4 . . ? C23' C22' H22C 110.4 . . ? O9' C22' H22D 110.4 . . ? C23' C22' H22D 110.4 . . ? H22C C22' H22D 108.6 . . ? O10' C23' C22' 107.7(8) . . ? O10' C23' H23C 110.2 . . ? C22' C23' H23C 110.2 . . ? O10' C23' H23D 110.2 . . ? C22' C23' H23D 110.2 . . ? H23C C23' H23D 108.5 . . ? O10' C24' C25' 104.2(8) . . ? O10' C24' H24C 110.9 . . ? C25' C24' H24C 110.9 . . ? O10' C24' H24D 110.9 . . ? C25' C24' H24D 110.9 . . ? H24C C24' H24D 108.9 . . ? O9' C25' C24' 102.4(10) . . ? O9' C25' H25C 111.3 . . ? C24' C25' H25C 111.3 . . ? O9' C25' H25D 111.3 . . ? C24' C25' H25D 111.3 . . ? H25C C25' H25D 109.2 . . ? C25' O9' C22' 102.9(11) . . ? C23' O10' C24' 108.2(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C2 57.8(3) . . . . ? C7 O1 C1 C6 -61.0(3) . . . . ? C8 O2 C2 C1 160.6(2) . . . . ? C8 O2 C2 C3 -81.7(3) . . . . ? O1 C1 C2 O2 65.7(3) . . . . ? C6 C1 C2 O2 -177.4(2) . . . . ? O1 C1 C2 C3 -53.6(3) . . . . ? C6 C1 C2 C3 63.3(3) . . . . ? C7 O3 C3 C2 -59.2(3) . . . . ? C7 O3 C3 C4 60.9(3) . . . . ? O2 C2 C3 O3 -63.1(3) . . . . ? C1 C2 C3 O3 53.8(3) . . . . ? O2 C2 C3 C4 178.5(2) . . . . ? C1 C2 C3 C4 -64.6(3) . . . . ? O3 C3 C4 O4 175.2(2) . . . . ? C2 C3 C4 O4 -65.4(3) . . . . ? O3 C3 C4 C5 -60.3(3) . . . . ? C2 C3 C4 C5 59.1(3) . . . . ? C7 O5 C5 C6 61.7(3) . . . . ? C7 O5 C5 C4 -60.3(3) . . . . ? O4 C4 C5 O5 179.8(2) . . . . ? C3 C4 C5 O5 59.7(3) . . . . ? O4 C4 C5 C6 63.8(3) . . . . ? C3 C4 C5 C6 -56.3(3) . . . . ? C15 O6 C6 C5 -153.0(2) . . . . ? C15 O6 C6 C1 88.4(3) . . . . ? O5 C5 C6 O6 178.5(2) . . . . ? C4 C5 C6 O6 -64.6(3) . . . . ? O5 C5 C6 C1 -60.8(3) . . . . ? C4 C5 C6 C1 56.1(3) . . . . ? O1 C1 C6 O6 -179.9(2) . . . . ? C2 C1 C6 O6 61.0(3) . . . . ? O1 C1 C6 C5 61.2(3) . . . . ? C2 C1 C6 C5 -58.0(3) . . . . ? C3 O3 C7 O1 63.6(3) . . . . ? C3 O3 C7 O5 -61.0(3) . . . . ? C1 O1 C7 O3 -62.5(3) . . . . ? C1 O1 C7 O5 62.5(3) . . . . ? C5 O5 C7 O3 61.2(3) . . . . ? C5 O5 C7 O1 -63.5(3) . . . . ? C2 O2 C8 O7 -1.4(4) . . . . ? C2 O2 C8 C9 179.4(2) . . . . ? O7 C8 C9 C10 -3.8(4) . . . . ? O2 C8 C9 C10 175.4(2) . . . . ? O7 C8 C9 C14 177.2(3) . . . . ? O2 C8 C9 C14 -3.6(4) . . . . ? C14 C9 C10 C11 0.7(4) . . . . ? C8 C9 C10 C11 -178.3(3) . . . . ? C9 C10 C11 C12 -0.3(4) . . . . ? C10 C11 C12 C13 -0.5(4) . . . . ? C10 C11 C12 Cl1 179.2(2) . . . . ? C11 C12 C13 C14 0.9(4) . . . . ? Cl1 C12 C13 C14 -178.8(2) . . . . ? C12 C13 C14 C9 -0.5(4) . . . . ? C10 C9 C14 C13 -0.3(4) . . . . ? C8 C9 C14 C13 178.7(3) . . . . ? C6 O6 C15 O8 -2.4(4) . . . . ? C6 O6 C15 C16 177.8(2) . . . . ? O8 C15 C16 C21 175.9(3) . . . . ? O6 C15 C16 C21 -4.3(4) . . . . ? O8 C15 C16 C17 -4.7(5) . . . . ? O6 C15 C16 C17 175.0(3) . . . . ? C21 C16 C17 C18 -2.4(5) . . . . ? C15 C16 C17 C18 178.2(3) . . . . ? C16 C17 C18 C19 0.1(6) . . . . ? C17 C18 C19 C20 2.3(6) . . . . ? C17 C18 C19 Cl2 -179.1(3) . . . . ? C18 C19 C20 C21 -2.1(6) . . . . ? Cl2 C19 C20 C21 179.2(3) . . . . ? C19 C20 C21 C16 -0.3(5) . . . . ? C17 C16 C21 C20 2.5(5) . . . . ? C15 C16 C21 C20 -178.1(3) . . . . ? O9 C22 C23 O10 50.7(19) . . . . ? O10 C24 C25 O9 -17(2) . . . . ? C24 C25 O9 C22 20(3) . . . . ? C23 C22 O9 C25 -35(2) . . . . ? C22 C23 O10 C24 -47.0(16) . . . . ? C25 C24 O10 C23 29.6(16) . . . . ? O9' C22' C23' O10' -62.3(13) . . . . ? O10' C24' C25' O9' 74.4(11) . . . . ? C24' C25' O9' C22' -74.3(14) . . . . ? C23' C22' O9' C25' 69.6(15) . . . . ? C22' C23' O10' C24' 62.4(11) . . . . ? C25' C24' O10' C23' -67.6(10) . . . . ? 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 O4 H4A O7 0.82(4) 2.02(2) 2.828(3) 171(5) 2_545 C23' H23D Cl2 0.99 2.76 3.607(7) 144.2 2_545 C24 H24A Cl2 0.99 2.79 3.587(12) 138.5 4_675 C23' H23D O3 0.99 2.51 3.286(6) 134.8 3_665 C25' H25C O8 0.99 2.51 3.481(8) 166.0 2 C7 H7 O10' 1.00 2.20 3.110(12) 150.3 3_665 C7 H7 O10 1.00 2.23 3.137(12) 150.6 3_665 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.595 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.061 #===END data_3G _database_code_depnum_ccdc_archive 'CCDC 752189' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate dimethyl sulphoxide solvate ; _chemical_name_common ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate dimethyl sulphoxide solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, C2 H6 O S' _chemical_formula_sum 'C23 H22 Cl2 O9 S' _chemical_formula_weight 545.37 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9731(13) _cell_length_b 10.2342(11) _cell_length_c 18.0469(19) _cell_angle_alpha 90.00 _cell_angle_beta 102.585(2) _cell_angle_gamma 90.00 _cell_volume 2338.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 5048 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 28.04 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8956 _exptl_absorpt_correction_T_max 0.9564 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11333 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4119 _reflns_number_gt 3752 _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 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^)+(0.0454P)^2^+2.9360P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4119 _refine_ls_number_parameters 382 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.148 _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 Cl1 Cl 0.04052(6) 1.19704(7) -0.20521(4) 0.0313(2) Uani 1 1 d . . . Cl2 Cl -0.10712(6) 0.71609(8) 0.50661(4) 0.0376(2) Uani 1 1 d . . . O1 O 0.13678(14) 0.44118(18) 0.03442(10) 0.0221(4) Uani 1 1 d . . . O2 O 0.14013(14) 0.71930(17) 0.05019(10) 0.0195(4) Uani 1 1 d . . . O3 O 0.30620(14) 0.52438(18) 0.07133(10) 0.0237(4) Uani 1 1 d . . . O4 O 0.28765(16) 0.58391(19) 0.26561(10) 0.0262(4) Uani 1 1 d D . . O5 O 0.26414(15) 0.32593(17) 0.12006(10) 0.0235(4) Uani 1 1 d . . . O6 O 0.08068(15) 0.47876(18) 0.22249(10) 0.0250(4) Uani 1 1 d . . . O7 O 0.19975(16) 0.88690(18) 0.12751(10) 0.0269(5) Uani 1 1 d . . . O8 O 0.00602(19) 0.2927(2) 0.25124(13) 0.0392(6) Uani 1 1 d . . . C1 C 0.1007(2) 0.5084(3) 0.09421(15) 0.0205(6) Uani 1 1 d . . . C2 C 0.1647(2) 0.6324(3) 0.11509(14) 0.0194(6) Uani 1 1 d . . . C3 C 0.2812(2) 0.5966(3) 0.13347(15) 0.0213(6) Uani 1 1 d . . . C4 C 0.3058(2) 0.5101(3) 0.20356(15) 0.0229(6) Uani 1 1 d . . . C5 C 0.2367(2) 0.3875(3) 0.18566(15) 0.0223(6) Uani 1 1 d . . . C6 C 0.1189(2) 0.4157(3) 0.16220(15) 0.0221(6) Uani 1 1 d . . . C7 C 0.2451(2) 0.4103(3) 0.05720(15) 0.0224(6) Uani 1 1 d . . . C8 C 0.1610(2) 0.8464(3) 0.06445(14) 0.0197(6) Uani 1 1 d . . . C9 C 0.13126(19) 0.9297(3) -0.00391(14) 0.0188(5) Uani 1 1 d . . . C10 C 0.1378(2) 1.0648(3) 0.00543(15) 0.0213(6) Uani 1 1 d . . . C11 C 0.1095(2) 1.1466(3) -0.05622(16) 0.0231(6) Uani 1 1 d . . . C12 C 0.0757(2) 1.0924(3) -0.12762(15) 0.0225(6) Uani 1 1 d . . . C13 C 0.0687(2) 0.9585(3) -0.13849(16) 0.0248(6) Uani 1 1 d . . . C14 C 0.0965(2) 0.8772(3) -0.07622(15) 0.0222(6) Uani 1 1 d . . . C15 C 0.0266(2) 0.4064(3) 0.26345(15) 0.0227(6) Uani 1 1 d . . . C16 C -0.0045(2) 0.4854(3) 0.32385(15) 0.0220(6) Uani 1 1 d . . . C17 C -0.0895(2) 0.4431(3) 0.35303(17) 0.0277(6) Uani 1 1 d . . . C18 C -0.1214(2) 0.5140(3) 0.40910(16) 0.0286(7) Uani 1 1 d . . . C19 C -0.0666(2) 0.6250(3) 0.43642(15) 0.0256(6) Uani 1 1 d . . . C20 C 0.0197(2) 0.6672(3) 0.41004(16) 0.0276(6) Uani 1 1 d . . . C21 C 0.0506(2) 0.5974(3) 0.35287(15) 0.0239(6) Uani 1 1 d . . . C22 C 0.5738(3) 0.5194(4) 0.1251(3) 0.0637(12) Uani 1 1 d . . . H22A H 0.5210 0.5856 0.1298 0.095 Uiso 1 1 calc R . . H22B H 0.5641 0.4421 0.1549 0.095 Uiso 1 1 calc R . . H22C H 0.5654 0.4949 0.0716 0.095 Uiso 1 1 calc R . . H1 H 0.029(2) 0.526(3) 0.0744(14) 0.014(7) Uiso 1 1 d . . . H2 H 0.146(2) 0.671(3) 0.1548(16) 0.021(7) Uiso 1 1 d . . . H3 H 0.324(2) 0.674(3) 0.1390(15) 0.018(7) Uiso 1 1 d . . . H4 H 0.379(2) 0.481(3) 0.2121(15) 0.019(7) Uiso 1 1 d . . . H5 H 0.251(2) 0.327(3) 0.2239(16) 0.023(7) Uiso 1 1 d . . . H6 H 0.082(2) 0.340(3) 0.1464(15) 0.017(7) Uiso 1 1 d . . . H7 H 0.264(2) 0.370(3) 0.0173(16) 0.017(7) Uiso 1 1 d . . . H10 H 0.159(2) 1.098(3) 0.0515(16) 0.018(7) Uiso 1 1 d . . . H11 H 0.111(2) 1.233(3) -0.0505(17) 0.026(8) Uiso 1 1 d . . . H13 H 0.048(2) 0.925(3) -0.1846(17) 0.022(7) Uiso 1 1 d . . . H14 H 0.092(2) 0.783(3) -0.0821(16) 0.022(7) Uiso 1 1 d . . . H17 H -0.124(2) 0.367(3) 0.3362(16) 0.025(8) Uiso 1 1 d . . . H18 H -0.174(2) 0.484(3) 0.4279(16) 0.025(8) Uiso 1 1 d . . . H20 H 0.052(2) 0.742(3) 0.4297(17) 0.027(8) Uiso 1 1 d . . . H21 H 0.105(2) 0.624(3) 0.3352(15) 0.016(7) Uiso 1 1 d . . . C23 C 0.7754(3) 0.4468(5) 0.1396(2) 0.0654(12) Uani 1 1 d . . . H23A H 0.7515 0.4216 0.0862 0.098 Uiso 1 1 calc R . . H23B H 0.7651 0.3736 0.1722 0.098 Uiso 1 1 calc R . . H23C H 0.8504 0.4699 0.1496 0.098 Uiso 1 1 calc R . . O9 O 0.7136(2) 0.6863(2) 0.10271(15) 0.0510(7) Uani 1 1 d . . . S1 S 0.70124(7) 0.58356(10) 0.15905(5) 0.0451(2) Uani 1 1 d . . . H4A H 0.299(3) 0.533(3) 0.3023(15) 0.046(11) Uiso 1 1 d 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 Cl1 0.0421(4) 0.0221(4) 0.0246(4) 0.0076(3) -0.0040(3) -0.0007(3) Cl2 0.0374(4) 0.0471(5) 0.0327(4) -0.0136(4) 0.0173(3) -0.0009(3) O1 0.0255(10) 0.0221(10) 0.0180(9) -0.0055(8) 0.0035(7) 0.0013(8) O2 0.0269(10) 0.0140(9) 0.0165(9) 0.0018(7) 0.0026(7) 0.0018(7) O3 0.0233(10) 0.0249(10) 0.0239(10) -0.0017(8) 0.0074(8) -0.0011(8) O4 0.0387(12) 0.0215(10) 0.0163(10) 0.0008(8) 0.0010(8) 0.0010(9) O5 0.0324(11) 0.0171(9) 0.0222(10) -0.0005(8) 0.0083(8) 0.0063(8) O6 0.0372(11) 0.0187(10) 0.0234(10) -0.0024(8) 0.0158(8) -0.0028(8) O7 0.0427(12) 0.0204(10) 0.0161(9) -0.0016(8) 0.0030(8) -0.0006(8) O8 0.0577(15) 0.0213(12) 0.0474(13) -0.0086(10) 0.0309(11) -0.0105(10) C1 0.0212(14) 0.0208(14) 0.0199(13) -0.0032(11) 0.0051(11) 0.0013(11) C2 0.0274(14) 0.0155(13) 0.0153(13) 0.0028(11) 0.0046(11) 0.0032(11) C3 0.0230(14) 0.0206(14) 0.0196(13) -0.0021(11) 0.0031(11) -0.0013(11) C4 0.0246(15) 0.0205(14) 0.0212(13) -0.0002(11) -0.0001(11) 0.0031(11) C5 0.0330(15) 0.0174(14) 0.0165(13) 0.0022(11) 0.0052(11) 0.0029(11) C6 0.0287(15) 0.0180(14) 0.0215(13) -0.0033(11) 0.0098(11) -0.0045(12) C7 0.0270(15) 0.0218(14) 0.0192(13) -0.0018(11) 0.0069(11) 0.0021(11) C8 0.0206(13) 0.0182(13) 0.0214(14) -0.0008(11) 0.0070(11) 0.0043(10) C9 0.0176(13) 0.0183(14) 0.0211(13) 0.0014(11) 0.0053(10) 0.0033(10) C10 0.0238(14) 0.0196(14) 0.0198(14) -0.0052(11) 0.0031(11) -0.0015(11) C11 0.0240(14) 0.0149(14) 0.0292(15) -0.0009(12) 0.0033(11) 0.0009(11) C12 0.0228(14) 0.0202(14) 0.0224(13) 0.0035(11) 0.0003(11) 0.0002(11) C13 0.0327(16) 0.0192(14) 0.0190(14) -0.0019(11) -0.0016(12) -0.0028(12) C14 0.0272(15) 0.0129(14) 0.0246(14) -0.0011(11) 0.0014(11) 0.0007(11) C15 0.0232(14) 0.0174(14) 0.0276(14) 0.0000(11) 0.0059(11) -0.0012(11) C16 0.0255(14) 0.0212(14) 0.0202(13) 0.0041(11) 0.0069(11) 0.0010(11) C17 0.0314(16) 0.0219(15) 0.0319(16) -0.0015(13) 0.0115(12) -0.0047(13) C18 0.0270(16) 0.0326(17) 0.0298(15) 0.0034(13) 0.0140(13) -0.0019(13) C19 0.0287(15) 0.0288(16) 0.0213(13) -0.0028(12) 0.0099(11) 0.0054(12) C20 0.0291(15) 0.0272(16) 0.0269(15) -0.0061(13) 0.0069(12) -0.0057(13) C21 0.0226(14) 0.0261(15) 0.0253(14) 0.0020(12) 0.0100(12) -0.0032(12) C22 0.046(2) 0.058(3) 0.089(3) 0.024(2) 0.022(2) -0.0011(19) C23 0.062(3) 0.072(3) 0.058(3) 0.003(2) 0.004(2) 0.032(2) O9 0.0631(16) 0.0427(15) 0.0579(15) -0.0095(12) 0.0368(13) -0.0081(12) S1 0.0468(5) 0.0564(6) 0.0339(4) -0.0069(4) 0.0126(4) 0.0056(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C12 1.743(3) . ? Cl2 C19 1.744(3) . ? O1 C7 1.411(3) . ? O1 C1 1.441(3) . ? O2 C8 1.342(3) . ? O2 C2 1.449(3) . ? O3 C7 1.403(3) . ? O3 C3 1.438(3) . ? O4 C4 1.413(3) . ? O4 H4A 0.831(18) . ? O5 C7 1.404(3) . ? O5 C5 1.453(3) . ? O6 C15 1.346(3) . ? O6 C6 1.442(3) . ? O7 C8 1.212(3) . ? O8 C15 1.203(3) . ? C1 C2 1.518(4) . ? C1 C6 1.528(4) . ? C1 H1 0.94(3) . ? C2 C3 1.520(4) . ? C2 H2 0.89(3) . ? C3 C4 1.520(4) . ? C3 H3 0.96(3) . ? C4 C5 1.534(4) . ? C4 H4 0.98(3) . ? C5 C6 1.522(4) . ? C5 H5 0.91(3) . ? C6 H6 0.92(3) . ? C7 H7 0.90(3) . ? C8 C9 1.480(4) . ? C9 C14 1.392(4) . ? C9 C10 1.394(4) . ? C10 C11 1.376(4) . ? C10 H10 0.89(3) . ? C11 C12 1.384(4) . ? C11 H11 0.89(3) . ? C12 C13 1.384(4) . ? C13 C14 1.382(4) . ? C13 H13 0.89(3) . ? C14 H14 0.97(3) . ? C15 C16 1.482(4) . ? C16 C17 1.391(4) . ? C16 C21 1.392(4) . ? C17 C18 1.380(4) . ? C17 H17 0.91(3) . ? C18 C19 1.373(4) . ? C18 H18 0.88(3) . ? C19 C20 1.378(4) . ? C20 C21 1.384(4) . ? C20 H20 0.91(3) . ? C21 H21 0.88(3) . ? C22 S1 1.760(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 S1 1.776(4) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O9 S1 1.495(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 C1 110.72(19) . . ? C8 O2 C2 116.09(19) . . ? C7 O3 C3 110.8(2) . . ? C4 O4 H4A 105(3) . . ? C7 O5 C5 111.13(19) . . ? C15 O6 C6 118.3(2) . . ? O1 C1 C2 109.7(2) . . ? O1 C1 C6 106.6(2) . . ? C2 C1 C6 109.8(2) . . ? O1 C1 H1 105.3(16) . . ? C2 C1 H1 112.2(16) . . ? C6 C1 H1 113.0(16) . . ? O2 C2 C1 107.5(2) . . ? O2 C2 C3 110.9(2) . . ? C1 C2 C3 108.4(2) . . ? O2 C2 H2 109.2(18) . . ? C1 C2 H2 109.8(18) . . ? C3 C2 H2 111.0(18) . . ? O3 C3 C4 107.9(2) . . ? O3 C3 C2 109.7(2) . . ? C4 C3 C2 109.9(2) . . ? O3 C3 H3 106.4(16) . . ? C4 C3 H3 112.5(16) . . ? C2 C3 H3 110.3(16) . . ? O4 C4 C3 107.9(2) . . ? O4 C4 C5 114.4(2) . . ? C3 C4 C5 107.1(2) . . ? O4 C4 H4 111.4(16) . . ? C3 C4 H4 109.4(16) . . ? C5 C4 H4 106.6(16) . . ? O5 C5 C6 105.4(2) . . ? O5 C5 C4 106.9(2) . . ? C6 C5 C4 114.1(2) . . ? O5 C5 H5 106.1(18) . . ? C6 C5 H5 111.3(18) . . ? C4 C5 H5 112.4(18) . . ? O6 C6 C5 111.4(2) . . ? O6 C6 C1 108.1(2) . . ? C5 C6 C1 108.1(2) . . ? O6 C6 H6 111.4(17) . . ? C5 C6 H6 110.7(17) . . ? C1 C6 H6 107.0(17) . . ? O3 C7 O5 111.8(2) . . ? O3 C7 O1 110.7(2) . . ? O5 C7 O1 111.2(2) . . ? O3 C7 H7 106.5(17) . . ? O5 C7 H7 109.5(18) . . ? O1 C7 H7 106.8(17) . . ? O7 C8 O2 122.4(2) . . ? O7 C8 C9 124.4(2) . . ? O2 C8 C9 113.2(2) . . ? C14 C9 C10 119.7(2) . . ? C14 C9 C8 122.1(2) . . ? C10 C9 C8 118.2(2) . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 119.8(18) . . ? C9 C10 H10 119.7(18) . . ? C10 C11 C12 118.9(3) . . ? C10 C11 H11 121.0(19) . . ? C12 C11 H11 120.0(19) . . ? C11 C12 C13 121.8(3) . . ? C11 C12 Cl1 118.4(2) . . ? C13 C12 Cl1 119.8(2) . . ? C14 C13 C12 118.9(3) . . ? C14 C13 H13 120.2(19) . . ? C12 C13 H13 120.9(19) . . ? C13 C14 C9 120.2(2) . . ? C13 C14 H14 120.7(17) . . ? C9 C14 H14 119.0(17) . . ? O8 C15 O6 123.5(3) . . ? O8 C15 C16 125.2(3) . . ? O6 C15 C16 111.2(2) . . ? C17 C16 C21 119.9(3) . . ? C17 C16 C15 118.3(2) . . ? C21 C16 C15 121.7(2) . . ? C18 C17 C16 120.2(3) . . ? C18 C17 H17 119.1(19) . . ? C16 C17 H17 120.7(19) . . ? C19 C18 C17 118.9(3) . . ? C19 C18 H18 122.2(19) . . ? C17 C18 H18 119(2) . . ? C18 C19 C20 122.1(3) . . ? C18 C19 Cl2 119.2(2) . . ? C20 C19 Cl2 118.7(2) . . ? C19 C20 C21 119.0(3) . . ? C19 C20 H20 118.2(19) . . ? C21 C20 H20 122.8(19) . . ? C20 C21 C16 119.8(3) . . ? C20 C21 H21 119.8(18) . . ? C16 C21 H21 120.3(18) . . ? S1 C22 H22A 109.5 . . ? S1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? S1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? S1 C23 H23A 109.5 . . ? S1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? S1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O9 S1 C22 104.90(18) . . ? O9 S1 C23 106.05(18) . . ? C22 S1 C23 98.4(2) . . ? 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 58.6(3) . . . . ? C7 O1 C1 C6 -60.3(3) . . . . ? C8 O2 C2 C1 159.5(2) . . . . ? C8 O2 C2 C3 -82.1(3) . . . . ? O1 C1 C2 O2 66.2(3) . . . . ? C6 C1 C2 O2 -177.0(2) . . . . ? O1 C1 C2 C3 -53.8(3) . . . . ? C6 C1 C2 C3 63.1(3) . . . . ? C7 O3 C3 C4 60.8(3) . . . . ? C7 O3 C3 C2 -59.0(3) . . . . ? O2 C2 C3 O3 -63.8(3) . . . . ? C1 C2 C3 O3 54.0(3) . . . . ? O2 C2 C3 C4 177.7(2) . . . . ? C1 C2 C3 C4 -64.5(3) . . . . ? O3 C3 C4 O4 176.3(2) . . . . ? C2 C3 C4 O4 -64.1(3) . . . . ? O3 C3 C4 C5 -60.1(3) . . . . ? C2 C3 C4 C5 59.5(3) . . . . ? C7 O5 C5 C6 61.7(3) . . . . ? C7 O5 C5 C4 -60.1(3) . . . . ? O4 C4 C5 O5 178.8(2) . . . . ? C3 C4 C5 O5 59.4(3) . . . . ? O4 C4 C5 C6 62.7(3) . . . . ? C3 C4 C5 C6 -56.7(3) . . . . ? C15 O6 C6 C5 -102.8(3) . . . . ? C15 O6 C6 C1 138.6(2) . . . . ? O5 C5 C6 O6 -179.49(19) . . . . ? C4 C5 C6 O6 -62.5(3) . . . . ? O5 C5 C6 C1 -60.9(3) . . . . ? C4 C5 C6 C1 56.0(3) . . . . ? O1 C1 C6 O6 -178.4(2) . . . . ? C2 C1 C6 O6 62.9(3) . . . . ? O1 C1 C6 C5 61.0(3) . . . . ? C2 C1 C6 C5 -57.7(3) . . . . ? C3 O3 C7 O5 -61.3(3) . . . . ? C3 O3 C7 O1 63.3(3) . . . . ? C5 O5 C7 O3 61.4(3) . . . . ? C5 O5 C7 O1 -62.9(3) . . . . ? C1 O1 C7 O3 -63.1(3) . . . . ? C1 O1 C7 O5 61.9(3) . . . . ? C2 O2 C8 O7 1.1(4) . . . . ? C2 O2 C8 C9 -178.4(2) . . . . ? O7 C8 C9 C14 173.7(3) . . . . ? O2 C8 C9 C14 -6.8(4) . . . . ? O7 C8 C9 C10 -6.9(4) . . . . ? O2 C8 C9 C10 172.6(2) . . . . ? C14 C9 C10 C11 0.4(4) . . . . ? C8 C9 C10 C11 -179.0(2) . . . . ? C9 C10 C11 C12 -0.7(4) . . . . ? C10 C11 C12 C13 0.6(4) . . . . ? C10 C11 C12 Cl1 -179.8(2) . . . . ? C11 C12 C13 C14 -0.1(4) . . . . ? Cl1 C12 C13 C14 -179.7(2) . . . . ? C12 C13 C14 C9 -0.2(4) . . . . ? C10 C9 C14 C13 0.1(4) . . . . ? C8 C9 C14 C13 179.5(3) . . . . ? C6 O6 C15 O8 -2.0(4) . . . . ? C6 O6 C15 C16 178.7(2) . . . . ? O8 C15 C16 C17 -21.8(4) . . . . ? O6 C15 C16 C17 157.5(2) . . . . ? O8 C15 C16 C21 156.5(3) . . . . ? O6 C15 C16 C21 -24.1(4) . . . . ? C21 C16 C17 C18 2.0(4) . . . . ? C15 C16 C17 C18 -179.7(3) . . . . ? C16 C17 C18 C19 -1.3(4) . . . . ? C17 C18 C19 C20 -0.5(5) . . . . ? C17 C18 C19 Cl2 179.4(2) . . . . ? C18 C19 C20 C21 1.6(4) . . . . ? Cl2 C19 C20 C21 -178.3(2) . . . . ? C19 C20 C21 C16 -0.9(4) . . . . ? C17 C16 C21 C20 -0.8(4) . . . . ? C15 C16 C21 C20 -179.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A O7 0.831(18) 1.96(2) 2.770(3) 166(4) 2_545 C11 H11 O1 0.89(3) 2.60(3) 3.411(3) 151(2) 1_565 C1 H1 O1 0.94(3) 2.60(3) 3.469(3) 154(2) 3_565 C17 H17 O9 0.91(3) 2.56(3) 3.270(4) 135(2) 2_545 C13 H13 O8 0.89(3) 2.56(3) 3.291(3) 141(2) 3_565 C5 H5 O4 0.91(3) 2.55(3) 3.263(3) 135(2) 2_545 C7 H7 O9 0.90(3) 2.32(3) 3.204(4) 165(2) 3_665 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.655 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.064 #===END data_3H _database_code_depnum_ccdc_archive 'CCDC 752190' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate 1,2-dichloroethane solvate ; _chemical_name_common ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate 1,2- dichloroethane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, C2 H4 Cl2' _chemical_formula_sum 'C23 H20 Cl4 O8' _chemical_formula_weight 566.19 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 monoclinic _symmetry_space_group_name_H-M 'P2 1/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.093(2) _cell_length_b 9.9108(17) _cell_length_c 20.260(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.433(3) _cell_angle_gamma 90.00 _cell_volume 2426.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 2061 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 26.15 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.536 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9159 _exptl_absorpt_correction_T_max 0.9549 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11676 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4214 _reflns_number_gt 3277 _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 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^)+(0.0536P)^2^+8.7789P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4214 _refine_ls_number_parameters 338 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.1685 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.042 _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 Cl1 Cl 1.22974(9) 1.20046(11) -0.13134(5) 0.0299(3) Uani 1 1 d . . . Cl2 Cl 0.40524(11) 0.63590(17) 0.31743(9) 0.0650(5) Uani 1 1 d . . . O1 O 1.1048(2) 0.4417(3) 0.07146(13) 0.0232(6) Uani 1 1 d . . . O2 O 1.0867(2) 0.7283(3) 0.08084(12) 0.0200(6) Uani 1 1 d . . . O3 O 1.2357(2) 0.5361(3) 0.14444(13) 0.0242(6) Uani 1 1 d . . . O4 O 1.0449(2) 0.5957(3) 0.27467(13) 0.0233(6) Uani 1 1 d D . . O5 O 1.1570(2) 0.3292(3) 0.16866(14) 0.0256(7) Uani 1 1 d . . . O6 O 0.8819(2) 0.4686(3) 0.18840(13) 0.0220(6) Uani 1 1 d . . . O7 O 1.0667(2) 0.9066(3) 0.14780(13) 0.0245(7) Uani 1 1 d . . . O8 O 0.7672(3) 0.3794(4) 0.10979(16) 0.0422(9) Uani 1 1 d . . . C1 C 1.0139(3) 0.5095(4) 0.10213(19) 0.0200(8) Uani 1 1 d . . . H1 H 0.9525 0.5278 0.0687 0.024 Uiso 1 1 calc R . . C2 C 1.0547(3) 0.6402(4) 0.13359(18) 0.0186(8) Uani 1 1 d . . . H2 H 0.9944 0.6829 0.1586 0.022 Uiso 1 1 calc R . . C3 C 1.1543(3) 0.6093(4) 0.18025(18) 0.0186(8) Uani 1 1 d . . . H3 H 1.1870 0.6952 0.1982 0.022 Uiso 1 1 calc R . . C4 C 1.1189(3) 0.5201(4) 0.23652(19) 0.0211(9) Uani 1 1 d . . . H4 H 1.1856 0.4961 0.2649 0.025 Uiso 1 1 calc R . . C5 C 1.0696(3) 0.3904(4) 0.2056(2) 0.0217(9) Uani 1 1 d . . . H5 H 1.0462 0.3276 0.2410 0.026 Uiso 1 1 calc R . . C6 C 0.9747(3) 0.4130(4) 0.15545(19) 0.0199(8) Uani 1 1 d . . . H6 H 0.9528 0.3249 0.1347 0.024 Uiso 1 1 calc R . . C7 C 1.1913(3) 0.4159(4) 0.1187(2) 0.0251(9) Uani 1 1 d . . . H7 H 1.2515 0.3687 0.0954 0.030 Uiso 1 1 calc R . . C8 C 1.0904(3) 0.8610(4) 0.09428(19) 0.0206(9) Uani 1 1 d . . . C9 C 1.1259(3) 0.9418(4) 0.03804(19) 0.0196(8) Uani 1 1 d . . . C10 C 1.1304(3) 1.0823(4) 0.04387(19) 0.0218(9) Uani 1 1 d . . . H10 H 1.1118 1.1236 0.0842 0.026 Uiso 1 1 calc R . . C11 C 1.1614(3) 1.1612(4) -0.0075(2) 0.0239(9) Uani 1 1 d . . . H11 H 1.1638 1.2566 -0.0033 0.029 Uiso 1 1 calc R . . C12 C 1.1893(3) 1.0995(4) -0.06612(19) 0.0228(9) Uani 1 1 d . . . C13 C 1.1848(3) 0.9608(4) -0.07373(19) 0.0233(9) Uani 1 1 d . . . H13 H 1.2029 0.9203 -0.1144 0.028 Uiso 1 1 calc R . . C14 C 1.1538(3) 0.8819(4) -0.02138(19) 0.0213(9) Uani 1 1 d . . . H14 H 1.1514 0.7865 -0.0258 0.026 Uiso 1 1 calc R . . C15 C 0.7805(3) 0.4418(4) 0.1606(2) 0.0251(9) Uani 1 1 d . . . C16 C 0.6900(3) 0.4979(4) 0.1999(2) 0.0247(9) Uani 1 1 d . . . C17 C 0.5821(4) 0.4764(5) 0.1768(2) 0.0395(12) Uani 1 1 d . . . H17 H 0.5685 0.4315 0.1359 0.047 Uiso 1 1 calc R . . C18 C 0.4946(4) 0.5193(6) 0.2123(3) 0.0440(13) Uani 1 1 d . . . H18 H 0.4206 0.5036 0.1966 0.053 Uiso 1 1 calc R . . C19 C 0.5162(4) 0.5855(5) 0.2713(3) 0.0405(12) Uani 1 1 d . . . C20 C 0.6223(4) 0.6120(6) 0.2938(3) 0.0457(14) Uani 1 1 d . . . H20 H 0.6356 0.6612 0.3336 0.055 Uiso 1 1 calc R . . C21 C 0.7100(4) 0.5666(5) 0.2583(2) 0.0343(11) Uani 1 1 d . . . H21 H 0.7839 0.5828 0.2741 0.041 Uiso 1 1 calc R . . H4A H 1.014(4) 0.543(5) 0.299(2) 0.051(17) Uiso 1 1 d D . . Cl3 Cl 0.6163(2) 0.3358(3) 0.38343(14) 0.1176(9) Uani 1 1 d D . . Cl4 Cl 0.4284(8) 0.3064(15) 0.5175(6) 0.087(2) Uani 0.20 1 d PD A 1 C22 C 0.561(3) 0.427(3) 0.4486(13) 0.091(3) Uani 0.20 1 d PDU A 1 H22A H 0.6018 0.5126 0.4549 0.109 Uiso 0.20 1 calc PR A 1 H22B H 0.4824 0.4488 0.4374 0.109 Uiso 0.20 1 calc PR A 1 C23 C 0.5681(19) 0.347(5) 0.5108(15) 0.100(3) Uani 0.20 1 d PDU A 1 H23A H 0.5964 0.4025 0.5487 0.120 Uiso 0.20 1 calc PR A 1 H23B H 0.6147 0.2661 0.5067 0.120 Uiso 0.20 1 calc PR A 1 Cl4A Cl 0.4317(4) 0.2270(9) 0.5297(4) 0.087(2) Uani 0.40 1 d PD A 2 C22A C 0.601(3) 0.217(3) 0.4421(14) 0.091(3) Uani 0.40 1 d PDU A 2 H22C H 0.5424 0.1542 0.4249 0.109 Uiso 0.40 1 calc PR A 2 H22D H 0.6704 0.1643 0.4451 0.109 Uiso 0.40 1 calc PR A 2 C23A C 0.5731(14) 0.251(3) 0.5107(10) 0.100(3) Uani 0.40 1 d PDU A 2 H23C H 0.5930 0.3462 0.5191 0.120 Uiso 0.40 1 calc PR A 2 H23D H 0.6197 0.1947 0.5414 0.120 Uiso 0.40 1 calc PR A 2 Cl4B Cl 0.4333(5) 0.1454(7) 0.5180(4) 0.087(2) Uani 0.40 1 d PD A 3 C22B C 0.591(3) 0.222(3) 0.4432(16) 0.091(3) Uani 0.40 1 d PDU A 3 H22E H 0.5674 0.1346 0.4241 0.109 Uiso 0.40 1 calc PR A 3 H22F H 0.6571 0.2086 0.4729 0.109 Uiso 0.40 1 calc PR A 3 C23B C 0.4960(17) 0.2902(18) 0.4801(11) 0.100(3) Uani 0.40 1 d PDU A 3 H23E H 0.4432 0.3366 0.4491 0.120 Uiso 0.40 1 calc PR A 3 H23F H 0.5248 0.3553 0.5136 0.120 Uiso 0.40 1 calc PR A 3 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 Cl1 0.0410(6) 0.0256(6) 0.0234(5) 0.0061(4) 0.0054(4) -0.0054(5) Cl2 0.0280(7) 0.0769(11) 0.0922(12) -0.0334(9) 0.0255(7) -0.0042(7) O1 0.0238(14) 0.0246(16) 0.0215(14) -0.0059(12) 0.0052(11) 0.0029(12) O2 0.0273(15) 0.0152(14) 0.0177(14) 0.0001(11) 0.0039(11) 0.0007(11) O3 0.0186(14) 0.0273(16) 0.0269(15) -0.0019(13) 0.0032(11) 0.0006(12) O4 0.0309(16) 0.0207(16) 0.0186(14) 0.0009(12) 0.0062(12) -0.0017(13) O5 0.0271(15) 0.0209(16) 0.0289(16) 0.0009(12) 0.0044(12) 0.0062(12) O6 0.0188(14) 0.0232(15) 0.0242(14) -0.0037(12) 0.0035(11) -0.0022(12) O7 0.0313(16) 0.0216(16) 0.0212(15) -0.0019(12) 0.0071(12) 0.0010(12) O8 0.0287(17) 0.058(2) 0.0399(19) -0.0227(18) -0.0015(14) -0.0013(16) C1 0.0189(19) 0.020(2) 0.021(2) -0.0045(17) 0.0017(15) 0.0020(16) C2 0.020(2) 0.018(2) 0.0183(19) 0.0011(16) 0.0054(15) -0.0006(16) C3 0.021(2) 0.015(2) 0.020(2) -0.0007(16) 0.0038(16) -0.0021(16) C4 0.023(2) 0.020(2) 0.020(2) 0.0018(17) -0.0012(16) 0.0014(17) C5 0.024(2) 0.019(2) 0.022(2) 0.0008(17) 0.0037(16) 0.0005(17) C6 0.021(2) 0.015(2) 0.025(2) -0.0023(16) 0.0048(16) 0.0013(16) C7 0.023(2) 0.023(2) 0.029(2) -0.0014(18) 0.0062(17) 0.0034(18) C8 0.019(2) 0.023(2) 0.020(2) -0.0010(17) 0.0008(16) 0.0023(16) C9 0.0190(19) 0.020(2) 0.0191(19) -0.0002(16) 0.0000(15) 0.0010(16) C10 0.026(2) 0.020(2) 0.019(2) -0.0055(17) 0.0031(16) -0.0002(17) C11 0.030(2) 0.017(2) 0.024(2) 0.0014(17) 0.0004(17) -0.0002(17) C12 0.023(2) 0.027(2) 0.018(2) 0.0048(17) 0.0011(16) -0.0032(17) C13 0.028(2) 0.023(2) 0.019(2) -0.0030(17) 0.0047(16) 0.0013(18) C14 0.027(2) 0.017(2) 0.020(2) 0.0009(16) 0.0002(16) 0.0003(17) C15 0.024(2) 0.023(2) 0.028(2) -0.0022(19) -0.0017(17) -0.0023(18) C16 0.022(2) 0.023(2) 0.029(2) 0.0000(18) 0.0024(17) -0.0030(17) C17 0.026(2) 0.051(3) 0.042(3) -0.012(2) -0.004(2) 0.004(2) C18 0.020(2) 0.051(3) 0.061(3) -0.009(3) -0.004(2) 0.001(2) C19 0.022(2) 0.040(3) 0.060(3) -0.006(3) 0.018(2) 0.001(2) C20 0.032(3) 0.057(4) 0.050(3) -0.028(3) 0.014(2) -0.010(2) C21 0.019(2) 0.038(3) 0.045(3) -0.010(2) 0.0050(19) -0.0063(19) Cl3 0.1146(19) 0.1072(19) 0.129(2) -0.0014(16) -0.0194(16) 0.0093(15) Cl4 0.0393(11) 0.134(7) 0.089(2) 0.023(4) 0.0183(12) 0.016(3) C22 0.078(6) 0.082(5) 0.111(6) -0.030(5) -0.006(5) 0.005(4) C23 0.087(6) 0.099(6) 0.114(6) -0.008(6) -0.010(5) 0.005(5) Cl4A 0.0393(11) 0.134(7) 0.089(2) 0.023(4) 0.0183(12) 0.016(3) C22A 0.078(6) 0.082(5) 0.111(6) -0.030(5) -0.006(5) 0.005(4) C23A 0.087(6) 0.099(6) 0.114(6) -0.008(6) -0.010(5) 0.005(5) Cl4B 0.0393(11) 0.134(7) 0.089(2) 0.023(4) 0.0183(12) 0.016(3) C22B 0.078(6) 0.082(5) 0.111(6) -0.030(5) -0.006(5) 0.005(4) C23B 0.087(6) 0.099(6) 0.114(6) -0.008(6) -0.010(5) 0.005(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 Cl1 C12 1.744(4) . ? Cl2 C19 1.741(5) . ? O1 C7 1.412(5) . ? O1 C1 1.450(4) . ? O2 C8 1.344(5) . ? O2 C2 1.445(4) . ? O3 C7 1.399(5) . ? O3 C3 1.444(5) . ? O4 C4 1.420(5) . ? O4 H4A 0.82(5) . ? O5 C7 1.403(5) . ? O5 C5 1.453(5) . ? O6 C15 1.355(5) . ? O6 C6 1.439(4) . ? O7 C8 1.220(5) . ? O8 C15 1.206(5) . ? C1 C2 1.517(5) . ? C1 C6 1.533(5) . ? C1 H1 1.0000 . ? C2 C3 1.530(5) . ? C2 H2 1.0000 . ? C3 C4 1.519(5) . ? C3 H3 1.0000 . ? C4 C5 1.539(6) . ? C4 H4 1.0000 . ? C5 C6 1.517(6) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.471(6) . ? C9 C14 1.396(5) . ? C9 C10 1.399(6) . ? C10 C11 1.367(6) . ? C10 H10 0.9500 . ? C11 C12 1.390(6) . ? C11 H11 0.9500 . ? C12 C13 1.384(6) . ? C13 C14 1.382(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.488(6) . ? C16 C21 1.378(6) . ? C16 C17 1.384(6) . ? C17 C18 1.372(7) . ? C17 H17 0.9500 . ? C18 C19 1.378(7) . ? C18 H18 0.9500 . ? C19 C20 1.369(7) . ? C20 C21 1.382(6) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? Cl3 C22B 1.689(17) . ? Cl3 C22A 1.692(17) . ? Cl3 C22 1.755(18) . ? Cl4 C23 1.748(19) . ? C22 C23 1.485(19) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? Cl4A C23A 1.784(15) . ? C22A C23A 1.482(19) . ? C22A H22C 0.9900 . ? C22A H22D 0.9900 . ? C23A H23C 0.9900 . ? C23A H23D 0.9900 . ? Cl4B C23B 1.809(16) . ? C22B C23B 1.550(18) . ? C22B H22E 0.9900 . ? C22B H22F 0.9900 . ? C23B H23E 0.9900 . ? C23B H23F 0.9900 . ? 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 110.3(3) . . ? C8 O2 C2 116.7(3) . . ? C7 O3 C3 110.9(3) . . ? C4 O4 H4A 108(4) . . ? C7 O5 C5 111.1(3) . . ? C15 O6 C6 116.2(3) . . ? O1 C1 C2 109.7(3) . . ? O1 C1 C6 106.0(3) . . ? C2 C1 C6 110.0(3) . . ? O1 C1 H1 110.4 . . ? C2 C1 H1 110.4 . . ? C6 C1 H1 110.4 . . ? O2 C2 C1 107.3(3) . . ? O2 C2 C3 110.5(3) . . ? C1 C2 C3 108.8(3) . . ? O2 C2 H2 110.1 . . ? C1 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? O3 C3 C4 107.7(3) . . ? O3 C3 C2 109.0(3) . . ? C4 C3 C2 109.9(3) . . ? O3 C3 H3 110.0 . . ? C4 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? O4 C4 C3 107.8(3) . . ? O4 C4 C5 114.8(3) . . ? C3 C4 C5 107.3(3) . . ? O4 C4 H4 108.9 . . ? C3 C4 H4 108.9 . . ? C5 C4 H4 108.9 . . ? O5 C5 C6 105.2(3) . . ? O5 C5 C4 106.3(3) . . ? C6 C5 C4 114.7(3) . . ? O5 C5 H5 110.1 . . ? C6 C5 H5 110.1 . . ? C4 C5 H5 110.1 . . ? O6 C6 C5 109.2(3) . . ? O6 C6 C1 111.0(3) . . ? C5 C6 C1 108.4(3) . . ? O6 C6 H6 109.4 . . ? C5 C6 H6 109.4 . . ? C1 C6 H6 109.4 . . ? O3 C7 O5 111.9(3) . . ? O3 C7 O1 111.1(3) . . ? O5 C7 O1 111.5(3) . . ? O3 C7 H7 107.4 . . ? O5 C7 H7 107.4 . . ? O1 C7 H7 107.4 . . ? O7 C8 O2 122.4(4) . . ? O7 C8 C9 125.0(4) . . ? O2 C8 C9 112.6(3) . . ? C14 C9 C10 119.1(4) . . ? C14 C9 C8 121.7(4) . . ? C10 C9 C8 119.2(4) . . ? C11 C10 C9 121.1(4) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 118.9(4) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C13 C12 C11 121.5(4) . . ? C13 C12 Cl1 119.8(3) . . ? C11 C12 Cl1 118.7(3) . . ? C14 C13 C12 119.1(4) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C9 120.3(4) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? O8 C15 O6 122.8(4) . . ? O8 C15 C16 125.1(4) . . ? O6 C15 C16 112.2(3) . . ? C21 C16 C17 119.7(4) . . ? C21 C16 C15 122.6(4) . . ? C17 C16 C15 117.7(4) . . ? C18 C17 C16 120.8(4) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 118.7(4) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 121.4(4) . . ? C20 C19 Cl2 119.9(4) . . ? C18 C19 Cl2 118.7(4) . . ? C19 C20 C21 119.6(5) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C16 C21 C20 119.8(4) . . ? C16 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C22B Cl3 C22 73.5(15) . . ? C22A Cl3 C22 76.8(13) . . ? C23 C22 Cl3 111(2) . . ? C23 C22 H22A 109.5 . . ? Cl3 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? Cl3 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C22 C23 Cl4 99.6(18) . . ? C22 C23 H23A 111.9 . . ? Cl4 C23 H23A 111.9 . . ? C22 C23 H23B 111.9 . . ? Cl4 C23 H23B 111.9 . . ? H23A C23 H23B 109.6 . . ? C23A C22A Cl3 122(2) . . ? C23A C22A H22C 106.7 . . ? Cl3 C22A H22C 106.7 . . ? C23A C22A H22D 106.7 . . ? Cl3 C22A H22D 106.7 . . ? H22C C22A H22D 106.6 . . ? C22A C23A Cl4A 115(2) . . ? C22A C23A H23C 108.4 . . ? Cl4A C23A H23C 108.4 . . ? C22A C23A H23D 108.4 . . ? Cl4A C23A H23D 108.4 . . ? H23C C23A H23D 107.5 . . ? C23B C22B Cl3 102.6(14) . . ? C23B C22B H22E 111.2 . . ? Cl3 C22B H22E 111.2 . . ? C23B C22B H22F 111.2 . . ? Cl3 C22B H22F 111.2 . . ? H22E C22B H22F 109.2 . . ? C22B C23B Cl4B 101.2(13) . . ? C22B C23B H23E 111.5 . . ? Cl4B C23B H23E 111.5 . . ? C22B C23B H23F 111.5 . . ? Cl4B C23B H23F 111.5 . . ? H23E C23B H23F 109.3 . . ? 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 C7 O1 C1 C2 58.2(4) . . . . ? C7 O1 C1 C6 -60.5(4) . . . . ? C8 O2 C2 C1 158.7(3) . . . . ? C8 O2 C2 C3 -82.8(4) . . . . ? O1 C1 C2 O2 65.8(4) . . . . ? C6 C1 C2 O2 -178.0(3) . . . . ? O1 C1 C2 C3 -53.7(4) . . . . ? C6 C1 C2 C3 62.5(4) . . . . ? C7 O3 C3 C4 60.3(4) . . . . ? C7 O3 C3 C2 -59.0(4) . . . . ? O2 C2 C3 O3 -63.8(4) . . . . ? C1 C2 C3 O3 53.8(4) . . . . ? O2 C2 C3 C4 178.4(3) . . . . ? C1 C2 C3 C4 -64.1(4) . . . . ? O3 C3 C4 O4 175.8(3) . . . . ? C2 C3 C4 O4 -65.5(4) . . . . ? O3 C3 C4 C5 -60.0(4) . . . . ? C2 C3 C4 C5 58.7(4) . . . . ? C7 O5 C5 C6 61.5(4) . . . . ? C7 O5 C5 C4 -60.6(4) . . . . ? O4 C4 C5 O5 179.6(3) . . . . ? C3 C4 C5 O5 59.8(4) . . . . ? O4 C4 C5 C6 63.7(4) . . . . ? C3 C4 C5 C6 -56.1(4) . . . . ? C15 O6 C6 C5 -152.4(3) . . . . ? C15 O6 C6 C1 88.1(4) . . . . ? O5 C5 C6 O6 177.6(3) . . . . ? C4 C5 C6 O6 -65.9(4) . . . . ? O5 C5 C6 C1 -61.3(4) . . . . ? C4 C5 C6 C1 55.2(4) . . . . ? O1 C1 C6 O6 -178.5(3) . . . . ? C2 C1 C6 O6 63.0(4) . . . . ? O1 C1 C6 C5 61.5(4) . . . . ? C2 C1 C6 C5 -56.9(4) . . . . ? C3 O3 C7 O5 -61.2(4) . . . . ? C3 O3 C7 O1 64.1(4) . . . . ? C5 O5 C7 O3 62.0(4) . . . . ? C5 O5 C7 O1 -63.1(4) . . . . ? C1 O1 C7 O3 -63.3(4) . . . . ? C1 O1 C7 O5 62.3(4) . . . . ? C2 O2 C8 O7 -1.0(5) . . . . ? C2 O2 C8 C9 178.8(3) . . . . ? O7 C8 C9 C14 178.7(4) . . . . ? O2 C8 C9 C14 -1.1(5) . . . . ? O7 C8 C9 C10 -2.1(6) . . . . ? O2 C8 C9 C10 178.1(3) . . . . ? C14 C9 C10 C11 0.2(6) . . . . ? C8 C9 C10 C11 -179.0(4) . . . . ? C9 C10 C11 C12 -0.5(6) . . . . ? C10 C11 C12 C13 1.0(6) . . . . ? C10 C11 C12 Cl1 -179.5(3) . . . . ? C11 C12 C13 C14 -1.2(6) . . . . ? Cl1 C12 C13 C14 179.3(3) . . . . ? C12 C13 C14 C9 0.9(6) . . . . ? C10 C9 C14 C13 -0.4(6) . . . . ? C8 C9 C14 C13 178.8(4) . . . . ? C6 O6 C15 O8 -2.8(6) . . . . ? C6 O6 C15 C16 177.3(3) . . . . ? O8 C15 C16 C21 178.9(5) . . . . ? O6 C15 C16 C21 -1.1(6) . . . . ? O8 C15 C16 C17 0.4(7) . . . . ? O6 C15 C16 C17 -179.6(4) . . . . ? C21 C16 C17 C18 -1.9(8) . . . . ? C15 C16 C17 C18 176.6(5) . . . . ? C16 C17 C18 C19 0.6(8) . . . . ? C17 C18 C19 C20 1.7(8) . . . . ? C17 C18 C19 Cl2 -178.3(4) . . . . ? C18 C19 C20 C21 -2.8(9) . . . . ? Cl2 C19 C20 C21 177.3(4) . . . . ? C17 C16 C21 C20 0.9(7) . . . . ? C15 C16 C21 C20 -177.6(5) . . . . ? C19 C20 C21 C16 1.4(8) . . . . ? C22B Cl3 C22 C23 18(2) . . . . ? C22A Cl3 C22 C23 15(3) . . . . ? Cl3 C22 C23 Cl4 -108(2) . . . . ? C22B Cl3 C22A C23A -54(18) . . . . ? C22 Cl3 C22A C23A -10(3) . . . . ? Cl3 C22A C23A Cl4A 101(3) . . . . ? C22A Cl3 C22B C23B 161 . . . . ? C22 Cl3 C22B C23B 26(2) . . . . ? Cl3 C22B C23B Cl4B 157(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C22 H22A Cl4A 0.99 2.63 3.46(3) 141.1 3_666 C23A H23D O8 0.99 2.33 3.29(2) 161.8 4_566 C22 H22A Cl4 0.99 1.92 2.73(3) 137.8 3_666 C18 H18 O3 0.95 2.45 3.370(5) 162.1 1_455 C11 H11 O1 0.95 2.50 3.294(5) 141.0 1_565 C5 H5 O4 1.00 2.56 3.265(5) 127.0 2_745 C14 H14 O8 0.95 2.59 3.313(5) 133.1 3_765 C7 H7 Cl4A 1.00 2.77 3.762(8) 172.1 4_665 C7 H7 Cl4B 1.00 2.76 3.688(7) 155.0 4_665 O4 H4A O7 0.82(5) 2.01(5) 2.825(4) 175(6) 2_745 C23 H23A Cl2 0.99 2.74 3.48(3) 132.3 3_666 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.965 _refine_diff_density_min -0.772 _refine_diff_density_rms 0.083 #===END data_3I _database_code_depnum_ccdc_archive 'CCDC 752191' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate acetonitrile solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate acetonitrile solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8 , C2 H3 N' _chemical_formula_sum 'C23 H19 Cl2 N O8' _chemical_formula_weight 508.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P(2) 1/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.074(10) _cell_length_b 9.861(8) _cell_length_c 20.003(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.894(13) _cell_angle_gamma 90.00 _cell_volume 2373(3) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 7187 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.49 _exptl_crystal_description 'square plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.68 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8002 _exptl_absorpt_correction_T_max 0.9419 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 21364 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4178 _reflns_number_gt 3590 _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 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^)+(0.0669P)^2^+0.8975P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4178 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Cl1 Cl 1.24645(6) 1.20804(6) -0.12916(3) 0.0476(2) Uani 1 1 d . . . Cl2 Cl 0.4320(8) 0.5778(10) 0.3396(5) 0.096(2) Uani 0.50 1 d P A 1 Cl2' Cl 0.4210(8) 0.6161(9) 0.3250(5) 0.105(3) Uani 0.50 1 d P A 2 O1 O 1.10994(12) 0.45299(15) 0.07167(7) 0.0341(4) Uani 1 1 d . . . O2 O 1.08585(12) 0.73876(14) 0.07997(7) 0.0313(3) Uani 1 1 d . . . O3 O 1.24046(12) 0.55563(16) 0.14756(8) 0.0360(4) Uani 1 1 d . . . O4 O 1.04966(13) 0.60527(15) 0.27611(7) 0.0333(4) Uani 1 1 d . . . O5 O 1.16888(13) 0.34287(15) 0.17116(8) 0.0371(4) Uani 1 1 d . . . O6 O 0.88849(12) 0.46955(14) 0.18714(7) 0.0327(4) Uani 1 1 d . . . O7 O 1.05813(14) 0.91981(15) 0.14453(7) 0.0390(4) Uani 1 1 d . . . O8 O 0.76931(16) 0.3692(2) 0.11025(10) 0.0629(6) Uani 1 1 d . . . C1 C 1.01705(18) 0.5166(2) 0.10095(10) 0.0288(5) Uani 1 1 d . . . C2 C 1.05493(18) 0.6507(2) 0.13350(10) 0.0275(4) Uani 1 1 d . . . C3 C 1.15620(18) 0.6244(2) 0.18216(10) 0.0303(5) Uani 1 1 d . . . C4 C 1.12503(18) 0.5323(2) 0.23907(10) 0.0297(5) Uani 1 1 d . . . C5 C 1.07965(19) 0.4001(2) 0.20670(11) 0.0322(5) Uani 1 1 d . . . C6 C 0.98178(18) 0.4183(2) 0.15453(11) 0.0309(5) Uani 1 1 d . . . C7 C 1.1994(2) 0.4319(2) 0.12053(11) 0.0362(5) Uani 1 1 d . . . C8 C 1.08774(17) 0.8728(2) 0.09298(10) 0.0284(4) Uani 1 1 d . . . C9 C 1.12946(17) 0.9527(2) 0.03772(10) 0.0275(4) Uani 1 1 d . . . C10 C 1.13507(19) 1.0941(2) 0.04365(11) 0.0330(5) Uani 1 1 d . . . C11 C 1.17219(19) 1.1718(2) -0.00704(11) 0.0347(5) Uani 1 1 d . . . C12 C 1.20310(18) 1.1082(2) -0.06426(10) 0.0326(5) Uani 1 1 d . . . C13 C 1.19845(19) 0.9679(2) -0.07151(11) 0.0349(5) Uani 1 1 d . . . C14 C 1.16180(18) 0.8905(2) -0.01998(10) 0.0303(5) Uani 1 1 d . . . C15 C 0.78604(19) 0.4329(2) 0.16139(11) 0.0368(5) Uani 1 1 d . . . C16 C 0.69817(18) 0.4808(2) 0.20350(11) 0.0366(5) Uani 1 1 d . A . C17 C 0.5877(2) 0.4508(4) 0.18338(18) 0.0704(10) Uani 1 1 d . . . C18 C 0.5044(3) 0.4876(4) 0.2226(2) 0.0876(13) Uani 1 1 d . A . C19 C 0.5311(2) 0.5539(3) 0.28178(17) 0.0648(9) Uani 1 1 d . . . C20 C 0.6391(2) 0.5883(3) 0.30212(16) 0.0551(7) Uani 1 1 d . A . C21 C 0.7228(2) 0.5513(3) 0.26246(13) 0.0422(6) Uani 1 1 d . . . H1 H 0.9606(17) 0.529(2) 0.0641(11) 0.023(5) Uiso 1 1 d . . . H2 H 0.9967(18) 0.693(2) 0.1546(10) 0.024(5) Uiso 1 1 d . . . H3 H 1.1898(18) 0.701(2) 0.1995(11) 0.028(6) Uiso 1 1 d . . . H4 H 1.1903(18) 0.511(2) 0.2664(10) 0.026(5) Uiso 1 1 d . . . H5 H 1.0629(19) 0.332(3) 0.2365(12) 0.035(6) Uiso 1 1 d . . . H6 H 0.9592(19) 0.341(2) 0.1328(11) 0.032(6) Uiso 1 1 d . . . H7 H 1.255(2) 0.391(2) 0.1002(11) 0.030(6) Uiso 1 1 d . . . H10 H 1.1166(19) 1.131(2) 0.0801(12) 0.033(6) Uiso 1 1 d . . . H11 H 1.175(2) 1.269(3) -0.0033(13) 0.051(7) Uiso 1 1 d . . . H13 H 1.220(2) 0.925(2) -0.1111(12) 0.040(6) Uiso 1 1 d . . . H14 H 1.156(2) 0.795(3) -0.0246(12) 0.039(6) Uiso 1 1 d . . . H17 H 0.570(3) 0.405(4) 0.1419(17) 0.086(11) Uiso 1 1 d . . . H18 H 0.431(4) 0.456(4) 0.211(2) 0.107(13) Uiso 1 1 d . . . H20 H 0.654(2) 0.633(3) 0.3399(15) 0.059(9) Uiso 1 1 d . . . H21 H 0.797(2) 0.569(3) 0.2774(13) 0.049(7) Uiso 1 1 d . . . H4A H 1.021(2) 0.555(3) 0.3005(15) 0.057(9) Uiso 1 1 d . . . C22 C 0.4313(4) 0.7170(7) 0.0484(3) 0.140(2) Uani 1 1 d . . . H22A H 0.3638 0.6651 0.0350 0.211 Uiso 1 1 calc R . . H22B H 0.4141 0.8141 0.0471 0.211 Uiso 1 1 calc R . . H22C H 0.4593 0.6913 0.0941 0.211 Uiso 1 1 calc R . . C23 C 0.5152(3) 0.6880(5) 0.0027(2) 0.0867(11) Uani 1 1 d . . . N1 N 0.5793(3) 0.6646(5) -0.03304(19) 0.1157(14) 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 Cl1 0.0684(4) 0.0368(3) 0.0392(3) 0.0106(2) 0.0127(3) -0.0083(3) Cl2 0.059(3) 0.103(4) 0.135(3) -0.039(3) 0.064(3) -0.017(2) Cl2' 0.0467(15) 0.122(6) 0.152(5) -0.074(5) 0.041(2) -0.016(3) O1 0.0415(9) 0.0312(8) 0.0312(8) -0.0053(6) 0.0133(7) 0.0035(6) O2 0.0492(9) 0.0215(7) 0.0253(7) 0.0009(6) 0.0154(6) 0.0005(6) O3 0.0323(8) 0.0382(9) 0.0392(8) -0.0015(7) 0.0129(6) -0.0004(7) O4 0.0466(9) 0.0281(8) 0.0274(8) 0.0009(6) 0.0157(7) -0.0005(7) O5 0.0416(9) 0.0292(8) 0.0424(9) 0.0020(7) 0.0140(7) 0.0096(7) O6 0.0322(8) 0.0297(8) 0.0378(8) -0.0055(6) 0.0116(6) -0.0040(6) O7 0.0542(10) 0.0307(8) 0.0350(8) -0.0059(6) 0.0208(7) 0.0002(7) O8 0.0481(11) 0.0812(15) 0.0589(12) -0.0353(11) 0.0009(9) 0.0018(10) C1 0.0331(11) 0.0268(11) 0.0274(11) -0.0032(8) 0.0075(9) 0.0019(8) C2 0.0352(11) 0.0240(10) 0.0249(10) 0.0013(8) 0.0124(9) 0.0005(9) C3 0.0356(12) 0.0266(11) 0.0302(11) -0.0030(9) 0.0108(9) -0.0031(9) C4 0.0339(12) 0.0289(11) 0.0269(10) 0.0023(8) 0.0053(9) 0.0021(9) C5 0.0401(12) 0.0241(10) 0.0340(11) 0.0049(9) 0.0137(9) 0.0042(9) C6 0.0373(12) 0.0208(10) 0.0363(12) -0.0066(9) 0.0126(9) -0.0022(9) C7 0.0382(13) 0.0339(12) 0.0388(12) -0.0017(10) 0.0158(10) 0.0058(10) C8 0.0327(11) 0.0249(10) 0.0282(10) -0.0025(8) 0.0067(8) 0.0020(8) C9 0.0307(11) 0.0254(10) 0.0267(10) -0.0004(8) 0.0037(8) 0.0016(8) C10 0.0439(13) 0.0261(11) 0.0298(11) -0.0054(9) 0.0076(9) 0.0022(9) C11 0.0435(13) 0.0219(11) 0.0384(12) 0.0008(9) 0.0028(10) -0.0001(9) C12 0.0386(12) 0.0287(11) 0.0308(11) 0.0066(9) 0.0048(9) -0.0039(9) C13 0.0454(13) 0.0308(11) 0.0298(11) -0.0019(9) 0.0113(10) -0.0003(10) C14 0.0382(12) 0.0226(11) 0.0308(11) -0.0009(8) 0.0078(9) 0.0011(9) C15 0.0385(13) 0.0327(12) 0.0393(13) -0.0032(10) 0.0033(10) -0.0028(10) C16 0.0343(12) 0.0320(12) 0.0439(13) -0.0023(10) 0.0064(10) -0.0029(9) C17 0.0395(15) 0.096(3) 0.075(2) -0.0410(19) 0.0036(14) -0.0066(15) C18 0.0320(16) 0.118(3) 0.113(3) -0.057(3) 0.0075(17) -0.0079(17) C19 0.0391(15) 0.0680(19) 0.091(2) -0.0284(17) 0.0290(15) -0.0101(13) C20 0.0455(15) 0.0601(18) 0.0622(18) -0.0244(15) 0.0192(13) -0.0087(13) C21 0.0323(13) 0.0447(14) 0.0507(14) -0.0082(11) 0.0092(11) -0.0074(11) C22 0.096(4) 0.186(6) 0.148(5) 0.012(4) 0.058(3) 0.033(3) C23 0.059(2) 0.125(3) 0.077(2) -0.012(2) 0.0114(18) 0.001(2) N1 0.071(2) 0.174(4) 0.106(3) -0.043(3) 0.031(2) -0.025(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 Cl1 C12 1.745(2) . ? Cl2 C19 1.749(9) . ? Cl2' C19 1.757(10) . ? O1 C7 1.409(3) . ? O1 C1 1.451(2) . ? O2 C8 1.347(3) . ? O2 C2 1.452(2) . ? O3 C7 1.408(3) . ? O3 C3 1.447(3) . ? O4 C4 1.418(3) . ? O4 H4A 0.80(3) . ? O5 C7 1.412(3) . ? O5 C5 1.454(3) . ? O6 C15 1.348(3) . ? O6 C6 1.441(3) . ? O7 C8 1.212(2) . ? O8 C15 1.203(3) . ? C1 C2 1.526(3) . ? C1 C6 1.532(3) . ? C1 H1 0.97(2) . ? C2 C3 1.519(3) . ? C2 H2 0.95(2) . ? C3 C4 1.528(3) . ? C3 H3 0.92(2) . ? C4 C5 1.535(3) . ? C4 H4 0.95(2) . ? C5 C6 1.519(3) . ? C5 H5 0.93(2) . ? C6 H6 0.91(2) . ? C7 H7 0.91(2) . ? C8 C9 1.480(3) . ? C9 C14 1.392(3) . ? C9 C10 1.401(3) . ? C10 C11 1.376(3) . ? C10 H10 0.86(2) . ? C11 C12 1.384(3) . ? C11 H11 0.96(3) . ? C12 C13 1.391(3) . ? C13 C14 1.385(3) . ? C13 H13 0.96(2) . ? C14 H14 0.95(3) . ? C15 C16 1.487(3) . ? C16 C21 1.380(3) . ? C16 C17 1.391(4) . ? C17 C18 1.377(4) . ? C17 H17 0.96(4) . ? C18 C19 1.366(5) . ? C18 H18 0.94(4) . ? C19 C20 1.375(4) . ? C20 C21 1.386(4) . ? C20 H20 0.88(3) . ? C21 H21 0.93(3) . ? C22 C23 1.451(5) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N1 1.121(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 C7 O1 C1 110.90(16) . . ? C8 O2 C2 116.46(15) . . ? C7 O3 C3 110.53(17) . . ? C4 O4 H4A 110(2) . . ? C7 O5 C5 111.01(16) . . ? C15 O6 C6 117.39(17) . . ? O1 C1 C2 109.44(17) . . ? O1 C1 C6 106.20(17) . . ? C2 C1 C6 109.93(17) . . ? O1 C1 H1 105.4(12) . . ? C2 C1 H1 112.3(12) . . ? C6 C1 H1 113.2(12) . . ? O2 C2 C3 109.34(17) . . ? O2 C2 C1 106.86(16) . . ? C3 C2 C1 108.72(18) . . ? O2 C2 H2 108.2(12) . . ? C3 C2 H2 112.1(12) . . ? C1 C2 H2 111.4(13) . . ? O3 C3 C2 109.50(17) . . ? O3 C3 C4 107.78(17) . . ? C2 C3 C4 110.06(18) . . ? O3 C3 H3 105.3(14) . . ? C2 C3 H3 114.1(14) . . ? C4 C3 H3 109.9(13) . . ? O4 C4 C3 107.29(17) . . ? O4 C4 C5 115.43(18) . . ? C3 C4 C5 106.99(18) . . ? O4 C4 H4 110.7(13) . . ? C3 C4 H4 108.7(13) . . ? C5 C4 H4 107.6(13) . . ? O5 C5 C6 105.97(17) . . ? O5 C5 C4 106.44(18) . . ? C6 C5 C4 114.73(18) . . ? O5 C5 H5 103.9(14) . . ? C6 C5 H5 109.0(14) . . ? C4 C5 H5 115.7(14) . . ? O6 C6 C5 108.83(17) . . ? O6 C6 C1 111.66(17) . . ? C5 C6 C1 107.99(18) . . ? O6 C6 H6 107.3(14) . . ? C5 C6 H6 114.4(14) . . ? C1 C6 H6 106.7(14) . . ? O3 C7 O1 111.25(18) . . ? O3 C7 O5 111.60(18) . . ? O1 C7 O5 111.00(19) . . ? O3 C7 H7 107.7(14) . . ? O1 C7 H7 107.8(14) . . ? O5 C7 H7 107.3(14) . . ? O7 C8 O2 122.57(18) . . ? O7 C8 C9 125.15(19) . . ? O2 C8 C9 112.28(16) . . ? C14 C9 C10 119.61(19) . . ? C14 C9 C8 121.46(19) . . ? C10 C9 C8 118.93(18) . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10 120.8(16) . . ? C9 C10 H10 118.7(16) . . ? C10 C11 C12 119.0(2) . . ? C10 C11 H11 120.6(16) . . ? C12 C11 H11 120.4(16) . . ? C11 C12 C13 121.71(19) . . ? C11 C12 Cl1 118.58(17) . . ? C13 C12 Cl1 119.71(17) . . ? C14 C13 C12 118.9(2) . . ? C14 C13 H13 119.8(15) . . ? C12 C13 H13 121.3(15) . . ? C13 C14 C9 120.2(2) . . ? C13 C14 H14 119.9(15) . . ? C9 C14 H14 119.8(15) . . ? O8 C15 O6 123.2(2) . . ? O8 C15 C16 124.9(2) . . ? O6 C15 C16 111.97(19) . . ? C21 C16 C17 119.1(2) . . ? C21 C16 C15 122.1(2) . . ? C17 C16 C15 118.8(2) . . ? C18 C17 C16 120.5(3) . . ? C18 C17 H17 120(2) . . ? C16 C17 H17 119(2) . . ? C19 C18 C17 119.3(3) . . ? C19 C18 H18 121(2) . . ? C17 C18 H18 119(2) . . ? C18 C19 C20 121.5(3) . . ? C18 C19 Cl2 120.8(4) . . ? C20 C19 Cl2 117.1(4) . . ? C18 C19 Cl2' 117.4(4) . . ? C20 C19 Cl2' 120.4(4) . . ? Cl2 C19 Cl2' 16.0(6) . . ? C19 C20 C21 119.0(3) . . ? C19 C20 H20 119.5(19) . . ? C21 C20 H20 121.4(19) . . ? C16 C21 C20 120.5(2) . . ? C16 C21 H21 119.8(16) . . ? C20 C21 H21 119.6(16) . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C23 C22 179.3(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 57.7(2) . . . . ? C7 O1 C1 C6 -60.9(2) . . . . ? C8 O2 C2 C3 -83.0(2) . . . . ? C8 O2 C2 C1 159.51(17) . . . . ? O1 C1 C2 O2 64.3(2) . . . . ? C6 C1 C2 O2 -179.45(16) . . . . ? O1 C1 C2 C3 -53.6(2) . . . . ? C6 C1 C2 C3 62.6(2) . . . . ? C7 O3 C3 C2 -59.1(2) . . . . ? C7 O3 C3 C4 60.6(2) . . . . ? O2 C2 C3 O3 -61.9(2) . . . . ? C1 C2 C3 O3 54.4(2) . . . . ? O2 C2 C3 C4 179.75(15) . . . . ? C1 C2 C3 C4 -63.9(2) . . . . ? O3 C3 C4 O4 175.08(16) . . . . ? C2 C3 C4 O4 -65.6(2) . . . . ? O3 C3 C4 C5 -60.5(2) . . . . ? C2 C3 C4 C5 58.9(2) . . . . ? C7 O5 C5 C6 61.4(2) . . . . ? C7 O5 C5 C4 -61.2(2) . . . . ? O4 C4 C5 O5 179.51(16) . . . . ? C3 C4 C5 O5 60.2(2) . . . . ? O4 C4 C5 C6 62.7(2) . . . . ? C3 C4 C5 C6 -56.6(2) . . . . ? C15 O6 C6 C5 -148.57(18) . . . . ? C15 O6 C6 C1 92.3(2) . . . . ? O5 C5 C6 O6 177.58(15) . . . . ? C4 C5 C6 O6 -65.3(2) . . . . ? O5 C5 C6 C1 -61.0(2) . . . . ? C4 C5 C6 C1 56.1(2) . . . . ? O1 C1 C6 O6 -179.37(16) . . . . ? C2 C1 C6 O6 62.3(2) . . . . ? O1 C1 C6 C5 61.0(2) . . . . ? C2 C1 C6 C5 -57.3(2) . . . . ? C3 O3 C7 O1 63.2(2) . . . . ? C3 O3 C7 O5 -61.3(2) . . . . ? C1 O1 C7 O3 -62.7(2) . . . . ? C1 O1 C7 O5 62.2(2) . . . . ? C5 O5 C7 O3 62.2(2) . . . . ? C5 O5 C7 O1 -62.5(2) . . . . ? C2 O2 C8 O7 -4.9(3) . . . . ? C2 O2 C8 C9 175.06(16) . . . . ? O7 C8 C9 C14 -180.0(2) . . . . ? O2 C8 C9 C14 0.0(3) . . . . ? O7 C8 C9 C10 -0.7(3) . . . . ? O2 C8 C9 C10 179.29(19) . . . . ? C14 C9 C10 C11 0.0(3) . . . . ? C8 C9 C10 C11 -179.2(2) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C10 C11 C12 Cl1 178.28(17) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? Cl1 C12 C13 C14 -178.77(17) . . . . ? C12 C13 C14 C9 0.5(3) . . . . ? C10 C9 C14 C13 -0.5(3) . . . . ? C8 C9 C14 C13 178.7(2) . . . . ? C6 O6 C15 O8 -6.0(3) . . . . ? C6 O6 C15 C16 174.21(17) . . . . ? O8 C15 C16 C21 178.7(3) . . . . ? O6 C15 C16 C21 -1.4(3) . . . . ? O8 C15 C16 C17 0.1(4) . . . . ? O6 C15 C16 C17 180.0(3) . . . . ? C21 C16 C17 C18 -1.8(5) . . . . ? C15 C16 C17 C18 176.9(3) . . . . ? C16 C17 C18 C19 -0.1(6) . . . . ? C17 C18 C19 C20 2.0(6) . . . . ? C17 C18 C19 Cl2 -169.4(5) . . . . ? C17 C18 C19 Cl2' 172.7(5) . . . . ? C18 C19 C20 C21 -1.9(5) . . . . ? Cl2 C19 C20 C21 169.8(4) . . . . ? Cl2' C19 C20 C21 -172.3(5) . . . . ? C17 C16 C21 C20 1.9(4) . . . . ? C15 C16 C21 C20 -176.7(2) . . . . ? C19 C20 C21 C16 -0.1(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 O4 H4A O7 0.80(3) 2.01(3) 2.813(2) 176(3) 2_745 C7 H7 N1 0.91(2) 2.56(2) 3.451(5) 166.2(19) 3_765 C11 H11 O1 0.96(3) 2.52(3) 3.307(3) 139(2) 1_565 C13 H13 Cl2 0.96(2) 2.82(3) 3.489(9) 127.6(18) 4_675 C14 H14 O8 0.95(3) 2.57(2) 3.281(3) 131.7(19) 3_765 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.382 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.060 #===END data_3J _database_code_depnum_ccdc_archive 'CCDC 752192' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate p-xylene solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate p- xylene solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, 0.5(C8 H10)' _chemical_formula_sum 'C25 H21 Cl2 O8' _chemical_formula_weight 520.32 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 monoclinic _symmetry_space_group_name_H-M 'P(2) 1/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6917(18) _cell_length_b 9.6018(15) _cell_length_c 21.103(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.329(3) _cell_angle_gamma 90.00 _cell_volume 2362.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 3925 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.39 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 0.325 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9198 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11522 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4133 _reflns_number_gt 3510 _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 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^)+(0.0370P)^2^+1.1759P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4133 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Cl1 Cl 0.71765(4) -0.22358(5) 1.14093(2) 0.02836(13) Uani 1 1 d . . . Cl2 Cl -0.08605(5) 0.42857(6) 0.64715(3) 0.04776(17) Uani 1 1 d . . . O1 O 0.65917(11) 0.53798(13) 0.92335(6) 0.0274(3) Uani 1 1 d . . . O2 O 0.61160(11) 0.25059(13) 0.91663(5) 0.0245(3) Uani 1 1 d . . . O3 O 0.77707(11) 0.41969(14) 0.85785(6) 0.0279(3) Uani 1 1 d . . . O4 O 0.55885(11) 0.38573(14) 0.72739(6) 0.0253(3) Uani 1 1 d . . . O5 O 0.71389(11) 0.64372(14) 0.83154(6) 0.0299(3) Uani 1 1 d . . . O6 O 0.41514(10) 0.54032(13) 0.80346(6) 0.0237(3) Uani 1 1 d . . . O7 O 0.57319(11) 0.06297(13) 0.85505(6) 0.0264(3) Uani 1 1 d . . . O8 O 0.30870(12) 0.64610(16) 0.87396(6) 0.0371(4) Uani 1 1 d . . . C1 C 0.55600(15) 0.48202(19) 0.89139(8) 0.0233(4) Uani 1 1 d . . . H1 H 0.4951 0.4727 0.9219 0.028 Uiso 1 1 calc R . . C2 C 0.58148(15) 0.34087(19) 0.86321(8) 0.0216(4) Uani 1 1 d . . . H2 H 0.5124 0.3044 0.8377 0.026 Uiso 1 1 calc R . . C3 C 0.68166(15) 0.35683(19) 0.82161(8) 0.0231(4) Uani 1 1 d . . . H3 H 0.7044 0.2637 0.8055 0.028 Uiso 1 1 calc R . . C4 C 0.64691(15) 0.45331(19) 0.76568(8) 0.0236(4) Uani 1 1 d . . . H4 H 0.7145 0.4674 0.7401 0.028 Uiso 1 1 calc R . . C5 C 0.61367(15) 0.59368(19) 0.79385(9) 0.0246(4) Uani 1 1 d . . . H5 H 0.5921 0.6611 0.7589 0.029 Uiso 1 1 calc R . . C6 C 0.51803(15) 0.58516(19) 0.83891(8) 0.0234(4) Uani 1 1 d . . . H6 H 0.5056 0.6789 0.8578 0.028 Uiso 1 1 calc R . . C7 C 0.74644(17) 0.5495(2) 0.88144(9) 0.0290(4) Uani 1 1 d . . . H7 H 0.8156 0.5890 0.9059 0.035 Uiso 1 1 calc R . . C8 C 0.60345(15) 0.11322(19) 0.90635(8) 0.0212(4) Uani 1 1 d . . . C9 C 0.63425(14) 0.03197(19) 0.96499(8) 0.0206(4) Uani 1 1 d . . . C10 C 0.65166(15) -0.11109(19) 0.96023(8) 0.0246(4) Uani 1 1 d . . . H10 H 0.6455 -0.1546 0.9197 0.029 Uiso 1 1 calc R . . C11 C 0.67785(16) -0.19004(19) 1.01416(8) 0.0255(4) Uani 1 1 d . . . H11 H 0.6910 -0.2874 1.0111 0.031 Uiso 1 1 calc R . . C12 C 0.68453(15) -0.12418(19) 1.07274(8) 0.0221(4) Uani 1 1 d . . . C13 C 0.66699(15) 0.01781(19) 1.07863(8) 0.0218(4) Uani 1 1 d . . . H13 H 0.6713 0.0605 1.1193 0.026 Uiso 1 1 calc R . . C14 C 0.64311(14) 0.09647(19) 1.02437(8) 0.0211(4) Uani 1 1 d . . . H14 H 0.6327 0.1943 1.0275 0.025 Uiso 1 1 calc R . . C15 C 0.31468(16) 0.58124(19) 0.82542(9) 0.0254(4) Uani 1 1 d . . . C16 C 0.21587(16) 0.53755(19) 0.78168(9) 0.0252(4) Uani 1 1 d . . . C17 C 0.10681(17) 0.5817(2) 0.79409(10) 0.0382(5) Uani 1 1 d . . . H17 H 0.0965 0.6356 0.8310 0.046 Uiso 1 1 calc R . . C18 C 0.01341(18) 0.5478(2) 0.75333(11) 0.0430(6) Uani 1 1 d . . . H18 H -0.0613 0.5783 0.7617 0.052 Uiso 1 1 calc R . . C19 C 0.03023(17) 0.4689(2) 0.70020(10) 0.0334(5) Uani 1 1 d . . . C20 C 0.13675(17) 0.4208(2) 0.68778(10) 0.0321(5) Uani 1 1 d . . . H20 H 0.1461 0.3644 0.6515 0.039 Uiso 1 1 calc R . . C21 C 0.23013(16) 0.4554(2) 0.72859(9) 0.0271(4) Uani 1 1 d . . . H21 H 0.3044 0.4230 0.7204 0.033 Uiso 1 1 calc R . . C22 C -0.0389(3) 0.2144(3) 0.95533(14) 0.0690(8) Uani 1 1 d . . . H22A H -0.0815 0.2162 0.9135 0.104 Uiso 1 1 calc R . . H22B H -0.0834 0.1637 0.9854 0.104 Uiso 1 1 calc R . . H22C H 0.0349 0.1678 0.9520 0.104 Uiso 1 1 calc R . . C23 C -0.01852(19) 0.3619(3) 0.97863(10) 0.0433(6) Uani 1 1 d . . . C24 C 0.0834(2) 0.5807(3) 0.97580(11) 0.0469(6) Uani 1 1 d . . . H24 H 0.1414 0.6350 0.9585 0.056 Uiso 1 1 calc R . . C25 C 0.0651(2) 0.4451(3) 0.95503(11) 0.0466(6) Uani 1 1 d . . . H25 H 0.1111 0.4083 0.9238 0.056 Uiso 1 1 calc R . . H4A H 0.526(2) 0.443(3) 0.7031(12) 0.047(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0352(3) 0.0272(3) 0.0225(2) 0.00755(19) 0.00087(18) 0.0023(2) Cl2 0.0311(3) 0.0468(4) 0.0625(4) -0.0074(3) -0.0160(3) 0.0025(2) O1 0.0323(7) 0.0274(7) 0.0213(7) -0.0032(5) -0.0053(5) -0.0034(6) O2 0.0364(7) 0.0199(7) 0.0163(6) 0.0017(5) -0.0038(5) -0.0012(6) O3 0.0240(7) 0.0300(8) 0.0285(7) -0.0005(6) -0.0050(5) -0.0002(6) O4 0.0300(7) 0.0261(8) 0.0188(7) 0.0018(6) -0.0040(5) 0.0012(6) O5 0.0305(7) 0.0265(7) 0.0315(7) 0.0041(6) -0.0052(6) -0.0079(6) O6 0.0235(7) 0.0241(7) 0.0231(7) -0.0017(5) -0.0010(5) 0.0025(5) O7 0.0357(7) 0.0249(7) 0.0178(7) -0.0027(5) -0.0032(5) -0.0018(6) O8 0.0355(8) 0.0453(9) 0.0309(8) -0.0141(7) 0.0056(6) -0.0006(7) C1 0.0259(10) 0.0249(10) 0.0187(9) -0.0020(8) -0.0008(7) -0.0018(8) C2 0.0268(10) 0.0216(10) 0.0156(8) 0.0026(7) -0.0039(7) -0.0010(8) C3 0.0254(9) 0.0227(10) 0.0207(9) -0.0014(7) -0.0020(7) 0.0011(8) C4 0.0247(10) 0.0260(10) 0.0201(9) 0.0028(8) 0.0008(7) -0.0022(8) C5 0.0263(10) 0.0223(10) 0.0243(10) 0.0045(8) -0.0034(7) -0.0040(8) C6 0.0274(10) 0.0208(10) 0.0212(9) -0.0024(7) -0.0036(7) -0.0012(8) C7 0.0305(11) 0.0263(11) 0.0291(10) 0.0015(8) -0.0058(8) -0.0052(8) C8 0.0206(9) 0.0227(10) 0.0205(9) -0.0012(7) 0.0017(7) -0.0015(7) C9 0.0198(9) 0.0218(10) 0.0199(9) -0.0004(7) -0.0001(7) -0.0023(7) C10 0.0281(10) 0.0245(10) 0.0209(9) -0.0024(8) -0.0001(7) -0.0027(8) C11 0.0309(10) 0.0189(10) 0.0267(10) 0.0000(8) 0.0014(8) 0.0007(8) C12 0.0206(9) 0.0254(10) 0.0202(9) 0.0061(7) 0.0000(7) -0.0014(7) C13 0.0228(9) 0.0250(10) 0.0174(9) -0.0020(7) 0.0009(7) -0.0011(8) C14 0.0210(9) 0.0194(9) 0.0224(9) -0.0004(7) -0.0007(7) -0.0012(7) C15 0.0300(10) 0.0206(10) 0.0259(10) 0.0023(8) 0.0045(8) 0.0004(8) C16 0.0273(10) 0.0221(10) 0.0262(10) 0.0042(8) 0.0025(8) 0.0010(8) C17 0.0313(11) 0.0437(13) 0.0402(12) -0.0113(10) 0.0065(9) 0.0034(10) C18 0.0248(11) 0.0499(15) 0.0544(14) -0.0111(11) 0.0035(10) 0.0059(10) C19 0.0276(11) 0.0289(11) 0.0424(12) 0.0023(9) -0.0057(9) 0.0007(9) C20 0.0320(11) 0.0318(12) 0.0319(11) -0.0042(9) -0.0020(9) 0.0031(9) C21 0.0248(10) 0.0272(11) 0.0292(10) 0.0009(8) 0.0018(8) 0.0047(8) C22 0.079(2) 0.0556(18) 0.0712(19) -0.0083(15) -0.0062(16) 0.0108(15) C23 0.0414(13) 0.0516(15) 0.0361(12) 0.0001(11) -0.0024(10) 0.0134(11) C24 0.0382(13) 0.0602(17) 0.0430(13) 0.0084(12) 0.0069(10) 0.0032(11) C25 0.0413(13) 0.0632(17) 0.0361(12) -0.0009(11) 0.0090(10) 0.0171(12) _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 Cl1 C12 1.7457(18) . ? Cl2 C19 1.738(2) . ? O1 C7 1.404(2) . ? O1 C1 1.441(2) . ? O2 C8 1.339(2) . ? O2 C2 1.444(2) . ? O3 C7 1.399(2) . ? O3 C3 1.437(2) . ? O4 C4 1.417(2) . ? O4 H4A 0.83(2) . ? O5 C7 1.418(2) . ? O5 C5 1.448(2) . ? O6 C15 1.353(2) . ? O6 C6 1.434(2) . ? O7 C8 1.213(2) . ? O8 C15 1.205(2) . ? C1 C2 1.519(3) . ? C1 C6 1.526(2) . ? C1 H1 1.0000 . ? C2 C3 1.524(2) . ? C2 H2 1.0000 . ? C3 C4 1.531(2) . ? C3 H3 1.0000 . ? C4 C5 1.535(3) . ? C4 H4 1.0000 . ? C5 C6 1.524(3) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.484(2) . ? C9 C10 1.393(3) . ? C9 C14 1.395(2) . ? C10 C11 1.382(3) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 C13 1.386(3) . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.484(3) . ? C16 C17 1.387(3) . ? C16 C21 1.391(3) . ? C17 C18 1.377(3) . ? C17 H17 0.9500 . ? C18 C19 1.380(3) . ? C18 H18 0.9500 . ? C19 C20 1.372(3) . ? C20 C21 1.379(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.512(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.384(3) 3_567 ? C23 C25 1.384(3) . ? C24 C23 1.384(3) 3_567 ? C24 C25 1.385(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? 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 110.91(13) . . ? C8 O2 C2 117.04(13) . . ? C7 O3 C3 110.76(14) . . ? C4 O4 H4A 109.3(17) . . ? C7 O5 C5 110.91(14) . . ? C15 O6 C6 116.73(14) . . ? O1 C1 C2 109.52(14) . . ? O1 C1 C6 106.57(14) . . ? C2 C1 C6 110.48(14) . . ? O1 C1 H1 110.1 . . ? C2 C1 H1 110.1 . . ? C6 C1 H1 110.1 . . ? O2 C2 C1 105.88(13) . . ? O2 C2 C3 110.94(14) . . ? C1 C2 C3 108.54(15) . . ? O2 C2 H2 110.5 . . ? C1 C2 H2 110.5 . . ? C3 C2 H2 110.5 . . ? O3 C3 C2 109.59(14) . . ? O3 C3 C4 107.84(14) . . ? C2 C3 C4 109.53(14) . . ? O3 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? C4 C3 H3 110.0 . . ? O4 C4 C3 107.56(14) . . ? O4 C4 C5 115.38(15) . . ? C3 C4 C5 107.03(14) . . ? O4 C4 H4 108.9 . . ? C3 C4 H4 108.9 . . ? C5 C4 H4 108.9 . . ? O5 C5 C6 106.07(14) . . ? O5 C5 C4 106.63(14) . . ? C6 C5 C4 114.44(15) . . ? O5 C5 H5 109.8 . . ? C6 C5 H5 109.8 . . ? C4 C5 H5 109.8 . . ? O6 C6 C5 108.47(14) . . ? O6 C6 C1 111.73(14) . . ? C5 C6 C1 107.49(15) . . ? O6 C6 H6 109.7 . . ? C5 C6 H6 109.7 . . ? C1 C6 H6 109.7 . . ? O3 C7 O1 111.82(15) . . ? O3 C7 O5 111.45(15) . . ? O1 C7 O5 110.54(15) . . ? O3 C7 H7 107.6 . . ? O1 C7 H7 107.6 . . ? O5 C7 H7 107.6 . . ? O7 C8 O2 123.28(16) . . ? O7 C8 C9 124.82(17) . . ? O2 C8 C9 111.89(14) . . ? C10 C9 C14 120.08(16) . . ? C10 C9 C8 119.06(16) . . ? C14 C9 C8 120.84(16) . . ? C11 C10 C9 120.38(17) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 118.58(17) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C11 C12 C13 122.02(16) . . ? C11 C12 Cl1 118.69(14) . . ? C13 C12 Cl1 119.29(13) . . ? C14 C13 C12 119.03(16) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C9 119.89(17) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? O8 C15 O6 123.27(17) . . ? O8 C15 C16 125.61(17) . . ? O6 C15 C16 111.11(15) . . ? C17 C16 C21 119.56(18) . . ? C17 C16 C15 118.67(17) . . ? C21 C16 C15 121.76(17) . . ? C18 C17 C16 120.5(2) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 118.83(19) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 121.83(19) . . ? C20 C19 Cl2 118.61(16) . . ? C18 C19 Cl2 119.56(16) . . ? C19 C20 C21 119.13(19) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C20 C21 C16 120.15(18) . . ? C20 C21 H21 119.9 . . ? C16 C21 H21 119.9 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C25 117.4(2) 3_567 . ? C24 C23 C22 121.2(2) 3_567 . ? C25 C23 C22 121.5(2) . . ? C23 C24 C25 121.0(2) 3_567 . ? C23 C24 H24 119.5 3_567 . ? C25 C24 H24 119.5 . . ? C23 C25 C24 121.7(2) . . ? C23 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? 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 57.82(18) . . . . ? C7 O1 C1 C6 -61.70(18) . . . . ? C8 O2 C2 C1 159.92(14) . . . . ? C8 O2 C2 C3 -82.51(18) . . . . ? O1 C1 C2 O2 65.28(17) . . . . ? C6 C1 C2 O2 -177.64(14) . . . . ? O1 C1 C2 C3 -53.89(18) . . . . ? C6 C1 C2 C3 63.20(18) . . . . ? C7 O3 C3 C2 -58.30(18) . . . . ? C7 O3 C3 C4 60.86(18) . . . . ? O2 C2 C3 O3 -61.73(18) . . . . ? C1 C2 C3 O3 54.20(18) . . . . ? O2 C2 C3 C4 -179.84(14) . . . . ? C1 C2 C3 C4 -63.91(18) . . . . ? O3 C3 C4 O4 175.49(13) . . . . ? C2 C3 C4 O4 -65.32(18) . . . . ? O3 C3 C4 C5 -59.96(18) . . . . ? C2 C3 C4 C5 59.24(18) . . . . ? C7 O5 C5 C6 61.53(18) . . . . ? C7 O5 C5 C4 -60.84(18) . . . . ? O4 C4 C5 O5 179.27(14) . . . . ? C3 C4 C5 O5 59.63(17) . . . . ? O4 C4 C5 C6 62.3(2) . . . . ? C3 C4 C5 C6 -57.31(19) . . . . ? C15 O6 C6 C5 -152.67(15) . . . . ? C15 O6 C6 C1 89.01(18) . . . . ? O5 C5 C6 O6 178.11(13) . . . . ? C4 C5 C6 O6 -64.63(19) . . . . ? O5 C5 C6 C1 -60.92(18) . . . . ? C4 C5 C6 C1 56.34(19) . . . . ? O1 C1 C6 O6 -179.98(13) . . . . ? C2 C1 C6 O6 61.13(19) . . . . ? O1 C1 C6 C5 61.12(17) . . . . ? C2 C1 C6 C5 -57.77(18) . . . . ? C3 O3 C7 O1 62.46(18) . . . . ? C3 O3 C7 O5 -61.83(18) . . . . ? C1 O1 C7 O3 -62.25(18) . . . . ? C1 O1 C7 O5 62.55(19) . . . . ? C5 O5 C7 O3 62.36(19) . . . . ? C5 O5 C7 O1 -62.65(19) . . . . ? C2 O2 C8 O7 0.5(2) . . . . ? C2 O2 C8 C9 -178.81(14) . . . . ? O7 C8 C9 C10 12.9(3) . . . . ? O2 C8 C9 C10 -167.79(15) . . . . ? O7 C8 C9 C14 -165.51(17) . . . . ? O2 C8 C9 C14 13.8(2) . . . . ? C14 C9 C10 C11 0.0(3) . . . . ? C8 C9 C10 C11 -178.51(16) . . . . ? C9 C10 C11 C12 1.0(3) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C10 C11 C12 Cl1 -179.97(14) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? Cl1 C12 C13 C14 178.68(13) . . . . ? C12 C13 C14 C9 1.6(3) . . . . ? C10 C9 C14 C13 -1.3(3) . . . . ? C8 C9 C14 C13 177.18(16) . . . . ? C6 O6 C15 O8 -3.7(3) . . . . ? C6 O6 C15 C16 175.43(14) . . . . ? O8 C15 C16 C17 4.8(3) . . . . ? O6 C15 C16 C17 -174.38(17) . . . . ? O8 C15 C16 C21 -175.95(19) . . . . ? O6 C15 C16 C21 4.9(2) . . . . ? C21 C16 C17 C18 -1.8(3) . . . . ? C15 C16 C17 C18 177.5(2) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C17 C18 C19 C20 1.5(3) . . . . ? C17 C18 C19 Cl2 -178.47(18) . . . . ? C18 C19 C20 C21 -1.8(3) . . . . ? Cl2 C19 C20 C21 178.22(16) . . . . ? C19 C20 C21 C16 0.2(3) . . . . ? C17 C16 C21 C20 1.5(3) . . . . ? C15 C16 C21 C20 -177.75(18) . . . . ? C24 C23 C25 C24 -0.2(4) 3_567 . . . ? C22 C23 C25 C24 179.4(2) . . . . ? C23 C24 C25 C23 0.2(4) 3_567 . . . ? 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 O4 H4A O7 0.83(2) 1.99(3) 2.8107(18) 172(2) 2_656 C21 H21 O7 0.95 2.60 3.175(2) 119.7 2_656 C11 H11 O1 0.95 2.51 3.237(2) 133.8 1_545 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.291 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.046 #===END data_3K _database_code_depnum_ccdc_archive 'CCDC 752193' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate benzene solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate benzene solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, 0.5(C6H6)2' _chemical_formula_sum 'C27 H22 Cl2 O8' _chemical_formula_weight 545.35 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' Cl Cl 0.1484 0.1585 '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 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 32.22(3) _cell_length_b 9.584(8) _cell_length_c 21.386(19) _cell_angle_alpha 90.00 _cell_angle_beta 129.72(3) _cell_angle_gamma 90.00 _cell_volume 5080(8) _cell_formula_units_Z 8 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 3327 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.33 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 0.306 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8585 _exptl_absorpt_correction_T_max 0.9634 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 14943 _diffrn_reflns_av_R_equivalents 0.1264 _diffrn_reflns_av_sigmaI/netI 0.1290 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4438 _reflns_number_gt 2776 _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 1.4.1' _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^)+(0.0809P)^2^+41.1214P] 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 4438 _refine_ls_number_parameters 350 _refine_ls_number_restraints 114 _refine_ls_R_factor_all 0.1790 _refine_ls_R_factor_gt 0.1154 _refine_ls_wR_factor_ref 0.2626 _refine_ls_wR_factor_gt 0.2338 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.107 _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 Cl1 Cl 0.15018(8) 0.97897(18) 0.52936(11) 0.0373(5) Uani 1 1 d . . . Cl2 Cl 0.54082(10) 0.3242(4) 0.48804(17) 0.0924(11) Uani 1 1 d . . . O1 O 0.1721(2) 0.2089(5) 0.3357(3) 0.0318(12) Uani 1 1 d . . . O2 O 0.19563(19) 0.4982(4) 0.3565(3) 0.0257(11) Uani 1 1 d . . . O3 O 0.11852(18) 0.3274(5) 0.2133(3) 0.0319(12) Uani 1 1 d . . . O4 O 0.22538(19) 0.3666(4) 0.2017(3) 0.0261(11) Uani 1 1 d . . . H4A H 0.2431 0.3080 0.1980 0.039 Uiso 1 1 calc R . . O5 O 0.14965(19) 0.1043(5) 0.2199(3) 0.0337(12) Uani 1 1 d . . . O6 O 0.29072(17) 0.2053(4) 0.3474(2) 0.0236(10) Uani 1 1 d . . . O7 O 0.21337(19) 0.6853(5) 0.3146(3) 0.0303(12) Uani 1 1 d . . . O8 O 0.3350(2) 0.0869(6) 0.4642(3) 0.0526(16) Uani 1 1 d . . . C1 C 0.2216(3) 0.2656(6) 0.3584(4) 0.0213(14) Uani 1 1 d . . . H1 H 0.2492 0.2740 0.4189 0.026 Uiso 1 1 calc R . . C2 C 0.2105(3) 0.4078(6) 0.3189(4) 0.0190(14) Uani 1 1 d . . . H2 H 0.2434 0.4441 0.3289 0.023 Uiso 1 1 calc R . . C3 C 0.1640(3) 0.3926(6) 0.2285(4) 0.0212(14) Uani 1 1 d . . . H3 H 0.1535 0.4864 0.2019 0.025 Uiso 1 1 calc R . . C4 C 0.1829(3) 0.2985(7) 0.1922(4) 0.0262(15) Uani 1 1 d . . . H4 H 0.1522 0.2854 0.1329 0.031 Uiso 1 1 calc R . . C5 C 0.1973(3) 0.1558(6) 0.2352(4) 0.0256(15) Uani 1 1 d . . . H5 H 0.2084 0.0895 0.2121 0.031 Uiso 1 1 calc R . . C6 C 0.2409(3) 0.1623(6) 0.3266(4) 0.0246(15) Uani 1 1 d . . . H6 H 0.2455 0.0678 0.3502 0.029 Uiso 1 1 calc R . . C7 C 0.1318(3) 0.1980(8) 0.2508(5) 0.0357(17) Uani 1 1 d . . . H7 H 0.0988 0.1575 0.2389 0.043 Uiso 1 1 calc R . . C8 C 0.1998(3) 0.6370(7) 0.3512(4) 0.0249(15) Uani 1 1 d . . . C9 C 0.1861(3) 0.7172(6) 0.3945(4) 0.0248(15) Uani 1 1 d . . . C10 C 0.1791(3) 0.8599(7) 0.3821(4) 0.0326(18) Uani 1 1 d . . . H10 H 0.1824 0.9026 0.3453 0.039 Uiso 1 1 calc R . . C11 C 0.1676(3) 0.9404(6) 0.4222(4) 0.0325(18) Uani 1 1 d . . . H11 H 0.1618 1.0379 0.4126 0.039 Uiso 1 1 calc R . . C12 C 0.1645(3) 0.8769(7) 0.4769(4) 0.0293(17) Uani 1 1 d . . . C13 C 0.1707(3) 0.7354(7) 0.4903(4) 0.0310(17) Uani 1 1 d . . . H13 H 0.1674 0.6933 0.5272 0.037 Uiso 1 1 calc R . . C14 C 0.1818(3) 0.6555(7) 0.4483(4) 0.0305(17) Uani 1 1 d . . . H14 H 0.1866 0.5575 0.4568 0.037 Uiso 1 1 calc R . . C15 C 0.3357(3) 0.1573(7) 0.4181(4) 0.0284(16) Uani 1 1 d . . . C16 C 0.3856(3) 0.1973(7) 0.4322(4) 0.0260(15) Uani 1 1 d . . . C17 C 0.4350(3) 0.1480(9) 0.4996(5) 0.048(2) Uani 1 1 d . . . H17 H 0.4360 0.0875 0.5358 0.058 Uiso 1 1 calc R . . C18 C 0.4828(4) 0.1824(11) 0.5168(6) 0.064(3) Uani 1 1 d . . . H18 H 0.5160 0.1438 0.5626 0.077 Uiso 1 1 calc R . . C19 C 0.4810(3) 0.2744(10) 0.4657(5) 0.048(2) Uani 1 1 d . . . C20 C 0.4322(3) 0.3252(10) 0.3974(5) 0.051(2) Uani 1 1 d . . . H20 H 0.4313 0.3858 0.3614 0.062 Uiso 1 1 calc R . . C21 C 0.3847(3) 0.2889(8) 0.3809(4) 0.0346(18) Uani 1 1 d . . . H21 H 0.3514 0.3263 0.3345 0.042 Uiso 1 1 calc R . . C22 C 0.0514(7) 0.5605(17) 0.2753(11) 0.162(6) Uani 1 1 d DU . . H22 H 0.0873 0.5526 0.2947 0.195 Uiso 1 1 calc R . . C23 C 0.0090(7) 0.5660(13) 0.1930(10) 0.153(5) Uani 1 1 d DU . . H23 H 0.0144 0.5692 0.1542 0.183 Uiso 1 1 calc R . . C24 C -0.0419(7) 0.5665(16) 0.1704(11) 0.148(5) Uani 1 1 d DU . . H24 H -0.0722 0.5713 0.1141 0.177 Uiso 1 1 calc R . . C25 C -0.0226(8) -0.0364(19) 0.2028(18) 0.130(7) Uani 0.50 1 d PGDU A 1 H25 H -0.0397 -0.1142 0.1673 0.156 Uiso 0.50 1 calc PR A 1 C26 C -0.0137(8) 0.085(3) 0.1772(14) 0.127(7) Uani 0.50 1 d PGDU A 1 H26 H -0.0246 0.0895 0.1241 0.152 Uiso 0.50 1 calc PR A 1 C27 C 0.0114(8) 0.1985(18) 0.2292(17) 0.127(7) Uani 0.50 1 d PGDU A 1 H27 H 0.0175 0.2812 0.2116 0.153 Uiso 0.50 1 calc PR A 1 C28 C 0.0274(7) 0.191(2) 0.3068(16) 0.131(7) Uani 0.50 1 d PGDU A 1 H28 H 0.0445 0.2692 0.3423 0.157 Uiso 0.50 1 calc PR A 1 C29 C 0.0184(8) 0.070(3) 0.3324(14) 0.132(7) Uani 0.50 1 d PGDU A 1 H29 H 0.0294 0.0655 0.3855 0.158 Uiso 0.50 1 calc PR A 1 C30 C -0.0066(9) -0.0435(19) 0.2804(19) 0.130(7) Uani 0.50 1 d PGDU A 1 H30 H -0.0127 -0.1262 0.2980 0.156 Uiso 0.50 1 calc PR A 1 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 Cl1 0.0514(12) 0.0293(10) 0.0481(11) -0.0111(8) 0.0396(10) -0.0005(9) Cl2 0.0352(14) 0.157(3) 0.0712(17) 0.0259(19) 0.0275(13) -0.0046(17) O1 0.048(3) 0.020(3) 0.047(3) 0.001(2) 0.040(3) -0.008(2) O2 0.051(3) 0.009(2) 0.043(3) -0.0034(19) 0.042(3) -0.006(2) O3 0.026(3) 0.026(3) 0.045(3) -0.001(2) 0.023(2) -0.001(2) O4 0.045(3) 0.014(2) 0.041(3) 0.003(2) 0.038(3) 0.004(2) O5 0.033(3) 0.019(3) 0.048(3) -0.014(2) 0.025(3) -0.014(2) O6 0.027(3) 0.019(2) 0.025(2) 0.0038(19) 0.016(2) 0.004(2) O7 0.054(3) 0.020(2) 0.046(3) 0.002(2) 0.045(3) 0.001(2) O8 0.053(4) 0.056(4) 0.048(3) 0.026(3) 0.032(3) 0.002(3) C1 0.032(4) 0.012(3) 0.029(3) -0.002(3) 0.024(3) -0.001(3) C2 0.030(4) 0.010(3) 0.027(3) 0.000(3) 0.023(3) 0.001(3) C3 0.026(4) 0.013(3) 0.031(4) 0.003(3) 0.021(3) 0.002(3) C4 0.033(4) 0.023(4) 0.031(4) -0.001(3) 0.024(3) 0.003(3) C5 0.031(4) 0.010(3) 0.037(4) -0.012(3) 0.022(3) -0.010(3) C6 0.029(4) 0.012(3) 0.037(4) -0.002(3) 0.023(3) -0.004(3) C7 0.035(5) 0.033(4) 0.045(4) 0.000(4) 0.028(4) -0.005(4) C8 0.037(4) 0.018(3) 0.030(4) 0.001(3) 0.026(4) -0.001(3) C9 0.042(4) 0.012(3) 0.038(4) -0.003(3) 0.033(4) -0.003(3) C10 0.055(5) 0.015(4) 0.052(5) 0.005(3) 0.045(4) 0.000(3) C11 0.060(5) 0.008(3) 0.051(5) 0.001(3) 0.045(5) 0.000(3) C12 0.047(5) 0.019(4) 0.041(4) -0.009(3) 0.037(4) -0.001(3) C13 0.053(5) 0.026(4) 0.035(4) 0.003(3) 0.038(4) -0.001(4) C14 0.058(5) 0.016(3) 0.043(4) -0.004(3) 0.043(4) -0.007(3) C15 0.034(4) 0.026(4) 0.024(4) -0.005(3) 0.018(4) -0.006(3) C16 0.031(4) 0.016(3) 0.024(3) -0.002(3) 0.015(3) 0.003(3) C17 0.039(5) 0.057(6) 0.036(4) 0.013(4) 0.018(4) 0.001(4) C18 0.040(6) 0.085(8) 0.054(6) 0.023(5) 0.024(5) 0.013(5) C19 0.029(5) 0.067(6) 0.039(4) 0.002(4) 0.018(4) -0.008(4) C20 0.029(5) 0.072(6) 0.044(5) 0.021(5) 0.019(4) 0.001(5) C21 0.036(5) 0.033(4) 0.031(4) 0.007(3) 0.019(4) 0.002(4) C22 0.141(9) 0.179(10) 0.134(9) 0.000(9) 0.072(8) -0.027(9) C23 0.140(9) 0.170(9) 0.125(8) -0.008(7) 0.074(7) -0.013(8) C24 0.137(9) 0.173(10) 0.121(8) -0.019(8) 0.076(8) 0.025(9) C25 0.127(10) 0.136(10) 0.117(9) 0.009(9) 0.074(8) -0.005(8) C26 0.125(10) 0.133(10) 0.116(9) 0.007(9) 0.075(8) -0.006(9) C27 0.125(10) 0.130(10) 0.123(9) 0.008(9) 0.077(8) 0.001(8) C28 0.130(10) 0.132(10) 0.120(9) 0.001(9) 0.075(8) 0.006(8) C29 0.129(10) 0.137(10) 0.120(9) 0.003(9) 0.075(8) 0.007(9) C30 0.128(10) 0.137(10) 0.119(9) 0.008(9) 0.076(8) 0.001(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C12 1.759(6) . ? Cl2 C19 1.729(8) . ? O1 C7 1.407(9) . ? O1 C1 1.442(8) . ? O2 C8 1.349(8) . ? O2 C2 1.454(7) . ? O3 C7 1.388(8) . ? O3 C3 1.428(7) . ? O4 C4 1.409(8) . ? O4 H4A 0.8400 . ? O5 C7 1.434(8) . ? O5 C5 1.439(8) . ? O6 C15 1.341(8) . ? O6 C6 1.425(7) . ? O7 C8 1.207(7) . ? O8 C15 1.207(8) . ? C1 C2 1.520(8) . ? C1 C6 1.541(8) . ? C1 H1 1.0000 . ? C2 C3 1.517(9) . ? C2 H2 1.0000 . ? C3 C4 1.546(8) . ? C3 H3 1.0000 . ? C4 C5 1.544(9) . ? C4 H4 1.0000 . ? C5 C6 1.512(9) . ? C5 H5 1.0000 . ? C6 H6 1.0000 . ? C7 H7 1.0000 . ? C8 C9 1.470(8) . ? C9 C14 1.376(8) . ? C9 C10 1.385(9) . ? C10 C11 1.371(9) . ? C10 H10 0.9500 . ? C11 C12 1.376(9) . ? C11 H11 0.9500 . ? C12 C13 1.374(9) . ? C13 C14 1.393(9) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.484(10) . ? C16 C17 1.379(10) . ? C16 C21 1.391(9) . ? C17 C18 1.375(12) . ? C17 H17 0.9500 . ? C18 C19 1.378(12) . ? C18 H18 0.9500 . ? C19 C20 1.382(11) . ? C20 C21 1.377(10) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.38(3) . ? C22 C24 1.38(3) 2 ? C22 H22 0.9500 . ? C23 C24 1.38(4) . ? C23 H23 0.9500 . ? C24 C22 1.38(3) 2 ? C24 H24 0.9500 . ? C25 C26 1.3900 . ? C25 C30 1.3900 . ? C25 H25 0.9500 . ? C26 C27 1.3900 . ? C26 H26 0.9500 . ? C27 C28 1.3900 . ? C27 H27 0.9500 . ? C28 C29 1.3900 . ? C28 H28 0.9500 . ? C29 C30 1.3900 . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? 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 111.9(5) . . ? C8 O2 C2 117.1(4) . . ? C7 O3 C3 111.5(5) . . ? C4 O4 H4A 109.5 . . ? C7 O5 C5 111.3(5) . . ? C15 O6 C6 116.3(5) . . ? O1 C1 C2 109.5(5) . . ? O1 C1 C6 106.3(5) . . ? C2 C1 C6 110.4(5) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C3 110.9(5) . . ? O2 C2 C1 105.7(4) . . ? C3 C2 C1 108.2(5) . . ? O2 C2 H2 110.7 . . ? C3 C2 H2 110.7 . . ? C1 C2 H2 110.7 . . ? O3 C3 C2 111.5(5) . . ? O3 C3 C4 107.9(5) . . ? C2 C3 C4 108.2(5) . . ? O3 C3 H3 109.8 . . ? C2 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? O4 C4 C5 115.4(5) . . ? O4 C4 C3 108.3(5) . . ? C5 C4 C3 106.4(5) . . ? O4 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? C3 C4 H4 108.8 . . ? O5 C5 C6 106.4(5) . . ? O5 C5 C4 107.3(5) . . ? C6 C5 C4 114.3(5) . . ? O5 C5 H5 109.6 . . ? C6 C5 H5 109.6 . . ? C4 C5 H5 109.6 . . ? O6 C6 C5 110.2(5) . . ? O6 C6 C1 111.6(5) . . ? C5 C6 C1 107.0(5) . . ? O6 C6 H6 109.3 . . ? C5 C6 H6 109.3 . . ? C1 C6 H6 109.3 . . ? O3 C7 O1 111.7(6) . . ? O3 C7 O5 111.1(5) . . ? O1 C7 O5 109.3(6) . . ? O3 C7 H7 108.2 . . ? O1 C7 H7 108.2 . . ? O5 C7 H7 108.2 . . ? O7 C8 O2 122.0(6) . . ? O7 C8 C9 125.9(6) . . ? O2 C8 C9 112.2(5) . . ? C14 C9 C10 119.6(6) . . ? C14 C9 C8 122.1(6) . . ? C10 C9 C8 118.2(6) . . ? C11 C10 C9 120.8(6) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 118.6(6) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 122.4(6) . . ? C13 C12 Cl1 118.5(5) . . ? C11 C12 Cl1 119.1(5) . . ? C12 C13 C14 118.0(6) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? C9 C14 C13 120.6(6) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? O8 C15 O6 122.7(7) . . ? O8 C15 C16 124.2(7) . . ? O6 C15 C16 113.0(5) . . ? C17 C16 C21 118.0(7) . . ? C17 C16 C15 120.0(6) . . ? C21 C16 C15 121.9(6) . . ? C18 C17 C16 123.0(8) . . ? C18 C17 H17 118.5 . . ? C16 C17 H17 118.5 . . ? C17 C18 C19 118.1(8) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? C18 C19 C20 120.4(8) . . ? C18 C19 Cl2 118.9(7) . . ? C20 C19 Cl2 120.7(6) . . ? C21 C20 C19 120.7(7) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C16 119.8(7) . . ? C20 C21 H21 120.1 . . ? C16 C21 H21 120.1 . . ? C23 C22 C24 120.1(17) . 2 ? C23 C22 H22 119.9 . . ? C24 C22 H22 119.9 2 . ? C22 C23 C24 115.7(17) . . ? C22 C23 H23 122.2 . . ? C24 C23 H23 122.2 . . ? C22 C24 C23 124.0(17) 2 . ? C22 C24 H24 118.0 2 . ? C23 C24 H24 118.0 . . ? C26 C25 C30 120.0 . . ? C26 C25 H25 120.0 . . ? C30 C25 H25 120.0 . . ? C27 C26 C25 120.0 . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 120.0 . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C29 C28 C27 120.0 . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C28 C29 C30 120.0 . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C29 C30 C25 120.0 . . ? C29 C30 H30 120.0 . . ? C25 C30 H30 120.0 . . ? 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 57.5(6) . . . . ? C7 O1 C1 C6 -61.8(6) . . . . ? C8 O2 C2 C3 -82.8(7) . . . . ? C8 O2 C2 C1 160.2(5) . . . . ? O1 C1 C2 O2 66.4(6) . . . . ? C6 C1 C2 O2 -176.8(5) . . . . ? O1 C1 C2 C3 -52.3(6) . . . . ? C6 C1 C2 C3 64.4(7) . . . . ? C7 O3 C3 C2 -56.8(6) . . . . ? C7 O3 C3 C4 61.8(6) . . . . ? O2 C2 C3 O3 -62.9(6) . . . . ? C1 C2 C3 O3 52.6(6) . . . . ? O2 C2 C3 C4 178.7(5) . . . . ? C1 C2 C3 C4 -65.8(6) . . . . ? O3 C3 C4 O4 175.8(5) . . . . ? C2 C3 C4 O4 -63.5(6) . . . . ? O3 C3 C4 C5 -59.5(7) . . . . ? C2 C3 C4 C5 61.2(6) . . . . ? C7 O5 C5 C6 62.8(7) . . . . ? C7 O5 C5 C4 -60.0(6) . . . . ? O4 C4 C5 O5 179.0(5) . . . . ? C3 C4 C5 O5 58.8(6) . . . . ? O4 C4 C5 C6 61.2(7) . . . . ? C3 C4 C5 C6 -59.0(7) . . . . ? C15 O6 C6 C5 -150.4(5) . . . . ? C15 O6 C6 C1 90.7(6) . . . . ? O5 C5 C6 O6 176.8(5) . . . . ? C4 C5 C6 O6 -64.9(7) . . . . ? O5 C5 C6 C1 -61.6(6) . . . . ? C4 C5 C6 C1 56.7(7) . . . . ? O1 C1 C6 O6 -178.4(5) . . . . ? C2 C1 C6 O6 62.9(7) . . . . ? O1 C1 C6 C5 60.9(6) . . . . ? C2 C1 C6 C5 -57.8(7) . . . . ? C3 O3 C7 O1 60.3(7) . . . . ? C3 O3 C7 O5 -62.0(7) . . . . ? C1 O1 C7 O3 -61.4(7) . . . . ? C1 O1 C7 O5 61.9(7) . . . . ? C5 O5 C7 O3 61.4(7) . . . . ? C5 O5 C7 O1 -62.2(7) . . . . ? C2 O2 C8 O7 2.6(9) . . . . ? C2 O2 C8 C9 -177.4(5) . . . . ? O7 C8 C9 C14 -166.4(7) . . . . ? O2 C8 C9 C14 13.7(10) . . . . ? O7 C8 C9 C10 11.5(11) . . . . ? O2 C8 C9 C10 -168.5(6) . . . . ? C14 C9 C10 C11 -0.5(12) . . . . ? C8 C9 C10 C11 -178.4(7) . . . . ? C9 C10 C11 C12 1.7(12) . . . . ? C10 C11 C12 C13 -2.4(12) . . . . ? C10 C11 C12 Cl1 179.6(6) . . . . ? C11 C12 C13 C14 1.8(12) . . . . ? Cl1 C12 C13 C14 179.8(6) . . . . ? C10 C9 C14 C13 -0.1(11) . . . . ? C8 C9 C14 C13 177.7(7) . . . . ? C12 C13 C14 C9 -0.5(11) . . . . ? C6 O6 C15 O8 -3.5(9) . . . . ? C6 O6 C15 C16 175.4(5) . . . . ? O8 C15 C16 C17 3.2(11) . . . . ? O6 C15 C16 C17 -175.6(6) . . . . ? O8 C15 C16 C21 -174.1(7) . . . . ? O6 C15 C16 C21 7.1(9) . . . . ? C21 C16 C17 C18 -1.7(12) . . . . ? C15 C16 C17 C18 -179.2(8) . . . . ? C16 C17 C18 C19 2.5(14) . . . . ? C17 C18 C19 C20 -2.7(15) . . . . ? C17 C18 C19 Cl2 177.7(7) . . . . ? C18 C19 C20 C21 2.4(14) . . . . ? Cl2 C19 C20 C21 -178.0(7) . . . . ? C19 C20 C21 C16 -1.6(13) . . . . ? C17 C16 C21 C20 1.3(11) . . . . ? C15 C16 C21 C20 178.7(7) . . . . ? C24 C22 C23 C24 -4.9(15) 2 . . . ? C22 C23 C24 C22 -0.7(16) . . . 2 ? C30 C25 C26 C27 0.0 . . . . ? C25 C26 C27 C28 0.0 . . . . ? C26 C27 C28 C29 0.0 . . . . ? C27 C28 C29 C30 0.0 . . . . ? C28 C29 C30 C25 0.0 . . . . ? C26 C25 C30 C29 0.0 . . . . ? 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 O4 H4A O7 0.84 1.98 2.813(6) 174.4 4_545 C11 H11 O1 0.95 2.49 3.227(8) 134.6 1_565 C14 H14 O8 0.95 2.60 3.239(8) 125.1 7_556 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.889 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.098 #===END data_3CT _database_code_depnum_ccdc_archive 'CCDC 752863' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate dichloromethane solvate ; _chemical_name_common ;2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate dichloromethane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8, 0.06(C H2 Cl2)' _chemical_formula_sum 'C21.06 H16.12 Cl2.12 O8' _chemical_formula_weight 472.33 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 monoclinic _symmetry_space_group_name_H-M 'P 2 1/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.962(2) _cell_length_b 10.1406(17) _cell_length_c 18.391(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.627(3) _cell_angle_gamma 90.00 _cell_volume 2358.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 2188 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 22.21 _exptl_crystal_description 'thin plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 970.2 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9024 _exptl_absorpt_correction_T_max 0.9597 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 11414 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4128 _reflns_number_gt 2902 _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 2.2' _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^)+(0.0781P)^2^+0.7766P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4128 _refine_ls_number_parameters 337 _refine_ls_number_restraints 101 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1586 _refine_ls_wR_factor_gt 0.1410 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.056 _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 Cl1 Cl 0.04970(9) 1.19519(9) -0.20444(5) 0.0891(4) Uani 1 1 d . . . Cl2 Cl -0.10598(12) 0.70362(18) 0.49711(9) 0.1494(7) Uani 1 1 d . A . O1 O 0.14304(16) 0.44899(19) 0.03502(10) 0.0532(5) Uani 1 1 d . . . O2 O 0.14090(15) 0.72682(17) 0.05242(9) 0.0476(5) Uani 1 1 d . . . O3 O 0.31049(16) 0.5393(2) 0.07044(11) 0.0582(5) Uani 1 1 d . . . O4 O 0.29620(18) 0.5901(2) 0.26237(12) 0.0595(6) Uani 1 1 d . . . O5 O 0.27467(18) 0.3359(2) 0.11697(11) 0.0622(6) Uani 1 1 d . . . O6 O 0.09354(17) 0.47349(19) 0.22225(11) 0.0587(6) Uani 1 1 d . A . O7 O 0.19439(18) 0.8981(2) 0.12772(10) 0.0642(6) Uani 1 1 d . . . O8 O -0.0053(8) 0.2999(8) 0.2343(5) 0.098(3) Uani 0.50 1 d PU A 1 O8' O -0.0477(7) 0.3494(10) 0.1991(5) 0.104(3) Uani 0.50 1 d PU A 2 C1 C 0.1072(2) 0.5123(3) 0.09493(14) 0.0458(7) Uani 1 1 d . . . H1 H 0.0312 0.5306 0.0801 0.055 Uiso 1 1 calc R . . C2 C 0.1682(2) 0.6396(3) 0.11571(13) 0.0431(6) Uani 1 1 d . . . H2 H 0.1487 0.6796 0.1593 0.052 Uiso 1 1 calc R . . C3 C 0.2852(2) 0.6084(3) 0.13258(14) 0.0481(7) Uani 1 1 d . . . H3 H 0.3262 0.6902 0.1418 0.058 Uiso 1 1 calc R . . C4 C 0.3134(2) 0.5187(3) 0.20012(15) 0.0525(7) Uani 1 1 d . . . H4 H 0.3885 0.4956 0.2084 0.063 Uiso 1 1 calc R . . C5 C 0.2476(2) 0.3933(3) 0.18184(15) 0.0522(7) Uani 1 1 d . . . H5 H 0.2643 0.3316 0.2238 0.063 Uiso 1 1 calc R . . C6 C 0.1292(2) 0.4175(3) 0.16059(15) 0.0503(7) Uani 1 1 d . . . H6 H 0.0924 0.3340 0.1461 0.060 Uiso 1 1 calc R . . C7 C 0.2521(3) 0.4236(3) 0.05608(18) 0.0595(8) Uani 1 1 d . . . C8 C 0.1591(2) 0.8559(3) 0.06591(15) 0.0459(6) Uani 1 1 d . . . C9 C 0.1317(2) 0.9366(3) -0.00212(14) 0.0439(6) Uani 1 1 d . . . C10 C 0.1397(2) 1.0730(3) 0.00467(17) 0.0525(7) Uani 1 1 d . . . C11 C 0.1141(3) 1.1518(3) -0.05748(18) 0.0583(8) Uani 1 1 d . . . C12 C 0.0811(2) 1.0943(3) -0.12616(16) 0.0564(8) Uani 1 1 d . . . C13 C 0.0729(3) 0.9596(3) -0.13442(18) 0.0602(8) Uani 1 1 d . . . C14 C 0.0980(2) 0.8810(3) -0.07218(16) 0.0533(8) Uani 1 1 d . . . C15 C 0.0153(3) 0.4182(3) 0.2460(2) 0.0704(10) Uani 1 1 d . . . C16 C -0.0107(3) 0.4875(3) 0.30949(19) 0.0619(8) Uani 1 1 d U A . C17 C -0.0995(3) 0.4497(5) 0.3350(3) 0.1054(14) Uani 1 1 d U . . H17 H -0.1398 0.3787 0.3128 0.127 Uiso 1 1 calc R A . C18 C -0.1284(4) 0.5156(5) 0.3926(3) 0.1119(15) Uani 1 1 d U A . H18 H -0.1887 0.4906 0.4088 0.134 Uiso 1 1 calc R . . C19 C -0.0683(3) 0.6177(4) 0.4259(2) 0.0870(12) Uani 1 1 d U . . C20 C 0.0197(3) 0.6553(4) 0.4021(2) 0.0819(11) Uani 1 1 d U A . H20 H 0.0603 0.7257 0.4249 0.098 Uiso 1 1 calc R . . C21 C 0.0483(3) 0.5897(3) 0.34481(17) 0.0618(8) Uani 1 1 d U . . H21 H 0.1092 0.6151 0.3295 0.074 Uiso 1 1 calc R A . H7 H 0.274(2) 0.382(3) 0.0157(17) 0.058(8) Uiso 1 1 d . . . H10 H 0.163(2) 1.111(3) 0.0520(18) 0.072(10) Uiso 1 1 d . . . H11 H 0.119(2) 1.247(3) -0.0545(17) 0.068(9) Uiso 1 1 d . . . H13 H 0.056(3) 0.915(4) -0.181(2) 0.089(12) Uiso 1 1 d . . . H14 H 0.093(2) 0.792(3) -0.0784(16) 0.055(8) Uiso 1 1 d . . . H4A H 0.294(3) 0.543(4) 0.296(2) 0.077(12) Uiso 1 1 d . . . C22 C 0.337(5) 0.551(6) 0.876(14) 0.119(16) Uiso 0.03 1 d PDU B 1 H22A H 0.3689 0.5908 0.9232 0.143 Uiso 0.03 1 calc PR B 1 H22B H 0.3480 0.6095 0.8362 0.143 Uiso 0.03 1 calc PR B 1 Cl3 Cl 0.394(3) 0.397(5) 0.867(3) 0.125(12) Uiso 0.03 1 d PDU B 1 Cl4 Cl 0.202(3) 0.526(5) 0.869(3) 0.113(11) Uiso 0.03 1 d PDU B 1 C22' C 0.304(4) 0.566(5) 0.866(14) 0.119(16) Uiso 0.03 1 d PDU C 2 H22C H 0.2890 0.6221 0.9049 0.143 Uiso 0.03 1 calc PR C 2 H22D H 0.3004 0.6180 0.8214 0.143 Uiso 0.03 1 calc PR C 2 Cl3' Cl 0.431(3) 0.495(5) 0.895(3) 0.115(11) Uiso 0.03 1 d PDU C 2 Cl4' Cl 0.214(3) 0.435(5) 0.848(3) 0.114(11) Uiso 0.03 1 d PDU C 2 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 Cl1 0.1182(8) 0.0664(6) 0.0706(6) 0.0279(5) -0.0057(5) -0.0021(5) Cl2 0.1357(11) 0.1891(15) 0.1522(12) -0.0967(11) 0.0943(10) -0.0448(10) O1 0.0683(13) 0.0521(12) 0.0387(10) -0.0099(9) 0.0107(9) 0.0006(10) O2 0.0686(13) 0.0351(10) 0.0348(9) 0.0005(8) 0.0017(8) 0.0049(9) O3 0.0627(13) 0.0619(13) 0.0537(12) 0.0019(10) 0.0204(10) 0.0020(11) O4 0.0902(16) 0.0453(12) 0.0378(11) 0.0037(10) 0.0028(10) -0.0020(11) O5 0.0846(15) 0.0455(11) 0.0587(13) 0.0000(10) 0.0204(11) 0.0182(11) O6 0.0831(14) 0.0465(11) 0.0541(12) -0.0123(9) 0.0318(11) -0.0182(11) O7 0.1034(17) 0.0452(12) 0.0390(11) -0.0067(9) 0.0049(11) -0.0017(11) O8 0.128(7) 0.062(4) 0.126(7) -0.031(4) 0.078(5) -0.038(4) O8' 0.087(5) 0.117(7) 0.116(6) -0.069(5) 0.041(4) -0.049(5) C1 0.0501(15) 0.0456(16) 0.0413(15) -0.0061(12) 0.0093(12) 0.0001(13) C2 0.0594(16) 0.0371(14) 0.0309(13) 0.0014(11) 0.0055(11) 0.0029(12) C3 0.0571(17) 0.0445(16) 0.0412(15) -0.0001(13) 0.0075(12) -0.0027(13) C4 0.0630(18) 0.0449(16) 0.0459(16) 0.0070(13) 0.0034(13) 0.0061(14) C5 0.076(2) 0.0378(15) 0.0424(15) 0.0021(12) 0.0123(14) 0.0079(14) C6 0.0735(19) 0.0354(14) 0.0455(15) -0.0079(12) 0.0206(14) -0.0094(14) C7 0.079(2) 0.0534(19) 0.0503(18) -0.0071(15) 0.0223(16) 0.0099(17) C8 0.0581(17) 0.0382(15) 0.0407(15) -0.0044(12) 0.0095(12) 0.0038(13) C9 0.0500(15) 0.0376(14) 0.0418(15) 0.0008(12) 0.0054(12) 0.0056(12) C10 0.0666(19) 0.0388(15) 0.0489(17) -0.0073(13) 0.0053(14) 0.0017(14) C11 0.071(2) 0.0351(16) 0.065(2) 0.0033(15) 0.0067(16) 0.0026(15) C12 0.0635(19) 0.0483(18) 0.0523(17) 0.0100(14) 0.0018(14) 0.0026(14) C13 0.082(2) 0.0477(19) 0.0436(17) 0.0018(15) -0.0018(16) -0.0034(16) C14 0.072(2) 0.0353(16) 0.0471(16) -0.0010(13) 0.0008(14) 0.0007(14) C15 0.071(2) 0.060(2) 0.088(3) -0.0225(19) 0.035(2) -0.0196(18) C16 0.0635(19) 0.0577(18) 0.073(2) -0.0115(16) 0.0325(16) -0.0126(15) C17 0.097(3) 0.111(3) 0.126(3) -0.054(3) 0.062(2) -0.046(2) C18 0.094(3) 0.128(3) 0.135(3) -0.048(3) 0.073(3) -0.036(3) C19 0.083(2) 0.100(3) 0.092(3) -0.035(2) 0.048(2) -0.019(2) C20 0.086(2) 0.093(3) 0.075(2) -0.032(2) 0.0366(19) -0.029(2) C21 0.0656(19) 0.068(2) 0.0588(18) -0.0116(16) 0.0276(15) -0.0155(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 Cl1 C12 1.741(3) . ? Cl2 C19 1.730(4) . ? O1 C7 1.406(4) . ? O1 C1 1.437(3) . ? O2 C8 1.343(3) . ? O2 C2 1.443(3) . ? O3 C7 1.390(4) . ? O3 C3 1.438(3) . ? O4 C4 1.413(4) . ? O4 H4A 0.79(4) . ? O5 C7 1.410(4) . ? O5 C5 1.438(3) . ? O6 C15 1.314(4) . ? O6 C6 1.432(3) . ? O7 C8 1.208(3) . ? O8 C15 1.238(8) . ? O8' C15 1.261(8) . ? C1 C2 1.519(4) . ? C1 C6 1.521(4) . ? C1 H1 0.9800 . ? C2 C3 1.514(4) . ? C2 H2 0.9800 . ? C3 C4 1.518(4) . ? C3 H3 0.9800 . ? C4 C5 1.527(4) . ? C4 H4 0.9800 . ? C5 C6 1.518(4) . ? C5 H5 0.9800 . ? C6 H6 0.9800 . ? C7 H7 0.95(3) . ? C8 C9 1.472(4) . ? C9 C14 1.387(4) . ? C9 C10 1.390(4) . ? C10 C11 1.375(4) . ? C10 H10 0.94(3) . ? C11 C12 1.372(4) . ? C11 H11 0.97(3) . ? C12 C13 1.375(4) . ? C13 C14 1.374(4) . ? C13 H13 0.95(4) . ? C14 H14 0.91(3) . ? C15 C16 1.464(4) . ? C16 C21 1.365(4) . ? C16 C17 1.388(5) . ? C17 C18 1.373(5) . ? C17 H17 0.9300 . ? C18 C19 1.358(6) . ? C18 H18 0.9300 . ? C19 C20 1.363(5) . ? C20 C21 1.364(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 Cl4 1.75(2) . ? C22 Cl3 1.75(2) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22' Cl4' 1.75(2) . ? C22' Cl3' 1.76(2) . ? C22' H22C 0.9700 . ? C22' H22D 0.9700 . ? 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 110.2(2) . . ? C8 O2 C2 116.48(19) . . ? C7 O3 C3 110.7(2) . . ? C4 O4 H4A 111(3) . . ? C7 O5 C5 111.0(2) . . ? C15 O6 C6 120.0(2) . . ? O1 C1 C2 109.6(2) . . ? O1 C1 C6 106.9(2) . . ? C2 C1 C6 109.9(2) . . ? O1 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? C6 C1 H1 110.2 . . ? O2 C2 C3 110.6(2) . . ? O2 C2 C1 107.21(19) . . ? C3 C2 C1 108.5(2) . . ? O2 C2 H2 110.2 . . ? C3 C2 H2 110.2 . . ? C1 C2 H2 110.2 . . ? O3 C3 C2 109.4(2) . . ? O3 C3 C4 107.6(2) . . ? C2 C3 C4 110.1(2) . . ? O3 C3 H3 109.9 . . ? C2 C3 H3 109.9 . . ? C4 C3 H3 109.9 . . ? O4 C4 C3 107.7(2) . . ? O4 C4 C5 115.2(2) . . ? C3 C4 C5 107.2(2) . . ? O4 C4 H4 108.9 . . ? C3 C4 H4 108.9 . . ? C5 C4 H4 108.9 . . ? O5 C5 C6 105.5(2) . . ? O5 C5 C4 107.1(2) . . ? C6 C5 C4 114.0(2) . . ? O5 C5 H5 110.0 . . ? C6 C5 H5 110.0 . . ? C4 C5 H5 110.0 . . ? O6 C6 C5 110.1(2) . . ? O6 C6 C1 109.9(2) . . ? C5 C6 C1 108.1(2) . . ? O6 C6 H6 109.6 . . ? C5 C6 H6 109.6 . . ? C1 C6 H6 109.6 . . ? O3 C7 O1 111.7(2) . . ? O3 C7 O5 111.8(2) . . ? O1 C7 O5 110.8(3) . . ? O3 C7 H7 106.2(18) . . ? O1 C7 H7 108.6(17) . . ? O5 C7 H7 107.4(18) . . ? O7 C8 O2 122.3(2) . . ? O7 C8 C9 125.0(2) . . ? O2 C8 C9 112.6(2) . . ? C14 C9 C10 119.3(3) . . ? C14 C9 C8 122.1(2) . . ? C10 C9 C8 118.5(2) . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10 120(2) . . ? C9 C10 H10 120(2) . . ? C12 C11 C10 119.2(3) . . ? C12 C11 H11 118.7(19) . . ? C10 C11 H11 122.1(19) . . ? C11 C12 C13 121.7(3) . . ? C11 C12 Cl1 118.7(2) . . ? C13 C12 Cl1 119.6(2) . . ? C14 C13 C12 119.0(3) . . ? C14 C13 H13 116(2) . . ? C12 C13 H13 124(2) . . ? C13 C14 C9 120.5(3) . . ? C13 C14 H14 118.3(18) . . ? C9 C14 H14 121.2(18) . . ? O8 C15 O6 120.6(5) . . ? O8' C15 O6 116.1(5) . . ? O8 C15 C16 121.7(5) . . ? O8' C15 C16 125.7(5) . . ? O6 C15 C16 112.9(3) . . ? C21 C16 C17 118.0(3) . . ? C21 C16 C15 122.7(3) . . ? C17 C16 C15 119.3(3) . . ? C18 C17 C16 120.8(4) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C19 C18 C17 119.5(4) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C20 120.4(3) . . ? C18 C19 Cl2 119.7(3) . . ? C20 C19 Cl2 119.8(3) . . ? C19 C20 C21 120.0(3) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C16 121.3(3) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? Cl4 C22 Cl3 107(2) . . ? Cl4 C22 H22A 110.2 . . ? Cl3 C22 H22A 110.2 . . ? Cl4 C22 H22B 110.2 . . ? Cl3 C22 H22B 110.2 . . ? H22A C22 H22B 108.5 . . ? Cl4' C22' Cl3' 107(2) . . ? Cl4' C22' H22C 110.3 . . ? Cl3' C22' H22C 110.3 . . ? Cl4' C22' H22D 110.3 . . ? Cl3' C22' H22D 110.3 . . ? H22C C22' H22D 108.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C2 58.2(3) . . . . ? C7 O1 C1 C6 -60.8(3) . . . . ? C8 O2 C2 C3 -81.9(3) . . . . ? C8 O2 C2 C1 160.0(2) . . . . ? O1 C1 C2 O2 65.0(3) . . . . ? C6 C1 C2 O2 -177.9(2) . . . . ? O1 C1 C2 C3 -54.4(3) . . . . ? C6 C1 C2 C3 62.7(3) . . . . ? C7 O3 C3 C2 -58.7(3) . . . . ? C7 O3 C3 C4 60.9(3) . . . . ? O2 C2 C3 O3 -63.0(3) . . . . ? C1 C2 C3 O3 54.3(3) . . . . ? O2 C2 C3 C4 178.9(2) . . . . ? C1 C2 C3 C4 -63.8(3) . . . . ? O3 C3 C4 O4 175.6(2) . . . . ? C2 C3 C4 O4 -65.3(3) . . . . ? O3 C3 C4 C5 -59.9(3) . . . . ? C2 C3 C4 C5 59.2(3) . . . . ? C7 O5 C5 C6 61.8(3) . . . . ? C7 O5 C5 C4 -60.0(3) . . . . ? O4 C4 C5 O5 179.2(2) . . . . ? C3 C4 C5 O5 59.4(3) . . . . ? O4 C4 C5 C6 62.9(3) . . . . ? C3 C4 C5 C6 -56.9(3) . . . . ? C15 O6 C6 C5 -126.5(3) . . . . ? C15 O6 C6 C1 114.6(3) . . . . ? O5 C5 C6 O6 179.2(2) . . . . ? C4 C5 C6 O6 -63.5(3) . . . . ? O5 C5 C6 C1 -60.7(3) . . . . ? C4 C5 C6 C1 56.5(3) . . . . ? O1 C1 C6 O6 -179.0(2) . . . . ? C2 C1 C6 O6 62.2(3) . . . . ? O1 C1 C6 C5 60.8(3) . . . . ? C2 C1 C6 C5 -58.0(3) . . . . ? C3 O3 C7 O1 63.2(3) . . . . ? C3 O3 C7 O5 -61.7(3) . . . . ? C1 O1 C7 O3 -62.9(3) . . . . ? C1 O1 C7 O5 62.5(3) . . . . ? C5 O5 C7 O3 61.7(3) . . . . ? C5 O5 C7 O1 -63.7(3) . . . . ? C2 O2 C8 O7 -1.4(4) . . . . ? C2 O2 C8 C9 178.4(2) . . . . ? O7 C8 C9 C14 175.7(3) . . . . ? O2 C8 C9 C14 -4.2(4) . . . . ? O7 C8 C9 C10 -4.5(4) . . . . ? O2 C8 C9 C10 175.6(3) . . . . ? C14 C9 C10 C11 0.3(5) . . . . ? C8 C9 C10 C11 -179.6(3) . . . . ? C9 C10 C11 C12 -0.3(5) . . . . ? C10 C11 C12 C13 0.0(5) . . . . ? C10 C11 C12 Cl1 -179.6(2) . . . . ? C11 C12 C13 C14 0.4(5) . . . . ? Cl1 C12 C13 C14 179.9(3) . . . . ? C12 C13 C14 C9 -0.4(5) . . . . ? C10 C9 C14 C13 0.1(5) . . . . ? C8 C9 C14 C13 179.9(3) . . . . ? C6 O6 C15 O8 23.9(7) . . . . ? C6 O6 C15 O8' -24.4(7) . . . . ? C6 O6 C15 C16 179.7(3) . . . . ? O8 C15 C16 C21 148.7(6) . . . . ? O8' C15 C16 C21 -160.0(7) . . . . ? O6 C15 C16 C21 -6.9(5) . . . . ? O8 C15 C16 C17 -31.9(8) . . . . ? O8' C15 C16 C17 19.4(9) . . . . ? O6 C15 C16 C17 172.6(4) . . . . ? C21 C16 C17 C18 1.9(7) . . . . ? C15 C16 C17 C18 -177.6(5) . . . . ? C16 C17 C18 C19 -1.2(8) . . . . ? C17 C18 C19 C20 0.5(8) . . . . ? C17 C18 C19 Cl2 178.5(4) . . . . ? C18 C19 C20 C21 -0.5(7) . . . . ? Cl2 C19 C20 C21 -178.5(3) . . . . ? C19 C20 C21 C16 1.2(6) . . . . ? C17 C16 C21 C20 -1.8(6) . . . . ? C15 C16 C21 C20 177.6(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 C13 H13 O8 0.95(4) 2.42(4) 3.220(9) 141(3) 3_565 C11 H11 O1 0.97(3) 2.60(3) 3.441(4) 145(2) 1_565 C5 H5 O4 0.98 2.60 3.329(4) 131.2 2_545 O4 H4A O7 0.79(4) 2.01(4) 2.790(3) 169(4) 2_545 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.409 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.048 #===END