Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Mohan M. Bhadbhade' _publ_contact_author_address ; Centre for Materials Characterization National Chemical Laboratory Dr Homi Bhabha Road Pashan Pune 411 008 INDIA ; _publ_contact_author_email MM.BHADBHADE@NCL.RES.IN _publ_section_title ; Crystal-to-Crystal Transformation Amongst Dimorphs of (p-halo benzoyl)-myo-inositol 1,3,5-orthoformates that Achieves Halogen Bonding Contacts ; loop_ _publ_author_name 'Mohan M Bhadbhade' 'Rajesh G Gonnade' 'Mysore S Shashidhar' # Attachment 'Form_II_1.cif' data_FormII_1 _database_code_depnum_ccdc_archive 'CCDC 655649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate ; _chemical_name_common '2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate' _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8' _chemical_formula_sum 'C21 H16 Br2 O8' _chemical_formula_weight 556.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8481(14) _cell_length_b 11.662(2) _cell_length_c 13.675(3) _cell_angle_alpha 107.123(4) _cell_angle_beta 99.175(4) _cell_angle_gamma 90.909(3) _cell_volume 1028.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2016 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 22.15 _exptl_crystal_description 'small block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 3.990 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5025 _exptl_absorpt_correction_T_max 0.5954 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7440 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3580 _reflns_number_gt 2567 _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 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003), Platon (Spek, 2002)' _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^)+(0.0468P)^2^+0.2118P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3580 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 -0.34905(8) 0.07807(5) 0.63028(5) 0.0973(2) Uani 1 1 d . . . Br2 Br 1.38232(8) 0.64622(5) 0.50387(4) 0.0813(2) Uani 1 1 d . . . O1 O 0.3162(3) 0.7935(2) 0.96644(17) 0.0411(6) Uani 1 1 d . . . O2 O 0.3479(3) 0.54187(19) 0.85223(17) 0.0409(6) Uani 1 1 d . . . O3 O 0.4952(3) 0.6885(2) 1.06578(17) 0.0424(6) Uani 1 1 d . . . O4 O 0.9258(4) 0.6794(3) 0.9422(2) 0.0582(8) Uani 1 1 d . . . O5 O 0.5962(3) 0.8854(2) 1.08424(17) 0.0455(6) Uani 1 1 d . . . O6 O 0.7045(3) 0.8073(2) 0.81874(17) 0.0425(6) Uani 1 1 d . . . O7 O 0.4527(4) 0.4642(3) 0.7023(2) 0.0873(11) Uani 1 1 d . . . O8 O 0.8603(4) 0.9899(2) 0.85996(19) 0.0509(7) Uani 1 1 d . . . C1 C 0.4287(5) 0.7529(3) 0.8836(3) 0.0350(8) Uani 1 1 d . . . C2 C 0.5087(5) 0.6333(3) 0.8820(3) 0.0347(8) Uani 1 1 d . . . C3 C 0.6198(5) 0.6429(3) 0.9892(3) 0.0387(8) Uani 1 1 d . . . C4 C 0.7993(5) 0.7305(3) 1.0132(3) 0.0432(9) Uani 1 1 d . . . C5 C 0.7247(5) 0.8499(3) 1.0074(3) 0.0418(9) Uani 1 1 d . . . C6 C 0.5987(5) 0.8463(3) 0.9043(3) 0.0375(8) Uani 1 1 d . . . C7 C 0.4358(5) 0.8011(3) 1.0628(3) 0.0445(9) Uani 1 1 d . . . C8 C 0.3364(5) 0.4616(3) 0.7578(3) 0.0449(9) Uani 1 1 d . . . C9 C 0.1668(5) 0.3722(3) 0.7315(3) 0.0413(8) Uani 1 1 d . . . C14 C 0.0035(5) 0.3899(4) 0.7805(3) 0.0458(9) Uani 1 1 d . . . C13 C -0.1511(6) 0.3025(4) 0.7502(3) 0.0540(10) Uani 1 1 d . . . C12 C -0.1366(6) 0.1987(4) 0.6737(3) 0.0590(11) Uani 1 1 d . . . C11 C 0.0229(8) 0.1793(4) 0.6241(4) 0.0698(13) Uani 1 1 d . . . C10 C 0.1738(7) 0.2667(4) 0.6521(3) 0.0642(12) Uani 1 1 d . . . C15 C 0.8409(5) 0.8867(3) 0.8100(3) 0.0386(8) Uani 1 1 d . . . C16 C 0.9636(5) 0.8268(3) 0.7315(2) 0.0365(8) Uani 1 1 d . . . C21 C 0.9460(6) 0.7042(4) 0.6840(3) 0.0486(10) Uani 1 1 d . . . C20 C 1.0706(6) 0.6503(4) 0.6165(3) 0.0545(10) Uani 1 1 d . . . C19 C 1.2126(6) 0.7206(4) 0.5968(3) 0.0527(10) Uani 1 1 d . . . C18 C 1.2338(6) 0.8430(4) 0.6431(3) 0.0544(11) Uani 1 1 d . . . C17 C 1.1082(6) 0.8945(4) 0.7108(3) 0.0464(9) Uani 1 1 d . . . H1 H 0.339(4) 0.751(2) 0.822(2) 0.017(7) Uiso 1 1 d . . . H2 H 0.589(5) 0.613(3) 0.837(2) 0.035(9) Uiso 1 1 d . . . H3 H 0.654(4) 0.568(3) 0.996(2) 0.032(9) Uiso 1 1 d . . . H4 H 0.862(4) 0.739(3) 1.082(3) 0.033(9) Uiso 1 1 d . . . H5 H 0.819(5) 0.904(3) 1.024(2) 0.037(9) Uiso 1 1 d . . . H6 H 0.556(4) 0.920(3) 0.905(2) 0.019(7) Uiso 1 1 d . . . H7 H 0.352(5) 0.831(3) 1.115(3) 0.043(9) Uiso 1 1 d . . . H14 H -0.003(5) 0.462(3) 0.833(3) 0.055(11) Uiso 1 1 d . . . H13 H -0.262(6) 0.314(3) 0.781(3) 0.063(12) Uiso 1 1 d . . . H11 H 0.027(6) 0.109(4) 0.572(3) 0.075(14) Uiso 1 1 d . . . H10 H 0.294(6) 0.256(3) 0.618(3) 0.061(11) Uiso 1 1 d . . . H21 H 0.854(5) 0.656(3) 0.695(2) 0.042(10) Uiso 1 1 d . . . H18 H 1.332(6) 0.885(3) 0.629(3) 0.062(12) Uiso 1 1 d . . . H17 H 1.116(5) 0.970(3) 0.737(3) 0.037(10) Uiso 1 1 d . . . H20 H 1.056(6) 0.562(4) 0.587(3) 0.074(13) Uiso 1 1 d . . . H4A H 1.021(6) 0.714(4) 0.958(3) 0.052(14) 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 0.0877(4) 0.0744(4) 0.1147(5) 0.0370(3) -0.0379(3) -0.0494(3) Br2 0.0904(4) 0.0985(4) 0.0729(3) 0.0329(3) 0.0491(3) 0.0399(3) O1 0.0323(12) 0.0460(15) 0.0462(14) 0.0136(12) 0.0109(11) 0.0034(10) O2 0.0384(13) 0.0359(13) 0.0413(13) 0.0003(11) 0.0095(10) -0.0133(10) O3 0.0464(14) 0.0420(15) 0.0418(13) 0.0152(11) 0.0119(11) -0.0016(11) O4 0.0279(15) 0.0627(19) 0.077(2) 0.0085(15) 0.0117(14) -0.0028(14) O5 0.0523(15) 0.0395(14) 0.0396(13) 0.0007(11) 0.0153(11) -0.0082(11) O6 0.0438(14) 0.0398(14) 0.0431(13) 0.0079(11) 0.0151(11) -0.0091(11) O7 0.078(2) 0.095(2) 0.0672(19) -0.0208(17) 0.0410(17) -0.0353(18) O8 0.0540(16) 0.0340(15) 0.0625(16) 0.0053(13) 0.0223(13) -0.0059(12) C1 0.0299(18) 0.040(2) 0.0349(18) 0.0116(15) 0.0047(15) -0.0005(15) C2 0.0276(17) 0.034(2) 0.0406(19) 0.0057(15) 0.0103(15) -0.0068(14) C3 0.0351(19) 0.032(2) 0.049(2) 0.0130(17) 0.0054(16) 0.0009(15) C4 0.0319(19) 0.050(2) 0.044(2) 0.0116(18) 0.0005(17) -0.0042(16) C5 0.036(2) 0.040(2) 0.044(2) 0.0059(17) 0.0087(17) -0.0131(17) C6 0.039(2) 0.028(2) 0.046(2) 0.0091(16) 0.0136(16) -0.0011(15) C7 0.049(2) 0.039(2) 0.048(2) 0.0103(17) 0.0212(19) -0.0012(17) C8 0.041(2) 0.041(2) 0.045(2) 0.0022(18) 0.0078(17) -0.0048(16) C9 0.041(2) 0.037(2) 0.0392(19) 0.0064(16) -0.0021(16) -0.0055(16) C14 0.044(2) 0.043(2) 0.046(2) 0.0130(19) -0.0034(17) -0.0050(18) C13 0.041(2) 0.055(3) 0.065(3) 0.024(2) -0.004(2) -0.0125(19) C12 0.060(3) 0.044(3) 0.063(3) 0.022(2) -0.026(2) -0.022(2) C11 0.082(3) 0.041(3) 0.066(3) -0.005(2) -0.005(3) -0.010(2) C10 0.062(3) 0.055(3) 0.062(3) -0.003(2) 0.009(2) -0.008(2) C15 0.0363(19) 0.041(2) 0.0401(19) 0.0139(17) 0.0068(15) -0.0032(16) C16 0.0366(19) 0.037(2) 0.0350(18) 0.0085(16) 0.0068(15) -0.0008(15) C21 0.045(2) 0.051(3) 0.046(2) 0.0079(19) 0.0081(18) -0.0103(19) C20 0.062(3) 0.050(3) 0.044(2) 0.001(2) 0.0107(19) 0.002(2) C19 0.050(2) 0.071(3) 0.042(2) 0.019(2) 0.0169(18) 0.015(2) C18 0.052(2) 0.064(3) 0.060(3) 0.028(2) 0.026(2) 0.004(2) C17 0.052(2) 0.041(3) 0.050(2) 0.016(2) 0.0172(18) -0.0001(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C12 1.902(4) . ? Br2 C19 1.890(3) . ? O1 C7 1.414(4) . ? O1 C1 1.441(4) . ? O2 C8 1.343(4) . ? O2 C2 1.442(4) . ? O3 C7 1.391(4) . ? O3 C3 1.442(4) . ? O4 C4 1.411(4) . ? O4 H4A 0.73(4) . ? O5 C7 1.398(4) . ? O5 C5 1.449(4) . ? O6 C15 1.348(4) . ? O6 C6 1.438(4) . ? O7 C8 1.190(4) . ? O8 C15 1.190(4) . ? C1 C2 1.502(5) . ? C1 C6 1.515(5) . ? C1 H1 0.96(3) . ? C2 C3 1.512(5) . ? C2 H2 0.87(3) . ? C3 C4 1.516(5) . ? C3 H3 0.93(3) . ? C4 C5 1.509(5) . ? C4 H4 0.94(3) . ? C5 C6 1.520(5) . ? C5 H5 0.85(3) . ? C6 H6 0.91(3) . ? C7 H7 0.97(3) . ? C8 C9 1.475(5) . ? C9 C14 1.380(5) . ? C9 C10 1.388(5) . ? C14 C13 1.382(5) . ? C14 H14 0.94(4) . ? C13 C12 1.364(6) . ? C13 H13 0.92(4) . ? C12 C11 1.364(6) . ? C11 C10 1.365(6) . ? C11 H11 0.92(4) . ? C10 H10 1.00(4) . ? C15 C16 1.487(4) . ? C16 C17 1.371(5) . ? C16 C21 1.381(5) . ? C21 C20 1.378(5) . ? C21 H21 0.89(3) . ? C20 C19 1.371(6) . ? C20 H20 0.98(4) . ? C19 C18 1.376(6) . ? C18 C17 1.379(5) . ? C18 H18 0.90(4) . ? C17 H17 0.84(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 110.1(2) . . ? C8 O2 C2 115.8(2) . . ? C7 O3 C3 110.1(3) . . ? C4 O4 H4A 109(3) . . ? C7 O5 C5 111.0(3) . . ? C15 O6 C6 117.1(3) . . ? O1 C1 C2 110.6(3) . . ? O1 C1 C6 106.9(3) . . ? C2 C1 C6 109.7(3) . . ? O1 C1 H1 105.2(15) . . ? C2 C1 H1 113.7(16) . . ? C6 C1 H1 110.3(16) . . ? O2 C2 C1 109.9(3) . . ? O2 C2 C3 110.3(3) . . ? C1 C2 C3 108.5(3) . . ? O2 C2 H2 108(2) . . ? C1 C2 H2 111(2) . . ? C3 C2 H2 109(2) . . ? O3 C3 C2 110.1(3) . . ? O3 C3 C4 108.3(3) . . ? C2 C3 C4 108.8(3) . . ? O3 C3 H3 105.3(18) . . ? C2 C3 H3 112.3(19) . . ? C4 C3 H3 112.0(19) . . ? O4 C4 C5 115.1(3) . . ? O4 C4 C3 107.1(3) . . ? C5 C4 C3 107.3(3) . . ? O4 C4 H4 110.3(18) . . ? C5 C4 H4 109.4(19) . . ? C3 C4 H4 107.3(19) . . ? O5 C5 C4 106.5(3) . . ? O5 C5 C6 105.9(3) . . ? C4 C5 C6 114.8(3) . . ? O5 C5 H5 107(2) . . ? C4 C5 H5 112(2) . . ? C6 C5 H5 111(2) . . ? O6 C6 C1 106.3(3) . . ? O6 C6 C5 112.5(3) . . ? C1 C6 C5 107.1(3) . . ? O6 C6 H6 107.2(17) . . ? C1 C6 H6 112.3(18) . . ? C5 C6 H6 111.4(18) . . ? O3 C7 O5 112.4(3) . . ? O3 C7 O1 111.0(3) . . ? O5 C7 O1 110.8(3) . . ? O3 C7 H7 109.1(19) . . ? O5 C7 H7 108(2) . . ? O1 C7 H7 105.6(19) . . ? O7 C8 O2 122.4(3) . . ? O7 C8 C9 124.6(3) . . ? O2 C8 C9 113.0(3) . . ? C14 C9 C10 119.6(4) . . ? C14 C9 C8 123.3(3) . . ? C10 C9 C8 117.1(3) . . ? C9 C14 C13 119.8(4) . . ? C9 C14 H14 120(2) . . ? C13 C14 H14 121(2) . . ? C12 C13 C14 118.9(4) . . ? C12 C13 H13 121(3) . . ? C14 C13 H13 121(3) . . ? C11 C12 C13 122.3(4) . . ? C11 C12 Br1 118.1(3) . . ? C13 C12 Br1 119.5(4) . . ? C12 C11 C10 118.9(4) . . ? C12 C11 H11 120(3) . . ? C10 C11 H11 121(3) . . ? C11 C10 C9 120.4(4) . . ? C11 C10 H10 122(2) . . ? C9 C10 H10 118(2) . . ? O8 C15 O6 123.9(3) . . ? O8 C15 C16 125.4(3) . . ? O6 C15 C16 110.7(3) . . ? C17 C16 C21 118.8(3) . . ? C17 C16 C15 118.9(3) . . ? C21 C16 C15 122.2(3) . . ? C20 C21 C16 120.9(4) . . ? C20 C21 H21 117(2) . . ? C16 C21 H21 122(2) . . ? C19 C20 C21 118.9(4) . . ? C19 C20 H20 123(2) . . ? C21 C20 H20 118(2) . . ? C20 C19 C18 121.5(3) . . ? C20 C19 Br2 118.7(3) . . ? C18 C19 Br2 119.8(3) . . ? C19 C18 C17 118.4(4) . . ? C19 C18 H18 118(2) . . ? C17 C18 H18 123(3) . . ? C16 C17 C18 121.6(4) . . ? C16 C17 H17 119(2) . . ? C18 C17 H17 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 57.6(3) . . . . ? C7 O1 C1 C6 -61.8(3) . . . . ? C8 O2 C2 C1 109.7(3) . . . . ? C8 O2 C2 C3 -130.7(3) . . . . ? O1 C1 C2 O2 67.9(3) . . . . ? C6 C1 C2 O2 -174.4(2) . . . . ? O1 C1 C2 C3 -52.8(3) . . . . ? C6 C1 C2 C3 64.9(3) . . . . ? C7 O3 C3 C2 -59.1(3) . . . . ? C7 O3 C3 C4 59.6(4) . . . . ? O2 C2 C3 O3 -67.2(3) . . . . ? C1 C2 C3 O3 53.3(3) . . . . ? O2 C2 C3 C4 174.3(3) . . . . ? C1 C2 C3 C4 -65.2(3) . . . . ? O3 C3 C4 O4 175.6(3) . . . . ? C2 C3 C4 O4 -64.8(4) . . . . ? O3 C3 C4 C5 -60.3(4) . . . . ? C2 C3 C4 C5 59.3(4) . . . . ? C7 O5 C5 C4 -60.7(4) . . . . ? C7 O5 C5 C6 61.9(4) . . . . ? O4 C4 C5 O5 179.0(3) . . . . ? C3 C4 C5 O5 59.9(3) . . . . ? O4 C4 C5 C6 62.2(4) . . . . ? C3 C4 C5 C6 -56.9(4) . . . . ? C15 O6 C6 C1 168.4(3) . . . . ? C15 O6 C6 C5 -74.7(4) . . . . ? O1 C1 C6 O6 -177.5(3) . . . . ? C2 C1 C6 O6 62.5(3) . . . . ? O1 C1 C6 C5 62.0(3) . . . . ? C2 C1 C6 C5 -58.0(3) . . . . ? O5 C5 C6 O6 -177.7(3) . . . . ? C4 C5 C6 O6 -60.5(4) . . . . ? O5 C5 C6 C1 -61.3(3) . . . . ? C4 C5 C6 C1 55.9(4) . . . . ? C3 O3 C7 O5 -60.6(3) . . . . ? C3 O3 C7 O1 64.0(3) . . . . ? C5 O5 C7 O3 61.9(4) . . . . ? C5 O5 C7 O1 -62.8(4) . . . . ? C1 O1 C7 O3 -63.3(3) . . . . ? C1 O1 C7 O5 62.3(3) . . . . ? C2 O2 C8 O7 1.0(5) . . . . ? C2 O2 C8 C9 -178.9(3) . . . . ? O7 C8 C9 C14 -160.0(4) . . . . ? O2 C8 C9 C14 19.9(5) . . . . ? O7 C8 C9 C10 18.8(6) . . . . ? O2 C8 C9 C10 -161.3(3) . . . . ? C10 C9 C14 C13 0.2(6) . . . . ? C8 C9 C14 C13 179.0(3) . . . . ? C9 C14 C13 C12 1.4(6) . . . . ? C14 C13 C12 C11 -1.7(6) . . . . ? C14 C13 C12 Br1 -179.4(3) . . . . ? C13 C12 C11 C10 0.2(7) . . . . ? Br1 C12 C11 C10 177.9(3) . . . . ? C12 C11 C10 C9 1.6(7) . . . . ? C14 C9 C10 C11 -1.8(6) . . . . ? C8 C9 C10 C11 179.4(4) . . . . ? C6 O6 C15 O8 -10.0(5) . . . . ? C6 O6 C15 C16 169.1(3) . . . . ? O8 C15 C16 C17 -2.2(5) . . . . ? O6 C15 C16 C17 178.8(3) . . . . ? O8 C15 C16 C21 173.3(4) . . . . ? O6 C15 C16 C21 -5.7(5) . . . . ? C17 C16 C21 C20 -0.3(6) . . . . ? C15 C16 C21 C20 -175.8(3) . . . . ? C16 C21 C20 C19 -0.3(6) . . . . ? C21 C20 C19 C18 0.4(6) . . . . ? C21 C20 C19 Br2 -179.8(3) . . . . ? C20 C19 C18 C17 0.1(6) . . . . ? Br2 C19 C18 C17 -179.8(3) . . . . ? C21 C16 C17 C18 0.8(6) . . . . ? C15 C16 C17 C18 176.4(3) . . . . ? C19 C18 C17 C16 -0.7(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 C3 H3 O2 0.93(3) 2.74(3) 3.465(4) 135(2) 2_667 C5 H5 O8 0.85(3) 2.55(3) 3.324(4) 151(3) 2_777 C6 H6 O5 0.91(3) 2.48(3) 3.392(4) 173(2) 2_677 C7 H7 O8 0.97(3) 2.54(3) 3.239(4) 129(2) 2_677 C14 H14 O4 0.94(4) 2.63(4) 3.551(5) 166(3) 1_455 C13 H13 O3 0.92(4) 2.84(4) 3.693(5) 155(3) 2_567 C10 H10 Br1 1.00(4) 3.25(4) 3.970(5) 130(3) 1_655 C18 H18 Br1 0.90(4) 3.11(4) 3.987(4) 166(3) 1_765 O4 H4A O1 0.73(4) 2.18(4) 2.894(4) 165(4) 1_655 C17 H17 O5 0.84(3) 2.94(3) 3.511(5) 127(3) 2_777 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.597 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.064 # Attachment 'Form_II_2.cif' data_FormII_2 _database_code_depnum_ccdc_archive 'CCDC 655650' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate ; _chemical_name_common '2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate' _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8' _chemical_formula_sum 'C21 H16 Cl2 O8' _chemical_formula_weight 467.24 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.794(5) _cell_length_b 11.545(9) _cell_length_c 13.565(10) _cell_angle_alpha 106.843(11) _cell_angle_beta 98.733(12) _cell_angle_gamma 91.059(12) _cell_volume 1004.4(13) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4258 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.4 _exptl_crystal_description 'small block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.372 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8909 _exptl_absorpt_correction_T_max 0.9429 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9304 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3506 _reflns_number_gt 3152 _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 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003), Platon (Spek, 2002)' _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^)+(0.0585P)^2^+0.4529P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3506 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 -0.35021(16) 0.08985(9) 0.13313(9) 0.1220(5) Uani 1 1 d . . . Cl2 Cl 1.39702(14) 0.65454(9) 0.01041(7) 0.0948(3) Uani 1 1 d . . . O1 O 0.3196(2) 0.79418(13) 0.46379(11) 0.0420(4) Uani 1 1 d . . . O2 O 0.3479(2) 0.54017(12) 0.35031(11) 0.0413(4) Uani 1 1 d . . . O3 O 0.4963(2) 0.68798(13) 0.56395(11) 0.0426(4) Uani 1 1 d . . . O4 O 0.9326(2) 0.67614(16) 0.43885(15) 0.0568(5) Uani 1 1 d . . . O5 O 0.6015(2) 0.88610(13) 0.58100(11) 0.0460(4) Uani 1 1 d . . . O6 O 0.7134(2) 0.80621(13) 0.31401(11) 0.0436(4) Uani 1 1 d . . . O7 O 0.4496(3) 0.4626(2) 0.19759(16) 0.0890(7) Uani 1 1 d . . . O8 O 0.8621(2) 0.99171(14) 0.35063(13) 0.0535(4) Uani 1 1 d . . . C1 C 0.4330(3) 0.75262(18) 0.37975(16) 0.0370(4) Uani 1 1 d . . . C2 C 0.5120(3) 0.63071(17) 0.37924(16) 0.0363(4) Uani 1 1 d . . . C3 C 0.6216(3) 0.64070(19) 0.48688(17) 0.0386(5) Uani 1 1 d . . . C4 C 0.8060(3) 0.7285(2) 0.51028(18) 0.0425(5) Uani 1 1 d . . . C5 C 0.7319(3) 0.85006(19) 0.50348(17) 0.0408(5) Uani 1 1 d . . . C6 C 0.6058(3) 0.84598(19) 0.39986(16) 0.0388(5) Uani 1 1 d . . . C7 C 0.4385(3) 0.80214(19) 0.56048(17) 0.0431(5) Uani 1 1 d . . . C8 C 0.3342(3) 0.46057(19) 0.25485(17) 0.0443(5) Uani 1 1 d . . . C9 C 0.1607(3) 0.37124(19) 0.22879(17) 0.0430(5) Uani 1 1 d . . . C10 C 0.1654(5) 0.2657(2) 0.1484(2) 0.0658(7) Uani 1 1 d . . . C11 C 0.0090(5) 0.1787(3) 0.1206(3) 0.0757(9) Uani 1 1 d . . . C12 C -0.1511(4) 0.1989(2) 0.1717(2) 0.0674(8) Uani 1 1 d . . . C13 C -0.1610(4) 0.3031(3) 0.2500(2) 0.0605(7) Uani 1 1 d . . . C14 C -0.0029(3) 0.3896(2) 0.2793(2) 0.0482(5) Uani 1 1 d . . . C15 C 0.8466(3) 0.88631(19) 0.30221(16) 0.0389(5) Uani 1 1 d . . . C16 C 0.9747(3) 0.82710(19) 0.22503(16) 0.0399(5) Uani 1 1 d . . . C17 C 1.1229(3) 0.8975(2) 0.20572(19) 0.0486(5) Uani 1 1 d . . . C18 C 1.2531(4) 0.8450(3) 0.1395(2) 0.0587(7) Uani 1 1 d . . . C19 C 1.2345(4) 0.7221(3) 0.09343(19) 0.0581(7) Uani 1 1 d . . . C20 C 1.0894(4) 0.6504(3) 0.1121(2) 0.0588(6) Uani 1 1 d . . . C21 C 0.9580(4) 0.7026(2) 0.17744(18) 0.0504(6) Uani 1 1 d . . . H1 H 0.347(3) 0.7496(18) 0.3201(17) 0.033(5) Uiso 1 1 d . . . H2 H 0.596(3) 0.6097(18) 0.3331(16) 0.031(5) Uiso 1 1 d . . . H3 H 0.650(3) 0.568(2) 0.4934(16) 0.035(5) Uiso 1 1 d . . . H4 H 0.867(4) 0.738(2) 0.582(2) 0.055(7) Uiso 1 1 d . . . H5 H 0.833(3) 0.908(2) 0.5230(17) 0.042(6) Uiso 1 1 d . . . H6 H 0.560(3) 0.919(2) 0.4051(17) 0.040(6) Uiso 1 1 d . . . H7 H 0.358(3) 0.8334(18) 0.6149(17) 0.036(5) Uiso 1 1 d . . . H10 H 0.273(5) 0.256(3) 0.114(2) 0.081(10) Uiso 1 1 d . . . H11 H 0.023(5) 0.113(3) 0.068(3) 0.097(11) Uiso 1 1 d . . . H13 H -0.275(5) 0.314(3) 0.285(2) 0.085(10) Uiso 1 1 d . . . H14 H -0.011(4) 0.460(2) 0.3306(19) 0.050(7) Uiso 1 1 d . . . H17 H 1.137(4) 0.979(2) 0.2372(19) 0.052(7) Uiso 1 1 d . . . H18 H 1.354(5) 0.891(3) 0.126(2) 0.078(9) Uiso 1 1 d . . . H20 H 1.077(4) 0.569(2) 0.083(2) 0.052(7) Uiso 1 1 d . . . H21 H 0.859(4) 0.653(2) 0.1888(19) 0.056(7) Uiso 1 1 d . . . H4A H 1.039(5) 0.717(3) 0.454(2) 0.080(10) 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 0.1105(7) 0.0918(7) 0.1491(9) 0.0542(6) -0.0518(7) -0.0616(6) Cl2 0.1037(7) 0.1192(7) 0.0811(6) 0.0360(5) 0.0583(5) 0.0507(5) O1 0.0329(7) 0.0443(8) 0.0518(9) 0.0150(7) 0.0142(6) 0.0078(6) O2 0.0389(8) 0.0364(7) 0.0435(8) 0.0019(6) 0.0117(6) -0.0092(6) O3 0.0438(8) 0.0416(8) 0.0460(8) 0.0158(6) 0.0133(6) 0.0022(6) O4 0.0292(8) 0.0588(10) 0.0772(12) 0.0101(9) 0.0133(8) 0.0028(7) O5 0.0508(9) 0.0387(8) 0.0437(8) 0.0015(6) 0.0147(7) -0.0046(6) O6 0.0469(8) 0.0395(8) 0.0448(8) 0.0084(6) 0.0177(7) -0.0053(6) O7 0.0797(14) 0.0974(16) 0.0664(12) -0.0242(11) 0.0398(11) -0.0336(11) O8 0.0536(10) 0.0378(9) 0.0687(11) 0.0087(8) 0.0233(8) -0.0025(7) C1 0.0304(10) 0.0420(11) 0.0387(11) 0.0121(9) 0.0057(9) 0.0014(8) C2 0.0293(10) 0.0337(10) 0.0444(11) 0.0065(9) 0.0118(9) -0.0031(8) C3 0.0354(11) 0.0323(10) 0.0505(12) 0.0147(9) 0.0092(9) 0.0045(8) C4 0.0303(10) 0.0477(12) 0.0463(12) 0.0114(10) 0.0019(9) 0.0006(9) C5 0.0345(11) 0.0384(11) 0.0449(12) 0.0043(9) 0.0093(9) -0.0082(9) C6 0.0399(11) 0.0328(11) 0.0459(12) 0.0112(9) 0.0146(9) 0.0028(9) C7 0.0456(12) 0.0395(11) 0.0442(12) 0.0073(9) 0.0180(10) 0.0018(9) C8 0.0411(12) 0.0434(12) 0.0436(12) 0.0040(9) 0.0093(10) 0.0012(9) C9 0.0430(12) 0.0378(11) 0.0423(11) 0.0079(9) -0.0025(9) -0.0009(9) C10 0.0655(17) 0.0532(15) 0.0630(17) -0.0032(12) 0.0029(14) -0.0014(13) C11 0.089(2) 0.0459(15) 0.0703(19) -0.0027(14) -0.0118(17) -0.0101(15) C12 0.0638(17) 0.0542(15) 0.0767(19) 0.0287(14) -0.0265(15) -0.0232(13) C13 0.0474(14) 0.0610(16) 0.0741(18) 0.0300(14) -0.0050(13) -0.0106(12) C14 0.0443(13) 0.0424(12) 0.0552(14) 0.0146(11) 0.0008(10) -0.0023(10) C15 0.0367(11) 0.0388(12) 0.0424(11) 0.0144(9) 0.0061(9) -0.0013(8) C16 0.0383(11) 0.0443(12) 0.0375(11) 0.0129(9) 0.0062(9) 0.0009(9) C17 0.0485(13) 0.0484(14) 0.0536(14) 0.0191(11) 0.0149(11) 0.0004(10) C18 0.0531(15) 0.0731(18) 0.0624(16) 0.0316(14) 0.0248(12) 0.0078(12) C19 0.0577(15) 0.0797(18) 0.0431(13) 0.0216(12) 0.0187(11) 0.0204(13) C20 0.0663(17) 0.0539(15) 0.0469(14) 0.0000(12) 0.0100(12) 0.0099(12) C21 0.0470(13) 0.0514(14) 0.0481(13) 0.0074(11) 0.0087(11) -0.0031(11) _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 1.731(3) . ? O1 C7 1.410(3) . ? O1 C1 1.444(2) . ? O2 C8 1.342(3) . ? O2 C2 1.441(2) . ? O3 C7 1.394(3) . ? O3 C3 1.439(3) . ? O4 C4 1.406(3) . ? O4 H4A 0.82(3) . ? O5 C7 1.398(3) . ? O5 C5 1.451(3) . ? O6 C15 1.341(2) . ? O6 C6 1.436(3) . ? O7 C8 1.189(3) . ? O8 C15 1.198(3) . ? C1 C2 1.514(3) . ? C1 C6 1.516(3) . ? C1 H1 0.92(2) . ? C2 C3 1.506(3) . ? C2 H2 0.90(2) . ? C3 C4 1.531(3) . ? C3 H3 0.89(2) . ? C4 C5 1.523(3) . ? C4 H4 0.97(3) . ? C5 C6 1.519(3) . ? C5 H5 0.91(2) . ? C6 H6 0.90(2) . ? C7 H7 0.98(2) . ? C8 C9 1.482(3) . ? C9 C14 1.381(3) . ? C9 C10 1.385(4) . ? C10 C11 1.378(4) . ? C10 H10 0.92(3) . ? C11 C12 1.365(5) . ? C11 H11 0.90(4) . ? C12 C13 1.365(4) . ? C13 C14 1.382(3) . ? C13 H13 0.96(3) . ? C14 H14 0.91(3) . ? C15 C16 1.485(3) . ? C16 C17 1.384(3) . ? C16 C21 1.389(3) . ? C17 C18 1.379(3) . ? C17 H17 0.91(3) . ? C18 C19 1.369(4) . ? C18 H18 0.93(3) . ? C19 C20 1.375(4) . ? C20 C21 1.377(3) . ? C20 H20 0.91(3) . ? C21 H21 0.93(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 110.49(16) . . ? C8 O2 C2 115.41(16) . . ? C7 O3 C3 110.23(15) . . ? C4 O4 H4A 110(2) . . ? C7 O5 C5 111.58(15) . . ? C15 O6 C6 117.43(16) . . ? O1 C1 C2 110.03(16) . . ? O1 C1 C6 106.89(16) . . ? C2 C1 C6 109.77(17) . . ? O1 C1 H1 105.4(13) . . ? C2 C1 H1 112.9(13) . . ? C6 C1 H1 111.6(13) . . ? O2 C2 C3 110.50(16) . . ? O2 C2 C1 109.43(16) . . ? C3 C2 C1 108.48(17) . . ? O2 C2 H2 109.0(13) . . ? C3 C2 H2 109.3(13) . . ? C1 C2 H2 110.0(13) . . ? O3 C3 C2 110.37(17) . . ? O3 C3 C4 108.33(17) . . ? C2 C3 C4 108.82(17) . . ? O3 C3 H3 104.5(13) . . ? C2 C3 H3 111.3(13) . . ? C4 C3 H3 113.4(13) . . ? O4 C4 C5 114.96(19) . . ? O4 C4 C3 107.26(18) . . ? C5 C4 C3 106.93(17) . . ? O4 C4 H4 112.3(15) . . ? C5 C4 H4 108.1(14) . . ? C3 C4 H4 106.9(15) . . ? O5 C5 C6 105.83(17) . . ? O5 C5 C4 106.05(17) . . ? C6 C5 C4 114.74(18) . . ? O5 C5 H5 105.8(14) . . ? C6 C5 H5 112.4(14) . . ? C4 C5 H5 111.3(14) . . ? O6 C6 C1 106.49(16) . . ? O6 C6 C5 112.28(18) . . ? C1 C6 C5 107.52(17) . . ? O6 C6 H6 112.0(14) . . ? C1 C6 H6 110.1(14) . . ? C5 C6 H6 108.4(14) . . ? O3 C7 O5 112.33(18) . . ? O3 C7 O1 110.64(16) . . ? O5 C7 O1 110.86(17) . . ? O3 C7 H7 108.7(12) . . ? O5 C7 H7 106.6(12) . . ? O1 C7 H7 107.6(12) . . ? O7 C8 O2 123.1(2) . . ? O7 C8 C9 124.0(2) . . ? O2 C8 C9 112.93(18) . . ? C14 C9 C10 119.6(2) . . ? C14 C9 C8 123.3(2) . . ? C10 C9 C8 117.1(2) . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 121(2) . . ? C9 C10 H10 119(2) . . ? C12 C11 C10 119.4(3) . . ? C12 C11 H11 126(2) . . ? C10 C11 H11 115(2) . . ? C11 C12 C13 121.8(2) . . ? C11 C12 Cl1 118.7(2) . . ? C13 C12 Cl1 119.4(3) . . ? C12 C13 C14 118.9(3) . . ? C12 C13 H13 119.5(19) . . ? C14 C13 H13 122(2) . . ? C9 C14 C13 120.3(3) . . ? C9 C14 H14 121.0(16) . . ? C13 C14 H14 118.7(16) . . ? O8 C15 O6 123.47(19) . . ? O8 C15 C16 124.88(19) . . ? O6 C15 C16 111.62(18) . . ? C17 C16 C21 119.5(2) . . ? C17 C16 C15 118.6(2) . . ? C21 C16 C15 121.72(19) . . ? C18 C17 C16 120.5(2) . . ? C18 C17 H17 119.1(16) . . ? C16 C17 H17 120.4(15) . . ? C19 C18 C17 119.1(2) . . ? C19 C18 H18 119.2(19) . . ? C17 C18 H18 121.6(19) . . ? C18 C19 C20 121.3(2) . . ? C18 C19 Cl2 119.8(2) . . ? C20 C19 Cl2 118.9(2) . . ? C19 C20 C21 119.7(3) . . ? C19 C20 H20 122.1(16) . . ? C21 C20 H20 118.2(16) . . ? C20 C21 C16 119.8(2) . . ? C20 C21 H21 118.8(16) . . ? C16 C21 H21 121.4(16) . . ? 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 -61.3(2) . . . . ? C8 O2 C2 C3 -132.26(19) . . . . ? C8 O2 C2 C1 108.4(2) . . . . ? O1 C1 C2 O2 68.1(2) . . . . ? C6 C1 C2 O2 -174.58(15) . . . . ? O1 C1 C2 C3 -52.6(2) . . . . ? C6 C1 C2 C3 64.8(2) . . . . ? C7 O3 C3 C2 -59.3(2) . . . . ? C7 O3 C3 C4 59.8(2) . . . . ? O2 C2 C3 O3 -66.7(2) . . . . ? C1 C2 C3 O3 53.3(2) . . . . ? O2 C2 C3 C4 174.56(15) . . . . ? C1 C2 C3 C4 -65.5(2) . . . . ? O3 C3 C4 O4 175.79(16) . . . . ? C2 C3 C4 O4 -64.2(2) . . . . ? O3 C3 C4 C5 -60.4(2) . . . . ? C2 C3 C4 C5 59.6(2) . . . . ? C7 O5 C5 C6 61.3(2) . . . . ? C7 O5 C5 C4 -61.0(2) . . . . ? O4 C4 C5 O5 178.63(16) . . . . ? C3 C4 C5 O5 59.7(2) . . . . ? O4 C4 C5 C6 62.2(2) . . . . ? C3 C4 C5 C6 -56.7(2) . . . . ? C15 O6 C6 C1 165.97(17) . . . . ? C15 O6 C6 C5 -76.6(2) . . . . ? O1 C1 C6 O6 -177.95(15) . . . . ? C2 C1 C6 O6 62.7(2) . . . . ? O1 C1 C6 C5 61.5(2) . . . . ? C2 C1 C6 C5 -57.8(2) . . . . ? O5 C5 C6 O6 -177.50(15) . . . . ? C4 C5 C6 O6 -60.9(2) . . . . ? O5 C5 C6 C1 -60.7(2) . . . . ? C4 C5 C6 C1 55.9(2) . . . . ? C3 O3 C7 O5 -60.5(2) . . . . ? C3 O3 C7 O1 64.0(2) . . . . ? C5 O5 C7 O3 62.1(2) . . . . ? C5 O5 C7 O1 -62.3(2) . . . . ? C1 O1 C7 O3 -63.6(2) . . . . ? C1 O1 C7 O5 61.7(2) . . . . ? C2 O2 C8 O7 0.8(3) . . . . ? C2 O2 C8 C9 -178.93(16) . . . . ? O7 C8 C9 C14 -159.8(3) . . . . ? O2 C8 C9 C14 19.9(3) . . . . ? O7 C8 C9 C10 19.2(4) . . . . ? O2 C8 C9 C10 -161.1(2) . . . . ? C14 C9 C10 C11 -1.3(4) . . . . ? C8 C9 C10 C11 179.7(3) . . . . ? C9 C10 C11 C12 1.3(5) . . . . ? C10 C11 C12 C13 -0.1(5) . . . . ? C10 C11 C12 Cl1 178.3(2) . . . . ? C11 C12 C13 C14 -1.0(4) . . . . ? Cl1 C12 C13 C14 -179.38(19) . . . . ? C10 C9 C14 C13 0.1(4) . . . . ? C8 C9 C14 C13 179.1(2) . . . . ? C12 C13 C14 C9 1.0(4) . . . . ? C6 O6 C15 O8 -9.6(3) . . . . ? C6 O6 C15 C16 168.49(17) . . . . ? O8 C15 C16 C17 -0.6(3) . . . . ? O6 C15 C16 C17 -178.67(19) . . . . ? O8 C15 C16 C21 175.1(2) . . . . ? O6 C15 C16 C21 -3.0(3) . . . . ? C21 C16 C17 C18 0.2(3) . . . . ? C15 C16 C17 C18 176.0(2) . . . . ? C16 C17 C18 C19 -0.3(4) . . . . ? C17 C18 C19 C20 -0.2(4) . . . . ? C17 C18 C19 Cl2 -179.80(19) . . . . ? C18 C19 C20 C21 0.8(4) . . . . ? Cl2 C19 C20 C21 -179.61(19) . . . . ? C19 C20 C21 C16 -0.9(4) . . . . ? C17 C16 C21 C20 0.4(3) . . . . ? C15 C16 C21 C20 -175.3(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 C17 H17 O5 0.91(3) 2.83(3) 3.480(3) 129.2(19) 2_776 O4 H4A O1 0.82(3) 2.06(3) 2.866(3) 168(3) 1_655 C3 H3 O2 0.89(2) 2.75(2) 3.440(3) 134.9(16) 2_666 C5 H5 O8 0.91(2) 2.50(2) 3.305(3) 148.5(18) 2_776 C6 H6 O5 0.90(2) 2.49(2) 3.380(3) 174.2(19) 2_676 C7 H7 O8 0.98(2) 2.51(2) 3.248(3) 132.3(15) 2_676 C13 H13 O3 0.96(3) 2.73(3) 3.630(4) 157(3) 2_566 C14 H14 O4 0.91(3) 2.57(3) 3.466(4) 166(2) 1_455 C18 H18 Cl1 0.93(3) 2.99(3) 3.898(4) 164(2) 1_765 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.475 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.048 # Attachment 'Form_I_1.cif' data_FormI_1 _database_code_depnum_ccdc_archive 'CCDC 655651' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate ; _chemical_name_common '2,6-di-O-p-bromobenzoyl-myo-inositol 1,3,5-orthoformate' _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br2 O8' _chemical_formula_sum 'C21 H16 Br2 O8' _chemical_formula_weight 556.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.825(3) _cell_length_b 8.330(4) _cell_length_c 18.181(9) _cell_angle_alpha 80.744(9) _cell_angle_beta 88.609(9) _cell_angle_gamma 83.038(10) _cell_volume 1012.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 876 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 18.4 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 4.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2390 _exptl_absorpt_correction_T_max 0.9090 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9754 _diffrn_reflns_av_R_equivalents 0.0886 _diffrn_reflns_av_sigmaI/netI 0.1096 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3529 _reflns_number_gt 1982 _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 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003), Platon (Spek, 2002)' _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^)+(0.0879P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3529 _refine_ls_number_parameters 341 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1264 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1491 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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 -0.21432(13) 0.66961(13) 0.50671(5) 0.0754(4) Uani 1 1 d . . . Br2 Br 1.55396(14) 1.38426(12) 0.65648(6) 0.0751(4) Uani 1 1 d . . . O1 O 0.3724(6) 0.8484(6) 0.9023(3) 0.0465(13) Uani 1 1 d . . . O2 O 0.4643(7) 0.7710(6) 0.7547(3) 0.0499(13) Uani 1 1 d . . . O3 O 0.5569(7) 0.5964(6) 0.9036(3) 0.0484(13) Uani 1 1 d . . . O4 O 1.0107(7) 0.7682(8) 0.8486(3) 0.0655(16) Uani 1 1 d . . . H4A H 1.1079 0.7789 0.8722 0.098 Uiso 1 1 calc R . . O5 O 0.6185(7) 0.7599(6) 0.9901(2) 0.0496(13) Uani 1 1 d . . . O6 O 0.7821(7) 1.0784(6) 0.8455(3) 0.0512(14) Uani 1 1 d . . . O7 O 0.5725(8) 0.9389(8) 0.6576(3) 0.0654(16) Uani 1 1 d . . . O8 O 0.8726(8) 1.2161(7) 0.9331(3) 0.0617(15) Uani 1 1 d . . . C1 C 0.5053(11) 0.9310(11) 0.8508(4) 0.047(2) Uani 1 1 d . . . C2 C 0.6102(11) 0.8156(9) 0.8030(4) 0.0450(19) Uani 1 1 d . . . C3 C 0.6999(10) 0.6645(9) 0.8526(4) 0.0415(18) Uani 1 1 d . . . C4 C 0.8626(12) 0.7141(12) 0.8983(5) 0.053(2) Uani 1 1 d . . . C5 C 0.7636(11) 0.8400(10) 0.9439(4) 0.047(2) Uani 1 1 d . . . C6 C 0.6542(10) 0.9924(10) 0.8978(4) 0.0432(19) Uani 1 1 d . . . C7 C 0.4750(11) 0.7110(10) 0.9471(4) 0.0453(19) Uani 1 1 d . . . C8 C 0.4579(11) 0.8479(9) 0.6835(4) 0.0428(18) Uani 1 1 d . . . C9 C 0.2930(10) 0.8060(9) 0.6418(4) 0.0424(18) Uani 1 1 d . . . C10 C 0.2883(12) 0.8478(11) 0.5645(5) 0.056(2) Uani 1 1 d . . . C11 C 0.1384(13) 0.8056(12) 0.5244(5) 0.061(2) Uani 1 1 d . . . C12 C -0.0079(11) 0.7278(10) 0.5615(4) 0.051(2) Uani 1 1 d . . . C13 C -0.0093(12) 0.6858(10) 0.6379(4) 0.051(2) Uani 1 1 d . . . C14 C 0.1415(11) 0.7262(10) 0.6782(4) 0.048(2) Uani 1 1 d . . . C15 C 0.8941(11) 1.1779(9) 0.8719(4) 0.0443(18) Uani 1 1 d . . . C16 C 1.0462(10) 1.2325(9) 0.8175(4) 0.0427(18) Uani 1 1 d . . . C17 C 1.1805(11) 1.3295(9) 0.8390(5) 0.0478(19) Uani 1 1 d . . . C18 C 1.3324(12) 1.3739(10) 0.7902(5) 0.056(2) Uani 1 1 d . . . C19 C 1.3481(11) 1.3234(9) 0.7218(5) 0.052(2) Uani 1 1 d . . . C20 C 1.2122(12) 1.2293(10) 0.7004(5) 0.053(2) Uani 1 1 d . . . C21 C 1.0638(11) 1.1843(10) 0.7479(4) 0.049(2) Uani 1 1 d . . . H1 H 0.443(8) 1.014(7) 0.823(3) 0.018(16) Uiso 1 1 d . . . H2 H 0.712(8) 0.871(6) 0.770(3) 0.015(13) Uiso 1 1 d . . . H3 H 0.766(8) 0.575(7) 0.820(3) 0.026(16) Uiso 1 1 d . . . H4 H 0.914(10) 0.633(8) 0.930(4) 0.04(2) Uiso 1 1 d . . . H5 H 0.846(11) 0.863(9) 0.974(4) 0.05(2) Uiso 1 1 d . . . H6 H 0.582(8) 1.067(7) 0.931(3) 0.025(16) Uiso 1 1 d . . . H7 H 0.383(9) 0.646(7) 0.983(3) 0.026(15) Uiso 1 1 d . . . H10 H 0.380(12) 0.908(10) 0.541(5) 0.07(3) Uiso 1 1 d . . . H11 H 0.134(8) 0.833(7) 0.476(3) 0.019(15) Uiso 1 1 d . . . H13 H -0.116(11) 0.624(9) 0.658(4) 0.06(2) Uiso 1 1 d . . . H14 H 0.128(9) 0.700(8) 0.731(4) 0.043(19) Uiso 1 1 d . . . H17 H 1.163(9) 1.380(7) 0.884(4) 0.034(18) Uiso 1 1 d . . . H18 H 1.432(10) 1.425(8) 0.805(3) 0.038(18) Uiso 1 1 d . . . H20 H 1.216(12) 1.201(9) 0.655(5) 0.06(3) Uiso 1 1 d . . . H21 H 0.967(8) 1.130(6) 0.730(3) 0.018(14) 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 0.0597(6) 0.1148(9) 0.0588(6) -0.0181(5) -0.0271(5) -0.0283(5) Br2 0.0610(6) 0.0829(7) 0.0842(7) -0.0077(5) 0.0196(5) -0.0313(5) O1 0.028(3) 0.061(3) 0.051(3) -0.009(3) -0.004(2) -0.011(2) O2 0.046(3) 0.066(3) 0.043(3) -0.006(3) -0.014(2) -0.028(3) O3 0.043(3) 0.053(3) 0.051(3) -0.008(3) -0.012(3) -0.017(3) O4 0.031(3) 0.116(5) 0.053(3) -0.015(3) -0.007(3) -0.019(3) O5 0.045(3) 0.072(4) 0.036(3) -0.008(2) -0.006(2) -0.023(3) O6 0.051(3) 0.070(4) 0.042(3) -0.014(3) -0.002(2) -0.038(3) O7 0.054(3) 0.090(4) 0.054(3) 0.005(3) -0.014(3) -0.032(3) O8 0.057(4) 0.084(4) 0.057(4) -0.032(3) 0.005(3) -0.033(3) C1 0.035(4) 0.055(5) 0.048(5) 0.002(4) -0.020(4) -0.012(4) C2 0.038(4) 0.065(5) 0.040(4) -0.017(4) -0.010(4) -0.026(4) C3 0.030(4) 0.048(5) 0.047(4) -0.007(4) -0.014(3) -0.006(4) C4 0.038(5) 0.070(6) 0.050(5) -0.003(5) -0.017(4) -0.013(4) C5 0.038(4) 0.070(6) 0.036(4) -0.008(4) -0.013(4) -0.023(4) C6 0.031(4) 0.065(5) 0.038(4) -0.014(4) -0.002(3) -0.020(4) C7 0.034(4) 0.058(5) 0.047(5) -0.006(4) -0.008(4) -0.018(4) C8 0.045(5) 0.052(5) 0.032(4) -0.004(4) -0.003(3) -0.012(4) C9 0.041(4) 0.050(5) 0.037(4) -0.009(4) -0.010(3) -0.005(4) C10 0.046(5) 0.067(6) 0.053(5) -0.001(4) -0.008(4) -0.014(4) C11 0.053(5) 0.093(7) 0.036(5) -0.003(5) -0.014(4) -0.007(5) C12 0.044(5) 0.068(5) 0.044(5) -0.012(4) -0.011(4) -0.007(4) C13 0.043(5) 0.064(6) 0.047(5) -0.001(4) -0.010(4) -0.015(4) C14 0.046(5) 0.068(6) 0.030(4) 0.001(4) -0.006(3) -0.020(4) C15 0.043(5) 0.042(5) 0.049(5) -0.006(4) -0.011(4) -0.011(4) C16 0.038(4) 0.047(5) 0.044(4) 0.001(4) -0.009(3) -0.015(3) C17 0.045(5) 0.054(5) 0.049(5) -0.013(4) -0.005(4) -0.020(4) C18 0.048(5) 0.061(6) 0.065(6) -0.007(4) -0.020(4) -0.026(4) C19 0.044(5) 0.050(5) 0.061(5) 0.002(4) -0.004(4) -0.020(4) C20 0.053(5) 0.066(6) 0.040(5) -0.004(4) -0.010(4) -0.014(4) C21 0.043(5) 0.065(5) 0.043(5) -0.008(4) -0.016(4) -0.025(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 Br1 C12 1.897(7) . ? Br2 C19 1.881(8) . ? O1 C7 1.413(8) . ? O1 C1 1.442(9) . ? O2 C8 1.349(8) . ? O2 C2 1.462(7) . ? O3 C7 1.394(9) . ? O3 C3 1.433(8) . ? O4 C4 1.405(9) . ? O4 H4A 0.8200 . ? O5 C7 1.404(8) . ? O5 C5 1.439(8) . ? O6 C15 1.342(8) . ? O6 C6 1.439(8) . ? O7 C8 1.191(8) . ? O8 C15 1.206(9) . ? C1 C2 1.504(11) . ? C1 C6 1.528(9) . ? C1 H1 0.86(6) . ? C2 C3 1.499(10) . ? C2 H2 1.01(5) . ? C3 C4 1.536(10) . ? C3 H3 1.08(6) . ? C4 C5 1.525(12) . ? C4 H4 0.86(6) . ? C5 C6 1.526(11) . ? C5 H5 0.85(8) . ? C6 H6 1.01(6) . ? C7 H7 1.02(6) . ? C8 C9 1.478(10) . ? C9 C14 1.393(10) . ? C9 C10 1.394(10) . ? C10 C11 1.380(11) . ? C10 H10 0.91(8) . ? C11 C12 1.362(11) . ? C11 H11 0.87(6) . ? C12 C13 1.377(10) . ? C13 C14 1.382(10) . ? C13 H13 0.97(7) . ? C14 H14 0.96(7) . ? C15 C16 1.477(10) . ? C16 C21 1.386(10) . ? C16 C17 1.394(9) . ? C17 C18 1.393(11) . ? C17 H17 0.97(6) . ? C18 C19 1.373(11) . ? C18 H18 0.91(7) . ? C19 C20 1.384(11) . ? C20 C21 1.363(11) . ? C20 H20 0.90(8) . ? C21 H21 0.94(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 C1 110.7(5) . . ? C8 O2 C2 116.7(5) . . ? C7 O3 C3 110.6(6) . . ? C4 O4 H4A 109.5 . . ? C7 O5 C5 111.5(5) . . ? C15 O6 C6 117.1(6) . . ? O1 C1 C2 110.8(6) . . ? O1 C1 C6 106.5(6) . . ? C2 C1 C6 110.1(6) . . ? O1 C1 H1 111(4) . . ? C2 C1 H1 110(4) . . ? C6 C1 H1 109(4) . . ? O2 C2 C3 109.2(5) . . ? O2 C2 C1 108.1(6) . . ? C3 C2 C1 108.7(6) . . ? O2 C2 H2 108(3) . . ? C3 C2 H2 112(3) . . ? C1 C2 H2 111(3) . . ? O3 C3 C2 111.3(6) . . ? O3 C3 C4 108.1(6) . . ? C2 C3 C4 107.6(6) . . ? O3 C3 H3 111(3) . . ? C2 C3 H3 110(3) . . ? C4 C3 H3 109(3) . . ? O4 C4 C5 115.6(7) . . ? O4 C4 C3 108.0(6) . . ? C5 C4 C3 107.0(6) . . ? O4 C4 H4 109(5) . . ? C5 C4 H4 106(5) . . ? C3 C4 H4 112(5) . . ? O5 C5 C4 106.3(6) . . ? O5 C5 C6 106.9(6) . . ? C4 C5 C6 114.6(7) . . ? O5 C5 H5 106(5) . . ? C4 C5 H5 110(5) . . ? C6 C5 H5 113(5) . . ? O6 C6 C5 112.3(6) . . ? O6 C6 C1 105.8(6) . . ? C5 C6 C1 106.1(6) . . ? O6 C6 H6 111(3) . . ? C5 C6 H6 111(3) . . ? C1 C6 H6 110(3) . . ? O3 C7 O5 111.8(6) . . ? O3 C7 O1 110.8(6) . . ? O5 C7 O1 110.5(6) . . ? O3 C7 H7 103(3) . . ? O5 C7 H7 108(3) . . ? O1 C7 H7 112(3) . . ? O7 C8 O2 123.6(7) . . ? O7 C8 C9 124.3(6) . . ? O2 C8 C9 112.2(6) . . ? C14 C9 C10 119.2(7) . . ? C14 C9 C8 121.4(6) . . ? C10 C9 C8 119.4(7) . . ? C11 C10 C9 120.2(8) . . ? C11 C10 H10 120(5) . . ? C9 C10 H10 119(5) . . ? C12 C11 C10 119.3(8) . . ? C12 C11 H11 120(4) . . ? C10 C11 H11 120(4) . . ? C11 C12 C13 122.2(7) . . ? C11 C12 Br1 119.5(6) . . ? C13 C12 Br1 118.3(6) . . ? C12 C13 C14 118.7(7) . . ? C12 C13 H13 115(4) . . ? C14 C13 H13 126(4) . . ? C13 C14 C9 120.4(7) . . ? C13 C14 H14 115(4) . . ? C9 C14 H14 125(4) . . ? O8 C15 O6 123.4(7) . . ? O8 C15 C16 124.7(7) . . ? O6 C15 C16 111.9(7) . . ? C21 C16 C17 119.7(7) . . ? C21 C16 C15 122.0(7) . . ? C17 C16 C15 118.2(7) . . ? C18 C17 C16 119.1(8) . . ? C18 C17 H17 118(4) . . ? C16 C17 H17 123(4) . . ? C19 C18 C17 120.2(7) . . ? C19 C18 H18 119(4) . . ? C17 C18 H18 121(4) . . ? C18 C19 C20 120.3(8) . . ? C18 C19 Br2 119.7(6) . . ? C20 C19 Br2 119.9(7) . . ? C21 C20 C19 119.9(8) . . ? C21 C20 H20 119(5) . . ? C19 C20 H20 121(5) . . ? C20 C21 C16 120.8(7) . . ? C20 C21 H21 118(3) . . ? C16 C21 H21 121(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 57.0(7) . . . . ? C7 O1 C1 C6 -62.8(8) . . . . ? C8 O2 C2 C3 -140.4(7) . . . . ? C8 O2 C2 C1 101.5(7) . . . . ? O1 C1 C2 O2 67.0(7) . . . . ? C6 C1 C2 O2 -175.4(5) . . . . ? O1 C1 C2 C3 -51.4(7) . . . . ? C6 C1 C2 C3 66.2(7) . . . . ? C7 O3 C3 C2 -58.1(7) . . . . ? C7 O3 C3 C4 59.9(7) . . . . ? O2 C2 C3 O3 -65.8(8) . . . . ? C1 C2 C3 O3 51.9(7) . . . . ? O2 C2 C3 C4 175.9(6) . . . . ? C1 C2 C3 C4 -66.3(7) . . . . ? O3 C3 C4 O4 175.2(6) . . . . ? C2 C3 C4 O4 -64.4(9) . . . . ? O3 C3 C4 C5 -59.8(8) . . . . ? C2 C3 C4 C5 60.6(8) . . . . ? C7 O5 C5 C4 -61.3(7) . . . . ? C7 O5 C5 C6 61.5(8) . . . . ? O4 C4 C5 O5 179.8(6) . . . . ? C3 C4 C5 O5 59.6(7) . . . . ? O4 C4 C5 C6 62.0(8) . . . . ? C3 C4 C5 C6 -58.2(8) . . . . ? C15 O6 C6 C5 -80.8(8) . . . . ? C15 O6 C6 C1 163.9(6) . . . . ? O5 C5 C6 O6 -176.4(5) . . . . ? C4 C5 C6 O6 -58.9(8) . . . . ? O5 C5 C6 C1 -61.3(8) . . . . ? C4 C5 C6 C1 56.2(8) . . . . ? O1 C1 C6 O6 -178.4(6) . . . . ? C2 C1 C6 O6 61.4(8) . . . . ? O1 C1 C6 C5 62.1(8) . . . . ? C2 C1 C6 C5 -58.1(8) . . . . ? C3 O3 C7 O5 -61.0(7) . . . . ? C3 O3 C7 O1 62.8(6) . . . . ? C5 O5 C7 O3 62.5(8) . . . . ? C5 O5 C7 O1 -61.4(8) . . . . ? C1 O1 C7 O3 -62.5(7) . . . . ? C1 O1 C7 O5 62.0(7) . . . . ? C2 O2 C8 O7 5.7(11) . . . . ? C2 O2 C8 C9 -174.4(6) . . . . ? O7 C8 C9 C14 -166.8(8) . . . . ? O2 C8 C9 C14 13.2(10) . . . . ? O7 C8 C9 C10 12.8(12) . . . . ? O2 C8 C9 C10 -167.1(7) . . . . ? C14 C9 C10 C11 -2.1(13) . . . . ? C8 C9 C10 C11 178.2(8) . . . . ? C9 C10 C11 C12 2.2(14) . . . . ? C10 C11 C12 C13 -1.7(14) . . . . ? C10 C11 C12 Br1 180.0(7) . . . . ? C11 C12 C13 C14 1.0(13) . . . . ? Br1 C12 C13 C14 179.4(6) . . . . ? C12 C13 C14 C9 -0.9(13) . . . . ? C10 C9 C14 C13 1.5(12) . . . . ? C8 C9 C14 C13 -178.9(7) . . . . ? C6 O6 C15 O8 -10.9(11) . . . . ? C6 O6 C15 C16 168.5(6) . . . . ? O8 C15 C16 C21 180.0(8) . . . . ? O6 C15 C16 C21 0.6(10) . . . . ? O8 C15 C16 C17 2.9(12) . . . . ? O6 C15 C16 C17 -176.5(6) . . . . ? C21 C16 C17 C18 -1.0(11) . . . . ? C15 C16 C17 C18 176.1(7) . . . . ? C16 C17 C18 C19 0.4(12) . . . . ? C17 C18 C19 C20 0.6(12) . . . . ? C17 C18 C19 Br2 -180.0(6) . . . . ? C18 C19 C20 C21 -1.0(12) . . . . ? Br2 C19 C20 C21 179.6(6) . . . . ? C19 C20 C21 C16 0.4(12) . . . . ? C17 C16 C21 C20 0.7(12) . . . . ? C15 C16 C21 C20 -176.4(7) . . . . ? 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 O1 0.82 2.07 2.867(7) 163.0 1_655 C20 H20 Br1 0.90(8) 2.96(8) 3.724(9) 144(6) 2_676 C17 H17 O5 0.97(6) 2.78(6) 3.362(9) 119(4) 2_777 C18 H18 O3 0.91(7) 2.67(7) 3.479(10) 148(5) 1_665 C14 H14 O4 0.96(7) 2.39(7) 3.264(10) 151(5) 1_455 C7 H7 O8 1.02(6) 2.58(6) 3.250(10) 123(4) 2_677 C7 H7 O3 1.02(6) 2.65(6) 3.441(9) 134(4) 2_667 C6 H6 O5 1.01(6) 2.47(7) 3.480(10) 175(5) 2_677 C5 H5 O8 0.85(8) 2.55(8) 3.322(9) 152(6) 2_777 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.887 _refine_diff_density_min -0.742 _refine_diff_density_rms 0.108 # Attachment 'Form_I_2.cif' data_FormI_2 _database_code_depnum_ccdc_archive 'CCDC 655652' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate ; _chemical_name_common '2,6-di-O-p-chlorobenzoyl-myo-inositol 1,3,5-orthoformate' _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Cl2 O8' _chemical_formula_sum 'C21 H16 Cl2 O8' _chemical_formula_weight 467.24 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.815(3) _cell_length_b 8.325(3) _cell_length_c 17.887(7) _cell_angle_alpha 80.140(7) _cell_angle_beta 87.493(8) _cell_angle_gamma 83.024(8) _cell_volume 992.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1345 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 19.9 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.377 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8042 _exptl_absorpt_correction_T_max 0.9829 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9248 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3463 _reflns_number_gt 2322 _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 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003), Platon (Spek, 2002)' _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^)+(0.0607P)^2^+0.1235P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3463 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0954 _refine_ls_R_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 -0.69234(16) 0.17066(16) 0.51027(6) 0.0901(4) Uani 1 1 d . . . Cl2 Cl 1.06482(17) 0.88360(14) 0.65839(7) 0.0903(4) Uani 1 1 d . . . O1 O -0.1230(3) 0.3500(3) 0.90011(12) 0.0438(6) Uani 1 1 d . . . O2 O -0.0225(3) 0.2686(3) 0.75100(11) 0.0461(6) Uani 1 1 d . . . O3 O 0.0632(3) 0.0983(3) 0.90322(12) 0.0455(6) Uani 1 1 d . . . O4 O 0.5200(4) 0.2703(4) 0.84655(15) 0.0640(8) Uani 1 1 d . . . O5 O 0.1180(3) 0.2641(3) 0.99019(11) 0.0484(6) Uani 1 1 d . . . O6 O 0.2915(3) 0.5804(3) 0.84118(12) 0.0493(6) Uani 1 1 d . . . O7 O 0.0834(4) 0.4406(3) 0.65095(13) 0.0662(7) Uani 1 1 d . . . O8 O 0.3751(3) 0.7173(3) 0.93025(13) 0.0563(7) Uani 1 1 d . . . C1 C 0.0130(5) 0.4330(4) 0.84678(18) 0.0400(8) Uani 1 1 d . . . C2 C 0.1184(5) 0.3165(4) 0.79846(18) 0.0388(8) Uani 1 1 d . . . C3 C 0.2102(5) 0.1665(4) 0.85084(19) 0.0425(8) Uani 1 1 d . . . C4 C 0.3690(5) 0.2145(5) 0.8975(2) 0.0484(9) Uani 1 1 d . . . C5 C 0.2677(5) 0.3429(4) 0.94231(19) 0.0443(8) Uani 1 1 d . . . C6 C 0.1608(5) 0.4928(4) 0.89418(18) 0.0423(8) Uani 1 1 d . . . C7 C -0.0215(5) 0.2143(4) 0.9462(2) 0.0460(9) Uani 1 1 d . . . C8 C -0.0313(5) 0.3473(4) 0.67769(18) 0.0439(8) Uani 1 1 d . . . C9 C -0.1958(5) 0.3023(4) 0.63714(18) 0.0414(8) Uani 1 1 d . . . C10 C -0.2003(6) 0.3423(5) 0.5589(2) 0.0616(11) Uani 1 1 d . . . C11 C -0.3526(6) 0.3027(6) 0.5197(2) 0.0703(13) Uani 1 1 d . . . C12 C -0.4998(5) 0.2219(5) 0.5591(2) 0.0561(10) Uani 1 1 d . . . C13 C -0.4994(6) 0.1841(5) 0.6356(2) 0.0553(10) Uani 1 1 d . . . C14 C -0.3466(5) 0.2231(4) 0.6745(2) 0.0477(9) Uani 1 1 d . . . C15 C 0.4003(5) 0.6823(4) 0.86797(19) 0.0412(8) Uani 1 1 d . . . C16 C 0.5581(4) 0.7360(4) 0.81276(17) 0.0392(8) Uani 1 1 d . . . C17 C 0.6937(5) 0.8281(4) 0.8355(2) 0.0453(8) Uani 1 1 d . . . C18 C 0.8489(6) 0.8738(4) 0.7884(2) 0.0549(10) Uani 1 1 d . . . C19 C 0.8677(5) 0.8275(4) 0.7184(2) 0.0539(9) Uani 1 1 d . . . C20 C 0.7333(6) 0.7373(5) 0.6938(2) 0.0559(10) Uani 1 1 d . . . C21 C 0.5796(5) 0.6915(5) 0.74173(19) 0.0479(9) Uani 1 1 d . . . H1 H -0.064(4) 0.521(4) 0.8156(16) 0.039(8) Uiso 1 1 d . . . H2 H 0.215(4) 0.365(3) 0.7671(15) 0.033(8) Uiso 1 1 d . . . H3 H 0.260(4) 0.087(4) 0.8220(16) 0.037(8) Uiso 1 1 d . . . H4 H 0.419(4) 0.123(4) 0.9337(17) 0.046(9) Uiso 1 1 d . . . H5 H 0.355(5) 0.374(4) 0.9750(17) 0.047(9) Uiso 1 1 d . . . H6 H 0.090(5) 0.565(4) 0.9275(18) 0.050(9) Uiso 1 1 d . . . H7 H -0.107(4) 0.168(3) 0.9792(16) 0.034(8) Uiso 1 1 d . . . H10 H -0.112(6) 0.396(5) 0.536(2) 0.075(14) Uiso 1 1 d . . . H11 H -0.356(5) 0.320(4) 0.470(2) 0.067(11) Uiso 1 1 d . . . H13 H -0.595(5) 0.125(4) 0.6610(19) 0.065(12) Uiso 1 1 d . . . H14 H -0.347(4) 0.198(3) 0.7238(18) 0.039(9) Uiso 1 1 d . . . H17 H 0.682(4) 0.860(3) 0.8809(17) 0.036(9) Uiso 1 1 d . . . H18 H 0.941(6) 0.930(5) 0.803(2) 0.084(14) Uiso 1 1 d . . . H20 H 0.740(5) 0.715(4) 0.648(2) 0.064(12) Uiso 1 1 d . . . H21 H 0.496(4) 0.631(4) 0.7272(16) 0.041(9) Uiso 1 1 d . . . H4A H 0.618(8) 0.290(6) 0.867(3) 0.12(2) 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 0.0779(8) 0.1306(11) 0.0710(7) -0.0242(7) -0.0288(6) -0.0285(7) Cl2 0.0787(8) 0.0767(8) 0.1125(10) -0.0057(6) 0.0441(7) -0.0271(6) O1 0.0327(12) 0.0455(14) 0.0529(13) -0.0052(11) 0.0019(10) -0.0096(10) O2 0.0485(13) 0.0545(15) 0.0392(12) -0.0037(11) -0.0103(10) -0.0239(11) O3 0.0478(13) 0.0380(13) 0.0519(14) -0.0072(11) -0.0015(11) -0.0107(11) O4 0.0331(14) 0.100(2) 0.0624(17) -0.0212(15) 0.0024(13) -0.0141(14) O5 0.0483(13) 0.0622(15) 0.0374(12) -0.0056(11) 0.0004(10) -0.0212(12) O6 0.0553(14) 0.0557(15) 0.0449(13) -0.0139(11) 0.0044(11) -0.0319(12) O7 0.0678(17) 0.0771(19) 0.0549(15) 0.0065(13) -0.0043(13) -0.0363(15) O8 0.0540(15) 0.0701(17) 0.0559(15) -0.0308(13) 0.0094(12) -0.0263(13) C1 0.0332(18) 0.040(2) 0.0467(19) -0.0029(16) -0.0028(15) -0.0107(16) C2 0.0341(18) 0.044(2) 0.0416(19) -0.0085(16) -0.0061(15) -0.0148(16) C3 0.0380(19) 0.046(2) 0.046(2) -0.0165(17) 0.0007(16) -0.0058(16) C4 0.0351(19) 0.058(2) 0.051(2) -0.0039(19) -0.0038(17) -0.0064(17) C5 0.0408(19) 0.057(2) 0.0382(18) -0.0068(17) -0.0027(16) -0.0203(18) C6 0.0431(19) 0.047(2) 0.0422(19) -0.0133(17) 0.0058(16) -0.0196(17) C7 0.042(2) 0.052(2) 0.046(2) -0.0068(18) 0.0012(17) -0.0171(18) C8 0.045(2) 0.042(2) 0.044(2) -0.0073(16) 0.0013(16) -0.0043(17) C9 0.0401(19) 0.043(2) 0.0412(19) -0.0059(15) -0.0063(15) -0.0036(15) C10 0.060(3) 0.081(3) 0.044(2) 0.001(2) 0.0008(19) -0.021(2) C11 0.072(3) 0.104(4) 0.036(2) -0.012(2) -0.012(2) -0.012(3) C12 0.052(2) 0.068(3) 0.052(2) -0.0166(19) -0.0112(18) -0.006(2) C13 0.049(2) 0.069(3) 0.050(2) -0.0056(19) -0.0096(18) -0.017(2) C14 0.049(2) 0.058(2) 0.036(2) -0.0052(17) -0.0060(17) -0.0092(18) C15 0.0405(19) 0.040(2) 0.046(2) -0.0106(16) -0.0066(16) -0.0085(15) C16 0.0377(18) 0.0378(19) 0.0432(19) -0.0060(15) -0.0033(15) -0.0094(15) C17 0.052(2) 0.039(2) 0.049(2) -0.0117(17) -0.0018(17) -0.0131(17) C18 0.052(2) 0.045(2) 0.070(3) -0.0066(19) 0.002(2) -0.0217(19) C19 0.050(2) 0.041(2) 0.066(2) 0.0044(18) 0.0114(18) -0.0088(17) C20 0.065(3) 0.057(3) 0.043(2) 0.0007(19) 0.002(2) -0.010(2) C21 0.048(2) 0.051(2) 0.047(2) -0.0067(17) -0.0068(17) -0.0159(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C12 1.741(4) . ? Cl2 C19 1.740(4) . ? O1 C7 1.406(4) . ? O1 C1 1.449(4) . ? O2 C8 1.362(4) . ? O2 C2 1.443(3) . ? O3 C7 1.392(4) . ? O3 C3 1.441(4) . ? O4 C4 1.412(4) . ? O4 H4A 0.82(5) . ? O5 C7 1.402(4) . ? O5 C5 1.448(4) . ? O6 C15 1.350(4) . ? O6 C6 1.439(4) . ? O7 C8 1.197(4) . ? O8 C15 1.199(4) . ? C1 C2 1.506(4) . ? C1 C6 1.524(4) . ? C1 H1 0.96(3) . ? C2 C3 1.513(4) . ? C2 H2 0.93(3) . ? C3 C4 1.525(5) . ? C3 H3 0.93(3) . ? C4 C5 1.526(5) . ? C4 H4 0.95(3) . ? C5 C6 1.515(5) . ? C5 H5 0.94(3) . ? C6 H6 0.99(3) . ? C7 H7 0.88(3) . ? C8 C9 1.479(4) . ? C9 C14 1.375(5) . ? C9 C10 1.383(5) . ? C10 C11 1.380(5) . ? C10 H10 0.85(4) . ? C11 C12 1.376(5) . ? C11 H11 0.88(3) . ? C12 C13 1.351(5) . ? C13 C14 1.378(5) . ? C13 H13 0.92(4) . ? C14 H14 0.87(3) . ? C15 C16 1.485(4) . ? C16 C21 1.380(5) . ? C16 C17 1.386(4) . ? C17 C18 1.373(5) . ? C17 H17 0.89(3) . ? C18 C19 1.368(5) . ? C18 H18 0.90(4) . ? C19 C20 1.383(5) . ? C20 C21 1.372(5) . ? C20 H20 0.88(4) . ? C21 H21 0.88(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 110.4(2) . . ? C8 O2 C2 116.9(2) . . ? C7 O3 C3 110.3(3) . . ? C4 O4 H4A 114(4) . . ? C7 O5 C5 110.8(2) . . ? C15 O6 C6 117.3(2) . . ? O1 C1 C2 110.5(3) . . ? O1 C1 C6 106.3(2) . . ? C2 C1 C6 110.2(3) . . ? O1 C1 H1 106.8(17) . . ? C2 C1 H1 110.1(17) . . ? C6 C1 H1 112.8(17) . . ? O2 C2 C1 109.3(3) . . ? O2 C2 C3 109.5(3) . . ? C1 C2 C3 108.0(3) . . ? O2 C2 H2 108.3(17) . . ? C1 C2 H2 111.4(17) . . ? C3 C2 H2 110.4(17) . . ? O3 C3 C2 110.4(3) . . ? O3 C3 C4 107.5(3) . . ? C2 C3 C4 109.7(3) . . ? O3 C3 H3 108.0(18) . . ? C2 C3 H3 108.9(17) . . ? C4 C3 H3 112.3(18) . . ? O4 C4 C3 107.5(3) . . ? O4 C4 C5 114.4(3) . . ? C3 C4 C5 106.9(3) . . ? O4 C4 H4 111.1(18) . . ? C3 C4 H4 110.3(19) . . ? C5 C4 H4 106.6(18) . . ? O5 C5 C6 106.4(3) . . ? O5 C5 C4 106.3(3) . . ? C6 C5 C4 114.6(3) . . ? O5 C5 H5 106.5(19) . . ? C6 C5 H5 110.4(19) . . ? C4 C5 H5 112.1(19) . . ? O6 C6 C5 112.5(3) . . ? O6 C6 C1 106.3(2) . . ? C5 C6 C1 107.4(3) . . ? O6 C6 H6 111.2(18) . . ? C5 C6 H6 109.5(18) . . ? C1 C6 H6 109.7(18) . . ? O3 C7 O5 112.1(3) . . ? O3 C7 O1 111.1(3) . . ? O5 C7 O1 111.0(3) . . ? O3 C7 H7 108.7(19) . . ? O5 C7 H7 105.4(18) . . ? O1 C7 H7 108.3(19) . . ? O7 C8 O2 122.4(3) . . ? O7 C8 C9 125.6(3) . . ? O2 C8 C9 112.0(3) . . ? C14 C9 C10 118.4(3) . . ? C14 C9 C8 122.4(3) . . ? C10 C9 C8 119.2(3) . . ? C11 C10 C9 120.4(4) . . ? C11 C10 H10 121(3) . . ? C9 C10 H10 119(3) . . ? C12 C11 C10 119.5(4) . . ? C12 C11 H11 117(2) . . ? C10 C11 H11 123(2) . . ? C13 C12 C11 120.9(4) . . ? C13 C12 Cl1 119.1(3) . . ? C11 C12 Cl1 119.9(3) . . ? C12 C13 C14 119.4(4) . . ? C12 C13 H13 120(2) . . ? C14 C13 H13 121(2) . . ? C9 C14 C13 121.3(3) . . ? C9 C14 H14 120(2) . . ? C13 C14 H14 119(2) . . ? O8 C15 O6 123.0(3) . . ? O8 C15 C16 125.3(3) . . ? O6 C15 C16 111.6(3) . . ? C21 C16 C17 119.3(3) . . ? C21 C16 C15 122.6(3) . . ? C17 C16 C15 118.0(3) . . ? C18 C17 C16 120.6(4) . . ? C18 C17 H17 118(2) . . ? C16 C17 H17 121(2) . . ? C19 C18 C17 119.1(4) . . ? C19 C18 H18 119(3) . . ? C17 C18 H18 122(3) . . ? C18 C19 C20 121.6(3) . . ? C18 C19 Cl2 119.5(3) . . ? C20 C19 Cl2 118.9(3) . . ? C21 C20 C19 118.7(4) . . ? C21 C20 H20 120(2) . . ? C19 C20 H20 121(2) . . ? C20 C21 C16 120.7(4) . . ? C20 C21 H21 119(2) . . ? C16 C21 H21 120(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 58.0(3) . . . . ? C7 O1 C1 C6 -61.6(3) . . . . ? C8 O2 C2 C1 99.8(3) . . . . ? C8 O2 C2 C3 -142.1(3) . . . . ? O1 C1 C2 O2 66.0(3) . . . . ? C6 C1 C2 O2 -176.8(2) . . . . ? O1 C1 C2 C3 -53.0(3) . . . . ? C6 C1 C2 C3 64.2(3) . . . . ? C7 O3 C3 C2 -59.0(3) . . . . ? C7 O3 C3 C4 60.7(3) . . . . ? O2 C2 C3 O3 -65.4(3) . . . . ? C1 C2 C3 O3 53.6(3) . . . . ? O2 C2 C3 C4 176.3(3) . . . . ? C1 C2 C3 C4 -64.8(3) . . . . ? O3 C3 C4 O4 175.9(3) . . . . ? C2 C3 C4 O4 -64.0(4) . . . . ? O3 C3 C4 C5 -60.9(3) . . . . ? C2 C3 C4 C5 59.3(4) . . . . ? C7 O5 C5 C6 61.4(3) . . . . ? C7 O5 C5 C4 -61.1(3) . . . . ? O4 C4 C5 O5 179.4(3) . . . . ? C3 C4 C5 O5 60.5(3) . . . . ? O4 C4 C5 C6 62.3(4) . . . . ? C3 C4 C5 C6 -56.6(4) . . . . ? C15 O6 C6 C5 -80.3(4) . . . . ? C15 O6 C6 C1 162.4(3) . . . . ? O5 C5 C6 O6 -177.7(2) . . . . ? C4 C5 C6 O6 -60.6(4) . . . . ? O5 C5 C6 C1 -61.1(3) . . . . ? C4 C5 C6 C1 56.0(4) . . . . ? O1 C1 C6 O6 -178.0(2) . . . . ? C2 C1 C6 O6 62.3(3) . . . . ? O1 C1 C6 C5 61.4(3) . . . . ? C2 C1 C6 C5 -58.3(3) . . . . ? C3 O3 C7 O5 -61.5(3) . . . . ? C3 O3 C7 O1 63.4(3) . . . . ? C5 O5 C7 O3 62.3(4) . . . . ? C5 O5 C7 O1 -62.6(3) . . . . ? C1 O1 C7 O3 -62.8(3) . . . . ? C1 O1 C7 O5 62.7(3) . . . . ? C2 O2 C8 O7 6.9(5) . . . . ? C2 O2 C8 C9 -173.4(3) . . . . ? O7 C8 C9 C14 -165.7(3) . . . . ? O2 C8 C9 C14 14.6(4) . . . . ? O7 C8 C9 C10 13.6(5) . . . . ? O2 C8 C9 C10 -166.1(3) . . . . ? C14 C9 C10 C11 -0.3(6) . . . . ? C8 C9 C10 C11 -179.6(4) . . . . ? C9 C10 C11 C12 -0.4(7) . . . . ? C10 C11 C12 C13 1.4(6) . . . . ? C10 C11 C12 Cl1 -179.8(3) . . . . ? C11 C12 C13 C14 -1.7(6) . . . . ? Cl1 C12 C13 C14 179.5(3) . . . . ? C10 C9 C14 C13 0.0(5) . . . . ? C8 C9 C14 C13 179.3(3) . . . . ? C12 C13 C14 C9 1.0(6) . . . . ? C6 O6 C15 O8 -9.3(5) . . . . ? C6 O6 C15 C16 167.6(3) . . . . ? O8 C15 C16 C21 180.0(3) . . . . ? O6 C15 C16 C21 3.2(4) . . . . ? O8 C15 C16 C17 3.0(5) . . . . ? O6 C15 C16 C17 -173.8(3) . . . . ? C21 C16 C17 C18 -0.5(5) . . . . ? C15 C16 C17 C18 176.5(3) . . . . ? C16 C17 C18 C19 0.2(5) . . . . ? C17 C18 C19 C20 0.6(6) . . . . ? C17 C18 C19 Cl2 -179.6(3) . . . . ? C18 C19 C20 C21 -1.0(6) . . . . ? Cl2 C19 C20 C21 179.1(3) . . . . ? C19 C20 C21 C16 0.7(5) . . . . ? C17 C16 C21 C20 0.1(5) . . . . ? C15 C16 C21 C20 -176.9(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 C20 H20 Cl1 0.88(4) 2.84(4) 3.615(4) 148(3) 2_566 C7 H7 O3 0.88(3) 2.78(3) 3.438(4) 132(2) 2_557 C18 H18 O3 0.90(4) 2.67(4) 3.476(5) 149(3) 1_665 C17 H17 O5 0.89(3) 2.71(3) 3.353(4) 130(2) 2_667 C14 H14 O4 0.87(3) 2.48(3) 3.245(5) 147(2) 1_455 C7 H7 O8 0.88(3) 2.59(3) 3.262(4) 134(2) 2_567 C6 H6 O5 0.99(3) 2.50(3) 3.484(4) 175(2) 2_567 C5 H5 O8 0.94(3) 2.52(3) 3.342(4) 147(2) 2_667 O4 H4A O1 0.82(5) 2.03(5) 2.844(3) 170(5) 1_655 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.412 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.050