# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_kms_bz _database_code_depnum_ccdc_archive 'CCDC 898287' #TrackingRef '13521_web_deposit_cif_file_0_KanaM.Sureshan_1345894179.KMS_BZ.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,4-di-O-benzoyl-myo-inositol _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 O8' _chemical_formula_sum 'C20 H20 O8' _chemical_formula_weight 388.36 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.385(4) _cell_length_b 11.708(4) _cell_length_c 10.799(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.286(6) _cell_angle_gamma 90.00 _cell_volume 1799.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1818 _cell_measurement_theta_min 2.814 _cell_measurement_theta_max 22.505 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9805 _exptl_absorpt_correction_T_max 0.9909 _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_reflns_number 8816 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3150 _reflns_number_gt 2370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT(Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0423P)^2^+0.2131P] 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 3150 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.23496(7) 0.80840(10) 0.07987(10) 0.0411(3) Uani 1 1 d . . . O2 O 0.35911(8) 0.66853(11) 0.25060(10) 0.0433(3) Uani 1 1 d . . . H2 H 0.3058 0.6614 0.2680 0.065 Uiso 1 1 calc R . . O3 O 0.48233(9) 0.52570(10) 0.13926(11) 0.0459(3) Uani 1 1 d . . . H3 H 0.4645 0.5165 0.2074 0.069 Uiso 1 1 calc R . . O4 O 0.60875(8) 0.69714(10) 0.08117(10) 0.0404(3) Uani 1 1 d . . . O5 O 0.56270(9) 0.92449(11) 0.14375(11) 0.0498(3) Uani 1 1 d . . . H5 H 0.5886 0.9552 0.0896 0.075 Uiso 1 1 calc R . . O6 O 0.36985(10) 0.98062(10) 0.05652(11) 0.0508(4) Uani 1 1 d . . . H6 H 0.3556 1.0250 0.1095 0.076 Uiso 1 1 calc R . . O7 O 0.18936(9) 0.84047(13) -0.12536(11) 0.0591(4) Uani 1 1 d . . . O8 O 0.68460(8) 0.61787(11) 0.25741(11) 0.0506(3) Uani 1 1 d . . . C1 C 0.33033(11) 0.78167(15) 0.05917(15) 0.0366(4) Uani 1 1 d . . . H1 H 0.3321 0.7767 -0.0310 0.044 Uiso 1 1 calc R . . C2 C 0.35601(11) 0.66622(14) 0.11830(15) 0.0361(4) Uani 1 1 d . . . H2A H 0.3102 0.6090 0.0823 0.043 Uiso 1 1 calc R . . C3 C 0.45272(11) 0.63341(14) 0.09090(15) 0.0372(4) Uani 1 1 d . . . H3A H 0.4490 0.6286 -0.0003 0.045 Uiso 1 1 calc R . . C4 C 0.52488(11) 0.72538(14) 0.13512(15) 0.0351(4) Uani 1 1 d . . . H4 H 0.5386 0.7256 0.2267 0.042 Uiso 1 1 calc R . . C5 C 0.49590(11) 0.84363(14) 0.08714(15) 0.0361(4) Uani 1 1 d . . . H5A H 0.4959 0.8452 -0.0036 0.043 Uiso 1 1 calc R . . C6 C 0.39747(11) 0.87401(14) 0.11401(15) 0.0367(4) Uani 1 1 d . . . H6A H 0.3972 0.8791 0.2045 0.044 Uiso 1 1 calc R . . C7 C 0.17071(12) 0.83037(15) -0.02084(16) 0.0383(4) Uani 1 1 d . . . C8 C 0.07402(11) 0.83802(14) 0.01097(15) 0.0367(4) Uani 1 1 d . . . C9 C 0.05306(13) 0.81364(16) 0.12934(16) 0.0458(5) Uani 1 1 d . . . H9 H 0.1007 0.7934 0.1931 0.055 Uiso 1 1 calc R . . C10 C -0.03877(13) 0.81939(17) 0.15252(18) 0.0542(5) Uani 1 1 d . . . H10 H -0.0526 0.8040 0.2323 0.065 Uiso 1 1 calc R . . C11 C -0.11014(13) 0.84783(17) 0.05796(19) 0.0524(5) Uani 1 1 d . . . H11 H -0.1719 0.8511 0.0740 0.063 Uiso 1 1 calc R . . C12 C -0.08993(13) 0.87129(17) -0.05956(18) 0.0520(5) Uani 1 1 d . . . H12 H -0.1380 0.8898 -0.1235 0.062 Uiso 1 1 calc R . . C13 C 0.00176(13) 0.86740(16) -0.08314(17) 0.0449(5) Uani 1 1 d . . . H13 H 0.0153 0.8846 -0.1627 0.054 Uiso 1 1 calc R . . C14 C 0.67689(11) 0.63529(15) 0.14578(16) 0.0378(4) Uani 1 1 d . . . C15 C 0.74318(11) 0.59061(15) 0.06406(16) 0.0395(4) Uani 1 1 d . . . C16 C 0.73540(13) 0.61998(17) -0.06092(18) 0.0500(5) Uani 1 1 d . . . H16 H 0.6889 0.6705 -0.0954 0.060 Uiso 1 1 calc R . . C17 C 0.79693(15) 0.5741(2) -0.1346(2) 0.0640(6) Uani 1 1 d . . . H17 H 0.7915 0.5937 -0.2188 0.077 Uiso 1 1 calc R . . C18 C 0.86602(15) 0.4997(2) -0.0843(2) 0.0687(7) Uani 1 1 d . . . H18 H 0.9073 0.4693 -0.1344 0.082 Uiso 1 1 calc R . . C19 C 0.87418(14) 0.4701(2) 0.0396(2) 0.0658(6) Uani 1 1 d . . . H19 H 0.9210 0.4198 0.0735 0.079 Uiso 1 1 calc R . . C20 C 0.81295(13) 0.51503(17) 0.11401(19) 0.0537(5) Uani 1 1 d . . . H20 H 0.8184 0.4946 0.1980 0.064 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 O1 0.0328(7) 0.0561(8) 0.0352(6) 0.0027(6) 0.0073(5) 0.0058(6) O2 0.0410(7) 0.0545(8) 0.0368(7) 0.0054(6) 0.0136(5) 0.0002(6) O3 0.0525(8) 0.0374(7) 0.0506(8) 0.0036(6) 0.0172(6) 0.0058(6) O4 0.0338(7) 0.0499(8) 0.0395(7) 0.0037(6) 0.0124(5) 0.0053(6) O5 0.0531(8) 0.0502(8) 0.0486(7) -0.0069(6) 0.0158(6) -0.0192(6) O6 0.0670(9) 0.0368(8) 0.0533(8) 0.0057(6) 0.0251(7) 0.0090(6) O7 0.0450(8) 0.0993(12) 0.0343(7) 0.0066(7) 0.0100(6) 0.0090(7) O8 0.0484(8) 0.0634(9) 0.0395(8) 0.0042(6) 0.0048(6) 0.0016(6) C1 0.0318(9) 0.0460(11) 0.0333(9) -0.0011(8) 0.0089(7) 0.0028(8) C2 0.0346(10) 0.0385(10) 0.0359(9) -0.0027(8) 0.0074(7) -0.0041(7) C3 0.0407(10) 0.0357(10) 0.0360(9) 0.0012(7) 0.0080(8) 0.0016(8) C4 0.0308(9) 0.0441(11) 0.0325(9) -0.0009(7) 0.0115(7) 0.0002(7) C5 0.0383(10) 0.0374(10) 0.0341(9) -0.0042(7) 0.0105(7) -0.0057(8) C6 0.0448(10) 0.0324(10) 0.0350(9) 0.0012(7) 0.0131(8) 0.0015(8) C7 0.0404(10) 0.0394(11) 0.0348(10) 0.0005(8) 0.0047(8) 0.0026(8) C8 0.0364(10) 0.0364(10) 0.0374(9) -0.0003(8) 0.0060(7) 0.0006(7) C9 0.0431(11) 0.0525(12) 0.0419(10) 0.0087(9) 0.0068(8) 0.0077(9) C10 0.0495(12) 0.0655(14) 0.0512(12) 0.0121(10) 0.0190(9) 0.0065(10) C11 0.0362(11) 0.0586(13) 0.0641(13) -0.0004(10) 0.0129(9) 0.0008(9) C12 0.0396(11) 0.0620(13) 0.0521(12) -0.0015(10) -0.0010(9) 0.0050(9) C13 0.0437(11) 0.0517(12) 0.0388(10) -0.0003(8) 0.0046(8) 0.0008(9) C14 0.0332(10) 0.0385(10) 0.0414(11) -0.0009(8) 0.0048(8) -0.0055(8) C15 0.0315(9) 0.0416(11) 0.0457(10) -0.0055(8) 0.0070(8) -0.0049(8) C16 0.0471(11) 0.0503(12) 0.0561(12) 0.0038(9) 0.0197(9) -0.0024(9) C17 0.0598(14) 0.0755(16) 0.0640(14) -0.0043(12) 0.0337(11) -0.0082(12) C18 0.0474(13) 0.0747(17) 0.0905(18) -0.0231(13) 0.0319(12) -0.0046(11) C19 0.0393(12) 0.0668(15) 0.0897(17) -0.0207(13) 0.0038(11) 0.0112(10) C20 0.0434(12) 0.0578(13) 0.0571(12) -0.0105(10) -0.0021(9) 0.0054(9) _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 O1 C7 1.3467(19) . ? O1 C1 1.4555(18) . ? O2 C2 1.4232(19) . ? O2 H2 0.8200 . ? O3 C3 1.407(2) . ? O3 H3 0.8200 . ? O4 C14 1.332(2) . ? O4 C4 1.4516(18) . ? O5 C5 1.4227(19) . ? O5 H5 0.8200 . ? O6 C6 1.4248(19) . ? O6 H6 0.8200 . ? O7 C7 1.2031(19) . ? O8 C14 1.2119(19) . ? C1 C6 1.512(2) . ? C1 C2 1.518(2) . ? C1 H1 0.9800 . ? C2 C3 1.513(2) . ? C2 H2A 0.9800 . ? C3 C4 1.524(2) . ? C3 H3A 0.9800 . ? C4 C5 1.515(2) . ? C4 H4 0.9800 . ? C5 C6 1.528(2) . ? C5 H5A 0.9800 . ? C6 H6A 0.9800 . ? C7 C8 1.483(2) . ? C8 C9 1.385(2) . ? C8 C13 1.388(2) . ? C9 C10 1.381(2) . ? C9 H9 0.9300 . ? C10 C11 1.380(3) . ? C10 H10 0.9300 . ? C11 C12 1.370(3) . ? C11 H11 0.9300 . ? C12 C13 1.380(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.485(2) . ? C15 C16 1.382(2) . ? C15 C20 1.388(3) . ? C16 C17 1.381(3) . ? C16 H16 0.9300 . ? C17 C18 1.374(3) . ? C17 H17 0.9300 . ? C18 C19 1.370(3) . ? C18 H18 0.9300 . ? C19 C20 1.379(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 118.00(12) . . ? C2 O2 H2 109.5 . . ? C3 O3 H3 109.5 . . ? C14 O4 C4 120.33(13) . . ? C5 O5 H5 109.5 . . ? C6 O6 H6 109.5 . . ? O1 C1 C6 110.43(13) . . ? O1 C1 C2 107.74(12) . . ? C6 C1 C2 111.64(13) . . ? O1 C1 H1 109.0 . . ? C6 C1 H1 109.0 . . ? C2 C1 H1 109.0 . . ? O2 C2 C3 107.73(13) . . ? O2 C2 C1 112.08(13) . . ? C3 C2 C1 108.59(13) . . ? O2 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? O3 C3 C2 113.11(13) . . ? O3 C3 C4 111.15(14) . . ? C2 C3 C4 111.30(14) . . ? O3 C3 H3A 107.0 . . ? C2 C3 H3A 107.0 . . ? C4 C3 H3A 107.0 . . ? O4 C4 C5 105.92(12) . . ? O4 C4 C3 106.34(13) . . ? C5 C4 C3 113.39(13) . . ? O4 C4 H4 110.3 . . ? C5 C4 H4 110.3 . . ? C3 C4 H4 110.3 . . ? O5 C5 C4 108.99(14) . . ? O5 C5 C6 110.52(13) . . ? C4 C5 C6 111.38(13) . . ? O5 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? O6 C6 C1 109.47(14) . . ? O6 C6 C5 109.22(13) . . ? C1 C6 C5 108.44(13) . . ? O6 C6 H6A 109.9 . . ? C1 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? O7 C7 O1 123.82(15) . . ? O7 C7 C8 123.71(15) . . ? O1 C7 C8 112.45(14) . . ? C9 C8 C13 119.16(16) . . ? C9 C8 C7 122.53(15) . . ? C13 C8 C7 118.28(15) . . ? C10 C9 C8 119.90(16) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C11 C10 C9 120.43(18) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 119.95(18) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.03(18) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 120.53(17) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? O8 C14 O4 124.57(15) . . ? O8 C14 C15 123.88(16) . . ? O4 C14 C15 111.55(15) . . ? C16 C15 C20 119.38(17) . . ? C16 C15 C14 121.64(16) . . ? C20 C15 C14 118.96(17) . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C16 120.4(2) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 120.11(19) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C15 120.24(19) . . ? C19 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? 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 C6 114.34(16) . . . . ? C7 O1 C1 C2 -123.49(15) . . . . ? O1 C1 C2 O2 -64.57(16) . . . . ? C6 C1 C2 O2 56.84(17) . . . . ? O1 C1 C2 C3 176.54(12) . . . . ? C6 C1 C2 C3 -62.05(17) . . . . ? O2 C2 C3 O3 59.92(17) . . . . ? C1 C2 C3 O3 -178.48(13) . . . . ? O2 C2 C3 C4 -66.06(17) . . . . ? C1 C2 C3 C4 55.53(18) . . . . ? C14 O4 C4 C5 145.31(14) . . . . ? C14 O4 C4 C3 -93.77(17) . . . . ? O3 C3 C4 O4 64.79(16) . . . . ? C2 C3 C4 O4 -168.15(12) . . . . ? O3 C3 C4 C5 -179.22(12) . . . . ? C2 C3 C4 C5 -52.16(18) . . . . ? O4 C4 C5 O5 -69.78(15) . . . . ? C3 C4 C5 O5 173.98(12) . . . . ? O4 C4 C5 C6 168.02(12) . . . . ? C3 C4 C5 C6 51.78(18) . . . . ? O1 C1 C6 O6 -59.56(16) . . . . ? C2 C1 C6 O6 -179.40(12) . . . . ? O1 C1 C6 C5 -178.63(12) . . . . ? C2 C1 C6 C5 61.54(17) . . . . ? O5 C5 C6 O6 64.38(17) . . . . ? C4 C5 C6 O6 -174.30(13) . . . . ? O5 C5 C6 C1 -176.39(13) . . . . ? C4 C5 C6 C1 -55.08(17) . . . . ? C1 O1 C7 O7 -7.8(2) . . . . ? C1 O1 C7 C8 170.89(13) . . . . ? O7 C7 C8 C9 172.66(18) . . . . ? O1 C7 C8 C9 -6.0(2) . . . . ? O7 C7 C8 C13 -5.3(3) . . . . ? O1 C7 C8 C13 176.05(15) . . . . ? C13 C8 C9 C10 -0.4(3) . . . . ? C7 C8 C9 C10 -178.31(17) . . . . ? C8 C9 C10 C11 0.9(3) . . . . ? C9 C10 C11 C12 -0.4(3) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C11 C12 C13 C8 1.0(3) . . . . ? C9 C8 C13 C12 -0.6(3) . . . . ? C7 C8 C13 C12 177.44(16) . . . . ? C4 O4 C14 O8 -15.4(2) . . . . ? C4 O4 C14 C15 165.02(13) . . . . ? O8 C14 C15 C16 -175.02(16) . . . . ? O4 C14 C15 C16 4.6(2) . . . . ? O8 C14 C15 C20 6.8(3) . . . . ? O4 C14 C15 C20 -173.63(15) . . . . ? C20 C15 C16 C17 0.0(3) . . . . ? C14 C15 C16 C17 -178.23(18) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? C17 C18 C19 C20 0.1(3) . . . . ? C18 C19 C20 C15 -0.3(3) . . . . ? C16 C15 C20 C19 0.3(3) . . . . ? C14 C15 C20 C19 178.53(17) . . . . ? 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 C1 H1 O2 0.98 2.53 3.466(2) 160.4 4_575 C12 H12 O8 0.93 2.69 3.549(2) 154.3 4_475 C9 H9 O7 0.93 2.68 3.552(2) 155.7 4_576 C3 H3A O3 0.98 2.63 3.345(2) 129.9 3_665 O6 H6 O8 0.82 1.96 2.7725(18) 174.2 2_655 O3 H3 O5 0.82 2.02 2.7843(18) 154.8 2_645 O2 H2 O7 0.82 2.16 2.9514(18) 160.7 4_576 O5 H5 O6 0.82 1.92 2.7309(17) 170.1 3_675 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.212 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.035