#------------------------------------------------------------------------------ #$Date: 2008-02-29 13:03:34 +0200 (Fri, 29 Feb 2008) $ #$Revision: 179 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2015263.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2015263 loop_ _publ_author_name 'Blake, Alexander J.' 'Gonz\'alez, Miguel A.' 'Gil-Gimeno, Maria J.' _publ_section_title ;\ (-)-(5S,8S,9R,10S,13R,14R)-\ 15-Acetoxy-15,16-dideoxy-16,17-epoxyspongian-16-one ; _journal_coeditor_code LN3004 _journal_issue 4 _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o208 _journal_page_last o210 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C22 H34 O4' _chemical_formula_moiety 'C22 H34 O4' _chemical_formula_sum 'C22 H34 O4' _chemical_formula_weight 362.49 _chemical_melting_point 419--421 _chemical_name_systematic ; (-)-(5S,8S,9R,10S,13R,14R)-15-Acetoxy-15,16-dideoxy-16,17-epoxyspongian-16-one ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C 2y' _symmetry_space_group_name_H-M 'C 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _cell_angle_alpha 90.00 _cell_angle_beta 94.235(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.377(2) _cell_length_b 6.0824(8) _cell_length_c 23.834(3) _cell_measurement_reflns_used 3476 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.6 _cell_volume 1933.9(5) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT and SHELXTL (Bruker, 2001)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'enCIFer (Allen et al., 2004) and PLATON' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.133 _diffrn_reflns_av_sigmaI/netI 0.080 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 5352 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.57 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_description tablet _exptl_crystal_F_000 792 _exptl_crystal_size_max 1.07 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.40 _refine_diff_density_min -0.27 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.92 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 2382 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.92 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0487 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.106P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.130 _refine_ls_wR_factor_ref 0.133 _reflns_number_gt 2200 _reflns_number_total 2382 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ln3004.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy C C1 0.17249(16) 0.5239(4) 0.64125(8) 0.0223(4) Uani d . 1 H H1A 0.1075 0.4550 0.6481 0.027 Uiso calc R 1 H H1B 0.1710 0.6774 0.6550 0.027 Uiso calc R 1 C C2 0.18436(16) 0.5260(5) 0.57783(8) 0.0261(5) Uani d . 1 H H2A 0.1790 0.3739 0.5631 0.031 Uiso calc R 1 H H2B 0.1295 0.6137 0.5587 0.031 Uiso calc R 1 C C3 0.28490(18) 0.6232(5) 0.56464(9) 0.0287(5) Uani d . 1 H H3A 0.2857 0.7812 0.5747 0.034 Uiso calc R 1 H H3B 0.2913 0.6124 0.5236 0.034 Uiso calc R 1 C C4 0.37618(16) 0.5113(4) 0.59559(8) 0.0233(5) Uani d . 1 C C5 0.35872(16) 0.4998(4) 0.65979(8) 0.0198(4) Uani d . 1 H H5 0.3554 0.6569 0.6719 0.024 Uiso calc R 1 C C6 0.44649(16) 0.4030(4) 0.69668(8) 0.0219(4) Uani d . 1 H H6A 0.4495 0.2422 0.6905 0.026 Uiso calc R 1 H H6B 0.5101 0.4678 0.6857 0.026 Uiso calc R 1 C C7 0.43527(15) 0.4490(4) 0.75898(8) 0.0213(4) Uani d . 1 H H7A 0.4386 0.6098 0.7653 0.026 Uiso calc R 1 H H7B 0.4923 0.3813 0.7815 0.026 Uiso calc R 1 C C8 0.33666(16) 0.3610(3) 0.78006(8) 0.0186(4) Uani d . 1 C C9 0.24753(15) 0.4441(3) 0.73928(8) 0.0182(4) Uani d . 1 H H9 0.2502 0.6079 0.7427 0.022 Uiso calc R 1 C C10 0.25741(16) 0.3985(3) 0.67533(8) 0.0177(4) Uani d . 1 C C11 0.14387(16) 0.3811(4) 0.75895(9) 0.0226(4) Uani d . 1 H H11A 0.0912 0.4600 0.7355 0.027 Uiso calc R 1 H H11B 0.1331 0.2215 0.7531 0.027 Uiso calc R 1 C C12 0.13324(16) 0.4360(4) 0.82095(8) 0.0233(4) Uani d . 1 H H12A 0.0707 0.3698 0.8330 0.028 Uiso calc R 1 H H12B 0.1286 0.5974 0.8255 0.028 Uiso calc R 1 C C13 0.22299(18) 0.3487(4) 0.85824(9) 0.0219(4) Uani d . 1 H H13 0.2150 0.3927 0.8981 0.026 Uiso calc R 1 C C14 0.31962(16) 0.4501(3) 0.83942(8) 0.0191(4) Uani d . 1 H H14 0.3080 0.6120 0.8356 0.023 Uiso calc R 1 O O15 0.38191(13) 0.5208(3) 0.93589(6) 0.0271(4) Uani d . 1 C C15 0.40754(18) 0.4176(4) 0.88379(8) 0.0232(5) Uani d . 1 H H15 0.4202 0.2588 0.8900 0.028 Uiso calc R 1 H H15B 0.4690 0.4853 0.8708 0.028 Uiso calc R 1 O O16 0.16935(14) -0.0141(3) 0.88247(8) 0.0368(4) Uani d . 1 C C16 0.21947(18) 0.0995(4) 0.85418(9) 0.0253(5) Uani d . 1 O O17 0.26571(13) 0.0020(3) 0.81182(7) 0.0271(4) Uani d . 1 C C17 0.34732(17) 0.1109(4) 0.78647(9) 0.0226(4) Uani d . 1 H H17A 0.3538 0.0464 0.7488 0.027 Uiso calc R 1 H H17B 0.4103 0.0794 0.8096 0.027 Uiso calc R 1 C C18 0.46733(19) 0.6582(5) 0.58765(10) 0.0331(6) Uani d . 1 H H18A 0.4714 0.6888 0.5475 0.050 Uiso calc R 1 H H18B 0.5285 0.5829 0.6024 0.050 Uiso calc R 1 H H18C 0.4603 0.7968 0.6080 0.050 Uiso calc R 1 C C19 0.3960(2) 0.2883(5) 0.56855(9) 0.0306(5) Uani d . 1 H H19A 0.4155 0.3111 0.5301 0.046 Uiso calc R 1 H H19B 0.3350 0.1986 0.5675 0.046 Uiso calc R 1 H H19C 0.4502 0.2126 0.5907 0.046 Uiso calc R 1 C C20 0.24679(17) 0.1503(4) 0.66120(9) 0.0233(4) Uani d . 1 H H20A 0.2072 0.0784 0.6889 0.035 Uiso calc R 1 H H20B 0.3134 0.0829 0.6622 0.035 Uiso calc R 1 H H20C 0.2130 0.1327 0.6236 0.035 Uiso calc R 1 O O21 0.43121(13) 0.8479(3) 0.90373(7) 0.0309(4) Uani d . 1 C C21 0.39490(18) 0.7387(4) 0.93946(8) 0.0260(5) Uani d . 1 C C22 0.3563(2) 0.8273(5) 0.99275(10) 0.0385(6) Uani d . 1 H H22A 0.3875 0.9701 1.0017 0.058 Uiso calc R 1 H H22B 0.3729 0.7244 1.0237 0.058 Uiso calc R 1 H H22C 0.2834 0.8450 0.9876 0.058 Uiso calc R 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0168(9) 0.0248(10) 0.0245(9) 0.0007(8) -0.0048(7) -0.0005(8) C2 0.0203(10) 0.0348(12) 0.0219(9) -0.0002(10) -0.0068(7) 0.0014(9) C3 0.0316(12) 0.0304(12) 0.0233(10) -0.0042(10) -0.0026(8) 0.0033(9) C4 0.0184(10) 0.0316(12) 0.0193(9) -0.0048(9) -0.0021(7) -0.0023(9) C5 0.0190(10) 0.0206(10) 0.0193(8) -0.0024(8) -0.0026(7) -0.0014(8) C6 0.0155(10) 0.0279(11) 0.0219(9) -0.0015(8) -0.0014(7) -0.0018(8) C7 0.0146(9) 0.0274(11) 0.0211(9) -0.0031(9) -0.0045(7) -0.0003(8) C8 0.0186(10) 0.0177(10) 0.0189(9) -0.0012(8) -0.0020(7) -0.0005(7) C9 0.0182(9) 0.0165(9) 0.0193(8) 0.0013(8) -0.0035(7) -0.0004(7) C10 0.0129(9) 0.0201(10) 0.0194(8) -0.0005(7) -0.0031(7) -0.0026(7) C11 0.0183(10) 0.0263(11) 0.0225(9) 0.0007(8) -0.0019(7) 0.0004(8) C12 0.0209(10) 0.0244(11) 0.0245(10) 0.0026(9) 0.0015(8) 0.0003(9) C13 0.0245(11) 0.0197(10) 0.0214(9) -0.0014(9) 0.0006(8) 0.0013(8) C14 0.0204(10) 0.0170(9) 0.0194(8) -0.0004(8) -0.0026(7) 0.0005(7) O15 0.0348(9) 0.0272(8) 0.0189(7) -0.0042(8) -0.0018(6) 0.0008(6) C15 0.0265(11) 0.0220(10) 0.0203(9) 0.0009(8) -0.0046(8) 0.0004(8) O16 0.0387(10) 0.0287(9) 0.0434(10) -0.0067(8) 0.0052(8) 0.0100(8) C16 0.0266(12) 0.0219(10) 0.0266(10) -0.0003(9) -0.0034(8) 0.0045(9) O17 0.0317(9) 0.0171(7) 0.0323(8) -0.0017(7) 0.0002(6) 0.0022(6) C17 0.0214(10) 0.0203(10) 0.0256(9) 0.0025(8) -0.0019(8) 0.0013(8) C18 0.0280(12) 0.0452(15) 0.0261(10) -0.0139(11) 0.0005(9) 0.0028(10) C19 0.0303(12) 0.0368(12) 0.0248(10) 0.0004(10) 0.0020(9) -0.0077(10) C20 0.0218(10) 0.0207(10) 0.0272(10) -0.0031(8) -0.0001(8) -0.0050(8) O21 0.0365(10) 0.0263(8) 0.0299(8) -0.0033(8) 0.0012(7) -0.0004(7) C21 0.0301(12) 0.0281(12) 0.0190(9) -0.0004(10) -0.0045(8) -0.0029(9) C22 0.0455(15) 0.0419(15) 0.0283(11) -0.0005(13) 0.0041(10) -0.0100(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.532(3) C1 C10 1.548(3) C1 H1A 0.9900 C1 H1B 0.9900 C2 C3 1.523(3) C2 H2A 0.9900 C2 H2B 0.9900 C3 C4 1.538(3) C3 H3A 0.9900 C3 H3B 0.9900 C4 C19 1.533(4) C4 C18 1.535(3) C4 C5 1.566(3) C5 C6 1.531(3) C5 C10 1.558(3) C5 H5 1.0000 C6 C7 1.529(3) C6 H6A 0.9900 C6 H6B 0.9900 C7 C8 1.542(3) C7 H7A 0.9900 C7 H7B 0.9900 C8 C17 1.534(3) C8 C14 1.548(3) C8 C9 1.566(3) C9 C11 1.545(3) C9 C10 1.564(3) C9 H9 1.0000 C10 C20 1.551(3) C11 C12 1.532(3) C11 H11A 0.9900 C11 H11B 0.9900 C12 C13 1.535(3) C12 H12A 0.9900 C12 H12B 0.9900 C13 C16 1.519(3) C13 C14 1.529(3) C13 H13 1.0000 C14 C15 1.535(3) C14 H14 1.0000 O15 C21 1.339(3) O15 C15 1.455(3) C15 H15 0.9900 C15 H15B 0.9900 O16 C16 1.204(3) C16 O17 1.359(3) O17 C17 1.447(3) C17 H17A 0.9900 C17 H17B 0.9900 C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 C19 H19A 0.9800 C19 H19B 0.9800 C19 H19C 0.9800 C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 O21 C21 1.210(3) C21 C22 1.505(3) C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C10 113.37(18) C2 C1 H1A 108.9 C10 C1 H1A 108.9 C2 C1 H1B 108.9 C10 C1 H1B 108.9 H1A C1 H1B 107.7 C3 C2 C1 111.37(17) C3 C2 H2A 109.4 C1 C2 H2A 109.4 C3 C2 H2B 109.4 C1 C2 H2B 109.4 H2A C2 H2B 108.0 C2 C3 C4 114.3(2) C2 C3 H3A 108.7 C4 C3 H3A 108.7 C2 C3 H3B 108.7 C4 C3 H3B 108.7 H3A C3 H3B 107.6 C19 C4 C18 107.43(19) C19 C4 C3 110.23(18) C18 C4 C3 107.0(2) C19 C4 C5 114.4(2) C18 C4 C5 108.89(17) C3 C4 C5 108.55(17) C6 C5 C10 110.79(17) C6 C5 C4 114.51(17) C10 C5 C4 116.42(16) C6 C5 H5 104.5 C10 C5 H5 104.5 C4 C5 H5 104.5 C7 C6 C5 111.16(17) C7 C6 H6A 109.4 C5 C6 H6A 109.4 C7 C6 H6B 109.4 C5 C6 H6B 109.4 H6A C6 H6B 108.0 C6 C7 C8 113.61(16) C6 C7 H7A 108.8 C8 C7 H7A 108.8 C6 C7 H7B 108.8 C8 C7 H7B 108.8 H7A C7 H7B 107.7 C17 C8 C7 107.54(19) C17 C8 C14 105.97(17) C7 C8 C14 111.32(16) C17 C8 C9 116.30(19) C7 C8 C9 108.42(16) C14 C8 C9 107.31(16) C11 C9 C10 113.20(16) C11 C9 C8 113.02(16) C10 C9 C8 115.61(16) C11 C9 H9 104.5 C10 C9 H9 104.5 C8 C9 H9 104.5 C1 C10 C20 108.29(18) C1 C10 C5 107.33(17) C20 C10 C5 113.61(18) C1 C10 C9 108.20(16) C20 C10 C9 111.80(17) C5 C10 C9 107.40(16) C12 C11 C9 112.84(18) C12 C11 H11A 109.0 C9 C11 H11A 109.0 C12 C11 H11B 109.0 C9 C11 H11B 109.0 H11A C11 H11B 107.8 C11 C12 C13 111.03(17) C11 C12 H12A 109.4 C13 C12 H12A 109.4 C11 C12 H12B 109.4 C13 C12 H12B 109.4 H12A C12 H12B 108.0 C16 C13 C14 114.0(2) C16 C13 C12 106.8(2) C14 C13 C12 109.43(17) C16 C13 H13 108.8 C14 C13 H13 108.8 C12 C13 H13 108.8 C13 C14 C15 111.54(17) C13 C14 C8 108.16(16) C15 C14 C8 115.32(18) C13 C14 H14 107.1 C15 C14 H14 107.1 C8 C14 H14 107.1 C21 O15 C15 116.34(18) O15 C15 C14 108.41(18) O15 C15 H15 110.0 C14 C15 H15 110.0 O15 C15 H15B 110.0 C14 C15 H15B 110.0 H15 C15 H15B 108.4 O16 C16 O17 117.9(2) O16 C16 C13 123.6(2) O17 C16 C13 118.0(2) C16 O17 C17 120.63(17) O17 C17 C8 115.34(19) O17 C17 H17A 108.4 C8 C17 H17A 108.4 O17 C17 H17B 108.4 C8 C17 H17B 108.4 H17A C17 H17B 107.5 C4 C18 H18A 109.5 C4 C18 H18B 109.5 H18A C18 H18B 109.5 C4 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C4 C19 H19A 109.5 C4 C19 H19B 109.5 H19A C19 H19B 109.5 C4 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C10 C20 H20A 109.5 C10 C20 H20B 109.5 H20A C20 H20B 109.5 C10 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 O21 C21 O15 123.8(2) O21 C21 C22 125.3(2) O15 C21 C22 110.9(2) C21 C22 H22A 109.5 C21 C22 H22B 109.5 H22A C22 H22B 109.5 C21 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 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 C10 C1 C2 C3 -56.6(3) C1 C2 C3 C4 54.7(3) C2 C3 C4 C19 75.4(2) C2 C3 C4 C18 -168.08(19) C2 C3 C4 C5 -50.7(3) C19 C4 C5 C6 59.6(2) C18 C4 C5 C6 -60.6(3) C3 C4 C5 C6 -176.84(19) C19 C4 C5 C10 -71.9(2) C18 C4 C5 C10 167.9(2) C3 C4 C5 C10 51.7(3) C10 C5 C6 C7 -60.0(2) C4 C5 C6 C7 165.89(18) C5 C6 C7 C8 57.3(2) C6 C7 C8 C17 75.4(2) C6 C7 C8 C14 -168.96(17) C6 C7 C8 C9 -51.1(2) C17 C8 C9 C11 63.3(2) C7 C8 C9 C11 -175.42(16) C14 C8 C9 C11 -55.1(2) C17 C8 C9 C10 -69.4(2) C7 C8 C9 C10 51.9(2) C14 C8 C9 C10 172.21(17) C2 C1 C10 C20 -68.7(2) C2 C1 C10 C5 54.3(2) C2 C1 C10 C9 169.90(18) C6 C5 C10 C1 173.53(16) C4 C5 C10 C1 -53.3(2) C6 C5 C10 C20 -66.8(2) C4 C5 C10 C20 66.4(2) C6 C5 C10 C9 57.4(2) C4 C5 C10 C9 -169.45(18) C11 C9 C10 C1 56.5(2) C8 C9 C10 C1 -170.88(17) C11 C9 C10 C20 -62.7(2) C8 C9 C10 C20 70.0(2) C11 C9 C10 C5 172.06(17) C8 C9 C10 C5 -55.3(2) C10 C9 C11 C12 -177.40(17) C8 C9 C11 C12 48.7(2) C9 C11 C12 C13 -49.5(2) C11 C12 C13 C16 -65.0(2) C11 C12 C13 C14 58.9(2) C16 C13 C14 C15 -75.3(2) C12 C13 C14 C15 165.17(18) C16 C13 C14 C8 52.5(2) C12 C13 C14 C8 -67.0(2) C17 C8 C14 C13 -61.2(2) C7 C8 C14 C13 -177.80(17) C9 C8 C14 C13 63.7(2) C17 C8 C14 C15 64.5(2) C7 C8 C14 C15 -52.2(2) C9 C8 C14 C15 -170.65(18) C21 O15 C15 C14 -80.9(2) C13 C14 C15 O15 -59.3(2) C8 C14 C15 O15 176.77(16) C14 C13 C16 O16 154.9(2) C12 C13 C16 O16 -84.2(3) C14 C13 C16 O17 -33.4(3) C12 C13 C16 O17 87.6(2) O16 C16 O17 C17 -163.0(2) C13 C16 O17 C17 24.8(3) C16 O17 C17 C8 -37.0(3) C7 C8 C17 O17 173.55(16) C14 C8 C17 O17 54.4(2) C9 C8 C17 O17 -64.7(2) C15 O15 C21 O21 -4.3(4) C15 O15 C21 C22 174.4(2) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C14 H14 O17 1_565 1.00 2.49 3.486(3) 171 Yes C15 H15 O21 1_545 0.99 2.52 3.509(3) 173 Yes