############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_global _audit_creation_method SHELXL-97 _journal_date_recd_electronic 2009-05-08 _journal_date_accepted 2009-05-11 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2009 _journal_volume 65 _journal_issue 6 _journal_page_first o1435 _journal_page_last o1435 _journal_paper_category QO _journal_coeditor_code TK2448 _publ_contact_author ; Dr. Seik Weng Ng Department of Chemistry University of Malaya 50603 Kuala Lumpur Malaysia ; _publ_contact_author_email seikweng@um.edu.my _publ_contact_author_fax '03 7967 4193' _publ_contact_author_phone '03 7967 6778' _publ_section_title ; 1-Hydroxy-2-methoxy-6-methyl-9,10-anthraquinone from Rennellia elliptica Korth. ; loop_ _publ_author_name _publ_author_address 'Ismail, Nor Hadiani' ; Faculty of Applied Sciences Universiti Teknologi MARA 40450 Shah Alam Selangor Darul Ehsan Malaysia ; 'Osman, Che Puteh' ; Faculty of Applied Sciences Universiti Teknologi MARA 40450 Shah Alam Selangor Darul Ehsan Malaysia ; 'Ahmad, Rohaya' ; Faculty of Applied Sciences Universiti Teknologi MARA 40450 Shah Alam Selangor Darul Ehsan Malaysia ; 'Awang, Khalijah' ; Department of Chemistry University of Malaya 50603 Kuala Lumpur Malaysia ; 'Ng, Seik Weng' ; Department of Chemistry University of Malaya 50603 Kuala Lumpur Malaysia ; _publ_section_synopsis . data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Hydroxy-2-methoxy-6-methyl-9,10-anthraquinone ; _chemical_name_common ? _chemical_formula_moiety 'C16 H12 O4' _chemical_formula_sum 'C16 H12 O4' _chemical_formula_iupac 'C16 H12 O4' _chemical_formula_weight 268.26 _chemical_melting_point ? _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1755(3) _cell_length_b 11.9082(5) _cell_length_c 14.9683(7) _cell_angle_alpha 91.409(3) _cell_angle_beta 100.603(3) _cell_angle_gamma 105.666(3) _cell_volume 1206.73(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1159 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 26.8 _cell_measurement_temperature 100(2) _exptl_crystal_description Plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type None _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6750 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_sigmaI/netI 0.091 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _reflns_number_total 4142 _reflns_number_gt 2248 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.146 _refine_ls_R_factor_gt 0.082 _refine_ls_wR_factor_gt 0.233 _refine_ls_wR_factor_ref 0.267 _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_restrained_S_all 1.08 _refine_ls_number_reflns 4142 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1397P)^2^+0.3435P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.59 _refine_diff_density_min -0.35 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'publCIF (Westrip, 2009)' 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 _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.2331(5) 0.2601(3) 0.5314(2) 0.0207(8) Uani d . 1 . . O O2 0.2924(5) 0.7172(3) 0.4917(2) 0.0219(9) Uani d . 1 . . O O3 0.3202(5) 0.6932(3) 0.3261(2) 0.0205(8) Uani d . 1 . . H H3 0.3084 0.7272 0.3737 0.031 Uiso calc R 1 . . O O4 0.3344(5) 0.5601(3) 0.1875(2) 0.0207(8) Uani d . 1 . . O O5 0.9299(6) 1.2275(3) 1.0962(2) 0.0327(10) Uani d . 1 . . O O6 0.5739(6) 0.7665(3) 1.0100(2) 0.0281(9) Uani d . 1 . . O O7 0.5636(6) 0.7944(3) 0.8409(2) 0.0297(10) Uani d . 1 . . H H7 0.5365 0.7587 0.8866 0.045 Uiso calc R 1 . . O O8 0.6524(5) 0.9285(3) 0.7122(2) 0.0279(9) Uani d . 1 . . C C1 0.1303(8) 0.4169(5) 0.8389(3) 0.0247(13) Uani d . 1 . . H H1A 0.2063 0.3608 0.8555 0.037 Uiso calc R 1 . . H H1B -0.0110 0.3773 0.8316 0.037 Uiso calc R 1 . . H H1C 0.1682 0.4806 0.8872 0.037 Uiso calc R 1 . . C C2 0.1725(7) 0.4662(4) 0.7505(3) 0.0188(11) Uani d . 1 . . C C3 0.1867(7) 0.3958(4) 0.6786(3) 0.0186(11) Uani d . 1 . . H H3A 0.1746 0.3153 0.6858 0.022 Uiso calc R 1 . . C C4 0.2183(7) 0.4406(4) 0.5959(3) 0.0163(11) Uani d . 1 . . C C5 0.2389(7) 0.3634(4) 0.5212(3) 0.0158(11) Uani d . 1 . . C C6 0.2613(7) 0.4126(4) 0.4328(3) 0.0155(11) Uani d . 1 . . C C7 0.2703(7) 0.3443(4) 0.3595(3) 0.0146(11) Uani d . 1 . . H H7A 0.2615 0.2640 0.3662 0.017 Uiso calc R 1 . . C C8 0.2921(7) 0.3884(4) 0.2752(3) 0.0187(12) Uani d . 1 . . H H8 0.2951 0.3385 0.2253 0.022 Uiso calc R 1 . . C C9 0.3092(7) 0.5067(4) 0.2654(3) 0.0179(11) Uani d . 1 . . C C10 0.3034(7) 0.5792(4) 0.3390(3) 0.0160(11) Uani d . 1 . . C C11 0.2798(7) 0.5340(4) 0.4234(3) 0.0153(11) Uani d . 1 . . C C12 0.2727(7) 0.6111(4) 0.4991(3) 0.0176(11) Uani d . 1 . . C C13 0.2400(7) 0.5601(4) 0.5865(3) 0.0143(11) Uani d . 1 . . C C14 0.2299(7) 0.6314(4) 0.6590(3) 0.0184(11) Uani d . 1 . . H H14 0.2462 0.7125 0.6527 0.022 Uiso calc R 1 . . C C15 0.1964(7) 0.5858(4) 0.7401(3) 0.0195(12) Uani d . 1 . . H H15 0.1894 0.6355 0.7893 0.023 Uiso calc R 1 . . C C16 0.3257(8) 0.4888(5) 0.1080(4) 0.0295(14) Uani d . 1 . . H H16A 0.3329 0.5367 0.0558 0.044 Uiso calc R 1 . . H H16B 0.2014 0.4261 0.0959 0.044 Uiso calc R 1 . . H H16C 0.4370 0.4546 0.1179 0.044 Uiso calc R 1 . . C C17 0.8428(9) 1.0596(5) 1.4057(3) 0.0262(13) Uani d . 1 . . H H17A 0.9719 1.1182 1.4193 0.039 Uiso calc R 1 . . H H17B 0.8450 0.9950 1.4449 0.039 Uiso calc R 1 . . H H17C 0.7409 1.0957 1.4171 0.039 Uiso calc R 1 . . C C18 0.7980(7) 1.0137(5) 1.3075(3) 0.0204(12) Uani d . 1 . . C C19 0.8440(7) 1.0856(5) 1.2383(3) 0.0204(12) Uani d . 1 . . H H19 0.9084 1.1664 1.2537 0.024 Uiso calc R 1 . . C C20 0.7990(7) 1.0432(4) 1.1479(3) 0.0167(11) Uani d . 1 . . C C21 0.8479(8) 1.1216(5) 1.0761(3) 0.0221(12) Uani d . 1 . . C C22 0.7990(7) 1.0732(4) 0.9807(3) 0.0206(12) Uani d . 1 . . C C23 0.8403(8) 1.1438(5) 0.9115(3) 0.0230(12) Uani d . 1 . . H H23 0.9019 1.2251 0.9259 0.028 Uiso calc R 1 . . C C24 0.7944(8) 1.0992(5) 0.8208(3) 0.0236(12) Uani d . 1 . . H H24 0.8261 1.1500 0.7745 0.028 Uiso calc R 1 . . C C25 0.7032(8) 0.9821(5) 0.7979(3) 0.0236(13) Uani d . 1 . . C C26 0.6581(7) 0.9084(4) 0.8672(4) 0.0218(12) Uani d . 1 . . C C27 0.7028(7) 0.9509(4) 0.9582(3) 0.0193(12) Uani d . 1 . . C C28 0.6543(7) 0.8737(4) 1.0285(3) 0.0196(12) Uani d . 1 . . C C29 0.7021(7) 0.9217(4) 1.1244(3) 0.0196(12) Uani d . 1 . . C C30 0.6537(7) 0.8511(5) 1.1930(3) 0.0221(12) Uani d . 1 . . H H30 0.5869 0.7705 1.1781 0.027 Uiso calc R 1 . . C C31 0.7009(8) 0.8955(4) 1.2837(3) 0.0224(12) Uani d . 1 . . H H31 0.6666 0.8449 1.3299 0.027 Uiso calc R 1 . . C C32 0.6916(9) 0.9996(6) 0.6386(4) 0.0317(14) Uani d . 1 . . H H32A 0.6461 0.9508 0.5809 0.047 Uiso calc R 1 . . H H32B 0.8338 1.0370 0.6471 0.047 Uiso calc R 1 . . H H32C 0.6216 1.0600 0.6374 0.047 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 O1 0.025(2) 0.0202(19) 0.0184(19) 0.0103(16) 0.0018(15) 0.0029(15) O2 0.027(2) 0.0162(19) 0.023(2) 0.0089(16) 0.0025(16) 0.0009(15) O3 0.026(2) 0.0153(18) 0.020(2) 0.0053(16) 0.0048(16) 0.0001(15) O4 0.023(2) 0.025(2) 0.0140(19) 0.0080(16) 0.0030(15) -0.0005(15) O5 0.048(3) 0.018(2) 0.025(2) -0.0013(19) 0.0036(19) -0.0023(16) O6 0.035(2) 0.018(2) 0.028(2) 0.0044(18) 0.0015(17) -0.0022(16) O7 0.037(2) 0.026(2) 0.024(2) 0.0076(19) 0.0049(18) -0.0012(17) O8 0.033(2) 0.038(2) 0.014(2) 0.0150(19) -0.0003(16) -0.0025(17) C1 0.021(3) 0.033(3) 0.024(3) 0.010(3) 0.011(2) 0.007(2) C2 0.011(3) 0.028(3) 0.017(3) 0.007(2) -0.001(2) 0.003(2) C3 0.012(3) 0.020(3) 0.023(3) 0.005(2) 0.000(2) 0.005(2) C4 0.006(2) 0.025(3) 0.017(3) 0.005(2) -0.002(2) -0.004(2) C5 0.008(3) 0.020(3) 0.019(3) 0.005(2) 0.000(2) 0.000(2) C6 0.008(3) 0.022(3) 0.015(3) 0.005(2) -0.003(2) 0.000(2) C7 0.010(3) 0.013(2) 0.020(3) 0.002(2) 0.004(2) 0.001(2) C8 0.016(3) 0.023(3) 0.016(3) 0.008(2) -0.001(2) -0.005(2) C9 0.013(3) 0.025(3) 0.016(3) 0.005(2) 0.002(2) 0.004(2) C10 0.010(3) 0.022(3) 0.015(3) 0.004(2) -0.001(2) 0.004(2) C11 0.011(3) 0.018(3) 0.015(3) 0.007(2) -0.004(2) -0.001(2) C12 0.010(3) 0.022(3) 0.019(3) 0.004(2) -0.002(2) 0.000(2) C13 0.007(2) 0.021(3) 0.016(3) 0.007(2) 0.0013(19) 0.002(2) C14 0.017(3) 0.019(3) 0.018(3) 0.007(2) -0.002(2) -0.001(2) C15 0.015(3) 0.027(3) 0.014(3) 0.006(2) -0.003(2) -0.005(2) C16 0.031(3) 0.034(3) 0.020(3) 0.003(3) 0.005(2) 0.000(2) C17 0.034(3) 0.027(3) 0.018(3) 0.011(3) -0.001(2) 0.002(2) C18 0.017(3) 0.028(3) 0.018(3) 0.013(2) 0.000(2) 0.002(2) C19 0.020(3) 0.022(3) 0.019(3) 0.009(2) -0.003(2) -0.002(2) C20 0.017(3) 0.023(3) 0.014(3) 0.013(2) 0.003(2) 0.000(2) C21 0.019(3) 0.025(3) 0.024(3) 0.011(3) 0.001(2) 0.004(2) C22 0.022(3) 0.025(3) 0.017(3) 0.012(2) 0.003(2) 0.004(2) C23 0.021(3) 0.026(3) 0.021(3) 0.005(2) 0.005(2) 0.000(2) C24 0.028(3) 0.031(3) 0.013(3) 0.010(3) 0.003(2) 0.005(2) C25 0.019(3) 0.042(3) 0.015(3) 0.015(3) 0.006(2) -0.002(2) C26 0.015(3) 0.022(3) 0.030(3) 0.010(2) 0.004(2) 0.000(2) C27 0.013(3) 0.025(3) 0.022(3) 0.010(2) 0.003(2) 0.002(2) C28 0.009(3) 0.026(3) 0.025(3) 0.008(2) 0.000(2) 0.000(2) C29 0.014(3) 0.020(3) 0.026(3) 0.010(2) -0.001(2) -0.002(2) C30 0.020(3) 0.025(3) 0.027(3) 0.012(2) 0.007(2) 0.007(2) C31 0.027(3) 0.022(3) 0.022(3) 0.012(2) 0.008(2) 0.010(2) C32 0.030(3) 0.056(4) 0.013(3) 0.017(3) 0.008(2) 0.005(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C5 . 1.235(6) ? O2 C12 . 1.243(6) ? O3 C10 . 1.351(6) ? O3 H3 . 0.8400 ? O4 C9 . 1.360(6) ? O4 C16 . 1.426(6) ? O5 C21 . 1.242(6) ? O6 C28 . 1.251(6) ? O7 C26 . 1.356(6) ? O7 H7 . 0.8400 ? O8 C25 . 1.359(6) ? O8 C32 . 1.429(6) ? C1 C2 . 1.509(7) ? C1 H1A . 0.9800 ? C1 H1B . 0.9800 ? C1 H1C . 0.9800 ? C2 C3 . 1.383(7) ? C2 C15 . 1.404(7) ? C3 C4 . 1.394(7) ? C3 H3A . 0.9500 ? C4 C13 . 1.402(7) ? C4 C5 . 1.483(7) ? C5 C6 . 1.478(7) ? C6 C7 . 1.372(7) ? C6 C11 . 1.428(7) ? C7 C8 . 1.397(7) ? C7 H7A . 0.9500 ? C8 C9 . 1.395(7) ? C8 H8 . 0.9500 ? C9 C10 . 1.397(7) ? C10 C11 . 1.406(7) ? C11 C12 . 1.459(7) ? C12 C13 . 1.487(7) ? C13 C14 . 1.386(7) ? C14 C15 . 1.377(7) ? C14 H14 . 0.9500 ? C15 H15 . 0.9500 ? C16 H16A . 0.9800 ? C16 H16B . 0.9800 ? C16 H16C . 0.9800 ? C17 C18 . 1.502(7) ? C17 H17A . 0.9800 ? C17 H17B . 0.9800 ? C17 H17C . 0.9800 ? C18 C19 . 1.390(7) ? C18 C31 . 1.396(7) ? C19 C20 . 1.382(7) ? C19 H19 . 0.9500 ? C20 C29 . 1.429(7) ? C20 C21 . 1.469(7) ? C21 C22 . 1.470(7) ? C22 C23 . 1.375(7) ? C22 C27 . 1.434(7) ? C23 C24 . 1.392(7) ? C23 H23 . 0.9500 ? C24 C25 . 1.376(8) ? C24 H24 . 0.9500 ? C25 C26 . 1.402(7) ? C26 C27 . 1.390(7) ? C27 C28 . 1.443(7) ? C28 C29 . 1.476(7) ? C29 C30 . 1.377(7) ? C30 C31 . 1.392(7) ? C30 H30 . 0.9500 ? C31 H31 . 0.9500 ? C32 H32A . 0.9800 ? C32 H32B . 0.9800 ? C32 H32C . 0.9800 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C10 O3 H3 . . 109.5 ? C9 O4 C16 . . 117.9(4) ? C26 O7 H7 . . 109.5 ? C25 O8 C32 . . 117.7(4) ? C2 C1 H1A . . 109.5 ? C2 C1 H1B . . 109.5 ? H1A C1 H1B . . 109.5 ? C2 C1 H1C . . 109.5 ? H1A C1 H1C . . 109.5 ? H1B C1 H1C . . 109.5 ? C3 C2 C15 . . 118.9(5) ? C3 C2 C1 . . 121.5(5) ? C15 C2 C1 . . 119.7(5) ? C2 C3 C4 . . 121.4(5) ? C2 C3 H3A . . 119.3 ? C4 C3 H3A . . 119.3 ? C3 C4 C13 . . 118.9(5) ? C3 C4 C5 . . 119.9(4) ? C13 C4 C5 . . 121.1(4) ? O1 C5 C6 . . 120.5(4) ? O1 C5 C4 . . 121.3(4) ? C6 C5 C4 . . 118.2(4) ? C7 C6 C11 . . 118.8(4) ? C7 C6 C5 . . 121.2(4) ? C11 C6 C5 . . 120.0(4) ? C6 C7 C8 . . 122.5(4) ? C6 C7 H7A . . 118.8 ? C8 C7 H7A . . 118.8 ? C9 C8 C7 . . 119.0(5) ? C9 C8 H8 . . 120.5 ? C7 C8 H8 . . 120.5 ? O4 C9 C10 . . 115.4(4) ? O4 C9 C8 . . 124.5(5) ? C10 C9 C8 . . 120.1(4) ? O3 C10 C9 . . 117.9(4) ? O3 C10 C11 . . 121.6(4) ? C9 C10 C11 . . 120.5(4) ? C10 C11 C6 . . 119.1(4) ? C10 C11 C12 . . 119.6(4) ? C6 C11 C12 . . 121.3(4) ? O2 C12 C11 . . 121.5(4) ? O2 C12 C13 . . 120.0(4) ? C11 C12 C13 . . 118.5(4) ? C14 C13 C4 . . 119.9(4) ? C14 C13 C12 . . 119.5(4) ? C4 C13 C12 . . 120.6(4) ? C15 C14 C13 . . 120.6(5) ? C15 C14 H14 . . 119.7 ? C13 C14 H14 . . 119.7 ? C14 C15 C2 . . 120.3(5) ? C14 C15 H15 . . 119.8 ? C2 C15 H15 . . 119.8 ? O4 C16 H16A . . 109.5 ? O4 C16 H16B . . 109.5 ? H16A C16 H16B . . 109.5 ? O4 C16 H16C . . 109.5 ? H16A C16 H16C . . 109.5 ? H16B C16 H16C . . 109.5 ? C18 C17 H17A . . 109.5 ? C18 C17 H17B . . 109.5 ? H17A C17 H17B . . 109.5 ? C18 C17 H17C . . 109.5 ? H17A C17 H17C . . 109.5 ? H17B C17 H17C . . 109.5 ? C19 C18 C31 . . 118.3(5) ? C19 C18 C17 . . 122.3(5) ? C31 C18 C17 . . 119.3(5) ? C20 C19 C18 . . 122.1(5) ? C20 C19 H19 . . 119.0 ? C18 C19 H19 . . 119.0 ? C19 C20 C29 . . 119.1(5) ? C19 C20 C21 . . 120.8(5) ? C29 C20 C21 . . 120.0(4) ? O5 C21 C22 . . 120.6(5) ? O5 C21 C20 . . 120.1(5) ? C22 C21 C20 . . 119.2(5) ? C23 C22 C27 . . 118.8(5) ? C23 C22 C21 . . 121.1(5) ? C27 C22 C21 . . 120.1(4) ? C22 C23 C24 . . 121.7(5) ? C22 C23 H23 . . 119.1 ? C24 C23 H23 . . 119.1 ? C25 C24 C23 . . 120.4(5) ? C25 C24 H24 . . 119.8 ? C23 C24 H24 . . 119.8 ? O8 C25 C24 . . 125.8(5) ? O8 C25 C26 . . 115.3(5) ? C24 C25 C26 . . 119.0(5) ? O7 C26 C27 . . 121.6(5) ? O7 C26 C25 . . 116.7(5) ? C27 C26 C25 . . 121.7(5) ? C26 C27 C22 . . 118.5(5) ? C26 C27 C28 . . 120.8(5) ? C22 C27 C28 . . 120.7(5) ? O6 C28 C27 . . 121.4(5) ? O6 C28 C29 . . 119.1(5) ? C27 C28 C29 . . 119.5(5) ? C30 C29 C20 . . 118.6(5) ? C30 C29 C28 . . 121.0(5) ? C20 C29 C28 . . 120.3(5) ? C29 C30 C31 . . 121.3(5) ? C29 C30 H30 . . 119.3 ? C31 C30 H30 . . 119.3 ? C30 C31 C18 . . 120.5(5) ? C30 C31 H31 . . 119.7 ? C18 C31 H31 . . 119.7 ? O8 C32 H32A . . 109.5 ? O8 C32 H32B . . 109.5 ? H32A C32 H32B . . 109.5 ? O8 C32 H32C . . 109.5 ? H32A C32 H32C . . 109.5 ? H32B C32 H32C . . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C15 C2 C3 C4 . . . . -1.8(7) ? C1 C2 C3 C4 . . . . 177.5(4) ? C2 C3 C4 C13 . . . . 1.3(7) ? C2 C3 C4 C5 . . . . 178.1(4) ? C3 C4 C5 O1 . . . . -1.6(7) ? C13 C4 C5 O1 . . . . 175.1(5) ? C3 C4 C5 C6 . . . . 176.7(4) ? C13 C4 C5 C6 . . . . -6.6(6) ? O1 C5 C6 C7 . . . . 1.9(7) ? C4 C5 C6 C7 . . . . -176.5(4) ? O1 C5 C6 C11 . . . . -176.2(4) ? C4 C5 C6 C11 . . . . 5.4(6) ? C11 C6 C7 C8 . . . . -1.7(7) ? C5 C6 C7 C8 . . . . -179.8(4) ? C6 C7 C8 C9 . . . . 1.3(7) ? C16 O4 C9 C10 . . . . -175.1(4) ? C16 O4 C9 C8 . . . . 5.6(7) ? C7 C8 C9 O4 . . . . 178.8(4) ? C7 C8 C9 C10 . . . . -0.4(7) ? O4 C9 C10 O3 . . . . 0.8(6) ? C8 C9 C10 O3 . . . . -179.9(4) ? O4 C9 C10 C11 . . . . -179.4(4) ? C8 C9 C10 C11 . . . . -0.1(7) ? O3 C10 C11 C6 . . . . 179.5(4) ? C9 C10 C11 C6 . . . . -0.2(7) ? O3 C10 C11 C12 . . . . 0.1(7) ? C9 C10 C11 C12 . . . . -179.6(4) ? C7 C6 C11 C10 . . . . 1.1(7) ? C5 C6 C11 C10 . . . . 179.2(4) ? C7 C6 C11 C12 . . . . -179.6(4) ? C5 C6 C11 C12 . . . . -1.4(7) ? C10 C11 C12 O2 . . . . -2.0(7) ? C6 C11 C12 O2 . . . . 178.7(4) ? C10 C11 C12 C13 . . . . 177.7(4) ? C6 C11 C12 C13 . . . . -1.7(7) ? C3 C4 C13 C14 . . . . 0.0(7) ? C5 C4 C13 C14 . . . . -176.7(4) ? C3 C4 C13 C12 . . . . -179.6(4) ? C5 C4 C13 C12 . . . . 3.6(7) ? O2 C12 C13 C14 . . . . 0.6(7) ? C11 C12 C13 C14 . . . . -179.1(4) ? O2 C12 C13 C4 . . . . -179.7(4) ? C11 C12 C13 C4 . . . . 0.6(6) ? C4 C13 C14 C15 . . . . -0.8(7) ? C12 C13 C14 C15 . . . . 178.9(4) ? C13 C14 C15 C2 . . . . 0.2(7) ? C3 C2 C15 C14 . . . . 1.1(7) ? C1 C2 C15 C14 . . . . -178.3(4) ? C31 C18 C19 C20 . . . . -0.9(7) ? C17 C18 C19 C20 . . . . -178.7(5) ? C18 C19 C20 C29 . . . . 0.0(7) ? C18 C19 C20 C21 . . . . 179.4(4) ? C19 C20 C21 O5 . . . . -0.3(7) ? C29 C20 C21 O5 . . . . 179.1(5) ? C19 C20 C21 C22 . . . . 179.6(4) ? C29 C20 C21 C22 . . . . -1.0(7) ? O5 C21 C22 C23 . . . . -0.8(8) ? C20 C21 C22 C23 . . . . 179.3(4) ? O5 C21 C22 C27 . . . . -179.5(5) ? C20 C21 C22 C27 . . . . 0.6(7) ? C27 C22 C23 C24 . . . . -1.1(7) ? C21 C22 C23 C24 . . . . -179.8(5) ? C22 C23 C24 C25 . . . . 0.7(8) ? C32 O8 C25 C24 . . . . -1.8(7) ? C32 O8 C25 C26 . . . . 178.9(4) ? C23 C24 C25 O8 . . . . -179.5(5) ? C23 C24 C25 C26 . . . . -0.2(7) ? O8 C25 C26 O7 . . . . -2.4(7) ? C24 C25 C26 O7 . . . . 178.3(4) ? O8 C25 C26 C27 . . . . 179.5(4) ? C24 C25 C26 C27 . . . . 0.2(7) ? O7 C26 C27 C22 . . . . -178.6(4) ? C25 C26 C27 C22 . . . . -0.5(7) ? O7 C26 C27 C28 . . . . 1.7(7) ? C25 C26 C27 C28 . . . . 179.7(4) ? C23 C22 C27 C26 . . . . 1.0(7) ? C21 C22 C27 C26 . . . . 179.7(4) ? C23 C22 C27 C28 . . . . -179.2(4) ? C21 C22 C27 C28 . . . . -0.5(7) ? C26 C27 C28 O6 . . . . 1.1(7) ? C22 C27 C28 O6 . . . . -178.6(5) ? C26 C27 C28 C29 . . . . -179.5(4) ? C22 C27 C28 C29 . . . . 0.8(7) ? C19 C20 C29 C30 . . . . 1.1(7) ? C21 C20 C29 C30 . . . . -178.3(4) ? C19 C20 C29 C28 . . . . -179.3(4) ? C21 C20 C29 C28 . . . . 1.3(7) ? O6 C28 C29 C30 . . . . -2.1(7) ? C27 C28 C29 C30 . . . . 178.4(4) ? O6 C28 C29 C20 . . . . 178.3(4) ? C27 C28 C29 C20 . . . . -1.2(7) ? C20 C29 C30 C31 . . . . -1.3(7) ? C28 C29 C30 C31 . . . . 179.1(4) ? C29 C30 C31 C18 . . . . 0.4(7) ? C19 C18 C31 C30 . . . . 0.7(7) ? C17 C18 C31 C30 . . . . 178.6(5) ? 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 O3 H3 O2 . 0.84 1.80 2.538(4) 147 yes O7 H7 O6 . 0.84 1.81 2.551(5) 146 yes