# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ; ? ; _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_volume ? _journal_year ? loop_ _publ_author_address ; Chemistry Section, M313, School of Biomedical and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; ; Chemistry Section, M313, School of Biomedical and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; ; Chemistry Section, M313, School of Biomedical and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; ; Chemistry Section, M313, School of Biomedical and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; _publ_contact_author_address ; Chemistry Section, M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; _publ_contact_author_email Alexandre.Sobolev@uwa.edu.au _publ_contact_author_fax '+618 6488 1005' _publ_contact_author_phone '+618 6488 3157' #TrackingRef '- CCDC_796805.cif' # 1. SUBMISSION DETAILS _publ_contact_author_name 'Dr. Alexandre N. Sobolev' _publ_contact_letter ; Please consider this submission for publication as a New paper in Chemical Communication. The figures, chemical structure diagram (scheme), Transfer of Copyright Agreement form and structure factor listing will be sent on receipt of your acknowledgement email or letter. ; _publ_requested_coeditor_name ? # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? #<< paper title text ; data_gk286 _database_code_depnum_ccdc_archive 'CCDC 796805' _publ_section_title_footnote ; ? #<< paper footnote text ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Mercury CSD 2.3 - New Features for the Visualization and Investigation of Crystal Structures C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, (2008), J. Appl. Cryst., 41, 466-470. G.M. Sheldrick, (2008). Acta Cryst., A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-p-Hydroxyphenyl-2,2,4-trimethylchroman ; _chemical_name_common 4-p-Hydroxyphenyl-2,2,4-trimethylchroman _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 O2' _chemical_formula_sum 'C18 H20 O2' _chemical_formula_weight 268.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_int_tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 26.7783(12) _cell_length_b 26.7783 _cell_length_c 10.9031(4) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 120.0 _cell_volume 6770.9(4) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12176 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 32.26 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9644 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire3 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48523 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 32.29 _reflns_number_total 5194 _reflns_number_gt 3511 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury CSD v. 2.3 (2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0740P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5194 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 O1 O 0.06446(4) 0.11877(4) 0.48203(8) 0.0287(2) Uani 1 1 d . . . H1 H 0.0840 0.1018 0.4896 0.043 Uiso 1 1 calc R . . O2 O 0.08799(3) 0.26203(3) -0.12882(7) 0.01902(18) Uani 1 1 d . . . C2 C 0.08817(4) 0.29875(5) -0.04104(10) 0.0159(2) Uani 1 1 d . . . C1 C 0.11127(5) 0.22497(5) -0.09479(10) 0.0164(2) Uani 1 1 d . . . C3 C 0.12080(4) 0.31337(4) 0.06691(10) 0.0153(2) Uani 1 1 d . . . C4 C 0.15886(4) 0.28777(5) 0.09781(10) 0.0149(2) Uani 1 1 d . . . C5 C 0.16598(5) 0.26003(5) -0.01967(9) 0.0163(2) Uani 1 1 d . . . H5A H 0.1951 0.2910 -0.0725 0.020 Uiso 1 1 calc R . . H5B H 0.1814 0.2345 0.0034 0.020 Uiso 1 1 calc R . . C6 C 0.21979(5) 0.33669(5) 0.13350(11) 0.0207(2) Uani 1 1 d . . . H6A H 0.2174 0.3557 0.2083 0.031 Uiso 1 1 calc R . . H6B H 0.2357 0.3649 0.0668 0.031 Uiso 1 1 calc R . . H6C H 0.2450 0.3205 0.1481 0.031 Uiso 1 1 calc R . . C7 C 0.11817(5) 0.35358(5) 0.14457(10) 0.0181(2) Uani 1 1 d . . . H7 H 0.1404 0.3645 0.2178 0.022 Uiso 1 1 calc R . . C8 C 0.08438(5) 0.37801(5) 0.11861(10) 0.0199(2) Uani 1 1 d . . . H8 H 0.0834 0.4051 0.1734 0.024 Uiso 1 1 calc R . . C9 C 0.05190(5) 0.36238(5) 0.01117(11) 0.0202(2) Uani 1 1 d . . . H9 H 0.0282 0.3785 -0.0074 0.024 Uiso 1 1 calc R . . C10 C 0.05415(5) 0.32343(5) -0.06840(10) 0.0185(2) Uani 1 1 d . . . H10 H 0.0324 0.3133 -0.1423 0.022 Uiso 1 1 calc R . . C11 C 0.13390(4) 0.24400(5) 0.20386(9) 0.0157(2) Uani 1 1 d . . . C12 C 0.16318(5) 0.21595(5) 0.24460(10) 0.0188(2) Uani 1 1 d . . . H12 H 0.1989 0.2252 0.2078 0.023 Uiso 1 1 calc R . . C13 C 0.14110(5) 0.17496(5) 0.33761(10) 0.0205(2) Uani 1 1 d . . . H13 H 0.1619 0.1568 0.3640 0.025 Uiso 1 1 calc R . . C14 C 0.08884(5) 0.16058(5) 0.39181(10) 0.0193(2) Uani 1 1 d . . . C15 C 0.05959(5) 0.18848(5) 0.35558(10) 0.0197(2) Uani 1 1 d . . . H15 H 0.0242 0.1796 0.3939 0.024 Uiso 1 1 calc R . . C16 C 0.08221(5) 0.22964(5) 0.26255(10) 0.0173(2) Uani 1 1 d . . . H16 H 0.0617 0.2485 0.2384 0.021 Uiso 1 1 calc R . . C17 C 0.12622(5) 0.20748(5) -0.21553(11) 0.0225(2) Uani 1 1 d . . . H17A H 0.0910 0.1849 -0.2636 0.034 Uiso 1 1 calc R . . H17B H 0.1444 0.1842 -0.1995 0.034 Uiso 1 1 calc R . . H17C H 0.1530 0.2421 -0.2616 0.034 Uiso 1 1 calc R . . C18 C 0.06374(5) 0.17227(5) -0.02898(11) 0.0206(2) Uani 1 1 d . . . H18A H 0.0302 0.1523 -0.0832 0.031 Uiso 1 1 calc R . . H18B H 0.0525 0.1846 0.0456 0.031 Uiso 1 1 calc R . . H18C H 0.0779 0.1461 -0.0071 0.031 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 0.0366(5) 0.0267(5) 0.0226(4) 0.0069(4) 0.0009(4) 0.0156(4) O2 0.0205(4) 0.0216(4) 0.0186(4) -0.0040(3) -0.0045(3) 0.0132(3) C2 0.0136(5) 0.0155(5) 0.0181(5) 0.0000(4) 0.0011(4) 0.0069(4) C1 0.0149(5) 0.0173(5) 0.0182(5) -0.0025(4) -0.0013(4) 0.0088(4) C3 0.0133(5) 0.0158(5) 0.0172(5) 0.0014(4) 0.0017(4) 0.0077(4) C4 0.0124(5) 0.0161(5) 0.0168(5) -0.0024(4) -0.0011(4) 0.0077(4) C5 0.0131(5) 0.0191(5) 0.0177(5) -0.0017(4) 0.0002(4) 0.0089(4) C6 0.0164(5) 0.0204(6) 0.0246(6) -0.0041(4) -0.0038(4) 0.0086(5) C7 0.0193(5) 0.0192(5) 0.0172(5) 0.0001(4) 0.0009(4) 0.0106(4) C8 0.0221(6) 0.0185(5) 0.0221(6) 0.0019(4) 0.0049(4) 0.0125(5) C9 0.0177(5) 0.0191(5) 0.0270(6) 0.0059(4) 0.0036(4) 0.0116(5) C10 0.0142(5) 0.0186(5) 0.0220(5) 0.0029(4) -0.0006(4) 0.0076(4) C11 0.0161(5) 0.0174(5) 0.0150(5) -0.0036(4) -0.0028(4) 0.0095(4) C12 0.0190(5) 0.0231(6) 0.0178(5) -0.0026(4) -0.0009(4) 0.0133(5) C13 0.0255(6) 0.0235(6) 0.0187(5) -0.0012(4) -0.0033(4) 0.0169(5) C14 0.0232(6) 0.0187(5) 0.0155(5) -0.0006(4) -0.0018(4) 0.0101(5) C15 0.0184(5) 0.0233(6) 0.0174(5) -0.0010(4) 0.0002(4) 0.0104(5) C16 0.0173(5) 0.0192(5) 0.0182(5) -0.0021(4) -0.0019(4) 0.0111(4) C17 0.0222(6) 0.0266(6) 0.0196(5) -0.0049(4) -0.0012(4) 0.0129(5) C18 0.0179(5) 0.0194(5) 0.0217(5) -0.0014(4) -0.0012(4) 0.0071(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 O1 C14 1.3843(14) . ? O1 H1 0.8500 . ? O2 C2 1.3706(13) . ? O2 C1 1.4592(13) . ? C2 C10 1.3990(15) . ? C2 C3 1.3999(15) . ? C1 C17 1.5167(15) . ? C1 C5 1.5243(15) . ? C1 C18 1.5266(16) . ? C3 C7 1.3990(15) . ? C3 C4 1.5235(15) . ? C4 C5 1.5398(14) . ? C4 C11 1.5409(15) . ? C4 C6 1.5467(15) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.3852(15) . ? C7 H7 0.9500 . ? C8 C9 1.3928(16) . ? C8 H8 0.9500 . ? C9 C10 1.3809(16) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.3932(15) . ? C11 C12 1.4016(15) . ? C12 C13 1.3906(16) . ? C12 H12 0.9500 . ? C13 C14 1.3845(16) . ? C13 H13 0.9500 . ? C14 C15 1.3831(16) . ? C15 C16 1.3939(15) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O1 H1 109.5 . . ? C2 O2 C1 117.45(8) . . ? O2 C2 C10 114.87(9) . . ? O2 C2 C3 124.44(9) . . ? C10 C2 C3 120.66(10) . . ? O2 C1 C17 104.95(9) . . ? O2 C1 C5 108.89(8) . . ? C17 C1 C5 109.61(9) . . ? O2 C1 C18 107.81(9) . . ? C17 C1 C18 110.44(9) . . ? C5 C1 C18 114.66(9) . . ? C7 C3 C2 117.35(10) . . ? C7 C3 C4 120.99(9) . . ? C2 C3 C4 121.64(9) . . ? C3 C4 C5 107.77(8) . . ? C3 C4 C11 112.03(8) . . ? C5 C4 C11 111.62(8) . . ? C3 C4 C6 109.54(9) . . ? C5 C4 C6 106.57(8) . . ? C11 C4 C6 109.15(8) . . ? C1 C5 C4 115.55(9) . . ? C1 C5 H5A 108.4 . . ? C4 C5 H5A 108.4 . . ? C1 C5 H5B 108.4 . . ? C4 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C3 122.41(10) . . ? C8 C7 H7 118.8 . . ? C3 C7 H7 118.8 . . ? C7 C8 C9 119.14(10) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 119.93(10) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C2 120.49(10) . . ? C9 C10 H10 119.8 . . ? C2 C10 H10 119.8 . . ? C16 C11 C12 116.83(10) . . ? C16 C11 C4 123.21(9) . . ? C12 C11 C4 119.96(9) . . ? C13 C12 C11 121.53(10) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C14 C13 C12 120.17(10) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 O1 118.32(10) . . ? C15 C14 C13 119.64(10) . . ? O1 C14 C13 122.04(10) . . ? C14 C15 C16 119.69(10) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C11 C16 C15 122.11(10) . . ? C11 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C1 C17 H17A 109.5 . . ? C1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C1 C18 H18A 109.5 . . ? C1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O2 C2 C10 -166.21(9) . . . . ? C1 O2 C2 C3 16.05(15) . . . . ? C2 O2 C1 C17 -159.31(9) . . . . ? C2 O2 C1 C5 -42.02(12) . . . . ? C2 O2 C1 C18 82.95(11) . . . . ? O2 C2 C3 C7 177.14(10) . . . . ? C10 C2 C3 C7 -0.48(16) . . . . ? O2 C2 C3 C4 -1.46(16) . . . . ? C10 C2 C3 C4 -179.08(10) . . . . ? C7 C3 C4 C5 -163.76(10) . . . . ? C2 C3 C4 C5 14.79(13) . . . . ? C7 C3 C4 C11 73.08(12) . . . . ? C2 C3 C4 C11 -108.37(11) . . . . ? C7 C3 C4 C6 -48.19(13) . . . . ? C2 C3 C4 C6 130.35(11) . . . . ? O2 C1 C5 C4 57.84(11) . . . . ? C17 C1 C5 C4 172.13(9) . . . . ? C18 C1 C5 C4 -63.01(12) . . . . ? C3 C4 C5 C1 -43.16(12) . . . . ? C11 C4 C5 C1 80.26(11) . . . . ? C6 C4 C5 C1 -160.66(9) . . . . ? C2 C3 C7 C8 0.85(16) . . . . ? C4 C3 C7 C8 179.45(10) . . . . ? C3 C7 C8 C9 -0.29(17) . . . . ? C7 C8 C9 C10 -0.65(16) . . . . ? C8 C9 C10 C2 1.01(16) . . . . ? O2 C2 C10 C9 -178.27(10) . . . . ? C3 C2 C10 C9 -0.44(16) . . . . ? C3 C4 C11 C16 0.63(14) . . . . ? C5 C4 C11 C16 -120.34(11) . . . . ? C6 C4 C11 C16 122.12(11) . . . . ? C3 C4 C11 C12 179.84(9) . . . . ? C5 C4 C11 C12 58.88(12) . . . . ? C6 C4 C11 C12 -58.66(12) . . . . ? C16 C11 C12 C13 1.17(16) . . . . ? C4 C11 C12 C13 -178.09(10) . . . . ? C11 C12 C13 C14 0.49(17) . . . . ? C12 C13 C14 C15 -1.99(17) . . . . ? C12 C13 C14 O1 177.99(10) . . . . ? O1 C14 C15 C16 -178.21(10) . . . . ? C13 C14 C15 C16 1.77(17) . . . . ? C12 C11 C16 C15 -1.40(16) . . . . ? C4 C11 C16 C15 177.83(10) . . . . ? C14 C15 C16 C11 -0.04(16) . . . . ? 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 O1 H1 O1 0.85 1.94 2.7855(9) 171.8 11_556 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.675 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.064 data_cmpnd02 _database_code_depnum_ccdc_archive 'CCDC 796806' #TrackingRef 'UWA_deposit_101014.cif' #data_gk260_299K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-p-Hydroxyphenyl-2,2,4-trimethylchroman isopropanol clathrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C18 H20 O2), C3 H8 O' _chemical_formula_sum 'C57 H68 O7' _chemical_formula_weight 865.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_int_tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 27.2014(10) _cell_length_b 27.2014 _cell_length_c 11.0239(3) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 120.0 _cell_volume 7064.0(3) _cell_formula_units_Z 6 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used 11301 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 32.18 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2796 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9023 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire3 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26572 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 32.27 _reflns_number_total 5279 _reflns_number_gt 3998 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury CSD v. 2.3 (2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1100P)^2^+3.8000P] 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 5279 _refine_ls_number_parameters 198 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1875 _refine_ls_wR_factor_gt 0.1786 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.008 _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 0.06662(7) 0.12469(6) 0.48197(12) 0.0710(4) Uani 1 1 d . . . H1 H 0.0841 0.1061 0.4860 0.107 Uiso 1 1 calc R . . O2 O 0.08768(4) 0.26271(4) -0.12617(9) 0.0464(2) Uani 1 1 d . . . C1 C 0.11078(5) 0.22651(5) -0.09332(11) 0.0373(3) Uani 1 1 d . . . C2 C 0.08782(5) 0.29877(5) -0.03952(11) 0.0370(3) Uani 1 1 d . . . C3 C 0.12023(5) 0.31345(5) 0.06639(11) 0.0349(2) Uani 1 1 d . . . C4 C 0.15780(5) 0.28840(5) 0.09669(11) 0.0338(2) Uani 1 1 d . . . C5 C 0.16449(5) 0.26098(6) -0.01958(11) 0.0369(3) Uani 1 1 d . . . H5A H 0.1925 0.2908 -0.0710 0.044 Uiso 1 1 calc R . . H5B H 0.1794 0.2364 0.0027 0.044 Uiso 1 1 calc R . . C6 C 0.21789(6) 0.33656(6) 0.13174(15) 0.0489(3) Uani 1 1 d . . . H6A H 0.2157 0.3549 0.2042 0.073 Uiso 1 1 calc R . . H6B H 0.2332 0.3637 0.0670 0.073 Uiso 1 1 calc R . . H6C H 0.2421 0.3209 0.1458 0.073 Uiso 1 1 calc R . . C7 C 0.11775(6) 0.35316(6) 0.14343(13) 0.0437(3) Uani 1 1 d . . . H7 H 0.1393 0.3639 0.2141 0.052 Uiso 1 1 calc R . . C8 C 0.08421(7) 0.37695(7) 0.11750(14) 0.0505(3) Uani 1 1 d . . . H8 H 0.0832 0.4031 0.1704 0.061 Uiso 1 1 calc R . . C9 C 0.05233(7) 0.36147(7) 0.01240(16) 0.0518(4) Uani 1 1 d . . . H9 H 0.0295 0.3770 -0.0054 0.062 Uiso 1 1 calc R . . C10 C 0.05422(6) 0.32298(6) -0.06643(14) 0.0460(3) Uani 1 1 d . . . H10 H 0.0331 0.3131 -0.1377 0.055 Uiso 1 1 calc R . . C11 C 0.13357(5) 0.24550(5) 0.20219(10) 0.0353(2) Uani 1 1 d . . . C12 C 0.16242(6) 0.21811(6) 0.24278(12) 0.0438(3) Uani 1 1 d . . . H12 H 0.1967 0.2267 0.2065 0.053 Uiso 1 1 calc R . . C13 C 0.14111(7) 0.17833(7) 0.33626(13) 0.0512(4) Uani 1 1 d . . . H13 H 0.1612 0.1608 0.3617 0.061 Uiso 1 1 calc R . . C14 C 0.09016(7) 0.16488(6) 0.39139(12) 0.0485(3) Uani 1 1 d . . . C15 C 0.06124(6) 0.19174(6) 0.35437(12) 0.0467(3) Uani 1 1 d . . . H15 H 0.0272 0.1833 0.3915 0.056 Uiso 1 1 calc R . . C16 C 0.08315(6) 0.23162(6) 0.26110(12) 0.0401(3) Uani 1 1 d . . . H16 H 0.0632 0.2496 0.2374 0.048 Uiso 1 1 calc R . . C17 C 0.12533(7) 0.20968(8) -0.21371(13) 0.0530(4) Uani 1 1 d . . . H17A H 0.0912 0.1879 -0.2599 0.080 Uiso 1 1 calc R . . H17B H 0.1431 0.1873 -0.1991 0.080 Uiso 1 1 calc R . . H17C H 0.1509 0.2432 -0.2581 0.080 Uiso 1 1 calc R . . C18 C 0.06435(6) 0.17464(6) -0.02861(13) 0.0477(3) Uani 1 1 d . . . H18A H 0.0558 0.1860 0.0473 0.072 Uiso 1 1 calc R . . H18B H 0.0771 0.1480 -0.0140 0.072 Uiso 1 1 calc R . . H18C H 0.0309 0.1572 -0.0783 0.072 Uiso 1 1 calc R . . O01 O -0.0143(4) 0.0070(5) 0.3734(6) 0.141(3) Uiso 0.33 1 d PD A -1 H01A H 0.0061 0.0399 0.4038 0.212 Uiso 0.33 1 calc PR A -1 C01 C -0.0078(3) 0.0098(4) 0.2553(7) 0.095(3) Uiso 0.33 1 d PD A -1 H01B H -0.0100 0.0436 0.2340 0.115 Uiso 0.33 1 calc PR A -1 C02 C -0.0537(4) -0.0353(4) 0.1802(9) 0.114(3) Uiso 0.33 1 d PD A -1 H02A H -0.0900 -0.0432 0.2108 0.170 Uiso 0.33 1 calc PR A -1 H02B H -0.0511 -0.0692 0.1839 0.170 Uiso 0.33 1 calc PR A -1 H02C H -0.0497 -0.0227 0.0976 0.170 Uiso 0.33 1 calc PR A -1 C03 C 0.0528(5) 0.0263(6) 0.2180(10) 0.128(3) Uiso 0.33 1 d PD A -1 H03A H 0.0793 0.0600 0.2606 0.192 Uiso 0.33 1 calc PR A -1 H03B H 0.0572 0.0332 0.1322 0.192 Uiso 0.33 1 calc PR A -1 H03C H 0.0598 -0.0040 0.2377 0.192 Uiso 0.33 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0976(10) 0.0668(8) 0.0508(6) 0.0185(6) 0.0076(6) 0.0428(8) O2 0.0522(6) 0.0510(5) 0.0437(5) -0.0073(4) -0.0127(4) 0.0316(5) C1 0.0374(6) 0.0399(6) 0.0364(6) -0.0034(4) -0.0013(4) 0.0206(5) C2 0.0332(5) 0.0364(6) 0.0418(6) 0.0035(4) 0.0004(4) 0.0177(5) C3 0.0341(5) 0.0351(5) 0.0379(6) 0.0027(4) 0.0024(4) 0.0190(5) C4 0.0300(5) 0.0373(6) 0.0357(5) -0.0028(4) -0.0019(4) 0.0181(4) C5 0.0321(5) 0.0434(6) 0.0370(6) -0.0012(5) 0.0024(4) 0.0202(5) C6 0.0363(6) 0.0470(7) 0.0583(8) -0.0076(6) -0.0090(6) 0.0171(6) C7 0.0514(7) 0.0439(7) 0.0416(6) 0.0003(5) 0.0028(5) 0.0282(6) C8 0.0587(8) 0.0473(7) 0.0567(8) 0.0055(6) 0.0122(7) 0.0348(7) C9 0.0479(7) 0.0510(8) 0.0691(9) 0.0146(7) 0.0092(7) 0.0341(7) C10 0.0386(6) 0.0460(7) 0.0559(8) 0.0077(6) -0.0042(5) 0.0232(6) C11 0.0376(6) 0.0395(6) 0.0324(5) -0.0042(4) -0.0039(4) 0.0220(5) C12 0.0490(7) 0.0540(8) 0.0403(6) -0.0022(5) -0.0029(5) 0.0347(6) C13 0.0696(9) 0.0583(8) 0.0431(7) -0.0003(6) -0.0078(6) 0.0451(8) C14 0.0657(9) 0.0478(7) 0.0343(6) 0.0006(5) -0.0021(6) 0.0299(7) C15 0.0495(7) 0.0520(8) 0.0386(6) 0.0028(5) 0.0045(5) 0.0255(6) C16 0.0419(6) 0.0463(7) 0.0376(6) 0.0014(5) 0.0010(5) 0.0262(5) C17 0.0573(9) 0.0618(9) 0.0407(7) -0.0095(6) 0.0006(6) 0.0303(7) C18 0.0432(7) 0.0426(7) 0.0481(7) -0.0021(5) -0.0007(5) 0.0146(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.3792(18) . ? O1 H1 0.8501 . ? O2 C2 1.3676(16) . ? O2 C1 1.4542(16) . ? C1 C5 1.5181(17) . ? C1 C17 1.5194(18) . ? C1 C18 1.5207(19) . ? C2 C3 1.3956(17) . ? C2 C10 1.3998(17) . ? C3 C7 1.4020(18) . ? C3 C4 1.5220(16) . ? C4 C5 1.5389(16) . ? C4 C11 1.5427(17) . ? C4 C6 1.5477(18) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.387(2) . ? C7 H7 0.9300 . ? C8 C9 1.381(2) . ? C8 H8 0.9300 . ? C9 C10 1.381(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C16 1.3882(17) . ? C11 C12 1.3985(17) . ? C12 C13 1.393(2) . ? C12 H12 0.9300 . ? C13 C14 1.385(2) . ? C13 H13 0.9300 . ? C14 C15 1.376(2) . ? C15 C16 1.3937(19) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O01 C01 1.311(9) . ? O01 H01A 0.8500 . ? C01 C02 1.489(10) . ? C01 C03 1.532(10) . ? C01 H01B 0.9800 . ? C02 H02A 0.9600 . ? C02 H02B 0.9600 . ? C02 H02C 0.9600 . ? C03 H03A 0.9600 . ? C03 H03B 0.9600 . ? C03 H03C 0.9600 . ? 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 C14 O1 H1 109.5 . . ? C2 O2 C1 117.67(9) . . ? O2 C1 C5 108.87(10) . . ? O2 C1 C17 104.62(11) . . ? C5 C1 C17 109.79(11) . . ? O2 C1 C18 107.79(11) . . ? C5 C1 C18 114.72(11) . . ? C17 C1 C18 110.54(12) . . ? O2 C2 C3 124.36(11) . . ? O2 C2 C10 114.90(12) . . ? C3 C2 C10 120.69(12) . . ? C2 C3 C7 117.41(11) . . ? C2 C3 C4 121.67(11) . . ? C7 C3 C4 120.90(11) . . ? C3 C4 C5 107.62(10) . . ? C3 C4 C11 112.05(9) . . ? C5 C4 C11 111.75(10) . . ? C3 C4 C6 109.71(10) . . ? C5 C4 C6 106.71(10) . . ? C11 C4 C6 108.85(10) . . ? C1 C5 C4 115.78(10) . . ? C1 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? C1 C5 H5B 108.3 . . ? C4 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C3 122.06(13) . . ? C8 C7 H7 119.0 . . ? C3 C7 H7 119.0 . . ? C9 C8 C7 119.35(14) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 120.23(13) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C2 120.25(14) . . ? C9 C10 H10 119.9 . . ? C2 C10 H10 119.9 . . ? C16 C11 C12 116.53(12) . . ? C16 C11 C4 123.29(10) . . ? C12 C11 C4 120.18(11) . . ? C13 C12 C11 121.60(13) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C14 C13 C12 120.17(13) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 O1 118.27(15) . . ? C15 C14 C13 119.46(13) . . ? O1 C14 C13 122.27(14) . . ? C14 C15 C16 119.77(13) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 122.46(12) . . ? C11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? C1 C17 H17A 109.5 . . ? C1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C1 C18 H18A 109.5 . . ? C1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C01 O01 H01A 109.5 . . ? O01 C01 C02 118.1(7) . . ? O01 C01 C03 112.2(6) . . ? C02 C01 C03 115.4(8) . . ? O01 C01 H01B 102.8 . . ? C02 C01 H01B 102.8 . . ? C03 C01 H01B 102.8 . . ? C01 C02 H02A 109.5 . . ? C01 C02 H02B 109.5 . . ? H02A C02 H02B 109.5 . . ? C01 C02 H02C 109.5 . . ? H02A C02 H02C 109.5 . . ? H02B C02 H02C 109.5 . . ? C01 C03 H03A 109.5 . . ? C01 C03 H03B 109.5 . . ? H03A C03 H03B 109.5 . . ? C01 C03 H03C 109.5 . . ? H03A C03 H03C 109.5 . . ? H03B C03 H03C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O2 C1 C5 -41.89(14) . . . . ? C2 O2 C1 C17 -159.19(12) . . . . ? C2 O2 C1 C18 83.13(13) . . . . ? C1 O2 C2 C3 16.29(18) . . . . ? C1 O2 C2 C10 -166.42(11) . . . . ? O2 C2 C3 C7 176.96(12) . . . . ? C10 C2 C3 C7 -0.18(19) . . . . ? O2 C2 C3 C4 -1.90(19) . . . . ? C10 C2 C3 C4 -179.03(11) . . . . ? C2 C3 C4 C5 14.97(15) . . . . ? C7 C3 C4 C5 -163.84(11) . . . . ? C2 C3 C4 C11 -108.27(13) . . . . ? C7 C3 C4 C11 72.92(14) . . . . ? C2 C3 C4 C6 130.71(13) . . . . ? C7 C3 C4 C6 -48.10(16) . . . . ? O2 C1 C5 C4 57.54(14) . . . . ? C17 C1 C5 C4 171.51(12) . . . . ? C18 C1 C5 C4 -63.31(15) . . . . ? C3 C4 C5 C1 -43.06(14) . . . . ? C11 C4 C5 C1 80.36(13) . . . . ? C6 C4 C5 C1 -160.76(11) . . . . ? C2 C3 C7 C8 0.6(2) . . . . ? C4 C3 C7 C8 179.50(12) . . . . ? C3 C7 C8 C9 -0.3(2) . . . . ? C7 C8 C9 C10 -0.5(2) . . . . ? C8 C9 C10 C2 0.9(2) . . . . ? O2 C2 C10 C9 -177.98(13) . . . . ? C3 C2 C10 C9 -0.6(2) . . . . ? C3 C4 C11 C16 0.35(16) . . . . ? C5 C4 C11 C16 -120.53(13) . . . . ? C6 C4 C11 C16 121.86(13) . . . . ? C3 C4 C11 C12 -179.98(11) . . . . ? C5 C4 C11 C12 59.14(14) . . . . ? C6 C4 C11 C12 -58.47(15) . . . . ? C16 C11 C12 C13 1.0(2) . . . . ? C4 C11 C12 C13 -178.73(12) . . . . ? C11 C12 C13 C14 0.1(2) . . . . ? C12 C13 C14 C15 -1.0(2) . . . . ? C12 C13 C14 O1 178.21(14) . . . . ? O1 C14 C15 C16 -178.50(13) . . . . ? C13 C14 C15 C16 0.7(2) . . . . ? C12 C11 C16 C15 -1.23(19) . . . . ? C4 C11 C16 C15 178.45(12) . . . . ? C14 C15 C16 C11 0.4(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 O1 H1 O1 0.85 2.12 2.9663(14) 173.2 11_556 O01 H01A O1 0.85 2.23 3.078(12) 174.7 . _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.453 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.050 data_cmpnd03 _database_code_depnum_ccdc_archive 'CCDC 796807' #TrackingRef 'UWA_deposit_101014.cif' #data_gk260_182K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-p-Hydroxyphenyl-2,2,4-trimethylchroman isopropanol clathrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C18 H20 O2), C3 H8 O' _chemical_formula_sum 'C57 H68 O7' _chemical_formula_weight 865.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_int_tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 27.0106(4) _cell_length_b 27.0106 _cell_length_c 10.9760(1) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 120.0 _cell_volume 6934.94(12) _cell_formula_units_Z 6 _cell_measurement_temperature 182(2) _cell_measurement_reflns_used 15935 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 32.18 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2796 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95155 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 182(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire3 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26137 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 32.24 _reflns_number_total 5148 _reflns_number_gt 4279 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury CSD v. 2.3 (2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^2^+9.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5148 _refine_ls_number_parameters 197 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1729 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.025 _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 O1 O 0.06564(6) 0.12353(6) 0.48350(11) 0.0476(3) Uani 1 1 d . . . H1 H 0.0869 0.1099 0.4985 0.071 Uiso 1 1 calc R . . O2 O 0.08808(4) 0.26311(5) -0.12821(9) 0.0314(2) Uani 1 1 d . . . C1 C 0.11093(6) 0.22621(6) -0.09441(11) 0.0268(2) Uani 1 1 d . . . C2 C 0.08824(5) 0.29935(6) -0.04081(11) 0.0263(2) Uani 1 1 d . . . C3 C 0.12078(5) 0.31390(5) 0.06614(11) 0.0253(2) Uani 1 1 d . . . C4 C 0.15851(5) 0.28845(6) 0.09654(11) 0.0246(2) Uani 1 1 d . . . C5 C 0.16528(5) 0.26079(6) -0.02036(11) 0.0267(2) Uani 1 1 d . . . H5A H 0.1941 0.2914 -0.0730 0.032 Uiso 1 1 calc R . . H5B H 0.1804 0.2354 0.0024 0.032 Uiso 1 1 calc R . . C6 C 0.21893(6) 0.33685(7) 0.13163(14) 0.0338(3) Uani 1 1 d . . . H6A H 0.2167 0.3557 0.2060 0.051 Uiso 1 1 calc R . . H6B H 0.2346 0.3648 0.0653 0.051 Uiso 1 1 calc R . . H6C H 0.2439 0.3207 0.1459 0.051 Uiso 1 1 calc R . . C7 C 0.11816(6) 0.35377(6) 0.14394(12) 0.0304(3) Uani 1 1 d . . . H7 H 0.1403 0.3647 0.2165 0.036 Uiso 1 1 calc R . . C8 C 0.08434(7) 0.37765(7) 0.11821(13) 0.0342(3) Uani 1 1 d . . . H8 H 0.0832 0.4043 0.1729 0.041 Uiso 1 1 calc R . . C9 C 0.05214(6) 0.36226(7) 0.01178(14) 0.0346(3) Uani 1 1 d . . . H9 H 0.0287 0.3783 -0.0063 0.042 Uiso 1 1 calc R . . C10 C 0.05424(6) 0.32371(6) -0.06762(13) 0.0309(3) Uani 1 1 d . . . H10 H 0.0325 0.3136 -0.1408 0.037 Uiso 1 1 calc R . . C11 C 0.13402(5) 0.24536(6) 0.20268(11) 0.0254(2) Uani 1 1 d . . . C12 C 0.16289(6) 0.21748(6) 0.24336(12) 0.0308(3) Uani 1 1 d . . . H12 H 0.1981 0.2261 0.2061 0.037 Uiso 1 1 calc R . . C13 C 0.14126(7) 0.17734(7) 0.33734(13) 0.0352(3) Uani 1 1 d . . . H13 H 0.1617 0.1591 0.3635 0.042 Uiso 1 1 calc R . . C14 C 0.08981(7) 0.16404(7) 0.39256(12) 0.0341(3) Uani 1 1 d . . . C15 C 0.06089(6) 0.19156(7) 0.35551(12) 0.0333(3) Uani 1 1 d . . . H15 H 0.0260 0.1832 0.3939 0.040 Uiso 1 1 calc R . . C16 C 0.08300(6) 0.23164(6) 0.26164(12) 0.0288(3) Uani 1 1 d . . . H16 H 0.0627 0.2502 0.2370 0.035 Uiso 1 1 calc R . . C17 C 0.12542(7) 0.20869(7) -0.21501(12) 0.0357(3) Uani 1 1 d . . . H17A H 0.0903 0.1863 -0.2623 0.054 Uiso 1 1 calc R . . H17B H 0.1434 0.1855 -0.1994 0.054 Uiso 1 1 calc R . . H17C H 0.1519 0.2430 -0.2610 0.054 Uiso 1 1 calc R . . C18 C 0.06390(6) 0.17436(6) -0.02873(13) 0.0331(3) Uani 1 1 d . . . H18A H 0.0554 0.1864 0.0490 0.050 Uiso 1 1 calc R . . H18B H 0.0766 0.1467 -0.0135 0.050 Uiso 1 1 calc R . . H18C H 0.0294 0.1566 -0.0794 0.050 Uiso 1 1 calc R . . O01 O -0.0137(3) 0.0007(4) 0.3750(4) 0.0712(16) Uiso 0.33 1 d PD A -1 H01A H 0.0061 0.0324 0.4116 0.107 Uiso 0.33 1 calc PR A -1 C01 C -0.0098(2) 0.0093(3) 0.2568(5) 0.0508(13) Uiso 0.33 1 d PD A -1 H01B H -0.0090 0.0463 0.2442 0.061 Uiso 0.33 1 calc PR A -1 C02 C -0.0534(4) -0.0316(4) 0.1725(7) 0.075(2) Uiso 0.33 1 d PD A -1 H02A H -0.0914 -0.0409 0.2012 0.112 Uiso 0.33 1 calc PR A -1 H02B H -0.0509 -0.0666 0.1692 0.112 Uiso 0.33 1 calc PR A -1 H02C H -0.0468 -0.0147 0.0910 0.112 Uiso 0.33 1 calc PR A -1 C03 C 0.0518(3) 0.0202(4) 0.2131(8) 0.075(2) Uiso 0.33 1 d PD A -1 H03A H 0.0820 0.0546 0.2530 0.113 Uiso 0.33 1 calc PR A -1 H03B H 0.0552 0.0255 0.1245 0.113 Uiso 0.33 1 calc PR A -1 H03C H 0.0558 -0.0128 0.2352 0.113 Uiso 0.33 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0610(8) 0.0504(7) 0.0338(6) 0.0139(5) 0.0055(5) 0.0296(6) O2 0.0347(5) 0.0399(5) 0.0264(4) -0.0040(4) -0.0062(4) 0.0236(4) C1 0.0274(6) 0.0338(6) 0.0226(5) -0.0016(4) 0.0000(4) 0.0177(5) C2 0.0239(5) 0.0307(6) 0.0257(5) 0.0026(4) 0.0016(4) 0.0147(5) C3 0.0244(5) 0.0303(6) 0.0238(5) 0.0022(4) 0.0023(4) 0.0156(5) C4 0.0222(5) 0.0311(6) 0.0226(5) -0.0016(4) -0.0010(4) 0.0150(5) C5 0.0238(5) 0.0357(6) 0.0234(5) -0.0007(4) 0.0020(4) 0.0170(5) C6 0.0256(6) 0.0367(7) 0.0370(7) -0.0045(5) -0.0045(5) 0.0141(5) C7 0.0349(6) 0.0347(7) 0.0258(6) 0.0010(5) 0.0028(5) 0.0206(6) C8 0.0397(7) 0.0361(7) 0.0343(7) 0.0040(5) 0.0081(5) 0.0247(6) C9 0.0324(7) 0.0372(7) 0.0417(7) 0.0098(6) 0.0064(5) 0.0231(6) C10 0.0263(6) 0.0352(7) 0.0332(6) 0.0063(5) -0.0004(5) 0.0168(5) C11 0.0266(6) 0.0320(6) 0.0206(5) -0.0023(4) -0.0015(4) 0.0168(5) C12 0.0350(7) 0.0404(7) 0.0255(6) -0.0014(5) -0.0008(5) 0.0252(6) C13 0.0468(8) 0.0427(8) 0.0277(6) 0.0001(5) -0.0032(5) 0.0309(7) C14 0.0443(8) 0.0363(7) 0.0225(5) 0.0009(5) -0.0007(5) 0.0208(6) C15 0.0340(7) 0.0416(7) 0.0246(6) 0.0026(5) 0.0029(5) 0.0192(6) C16 0.0288(6) 0.0375(7) 0.0237(5) 0.0008(5) 0.0006(4) 0.0192(5) C17 0.0389(7) 0.0467(8) 0.0247(6) -0.0055(5) 0.0007(5) 0.0237(6) C18 0.0300(6) 0.0356(7) 0.0298(6) -0.0010(5) 0.0001(5) 0.0135(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.3804(18) . ? O1 H1 0.8400 . ? O2 C2 1.3690(16) . ? O2 C1 1.4582(16) . ? C1 C17 1.5214(18) . ? C1 C18 1.522(2) . ? C1 C5 1.5221(18) . ? C2 C3 1.3998(17) . ? C2 C10 1.4027(18) . ? C3 C7 1.4036(18) . ? C3 C4 1.5241(17) . ? C4 C5 1.5410(17) . ? C4 C11 1.5426(18) . ? C4 C6 1.5452(18) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.3856(19) . ? C7 H7 0.9500 . ? C8 C9 1.390(2) . ? C8 H8 0.9500 . ? C9 C10 1.381(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.3945(17) . ? C11 C12 1.4006(18) . ? C12 C13 1.395(2) . ? C12 H12 0.9500 . ? C13 C14 1.389(2) . ? C13 H13 0.9500 . ? C14 C15 1.382(2) . ? C15 C16 1.3941(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O01 C01 1.313(7) . ? O01 H01A 0.8500 . ? C01 C02 1.471(8) . ? C01 C03 1.611(8) . ? C01 H01B 1.0000 . ? C02 H02A 0.9800 . ? C02 H02B 0.9800 . ? C02 H02C 0.9800 . ? C03 H03A 0.9800 . ? C03 H03B 0.9800 . ? C03 H03C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O1 H1 109.5 . . ? C2 O2 C1 117.34(10) . . ? O2 C1 C17 104.70(10) . . ? O2 C1 C18 107.80(11) . . ? C17 C1 C18 110.62(12) . . ? O2 C1 C5 108.93(11) . . ? C17 C1 C5 109.65(11) . . ? C18 C1 C5 114.64(11) . . ? O2 C2 C3 124.44(11) . . ? O2 C2 C10 114.82(11) . . ? C3 C2 C10 120.70(12) . . ? C2 C3 C7 117.40(12) . . ? C2 C3 C4 121.63(11) . . ? C7 C3 C4 120.95(11) . . ? C3 C4 C5 107.73(10) . . ? C3 C4 C11 112.00(10) . . ? C5 C4 C11 111.90(10) . . ? C3 C4 C6 109.55(11) . . ? C5 C4 C6 106.65(10) . . ? C11 C4 C6 108.85(10) . . ? C1 C5 C4 115.48(10) . . ? C1 C5 H5A 108.4 . . ? C4 C5 H5A 108.4 . . ? C1 C5 H5B 108.4 . . ? C4 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C3 122.08(13) . . ? C8 C7 H7 119.0 . . ? C3 C7 H7 119.0 . . ? C7 C8 C9 119.44(13) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 120.04(13) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C2 120.32(13) . . ? C9 C10 H10 119.8 . . ? C2 C10 H10 119.8 . . ? C16 C11 C12 116.81(12) . . ? C16 C11 C4 123.01(11) . . ? C12 C11 C4 120.17(11) . . ? C13 C12 C11 121.60(13) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C14 C13 C12 119.98(13) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? O1 C14 C15 117.96(14) . . ? O1 C14 C13 122.42(14) . . ? C15 C14 C13 119.62(13) . . ? C14 C15 C16 119.82(13) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 122.15(12) . . ? C11 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C1 C17 H17A 109.5 . . ? C1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C1 C18 H18A 109.5 . . ? C1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C01 O01 H01A 109.5 . . ? O01 C01 C02 121.7(6) . . ? O01 C01 C03 108.1(4) . . ? C02 C01 C03 108.4(6) . . ? O01 C01 H01B 105.9 . . ? C02 C01 H01B 105.9 . . ? C03 C01 H01B 105.9 . . ? C01 C02 H02A 109.5 . . ? C01 C02 H02B 109.5 . . ? H02A C02 H02B 109.5 . . ? C01 C02 H02C 109.5 . . ? H02A C02 H02C 109.5 . . ? H02B C02 H02C 109.5 . . ? C01 C03 H03A 109.5 . . ? C01 C03 H03B 109.5 . . ? H03A C03 H03B 109.5 . . ? C01 C03 H03C 109.5 . . ? H03A C03 H03C 109.5 . . ? H03B C03 H03C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O2 C1 C17 -159.76(11) . . . . ? C2 O2 C1 C18 82.43(14) . . . . ? C2 O2 C1 C5 -42.54(14) . . . . ? C1 O2 C2 C3 16.64(18) . . . . ? C1 O2 C2 C10 -165.70(11) . . . . ? O2 C2 C3 C7 177.11(12) . . . . ? C10 C2 C3 C7 -0.42(19) . . . . ? O2 C2 C3 C4 -1.8(2) . . . . ? C10 C2 C3 C4 -179.36(12) . . . . ? C2 C3 C4 C5 14.79(16) . . . . ? C7 C3 C4 C5 -164.11(12) . . . . ? C2 C3 C4 C11 -108.69(13) . . . . ? C7 C3 C4 C11 72.41(15) . . . . ? C2 C3 C4 C6 130.43(13) . . . . ? C7 C3 C4 C6 -48.47(16) . . . . ? O2 C1 C5 C4 58.01(14) . . . . ? C17 C1 C5 C4 172.04(12) . . . . ? C18 C1 C5 C4 -62.85(15) . . . . ? C3 C4 C5 C1 -43.03(15) . . . . ? C11 C4 C5 C1 80.50(13) . . . . ? C6 C4 C5 C1 -160.57(11) . . . . ? C2 C3 C7 C8 0.9(2) . . . . ? C4 C3 C7 C8 179.81(13) . . . . ? C3 C7 C8 C9 -0.5(2) . . . . ? C7 C8 C9 C10 -0.3(2) . . . . ? C8 C9 C10 C2 0.8(2) . . . . ? O2 C2 C10 C9 -178.13(12) . . . . ? C3 C2 C10 C9 -0.4(2) . . . . ? C3 C4 C11 C16 0.55(17) . . . . ? C5 C4 C11 C16 -120.55(13) . . . . ? C6 C4 C11 C16 121.83(13) . . . . ? C3 C4 C11 C12 179.88(12) . . . . ? C5 C4 C11 C12 58.79(15) . . . . ? C6 C4 C11 C12 -58.84(15) . . . . ? C16 C11 C12 C13 0.8(2) . . . . ? C4 C11 C12 C13 -178.57(12) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? C12 C13 C14 O1 178.12(14) . . . . ? C12 C13 C14 C15 -1.3(2) . . . . ? O1 C14 C15 C16 -178.25(13) . . . . ? C13 C14 C15 C16 1.2(2) . . . . ? C12 C11 C16 C15 -0.9(2) . . . . ? C4 C11 C16 C15 178.44(12) . . . . ? C14 C15 C16 C11 -0.1(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 O1 H1 O1 0.84 2.09 2.9141(13) 166.0 11_556 O01 H01A O1 0.85 2.30 3.148(9) 171.7 . _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.683 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.059 data_cmpnd04 _database_code_depnum_ccdc_archive 'CCDC 796808' #TrackingRef 'UWA_deposit_101014.cif' #data_gk260_100K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-p-Hydroxyphenyl-2,2,4-trimethylchroman isopropanol clathrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C18 H20 O2), C3 H8 O' _chemical_formula_sum 'C57 H68 O7' _chemical_formula_weight 865.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_int_tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 53.9718(10) _cell_length_b 53.9718 _cell_length_c 11.0324(3) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 120.0 _cell_volume 27831.3(9) _cell_formula_units_Z 24 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 45480 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 28.23 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 11184 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98262 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire3 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 64482 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -70 _diffrn_reflns_limit_h_max 70 _diffrn_reflns_limit_k_min -69 _diffrn_reflns_limit_k_max 70 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 28.32 _reflns_number_total 14214 _reflns_number_gt 11522 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury CSD v. 2.3 (2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0600P)^2^+52.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14214 _refine_ls_number_parameters 793 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 O1A O 0.26576(2) 0.13584(2) 0.18391(10) 0.0208(2) Uani 1 1 d . . . H1A H 0.2685 0.1521 0.1620 0.031 Uiso 1 1 calc R . . O2A O 0.19901(2) 0.12664(2) 0.80445(9) 0.0182(2) Uani 1 1 d . . . C1A C 0.21855(3) 0.11653(3) 0.76903(13) 0.0167(3) Uani 1 1 d . . . C2A C 0.18039(3) 0.12587(3) 0.71760(13) 0.0162(3) Uani 1 1 d . . . C3A C 0.17327(3) 0.10933(3) 0.61186(13) 0.0155(3) Uani 1 1 d . . . C4A C 0.18691(3) 0.09121(3) 0.58174(13) 0.0151(3) Uani 1 1 d . . . C5A C 0.20178(3) 0.08893(3) 0.69695(13) 0.0161(3) Uani 1 1 d . . . H5AA H 0.1870 0.0743 0.7507 0.019 Uiso 1 1 calc R . . H5AB H 0.2150 0.0821 0.6734 0.019 Uiso 1 1 calc R . . C6A C 0.16330(3) 0.06047(3) 0.54839(14) 0.0195(3) Uani 1 1 d . . . H6AA H 0.1499 0.0522 0.6162 0.029 Uiso 1 1 calc R . . H6AB H 0.1721 0.0487 0.5316 0.029 Uiso 1 1 calc R . . H6AC H 0.1530 0.0611 0.4763 0.029 Uiso 1 1 calc R . . C7A C 0.15301(3) 0.10989(3) 0.53409(14) 0.0177(3) Uani 1 1 d . . . H7A H 0.1476 0.0985 0.4628 0.021 Uiso 1 1 calc R . . C8A C 0.14060(3) 0.12649(3) 0.55783(14) 0.0202(3) Uani 1 1 d . . . H8A H 0.1272 0.1267 0.5028 0.024 Uiso 1 1 calc R . . C9A C 0.14801(3) 0.14283(3) 0.66341(15) 0.0202(3) Uani 1 1 d . . . H9A H 0.1397 0.1543 0.6806 0.024 Uiso 1 1 calc R . . C10A C 0.16754(3) 0.14228(3) 0.74334(14) 0.0192(3) Uani 1 1 d . . . H10A H 0.1722 0.1531 0.8161 0.023 Uiso 1 1 calc R . . C11A C 0.20779(3) 0.10382(3) 0.47392(13) 0.0153(3) Uani 1 1 d . . . C12A C 0.22325(3) 0.09069(3) 0.43563(13) 0.0173(3) Uani 1 1 d . . . H12A H 0.2207 0.0741 0.4768 0.021 Uiso 1 1 calc R . . C13A C 0.24222(3) 0.10134(3) 0.33919(14) 0.0186(3) Uani 1 1 d . . . H13A H 0.2525 0.0921 0.3152 0.022 Uiso 1 1 calc R . . C14A C 0.24619(3) 0.12554(3) 0.27758(13) 0.0174(3) Uani 1 1 d . . . C15A C 0.23117(3) 0.13893(3) 0.31303(13) 0.0170(3) Uani 1 1 d . . . H15A H 0.2337 0.1554 0.2712 0.020 Uiso 1 1 calc R . . C16A C 0.21223(3) 0.12803(3) 0.41046(13) 0.0161(3) Uani 1 1 d . . . H16A H 0.2021 0.1374 0.4343 0.019 Uiso 1 1 calc R . . C17A C 0.22872(3) 0.11043(3) 0.88830(14) 0.0213(3) Uani 1 1 d . . . H17A H 0.2396 0.1283 0.9338 0.032 Uiso 1 1 calc R . . H17B H 0.2409 0.1022 0.8717 0.032 Uiso 1 1 calc R . . H17C H 0.2121 0.0969 0.9362 0.032 Uiso 1 1 calc R . . C18A C 0.24357(3) 0.14072(3) 0.70088(14) 0.0200(3) Uani 1 1 d . . . H18A H 0.2532 0.1576 0.7534 0.030 Uiso 1 1 calc R . . H18B H 0.2364 0.1455 0.6281 0.030 Uiso 1 1 calc R . . H18C H 0.2572 0.1346 0.6773 0.030 Uiso 1 1 calc R . . O1B O 0.33783(2) 0.22428(2) 0.17295(10) 0.0246(3) Uani 1 1 d . . . H1B H 0.3474 0.2168 0.1458 0.037 Uiso 1 1 calc R . . O2B O 0.41452(2) 0.28700(2) 0.78831(9) 0.0187(2) Uani 1 1 d . . . C1B C 0.38446(3) 0.26968(3) 0.75489(13) 0.0168(3) Uani 1 1 d . . . C2B C 0.43295(3) 0.30442(3) 0.70015(13) 0.0160(3) Uani 1 1 d . . . C3B C 0.42432(3) 0.31163(3) 0.59220(13) 0.0156(3) Uani 1 1 d . . . C4B C 0.39299(3) 0.30216(3) 0.56731(13) 0.0148(3) Uani 1 1 d . . . C5B C 0.37576(3) 0.28843(3) 0.68453(13) 0.0162(3) Uani 1 1 d . . . H5BA H 0.3777 0.3039 0.7387 0.019 Uiso 1 1 calc R . . H5BB H 0.3553 0.2767 0.6628 0.019 Uiso 1 1 calc R . . C6B C 0.39059(3) 0.32913(3) 0.54204(14) 0.0187(3) Uani 1 1 d . . . H6BA H 0.4013 0.3386 0.4683 0.028 Uiso 1 1 calc R . . H6BB H 0.3985 0.3423 0.6107 0.028 Uiso 1 1 calc R . . H6BC H 0.3704 0.3235 0.5311 0.028 Uiso 1 1 calc R . . C7B C 0.44588(3) 0.33031(3) 0.51266(14) 0.0187(3) Uani 1 1 d . . . H7B H 0.4406 0.3354 0.4386 0.022 Uiso 1 1 calc R . . C8B C 0.47470(3) 0.34157(3) 0.53869(14) 0.0207(3) Uani 1 1 d . . . H8B H 0.4888 0.3540 0.4826 0.025 Uiso 1 1 calc R . . C9B C 0.48277(3) 0.33454(3) 0.64741(15) 0.0203(3) Uani 1 1 d . . . H9B H 0.5025 0.3424 0.6665 0.024 Uiso 1 1 calc R . . C10B C 0.46198(3) 0.31604(3) 0.72767(14) 0.0187(3) Uani 1 1 d . . . H10B H 0.4675 0.3112 0.8018 0.022 Uiso 1 1 calc R . . C11B C 0.38016(3) 0.28159(3) 0.45830(13) 0.0160(3) Uani 1 1 d . . . C12B C 0.35218(3) 0.27332(3) 0.42255(13) 0.0183(3) Uani 1 1 d . . . H12B H 0.3420 0.2807 0.4653 0.022 Uiso 1 1 calc R . . C13B C 0.33880(3) 0.25468(3) 0.32691(14) 0.0198(3) Uani 1 1 d . . . H13B H 0.3199 0.2498 0.3040 0.024 Uiso 1 1 calc R . . C14B C 0.35295(3) 0.24315(3) 0.26484(14) 0.0195(3) Uani 1 1 d . . . C15B C 0.38064(3) 0.25077(3) 0.29694(14) 0.0204(3) Uani 1 1 d . . . H15B H 0.3905 0.2430 0.2544 0.025 Uiso 1 1 calc R . . C16B C 0.39417(3) 0.27015(3) 0.39323(13) 0.0183(3) Uani 1 1 d . . . H16B H 0.4133 0.2755 0.4141 0.022 Uiso 1 1 calc R . . C17B C 0.36847(3) 0.26073(3) 0.87498(14) 0.0213(3) Uani 1 1 d . . . H17D H 0.3711 0.2777 0.9183 0.032 Uiso 1 1 calc R . . H17E H 0.3760 0.2508 0.9243 0.032 Uiso 1 1 calc R . . H17F H 0.3480 0.2479 0.8597 0.032 Uiso 1 1 calc R . . C18B C 0.38089(4) 0.24355(3) 0.68543(14) 0.0220(3) Uani 1 1 d . . . H18D H 0.3870 0.2328 0.7367 0.033 Uiso 1 1 calc R . . H18E H 0.3926 0.2498 0.6118 0.033 Uiso 1 1 calc R . . H18F H 0.3607 0.2313 0.6633 0.033 Uiso 1 1 calc R . . O1C O 0.38548(2) 0.14173(2) 0.19376(10) 0.0218(2) Uani 1 1 d . . . H1C H 0.3674 0.1329 0.1865 0.033 Uiso 1 1 calc R . . O2C O 0.38362(2) 0.07726(2) 0.81215(9) 0.0173(2) Uani 1 1 d . . . C1C C 0.39680(3) 0.10719(3) 0.77500(13) 0.0167(3) Uani 1 1 d . . . C2C C 0.38158(3) 0.05807(3) 0.72566(13) 0.0154(3) Uani 1 1 d . . . C3C C 0.39795(3) 0.06560(3) 0.61937(13) 0.0151(3) Uani 1 1 d . . . C4C C 0.41949(3) 0.09662(3) 0.58903(13) 0.0155(3) Uani 1 1 d . . . C5C C 0.42393(3) 0.11482(3) 0.70338(13) 0.0164(3) Uani 1 1 d . . . H5CA H 0.4375 0.1129 0.7577 0.020 Uiso 1 1 calc R . . H5CB H 0.4330 0.1352 0.6789 0.020 Uiso 1 1 calc R . . C6C C 0.44884(3) 0.09949(3) 0.55845(14) 0.0202(3) Uani 1 1 d . . . H6CA H 0.4552 0.0925 0.6268 0.030 Uiso 1 1 calc R . . H6CB H 0.4629 0.1196 0.5432 0.030 Uiso 1 1 calc R . . H6CC H 0.4470 0.0882 0.4860 0.030 Uiso 1 1 calc R . . C7C C 0.39406(3) 0.04337(3) 0.54172(14) 0.0175(3) Uani 1 1 d . . . H7C H 0.4051 0.0479 0.4696 0.021 Uiso 1 1 calc R . . C8C C 0.37466(3) 0.01495(3) 0.56671(14) 0.0192(3) Uani 1 1 d . . . H8C H 0.3723 0.0004 0.5118 0.023 Uiso 1 1 calc R . . C9C C 0.35865(3) 0.00795(3) 0.67296(14) 0.0193(3) Uani 1 1 d . . . H9C H 0.3453 -0.0115 0.6909 0.023 Uiso 1 1 calc R . . C10C C 0.36222(3) 0.02935(3) 0.75254(14) 0.0176(3) Uani 1 1 d . . . H10C H 0.3515 0.0245 0.8257 0.021 Uiso 1 1 calc R . . C11C C 0.40968(3) 0.10757(3) 0.48063(13) 0.0153(3) Uani 1 1 d . . . C12C C 0.42727(3) 0.13555(3) 0.43900(14) 0.0183(3) Uani 1 1 d . . . H12C H 0.4452 0.1472 0.4773 0.022 Uiso 1 1 calc R . . C13C C 0.41921(3) 0.14666(3) 0.34349(14) 0.0190(3) Uani 1 1 d . . . H13C H 0.4316 0.1657 0.3167 0.023 Uiso 1 1 calc R . . C14C C 0.39304(3) 0.12988(3) 0.28710(13) 0.0175(3) Uani 1 1 d . . . C15C C 0.37510(3) 0.10198(3) 0.32628(13) 0.0179(3) Uani 1 1 d . . . H15C H 0.3571 0.0904 0.2879 0.021 Uiso 1 1 calc R . . C16C C 0.38358(3) 0.09112(3) 0.42191(13) 0.0165(3) Uani 1 1 d . . . H16C H 0.3713 0.0720 0.4479 0.020 Uiso 1 1 calc R . . C17C C 0.40498(3) 0.12417(3) 0.89258(14) 0.0215(3) Uani 1 1 d . . . H17G H 0.3876 0.1194 0.9386 0.032 Uiso 1 1 calc R . . H17H H 0.4153 0.1447 0.8741 0.032 Uiso 1 1 calc R . . H17I H 0.4172 0.1193 0.9407 0.032 Uiso 1 1 calc R . . C18C C 0.37436(3) 0.11101(3) 0.70678(14) 0.0197(3) Uani 1 1 d . . . H18G H 0.3579 0.1057 0.7597 0.030 Uiso 1 1 calc R . . H18H H 0.3682 0.0988 0.6347 0.030 Uiso 1 1 calc R . . H18I H 0.3826 0.1310 0.6821 0.030 Uiso 1 1 calc R . . O1D O 0.06035(3) 0.03377(2) 0.48751(10) 0.0250(3) Uani 1 1 d . . . H1D H 0.0505 0.0421 0.4940 0.037 Uiso 1 1 calc R . . O2D O 0.13182(2) 0.04826(2) -0.11988(9) 0.0196(2) Uani 1 1 d . . . C1D C 0.11190(3) 0.05815(3) -0.08801(13) 0.0175(3) Uani 1 1 d . . . C2D C 0.15064(3) 0.04992(3) -0.03211(13) 0.0168(3) Uani 1 1 d . . . C3D C 0.15695(3) 0.06637(3) 0.07361(13) 0.0157(3) Uani 1 1 d . . . C4D C 0.14232(3) 0.08364(3) 0.10228(13) 0.0153(3) Uani 1 1 d . . . C5D C 0.12778(3) 0.08571(3) -0.01479(13) 0.0163(3) Uani 1 1 d . . . H5DA H 0.1141 0.0921 0.0072 0.020 Uiso 1 1 calc R . . H5DB H 0.1426 0.1006 -0.0673 0.020 Uiso 1 1 calc R . . C6D C 0.16508(3) 0.11461(3) 0.13657(14) 0.0188(3) Uani 1 1 d . . . H6DA H 0.1750 0.1144 0.2107 0.028 Uiso 1 1 calc R . . H6DB H 0.1557 0.1259 0.1503 0.028 Uiso 1 1 calc R . . H6DC H 0.1790 0.1231 0.0705 0.028 Uiso 1 1 calc R . . C7D C 0.17774(3) 0.06692(3) 0.15167(13) 0.0181(3) Uani 1 1 d . . . H7D H 0.1825 0.0780 0.2236 0.022 Uiso 1 1 calc R . . C8D C 0.19160(3) 0.05172(3) 0.12689(14) 0.0204(3) Uani 1 1 d . . . H8D H 0.2056 0.0524 0.1814 0.025 Uiso 1 1 calc R . . C9D C 0.18489(3) 0.03539(3) 0.02157(14) 0.0206(3) Uani 1 1 d . . . H9D H 0.1942 0.0248 0.0041 0.025 Uiso 1 1 calc R . . C10D C 0.16463(3) 0.03459(3) -0.05760(14) 0.0194(3) Uani 1 1 d . . . H10D H 0.1602 0.0236 -0.1298 0.023 Uiso 1 1 calc R . . C11D C 0.12090(3) 0.07051(3) 0.20797(13) 0.0152(3) Uani 1 1 d . . . C12D C 0.10591(3) 0.08380(3) 0.24921(13) 0.0170(3) Uani 1 1 d . . . H12D H 0.1095 0.1012 0.2126 0.020 Uiso 1 1 calc R . . C13D C 0.08591(3) 0.07220(3) 0.34246(13) 0.0184(3) Uani 1 1 d . . . H13D H 0.0761 0.0817 0.3690 0.022 Uiso 1 1 calc R . . C14D C 0.08041(3) 0.04666(3) 0.39661(13) 0.0185(3) Uani 1 1 d . . . C15D C 0.09521(3) 0.03324(3) 0.35863(14) 0.0194(3) Uani 1 1 d . . . H15D H 0.0917 0.0159 0.3959 0.023 Uiso 1 1 calc R . . C16D C 0.11520(3) 0.04519(3) 0.26575(13) 0.0173(3) Uani 1 1 d . . . H16D H 0.1253 0.0358 0.2409 0.021 Uiso 1 1 calc R . . C17D C 0.10258(4) 0.06439(4) -0.20898(14) 0.0222(3) Uani 1 1 d . . . H17J H 0.0924 0.0467 -0.2560 0.033 Uiso 1 1 calc R . . H17K H 0.1195 0.0784 -0.2542 0.033 Uiso 1 1 calc R . . H17L H 0.0899 0.0722 -0.1947 0.033 Uiso 1 1 calc R . . C18D C 0.08652(3) 0.03373(3) -0.02275(14) 0.0209(3) Uani 1 1 d . . . H18J H 0.0776 0.0169 -0.0755 0.031 Uiso 1 1 calc R . . H18K H 0.0725 0.0396 -0.0027 0.031 Uiso 1 1 calc R . . H18L H 0.0932 0.0291 0.0519 0.031 Uiso 1 1 calc R . . O10 O 0.31349(3) 0.13969(3) 0.29187(13) 0.0420(4) Uani 1 1 d . . . H10 H 0.3005 0.1422 0.2600 0.063 Uiso 1 1 calc R . . C11 C 0.32966(6) 0.16188(7) 0.3677(3) 0.0696(9) Uani 1 1 d . . . H11 H 0.3425 0.1774 0.3107 0.083 Uiso 1 1 calc R . . C12 C 0.34991(4) 0.15784(5) 0.44261(19) 0.0404(5) Uani 1 1 d . . . H121 H 0.3589 0.1495 0.3931 0.061 Uiso 1 1 calc R . . H122 H 0.3396 0.1450 0.5102 0.061 Uiso 1 1 calc R . . H123 H 0.3646 0.1764 0.4744 0.061 Uiso 1 1 calc R . . C13 C 0.31432(4) 0.17476(4) 0.43247(18) 0.0357(4) Uani 1 1 d . . . H131 H 0.3016 0.1769 0.3757 0.054 Uiso 1 1 calc R . . H132 H 0.3283 0.1936 0.4646 0.054 Uiso 1 1 calc R . . H133 H 0.3031 0.1622 0.4994 0.054 Uiso 1 1 calc R . . O20 O -0.0017(4) 0.0044(2) 0.3723(3) 0.039(2) Uani 0.33 1 d PD A -1 H20 H -0.0195 -0.0080 0.3728 0.058 Uiso 0.33 1 calc PR A -1 C21 C 0.00764(14) 0.01112(10) 0.2544(4) 0.0230(11) Uani 0.33 1 d P A -1 H21 H 0.0239 0.0313 0.2577 0.028 Uiso 0.33 1 calc PR A -1 C22 C -0.01292(15) 0.01174(17) 0.1701(5) 0.0404(15) Uani 0.33 1 d PD A -1 H221 H -0.0206 0.0232 0.2047 0.061 Uiso 0.33 1 calc PR A -1 H222 H -0.0286 -0.0078 0.1558 0.061 Uiso 0.33 1 calc PR A -1 H223 H -0.0033 0.0202 0.0931 0.061 Uiso 0.33 1 calc PR A -1 C23 C 0.02091(14) -0.00630(14) 0.2113(5) 0.0332(13) Uani 0.33 1 d PD A -1 H231 H 0.0342 -0.0059 0.2730 0.050 Uiso 0.33 1 calc PR A -1 H232 H 0.0313 0.0019 0.1356 0.050 Uiso 0.33 1 calc PR A -1 H233 H 0.0058 -0.0261 0.1973 0.050 Uiso 0.33 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0243(6) 0.0218(6) 0.0182(5) 0.0033(4) 0.0044(4) 0.0130(5) O2A 0.0186(5) 0.0198(5) 0.0177(5) -0.0035(4) -0.0024(4) 0.0108(4) C1A 0.0166(7) 0.0162(7) 0.0177(7) 0.0006(6) -0.0003(6) 0.0086(6) C2A 0.0137(7) 0.0147(7) 0.0181(7) 0.0018(5) 0.0011(5) 0.0056(6) C3A 0.0151(7) 0.0135(7) 0.0172(7) 0.0027(5) 0.0025(5) 0.0065(6) C4A 0.0155(7) 0.0130(7) 0.0166(7) 0.0000(5) -0.0009(5) 0.0069(6) C5A 0.0184(7) 0.0138(7) 0.0160(7) 0.0022(5) 0.0001(5) 0.0079(6) C6A 0.0199(7) 0.0145(7) 0.0222(8) -0.0010(6) -0.0011(6) 0.0072(6) C7A 0.0162(7) 0.0181(7) 0.0176(7) 0.0005(6) 0.0009(6) 0.0076(6) C8A 0.0181(7) 0.0219(8) 0.0231(8) 0.0046(6) 0.0008(6) 0.0119(6) C9A 0.0159(7) 0.0175(7) 0.0290(8) 0.0025(6) 0.0056(6) 0.0096(6) C10A 0.0180(7) 0.0157(7) 0.0219(8) -0.0007(6) 0.0037(6) 0.0069(6) C11A 0.0163(7) 0.0149(7) 0.0134(7) -0.0016(5) -0.0025(5) 0.0068(6) C12A 0.0203(7) 0.0145(7) 0.0177(7) 0.0011(5) -0.0010(6) 0.0092(6) C13A 0.0208(7) 0.0184(7) 0.0194(7) -0.0021(6) -0.0009(6) 0.0119(6) C14A 0.0174(7) 0.0189(7) 0.0135(7) -0.0013(6) -0.0012(5) 0.0074(6) C15A 0.0202(7) 0.0143(7) 0.0161(7) 0.0002(5) -0.0025(6) 0.0084(6) C16A 0.0174(7) 0.0151(7) 0.0170(7) -0.0017(5) -0.0019(5) 0.0091(6) C17A 0.0230(8) 0.0224(8) 0.0178(8) 0.0004(6) -0.0031(6) 0.0108(7) C18A 0.0187(7) 0.0182(7) 0.0199(8) 0.0005(6) -0.0008(6) 0.0067(6) O1B 0.0221(6) 0.0272(6) 0.0248(6) -0.0080(5) -0.0052(5) 0.0125(5) O2B 0.0158(5) 0.0202(5) 0.0185(5) 0.0038(4) 0.0001(4) 0.0078(4) C1B 0.0153(7) 0.0156(7) 0.0176(7) 0.0019(5) 0.0010(5) 0.0064(6) C2B 0.0168(7) 0.0150(7) 0.0174(7) -0.0004(5) 0.0017(5) 0.0088(6) C3B 0.0140(7) 0.0156(7) 0.0172(7) -0.0016(5) 0.0010(5) 0.0075(6) C4B 0.0134(7) 0.0156(7) 0.0157(7) 0.0006(5) 0.0010(5) 0.0076(6) C5B 0.0151(7) 0.0182(7) 0.0161(7) -0.0005(5) 0.0017(5) 0.0090(6) C6B 0.0182(7) 0.0153(7) 0.0231(8) 0.0003(6) -0.0012(6) 0.0086(6) C7B 0.0188(7) 0.0203(7) 0.0166(7) 0.0005(6) 0.0013(6) 0.0096(6) C8B 0.0175(7) 0.0216(8) 0.0217(8) -0.0003(6) 0.0043(6) 0.0089(6) C9B 0.0138(7) 0.0209(8) 0.0263(8) -0.0040(6) -0.0003(6) 0.0088(6) C10B 0.0194(7) 0.0202(7) 0.0206(8) -0.0016(6) -0.0017(6) 0.0129(6) C11B 0.0176(7) 0.0143(7) 0.0151(7) 0.0024(5) 0.0018(5) 0.0072(6) C12B 0.0186(7) 0.0172(7) 0.0181(7) 0.0022(6) 0.0019(6) 0.0082(6) C13B 0.0162(7) 0.0199(7) 0.0206(8) 0.0033(6) -0.0006(6) 0.0070(6) C14B 0.0213(8) 0.0163(7) 0.0165(7) 0.0018(6) -0.0007(6) 0.0060(6) C15B 0.0248(8) 0.0200(7) 0.0182(7) 0.0015(6) 0.0045(6) 0.0125(7) C16B 0.0177(7) 0.0202(7) 0.0173(7) 0.0023(6) 0.0025(6) 0.0097(6) C17B 0.0219(8) 0.0212(8) 0.0186(8) 0.0034(6) 0.0040(6) 0.0090(6) C18B 0.0268(8) 0.0186(8) 0.0220(8) 0.0015(6) 0.0034(6) 0.0124(7) O1C 0.0228(6) 0.0213(6) 0.0206(6) 0.0048(4) -0.0011(4) 0.0106(5) O2C 0.0204(5) 0.0144(5) 0.0163(5) 0.0005(4) 0.0033(4) 0.0080(4) C1C 0.0180(7) 0.0134(7) 0.0170(7) -0.0002(5) 0.0019(6) 0.0067(6) C2C 0.0149(7) 0.0154(7) 0.0169(7) -0.0006(5) -0.0016(5) 0.0084(6) C3C 0.0138(7) 0.0148(7) 0.0173(7) -0.0001(5) -0.0020(5) 0.0076(6) C4C 0.0137(7) 0.0141(7) 0.0169(7) -0.0014(5) 0.0006(5) 0.0057(6) C5C 0.0142(7) 0.0149(7) 0.0170(7) -0.0017(5) -0.0004(5) 0.0050(6) C6C 0.0159(7) 0.0207(8) 0.0237(8) 0.0000(6) 0.0028(6) 0.0088(6) C7C 0.0180(7) 0.0184(7) 0.0176(7) -0.0006(6) -0.0011(6) 0.0103(6) C8C 0.0205(7) 0.0152(7) 0.0238(8) -0.0038(6) -0.0050(6) 0.0104(6) C9C 0.0170(7) 0.0139(7) 0.0271(8) 0.0023(6) -0.0031(6) 0.0077(6) C10C 0.0148(7) 0.0171(7) 0.0208(7) 0.0039(6) 0.0006(6) 0.0080(6) C11C 0.0161(7) 0.0138(7) 0.0149(7) -0.0017(5) 0.0021(5) 0.0067(6) C12C 0.0164(7) 0.0149(7) 0.0193(7) -0.0019(6) 0.0009(6) 0.0046(6) C13C 0.0205(7) 0.0127(7) 0.0201(7) 0.0010(6) 0.0035(6) 0.0056(6) C14C 0.0226(8) 0.0179(7) 0.0143(7) 0.0017(5) 0.0028(6) 0.0120(6) C15C 0.0179(7) 0.0155(7) 0.0182(7) -0.0022(6) -0.0006(6) 0.0068(6) C16C 0.0173(7) 0.0131(7) 0.0169(7) -0.0001(5) 0.0020(6) 0.0059(6) C17C 0.0237(8) 0.0201(8) 0.0179(7) -0.0040(6) 0.0020(6) 0.0089(6) C18C 0.0202(7) 0.0189(7) 0.0214(8) 0.0018(6) 0.0030(6) 0.0106(6) O1D 0.0326(6) 0.0247(6) 0.0212(6) 0.0070(5) 0.0116(5) 0.0171(5) O2D 0.0245(6) 0.0222(5) 0.0160(5) -0.0037(4) -0.0019(4) 0.0147(5) C1D 0.0218(7) 0.0179(7) 0.0154(7) -0.0008(6) -0.0001(6) 0.0120(6) C2D 0.0184(7) 0.0146(7) 0.0164(7) 0.0018(5) 0.0022(6) 0.0075(6) C3D 0.0178(7) 0.0130(7) 0.0164(7) 0.0016(5) 0.0027(5) 0.0079(6) C4D 0.0190(7) 0.0135(7) 0.0144(7) 0.0004(5) 0.0005(5) 0.0089(6) C5D 0.0209(7) 0.0144(7) 0.0154(7) 0.0016(5) 0.0004(6) 0.0101(6) C6D 0.0206(7) 0.0146(7) 0.0211(8) -0.0010(6) -0.0010(6) 0.0087(6) C7D 0.0219(8) 0.0179(7) 0.0155(7) 0.0013(6) 0.0011(6) 0.0106(6) C8D 0.0215(8) 0.0212(8) 0.0204(8) 0.0033(6) 0.0005(6) 0.0120(7) C9D 0.0244(8) 0.0178(7) 0.0238(8) 0.0031(6) 0.0054(6) 0.0137(6) C10D 0.0232(8) 0.0163(7) 0.0191(7) 0.0000(6) 0.0045(6) 0.0101(6) C11D 0.0186(7) 0.0147(7) 0.0116(6) -0.0022(5) -0.0030(5) 0.0078(6) C12D 0.0222(7) 0.0152(7) 0.0154(7) 0.0005(5) -0.0015(6) 0.0108(6) C13D 0.0228(8) 0.0200(7) 0.0163(7) -0.0006(6) 0.0003(6) 0.0137(6) C14D 0.0224(8) 0.0199(7) 0.0127(7) 0.0008(6) 0.0012(6) 0.0101(6) C15D 0.0267(8) 0.0163(7) 0.0166(7) 0.0022(6) 0.0007(6) 0.0118(6) C16D 0.0236(8) 0.0165(7) 0.0155(7) -0.0012(5) -0.0004(6) 0.0127(6) C17D 0.0283(8) 0.0243(8) 0.0161(7) -0.0012(6) -0.0034(6) 0.0148(7) C18D 0.0236(8) 0.0183(7) 0.0193(8) -0.0014(6) -0.0010(6) 0.0093(6) O10 0.0396(8) 0.0628(10) 0.0416(8) -0.0249(7) -0.0166(6) 0.0391(8) C11 0.0715(17) 0.084(2) 0.086(2) -0.0577(17) -0.0474(15) 0.0637(17) C12 0.0339(10) 0.0521(13) 0.0417(11) -0.0131(10) -0.0086(9) 0.0264(10) C13 0.0399(11) 0.0359(10) 0.0397(11) -0.0091(8) -0.0061(8) 0.0252(9) O20 0.067(5) 0.028(3) 0.0202(13) -0.007(3) 0.002(5) 0.0225(18) C21 0.029(5) 0.020(3) 0.023(2) -0.0013(17) 0.000(2) 0.014(3) C22 0.046(4) 0.068(5) 0.026(3) 0.001(3) -0.002(3) 0.042(4) C23 0.046(4) 0.045(4) 0.028(3) -0.002(3) 0.001(3) 0.037(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C14A 1.3804(18) . ? O1A H1A 0.8500 . ? O2A C2A 1.3740(18) . ? O2A C1A 1.4620(17) . ? C1A C17A 1.524(2) . ? C1A C5A 1.524(2) . ? C1A C18A 1.527(2) . ? C2A C10A 1.400(2) . ? C2A C3A 1.401(2) . ? C3A C7A 1.402(2) . ? C3A C4A 1.526(2) . ? C4A C5A 1.541(2) . ? C4A C11A 1.543(2) . ? C4A C6A 1.548(2) . ? C5A H5AA 0.9900 . ? C5A H5AB 0.9900 . ? C6A H6AA 0.9800 . ? C6A H6AB 0.9800 . ? C6A H6AC 0.9800 . ? C7A C8A 1.386(2) . ? C7A H7A 0.9500 . ? C8A C9A 1.394(2) . ? C8A H8A 0.9500 . ? C9A C10A 1.386(2) . ? C9A H9A 0.9500 . ? C10A H10A 0.9500 . ? C11A C16A 1.394(2) . ? C11A C12A 1.403(2) . ? C12A C13A 1.386(2) . ? C12A H12A 0.9500 . ? C13A C14A 1.391(2) . ? C13A H13A 0.9500 . ? C14A C15A 1.385(2) . ? C15A C16A 1.394(2) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? O1B C14B 1.3784(18) . ? O1B H1B 0.8500 . ? O2B C2B 1.3724(18) . ? O2B C1B 1.4580(18) . ? C1B C17B 1.522(2) . ? C1B C5B 1.524(2) . ? C1B C18B 1.530(2) . ? C2B C10B 1.399(2) . ? C2B C3B 1.403(2) . ? C3B C7B 1.403(2) . ? C3B C4B 1.5268(19) . ? C4B C11B 1.546(2) . ? C4B C5B 1.5482(19) . ? C4B C6B 1.550(2) . ? C5B H5BA 0.9900 . ? C5B H5BB 0.9900 . ? C6B H6BA 0.9800 . ? C6B H6BB 0.9800 . ? C6B H6BC 0.9800 . ? C7B C8B 1.388(2) . ? C7B H7B 0.9500 . ? C8B C9B 1.392(2) . ? C8B H8B 0.9500 . ? C9B C10B 1.386(2) . ? C9B H9B 0.9500 . ? C10B H10B 0.9500 . ? C11B C16B 1.391(2) . ? C11B C12B 1.400(2) . ? C12B C13B 1.386(2) . ? C12B H12B 0.9500 . ? C13B C14B 1.384(2) . ? C13B H13B 0.9500 . ? C14B C15B 1.383(2) . ? C15B C16B 1.411(2) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 0.9800 . ? O1C C14C 1.3772(18) . ? O1C H1C 0.8500 . ? O2C C2C 1.3715(17) . ? O2C C1C 1.4609(17) . ? C1C C17C 1.521(2) . ? C1C C18C 1.525(2) . ? C1C C5C 1.528(2) . ? C2C C3C 1.401(2) . ? C2C C10C 1.401(2) . ? C3C C7C 1.402(2) . ? C3C C4C 1.523(2) . ? C4C C11C 1.540(2) . ? C4C C5C 1.5420(19) . ? C4C C6C 1.550(2) . ? C5C H5CA 0.9900 . ? C5C H5CB 0.9900 . ? C6C H6CA 0.9800 . ? C6C H6CB 0.9800 . ? C6C H6CC 0.9800 . ? C7C C8C 1.385(2) . ? C7C H7C 0.9500 . ? C8C C9C 1.392(2) . ? C8C H8C 0.9500 . ? C9C C10C 1.385(2) . ? C9C H9C 0.9500 . ? C10C H10C 0.9500 . ? C11C C16C 1.394(2) . ? C11C C12C 1.400(2) . ? C12C C13C 1.386(2) . ? C12C H12C 0.9500 . ? C13C C14C 1.387(2) . ? C13C H13C 0.9500 . ? C14C C15C 1.390(2) . ? C15C C16C 1.391(2) . ? C15C H15C 0.9500 . ? C16C H16C 0.9500 . ? C17C H17G 0.9800 . ? C17C H17H 0.9800 . ? C17C H17I 0.9800 . ? C18C H18G 0.9800 . ? C18C H18H 0.9800 . ? C18C H18I 0.9800 . ? O1D C14D 1.3814(18) . ? O1D H1D 0.8500 . ? O2D C2D 1.3736(18) . ? O2D C1D 1.4622(18) . ? C1D C17D 1.522(2) . ? C1D C5D 1.525(2) . ? C1D C18D 1.525(2) . ? C2D C10D 1.399(2) . ? C2D C3D 1.401(2) . ? C3D C7D 1.403(2) . ? C3D C4D 1.5255(19) . ? C4D C11D 1.543(2) . ? C4D C5D 1.544(2) . ? C4D C6D 1.547(2) . ? C5D H5DA 0.9900 . ? C5D H5DB 0.9900 . ? C6D H6DA 0.9800 . ? C6D H6DB 0.9800 . ? C6D H6DC 0.9800 . ? C7D C8D 1.386(2) . ? C7D H7D 0.9500 . ? C8D C9D 1.392(2) . ? C8D H8D 0.9500 . ? C9D C10D 1.383(2) . ? C9D H9D 0.9500 . ? C10D H10D 0.9500 . ? C11D C16D 1.396(2) . ? C11D C12D 1.399(2) . ? C12D C13D 1.393(2) . ? C12D H12D 0.9500 . ? C13D C14D 1.392(2) . ? C13D H13D 0.9500 . ? C14D C15D 1.385(2) . ? C15D C16D 1.391(2) . ? C15D H15D 0.9500 . ? C16D H16D 0.9500 . ? C17D H17J 0.9800 . ? C17D H17K 0.9800 . ? C17D H17L 0.9800 . ? C18D H18J 0.9800 . ? C18D H18K 0.9800 . ? C18D H18L 0.9800 . ? O10 C11 1.361(3) . ? O10 H10 0.8500 . ? C11 C12 1.470(3) . ? C11 C13 1.501(3) . ? C11 H11 1.0000 . ? C12 H121 0.9800 . ? C12 H122 0.9800 . ? C12 H123 0.9800 . ? C13 H131 0.9800 . ? C13 H132 0.9800 . ? C13 H133 0.9800 . ? O20 C21 1.377(8) . ? O20 H20 0.8500 . ? C21 C22 1.462(8) . ? C21 C23 1.515(8) . ? C21 H21 1.0000 . ? C22 H221 0.9800 . ? C22 H222 0.9800 . ? C22 H223 0.9800 . ? C23 H231 0.9800 . ? C23 H232 0.9800 . ? C23 H233 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14A O1A H1A 109.5 . . ? C2A O2A C1A 117.09(11) . . ? O2A C1A C17A 104.77(12) . . ? O2A C1A C5A 108.53(11) . . ? C17A C1A C5A 109.95(12) . . ? O2A C1A C18A 107.88(12) . . ? C17A C1A C18A 110.48(12) . . ? C5A C1A C18A 114.71(12) . . ? O2A C2A C10A 115.19(13) . . ? O2A C2A C3A 124.30(13) . . ? C10A C2A C3A 120.47(14) . . ? C2A C3A C7A 117.68(13) . . ? C2A C3A C4A 121.54(13) . . ? C7A C3A C4A 120.78(13) . . ? C3A C4A C5A 108.01(12) . . ? C3A C4A C11A 111.43(12) . . ? C5A C4A C11A 112.12(12) . . ? C3A C4A C6A 109.63(12) . . ? C5A C4A C6A 107.03(12) . . ? C11A C4A C6A 108.52(12) . . ? C1A C5A C4A 115.51(12) . . ? C1A C5A H5AA 108.4 . . ? C4A C5A H5AA 108.4 . . ? C1A C5A H5AB 108.4 . . ? C4A C5A H5AB 108.4 . . ? H5AA C5A H5AB 107.5 . . ? C4A C6A H6AA 109.5 . . ? C4A C6A H6AB 109.5 . . ? H6AA C6A H6AB 109.5 . . ? C4A C6A H6AC 109.5 . . ? H6AA C6A H6AC 109.5 . . ? H6AB C6A H6AC 109.5 . . ? C8A C7A C3A 122.17(14) . . ? C8A C7A H7A 118.9 . . ? C3A C7A H7A 118.9 . . ? C7A C8A C9A 119.26(14) . . ? C7A C8A H8A 120.4 . . ? C9A C8A H8A 120.4 . . ? C10A C9A C8A 119.92(14) . . ? C10A C9A H9A 120.0 . . ? C8A C9A H9A 120.0 . . ? C9A C10A C2A 120.47(14) . . ? C9A C10A H10A 119.8 . . ? C2A C10A H10A 119.8 . . ? C16A C11A C12A 117.10(13) . . ? C16A C11A C4A 123.08(13) . . ? C12A C11A C4A 119.82(13) . . ? C13A C12A C11A 121.63(14) . . ? C13A C12A H12A 119.2 . . ? C11A C12A H12A 119.2 . . ? C12A C13A C14A 119.94(14) . . ? C12A C13A H13A 120.0 . . ? C14A C13A H13A 120.0 . . ? O1A C14A C15A 122.07(13) . . ? O1A C14A C13A 118.13(13) . . ? C15A C14A C13A 119.78(14) . . ? C14A C15A C16A 119.63(13) . . ? C14A C15A H15A 120.2 . . ? C16A C15A H15A 120.2 . . ? C11A C16A C15A 121.92(14) . . ? C11A C16A H16A 119.0 . . ? C15A C16A H16A 119.0 . . ? C1A C17A H17A 109.5 . . ? C1A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C1A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C1A C18A H18A 109.5 . . ? C1A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C1A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C14B O1B H1B 109.5 . . ? C2B O2B C1B 116.92(11) . . ? O2B C1B C17B 104.84(12) . . ? O2B C1B C5B 108.46(11) . . ? C17B C1B C5B 109.87(12) . . ? O2B C1B C18B 107.73(12) . . ? C17B C1B C18B 110.70(12) . . ? C5B C1B C18B 114.73(12) . . ? O2B C2B C10B 114.74(13) . . ? O2B C2B C3B 124.36(13) . . ? C10B C2B C3B 120.84(14) . . ? C7B C3B C2B 117.34(13) . . ? C7B C3B C4B 120.67(13) . . ? C2B C3B C4B 121.70(13) . . ? C3B C4B C11B 113.82(12) . . ? C3B C4B C5B 108.03(12) . . ? C11B C4B C5B 111.10(12) . . ? C3B C4B C6B 108.45(12) . . ? C11B C4B C6B 108.47(12) . . ? C5B C4B C6B 106.70(11) . . ? C1B C5B C4B 115.63(12) . . ? C1B C5B H5BA 108.4 . . ? C4B C5B H5BA 108.4 . . ? C1B C5B H5BB 108.4 . . ? C4B C5B H5BB 108.4 . . ? H5BA C5B H5BB 107.4 . . ? C4B C6B H6BA 109.5 . . ? C4B C6B H6BB 109.5 . . ? H6BA C6B H6BB 109.5 . . ? C4B C6B H6BC 109.5 . . ? H6BA C6B H6BC 109.5 . . ? H6BB C6B H6BC 109.5 . . ? C8B C7B C3B 122.07(14) . . ? C8B C7B H7B 119.0 . . ? C3B C7B H7B 119.0 . . ? C7B C8B C9B 119.59(14) . . ? C7B C8B H8B 120.2 . . ? C9B C8B H8B 120.2 . . ? C10B C9B C8B 119.75(14) . . ? C10B C9B H9B 120.1 . . ? C8B C9B H9B 120.1 . . ? C9B C10B C2B 120.40(14) . . ? C9B C10B H10B 119.8 . . ? C2B C10B H10B 119.8 . . ? C16B C11B C12B 116.88(14) . . ? C16B C11B C4B 124.92(13) . . ? C12B C11B C4B 118.19(13) . . ? C13B C12B C11B 122.22(14) . . ? C13B C12B H12B 118.9 . . ? C11B C12B H12B 118.9 . . ? C14B C13B C12B 119.92(14) . . ? C14B C13B H13B 120.0 . . ? C12B C13B H13B 120.0 . . ? O1B C14B C15B 124.09(14) . . ? O1B C14B C13B 116.12(14) . . ? C15B C14B C13B 119.79(14) . . ? C14B C15B C16B 119.66(14) . . ? C14B C15B H15B 120.2 . . ? C16B C15B H15B 120.2 . . ? C11B C16B C15B 121.50(14) . . ? C11B C16B H16B 119.2 . . ? C15B C16B H16B 119.2 . . ? C1B C17B H17D 109.5 . . ? C1B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C1B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C1B C18B H18D 109.5 . . ? C1B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C1B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C14C O1C H1C 109.5 . . ? C2C O2C C1C 116.78(11) . . ? O2C C1C C17C 105.14(12) . . ? O2C C1C C18C 107.91(12) . . ? C17C C1C C18C 110.51(12) . . ? O2C C1C C5C 108.31(11) . . ? C17C C1C C5C 109.15(12) . . ? C18C C1C C5C 115.29(12) . . ? O2C C2C C3C 124.23(13) . . ? O2C C2C C10C 114.97(13) . . ? C3C C2C C10C 120.76(13) . . ? C2C C3C C7C 117.43(13) . . ? C2C C3C C4C 121.79(13) . . ? C7C C3C C4C 120.77(13) . . ? C3C C4C C11C 111.86(12) . . ? C3C C4C C5C 108.08(12) . . ? C11C C4C C5C 111.39(12) . . ? C3C C4C C6C 109.75(12) . . ? C11C C4C C6C 108.83(12) . . ? C5C C4C C6C 106.78(12) . . ? C1C C5C C4C 115.37(12) . . ? C1C C5C H5CA 108.4 . . ? C4C C5C H5CA 108.4 . . ? C1C C5C H5CB 108.4 . . ? C4C C5C H5CB 108.4 . . ? H5CA C5C H5CB 107.5 . . ? C4C C6C H6CA 109.5 . . ? C4C C6C H6CB 109.5 . . ? H6CA C6C H6CB 109.5 . . ? C4C C6C H6CC 109.5 . . ? H6CA C6C H6CC 109.5 . . ? H6CB C6C H6CC 109.5 . . ? C8C C7C C3C 122.18(14) . . ? C8C C7C H7C 118.9 . . ? C3C C7C H7C 118.9 . . ? C7C C8C C9C 119.43(14) . . ? C7C C8C H8C 120.3 . . ? C9C C8C H8C 120.3 . . ? C10C C9C C8C 119.92(14) . . ? C10C C9C H9C 120.0 . . ? C8C C9C H9C 120.0 . . ? C9C C10C C2C 120.28(14) . . ? C9C C10C H10C 119.9 . . ? C2C C10C H10C 119.9 . . ? C16C C11C C12C 117.32(14) . . ? C16C C11C C4C 123.26(13) . . ? C12C C11C C4C 119.41(13) . . ? C13C C12C C11C 121.76(14) . . ? C13C C12C H12C 119.1 . . ? C11C C12C H12C 119.1 . . ? C12C C13C C14C 119.73(14) . . ? C12C C13C H13C 120.1 . . ? C14C C13C H13C 120.1 . . ? O1C C14C C13C 118.25(13) . . ? O1C C14C C15C 121.86(14) . . ? C13C C14C C15C 119.88(14) . . ? C14C C15C C16C 119.64(14) . . ? C14C C15C H15C 120.2 . . ? C16C C15C H15C 120.2 . . ? C15C C16C C11C 121.67(14) . . ? C15C C16C H16C 119.2 . . ? C11C C16C H16C 119.2 . . ? C1C C17C H17G 109.5 . . ? C1C C17C H17H 109.5 . . ? H17G C17C H17H 109.5 . . ? C1C C17C H17I 109.5 . . ? H17G C17C H17I 109.5 . . ? H17H C17C H17I 109.5 . . ? C1C C18C H18G 109.5 . . ? C1C C18C H18H 109.5 . . ? H18G C18C H18H 109.5 . . ? C1C C18C H18I 109.5 . . ? H18G C18C H18I 109.5 . . ? H18H C18C H18I 109.5 . . ? C14D O1D H1D 109.5 . . ? C2D O2D C1D 117.49(11) . . ? O2D C1D C17D 104.74(12) . . ? O2D C1D C5D 109.03(12) . . ? C17D C1D C5D 109.60(12) . . ? O2D C1D C18D 107.75(12) . . ? C17D C1D C18D 110.59(13) . . ? C5D C1D C18D 114.62(12) . . ? O2D C2D C10D 114.83(13) . . ? O2D C2D C3D 124.44(13) . . ? C10D C2D C3D 120.67(14) . . ? C2D C3D C7D 117.56(13) . . ? C2D C3D C4D 121.59(13) . . ? C7D C3D C4D 120.83(13) . . ? C3D C4D C11D 111.99(12) . . ? C3D C4D C5D 107.93(12) . . ? C11D C4D C5D 111.96(12) . . ? C3D C4D C6D 109.69(12) . . ? C11D C4D C6D 108.62(11) . . ? C5D C4D C6D 106.50(11) . . ? C1D C5D C4D 115.51(12) . . ? C1D C5D H5DA 108.4 . . ? C4D C5D H5DA 108.4 . . ? C1D C5D H5DB 108.4 . . ? C4D C5D H5DB 108.4 . . ? H5DA C5D H5DB 107.5 . . ? C4D C6D H6DA 109.5 . . ? C4D C6D H6DB 109.5 . . ? H6DA C6D H6DB 109.5 . . ? C4D C6D H6DC 109.5 . . ? H6DA C6D H6DC 109.5 . . ? H6DB C6D H6DC 109.5 . . ? C8D C7D C3D 121.94(14) . . ? C8D C7D H7D 119.0 . . ? C3D C7D H7D 119.0 . . ? C7D C8D C9D 119.52(14) . . ? C7D C8D H8D 120.2 . . ? C9D C8D H8D 120.2 . . ? C10D C9D C8D 119.88(14) . . ? C10D C9D H9D 120.1 . . ? C8D C9D H9D 120.1 . . ? C9D C10D C2D 120.43(14) . . ? C9D C10D H10D 119.8 . . ? C2D C10D H10D 119.8 . . ? C16D C11D C12D 116.94(13) . . ? C16D C11D C4D 122.83(13) . . ? C12D C11D C4D 120.23(13) . . ? C13D C12D C11D 121.77(13) . . ? C13D C12D H12D 119.1 . . ? C11D C12D H12D 119.1 . . ? C14D C13D C12D 119.75(14) . . ? C14D C13D H13D 120.1 . . ? C12D C13D H13D 120.1 . . ? O1D C14D C15D 117.93(13) . . ? O1D C14D C13D 122.39(14) . . ? C15D C14D C13D 119.68(14) . . ? C14D C15D C16D 119.81(14) . . ? C14D C15D H15D 120.1 . . ? C16D C15D H15D 120.1 . . ? C15D C16D C11D 122.03(14) . . ? C15D C16D H16D 119.0 . . ? C11D C16D H16D 119.0 . . ? C1D C17D H17J 109.5 . . ? C1D C17D H17K 109.5 . . ? H17J C17D H17K 109.5 . . ? C1D C17D H17L 109.5 . . ? H17J C17D H17L 109.5 . . ? H17K C17D H17L 109.5 . . ? C1D C18D H18J 109.5 . . ? C1D C18D H18K 109.5 . . ? H18J C18D H18K 109.5 . . ? C1D C18D H18L 109.5 . . ? H18J C18D H18L 109.5 . . ? H18K C18D H18L 109.5 . . ? C11 O10 H10 109.5 . . ? O10 C11 C12 114.4(2) . . ? O10 C11 C13 116.1(2) . . ? C12 C11 C13 115.1(2) . . ? O10 C11 H11 102.9 . . ? C12 C11 H11 102.9 . . ? C13 C11 H11 102.9 . . ? C11 C12 H121 109.5 . . ? C11 C12 H122 109.5 . . ? H121 C12 H122 109.5 . . ? C11 C12 H123 109.5 . . ? H121 C12 H123 109.5 . . ? H122 C12 H123 109.5 . . ? C11 C13 H131 109.5 . . ? C11 C13 H132 109.5 . . ? H131 C13 H132 109.5 . . ? C11 C13 H133 109.5 . . ? H131 C13 H133 109.5 . . ? H132 C13 H133 109.5 . . ? C21 O20 H20 109.5 . . ? O20 C21 C22 115.1(8) . . ? O20 C21 C23 111.1(5) . . ? C22 C21 C23 114.4(4) . . ? O20 C21 H21 105.0 . . ? C22 C21 H21 105.0 . . ? C23 C21 H21 105.0 . . ? C21 C22 H221 109.5 . . ? C21 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? C21 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? C21 C23 H231 109.5 . . ? C21 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? C21 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2A O2A C1A C17A -161.54(12) . . . . ? C2A O2A C1A C5A -44.12(16) . . . . ? C2A O2A C1A C18A 80.74(15) . . . . ? C1A O2A C2A C10A -163.97(12) . . . . ? C1A O2A C2A C3A 18.4(2) . . . . ? O2A C2A C3A C7A 177.45(13) . . . . ? C10A C2A C3A C7A 0.0(2) . . . . ? O2A C2A C3A C4A -2.4(2) . . . . ? C10A C2A C3A C4A -179.88(13) . . . . ? C2A C3A C4A C5A 14.23(18) . . . . ? C7A C3A C4A C5A -165.62(13) . . . . ? C2A C3A C4A C11A -109.34(15) . . . . ? C7A C3A C4A C11A 70.82(17) . . . . ? C2A C3A C4A C6A 130.52(14) . . . . ? C7A C3A C4A C6A -49.33(18) . . . . ? O2A C1A C5A C4A 58.44(16) . . . . ? C17A C1A C5A C4A 172.50(12) . . . . ? C18A C1A C5A C4A -62.28(17) . . . . ? C3A C4A C5A C1A -42.56(16) . . . . ? C11A C4A C5A C1A 80.59(15) . . . . ? C6A C4A C5A C1A -160.53(12) . . . . ? C2A C3A C7A C8A 1.3(2) . . . . ? C4A C3A C7A C8A -178.89(14) . . . . ? C3A C7A C8A C9A -1.2(2) . . . . ? C7A C8A C9A C10A -0.2(2) . . . . ? C8A C9A C10A C2A 1.4(2) . . . . ? O2A C2A C10A C9A -178.98(13) . . . . ? C3A C2A C10A C9A -1.3(2) . . . . ? C3A C4A C11A C16A -2.60(19) . . . . ? C5A C4A C11A C16A -123.80(15) . . . . ? C6A C4A C11A C16A 118.20(15) . . . . ? C3A C4A C11A C12A 177.64(13) . . . . ? C5A C4A C11A C12A 56.44(17) . . . . ? C6A C4A C11A C12A -61.56(17) . . . . ? C16A C11A C12A C13A 0.2(2) . . . . ? C4A C11A C12A C13A -179.99(13) . . . . ? C11A C12A C13A C14A -0.3(2) . . . . ? C12A C13A C14A O1A 178.51(13) . . . . ? C12A C13A C14A C15A 0.1(2) . . . . ? O1A C14A C15A C16A -178.23(13) . . . . ? C13A C14A C15A C16A 0.1(2) . . . . ? C12A C11A C16A C15A 0.0(2) . . . . ? C4A C11A C16A C15A -179.78(13) . . . . ? C14A C15A C16A C11A -0.2(2) . . . . ? C2B O2B C1B C17B -162.03(12) . . . . ? C2B O2B C1B C5B -44.70(16) . . . . ? C2B O2B C1B C18B 80.03(15) . . . . ? C1B O2B C2B C10B -167.48(12) . . . . ? C1B O2B C2B C3B 15.4(2) . . . . ? O2B C2B C3B C7B 178.41(13) . . . . ? C10B C2B C3B C7B 1.4(2) . . . . ? O2B C2B C3B C4B 4.6(2) . . . . ? C10B C2B C3B C4B -172.44(13) . . . . ? C7B C3B C4B C11B 70.40(17) . . . . ? C2B C3B C4B C11B -115.96(15) . . . . ? C7B C3B C4B C5B -165.71(13) . . . . ? C2B C3B C4B C5B 7.93(18) . . . . ? C7B C3B C4B C6B -50.42(18) . . . . ? C2B C3B C4B C6B 123.23(15) . . . . ? O2B C1B C5B C4B 58.87(16) . . . . ? C17B C1B C5B C4B 172.93(12) . . . . ? C18B C1B C5B C4B -61.61(17) . . . . ? C3B C4B C5B C1B -39.62(16) . . . . ? C11B C4B C5B C1B 85.90(15) . . . . ? C6B C4B C5B C1B -156.05(12) . . . . ? C2B C3B C7B C8B -0.5(2) . . . . ? C4B C3B C7B C8B 173.42(14) . . . . ? C3B C7B C8B C9B -0.7(2) . . . . ? C7B C8B C9B C10B 1.0(2) . . . . ? C8B C9B C10B C2B -0.1(2) . . . . ? O2B C2B C10B C9B -178.41(13) . . . . ? C3B C2B C10B C9B -1.1(2) . . . . ? C3B C4B C11B C16B 5.6(2) . . . . ? C5B C4B C11B C16B -116.58(15) . . . . ? C6B C4B C11B C16B 126.44(15) . . . . ? C3B C4B C11B C12B -175.40(13) . . . . ? C5B C4B C11B C12B 62.38(17) . . . . ? C6B C4B C11B C12B -54.59(17) . . . . ? C16B C11B C12B C13B -0.1(2) . . . . ? C4B C11B C12B C13B -179.15(13) . . . . ? C11B C12B C13B C14B 1.3(2) . . . . ? C12B C13B C14B O1B 178.47(13) . . . . ? C12B C13B C14B C15B -1.4(2) . . . . ? O1B C14B C15B C16B -179.51(14) . . . . ? C13B C14B C15B C16B 0.3(2) . . . . ? C12B C11B C16B C15B -1.0(2) . . . . ? C4B C11B C16B C15B 178.00(13) . . . . ? C14B C15B C16B C11B 0.9(2) . . . . ? C2C O2C C1C C17C -162.14(12) . . . . ? C2C O2C C1C C18C 79.90(15) . . . . ? C2C O2C C1C C5C -45.55(16) . . . . ? C1C O2C C2C C3C 19.2(2) . . . . ? C1C O2C C2C C10C -163.03(12) . . . . ? O2C C2C C3C C7C 177.87(13) . . . . ? C10C C2C C3C C7C 0.2(2) . . . . ? O2C C2C C3C C4C -1.3(2) . . . . ? C10C C2C C3C C4C -178.98(13) . . . . ? C2C C3C C4C C11C -110.58(15) . . . . ? C7C C3C C4C C11C 70.23(17) . . . . ? C2C C3C C4C C5C 12.41(18) . . . . ? C7C C3C C4C C5C -166.78(13) . . . . ? C2C C3C C4C C6C 128.51(14) . . . . ? C7C C3C C4C C6C -50.68(18) . . . . ? O2C C1C C5C C4C 58.83(16) . . . . ? C17C C1C C5C C4C 172.80(12) . . . . ? C18C C1C C5C C4C -62.14(17) . . . . ? C3C C4C C5C C1C -41.36(16) . . . . ? C11C C4C C5C C1C 81.92(15) . . . . ? C6C C4C C5C C1C -159.38(12) . . . . ? C2C C3C C7C C8C 0.8(2) . . . . ? C4C C3C C7C C8C 179.99(13) . . . . ? C3C C7C C8C C9C -0.9(2) . . . . ? C7C C8C C9C C10C 0.0(2) . . . . ? C8C C9C C10C C2C 1.0(2) . . . . ? O2C C2C C10C C9C -178.94(13) . . . . ? C3C C2C C10C C9C -1.1(2) . . . . ? C3C C4C C11C C16C 2.58(19) . . . . ? C5C C4C C11C C16C -118.52(15) . . . . ? C6C C4C C11C C16C 124.02(15) . . . . ? C3C C4C C11C C12C -178.73(13) . . . . ? C5C C4C C11C C12C 60.17(17) . . . . ? C6C C4C C11C C12C -57.29(17) . . . . ? C16C C11C C12C C13C 0.1(2) . . . . ? C4C C11C C12C C13C -178.64(13) . . . . ? C11C C12C C13C C14C 0.2(2) . . . . ? C12C C13C C14C O1C 178.95(13) . . . . ? C12C C13C C14C C15C -0.3(2) . . . . ? O1C C14C C15C C16C -179.23(13) . . . . ? C13C C14C C15C C16C 0.0(2) . . . . ? C14C C15C C16C C11C 0.4(2) . . . . ? C12C C11C C16C C15C -0.4(2) . . . . ? C4C C11C C16C C15C 178.27(13) . . . . ? C2D O2D C1D C17D 159.14(12) . . . . ? C2D O2D C1D C5D 41.90(16) . . . . ? C2D O2D C1D C18D -83.07(15) . . . . ? C1D O2D C2D C10D 166.49(12) . . . . ? C1D O2D C2D C3D -16.2(2) . . . . ? O2D C2D C3D C7D -176.92(13) . . . . ? C10D C2D C3D C7D 0.2(2) . . . . ? O2D C2D C3D C4D 1.8(2) . . . . ? C10D C2D C3D C4D 178.99(13) . . . . ? C2D C3D C4D C11D 108.70(15) . . . . ? C7D C3D C4D C11D -72.59(17) . . . . ? C2D C3D C4D C5D -14.97(18) . . . . ? C7D C3D C4D C5D 163.74(13) . . . . ? C2D C3D C4D C6D -130.62(14) . . . . ? C7D C3D C4D C6D 48.09(18) . . . . ? O2D C1D C5D C4D -57.45(16) . . . . ? C17D C1D C5D C4D -171.57(13) . . . . ? C18D C1D C5D C4D 63.40(17) . . . . ? C3D C4D C5D C1D 42.98(16) . . . . ? C11D C4D C5D C1D -80.71(15) . . . . ? C6D C4D C5D C1D 160.71(12) . . . . ? C2D C3D C7D C8D -0.4(2) . . . . ? C4D C3D C7D C8D -179.17(14) . . . . ? C3D C7D C8D C9D 0.1(2) . . . . ? C7D C8D C9D C10D 0.4(2) . . . . ? C8D C9D C10D C2D -0.5(2) . . . . ? O2D C2D C10D C9D 177.64(13) . . . . ? C3D C2D C10D C9D 0.2(2) . . . . ? C3D C4D C11D C16D -2.28(19) . . . . ? C5D C4D C11D C16D 119.10(15) . . . . ? C6D C4D C11D C16D -123.58(15) . . . . ? C3D C4D C11D C12D 178.45(13) . . . . ? C5D C4D C11D C12D -60.17(17) . . . . ? C6D C4D C11D C12D 57.16(17) . . . . ? C16D C11D C12D C13D -0.9(2) . . . . ? C4D C11D C12D C13D 178.46(13) . . . . ? C11D C12D C13D C14D -0.2(2) . . . . ? C12D C13D C14D O1D -178.46(14) . . . . ? C12D C13D C14D C15D 1.1(2) . . . . ? O1D C14D C15D C16D 178.78(14) . . . . ? C13D C14D C15D C16D -0.8(2) . . . . ? C14D C15D C16D C11D -0.4(2) . . . . ? C12D C11D C16D C15D 1.2(2) . . . . ? C4D C11D C16D C15D -178.13(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1A O1C 0.85 1.90 2.7357(15) 167.3 13 O1B H1B O10 0.85 1.84 2.6260(17) 153.1 13 O1C H1C O1B 0.85 1.84 2.6835(16) 170.8 13 O1D H1D O1D 0.85 1.99 2.8410(12) 178.0 12_556 O10 H10 O1A 0.85 1.92 2.7500(17) 163.4 . O20 H20 O1D 0.85 2.47 3.183(16) 141.6 10_556 _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.145 _refine_diff_density_min -0.970 _refine_diff_density_rms 0.048 data_cmpnd05 _database_code_depnum_ccdc_archive 'CCDC 796809' #TrackingRef 'UWA_deposit_101014.cif' #data_gk250_015K _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-p-Hydroxyphenyl-2,2,4-trimethylchroman isopropanol clathrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C18 H20 O2), C3 H8 O' _chemical_formula_sum 'C57 H68 O7' _chemical_formula_weight 865.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_int_tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 53.7098(13) _cell_length_b 53.7098 _cell_length_c 10.9911(3) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 120.0 _cell_volume 27458.6(10) _cell_formula_units_Z 24 _cell_measurement_temperature 15(2) _cell_measurement_reflns_used 9942 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 18.54 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 11184 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? #0.9959 _exptl_absorpt_correction_T_max ? #0.9990 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 15(2) _diffrn_radiation_wavelength 0.41328 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator 'diamond double-crystal' _diffrn_measurement_device_type 'Bruker SMART 6000, APEX II' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 15.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 835170 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 121 _diffrn_reflns_limit_k_min -122 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.11 _diffrn_reflns_theta_max 28.57 _reflns_number_total 70274 _reflns_number_gt 53909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Diffractometer control software' _computing_cell_refinement 'Bruker SAINT V7.68A' _computing_data_reduction 'Bruker SAINT V7.68A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury CSD v. 2.3 (2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0600P)^2^+52.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 70274 _refine_ls_number_parameters 830 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1811 _refine_ls_wR_factor_gt 0.1711 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.265614(12) 0.135607(11) 0.18305(5) 0.01165(7) Uani 1 1 d . . . H1A H 0.2684 0.1520 0.1610 0.017 Uiso 1 1 calc R . . O2A O 0.198822(10) 0.126514(10) 0.80483(4) 0.00964(6) Uani 1 1 d . . . C1A C 0.218472(13) 0.116473(12) 0.76964(5) 0.00881(7) Uani 1 1 d . . . C2A C 0.180259(13) 0.125753(12) 0.71803(5) 0.00872(7) Uani 1 1 d . . . C3A C 0.173119(13) 0.109124(13) 0.61190(5) 0.00895(7) Uani 1 1 d . . . C4A C 0.186767(13) 0.090971(12) 0.58198(5) 0.00864(7) Uani 1 1 d . . . C5A C 0.201757(14) 0.088687(13) 0.69757(6) 0.00935(7) Uani 1 1 d . . . H5AA H 0.1870 0.0739 0.7515 0.011 Uiso 1 1 calc R . . H5AB H 0.2151 0.0819 0.6739 0.011 Uiso 1 1 calc R . . C6A C 0.163140(15) 0.060152(13) 0.54877(6) 0.01138(8) Uani 1 1 d . . . H6AA H 0.1497 0.0518 0.6168 0.017 Uiso 1 1 calc R . . H6AB H 0.1720 0.0484 0.5320 0.017 Uiso 1 1 calc R . . H6AC H 0.1528 0.0607 0.4764 0.017 Uiso 1 1 calc R . . C7A C 0.152765(14) 0.109624(14) 0.53353(6) 0.01028(7) Uani 1 1 d . . . H7A H 0.1473 0.0981 0.4621 0.012 Uiso 1 1 calc R . . C8A C 0.140313(14) 0.126380(14) 0.55703(6) 0.01096(8) Uani 1 1 d . . . H8A H 0.1269 0.1266 0.5016 0.013 Uiso 1 1 calc R . . C9A C 0.147762(14) 0.142894(14) 0.66289(6) 0.01087(8) Uani 1 1 d . . . H9A H 0.1394 0.1545 0.6798 0.013 Uiso 1 1 calc R . . C10A C 0.167357(14) 0.142328(13) 0.74352(6) 0.01014(7) Uani 1 1 d . . . H10A H 0.1721 0.1532 0.8165 0.012 Uiso 1 1 calc R . . C11A C 0.207679(13) 0.103570(13) 0.47426(5) 0.00912(7) Uani 1 1 d . . . C12A C 0.223189(14) 0.090332(13) 0.43602(6) 0.01058(8) Uani 1 1 d . . . H12A H 0.2206 0.0737 0.4775 0.013 Uiso 1 1 calc R . . C13A C 0.242238(15) 0.100985(14) 0.33895(6) 0.01099(8) Uani 1 1 d . . . H13A H 0.2526 0.0917 0.3148 0.013 Uiso 1 1 calc R . . C14A C 0.246116(14) 0.125337(13) 0.27707(6) 0.01006(7) Uani 1 1 d . . . C15A C 0.231027(14) 0.138828(13) 0.31275(6) 0.01029(8) Uani 1 1 d . . . H15A H 0.2336 0.1554 0.2707 0.012 Uiso 1 1 calc R . . C16A C 0.212067(14) 0.127917(13) 0.41053(6) 0.00987(7) Uani 1 1 d . . . H16A H 0.2018 0.1373 0.4345 0.012 Uiso 1 1 calc R . . C17A C 0.228848(15) 0.110398(14) 0.88887(6) 0.01142(8) Uani 1 1 d . . . H17A H 0.2398 0.1284 0.9345 0.017 Uiso 1 1 calc R . . H17B H 0.2412 0.1022 0.8717 0.017 Uiso 1 1 calc R . . H17C H 0.2123 0.0967 0.9372 0.017 Uiso 1 1 calc R . . C18A C 0.243585(14) 0.140786(14) 0.70102(6) 0.01159(8) Uani 1 1 d . . . H18A H 0.2532 0.1577 0.7537 0.017 Uiso 1 1 calc R . . H18B H 0.2364 0.1456 0.6281 0.017 Uiso 1 1 calc R . . H18C H 0.2573 0.1346 0.6772 0.017 Uiso 1 1 calc R . . O1B O 0.337723(12) 0.224193(12) 0.17299(5) 0.01248(7) Uani 1 1 d . . . H1B H 0.3473 0.2167 0.1459 0.019 Uiso 1 1 calc R . . O2B O 0.414569(10) 0.287197(10) 0.78958(4) 0.00948(6) Uani 1 1 d . . . C1B C 0.384477(12) 0.269704(12) 0.75590(5) 0.00852(7) Uani 1 1 d . . . C2B C 0.432994(12) 0.304583(13) 0.70152(5) 0.00870(7) Uani 1 1 d . . . C3B C 0.424336(12) 0.311812(13) 0.59320(5) 0.00854(7) Uani 1 1 d . . . C4B C 0.392964(12) 0.302253(12) 0.56813(5) 0.00775(6) Uani 1 1 d . . . C5B C 0.375621(12) 0.288478(13) 0.68530(5) 0.00844(7) Uani 1 1 d . . . H5BA H 0.3775 0.3040 0.7397 0.010 Uiso 1 1 calc R . . H5BB H 0.3551 0.2766 0.6633 0.010 Uiso 1 1 calc R . . C6B C 0.390483(14) 0.329298(13) 0.54304(6) 0.01028(8) Uani 1 1 d . . . H6BA H 0.4012 0.3388 0.4691 0.015 Uiso 1 1 calc R . . H6BB H 0.3984 0.3426 0.6120 0.015 Uiso 1 1 calc R . . H6BC H 0.3702 0.3236 0.5322 0.015 Uiso 1 1 calc R . . C7B C 0.445968(13) 0.330505(14) 0.51306(6) 0.01033(8) Uani 1 1 d . . . H7B H 0.4406 0.3355 0.4387 0.012 Uiso 1 1 calc R . . C8B C 0.474975(13) 0.341890(15) 0.53906(6) 0.01109(8) Uani 1 1 d . . . H8B H 0.4892 0.3544 0.4828 0.013 Uiso 1 1 calc R . . C9B C 0.483139(13) 0.334823(14) 0.64843(6) 0.01103(8) Uani 1 1 d . . . H9B H 0.5029 0.3427 0.6675 0.013 Uiso 1 1 calc R . . C10B C 0.462258(13) 0.316295(14) 0.72905(6) 0.00996(7) Uani 1 1 d . . . H10B H 0.4678 0.3115 0.8036 0.012 Uiso 1 1 calc R . . C11B C 0.380127(13) 0.281708(13) 0.45919(5) 0.00896(7) Uani 1 1 d . . . C12B C 0.351931(13) 0.273499(14) 0.42300(6) 0.01021(7) Uani 1 1 d . . . H12B H 0.3418 0.2811 0.4656 0.012 Uiso 1 1 calc R . . C13B C 0.338499(13) 0.254717(14) 0.32715(6) 0.01062(8) Uani 1 1 d . . . H13B H 0.3195 0.2498 0.3042 0.013 Uiso 1 1 calc R . . C14B C 0.352760(13) 0.243028(13) 0.26457(6) 0.01016(7) Uani 1 1 d . . . C15B C 0.380718(14) 0.250744(14) 0.29756(6) 0.01099(8) Uani 1 1 d . . . H15B H 0.3907 0.2429 0.2553 0.013 Uiso 1 1 calc R . . C16B C 0.394153(14) 0.270148(14) 0.39372(6) 0.01058(8) Uani 1 1 d . . . H16B H 0.4134 0.2755 0.4147 0.013 Uiso 1 1 calc R . . C17B C 0.368284(14) 0.260610(14) 0.87602(6) 0.01109(8) Uani 1 1 d . . . H17D H 0.3709 0.2777 0.9197 0.017 Uiso 1 1 calc R . . H17E H 0.3758 0.2506 0.9256 0.017 Uiso 1 1 calc R . . H17F H 0.3478 0.2477 0.8602 0.017 Uiso 1 1 calc R . . C18B C 0.380989(15) 0.243475(14) 0.68638(6) 0.01168(8) Uani 1 1 d . . . H18D H 0.3872 0.2327 0.7380 0.018 Uiso 1 1 calc R . . H18E H 0.3928 0.2498 0.6126 0.018 Uiso 1 1 calc R . . H18F H 0.3608 0.2311 0.6640 0.018 Uiso 1 1 calc R . . O1C O 0.385665(11) 0.141933(11) 0.19299(5) 0.01158(7) Uani 1 1 d . . . H1C H 0.3675 0.1330 0.1858 0.017 Uiso 1 1 calc R . . O2C O 0.383705(10) 0.077250(10) 0.81213(4) 0.00927(6) Uani 1 1 d . . . C1C C 0.396797(13) 0.107185(12) 0.77497(5) 0.00878(7) Uani 1 1 d . . . C2C C 0.381608(12) 0.058012(12) 0.72559(5) 0.00817(7) Uani 1 1 d . . . C3C C 0.398059(12) 0.065576(12) 0.61889(5) 0.00809(7) Uani 1 1 d . . . C4C C 0.419715(12) 0.096691(12) 0.58899(5) 0.00848(7) Uani 1 1 d . . . C5C C 0.424057(13) 0.114995(13) 0.70327(6) 0.00942(7) Uani 1 1 d . . . H5CA H 0.4377 0.1132 0.7579 0.011 Uiso 1 1 calc R . . H5CB H 0.4330 0.1354 0.6784 0.011 Uiso 1 1 calc R . . C6C C 0.449207(13) 0.099578(14) 0.55891(6) 0.01136(8) Uani 1 1 d . . . H6CA H 0.4556 0.0925 0.6277 0.017 Uiso 1 1 calc R . . H6CB H 0.4633 0.1198 0.5437 0.017 Uiso 1 1 calc R . . H6CC H 0.4474 0.0882 0.4863 0.017 Uiso 1 1 calc R . . C7C C 0.394205(13) 0.043331(12) 0.54058(6) 0.00936(7) Uani 1 1 d . . . H7C H 0.4053 0.0480 0.4683 0.011 Uiso 1 1 calc R . . C8C C 0.374620(13) 0.014703(13) 0.56532(6) 0.00986(7) Uani 1 1 d . . . H8C H 0.3723 0.0001 0.5100 0.012 Uiso 1 1 calc R . . C9C C 0.358448(13) 0.007593(13) 0.67213(6) 0.00999(7) Uani 1 1 d . . . H9C H 0.3450 -0.0119 0.6899 0.012 Uiso 1 1 calc R . . C10C C 0.362092(13) 0.029132(13) 0.75229(6) 0.00947(7) Uani 1 1 d . . . H10C H 0.3513 0.0243 0.8256 0.011 Uiso 1 1 calc R . . C11C C 0.409935(13) 0.107639(12) 0.48054(5) 0.00893(7) Uani 1 1 d . . . C12C C 0.427702(13) 0.135782(13) 0.43914(6) 0.01016(7) Uani 1 1 d . . . H12C H 0.4457 0.1475 0.4778 0.012 Uiso 1 1 calc R . . C13C C 0.419639(14) 0.147002(13) 0.34292(6) 0.01043(8) Uani 1 1 d . . . H13C H 0.4321 0.1661 0.3160 0.013 Uiso 1 1 calc R . . C14C C 0.393236(13) 0.130060(13) 0.28614(6) 0.00951(7) Uani 1 1 d . . . C15C C 0.375169(14) 0.101972(13) 0.32540(6) 0.01007(7) Uani 1 1 d . . . H15C H 0.3572 0.0903 0.2868 0.012 Uiso 1 1 calc R . . C16C C 0.383662(13) 0.091071(13) 0.42144(6) 0.00957(7) Uani 1 1 d . . . H16C H 0.3713 0.0719 0.4475 0.011 Uiso 1 1 calc R . . C17C C 0.404984(15) 0.124360(14) 0.89257(6) 0.01161(8) Uani 1 1 d . . . H17G H 0.3875 0.1196 0.9388 0.017 Uiso 1 1 calc R . . H17H H 0.4153 0.1449 0.8737 0.017 Uiso 1 1 calc R . . H17I H 0.4174 0.1196 0.9411 0.017 Uiso 1 1 calc R . . C18C C 0.374140(14) 0.110928(14) 0.70625(6) 0.01075(8) Uani 1 1 d . . . H18G H 0.3576 0.1056 0.7594 0.016 Uiso 1 1 calc R . . H18H H 0.3679 0.0986 0.6341 0.016 Uiso 1 1 calc R . . H18I H 0.3824 0.1310 0.6812 0.016 Uiso 1 1 calc R . . O1D O 0.060180(16) 0.033820(14) 0.48807(6) 0.01800(10) Uani 1 1 d . . . H1D H 0.0503 0.0421 0.4946 0.027 Uiso 1 1 calc R . . O2D O 0.131884(13) 0.048369(12) -0.12046(5) 0.01196(7) Uani 1 1 d . . . C1D C 0.111842(16) 0.058126(14) -0.08849(6) 0.01120(8) Uani 1 1 d . . . C2D C 0.150647(15) 0.049945(13) -0.03284(6) 0.01035(8) Uani 1 1 d . . . C3D C 0.156973(14) 0.066433(13) 0.07356(5) 0.00959(7) Uani 1 1 d . . . C4D C 0.142333(14) 0.083772(12) 0.10213(5) 0.00912(7) Uani 1 1 d . . . C5D C 0.127732(15) 0.085831(13) -0.01508(6) 0.01048(8) Uani 1 1 d . . . H5DA H 0.1139 0.0922 0.0070 0.013 Uiso 1 1 calc R . . H5DB H 0.1426 0.1009 -0.0678 0.013 Uiso 1 1 calc R . . C6D C 0.165192(15) 0.114833(13) 0.13615(6) 0.01148(8) Uani 1 1 d . . . H6DA H 0.1751 0.1146 0.2106 0.017 Uiso 1 1 calc R . . H6DB H 0.1558 0.1262 0.1498 0.017 Uiso 1 1 calc R . . H6DC H 0.1791 0.1233 0.0697 0.017 Uiso 1 1 calc R . . C7D C 0.177826(15) 0.066950(14) 0.15198(6) 0.01076(8) Uani 1 1 d . . . H7D H 0.1826 0.0781 0.2242 0.013 Uiso 1 1 calc R . . C8D C 0.191778(16) 0.051642(14) 0.12743(6) 0.01176(8) Uani 1 1 d . . . H8D H 0.2058 0.0523 0.1824 0.014 Uiso 1 1 calc R . . C9D C 0.185086(16) 0.035254(14) 0.02135(6) 0.01201(8) Uani 1 1 d . . . H9D H 0.1945 0.0247 0.0038 0.014 Uiso 1 1 calc R . . C10D C 0.164718(16) 0.034481(14) -0.05823(6) 0.01153(8) Uani 1 1 d . . . H10D H 0.1602 0.0234 -0.1306 0.014 Uiso 1 1 calc R . . C11D C 0.120864(14) 0.070605(12) 0.20785(5) 0.00923(7) Uani 1 1 d . . . C12D C 0.105867(14) 0.084093(13) 0.24936(6) 0.01029(8) Uani 1 1 d . . . H12D H 0.1095 0.1016 0.2127 0.012 Uiso 1 1 calc R . . C13D C 0.085793(16) 0.072448(14) 0.34298(6) 0.01168(8) Uani 1 1 d . . . H13D H 0.0759 0.0820 0.3697 0.014 Uiso 1 1 calc R . . C14D C 0.080185(17) 0.046697(15) 0.39738(6) 0.01262(9) Uani 1 1 d . . . C15D C 0.095093(17) 0.033140(14) 0.35908(6) 0.01286(9) Uani 1 1 d . . . H15D H 0.0916 0.0157 0.3966 0.015 Uiso 1 1 calc R . . C16D C 0.115171(15) 0.045146(13) 0.26558(6) 0.01113(8) Uani 1 1 d . . . H16D H 0.1253 0.0357 0.2404 0.013 Uiso 1 1 calc R . . C17D C 0.102344(19) 0.064414(17) -0.20942(6) 0.01494(10) Uani 1 1 d . . . H17J H 0.0921 0.0466 -0.2567 0.022 Uiso 1 1 calc R . . H17K H 0.1193 0.0785 -0.2549 0.022 Uiso 1 1 calc R . . H17L H 0.0895 0.0722 -0.1945 0.022 Uiso 1 1 calc R . . C18D C 0.086442(17) 0.033620(15) -0.02279(6) 0.01382(9) Uani 1 1 d . . . H18J H 0.0775 0.0167 -0.0757 0.021 Uiso 1 1 calc R . . H18K H 0.0723 0.0395 -0.0024 0.021 Uiso 1 1 calc R . . H18L H 0.0932 0.0290 0.0520 0.021 Uiso 1 1 calc R . . O10 O 0.31197(2) 0.13749(2) 0.29785(9) 0.01214(12) Uani 0.66667 1 d P A 1 H10 H 0.3016 0.1405 0.2486 0.018 Uiso 0.66667 1 calc PR A 1 C11 C 0.33144(2) 0.16397(2) 0.35980(9) 0.01046(11) Uani 0.66667 1 d P A 1 H11 H 0.3440 0.1786 0.2984 0.013 Uiso 0.66667 1 calc PR A 1 C12 C 0.34990(5) 0.15750(5) 0.44284(16) 0.0118(2) Uani 0.66667 1 d P A 1 H121 H 0.3601 0.1501 0.3947 0.018 Uiso 0.66667 1 calc PR A 1 H122 H 0.3377 0.1431 0.5031 0.018 Uiso 0.66667 1 calc PR A 1 H123 H 0.3639 0.1751 0.4846 0.018 Uiso 0.66667 1 calc PR A 1 C13 C 0.31452(6) 0.17526(6) 0.42982(16) 0.0120(3) Uani 0.66667 1 d P A 1 H131 H 0.3033 0.1797 0.3725 0.018 Uiso 0.66667 1 calc PR A 1 H132 H 0.3279 0.1927 0.4743 0.018 Uiso 0.66667 1 calc PR A 1 H133 H 0.3015 0.1606 0.4875 0.018 Uiso 0.66667 1 calc PR A 1 O10' O 0.31729(5) 0.14580(6) 0.2756(2) 0.0174(3) Uani 0.33333 1 d P B 2 H10' H 0.3011 0.1433 0.2524 0.026 Uiso 0.33333 1 calc PR B 2 C11' C 0.32056(5) 0.15157(5) 0.4051(2) 0.0155(3) Uani 0.33333 1 d P B 2 H11' H 0.3065 0.1336 0.4484 0.019 Uiso 0.33333 1 calc PR B 2 C12' C 0.35032(19) 0.1591(2) 0.4456(8) 0.0398(17) Uani 0.33333 1 d P B 2 H124 H 0.3543 0.1440 0.4198 0.060 Uiso 0.33333 1 calc PR B 2 H125 H 0.3516 0.1609 0.5344 0.060 Uiso 0.33333 1 calc PR B 2 H126 H 0.3644 0.1775 0.4089 0.060 Uiso 0.33333 1 calc PR B 2 C13' C 0.31419(19) 0.17512(18) 0.4394(8) 0.0352(17) Uani 0.33333 1 d P B 2 H134 H 0.2942 0.1690 0.4193 0.053 Uiso 0.33333 1 calc PR B 2 H135 H 0.3270 0.1927 0.3942 0.053 Uiso 0.33333 1 calc PR B 2 H136 H 0.3173 0.1789 0.5269 0.053 Uiso 0.33333 1 calc PR B 2 O20 O -0.00422(7) 0.00275(7) 0.37289(15) 0.0187(3) Uani 0.33333 1 d PD C -1 H20 H -0.0219 -0.0096 0.3648 0.028 Uiso 0.33333 1 calc PR C -1 C21 C 0.00857(5) 0.01203(4) 0.25558(18) 0.0119(2) Uani 0.33333 1 d P C -1 H21 H 0.0246 0.0324 0.2629 0.014 Uiso 0.33333 1 calc PR C -1 C22 C -0.01316(5) 0.01152(6) 0.1680(2) 0.0160(3) Uani 0.33333 1 d PD C -1 H221 H -0.0212 0.0229 0.2010 0.024 Uiso 0.33333 1 calc PR C -1 H222 H -0.0286 -0.0084 0.1560 0.024 Uiso 0.33333 1 calc PR C -1 H223 H -0.0038 0.0196 0.0899 0.024 Uiso 0.33333 1 calc PR C -1 C23 C 0.02123(6) -0.00617(6) 0.2118(2) 0.0176(4) Uani 0.33333 1 d PD C -1 H231 H 0.0346 -0.0059 0.2732 0.026 Uiso 0.33333 1 calc PR C -1 H232 H 0.0315 0.0017 0.1352 0.026 Uiso 0.33333 1 calc PR C -1 H233 H 0.0057 -0.0260 0.1990 0.026 Uiso 0.33333 1 calc PR C -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.01334(17) 0.01215(16) 0.01083(16) 0.00208(13) 0.00276(13) 0.00739(14) O2A 0.01034(14) 0.01043(14) 0.00974(14) -0.00163(11) -0.00184(11) 0.00638(12) C1A 0.00979(17) 0.00818(16) 0.00912(17) 0.00021(13) -0.00046(14) 0.00500(14) C2A 0.00942(17) 0.00830(16) 0.00937(17) -0.00050(13) -0.00075(14) 0.00511(14) C3A 0.01026(17) 0.00849(16) 0.00921(17) -0.00022(13) -0.00068(14) 0.00552(14) C4A 0.01059(17) 0.00756(16) 0.00862(16) -0.00009(13) -0.00054(14) 0.00518(14) C5A 0.01170(18) 0.00785(16) 0.00920(17) 0.00020(13) -0.00079(14) 0.00542(15) C6A 0.0128(2) 0.00847(17) 0.0123(2) -0.00115(15) -0.00117(16) 0.00495(16) C7A 0.01143(19) 0.01109(18) 0.01000(18) -0.00068(15) -0.00128(15) 0.00690(16) C8A 0.01163(19) 0.01209(19) 0.01133(19) 0.00006(15) -0.00107(15) 0.00756(17) C9A 0.01105(19) 0.01100(19) 0.0127(2) -0.00020(16) -0.00003(16) 0.00717(16) C10A 0.01057(18) 0.00994(18) 0.01108(19) -0.00145(15) -0.00057(15) 0.00600(15) C11A 0.01140(18) 0.00808(16) 0.00878(17) 0.00034(13) 0.00004(14) 0.00555(15) C12A 0.0136(2) 0.00991(18) 0.01037(18) 0.00159(15) 0.00160(15) 0.00752(16) C13A 0.0138(2) 0.01058(18) 0.01084(19) 0.00120(15) 0.00184(16) 0.00782(17) C14A 0.01181(19) 0.01013(18) 0.00917(17) 0.00074(14) 0.00101(14) 0.00619(16) C15A 0.0129(2) 0.00929(17) 0.00995(18) 0.00112(14) 0.00089(15) 0.00648(16) C16A 0.01237(19) 0.00884(17) 0.00984(18) 0.00087(14) 0.00053(15) 0.00638(15) C17A 0.0128(2) 0.0120(2) 0.01040(19) 0.00036(15) -0.00188(16) 0.00688(17) C18A 0.01090(19) 0.01031(19) 0.0120(2) 0.00115(15) 0.00050(16) 0.00415(16) O1B 0.01136(16) 0.01324(17) 0.01286(17) -0.00402(14) -0.00252(13) 0.00616(14) O2B 0.00735(13) 0.01076(14) 0.00941(14) 0.00241(11) 0.00072(11) 0.00384(11) C1B 0.00767(16) 0.00849(16) 0.00924(17) 0.00081(13) 0.00097(13) 0.00391(13) C2B 0.00749(15) 0.00942(17) 0.00919(17) 0.00094(13) 0.00073(13) 0.00422(14) C3B 0.00715(15) 0.00963(17) 0.00875(16) 0.00102(13) 0.00090(13) 0.00413(14) C4B 0.00738(15) 0.00798(15) 0.00805(16) 0.00037(13) 0.00053(12) 0.00396(13) C5B 0.00793(16) 0.00921(16) 0.00891(16) 0.00087(13) 0.00114(13) 0.00482(14) C6B 0.01039(18) 0.00836(17) 0.0126(2) 0.00091(15) 0.00008(15) 0.00507(15) C7B 0.00820(17) 0.01212(19) 0.00983(18) 0.00191(15) 0.00138(14) 0.00444(15) C8B 0.00813(17) 0.0128(2) 0.01141(19) 0.00151(16) 0.00169(15) 0.00457(15) C9B 0.00808(17) 0.0124(2) 0.0123(2) 0.00059(16) 0.00083(15) 0.00494(15) C10B 0.00791(16) 0.01140(18) 0.01098(18) 0.00100(15) 0.00021(14) 0.00514(15) C11B 0.00921(17) 0.00877(16) 0.00879(17) -0.00024(13) 0.00035(13) 0.00441(14) C12B 0.00924(17) 0.01046(18) 0.01055(18) -0.00079(15) -0.00055(14) 0.00464(15) C13B 0.00929(17) 0.01073(18) 0.01140(19) -0.00075(15) -0.00059(15) 0.00468(15) C14B 0.00973(17) 0.01000(18) 0.01023(18) -0.00082(14) -0.00053(14) 0.00455(15) C15B 0.00993(18) 0.01205(19) 0.01141(19) -0.00146(16) 0.00019(15) 0.00582(16) C16B 0.00994(18) 0.01150(19) 0.01082(19) -0.00097(15) 0.00041(15) 0.00576(16) C17B 0.01098(19) 0.01195(19) 0.00998(18) 0.00209(15) 0.00253(15) 0.00545(16) C18B 0.0138(2) 0.00968(18) 0.0126(2) 0.00021(15) 0.00134(17) 0.00662(17) O1C 0.01159(16) 0.01113(15) 0.01184(16) 0.00211(13) -0.00094(13) 0.00556(13) O2C 0.01102(14) 0.00752(13) 0.00907(14) -0.00037(11) 0.00176(11) 0.00449(11) C1C 0.00923(17) 0.00769(16) 0.00908(17) -0.00082(13) 0.00074(13) 0.00399(14) C2C 0.00801(16) 0.00731(15) 0.00911(17) -0.00044(13) 0.00057(13) 0.00377(13) C3C 0.00787(15) 0.00698(15) 0.00893(16) -0.00045(13) 0.00072(13) 0.00334(13) C4C 0.00780(16) 0.00756(15) 0.00924(17) -0.00056(13) 0.00078(13) 0.00320(13) C5C 0.00839(16) 0.00836(16) 0.00976(17) -0.00166(14) 0.00048(14) 0.00287(14) C6C 0.00862(17) 0.01140(19) 0.0136(2) -0.00034(16) 0.00142(15) 0.00467(15) C7C 0.00983(17) 0.00789(16) 0.00995(18) -0.00118(13) 0.00046(14) 0.00411(14) C8C 0.01015(18) 0.00765(16) 0.01135(19) -0.00140(14) -0.00032(15) 0.00412(14) C9C 0.00948(17) 0.00736(16) 0.0126(2) 0.00008(14) 0.00011(15) 0.00380(14) C10C 0.00915(17) 0.00815(16) 0.01084(18) 0.00056(14) 0.00120(14) 0.00413(14) C11C 0.00929(17) 0.00746(16) 0.00902(17) -0.00012(13) 0.00066(13) 0.00343(14) C12C 0.00964(17) 0.00833(17) 0.01092(18) 0.00023(14) -0.00017(14) 0.00330(14) C13C 0.01052(18) 0.00859(17) 0.01112(19) 0.00077(14) 0.00021(15) 0.00399(15) C14C 0.01045(18) 0.00888(17) 0.00939(17) 0.00082(14) 0.00030(14) 0.00497(15) C15C 0.01071(18) 0.00848(17) 0.01021(18) 0.00064(14) -0.00052(14) 0.00419(15) C16C 0.00991(17) 0.00768(16) 0.01002(18) 0.00075(14) 0.00025(14) 0.00357(14) C17C 0.0134(2) 0.01067(19) 0.01039(19) -0.00236(15) 0.00048(16) 0.00576(17) C18C 0.01083(18) 0.01063(18) 0.01139(19) 0.00051(15) 0.00069(15) 0.00582(16) O1D 0.0275(3) 0.0164(2) 0.0141(2) 0.00683(16) 0.01073(19) 0.0139(2) O2D 0.01804(19) 0.01248(16) 0.00831(14) -0.00162(12) -0.00145(13) 0.00985(15) C1D 0.0168(2) 0.01065(19) 0.00799(17) -0.00053(14) -0.00112(16) 0.00822(18) C2D 0.0151(2) 0.00909(17) 0.00824(17) 0.00001(14) 0.00035(15) 0.00712(16) C3D 0.0135(2) 0.00855(16) 0.00801(17) 0.00018(13) 0.00031(14) 0.00646(15) C4D 0.01283(19) 0.00789(16) 0.00757(16) 0.00018(13) 0.00000(14) 0.00588(15) C5D 0.0160(2) 0.00927(17) 0.00800(17) 0.00038(14) -0.00063(15) 0.00768(17) C6D 0.0138(2) 0.00834(17) 0.0122(2) -0.00055(15) -0.00032(16) 0.00539(16) C7D 0.0146(2) 0.01052(18) 0.00902(18) 0.00019(14) -0.00009(15) 0.00771(17) C8D 0.0155(2) 0.01143(19) 0.01086(19) 0.00073(15) 0.00053(17) 0.00866(18) C9D 0.0159(2) 0.01097(19) 0.0116(2) 0.00054(16) 0.00165(17) 0.00851(18) C10D 0.0164(2) 0.01033(18) 0.00990(19) -0.00017(15) 0.00128(16) 0.00817(17) C11D 0.01327(19) 0.00798(16) 0.00751(16) 0.00031(13) -0.00005(14) 0.00611(15) C12D 0.0139(2) 0.00948(17) 0.00925(17) 0.00119(14) 0.00088(15) 0.00717(16) C13D 0.0161(2) 0.01119(19) 0.01006(19) 0.00212(15) 0.00228(16) 0.00854(18) C14D 0.0188(2) 0.0116(2) 0.00927(19) 0.00265(15) 0.00356(17) 0.00897(19) C15D 0.0201(3) 0.01057(19) 0.01003(19) 0.00267(15) 0.00342(18) 0.00920(19) C16D 0.0169(2) 0.00909(17) 0.00924(18) 0.00126(14) 0.00157(16) 0.00786(17) C17D 0.0232(3) 0.0167(2) 0.00871(19) -0.00079(17) -0.00288(19) 0.0128(2) C18D 0.0182(3) 0.0118(2) 0.0106(2) -0.00077(16) -0.00040(18) 0.00689(19) O10 0.0115(3) 0.0122(3) 0.0140(3) -0.0020(2) -0.0017(2) 0.0069(2) C11 0.0101(3) 0.0105(3) 0.0107(3) -0.0002(2) 0.0007(2) 0.0052(2) C12 0.0110(5) 0.0146(5) 0.0116(4) -0.0039(4) -0.0043(4) 0.0078(4) C13 0.0148(7) 0.0128(7) 0.0107(4) -0.0028(3) -0.0005(4) 0.0086(6) O10' 0.0162(8) 0.0252(10) 0.0147(7) -0.0044(7) -0.0027(6) 0.0134(7) C11' 0.0180(8) 0.0184(8) 0.0142(7) 0.0039(6) 0.0035(6) 0.0122(7) C12' 0.029(3) 0.046(4) 0.055(4) -0.004(3) 0.000(3) 0.026(3) C13' 0.022(2) 0.019(2) 0.071(4) -0.001(3) -0.003(3) 0.015(2) O20 0.0224(12) 0.0201(10) 0.0108(5) 0.0015(6) 0.0069(6) 0.0086(6) C21 0.0172(7) 0.0113(6) 0.0098(6) 0.0002(5) 0.0006(5) 0.0091(5) C22 0.0165(8) 0.0217(9) 0.0143(7) -0.0006(6) -0.0029(6) 0.0128(7) C23 0.0233(9) 0.0243(10) 0.0154(8) -0.0055(7) -0.0040(7) 0.0195(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 O1A C14A 1.3752(8) . ? O1A H1A 0.8500 . ? O2A C2A 1.3657(7) . ? O2A C1A 1.4572(7) . ? C1A C17A 1.5219(9) . ? C1A C5A 1.5234(8) . ? C1A C18A 1.5271(9) . ? C2A C3A 1.4011(8) . ? C2A C10A 1.4029(8) . ? C3A C7A 1.4025(8) . ? C3A C4A 1.5201(8) . ? C4A C11A 1.5365(9) . ? C4A C5A 1.5415(8) . ? C4A C6A 1.5437(9) . ? C5A H5AA 0.9900 . ? C5A H5AB 0.9900 . ? C6A H6AA 0.9800 . ? C6A H6AB 0.9800 . ? C6A H6AC 0.9800 . ? C7A C8A 1.3878(9) . ? C7A H7A 0.9500 . ? C8A C9A 1.3948(9) . ? C8A H8A 0.9500 . ? C9A C10A 1.3878(9) . ? C9A H9A 0.9500 . ? C10A H10A 0.9500 . ? C11A C16A 1.3958(8) . ? C11A C12A 1.4030(8) . ? C12A C13A 1.3882(9) . ? C12A H12A 0.9500 . ? C13A C14A 1.3943(9) . ? C13A H13A 0.9500 . ? C14A C15A 1.3867(9) . ? C15A C16A 1.3923(9) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? O1B C14B 1.3681(8) . ? O1B H1B 0.8500 . ? O2B C2B 1.3652(7) . ? O2B C1B 1.4538(7) . ? C1B C17B 1.5210(8) . ? C1B C5B 1.5247(8) . ? C1B C18B 1.5295(9) . ? C2B C3B 1.4018(8) . ? C2B C10B 1.4032(8) . ? C3B C7B 1.4025(8) . ? C3B C4B 1.5210(8) . ? C4B C11B 1.5382(8) . ? C4B C5B 1.5442(8) . ? C4B C6B 1.5484(8) . ? C5B H5BA 0.9900 . ? C5B H5BB 0.9900 . ? C6B H6BA 0.9800 . ? C6B H6BB 0.9800 . ? C6B H6BC 0.9800 . ? C7B C8B 1.3893(9) . ? C7B H7B 0.9500 . ? C8B C9B 1.3956(9) . ? C8B H8B 0.9500 . ? C9B C10B 1.3847(9) . ? C9B H9B 0.9500 . ? C10B H10B 0.9500 . ? C11B C16B 1.3923(9) . ? C11B C12B 1.4065(9) . ? C12B C13B 1.3857(9) . ? C12B H12B 0.9500 . ? C13B C14B 1.3910(9) . ? C13B H13B 0.9500 . ? C14B C15B 1.3913(9) . ? C15B C16B 1.4042(9) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 0.9800 . ? O1C C14C 1.3710(8) . ? O1C H1C 0.8500 . ? O2C C2C 1.3670(7) . ? O2C C1C 1.4546(7) . ? C1C C17C 1.5197(9) . ? C1C C5C 1.5253(8) . ? C1C C18C 1.5285(9) . ? C2C C3C 1.4008(8) . ? C2C C10C 1.4018(8) . ? C3C C7C 1.4014(8) . ? C3C C4C 1.5199(8) . ? C4C C11C 1.5334(9) . ? C4C C5C 1.5392(8) . ? C4C C6C 1.5481(8) . ? C5C H5CA 0.9900 . ? C5C H5CB 0.9900 . ? C6C H6CA 0.9800 . ? C6C H6CB 0.9800 . ? C6C H6CC 0.9800 . ? C7C C8C 1.3882(8) . ? C7C H7C 0.9500 . ? C8C C9C 1.3953(9) . ? C8C H8C 0.9500 . ? C9C C10C 1.3879(9) . ? C9C H9C 0.9500 . ? C10C H10C 0.9500 . ? C11C C16C 1.3962(9) . ? C11C C12C 1.4000(8) . ? C12C C13C 1.3893(9) . ? C12C H12C 0.9500 . ? C13C C14C 1.3922(9) . ? C13C H13C 0.9500 . ? C14C C15C 1.3927(8) . ? C15C C16C 1.3901(9) . ? C15C H15C 0.9500 . ? C16C H16C 0.9500 . ? C17C H17G 0.9800 . ? C17C H17H 0.9800 . ? C17C H17I 0.9800 . ? C18C H18G 0.9800 . ? C18C H18H 0.9800 . ? C18C H18I 0.9800 . ? O1D C14D 1.3724(9) . ? O1D H1D 0.8500 . ? O2D C2D 1.3656(8) . ? O2D C1D 1.4563(9) . ? C1D C17D 1.5210(9) . ? C1D C18D 1.5230(10) . ? C1D C5D 1.5244(9) . ? C2D C3D 1.4023(8) . ? C2D C10D 1.4024(9) . ? C3D C7D 1.4025(9) . ? C3D C4D 1.5219(8) . ? C4D C11D 1.5377(9) . ? C4D C5D 1.5407(9) . ? C4D C6D 1.5434(9) . ? C5D H5DA 0.9900 . ? C5D H5DB 0.9900 . ? C6D H6DA 0.9800 . ? C6D H6DB 0.9800 . ? C6D H6DC 0.9800 . ? C7D C8D 1.3879(9) . ? C7D H7D 0.9500 . ? C8D C9D 1.3954(9) . ? C8D H8D 0.9500 . ? C9D C10D 1.3849(10) . ? C9D H9D 0.9500 . ? C10D H10D 0.9500 . ? C11D C16D 1.3956(8) . ? C11D C12D 1.4019(9) . ? C12D C13D 1.3921(9) . ? C12D H12D 0.9500 . ? C13D C14D 1.3945(9) . ? C13D H13D 0.9500 . ? C14D C15D 1.3898(10) . ? C15D C16D 1.3927(9) . ? C15D H15D 0.9500 . ? C16D H16D 0.9500 . ? C17D H17J 0.9800 . ? C17D H17K 0.9800 . ? C17D H17L 0.9800 . ? C18D H18J 0.9800 . ? C18D H18K 0.9800 . ? C18D H18L 0.9800 . ? O10 C11 1.4468(13) . ? O10 H10 0.8500 . ? C11 C12 1.510(2) . ? C11 C13 1.529(3) . ? C11 H11 1.0000 . ? C12 H121 0.9800 . ? C12 H122 0.9800 . ? C12 H123 0.9800 . ? C13 H131 0.9800 . ? C13 H132 0.9800 . ? C13 H133 0.9800 . ? O10' C11' 1.448(3) . ? O10' H10' 0.8500 . ? C11' C12' 1.506(9) . ? C11' C13' 1.514(8) . ? C11' H11' 1.0000 . ? C12' H124 0.9800 . ? C12' H125 0.9800 . ? C12' H126 0.9800 . ? C13' H134 0.9800 . ? C13' H135 0.9800 . ? C13' H136 0.9800 . ? O20 C21 1.429(3) . ? O20 H20 0.8500 . ? C21 C22 1.502(3) . ? C21 C23 1.522(3) . ? C21 H21 1.0000 . ? C22 H221 0.9800 . ? C22 H222 0.9800 . ? C22 H223 0.9800 . ? C23 H231 0.9800 . ? C23 H232 0.9800 . ? C23 H233 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14A O1A H1A 109.5 . . ? C2A O2A C1A 117.16(5) . . ? O2A C1A C17A 105.15(5) . . ? O2A C1A C5A 108.63(5) . . ? C17A C1A C5A 109.71(5) . . ? O2A C1A C18A 107.95(5) . . ? C17A C1A C18A 110.31(5) . . ? C5A C1A C18A 114.63(5) . . ? O2A C2A C3A 124.31(5) . . ? O2A C2A C10A 115.24(5) . . ? C3A C2A C10A 120.41(5) . . ? C2A C3A C7A 117.82(5) . . ? C2A C3A C4A 121.53(5) . . ? C7A C3A C4A 120.65(5) . . ? C3A C4A C11A 111.41(5) . . ? C3A C4A C5A 108.14(5) . . ? C11A C4A C5A 111.98(5) . . ? C3A C4A C6A 109.72(5) . . ? C11A C4A C6A 108.54(5) . . ? C5A C4A C6A 106.95(5) . . ? C1A C5A C4A 115.21(5) . . ? C1A C5A H5AA 108.5 . . ? C4A C5A H5AA 108.5 . . ? C1A C5A H5AB 108.5 . . ? C4A C5A H5AB 108.5 . . ? H5AA C5A H5AB 107.5 . . ? C4A C6A H6AA 109.5 . . ? C4A C6A H6AB 109.5 . . ? H6AA C6A H6AB 109.5 . . ? C4A C6A H6AC 109.5 . . ? H6AA C6A H6AC 109.5 . . ? H6AB C6A H6AC 109.5 . . ? C8A C7A C3A 122.08(6) . . ? C8A C7A H7A 119.0 . . ? C3A C7A H7A 119.0 . . ? C7A C8A C9A 119.32(6) . . ? C7A C8A H8A 120.3 . . ? C9A C8A H8A 120.3 . . ? C10A C9A C8A 119.88(6) . . ? C10A C9A H9A 120.1 . . ? C8A C9A H9A 120.1 . . ? C9A C10A C2A 120.47(6) . . ? C9A C10A H10A 119.8 . . ? C2A C10A H10A 119.8 . . ? C16A C11A C12A 117.35(6) . . ? C16A C11A C4A 122.90(5) . . ? C12A C11A C4A 119.75(5) . . ? C13A C12A C11A 121.56(6) . . ? C13A C12A H12A 119.2 . . ? C11A C12A H12A 119.2 . . ? C12A C13A C14A 119.68(6) . . ? C12A C13A H13A 120.2 . . ? C14A C13A H13A 120.2 . . ? O1A C14A C15A 121.98(6) . . ? O1A C14A C13A 118.00(6) . . ? C15A C14A C13A 120.00(6) . . ? C14A C15A C16A 119.60(6) . . ? C14A C15A H15A 120.2 . . ? C16A C15A H15A 120.2 . . ? C15A C16A C11A 121.81(6) . . ? C15A C16A H16A 119.1 . . ? C11A C16A H16A 119.1 . . ? C1A C17A H17A 109.5 . . ? C1A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C1A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C1A C18A H18A 109.5 . . ? C1A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C1A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C14B O1B H1B 109.5 . . ? C2B O2B C1B 116.93(5) . . ? O2B C1B C17B 105.01(5) . . ? O2B C1B C5B 108.41(5) . . ? C17B C1B C5B 109.68(5) . . ? O2B C1B C18B 107.88(5) . . ? C17B C1B C18B 110.54(5) . . ? C5B C1B C18B 114.82(5) . . ? O2B C2B C3B 124.34(5) . . ? O2B C2B C10B 114.84(5) . . ? C3B C2B C10B 120.75(5) . . ? C2B C3B C7B 117.44(5) . . ? C2B C3B C4B 121.68(5) . . ? C7B C3B C4B 120.61(5) . . ? C3B C4B C11B 114.00(5) . . ? C3B C4B C5B 108.16(5) . . ? C11B C4B C5B 111.03(5) . . ? C3B C4B C6B 108.42(5) . . ? C11B C4B C6B 108.44(5) . . ? C5B C4B C6B 106.49(5) . . ? C1B C5B C4B 115.37(5) . . ? C1B C5B H5BA 108.4 . . ? C4B C5B H5BA 108.4 . . ? C1B C5B H5BB 108.4 . . ? C4B C5B H5BB 108.4 . . ? H5BA C5B H5BB 107.5 . . ? C4B C6B H6BA 109.5 . . ? C4B C6B H6BB 109.5 . . ? H6BA C6B H6BB 109.5 . . ? C4B C6B H6BC 109.5 . . ? H6BA C6B H6BC 109.5 . . ? H6BB C6B H6BC 109.5 . . ? C8B C7B C3B 122.09(6) . . ? C8B C7B H7B 119.0 . . ? C3B C7B H7B 119.0 . . ? C7B C8B C9B 119.54(6) . . ? C7B C8B H8B 120.2 . . ? C9B C8B H8B 120.2 . . ? C10B C9B C8B 119.67(6) . . ? C10B C9B H9B 120.2 . . ? C8B C9B H9B 120.2 . . ? C9B C10B C2B 120.49(6) . . ? C9B C10B H10B 119.8 . . ? C2B C10B H10B 119.8 . . ? C16B C11B C12B 116.87(6) . . ? C16B C11B C4B 125.02(5) . . ? C12B C11B C4B 118.11(5) . . ? C13B C12B C11B 122.02(6) . . ? C13B C12B H12B 119.0 . . ? C11B C12B H12B 119.0 . . ? C12B C13B C14B 120.06(6) . . ? C12B C13B H13B 120.0 . . ? C14B C13B H13B 120.0 . . ? O1B C14B C13B 116.29(6) . . ? O1B C14B C15B 124.21(6) . . ? C13B C14B C15B 119.51(6) . . ? C14B C15B C16B 119.66(6) . . ? C14B C15B H15B 120.2 . . ? C16B C15B H15B 120.2 . . ? C11B C16B C15B 121.88(6) . . ? C11B C16B H16B 119.1 . . ? C15B C16B H16B 119.1 . . ? C1B C17B H17D 109.5 . . ? C1B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C1B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C1B C18B H18D 109.5 . . ? C1B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C1B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C14C O1C H1C 109.5 . . ? C2C O2C C1C 116.85(5) . . ? O2C C1C C17C 105.39(5) . . ? O2C C1C C5C 108.43(5) . . ? C17C C1C C5C 109.02(5) . . ? O2C C1C C18C 107.91(5) . . ? C17C C1C C18C 110.38(5) . . ? C5C C1C C18C 115.24(5) . . ? O2C C2C C3C 124.17(5) . . ? O2C C2C C10C 115.10(5) . . ? C3C C2C C10C 120.69(5) . . ? C2C C3C C7C 117.65(5) . . ? C2C C3C C4C 121.66(5) . . ? C7C C3C C4C 120.68(5) . . ? C3C C4C C11C 111.66(5) . . ? C3C C4C C5C 108.31(5) . . ? C11C C4C C5C 111.16(5) . . ? C3C C4C C6C 109.79(5) . . ? C11C C4C C6C 108.97(5) . . ? C5C C4C C6C 106.83(5) . . ? C1C C5C C4C 115.34(5) . . ? C1C C5C H5CA 108.4 . . ? C4C C5C H5CA 108.4 . . ? C1C C5C H5CB 108.4 . . ? C4C C5C H5CB 108.4 . . ? H5CA C5C H5CB 107.5 . . ? C4C C6C H6CA 109.5 . . ? C4C C6C H6CB 109.5 . . ? H6CA C6C H6CB 109.5 . . ? C4C C6C H6CC 109.5 . . ? H6CA C6C H6CC 109.5 . . ? H6CB C6C H6CC 109.5 . . ? C8C C7C C3C 122.08(6) . . ? C8C C7C H7C 119.0 . . ? C3C C7C H7C 119.0 . . ? C7C C8C C9C 119.42(5) . . ? C7C C8C H8C 120.3 . . ? C9C C8C H8C 120.3 . . ? C10C C9C C8C 119.80(5) . . ? C10C C9C H9C 120.1 . . ? C8C C9C H9C 120.1 . . ? C9C C10C C2C 120.35(6) . . ? C9C C10C H10C 119.8 . . ? C2C C10C H10C 119.8 . . ? C16C C11C C12C 117.58(6) . . ? C16C C11C C4C 123.23(5) . . ? C12C C11C C4C 119.17(5) . . ? C13C C12C C11C 121.58(6) . . ? C13C C12C H12C 119.2 . . ? C11C C12C H12C 119.2 . . ? C12C C13C C14C 119.62(6) . . ? C12C C13C H13C 120.2 . . ? C14C C13C H13C 120.2 . . ? O1C C14C C13C 118.22(5) . . ? O1C C14C C15C 121.81(6) . . ? C13C C14C C15C 119.97(6) . . ? C16C C15C C14C 119.59(6) . . ? C16C C15C H15C 120.2 . . ? C14C C15C H15C 120.2 . . ? C15C C16C C11C 121.65(5) . . ? C15C C16C H16C 119.2 . . ? C11C C16C H16C 119.2 . . ? C1C C17C H17G 109.5 . . ? C1C C17C H17H 109.5 . . ? H17G C17C H17H 109.5 . . ? C1C C17C H17I 109.5 . . ? H17G C17C H17I 109.5 . . ? H17H C17C H17I 109.5 . . ? C1C C18C H18G 109.5 . . ? C1C C18C H18H 109.5 . . ? H18G C18C H18H 109.5 . . ? C1C C18C H18I 109.5 . . ? H18G C18C H18I 109.5 . . ? H18H C18C H18I 109.5 . . ? C14D O1D H1D 109.5 . . ? C2D O2D C1D 117.57(5) . . ? O2D C1D C17D 105.03(5) . . ? O2D C1D C18D 107.90(5) . . ? C17D C1D C18D 110.57(6) . . ? O2D C1D C5D 108.98(6) . . ? C17D C1D C5D 109.39(5) . . ? C18D C1D C5D 114.52(5) . . ? O2D C2D C3D 124.44(6) . . ? O2D C2D C10D 114.99(5) . . ? C3D C2D C10D 120.52(6) . . ? C2D C3D C7D 117.64(6) . . ? C2D C3D C4D 121.49(6) . . ? C7D C3D C4D 120.85(5) . . ? C3D C4D C11D 111.87(5) . . ? C3D C4D C5D 107.98(5) . . ? C11D C4D C5D 111.92(5) . . ? C3D C4D C6D 109.65(5) . . ? C11D C4D C6D 108.81(5) . . ? C5D C4D C6D 106.46(5) . . ? C1D C5D C4D 115.41(5) . . ? C1D C5D H5DA 108.4 . . ? C4D C5D H5DA 108.4 . . ? C1D C5D H5DB 108.4 . . ? C4D C5D H5DB 108.4 . . ? H5DA C5D H5DB 107.5 . . ? C4D C6D H6DA 109.5 . . ? C4D C6D H6DB 109.5 . . ? H6DA C6D H6DB 109.5 . . ? C4D C6D H6DC 109.5 . . ? H6DA C6D H6DC 109.5 . . ? H6DB C6D H6DC 109.5 . . ? C8D C7D C3D 122.08(6) . . ? C8D C7D H7D 119.0 . . ? C3D C7D H7D 119.0 . . ? C7D C8D C9D 119.41(6) . . ? C7D C8D H8D 120.3 . . ? C9D C8D H8D 120.3 . . ? C10D C9D C8D 119.81(6) . . ? C10D C9D H9D 120.1 . . ? C8D C9D H9D 120.1 . . ? C9D C10D C2D 120.54(6) . . ? C9D C10D H10D 119.7 . . ? C2D C10D H10D 119.7 . . ? C16D C11D C12D 117.22(6) . . ? C16D C11D C4D 122.73(5) . . ? C12D C11D C4D 120.05(5) . . ? C13D C12D C11D 121.63(6) . . ? C13D C12D H12D 119.2 . . ? C11D C12D H12D 119.2 . . ? C12D C13D C14D 119.82(6) . . ? C12D C13D H13D 120.1 . . ? C14D C13D H13D 120.1 . . ? O1D C14D C15D 117.83(6) . . ? O1D C14D C13D 122.53(6) . . ? C15D C14D C13D 119.64(6) . . ? C14D C15D C16D 119.77(6) . . ? C14D C15D H15D 120.1 . . ? C16D C15D H15D 120.1 . . ? C15D C16D C11D 121.92(6) . . ? C15D C16D H16D 119.0 . . ? C11D C16D H16D 119.0 . . ? C1D C17D H17J 109.5 . . ? C1D C17D H17K 109.5 . . ? H17J C17D H17K 109.5 . . ? C1D C17D H17L 109.5 . . ? H17J C17D H17L 109.5 . . ? H17K C17D H17L 109.5 . . ? C1D C18D H18J 109.5 . . ? C1D C18D H18K 109.5 . . ? H18J C18D H18K 109.5 . . ? C1D C18D H18L 109.5 . . ? H18J C18D H18L 109.5 . . ? H18K C18D H18L 109.5 . . ? C11 O10 H10 109.5 . . ? O10 C11 C12 107.04(11) . . ? O10 C11 C13 110.26(12) . . ? C12 C11 C13 112.07(13) . . ? O10 C11 H11 109.1 . . ? C12 C11 H11 109.1 . . ? C13 C11 H11 109.1 . . ? C11 C12 H121 109.5 . . ? C11 C12 H122 109.5 . . ? H121 C12 H122 109.5 . . ? C11 C12 H123 109.5 . . ? H121 C12 H123 109.5 . . ? H122 C12 H123 109.5 . . ? C11 C13 H131 109.5 . . ? C11 C13 H132 109.5 . . ? H131 C13 H132 109.5 . . ? C11 C13 H133 109.5 . . ? H131 C13 H133 109.5 . . ? H132 C13 H133 109.5 . . ? C11' O10' H10' 109.5 . . ? O10' C11' C12' 110.3(4) . . ? O10' C11' C13' 111.7(4) . . ? C12' C11' C13' 110.7(5) . . ? O10' C11' H11' 108.0 . . ? C12' C11' H11' 108.0 . . ? C13' C11' H11' 108.0 . . ? C11' C12' H124 109.5 . . ? C11' C12' H125 109.5 . . ? H124 C12' H125 109.5 . . ? C11' C12' H126 109.5 . . ? H124 C12' H126 109.5 . . ? H125 C12' H126 109.5 . . ? C11' C13' H134 109.5 . . ? C11' C13' H135 109.5 . . ? H134 C13' H135 109.5 . . ? C11' C13' H136 109.5 . . ? H134 C13' H136 109.5 . . ? H135 C13' H136 109.5 . . ? C21 O20 H20 109.5 . . ? O20 C21 C22 109.8(2) . . ? O20 C21 C23 110.64(18) . . ? C22 C21 C23 112.23(18) . . ? O20 C21 H21 108.0 . . ? C22 C21 H21 108.0 . . ? C23 C21 H21 108.0 . . ? C21 C22 H221 109.5 . . ? C21 C22 H222 109.5 . . ? H221 C22 H222 109.5 . . ? C21 C22 H223 109.5 . . ? H221 C22 H223 109.5 . . ? H222 C22 H223 109.5 . . ? C21 C23 H231 109.5 . . ? C21 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? C21 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2A O2A C1A C17A -161.81(5) . . . . ? C2A O2A C1A C5A -44.42(7) . . . . ? C2A O2A C1A C18A 80.44(6) . . . . ? C1A O2A C2A C3A 18.67(9) . . . . ? C1A O2A C2A C10A -163.63(5) . . . . ? O2A C2A C3A C7A 177.36(6) . . . . ? C10A C2A C3A C7A -0.23(9) . . . . ? O2A C2A C3A C4A -2.43(9) . . . . ? C10A C2A C3A C4A 179.98(6) . . . . ? C2A C3A C4A C11A -109.36(6) . . . . ? C7A C3A C4A C11A 70.86(7) . . . . ? C2A C3A C4A C5A 14.10(8) . . . . ? C7A C3A C4A C5A -165.68(6) . . . . ? C2A C3A C4A C6A 130.41(6) . . . . ? C7A C3A C4A C6A -49.36(8) . . . . ? O2A C1A C5A C4A 58.30(7) . . . . ? C17A C1A C5A C4A 172.74(5) . . . . ? C18A C1A C5A C4A -62.52(7) . . . . ? C3A C4A C5A C1A -42.25(7) . . . . ? C11A C4A C5A C1A 80.87(6) . . . . ? C6A C4A C5A C1A -160.35(5) . . . . ? C2A C3A C7A C8A 1.46(10) . . . . ? C4A C3A C7A C8A -178.76(6) . . . . ? C3A C7A C8A C9A -1.22(10) . . . . ? C7A C8A C9A C10A -0.27(10) . . . . ? C8A C9A C10A C2A 1.46(10) . . . . ? O2A C2A C10A C9A -179.01(6) . . . . ? C3A C2A C10A C9A -1.21(10) . . . . ? C3A C4A C11A C16A -2.69(8) . . . . ? C5A C4A C11A C16A -123.94(6) . . . . ? C6A C4A C11A C16A 118.22(6) . . . . ? C3A C4A C11A C12A 177.68(6) . . . . ? C5A C4A C11A C12A 56.44(7) . . . . ? C6A C4A C11A C12A -61.40(7) . . . . ? C16A C11A C12A C13A 0.20(10) . . . . ? C4A C11A C12A C13A 179.84(6) . . . . ? C11A C12A C13A C14A -0.27(10) . . . . ? C12A C13A C14A O1A 178.65(6) . . . . ? C12A C13A C14A C15A 0.14(10) . . . . ? O1A C14A C15A C16A -178.41(6) . . . . ? C13A C14A C15A C16A 0.05(10) . . . . ? C14A C15A C16A C11A -0.12(10) . . . . ? C12A C11A C16A C15A -0.01(9) . . . . ? C4A C11A C16A C15A -179.64(6) . . . . ? C2B O2B C1B C17B -162.28(5) . . . . ? C2B O2B C1B C5B -45.11(7) . . . . ? C2B O2B C1B C18B 79.80(6) . . . . ? C1B O2B C2B C3B 15.78(9) . . . . ? C1B O2B C2B C10B -167.05(5) . . . . ? O2B C2B C3B C7B 178.52(6) . . . . ? C10B C2B C3B C7B 1.51(9) . . . . ? O2B C2B C3B C4B 4.34(9) . . . . ? C10B C2B C3B C4B -172.66(6) . . . . ? C2B C3B C4B C11B -115.99(6) . . . . ? C7B C3B C4B C11B 70.02(7) . . . . ? C2B C3B C4B C5B 8.03(7) . . . . ? C7B C3B C4B C5B -165.96(6) . . . . ? C2B C3B C4B C6B 123.13(6) . . . . ? C7B C3B C4B C6B -50.87(7) . . . . ? O2B C1B C5B C4B 58.97(6) . . . . ? C17B C1B C5B C4B 173.10(5) . . . . ? C18B C1B C5B C4B -61.73(7) . . . . ? C3B C4B C5B C1B -39.58(7) . . . . ? C11B C4B C5B C1B 86.20(6) . . . . ? C6B C4B C5B C1B -155.94(5) . . . . ? C2B C3B C7B C8B -0.70(10) . . . . ? C4B C3B C7B C8B 173.54(6) . . . . ? C3B C7B C8B C9B -0.43(10) . . . . ? C7B C8B C9B C10B 0.77(10) . . . . ? C8B C9B C10B C2B 0.04(10) . . . . ? O2B C2B C10B C9B -178.49(6) . . . . ? C3B C2B C10B C9B -1.21(10) . . . . ? C3B C4B C11B C16B 5.82(8) . . . . ? C5B C4B C11B C16B -116.64(6) . . . . ? C6B C4B C11B C16B 126.70(6) . . . . ? C3B C4B C11B C12B -175.06(5) . . . . ? C5B C4B C11B C12B 62.48(7) . . . . ? C6B C4B C11B C12B -54.19(7) . . . . ? C16B C11B C12B C13B 0.25(9) . . . . ? C4B C11B C12B C13B -178.93(6) . . . . ? C11B C12B C13B C14B 0.94(10) . . . . ? C12B C13B C14B O1B 178.58(6) . . . . ? C12B C13B C14B C15B -1.14(10) . . . . ? O1B C14B C15B C16B -179.53(6) . . . . ? C13B C14B C15B C16B 0.17(10) . . . . ? C12B C11B C16B C15B -1.25(9) . . . . ? C4B C11B C16B C15B 177.87(6) . . . . ? C14B C15B C16B C11B 1.06(10) . . . . ? C2C O2C C1C C17C -162.48(5) . . . . ? C2C O2C C1C C5C -45.86(7) . . . . ? C2C O2C C1C C18C 79.59(6) . . . . ? C1C O2C C2C C3C 19.54(8) . . . . ? C1C O2C C2C C10C -162.62(5) . . . . ? O2C C2C C3C C7C 177.86(6) . . . . ? C10C C2C C3C C7C 0.14(9) . . . . ? O2C C2C C3C C4C -1.24(9) . . . . ? C10C C2C C3C C4C -178.96(5) . . . . ? C2C C3C C4C C11C -110.80(6) . . . . ? C7C C3C C4C C11C 70.12(7) . . . . ? C2C C3C C4C C5C 11.91(8) . . . . ? C7C C3C C4C C5C -167.16(5) . . . . ? C2C C3C C4C C6C 128.22(6) . . . . ? C7C C3C C4C C6C -50.85(7) . . . . ? O2C C1C C5C C4C 58.56(7) . . . . ? C17C C1C C5C C4C 172.81(5) . . . . ? C18C C1C C5C C4C -62.46(7) . . . . ? C3C C4C C5C C1C -40.74(7) . . . . ? C11C C4C C5C C1C 82.29(6) . . . . ? C6C C4C C5C C1C -158.94(5) . . . . ? C2C C3C C7C C8C 0.85(9) . . . . ? C4C C3C C7C C8C 179.96(6) . . . . ? C3C C7C C8C C9C -0.92(10) . . . . ? C7C C8C C9C C10C -0.01(9) . . . . ? C8C C9C C10C C2C 0.98(9) . . . . ? O2C C2C C10C C9C -178.97(6) . . . . ? C3C C2C C10C C9C -1.05(9) . . . . ? C3C C4C C11C C16C 2.68(8) . . . . ? C5C C4C C11C C16C -118.39(6) . . . . ? C6C C4C C11C C16C 124.13(6) . . . . ? C3C C4C C11C C12C -178.68(5) . . . . ? C5C C4C C11C C12C 60.25(7) . . . . ? C6C C4C C11C C12C -57.23(7) . . . . ? C16C C11C C12C C13C 0.08(9) . . . . ? C4C C11C C12C C13C -178.64(6) . . . . ? C11C C12C C13C C14C 0.32(10) . . . . ? C12C C13C C14C O1C 178.79(6) . . . . ? C12C C13C C14C C15C -0.42(10) . . . . ? O1C C14C C15C C16C -179.06(6) . . . . ? C13C C14C C15C C16C 0.12(9) . . . . ? C14C C15C C16C C11C 0.29(10) . . . . ? C12C C11C C16C C15C -0.39(9) . . . . ? C4C C11C C16C C15C 178.27(6) . . . . ? C2D O2D C1D C17D 159.43(6) . . . . ? C2D O2D C1D C18D -82.60(7) . . . . ? C2D O2D C1D C5D 42.31(7) . . . . ? C1D O2D C2D C3D -16.51(9) . . . . ? C1D O2D C2D C10D 166.06(6) . . . . ? O2D C2D C3D C7D -176.87(6) . . . . ? C10D C2D C3D C7D 0.43(9) . . . . ? O2D C2D C3D C4D 1.73(10) . . . . ? C10D C2D C3D C4D 179.03(6) . . . . ? C2D C3D C4D C11D 108.87(7) . . . . ? C7D C3D C4D C11D -72.57(7) . . . . ? C2D C3D C4D C5D -14.72(8) . . . . ? C7D C3D C4D C5D 163.84(6) . . . . ? C2D C3D C4D C6D -130.32(6) . . . . ? C7D C3D C4D C6D 48.24(8) . . . . ? O2D C1D C5D C4D -57.58(7) . . . . ? C17D C1D C5D C4D -171.90(6) . . . . ? C18D C1D C5D C4D 63.36(8) . . . . ? C3D C4D C5D C1D 42.78(7) . . . . ? C11D C4D C5D C1D -80.78(7) . . . . ? C6D C4D C5D C1D 160.45(6) . . . . ? C2D C3D C7D C8D -0.57(10) . . . . ? C4D C3D C7D C8D -179.18(6) . . . . ? C3D C7D C8D C9D 0.29(10) . . . . ? C7D C8D C9D C10D 0.15(10) . . . . ? C8D C9D C10D C2D -0.28(10) . . . . ? O2D C2D C10D C9D 177.53(6) . . . . ? C3D C2D C10D C9D -0.02(10) . . . . ? C3D C4D C11D C16D -2.31(8) . . . . ? C5D C4D C11D C16D 119.02(7) . . . . ? C6D C4D C11D C16D -123.61(6) . . . . ? C3D C4D C11D C12D 178.26(6) . . . . ? C5D C4D C11D C12D -60.41(7) . . . . ? C6D C4D C11D C12D 56.96(7) . . . . ? C16D C11D C12D C13D -0.95(10) . . . . ? C4D C11D C12D C13D 178.51(6) . . . . ? C11D C12D C13D C14D -0.20(11) . . . . ? C12D C13D C14D O1D -178.47(7) . . . . ? C12D C13D C14D C15D 1.17(11) . . . . ? O1D C14D C15D C16D 178.70(7) . . . . ? C13D C14D C15D C16D -0.95(11) . . . . ? C14D C15D C16D C11D -0.24(11) . . . . ? C12D C11D C16D C15D 1.17(10) . . . . ? C4D C11D C16D C15D -178.28(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 O1A H1A O1C 0.85 1.89 2.7215(7) 166.9 13 O1B H1B O10 0.85 1.83 2.6117(11) 153.1 13 O1C H1C O1B 0.85 1.83 2.6732(7) 170.8 13 O1D H1D O1D 0.85 1.97 2.8186(7) 178.1 12_556 O10 H10 O1A 0.85 1.95 2.7477(11) 155.5 . O10' H10' O1A 0.85 1.90 2.742(2) 172.9 . O20 H20 O1D 0.85 2.42 3.053(3) 131.9 10_556 _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 28.57 _diffrn_measured_fraction_theta_full 0.887 _refine_diff_density_max 1.910 _refine_diff_density_min -0.732 _refine_diff_density_rms 0.098