# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name M.Crisma _publ_contact_author_email marco.crisma@unipd.it loop_ _publ_author_name F.Fabris 'O.De Lucchi' I.Nardini M.Crisma C.Zonta data_mc41c _database_code_depnum_ccdc_archive 'CCDC 690687' #TrackingRef '- mc41c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1R,2R,4S,5R,6R,8S,9R,10R,12S)-3,4,7,8,11,12-hexahydro-2,6,10-trihydroxy- 1,5,9,13,13',14,14',15,15'-nonamethyl-1,4:5,8:9,12-trimethanotriphenylene x 2.5 H2O ; _chemical_name_common ; (1R,2R,4S,5R,6R,8S,9R,10R,12S)-3,4,7,8,11,12-hexahydro-2,6,10- trihydroxy-1,5,9,13,13',14,14',15,15'-nonamethyl-1,4:5,8:9,12- trimethanotriphenylene x 2.5 H2O ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H47 O5.50' _chemical_formula_weight 495.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M 'P 65 2 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' 'y, x, -z+2/3' 'x-y, -y, -z' '-x, -x+y, -z+1/3' '-y, -x, -z+1/6' '-x+y, y, -z+1/2' 'x, x-y, -z+5/6' _cell_length_a 10.913(2) _cell_length_b 10.913(2) _cell_length_c 81.73(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8429(3) _cell_formula_units_Z 12 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 12 _cell_measurement_theta_max 20 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3252 _exptl_absorpt_coefficient_mu 0.626 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Philips PW1100 diffractometer' _diffrn_measurement_method '\q-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 4993 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 91 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 60.17 _reflns_number_total 4196 _reflns_number_gt 3539 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR2002 (Burla et al. 2002)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0910P)^2^+1.7206P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.8(4) _refine_ls_number_reflns 4196 _refine_ls_number_parameters 341 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1504 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 C1 C 0.5522(3) 0.9131(3) 0.79394(3) 0.0403(6) Uani 1 1 d . . . C2 C 0.6043(3) 1.0604(3) 0.79371(3) 0.0408(6) Uani 1 1 d . . . C3 C 0.7452(3) 1.1525(3) 0.79063(3) 0.0422(6) Uani 1 1 d . . . C4 C 0.8380(3) 1.0995(3) 0.78774(3) 0.0426(6) Uani 1 1 d . . . C5 C 0.7876(3) 0.9570(3) 0.78791(3) 0.0423(6) Uani 1 1 d . . . C6 C 0.6415(3) 0.8619(3) 0.79091(3) 0.0395(6) Uani 1 1 d . . . C7 C 0.3977(3) 0.8450(3) 0.79802(4) 0.0492(7) Uani 1 1 d . . . H7 H 0.3407 0.7445 0.7952 0.059 Uiso 1 1 calc R . . C8 C 0.3925(3) 0.8816(3) 0.81632(4) 0.0584(8) Uani 1 1 d . . . H8A H 0.2969 0.8293 0.8206 0.070 Uiso 1 1 calc R . . H8B H 0.4538 0.8611 0.8230 0.070 Uiso 1 1 calc R . . C9 C 0.4460(3) 1.0418(3) 0.81586(4) 0.0587(8) Uani 1 1 d . . . H9 H 0.3704 1.0594 0.8194 0.070 Uiso 1 1 calc R . . O1 O 0.5664(2) 1.1164(2) 0.82622(3) 0.0693(6) Uani 1 1 d . . . HO1 H 0.5770 1.1945 0.8284 0.104 Uiso 1 1 calc R . . C10 C 0.4787(3) 1.0807(3) 0.79730(4) 0.0502(7) Uani 1 1 d . . . C11 C 0.4904(3) 1.2205(3) 0.79262(5) 0.0708(9) Uani 1 1 d . . . H11A H 0.5136 1.2386 0.7812 0.106 Uiso 1 1 calc R . . H11B H 0.5633 1.2951 0.7990 0.106 Uiso 1 1 calc R . . H11C H 0.4018 1.2163 0.7947 0.106 Uiso 1 1 calc R . . C12 C 0.3572(3) 0.9442(3) 0.78907(4) 0.0577(8) Uani 1 1 d . . . C13 C 0.2081(4) 0.9137(4) 0.79282(6) 0.0884(12) Uani 1 1 d . . . H13A H 0.2016 0.9327 0.8042 0.133 Uiso 1 1 calc R . . H13B H 0.1418 0.8163 0.7905 0.133 Uiso 1 1 calc R . . H13C H 0.1867 0.9731 0.7862 0.133 Uiso 1 1 calc R . . C14 C 0.3734(4) 0.9419(4) 0.77038(4) 0.0768(10) Uani 1 1 d . . . H14A H 0.3495 1.0068 0.7654 0.115 Uiso 1 1 calc R . . H14B H 0.3114 0.8481 0.7663 0.115 Uiso 1 1 calc R . . H14C H 0.4695 0.9693 0.7678 0.115 Uiso 1 1 calc R . . C15 C 0.8342(3) 1.3112(3) 0.78996(4) 0.0525(7) Uani 1 1 d . . . H15 H 0.7822 1.3615 0.7880 0.063 Uiso 1 1 calc R . . C16 C 0.9248(4) 1.3535(3) 0.80570(4) 0.0681(9) Uani 1 1 d . . . H16A H 0.9759 1.4553 0.8072 0.082 Uiso 1 1 calc R . . H16B H 0.8669 1.3091 0.8153 0.082 Uiso 1 1 calc R . . C17 C 1.0267(3) 1.2975(3) 0.80244(4) 0.0677(9) Uani 1 1 d . . . H17 H 1.1228 1.3789 0.8017 0.081 Uiso 1 1 calc R . . O2 O 1.0263(3) 1.2044(3) 0.81466(3) 0.0822(8) Uani 1 1 d . . . HO2 H 0.9447 1.1499 0.8175 0.123 Uiso 1 1 calc R . . C18 C 0.9842(3) 1.2283(3) 0.78521(4) 0.0519(7) Uani 1 1 d . . . C19 C 1.0957(3) 1.2052(4) 0.77716(5) 0.0760(10) Uani 1 1 d . . . H19A H 1.0598 1.1557 0.7670 0.114 Uiso 1 1 calc R . . H19B H 1.1196 1.1502 0.7843 0.114 Uiso 1 1 calc R . . H19C H 1.1787 1.2950 0.7751 0.114 Uiso 1 1 calc R . . C20 C 0.9435(3) 1.3311(3) 0.77663(4) 0.0561(7) Uani 1 1 d . . . C21 C 0.8778(4) 1.2807(4) 0.75965(4) 0.0703(9) Uani 1 1 d . . . H21A H 0.9502 1.2939 0.7520 0.105 Uiso 1 1 calc R . . H21B H 0.8347 1.3344 0.7562 0.105 Uiso 1 1 calc R . . H21C H 0.8074 1.1822 0.7601 0.105 Uiso 1 1 calc R . . C22 C 1.0665(4) 1.4840(3) 0.77490(5) 0.0790(11) Uani 1 1 d . . . H22A H 1.0316 1.5424 0.7705 0.119 Uiso 1 1 calc R . . H22B H 1.1366 1.4858 0.7676 0.119 Uiso 1 1 calc R . . H22C H 1.1082 1.5192 0.7854 0.119 Uiso 1 1 calc R . . C23 C 0.8531(3) 0.8647(3) 0.78566(3) 0.0486(7) Uani 1 1 d . . . H23 H 0.9448 0.9098 0.7801 0.058 Uiso 1 1 calc R . . C24 C 0.8515(3) 0.8033(3) 0.80286(4) 0.0545(7) Uani 1 1 d . . . H24A H 0.9055 0.7546 0.8029 0.065 Uiso 1 1 calc R . . H24B H 0.8895 0.8771 0.8111 0.065 Uiso 1 1 calc R . . C25 C 0.6932(3) 0.6993(3) 0.80574(3) 0.0485(7) Uani 1 1 d . . . H25 H 0.6776 0.6029 0.8064 0.058 Uiso 1 1 calc R . . O3 O 0.6390(2) 0.7295(2) 0.82034(2) 0.0523(5) Uani 1 1 d . . . HO3 H 0.6877 0.8137 0.8226 0.079 Uiso 1 1 calc R . . C26 C 0.6201(3) 0.7130(3) 0.79015(3) 0.0426(6) Uani 1 1 d . . . C27 C 0.4717(3) 0.5910(3) 0.78752(4) 0.0587(8) Uani 1 1 d . . . H27A H 0.4319 0.6083 0.7779 0.088 Uiso 1 1 calc R . . H27B H 0.4144 0.5819 0.7969 0.088 Uiso 1 1 calc R . . H27C H 0.4746 0.5051 0.7861 0.088 Uiso 1 1 calc R . . C28 C 0.7336(3) 0.7361(3) 0.77685(3) 0.0496(7) Uani 1 1 d . . . C29 C 0.6982(4) 0.7711(3) 0.76002(3) 0.0632(8) Uani 1 1 d . . . H29A H 0.7804 0.8081 0.7531 0.095 Uiso 1 1 calc R . . H29B H 0.6691 0.8404 0.7612 0.095 Uiso 1 1 calc R . . H29C H 0.6229 0.6868 0.7552 0.095 Uiso 1 1 calc R . . C30 C 0.7593(4) 0.6107(3) 0.77506(4) 0.0675(9) Uani 1 1 d . . . H30A H 0.8402 0.6375 0.7682 0.101 Uiso 1 1 calc R . . H30B H 0.6776 0.5321 0.7702 0.101 Uiso 1 1 calc R . . H30C H 0.7762 0.5839 0.7856 0.101 Uiso 1 1 calc R . . O1W O 0.7595(3) 1.0230(3) 0.82972(3) 0.0763(7) Uani 1 1 d D . . H1WA H 0.691(4) 1.029(7) 0.8269(7) 0.22(3) Uiso 1 1 d D . . H1WB H 0.762(6) 1.022(7) 0.83977(14) 0.19(3) Uiso 1 1 d D . . O2W O 1.2620(3) 1.2620(3) 0.8333 0.0941(12) Uani 1 2 d SD . . H2WA H 1.189(3) 1.235(5) 0.8280(5) 0.14(2) Uiso 1 1 d D . . O3W O 0.5559(3) 1.3571(3) 0.83388(6) 0.1226(13) Uani 1 1 d DU . . H3WA H 0.612(3) 1.437(2) 0.8371(4) 0.104(14) Uiso 1 1 d D . . H3WB H 0.474(2) 1.340(6) 0.8326(6) 0.15(2) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0331(13) 0.0390(14) 0.0480(14) -0.0012(11) -0.0038(11) 0.0174(12) C2 0.0380(14) 0.0396(14) 0.0477(13) 0.0000(11) -0.0019(11) 0.0215(12) C3 0.0420(15) 0.0382(14) 0.0487(13) 0.0007(11) -0.0017(11) 0.0218(12) C4 0.0326(13) 0.0419(15) 0.0510(14) 0.0039(11) 0.0000(11) 0.0169(12) C5 0.0368(13) 0.0415(15) 0.0509(14) 0.0021(12) 0.0009(11) 0.0212(12) C6 0.0356(14) 0.0385(14) 0.0455(13) -0.0017(11) -0.0034(11) 0.0193(11) C7 0.0336(14) 0.0406(15) 0.0738(18) 0.0003(13) 0.0037(13) 0.0189(12) C8 0.0535(17) 0.0519(17) 0.0694(18) 0.0092(14) 0.0177(15) 0.0259(15) C9 0.0515(17) 0.0524(17) 0.0779(19) -0.0006(15) 0.0147(15) 0.0303(15) O1 0.0784(16) 0.0611(14) 0.0722(13) -0.0096(11) 0.0035(12) 0.0378(13) C10 0.0405(15) 0.0442(15) 0.0728(18) 0.0022(13) 0.0051(13) 0.0264(13) C11 0.061(2) 0.0552(19) 0.111(3) 0.0084(18) 0.0056(18) 0.0396(17) C12 0.0398(16) 0.0556(18) 0.082(2) -0.0019(15) -0.0066(14) 0.0275(14) C13 0.0468(19) 0.077(3) 0.151(4) 0.003(2) -0.003(2) 0.0378(19) C14 0.064(2) 0.080(2) 0.092(2) -0.0068(19) -0.0324(19) 0.040(2) C15 0.0493(17) 0.0398(15) 0.0701(18) 0.0024(13) 0.0014(14) 0.0236(14) C16 0.066(2) 0.0471(18) 0.076(2) -0.0084(15) -0.0112(17) 0.0168(16) C17 0.0479(18) 0.0500(18) 0.088(2) 0.0054(16) -0.0158(16) 0.0118(15) O2 0.0644(15) 0.0747(16) 0.0894(16) 0.0150(13) -0.0282(13) 0.0212(12) C18 0.0355(15) 0.0474(16) 0.0706(18) 0.0094(14) -0.0002(12) 0.0191(13) C19 0.0444(18) 0.062(2) 0.119(3) 0.024(2) 0.0194(18) 0.0252(16) C20 0.0487(16) 0.0438(16) 0.0706(19) 0.0111(14) 0.0032(14) 0.0192(13) C21 0.072(2) 0.075(2) 0.0643(19) 0.0193(17) 0.0100(16) 0.0372(19) C22 0.059(2) 0.0510(19) 0.116(3) 0.0228(19) 0.010(2) 0.0195(17) C23 0.0360(14) 0.0490(16) 0.0676(17) 0.0095(13) 0.0049(12) 0.0262(13) C24 0.0457(16) 0.0579(18) 0.0672(18) 0.0122(14) 0.0030(13) 0.0313(15) C25 0.0446(15) 0.0478(16) 0.0574(16) 0.0081(12) 0.0065(12) 0.0263(13) O3 0.0541(11) 0.0523(11) 0.0517(10) 0.0038(9) 0.0044(9) 0.0275(9) C26 0.0371(14) 0.0400(14) 0.0513(15) 0.0026(11) 0.0012(11) 0.0198(12) C27 0.0529(17) 0.0427(16) 0.078(2) -0.0049(14) -0.0066(15) 0.0218(14) C28 0.0552(17) 0.0468(16) 0.0549(15) 0.0077(13) 0.0103(13) 0.0315(14) C29 0.083(2) 0.066(2) 0.0499(16) -0.0026(15) 0.0053(15) 0.0450(18) C30 0.081(2) 0.061(2) 0.076(2) 0.0062(16) 0.0183(18) 0.0465(18) O1W 0.0915(18) 0.0723(16) 0.0688(15) -0.0005(11) -0.0119(12) 0.0437(14) O2W 0.0658(15) 0.0658(15) 0.137(3) 0.0261(13) -0.0261(13) 0.0227(18) O3W 0.0710(18) 0.079(2) 0.221(4) -0.066(2) -0.029(2) 0.0392(16) _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 C1 C6 1.367(4) . ? C1 C2 1.412(4) . ? C1 C7 1.501(4) . ? C2 C3 1.376(4) . ? C2 C10 1.522(4) . ? C3 C4 1.415(4) . ? C3 C15 1.504(4) . ? C4 C5 1.366(4) . ? C4 C18 1.524(4) . ? C5 C6 1.423(4) . ? C5 C23 1.510(3) . ? C6 C26 1.522(4) . ? C7 C12 1.543(4) . ? C7 C8 1.556(4) . ? C8 C9 1.543(4) . ? C9 O1 1.427(4) . ? C9 C10 1.568(4) . ? C10 C11 1.514(4) . ? C10 C12 1.567(4) . ? C12 C13 1.521(4) . ? C12 C14 1.539(5) . ? C15 C16 1.546(4) . ? C15 C20 1.549(4) . ? C16 C17 1.536(5) . ? C17 O2 1.423(4) . ? C17 C18 1.555(5) . ? C18 C19 1.512(4) . ? C18 C20 1.563(4) . ? C20 C21 1.533(5) . ? C20 C22 1.538(4) . ? C23 C28 1.535(4) . ? C23 C24 1.554(4) . ? C24 C25 1.539(4) . ? C25 O3 1.441(3) . ? C25 C26 1.550(4) . ? C26 C27 1.512(4) . ? C26 C28 1.570(4) . ? C28 C29 1.528(4) . ? C28 C30 1.536(4) . ? 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 C6 C1 C2 120.0(2) . . ? C6 C1 C7 133.7(2) . . ? C2 C1 C7 106.2(2) . . ? C3 C2 C1 120.0(2) . . ? C3 C2 C10 133.5(2) . . ? C1 C2 C10 106.5(2) . . ? C2 C3 C4 119.9(2) . . ? C2 C3 C15 133.6(2) . . ? C4 C3 C15 106.4(2) . . ? C5 C4 C3 120.1(2) . . ? C5 C4 C18 133.7(2) . . ? C3 C4 C18 106.2(2) . . ? C4 C5 C6 119.9(2) . . ? C4 C5 C23 134.7(2) . . ? C6 C5 C23 105.4(2) . . ? C1 C6 C5 120.0(2) . . ? C1 C6 C26 133.1(2) . . ? C5 C6 C26 106.9(2) . . ? C1 C7 C12 101.1(2) . . ? C1 C7 C8 105.2(2) . . ? C12 C7 C8 102.5(2) . . ? C9 C8 C7 103.0(2) . . ? O1 C9 C8 110.5(3) . . ? O1 C9 C10 113.5(2) . . ? C8 C9 C10 103.7(2) . . ? C11 C10 C2 118.0(2) . . ? C11 C10 C9 114.2(3) . . ? C2 C10 C9 104.3(2) . . ? C11 C10 C12 117.0(3) . . ? C2 C10 C12 100.0(2) . . ? C9 C10 C12 100.8(2) . . ? C13 C12 C14 108.4(3) . . ? C13 C12 C7 113.7(3) . . ? C14 C12 C7 112.6(3) . . ? C13 C12 C10 115.2(3) . . ? C14 C12 C10 113.1(3) . . ? C7 C12 C10 93.5(2) . . ? C3 C15 C16 105.2(2) . . ? C3 C15 C20 101.3(2) . . ? C16 C15 C20 102.1(2) . . ? C17 C16 C15 102.7(3) . . ? O2 C17 C16 114.7(3) . . ? O2 C17 C18 113.2(3) . . ? C16 C17 C18 104.5(2) . . ? C19 C18 C4 117.7(3) . . ? C19 C18 C17 113.9(3) . . ? C4 C18 C17 104.2(2) . . ? C19 C18 C20 117.7(3) . . ? C4 C18 C20 100.4(2) . . ? C17 C18 C20 100.4(2) . . ? C21 C20 C22 107.7(3) . . ? C21 C20 C15 113.4(3) . . ? C22 C20 C15 114.2(3) . . ? C21 C20 C18 113.5(3) . . ? C22 C20 C18 114.4(3) . . ? C15 C20 C18 93.4(2) . . ? C5 C23 C28 101.4(2) . . ? C5 C23 C24 105.8(2) . . ? C28 C23 C24 102.1(2) . . ? C25 C24 C23 102.8(2) . . ? O3 C25 C24 113.3(2) . . ? O3 C25 C26 111.7(2) . . ? C24 C25 C26 104.2(2) . . ? C27 C26 C6 118.1(2) . . ? C27 C26 C25 114.1(2) . . ? C6 C26 C25 104.9(2) . . ? C27 C26 C28 117.0(2) . . ? C6 C26 C28 99.7(2) . . ? C25 C26 C28 100.5(2) . . ? C29 C28 C30 108.6(2) . . ? C29 C28 C23 113.5(2) . . ? C30 C28 C23 114.2(3) . . ? C29 C28 C26 112.7(2) . . ? C30 C28 C26 113.8(2) . . ? C23 C28 C26 93.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.8(4) . . . . ? C7 C1 C2 C3 178.6(2) . . . . ? C6 C1 C2 C10 179.3(3) . . . . ? C7 C1 C2 C10 -1.3(3) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C10 C2 C3 C4 179.7(3) . . . . ? C1 C2 C3 C15 -178.0(3) . . . . ? C10 C2 C3 C15 1.9(5) . . . . ? C2 C3 C4 C5 0.5(4) . . . . ? C15 C3 C4 C5 178.8(2) . . . . ? C2 C3 C4 C18 -178.7(2) . . . . ? C15 C3 C4 C18 -0.4(3) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C18 C4 C5 C6 179.1(3) . . . . ? C3 C4 C5 C23 -179.0(3) . . . . ? C18 C4 C5 C23 -0.1(5) . . . . ? C2 C1 C6 C5 1.5(4) . . . . ? C7 C1 C6 C5 -177.7(3) . . . . ? C2 C1 C6 C26 -179.6(3) . . . . ? C7 C1 C6 C26 1.2(5) . . . . ? C4 C5 C6 C1 -1.3(4) . . . . ? C23 C5 C6 C1 178.2(2) . . . . ? C4 C5 C6 C26 179.6(3) . . . . ? C23 C5 C6 C26 -0.9(3) . . . . ? C6 C1 C7 C12 -145.1(3) . . . . ? C2 C1 C7 C12 35.7(3) . . . . ? C6 C1 C7 C8 108.6(3) . . . . ? C2 C1 C7 C8 -70.7(3) . . . . ? C1 C7 C8 C9 70.1(3) . . . . ? C12 C7 C8 C9 -35.2(3) . . . . ? C7 C8 C9 O1 -122.9(2) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C3 C2 C10 C11 19.3(5) . . . . ? C1 C2 C10 C11 -160.8(3) . . . . ? C3 C2 C10 C9 -108.7(3) . . . . ? C1 C2 C10 C9 71.2(3) . . . . ? C3 C2 C10 C12 147.3(3) . . . . ? C1 C2 C10 C12 -32.8(3) . . . . ? O1 C9 C10 C11 -77.7(3) . . . . ? C8 C9 C10 C11 162.4(3) . . . . ? O1 C9 C10 C2 52.5(3) . . . . ? C8 C9 C10 C2 -67.5(3) . . . . ? O1 C9 C10 C12 155.9(2) . . . . ? C8 C9 C10 C12 36.0(3) . . . . ? C1 C7 C12 C13 -172.1(3) . . . . ? C8 C7 C12 C13 -63.6(3) . . . . ? C1 C7 C12 C14 64.1(3) . . . . ? C8 C7 C12 C14 172.6(3) . . . . ? C1 C7 C12 C10 -52.7(2) . . . . ? C8 C7 C12 C10 55.8(3) . . . . ? C11 C10 C12 C13 -61.9(4) . . . . ? C2 C10 C12 C13 169.5(3) . . . . ? C9 C10 C12 C13 62.6(3) . . . . ? C11 C10 C12 C14 63.6(3) . . . . ? C2 C10 C12 C14 -65.1(3) . . . . ? C9 C10 C12 C14 -171.9(2) . . . . ? C11 C10 C12 C7 179.9(3) . . . . ? C2 C10 C12 C7 51.2(2) . . . . ? C9 C10 C12 C7 -55.6(2) . . . . ? C2 C3 C15 C16 106.6(4) . . . . ? C4 C3 C15 C16 -71.4(3) . . . . ? C2 C3 C15 C20 -147.4(3) . . . . ? C4 C3 C15 C20 34.7(3) . . . . ? C3 C15 C16 C17 69.5(3) . . . . ? C20 C15 C16 C17 -35.9(3) . . . . ? C15 C16 C17 O2 -124.8(3) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C5 C4 C18 C19 18.4(5) . . . . ? C3 C4 C18 C19 -162.7(3) . . . . ? C5 C4 C18 C17 -108.9(3) . . . . ? C3 C4 C18 C17 70.1(3) . . . . ? C5 C4 C18 C20 147.5(3) . . . . ? C3 C4 C18 C20 -33.6(3) . . . . ? O2 C17 C18 C19 -72.1(4) . . . . ? C16 C17 C18 C19 162.4(3) . . . . ? O2 C17 C18 C4 57.5(3) . . . . ? C16 C17 C18 C4 -68.1(3) . . . . ? O2 C17 C18 C20 161.1(3) . . . . ? C16 C17 C18 C20 35.6(3) . . . . ? C3 C15 C20 C21 65.4(3) . . . . ? C16 C15 C20 C21 173.8(3) . . . . ? C3 C15 C20 C22 -170.7(3) . . . . ? C16 C15 C20 C22 -62.3(3) . . . . ? C3 C15 C20 C18 -52.1(3) . . . . ? C16 C15 C20 C18 56.4(3) . . . . ? C19 C18 C20 C21 63.0(4) . . . . ? C4 C18 C20 C21 -66.0(3) . . . . ? C17 C18 C20 C21 -172.8(3) . . . . ? C19 C18 C20 C22 -61.1(4) . . . . ? C4 C18 C20 C22 169.9(3) . . . . ? C17 C18 C20 C22 63.1(3) . . . . ? C19 C18 C20 C15 -179.6(3) . . . . ? C4 C18 C20 C15 51.3(3) . . . . ? C17 C18 C20 C15 -55.4(2) . . . . ? C4 C5 C23 C28 -145.0(3) . . . . ? C6 C5 C23 C28 35.6(3) . . . . ? C4 C5 C23 C24 108.8(3) . . . . ? C6 C5 C23 C24 -70.5(3) . . . . ? C5 C23 C24 C25 70.1(3) . . . . ? C28 C23 C24 C25 -35.6(3) . . . . ? C23 C24 C25 O3 -122.4(2) . . . . ? C23 C24 C25 C26 -0.8(3) . . . . ? C1 C6 C26 C27 20.2(4) . . . . ? C5 C6 C26 C27 -160.9(2) . . . . ? C1 C6 C26 C25 -108.2(3) . . . . ? C5 C6 C26 C25 70.7(3) . . . . ? C1 C6 C26 C28 148.1(3) . . . . ? C5 C6 C26 C28 -33.0(3) . . . . ? O3 C25 C26 C27 -75.5(3) . . . . ? C24 C25 C26 C27 161.8(2) . . . . ? O3 C25 C26 C6 55.3(3) . . . . ? C24 C25 C26 C6 -67.4(3) . . . . ? O3 C25 C26 C28 158.4(2) . . . . ? C24 C25 C26 C28 35.7(3) . . . . ? C5 C23 C28 C29 63.6(3) . . . . ? C24 C23 C28 C29 172.6(2) . . . . ? C5 C23 C28 C30 -171.2(2) . . . . ? C24 C23 C28 C30 -62.2(3) . . . . ? C5 C23 C28 C26 -53.1(2) . . . . ? C24 C23 C28 C26 56.0(2) . . . . ? C27 C26 C28 C29 62.8(3) . . . . ? C6 C26 C28 C29 -65.9(3) . . . . ? C25 C26 C28 C29 -173.2(2) . . . . ? C27 C26 C28 C30 -61.4(3) . . . . ? C6 C26 C28 C30 170.0(3) . . . . ? C25 C26 C28 C30 62.7(3) . . . . ? C27 C26 C28 C23 -179.9(2) . . . . ? C6 C26 C28 C23 51.5(2) . . . . ? C25 C26 C28 C23 -55.8(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 HO1 O3W 0.82 1.95 2.758(4) 167.1 . O2 HO2 O1W 0.82 2.05 2.855(4) 167.5 . O3 HO3 O1W 0.82 2.09 2.892(3) 164.7 . O1W H1WA O1 0.821(10) 2.01(3) 2.777(3) 156(6) . O2W H2WA O2 0.822(11) 1.966(15) 2.779(3) 170(5) . O3W H3WA O3 0.820(11) 2.060(14) 2.874(3) 172(6) 7_566 O3W H3WB O2W 0.822(11) 2.030(18) 2.835(4) 166(6) 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 60.17 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.191 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.045 #===END=== data_mc41n _database_code_depnum_ccdc_archive 'CCDC 793277' #TrackingRef 'mc41n[revised].cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1R,2R,4S,5R,6R,8S,9R,10R,12S)-3,4,7,8,11,12-hexahydro-2,6,10-trihydroxy- 1,5,9,13,13',14,14',15,15'-nonamethyl-1,4:5,8:9,12-trimethanotriphenylene x 2.5 H2O ; _chemical_name_common ; (1R,2R,4S,5R,6R,8S,9R,10R,12S)-3,4,7,8,11,12-hexahydro-2,6,10- trihydroxy-1,5,9,13,13',14,14',15,15'-nonamethyl-1,4:5,8:9,12- trimethanotriphenylene x 2.5 H2O ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H47 O5.50' _chemical_formula_weight 495.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_length_neutron _atom_type_scat_source C C 6.6484 'Neutron Scattering Lengths, Neutron Data Booklet, 2nd Ed.1.1-1 ILL, 2003.' H H -3.7409 'Neutron Scattering Lengths, Neutron Data Booklet, 2nd Ed.1.1-1 ILL, 2003.' O O 5.805 'Neutron Scattering Lengths, Neutron Data Booklet, 2nd Ed.1.1-1 ILL, 2003.' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M 'P 65 2 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' 'y, x, -z+2/3' 'x-y, -y, -z' '-x, -x+y, -z+1/3' '-y, -x, -z+1/6' '-x+y, y, -z+1/2' 'x, x-y, -z+5/6' _cell_length_a 10.8602(10) _cell_length_b 10.8602(10) _cell_length_c 81.052(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8278.8(15) _cell_formula_units_Z 12 _cell_measurement_temperature 20(2) _cell_measurement_reflns_used 2587 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 61.71 _exptl_crystal_description 'truncated hexagonal pyramid' _exptl_crystal_colour colourless _exptl_crystal_size_max 4.0 _exptl_crystal_size_mid 4.0 _exptl_crystal_size_min 2.7 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 '667 fermi' _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type 'gaussian, and attenuation by Displex cans' _exptl_absorpt_correction_T_min 0.310 _exptl_absorpt_correction_T_max 0.527 _exptl_absorpt_process_details 'programs D19abs, D19abscan ' _exptl_special_details ; Crystal mounted on the ILL D19 diffractometer with a horizontally curved position-sensitive gas detector. Multi-wire gas counter, 256 vertical pixels anodes, 640 horizontal pixels, subtending 120 deg (horiz), 30 deg (vert). Reflections (2theta <123.52 deg) were measured to pre-set monitor counts, using omega step-scans, and typical counting time 10 s per step. Typical omega scans: 80 deg in 0.07 deg steps. ; _diffrn_ambient_temperature 20(2) _diffrn_radiation_wavelength 1.45970 _diffrn_radiation_type neutron _diffrn_radiation_source 'ILL High Flux reactor, H1 thermal beam' _diffrn_radiation_monochromator Cu220 _diffrn_measurement_device_type 'ILL D19 position-sensitive detector 4-circle diffractometer' _diffrn_measurement_method 'omega step-scans ' _diffrn_detector_area_resol_mean '1.56mm vert, 2.50mm horiz' _diffrn_standards_number 5 _diffrn_standards_interval_time '3 hours' _diffrn_standards_decay_% 0 _diffrn_reflns_number 14723 _diffrn_reflns_av_R_equivalents 0.1409 _diffrn_reflns_av_sigmaI/netI 0.0759 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -53 _diffrn_reflns_limit_l_max 97 _diffrn_reflns_theta_min 4.45 _diffrn_reflns_theta_max 61.86 _reflns_number_total 4878 _reflns_number_gt 4512 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ILL Mad' _computing_cell_refinement 'ILL Rafd19 ' _computing_data_reduction 'ILL Retreat ' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. The starting structural model for refinement was provided by the non-H atomic coordinates of the same structure solved and refined by X-ray diffraction (CCDC 690687). The choice of space group P6(5)22, rather than its enantiomorph P6(1)22, was based upon the known stereochemistry of the compound. ; _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^)+(0.0981P)^2^+112.4007P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'full anisotropic refinement' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00074(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 4878 _refine_ls_number_parameters 775 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0795 _refine_ls_wR_factor_ref 0.2032 _refine_ls_wR_factor_gt 0.1934 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _refine_ls_shift/su_max 1.207 _refine_ls_shift/su_mean 0.002 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 0.5725(5) 1.1210(6) 0.82685(6) 0.0316(10) Uani 1 1 d . . . H01A H 0.5847(11) 1.2117(11) 0.82949(10) 0.043(3) Uani 0.99(5) 1 d P . . O2 O 1.0335(6) 1.2080(5) 0.81451(6) 0.0319(10) Uani 1 1 d . . . H02A H 0.9382(10) 1.1446(11) 0.81821(11) 0.041(3) Uani 0.93(4) 1 d P . . O3 O 0.6443(6) 0.7352(6) 0.82039(7) 0.0296(10) Uani 1 1 d . . . H03C H 0.679(2) 0.707(2) 0.8300(3) 0.045(8) Uani 0.52(3) 1 d P A 1 H03D H 0.6783(19) 0.8390(19) 0.8217(2) 0.033(6) Uani 0.47(3) 1 d P B 2 C1 C 0.5537(4) 0.9150(4) 0.79409(4) 0.0243(8) Uani 1 1 d . . . C2 C 0.6067(4) 1.0659(4) 0.79384(4) 0.0237(7) Uani 1 1 d . . . C3 C 0.7487(4) 1.1583(4) 0.79064(4) 0.0251(7) Uani 1 1 d . . . C4 C 0.8439(4) 1.1050(4) 0.78745(4) 0.0247(8) Uani 1 1 d . . . C5 C 0.7925(4) 0.9604(4) 0.78756(4) 0.0245(7) Uani 1 1 d . . . C6 C 0.6451(4) 0.8648(4) 0.79084(4) 0.0245(8) Uani 1 1 d . . . C7 C 0.3991(4) 0.8463(4) 0.79832(5) 0.0251(8) Uani 1 1 d . . . H7 H 0.3341(9) 0.7366(9) 0.79542(10) 0.0382(17) Uani 1 1 d . . . C8 C 0.3964(5) 0.8849(4) 0.81697(5) 0.0295(9) Uani 1 1 d . . . H8A H 0.2888(10) 0.8268(9) 0.82195(11) 0.0433(19) Uani 1 1 d . . . H8B H 0.4633(10) 0.8586(10) 0.82427(11) 0.0442(19) Uani 1 1 d . . . C9 C 0.4514(4) 1.0456(4) 0.81665(5) 0.0287(8) Uani 1 1 d . . . H9 H 0.3699(9) 1.0692(9) 0.82107(10) 0.0386(17) Uani 1 1 d . . . C10 C 0.4817(4) 1.0868(4) 0.79775(5) 0.0266(8) Uani 1 1 d . . . C11 C 0.4917(4) 1.2258(4) 0.79341(5) 0.0301(9) Uani 1 1 d . . . H11A H 0.5155(11) 1.2508(9) 0.78020(10) 0.045(2) Uani 1 1 d . . . H11B H 0.5726(10) 1.3129(9) 0.80038(13) 0.047(2) Uani 1 1 d . . . H11C H 0.3929(10) 1.2235(10) 0.79591(13) 0.048(2) Uani 1 1 d . . . C12 C 0.3578(4) 0.9476(4) 0.78976(5) 0.0282(8) Uani 1 1 d . . . C13 C 0.2086(4) 0.9178(4) 0.79374(5) 0.0307(9) Uani 1 1 d . . . H13A H 0.1864(10) 0.9152(12) 0.80711(12) 0.051(2) Uani 1 1 d . . . H13B H 0.1309(9) 0.8133(10) 0.78894(14) 0.051(2) Uani 1 1 d . . . H13C H 0.1892(11) 0.9961(12) 0.78787(16) 0.060(3) Uani 1 1 d . . . C14 C 0.3693(5) 0.9460(5) 0.77071(5) 0.0326(9) Uani 1 1 d . . . H14A H 0.3462(12) 1.0225(11) 0.76535(12) 0.050(2) Uani 1 1 d . . . H14B H 0.2941(12) 0.8424(11) 0.76621(12) 0.053(2) Uani 1 1 d . . . H14C H 0.4712(10) 0.9694(12) 0.76678(11) 0.050(2) Uani 1 1 d . . . C15 C 0.8379(4) 1.3181(4) 0.79012(4) 0.0256(8) Uani 1 1 d . . . H15 H 0.7820(9) 1.3738(9) 0.78816(10) 0.0385(17) Uani 1 1 d . . . C16 C 0.9313(4) 1.3596(4) 0.80581(5) 0.0292(9) Uani 1 1 d . . . H16A H 0.9897(10) 1.4716(10) 0.80805(11) 0.0461(19) Uani 1 1 d . . . H16B H 0.8655(10) 1.3102(11) 0.81707(11) 0.047(2) Uani 1 1 d . . . C17 C 1.0349(5) 1.3035(5) 0.80253(5) 0.0312(9) Uani 1 1 d . . . H17 H 1.1418(10) 1.3893(10) 0.80205(10) 0.0403(17) Uani 1 1 d . . . C18 C 0.9893(4) 1.2336(4) 0.78493(4) 0.0261(8) Uani 1 1 d . . . C19 C 1.1026(5) 1.2132(5) 0.77648(5) 0.0314(9) Uani 1 1 d . . . H19A H 1.0638(11) 1.1551(12) 0.76487(10) 0.049(2) Uani 1 1 d . . . H19B H 1.1349(11) 1.1529(11) 0.78421(12) 0.048(2) Uani 1 1 d . . . H19C H 1.1966(11) 1.3133(11) 0.77386(14) 0.055(2) Uani 1 1 d . . . C20 C 0.9484(4) 1.3394(4) 0.77638(5) 0.0294(8) Uani 1 1 d . . . C21 C 0.8805(5) 1.2898(4) 0.75931(5) 0.0311(9) Uani 1 1 d . . . H21A H 0.9584(11) 1.2963(12) 0.75032(12) 0.055(2) Uani 1 1 d . . . H21B H 0.8430(13) 1.3584(11) 0.75473(13) 0.056(2) Uani 1 1 d . . . H21C H 0.7925(11) 1.1831(11) 0.75938(11) 0.050(2) Uani 1 1 d . . . C22 C 1.0707(4) 1.4918(4) 0.77470(5) 0.0321(9) Uani 1 1 d . . . H22A H 1.0303(11) 1.5594(10) 0.77081(13) 0.051(2) Uani 1 1 d . . . H22B H 1.1476(11) 1.4998(11) 0.76530(13) 0.054(2) Uani 1 1 d . . . H22C H 1.1305(11) 1.5383(10) 0.78606(12) 0.052(2) Uani 1 1 d . . . C23 C 0.8586(4) 0.8691(4) 0.78517(5) 0.0277(8) Uani 1 1 d . . . H23 H 0.9596(9) 0.9146(9) 0.77879(11) 0.0410(18) Uani 1 1 d . . . C24 C 0.8590(4) 0.8074(5) 0.80253(5) 0.0299(9) Uani 1 1 d . . . H24A H 0.9171(10) 0.7518(10) 0.80270(11) 0.0431(19) Uani 1 1 d . . . H24B H 0.9036(10) 0.8929(10) 0.81191(11) 0.0449(19) Uani 1 1 d . . . C25 C 0.6985(4) 0.7033(4) 0.80581(4) 0.0245(8) Uani 1 1 d . . . H25 H 0.6738(9) 0.5946(9) 0.80738(11) 0.0408(18) Uani 1 1 d . . . C26 C 0.6221(4) 0.7154(4) 0.79000(4) 0.0256(8) Uani 1 1 d . . . C27 C 0.4738(4) 0.5912(4) 0.78774(5) 0.0275(8) Uani 1 1 d . . . H27A H 0.4227(10) 0.6082(10) 0.77722(13) 0.049(2) Uani 1 1 d . . . H27B H 0.4036(11) 0.5754(10) 0.79827(12) 0.048(2) Uani 1 1 d . . . H27C H 0.4725(9) 0.4919(9) 0.78582(12) 0.046(2) Uani 1 1 d . . . C28 C 0.7349(4) 0.7363(4) 0.77639(5) 0.0279(8) Uani 1 1 d . . . C29 C 0.6978(4) 0.7718(4) 0.75945(5) 0.0301(9) Uani 1 1 d . . . H29A H 0.7878(10) 0.8046(11) 0.75091(11) 0.051(2) Uani 1 1 d . . . H29B H 0.6727(12) 0.8541(10) 0.76005(12) 0.049(2) Uani 1 1 d . . . H29C H 0.6102(11) 0.6772(11) 0.75411(12) 0.053(2) Uani 1 1 d . . . C30 C 0.7607(4) 0.6107(5) 0.77447(5) 0.0303(9) Uani 1 1 d . . . H30A H 0.8485(11) 0.6378(11) 0.76594(11) 0.049(2) Uani 1 1 d . . . H30B H 0.6686(11) 0.5216(11) 0.76933(13) 0.050(2) Uani 1 1 d . . . H30C H 0.7859(13) 0.5765(12) 0.78588(12) 0.053(2) Uani 1 1 d . . . O1W O 0.7674(6) 1.0286(8) 0.82942(7) 0.032(3) Uani 0.95(3) 1 d P . . H1WA H 0.7003(11) 1.0637(10) 0.82820(12) 0.040(4) Uani 0.94(5) 1 d P . . H1WC H 0.730(3) 0.938(3) 0.8255(3) 0.048(6) Uani 0.50(4) 1 d P C 1 H1WD H 0.775(2) 1.026(2) 0.8414(2) 0.048(6) Uani 0.47(3) 1 d P D 2 O2W O 1.2712(7) 1.2712(7) 0.8333 0.0335(14) Uani 1 2 d S . . H2WA H 1.1897(11) 1.2453(11) 0.82655(11) 0.050(4) Uani 1.00(5) 1 d . . . O3W O 0.5670(7) 1.3667(7) 0.83257(8) 0.038(3) Uani 0.96(4) 1 d P . . H3WA H 0.6188(12) 1.4517(12) 0.83854(13) 0.045(4) Uani 0.95(5) 1 d P . . H3WB H 0.4701(11) 1.3443(11) 0.83202(13) 0.047(4) Uani 0.96(5) 1 d P . . 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 0.035(3) 0.030(3) 0.026(2) -0.0017(19) 0.0001(18) 0.014(2) H01A 0.059(6) 0.037(6) 0.038(5) -0.010(4) -0.007(4) 0.030(4) O2 0.029(3) 0.032(2) 0.032(2) 0.002(2) -0.003(2) 0.013(2) H02A 0.031(6) 0.044(6) 0.043(5) 0.014(4) 0.009(4) 0.014(5) O3 0.034(2) 0.029(3) 0.026(2) 0.0020(19) -0.001(2) 0.017(2) H03C 0.043(9) 0.044(9) 0.06(2) 0.004(9) -0.011(9) 0.028(8) H03D 0.042(9) 0.015(15) 0.042(8) 0.013(8) 0.011(7) 0.015(8) C1 0.0235(18) 0.0247(18) 0.0270(16) 0.0013(14) 0.0014(14) 0.0137(15) C2 0.0198(17) 0.0204(17) 0.0282(16) 0.0016(13) 0.0021(14) 0.0082(14) C3 0.0258(18) 0.0245(18) 0.0253(15) 0.0008(14) 0.0023(14) 0.0128(15) C4 0.0273(19) 0.0207(17) 0.0272(16) 0.0016(14) 0.0014(14) 0.0127(15) C5 0.0235(17) 0.0201(17) 0.0270(16) 0.0009(14) 0.0014(14) 0.0088(15) C6 0.0270(19) 0.0257(19) 0.0243(15) -0.0026(14) 0.0028(14) 0.0158(16) C7 0.0215(17) 0.025(2) 0.0272(17) 0.0023(15) 0.0028(14) 0.0101(16) H7 0.042(4) 0.031(4) 0.041(4) -0.002(3) -0.005(3) 0.017(4) C8 0.031(2) 0.0271(19) 0.0303(18) -0.0016(16) 0.0025(18) 0.0139(17) H8A 0.038(5) 0.036(4) 0.052(4) -0.001(4) 0.005(4) 0.016(4) H8B 0.045(5) 0.045(5) 0.044(4) -0.008(4) -0.006(4) 0.024(4) C9 0.0282(19) 0.0282(19) 0.0306(18) -0.0035(16) -0.0005(16) 0.0147(16) H9 0.033(4) 0.041(4) 0.044(4) -0.003(3) -0.004(3) 0.020(4) C10 0.0250(18) 0.0224(17) 0.0337(18) -0.0011(15) 0.0001(15) 0.0128(15) C11 0.031(2) 0.026(2) 0.033(2) -0.0004(17) 0.0013(17) 0.0150(18) H11A 0.060(6) 0.035(4) 0.040(4) 0.008(3) 0.011(4) 0.023(4) H11B 0.046(5) 0.023(4) 0.065(5) 0.001(4) 0.002(4) 0.012(4) H11C 0.037(4) 0.045(5) 0.069(5) 0.010(4) 0.011(4) 0.025(4) C12 0.0227(19) 0.0274(19) 0.0327(19) -0.0019(15) -0.0051(15) 0.0112(15) C13 0.025(2) 0.028(2) 0.037(2) -0.0027(17) -0.0004(17) 0.0105(18) H13A 0.041(5) 0.061(6) 0.052(5) 0.001(4) 0.002(4) 0.026(4) H13B 0.021(4) 0.035(5) 0.080(6) -0.011(4) -0.002(4) 0.003(4) H13C 0.041(5) 0.053(6) 0.082(7) 0.009(5) 0.001(5) 0.021(5) C14 0.035(2) 0.036(2) 0.0276(18) -0.0011(17) -0.0052(17) 0.019(2) H14A 0.067(6) 0.051(5) 0.051(5) 0.006(4) 0.001(5) 0.042(5) H14B 0.054(5) 0.042(5) 0.048(5) -0.004(4) 0.004(4) 0.013(5) H14C 0.036(5) 0.071(6) 0.045(4) -0.006(4) -0.007(4) 0.028(4) C15 0.0271(18) 0.0214(18) 0.0277(17) 0.0006(14) 0.0026(15) 0.0117(16) H15 0.035(4) 0.044(4) 0.041(4) 0.002(3) 0.000(3) 0.024(4) C16 0.0327(19) 0.031(2) 0.0267(18) 0.0022(16) 0.0012(17) 0.0184(18) H16A 0.043(4) 0.034(5) 0.055(5) 0.000(4) 0.000(4) 0.015(4) H16B 0.046(5) 0.059(6) 0.040(4) 0.001(4) 0.005(4) 0.029(4) C17 0.034(2) 0.033(2) 0.0313(19) 0.0004(16) -0.0033(17) 0.020(2) H17 0.036(5) 0.039(4) 0.042(4) 0.001(3) -0.005(3) 0.017(4) C18 0.0196(17) 0.0250(18) 0.0286(17) 0.0004(15) 0.0032(14) 0.0074(15) C19 0.031(2) 0.033(2) 0.0319(19) -0.0016(18) 0.0005(17) 0.017(2) H19A 0.055(5) 0.058(6) 0.039(4) -0.012(4) -0.003(4) 0.033(5) H19B 0.047(5) 0.046(5) 0.058(5) -0.002(4) 0.001(4) 0.029(4) H19C 0.047(5) 0.038(5) 0.077(6) 0.004(5) 0.013(5) 0.019(5) C20 0.0289(18) 0.0249(18) 0.0318(18) 0.0009(16) 0.0020(16) 0.0116(16) C21 0.030(2) 0.029(2) 0.0306(19) 0.0040(16) 0.0037(18) 0.0118(19) H21A 0.046(5) 0.069(6) 0.049(4) -0.013(5) 0.003(5) 0.028(5) H21B 0.067(6) 0.052(5) 0.059(5) -0.009(5) -0.011(5) 0.038(5) H21C 0.052(5) 0.044(5) 0.042(4) -0.011(4) -0.006(4) 0.015(5) C22 0.030(2) 0.031(2) 0.034(2) 0.0014(17) -0.0023(19) 0.0142(18) H22A 0.056(6) 0.041(5) 0.068(6) 0.003(4) -0.002(5) 0.033(5) H22B 0.050(5) 0.045(5) 0.063(5) -0.005(4) 0.015(5) 0.020(4) H22C 0.047(5) 0.041(5) 0.051(5) 0.001(4) -0.015(4) 0.010(4) C23 0.028(2) 0.0277(18) 0.0293(17) -0.0014(15) -0.0002(16) 0.0158(17) H23 0.033(4) 0.036(4) 0.052(4) -0.005(4) -0.001(4) 0.015(3) C24 0.0268(19) 0.031(2) 0.0286(18) 0.0034(17) 0.0005(16) 0.0122(18) H24A 0.039(4) 0.041(4) 0.049(4) 0.003(4) 0.004(4) 0.020(4) H24B 0.044(5) 0.045(5) 0.043(4) 0.003(4) 0.001(4) 0.020(4) C25 0.0236(18) 0.0262(19) 0.0230(16) 0.0031(14) 0.0050(14) 0.0119(15) H25 0.037(4) 0.038(5) 0.045(4) 0.000(4) 0.002(3) 0.017(3) C26 0.0278(19) 0.0220(18) 0.0261(16) 0.0016(14) 0.0020(15) 0.0118(16) C27 0.0272(19) 0.029(2) 0.0266(18) 0.0000(15) 0.0008(17) 0.0139(16) H27A 0.034(4) 0.045(5) 0.061(5) 0.013(4) -0.002(4) 0.015(4) H27B 0.052(5) 0.040(4) 0.048(4) 0.003(4) 0.017(4) 0.020(4) H27C 0.031(4) 0.033(4) 0.068(5) 0.005(4) 0.008(4) 0.011(3) C28 0.035(2) 0.0247(18) 0.0272(16) 0.0023(15) 0.0006(16) 0.0171(16) C29 0.032(2) 0.030(2) 0.0292(18) 0.0016(17) 0.0011(18) 0.0167(19) H29A 0.047(5) 0.066(6) 0.041(4) 0.005(4) 0.008(4) 0.030(5) H29B 0.065(6) 0.040(5) 0.052(5) 0.005(4) -0.006(4) 0.034(5) H29C 0.052(5) 0.046(5) 0.050(5) -0.005(4) -0.015(4) 0.017(5) C30 0.031(2) 0.028(2) 0.033(2) -0.0002(17) 0.0014(19) 0.0151(18) H30A 0.055(5) 0.059(6) 0.043(4) 0.008(4) 0.019(4) 0.036(5) H30B 0.045(5) 0.044(5) 0.058(5) -0.009(4) -0.006(4) 0.021(5) H30C 0.069(6) 0.053(5) 0.048(5) 0.012(4) 0.006(5) 0.038(5) O1W 0.038(3) 0.037(5) 0.024(3) 0.002(2) 0.000(2) 0.021(3) H1WA 0.041(6) 0.040(5) 0.049(5) -0.006(4) -0.010(4) 0.028(4) H1WC 0.066(13) 0.029(18) 0.061(11) -0.004(10) 0.000(10) 0.032(12) H1WD 0.061(13) 0.056(12) 0.032(12) 0.008(8) 0.004(9) 0.034(10) O2W 0.028(2) 0.028(2) 0.036(3) 0.0019(17) -0.0019(17) 0.008(3) H2WA 0.044(6) 0.061(6) 0.046(5) -0.003(4) -0.009(4) 0.028(5) O3W 0.027(4) 0.031(4) 0.052(4) -0.010(3) -0.004(2) 0.011(3) H3WA 0.048(6) 0.032(7) 0.052(6) -0.018(5) -0.011(5) 0.018(5) H3WB 0.028(7) 0.056(6) 0.060(6) -0.011(5) -0.001(4) 0.023(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 C9 1.416(6) . ? O1 H01A 0.950(13) . ? O2 C17 1.415(6) . ? O2 H02A 0.960(13) . ? O3 C25 1.437(6) . ? O3 H03C 0.98(3) . ? O3 H03D 1.000(19) . ? C1 C6 1.376(5) . ? C1 C2 1.440(5) . ? C1 C7 1.497(5) . ? C2 C3 1.380(5) . ? C2 C10 1.518(5) . ? C3 C4 1.438(5) . ? C3 C15 1.506(5) . ? C4 C5 1.379(5) . ? C4 C18 1.509(5) . ? C5 C6 1.431(5) . ? C5 C23 1.500(5) . ? C6 C26 1.515(5) . ? C7 C12 1.546(5) . ? C7 C8 1.572(5) . ? C7 H7 1.064(9) . ? C8 C9 1.537(6) . ? C8 H8A 1.091(10) . ? C8 H8B 1.080(11) . ? C9 C10 1.584(5) . ? C9 H9 1.097(9) . ? C10 C11 1.501(5) . ? C10 C12 1.576(5) . ? C11 H11A 1.103(9) . ? C11 H11B 1.074(11) . ? C11 H11C 1.079(10) . ? C12 C13 1.519(6) . ? C12 C14 1.549(5) . ? C13 H13A 1.107(10) . ? C13 H13B 1.092(10) . ? C13 H13C 1.084(13) . ? C14 H14A 1.073(10) . ? C14 H14B 1.071(11) . ? C14 H14C 1.053(11) . ? C15 C16 1.547(5) . ? C15 C20 1.568(5) . ? C15 H15 1.062(9) . ? C16 C17 1.547(5) . ? C16 H16A 1.069(10) . ? C16 H16B 1.117(10) . ? C17 C18 1.575(5) . ? C17 H17 1.066(11) . ? C18 C19 1.519(5) . ? C18 C20 1.584(6) . ? C19 H19A 1.093(9) . ? C19 H19B 1.083(11) . ? C19 H19C 1.076(11) . ? C20 C22 1.524(6) . ? C20 C21 1.533(6) . ? C21 H21A 1.093(11) . ? C21 H21B 1.077(11) . ? C21 H21C 1.072(11) . ? C22 H22A 1.073(9) . ? C22 H22B 1.101(11) . ? C22 H22C 1.094(10) . ? C23 C24 1.560(5) . ? C23 C28 1.567(6) . ? C23 H23 1.083(10) . ? C24 C25 1.555(5) . ? C24 H24A 1.070(10) . ? C24 H24B 1.107(11) . ? C25 C26 1.567(5) . ? C25 H25 1.079(10) . ? C26 C27 1.508(6) . ? C26 C28 1.578(5) . ? C27 H27A 1.082(10) . ? C27 H27B 1.099(9) . ? C27 H27C 1.083(10) . ? C28 C30 1.531(6) . ? C28 C29 1.534(5) . ? C29 H29A 1.102(10) . ? C29 H29B 1.058(10) . ? C29 H29C 1.082(11) . ? C30 H30A 1.092(9) . ? C30 H30B 1.069(11) . ? C30 H30C 1.082(10) . ? O1W H1WA 0.981(12) . ? O1W H1WC 0.91(3) . ? O1W H1WD 0.98(2) . ? O2W H2WA 0.956(12) . ? O3W H3WA 0.940(16) . ? O3W H3WB 0.956(14) . ? 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 C9 O1 H01A 109.8(7) . . ? C17 O2 H02A 110.6(7) . . ? C25 O3 H03C 108.4(14) . . ? C25 O3 H03D 113.1(10) . . ? H03C O3 H03D 106.5(15) . . ? C6 C1 C2 119.4(4) . . ? C6 C1 C7 134.3(4) . . ? C2 C1 C7 106.3(3) . . ? C3 C2 C1 119.7(3) . . ? C3 C2 C10 133.5(4) . . ? C1 C2 C10 106.8(3) . . ? C2 C3 C4 120.5(4) . . ? C2 C3 C15 133.2(3) . . ? C4 C3 C15 106.3(3) . . ? C5 C4 C3 119.6(4) . . ? C5 C4 C18 134.0(4) . . ? C3 C4 C18 106.4(3) . . ? C4 C5 C6 119.8(3) . . ? C4 C5 C23 134.2(4) . . ? C6 C5 C23 106.0(3) . . ? C1 C6 C5 120.9(4) . . ? C1 C6 C26 131.9(4) . . ? C5 C6 C26 107.1(3) . . ? C1 C7 C12 101.2(3) . . ? C1 C7 C8 104.7(3) . . ? C12 C7 C8 101.0(3) . . ? C1 C7 H7 117.2(6) . . ? C12 C7 H7 115.6(6) . . ? C8 C7 H7 114.9(5) . . ? C9 C8 C7 103.8(3) . . ? C9 C8 H8A 111.0(6) . . ? C7 C8 H8A 111.0(6) . . ? C9 C8 H8B 112.2(7) . . ? C7 C8 H8B 110.6(6) . . ? H8A C8 H8B 108.2(8) . . ? O1 C9 C8 111.6(4) . . ? O1 C9 C10 113.5(4) . . ? C8 C9 C10 104.1(3) . . ? O1 C9 H9 107.4(6) . . ? C8 C9 H9 111.0(6) . . ? C10 C9 H9 109.1(5) . . ? C11 C10 C2 118.8(3) . . ? C11 C10 C12 117.8(3) . . ? C2 C10 C12 99.8(3) . . ? C11 C10 C9 114.3(3) . . ? C2 C10 C9 103.6(3) . . ? C12 C10 C9 99.8(3) . . ? C10 C11 H11A 111.4(6) . . ? C10 C11 H11B 112.3(6) . . ? H11A C11 H11B 107.8(8) . . ? C10 C11 H11C 111.2(6) . . ? H11A C11 H11C 107.2(8) . . ? H11B C11 H11C 106.7(8) . . ? C13 C12 C7 114.3(3) . . ? C13 C12 C14 107.0(3) . . ? C7 C12 C14 112.7(3) . . ? C13 C12 C10 115.2(3) . . ? C7 C12 C10 94.9(3) . . ? C14 C12 C10 112.7(3) . . ? C12 C13 H13A 114.1(6) . . ? C12 C13 H13B 109.4(6) . . ? H13A C13 H13B 106.1(9) . . ? C12 C13 H13C 110.1(7) . . ? H13A C13 H13C 108.9(9) . . ? H13B C13 H13C 107.9(9) . . ? C12 C14 H14A 110.1(6) . . ? C12 C14 H14B 109.2(6) . . ? H14A C14 H14B 108.9(10) . . ? C12 C14 H14C 112.3(6) . . ? H14A C14 H14C 108.3(10) . . ? H14B C14 H14C 107.9(9) . . ? C3 C15 C16 105.3(3) . . ? C3 C15 C20 101.2(3) . . ? C16 C15 C20 101.5(3) . . ? C3 C15 H15 116.1(6) . . ? C16 C15 H15 115.8(6) . . ? C20 C15 H15 115.0(6) . . ? C17 C16 C15 104.1(3) . . ? C17 C16 H16A 110.1(7) . . ? C15 C16 H16A 113.6(6) . . ? C17 C16 H16B 111.6(6) . . ? C15 C16 H16B 111.2(6) . . ? H16A C16 H16B 106.3(8) . . ? O2 C17 C16 115.3(4) . . ? O2 C17 C18 112.5(4) . . ? C16 C17 C18 103.3(3) . . ? O2 C17 H17 105.9(6) . . ? C16 C17 H17 110.5(6) . . ? C18 C17 H17 109.4(5) . . ? C4 C18 C19 118.4(4) . . ? C4 C18 C17 104.8(3) . . ? C19 C18 C17 113.3(3) . . ? C4 C18 C20 100.8(3) . . ? C19 C18 C20 116.7(3) . . ? C17 C18 C20 100.4(3) . . ? C18 C19 H19A 111.4(6) . . ? C18 C19 H19B 111.0(6) . . ? H19A C19 H19B 107.3(8) . . ? C18 C19 H19C 111.7(6) . . ? H19A C19 H19C 108.1(9) . . ? H19B C19 H19C 107.2(9) . . ? C22 C20 C21 107.8(3) . . ? C22 C20 C15 114.3(3) . . ? C21 C20 C15 113.0(3) . . ? C22 C20 C18 114.8(3) . . ? C21 C20 C18 113.6(3) . . ? C15 C20 C18 93.0(3) . . ? C20 C21 H21A 111.0(7) . . ? C20 C21 H21B 110.5(7) . . ? H21A C21 H21B 105.9(9) . . ? C20 C21 H21C 112.8(6) . . ? H21A C21 H21C 108.4(9) . . ? H21B C21 H21C 108.0(10) . . ? C20 C22 H22A 109.7(7) . . ? C20 C22 H22B 111.2(7) . . ? H22A C22 H22B 107.2(9) . . ? C20 C22 H22C 114.9(6) . . ? H22A C22 H22C 106.4(9) . . ? H22B C22 H22C 107.1(9) . . ? C5 C23 C24 105.8(3) . . ? C5 C23 C28 101.2(3) . . ? C24 C23 C28 101.5(3) . . ? C5 C23 H23 118.1(6) . . ? C24 C23 H23 114.0(6) . . ? C28 C23 H23 114.2(6) . . ? C25 C24 C23 102.9(3) . . ? C25 C24 H24A 110.6(6) . . ? C23 C24 H24A 112.5(6) . . ? C25 C24 H24B 110.8(6) . . ? C23 C24 H24B 110.7(6) . . ? H24A C24 H24B 109.3(8) . . ? O3 C25 C24 114.2(4) . . ? O3 C25 C26 110.8(4) . . ? C24 C25 C26 104.3(3) . . ? O3 C25 H25 105.1(6) . . ? C24 C25 H25 113.0(6) . . ? C26 C25 H25 109.6(6) . . ? C27 C26 C6 119.5(3) . . ? C27 C26 C25 113.4(3) . . ? C6 C26 C25 104.0(3) . . ? C27 C26 C28 116.7(3) . . ? C6 C26 C28 100.2(3) . . ? C25 C26 C28 100.3(3) . . ? C26 C27 H27A 110.7(6) . . ? C26 C27 H27B 113.1(6) . . ? H27A C27 H27B 105.3(9) . . ? C26 C27 H27C 112.6(6) . . ? H27A C27 H27C 107.7(8) . . ? H27B C27 H27C 107.0(8) . . ? C30 C28 C29 108.7(3) . . ? C30 C28 C23 114.3(3) . . ? C29 C28 C23 112.8(3) . . ? C30 C28 C26 114.7(3) . . ? C29 C28 C26 112.3(3) . . ? C23 C28 C26 93.5(3) . . ? C28 C29 H29A 109.9(6) . . ? C28 C29 H29B 112.4(6) . . ? H29A C29 H29B 108.5(9) . . ? C28 C29 H29C 109.6(6) . . ? H29A C29 H29C 105.8(9) . . ? H29B C29 H29C 110.2(9) . . ? C28 C30 H30A 110.4(6) . . ? C28 C30 H30B 110.0(7) . . ? H30A C30 H30B 107.0(9) . . ? C28 C30 H30C 114.1(7) . . ? H30A C30 H30C 107.3(9) . . ? H30B C30 H30C 107.7(10) . . ? H1WA O1W H1WC 111.2(16) . . ? H1WA O1W H1WD 101.5(14) . . ? H1WC O1W H1WD 108.7(19) . . ? H3WA O3W H3WB 108.3(11) . . ? 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 H01A O3W 0.950(13) 1.804(12) 2.737(9) 166.7(9) . O2 H02A O1W 0.960(13) 1.875(11) 2.824(8) 169.2(9) . O3 H03D O1W 1.000(19) 1.891(18) 2.866(9) 163.8(15) . O3 H03C O3 0.98(3) 1.732(18) 2.707(15) 175.2(18) 7_556 O1W H1WA O1 0.981(12) 1.786(11) 2.767(9) 176.9(11) . O1W H1WC O3 0.91(3) 1.96(2) 2.866(9) 171.8(19) . O2W H2WA O2 0.956(12) 1.819(11) 2.773(7) 175.1(10) . O3W H3WA O3 0.940(16) 1.929(12) 2.856(9) 168.0(10) 7_566 O3W H3WB O2W 0.956(14) 1.895(11) 2.841(9) 169.5(11) 1_455 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 61.86 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.874 _refine_diff_density_min -0.951 _refine_diff_density_rms 0.189 #===END===