# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email ycchenhuaxi@yahoo.com.cn _publ_contact_author_name 'Ying-Chun Chen' loop_ _publ_author_name 'Ying-Chun Chen' 'Jun-Long Li' 'Si-Li Zhou' 'Peng-Qiao Chen' 'Lin Dong' 'Tian-Yu Liu' data_5i _database_code_depnum_ccdc_archive 'CCDC 862846' #TrackingRef '- 5i.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 O5' _chemical_formula_weight 378.41 _chemical_absolute_configuration ad 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 triclinic _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.7512(3) _cell_length_b 8.1381(3) _cell_length_c 8.4256(3) _cell_angle_alpha 69.558(3) _cell_angle_beta 79.669(3) _cell_angle_gamma 74.031(3) _cell_volume 476.75(3) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 5874 _cell_measurement_theta_min 5.9584 _cell_measurement_theta_max 69.5107 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.756 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7520 _exptl_absorpt_correction_T_max 0.7779 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5866 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.96 _diffrn_reflns_theta_max 66.58 _reflns_number_total 2997 _reflns_number_gt 2987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0426P)^2^+0.0419P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(14) _refine_ls_number_reflns 2997 _refine_ls_number_parameters 256 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0737 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.017 _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 O3 O 0.79465(16) 1.05274(13) -0.33852(13) 0.0556(3) Uani 1 1 d . . . H3 H 0.7678 0.9588 -0.3290 0.083 Uiso 1 1 calc R . . O5 O 0.50435(16) 1.64126(14) -0.31760(16) 0.0606(3) Uani 1 1 d . . . O1 O 0.42737(16) 1.02708(15) -0.08870(18) 0.0739(4) Uani 1 1 d . . . O2 O 0.85950(15) 0.89504(15) 0.18249(14) 0.0588(3) Uani 1 1 d . . . O4 O 0.7451(2) 1.70894(16) -0.2701(2) 0.0823(4) Uani 1 1 d . . . C17 C 0.6152(2) 1.29253(18) -0.14183(19) 0.0461(3) Uani 1 1 d . . . H17 H 0.4957 1.3351 -0.1668 0.055 Uiso 1 1 calc R . . C4 C 0.5101(2) 0.66592(19) 0.17034(19) 0.0501(3) Uani 1 1 d . . . C12 C 0.69474(18) 1.09720(17) -0.05963(17) 0.0439(3) Uani 1 1 d . . . C13 C 0.7720(2) 1.0806(2) 0.1028(2) 0.0530(4) Uani 1 1 d . . . H13 H 0.6731 1.1196 0.1817 0.064 Uiso 1 1 calc R . . C19 C 0.85494(19) 1.03837(17) -0.18422(18) 0.0443(3) Uani 1 1 d . . . H19 H 0.9180 0.9136 -0.1303 0.053 Uiso 1 1 calc R . . C18 C 0.9845(2) 1.1629(2) -0.2240(2) 0.0540(4) Uani 1 1 d . . . H18B H 0.9965 1.2236 -0.3457 0.065 Uiso 1 1 calc R . . H18A H 1.1025 1.0910 -0.1906 0.065 Uiso 1 1 calc R . . C15 C 0.9188(2) 1.3053(2) -0.1307(2) 0.0552(4) Uani 1 1 d . . . C10 C 0.6092(2) 0.8056(2) 0.12398(19) 0.0479(3) Uani 1 1 d . . . C11 C 0.56130(19) 0.97903(18) -0.01237(18) 0.0472(3) Uani 1 1 d . . . C16 C 0.7265(2) 1.40125(19) -0.1768(2) 0.0498(3) Uani 1 1 d . . . C14 C 0.9069(2) 1.1981(2) 0.0609(2) 0.0638(5) Uani 1 1 d . . . H14A H 1.0246 1.1230 0.0918 0.077 Uiso 1 1 calc R . . H14B H 0.8700 1.2812 0.1265 0.077 Uiso 1 1 calc R . . C8 C 0.8214(3) 0.6058(2) 0.3327(2) 0.0630(4) Uani 1 1 d . . . H8 H 0.9253 0.5856 0.3840 0.076 Uiso 1 1 calc R . . C1 C 0.3253(3) 0.3861(3) 0.2784(3) 0.0858(6) Uani 1 1 d . . . H1 H 0.2629 0.2949 0.3137 0.103 Uiso 1 1 calc R . . C21 C 0.6646(2) 1.59850(19) -0.2578(2) 0.0540(4) Uani 1 1 d . . . C22 C 0.4314(3) 1.8293(2) -0.4062(3) 0.0662(4) Uani 1 1 d . . . H22A H 0.5143 1.8747 -0.5025 0.079 Uiso 1 1 calc R . . H22B H 0.4122 1.9005 -0.3305 0.079 Uiso 1 1 calc R . . C3 C 0.3549(2) 0.6820(2) 0.0963(2) 0.0603(4) Uani 1 1 d . . . H3A H 0.3119 0.7873 0.0105 0.072 Uiso 1 1 calc R . . C9 C 0.7592(2) 0.7730(2) 0.20902(18) 0.0510(4) Uani 1 1 d . . . C23 C 0.2571(3) 1.8411(3) -0.4653(3) 0.0835(6) Uani 1 1 d . . . H23C H 0.2049 1.9645 -0.5249 0.125 Uiso 1 1 calc R . . H23B H 0.1763 1.7962 -0.3689 0.125 Uiso 1 1 calc R . . H23A H 0.2779 1.7703 -0.5401 0.125 Uiso 1 1 calc R . . C7 C 0.7287(3) 0.4755(2) 0.3759(2) 0.0672(5) Uani 1 1 d . . . H7 H 0.7700 0.3660 0.4576 0.081 Uiso 1 1 calc R . . C20 C 1.0552(3) 1.4225(3) -0.1742(3) 0.0817(6) Uani 1 1 d . . . H20A H 1.1719 1.3474 -0.1454 0.123 Uiso 1 1 calc R . . H20C H 1.0187 1.5061 -0.1109 0.123 Uiso 1 1 calc R . . H20B H 1.0607 1.4877 -0.2938 0.123 Uiso 1 1 calc R . . C2 C 0.2658(3) 0.5455(3) 0.1482(3) 0.0752(5) Uani 1 1 d . . . H2 H 0.1644 0.5589 0.0962 0.090 Uiso 1 1 calc R . . C5 C 0.5714(2) 0.5013(2) 0.3005(2) 0.0592(4) Uani 1 1 d . . . C6 C 0.4742(3) 0.3655(2) 0.3526(3) 0.0761(5) Uani 1 1 d . . . H6 H 0.5130 0.2598 0.4397 0.091 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 O3 0.0798(7) 0.0372(5) 0.0541(6) -0.0122(4) -0.0152(5) -0.0176(5) O5 0.0632(7) 0.0338(5) 0.0797(7) -0.0160(5) -0.0079(5) -0.0048(4) O1 0.0613(7) 0.0498(6) 0.1021(9) 0.0060(6) -0.0378(7) -0.0194(5) O2 0.0603(7) 0.0563(6) 0.0586(6) -0.0129(5) -0.0215(5) -0.0083(5) O4 0.0872(9) 0.0405(6) 0.1283(12) -0.0277(7) -0.0195(8) -0.0220(6) C17 0.0416(7) 0.0359(7) 0.0598(8) -0.0164(6) -0.0081(6) -0.0038(6) C4 0.0526(8) 0.0406(8) 0.0495(8) -0.0128(6) 0.0053(6) -0.0073(6) C12 0.0443(8) 0.0355(7) 0.0533(8) -0.0151(6) -0.0106(6) -0.0063(6) C13 0.0569(9) 0.0502(8) 0.0557(8) -0.0219(7) -0.0128(7) -0.0068(7) C19 0.0460(7) 0.0316(6) 0.0539(7) -0.0125(5) -0.0127(6) -0.0029(5) C18 0.0420(8) 0.0476(8) 0.0743(10) -0.0226(7) -0.0084(7) -0.0073(6) C15 0.0491(8) 0.0452(8) 0.0792(10) -0.0243(7) -0.0140(7) -0.0124(7) C10 0.0497(8) 0.0422(7) 0.0470(7) -0.0125(6) -0.0022(6) -0.0067(6) C11 0.0437(8) 0.0381(7) 0.0567(8) -0.0103(6) -0.0103(6) -0.0071(6) C16 0.0504(8) 0.0383(7) 0.0656(9) -0.0236(7) -0.0055(7) -0.0087(6) C14 0.0671(11) 0.0620(10) 0.0777(11) -0.0345(9) -0.0229(9) -0.0130(8) C8 0.0664(11) 0.0609(10) 0.0479(8) -0.0096(7) -0.0109(7) 0.0006(8) C1 0.0986(16) 0.0551(10) 0.1003(16) -0.0193(10) 0.0163(13) -0.0358(11) C21 0.0593(9) 0.0377(7) 0.0684(9) -0.0241(7) -0.0005(7) -0.0105(7) C22 0.0754(12) 0.0360(7) 0.0746(11) -0.0131(7) -0.0021(9) -0.0018(7) C3 0.0632(10) 0.0498(9) 0.0655(9) -0.0137(7) -0.0004(8) -0.0186(8) C9 0.0543(9) 0.0486(8) 0.0445(8) -0.0122(6) -0.0055(7) -0.0057(7) C23 0.0790(14) 0.0568(10) 0.1005(15) -0.0217(10) -0.0130(11) 0.0058(10) C7 0.0840(13) 0.0484(9) 0.0477(9) -0.0021(7) -0.0034(8) 0.0002(9) C20 0.0621(11) 0.0638(11) 0.1324(18) -0.0349(11) -0.0231(11) -0.0217(9) C2 0.0749(13) 0.0641(11) 0.0896(14) -0.0231(10) 0.0051(10) -0.0307(10) C5 0.0713(11) 0.0434(8) 0.0510(8) -0.0124(7) 0.0078(8) -0.0063(7) C6 0.0935(14) 0.0451(9) 0.0725(11) -0.0064(8) 0.0126(10) -0.0175(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 O3 C19 1.4156(17) . ? O3 H3 0.8200 . ? O5 C21 1.334(2) . ? O5 C22 1.4480(19) . ? O1 C11 1.2185(18) . ? O2 C9 1.3592(19) . ? O2 C13 1.4435(19) . ? O4 C21 1.1952(19) . ? C17 C16 1.327(2) . ? C17 C12 1.4938(18) . ? C17 H17 0.9300 . ? C4 C3 1.407(2) . ? C4 C5 1.426(2) . ? C4 C10 1.449(2) . ? C12 C11 1.5117(18) . ? C12 C13 1.5394(18) . ? C12 C19 1.559(2) . ? C13 C14 1.521(2) . ? C13 H13 0.9800 . ? C19 C18 1.5329(18) . ? C19 H19 0.9800 . ? C18 C15 1.546(2) . ? C18 H18B 0.9700 . ? C18 H18A 0.9700 . ? C15 C20 1.528(2) . ? C15 C16 1.529(2) . ? C15 C14 1.544(3) . ? C10 C9 1.390(2) . ? C10 C11 1.4770(19) . ? C16 C21 1.484(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C8 C7 1.353(3) . ? C8 C9 1.414(2) . ? C8 H8 0.9300 . ? C1 C6 1.353(3) . ? C1 C2 1.399(3) . ? C1 H1 0.9300 . ? C22 C23 1.489(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C3 C2 1.370(2) . ? C3 H3A 0.9300 . ? C23 H23C 0.9600 . ? C23 H23B 0.9600 . ? C23 H23A 0.9600 . ? C7 C5 1.406(3) . ? C7 H7 0.9300 . ? C20 H20A 0.9600 . ? C20 H20C 0.9600 . ? C20 H20B 0.9600 . ? C2 H2 0.9300 . ? C5 C6 1.408(3) . ? C6 H6 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 O3 H3 109.5 . . ? C21 O5 C22 117.46(13) . . ? C9 O2 C13 115.43(11) . . ? C16 C17 C12 115.53(12) . . ? C16 C17 H17 122.2 . . ? C12 C17 H17 122.2 . . ? C3 C4 C5 117.26(14) . . ? C3 C4 C10 124.28(13) . . ? C5 C4 C10 118.45(15) . . ? C17 C12 C11 113.99(11) . . ? C17 C12 C13 107.19(11) . . ? C11 C12 C13 108.91(11) . . ? C17 C12 C19 106.99(11) . . ? C11 C12 C19 111.53(11) . . ? C13 C12 C19 107.98(11) . . ? O2 C13 C14 109.54(13) . . ? O2 C13 C12 109.45(11) . . ? C14 C13 C12 110.65(13) . . ? O2 C13 H13 109.1 . . ? C14 C13 H13 109.1 . . ? C12 C13 H13 109.1 . . ? O3 C19 C18 108.62(11) . . ? O3 C19 C12 111.34(11) . . ? C18 C19 C12 108.27(11) . . ? O3 C19 H19 109.5 . . ? C18 C19 H19 109.5 . . ? C12 C19 H19 109.5 . . ? C19 C18 C15 112.11(12) . . ? C19 C18 H18B 109.2 . . ? C15 C18 H18B 109.2 . . ? C19 C18 H18A 109.2 . . ? C15 C18 H18A 109.2 . . ? H18B C18 H18A 107.9 . . ? C20 C15 C16 116.93(13) . . ? C20 C15 C14 110.80(14) . . ? C16 C15 C14 107.23(14) . . ? C20 C15 C18 109.24(14) . . ? C16 C15 C18 106.14(11) . . ? C14 C15 C18 105.86(12) . . ? C9 C10 C4 118.40(13) . . ? C9 C10 C11 118.46(13) . . ? C4 C10 C11 123.12(13) . . ? O1 C11 C10 124.37(13) . . ? O1 C11 C12 119.99(12) . . ? C10 C11 C12 115.61(12) . . ? C17 C16 C21 121.05(13) . . ? C17 C16 C15 114.44(12) . . ? C21 C16 C15 124.49(13) . . ? C13 C14 C15 110.41(12) . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C7 C8 C9 119.54(16) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C6 C1 C2 119.52(18) . . ? C6 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? O4 C21 O5 122.69(14) . . ? O4 C21 C16 125.55(15) . . ? O5 C21 C16 111.76(12) . . ? O5 C22 C23 107.23(15) . . ? O5 C22 H22A 110.3 . . ? C23 C22 H22A 110.3 . . ? O5 C22 H22B 110.3 . . ? C23 C22 H22B 110.3 . . ? H22A C22 H22B 108.5 . . ? C2 C3 C4 121.24(16) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? O2 C9 C10 124.27(12) . . ? O2 C9 C8 113.79(14) . . ? C10 C9 C8 121.94(15) . . ? C22 C23 H23C 109.5 . . ? C22 C23 H23B 109.5 . . ? H23C C23 H23B 109.5 . . ? C22 C23 H23A 109.5 . . ? H23C C23 H23A 109.5 . . ? H23B C23 H23A 109.5 . . ? C8 C7 C5 121.74(14) . . ? C8 C7 H7 119.1 . . ? C5 C7 H7 119.1 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? C3 C2 C1 121.0(2) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C7 C5 C6 120.43(16) . . ? C7 C5 C4 119.82(15) . . ? C6 C5 C4 119.76(18) . . ? C1 C6 C5 121.23(18) . . ? C1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? 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 C16 C17 C12 C11 176.61(13) . . . . ? C16 C17 C12 C13 56.01(17) . . . . ? C16 C17 C12 C19 -59.61(15) . . . . ? C9 O2 C13 C14 -172.88(12) . . . . ? C9 O2 C13 C12 -51.40(17) . . . . ? C17 C12 C13 O2 -176.88(13) . . . . ? C11 C12 C13 O2 59.35(15) . . . . ? C19 C12 C13 O2 -61.92(15) . . . . ? C17 C12 C13 C14 -56.08(16) . . . . ? C11 C12 C13 C14 -179.85(13) . . . . ? C19 C12 C13 C14 58.88(15) . . . . ? C17 C12 C19 O3 -63.97(13) . . . . ? C11 C12 C19 O3 61.31(13) . . . . ? C13 C12 C19 O3 -179.06(11) . . . . ? C17 C12 C19 C18 55.36(13) . . . . ? C11 C12 C19 C18 -179.36(11) . . . . ? C13 C12 C19 C18 -59.72(13) . . . . ? O3 C19 C18 C15 121.09(13) . . . . ? C12 C19 C18 C15 0.06(16) . . . . ? C19 C18 C15 C20 179.25(14) . . . . ? C19 C18 C15 C16 -53.86(16) . . . . ? C19 C18 C15 C14 59.90(15) . . . . ? C3 C4 C10 C9 179.12(15) . . . . ? C5 C4 C10 C9 -0.3(2) . . . . ? C3 C4 C10 C11 -2.5(2) . . . . ? C5 C4 C10 C11 178.09(14) . . . . ? C9 C10 C11 O1 -175.46(16) . . . . ? C4 C10 C11 O1 6.2(2) . . . . ? C9 C10 C11 C12 6.6(2) . . . . ? C4 C10 C11 C12 -171.72(13) . . . . ? C17 C12 C11 O1 25.1(2) . . . . ? C13 C12 C11 O1 144.68(15) . . . . ? C19 C12 C11 O1 -96.23(17) . . . . ? C17 C12 C11 C10 -156.93(12) . . . . ? C13 C12 C11 C10 -37.30(17) . . . . ? C19 C12 C11 C10 81.78(15) . . . . ? C12 C17 C16 C21 -179.73(13) . . . . ? C12 C17 C16 C15 1.62(19) . . . . ? C20 C15 C16 C17 177.72(16) . . . . ? C14 C15 C16 C17 -57.22(17) . . . . ? C18 C15 C16 C17 55.59(17) . . . . ? C20 C15 C16 C21 -0.9(2) . . . . ? C14 C15 C16 C21 124.18(15) . . . . ? C18 C15 C16 C21 -123.00(15) . . . . ? O2 C13 C14 C15 123.40(14) . . . . ? C12 C13 C14 C15 2.65(18) . . . . ? C20 C15 C14 C13 -179.51(14) . . . . ? C16 C15 C14 C13 51.81(16) . . . . ? C18 C15 C14 C13 -61.19(16) . . . . ? C22 O5 C21 O4 2.4(2) . . . . ? C22 O5 C21 C16 -177.52(14) . . . . ? C17 C16 C21 O4 167.77(17) . . . . ? C15 C16 C21 O4 -13.7(3) . . . . ? C17 C16 C21 O5 -12.3(2) . . . . ? C15 C16 C21 O5 166.24(15) . . . . ? C21 O5 C22 C23 177.98(17) . . . . ? C5 C4 C3 C2 0.5(2) . . . . ? C10 C4 C3 C2 -178.91(16) . . . . ? C13 O2 C9 C10 19.6(2) . . . . ? C13 O2 C9 C8 -160.56(14) . . . . ? C4 C10 C9 O2 -177.32(13) . . . . ? C11 C10 C9 O2 4.3(2) . . . . ? C4 C10 C9 C8 2.9(2) . . . . ? C11 C10 C9 C8 -175.52(15) . . . . ? C7 C8 C9 O2 177.26(15) . . . . ? C7 C8 C9 C10 -2.9(2) . . . . ? C9 C8 C7 C5 0.2(3) . . . . ? C4 C3 C2 C1 0.8(3) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? C8 C7 C5 C6 -177.65(16) . . . . ? C8 C7 C5 C4 2.4(2) . . . . ? C3 C4 C5 C7 178.25(16) . . . . ? C10 C4 C5 C7 -2.3(2) . . . . ? C3 C4 C5 C6 -1.7(2) . . . . ? C10 C4 C5 C6 177.72(15) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? C7 C5 C6 C1 -178.24(19) . . . . ? C4 C5 C6 C1 1.7(3) . . . . ? 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 O3 H3 O4 0.82 1.97 2.7737(14) 167.2 1_545 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 66.58 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.109 _refine_diff_density_min -0.105 _refine_diff_density_rms 0.019