data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email jlzhang@chem.ecnu.edu.cn _publ_contact_author_name 'Junliang Zhang' loop_ _publ_author_name 'Junliang Zhang' 'Hongyin Gao' data_z_3a _database_code_depnum_ccdc_archive 'CCDC 784918' #TrackingRef '3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H28 O2' _chemical_formula_weight 516.60 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 20.5140(6) _cell_length_b 14.3651(4) _cell_length_c 9.3329(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2750.27(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.430 _exptl_crystal_size_mid 0.301 _exptl_crystal_size_min 0.229 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.791935 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31013 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4732 _reflns_number_gt 4195 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.3126P] 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 0.6(10) _refine_ls_number_reflns 4732 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.13279(5) 0.12423(7) 0.22651(12) 0.0342(2) Uani 1 1 d . . . O2 O 0.23519(6) 0.17559(8) 0.64465(13) 0.0472(3) Uani 1 1 d . . . C1 C 0.16467(11) 0.27524(14) 0.8338(2) 0.0587(5) Uani 1 1 d . . . H1A H 0.2070 0.2555 0.8529 0.070 Uiso 1 1 calc R . . C2 C 0.13082(14) 0.32368(16) 0.9368(2) 0.0754(7) Uani 1 1 d . . . H2A H 0.1501 0.3351 1.0253 0.090 Uiso 1 1 calc R . . C3 C 0.06886(13) 0.35535(16) 0.9103(2) 0.0716(7) Uani 1 1 d . . . H3A H 0.0464 0.3890 0.9796 0.086 Uiso 1 1 calc R . . C4 C 0.04087(12) 0.33684(16) 0.7816(2) 0.0683(6) Uani 1 1 d . . . H4A H -0.0011 0.3582 0.7627 0.082 Uiso 1 1 calc R . . C5 C 0.07393(10) 0.28673(15) 0.6785(2) 0.0573(5) Uani 1 1 d . . . H5A H 0.0535 0.2739 0.5918 0.069 Uiso 1 1 calc R . . C6 C 0.13678(9) 0.25517(11) 0.70125(18) 0.0423(4) Uani 1 1 d . . . C7 C 0.17364(8) 0.20023(11) 0.59694(19) 0.0397(4) Uani 1 1 d . . . C8 C 0.26177(9) 0.11584(13) 0.5471(2) 0.0460(4) Uani 1 1 d . . . C9 C 0.21991(8) 0.10245(11) 0.43798(19) 0.0380(4) Uani 1 1 d . . . C10 C 0.16345(8) 0.15849(11) 0.46740(18) 0.0365(4) Uani 1 1 d . . . C11 C 0.10584(8) 0.14639(11) 0.36649(17) 0.0358(4) Uani 1 1 d . . . C12 C 0.07616(8) 0.05377(11) 0.40989(19) 0.0375(4) Uani 1 1 d . . . C13 C 0.03074(9) 0.03190(13) 0.5141(2) 0.0477(5) Uani 1 1 d . . . H13A H 0.0098 0.0785 0.5656 0.057 Uiso 1 1 calc R . . C14 C 0.01725(10) -0.06074(14) 0.5400(2) 0.0569(5) Uani 1 1 d . . . H14A H -0.0133 -0.0768 0.6093 0.068 Uiso 1 1 calc R . . C15 C 0.04863(10) -0.12959(14) 0.4641(3) 0.0595(5) Uani 1 1 d . . . H15A H 0.0386 -0.1917 0.4819 0.071 Uiso 1 1 calc R . . C16 C 0.09499(9) -0.10768(12) 0.3615(2) 0.0499(5) Uani 1 1 d . . . H16A H 0.1163 -0.1545 0.3111 0.060 Uiso 1 1 calc R . . C17 C 0.10892(8) -0.01528(11) 0.33540(18) 0.0378(4) Uani 1 1 d . . . C18 C 0.15842(8) 0.03074(10) 0.23587(18) 0.0354(4) Uani 1 1 d . . . C19 C 0.22707(8) 0.04080(11) 0.30783(18) 0.0375(4) Uani 1 1 d . . . H19A H 0.2411 -0.0209 0.3401 0.045 Uiso 1 1 calc R . . C20 C 0.16277(8) -0.01161(11) 0.08779(18) 0.0377(4) Uani 1 1 d . . . C21 C 0.18864(9) -0.10046(12) 0.0700(2) 0.0503(5) Uani 1 1 d . . . H21A H 0.2031 -0.1335 0.1496 0.060 Uiso 1 1 calc R . . C22 C 0.19313(11) -0.14004(13) -0.0640(3) 0.0615(6) Uani 1 1 d . . . H22A H 0.2098 -0.1999 -0.0741 0.074 Uiso 1 1 calc R . . C23 C 0.17318(12) -0.09179(14) -0.1822(2) 0.0654(6) Uani 1 1 d . . . H23A H 0.1763 -0.1185 -0.2728 0.079 Uiso 1 1 calc R . . C24 C 0.14834(11) -0.00321(14) -0.1664(2) 0.0610(5) Uani 1 1 d . . . H24A H 0.1349 0.0300 -0.2467 0.073 Uiso 1 1 calc R . . C25 C 0.14324(9) 0.03638(12) -0.0325(2) 0.0455(4) Uani 1 1 d . . . H25A H 0.1264 0.0962 -0.0232 0.055 Uiso 1 1 calc R . . C26 C 0.27427(9) 0.16767(13) 0.1513(2) 0.0482(4) Uani 1 1 d . . . H26A H 0.2430 0.2084 0.1871 0.058 Uiso 1 1 calc R . . C27 C 0.31726(10) 0.19814(16) 0.0484(2) 0.0599(5) Uani 1 1 d . . . H27A H 0.3147 0.2590 0.0149 0.072 Uiso 1 1 calc R . . C28 C 0.36372(11) 0.13923(19) -0.0049(2) 0.0722(7) Uani 1 1 d . . . H28A H 0.3921 0.1595 -0.0761 0.087 Uiso 1 1 calc R . . C29 C 0.36826(11) 0.0504(2) 0.0468(3) 0.0736(7) Uani 1 1 d . . . H29A H 0.4006 0.0109 0.0127 0.088 Uiso 1 1 calc R . . C30 C 0.32508(9) 0.01909(14) 0.1494(2) 0.0561(5) Uani 1 1 d . . . H30A H 0.3284 -0.0416 0.1832 0.067 Uiso 1 1 calc R . . C31 C 0.27689(8) 0.07696(12) 0.20248(19) 0.0408(4) Uani 1 1 d . . . C32 C -0.00450(9) 0.22313(13) 0.3360(2) 0.0496(4) Uani 1 1 d . . . H32A H -0.0245 0.1655 0.3473 0.059 Uiso 1 1 calc R . . C33 C -0.04202(10) 0.30179(15) 0.3131(3) 0.0640(6) Uani 1 1 d . . . H33A H -0.0872 0.2968 0.3101 0.077 Uiso 1 1 calc R . . C34 C -0.01316(12) 0.38700(14) 0.2949(2) 0.0626(6) Uani 1 1 d . . . H34A H -0.0387 0.4399 0.2820 0.075 Uiso 1 1 calc R . . C35 C 0.05355(11) 0.39395(13) 0.2958(2) 0.0560(5) Uani 1 1 d . . . H35A H 0.0733 0.4513 0.2797 0.067 Uiso 1 1 calc R . . C36 C 0.09138(10) 0.31634(11) 0.3204(2) 0.0459(4) Uani 1 1 d . . . H36A H 0.1365 0.3219 0.3224 0.055 Uiso 1 1 calc R . . C37 C 0.06271(8) 0.23005(11) 0.34205(18) 0.0384(4) Uani 1 1 d . . . C38 C 0.32770(11) 0.07962(17) 0.5813(3) 0.0723(7) Uani 1 1 d . . . H38A H 0.3421 0.0393 0.5056 0.108 Uiso 1 1 calc R . . H38B H 0.3261 0.0454 0.6696 0.108 Uiso 1 1 calc R . . H38C H 0.3576 0.1307 0.5908 0.108 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 0.0376(6) 0.0354(5) 0.0296(6) -0.0008(5) 0.0000(5) 0.0024(5) O2 0.0465(7) 0.0596(7) 0.0356(7) -0.0080(6) -0.0075(6) 0.0012(6) C1 0.0746(14) 0.0622(12) 0.0393(11) -0.0068(9) -0.0052(10) 0.0075(10) C2 0.111(2) 0.0795(15) 0.0358(12) -0.0142(11) -0.0034(13) 0.0098(14) C3 0.0950(19) 0.0739(14) 0.0459(13) -0.0153(11) 0.0199(12) 0.0085(13) C4 0.0677(15) 0.0845(15) 0.0528(14) -0.0131(11) 0.0131(11) 0.0090(12) C5 0.0532(12) 0.0763(13) 0.0425(12) -0.0114(9) 0.0029(9) -0.0003(10) C6 0.0547(11) 0.0417(8) 0.0303(9) -0.0018(7) 0.0042(8) -0.0052(8) C7 0.0404(10) 0.0431(9) 0.0357(9) 0.0000(7) -0.0019(8) -0.0016(7) C8 0.0421(10) 0.0556(10) 0.0403(10) -0.0041(8) -0.0046(9) 0.0033(8) C9 0.0372(9) 0.0438(8) 0.0331(9) -0.0001(7) -0.0013(8) 0.0005(7) C10 0.0365(9) 0.0396(8) 0.0332(9) -0.0008(7) -0.0007(7) -0.0011(7) C11 0.0347(9) 0.0422(9) 0.0304(9) -0.0023(7) 0.0011(7) 0.0002(7) C12 0.0346(9) 0.0449(9) 0.0330(9) 0.0016(7) -0.0048(7) 0.0002(7) C13 0.0416(10) 0.0586(11) 0.0429(11) 0.0028(9) 0.0027(9) 0.0009(8) C14 0.0478(11) 0.0672(13) 0.0556(13) 0.0193(10) 0.0076(10) -0.0033(10) C15 0.0592(13) 0.0492(10) 0.0700(14) 0.0174(10) 0.0067(12) -0.0072(9) C16 0.0524(11) 0.0434(9) 0.0539(12) 0.0025(9) -0.0001(10) -0.0008(8) C17 0.0366(9) 0.0422(9) 0.0346(10) 0.0018(8) -0.0050(8) -0.0023(7) C18 0.0365(9) 0.0343(8) 0.0356(9) -0.0003(7) -0.0010(8) 0.0002(7) C19 0.0377(9) 0.0412(8) 0.0337(9) -0.0018(7) -0.0021(7) 0.0041(7) C20 0.0356(9) 0.0395(8) 0.0381(9) -0.0041(7) 0.0002(8) -0.0038(7) C21 0.0580(12) 0.0469(10) 0.0460(12) -0.0045(9) -0.0035(9) 0.0069(8) C22 0.0796(15) 0.0480(10) 0.0567(14) -0.0169(10) 0.0040(12) 0.0050(10) C23 0.0911(16) 0.0628(13) 0.0424(13) -0.0179(10) 0.0029(12) -0.0045(11) C24 0.0833(14) 0.0627(13) 0.0369(11) -0.0013(10) -0.0028(11) -0.0036(11) C25 0.0558(11) 0.0416(9) 0.0392(10) -0.0032(8) 0.0006(9) -0.0012(8) C26 0.0403(10) 0.0550(10) 0.0494(11) -0.0036(9) 0.0023(9) -0.0059(8) C27 0.0565(13) 0.0744(14) 0.0488(13) 0.0013(10) 0.0053(10) -0.0184(10) C28 0.0625(15) 0.1048(19) 0.0493(14) -0.0154(13) 0.0180(11) -0.0285(14) C29 0.0537(13) 0.0931(18) 0.0741(17) -0.0314(14) 0.0222(13) -0.0016(12) C30 0.0470(11) 0.0619(11) 0.0594(13) -0.0153(10) 0.0059(10) 0.0048(9) C31 0.0358(9) 0.0503(10) 0.0363(10) -0.0095(8) -0.0044(8) -0.0025(7) C32 0.0454(11) 0.0514(10) 0.0518(11) -0.0080(9) -0.0092(9) 0.0068(8) C33 0.0488(12) 0.0700(13) 0.0732(15) -0.0112(11) -0.0153(11) 0.0160(10) C34 0.0726(15) 0.0539(11) 0.0613(14) -0.0075(10) -0.0133(11) 0.0227(11) C35 0.0797(16) 0.0433(10) 0.0450(11) -0.0016(8) -0.0049(10) 0.0051(10) C36 0.0513(11) 0.0473(10) 0.0390(10) -0.0030(8) 0.0014(9) 0.0026(8) C37 0.0430(10) 0.0431(9) 0.0290(9) -0.0054(7) -0.0013(8) 0.0049(7) C38 0.0567(13) 0.0975(17) 0.0627(15) -0.0166(13) -0.0202(12) 0.0189(12) _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 C18 1.4449(18) . ? O1 C11 1.4538(19) . ? O2 C8 1.365(2) . ? O2 C7 1.385(2) . ? C1 C2 1.375(3) . ? C1 C6 1.393(3) . ? C1 H1A 0.9300 . ? C2 C3 1.373(3) . ? C2 H2A 0.9300 . ? C3 C4 1.358(3) . ? C3 H3A 0.9300 . ? C4 C5 1.380(3) . ? C4 H4A 0.9300 . ? C5 C6 1.383(3) . ? C5 H5A 0.9300 . ? C6 C7 1.464(2) . ? C7 C10 1.366(2) . ? C8 C9 1.346(2) . ? C8 C38 1.484(3) . ? C9 C10 1.437(2) . ? C9 C19 1.510(2) . ? C10 C11 1.521(2) . ? C11 C37 1.510(2) . ? C11 C12 1.518(2) . ? C12 C13 1.383(2) . ? C12 C17 1.385(2) . ? C13 C14 1.381(3) . ? C13 H13A 0.9300 . ? C14 C15 1.376(3) . ? C14 H14A 0.9300 . ? C15 C16 1.386(3) . ? C15 H15A 0.9300 . ? C16 C17 1.379(2) . ? C16 H16A 0.9300 . ? C17 C18 1.527(2) . ? C18 C20 1.513(2) . ? C18 C19 1.567(2) . ? C19 C31 1.510(2) . ? C19 H19A 0.9800 . ? C20 C25 1.377(2) . ? C20 C21 1.392(2) . ? C21 C22 1.377(3) . ? C21 H21A 0.9300 . ? C22 C23 1.366(3) . ? C22 H22A 0.9300 . ? C23 C24 1.379(3) . ? C23 H23A 0.9300 . ? C24 C25 1.377(3) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 C27 1.375(3) . ? C26 C31 1.389(2) . ? C26 H26A 0.9300 . ? C27 C28 1.368(3) . ? C27 H27A 0.9300 . ? C28 C29 1.368(3) . ? C28 H28A 0.9300 . ? C29 C30 1.380(3) . ? C29 H29A 0.9300 . ? C30 C31 1.383(2) . ? C30 H30A 0.9300 . ? C32 C37 1.383(2) . ? C32 C33 1.384(3) . ? C32 H32A 0.9300 . ? C33 C34 1.370(3) . ? C33 H33A 0.9300 . ? C34 C35 1.372(3) . ? C34 H34A 0.9300 . ? C35 C36 1.378(3) . ? C35 H35A 0.9300 . ? C36 C37 1.387(2) . ? C36 H36A 0.9300 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 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 C18 O1 C11 106.71(11) . . ? C8 O2 C7 108.09(13) . . ? C2 C1 C6 121.2(2) . . ? C2 C1 H1A 119.4 . . ? C6 C1 H1A 119.4 . . ? C3 C2 C1 120.6(2) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C4 C3 C2 119.1(2) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C4 C5 C6 121.5(2) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C5 C6 C1 116.83(17) . . ? C5 C6 C7 123.80(16) . . ? C1 C6 C7 119.34(17) . . ? C10 C7 O2 108.18(14) . . ? C10 C7 C6 138.29(16) . . ? O2 C7 C6 113.26(15) . . ? C9 C8 O2 109.86(15) . . ? C9 C8 C38 133.97(18) . . ? O2 C8 C38 116.17(16) . . ? C8 C9 C10 106.84(15) . . ? C8 C9 C19 129.07(15) . . ? C10 C9 C19 124.09(15) . . ? C7 C10 C9 106.96(15) . . ? C7 C10 C11 135.83(15) . . ? C9 C10 C11 116.35(14) . . ? O1 C11 C37 105.16(13) . . ? O1 C11 C12 101.56(12) . . ? C37 C11 C12 120.19(14) . . ? O1 C11 C10 106.61(12) . . ? C37 C11 C10 117.25(13) . . ? C12 C11 C10 104.27(13) . . ? C13 C12 C17 121.14(16) . . ? C13 C12 C11 131.06(16) . . ? C17 C12 C11 107.40(14) . . ? C14 C13 C12 118.49(18) . . ? C14 C13 H13A 120.8 . . ? C12 C13 H13A 120.8 . . ? C15 C14 C13 120.60(19) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C14 C15 C16 120.88(17) . . ? C14 C15 H15A 119.6 . . ? C16 C15 H15A 119.6 . . ? C17 C16 C15 118.86(18) . . ? C17 C16 H16A 120.6 . . ? C15 C16 H16A 120.6 . . ? C16 C17 C12 119.99(17) . . ? C16 C17 C18 131.44(16) . . ? C12 C17 C18 108.54(14) . . ? O1 C18 C20 109.88(13) . . ? O1 C18 C17 101.37(12) . . ? C20 C18 C17 114.90(13) . . ? O1 C18 C19 105.49(12) . . ? C20 C18 C19 112.07(13) . . ? C17 C18 C19 112.14(14) . . ? C9 C19 C31 112.81(13) . . ? C9 C19 C18 108.15(13) . . ? C31 C19 C18 111.16(14) . . ? C9 C19 H19A 108.2 . . ? C31 C19 H19A 108.2 . . ? C18 C19 H19A 108.2 . . ? C25 C20 C21 118.18(16) . . ? C25 C20 C18 121.77(14) . . ? C21 C20 C18 120.03(15) . . ? C22 C21 C20 120.84(19) . . ? C22 C21 H21A 119.6 . . ? C20 C21 H21A 119.6 . . ? C23 C22 C21 120.27(18) . . ? C23 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? C22 C23 C24 119.51(19) . . ? C22 C23 H23A 120.2 . . ? C24 C23 H23A 120.2 . . ? C25 C24 C23 120.4(2) . . ? C25 C24 H24A 119.8 . . ? C23 C24 H24A 119.8 . . ? C24 C25 C20 120.74(17) . . ? C24 C25 H25A 119.6 . . ? C20 C25 H25A 119.6 . . ? C27 C26 C31 120.92(19) . . ? C27 C26 H26A 119.5 . . ? C31 C26 H26A 119.5 . . ? C28 C27 C26 120.3(2) . . ? C28 C27 H27A 119.9 . . ? C26 C27 H27A 119.9 . . ? C29 C28 C27 119.7(2) . . ? C29 C28 H28A 120.1 . . ? C27 C28 H28A 120.1 . . ? C28 C29 C30 120.3(2) . . ? C28 C29 H29A 119.8 . . ? C30 C29 H29A 119.8 . . ? C29 C30 C31 120.8(2) . . ? C29 C30 H30A 119.6 . . ? C31 C30 H30A 119.6 . . ? C30 C31 C26 117.92(17) . . ? C30 C31 C19 120.67(16) . . ? C26 C31 C19 121.35(15) . . ? C37 C32 C33 120.13(18) . . ? C37 C32 H32A 119.9 . . ? C33 C32 H32A 119.9 . . ? C34 C33 C32 120.55(19) . . ? C34 C33 H33A 119.7 . . ? C32 C33 H33A 119.7 . . ? C33 C34 C35 119.68(18) . . ? C33 C34 H34A 120.2 . . ? C35 C34 H34A 120.2 . . ? C34 C35 C36 120.26(19) . . ? C34 C35 H35A 119.9 . . ? C36 C35 H35A 119.9 . . ? C35 C36 C37 120.59(19) . . ? C35 C36 H36A 119.7 . . ? C37 C36 H36A 119.7 . . ? C32 C37 C36 118.73(16) . . ? C32 C37 C11 122.21(15) . . ? C36 C37 C11 119.02(15) . . ? C8 C38 H38A 109.5 . . ? C8 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C8 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 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 C6 C1 C2 C3 -1.4(3) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 -1.2(4) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? C4 C5 C6 C7 178.75(19) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C2 C1 C6 C7 -177.56(19) . . . . ? C8 O2 C7 C10 -2.33(18) . . . . ? C8 O2 C7 C6 172.86(14) . . . . ? C5 C6 C7 C10 -6.0(3) . . . . ? C1 C6 C7 C10 171.8(2) . . . . ? C5 C6 C7 O2 -179.12(17) . . . . ? C1 C6 C7 O2 -1.3(2) . . . . ? C7 O2 C8 C9 0.9(2) . . . . ? C7 O2 C8 C38 -178.66(17) . . . . ? O2 C8 C9 C10 0.9(2) . . . . ? C38 C8 C9 C10 -179.7(2) . . . . ? O2 C8 C9 C19 -178.33(16) . . . . ? C38 C8 C9 C19 1.1(4) . . . . ? O2 C7 C10 C9 2.81(18) . . . . ? C6 C7 C10 C9 -170.53(19) . . . . ? O2 C7 C10 C11 171.31(17) . . . . ? C6 C7 C10 C11 -2.0(3) . . . . ? C8 C9 C10 C7 -2.29(19) . . . . ? C19 C9 C10 C7 176.96(15) . . . . ? C8 C9 C10 C11 -173.37(15) . . . . ? C19 C9 C10 C11 5.9(2) . . . . ? C18 O1 C11 C37 -163.66(12) . . . . ? C18 O1 C11 C12 -37.70(14) . . . . ? C18 O1 C11 C10 71.18(15) . . . . ? C7 C10 C11 O1 160.23(18) . . . . ? C9 C10 C11 O1 -32.05(18) . . . . ? C7 C10 C11 C37 42.8(3) . . . . ? C9 C10 C11 C37 -149.48(15) . . . . ? C7 C10 C11 C12 -92.8(2) . . . . ? C9 C10 C11 C12 74.91(17) . . . . ? O1 C11 C12 C13 -163.09(17) . . . . ? C37 C11 C12 C13 -47.8(3) . . . . ? C10 C11 C12 C13 86.2(2) . . . . ? O1 C11 C12 C17 24.28(16) . . . . ? C37 C11 C12 C17 139.61(15) . . . . ? C10 C11 C12 C17 -86.40(16) . . . . ? C17 C12 C13 C14 -1.8(3) . . . . ? C11 C12 C13 C14 -173.54(18) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? C14 C15 C16 C17 -0.6(3) . . . . ? C15 C16 C17 C12 -0.8(3) . . . . ? C15 C16 C17 C18 177.13(18) . . . . ? C13 C12 C17 C16 2.0(3) . . . . ? C11 C12 C17 C16 175.54(16) . . . . ? C13 C12 C17 C18 -176.36(15) . . . . ? C11 C12 C17 C18 -2.84(18) . . . . ? C11 O1 C18 C20 157.76(13) . . . . ? C11 O1 C18 C17 35.79(15) . . . . ? C11 O1 C18 C19 -81.25(14) . . . . ? C16 C17 C18 O1 162.06(18) . . . . ? C12 C17 C18 O1 -19.80(17) . . . . ? C16 C17 C18 C20 43.6(3) . . . . ? C12 C17 C18 C20 -138.22(14) . . . . ? C16 C17 C18 C19 -85.9(2) . . . . ? C12 C17 C18 C19 92.28(15) . . . . ? C8 C9 C19 C31 -71.0(2) . . . . ? C10 C9 C19 C31 109.90(18) . . . . ? C8 C9 C19 C18 165.62(17) . . . . ? C10 C9 C19 C18 -13.5(2) . . . . ? O1 C18 C19 C9 47.81(16) . . . . ? C20 C18 C19 C9 167.36(13) . . . . ? C17 C18 C19 C9 -61.68(16) . . . . ? O1 C18 C19 C31 -76.54(15) . . . . ? C20 C18 C19 C31 43.01(17) . . . . ? C17 C18 C19 C31 173.97(13) . . . . ? O1 C18 C20 C25 -0.8(2) . . . . ? C17 C18 C20 C25 112.70(17) . . . . ? C19 C18 C20 C25 -117.76(17) . . . . ? O1 C18 C20 C21 177.47(15) . . . . ? C17 C18 C20 C21 -69.0(2) . . . . ? C19 C18 C20 C21 60.5(2) . . . . ? C25 C20 C21 C22 -1.5(3) . . . . ? C18 C20 C21 C22 -179.85(18) . . . . ? C20 C21 C22 C23 1.1(3) . . . . ? C21 C22 C23 C24 -0.2(3) . . . . ? C22 C23 C24 C25 -0.4(3) . . . . ? C23 C24 C25 C20 0.0(3) . . . . ? C21 C20 C25 C24 0.9(3) . . . . ? C18 C20 C25 C24 179.26(18) . . . . ? C31 C26 C27 C28 -0.3(3) . . . . ? C26 C27 C28 C29 -1.5(3) . . . . ? C27 C28 C29 C30 1.9(3) . . . . ? C28 C29 C30 C31 -0.5(3) . . . . ? C29 C30 C31 C26 -1.2(3) . . . . ? C29 C30 C31 C19 176.13(18) . . . . ? C27 C26 C31 C30 1.6(3) . . . . ? C27 C26 C31 C19 -175.71(17) . . . . ? C9 C19 C31 C30 130.25(17) . . . . ? C18 C19 C31 C30 -108.08(18) . . . . ? C9 C19 C31 C26 -52.5(2) . . . . ? C18 C19 C31 C26 69.15(19) . . . . ? C37 C32 C33 C34 0.6(3) . . . . ? C32 C33 C34 C35 1.6(3) . . . . ? C33 C34 C35 C36 -2.5(3) . . . . ? C34 C35 C36 C37 1.1(3) . . . . ? C33 C32 C37 C36 -2.0(3) . . . . ? C33 C32 C37 C11 -179.89(18) . . . . ? C35 C36 C37 C32 1.1(3) . . . . ? C35 C36 C37 C11 179.09(17) . . . . ? O1 C11 C37 C32 103.25(18) . . . . ? C12 C11 C37 C32 -10.2(2) . . . . ? C10 C11 C37 C32 -138.54(17) . . . . ? O1 C11 C37 C36 -74.64(18) . . . . ? C12 C11 C37 C36 171.92(15) . . . . ? C10 C11 C37 C36 43.6(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.088 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.025 # Attachment '4a.cif' data_z_4a _database_code_depnum_ccdc_archive 'CCDC 784919' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H28 O2' _chemical_formula_weight 516.60 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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 16.4516(5) _cell_length_b 10.4221(3) _cell_length_c 15.5783(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2671.06(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.448 _exptl_crystal_size_mid 0.257 _exptl_crystal_size_min 0.236 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.868250 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29372 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4698 _reflns_number_gt 4603 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.4455P] 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 1.2(8) _refine_ls_number_reflns 4698 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0272 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 O1 O 0.24784(5) 0.94216(8) 0.56507(6) 0.02329(19) Uani 1 1 d . . . O2 O 0.12487(5) 1.11193(9) 0.79177(6) 0.0280(2) Uani 1 1 d . . . C1 C 0.07756(9) 1.35853(14) 0.76961(10) 0.0344(3) Uani 1 1 d . . . H1A H 0.0497 1.3048 0.8092 0.041 Uiso 1 1 calc R . . C2 C 0.06502(10) 1.48983(15) 0.77176(11) 0.0394(4) Uani 1 1 d . . . H2A H 0.0289 1.5255 0.8129 0.047 Uiso 1 1 calc R . . C3 C 0.10470(9) 1.56950(14) 0.71454(12) 0.0381(4) Uani 1 1 d . . . H3A H 0.0972 1.6598 0.7172 0.046 Uiso 1 1 calc R . . C4 C 0.15525(9) 1.51637(14) 0.65358(11) 0.0362(3) Uani 1 1 d . . . H4A H 0.1814 1.5704 0.6130 0.043 Uiso 1 1 calc R . . C5 C 0.16836(8) 1.38555(13) 0.65075(10) 0.0310(3) Uani 1 1 d . . . H5A H 0.2033 1.3507 0.6082 0.037 Uiso 1 1 calc R . . C6 C 0.13079(8) 1.30408(13) 0.70973(9) 0.0264(3) Uani 1 1 d . . . C7 C 0.15091(7) 1.16741(13) 0.71615(8) 0.0246(3) Uani 1 1 d . . . C8 C 0.15900(8) 0.99247(13) 0.79718(9) 0.0274(3) Uani 1 1 d . . . C9 C 0.20596(8) 0.97040(12) 0.72772(9) 0.0243(3) Uani 1 1 d . . . C10 C 0.19804(7) 1.08133(12) 0.67314(8) 0.0227(3) Uani 1 1 d . . . C11 C 0.24242(7) 1.07762(11) 0.58757(8) 0.0234(3) Uani 1 1 d . . . C12 C 0.33048(7) 1.10876(13) 0.60677(8) 0.0236(3) Uani 1 1 d . . . C13 C 0.37083(8) 1.22496(13) 0.60771(10) 0.0296(3) Uani 1 1 d . . . H13A H 0.3435 1.3019 0.5922 0.035 Uiso 1 1 calc R . . C14 C 0.45179(9) 1.22696(14) 0.63163(11) 0.0369(3) Uani 1 1 d . . . H14A H 0.4811 1.3054 0.6307 0.044 Uiso 1 1 calc R . . C15 C 0.49017(9) 1.11507(15) 0.65692(11) 0.0392(4) Uani 1 1 d . . . H15A H 0.5457 1.1178 0.6734 0.047 Uiso 1 1 calc R . . C16 C 0.44895(8) 0.99880(14) 0.65869(10) 0.0316(3) Uani 1 1 d . . . H16A H 0.4753 0.9230 0.6780 0.038 Uiso 1 1 calc R . . C17 C 0.36882(8) 0.99553(12) 0.63175(8) 0.0245(3) Uani 1 1 d . . . C18 C 0.30737(8) 0.88591(12) 0.62227(8) 0.0242(3) Uani 1 1 d . . . C19 C 0.25843(8) 0.85537(12) 0.70713(9) 0.0245(3) Uani 1 1 d . . . H19A H 0.2206 0.7833 0.6931 0.029 Uiso 1 1 calc R . . C20 C 0.33910(8) 0.76301(12) 0.58190(9) 0.0254(3) Uani 1 1 d . . . C21 C 0.40872(9) 0.70200(14) 0.61224(10) 0.0336(3) Uani 1 1 d . . . H21A H 0.4375 0.7378 0.6593 0.040 Uiso 1 1 calc R . . C22 C 0.43647(9) 0.58993(14) 0.57470(11) 0.0386(3) Uani 1 1 d . . . H22A H 0.4843 0.5500 0.5959 0.046 Uiso 1 1 calc R . . C23 C 0.39525(10) 0.53604(14) 0.50700(11) 0.0376(3) Uani 1 1 d . . . H23A H 0.4150 0.4601 0.4805 0.045 Uiso 1 1 calc R . . C24 C 0.32470(11) 0.59364(15) 0.47783(10) 0.0382(3) Uani 1 1 d . . . H24A H 0.2951 0.5556 0.4321 0.046 Uiso 1 1 calc R . . C25 C 0.29682(9) 0.70606(13) 0.51465(9) 0.0306(3) Uani 1 1 d . . . H25A H 0.2484 0.7447 0.4938 0.037 Uiso 1 1 calc R . . C26 C 0.35328(9) 0.89526(14) 0.83373(9) 0.0314(3) Uani 1 1 d . . . H26A H 0.3488 0.9849 0.8238 0.038 Uiso 1 1 calc R . . C27 C 0.40216(9) 0.85058(16) 0.89994(10) 0.0365(3) Uani 1 1 d . . . H27A H 0.4312 0.9098 0.9348 0.044 Uiso 1 1 calc R . . C28 C 0.40883(9) 0.72049(16) 0.91545(10) 0.0384(4) Uani 1 1 d . . . H28A H 0.4423 0.6903 0.9609 0.046 Uiso 1 1 calc R . . C29 C 0.36689(10) 0.63497(15) 0.86495(10) 0.0373(3) Uani 1 1 d . . . H29A H 0.3713 0.5454 0.8755 0.045 Uiso 1 1 calc R . . C30 C 0.31814(9) 0.67934(13) 0.79863(10) 0.0310(3) Uani 1 1 d . . . H30A H 0.2893 0.6196 0.7641 0.037 Uiso 1 1 calc R . . C31 C 0.31077(8) 0.81004(13) 0.78180(8) 0.0264(3) Uani 1 1 d . . . C32 C 0.24663(9) 1.19562(13) 0.44592(9) 0.0292(3) Uani 1 1 d . . . H32A H 0.3042 1.1897 0.4472 0.035 Uiso 1 1 calc R . . C33 C 0.20845(10) 1.25433(15) 0.37673(10) 0.0357(3) Uani 1 1 d . . . H33A H 0.2400 1.2887 0.3311 0.043 Uiso 1 1 calc R . . C34 C 0.12482(10) 1.26291(15) 0.37409(10) 0.0369(3) Uani 1 1 d . . . H34A H 0.0987 1.3027 0.3266 0.044 Uiso 1 1 calc R . . C35 C 0.07922(9) 1.21358(15) 0.44060(10) 0.0351(3) Uani 1 1 d . . . H35A H 0.0216 1.2201 0.4391 0.042 Uiso 1 1 calc R . . C36 C 0.11708(8) 1.15449(13) 0.50963(9) 0.0299(3) Uani 1 1 d . . . H36A H 0.0852 1.1198 0.5549 0.036 Uiso 1 1 calc R . . C37 C 0.20131(8) 1.14555(12) 0.51315(8) 0.0239(3) Uani 1 1 d . . . C38 C 0.13608(10) 0.91599(16) 0.87357(10) 0.0390(4) Uani 1 1 d . . . H38A H 0.1637 0.8327 0.8716 0.059 Uiso 1 1 calc R . . H38B H 0.0771 0.9027 0.8740 0.059 Uiso 1 1 calc R . . H38C H 0.1523 0.9620 0.9257 0.059 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 0.0253(4) 0.0211(4) 0.0235(5) 0.0005(4) -0.0034(4) 0.0003(4) O2 0.0276(5) 0.0305(5) 0.0258(5) 0.0023(4) 0.0027(4) 0.0023(4) C1 0.0305(7) 0.0394(8) 0.0334(8) 0.0005(6) -0.0002(6) 0.0071(6) C2 0.0366(8) 0.0407(8) 0.0410(9) -0.0069(7) -0.0015(7) 0.0128(7) C3 0.0344(8) 0.0273(7) 0.0527(9) -0.0050(7) -0.0133(7) 0.0058(6) C4 0.0339(7) 0.0298(7) 0.0448(9) 0.0020(7) -0.0054(6) -0.0043(6) C5 0.0278(7) 0.0302(7) 0.0351(8) -0.0024(6) -0.0007(6) -0.0002(6) C6 0.0223(6) 0.0290(7) 0.0281(7) -0.0020(6) -0.0057(5) 0.0019(5) C7 0.0213(6) 0.0293(7) 0.0232(6) 0.0037(6) -0.0029(5) -0.0025(5) C8 0.0248(6) 0.0293(7) 0.0280(7) 0.0041(6) -0.0015(6) -0.0008(5) C9 0.0229(6) 0.0246(6) 0.0253(6) 0.0018(5) -0.0034(5) -0.0033(5) C10 0.0205(6) 0.0233(6) 0.0245(6) 0.0019(5) -0.0029(5) -0.0035(5) C11 0.0248(6) 0.0207(6) 0.0245(7) 0.0011(5) 0.0003(5) -0.0007(5) C12 0.0236(6) 0.0264(7) 0.0208(6) 0.0021(5) 0.0008(5) 0.0000(5) C13 0.0304(7) 0.0251(6) 0.0332(7) 0.0048(6) -0.0004(6) -0.0023(6) C14 0.0324(7) 0.0314(7) 0.0470(9) 0.0039(7) -0.0039(6) -0.0097(6) C15 0.0242(7) 0.0426(8) 0.0507(9) 0.0037(7) -0.0079(7) -0.0056(6) C16 0.0259(7) 0.0299(7) 0.0389(8) 0.0040(6) -0.0042(6) 0.0017(5) C17 0.0261(6) 0.0251(6) 0.0222(6) 0.0012(5) 0.0020(5) -0.0002(5) C18 0.0242(6) 0.0241(6) 0.0243(7) 0.0025(5) -0.0030(5) -0.0001(5) C19 0.0254(6) 0.0220(6) 0.0262(7) 0.0027(5) -0.0006(5) -0.0038(5) C20 0.0283(6) 0.0230(6) 0.0249(7) 0.0046(5) 0.0018(5) -0.0017(5) C21 0.0330(7) 0.0299(7) 0.0378(8) 0.0004(6) -0.0044(6) 0.0027(6) C22 0.0373(8) 0.0312(7) 0.0472(9) 0.0047(7) -0.0004(7) 0.0082(6) C23 0.0522(9) 0.0246(7) 0.0360(8) 0.0036(6) 0.0069(7) 0.0078(7) C24 0.0558(10) 0.0289(7) 0.0297(8) -0.0017(6) -0.0040(7) 0.0007(7) C25 0.0365(7) 0.0267(7) 0.0286(7) 0.0016(6) -0.0042(6) 0.0011(6) C26 0.0339(7) 0.0286(7) 0.0317(8) 0.0007(6) -0.0007(6) 0.0022(6) C27 0.0351(8) 0.0454(9) 0.0290(7) -0.0072(7) -0.0044(6) 0.0056(7) C28 0.0371(8) 0.0501(10) 0.0280(7) 0.0052(7) -0.0033(6) 0.0133(7) C29 0.0425(8) 0.0315(8) 0.0380(8) 0.0103(7) 0.0047(7) 0.0095(6) C30 0.0347(7) 0.0253(7) 0.0330(7) 0.0035(6) 0.0018(6) 0.0005(6) C31 0.0276(6) 0.0279(7) 0.0239(7) 0.0025(5) 0.0036(5) 0.0005(5) C32 0.0312(7) 0.0284(7) 0.0281(7) 0.0007(6) 0.0011(5) 0.0044(6) C33 0.0464(9) 0.0348(8) 0.0260(7) 0.0054(6) 0.0031(6) 0.0061(7) C34 0.0504(9) 0.0314(8) 0.0289(8) 0.0006(6) -0.0101(7) 0.0105(7) C35 0.0316(7) 0.0364(8) 0.0373(8) -0.0030(6) -0.0088(6) 0.0048(6) C36 0.0294(7) 0.0301(7) 0.0302(7) 0.0003(6) -0.0030(6) -0.0018(6) C37 0.0277(6) 0.0207(6) 0.0233(6) -0.0017(5) -0.0024(5) 0.0008(5) C38 0.0432(9) 0.0390(9) 0.0348(8) 0.0095(7) 0.0087(7) -0.0012(7) _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 C18 1.4481(15) . ? O1 C11 1.4574(14) . ? O2 C8 1.3683(16) . ? O2 C7 1.3805(16) . ? C1 C2 1.384(2) . ? C1 C6 1.400(2) . ? C1 H1A 0.9500 . ? C2 C3 1.382(2) . ? C2 H2A 0.9500 . ? C3 C4 1.378(2) . ? C3 H3A 0.9500 . ? C4 C5 1.381(2) . ? C4 H4A 0.9500 . ? C5 C6 1.395(2) . ? C5 H5A 0.9500 . ? C6 C7 1.4657(19) . ? C7 C10 1.3620(19) . ? C8 C9 1.349(2) . ? C8 C38 1.481(2) . ? C9 C10 1.4410(18) . ? C9 C19 1.5116(18) . ? C10 C11 1.5203(18) . ? C11 C12 1.5146(17) . ? C11 C37 1.5175(17) . ? C12 C13 1.3810(19) . ? C12 C17 1.3936(18) . ? C13 C14 1.383(2) . ? C13 H13A 0.9500 . ? C14 C15 1.383(2) . ? C14 H14A 0.9500 . ? C15 C16 1.389(2) . ? C15 H15A 0.9500 . ? C16 C17 1.3838(19) . ? C16 H16A 0.9500 . ? C17 C18 1.5327(18) . ? C18 C20 1.5194(19) . ? C18 C19 1.5802(18) . ? C19 C31 1.5225(18) . ? C19 H19A 1.0000 . ? C20 C25 1.3906(19) . ? C20 C21 1.393(2) . ? C21 C22 1.384(2) . ? C21 H21A 0.9500 . ? C22 C23 1.374(2) . ? C22 H22A 0.9500 . ? C23 C24 1.384(2) . ? C23 H23A 0.9500 . ? C24 C25 1.383(2) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 C27 1.388(2) . ? C26 C31 1.390(2) . ? C26 H26A 0.9500 . ? C27 C28 1.381(2) . ? C27 H27A 0.9500 . ? C28 C29 1.375(2) . ? C28 H28A 0.9500 . ? C29 C30 1.387(2) . ? C29 H29A 0.9500 . ? C30 C31 1.3924(19) . ? C30 H30A 0.9500 . ? C32 C37 1.3874(19) . ? C32 C33 1.390(2) . ? C32 H32A 0.9500 . ? C33 C34 1.379(2) . ? C33 H33A 0.9500 . ? C34 C35 1.379(2) . ? C34 H34A 0.9500 . ? C35 C36 1.387(2) . ? C35 H35A 0.9500 . ? C36 C37 1.3900(19) . ? C36 H36A 0.9500 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 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 C18 O1 C11 106.59(8) . . ? C8 O2 C7 107.84(10) . . ? C2 C1 C6 120.68(14) . . ? C2 C1 H1A 119.7 . . ? C6 C1 H1A 119.7 . . ? C3 C2 C1 120.52(15) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C4 C3 C2 119.20(14) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 120.85(15) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C4 C5 C6 120.70(14) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C6 C1 117.98(13) . . ? C5 C6 C7 122.43(12) . . ? C1 C6 C7 119.33(13) . . ? C10 C7 O2 108.69(11) . . ? C10 C7 C6 137.32(13) . . ? O2 C7 C6 113.28(11) . . ? C9 C8 O2 109.92(12) . . ? C9 C8 C38 134.29(14) . . ? O2 C8 C38 115.77(12) . . ? C8 C9 C10 106.53(12) . . ? C8 C9 C19 129.22(12) . . ? C10 C9 C19 124.24(12) . . ? C7 C10 C9 106.84(12) . . ? C7 C10 C11 136.17(12) . . ? C9 C10 C11 116.97(11) . . ? O1 C11 C12 101.33(9) . . ? O1 C11 C37 107.19(10) . . ? C12 C11 C37 118.50(11) . . ? O1 C11 C10 105.36(10) . . ? C12 C11 C10 106.30(10) . . ? C37 C11 C10 116.36(10) . . ? C13 C12 C17 121.47(12) . . ? C13 C12 C11 130.52(12) . . ? C17 C12 C11 107.86(11) . . ? C12 C13 C14 118.61(13) . . ? C12 C13 H13A 120.7 . . ? C14 C13 H13A 120.7 . . ? C13 C14 C15 120.23(13) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C14 C15 C16 121.22(13) . . ? C14 C15 H15A 119.4 . . ? C16 C15 H15A 119.4 . . ? C17 C16 C15 118.72(13) . . ? C17 C16 H16A 120.6 . . ? C15 C16 H16A 120.6 . . ? C16 C17 C12 119.67(12) . . ? C16 C17 C18 132.53(12) . . ? C12 C17 C18 107.80(11) . . ? O1 C18 C20 108.60(10) . . ? O1 C18 C17 101.75(10) . . ? C20 C18 C17 116.21(11) . . ? O1 C18 C19 104.58(10) . . ? C20 C18 C19 110.58(10) . . ? C17 C18 C19 113.93(10) . . ? C9 C19 C31 114.01(11) . . ? C9 C19 C18 107.98(10) . . ? C31 C19 C18 114.42(10) . . ? C9 C19 H19A 106.6 . . ? C31 C19 H19A 106.6 . . ? C18 C19 H19A 106.6 . . ? C25 C20 C21 118.18(13) . . ? C25 C20 C18 119.98(12) . . ? C21 C20 C18 121.80(12) . . ? C22 C21 C20 120.88(14) . . ? C22 C21 H21A 119.6 . . ? C20 C21 H21A 119.6 . . ? C23 C22 C21 120.44(14) . . ? C23 C22 H22A 119.8 . . ? C21 C22 H22A 119.8 . . ? C22 C23 C24 119.27(14) . . ? C22 C23 H23A 120.4 . . ? C24 C23 H23A 120.4 . . ? C25 C24 C23 120.64(14) . . ? C25 C24 H24A 119.7 . . ? C23 C24 H24A 119.7 . . ? C24 C25 C20 120.55(13) . . ? C24 C25 H25A 119.7 . . ? C20 C25 H25A 119.7 . . ? C27 C26 C31 120.63(14) . . ? C27 C26 H26A 119.7 . . ? C31 C26 H26A 119.7 . . ? C28 C27 C26 120.34(15) . . ? C28 C27 H27A 119.8 . . ? C26 C27 H27A 119.8 . . ? C29 C28 C27 119.77(14) . . ? C29 C28 H28A 120.1 . . ? C27 C28 H28A 120.1 . . ? C28 C29 C30 120.01(14) . . ? C28 C29 H29A 120.0 . . ? C30 C29 H29A 120.0 . . ? C29 C30 C31 121.11(14) . . ? C29 C30 H30A 119.4 . . ? C31 C30 H30A 119.4 . . ? C26 C31 C30 118.14(13) . . ? C26 C31 C19 122.07(12) . . ? C30 C31 C19 119.78(12) . . ? C37 C32 C33 120.54(13) . . ? C37 C32 H32A 119.7 . . ? C33 C32 H32A 119.7 . . ? C34 C33 C32 120.17(14) . . ? C34 C33 H33A 119.9 . . ? C32 C33 H33A 119.9 . . ? C35 C34 C33 119.75(13) . . ? C35 C34 H34A 120.1 . . ? C33 C34 H34A 120.1 . . ? C34 C35 C36 120.26(14) . . ? C34 C35 H35A 119.9 . . ? C36 C35 H35A 119.9 . . ? C35 C36 C37 120.53(14) . . ? C35 C36 H36A 119.7 . . ? C37 C36 H36A 119.7 . . ? C32 C37 C36 118.74(13) . . ? C32 C37 C11 120.84(12) . . ? C36 C37 C11 120.38(12) . . ? C8 C38 H38A 109.5 . . ? C8 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C8 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 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 C6 C1 C2 C3 0.2(2) . . . . ? C1 C2 C3 C4 1.8(2) . . . . ? C2 C3 C4 C5 -1.9(2) . . . . ? C3 C4 C5 C6 -0.1(2) . . . . ? C4 C5 C6 C1 2.1(2) . . . . ? C4 C5 C6 C7 -171.97(13) . . . . ? C2 C1 C6 C5 -2.2(2) . . . . ? C2 C1 C6 C7 172.11(13) . . . . ? C8 O2 C7 C10 2.49(13) . . . . ? C8 O2 C7 C6 -169.57(11) . . . . ? C5 C6 C7 C10 -5.7(2) . . . . ? C1 C6 C7 C10 -179.70(14) . . . . ? C5 C6 C7 O2 163.21(12) . . . . ? C1 C6 C7 O2 -10.82(17) . . . . ? C7 O2 C8 C9 0.17(14) . . . . ? C7 O2 C8 C38 -178.33(12) . . . . ? O2 C8 C9 C10 -2.59(14) . . . . ? C38 C8 C9 C10 175.53(16) . . . . ? O2 C8 C9 C19 177.01(12) . . . . ? C38 C8 C9 C19 -4.9(3) . . . . ? O2 C7 C10 C9 -4.01(13) . . . . ? C6 C7 C10 C9 165.21(15) . . . . ? O2 C7 C10 C11 177.56(13) . . . . ? C6 C7 C10 C11 -13.2(3) . . . . ? C8 C9 C10 C7 4.07(14) . . . . ? C19 C9 C10 C7 -175.55(12) . . . . ? C8 C9 C10 C11 -177.15(11) . . . . ? C19 C9 C10 C11 3.23(18) . . . . ? C18 O1 C11 C12 38.25(11) . . . . ? C18 O1 C11 C37 163.11(10) . . . . ? C18 O1 C11 C10 -72.35(11) . . . . ? C7 C10 C11 O1 -154.00(14) . . . . ? C9 C10 C11 O1 27.69(14) . . . . ? C7 C10 C11 C12 98.99(16) . . . . ? C9 C10 C11 C12 -79.33(13) . . . . ? C7 C10 C11 C37 -35.4(2) . . . . ? C9 C10 C11 C37 146.25(11) . . . . ? O1 C11 C12 C13 158.79(14) . . . . ? C37 C11 C12 C13 41.9(2) . . . . ? C10 C11 C12 C13 -91.32(17) . . . . ? O1 C11 C12 C17 -25.66(13) . . . . ? C37 C11 C12 C17 -142.52(11) . . . . ? C10 C11 C12 C17 84.22(12) . . . . ? C17 C12 C13 C14 2.0(2) . . . . ? C11 C12 C13 C14 177.00(14) . . . . ? C12 C13 C14 C15 -2.3(2) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C14 C15 C16 C17 2.2(2) . . . . ? C15 C16 C17 C12 -2.5(2) . . . . ? C15 C16 C17 C18 177.48(15) . . . . ? C13 C12 C17 C16 0.4(2) . . . . ? C11 C12 C17 C16 -175.62(12) . . . . ? C13 C12 C17 C18 -179.54(13) . . . . ? C11 C12 C17 C18 4.43(14) . . . . ? C11 O1 C18 C20 -158.68(10) . . . . ? C11 O1 C18 C17 -35.59(11) . . . . ? C11 O1 C18 C19 83.24(11) . . . . ? C16 C17 C18 O1 -161.26(14) . . . . ? C12 C17 C18 O1 18.68(13) . . . . ? C16 C17 C18 C20 -43.5(2) . . . . ? C12 C17 C18 C20 136.42(12) . . . . ? C16 C17 C18 C19 86.81(18) . . . . ? C12 C17 C18 C19 -93.26(13) . . . . ? C8 C9 C19 C31 -45.81(18) . . . . ? C10 C9 C19 C31 133.72(13) . . . . ? C8 C9 C19 C18 -174.16(13) . . . . ? C10 C9 C19 C18 5.37(16) . . . . ? O1 C18 C19 C9 -44.69(12) . . . . ? C20 C18 C19 C9 -161.42(10) . . . . ? C17 C18 C19 C9 65.53(14) . . . . ? O1 C18 C19 C31 -172.81(10) . . . . ? C20 C18 C19 C31 70.47(14) . . . . ? C17 C18 C19 C31 -62.59(14) . . . . ? O1 C18 C20 C25 -16.14(16) . . . . ? C17 C18 C20 C25 -130.04(13) . . . . ? C19 C18 C20 C25 98.06(14) . . . . ? O1 C18 C20 C21 166.07(12) . . . . ? C17 C18 C20 C21 52.17(17) . . . . ? C19 C18 C20 C21 -79.72(15) . . . . ? C25 C20 C21 C22 2.0(2) . . . . ? C18 C20 C21 C22 179.82(13) . . . . ? C20 C21 C22 C23 -0.6(2) . . . . ? C21 C22 C23 C24 -1.3(2) . . . . ? C22 C23 C24 C25 1.7(2) . . . . ? C23 C24 C25 C20 -0.2(2) . . . . ? C21 C20 C25 C24 -1.6(2) . . . . ? C18 C20 C25 C24 -179.47(13) . . . . ? C31 C26 C27 C28 -0.4(2) . . . . ? C26 C27 C28 C29 0.1(2) . . . . ? C27 C28 C29 C30 0.0(2) . . . . ? C28 C29 C30 C31 0.1(2) . . . . ? C27 C26 C31 C30 0.5(2) . . . . ? C27 C26 C31 C19 -178.32(13) . . . . ? C29 C30 C31 C26 -0.4(2) . . . . ? C29 C30 C31 C19 178.47(13) . . . . ? C9 C19 C31 C26 -43.77(17) . . . . ? C18 C19 C31 C26 81.22(15) . . . . ? C9 C19 C31 C30 137.39(13) . . . . ? C18 C19 C31 C30 -97.62(15) . . . . ? C37 C32 C33 C34 -0.3(2) . . . . ? C32 C33 C34 C35 0.3(2) . . . . ? C33 C34 C35 C36 -0.6(2) . . . . ? C34 C35 C36 C37 0.7(2) . . . . ? C33 C32 C37 C36 0.4(2) . . . . ? C33 C32 C37 C11 178.07(12) . . . . ? C35 C36 C37 C32 -0.7(2) . . . . ? C35 C36 C37 C11 -178.32(12) . . . . ? O1 C11 C37 C32 -89.88(13) . . . . ? C12 C11 C37 C32 23.82(17) . . . . ? C10 C11 C37 C32 152.55(12) . . . . ? O1 C11 C37 C36 87.71(14) . . . . ? C12 C11 C37 C36 -158.58(12) . . . . ? C10 C11 C37 C36 -29.86(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.165 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.028 # Attachment '4k.cif' data_z_4k _database_code_depnum_ccdc_archive 'CCDC 784920' #TrackingRef '4k.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H32 O2' _chemical_formula_weight 508.63 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7864(2) _cell_length_b 14.5065(4) _cell_length_c 19.1323(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.5040(10) _cell_angle_gamma 90.00 _cell_volume 2678.86(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9687 _exptl_absorpt_correction_T_max 0.9768 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30580 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4717 _reflns_number_gt 3719 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.9408P] 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 4717 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 O1 O 0.43408(12) 1.12979(8) 0.08172(6) 0.0399(3) Uani 1 1 d . . . O2 O 0.60452(13) 0.86509(8) 0.18220(7) 0.0453(3) Uani 1 1 d . . . C1 C 0.1769(2) 1.09217(15) -0.06094(10) 0.0514(5) Uani 1 1 d . . . H1A H 0.2065 1.0334 -0.0708 0.062 Uiso 1 1 calc R . . C2 C 0.0960(2) 1.14232(17) -0.11405(11) 0.0597(6) Uani 1 1 d . . . H2A H 0.0712 1.1166 -0.1589 0.072 Uiso 1 1 calc R . . C3 C 0.0525(2) 1.22898(18) -0.10121(13) 0.0681(6) Uani 1 1 d . . . H3A H -0.0010 1.2627 -0.1370 0.082 Uiso 1 1 calc R . . C4 C 0.0887(3) 1.26560(18) -0.03480(15) 0.0882(9) Uani 1 1 d . . . H4A H 0.0593 1.3246 -0.0254 0.106 Uiso 1 1 calc R . . C5 C 0.1683(3) 1.21574(16) 0.01838(13) 0.0733(7) Uani 1 1 d . . . H5A H 0.1917 1.2416 0.0632 0.088 Uiso 1 1 calc R . . C6 C 0.21392(18) 1.12803(13) 0.00610(10) 0.0446(4) Uani 1 1 d . . . C7 C 0.5558(2) 1.27020(13) 0.20273(11) 0.0553(5) Uani 1 1 d . . . H7A H 0.4630 1.2795 0.2061 0.066 Uiso 1 1 calc R . . C8 C 0.6507(2) 1.33980(15) 0.22257(14) 0.0678(6) Uani 1 1 d . . . H8A H 0.6219 1.3952 0.2398 0.081 Uiso 1 1 calc R . . C9 C 0.7874(2) 1.32715(15) 0.21693(13) 0.0655(6) Uani 1 1 d . . . H9A H 0.8516 1.3737 0.2306 0.079 Uiso 1 1 calc R . . C10 C 0.8289(2) 1.24566(14) 0.19108(13) 0.0632(6) Uani 1 1 d . . . H10A H 0.9213 1.2373 0.1866 0.076 Uiso 1 1 calc R . . C11 C 0.73450(19) 1.17604(13) 0.17171(11) 0.0510(5) Uani 1 1 d . . . H11A H 0.7637 1.1209 0.1542 0.061 Uiso 1 1 calc R . . C12 C 0.59688(17) 1.18718(12) 0.17806(9) 0.0396(4) Uani 1 1 d . . . C13 C 0.7284(2) 1.04736(14) 0.31009(11) 0.0538(5) Uani 1 1 d . . . H13A H 0.6661 1.0946 0.2954 0.065 Uiso 1 1 calc R . . C14 C 0.8239(3) 1.05797(17) 0.37106(12) 0.0663(6) Uani 1 1 d . . . H14A H 0.8256 1.1124 0.3968 0.080 Uiso 1 1 calc R . . C15 C 0.9161(3) 0.98924(19) 0.39416(12) 0.0720(7) Uani 1 1 d . . . H15A H 0.9821 0.9975 0.4346 0.086 Uiso 1 1 calc R . . C16 C 0.9103(2) 0.90778(18) 0.35684(12) 0.0664(6) Uani 1 1 d . . . H16A H 0.9708 0.8601 0.3731 0.080 Uiso 1 1 calc R . . C17 C 0.8155(2) 0.89613(15) 0.29559(10) 0.0529(5) Uani 1 1 d . . . H17A H 0.8126 0.8407 0.2710 0.063 Uiso 1 1 calc R . . C18 C 0.72407(18) 0.96686(13) 0.27023(9) 0.0428(4) Uani 1 1 d . . . C19 C 0.4359(2) 0.78113(14) 0.09218(12) 0.0587(5) Uani 1 1 d . . . H19A H 0.3973 0.7471 0.1280 0.070 Uiso 1 1 calc R . . H19B H 0.5028 0.7420 0.0744 0.070 Uiso 1 1 calc R . . C20 C 0.3199(2) 0.80843(14) 0.03130(11) 0.0558(5) Uani 1 1 d . . . H20A H 0.3591 0.8140 -0.0119 0.067 Uiso 1 1 calc R . . H20B H 0.2518 0.7593 0.0243 0.067 Uiso 1 1 calc R . . C21 C 0.2461(2) 0.89904(13) 0.04355(11) 0.0496(5) Uani 1 1 d . . . H21A H 0.1709 0.9099 0.0046 0.059 Uiso 1 1 calc R . . H21B H 0.2073 0.8948 0.0869 0.059 Uiso 1 1 calc R . . C22 C 0.34937(17) 0.97917(12) 0.04896(9) 0.0403(4) Uani 1 1 d . . . H22A H 0.3857 0.9820 0.0042 0.048 Uiso 1 1 calc R . . C23 C 0.46679(17) 0.95317(12) 0.10610(9) 0.0390(4) Uani 1 1 d . . . C24 C 0.54337(16) 1.01215(12) 0.15795(9) 0.0371(4) Uani 1 1 d . . . C25 C 0.62594(17) 0.95589(12) 0.20443(9) 0.0398(4) Uani 1 1 d . . . C26 C 0.50426(19) 0.86617(12) 0.12335(10) 0.0438(4) Uani 1 1 d . . . C27 C 0.30414(17) 1.07778(12) 0.06595(9) 0.0401(4) Uani 1 1 d . . . C28 C 0.49246(17) 1.11181(12) 0.15547(9) 0.0377(4) Uani 1 1 d . . . C29 C 0.25272(17) 1.08339(12) 0.13657(9) 0.0404(4) Uani 1 1 d . . . C30 C 0.12206(19) 1.06646(13) 0.15268(11) 0.0493(5) Uani 1 1 d . . . H30A H 0.0491 1.0498 0.1174 0.059 Uiso 1 1 calc R . . C31 C 0.1024(2) 1.07486(14) 0.22237(12) 0.0559(5) Uani 1 1 d . . . H31A H 0.0155 1.0632 0.2341 0.067 Uiso 1 1 calc R . . C32 C 0.2102(2) 1.10039(15) 0.27467(11) 0.0557(5) Uani 1 1 d . . . H32A H 0.1947 1.1069 0.3211 0.067 Uiso 1 1 calc R . . C33 C 0.3419(2) 1.11651(13) 0.25885(10) 0.0477(5) Uani 1 1 d . . . H33A H 0.4149 1.1327 0.2942 0.057 Uiso 1 1 calc R . . C34 C 0.36137(17) 1.10782(11) 0.18921(9) 0.0388(4) Uani 1 1 d . . . C01 C 0.3798(18) 0.9457(8) 0.4685(6) 0.320(8) Uani 1 1 d . . . H01A H 0.3177 0.9162 0.4302 0.383 Uiso 1 1 calc R . . H01B H 0.3538 0.9280 0.5134 0.383 Uiso 1 1 calc R . . C02 C 0.3791(12) 1.0289(13) 0.4614(6) 0.348(9) Uani 1 1 d . . . H02A H 0.2846 1.0495 0.4459 0.418 Uiso 1 1 calc R . . H02B H 0.4327 1.0451 0.4248 0.418 Uiso 1 1 calc R . . C03 C 0.4429(14) 1.0827(7) 0.5345(6) 0.273(5) Uani 1 1 d . . . H03A H 0.4107 1.0573 0.5757 0.327 Uiso 1 1 calc R . . H03B H 0.4257 1.1486 0.5316 0.327 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 0.0379(6) 0.0416(7) 0.0391(7) 0.0012(5) 0.0035(5) -0.0050(5) O2 0.0474(7) 0.0397(7) 0.0473(7) -0.0017(5) 0.0033(6) 0.0029(5) C1 0.0473(11) 0.0603(12) 0.0455(11) 0.0010(9) 0.0040(9) 0.0004(9) C2 0.0523(12) 0.0815(16) 0.0428(11) 0.0056(10) 0.0008(9) -0.0033(11) C3 0.0640(14) 0.0744(16) 0.0599(14) 0.0208(12) -0.0077(11) 0.0033(12) C4 0.110(2) 0.0596(15) 0.0821(19) 0.0031(13) -0.0224(16) 0.0235(14) C5 0.0948(18) 0.0567(13) 0.0581(14) -0.0042(11) -0.0178(13) 0.0163(12) C6 0.0395(9) 0.0482(10) 0.0447(11) 0.0035(8) 0.0025(8) -0.0038(8) C7 0.0490(11) 0.0460(11) 0.0734(14) -0.0112(10) 0.0174(10) -0.0046(9) C8 0.0733(15) 0.0442(12) 0.0904(18) -0.0197(11) 0.0264(13) -0.0129(10) C9 0.0619(13) 0.0498(12) 0.0824(16) -0.0068(11) 0.0050(12) -0.0213(10) C10 0.0418(10) 0.0505(12) 0.0958(17) 0.0039(11) 0.0072(11) -0.0077(9) C11 0.0421(10) 0.0419(10) 0.0689(13) -0.0013(9) 0.0088(9) -0.0007(8) C12 0.0400(9) 0.0386(9) 0.0392(10) 0.0003(7) 0.0037(7) -0.0022(7) C13 0.0589(12) 0.0521(12) 0.0478(12) -0.0017(9) 0.0008(9) 0.0019(9) C14 0.0790(15) 0.0663(14) 0.0485(12) -0.0083(10) -0.0044(11) -0.0048(12) C15 0.0692(15) 0.0925(18) 0.0480(13) -0.0027(12) -0.0092(11) -0.0002(13) C16 0.0613(13) 0.0823(16) 0.0523(13) 0.0082(11) -0.0004(10) 0.0185(12) C17 0.0532(11) 0.0571(12) 0.0475(11) 0.0004(9) 0.0059(9) 0.0090(9) C18 0.0395(9) 0.0488(10) 0.0403(10) 0.0029(8) 0.0070(8) -0.0003(8) C19 0.0704(14) 0.0419(11) 0.0606(13) -0.0069(9) 0.0016(11) -0.0041(9) C20 0.0628(12) 0.0466(11) 0.0558(12) -0.0089(9) 0.0031(10) -0.0135(9) C21 0.0454(10) 0.0501(11) 0.0512(11) -0.0026(9) 0.0022(9) -0.0108(8) C22 0.0384(9) 0.0437(10) 0.0385(10) -0.0022(7) 0.0051(7) -0.0048(7) C23 0.0373(9) 0.0402(10) 0.0403(10) -0.0026(7) 0.0087(7) -0.0031(7) C24 0.0337(8) 0.0389(9) 0.0392(9) -0.0026(7) 0.0077(7) -0.0029(7) C25 0.0387(9) 0.0389(9) 0.0420(10) -0.0033(8) 0.0074(7) -0.0020(7) C26 0.0459(10) 0.0412(10) 0.0434(10) -0.0045(8) 0.0048(8) -0.0011(8) C27 0.0344(9) 0.0439(10) 0.0411(10) 0.0001(8) 0.0031(7) -0.0042(7) C28 0.0371(9) 0.0390(9) 0.0363(9) -0.0015(7) 0.0037(7) -0.0012(7) C29 0.0376(9) 0.0379(9) 0.0456(10) 0.0002(7) 0.0067(8) 0.0017(7) C30 0.0366(9) 0.0526(11) 0.0583(12) 0.0026(9) 0.0071(8) 0.0010(8) C31 0.0442(11) 0.0610(13) 0.0672(14) 0.0064(10) 0.0228(10) 0.0051(9) C32 0.0586(12) 0.0615(13) 0.0517(12) 0.0005(10) 0.0228(10) 0.0072(10) C33 0.0485(11) 0.0499(11) 0.0449(11) -0.0040(8) 0.0086(8) 0.0015(8) C34 0.0379(9) 0.0346(9) 0.0441(10) -0.0014(7) 0.0073(7) 0.0013(7) C01 0.54(3) 0.223(9) 0.234(10) 0.061(7) 0.185(13) -0.067(11) C02 0.315(13) 0.47(2) 0.221(10) 0.229(14) -0.063(9) -0.064(14) C03 0.343(13) 0.284(11) 0.237(10) 0.036(8) 0.179(11) -0.020(10) _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 C28 1.456(2) . ? O1 C27 1.467(2) . ? O2 C26 1.366(2) . ? O2 C25 1.389(2) . ? C1 C6 1.376(3) . ? C1 C2 1.387(3) . ? C1 H1A 0.9300 . ? C2 C3 1.363(3) . ? C2 H2A 0.9300 . ? C3 C4 1.369(3) . ? C3 H3A 0.9300 . ? C4 C5 1.380(3) . ? C4 H4A 0.9300 . ? C5 C6 1.381(3) . ? C5 H5A 0.9300 . ? C6 C27 1.513(2) . ? C7 C12 1.378(3) . ? C7 C8 1.382(3) . ? C7 H7A 0.9300 . ? C8 C9 1.372(3) . ? C8 H8A 0.9300 . ? C9 C10 1.369(3) . ? C9 H9A 0.9300 . ? C10 C11 1.378(3) . ? C10 H10A 0.9300 . ? C11 C12 1.382(3) . ? C11 H11A 0.9300 . ? C12 C28 1.510(2) . ? C13 C14 1.377(3) . ? C13 C18 1.391(3) . ? C13 H13A 0.9300 . ? C14 C15 1.369(3) . ? C14 H14A 0.9300 . ? C15 C16 1.377(4) . ? C15 H15A 0.9300 . ? C16 C17 1.380(3) . ? C16 H16A 0.9300 . ? C17 C18 1.395(3) . ? C17 H17A 0.9300 . ? C18 C25 1.461(2) . ? C19 C26 1.481(3) . ? C19 C20 1.538(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.536(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.532(2) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.498(2) . ? C22 C27 1.548(2) . ? C22 H22A 0.9800 . ? C23 C26 1.340(2) . ? C23 C24 1.426(2) . ? C24 C25 1.368(2) . ? C24 C28 1.527(2) . ? C27 C29 1.520(2) . ? C28 C34 1.530(2) . ? C29 C34 1.385(2) . ? C29 C30 1.386(2) . ? C30 C31 1.384(3) . ? C30 H30A 0.9300 . ? C31 C32 1.380(3) . ? C31 H31A 0.9300 . ? C32 C33 1.391(3) . ? C32 H32A 0.9300 . ? C33 C34 1.382(3) . ? C33 H33A 0.9300 . ? C01 C02 1.215(15) . ? C01 C03 1.793(16) 3_676 ? C01 H01A 0.9700 . ? C01 H01B 0.9700 . ? C02 C03 1.632(15) . ? C02 H02A 0.9700 . ? C02 H02B 0.9700 . ? C03 C01 1.793(16) 3_676 ? C03 H03A 0.9700 . ? C03 H03B 0.9700 . ? 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 C28 O1 C27 107.19(12) . . ? C26 O2 C25 107.04(13) . . ? C6 C1 C2 121.0(2) . . ? C6 C1 H1A 119.5 . . ? C2 C1 H1A 119.5 . . ? C3 C2 C1 120.6(2) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C2 C3 C4 119.0(2) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C3 C4 C5 120.6(2) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C4 C5 C6 121.1(2) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 117.64(18) . . ? C1 C6 C27 123.67(18) . . ? C5 C6 C27 118.67(17) . . ? C12 C7 C8 120.76(19) . . ? C12 C7 H7A 119.6 . . ? C8 C7 H7A 119.6 . . ? C9 C8 C7 120.1(2) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C10 C9 C8 119.69(19) . . ? C10 C9 H9A 120.2 . . ? C8 C9 H9A 120.2 . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C10 C11 C12 120.72(19) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C7 C12 C11 118.47(17) . . ? C7 C12 C28 120.59(16) . . ? C11 C12 C28 120.89(16) . . ? C14 C13 C18 120.88(19) . . ? C14 C13 H13A 119.6 . . ? C18 C13 H13A 119.6 . . ? C15 C14 C13 120.7(2) . . ? C15 C14 H14A 119.6 . . ? C13 C14 H14A 119.6 . . ? C14 C15 C16 119.3(2) . . ? C14 C15 H15A 120.4 . . ? C16 C15 H15A 120.4 . . ? C15 C16 C17 120.7(2) . . ? C15 C16 H16A 119.7 . . ? C17 C16 H16A 119.7 . . ? C16 C17 C18 120.5(2) . . ? C16 C17 H17A 119.7 . . ? C18 C17 H17A 119.7 . . ? C13 C18 C17 117.83(18) . . ? C13 C18 C25 121.34(16) . . ? C17 C18 C25 120.82(17) . . ? C26 C19 C20 108.57(16) . . ? C26 C19 H19A 110.0 . . ? C20 C19 H19A 110.0 . . ? C26 C19 H19B 110.0 . . ? C20 C19 H19B 110.0 . . ? H19A C19 H19B 108.4 . . ? C21 C20 C19 114.29(16) . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C22 C21 C20 109.78(15) . . ? C22 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? C22 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C23 C22 C21 106.02(14) . . ? C23 C22 C27 106.92(14) . . ? C21 C22 C27 120.47(15) . . ? C23 C22 H22A 107.6 . . ? C21 C22 H22A 107.6 . . ? C27 C22 H22A 107.6 . . ? C26 C23 C24 107.62(16) . . ? C26 C23 C22 124.24(16) . . ? C24 C23 C22 127.49(15) . . ? C25 C24 C23 106.29(15) . . ? C25 C24 C28 137.68(16) . . ? C23 C24 C28 114.53(14) . . ? C24 C25 O2 108.87(15) . . ? C24 C25 C18 136.79(16) . . ? O2 C25 C18 114.31(15) . . ? C23 C26 O2 110.11(15) . . ? C23 C26 C19 126.73(17) . . ? O2 C26 C19 122.53(16) . . ? O1 C27 C6 106.60(13) . . ? O1 C27 C29 101.10(13) . . ? C6 C27 C29 114.18(14) . . ? O1 C27 C22 104.50(13) . . ? C6 C27 C22 115.97(15) . . ? C29 C27 C22 112.61(14) . . ? O1 C28 C12 106.64(13) . . ? O1 C28 C24 105.88(13) . . ? C12 C28 C24 118.34(14) . . ? O1 C28 C34 101.16(13) . . ? C12 C28 C34 118.79(14) . . ? C24 C28 C34 104.07(13) . . ? C34 C29 C30 120.64(17) . . ? C34 C29 C27 109.46(14) . . ? C30 C29 C27 129.88(17) . . ? C31 C30 C29 118.62(19) . . ? C31 C30 H30A 120.7 . . ? C29 C30 H30A 120.7 . . ? C32 C31 C30 120.74(18) . . ? C32 C31 H31A 119.6 . . ? C30 C31 H31A 119.6 . . ? C31 C32 C33 120.82(19) . . ? C31 C32 H32A 119.6 . . ? C33 C32 H32A 119.6 . . ? C34 C33 C32 118.33(18) . . ? C34 C33 H33A 120.8 . . ? C32 C33 H33A 120.8 . . ? C33 C34 C29 120.85(16) . . ? C33 C34 C28 131.47(16) . . ? C29 C34 C28 107.43(15) . . ? C02 C01 C03 102.3(11) . 3_676 ? C02 C01 H01A 111.3 . . ? C03 C01 H01A 111.3 3_676 . ? C02 C01 H01B 111.3 . . ? C03 C01 H01B 111.3 3_676 . ? H01A C01 H01B 109.2 . . ? C01 C02 C03 112.7(9) . . ? C01 C02 H02A 109.1 . . ? C03 C02 H02A 109.1 . . ? C01 C02 H02B 109.1 . . ? C03 C02 H02B 109.1 . . ? H02A C02 H02B 107.8 . . ? C02 C03 C01 95.7(8) . 3_676 ? C02 C03 H03A 112.6 . . ? C01 C03 H03A 112.6 3_676 . ? C02 C03 H03B 112.6 . . ? C01 C03 H03B 112.6 3_676 . ? H03A C03 H03B 110.1 . . ? 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 0.7(3) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C2 C1 C6 C27 -178.75(17) . . . . ? C4 C5 C6 C1 -0.1(4) . . . . ? C4 C5 C6 C27 178.4(2) . . . . ? C12 C7 C8 C9 0.9(4) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? C8 C9 C10 C11 -0.9(4) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C8 C7 C12 C11 -1.8(3) . . . . ? C8 C7 C12 C28 -179.1(2) . . . . ? C10 C11 C12 C7 1.4(3) . . . . ? C10 C11 C12 C28 178.71(19) . . . . ? C18 C13 C14 C15 -0.4(3) . . . . ? C13 C14 C15 C16 -1.9(4) . . . . ? C14 C15 C16 C17 2.0(4) . . . . ? C15 C16 C17 C18 0.2(3) . . . . ? C14 C13 C18 C17 2.5(3) . . . . ? C14 C13 C18 C25 -178.24(19) . . . . ? C16 C17 C18 C13 -2.4(3) . . . . ? C16 C17 C18 C25 178.38(18) . . . . ? C26 C19 C20 C21 -34.4(2) . . . . ? C19 C20 C21 C22 62.9(2) . . . . ? C20 C21 C22 C23 -54.84(19) . . . . ? C20 C21 C22 C27 -176.19(16) . . . . ? C21 C22 C23 C26 27.8(2) . . . . ? C27 C22 C23 C26 157.55(17) . . . . ? C21 C22 C23 C24 -141.79(17) . . . . ? C27 C22 C23 C24 -12.1(2) . . . . ? C26 C23 C24 C25 0.59(19) . . . . ? C22 C23 C24 C25 171.61(16) . . . . ? C26 C23 C24 C28 -167.94(15) . . . . ? C22 C23 C24 C28 3.1(2) . . . . ? C23 C24 C25 O2 1.07(18) . . . . ? C28 C24 C25 O2 165.48(18) . . . . ? C23 C24 C25 C18 -176.66(19) . . . . ? C28 C24 C25 C18 -12.2(4) . . . . ? C26 O2 C25 C24 -2.31(18) . . . . ? C26 O2 C25 C18 175.98(14) . . . . ? C13 C18 C25 C24 16.0(3) . . . . ? C17 C18 C25 C24 -164.8(2) . . . . ? C13 C18 C25 O2 -161.63(17) . . . . ? C17 C18 C25 O2 17.6(2) . . . . ? C24 C23 C26 O2 -2.1(2) . . . . ? C22 C23 C26 O2 -173.46(15) . . . . ? C24 C23 C26 C19 168.95(19) . . . . ? C22 C23 C26 C19 -2.4(3) . . . . ? C25 O2 C26 C23 2.73(19) . . . . ? C25 O2 C26 C19 -168.75(17) . . . . ? C20 C19 C26 C23 4.7(3) . . . . ? C20 C19 C26 O2 174.73(17) . . . . ? C28 O1 C27 C6 153.91(13) . . . . ? C28 O1 C27 C29 34.30(15) . . . . ? C28 O1 C27 C22 -82.79(15) . . . . ? C1 C6 C27 O1 113.18(19) . . . . ? C5 C6 C27 O1 -65.2(2) . . . . ? C1 C6 C27 C29 -136.08(18) . . . . ? C5 C6 C27 C29 45.5(2) . . . . ? C1 C6 C27 C22 -2.7(2) . . . . ? C5 C6 C27 C22 178.96(19) . . . . ? C23 C22 C27 O1 47.29(16) . . . . ? C21 C22 C27 O1 168.21(15) . . . . ? C23 C22 C27 C6 164.31(14) . . . . ? C21 C22 C27 C6 -74.8(2) . . . . ? C23 C22 C27 C29 -61.56(17) . . . . ? C21 C22 C27 C29 59.4(2) . . . . ? C27 O1 C28 C12 -161.79(13) . . . . ? C27 O1 C28 C24 71.33(15) . . . . ? C27 O1 C28 C34 -36.95(15) . . . . ? C7 C12 C28 O1 85.8(2) . . . . ? C11 C12 C28 O1 -91.47(19) . . . . ? C7 C12 C28 C24 -155.14(17) . . . . ? C11 C12 C28 C24 27.6(2) . . . . ? C7 C12 C28 C34 -27.5(2) . . . . ? C11 C12 C28 C34 155.28(17) . . . . ? C25 C24 C28 O1 166.45(19) . . . . ? C23 C24 C28 O1 -30.02(18) . . . . ? C25 C24 C28 C12 47.0(3) . . . . ? C23 C24 C28 C12 -149.47(15) . . . . ? C25 C24 C28 C34 -87.4(2) . . . . ? C23 C24 C28 C34 76.17(17) . . . . ? O1 C27 C29 C34 -17.74(17) . . . . ? C6 C27 C29 C34 -131.77(16) . . . . ? C22 C27 C29 C34 93.25(17) . . . . ? O1 C27 C29 C30 163.65(18) . . . . ? C6 C27 C29 C30 49.6(3) . . . . ? C22 C27 C29 C30 -85.4(2) . . . . ? C34 C29 C30 C31 0.3(3) . . . . ? C27 C29 C30 C31 178.75(18) . . . . ? C29 C30 C31 C32 0.6(3) . . . . ? C30 C31 C32 C33 -1.3(3) . . . . ? C31 C32 C33 C34 1.1(3) . . . . ? C32 C33 C34 C29 -0.2(3) . . . . ? C32 C33 C34 C28 -173.61(18) . . . . ? C30 C29 C34 C33 -0.5(3) . . . . ? C27 C29 C34 C33 -179.23(16) . . . . ? C30 C29 C34 C28 174.36(16) . . . . ? C27 C29 C34 C28 -4.40(19) . . . . ? O1 C28 C34 C33 -160.97(18) . . . . ? C12 C28 C34 C33 -44.8(3) . . . . ? C24 C28 C34 C33 89.3(2) . . . . ? O1 C28 C34 C29 24.96(17) . . . . ? C12 C28 C34 C29 141.16(16) . . . . ? C24 C28 C34 C29 -84.73(16) . . . . ? C03 C01 C02 C03 -78.4(11) 3_676 . . . ? C01 C02 C03 C01 74.2(13) . . . 3_676 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.372 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.035 # Attachment '4l.cif' data_z_41 _database_code_depnum_ccdc_archive 'CCDC 784921' #TrackingRef '4l.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H24 O3' _chemical_formula_weight 516.56 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6485(4) _cell_length_b 13.5871(4) _cell_length_c 15.6450(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.2360(10) _cell_angle_gamma 90.00 _cell_volume 2681.35(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9740 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30287 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4719 _reflns_number_gt 3910 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+0.7162P] 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 4719 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.05665(8) 0.99650(7) 0.10772(7) 0.0517(3) Uani 1 1 d . . . O2 O 0.19945(7) 0.69530(7) 0.09760(6) 0.0440(2) Uani 1 1 d . . . O3 O 0.36383(8) 0.91578(8) 0.13168(7) 0.0574(3) Uani 1 1 d . . . C1 C 0.48656(14) 0.71629(15) 0.11420(14) 0.0746(5) Uani 1 1 d . . . H1A H 0.4956 0.7840 0.1096 0.090 Uiso 1 1 calc R . . C2 C 0.57279(17) 0.65412(19) 0.10909(17) 0.0936(7) Uani 1 1 d . . . H2A H 0.6393 0.6804 0.1014 0.112 Uiso 1 1 calc R . . C3 C 0.56089(18) 0.55482(18) 0.11530(17) 0.0950(7) Uani 1 1 d . . . H3A H 0.6191 0.5134 0.1126 0.114 Uiso 1 1 calc R . . C4 C 0.46310(19) 0.51675(17) 0.12543(19) 0.1027(8) Uani 1 1 d . . . H4A H 0.4543 0.4489 0.1288 0.123 Uiso 1 1 calc R . . C5 C 0.37677(16) 0.57810(14) 0.13067(15) 0.0794(6) Uani 1 1 d . . . H5A H 0.3103 0.5511 0.1375 0.095 Uiso 1 1 calc R . . C6 C 0.38793(12) 0.67874(12) 0.12597(9) 0.0507(4) Uani 1 1 d . . . C7 C 0.00090(17) 0.57502(13) 0.17274(12) 0.0704(5) Uani 1 1 d . . . H7A H 0.0404 0.5674 0.2249 0.084 Uiso 1 1 calc R . . C8 C -0.0774(2) 0.50782(14) 0.14842(15) 0.0870(7) Uani 1 1 d . . . H8A H -0.0917 0.4564 0.1851 0.104 Uiso 1 1 calc R . . C9 C -0.13397(15) 0.51607(14) 0.07109(14) 0.0728(5) Uani 1 1 d . . . H9A H -0.1861 0.4701 0.0547 0.087 Uiso 1 1 calc R . . C10 C -0.11351(14) 0.59237(14) 0.01778(13) 0.0675(5) Uani 1 1 d . . . H10A H -0.1511 0.5978 -0.0354 0.081 Uiso 1 1 calc R . . C11 C -0.03727(12) 0.66119(12) 0.04264(11) 0.0559(4) Uani 1 1 d . . . H11A H -0.0250 0.7136 0.0065 0.067 Uiso 1 1 calc R . . C12 C 0.02115(11) 0.65335(10) 0.12053(9) 0.0447(3) Uani 1 1 d . . . C13 C -0.14164(14) 0.83024(13) 0.18834(12) 0.0638(5) Uani 1 1 d . . . H13A H -0.1014 0.7745 0.2023 0.077 Uiso 1 1 calc R . . C14 C -0.24449(15) 0.83538(16) 0.21069(14) 0.0774(6) Uani 1 1 d . . . H14A H -0.2734 0.7832 0.2395 0.093 Uiso 1 1 calc R . . C15 C -0.30500(15) 0.91777(16) 0.19049(15) 0.0803(6) Uani 1 1 d . . . H15A H -0.3747 0.9213 0.2055 0.096 Uiso 1 1 calc R . . C16 C -0.26174(15) 0.99442(14) 0.14812(14) 0.0740(5) Uani 1 1 d . . . H16A H -0.3023 1.0502 0.1346 0.089 Uiso 1 1 calc R . . C17 C -0.15919(13) 0.98965(12) 0.12549(11) 0.0566(4) Uani 1 1 d . . . H17A H -0.1310 1.0422 0.0966 0.068 Uiso 1 1 calc R . . C18 C -0.09695(12) 0.90737(11) 0.14508(9) 0.0479(4) Uani 1 1 d . . . C19 C 0.24340(13) 1.05246(12) 0.09104(10) 0.0540(4) Uani 1 1 d . . . C20 C 0.23215(16) 1.15184(13) 0.07305(13) 0.0706(5) Uani 1 1 d . . . H20A H 0.1648 1.1784 0.0616 0.085 Uiso 1 1 calc R . . C21 C 0.32005(18) 1.21152(15) 0.07204(16) 0.0883(7) Uani 1 1 d . . . H21A H 0.3120 1.2782 0.0598 0.106 Uiso 1 1 calc R . . C22 C 0.41914(18) 1.17285(16) 0.08894(17) 0.0939(7) Uani 1 1 d . . . H22A H 0.4782 1.2135 0.0880 0.113 Uiso 1 1 calc R . . C23 C 0.43268(16) 1.07396(15) 0.10741(15) 0.0811(6) Uani 1 1 d . . . H23A H 0.5004 1.0485 0.1192 0.097 Uiso 1 1 calc R . . C24 C 0.34585(13) 1.01333(12) 0.10827(11) 0.0568(4) Uani 1 1 d . . . C25 C 0.29021(11) 0.84519(11) 0.09222(9) 0.0463(3) Uani 1 1 d . . . H25A H 0.3048 0.8363 0.0321 0.056 Uiso 1 1 calc R . . C26 C 0.18143(12) 0.88402(11) 0.09673(9) 0.0446(3) Uani 1 1 d . . . C27 C 0.16061(12) 0.98030(11) 0.09428(10) 0.0493(4) Uani 1 1 d . . . C28 C 0.01272(12) 0.90435(10) 0.12333(9) 0.0461(3) Uani 1 1 d . . . C29 C 0.08882(11) 0.83346(10) 0.11669(8) 0.0428(3) Uani 1 1 d . . . C30 C 0.10814(11) 0.72630(10) 0.14303(9) 0.0423(3) Uani 1 1 d . . . C31 C 0.29279(11) 0.74358(10) 0.13763(9) 0.0439(3) Uani 1 1 d . . . C32 C 0.26542(11) 0.75209(10) 0.22993(9) 0.0429(3) Uani 1 1 d . . . C33 C 0.33035(13) 0.77735(11) 0.30145(9) 0.0511(4) Uani 1 1 d . . . H33A H 0.4020 0.7905 0.2974 0.061 Uiso 1 1 calc R . . C34 C 0.28531(14) 0.78245(12) 0.37951(10) 0.0552(4) Uani 1 1 d . . . H34A H 0.3272 0.7995 0.4286 0.066 Uiso 1 1 calc R . . C35 C 0.17951(14) 0.76258(11) 0.38506(9) 0.0548(4) Uani 1 1 d . . . H35A H 0.1513 0.7648 0.4382 0.066 Uiso 1 1 calc R . . C36 C 0.11398(13) 0.73922(11) 0.31279(9) 0.0483(4) Uani 1 1 d . . . H36A H 0.0422 0.7270 0.3168 0.058 Uiso 1 1 calc R . . C37 C 0.15838(11) 0.73459(10) 0.23469(9) 0.0416(3) Uani 1 1 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 O1 0.0558(6) 0.0398(6) 0.0586(6) 0.0043(5) -0.0028(5) 0.0020(5) O2 0.0502(6) 0.0452(6) 0.0362(5) -0.0023(4) 0.0015(4) 0.0018(4) O3 0.0551(6) 0.0505(6) 0.0643(7) 0.0056(5) -0.0107(5) -0.0050(5) C1 0.0599(11) 0.0656(12) 0.0999(15) -0.0033(10) 0.0162(10) 0.0024(9) C2 0.0600(12) 0.0962(18) 0.128(2) -0.0070(14) 0.0277(12) 0.0080(11) C3 0.0741(14) 0.0879(17) 0.126(2) -0.0018(14) 0.0286(13) 0.0291(12) C4 0.0869(16) 0.0647(13) 0.161(2) 0.0060(14) 0.0371(16) 0.0228(12) C5 0.0658(11) 0.0563(11) 0.1189(17) 0.0070(11) 0.0246(11) 0.0100(9) C6 0.0536(9) 0.0564(9) 0.0424(8) 0.0004(7) 0.0058(7) 0.0070(7) C7 0.1013(14) 0.0487(10) 0.0585(10) 0.0081(8) -0.0126(10) -0.0155(9) C8 0.1214(18) 0.0546(11) 0.0831(14) 0.0112(10) -0.0049(13) -0.0321(11) C9 0.0665(11) 0.0558(11) 0.0944(15) -0.0056(10) -0.0045(10) -0.0140(9) C10 0.0550(10) 0.0673(11) 0.0772(12) -0.0010(9) -0.0155(9) -0.0042(8) C11 0.0518(9) 0.0569(10) 0.0575(10) 0.0076(8) -0.0061(7) -0.0032(7) C12 0.0497(8) 0.0394(8) 0.0448(8) -0.0004(6) 0.0016(6) 0.0029(6) C13 0.0643(10) 0.0569(10) 0.0711(11) 0.0098(8) 0.0112(9) 0.0106(8) C14 0.0707(12) 0.0738(13) 0.0904(14) 0.0093(11) 0.0236(11) 0.0002(10) C15 0.0576(11) 0.0813(14) 0.1034(16) -0.0042(12) 0.0165(10) 0.0097(10) C16 0.0603(11) 0.0625(11) 0.0985(15) -0.0025(10) 0.0018(10) 0.0148(9) C17 0.0577(10) 0.0486(9) 0.0620(10) -0.0025(7) -0.0053(8) 0.0043(7) C18 0.0528(9) 0.0446(8) 0.0451(8) -0.0052(6) -0.0040(6) 0.0034(7) C19 0.0625(10) 0.0476(9) 0.0506(9) 0.0042(7) -0.0051(7) -0.0065(7) C20 0.0734(12) 0.0496(10) 0.0865(13) 0.0111(9) -0.0092(10) -0.0058(9) C21 0.0914(15) 0.0524(11) 0.1174(18) 0.0171(11) -0.0159(13) -0.0205(11) C22 0.0810(14) 0.0700(13) 0.1261(19) 0.0213(13) -0.0232(13) -0.0306(11) C23 0.0646(12) 0.0695(13) 0.1055(16) 0.0154(11) -0.0187(11) -0.0173(10) C24 0.0627(10) 0.0509(9) 0.0548(9) 0.0053(7) -0.0089(8) -0.0081(8) C25 0.0505(8) 0.0476(8) 0.0403(7) 0.0014(6) -0.0010(6) -0.0036(7) C26 0.0517(8) 0.0437(8) 0.0375(7) 0.0041(6) -0.0030(6) -0.0003(6) C27 0.0529(9) 0.0453(8) 0.0486(8) 0.0059(7) -0.0031(7) 0.0006(7) C28 0.0551(9) 0.0400(8) 0.0423(8) 0.0035(6) -0.0028(6) 0.0008(6) C29 0.0506(8) 0.0408(8) 0.0361(7) 0.0020(6) -0.0034(6) -0.0005(6) C30 0.0489(8) 0.0405(8) 0.0372(7) 0.0015(6) 0.0018(6) 0.0033(6) C31 0.0485(8) 0.0448(8) 0.0381(7) 0.0005(6) 0.0002(6) 0.0021(6) C32 0.0524(8) 0.0380(7) 0.0378(7) 0.0025(6) -0.0006(6) 0.0064(6) C33 0.0565(9) 0.0498(9) 0.0453(8) 0.0023(7) -0.0071(7) 0.0043(7) C34 0.0735(11) 0.0514(9) 0.0385(8) -0.0015(7) -0.0096(7) 0.0066(8) C35 0.0790(12) 0.0503(9) 0.0352(8) 0.0008(6) 0.0057(7) 0.0128(8) C36 0.0589(9) 0.0443(8) 0.0420(8) 0.0035(6) 0.0064(7) 0.0062(7) C37 0.0533(8) 0.0332(7) 0.0378(7) 0.0018(6) -0.0001(6) 0.0061(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 C27 1.3648(18) . ? O1 C28 1.3985(17) . ? O2 C31 1.4516(17) . ? O2 C30 1.4621(16) . ? O3 C24 1.3894(19) . ? O3 C25 1.4433(18) . ? C1 C6 1.373(2) . ? C1 C2 1.387(3) . ? C1 H1A 0.9300 . ? C2 C3 1.362(3) . ? C2 H2A 0.9300 . ? C3 C4 1.361(3) . ? C3 H3A 0.9300 . ? C4 C5 1.381(3) . ? C4 H4A 0.9300 . ? C5 C6 1.377(2) . ? C5 H5A 0.9300 . ? C6 C31 1.513(2) . ? C7 C12 1.377(2) . ? C7 C8 1.380(3) . ? C7 H7A 0.9300 . ? C8 C9 1.364(3) . ? C8 H8A 0.9300 . ? C9 C10 1.367(3) . ? C9 H9A 0.9300 . ? C10 C11 1.379(2) . ? C10 H10A 0.9300 . ? C11 C12 1.382(2) . ? C11 H11A 0.9300 . ? C12 C30 1.503(2) . ? C13 C14 1.374(2) . ? C13 C18 1.390(2) . ? C13 H13A 0.9300 . ? C14 C15 1.379(3) . ? C14 H14A 0.9300 . ? C15 C16 1.370(3) . ? C15 H15A 0.9300 . ? C16 C17 1.371(2) . ? C16 H16A 0.9300 . ? C17 C18 1.388(2) . ? C17 H17A 0.9300 . ? C18 C28 1.453(2) . ? C19 C20 1.385(2) . ? C19 C24 1.408(2) . ? C19 C27 1.438(2) . ? C20 C21 1.377(3) . ? C20 H20A 0.9300 . ? C21 C22 1.367(3) . ? C21 H21A 0.9300 . ? C22 C23 1.382(3) . ? C22 H22A 0.9300 . ? C23 C24 1.374(2) . ? C23 H23A 0.9300 . ? C25 C26 1.480(2) . ? C25 C31 1.552(2) . ? C25 H25A 0.9800 . ? C26 C27 1.334(2) . ? C26 C29 1.413(2) . ? C28 C29 1.371(2) . ? C29 C30 1.5279(19) . ? C30 C37 1.5291(19) . ? C31 C32 1.5139(19) . ? C32 C33 1.381(2) . ? C32 C37 1.382(2) . ? C33 C34 1.387(2) . ? C33 H33A 0.9300 . ? C34 C35 1.374(2) . ? C34 H34A 0.9300 . ? C35 C36 1.388(2) . ? C35 H35A 0.9300 . ? C36 C37 1.383(2) . ? C36 H36A 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 C27 O1 C28 106.40(11) . . ? C31 O2 C30 107.85(10) . . ? C24 O3 C25 115.68(11) . . ? C6 C1 C2 120.52(19) . . ? C6 C1 H1A 119.7 . . ? C2 C1 H1A 119.7 . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 120.77(19) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C1 C6 C5 118.29(16) . . ? C1 C6 C31 122.58(15) . . ? C5 C6 C31 119.08(15) . . ? C12 C7 C8 120.60(17) . . ? C12 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C9 C8 C7 120.60(18) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 C10 119.53(17) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C9 C10 C11 120.15(17) . . ? C9 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C10 C11 C12 120.92(16) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C7 C12 C11 118.16(15) . . ? C7 C12 C30 122.39(14) . . ? C11 C12 C30 119.35(13) . . ? C14 C13 C18 120.82(17) . . ? C14 C13 H13A 119.6 . . ? C18 C13 H13A 119.6 . . ? C13 C14 C15 120.19(18) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C16 C15 C14 119.54(18) . . ? C16 C15 H15A 120.2 . . ? C14 C15 H15A 120.2 . . ? C15 C16 C17 120.55(18) . . ? C15 C16 H16A 119.7 . . ? C17 C16 H16A 119.7 . . ? C16 C17 C18 120.85(17) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C17 C18 C13 118.05(15) . . ? C17 C18 C28 120.43(14) . . ? C13 C18 C28 121.48(14) . . ? C20 C19 C24 119.10(16) . . ? C20 C19 C27 127.44(16) . . ? C24 C19 C27 113.45(14) . . ? C21 C20 C19 120.38(19) . . ? C21 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? C22 C21 C20 120.07(19) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 C22 C23 120.78(19) . . ? C21 C22 H22A 119.6 . . ? C23 C22 H22A 119.6 . . ? C24 C23 C22 119.88(19) . . ? C24 C23 H23A 120.1 . . ? C22 C23 H23A 120.1 . . ? C23 C24 O3 117.34(16) . . ? C23 C24 C19 119.79(16) . . ? O3 C24 C19 122.75(14) . . ? O3 C25 C26 108.38(12) . . ? O3 C25 C31 113.85(11) . . ? C26 C25 C31 106.47(12) . . ? O3 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? C31 C25 H25A 109.3 . . ? C27 C26 C29 108.54(13) . . ? C27 C26 C25 122.02(14) . . ? C29 C26 C25 128.76(13) . . ? C26 C27 O1 110.12(13) . . ? C26 C27 C19 121.79(15) . . ? O1 C27 C19 127.43(14) . . ? C29 C28 O1 109.00(12) . . ? C29 C28 C18 136.49(14) . . ? O1 C28 C18 114.46(12) . . ? C28 C29 C26 105.86(13) . . ? C28 C29 C30 138.44(13) . . ? C26 C29 C30 113.84(12) . . ? O2 C30 C12 106.68(11) . . ? O2 C30 C29 105.06(11) . . ? C12 C30 C29 117.74(12) . . ? O2 C30 C37 100.88(10) . . ? C12 C30 C37 120.96(12) . . ? C29 C30 C37 103.28(11) . . ? O2 C31 C6 108.27(11) . . ? O2 C31 C32 102.13(11) . . ? C6 C31 C32 113.54(12) . . ? O2 C31 C25 102.45(11) . . ? C6 C31 C25 116.92(12) . . ? C32 C31 C25 111.73(12) . . ? C33 C32 C37 121.68(13) . . ? C33 C32 C31 128.86(14) . . ? C37 C32 C31 109.40(12) . . ? C32 C33 C34 117.87(15) . . ? C32 C33 H33A 121.1 . . ? C34 C33 H33A 121.1 . . ? C35 C34 C33 120.73(14) . . ? C35 C34 H34A 119.6 . . ? C33 C34 H34A 119.6 . . ? C34 C35 C36 121.27(14) . . ? C34 C35 H35A 119.4 . . ? C36 C35 H35A 119.4 . . ? C37 C36 C35 118.22(15) . . ? C37 C36 H36A 120.9 . . ? C35 C36 H36A 120.9 . . ? C32 C37 C36 120.20(13) . . ? C32 C37 C30 107.64(12) . . ? C36 C37 C30 131.61(13) . . ? 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 0.3(4) . . . . ? C1 C2 C3 C4 0.9(4) . . . . ? C2 C3 C4 C5 -1.0(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C2 C1 C6 C5 -1.4(3) . . . . ? C2 C1 C6 C31 175.99(18) . . . . ? C4 C5 C6 C1 1.3(3) . . . . ? C4 C5 C6 C31 -176.1(2) . . . . ? C12 C7 C8 C9 2.0(3) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? C9 C10 C11 C12 1.4(3) . . . . ? C8 C7 C12 C11 -1.5(3) . . . . ? C8 C7 C12 C30 -177.83(18) . . . . ? C10 C11 C12 C7 -0.2(2) . . . . ? C10 C11 C12 C30 176.26(15) . . . . ? C18 C13 C14 C15 -0.1(3) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C16 C17 C18 C13 -0.1(2) . . . . ? C16 C17 C18 C28 -177.97(16) . . . . ? C14 C13 C18 C17 0.2(3) . . . . ? C14 C13 C18 C28 178.08(17) . . . . ? C24 C19 C20 C21 0.0(3) . . . . ? C27 C19 C20 C21 -179.69(18) . . . . ? C19 C20 C21 C22 -0.1(4) . . . . ? C20 C21 C22 C23 -0.2(4) . . . . ? C21 C22 C23 C24 0.5(4) . . . . ? C22 C23 C24 O3 -176.7(2) . . . . ? C22 C23 C24 C19 -0.6(3) . . . . ? C25 O3 C24 C23 -149.01(16) . . . . ? C25 O3 C24 C19 35.0(2) . . . . ? C20 C19 C24 C23 0.3(3) . . . . ? C27 C19 C24 C23 -179.96(17) . . . . ? C20 C19 C24 O3 176.22(16) . . . . ? C27 C19 C24 O3 -4.1(2) . . . . ? C24 O3 C25 C26 -45.56(17) . . . . ? C24 O3 C25 C31 -163.82(13) . . . . ? O3 C25 C26 C27 31.40(18) . . . . ? C31 C25 C26 C27 154.26(14) . . . . ? O3 C25 C26 C29 -138.06(14) . . . . ? C31 C25 C26 C29 -15.2(2) . . . . ? C29 C26 C27 O1 -2.86(17) . . . . ? C25 C26 C27 O1 -174.21(12) . . . . ? C29 C26 C27 C19 168.46(13) . . . . ? C25 C26 C27 C19 -2.9(2) . . . . ? C28 O1 C27 C26 2.89(16) . . . . ? C28 O1 C27 C19 -167.82(14) . . . . ? C20 C19 C27 C26 167.47(18) . . . . ? C24 C19 C27 C26 -12.2(2) . . . . ? C20 C19 C27 O1 -22.8(3) . . . . ? C24 C19 C27 O1 157.49(15) . . . . ? C27 O1 C28 C29 -1.81(15) . . . . ? C27 O1 C28 C18 175.97(12) . . . . ? C17 C18 C28 C29 -164.25(17) . . . . ? C13 C18 C28 C29 17.9(3) . . . . ? C17 C18 C28 O1 18.8(2) . . . . ? C13 C18 C28 O1 -159.02(14) . . . . ? O1 C28 C29 C26 0.14(15) . . . . ? C18 C28 C29 C26 -176.93(16) . . . . ? O1 C28 C29 C30 162.70(15) . . . . ? C18 C28 C29 C30 -14.4(3) . . . . ? C27 C26 C29 C28 1.64(16) . . . . ? C25 C26 C29 C28 172.23(14) . . . . ? C27 C26 C29 C30 -165.80(12) . . . . ? C25 C26 C29 C30 4.8(2) . . . . ? C31 O2 C30 C12 -162.35(11) . . . . ? C31 O2 C30 C29 71.93(12) . . . . ? C31 O2 C30 C37 -35.17(13) . . . . ? C7 C12 C30 O2 97.12(17) . . . . ? C11 C12 C30 O2 -79.16(16) . . . . ? C7 C12 C30 C29 -145.24(16) . . . . ? C11 C12 C30 C29 38.49(19) . . . . ? C7 C12 C30 C37 -17.1(2) . . . . ? C11 C12 C30 C37 166.67(13) . . . . ? C28 C29 C30 O2 169.05(16) . . . . ? C26 C29 C30 O2 -29.32(15) . . . . ? C28 C29 C30 C12 50.5(2) . . . . ? C26 C29 C30 C12 -147.83(12) . . . . ? C28 C29 C30 C37 -85.6(2) . . . . ? C26 C29 C30 C37 76.00(14) . . . . ? C30 O2 C31 C6 151.45(11) . . . . ? C30 O2 C31 C32 31.38(13) . . . . ? C30 O2 C31 C25 -84.42(12) . . . . ? C1 C6 C31 O2 145.50(16) . . . . ? C5 C6 C31 O2 -37.2(2) . . . . ? C1 C6 C31 C32 -101.84(18) . . . . ? C5 C6 C31 C32 75.5(2) . . . . ? C1 C6 C31 C25 30.5(2) . . . . ? C5 C6 C31 C25 -152.14(16) . . . . ? O3 C25 C31 O2 168.81(11) . . . . ? C26 C25 C31 O2 49.45(13) . . . . ? O3 C25 C31 C6 -73.01(16) . . . . ? C26 C25 C31 C6 167.63(12) . . . . ? O3 C25 C31 C32 60.17(16) . . . . ? C26 C25 C31 C32 -59.18(15) . . . . ? O2 C31 C32 C33 168.41(14) . . . . ? C6 C31 C32 C33 52.1(2) . . . . ? C25 C31 C32 C33 -82.75(18) . . . . ? O2 C31 C32 C37 -14.44(14) . . . . ? C6 C31 C32 C37 -130.77(13) . . . . ? C25 C31 C32 C37 94.40(14) . . . . ? C37 C32 C33 C34 1.5(2) . . . . ? C31 C32 C33 C34 178.38(14) . . . . ? C32 C33 C34 C35 0.2(2) . . . . ? C33 C34 C35 C36 -1.6(2) . . . . ? C34 C35 C36 C37 1.2(2) . . . . ? C33 C32 C37 C36 -2.0(2) . . . . ? C31 C32 C37 C36 -179.34(12) . . . . ? C33 C32 C37 C30 170.45(13) . . . . ? C31 C32 C37 C30 -6.94(15) . . . . ? C35 C36 C37 C32 0.6(2) . . . . ? C35 C36 C37 C30 -169.73(14) . . . . ? O2 C30 C37 C32 25.32(13) . . . . ? C12 C30 C37 C32 142.45(13) . . . . ? C29 C30 C37 C32 -83.18(13) . . . . ? O2 C30 C37 C36 -163.48(14) . . . . ? C12 C30 C37 C36 -46.3(2) . . . . ? C29 C30 C37 C36 88.03(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.159 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.053