# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_tae-2 _database_code_depnum_ccdc_archive 'CCDC 921515' #TrackingRef 'web_deposit_cif_file_0_YifeiLiu_1358991452.TAE-2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 O4' _chemical_formula_sum 'C30 H28 O4' _chemical_formula_weight 452.52 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 P21/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 9.689(4) _cell_length_b 15.769(9) _cell_length_c 18.511(7) _cell_angle_alpha 90.00 _cell_angle_beta 119.760(17) _cell_angle_gamma 90.00 _cell_volume 2455.2(19) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 12616 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 27.44 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9698 _exptl_absorpt_correction_T_max 0.9872 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 22898 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5563 _reflns_number_gt 2883 _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^)+(0.0763P)^2^+0.1306P] 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 5563 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1162 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1673 _refine_ls_wR_factor_gt 0.1388 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1317(3) 0.61891(16) 0.70430(17) 0.0703(7) Uani 1 1 d . . . C2 C 1.0803(3) 0.65098(17) 0.62608(17) 0.0699(7) Uani 1 1 d . . . H2 H 1.1476 0.6507 0.6037 0.084 Uiso 1 1 calc R . . C3 C 0.9276(3) 0.68394(15) 0.58041(15) 0.0588(6) Uani 1 1 d . . . H3 H 0.8935 0.7049 0.5272 0.071 Uiso 1 1 calc R . . C4 C 0.8250(2) 0.68642(14) 0.61209(13) 0.0515(5) Uani 1 1 d . . . C5 C 0.8787(3) 0.65166(17) 0.69066(14) 0.0653(7) Uani 1 1 d . . . H5 H 0.8111 0.6506 0.7129 0.078 Uiso 1 1 calc R . . C6 C 1.0297(3) 0.61881(18) 0.73624(16) 0.0751(8) Uani 1 1 d . . . H6 H 1.0632 0.5964 0.7889 0.090 Uiso 1 1 calc R . . C7 C 0.5548(2) 0.60089(14) 0.46560(13) 0.0521(5) Uani 1 1 d . . . H7 H 0.6117 0.5660 0.5116 0.062 Uiso 1 1 calc R . . C8 C 0.4631(3) 0.56418(15) 0.38887(13) 0.0557(5) Uani 1 1 d . . . H8 H 0.4574 0.5054 0.3837 0.067 Uiso 1 1 calc R . . C9 C 0.3789(2) 0.61469(15) 0.31921(13) 0.0530(5) Uani 1 1 d . . . C10 C 0.3894(3) 0.70109(16) 0.32767(13) 0.0573(6) Uani 1 1 d . . . H10 H 0.3348 0.7355 0.2811 0.069 Uiso 1 1 calc R . . C11 C 0.4816(3) 0.73748(15) 0.40597(14) 0.0572(6) Uani 1 1 d . . . H11 H 0.4870 0.7963 0.4108 0.069 Uiso 1 1 calc R . . C12 C 0.5656(2) 0.68847(14) 0.47694(12) 0.0487(5) Uani 1 1 d . . . C13 C 0.6627(2) 0.72393(14) 0.56241(13) 0.0497(5) Uani 1 1 d . . . C14 C 0.6079(2) 0.78432(14) 0.59405(13) 0.0504(5) Uani 1 1 d . . . C15 C 0.7094(2) 0.82109(14) 0.67878(13) 0.0495(5) Uani 1 1 d . . . C16 C 0.8536(3) 0.85991(16) 0.70279(15) 0.0606(6) Uani 1 1 d . . . H16 H 0.8877 0.8656 0.6641 0.073 Uiso 1 1 calc R . . C17 C 0.9490(3) 0.89059(15) 0.78269(15) 0.0600(6) Uani 1 1 d . . . H17 H 1.0466 0.9154 0.7976 0.072 Uiso 1 1 calc R . . C18 C 0.8977(2) 0.88403(14) 0.83977(14) 0.0535(5) Uani 1 1 d . . . C19 C 0.7518(2) 0.84777(15) 0.81684(14) 0.0569(6) Uani 1 1 d . . . H19 H 0.7165 0.8438 0.8552 0.068 Uiso 1 1 calc R . . C20 C 0.6588(2) 0.81752(15) 0.73727(14) 0.0545(6) Uani 1 1 d . . . H20 H 0.5599 0.7942 0.7221 0.065 Uiso 1 1 calc R . . C21 C 0.4432(2) 0.81928(14) 0.54851(13) 0.0491(5) Uani 1 1 d . . . C22 C 0.4189(3) 0.90628(15) 0.53754(15) 0.0604(6) Uani 1 1 d . . . H22 H 0.5063 0.9424 0.5599 0.072 Uiso 1 1 calc R . . C23 C 0.2682(3) 0.94017(17) 0.49426(15) 0.0666(7) Uani 1 1 d . . . H23 H 0.2550 0.9985 0.4862 0.080 Uiso 1 1 calc R . . C24 C 0.1368(3) 0.88797(17) 0.46293(14) 0.0602(6) Uani 1 1 d . . . C25 C 0.1569(3) 0.80172(17) 0.47459(14) 0.0615(6) Uani 1 1 d . . . H25 H 0.0691 0.7660 0.4543 0.074 Uiso 1 1 calc R . . C26 C 0.3095(2) 0.76851(15) 0.51685(14) 0.0574(6) Uani 1 1 d . . . H26 H 0.3222 0.7101 0.5241 0.069 Uiso 1 1 calc R . . C27 C 1.3794(4) 0.5694(3) 0.7257(3) 0.1394(16) Uani 1 1 d . . . H27A H 1.3243 0.5366 0.6755 0.209 Uiso 1 1 calc R . . H27B H 1.4701 0.5382 0.7661 0.209 Uiso 1 1 calc R . . H27C H 1.4139 0.6220 0.7138 0.209 Uiso 1 1 calc R . . C28 C 0.2077(3) 0.61997(19) 0.17170(14) 0.0760(8) Uani 1 1 d . . . H28A H 0.1404 0.6607 0.1777 0.114 Uiso 1 1 calc R . . H28B H 0.1441 0.5828 0.1260 0.114 Uiso 1 1 calc R . . H28C H 0.2831 0.6490 0.1612 0.114 Uiso 1 1 calc R . . C29 C 1.1274(3) 0.95435(17) 0.94618(16) 0.0753(8) Uani 1 1 d . . . H29A H 1.2006 0.9161 0.9424 0.113 Uiso 1 1 calc R . . H29B H 1.1707 0.9731 1.0027 0.113 Uiso 1 1 calc R . . H29C H 1.1099 1.0024 0.9108 0.113 Uiso 1 1 calc R . . C30 C -0.1459(3) 0.8797(2) 0.3958(2) 0.1053(11) Uani 1 1 d . . . H30A H -0.1488 0.8349 0.3600 0.158 Uiso 1 1 calc R . . H30B H -0.2376 0.9152 0.3662 0.158 Uiso 1 1 calc R . . H30C H -0.1457 0.8557 0.4436 0.158 Uiso 1 1 calc R . . O1 O 1.2809(2) 0.58527(15) 0.75596(14) 0.1111(8) Uani 1 1 d . . . O2 O 0.28989(19) 0.57183(12) 0.24588(9) 0.0720(5) Uani 1 1 d . . . O3 O 0.98147(19) 0.91228(12) 0.92056(10) 0.0746(5) Uani 1 1 d . . . O4 O -0.0073(2) 0.92825(13) 0.42194(11) 0.0854(6) 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 C1 0.0519(14) 0.0590(16) 0.0722(17) -0.0188(13) 0.0097(12) 0.0040(11) C2 0.0568(14) 0.0691(18) 0.0869(19) -0.0135(14) 0.0380(13) -0.0037(12) C3 0.0601(14) 0.0603(15) 0.0615(14) 0.0006(11) 0.0344(11) 0.0036(11) C4 0.0572(13) 0.0505(13) 0.0486(12) -0.0031(10) 0.0276(10) 0.0033(10) C5 0.0708(15) 0.0746(17) 0.0526(13) 0.0021(12) 0.0323(12) 0.0161(12) C6 0.0800(18) 0.0798(19) 0.0486(14) -0.0027(12) 0.0191(13) 0.0183(14) C7 0.0566(12) 0.0506(14) 0.0486(12) 0.0077(10) 0.0257(10) 0.0093(10) C8 0.0657(13) 0.0463(13) 0.0555(13) 0.0007(11) 0.0305(11) 0.0003(10) C9 0.0503(12) 0.0635(16) 0.0479(12) -0.0033(11) 0.0263(10) 0.0019(10) C10 0.0638(14) 0.0631(16) 0.0448(12) 0.0102(11) 0.0268(10) 0.0126(11) C11 0.0732(15) 0.0484(14) 0.0564(14) 0.0050(11) 0.0369(12) 0.0100(11) C12 0.0543(12) 0.0508(13) 0.0479(12) 0.0021(10) 0.0307(10) 0.0074(9) C13 0.0528(12) 0.0502(13) 0.0508(12) 0.0000(10) 0.0292(10) 0.0025(9) C14 0.0545(12) 0.0517(13) 0.0509(12) 0.0000(10) 0.0306(10) -0.0001(9) C15 0.0492(12) 0.0490(13) 0.0549(13) -0.0055(10) 0.0293(10) 0.0003(9) C16 0.0595(13) 0.0699(16) 0.0652(15) -0.0102(12) 0.0407(12) -0.0087(11) C17 0.0506(12) 0.0626(15) 0.0722(16) -0.0092(12) 0.0346(11) -0.0085(10) C18 0.0530(12) 0.0517(14) 0.0542(13) -0.0077(10) 0.0254(10) -0.0040(10) C19 0.0538(12) 0.0679(16) 0.0563(13) -0.0070(11) 0.0329(10) -0.0068(11) C20 0.0480(11) 0.0623(15) 0.0590(14) -0.0061(11) 0.0309(10) -0.0044(10) C21 0.0544(12) 0.0499(13) 0.0480(12) -0.0008(10) 0.0292(10) 0.0018(10) C22 0.0634(14) 0.0530(15) 0.0658(15) 0.0000(11) 0.0329(12) -0.0020(11) C23 0.0748(16) 0.0543(16) 0.0703(16) 0.0085(12) 0.0359(13) 0.0107(12) C24 0.0568(13) 0.0715(17) 0.0472(13) 0.0011(11) 0.0220(10) 0.0116(12) C25 0.0566(13) 0.0656(17) 0.0593(14) -0.0088(12) 0.0264(11) -0.0027(11) C26 0.0596(14) 0.0523(15) 0.0628(14) -0.0054(11) 0.0323(11) 0.0010(11) C27 0.071(2) 0.118(3) 0.204(4) -0.023(3) 0.049(3) 0.003(2) C28 0.0630(15) 0.107(2) 0.0488(14) 0.0044(14) 0.0210(12) -0.0061(14) C29 0.0582(14) 0.0685(18) 0.0731(17) -0.0004(13) 0.0128(12) -0.0149(12) C30 0.0553(17) 0.126(3) 0.110(3) 0.002(2) 0.0221(16) 0.0129(17) O1 0.0591(12) 0.1056(18) 0.1290(19) -0.0376(14) 0.0167(11) 0.0118(11) O2 0.0781(11) 0.0753(12) 0.0495(10) -0.0041(8) 0.0217(8) -0.0029(9) O3 0.0694(11) 0.0882(13) 0.0592(10) -0.0177(9) 0.0265(8) -0.0241(9) O4 0.0649(11) 0.0896(14) 0.0810(13) 0.0066(10) 0.0204(9) 0.0211(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 C1 C2 1.373(4) . ? C1 C6 1.380(4) . ? C1 O1 1.383(3) . ? C2 C3 1.391(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(3) . ? C3 H3 0.9300 . ? C4 C5 1.391(3) . ? C4 C13 1.494(3) . ? C5 C6 1.377(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.374(3) . ? C7 C12 1.393(3) . ? C7 H7 0.9300 . ? C8 C9 1.385(3) . ? C8 H8 0.9300 . ? C9 C10 1.369(3) . ? C9 O2 1.372(3) . ? C10 C11 1.394(3) . ? C10 H10 0.9300 . ? C11 C12 1.387(3) . ? C11 H11 0.9300 . ? C12 C13 1.491(3) . ? C13 C14 1.357(3) . ? C14 C21 1.491(3) . ? C14 C15 1.494(3) . ? C15 C16 1.381(3) . ? C15 C20 1.394(3) . ? C16 C17 1.385(3) . ? C16 H16 0.9300 . ? C17 C18 1.377(3) . ? C17 H17 0.9300 . ? C18 O3 1.374(3) . ? C18 C19 1.382(3) . ? C19 C20 1.375(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C26 1.382(3) . ? C21 C22 1.390(3) . ? C22 C23 1.378(3) . ? C22 H22 0.9300 . ? C23 C24 1.379(3) . ? C23 H23 0.9300 . ? C24 O4 1.370(3) . ? C24 C25 1.376(4) . ? C25 C26 1.387(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 O1 1.349(4) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 O2 1.418(3) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 O3 1.413(3) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 O4 1.407(4) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 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 C2 C1 C6 119.4(2) . . ? C2 C1 O1 125.3(3) . . ? C6 C1 O1 115.3(3) . . ? C1 C2 C3 119.9(2) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 121.7(2) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 117.2(2) . . ? C3 C4 C13 120.6(2) . . ? C5 C4 C13 122.2(2) . . ? C6 C5 C4 121.4(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 120.4(3) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? C8 C7 C12 122.3(2) . . ? C8 C7 H7 118.8 . . ? C12 C7 H7 118.8 . . ? C7 C8 C9 120.0(2) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 O2 125.3(2) . . ? C10 C9 C8 119.3(2) . . ? O2 C9 C8 115.4(2) . . ? C9 C10 C11 120.1(2) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 121.8(2) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C7 116.4(2) . . ? C11 C12 C13 124.1(2) . . ? C7 C12 C13 119.50(19) . . ? C14 C13 C12 123.07(19) . . ? C14 C13 C4 122.00(19) . . ? C12 C13 C4 114.92(18) . . ? C13 C14 C21 123.60(19) . . ? C13 C14 C15 122.06(19) . . ? C21 C14 C15 114.34(18) . . ? C16 C15 C20 117.2(2) . . ? C16 C15 C14 122.94(19) . . ? C20 C15 C14 119.83(19) . . ? C15 C16 C17 122.0(2) . . ? C15 C16 H16 119.0 . . ? C17 C16 H16 119.0 . . ? C18 C17 C16 119.3(2) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? O3 C18 C17 124.6(2) . . ? O3 C18 C19 115.5(2) . . ? C17 C18 C19 119.9(2) . . ? C20 C19 C18 119.9(2) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C15 121.5(2) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? C26 C21 C22 117.1(2) . . ? C26 C21 C14 122.7(2) . . ? C22 C21 C14 120.23(19) . . ? C23 C22 C21 121.4(2) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 120.3(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? O4 C24 C25 124.9(2) . . ? O4 C24 C23 115.5(2) . . ? C25 C24 C23 119.6(2) . . ? C24 C25 C26 119.4(2) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C21 C26 C25 122.2(2) . . ? C21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? O1 C27 H27A 109.5 . . ? O1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O2 C28 H28A 109.5 . . ? O2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O3 C29 H29A 109.5 . . ? O3 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O3 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O4 C30 H30A 109.5 . . ? O4 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O4 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 O1 C1 119.8(3) . . ? C9 O2 C28 118.0(2) . . ? C18 O3 C29 118.0(2) . . ? C24 O4 C30 118.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.8(4) . . . . ? O1 C1 C2 C3 -179.3(2) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C2 C3 C4 C5 -2.3(3) . . . . ? C2 C3 C4 C13 178.6(2) . . . . ? C3 C4 C5 C6 2.2(4) . . . . ? C13 C4 C5 C6 -178.7(2) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C2 C1 C6 C5 -0.9(4) . . . . ? O1 C1 C6 C5 179.2(2) . . . . ? C12 C7 C8 C9 0.9(3) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? C7 C8 C9 O2 -179.4(2) . . . . ? O2 C9 C10 C11 178.7(2) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C10 C11 C12 C7 1.0(3) . . . . ? C10 C11 C12 C13 -178.4(2) . . . . ? C8 C7 C12 C11 -1.6(3) . . . . ? C8 C7 C12 C13 177.7(2) . . . . ? C11 C12 C13 C14 48.6(3) . . . . ? C7 C12 C13 C14 -130.8(2) . . . . ? C11 C12 C13 C4 -132.9(2) . . . . ? C7 C12 C13 C4 47.8(3) . . . . ? C3 C4 C13 C14 -128.2(2) . . . . ? C5 C4 C13 C14 52.8(3) . . . . ? C3 C4 C13 C12 53.2(3) . . . . ? C5 C4 C13 C12 -125.8(2) . . . . ? C12 C13 C14 C21 2.6(3) . . . . ? C4 C13 C14 C21 -175.91(19) . . . . ? C12 C13 C14 C15 -177.76(19) . . . . ? C4 C13 C14 C15 3.7(3) . . . . ? C13 C14 C15 C16 56.9(3) . . . . ? C21 C14 C15 C16 -123.4(2) . . . . ? C13 C14 C15 C20 -123.6(2) . . . . ? C21 C14 C15 C20 56.1(3) . . . . ? C20 C15 C16 C17 3.1(3) . . . . ? C14 C15 C16 C17 -177.4(2) . . . . ? C15 C16 C17 C18 -1.4(4) . . . . ? C16 C17 C18 O3 -179.8(2) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? O3 C18 C19 C20 -180.0(2) . . . . ? C17 C18 C19 C20 0.7(3) . . . . ? C18 C19 C20 C15 1.2(4) . . . . ? C16 C15 C20 C19 -3.0(3) . . . . ? C14 C15 C20 C19 177.5(2) . . . . ? C13 C14 C21 C26 54.9(3) . . . . ? C15 C14 C21 C26 -124.8(2) . . . . ? C13 C14 C21 C22 -126.2(2) . . . . ? C15 C14 C21 C22 54.1(3) . . . . ? C26 C21 C22 C23 -2.4(3) . . . . ? C14 C21 C22 C23 178.7(2) . . . . ? C21 C22 C23 C24 2.1(4) . . . . ? C22 C23 C24 O4 179.2(2) . . . . ? C22 C23 C24 C25 -0.4(4) . . . . ? O4 C24 C25 C26 179.6(2) . . . . ? C23 C24 C25 C26 -0.8(3) . . . . ? C22 C21 C26 C25 1.1(3) . . . . ? C14 C21 C26 C25 180.0(2) . . . . ? C24 C25 C26 C21 0.5(3) . . . . ? C2 C1 O1 C27 -10.9(4) . . . . ? C6 C1 O1 C27 168.9(3) . . . . ? C10 C9 O2 C28 3.4(3) . . . . ? C8 C9 O2 C28 -176.7(2) . . . . ? C17 C18 O3 C29 2.9(3) . . . . ? C19 C18 O3 C29 -176.4(2) . . . . ? C25 C24 O4 C30 5.9(4) . . . . ? C23 C24 O4 C30 -173.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.486 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.035 data_tae _database_code_depnum_ccdc_archive 'CCDC 921516' #TrackingRef 'web_deposit_cif_file_1_YifeiLiu_1358991452.TAE.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 O4' _chemical_formula_sum 'C30 H28 O4' _chemical_formula_weight 452.52 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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 19.567(12) _cell_length_b 5.624(4) _cell_length_c 13.776(12) _cell_angle_alpha 90.00 _cell_angle_beta 125.66(3) _cell_angle_gamma 90.00 _cell_volume 1231.7(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9574 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 6061 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2668 _reflns_number_gt 1958 _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^)+(0.0550P)^2^+0.0412P] 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 0.3(16) _refine_ls_number_reflns 2668 _refine_ls_number_parameters 156 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 C1 C 0.38075(12) 0.2476(4) 0.09195(15) 0.0545(5) Uani 1 1 d . . . C2 C 0.36681(13) 0.0603(4) 0.14273(16) 0.0573(5) Uani 1 1 d . . . H2 H 0.3268 -0.0544 0.0943 0.069 Uiso 1 1 calc R . . C3 C 0.41209(12) 0.0424(3) 0.26551(16) 0.0550(5) Uani 1 1 d . . . H3 H 0.4015 -0.0837 0.2987 0.066 Uiso 1 1 calc R . . C4 C 0.47311(11) 0.2093(3) 0.34042(15) 0.0470(4) Uani 1 1 d . . . C5 C 0.48878(12) 0.3897(4) 0.28684(16) 0.0540(5) Uani 1 1 d . . . H5 H 0.5315 0.4984 0.3349 0.065 Uiso 1 1 calc R . . C6 C 0.44249(13) 0.4119(4) 0.16396(17) 0.0583(5) Uani 1 1 d . . . H6 H 0.4530 0.5369 0.1301 0.070 Uiso 1 1 calc R . . C7 C 0.51989(11) 0.2068(3) 0.47309(15) 0.0486(4) Uani 1 1 d . . . C8 C 0.61360(10) 0.2265(3) 0.54232(14) 0.0463(4) Uani 1 1 d . . . C9 C 0.65898(12) 0.0640(4) 0.52476(14) 0.0508(4) Uani 1 1 d . . . H9 H 0.6305 -0.0579 0.4695 0.061 Uiso 1 1 calc R . . C10 C 0.74540(12) 0.0793(4) 0.58755(15) 0.0519(4) Uani 1 1 d . . . H10 H 0.7747 -0.0323 0.5753 0.062 Uiso 1 1 calc R . . C11 C 0.78799(11) 0.2616(3) 0.66869(15) 0.0483(4) Uani 1 1 d . . . C12 C 0.74416(12) 0.4285(4) 0.68566(17) 0.0587(5) Uani 1 1 d . . . H12 H 0.7724 0.5533 0.7390 0.070 Uiso 1 1 calc R . . C13 C 0.65789(12) 0.4081(4) 0.62251(18) 0.0573(5) Uani 1 1 d . . . H13 H 0.6287 0.5208 0.6345 0.069 Uiso 1 1 calc R . . C14 C 0.3373(2) 0.4578(5) -0.0855(2) 0.0955(9) Uani 1 1 d . . . H14A H 0.3920 0.4614 -0.0696 0.143 Uiso 1 1 calc R . . H14B H 0.3294 0.5987 -0.0538 0.143 Uiso 1 1 calc R . . H14C H 0.2951 0.4510 -0.1702 0.143 Uiso 1 1 calc R . . C15 C 0.91833(14) 0.4582(5) 0.8054(2) 0.0854(8) Uani 1 1 d . . . H15A H 0.9133 0.4544 0.8707 0.128 Uiso 1 1 calc R . . H15B H 0.8954 0.6046 0.7623 0.128 Uiso 1 1 calc R . . H15C H 0.9766 0.4470 0.8358 0.128 Uiso 1 1 calc R . . O1 O 0.33054(10) 0.2544(3) -0.03074(11) 0.0767(5) Uani 1 1 d . . . O2 O 0.87352(8) 0.2640(3) 0.72784(13) 0.0667(4) 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 C1 0.0578(11) 0.0555(10) 0.0459(9) 0.0015(10) 0.0279(8) 0.0076(10) C2 0.0570(11) 0.0536(11) 0.0527(10) -0.0092(10) 0.0272(9) -0.0070(10) C3 0.0614(12) 0.0490(10) 0.0563(10) -0.0009(9) 0.0353(9) -0.0081(9) C4 0.0455(9) 0.0458(9) 0.0491(9) 0.0009(8) 0.0273(7) 0.0010(8) C5 0.0537(11) 0.0497(10) 0.0544(10) -0.0030(9) 0.0292(9) -0.0086(9) C6 0.0662(13) 0.0538(11) 0.0562(11) 0.0077(10) 0.0363(10) -0.0011(10) C7 0.0512(10) 0.0432(9) 0.0504(9) -0.0006(9) 0.0291(8) -0.0004(8) C8 0.0469(9) 0.0463(9) 0.0462(8) 0.0006(9) 0.0275(8) -0.0009(8) C9 0.0542(11) 0.0509(10) 0.0426(9) -0.0048(8) 0.0255(8) 0.0012(9) C10 0.0550(11) 0.0546(10) 0.0470(9) 0.0026(9) 0.0302(8) 0.0118(9) C11 0.0451(9) 0.0537(10) 0.0459(8) 0.0080(9) 0.0265(7) 0.0024(9) C12 0.0525(12) 0.0528(10) 0.0665(12) -0.0147(10) 0.0322(10) -0.0108(9) C13 0.0524(11) 0.0502(10) 0.0726(12) -0.0131(10) 0.0383(10) -0.0013(9) C14 0.138(3) 0.0820(17) 0.0591(12) 0.0145(13) 0.0536(15) 0.0088(17) C15 0.0507(13) 0.0886(17) 0.0986(18) -0.0124(16) 0.0333(13) -0.0170(13) O1 0.0914(11) 0.0756(10) 0.0455(7) 0.0034(7) 0.0299(7) 0.0021(9) O2 0.0469(7) 0.0748(10) 0.0737(8) -0.0016(8) 0.0325(6) 0.0009(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 C1 O1 1.374(2) . ? C1 C2 1.377(3) . ? C1 C6 1.378(3) . ? C2 C3 1.382(3) . ? C2 H2 0.9300 . ? C3 C4 1.391(3) . ? C3 H3 0.9300 . ? C4 C5 1.390(3) . ? C4 C7 1.493(3) . ? C5 C6 1.383(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C7 1.352(4) 2_656 ? C7 C8 1.498(3) . ? C8 C13 1.378(3) . ? C8 C9 1.390(3) . ? C9 C10 1.382(3) . ? C9 H9 0.9300 . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C11 O2 1.369(2) . ? C11 C12 1.380(3) . ? C12 C13 1.381(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O1 1.419(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O2 1.418(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 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 O1 C1 C2 115.78(18) . . ? O1 C1 C6 124.40(18) . . ? C2 C1 C6 119.82(16) . . ? C1 C2 C3 120.14(18) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 121.31(18) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 117.28(16) . . ? C5 C4 C7 119.30(17) . . ? C3 C4 C7 123.40(17) . . ? C6 C5 C4 121.72(18) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C1 C6 C5 119.62(18) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C7 C7 C4 122.2(2) 2_656 . ? C7 C7 C8 122.2(2) 2_656 . ? C4 C7 C8 115.34(15) . . ? C13 C8 C9 117.37(17) . . ? C13 C8 C7 121.98(17) . . ? C9 C8 C7 120.62(17) . . ? C10 C9 C8 121.51(17) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C11 C10 C9 119.58(17) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? O2 C11 C12 123.85(17) . . ? O2 C11 C10 116.12(16) . . ? C12 C11 C10 120.02(17) . . ? C11 C12 C13 119.27(18) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C8 C13 C12 122.22(19) . . ? C8 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C1 O1 C14 117.09(19) . . ? C11 O2 C15 117.42(18) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.102 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.026