# 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_a2 _database_code_depnum_ccdc_archive 'CCDC 727724' #TrackingRef '204-CIF-2g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H20 O1' _chemical_formula_sum 'C28 H20 O1' _chemical_formula_weight 372.44 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.3616(15) _cell_length_b 11.6419(15) _cell_length_c 14.8370(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.197(2) _cell_angle_gamma 90.00 _cell_volume 1951.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1900 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 21.69 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.985 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details SADABS;Bruker,2000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11980 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0821 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.25 _reflns_number_total 4705 _reflns_number_gt 2163 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4705 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1055 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0711 _refine_ls_wR_factor_gt 0.0625 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _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 C9A C -0.00707(12) 0.54212(12) 0.22119(9) 0.0387(4) Uani 1 1 d . . . C10A C -0.09564(12) 0.45636(12) 0.22868(10) 0.0398(4) Uani 1 1 d . . . C1A C -0.14406(12) 0.44382(13) 0.31228(10) 0.0438(4) Uani 1 1 d . . . C11A C 0.03883(12) 0.56501(12) 0.12999(9) 0.0426(4) Uani 1 1 d . . . H11A H 0.0480 0.4913 0.0997 0.051 Uiso 1 1 calc R . . C8A C 0.03067(12) 0.60661(12) 0.29558(10) 0.0439(4) Uani 1 1 d . . . H8AA H 0.0887 0.6620 0.2910 0.053 Uiso 1 1 calc R . . C13A C -0.16341(13) 0.62584(13) 0.03794(9) 0.0496(4) Uani 1 1 d . . . H13A H -0.2051 0.5638 0.0579 0.060 Uiso 1 1 calc R . . C6A C -0.10163(13) 0.51332(13) 0.38656(10) 0.0514(4) Uani 1 1 d . . . H6AA H -0.1331 0.5052 0.4415 0.062 Uiso 1 1 calc R . . C12A C -0.04448(13) 0.64104(13) 0.06748(9) 0.0434(4) Uani 1 1 d . . . C26A C 0.26713(13) 0.60001(13) 0.17594(10) 0.0476(4) Uani 1 1 d . . . O1A O -0.33542(10) 0.70004(10) -0.05589(7) 0.0723(3) Uani 1 1 d . . . C2A C -0.13859(13) 0.38253(13) 0.15654(10) 0.0519(4) Uani 1 1 d . . . H2AA H -0.1070 0.3878 0.1014 0.062 Uiso 1 1 calc R . . C27A C 0.15480(13) 0.63062(13) 0.13264(10) 0.0450(4) Uani 1 1 d . . . C7A C -0.01558(13) 0.59161(13) 0.37857(10) 0.0504(4) Uani 1 1 d . . . H7AA H 0.0131 0.6357 0.4284 0.060 Uiso 1 1 calc R . . C17A C 0.01735(14) 0.73597(14) 0.03996(10) 0.0501(4) Uani 1 1 d . . . C18A C 0.13938(14) 0.72927(13) 0.08101(10) 0.0488(4) Uani 1 1 d . . . C5A C -0.23401(13) 0.36102(15) 0.31958(12) 0.0596(5) Uani 1 1 d . . . H5AA H -0.2667 0.3532 0.3741 0.072 Uiso 1 1 calc R . . C21A C 0.36343(14) 0.67714(15) 0.16708(11) 0.0541(4) Uani 1 1 d . . . C14A C -0.21896(15) 0.70564(15) -0.02231(11) 0.0552(4) Uani 1 1 d . . . C25A C 0.29040(14) 0.49737(14) 0.22506(10) 0.0574(4) Uani 1 1 d . . . H25A H 0.2289 0.4465 0.2319 0.069 Uiso 1 1 calc R . . C22A C 0.47620(15) 0.64781(16) 0.20838(12) 0.0677(5) Uani 1 1 d . . . H22A H 0.5389 0.6980 0.2038 0.081 Uiso 1 1 calc R . . C19A C 0.23493(15) 0.80454(14) 0.07299(11) 0.0633(5) Uani 1 1 d . . . H19A H 0.2238 0.8712 0.0386 0.076 Uiso 1 1 calc R . . C20A C 0.34299(15) 0.77889(15) 0.11586(11) 0.0642(5) Uani 1 1 d . . . H20A H 0.4054 0.8296 0.1115 0.077 Uiso 1 1 calc R . . C3A C -0.22535(14) 0.30398(14) 0.16636(12) 0.0643(5) Uani 1 1 d . . . H3AA H -0.2529 0.2572 0.1178 0.077 Uiso 1 1 calc R . . C16A C -0.03941(16) 0.81538(14) -0.02066(10) 0.0617(5) Uani 1 1 d . . . H16A H 0.0014 0.8786 -0.0396 0.074 Uiso 1 1 calc R . . C4A C -0.27306(14) 0.29329(15) 0.24856(13) 0.0694(5) Uani 1 1 d . . . H4AA H -0.3320 0.2393 0.2546 0.083 Uiso 1 1 calc R . . C15A C -0.15696(16) 0.79844(15) -0.05194(11) 0.0649(5) Uani 1 1 d . . . H15A H -0.1950 0.8498 -0.0933 0.078 Uiso 1 1 calc R . . C24A C 0.40287(16) 0.47164(15) 0.26293(11) 0.0686(5) Uani 1 1 d . . . H24A H 0.4172 0.4030 0.2942 0.082 Uiso 1 1 calc R . . C23A C 0.49625(15) 0.54817(17) 0.25477(12) 0.0722(5) Uani 1 1 d . . . H23A H 0.5721 0.5306 0.2812 0.087 Uiso 1 1 calc R . . C28A C -0.40552(14) 0.61001(16) -0.02569(12) 0.0799(6) Uani 1 1 d . . . H28A H -0.4847 0.6158 -0.0554 0.120 Uiso 1 1 calc R . . H28B H -0.4072 0.6159 0.0387 0.120 Uiso 1 1 calc R . . H28C H -0.3721 0.5373 -0.0399 0.120 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 C9A 0.0387(9) 0.0387(9) 0.0390(10) 0.0023(7) 0.0055(7) 0.0044(7) C10A 0.0368(9) 0.0393(9) 0.0432(10) 0.0004(7) 0.0044(7) 0.0019(7) C1A 0.0404(9) 0.0474(11) 0.0441(10) 0.0072(8) 0.0072(8) 0.0056(8) C11A 0.0481(9) 0.0410(10) 0.0398(9) -0.0014(7) 0.0096(7) -0.0024(8) C8A 0.0459(9) 0.0438(10) 0.0421(10) 0.0014(8) 0.0048(8) -0.0010(7) C13A 0.0562(11) 0.0500(11) 0.0425(10) -0.0010(8) 0.0054(8) 0.0036(9) C6A 0.0538(10) 0.0609(12) 0.0409(10) 0.0054(9) 0.0122(8) 0.0106(9) C12A 0.0517(10) 0.0446(10) 0.0349(9) -0.0011(7) 0.0084(7) 0.0002(8) C26A 0.0483(10) 0.0496(11) 0.0469(10) -0.0038(8) 0.0149(8) -0.0022(9) O1A 0.0613(8) 0.0737(9) 0.0779(9) 0.0104(7) -0.0102(7) 0.0026(7) C2A 0.0557(11) 0.0484(11) 0.0516(11) 0.0005(8) 0.0054(8) -0.0059(8) C27A 0.0468(10) 0.0464(10) 0.0435(10) -0.0030(8) 0.0128(8) -0.0026(8) C7A 0.0564(11) 0.0552(11) 0.0389(10) -0.0057(8) 0.0027(8) 0.0042(9) C17A 0.0577(11) 0.0521(11) 0.0416(10) 0.0009(8) 0.0104(8) -0.0013(9) C18A 0.0554(11) 0.0474(11) 0.0456(10) 0.0012(8) 0.0146(8) -0.0076(9) C5A 0.0541(11) 0.0660(13) 0.0611(12) 0.0126(10) 0.0165(9) -0.0043(9) C21A 0.0476(11) 0.0606(12) 0.0557(11) -0.0084(9) 0.0138(9) -0.0072(9) C14A 0.0561(12) 0.0614(12) 0.0470(11) -0.0038(9) -0.0002(9) 0.0064(10) C25A 0.0484(11) 0.0619(12) 0.0627(12) 0.0021(9) 0.0098(9) 0.0004(9) C22A 0.0540(12) 0.0779(15) 0.0723(14) -0.0125(11) 0.0116(10) -0.0136(11) C19A 0.0714(13) 0.0575(12) 0.0631(12) 0.0079(9) 0.0166(10) -0.0114(10) C20A 0.0622(13) 0.0616(13) 0.0709(13) -0.0011(10) 0.0163(10) -0.0184(10) C3A 0.0636(12) 0.0599(12) 0.0676(13) -0.0048(10) -0.0005(10) -0.0164(10) C16A 0.0748(13) 0.0579(12) 0.0532(12) 0.0132(9) 0.0103(10) -0.0007(10) C4A 0.0582(12) 0.0697(14) 0.0808(15) 0.0085(11) 0.0093(11) -0.0199(10) C15A 0.0746(13) 0.0634(13) 0.0561(12) 0.0155(10) 0.0037(10) 0.0079(11) C24A 0.0617(12) 0.0732(14) 0.0716(13) 0.0073(10) 0.0097(10) 0.0098(11) C23A 0.0505(12) 0.0896(16) 0.0758(14) -0.0080(12) 0.0039(10) 0.0026(12) C28A 0.0601(12) 0.0917(15) 0.0873(15) 0.0024(12) 0.0050(10) -0.0044(11) _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 C9A C8A 1.3652(17) . ? C9A C10A 1.4304(17) . ? C9A C11A 1.5253(17) . ? C10A C1A 1.4175(18) . ? C10A C2A 1.4177(18) . ? C1A C6A 1.4096(18) . ? C1A C5A 1.4175(19) . ? C11A C27A 1.5198(17) . ? C11A C12A 1.5330(18) . ? C11A H11A 0.9800 . ? C8A C7A 1.4009(18) . ? C8A H8AA 0.9300 . ? C13A C12A 1.3861(18) . ? C13A C14A 1.3924(19) . ? C13A H13A 0.9300 . ? C6A C7A 1.3511(18) . ? C6A H6AA 0.9300 . ? C12A C17A 1.3941(18) . ? C26A C25A 1.4098(19) . ? C26A C27A 1.4112(19) . ? C26A C21A 1.4323(19) . ? O1A C14A 1.3642(17) . ? O1A C28A 1.4180(17) . ? C2A C3A 1.3639(18) . ? C2A H2AA 0.9300 . ? C27A C18A 1.3811(18) . ? C7A H7AA 0.9300 . ? C17A C16A 1.3980(19) . ? C17A C18A 1.4550(19) . ? C18A C19A 1.4102(19) . ? C5A C4A 1.352(2) . ? C5A H5AA 0.9300 . ? C21A C22A 1.401(2) . ? C21A C20A 1.413(2) . ? C14A C15A 1.387(2) . ? C25A C24A 1.3723(19) . ? C25A H25A 0.9300 . ? C22A C23A 1.356(2) . ? C22A H22A 0.9300 . ? C19A C20A 1.354(2) . ? C19A H19A 0.9300 . ? C20A H20A 0.9300 . ? C3A C4A 1.393(2) . ? C3A H3AA 0.9300 . ? C16A C15A 1.3799(19) . ? C16A H16A 0.9300 . ? C4A H4AA 0.9300 . ? C15A H15A 0.9300 . ? C24A C23A 1.401(2) . ? C24A H24A 0.9300 . ? C23A H23A 0.9300 . ? C28A H28A 0.9600 . ? C28A H28B 0.9600 . ? C28A H28C 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 C8A C9A C10A 118.90(13) . . ? C8A C9A C11A 120.90(13) . . ? C10A C9A C11A 120.12(13) . . ? C1A C10A C2A 117.63(14) . . ? C1A C10A C9A 118.86(13) . . ? C2A C10A C9A 123.52(13) . . ? C6A C1A C5A 121.27(14) . . ? C6A C1A C10A 119.52(14) . . ? C5A C1A C10A 119.21(14) . . ? C27A C11A C9A 116.32(12) . . ? C27A C11A C12A 101.69(11) . . ? C9A C11A C12A 112.93(11) . . ? C27A C11A H11A 108.5 . . ? C9A C11A H11A 108.5 . . ? C12A C11A H11A 108.5 . . ? C9A C8A C7A 121.82(14) . . ? C9A C8A H8AA 119.1 . . ? C7A C8A H8AA 119.1 . . ? C12A C13A C14A 118.47(15) . . ? C12A C13A H13A 120.8 . . ? C14A C13A H13A 120.8 . . ? C7A C6A C1A 120.55(14) . . ? C7A C6A H6AA 119.7 . . ? C1A C6A H6AA 119.7 . . ? C13A C12A C17A 120.89(14) . . ? C13A C12A C11A 129.41(14) . . ? C17A C12A C11A 109.70(13) . . ? C25A C26A C27A 124.01(15) . . ? C25A C26A C21A 118.45(15) . . ? C27A C26A C21A 117.53(15) . . ? C14A O1A C28A 118.40(13) . . ? C3A C2A C10A 121.31(15) . . ? C3A C2A H2AA 119.3 . . ? C10A C2A H2AA 119.3 . . ? C18A C27A C26A 121.12(14) . . ? C18A C27A C11A 110.23(13) . . ? C26A C27A C11A 128.60(14) . . ? C6A C7A C8A 120.32(14) . . ? C6A C7A H7AA 119.8 . . ? C8A C7A H7AA 119.8 . . ? C12A C17A C16A 120.04(15) . . ? C12A C17A C18A 108.81(14) . . ? C16A C17A C18A 131.10(16) . . ? C27A C18A C19A 120.71(15) . . ? C27A C18A C17A 109.57(14) . . ? C19A C18A C17A 129.71(16) . . ? C4A C5A C1A 121.05(15) . . ? C4A C5A H5AA 119.5 . . ? C1A C5A H5AA 119.5 . . ? C22A C21A C20A 121.92(16) . . ? C22A C21A C26A 118.59(16) . . ? C20A C21A C26A 119.48(16) . . ? O1A C14A C15A 115.29(15) . . ? O1A C14A C13A 123.87(16) . . ? C15A C14A C13A 120.84(16) . . ? C24A C25A C26A 120.73(15) . . ? C24A C25A H25A 119.6 . . ? C26A C25A H25A 119.6 . . ? C23A C22A C21A 121.74(17) . . ? C23A C22A H22A 119.1 . . ? C21A C22A H22A 119.1 . . ? C20A C19A C18A 119.39(16) . . ? C20A C19A H19A 120.3 . . ? C18A C19A H19A 120.3 . . ? C19A C20A C21A 121.72(16) . . ? C19A C20A H20A 119.1 . . ? C21A C20A H20A 119.1 . . ? C2A C3A C4A 120.50(16) . . ? C2A C3A H3AA 119.7 . . ? C4A C3A H3AA 119.7 . . ? C15A C16A C17A 118.97(16) . . ? C15A C16A H16A 120.5 . . ? C17A C16A H16A 120.5 . . ? C5A C4A C3A 120.29(16) . . ? C5A C4A H4AA 119.9 . . ? C3A C4A H4AA 119.9 . . ? C16A C15A C14A 120.73(16) . . ? C16A C15A H15A 119.6 . . ? C14A C15A H15A 119.6 . . ? C25A C24A C23A 120.42(17) . . ? C25A C24A H24A 119.8 . . ? C23A C24A H24A 119.8 . . ? C22A C23A C24A 120.06(17) . . ? C22A C23A H23A 120.0 . . ? C24A C23A H23A 120.0 . . ? O1A C28A H28A 109.5 . . ? O1A C28A H28B 109.5 . . ? H28A C28A H28B 109.5 . . ? O1A C28A H28C 109.5 . . ? H28A C28A H28C 109.5 . . ? H28B C28A H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.164 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.035 data_a _database_code_depnum_ccdc_archive 'CCDC 727725' #TrackingRef '203-CIF-2f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H18' _chemical_formula_weight 342.43 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M ' P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.975(3) _cell_length_b 7.2022(15) _cell_length_c 19.200(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.338(3) _cell_angle_gamma 90.00 _cell_volume 1789.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1456 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 24.83 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details SADABS;Bruker,2000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9854 _diffrn_reflns_av_R_equivalents 0.1459 _diffrn_reflns_av_sigmaI/netI 0.1626 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.99 _reflns_number_total 6883 _reflns_number_gt 2986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6883 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1354 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1471 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 C15' C 0.4145(3) 0.9080(4) 0.40201(15) 0.0439(8) Uani 1 1 d . . . C19' C -0.0203(3) 1.0577(4) 0.26657(17) 0.0477(9) Uani 1 1 d . . . C17' C 0.2891(3) 1.1270(4) 0.34957(16) 0.0437(8) Uani 1 1 d . . . C18' C 0.1808(3) 1.1279(4) 0.31993(16) 0.0452(8) Uani 1 1 d . . . C21' C 0.1372(2) 0.9579(4) 0.33168(15) 0.0417(8) Uani 1 1 d . . . C20' C 0.0345(3) 0.9130(4) 0.30544(16) 0.0433(8) Uani 1 1 d . . . C13' C 0.2158(2) 0.8323(4) 0.37262(15) 0.0389(7) Uani 1 1 d . . . H13A H 0.2286 0.7207 0.3454 0.047 Uiso 1 1 calc R . . C16' C 0.4909(3) 1.0477(4) 0.39740(17) 0.0487(9) Uani 1 1 d . . . C14' C 0.3114(2) 0.9565(4) 0.37720(15) 0.0430(8) Uani 1 1 d . . . C23' C 0.1799(2) 0.7779(4) 0.44391(16) 0.0435(8) Uani 1 1 d . . . C8' C 0.0251(3) 1.2278(5) 0.25632(17) 0.0538(9) Uani 1 1 d . . . H8'A H -0.0122 1.3178 0.2305 0.065 Uiso 1 1 calc R . . C7' C 0.1246(3) 1.2687(4) 0.28329(17) 0.0543(9) Uani 1 1 d . . . H7'A H 0.1532 1.3855 0.2774 0.065 Uiso 1 1 calc R . . C24' C 0.1482(3) 0.9155(5) 0.48804(17) 0.0512(9) Uani 1 1 d . . . H24A H 0.1507 1.0396 0.4749 0.061 Uiso 1 1 calc R . . C1' C 0.4440(3) 0.7296(5) 0.42544(16) 0.0525(9) Uani 1 1 d . . . H1'A H 0.3945 0.6372 0.4284 0.063 Uiso 1 1 calc R . . C6' C 0.3650(3) 1.2671(5) 0.34708(17) 0.0557(10) Uani 1 1 d . . . H6'A H 0.3482 1.3845 0.3294 0.067 Uiso 1 1 calc R . . C5' C 0.4632(3) 1.2247(5) 0.37136(18) 0.0566(10) Uani 1 1 d . . . H5'A H 0.5139 1.3158 0.3708 0.068 Uiso 1 1 calc R . . C12' C -0.1205(3) 1.0128(5) 0.23614(18) 0.0604(10) Uani 1 1 d . . . H12A H -0.1568 1.1013 0.2089 0.072 Uiso 1 1 calc R . . C2' C 0.5467(3) 0.6916(5) 0.44402(18) 0.0605(10) Uani 1 1 d . . . H2'A H 0.5661 0.5735 0.4595 0.073 Uiso 1 1 calc R . . C11' C -0.0132(3) 0.7440(5) 0.31484(18) 0.0541(9) Uani 1 1 d . . . H11A H 0.0218 0.6533 0.3417 0.065 Uiso 1 1 calc R . . C9' C -0.1109(3) 0.7065(5) 0.2855(2) 0.0693(11) Uani 1 1 d . . . H9'A H -0.1412 0.5913 0.2920 0.083 Uiso 1 1 calc R . . C4' C 0.5957(3) 1.0024(5) 0.41810(19) 0.0624(10) Uani 1 1 d . . . H4'A H 0.6464 1.0934 0.4166 0.075 Uiso 1 1 calc R . . C3' C 0.6223(3) 0.8304(5) 0.43967(19) 0.0638(10) Uani 1 1 d . . . H3'A H 0.6914 0.8027 0.4518 0.077 Uiso 1 1 calc R . . C25' C 0.1127(3) 0.8669(6) 0.55184(18) 0.0659(11) Uani 1 1 d . . . H25A H 0.0907 0.9591 0.5812 0.079 Uiso 1 1 calc R . . C22' C 0.1770(3) 0.5958(4) 0.46480(19) 0.0626(11) Uani 1 1 d . . . H22A H 0.1992 0.5029 0.4358 0.075 Uiso 1 1 calc R . . C10' C -0.1647(3) 0.8447(5) 0.2457(2) 0.0698(11) Uani 1 1 d . . . H10A H -0.2309 0.8207 0.2257 0.084 Uiso 1 1 calc R . . C27' C 0.1411(3) 0.5495(6) 0.5290(2) 0.0801(13) Uani 1 1 d . . . H27A H 0.1386 0.4258 0.5425 0.096 Uiso 1 1 calc R . . C26' C 0.1097(3) 0.6856(6) 0.5721(2) 0.0728(12) Uani 1 1 d . . . H26A H 0.0862 0.6547 0.6152 0.087 Uiso 1 1 calc R . . C20 C 0.0871(3) 0.4079(4) 0.09879(16) 0.0415(8) Uani 1 1 d . . . C17 C 0.3194(3) 0.6290(4) 0.17969(16) 0.0441(8) Uani 1 1 d . . . C18 C 0.2114(3) 0.6268(4) 0.15042(16) 0.0447(8) Uani 1 1 d . . . C16 C 0.5209(3) 0.5561(4) 0.23373(17) 0.0471(8) Uani 1 1 d . . . C15 C 0.4651(2) 0.4144(4) 0.19409(16) 0.0448(8) Uani 1 1 d . . . C21 C 0.1877(2) 0.4550(4) 0.12237(15) 0.0393(8) Uani 1 1 d . . . C14 C 0.3623(3) 0.4562(4) 0.16803(15) 0.0423(8) Uani 1 1 d . . . C19 C 0.0101(3) 0.5498(5) 0.10283(16) 0.0492(9) Uani 1 1 d . . . C13 C 0.2846(2) 0.3330(4) 0.12734(15) 0.0387(8) Uani 1 1 d . . . H13B H 0.2721 0.2215 0.1547 0.046 Uiso 1 1 calc R . . C22 C 0.3201(2) 0.2764(4) 0.05630(16) 0.0396(8) Uani 1 1 d . . . C8 C 0.0374(3) 0.7241(5) 0.12908(18) 0.0571(10) Uani 1 1 d . . . H8A H -0.0132 0.8153 0.1300 0.069 Uiso 1 1 calc R . . C12 C 0.0554(3) 0.2312(5) 0.07412(17) 0.0531(9) Uani 1 1 d . . . H12B H 0.1056 0.1405 0.0701 0.064 Uiso 1 1 calc R . . C5 C 0.4740(3) 0.7305(5) 0.24396(17) 0.0571(10) Uani 1 1 d . . . H5A H 0.5109 0.8222 0.2692 0.069 Uiso 1 1 calc R . . C6 C 0.3756(3) 0.7659(5) 0.21740(17) 0.0553(10) Uani 1 1 d . . . H6A H 0.3459 0.8812 0.2244 0.066 Uiso 1 1 calc R . . C7 C 0.1348(3) 0.7652(4) 0.15327(17) 0.0507(9) Uani 1 1 d . . . H7A H 0.1513 0.8821 0.1714 0.061 Uiso 1 1 calc R . . C23 C 0.3528(2) 0.4123(5) 0.01216(17) 0.0519(9) Uani 1 1 d . . . H23A H 0.3517 0.5361 0.0259 0.062 Uiso 1 1 calc R . . C11 C -0.0466(3) 0.1858(5) 0.05561(17) 0.0597(10) Uani 1 1 d . . . H11B H -0.0656 0.0667 0.0410 0.072 Uiso 1 1 calc R . . C9 C -0.0942(3) 0.5005(5) 0.08211(19) 0.0610(10) Uani 1 1 d . . . H9A H -0.1453 0.5905 0.0841 0.073 Uiso 1 1 calc R . . C4 C 0.6212(3) 0.5141(5) 0.26352(18) 0.0623(10) Uani 1 1 d . . . H4A H 0.6586 0.6035 0.2897 0.075 Uiso 1 1 calc R . . C1 C 0.5128(2) 0.2435(4) 0.18473(17) 0.0515(9) Uani 1 1 d . . . H1A H 0.4779 0.1511 0.1586 0.062 Uiso 1 1 calc R . . C2 C 0.6102(3) 0.2112(5) 0.2136(2) 0.0661(11) Uani 1 1 d . . . H2A H 0.6416 0.0978 0.2059 0.079 Uiso 1 1 calc R . . C10 C -0.1215(3) 0.3301(5) 0.05999(19) 0.0636(11) Uani 1 1 d . . . H10B H -0.1907 0.3050 0.0472 0.076 Uiso 1 1 calc R . . C24 C 0.3873(3) 0.3669(6) -0.05226(18) 0.0654(11) Uani 1 1 d . . . H24B H 0.4081 0.4595 -0.0819 0.079 Uiso 1 1 calc R . . C27 C 0.3226(3) 0.0957(5) 0.03513(19) 0.0659(11) Uani 1 1 d . . . H27B H 0.3004 0.0029 0.0642 0.079 Uiso 1 1 calc R . . C3 C 0.6634(3) 0.3436(5) 0.2542(2) 0.0677(11) Uani 1 1 d . . . H3A H 0.7285 0.3160 0.2752 0.081 Uiso 1 1 calc R . . C25 C 0.3904(3) 0.1840(6) -0.0717(2) 0.0723(12) Uani 1 1 d . . . H25B H 0.4151 0.1525 -0.1144 0.087 Uiso 1 1 calc R . . C26 C 0.3578(3) 0.0477(6) -0.0293(2) 0.0848(14) Uani 1 1 d . . . H26B H 0.3589 -0.0760 -0.0432 0.102 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 C15' 0.048(2) 0.055(2) 0.0297(18) -0.0064(15) 0.0072(16) -0.0013(17) C19' 0.051(2) 0.055(2) 0.038(2) 0.0050(16) 0.0119(17) 0.0123(18) C17' 0.053(2) 0.040(2) 0.039(2) -0.0030(15) 0.0113(17) -0.0076(16) C18' 0.057(2) 0.046(2) 0.0336(19) 0.0014(15) 0.0088(17) 0.0039(17) C21' 0.049(2) 0.046(2) 0.0305(18) -0.0009(14) 0.0041(16) 0.0033(16) C20' 0.043(2) 0.052(2) 0.0360(19) 0.0034(15) 0.0078(16) 0.0055(16) C13' 0.0388(19) 0.0391(18) 0.0388(19) -0.0002(14) 0.0032(15) -0.0002(14) C16' 0.055(2) 0.048(2) 0.045(2) -0.0112(16) 0.0133(18) -0.0069(17) C14' 0.048(2) 0.050(2) 0.0318(18) -0.0065(15) 0.0096(16) -0.0005(16) C23' 0.0341(19) 0.057(2) 0.0392(19) 0.0055(16) 0.0006(15) 0.0029(15) C8' 0.064(3) 0.057(2) 0.041(2) 0.0101(17) 0.0081(19) 0.015(2) C7' 0.071(3) 0.048(2) 0.045(2) 0.0008(16) 0.012(2) 0.0037(19) C24' 0.052(2) 0.058(2) 0.044(2) 0.0055(17) 0.0082(18) 0.0047(17) C1' 0.050(2) 0.064(2) 0.044(2) -0.0067(17) 0.0045(18) 0.0017(18) C6' 0.070(3) 0.051(2) 0.047(2) -0.0051(17) 0.015(2) -0.0032(19) C5' 0.058(3) 0.062(2) 0.051(2) -0.0134(18) 0.011(2) -0.0138(19) C12' 0.042(2) 0.083(3) 0.056(2) 0.009(2) 0.0030(19) 0.020(2) C2' 0.059(3) 0.070(3) 0.052(2) -0.0039(18) -0.001(2) 0.007(2) C11' 0.045(2) 0.061(2) 0.055(2) 0.0077(18) -0.0017(19) 0.0064(18) C9' 0.045(2) 0.076(3) 0.085(3) 0.009(2) -0.006(2) -0.002(2) C4' 0.052(3) 0.074(3) 0.061(3) -0.013(2) 0.004(2) -0.012(2) C3' 0.049(2) 0.078(3) 0.065(3) -0.012(2) -0.001(2) -0.006(2) C25' 0.058(3) 0.100(3) 0.040(2) -0.005(2) 0.0075(19) 0.016(2) C22' 0.075(3) 0.051(2) 0.064(3) 0.0122(19) 0.020(2) 0.0041(19) C10' 0.044(2) 0.080(3) 0.085(3) 0.019(2) -0.001(2) 0.005(2) C27' 0.092(3) 0.078(3) 0.073(3) 0.030(2) 0.025(3) 0.012(2) C26' 0.069(3) 0.098(3) 0.053(3) 0.024(2) 0.015(2) 0.011(2) C20 0.049(2) 0.0421(19) 0.0337(18) 0.0042(14) 0.0049(16) 0.0055(16) C17 0.057(2) 0.047(2) 0.0287(18) -0.0018(14) 0.0080(17) -0.0021(17) C18 0.058(2) 0.042(2) 0.0351(19) 0.0048(14) 0.0113(17) 0.0109(16) C16 0.048(2) 0.055(2) 0.039(2) -0.0061(16) 0.0101(17) -0.0080(17) C15 0.045(2) 0.055(2) 0.0356(19) -0.0020(15) 0.0073(16) 0.0004(17) C21 0.046(2) 0.0370(18) 0.0351(18) 0.0030(14) 0.0070(16) 0.0050(15) C14 0.049(2) 0.048(2) 0.0300(18) -0.0028(14) 0.0049(16) 0.0020(16) C19 0.050(2) 0.060(2) 0.039(2) 0.0109(16) 0.0090(17) 0.0132(18) C13 0.042(2) 0.0404(18) 0.0344(18) 0.0001(14) 0.0052(15) 0.0033(15) C22 0.0342(19) 0.0443(19) 0.0401(19) -0.0035(15) 0.0023(15) 0.0013(14) C8 0.068(3) 0.048(2) 0.057(2) 0.0080(18) 0.016(2) 0.0174(19) C12 0.049(2) 0.067(2) 0.043(2) 0.0074(17) 0.0023(18) 0.0115(19) C5 0.069(3) 0.062(2) 0.041(2) -0.0098(17) 0.010(2) -0.011(2) C6 0.071(3) 0.054(2) 0.042(2) -0.0040(17) 0.011(2) 0.0074(19) C7 0.066(3) 0.041(2) 0.046(2) -0.0007(15) 0.0098(19) 0.0062(18) C23 0.049(2) 0.063(2) 0.044(2) -0.0036(17) 0.0002(18) 0.0039(17) C11 0.056(3) 0.074(3) 0.049(2) 0.0051(18) -0.0025(19) 0.006(2) C9 0.054(3) 0.068(3) 0.062(3) 0.013(2) 0.008(2) 0.016(2) C4 0.048(2) 0.086(3) 0.053(2) -0.011(2) 0.004(2) -0.015(2) C1 0.041(2) 0.056(2) 0.056(2) -0.0077(17) 0.0011(18) 0.0005(17) C2 0.043(2) 0.074(3) 0.080(3) -0.017(2) -0.002(2) 0.0043(19) C10 0.048(2) 0.080(3) 0.062(3) 0.012(2) -0.001(2) 0.011(2) C24 0.058(3) 0.098(3) 0.041(2) 0.002(2) 0.008(2) 0.000(2) C27 0.075(3) 0.067(3) 0.058(2) -0.011(2) 0.021(2) 0.003(2) C3 0.037(2) 0.082(3) 0.083(3) -0.018(2) -0.003(2) 0.000(2) C25 0.070(3) 0.098(3) 0.051(3) -0.022(2) 0.020(2) -0.008(2) C26 0.087(3) 0.096(3) 0.074(3) -0.037(3) 0.022(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C15' C1' 1.405(4) . ? C15' C16' 1.420(4) . ? C15' C14' 1.429(4) . ? C19' C8' 1.379(4) . ? C19' C12' 1.422(5) . ? C19' C20' 1.438(4) . ? C17' C14' 1.360(4) . ? C17' C6' 1.414(4) . ? C17' C18' 1.475(4) . ? C18' C21' 1.375(4) . ? C18' C7' 1.407(4) . ? C21' C20' 1.425(4) . ? C21' C13' 1.534(4) . ? C20' C11' 1.384(4) . ? C13' C14' 1.526(4) . ? C13' C23' 1.530(4) . ? C13' H13A 0.9800 . ? C16' C5' 1.406(4) . ? C16' C4' 1.426(5) . ? C23' C22' 1.372(4) . ? C23' C24' 1.386(4) . ? C8' C7' 1.385(4) . ? C8' H8'A 0.9300 . ? C7' H7'A 0.9300 . ? C24' C25' 1.386(4) . ? C24' H24A 0.9300 . ? C1' C2' 1.380(4) . ? C1' H1'A 0.9300 . ? C6' C5' 1.358(5) . ? C6' H6'A 0.9300 . ? C5' H5'A 0.9300 . ? C12' C10' 1.358(5) . ? C12' H12A 0.9300 . ? C2' C3' 1.408(5) . ? C2' H2'A 0.9300 . ? C11' C9' 1.374(4) . ? C11' H11A 0.9300 . ? C9' C10' 1.408(5) . ? C9' H9'A 0.9300 . ? C4' C3' 1.343(4) . ? C4' H4'A 0.9300 . ? C3' H3'A 0.9300 . ? C25' C26' 1.364(5) . ? C25' H25A 0.9300 . ? C22' C27' 1.390(5) . ? C22' H22A 0.9300 . ? C10' H10A 0.9300 . ? C27' C26' 1.365(5) . ? C27' H27A 0.9300 . ? C26' H26A 0.9300 . ? C20 C21 1.391(4) . ? C20 C12 1.408(4) . ? C20 C19 1.435(4) . ? C17 C14 1.389(4) . ? C17 C6 1.395(4) . ? C17 C18 1.470(4) . ? C18 C21 1.375(4) . ? C18 C7 1.411(4) . ? C16 C4 1.415(5) . ? C16 C5 1.415(4) . ? C16 C15 1.436(4) . ? C15 C1 1.396(4) . ? C15 C14 1.421(4) . ? C21 C13 1.532(4) . ? C14 C13 1.515(4) . ? C19 C8 1.389(4) . ? C19 C9 1.427(5) . ? C13 C22 1.527(4) . ? C13 H13B 0.9800 . ? C22 C27 1.364(4) . ? C22 C23 1.383(4) . ? C8 C7 1.346(5) . ? C8 H8A 0.9300 . ? C12 C11 1.384(4) . ? C12 H12B 0.9300 . ? C5 C6 1.363(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C23 C24 1.386(4) . ? C23 H23A 0.9300 . ? C11 C10 1.430(4) . ? C11 H11B 0.9300 . ? C9 C10 1.338(4) . ? C9 H9A 0.9300 . ? C4 C3 1.362(4) . ? C4 H4A 0.9300 . ? C1 C2 1.361(4) . ? C1 H1A 0.9300 . ? C2 C3 1.382(5) . ? C2 H2A 0.9300 . ? C10 H10B 0.9300 . ? C24 C25 1.371(4) . ? C24 H24B 0.9300 . ? C27 C26 1.394(5) . ? C27 H27B 0.9300 . ? C3 H3A 0.9300 . ? C25 C26 1.364(5) . ? C25 H25B 0.9300 . ? C26 H26B 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 C1' C15' C16' 119.5(3) . . ? C1' C15' C14' 123.8(3) . . ? C16' C15' C14' 116.5(3) . . ? C8' C19' C12' 122.0(3) . . ? C8' C19' C20' 121.2(3) . . ? C12' C19' C20' 116.7(3) . . ? C14' C17' C6' 122.0(3) . . ? C14' C17' C18' 108.9(3) . . ? C6' C17' C18' 129.0(3) . . ? C21' C18' C7' 121.3(3) . . ? C21' C18' C17' 108.9(3) . . ? C7' C18' C17' 129.8(3) . . ? C18' C21' C20' 122.0(3) . . ? C18' C21' C13' 110.1(3) . . ? C20' C21' C13' 127.9(3) . . ? C11' C20' C21' 124.7(3) . . ? C11' C20' C19' 119.7(3) . . ? C21' C20' C19' 115.6(3) . . ? C14' C13' C23' 113.6(3) . . ? C14' C13' C21' 100.9(2) . . ? C23' C13' C21' 111.9(2) . . ? C14' C13' H13A 110.0 . . ? C23' C13' H13A 110.0 . . ? C21' C13' H13A 110.0 . . ? C5' C16' C15' 120.3(3) . . ? C5' C16' C4' 121.3(3) . . ? C15' C16' C4' 118.5(3) . . ? C17' C14' C15' 121.2(3) . . ? C17' C14' C13' 111.0(3) . . ? C15' C14' C13' 127.7(3) . . ? C22' C23' C24' 119.3(3) . . ? C22' C23' C13' 121.5(3) . . ? C24' C23' C13' 119.2(3) . . ? C19' C8' C7' 122.1(3) . . ? C19' C8' H8'A 119.0 . . ? C7' C8' H8'A 119.0 . . ? C8' C7' C18' 117.9(3) . . ? C8' C7' H7'A 121.1 . . ? C18' C7' H7'A 121.1 . . ? C25' C24' C23' 119.6(3) . . ? C25' C24' H24A 120.2 . . ? C23' C24' H24A 120.2 . . ? C2' C1' C15' 119.9(3) . . ? C2' C1' H1'A 120.0 . . ? C15' C1' H1'A 120.0 . . ? C5' C6' C17' 117.7(3) . . ? C5' C6' H6'A 121.1 . . ? C17' C6' H6'A 121.1 . . ? C6' C5' C16' 122.3(3) . . ? C6' C5' H5'A 118.9 . . ? C16' C5' H5'A 118.9 . . ? C10' C12' C19' 122.0(3) . . ? C10' C12' H12A 119.0 . . ? C19' C12' H12A 119.0 . . ? C1' C2' C3' 120.5(4) . . ? C1' C2' H2'A 119.7 . . ? C3' C2' H2'A 119.7 . . ? C9' C11' C20' 121.9(3) . . ? C9' C11' H11A 119.1 . . ? C20' C11' H11A 119.1 . . ? C11' C9' C10' 119.1(4) . . ? C11' C9' H9'A 120.4 . . ? C10' C9' H9'A 120.4 . . ? C3' C4' C16' 121.0(3) . . ? C3' C4' H4'A 119.5 . . ? C16' C4' H4'A 119.5 . . ? C4' C3' C2' 120.6(4) . . ? C4' C3' H3'A 119.7 . . ? C2' C3' H3'A 119.7 . . ? C26' C25' C24' 120.8(3) . . ? C26' C25' H25A 119.6 . . ? C24' C25' H25A 119.6 . . ? C23' C22' C27' 120.4(3) . . ? C23' C22' H22A 119.8 . . ? C27' C22' H22A 119.8 . . ? C12' C10' C9' 120.4(4) . . ? C12' C10' H10A 119.8 . . ? C9' C10' H10A 119.8 . . ? C26' C27' C22' 120.1(4) . . ? C26' C27' H27A 120.0 . . ? C22' C27' H27A 120.0 . . ? C25' C26' C27' 119.8(4) . . ? C25' C26' H26A 120.1 . . ? C27' C26' H26A 120.1 . . ? C21 C20 C12 125.0(3) . . ? C21 C20 C19 116.6(3) . . ? C12 C20 C19 118.4(3) . . ? C14 C17 C6 121.1(3) . . ? C14 C17 C18 108.1(3) . . ? C6 C17 C18 130.7(3) . . ? C21 C18 C7 120.9(3) . . ? C21 C18 C17 109.8(3) . . ? C7 C18 C17 129.1(3) . . ? C4 C16 C5 121.7(3) . . ? C4 C16 C15 118.3(3) . . ? C5 C16 C15 120.0(3) . . ? C1 C15 C14 123.7(3) . . ? C1 C15 C16 119.0(3) . . ? C14 C15 C16 117.3(3) . . ? C18 C21 C20 121.6(3) . . ? C18 C21 C13 109.5(3) . . ? C20 C21 C13 128.8(3) . . ? C17 C14 C15 120.7(3) . . ? C17 C14 C13 110.5(3) . . ? C15 C14 C13 128.9(3) . . ? C8 C19 C9 122.5(3) . . ? C8 C19 C20 120.3(3) . . ? C9 C19 C20 117.2(3) . . ? C14 C13 C22 112.5(2) . . ? C14 C13 C21 102.0(2) . . ? C22 C13 C21 113.5(2) . . ? C14 C13 H13B 109.5 . . ? C22 C13 H13B 109.5 . . ? C21 C13 H13B 109.5 . . ? C27 C22 C23 118.5(3) . . ? C27 C22 C13 122.4(3) . . ? C23 C22 C13 119.1(3) . . ? C7 C8 C19 122.1(3) . . ? C7 C8 H8A 119.0 . . ? C19 C8 H8A 119.0 . . ? C11 C12 C20 123.3(3) . . ? C11 C12 H12B 118.3 . . ? C20 C12 H12B 118.3 . . ? C6 C5 C16 120.9(3) . . ? C6 C5 H5A 119.5 . . ? C16 C5 H5A 119.5 . . ? C5 C6 C17 120.0(3) . . ? C5 C6 H6A 120.0 . . ? C17 C6 H6A 120.0 . . ? C8 C7 C18 118.5(3) . . ? C8 C7 H7A 120.8 . . ? C18 C7 H7A 120.8 . . ? C22 C23 C24 121.0(3) . . ? C22 C23 H23A 119.5 . . ? C24 C23 H23A 119.5 . . ? C12 C11 C10 117.0(3) . . ? C12 C11 H11B 121.5 . . ? C10 C11 H11B 121.5 . . ? C10 C9 C19 122.7(3) . . ? C10 C9 H9A 118.7 . . ? C19 C9 H9A 118.7 . . ? C3 C4 C16 120.4(3) . . ? C3 C4 H4A 119.8 . . ? C16 C4 H4A 119.8 . . ? C2 C1 C15 120.4(3) . . ? C2 C1 H1A 119.8 . . ? C15 C1 H1A 119.8 . . ? C1 C2 C3 121.4(3) . . ? C1 C2 H2A 119.3 . . ? C3 C2 H2A 119.3 . . ? C9 C10 C11 121.4(4) . . ? C9 C10 H10B 119.3 . . ? C11 C10 H10B 119.3 . . ? C25 C24 C23 119.2(3) . . ? C25 C24 H24B 120.4 . . ? C23 C24 H24B 120.4 . . ? C22 C27 C26 121.2(4) . . ? C22 C27 H27B 119.4 . . ? C26 C27 H27B 119.4 . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C26 C25 C24 120.8(3) . . ? C26 C25 H25B 119.6 . . ? C24 C25 H25B 119.6 . . ? C25 C26 C27 119.3(4) . . ? C25 C26 H26B 120.4 . . ? C27 C26 H26B 120.4 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.222 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.061 data_01 _database_code_depnum_ccdc_archive 'CCDC 727726' #TrackingRef '201-CIF-2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 O3' _chemical_formula_sum 'C22 H20 O3' _chemical_formula_weight 332.38 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 15.412(2) _cell_length_b 5.8149(9) _cell_length_c 19.488(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.633(2) _cell_angle_gamma 90.00 _cell_volume 1734.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2026 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 23.17 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details SADABS;Bruker,2000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8982 _diffrn_reflns_av_R_equivalents 0.1022 _diffrn_reflns_av_sigmaI/netI 0.0795 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3388 _reflns_number_gt 2108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0213P)^2^+0.0230P] 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 SHELXL _refine_ls_extinction_coef 0.0066(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3388 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 O2 O 0.05541(8) 0.4720(2) 0.43440(6) 0.0591(4) Uani 1 1 d . . . C19 C 0.22121(11) 0.4194(3) 0.17065(8) 0.0439(4) Uani 1 1 d . . . C8 C 0.16196(10) 0.4062(3) 0.27674(8) 0.0425(4) Uani 1 1 d . . . C14 C 0.16549(11) 0.6082(3) 0.17419(8) 0.0437(4) Uani 1 1 d . . . C7 C 0.22091(10) 0.2698(3) 0.23478(8) 0.0438(4) Uani 1 1 d . . . H7 H 0.1912 0.1254 0.2208 0.053 Uiso 1 1 calc R . . C13 C 0.12989(10) 0.6016(3) 0.24064(8) 0.0431(4) Uani 1 1 d . . . C3 C 0.31054(11) 0.2107(3) 0.27149(8) 0.0439(4) Uani 1 1 d . . . C10 C 0.08299(11) 0.5044(3) 0.37070(9) 0.0467(5) Uani 1 1 d . . . C9 C 0.13867(11) 0.3547(3) 0.34161(8) 0.0473(5) Uani 1 1 d . . . H9 H 0.1598 0.2232 0.3651 0.057 Uiso 1 1 calc R . . C11 C 0.05092(11) 0.6996(3) 0.33551(9) 0.0497(5) Uani 1 1 d . . . H11 H 0.0135 0.7977 0.3557 0.060 Uiso 1 1 calc R . . O3 O 0.29859(9) 0.4902(3) 0.00476(6) 0.0717(4) Uani 1 1 d . . . C18 C 0.26539(12) 0.3848(3) 0.11419(9) 0.0520(5) Uani 1 1 d . . . H18 H 0.3027 0.2598 0.1125 0.062 Uiso 1 1 calc R . . C15 C 0.15339(11) 0.7596(3) 0.11919(9) 0.0526(5) Uani 1 1 d . . . H15 H 0.1159 0.8845 0.1207 0.063 Uiso 1 1 calc R . . C12 C 0.07416(11) 0.7494(3) 0.27082(9) 0.0485(5) Uani 1 1 d . . . H12 H 0.0527 0.8809 0.2475 0.058 Uiso 1 1 calc R . . C2 C 0.35392(11) 0.3633(3) 0.31747(9) 0.0497(5) Uani 1 1 d . . . H2 H 0.3281 0.5033 0.3261 0.060 Uiso 1 1 calc R . . O1 O 0.47230(9) 0.4759(3) 0.39565(7) 0.0793(5) Uani 1 1 d . . . C1 C 0.43622(12) 0.3099(4) 0.35121(9) 0.0556(5) Uani 1 1 d . . . C17 C 0.25317(12) 0.5409(3) 0.05940(9) 0.0523(5) Uani 1 1 d . . . C5 C 0.43193(13) -0.0474(4) 0.29212(10) 0.0634(6) Uani 1 1 d . . . H5 H 0.4582 -0.1866 0.2832 0.076 Uiso 1 1 calc R . . C4 C 0.35003(13) 0.0040(3) 0.25849(9) 0.0548(5) Uani 1 1 d . . . H4 H 0.3217 -0.1000 0.2273 0.066 Uiso 1 1 calc R . . C6 C 0.47500(13) 0.1037(4) 0.33838(10) 0.0624(6) Uani 1 1 d . . . H6 H 0.5298 0.0669 0.3608 0.075 Uiso 1 1 calc R . . C16 C 0.19730(12) 0.7245(3) 0.06183(9) 0.0569(5) Uani 1 1 d . . . H16 H 0.1889 0.8259 0.0247 0.068 Uiso 1 1 calc R . . C22 C 0.28794(14) 0.6397(4) -0.05400(10) 0.0773(7) Uani 1 1 d . . . H22A H 0.2275 0.6436 -0.0726 0.116 Uiso 1 1 calc R . . H22B H 0.3224 0.5839 -0.0885 0.116 Uiso 1 1 calc R . . H22C H 0.3068 0.7919 -0.0402 0.116 Uiso 1 1 calc R . . C21 C 0.07950(14) 0.2656(4) 0.46993(10) 0.0730(6) Uani 1 1 d . . . H21A H 0.0567 0.1368 0.4427 0.110 Uiso 1 1 calc R . . H21B H 0.0561 0.2648 0.5135 0.110 Uiso 1 1 calc R . . H21C H 0.1420 0.2550 0.4777 0.110 Uiso 1 1 calc R . . C20 C 0.55693(14) 0.4329(5) 0.43030(13) 0.0989(9) Uani 1 1 d . . . H20A H 0.5553 0.2981 0.4586 0.148 Uiso 1 1 calc R . . H20B H 0.5755 0.5624 0.4589 0.148 Uiso 1 1 calc R . . H20C H 0.5972 0.4092 0.3969 0.148 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 O2 0.0581(8) 0.0747(9) 0.0464(8) -0.0027(7) 0.0142(6) 0.0098(7) C19 0.0400(10) 0.0501(11) 0.0402(10) -0.0025(8) -0.0009(8) -0.0011(8) C8 0.0358(9) 0.0466(10) 0.0443(10) -0.0038(8) 0.0014(8) 0.0001(8) C14 0.0375(9) 0.0485(11) 0.0436(10) -0.0010(8) -0.0022(8) -0.0010(8) C7 0.0438(10) 0.0430(10) 0.0443(10) -0.0010(8) 0.0042(8) 0.0017(8) C13 0.0359(9) 0.0463(11) 0.0457(10) -0.0027(8) -0.0013(8) -0.0017(8) C3 0.0464(10) 0.0460(11) 0.0405(10) 0.0052(8) 0.0099(8) 0.0045(9) C10 0.0374(10) 0.0603(12) 0.0420(10) -0.0073(9) 0.0025(8) -0.0017(9) C9 0.0420(10) 0.0538(11) 0.0455(11) 0.0003(9) 0.0030(8) 0.0044(9) C11 0.0416(10) 0.0526(12) 0.0544(12) -0.0097(9) 0.0035(9) 0.0038(9) O3 0.0750(10) 0.0951(11) 0.0473(8) 0.0090(7) 0.0169(7) 0.0093(8) C18 0.0493(11) 0.0606(12) 0.0457(11) 0.0010(9) 0.0038(9) 0.0079(9) C15 0.0478(11) 0.0561(12) 0.0519(11) 0.0023(9) -0.0032(9) 0.0045(9) C12 0.0418(10) 0.0483(11) 0.0537(11) 0.0004(9) -0.0012(8) 0.0037(9) C2 0.0475(11) 0.0522(11) 0.0493(11) 0.0022(9) 0.0047(8) 0.0088(9) O1 0.0619(9) 0.0934(11) 0.0762(10) -0.0058(8) -0.0198(8) 0.0022(8) C1 0.0495(11) 0.0672(14) 0.0491(11) 0.0080(10) 0.0020(9) 0.0013(10) C17 0.0472(11) 0.0688(13) 0.0401(11) -0.0014(9) 0.0019(9) -0.0035(10) C5 0.0628(13) 0.0600(14) 0.0705(14) 0.0097(11) 0.0209(11) 0.0216(11) C4 0.0591(12) 0.0531(12) 0.0533(12) 0.0019(9) 0.0116(9) 0.0093(10) C6 0.0481(11) 0.0754(15) 0.0637(13) 0.0178(11) 0.0065(10) 0.0140(11) C16 0.0574(12) 0.0686(14) 0.0429(11) 0.0096(9) -0.0024(9) -0.0004(11) C22 0.0828(16) 0.1033(18) 0.0460(12) 0.0132(11) 0.0087(11) -0.0033(14) C21 0.0924(16) 0.0772(16) 0.0528(12) 0.0068(11) 0.0222(11) 0.0158(13) C20 0.0553(15) 0.147(2) 0.0882(17) -0.0005(17) -0.0178(13) -0.0066(15) _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 O2 C10 1.371(2) . ? O2 C21 1.414(2) . ? C19 C18 1.374(2) . ? C19 C14 1.400(2) . ? C19 C7 1.523(2) . ? C8 C9 1.386(2) . ? C8 C13 1.397(2) . ? C8 C7 1.515(2) . ? C14 C15 1.383(2) . ? C14 C13 1.464(2) . ? C7 C3 1.520(2) . ? C7 H7 0.9800 . ? C13 C12 1.393(2) . ? C3 C2 1.378(2) . ? C3 C4 1.384(2) . ? C10 C11 1.387(2) . ? C10 C9 1.388(2) . ? C9 H9 0.9300 . ? C11 C12 1.380(2) . ? C11 H11 0.9300 . ? O3 C17 1.372(2) . ? O3 C22 1.432(2) . ? C18 C17 1.398(2) . ? C18 H18 0.9300 . ? C15 C16 1.387(3) . ? C15 H15 0.9300 . ? C12 H12 0.9300 . ? C2 C1 1.395(2) . ? C2 H2 0.9300 . ? O1 C1 1.371(2) . ? O1 C20 1.420(2) . ? C1 C6 1.376(3) . ? C17 C16 1.376(3) . ? C5 C6 1.374(3) . ? C5 C4 1.386(2) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C6 H6 0.9300 . ? C16 H16 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C10 O2 C21 117.96(14) . . ? C18 C19 C14 121.18(16) . . ? C18 C19 C7 128.46(16) . . ? C14 C19 C7 110.33(15) . . ? C9 C8 C13 121.42(16) . . ? C9 C8 C7 127.87(15) . . ? C13 C8 C7 110.71(15) . . ? C15 C14 C19 119.30(17) . . ? C15 C14 C13 132.17(16) . . ? C19 C14 C13 108.52(14) . . ? C8 C7 C3 115.69(14) . . ? C8 C7 C19 101.69(14) . . ? C3 C7 C19 115.24(14) . . ? C8 C7 H7 107.9 . . ? C3 C7 H7 107.9 . . ? C19 C7 H7 107.9 . . ? C12 C13 C8 119.28(16) . . ? C12 C13 C14 132.07(16) . . ? C8 C13 C14 108.65(15) . . ? C2 C3 C4 119.20(16) . . ? C2 C3 C7 120.46(15) . . ? C4 C3 C7 120.34(16) . . ? O2 C10 C11 115.46(16) . . ? O2 C10 C9 123.68(16) . . ? C11 C10 C9 120.86(16) . . ? C8 C9 C10 118.32(16) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C12 C11 C10 120.52(17) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C17 O3 C22 117.92(16) . . ? C19 C18 C17 118.76(17) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C14 C15 C16 119.76(17) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C12 C13 119.60(16) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C3 C2 C1 120.63(17) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C1 O1 C20 117.37(17) . . ? O1 C1 C6 125.14(17) . . ? O1 C1 C2 114.92(17) . . ? C6 C1 C2 119.94(19) . . ? O3 C17 C16 124.81(17) . . ? O3 C17 C18 114.68(17) . . ? C16 C17 C18 120.49(17) . . ? C6 C5 C4 121.12(18) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C4 C3 119.78(18) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C5 C6 C1 119.32(18) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C17 C16 C15 120.48(17) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O1 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.175 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.042 data_qqq _database_code_depnum_ccdc_archive 'CCDC 727727' #TrackingRef '202-CIF-2e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H20 O2' _chemical_formula_sum 'C25 H20 O2' _chemical_formula_weight 352.43 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)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.533(2) _cell_length_b 6.5954(13) _cell_length_c 26.832(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.565(3) _cell_angle_gamma 90.00 _cell_volume 1847.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2851 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 26.04 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details SADABS;Bruker,2000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11008 _diffrn_reflns_av_R_equivalents 0.1243 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.19 _reflns_number_total 4384 _reflns_number_gt 2556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0450P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4384 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _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 0.58106(12) 0.6501(2) 0.16728(5) 0.0437(3) Uani 1 1 d . . . H1A H 0.6211 0.7727 0.1829 0.052 Uiso 1 1 calc R . . C2 C 0.47592(14) 0.5345(2) 0.24650(5) 0.0509(4) Uani 1 1 d . . . C3 C 0.47328(13) 0.8895(2) 0.10277(5) 0.0464(3) Uani 1 1 d . . . H3A H 0.5430 0.9758 0.1103 0.056 Uiso 1 1 calc R . . O1 O 0.37643(12) 1.10914(19) 0.03550(4) 0.0772(4) Uani 1 1 d . . . C4 C 0.46648(13) 0.7109(2) 0.12959(5) 0.0429(3) Uani 1 1 d . . . C5 C 0.68018(13) 0.5331(2) 0.14229(5) 0.0473(4) Uani 1 1 d . . . C6 C 0.36073(13) 0.5859(2) 0.11921(5) 0.0517(4) Uani 1 1 d . . . H6A H 0.3551 0.4669 0.1374 0.062 Uiso 1 1 calc R . . C7 C 0.55472(13) 0.5038(2) 0.20836(5) 0.0469(3) Uani 1 1 d . . . C8 C 0.37592(14) 0.9394(2) 0.06461(5) 0.0540(4) Uani 1 1 d . . . C9 C 0.70365(14) 0.3458(2) 0.16520(6) 0.0526(4) Uani 1 1 d . . . C10 C 0.62584(14) 0.3293(2) 0.20645(5) 0.0524(4) Uani 1 1 d . . . C11 C 0.47166(15) 0.3758(3) 0.28273(6) 0.0592(4) Uani 1 1 d . . . C12 C 0.74437(13) 0.5952(2) 0.10316(6) 0.0541(4) Uani 1 1 d . . . H12A H 0.7270 0.7201 0.0877 0.065 Uiso 1 1 calc R . . C13 C 0.40338(15) 0.7112(2) 0.25110(6) 0.0569(4) Uani 1 1 d . . . H13A H 0.4054 0.8153 0.2278 0.068 Uiso 1 1 calc R . . O2 O 0.90896(11) 0.5097(2) 0.05054(5) 0.0823(4) Uani 1 1 d . . . C14 C 0.27132(15) 0.8137(3) 0.05421(6) 0.0625(4) Uani 1 1 d . . . H14A H 0.2062 0.8472 0.0287 0.075 Uiso 1 1 calc R . . C15 C 0.83572(15) 0.4652(3) 0.08759(6) 0.0622(4) Uani 1 1 d . . . C16 C 0.26298(14) 0.6392(3) 0.08145(6) 0.0619(4) Uani 1 1 d . . . H16A H 0.1915 0.5561 0.0746 0.074 Uiso 1 1 calc R . . C17 C 0.33010(16) 0.7321(3) 0.28920(6) 0.0696(5) Uani 1 1 d . . . H17A H 0.2830 0.8501 0.2916 0.084 Uiso 1 1 calc R . . C18 C 0.85871(17) 0.2776(3) 0.11024(7) 0.0724(5) Uani 1 1 d . . . H18A H 0.9192 0.1918 0.0991 0.087 Uiso 1 1 calc R . . C19 C 0.62070(17) 0.1738(2) 0.24217(7) 0.0662(5) Uani 1 1 d . . . H19A H 0.6683 0.0558 0.2405 0.079 Uiso 1 1 calc R . . C20 C 0.39389(19) 0.4052(3) 0.32134(6) 0.0754(6) Uani 1 1 d . . . H20A H 0.3898 0.3035 0.3451 0.091 Uiso 1 1 calc R . . C21 C 0.79343(16) 0.2153(3) 0.14911(7) 0.0660(5) Uani 1 1 d . . . H21A H 0.8093 0.0891 0.1641 0.079 Uiso 1 1 calc R . . C22 C 0.54514(18) 0.1988(3) 0.27905(7) 0.0677(5) Uani 1 1 d . . . H22A H 0.5417 0.0961 0.3026 0.081 Uiso 1 1 calc R . . C23 C 0.32553(18) 0.5768(4) 0.32466(7) 0.0784(6) Uani 1 1 d . . . H23A H 0.2754 0.5920 0.3505 0.094 Uiso 1 1 calc R . . C24 C 0.4871(2) 1.2333(3) 0.04099(6) 0.0760(5) Uani 1 1 d . . . H24A H 0.4757 1.3421 0.0171 0.114 Uiso 1 1 calc R . . H24B H 0.5601 1.1538 0.0352 0.114 Uiso 1 1 calc R . . H24C H 0.5006 1.2881 0.0744 0.114 Uiso 1 1 calc R . . C25 C 0.89794(19) 0.7057(3) 0.02916(8) 0.0858(6) Uani 1 1 d . . . H25A H 0.9562 0.7186 0.0047 0.129 Uiso 1 1 calc R . . H25B H 0.9183 0.8053 0.0551 0.129 Uiso 1 1 calc R . . H25C H 0.8119 0.7264 0.0132 0.129 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 C1 0.0358(7) 0.0471(8) 0.0478(8) -0.0011(6) 0.0037(6) 0.0016(6) C2 0.0411(8) 0.0624(9) 0.0471(8) 0.0044(7) -0.0021(6) -0.0108(7) C3 0.0380(7) 0.0520(9) 0.0490(8) -0.0012(7) 0.0053(6) 0.0041(6) O1 0.0763(9) 0.0788(8) 0.0710(8) 0.0214(6) -0.0103(6) 0.0055(7) C4 0.0342(7) 0.0529(8) 0.0425(7) -0.0036(6) 0.0086(5) 0.0059(6) C5 0.0339(7) 0.0537(9) 0.0522(8) -0.0037(7) -0.0021(6) 0.0055(6) C6 0.0417(8) 0.0633(10) 0.0509(8) -0.0005(7) 0.0093(6) -0.0017(7) C7 0.0388(7) 0.0512(8) 0.0485(8) 0.0019(7) -0.0027(6) -0.0024(7) C8 0.0494(9) 0.0650(10) 0.0475(8) 0.0046(7) 0.0058(7) 0.0098(7) C9 0.0425(8) 0.0537(9) 0.0575(9) -0.0076(7) -0.0090(7) 0.0054(7) C10 0.0482(8) 0.0493(9) 0.0553(9) 0.0000(7) -0.0095(7) -0.0007(7) C11 0.0522(9) 0.0690(11) 0.0527(9) 0.0112(8) -0.0071(7) -0.0190(8) C12 0.0381(8) 0.0662(10) 0.0571(9) -0.0042(8) 0.0029(7) 0.0105(7) C13 0.0472(9) 0.0718(11) 0.0519(9) 0.0054(8) 0.0067(7) -0.0010(8) O2 0.0603(8) 0.1126(11) 0.0778(8) -0.0062(8) 0.0236(6) 0.0267(8) C14 0.0436(9) 0.0883(12) 0.0528(9) 0.0013(9) -0.0040(7) 0.0057(8) C15 0.0434(9) 0.0837(12) 0.0587(9) -0.0130(9) 0.0042(7) 0.0119(8) C16 0.0381(8) 0.0864(12) 0.0602(9) -0.0091(9) 0.0031(7) -0.0063(8) C17 0.0525(10) 0.0978(13) 0.0603(10) 0.0002(9) 0.0138(8) 0.0022(9) C18 0.0556(10) 0.0823(13) 0.0760(11) -0.0205(10) -0.0033(9) 0.0276(9) C19 0.0706(11) 0.0514(9) 0.0695(11) 0.0047(8) -0.0167(9) -0.0014(8) C20 0.0667(12) 0.1050(15) 0.0529(10) 0.0177(10) 0.0014(9) -0.0306(12) C21 0.0605(11) 0.0597(10) 0.0728(11) -0.0077(9) -0.0098(9) 0.0173(8) C22 0.0738(12) 0.0628(11) 0.0606(10) 0.0160(8) -0.0139(9) -0.0171(9) C23 0.0597(11) 0.1180(16) 0.0593(11) 0.0059(11) 0.0149(9) -0.0154(12) C24 0.0921(14) 0.0705(12) 0.0646(11) 0.0115(9) 0.0078(10) -0.0034(11) C25 0.0664(13) 0.1172(17) 0.0781(12) 0.0032(12) 0.0257(10) 0.0182(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 C1 C7 1.5176(19) . ? C1 C4 1.5229(19) . ? C1 C5 1.5229(19) . ? C1 H1A 0.9800 . ? C2 C13 1.408(2) . ? C2 C7 1.414(2) . ? C2 C11 1.433(2) . ? C3 C4 1.3870(19) . ? C3 C8 1.3899(19) . ? C3 H3A 0.9300 . ? O1 C8 1.3655(18) . ? O1 C24 1.416(2) . ? C4 C6 1.3846(19) . ? C5 C12 1.383(2) . ? C5 C9 1.387(2) . ? C6 C16 1.391(2) . ? C6 H6A 0.9300 . ? C7 C10 1.378(2) . ? C8 C14 1.378(2) . ? C9 C21 1.389(2) . ? C9 C10 1.466(2) . ? C10 C19 1.410(2) . ? C11 C22 1.411(2) . ? C11 C20 1.416(3) . ? C12 C15 1.393(2) . ? C12 H12A 0.9300 . ? C13 C17 1.367(2) . ? C13 H13A 0.9300 . ? O2 C15 1.368(2) . ? O2 C25 1.413(2) . ? C14 C16 1.372(2) . ? C14 H14A 0.9300 . ? C15 C18 1.386(2) . ? C16 H16A 0.9300 . ? C17 C23 1.403(3) . ? C17 H17A 0.9300 . ? C18 C21 1.385(2) . ? C18 H18A 0.9300 . ? C19 C22 1.359(2) . ? C19 H19A 0.9300 . ? C20 C23 1.351(3) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 H23A 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 C7 C1 C4 116.44(11) . . ? C7 C1 C5 101.49(11) . . ? C4 C1 C5 111.73(11) . . ? C7 C1 H1A 108.9 . . ? C4 C1 H1A 108.9 . . ? C5 C1 H1A 108.9 . . ? C13 C2 C7 123.97(13) . . ? C13 C2 C11 118.64(14) . . ? C7 C2 C11 117.39(14) . . ? C4 C3 C8 119.99(14) . . ? C4 C3 H3A 120.0 . . ? C8 C3 H3A 120.0 . . ? C8 O1 C24 118.66(12) . . ? C6 C4 C3 119.78(13) . . ? C6 C4 C1 121.52(13) . . ? C3 C4 C1 118.55(12) . . ? C12 C5 C9 121.55(14) . . ? C12 C5 C1 128.04(13) . . ? C9 C5 C1 110.39(13) . . ? C4 C6 C16 119.62(14) . . ? C4 C6 H6A 120.2 . . ? C16 C6 H6A 120.2 . . ? C10 C7 C2 121.34(13) . . ? C10 C7 C1 110.59(13) . . ? C2 C7 C1 127.98(13) . . ? O1 C8 C14 116.15(13) . . ? O1 C8 C3 123.88(15) . . ? C14 C8 C3 119.96(14) . . ? C5 C9 C21 120.20(15) . . ? C5 C9 C10 108.43(13) . . ? C21 C9 C10 131.30(15) . . ? C7 C10 C19 120.83(15) . . ? C7 C10 C9 109.07(13) . . ? C19 C10 C9 130.03(15) . . ? C22 C11 C20 122.66(16) . . ? C22 C11 C2 119.36(15) . . ? C20 C11 C2 117.97(17) . . ? C5 C12 C15 118.12(15) . . ? C5 C12 H12A 120.9 . . ? C15 C12 H12A 120.9 . . ? C17 C13 C2 121.04(15) . . ? C17 C13 H13A 119.5 . . ? C2 C13 H13A 119.5 . . ? C15 O2 C25 117.84(13) . . ? C16 C14 C8 120.15(14) . . ? C16 C14 H14A 119.9 . . ? C8 C14 H14A 119.9 . . ? O2 C15 C18 115.30(15) . . ? O2 C15 C12 124.32(17) . . ? C18 C15 C12 120.37(16) . . ? C14 C16 C6 120.46(15) . . ? C14 C16 H16A 119.8 . . ? C6 C16 H16A 119.8 . . ? C13 C17 C23 120.45(18) . . ? C13 C17 H17A 119.8 . . ? C23 C17 H17A 119.8 . . ? C21 C18 C15 121.31(15) . . ? C21 C18 H18A 119.3 . . ? C15 C18 H18A 119.3 . . ? C22 C19 C10 119.06(16) . . ? C22 C19 H19A 120.5 . . ? C10 C19 H19A 120.5 . . ? C23 C20 C11 121.86(17) . . ? C23 C20 H20A 119.1 . . ? C11 C20 H20A 119.1 . . ? C18 C21 C9 118.43(16) . . ? C18 C21 H21A 120.8 . . ? C9 C21 H21A 120.8 . . ? C19 C22 C11 122.01(15) . . ? C19 C22 H22A 119.0 . . ? C11 C22 H22A 119.0 . . ? C20 C23 C17 120.04(17) . . ? C20 C23 H23A 120.0 . . ? C17 C23 H23A 120.0 . . ? O1 C24 H24A 109.5 . . ? O1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O2 C25 H25A 109.5 . . ? O2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.19 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.160 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.041