# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Science # This journal is © The Royal Society of Chemistry and Owner Societies 2011 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_cambridge 0171 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email bpatrick@chem.ubc.ca _publ_contact_author_name 'Brian Patrick' loop_ _publ_author_name G.Kuzmanich 'Arunkumar Natarajan' 'Yanhui Shi' 'Brian Patrick' J.Scheffer 'Miguel A. Garcia-Garibay' data_1e _database_code_depnum_ccdc_archive 'CCDC 837497' #TrackingRef 'gg3606S.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H22 O' _chemical_formula_sum 'C27 H22 O' _chemical_formula_weight 362.45 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4338(12) _cell_length_b 9.8839(13) _cell_length_c 10.8606(14) _cell_angle_alpha 84.0480(10) _cell_angle_beta 85.7020(10) _cell_angle_gamma 77.0710(10) _cell_volume 980.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3937 _cell_measurement_theta_min 4.26 _cell_measurement_theta_max 28.21 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9621 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method '\w and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8819 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 28.27 _reflns_number_total 4728 _reflns_number_gt 3972 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0497P)^2^+0.3387P] 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 4728 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.07989(9) 0.17450(9) 0.71441(7) 0.02054(18) Uani 1 1 d . . . C1 C 0.79564(12) 0.18765(11) 0.65403(10) 0.0156(2) Uani 1 1 d . . . C2 C 0.86467(12) 0.18090(12) 0.53550(10) 0.0184(2) Uani 1 1 d . . . H2 H 0.9345 0.2359 0.5113 0.022 Uiso 1 1 calc R . . C3 C 0.83298(13) 0.09539(12) 0.45266(10) 0.0209(2) Uani 1 1 d . . . H3 H 0.8823 0.0908 0.3732 0.025 Uiso 1 1 calc R . . C4 C 0.72922(13) 0.01644(12) 0.48575(11) 0.0217(2) Uani 1 1 d . . . H4 H 0.7068 -0.0418 0.4291 0.026 Uiso 1 1 calc R . . C5 C 0.65868(13) 0.02337(12) 0.60214(11) 0.0212(2) Uani 1 1 d . . . H5 H 0.5872 -0.0300 0.6251 0.025 Uiso 1 1 calc R . . C6 C 0.69181(12) 0.10833(11) 0.68605(10) 0.0185(2) Uani 1 1 d . . . H6 H 0.6429 0.1119 0.7657 0.022 Uiso 1 1 calc R . . C7 C 0.82684(11) 0.29282(11) 0.73782(9) 0.0141(2) Uani 1 1 d . . . C8 C 0.75159(12) 0.43579(11) 0.67756(10) 0.0157(2) Uani 1 1 d . . . C9 C 0.82782(13) 0.52288(12) 0.60478(10) 0.0196(2) Uani 1 1 d . . . H9 H 0.9313 0.4996 0.5997 0.023 Uiso 1 1 calc R . . C10 C 0.75453(14) 0.64389(13) 0.53925(11) 0.0241(3) Uani 1 1 d . . . H10 H 0.8082 0.7026 0.4903 0.029 Uiso 1 1 calc R . . C11 C 0.60360(14) 0.67882(12) 0.54530(11) 0.0236(3) Uani 1 1 d . . . H11 H 0.5536 0.7612 0.5005 0.028 Uiso 1 1 calc R . . C12 C 0.52610(13) 0.59262(12) 0.61718(11) 0.0219(2) Uani 1 1 d . . . H12 H 0.4227 0.6161 0.6217 0.026 Uiso 1 1 calc R . . C13 C 0.59926(12) 0.47236(12) 0.68237(10) 0.0184(2) Uani 1 1 d . . . H13 H 0.5451 0.4139 0.7311 0.022 Uiso 1 1 calc R . . C14 C 0.77926(11) 0.26653(11) 0.87568(10) 0.0153(2) Uani 1 1 d . . . C15 C 0.82036(12) 0.13202(12) 0.93508(10) 0.0175(2) Uani 1 1 d . . . H15 H 0.8714 0.0581 0.8887 0.021 Uiso 1 1 calc R . . C16 C 0.78744(12) 0.10524(12) 1.06098(11) 0.0206(2) Uani 1 1 d . . . H16 H 0.8140 0.0132 1.0997 0.025 Uiso 1 1 calc R . . C17 C 0.71541(13) 0.21369(13) 1.13007(10) 0.0219(2) Uani 1 1 d . . . H17 H 0.6921 0.1957 1.2160 0.026 Uiso 1 1 calc R . . C18 C 0.67785(13) 0.34802(13) 1.07310(10) 0.0210(2) Uani 1 1 d . . . H18 H 0.6297 0.4222 1.1205 0.025 Uiso 1 1 calc R . . C19 C 0.71030(12) 0.37498(12) 0.94692(10) 0.0176(2) Uani 1 1 d . . . H19 H 0.6854 0.4676 0.9090 0.021 Uiso 1 1 calc R . . C20 C 0.99381(12) 0.27605(11) 0.74754(10) 0.0155(2) Uani 1 1 d . . . C21 C 1.04663(12) 0.38561(12) 0.81084(11) 0.0189(2) Uani 1 1 d . . . H21A H 1.0974 0.4409 0.7483 0.023 Uiso 1 1 calc R . . H21B H 0.9617 0.4500 0.8473 0.023 Uiso 1 1 calc R . . C22 C 1.14881(12) 0.31905(11) 0.91151(10) 0.0177(2) Uani 1 1 d . . . C23 C 1.09583(13) 0.29991(12) 1.03379(11) 0.0206(2) Uani 1 1 d . . . H23 H 0.9945 0.3285 1.0541 0.025 Uiso 1 1 calc R . . C24 C 1.19043(14) 0.23904(13) 1.12648(11) 0.0242(3) Uani 1 1 d . . . H24 H 1.1534 0.2267 1.2097 0.029 Uiso 1 1 calc R . . C25 C 1.33813(14) 0.19650(13) 1.09783(12) 0.0253(3) Uani 1 1 d . . . H25 H 1.4026 0.1562 1.1614 0.030 Uiso 1 1 calc R . . C26 C 1.39174(13) 0.21296(14) 0.97587(12) 0.0258(3) Uani 1 1 d . . . H26 H 1.4929 0.1826 0.9557 0.031 Uiso 1 1 calc R . . C27 C 1.29752(13) 0.27386(13) 0.88341(11) 0.0221(2) Uani 1 1 d . . . H27 H 1.3348 0.2848 0.8001 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0183(4) 0.0213(4) 0.0205(4) -0.0060(3) -0.0012(3) 0.0008(3) C1 0.0163(5) 0.0129(5) 0.0159(5) -0.0018(4) -0.0037(4) 0.0016(4) C2 0.0179(5) 0.0183(5) 0.0176(5) -0.0015(4) -0.0018(4) -0.0006(4) C3 0.0213(5) 0.0216(6) 0.0169(5) -0.0042(4) -0.0036(4) 0.0034(4) C4 0.0257(6) 0.0168(5) 0.0214(6) -0.0051(4) -0.0089(5) 0.0017(4) C5 0.0232(6) 0.0166(5) 0.0245(6) -0.0018(4) -0.0057(4) -0.0043(4) C6 0.0203(5) 0.0159(5) 0.0181(5) -0.0015(4) -0.0021(4) -0.0009(4) C7 0.0147(5) 0.0126(5) 0.0141(5) -0.0013(4) -0.0007(4) -0.0011(4) C8 0.0189(5) 0.0132(5) 0.0138(5) -0.0028(4) -0.0021(4) 0.0000(4) C9 0.0199(5) 0.0187(5) 0.0184(5) 0.0001(4) 0.0000(4) -0.0019(4) C10 0.0305(6) 0.0186(6) 0.0217(6) 0.0031(4) -0.0005(5) -0.0048(5) C11 0.0310(6) 0.0151(5) 0.0218(6) -0.0001(4) -0.0070(5) 0.0024(5) C12 0.0206(6) 0.0211(6) 0.0221(6) -0.0053(4) -0.0047(4) 0.0024(4) C13 0.0188(5) 0.0177(5) 0.0183(5) -0.0030(4) -0.0007(4) -0.0025(4) C14 0.0147(5) 0.0172(5) 0.0142(5) -0.0012(4) -0.0010(4) -0.0038(4) C15 0.0171(5) 0.0168(5) 0.0181(5) -0.0012(4) -0.0026(4) -0.0025(4) C16 0.0200(5) 0.0213(6) 0.0199(5) 0.0044(4) -0.0051(4) -0.0047(4) C17 0.0207(6) 0.0310(6) 0.0141(5) 0.0011(4) -0.0018(4) -0.0068(5) C18 0.0197(5) 0.0261(6) 0.0170(5) -0.0058(4) 0.0008(4) -0.0033(5) C19 0.0182(5) 0.0169(5) 0.0174(5) -0.0019(4) -0.0013(4) -0.0027(4) C20 0.0170(5) 0.0155(5) 0.0133(5) 0.0004(4) -0.0005(4) -0.0029(4) C21 0.0196(5) 0.0157(5) 0.0216(5) -0.0011(4) -0.0031(4) -0.0039(4) C22 0.0191(5) 0.0152(5) 0.0203(5) -0.0023(4) -0.0033(4) -0.0060(4) C23 0.0191(5) 0.0214(6) 0.0226(6) -0.0055(4) -0.0001(4) -0.0058(4) C24 0.0280(6) 0.0263(6) 0.0202(6) -0.0019(5) -0.0015(5) -0.0098(5) C25 0.0246(6) 0.0269(6) 0.0256(6) 0.0019(5) -0.0088(5) -0.0077(5) C26 0.0177(6) 0.0305(6) 0.0295(6) -0.0015(5) -0.0032(5) -0.0054(5) C27 0.0205(6) 0.0262(6) 0.0211(5) -0.0014(5) -0.0005(4) -0.0091(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C20 1.2094(13) . ? C1 C6 1.3896(16) . ? C1 C2 1.3994(15) . ? C1 C7 1.5391(15) . ? C2 C3 1.3872(16) . ? C2 H2 0.9500 . ? C3 C4 1.3882(18) . ? C3 H3 0.9500 . ? C4 C5 1.3846(17) . ? C4 H4 0.9500 . ? C5 C6 1.3972(16) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.5355(14) . ? C7 C14 1.5432(14) . ? C7 C20 1.5570(15) . ? C8 C9 1.3905(16) . ? C8 C13 1.3996(15) . ? C9 C10 1.3937(16) . ? C9 H9 0.9500 . ? C10 C11 1.3862(18) . ? C10 H10 0.9500 . ? C11 C12 1.3875(18) . ? C11 H11 0.9500 . ? C12 C13 1.3864(16) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.3983(15) . ? C14 C15 1.4011(15) . ? C15 C16 1.3907(15) . ? C15 H15 0.9500 . ? C16 C17 1.3923(17) . ? C16 H16 0.9500 . ? C17 C18 1.3868(17) . ? C17 H17 0.9500 . ? C18 C19 1.3931(15) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.5299(15) . ? C21 C22 1.5107(15) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.3929(16) . ? C22 C27 1.3944(16) . ? C23 C24 1.3930(17) . ? C23 H23 0.9500 . ? C24 C25 1.3839(18) . ? C24 H24 0.9500 . ? C25 C26 1.3887(18) . ? C25 H25 0.9500 . ? C26 C27 1.3892(17) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.21(10) . . ? C6 C1 C7 122.90(10) . . ? C2 C1 C7 118.61(10) . . ? C3 C2 C1 121.18(11) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 120.09(11) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.38(11) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.50(11) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 120.62(10) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C1 104.51(8) . . ? C8 C7 C14 113.63(8) . . ? C1 C7 C14 114.32(9) . . ? C8 C7 C20 113.50(9) . . ? C1 C7 C20 110.73(8) . . ? C14 C7 C20 100.46(8) . . ? C9 C8 C13 118.18(10) . . ? C9 C8 C7 122.47(10) . . ? C13 C8 C7 118.81(10) . . ? C8 C9 C10 120.90(11) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 120.19(11) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.54(11) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 120.17(11) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 121.02(11) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C19 C14 C15 118.53(10) . . ? C19 C14 C7 122.16(9) . . ? C15 C14 C7 118.94(9) . . ? C16 C15 C14 120.93(10) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 119.84(11) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 119.78(10) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 120.47(11) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 120.39(10) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? O1 C20 C21 120.11(10) . . ? O1 C20 C7 121.46(10) . . ? C21 C20 C7 118.22(9) . . ? C22 C21 C20 111.48(9) . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21B 109.3 . . ? C20 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C27 118.81(10) . . ? C23 C22 C21 120.57(10) . . ? C27 C22 C21 120.61(10) . . ? C22 C23 C24 120.43(11) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 120.27(11) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 119.76(11) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C25 C26 C27 120.01(11) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C26 C27 C22 120.72(11) . . ? C26 C27 H27 119.6 . . ? C22 C27 H27 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.29(16) . . . . ? C7 C1 C2 C3 -175.36(10) . . . . ? C1 C2 C3 C4 1.21(17) . . . . ? C2 C3 C4 C5 -0.38(17) . . . . ? C3 C4 C5 C6 -0.34(17) . . . . ? C2 C1 C6 C5 0.56(16) . . . . ? C7 C1 C6 C5 174.36(10) . . . . ? C4 C5 C6 C1 0.24(17) . . . . ? C6 C1 C7 C8 -103.37(11) . . . . ? C2 C1 C7 C8 70.40(11) . . . . ? C6 C1 C7 C14 21.47(14) . . . . ? C2 C1 C7 C14 -164.76(9) . . . . ? C6 C1 C7 C20 134.06(10) . . . . ? C2 C1 C7 C20 -52.17(12) . . . . ? C1 C7 C8 C9 -101.57(12) . . . . ? C14 C7 C8 C9 133.14(11) . . . . ? C20 C7 C8 C9 19.17(14) . . . . ? C1 C7 C8 C13 69.92(12) . . . . ? C14 C7 C8 C13 -55.36(13) . . . . ? C20 C7 C8 C13 -169.33(9) . . . . ? C13 C8 C9 C10 0.54(17) . . . . ? C7 C8 C9 C10 172.08(10) . . . . ? C8 C9 C10 C11 -0.37(18) . . . . ? C9 C10 C11 C12 0.12(19) . . . . ? C10 C11 C12 C13 -0.05(18) . . . . ? C11 C12 C13 C8 0.24(17) . . . . ? C9 C8 C13 C12 -0.48(16) . . . . ? C7 C8 C13 C12 -172.33(10) . . . . ? C8 C7 C14 C19 -18.03(14) . . . . ? C1 C7 C14 C19 -137.89(10) . . . . ? C20 C7 C14 C19 103.52(11) . . . . ? C8 C7 C14 C15 169.08(10) . . . . ? C1 C7 C14 C15 49.22(13) . . . . ? C20 C7 C14 C15 -69.37(11) . . . . ? C19 C14 C15 C16 2.98(16) . . . . ? C7 C14 C15 C16 176.13(10) . . . . ? C14 C15 C16 C17 -1.39(17) . . . . ? C15 C16 C17 C18 -0.47(17) . . . . ? C16 C17 C18 C19 0.69(18) . . . . ? C17 C18 C19 C14 0.95(17) . . . . ? C15 C14 C19 C18 -2.75(16) . . . . ? C7 C14 C19 C18 -175.67(10) . . . . ? C8 C7 C20 O1 -131.46(11) . . . . ? C1 C7 C20 O1 -14.28(14) . . . . ? C14 C7 C20 O1 106.89(11) . . . . ? C8 C7 C20 C21 53.80(12) . . . . ? C1 C7 C20 C21 170.98(9) . . . . ? C14 C7 C20 C21 -67.84(11) . . . . ? O1 C20 C21 C22 -47.14(14) . . . . ? C7 C20 C21 C22 127.68(10) . . . . ? C20 C21 C22 C23 -92.67(12) . . . . ? C20 C21 C22 C27 86.40(13) . . . . ? C27 C22 C23 C24 1.19(17) . . . . ? C21 C22 C23 C24 -179.73(11) . . . . ? C22 C23 C24 C25 -0.23(18) . . . . ? C23 C24 C25 C26 -0.86(19) . . . . ? C24 C25 C26 C27 0.96(19) . . . . ? C25 C26 C27 C22 0.02(19) . . . . ? C23 C22 C27 C26 -1.09(17) . . . . ? C21 C22 C27 C26 179.83(11) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.25 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.355 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.041 # Attachment 'js223.cif' data_1b _database_code_depnum_ccdc_archive 'CCDC 837498' #TrackingRef 'js223.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 O' _chemical_formula_weight 314.41 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 16.115(3) _cell_length_b 14.052(3) _cell_length_c 7.5090(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.180(10) _cell_angle_gamma 90.00 _cell_volume 1699.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2692 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 24.12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/ADSC CCD' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5656 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.1014 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2963 _reflns_number_gt 1578 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0232P)^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 cnostr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0034(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2963 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0630 _refine_ls_wR_factor_gt 0.0554 _refine_ls_goodness_of_fit_ref 0.781 _refine_ls_restrained_S_all 0.781 _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 0.26151(11) -0.02940(13) 0.1382(2) 0.0198(4) Uani 1 1 d . . . C2 C 0.32234(11) -0.08533(13) 0.02124(19) 0.0188(4) Uani 1 1 d . . . C3 C 0.40793(11) -0.08091(13) 0.0474(2) 0.0239(5) Uani 1 1 d . . . H3 H 0.4310 -0.0427 0.1412 0.029 Uiso 1 1 calc R . . C4 C 0.46060(12) -0.13125(13) -0.0609(2) 0.0302(5) Uani 1 1 d . . . H4 H 0.5190 -0.1274 -0.0405 0.036 Uiso 1 1 calc R . . C5 C 0.42812(13) -0.18663(14) -0.1974(2) 0.0329(5) Uani 1 1 d . . . H5 H 0.4639 -0.2217 -0.2707 0.039 Uiso 1 1 calc R . . C6 C 0.34328(13) -0.19094(13) -0.2271(2) 0.0292(5) Uani 1 1 d . . . H6 H 0.3206 -0.2289 -0.3217 0.035 Uiso 1 1 calc R . . C7 C 0.29106(12) -0.14060(13) -0.1205(2) 0.0248(5) Uani 1 1 d . . . H7 H 0.2328 -0.1436 -0.1439 0.030 Uiso 1 1 calc R . . C8 C 0.20568(11) 0.03618(13) 0.0177(2) 0.0209(4) Uani 1 1 d . . . C9 C 0.23743(12) 0.07774(13) -0.1336(2) 0.0273(5) Uani 1 1 d . . . H9 H 0.2923 0.0626 -0.1660 0.033 Uiso 1 1 calc R . . C10 C 0.19085(12) 0.14048(14) -0.2376(2) 0.0321(5) Uani 1 1 d . . . H10 H 0.2138 0.1678 -0.3405 0.039 Uiso 1 1 calc R . . C11 C 0.11137(12) 0.16362(14) -0.1929(2) 0.0339(5) Uani 1 1 d . . . H11 H 0.0796 0.2076 -0.2633 0.041 Uiso 1 1 calc R . . C12 C 0.07822(12) 0.12227(14) -0.0447(2) 0.0373(6) Uani 1 1 d . . . H12 H 0.0231 0.1371 -0.0138 0.045 Uiso 1 1 calc R . . C13 C 0.12513(12) 0.05909(14) 0.0591(2) 0.0306(5) Uani 1 1 d . . . H13 H 0.1015 0.0310 0.1605 0.037 Uiso 1 1 calc R . . C14 C 0.30903(11) 0.02943(13) 0.2813(2) 0.0196(4) Uani 1 1 d . . . C15 C 0.31033(11) 0.12830(14) 0.2808(2) 0.0258(5) Uani 1 1 d . . . H15 H 0.2794 0.1619 0.1909 0.031 Uiso 1 1 calc R . . C16 C 0.35599(12) 0.17859(14) 0.4093(2) 0.0316(5) Uani 1 1 d . . . H16 H 0.3563 0.2462 0.4064 0.038 Uiso 1 1 calc R . . C17 C 0.40088(12) 0.13139(15) 0.5407(2) 0.0323(5) Uani 1 1 d . . . H17 H 0.4323 0.1662 0.6282 0.039 Uiso 1 1 calc R . . C18 C 0.40021(12) 0.03313(15) 0.5456(2) 0.0283(5) Uani 1 1 d . . . H18 H 0.4309 0.0002 0.6369 0.034 Uiso 1 1 calc R . . C19 C 0.35482(11) -0.01708(13) 0.4173(2) 0.0233(5) Uani 1 1 d . . . H19 H 0.3547 -0.0847 0.4215 0.028 Uiso 1 1 calc R . . C20 C 0.20160(12) -0.10180(13) 0.2293(2) 0.0262(5) Uani 1 1 d . . . C21 C 0.17055(11) -0.08155(14) 0.4137(2) 0.0300(5) Uani 1 1 d . . . H21A H 0.2121 -0.1048 0.5040 0.036 Uiso 1 1 calc R . . H21B H 0.1653 -0.0119 0.4291 0.036 Uiso 1 1 calc R . . C22 C 0.08795(11) -0.12755(14) 0.4467(2) 0.0340(5) Uani 1 1 d . . . H22A H 0.0930 -0.1971 0.4284 0.041 Uiso 1 1 calc R . . H22B H 0.0463 -0.1033 0.3576 0.041 Uiso 1 1 calc R . . C23 C 0.05681(12) -0.10974(15) 0.6315(2) 0.0430(6) Uani 1 1 d . . . H23A H 0.0933 -0.1419 0.7199 0.065 Uiso 1 1 calc R . . H23B H 0.0002 -0.1346 0.6387 0.065 Uiso 1 1 calc R . . H23C H 0.0568 -0.0412 0.6554 0.065 Uiso 1 1 calc R . . O1 O 0.17843(9) -0.17263(10) 0.15112(17) 0.0475(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 0.0185(11) 0.0206(11) 0.0202(9) 0.0012(8) 0.0010(8) -0.0021(9) C2 0.0224(12) 0.0162(10) 0.0178(9) 0.0026(8) 0.0015(8) -0.0008(9) C3 0.0275(13) 0.0212(11) 0.0232(9) -0.0010(9) 0.0027(9) 0.0008(10) C4 0.0279(13) 0.0299(12) 0.0330(10) 0.0015(11) 0.0031(9) 0.0053(11) C5 0.0442(15) 0.0244(13) 0.0310(11) 0.0022(10) 0.0131(10) 0.0116(11) C6 0.0453(15) 0.0192(12) 0.0233(10) -0.0018(9) 0.0050(10) 0.0015(11) C7 0.0286(12) 0.0233(12) 0.0225(9) 0.0013(9) 0.0020(9) -0.0020(10) C8 0.0191(12) 0.0229(11) 0.0203(9) -0.0030(8) -0.0017(8) 0.0006(9) C9 0.0237(12) 0.0247(12) 0.0335(10) 0.0031(10) 0.0015(9) 0.0003(11) C10 0.0331(14) 0.0302(13) 0.0329(11) 0.0068(10) -0.0005(10) -0.0028(11) C11 0.0352(14) 0.0271(13) 0.0382(11) 0.0015(10) -0.0119(10) 0.0065(11) C12 0.0257(13) 0.0468(15) 0.0395(12) -0.0007(11) 0.0026(10) 0.0114(11) C13 0.0286(13) 0.0374(14) 0.0260(10) 0.0035(9) 0.0018(9) 0.0051(11) C14 0.0208(11) 0.0184(11) 0.0201(9) -0.0011(9) 0.0067(8) -0.0013(9) C15 0.0281(12) 0.0282(12) 0.0211(9) -0.0001(10) 0.0014(8) -0.0002(11) C16 0.0398(14) 0.0247(12) 0.0306(10) -0.0028(10) 0.0065(10) -0.0045(11) C17 0.0319(13) 0.0373(15) 0.0279(11) -0.0115(11) 0.0032(9) -0.0108(12) C18 0.0261(12) 0.0380(14) 0.0206(10) 0.0019(10) -0.0008(9) -0.0012(11) C19 0.0245(12) 0.0228(11) 0.0229(9) 0.0014(9) 0.0034(8) -0.0016(10) C20 0.0250(12) 0.0231(13) 0.0301(10) -0.0002(9) -0.0014(9) -0.0005(10) C21 0.0269(12) 0.0340(13) 0.0292(10) 0.0033(10) 0.0033(9) -0.0036(11) C22 0.0294(13) 0.0372(13) 0.0358(11) 0.0063(10) 0.0078(9) -0.0053(11) C23 0.0350(14) 0.0508(17) 0.0441(11) 0.0041(11) 0.0120(10) -0.0036(11) O1 0.0541(11) 0.0388(10) 0.0509(9) -0.0133(8) 0.0186(8) -0.0225(8) _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 C14 1.537(2) . ? C1 C8 1.554(2) . ? C1 C2 1.554(2) . ? C1 C20 1.577(2) . ? C2 C3 1.387(2) . ? C2 C7 1.396(2) . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C4 C5 1.375(2) . ? C4 H4 0.9500 . ? C5 C6 1.378(3) . ? C5 H5 0.9500 . ? C6 C7 1.378(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.384(2) . ? C8 C9 1.392(2) . ? C9 C10 1.381(2) . ? C9 H9 0.9500 . ? C10 C11 1.375(2) . ? C10 H10 0.9500 . ? C11 C12 1.381(2) . ? C11 H11 0.9500 . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.389(2) . ? C14 C19 1.399(2) . ? C15 C16 1.385(2) . ? C15 H15 0.9500 . ? C16 C17 1.372(2) . ? C16 H16 0.9500 . ? C17 C18 1.381(2) . ? C17 H17 0.9500 . ? C18 C19 1.381(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 O1 1.2076(19) . ? C20 C21 1.517(2) . ? C21 C22 1.509(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.514(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 C1 C8 110.51(14) . . ? C14 C1 C2 111.03(14) . . ? C8 C1 C2 109.54(13) . . ? C14 C1 C20 109.91(13) . . ? C8 C1 C20 106.55(14) . . ? C2 C1 C20 109.20(14) . . ? C3 C2 C7 117.46(16) . . ? C3 C2 C1 122.85(15) . . ? C7 C2 C1 119.66(16) . . ? C2 C3 C4 121.33(16) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 120.02(18) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.53(18) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C7 120.48(17) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 121.16(18) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? C13 C8 C9 117.56(17) . . ? C13 C8 C1 122.29(15) . . ? C9 C8 C1 120.08(16) . . ? C10 C9 C8 121.38(18) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C11 C10 C9 120.28(18) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.32(18) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C12 C13 120.21(18) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C13 C12 121.23(17) . . ? C8 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C19 117.49(17) . . ? C15 C14 C1 122.89(16) . . ? C19 C14 C1 119.61(16) . . ? C16 C15 C14 121.07(18) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C17 C16 C15 120.40(19) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.85(19) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 119.78(19) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C14 121.40(18) . . ? C18 C19 H19 119.3 . . ? C14 C19 H19 119.3 . . ? O1 C20 C21 119.47(17) . . ? O1 C20 C1 120.25(16) . . ? C21 C20 C1 120.25(16) . . ? C22 C21 C20 113.15(15) . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.8 . . ? C21 C22 C23 113.87(15) . . ? C21 C22 H22A 108.8 . . ? C23 C22 H22A 108.8 . . ? C21 C22 H22B 108.8 . . ? C23 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C3 0.1(2) . . . . ? C8 C1 C2 C3 122.47(18) . . . . ? C20 C1 C2 C3 -121.20(18) . . . . ? C14 C1 C2 C7 -177.83(16) . . . . ? C8 C1 C2 C7 -55.5(2) . . . . ? C20 C1 C2 C7 60.82(19) . . . . ? C7 C2 C3 C4 -1.4(3) . . . . ? C1 C2 C3 C4 -179.40(15) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C2 -1.0(3) . . . . ? C3 C2 C7 C6 1.8(3) . . . . ? C1 C2 C7 C6 179.88(15) . . . . ? C14 C1 C8 C13 -88.4(2) . . . . ? C2 C1 C8 C13 149.01(17) . . . . ? C20 C1 C8 C13 31.0(2) . . . . ? C14 C1 C8 C9 88.63(19) . . . . ? C2 C1 C8 C9 -34.0(2) . . . . ? C20 C1 C8 C9 -152.00(16) . . . . ? C13 C8 C9 C10 0.8(3) . . . . ? C1 C8 C9 C10 -176.32(17) . . . . ? C8 C9 C10 C11 0.2(3) . . . . ? C9 C10 C11 C12 -1.1(3) . . . . ? C10 C11 C12 C13 0.9(3) . . . . ? C9 C8 C13 C12 -1.0(3) . . . . ? C1 C8 C13 C12 176.08(17) . . . . ? C11 C12 C13 C8 0.2(3) . . . . ? C8 C1 C14 C15 -9.3(2) . . . . ? C2 C1 C14 C15 112.45(18) . . . . ? C20 C1 C14 C15 -126.62(18) . . . . ? C8 C1 C14 C19 172.06(15) . . . . ? C2 C1 C14 C19 -66.2(2) . . . . ? C20 C1 C14 C19 54.7(2) . . . . ? C19 C14 C15 C16 0.7(3) . . . . ? C1 C14 C15 C16 -178.01(16) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C15 C16 C17 C18 -0.3(3) . . . . ? C16 C17 C18 C19 0.5(3) . . . . ? C17 C18 C19 C14 0.0(3) . . . . ? C15 C14 C19 C18 -0.5(3) . . . . ? C1 C14 C19 C18 178.19(16) . . . . ? C14 C1 C20 O1 -157.14(17) . . . . ? C8 C1 C20 O1 83.1(2) . . . . ? C2 C1 C20 O1 -35.1(2) . . . . ? C14 C1 C20 C21 24.7(2) . . . . ? C8 C1 C20 C21 -95.06(18) . . . . ? C2 C1 C20 C21 146.72(15) . . . . ? O1 C20 C21 C22 -25.1(2) . . . . ? C1 C20 C21 C22 153.10(17) . . . . ? C20 C21 C22 C23 178.83(16) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.123 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.030 # Attachment 'js224.cif' data_1d _database_code_depnum_ccdc_archive 'CCDC 837499' #TrackingRef 'js224.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 O' _chemical_formula_weight 328.43 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 16.034(2) _cell_length_b 8.5909(7) _cell_length_c 15.611(2) _cell_angle_alpha 90.00 _cell_angle_beta 119.895(6) _cell_angle_gamma 90.00 _cell_volume 1864.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4678 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 27.33 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.695 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/ADSC CCD' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3385 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 27.54 _reflns_number_total 1946 _reflns_number_gt 1751 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0526P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(15) _refine_ls_number_reflns 1946 _refine_ls_number_parameters 229 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0764 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.026 _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 0.57506(13) 0.1453(2) 0.28309(12) 0.0236(4) Uani 1 1 d . . . C2 C 0.66170(14) 0.2586(2) 0.33940(14) 0.0304(4) Uani 1 1 d . . . C3 C 0.62174(17) 0.4091(2) 0.35884(17) 0.0420(5) Uani 1 1 d . . . H3A H 0.6751 0.4787 0.4008 0.063 Uiso 1 1 calc R . . H3B H 0.5854 0.3837 0.3922 0.063 Uiso 1 1 calc R . . H3C H 0.5792 0.4609 0.2959 0.063 Uiso 1 1 calc R . . C4 C 0.72796(17) 0.1818(3) 0.43984(16) 0.0485(6) Uani 1 1 d . . . H4A H 0.7539 0.0847 0.4296 0.073 Uiso 1 1 calc R . . H4B H 0.6912 0.1592 0.4731 0.073 Uiso 1 1 calc R . . H4C H 0.7810 0.2525 0.4808 0.073 Uiso 1 1 calc R . . C5 C 0.72150(16) 0.3009(3) 0.29088(18) 0.0454(5) Uani 1 1 d . . . H5A H 0.7755 0.3672 0.3357 0.068 Uiso 1 1 calc R . . H5B H 0.6810 0.3569 0.2290 0.068 Uiso 1 1 calc R . . H5C H 0.7461 0.2055 0.2769 0.068 Uiso 1 1 calc R . . C6 C 0.55582(13) 0.04331(18) 0.19081(13) 0.0222(3) Uani 1 1 d . . . C7 C 0.46647(13) -0.0594(2) 0.16090(12) 0.0240(4) Uani 1 1 d . . . C8 C 0.46554(15) -0.2204(2) 0.14856(14) 0.0324(4) Uani 1 1 d . . . H8 H 0.5229 -0.2728 0.1618 0.039 Uiso 1 1 calc R . . C9 C 0.38091(18) -0.3045(3) 0.11690(18) 0.0447(5) Uani 1 1 d . . . H9 H 0.3812 -0.4140 0.1085 0.054 Uiso 1 1 calc R . . C10 C 0.29735(18) -0.2321(3) 0.09764(17) 0.0457(6) Uani 1 1 d . . . H10 H 0.2403 -0.2912 0.0767 0.055 Uiso 1 1 calc R . . C11 C 0.29633(15) -0.0724(3) 0.10880(14) 0.0379(5) Uani 1 1 d . . . H11 H 0.2386 -0.0213 0.0956 0.046 Uiso 1 1 calc R . . C12 C 0.38002(14) 0.0126(2) 0.13933(14) 0.0304(4) Uani 1 1 d . . . H12 H 0.3785 0.1224 0.1457 0.037 Uiso 1 1 calc R . . C13 C 0.53009(12) 0.14355(19) 0.09906(13) 0.0226(4) Uani 1 1 d . . . C14 C 0.51610(14) 0.0741(2) 0.01198(14) 0.0292(4) Uani 1 1 d . . . H14 H 0.5253 -0.0350 0.0108 0.035 Uiso 1 1 calc R . . C15 C 0.48914(14) 0.1608(2) -0.07260(14) 0.0333(5) Uani 1 1 d . . . H15 H 0.4803 0.1110 -0.1309 0.040 Uiso 1 1 calc R . . C16 C 0.47495(15) 0.3195(2) -0.07266(15) 0.0340(4) Uani 1 1 d . . . H16 H 0.4583 0.3794 -0.1301 0.041 Uiso 1 1 calc R . . C17 C 0.48514(16) 0.3900(2) 0.01106(16) 0.0355(5) Uani 1 1 d . . . H17 H 0.4742 0.4987 0.0111 0.043 Uiso 1 1 calc R . . C18 C 0.51155(14) 0.3024(2) 0.09596(14) 0.0289(4) Uani 1 1 d . . . H18 H 0.5170 0.3521 0.1529 0.035 Uiso 1 1 calc R . . C19 C 0.64761(13) -0.05736(19) 0.22722(13) 0.0246(4) Uani 1 1 d . . . C20 C 0.67622(14) -0.1523(2) 0.31008(14) 0.0285(4) Uani 1 1 d . . . H20 H 0.6378 -0.1566 0.3407 0.034 Uiso 1 1 calc R . . C21 C 0.75991(15) -0.2405(2) 0.34832(15) 0.0342(5) Uani 1 1 d . . . H21 H 0.7783 -0.3037 0.4049 0.041 Uiso 1 1 calc R . . C22 C 0.81645(16) -0.2366(2) 0.30451(17) 0.0390(5) Uani 1 1 d . . . H22 H 0.8734 -0.2974 0.3303 0.047 Uiso 1 1 calc R . . C23 C 0.78910(16) -0.1433(2) 0.22278(17) 0.0413(5) Uani 1 1 d . . . H23 H 0.8278 -0.1395 0.1925 0.050 Uiso 1 1 calc R . . C24 C 0.70573(14) -0.0552(2) 0.18438(15) 0.0327(4) Uani 1 1 d . . . H24 H 0.6879 0.0078 0.1278 0.039 Uiso 1 1 calc R . . O1 O 0.52312(10) 0.12948(16) 0.31781(10) 0.0347(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0289(10) 0.0194(8) 0.0253(9) 0.0034(7) 0.0155(8) 0.0042(7) C2 0.0318(11) 0.0285(10) 0.0327(10) -0.0051(8) 0.0173(9) -0.0012(8) C3 0.0511(14) 0.0283(11) 0.0467(12) -0.0109(9) 0.0243(11) -0.0025(10) C4 0.0450(14) 0.0464(13) 0.0334(12) -0.0058(10) 0.0040(10) 0.0003(10) C5 0.0368(13) 0.0505(13) 0.0547(14) -0.0154(11) 0.0273(11) -0.0168(10) C6 0.0274(9) 0.0178(7) 0.0271(8) 0.0014(7) 0.0178(7) 0.0016(7) C7 0.0296(10) 0.0236(9) 0.0224(8) 0.0016(7) 0.0156(8) -0.0012(7) C8 0.0393(11) 0.0239(9) 0.0357(10) 0.0000(8) 0.0200(10) -0.0016(8) C9 0.0524(14) 0.0298(10) 0.0487(13) -0.0006(10) 0.0228(11) -0.0139(11) C10 0.0443(14) 0.0504(14) 0.0433(13) 0.0036(10) 0.0227(11) -0.0222(11) C11 0.0300(11) 0.0535(13) 0.0344(11) 0.0092(10) 0.0191(9) -0.0019(9) C12 0.0331(10) 0.0317(10) 0.0326(9) 0.0041(8) 0.0209(8) 0.0013(8) C13 0.0248(9) 0.0203(8) 0.0276(9) 0.0014(8) 0.0168(8) -0.0004(7) C14 0.0370(11) 0.0225(9) 0.0339(9) 0.0010(8) 0.0222(9) 0.0014(8) C15 0.0387(12) 0.0404(12) 0.0288(9) -0.0003(8) 0.0229(9) -0.0012(9) C16 0.0365(11) 0.0363(11) 0.0319(10) 0.0110(9) 0.0190(9) 0.0001(9) C17 0.0420(12) 0.0237(9) 0.0406(10) 0.0072(9) 0.0204(10) 0.0028(9) C18 0.0360(11) 0.0233(9) 0.0307(9) 0.0005(8) 0.0192(9) 0.0026(8) C19 0.0284(9) 0.0176(8) 0.0320(9) -0.0004(7) 0.0182(8) 0.0011(7) C20 0.0330(11) 0.0257(9) 0.0316(9) 0.0024(8) 0.0196(8) 0.0018(8) C21 0.0388(12) 0.0279(10) 0.0343(10) 0.0060(8) 0.0171(9) 0.0083(8) C22 0.0351(12) 0.0311(10) 0.0526(12) 0.0026(10) 0.0232(10) 0.0115(9) C23 0.0469(13) 0.0354(11) 0.0616(14) 0.0067(10) 0.0421(12) 0.0113(9) C24 0.0414(12) 0.0260(10) 0.0438(11) 0.0079(8) 0.0311(10) 0.0070(8) O1 0.0426(8) 0.0361(7) 0.0382(7) -0.0058(6) 0.0298(7) -0.0043(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.207(2) . ? C1 C2 1.560(3) . ? C1 C6 1.580(2) . ? C2 C5 1.532(3) . ? C2 C4 1.537(3) . ? C2 C3 1.539(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C13 1.541(2) . ? C6 C7 1.543(3) . ? C6 C19 1.550(2) . ? C7 C8 1.395(3) . ? C7 C12 1.397(3) . ? C8 C9 1.393(3) . ? C8 H8 0.9500 . ? C9 C10 1.368(4) . ? C9 H9 0.9500 . ? C10 C11 1.384(3) . ? C10 H10 0.9500 . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.392(2) . ? C13 C14 1.396(3) . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C16 C17 1.374(3) . ? C16 H16 0.9500 . ? C17 C18 1.394(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.392(2) . ? C19 C20 1.399(3) . ? C20 C21 1.390(3) . ? C20 H20 0.9500 . ? C21 C22 1.382(3) . ? C21 H21 0.9500 . ? C22 C23 1.380(3) . ? C22 H22 0.9500 . ? C23 C24 1.386(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 115.93(15) . . ? O1 C1 C6 118.85(16) . . ? C2 C1 C6 125.07(15) . . ? C5 C2 C4 108.74(19) . . ? C5 C2 C3 108.86(18) . . ? C4 C2 C3 107.68(17) . . ? C5 C2 C1 118.04(16) . . ? C4 C2 C1 105.98(16) . . ? C3 C2 C1 107.11(16) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C13 C6 C7 105.08(14) . . ? C13 C6 C19 114.71(14) . . ? C7 C6 C19 111.14(12) . . ? C13 C6 C1 112.20(13) . . ? C7 C6 C1 108.84(14) . . ? C19 C6 C1 104.88(14) . . ? C8 C7 C12 117.67(18) . . ? C8 C7 C6 123.55(17) . . ? C12 C7 C6 118.67(16) . . ? C9 C8 C7 120.3(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 121.1(2) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 119.6(2) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 119.7(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C7 121.56(19) . . ? C11 C12 H12 119.2 . . ? C7 C12 H12 119.2 . . ? C18 C13 C14 117.20(16) . . ? C18 C13 C6 122.25(15) . . ? C14 C13 C6 120.31(14) . . ? C15 C14 C13 121.39(16) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 C15 C14 120.30(18) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.52(18) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.11(18) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C13 C18 C17 121.38(18) . . ? C13 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C24 C19 C20 117.56(16) . . ? C24 C19 C6 123.84(16) . . ? C20 C19 C6 118.56(15) . . ? C21 C20 C19 121.07(17) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C20 120.38(18) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C23 C22 C21 119.13(18) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 120.71(19) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C23 C24 C19 121.14(18) . . ? C23 C24 H24 119.4 . . ? C19 C24 H24 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C5 -171.52(18) . . . . ? C6 C1 C2 C5 13.1(3) . . . . ? O1 C1 C2 C4 66.4(2) . . . . ? C6 C1 C2 C4 -108.94(19) . . . . ? O1 C1 C2 C3 -48.4(2) . . . . ? C6 C1 C2 C3 136.30(17) . . . . ? O1 C1 C6 C13 117.41(17) . . . . ? C2 C1 C6 C13 -67.4(2) . . . . ? O1 C1 C6 C7 1.5(2) . . . . ? C2 C1 C6 C7 176.77(16) . . . . ? O1 C1 C6 C19 -117.46(17) . . . . ? C2 C1 C6 C19 57.76(19) . . . . ? C13 C6 C7 C8 112.07(18) . . . . ? C19 C6 C7 C8 -12.6(2) . . . . ? C1 C6 C7 C8 -127.58(17) . . . . ? C13 C6 C7 C12 -64.10(18) . . . . ? C19 C6 C7 C12 171.27(14) . . . . ? C1 C6 C7 C12 56.26(19) . . . . ? C12 C7 C8 C9 -0.7(3) . . . . ? C6 C7 C8 C9 -176.94(18) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C11 0.6(4) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C7 -1.1(3) . . . . ? C8 C7 C12 C11 1.4(3) . . . . ? C6 C7 C12 C11 177.81(16) . . . . ? C7 C6 C13 C18 108.63(18) . . . . ? C19 C6 C13 C18 -129.02(18) . . . . ? C1 C6 C13 C18 -9.5(2) . . . . ? C7 C6 C13 C14 -65.6(2) . . . . ? C19 C6 C13 C14 56.8(2) . . . . ? C1 C6 C13 C14 176.31(16) . . . . ? C18 C13 C14 C15 2.8(3) . . . . ? C6 C13 C14 C15 177.35(17) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 -1.8(3) . . . . ? C15 C16 C17 C18 1.3(3) . . . . ? C14 C13 C18 C17 -3.4(3) . . . . ? C6 C13 C18 C17 -177.75(17) . . . . ? C16 C17 C18 C13 1.3(3) . . . . ? C13 C6 C19 C24 2.5(2) . . . . ? C7 C6 C19 C24 121.47(19) . . . . ? C1 C6 C19 C24 -121.09(18) . . . . ? C13 C6 C19 C20 -179.88(16) . . . . ? C7 C6 C19 C20 -60.9(2) . . . . ? C1 C6 C19 C20 56.58(19) . . . . ? C24 C19 C20 C21 0.3(3) . . . . ? C6 C19 C20 C21 -177.49(18) . . . . ? C19 C20 C21 C22 -0.4(3) . . . . ? C20 C21 C22 C23 0.5(3) . . . . ? C21 C22 C23 C24 -0.5(3) . . . . ? C22 C23 C24 C19 0.4(3) . . . . ? C20 C19 C24 C23 -0.3(3) . . . . ? C6 C19 C24 C23 177.39(18) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 0.145 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.028 # Attachment 'js226.cif' data_1c _database_code_depnum_ccdc_archive 'CCDC 837500' #TrackingRef 'js226.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 O' _chemical_formula_weight 314.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Aba2 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' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/2, y+1, z+1/2' 'x+1/2, -y+1, z+1/2' _cell_length_a 17.1668(14) _cell_length_b 25.851(2) _cell_length_c 16.0760(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7134.3(10) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6971 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 25.02 _exptl_crystal_description chip _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2688 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.803 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/ADSC CCD' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7339 _diffrn_reflns_av_R_equivalents 0.0590 _diffrn_reflns_av_sigmaI/netI 0.0915 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 27.55 _reflns_number_total 7339 _reflns_number_gt 4895 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0230P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2.9(10) _refine_ls_number_reflns 7339 _refine_ls_number_parameters 437 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0590 _refine_ls_wR_factor_gt 0.0536 _refine_ls_goodness_of_fit_ref 0.825 _refine_ls_restrained_S_all 0.825 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.27343(11) 0.17978(7) 0.04746(11) 0.0261(5) Uani 1 1 d . . . C2 C 0.27878(9) 0.12544(6) 0.08986(10) 0.0204(4) Uani 1 1 d . . . C3 C 0.32078(9) 0.12811(7) 0.17401(11) 0.0210(4) Uani 1 1 d . . . C4 C 0.36174(10) 0.08624(7) 0.20660(11) 0.0264(4) Uani 1 1 d . . . H4 H 0.3679 0.0558 0.1742 0.032 Uiso 1 1 calc R . . C5 C 0.39354(10) 0.08843(9) 0.28566(12) 0.0354(5) Uani 1 1 d . . . H5 H 0.4227 0.0600 0.3063 0.042 Uiso 1 1 calc R . . C6 C 0.38317(10) 0.13180(9) 0.33485(12) 0.0378(5) Uani 1 1 d . . . H6 H 0.4052 0.1333 0.3890 0.045 Uiso 1 1 calc R . . C7 C 0.34065(11) 0.17275(8) 0.30461(13) 0.0358(5) Uani 1 1 d . . . H7 H 0.3323 0.2024 0.3384 0.043 Uiso 1 1 calc R . . C8 C 0.30989(10) 0.17082(7) 0.22487(11) 0.0278(4) Uani 1 1 d . . . H8 H 0.2807 0.1994 0.2047 0.033 Uiso 1 1 calc R . . C9 C 0.19813(10) 0.10280(7) 0.11063(10) 0.0213(4) Uani 1 1 d . . . C10 C 0.18710(10) 0.04963(7) 0.11002(10) 0.0272(5) Uani 1 1 d . . . H10 H 0.2275 0.0278 0.0902 0.033 Uiso 1 1 calc R . . C11 C 0.11776(10) 0.02786(8) 0.13794(11) 0.0315(5) Uani 1 1 d . . . H11 H 0.1110 -0.0086 0.1373 0.038 Uiso 1 1 calc R . . C12 C 0.05865(10) 0.05961(8) 0.16667(11) 0.0323(5) Uani 1 1 d . . . H12 H 0.0110 0.0450 0.1852 0.039 Uiso 1 1 calc R . . C13 C 0.06895(10) 0.11242(8) 0.16835(12) 0.0323(5) Uani 1 1 d . . . H13 H 0.0284 0.1342 0.1881 0.039 Uiso 1 1 calc R . . C14 C 0.13842(10) 0.13384(7) 0.14131(11) 0.0294(5) Uani 1 1 d . . . H14 H 0.1454 0.1703 0.1437 0.035 Uiso 1 1 calc R . . C15 C 0.32086(10) 0.09486(6) 0.02077(11) 0.0211(4) Uani 1 1 d . . . C16 C 0.27870(10) 0.08144(7) -0.05006(11) 0.0292(5) Uani 1 1 d . . . H16 H 0.2242 0.0878 -0.0514 0.035 Uiso 1 1 calc R . . C17 C 0.31425(12) 0.05917(8) -0.11841(12) 0.0351(5) Uani 1 1 d . . . H17 H 0.2845 0.0510 -0.1665 0.042 Uiso 1 1 calc R . . C18 C 0.39367(12) 0.04882(8) -0.11652(13) 0.0354(5) Uani 1 1 d . . . H18 H 0.4183 0.0326 -0.1625 0.043 Uiso 1 1 calc R . . C19 C 0.43628(11) 0.06236(7) -0.04744(12) 0.0288(5) Uani 1 1 d . . . H19 H 0.4906 0.0555 -0.0462 0.035 Uiso 1 1 calc R . . C20 C 0.40096(10) 0.08583(7) 0.02041(11) 0.0232(4) Uani 1 1 d . . . H20 H 0.4316 0.0958 0.0670 0.028 Uiso 1 1 calc R . . C21 C 0.34884(11) 0.21016(7) 0.03736(13) 0.0333(5) Uani 1 1 d . . . H21 H 0.3904 0.1932 0.0713 0.040 Uiso 1 1 calc R . . C22 C 0.37374(12) 0.20994(8) -0.05419(13) 0.0471(6) Uani 1 1 d . . . H22A H 0.3802 0.1742 -0.0731 0.071 Uiso 1 1 calc R . . H22B H 0.4232 0.2285 -0.0601 0.071 Uiso 1 1 calc R . . H22C H 0.3337 0.2270 -0.0879 0.071 Uiso 1 1 calc R . . C23 C 0.33795(13) 0.26590(7) 0.06813(15) 0.0496(6) Uani 1 1 d . . . H23A H 0.2956 0.2824 0.0370 0.074 Uiso 1 1 calc R . . H23B H 0.3863 0.2854 0.0596 0.074 Uiso 1 1 calc R . . H23C H 0.3250 0.2656 0.1275 0.074 Uiso 1 1 calc R . . C24 C 0.34785(9) -0.18733(7) 0.23912(10) 0.0204(4) Uani 1 1 d . . . C25 C 0.31452(9) -0.13397(6) 0.26851(10) 0.0183(4) Uani 1 1 d . . . C26 C 0.23119(9) -0.13925(6) 0.30322(11) 0.0200(4) Uani 1 1 d . . . C27 C 0.17426(10) -0.10211(7) 0.28836(11) 0.0280(5) Uani 1 1 d . . . H27 H 0.1859 -0.0733 0.2539 0.034 Uiso 1 1 calc R . . C28 C 0.10061(11) -0.10667(8) 0.32322(12) 0.0353(5) Uani 1 1 d . . . H28 H 0.0623 -0.0812 0.3117 0.042 Uiso 1 1 calc R . . C29 C 0.08246(11) -0.14759(8) 0.37412(13) 0.0386(6) Uani 1 1 d . . . H29 H 0.0317 -0.1507 0.3970 0.046 Uiso 1 1 calc R . . C30 C 0.13883(11) -0.18411(8) 0.39169(12) 0.0346(5) Uani 1 1 d . . . H30 H 0.1271 -0.2124 0.4273 0.042 Uiso 1 1 calc R . . C31 C 0.21245(10) -0.17943(7) 0.35732(11) 0.0270(5) Uani 1 1 d . . . H31 H 0.2512 -0.2043 0.3710 0.032 Uiso 1 1 calc R . . C32 C 0.36253(9) -0.10982(7) 0.33913(10) 0.0199(4) Uani 1 1 d . . . C33 C 0.35650(10) -0.05703(7) 0.35647(11) 0.0260(4) Uani 1 1 d . . . H33 H 0.3248 -0.0357 0.3223 0.031 Uiso 1 1 calc R . . C34 C 0.39632(12) -0.03539(8) 0.42303(11) 0.0348(5) Uani 1 1 d . . . H34 H 0.3923 0.0007 0.4337 0.042 Uiso 1 1 calc R . . C35 C 0.44178(11) -0.06614(8) 0.47380(11) 0.0342(5) Uani 1 1 d . . . H35 H 0.4696 -0.0512 0.5189 0.041 Uiso 1 1 calc R . . C36 C 0.44676(10) -0.11847(8) 0.45896(11) 0.0309(5) Uani 1 1 d . . . H36 H 0.4774 -0.1397 0.4943 0.037 Uiso 1 1 calc R . . C37 C 0.40696(10) -0.14024(7) 0.39229(11) 0.0244(4) Uani 1 1 d . . . H37 H 0.4102 -0.1765 0.3829 0.029 Uiso 1 1 calc R . . C38 C 0.31778(10) -0.10297(6) 0.18658(10) 0.0211(4) Uani 1 1 d . . . C39 C 0.26314(11) -0.11341(7) 0.12429(11) 0.0275(5) Uani 1 1 d . . . H39 H 0.2214 -0.1365 0.1356 0.033 Uiso 1 1 calc R . . C40 C 0.26877(12) -0.09075(7) 0.04657(12) 0.0348(5) Uani 1 1 d . . . H40 H 0.2309 -0.0983 0.0052 0.042 Uiso 1 1 calc R . . C41 C 0.32948(12) -0.05702(8) 0.02880(12) 0.0379(5) Uani 1 1 d . . . H41 H 0.3334 -0.0413 -0.0244 0.046 Uiso 1 1 calc R . . C42 C 0.38399(12) -0.04672(7) 0.08960(12) 0.0344(5) Uani 1 1 d . . . H42 H 0.4257 -0.0237 0.0779 0.041 Uiso 1 1 calc R . . C43 C 0.37880(11) -0.06947(7) 0.16773(11) 0.0263(4) Uani 1 1 d . . . H43 H 0.4172 -0.0621 0.2086 0.032 Uiso 1 1 calc R . . C44 C 0.43181(9) -0.19027(7) 0.20677(11) 0.0252(4) Uani 1 1 d . . . H44 H 0.4601 -0.1576 0.2209 0.030 Uiso 1 1 calc R . . C45 C 0.42797(11) -0.19679(8) 0.11173(11) 0.0368(5) Uani 1 1 d . . . H45A H 0.4807 -0.2016 0.0897 0.055 Uiso 1 1 calc R . . H45B H 0.4046 -0.1658 0.0869 0.055 Uiso 1 1 calc R . . H45C H 0.3961 -0.2271 0.0981 0.055 Uiso 1 1 calc R . . C46 C 0.47416(10) -0.23662(7) 0.24523(13) 0.0361(5) Uani 1 1 d . . . H46A H 0.4816 -0.2306 0.3049 0.054 Uiso 1 1 calc R . . H46B H 0.5250 -0.2409 0.2184 0.054 Uiso 1 1 calc R . . H46C H 0.4430 -0.2680 0.2370 0.054 Uiso 1 1 calc R . . O1 O 0.21345(7) 0.19565(5) 0.01705(8) 0.0366(3) Uani 1 1 d . . . O2 O 0.30672(6) -0.22534(4) 0.23481(8) 0.0298(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0272(11) 0.0255(11) 0.0257(11) 0.0014(9) 0.0049(9) 0.0071(9) C2 0.0193(9) 0.0181(10) 0.0238(10) 0.0026(8) 0.0014(8) 0.0014(8) C3 0.0161(9) 0.0223(11) 0.0244(10) 0.0027(9) 0.0036(8) -0.0036(8) C4 0.0271(10) 0.0241(11) 0.0279(11) 0.0041(9) 0.0032(9) 0.0031(9) C5 0.0262(11) 0.0458(14) 0.0342(12) 0.0165(11) 0.0008(10) 0.0066(10) C6 0.0270(11) 0.0606(16) 0.0259(12) 0.0034(11) -0.0029(9) -0.0116(11) C7 0.0352(11) 0.0360(14) 0.0361(13) -0.0096(11) 0.0044(10) -0.0122(10) C8 0.0260(10) 0.0253(11) 0.0320(12) 0.0014(10) 0.0013(9) -0.0024(9) C9 0.0178(10) 0.0260(11) 0.0201(10) -0.0002(9) -0.0013(8) -0.0007(8) C10 0.0258(10) 0.0275(12) 0.0284(11) -0.0017(9) 0.0030(9) 0.0012(9) C11 0.0345(12) 0.0307(12) 0.0294(11) -0.0061(10) 0.0016(10) -0.0125(10) C12 0.0199(10) 0.0529(15) 0.0241(10) -0.0048(10) 0.0012(9) -0.0129(10) C13 0.0211(10) 0.0399(14) 0.0360(12) -0.0035(10) 0.0049(9) 0.0030(9) C14 0.0265(10) 0.0240(11) 0.0378(12) -0.0002(10) 0.0030(9) 0.0011(9) C15 0.0238(10) 0.0158(10) 0.0236(10) 0.0074(8) 0.0029(9) 0.0011(8) C16 0.0266(10) 0.0325(12) 0.0285(11) 0.0075(10) 0.0009(10) 0.0017(9) C17 0.0421(13) 0.0419(14) 0.0214(11) 0.0010(10) 0.0021(10) -0.0019(11) C18 0.0448(13) 0.0334(12) 0.0280(12) 0.0038(10) 0.0153(11) 0.0052(10) C19 0.0277(10) 0.0265(12) 0.0322(11) 0.0106(10) 0.0097(10) 0.0054(9) C20 0.0252(10) 0.0212(10) 0.0232(10) 0.0076(9) 0.0034(9) -0.0003(8) C21 0.0279(11) 0.0263(11) 0.0458(13) 0.0138(10) 0.0053(10) 0.0026(9) C22 0.0485(14) 0.0357(14) 0.0571(15) 0.0214(12) 0.0254(12) 0.0112(11) C23 0.0592(16) 0.0276(13) 0.0621(16) 0.0098(12) 0.0074(13) -0.0043(11) C24 0.0222(9) 0.0216(11) 0.0173(10) 0.0023(8) -0.0037(8) -0.0001(9) C25 0.0197(9) 0.0172(10) 0.0181(9) 0.0029(8) -0.0007(8) -0.0011(8) C26 0.0210(9) 0.0197(10) 0.0192(10) -0.0042(9) -0.0030(8) -0.0034(8) C27 0.0306(11) 0.0300(12) 0.0234(11) 0.0025(9) -0.0012(9) 0.0039(9) C28 0.0251(11) 0.0460(15) 0.0348(12) -0.0058(11) -0.0031(10) 0.0099(10) C29 0.0261(11) 0.0465(15) 0.0431(14) -0.0141(12) 0.0084(10) -0.0055(11) C30 0.0398(13) 0.0286(13) 0.0355(12) -0.0014(10) 0.0128(10) -0.0055(11) C31 0.0282(11) 0.0254(11) 0.0275(11) 0.0026(9) 0.0043(9) 0.0028(9) C32 0.0197(9) 0.0228(11) 0.0173(10) 0.0006(8) 0.0032(8) -0.0054(8) C33 0.0354(11) 0.0217(12) 0.0209(10) 0.0019(9) -0.0003(9) -0.0028(9) C34 0.0519(14) 0.0261(12) 0.0265(12) -0.0053(10) 0.0055(10) -0.0132(11) C35 0.0389(12) 0.0447(14) 0.0189(11) -0.0077(10) 0.0019(9) -0.0144(10) C36 0.0274(11) 0.0443(14) 0.0210(11) 0.0035(10) -0.0005(9) 0.0008(10) C37 0.0281(10) 0.0229(11) 0.0222(10) -0.0014(9) 0.0013(9) -0.0011(9) C38 0.0290(10) 0.0174(10) 0.0171(10) -0.0014(8) 0.0022(8) 0.0036(8) C39 0.0346(11) 0.0261(11) 0.0219(11) -0.0017(9) -0.0004(9) 0.0045(9) C40 0.0478(13) 0.0339(12) 0.0227(12) -0.0020(10) -0.0044(10) 0.0134(11) C41 0.0604(14) 0.0311(13) 0.0222(11) 0.0077(10) 0.0117(11) 0.0149(11) C42 0.0458(13) 0.0233(12) 0.0342(13) 0.0031(10) 0.0168(11) 0.0021(10) C43 0.0351(11) 0.0221(11) 0.0216(10) -0.0016(9) 0.0046(9) 0.0006(9) C44 0.0238(10) 0.0233(11) 0.0285(11) -0.0027(9) 0.0035(8) -0.0033(8) C45 0.0367(12) 0.0409(13) 0.0329(12) -0.0046(10) 0.0090(10) 0.0035(10) C46 0.0286(11) 0.0360(13) 0.0437(12) -0.0030(11) -0.0012(10) 0.0058(9) O1 0.0305(8) 0.0374(9) 0.0418(9) 0.0115(7) -0.0022(7) 0.0110(6) O2 0.0282(7) 0.0216(7) 0.0395(8) -0.0048(7) 0.0034(6) -0.0055(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2113(19) . ? C1 C21 1.523(2) . ? C1 C2 1.564(2) . ? C2 C3 1.535(2) . ? C2 C9 1.540(2) . ? C2 C15 1.543(2) . ? C3 C8 1.386(2) . ? C3 C4 1.393(2) . ? C4 C5 1.384(2) . ? C4 H4 0.9500 . ? C5 C6 1.383(3) . ? C5 H5 0.9500 . ? C6 C7 1.375(3) . ? C6 H6 0.9500 . ? C7 C8 1.387(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.387(2) . ? C9 C14 1.392(2) . ? C10 C11 1.391(2) . ? C10 H10 0.9500 . ? C11 C12 1.384(2) . ? C11 H11 0.9500 . ? C12 C13 1.377(3) . ? C12 H12 0.9500 . ? C13 C14 1.385(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.393(2) . ? C15 C20 1.395(2) . ? C16 C17 1.383(2) . ? C16 H16 0.9500 . ? C17 C18 1.390(3) . ? C17 H17 0.9500 . ? C18 C19 1.375(3) . ? C18 H18 0.9500 . ? C19 C20 1.388(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.533(3) . ? C21 C23 1.535(3) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 O2 1.2120(18) . ? C24 C44 1.534(2) . ? C24 C25 1.566(2) . ? C25 C32 1.535(2) . ? C25 C26 1.542(2) . ? C25 C38 1.543(2) . ? C26 C27 1.391(2) . ? C26 C31 1.392(2) . ? C27 C28 1.388(2) . ? C27 H27 0.9500 . ? C28 C29 1.373(3) . ? C28 H28 0.9500 . ? C29 C30 1.381(3) . ? C29 H29 0.9500 . ? C30 C31 1.385(2) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 C37 1.390(2) . ? C32 C33 1.397(2) . ? C33 C34 1.388(2) . ? C33 H33 0.9500 . ? C34 C35 1.381(3) . ? C34 H34 0.9500 . ? C35 C36 1.376(3) . ? C35 H35 0.9500 . ? C36 C37 1.390(2) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 C43 1.393(2) . ? C38 C39 1.398(2) . ? C39 C40 1.383(2) . ? C39 H39 0.9500 . ? C40 C41 1.389(3) . ? C40 H40 0.9500 . ? C41 C42 1.379(3) . ? C41 H41 0.9500 . ? C42 C43 1.390(2) . ? C42 H42 0.9500 . ? C43 H43 0.9500 . ? C44 C46 1.532(2) . ? C44 C45 1.539(2) . ? C44 H44 1.0000 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C21 120.33(17) . . ? O1 C1 C2 121.99(16) . . ? C21 C1 C2 117.37(15) . . ? C3 C2 C9 104.39(13) . . ? C3 C2 C15 115.96(13) . . ? C9 C2 C15 112.48(14) . . ? C3 C2 C1 111.79(14) . . ? C9 C2 C1 112.52(14) . . ? C15 C2 C1 100.02(13) . . ? C8 C3 C4 117.71(16) . . ? C8 C3 C2 119.50(15) . . ? C4 C3 C2 122.26(16) . . ? C5 C4 C3 120.83(18) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 120.48(19) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 119.35(19) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 120.08(19) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C3 C8 C7 121.48(18) . . ? C3 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C10 C9 C14 118.23(17) . . ? C10 C9 C2 119.85(16) . . ? C14 C9 C2 121.33(16) . . ? C9 C10 C11 121.03(18) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 119.66(19) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 120.02(18) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.05(18) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 120.99(18) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? C16 C15 C20 117.85(16) . . ? C16 C15 C2 118.21(15) . . ? C20 C15 C2 123.39(16) . . ? C17 C16 C15 121.60(17) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 119.73(19) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 119.38(18) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 120.91(17) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C15 120.48(17) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? C1 C21 C22 109.74(16) . . ? C1 C21 C23 110.25(16) . . ? C22 C21 C23 110.29(16) . . ? C1 C21 H21 108.8 . . ? C22 C21 H21 108.8 . . ? C23 C21 H21 108.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O2 C24 C44 119.19(15) . . ? O2 C24 C25 121.23(14) . . ? C44 C24 C25 119.28(15) . . ? C32 C25 C26 105.45(13) . . ? C32 C25 C38 113.62(13) . . ? C26 C25 C38 112.88(13) . . ? C32 C25 C24 112.64(13) . . ? C26 C25 C24 111.73(13) . . ? C38 C25 C24 100.75(13) . . ? C27 C26 C31 117.39(16) . . ? C27 C26 C25 121.92(16) . . ? C31 C26 C25 120.44(15) . . ? C28 C27 C26 120.80(18) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C29 C28 C27 120.85(19) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 119.31(18) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C29 C30 C31 119.88(19) . . ? C29 C30 H30 120.1 . . ? C31 C30 H30 120.1 . . ? C30 C31 C26 121.69(17) . . ? C30 C31 H31 119.2 . . ? C26 C31 H31 119.2 . . ? C37 C32 C33 118.09(16) . . ? C37 C32 C25 121.29(16) . . ? C33 C32 C25 120.33(15) . . ? C34 C33 C32 120.76(18) . . ? C34 C33 H33 119.6 . . ? C32 C33 H33 119.6 . . ? C35 C34 C33 120.13(19) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C36 C35 C34 119.89(18) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C35 C36 C37 120.08(18) . . ? C35 C36 H36 120.0 . . ? C37 C36 H36 120.0 . . ? C32 C37 C36 120.99(18) . . ? C32 C37 H37 119.5 . . ? C36 C37 H37 119.5 . . ? C43 C38 C39 117.95(16) . . ? C43 C38 C25 122.42(15) . . ? C39 C38 C25 119.13(15) . . ? C40 C39 C38 121.21(17) . . ? C40 C39 H39 119.4 . . ? C38 C39 H39 119.4 . . ? C39 C40 C41 120.28(18) . . ? C39 C40 H40 119.9 . . ? C41 C40 H40 119.9 . . ? C42 C41 C40 118.99(18) . . ? C42 C41 H41 120.5 . . ? C40 C41 H41 120.5 . . ? C41 C42 C43 121.01(18) . . ? C41 C42 H42 119.5 . . ? C43 C42 H42 119.5 . . ? C42 C43 C38 120.54(18) . . ? C42 C43 H43 119.7 . . ? C38 C43 H43 119.7 . . ? C46 C44 C24 110.35(14) . . ? C46 C44 C45 109.59(15) . . ? C24 C44 C45 107.57(14) . . ? C46 C44 H44 109.8 . . ? C24 C44 H44 109.8 . . ? C45 C44 H44 109.8 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C44 C46 H46A 109.5 . . ? C44 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C44 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -133.62(17) . . . . ? C21 C1 C2 C3 52.73(19) . . . . ? O1 C1 C2 C9 -16.5(2) . . . . ? C21 C1 C2 C9 169.83(15) . . . . ? O1 C1 C2 C15 103.06(18) . . . . ? C21 C1 C2 C15 -70.59(18) . . . . ? C9 C2 C3 C8 -85.31(18) . . . . ? C15 C2 C3 C8 150.36(15) . . . . ? C1 C2 C3 C8 36.6(2) . . . . ? C9 C2 C3 C4 86.11(18) . . . . ? C15 C2 C3 C4 -38.2(2) . . . . ? C1 C2 C3 C4 -151.99(15) . . . . ? C8 C3 C4 C5 -3.0(2) . . . . ? C2 C3 C4 C5 -174.59(15) . . . . ? C3 C4 C5 C6 2.0(3) . . . . ? C4 C5 C6 C7 0.2(3) . . . . ? C5 C6 C7 C8 -1.3(3) . . . . ? C4 C3 C8 C7 2.0(2) . . . . ? C2 C3 C8 C7 173.81(15) . . . . ? C6 C7 C8 C3 0.1(3) . . . . ? C3 C2 C9 C10 -89.41(18) . . . . ? C15 C2 C9 C10 37.1(2) . . . . ? C1 C2 C9 C10 149.17(15) . . . . ? C3 C2 C9 C14 81.56(19) . . . . ? C15 C2 C9 C14 -151.91(16) . . . . ? C1 C2 C9 C14 -39.9(2) . . . . ? C14 C9 C10 C11 1.1(3) . . . . ? C2 C9 C10 C11 172.33(16) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C9 1.3(3) . . . . ? C10 C9 C14 C13 -1.8(3) . . . . ? C2 C9 C14 C13 -172.90(17) . . . . ? C3 C2 C15 C16 166.07(15) . . . . ? C9 C2 C15 C16 46.0(2) . . . . ? C1 C2 C15 C16 -73.58(18) . . . . ? C3 C2 C15 C20 -22.6(2) . . . . ? C9 C2 C15 C20 -142.65(16) . . . . ? C1 C2 C15 C20 97.73(18) . . . . ? C20 C15 C16 C17 1.0(3) . . . . ? C2 C15 C16 C17 172.75(16) . . . . ? C15 C16 C17 C18 1.2(3) . . . . ? C16 C17 C18 C19 -1.9(3) . . . . ? C17 C18 C19 C20 0.4(3) . . . . ? C18 C19 C20 C15 1.8(3) . . . . ? C16 C15 C20 C19 -2.5(2) . . . . ? C2 C15 C20 C19 -173.80(15) . . . . ? O1 C1 C21 C22 -66.8(2) . . . . ? C2 C1 C21 C22 106.94(17) . . . . ? O1 C1 C21 C23 54.9(2) . . . . ? C2 C1 C21 C23 -131.38(17) . . . . ? O2 C24 C25 C32 127.92(16) . . . . ? C44 C24 C25 C32 -58.40(19) . . . . ? O2 C24 C25 C26 9.4(2) . . . . ? C44 C24 C25 C26 -176.89(14) . . . . ? O2 C24 C25 C38 -110.68(18) . . . . ? C44 C24 C25 C38 63.00(17) . . . . ? C32 C25 C26 C27 95.80(18) . . . . ? C38 C25 C26 C27 -28.8(2) . . . . ? C24 C25 C26 C27 -141.51(16) . . . . ? C32 C25 C26 C31 -78.23(19) . . . . ? C38 C25 C26 C31 157.17(15) . . . . ? C24 C25 C26 C31 44.5(2) . . . . ? C31 C26 C27 C28 -3.0(3) . . . . ? C25 C26 C27 C28 -177.26(16) . . . . ? C26 C27 C28 C29 0.9(3) . . . . ? C27 C28 C29 C30 1.0(3) . . . . ? C28 C29 C30 C31 -0.7(3) . . . . ? C29 C30 C31 C26 -1.6(3) . . . . ? C27 C26 C31 C30 3.5(3) . . . . ? C25 C26 C31 C30 177.75(16) . . . . ? C26 C25 C32 C37 96.85(17) . . . . ? C38 C25 C32 C37 -139.02(15) . . . . ? C24 C25 C32 C37 -25.3(2) . . . . ? C26 C25 C32 C33 -76.87(18) . . . . ? C38 C25 C32 C33 47.3(2) . . . . ? C24 C25 C32 C33 161.03(15) . . . . ? C37 C32 C33 C34 2.5(3) . . . . ? C25 C32 C33 C34 176.41(16) . . . . ? C32 C33 C34 C35 -0.9(3) . . . . ? C33 C34 C35 C36 -0.8(3) . . . . ? C34 C35 C36 C37 0.9(3) . . . . ? C33 C32 C37 C36 -2.5(2) . . . . ? C25 C32 C37 C36 -176.31(15) . . . . ? C35 C36 C37 C32 0.8(3) . . . . ? C32 C25 C38 C43 23.3(2) . . . . ? C26 C25 C38 C43 143.29(16) . . . . ? C24 C25 C38 C43 -97.43(17) . . . . ? C32 C25 C38 C39 -164.96(15) . . . . ? C26 C25 C38 C39 -45.0(2) . . . . ? C24 C25 C38 C39 74.33(17) . . . . ? C43 C38 C39 C40 -0.8(2) . . . . ? C25 C38 C39 C40 -172.91(16) . . . . ? C38 C39 C40 C41 0.2(3) . . . . ? C39 C40 C41 C42 0.3(3) . . . . ? C40 C41 C42 C43 -0.1(3) . . . . ? C41 C42 C43 C38 -0.5(3) . . . . ? C39 C38 C43 C42 1.0(2) . . . . ? C25 C38 C43 C42 172.81(16) . . . . ? O2 C24 C44 C46 -52.0(2) . . . . ? C25 C24 C44 C46 134.23(16) . . . . ? O2 C24 C44 C45 67.5(2) . . . . ? C25 C24 C44 C45 -106.26(17) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.164 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.036