# Electronic Supplementary Material (ESI) for Chemical Communications # 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_global data_ywj-7 #TrackingRef 'm-OC3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H34 O2' _chemical_formula_sum 'C36 H34 O2' _chemical_formula_weight 498.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 5.4269(11) _cell_length_b 8.9384(18) _cell_length_c 14.968(3) _cell_angle_alpha 74.64(3) _cell_angle_beta 81.57(3) _cell_angle_gamma 77.00(3) _cell_volume 679.3(2) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 266 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9639 _exptl_absorpt_correction_T_max 0.9782 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5374 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2391 _reflns_number_gt 1603 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1031P)^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 2391 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1594 _refine_ls_wR_factor_gt 0.1350 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 0.1259(4) 0.2694(2) 0.52322(14) 0.0546(5) Uani 1 1 d . . . H1 H 0.1426 0.3700 0.4880 0.065 Uiso 1 1 calc R . . C2 C -0.0786(4) 0.2528(3) 0.58555(16) 0.0620(6) Uani 1 1 d . . . H2 H -0.2001 0.3415 0.5929 0.074 Uiso 1 1 calc R . . C3 C -0.1090(4) 0.1020(3) 0.63947(15) 0.0632(6) Uani 1 1 d . . . H3 H -0.2514 0.0915 0.6818 0.076 Uiso 1 1 calc R . . C4 C 0.0668(4) -0.0271(2) 0.63017(14) 0.0556(5) Uani 1 1 d . . . H4 H 0.0434 -0.1257 0.6666 0.067 Uiso 1 1 calc R . . C5 C 0.2875(3) -0.0170(2) 0.56615(12) 0.0452(5) Uani 1 1 d . . . C6 C 0.3175(4) 0.1365(2) 0.50990(12) 0.0447(5) Uani 1 1 d . . . C7 C 0.5282(4) 0.1524(2) 0.44363(12) 0.0456(5) Uani 1 1 d . . . C8 C 0.5631(4) 0.3106(2) 0.38639(14) 0.0539(5) Uani 1 1 d . . . H8 H 0.6445 0.3669 0.4130 0.065 Uiso 1 1 calc R . . C9 C 0.4947(4) 0.3785(2) 0.30514(14) 0.0608(6) Uani 1 1 d . . . H9 H 0.4109 0.3220 0.2796 0.073 Uiso 1 1 calc R . . C10 C 0.5301(4) 0.5341(2) 0.24612(13) 0.0472(5) Uani 1 1 d . . . C11 C 0.6810(4) 0.6233(2) 0.26833(14) 0.0531(5) Uani 1 1 d . . . H11 H 0.7675 0.5841 0.3215 0.064 Uiso 1 1 calc R . . C12 C 0.7029(4) 0.7699(2) 0.21163(14) 0.0542(5) Uani 1 1 d . . . H12 H 0.8028 0.8291 0.2276 0.065 Uiso 1 1 calc R . . C13 C 0.5793(4) 0.8302(2) 0.13176(14) 0.0508(5) Uani 1 1 d . . . H13 H 0.5943 0.9296 0.0944 0.061 Uiso 1 1 calc R . . C14 C 0.4325(3) 0.7410(2) 0.10785(13) 0.0438(4) Uani 1 1 d . . . C15 C 0.4087(4) 0.5939(2) 0.16462(13) 0.0498(5) Uani 1 1 d . . . H15 H 0.3104 0.5343 0.1481 0.060 Uiso 1 1 calc R . . C16 C 0.1757(4) 0.7189(2) -0.00437(13) 0.0510(5) Uani 1 1 d . . . H16A H 0.0438 0.6868 0.0435 0.061 Uiso 1 1 calc R . . H16B H 0.2865 0.6246 -0.0180 0.061 Uiso 1 1 calc R . . C17 C 0.0593(4) 0.8219(2) -0.09080(14) 0.0584(5) Uani 1 1 d . . . H17A H 0.1929 0.8502 -0.1389 0.070 Uiso 1 1 calc R . . H17B H -0.0432 0.9186 -0.0773 0.070 Uiso 1 1 calc R . . C18 C -0.1058(4) 0.7363(3) -0.12585(16) 0.0702(7) Uani 1 1 d . . . H18A H -0.0035 0.6419 -0.1407 0.105 Uiso 1 1 calc R . . H18B H -0.1793 0.8043 -0.1805 0.105 Uiso 1 1 calc R . . H18C H -0.2386 0.7087 -0.0784 0.105 Uiso 1 1 calc R . . O1 O 0.3179(3) 0.80899(15) 0.02701(9) 0.0579(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 0.0740(13) 0.0338(10) 0.0529(12) -0.0045(9) -0.0141(10) -0.0062(9) C2 0.0705(14) 0.0501(12) 0.0614(14) -0.0159(10) -0.0086(11) 0.0010(10) C3 0.0651(13) 0.0623(14) 0.0568(13) -0.0099(11) -0.0006(11) -0.0096(11) C4 0.0662(12) 0.0505(12) 0.0457(11) -0.0002(9) -0.0067(9) -0.0151(10) C5 0.0608(11) 0.0373(10) 0.0356(10) 0.0002(8) -0.0133(8) -0.0108(8) C6 0.0622(11) 0.0328(9) 0.0383(10) -0.0015(7) -0.0169(9) -0.0080(8) C7 0.0632(11) 0.0327(9) 0.0394(10) 0.0018(8) -0.0165(9) -0.0115(8) C8 0.0747(13) 0.0353(10) 0.0513(12) 0.0026(8) -0.0198(10) -0.0166(9) C9 0.0907(15) 0.0442(11) 0.0509(12) 0.0080(9) -0.0256(11) -0.0304(11) C10 0.0623(11) 0.0345(10) 0.0418(10) -0.0002(8) -0.0084(9) -0.0117(8) C11 0.0652(12) 0.0448(11) 0.0477(11) 0.0030(9) -0.0173(9) -0.0166(9) C12 0.0646(12) 0.0441(11) 0.0558(12) -0.0022(9) -0.0110(10) -0.0224(9) C13 0.0609(11) 0.0360(10) 0.0504(11) 0.0053(8) -0.0047(9) -0.0181(9) C14 0.0520(10) 0.0346(9) 0.0388(9) 0.0024(7) -0.0047(8) -0.0094(8) C15 0.0646(11) 0.0395(10) 0.0442(11) 0.0037(8) -0.0113(9) -0.0204(9) C16 0.0633(12) 0.0408(10) 0.0470(11) 0.0009(8) -0.0082(9) -0.0177(9) C17 0.0739(13) 0.0516(12) 0.0471(12) 0.0035(9) -0.0153(10) -0.0190(10) C18 0.0784(14) 0.0806(16) 0.0546(13) -0.0025(11) -0.0130(11) -0.0337(13) O1 0.0793(9) 0.0431(8) 0.0500(8) 0.0111(6) -0.0230(7) -0.0249(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.350(3) . ? C1 C6 1.429(3) . ? C2 C3 1.407(3) . ? C3 C4 1.346(3) . ? C4 C5 1.424(3) . ? C5 C7 1.411(3) 2_656 ? C5 C6 1.437(2) . ? C6 C7 1.406(3) . ? C7 C5 1.411(3) 2_656 ? C7 C8 1.483(2) . ? C8 C9 1.275(3) . ? C9 C10 1.474(3) . ? C10 C11 1.390(2) . ? C10 C15 1.393(2) . ? C11 C12 1.379(3) . ? C12 C13 1.379(3) . ? C13 C14 1.385(2) . ? C14 O1 1.372(2) . ? C14 C15 1.386(3) . ? C16 O1 1.432(2) . ? C16 C17 1.506(3) . ? C17 C18 1.524(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.67(19) . . ? C1 C2 C3 120.3(2) . . ? C4 C3 C2 120.4(2) . . ? C3 C4 C5 121.82(19) . . ? C7 C5 C4 121.83(17) 2_656 . ? C7 C5 C6 120.20(17) 2_656 . ? C4 C5 C6 117.97(17) . . ? C7 C6 C1 122.02(17) . . ? C7 C6 C5 120.21(16) . . ? C1 C6 C5 117.76(18) . . ? C6 C7 C5 119.58(16) . 2_656 ? C6 C7 C8 120.59(17) . . ? C5 C7 C8 119.79(18) 2_656 . ? C9 C8 C7 127.76(17) . . ? C8 C9 C10 128.98(17) . . ? C11 C10 C15 118.64(16) . . ? C11 C10 C9 122.57(17) . . ? C15 C10 C9 118.78(16) . . ? C12 C11 C10 120.14(17) . . ? C13 C12 C11 121.19(16) . . ? C12 C13 C14 119.23(17) . . ? O1 C14 C13 115.52(16) . . ? O1 C14 C15 124.51(15) . . ? C13 C14 C15 119.96(17) . . ? C14 C15 C10 120.82(16) . . ? O1 C16 C17 107.85(14) . . ? C16 C17 C18 110.87(16) . . ? C14 O1 C16 118.21(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.233 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 933367' ####################################################################### # # 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_global # Attachment 'o-OC3.cif' data_1 #TrackingRef 'o-OC3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H34 N0 O2' _chemical_formula_weight 498.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.105(12) _cell_length_b 8.65(2) _cell_length_c 15.66(4) _cell_angle_alpha 85.57(3) _cell_angle_beta 82.78(3) _cell_angle_gamma 85.67(3) _cell_volume 683(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 567 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 21.07 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 266 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9841 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3852 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2359 _reflns_number_gt 1220 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.0116P] 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 0.032(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2359 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1254 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1453 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.3011(4) 0.1531(2) 0.32542(12) 0.0555(6) Uani 1 1 d . . . C2 C 0.7878(6) 0.4992(3) 0.06730(16) 0.0443(7) Uani 1 1 d . . . C3 C 0.8264(6) 0.6347(3) 0.00923(17) 0.0463(7) Uani 1 1 d . . . C4 C 1.1482(6) 0.0334(3) 0.31664(17) 0.0462(7) Uani 1 1 d . . . C5 C 0.9629(6) 0.3665(3) 0.05758(17) 0.0458(7) Uani 1 1 d . . . C6 C 1.0123(5) 0.0487(3) 0.24409(17) 0.0454(7) Uani 1 1 d . . . C7 C 1.1205(6) -0.0943(3) 0.37515(18) 0.0566(9) Uani 1 1 d . . . H7 H 1.2111 -0.1037 0.4234 0.068 Uiso 1 1 calc R . . C8 C 0.9232(6) 0.2268(3) 0.11770(18) 0.0599(9) Uani 1 1 d . . . H8 H 0.7945 0.1628 0.1068 0.072 Uiso 1 1 calc R . . C9 C 0.6448(6) 0.7666(3) 0.02283(19) 0.0578(9) Uani 1 1 d . . . H9 H 0.6682 0.8565 -0.0131 0.069 Uiso 1 1 calc R . . C10 C 0.8214(6) -0.1955(3) 0.2908(2) 0.0626(9) Uani 1 1 d . . . H10 H 0.7102 -0.2719 0.2825 0.075 Uiso 1 1 calc R . . C11 C 1.0451(6) 0.1847(3) 0.18233(18) 0.0574(9) Uani 1 1 d . . . H11 H 1.1741 0.2494 0.1920 0.069 Uiso 1 1 calc R . . C12 C 0.5708(6) 0.5043(4) 0.13363(18) 0.0588(9) Uani 1 1 d . . . H12 H 0.5448 0.4179 0.1721 0.071 Uiso 1 1 calc R . . C13 C 0.9575(6) -0.2074(3) 0.3613(2) 0.0621(9) Uani 1 1 d . . . H13 H 0.9395 -0.2933 0.4006 0.075 Uiso 1 1 calc R . . C14 C 0.8519(6) -0.0686(3) 0.23242(18) 0.0560(8) Uani 1 1 d . . . H14 H 0.7625 -0.0614 0.1839 0.067 Uiso 1 1 calc R . . C15 C 1.4370(6) 0.1511(3) 0.40005(18) 0.0589(9) Uani 1 1 d . . . H15A H 1.5671 0.0635 0.4010 0.071 Uiso 1 1 calc R . . H15B H 1.3127 0.1424 0.4521 0.071 Uiso 1 1 calc R . . C16 C 0.4397(7) 0.7647(4) 0.0865(2) 0.0666(9) Uani 1 1 d . . . H16 H 0.3236 0.8522 0.0933 0.080 Uiso 1 1 calc R . . C17 C 0.4012(7) 0.6314(4) 0.14222(19) 0.0668(9) Uani 1 1 d . . . H17 H 0.2582 0.6305 0.1853 0.080 Uiso 1 1 calc R . . C24 C 1.5706(7) 0.3012(4) 0.3948(2) 0.0699(10) Uani 1 1 d . . . H24A H 1.6910 0.3086 0.3418 0.084 Uiso 1 1 calc R . . H24B H 1.6746 0.3001 0.4426 0.084 Uiso 1 1 calc R . . C25 C 1.3790(7) 0.4428(4) 0.3970(2) 0.0824(11) Uani 1 1 d . . . H25A H 1.2804 0.4472 0.3485 0.124 Uiso 1 1 calc R . . H25B H 1.4751 0.5345 0.3946 0.124 Uiso 1 1 calc R . . H25C H 1.2595 0.4367 0.4495 0.124 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 0.0624(14) 0.0587(12) 0.0489(12) 0.0090(9) -0.0229(10) -0.0114(11) C2 0.0457(18) 0.0527(17) 0.0367(16) -0.0002(13) -0.0114(14) -0.0102(15) C3 0.0512(19) 0.0483(17) 0.0428(17) 0.0005(14) -0.0187(15) -0.0080(15) C4 0.0465(19) 0.0438(17) 0.0464(17) 0.0028(14) -0.0023(14) -0.0020(15) C5 0.0494(19) 0.0536(18) 0.0372(16) 0.0086(13) -0.0154(14) -0.0161(15) C6 0.0481(19) 0.0461(17) 0.0406(17) 0.0043(13) -0.0029(14) -0.0054(15) C7 0.062(2) 0.0533(19) 0.0496(19) 0.0133(16) -0.0063(16) 0.0079(17) C8 0.072(2) 0.0578(19) 0.0549(19) 0.0138(15) -0.0268(17) -0.0254(17) C9 0.066(2) 0.0555(19) 0.053(2) -0.0024(15) -0.0159(18) -0.0016(18) C10 0.074(2) 0.0504(19) 0.061(2) 0.0003(16) 0.0051(18) -0.0148(17) C11 0.072(2) 0.0579(19) 0.0468(18) 0.0127(15) -0.0218(16) -0.0267(17) C12 0.058(2) 0.068(2) 0.0515(19) 0.0035(16) -0.0090(17) -0.0151(18) C13 0.073(2) 0.0448(18) 0.062(2) 0.0150(16) 0.0082(18) -0.0010(18) C14 0.064(2) 0.0554(18) 0.0488(18) 0.0013(15) -0.0040(15) -0.0131(17) C15 0.065(2) 0.065(2) 0.0475(18) -0.0003(15) -0.0214(16) 0.0084(17) C16 0.067(2) 0.069(2) 0.065(2) -0.0129(18) -0.0123(19) 0.0057(19) C17 0.059(2) 0.084(2) 0.058(2) -0.0076(19) -0.0021(17) -0.009(2) C24 0.077(3) 0.074(2) 0.063(2) -0.0078(17) -0.0278(18) -0.001(2) C25 0.104(3) 0.064(2) 0.078(2) -0.0007(18) -0.009(2) -0.002(2) _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 C4 1.368(4) . ? O1 C15 1.431(4) . ? C2 C5 1.406(4) . ? C2 C12 1.421(4) . ? C2 C3 1.437(4) . ? C3 C5 1.403(4) 2_765 ? C3 C9 1.427(4) . ? C4 C7 1.384(4) . ? C4 C6 1.397(4) . ? C5 C3 1.403(4) 2_765 ? C5 C8 1.484(4) . ? C6 C14 1.387(4) . ? C6 C11 1.470(4) . ? C7 C13 1.377(5) . ? C7 H7 0.9300 . ? C8 C11 1.270(4) . ? C8 H8 0.9300 . ? C9 C16 1.352(4) . ? C9 H9 0.9300 . ? C10 C13 1.371(5) . ? C10 C14 1.379(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C17 1.352(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C24 1.504(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.402(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C24 C25 1.508(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? 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 C4 O1 C15 119.3(2) . . ? C5 C2 C12 121.9(3) . . ? C5 C2 C3 119.9(3) . . ? C12 C2 C3 118.2(3) . . ? C5 C3 C9 122.6(3) 2_765 . ? C5 C3 C2 119.9(3) 2_765 . ? C9 C3 C2 117.5(3) . . ? O1 C4 C7 123.9(3) . . ? O1 C4 C6 115.4(2) . . ? C7 C4 C6 120.7(3) . . ? C3 C5 C2 120.2(2) 2_765 . ? C3 C5 C8 119.9(3) 2_765 . ? C2 C5 C8 119.9(3) . . ? C14 C6 C4 117.9(3) . . ? C14 C6 C11 122.1(3) . . ? C4 C6 C11 120.0(3) . . ? C13 C7 C4 119.5(3) . . ? C13 C7 H7 120.3 . . ? C4 C7 H7 120.3 . . ? C11 C8 C5 127.4(3) . . ? C11 C8 H8 116.3 . . ? C5 C8 H8 116.3 . . ? C16 C9 C3 121.8(3) . . ? C16 C9 H9 119.1 . . ? C3 C9 H9 119.1 . . ? C13 C10 C14 119.0(3) . . ? C13 C10 H10 120.5 . . ? C14 C10 H10 120.5 . . ? C8 C11 C6 129.6(3) . . ? C8 C11 H11 115.2 . . ? C6 C11 H11 115.2 . . ? C17 C12 C2 121.7(3) . . ? C17 C12 H12 119.1 . . ? C2 C12 H12 119.1 . . ? C10 C13 C7 121.2(3) . . ? C10 C13 H13 119.4 . . ? C7 C13 H13 119.4 . . ? C10 C14 C6 121.8(3) . . ? C10 C14 H14 119.1 . . ? C6 C14 H14 119.1 . . ? O1 C15 C24 107.1(2) . . ? O1 C15 H15A 110.3 . . ? C24 C15 H15A 110.3 . . ? O1 C15 H15B 110.3 . . ? C24 C15 H15B 110.3 . . ? H15A C15 H15B 108.6 . . ? C9 C16 C17 120.4(3) . . ? C9 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C12 C17 C16 120.3(3) . . ? C12 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C15 C24 C25 113.3(3) . . ? C15 C24 H24A 108.9 . . ? C25 C24 H24A 108.9 . . ? C15 C24 H24B 108.9 . . ? C25 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C5 C2 C3 C5 0.7(4) . . . 2_765 ? C12 C2 C3 C5 -179.4(3) . . . 2_765 ? C5 C2 C3 C9 -179.2(2) . . . . ? C12 C2 C3 C9 0.7(4) . . . . ? C15 O1 C4 C7 -1.7(4) . . . . ? C15 O1 C4 C6 176.9(2) . . . . ? C12 C2 C5 C3 179.4(3) . . . 2_765 ? C3 C2 C5 C3 -0.7(4) . . . 2_765 ? C12 C2 C5 C8 0.0(4) . . . . ? C3 C2 C5 C8 179.8(3) . . . . ? O1 C4 C6 C14 -179.3(2) . . . . ? C7 C4 C6 C14 -0.6(4) . . . . ? O1 C4 C6 C11 1.6(4) . . . . ? C7 C4 C6 C11 -179.7(3) . . . . ? O1 C4 C7 C13 178.7(3) . . . . ? C6 C4 C7 C13 0.2(4) . . . . ? C3 C5 C8 C11 80.3(5) 2_765 . . . ? C2 C5 C8 C11 -100.2(4) . . . . ? C5 C3 C9 C16 178.6(3) 2_765 . . . ? C2 C3 C9 C16 -1.5(4) . . . . ? C5 C8 C11 C6 179.5(3) . . . . ? C14 C6 C11 C8 8.1(5) . . . . ? C4 C6 C11 C8 -172.9(3) . . . . ? C5 C2 C12 C17 -179.3(3) . . . . ? C3 C2 C12 C17 0.9(4) . . . . ? C14 C10 C13 C7 0.8(5) . . . . ? C4 C7 C13 C10 -0.2(4) . . . . ? C13 C10 C14 C6 -1.3(5) . . . . ? C4 C6 C14 C10 1.2(4) . . . . ? C11 C6 C14 C10 -179.7(3) . . . . ? C4 O1 C15 C24 -176.0(2) . . . . ? C3 C9 C16 C17 0.7(5) . . . . ? C2 C12 C17 C16 -1.7(5) . . . . ? C9 C16 C17 C12 0.9(5) . . . . ? O1 C15 C24 C25 62.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.162 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 933368' ####################################################################### # # 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_global # Attachment 'p-OC3.CIF' data_ywj-1 #TrackingRef 'p-OC3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H34 O2' _chemical_formula_weight 498.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4312(11) _cell_length_b 8.8724(18) _cell_length_c 15.066(3) _cell_angle_alpha 102.61(3) _cell_angle_beta 98.34(3) _cell_angle_gamma 101.81(3) _cell_volume 679.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 266 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9798 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5384 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2392 _reflns_number_gt 1370 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1285P)^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 2392 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1939 _refine_ls_wR_factor_gt 0.1556 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.003 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 0.8348(5) 0.9668(3) 0.37292(17) 0.0645(7) Uani 1 1 d . . . H1 H 0.8251 0.8673 0.3346 0.077 Uiso 1 1 calc R . . C2 C 1.0119(6) 1.0947(3) 0.36765(19) 0.0713(8) Uani 1 1 d . . . H2 H 1.1250 1.0822 0.3274 0.086 Uiso 1 1 calc R . . C3 C 1.0239(6) 1.2472(3) 0.42371(19) 0.0706(8) Uani 1 1 d . . . H3 H 1.1420 1.3355 0.4187 0.085 Uiso 1 1 calc R . . C4 C 0.8670(5) 1.2659(3) 0.48399(18) 0.0627(7) Uani 1 1 d . . . H4 H 0.8794 1.3675 0.5202 0.075 Uiso 1 1 calc R . . C5 C 0.6809(5) 1.1346(2) 0.49442(16) 0.0541(7) Uani 1 1 d . . . C6 C 0.6625(5) 0.9804(2) 0.43572(15) 0.0543(6) Uani 1 1 d . . . C7 C 0.4781(5) 0.8470(2) 0.44092(16) 0.0541(7) Uani 1 1 d . . . C8 C 0.4698(5) 0.6883(3) 0.38164(17) 0.0669(8) Uani 1 1 d . . . H8 H 0.6027 0.6437 0.4005 0.080 Uiso 1 1 calc R . . C9 C 0.3089(5) 0.6033(3) 0.30873(16) 0.0576(7) Uani 1 1 d . . . H9 H 0.1737 0.6451 0.2886 0.069 Uiso 1 1 calc R . . C10 C 0.3147(4) 0.4454(2) 0.25291(15) 0.0513(6) Uani 1 1 d . . . C11 C 0.1286(5) 0.3643(3) 0.17308(16) 0.0580(7) Uani 1 1 d . . . H11 H -0.0002 0.4115 0.1537 0.070 Uiso 1 1 calc R . . C12 C 0.1332(5) 0.2161(3) 0.12299(16) 0.0586(7) Uani 1 1 d . . . H12 H 0.0096 0.1654 0.0694 0.070 Uiso 1 1 calc R . . C13 C 0.3174(4) 0.1420(2) 0.15084(15) 0.0517(6) Uani 1 1 d . . . C14 C 0.5039(5) 0.2190(3) 0.22895(18) 0.0641(7) Uani 1 1 d . . . H14 H 0.6313 0.1705 0.2481 0.077 Uiso 1 1 calc R . . C15 C 0.5000(5) 0.3683(3) 0.27838(18) 0.0633(7) Uani 1 1 d . . . H15 H 0.6270 0.4194 0.3309 0.076 Uiso 1 1 calc R . . C16 C 0.4943(6) -0.0864(3) 0.1295(2) 0.0767(8) Uani 1 1 d . . . H16A H 0.4830 -0.0957 0.1919 0.092 Uiso 1 1 calc R . . H16B H 0.6639 -0.0223 0.1317 0.092 Uiso 1 1 calc R . . C17 C 0.4596(6) -0.2452(3) 0.0683(2) 0.0844(9) Uani 1 1 d . . . H17A H 0.4614 -0.2371 0.0053 0.101 Uiso 1 1 calc R . . H17B H 0.2946 -0.3119 0.0690 0.101 Uiso 1 1 calc R . . C18 C 0.6724(7) -0.3207(4) 0.1001(2) 0.0924(10) Uani 1 1 d . . . H18A H 0.8353 -0.2556 0.0983 0.139 Uiso 1 1 calc R . . H18B H 0.6469 -0.4249 0.0596 0.139 Uiso 1 1 calc R . . H18C H 0.6695 -0.3293 0.1624 0.139 Uiso 1 1 calc R . . O1 O 0.3044(3) -0.00827(18) 0.09812(12) 0.0677(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0715(17) 0.0594(15) 0.0570(15) 0.0089(11) -0.0048(13) 0.0225(14) C2 0.0705(18) 0.0792(18) 0.0646(16) 0.0239(14) 0.0038(13) 0.0200(15) C3 0.0732(19) 0.0583(15) 0.0722(18) 0.0234(13) -0.0035(15) 0.0038(14) C4 0.0741(17) 0.0426(12) 0.0625(16) 0.0124(11) -0.0077(14) 0.0107(12) C5 0.0591(15) 0.0387(11) 0.0535(13) 0.0077(10) -0.0116(12) 0.0079(11) C6 0.0611(15) 0.0448(12) 0.0487(13) 0.0065(10) -0.0107(11) 0.0155(11) C7 0.0616(15) 0.0382(11) 0.0524(13) 0.0039(10) -0.0116(11) 0.0141(11) C8 0.0750(17) 0.0430(12) 0.0679(16) -0.0024(11) -0.0166(13) 0.0211(12) C9 0.0647(15) 0.0490(12) 0.0528(13) 0.0023(10) -0.0035(11) 0.0218(12) C10 0.0543(14) 0.0437(11) 0.0503(13) 0.0060(10) 0.0021(10) 0.0116(10) C11 0.0596(15) 0.0514(13) 0.0542(14) 0.0002(10) -0.0052(11) 0.0196(11) C12 0.0604(15) 0.0527(13) 0.0504(13) -0.0006(10) -0.0043(11) 0.0121(11) C13 0.0570(14) 0.0425(11) 0.0503(13) 0.0040(10) 0.0084(11) 0.0103(11) C14 0.0577(15) 0.0532(13) 0.0716(16) 0.0022(11) -0.0063(12) 0.0199(12) C15 0.0614(15) 0.0496(13) 0.0617(15) -0.0036(11) -0.0129(12) 0.0121(11) C16 0.0708(18) 0.0594(15) 0.092(2) 0.0038(14) 0.0031(15) 0.0245(14) C17 0.094(2) 0.0641(16) 0.090(2) 0.0034(15) 0.0130(18) 0.0305(17) C18 0.096(2) 0.0757(18) 0.109(2) 0.0138(17) 0.0172(19) 0.0424(18) O1 0.0754(12) 0.0469(9) 0.0688(11) -0.0055(8) 0.0015(9) 0.0195(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.354(4) . ? C1 C6 1.428(4) . ? C1 H1 0.9300 . ? C2 C3 1.413(4) . ? C2 H2 0.9300 . ? C3 C4 1.340(4) . ? C3 H3 0.9300 . ? C4 C5 1.431(4) . ? C4 H4 0.9300 . ? C5 C7 1.398(4) 2_676 ? C5 C6 1.434(3) . ? C6 C7 1.409(3) . ? C7 C5 1.398(4) 2_676 ? C7 C8 1.482(3) . ? C8 C9 1.277(3) . ? C8 H8 0.9300 . ? C9 C10 1.477(3) . ? C9 H9 0.9300 . ? C10 C15 1.383(3) . ? C10 C11 1.399(3) . ? C11 C12 1.372(3) . ? C11 H11 0.9300 . ? C12 C13 1.370(3) . ? C12 H12 0.9300 . ? C13 C14 1.377(3) . ? C13 O1 1.377(2) . ? C14 C15 1.377(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O1 1.436(3) . ? C16 C17 1.464(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.520(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.8(3) . . ? C2 C1 H1 119.1 . . ? C6 C1 H1 119.1 . . ? C1 C2 C3 119.6(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 122.1(2) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C7 C5 C4 122.3(2) 2_676 . ? C7 C5 C6 120.3(2) 2_676 . ? C4 C5 C6 117.4(3) . . ? C7 C6 C1 121.7(2) . . ? C7 C6 C5 120.1(2) . . ? C1 C6 C5 118.2(2) . . ? C5 C7 C6 119.6(2) 2_676 . ? C5 C7 C8 121.5(2) 2_676 . ? C6 C7 C8 118.8(3) . . ? C9 C8 C7 130.1(2) . . ? C9 C8 H8 114.9 . . ? C7 C8 H8 114.9 . . ? C8 C9 C10 126.9(2) . . ? C8 C9 H9 116.6 . . ? C10 C9 H9 116.6 . . ? C15 C10 C11 116.62(19) . . ? C15 C10 C9 121.7(2) . . ? C11 C10 C9 121.67(19) . . ? C12 C11 C10 121.1(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 120.9(2) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.5(2) . . ? C12 C13 O1 117.25(19) . . ? C14 C13 O1 123.3(2) . . ? C13 C14 C15 119.4(2) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C10 C15 C14 122.6(2) . . ? C10 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? O1 C16 C17 111.6(2) . . ? O1 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? O1 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 110.3(3) . . ? C16 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? C16 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C13 O1 C16 116.70(18) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.212 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 933369'