# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_100628b_0m _database_code_depnum_ccdc_archive 'CCDC 895476' #TrackingRef '3a-CCDC_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 O2' _chemical_formula_weight 264.31 _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6233(18) _cell_length_b 5.3529(10) _cell_length_c 13.578(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.032(3) _cell_angle_gamma 90.00 _cell_volume 699.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1437 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 24.12 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9494 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3587 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2227 _reflns_number_gt 1824 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.0392P] 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 -0.2(14) _refine_ls_number_reflns 2227 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _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 0.7029(2) 0.4264(5) 0.56298(19) 0.0804(7) Uani 1 1 d . . . H1 H 0.7688 0.4238 0.5137 0.097 Uiso 1 1 calc R . . C2 C 0.6026(2) 0.2476(5) 0.56619(18) 0.0792(6) Uani 1 1 d . . . H2 H 0.5985 0.1245 0.5179 0.095 Uiso 1 1 calc R . . C3 C 0.5069(2) 0.2476(4) 0.64055(16) 0.0679(6) Uani 1 1 d . . . H3 H 0.4398 0.1227 0.6422 0.082 Uiso 1 1 calc R . . C4 C 0.50878(19) 0.4297(4) 0.71281(15) 0.0570(5) Uani 1 1 d . . . C5 C 0.6103(2) 0.6128(4) 0.70728(16) 0.0736(6) Uani 1 1 d . . . H5 H 0.6137 0.7388 0.7544 0.088 Uiso 1 1 calc R . . C6 C 0.7057(3) 0.6110(5) 0.63353(18) 0.0828(7) Uani 1 1 d . . . H6 H 0.7728 0.7357 0.6311 0.099 Uiso 1 1 calc R . . C7 C 0.40941(19) 0.4248(3) 0.79355(15) 0.0562(5) Uani 1 1 d . . . C8 C 0.3960(2) 0.5922(4) 0.86585(15) 0.0609(5) Uani 1 1 d . . . H8 H 0.4424 0.7442 0.8620 0.073 Uiso 1 1 calc R . . C9 C 0.3109(2) 0.5405(3) 0.94964(14) 0.0574(5) Uani 1 1 d . . . C10 C 0.3210(2) 0.6704(4) 1.03843(16) 0.0690(6) Uani 1 1 d . . . H10 H 0.3807 0.8066 1.0437 0.083 Uiso 1 1 calc R . . C11 C 0.2447(2) 0.6012(5) 1.11796(16) 0.0739(6) Uani 1 1 d . . . H11 H 0.2534 0.6902 1.1766 0.089 Uiso 1 1 calc R . . C12 C 0.1550(2) 0.4005(5) 1.11196(15) 0.0698(6) Uani 1 1 d . . . H12 H 0.1036 0.3533 1.1662 0.084 Uiso 1 1 calc R . . C13 C 0.1426(2) 0.2703(4) 1.02424(14) 0.0631(5) Uani 1 1 d . . . H13 H 0.0823 0.1348 1.0196 0.076 Uiso 1 1 calc R . . C14 C 0.2185(2) 0.3393(4) 0.94365(14) 0.0554(5) Uani 1 1 d . . . C15 C 0.20169(18) 0.2193(4) 0.84433(13) 0.0570(5) Uani 1 1 d . . . H15 H 0.1681 0.0483 0.8538 0.068 Uiso 1 1 calc R . . C16 C 0.0955(2) 0.3586(4) 0.78009(13) 0.0594(5) Uani 1 1 d . . . H16A H 0.0064 0.3574 0.8123 0.071 Uiso 1 1 calc R . . H16B H 0.1246 0.5313 0.7736 0.071 Uiso 1 1 calc R . . C17 C 0.0786(2) 0.2449(4) 0.67853(14) 0.0614(5) Uani 1 1 d . . . O1 O 0.33273(13) 0.2074(2) 0.79415(9) 0.0587(3) Uani 1 1 d . . . O2 O 0.0479(2) 0.0288(3) 0.66867(12) 0.1042(6) Uani 1 1 d . . . C18 C 0.1020(3) 0.4090(5) 0.59379(15) 0.0833(7) Uani 1 1 d . . . H18A H 0.1984 0.4550 0.5922 0.125 Uiso 1 1 calc R . . H18B H 0.0462 0.5567 0.5997 0.125 Uiso 1 1 calc R . . H18C H 0.0769 0.3227 0.5341 0.125 Uiso 1 1 calc R . . _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 0.0714(14) 0.0742(16) 0.0962(17) 0.0033(14) 0.0135(12) 0.0033(13) C2 0.0774(14) 0.0667(15) 0.0939(15) -0.0154(13) 0.0101(12) 0.0009(15) C3 0.0614(12) 0.0540(13) 0.0884(14) -0.0056(11) 0.0014(10) 0.0003(12) C4 0.0527(10) 0.0462(10) 0.0719(12) 0.0046(9) -0.0090(9) 0.0038(9) C5 0.0800(14) 0.0570(13) 0.0837(14) -0.0051(12) -0.0025(12) -0.0099(12) C6 0.0786(15) 0.0710(16) 0.0988(17) 0.0031(14) 0.0052(13) -0.0180(13) C7 0.0567(10) 0.0358(9) 0.0755(13) -0.0004(9) -0.0112(9) 0.0018(9) C8 0.0632(12) 0.0375(11) 0.0815(13) -0.0015(10) -0.0103(10) -0.0025(9) C9 0.0613(11) 0.0440(11) 0.0664(12) -0.0026(9) -0.0129(9) 0.0059(10) C10 0.0690(13) 0.0566(13) 0.0807(14) -0.0126(11) -0.0169(11) -0.0010(11) C11 0.0792(14) 0.0737(16) 0.0679(13) -0.0194(12) -0.0200(11) 0.0131(13) C12 0.0771(13) 0.0724(16) 0.0594(12) 0.0025(11) -0.0094(10) 0.0086(13) C13 0.0731(13) 0.0505(12) 0.0655(12) 0.0008(10) -0.0085(10) 0.0023(11) C14 0.0632(11) 0.0428(10) 0.0598(11) 0.0002(9) -0.0109(9) 0.0071(9) C15 0.0632(11) 0.0399(10) 0.0679(11) -0.0013(9) -0.0027(9) -0.0040(10) C16 0.0642(12) 0.0491(12) 0.0648(11) -0.0053(9) -0.0041(9) -0.0022(10) C17 0.0629(12) 0.0551(13) 0.0659(12) -0.0057(10) -0.0051(9) -0.0021(11) O1 0.0632(7) 0.0360(7) 0.0768(8) -0.0051(6) 0.0018(6) -0.0020(6) O2 0.1655(17) 0.0625(11) 0.0841(11) -0.0148(9) -0.0065(11) -0.0315(13) C18 0.1064(17) 0.0791(16) 0.0642(14) 0.0008(11) -0.0010(12) 0.0122(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _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 1.360(3) . ? C1 C6 1.376(3) . ? C1 H1 0.9300 . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(3) . ? C3 H3 0.9300 . ? C4 C5 1.386(3) . ? C4 C7 1.468(3) . ? C5 C6 1.371(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.337(3) . ? C7 O1 1.378(2) . ? C8 C9 1.441(3) . ? C8 H8 0.9300 . ? C9 C10 1.394(3) . ? C9 C14 1.398(3) . ? C10 C11 1.368(3) . ? C10 H10 0.9300 . ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 C13 1.383(3) . ? C12 H12 0.9300 . ? C13 C14 1.377(3) . ? C13 H13 0.9300 . ? C14 C15 1.500(3) . ? C15 O1 1.446(2) . ? C15 C16 1.526(3) . ? C15 H15 0.9800 . ? C16 C17 1.514(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O2 1.201(3) . ? C17 C18 1.468(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.2(2) . . ? C2 C1 H1 120.4 . . ? C6 C1 H1 120.4 . . ? C1 C2 C3 120.5(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 117.38(19) . . ? C3 C4 C7 121.11(19) . . ? C5 C4 C7 121.49(19) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C8 C7 O1 120.19(18) . . ? C8 C7 C4 127.50(19) . . ? O1 C7 C4 112.08(17) . . ? C7 C8 C9 120.97(18) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C14 117.96(19) . . ? C10 C9 C8 123.75(18) . . ? C14 C9 C8 118.18(17) . . ? C11 C10 C9 121.2(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.6(2) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 119.2(2) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C9 120.42(18) . . ? C13 C14 C15 123.35(19) . . ? C9 C14 C15 116.11(18) . . ? O1 C15 C14 111.22(15) . . ? O1 C15 C16 109.44(15) . . ? C14 C15 C16 111.40(16) . . ? O1 C15 H15 108.2 . . ? C14 C15 H15 108.2 . . ? C16 C15 H15 108.2 . . ? C17 C16 C15 112.61(16) . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? O2 C17 C18 122.0(2) . . ? O2 C17 C16 120.8(2) . . ? C18 C17 C16 117.2(2) . . ? C7 O1 C15 115.94(14) . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.104 _refine_diff_density_min -0.103 _refine_diff_density_rms 0.023 data_120424a_0m _database_code_depnum_ccdc_archive 'CCDC 895477' #TrackingRef '3f-II-CCDC_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 O2' _chemical_formula_weight 290.34 _chemical_absolute_configuration unk _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.5018(11) _cell_length_b 10.356(2) _cell_length_c 13.085(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.640(3) _cell_angle_gamma 90.00 _cell_volume 745.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2410 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.39 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9601 _exptl_absorpt_correction_T_max 0.9758 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3741 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.23 _reflns_number_total 2433 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0271P)^2^+0.1118P] 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 0.1(11) _refine_ls_number_reflns 2433 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0670 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.2387(3) 0.92607(17) 0.29235(12) 0.0221(4) Uani 1 1 d . . . C2 C 1.1805(3) 1.06345(17) 0.32308(13) 0.0265(4) Uani 1 1 d . . . H2A H 1.3072 1.1237 0.2998 0.032 Uiso 1 1 calc R . . H2B H 1.1693 1.0707 0.3982 0.032 Uiso 1 1 calc R . . C3 C 0.9347(3) 1.09320(17) 0.27018(13) 0.0255(4) Uani 1 1 d . . . H3A H 0.7994 1.0767 0.3167 0.031 Uiso 1 1 calc R . . H3B H 0.9271 1.1843 0.2474 0.031 Uiso 1 1 calc R . . C4 C 0.9224(3) 1.00119(17) 0.17863(13) 0.0231(4) Uani 1 1 d . . . H4A H 1.0174 1.0350 0.1214 0.028 Uiso 1 1 calc R . . H4B H 0.7522 0.9872 0.1546 0.028 Uiso 1 1 calc R . . C5 C 1.0344(3) 0.87632(16) 0.22141(11) 0.0195(3) Uani 1 1 d . . . H5 H 0.9106 0.8344 0.2650 0.023 Uiso 1 1 calc R . . C6 C 1.1170(3) 0.77585(15) 0.14420(12) 0.0198(3) Uani 1 1 d . . . H6 H 1.2710 0.8073 0.1139 0.024 Uiso 1 1 calc R . . C7 C 0.9321(3) 0.75514(15) 0.05822(12) 0.0187(3) Uani 1 1 d . . . C8 C 0.9341(3) 0.82441(16) -0.03207(12) 0.0218(4) Uani 1 1 d . . . H8 H 1.0637 0.8824 -0.0445 0.026 Uiso 1 1 calc R . . C9 C 0.7470(3) 0.80930(16) -0.10455(12) 0.0232(4) Uani 1 1 d . . . H9 H 0.7465 0.8581 -0.1660 0.028 Uiso 1 1 calc R . . C10 C 0.5609(3) 0.72267(17) -0.08686(12) 0.0237(4) Uani 1 1 d . . . H10 H 0.4326 0.7126 -0.1363 0.028 Uiso 1 1 calc R . . C11 C 0.5603(3) 0.65085(17) 0.00217(12) 0.0214(3) Uani 1 1 d . . . H11 H 0.4333 0.5906 0.0129 0.026 Uiso 1 1 calc R . . C12 C 0.7456(3) 0.66637(16) 0.07655(11) 0.0188(3) Uani 1 1 d . . . C13 C 0.7577(3) 0.59482(16) 0.17234(12) 0.0198(3) Uani 1 1 d . . . H13 H 0.6173 0.5517 0.1957 0.024 Uiso 1 1 calc R . . C14 C 0.9664(3) 0.58954(15) 0.22778(12) 0.0192(3) Uani 1 1 d . . . C15 C 1.0160(3) 0.51334(16) 0.32121(12) 0.0220(4) Uani 1 1 d . . . C16 C 0.8566(3) 0.41799(17) 0.35302(12) 0.0263(4) Uani 1 1 d . . . H16 H 0.7096 0.4029 0.3151 0.032 Uiso 1 1 calc R . . C17 C 0.9103(3) 0.34497(18) 0.43945(13) 0.0326(4) Uani 1 1 d . . . H17 H 0.7994 0.2806 0.4606 0.039 Uiso 1 1 calc R . . C18 C 1.1242(3) 0.3652(2) 0.49520(13) 0.0350(5) Uani 1 1 d . . . H18 H 1.1623 0.3138 0.5536 0.042 Uiso 1 1 calc R . . C19 C 1.2814(3) 0.4607(2) 0.46535(14) 0.0357(5) Uani 1 1 d . . . H19 H 1.4276 0.4753 0.5040 0.043 Uiso 1 1 calc R . . C20 C 1.2295(3) 0.53572(18) 0.37969(13) 0.0289(4) Uani 1 1 d . . . H20 H 1.3383 0.6022 0.3607 0.035 Uiso 1 1 calc R . . O1 O 1.4231(2) 0.86792(13) 0.31602(9) 0.0334(3) Uani 1 1 d . . . O2 O 1.16871(18) 0.65608(11) 0.19674(8) 0.0205(2) Uani 1 1 d . . . _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 0.0205(8) 0.0280(9) 0.0178(8) -0.0004(7) 0.0002(6) -0.0021(7) C2 0.0288(9) 0.0262(10) 0.0243(9) -0.0018(7) -0.0052(7) -0.0034(7) C3 0.0264(9) 0.0252(9) 0.0247(9) -0.0024(7) -0.0034(7) 0.0020(7) C4 0.0217(8) 0.0235(9) 0.0238(9) -0.0002(7) -0.0054(7) 0.0002(7) C5 0.0169(7) 0.0229(9) 0.0187(8) 0.0001(7) 0.0006(6) 0.0000(6) C6 0.0152(7) 0.0233(9) 0.0206(8) 0.0016(7) -0.0007(6) -0.0010(6) C7 0.0164(7) 0.0203(9) 0.0195(8) -0.0025(7) 0.0012(6) 0.0024(6) C8 0.0222(8) 0.0208(9) 0.0225(8) -0.0021(7) 0.0027(7) -0.0021(7) C9 0.0264(8) 0.0251(10) 0.0180(8) 0.0011(7) 0.0005(7) 0.0040(7) C10 0.0230(8) 0.0288(10) 0.0189(8) -0.0030(7) -0.0047(7) 0.0023(7) C11 0.0170(8) 0.0247(9) 0.0224(8) -0.0036(7) 0.0000(6) -0.0005(7) C12 0.0166(7) 0.0213(9) 0.0184(8) -0.0022(7) 0.0015(6) 0.0035(6) C13 0.0173(7) 0.0220(9) 0.0202(8) -0.0005(7) 0.0020(6) 0.0004(6) C14 0.0193(8) 0.0188(9) 0.0196(8) -0.0040(7) 0.0026(6) 0.0017(6) C15 0.0237(8) 0.0248(10) 0.0175(8) -0.0040(7) 0.0020(7) 0.0085(7) C16 0.0310(9) 0.0268(10) 0.0212(8) -0.0021(7) 0.0000(7) 0.0031(7) C17 0.0486(11) 0.0260(10) 0.0235(9) 0.0016(8) 0.0074(8) 0.0061(8) C18 0.0475(11) 0.0409(12) 0.0168(8) 0.0033(8) 0.0013(8) 0.0194(9) C19 0.0318(10) 0.0546(14) 0.0204(9) -0.0009(9) -0.0020(7) 0.0133(9) C20 0.0256(9) 0.0395(12) 0.0214(9) -0.0012(8) -0.0016(7) 0.0069(8) O1 0.0236(6) 0.0407(8) 0.0351(7) -0.0081(6) -0.0109(5) 0.0058(6) O2 0.0149(5) 0.0237(6) 0.0228(6) 0.0006(5) -0.0009(4) 0.0021(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. ; _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 1.213(2) . ? C1 C2 1.515(2) . ? C1 C5 1.527(2) . ? C2 C3 1.533(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.531(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.531(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.528(2) . ? C5 H5 1.0000 . ? C6 O2 1.443(2) . ? C6 C7 1.510(2) . ? C6 H6 1.0000 . ? C7 C8 1.382(2) . ? C7 C12 1.403(2) . ? C8 C9 1.389(2) . ? C8 H8 0.9500 . ? C9 C10 1.386(2) . ? C9 H9 0.9500 . ? C10 C11 1.382(2) . ? C10 H10 0.9500 . ? C11 C12 1.399(2) . ? C11 H11 0.9500 . ? C12 C13 1.456(2) . ? C13 C14 1.342(2) . ? C13 H13 0.9500 . ? C14 O2 1.3801(18) . ? C14 C15 1.474(2) . ? C15 C16 1.392(2) . ? C15 C20 1.403(2) . ? C16 C17 1.385(2) . ? C16 H16 0.9500 . ? C17 C18 1.383(3) . ? C17 H17 0.9500 . ? C18 C19 1.377(3) . ? C18 H18 0.9500 . ? C19 C20 1.387(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? _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 125.45(15) . . ? O1 C1 C5 125.73(15) . . ? C2 C1 C5 108.71(14) . . ? C1 C2 C3 105.01(13) . . ? C1 C2 H2A 110.7 . . ? C3 C2 H2A 110.7 . . ? C1 C2 H2B 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C4 C3 C2 104.30(13) . . ? C4 C3 H3A 110.9 . . ? C2 C3 H3A 110.9 . . ? C4 C3 H3B 110.9 . . ? C2 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? C3 C4 C5 103.37(13) . . ? C3 C4 H4A 111.1 . . ? C5 C4 H4A 111.1 . . ? C3 C4 H4B 111.1 . . ? C5 C4 H4B 111.1 . . ? H4A C4 H4B 109.1 . . ? C1 C5 C6 113.82(12) . . ? C1 C5 C4 102.64(13) . . ? C6 C5 C4 117.22(13) . . ? C1 C5 H5 107.6 . . ? C6 C5 H5 107.6 . . ? C4 C5 H5 107.6 . . ? O2 C6 C7 110.63(12) . . ? O2 C6 C5 109.19(12) . . ? C7 C6 C5 112.48(12) . . ? O2 C6 H6 108.1 . . ? C7 C6 H6 108.1 . . ? C5 C6 H6 108.1 . . ? C8 C7 C12 120.66(14) . . ? C8 C7 C6 122.76(14) . . ? C12 C7 C6 116.47(13) . . ? C7 C8 C9 120.08(15) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 119.72(16) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C11 C10 C9 120.58(15) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.36(15) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 118.57(14) . . ? C11 C12 C13 123.71(15) . . ? C7 C12 C13 117.71(14) . . ? C14 C13 C12 120.23(14) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 O2 120.36(14) . . ? C13 C14 C15 127.27(14) . . ? O2 C14 C15 112.32(12) . . ? C16 C15 C20 118.61(15) . . ? C16 C15 C14 121.64(14) . . ? C20 C15 C14 119.75(15) . . ? C17 C16 C15 120.67(17) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 120.40(18) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 119.43(17) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 120.98(18) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C15 119.88(18) . . ? C19 C20 H20 120.1 . . ? C15 C20 H20 120.1 . . ? C14 O2 C6 114.82(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.110 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.031 data_120329a_0m _database_code_depnum_ccdc_archive 'CCDC 895478' #TrackingRef '5f-CCDC_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 O2' _chemical_formula_weight 290.34 _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _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 5.3352(7) _cell_length_b 11.2818(16) _cell_length_c 25.012(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.848(4) _cell_angle_gamma 90.00 _cell_volume 1478.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 940 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 23.56 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9772 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7262 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2674 _reflns_number_gt 1782 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.4097P] 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 2674 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6413(3) 0.43770(13) 0.83429(6) 0.0269(4) Uani 1 1 d . . . O2 O 0.4277(3) 0.16237(13) 0.95343(6) 0.0304(4) Uani 1 1 d . . . C1 C 0.7422(4) 0.62451(19) 0.90802(9) 0.0247(5) Uani 1 1 d . . . H1 H 0.5835 0.6241 0.8833 0.030 Uiso 1 1 calc R . . C2 C 0.7939(4) 0.7136(2) 0.94621(9) 0.0283(6) Uani 1 1 d . . . H2 H 0.6702 0.7733 0.9480 0.034 Uiso 1 1 calc R . . C3 C 1.0259(4) 0.71600(19) 0.98190(9) 0.0260(5) Uani 1 1 d . . . H3 H 1.0622 0.7775 1.0082 0.031 Uiso 1 1 calc R . . C4 C 1.2047(4) 0.62877(19) 0.97921(9) 0.0273(6) Uani 1 1 d . . . H4 H 1.3645 0.6308 1.0035 0.033 Uiso 1 1 calc R . . C5 C 1.1525(4) 0.53853(19) 0.94134(8) 0.0238(5) Uani 1 1 d . . . H5 H 1.2761 0.4786 0.9400 0.029 Uiso 1 1 calc R . . C6 C 0.9186(4) 0.53511(18) 0.90508(8) 0.0200(5) Uani 1 1 d . . . C7 C 0.8496(4) 0.43849(18) 0.86435(8) 0.0200(5) Uani 1 1 d . . . C8 C 1.0428(4) 0.34037(18) 0.86206(8) 0.0202(5) Uani 1 1 d . . . H8A H 1.2096 0.3769 0.8601 0.024 Uiso 1 1 calc R . . H8B H 1.0643 0.2941 0.8962 0.024 Uiso 1 1 calc R . . C9 C 0.9710(4) 0.25698(18) 0.81472(8) 0.0187(5) Uani 1 1 d . . . C10 C 1.1039(4) 0.26569(19) 0.77192(9) 0.0228(5) Uani 1 1 d . . . H10 H 1.2375 0.3221 0.7740 0.027 Uiso 1 1 calc R . . C11 C 1.0454(4) 0.19391(19) 0.72648(9) 0.0237(5) Uani 1 1 d . . . H11 H 1.1389 0.2007 0.6978 0.028 Uiso 1 1 calc R . . C12 C 0.8501(4) 0.11222(19) 0.72297(9) 0.0238(5) Uani 1 1 d . . . H12 H 0.8058 0.0645 0.6913 0.029 Uiso 1 1 calc R . . C13 C 0.7192(4) 0.09958(19) 0.76515(9) 0.0227(5) Uani 1 1 d . . . H13 H 0.5873 0.0421 0.7624 0.027 Uiso 1 1 calc R . . C14 C 0.7773(4) 0.17015(18) 0.81213(8) 0.0187(5) Uani 1 1 d . . . C15 C 0.6455(4) 0.15606(18) 0.85790(8) 0.0202(5) Uani 1 1 d . . . H15 H 0.6809 0.2166 0.8846 0.024 Uiso 1 1 calc R . . C16 C 0.4822(4) 0.07216(18) 0.86885(8) 0.0193(5) Uani 1 1 d . . . C17 C 0.3731(4) -0.03736(19) 0.83885(9) 0.0268(5) Uani 1 1 d . . . H17A H 0.5107 -0.0943 0.8357 0.032 Uiso 1 1 calc R . . H17B H 0.2814 -0.0168 0.8018 0.032 Uiso 1 1 calc R . . C18 C 0.1877(5) -0.0912(2) 0.87273(9) 0.0314(6) Uani 1 1 d . . . H18A H 0.0093 -0.0822 0.8532 0.038 Uiso 1 1 calc R . . H18B H 0.2235 -0.1767 0.8789 0.038 Uiso 1 1 calc R . . C19 C 0.2255(4) -0.02575(19) 0.92675(9) 0.0281(6) Uani 1 1 d . . . H19A H 0.0589 -0.0019 0.9353 0.034 Uiso 1 1 calc R . . H19B H 0.3145 -0.0770 0.9565 0.034 Uiso 1 1 calc R . . C20 C 0.3840(4) 0.08157(19) 0.92044(9) 0.0215(5) Uani 1 1 d . . . _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 0.0230(9) 0.0227(9) 0.0323(9) -0.0037(7) -0.0017(7) 0.0011(7) O2 0.0391(10) 0.0270(9) 0.0270(9) -0.0068(7) 0.0112(7) -0.0053(8) C1 0.0229(12) 0.0263(13) 0.0262(13) -0.0014(10) 0.0080(10) -0.0021(10) C2 0.0291(14) 0.0230(13) 0.0352(15) -0.0033(11) 0.0124(11) 0.0001(10) C3 0.0369(14) 0.0215(12) 0.0217(13) -0.0049(10) 0.0113(10) -0.0086(11) C4 0.0289(13) 0.0280(13) 0.0240(13) -0.0009(10) 0.0024(10) -0.0083(11) C5 0.0267(13) 0.0210(12) 0.0247(13) 0.0011(10) 0.0069(10) -0.0010(10) C6 0.0210(11) 0.0205(11) 0.0201(12) 0.0014(9) 0.0079(9) -0.0038(9) C7 0.0191(11) 0.0191(12) 0.0227(12) 0.0040(9) 0.0064(9) -0.0023(9) C8 0.0186(11) 0.0184(11) 0.0231(12) -0.0004(9) 0.0025(9) -0.0009(9) C9 0.0172(11) 0.0171(11) 0.0210(12) -0.0001(9) 0.0016(9) 0.0045(9) C10 0.0213(12) 0.0217(12) 0.0257(13) 0.0016(10) 0.0051(10) 0.0014(10) C11 0.0269(13) 0.0237(13) 0.0227(13) 0.0029(10) 0.0101(10) 0.0023(10) C12 0.0274(13) 0.0235(12) 0.0212(13) -0.0025(10) 0.0063(10) 0.0023(10) C13 0.0222(12) 0.0203(12) 0.0247(13) -0.0011(10) 0.0024(10) 0.0000(10) C14 0.0214(12) 0.0173(11) 0.0174(12) 0.0024(9) 0.0037(9) 0.0034(9) C15 0.0221(12) 0.0178(11) 0.0200(12) -0.0028(9) 0.0024(9) 0.0001(9) C16 0.0196(11) 0.0174(11) 0.0196(12) 0.0005(9) 0.0007(9) 0.0030(9) C17 0.0276(12) 0.0259(13) 0.0270(13) -0.0036(10) 0.0059(10) -0.0048(10) C18 0.0352(14) 0.0271(13) 0.0321(15) -0.0002(11) 0.0069(11) -0.0078(11) C19 0.0282(13) 0.0279(13) 0.0303(14) 0.0015(11) 0.0114(11) -0.0029(11) C20 0.0193(12) 0.0212(12) 0.0237(13) 0.0024(10) 0.0031(9) 0.0033(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _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 C7 1.219(2) . ? O2 C20 1.222(2) . ? C1 C2 1.378(3) . ? C1 C6 1.391(3) . ? C1 H1 0.9500 . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? C5 C6 1.398(3) . ? C5 H5 0.9500 . ? C6 C7 1.490(3) . ? C7 C8 1.521(3) . ? C8 C9 1.504(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.395(3) . ? C9 C14 1.416(3) . ? C10 C11 1.382(3) . ? C10 H10 0.9500 . ? C11 C12 1.381(3) . ? C11 H11 0.9500 . ? C12 C13 1.378(3) . ? C12 H12 0.9500 . ? C13 C14 1.405(3) . ? C13 H13 0.9500 . ? C14 C15 1.461(3) . ? C15 C16 1.349(3) . ? C15 H15 0.9500 . ? C16 C20 1.485(3) . ? C16 C17 1.505(3) . ? C17 C18 1.543(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.519(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.502(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? _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 121.1(2) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C1 C2 C3 119.9(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.4(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 118.4(2) . . ? C1 C6 C7 118.94(19) . . ? C5 C6 C7 122.6(2) . . ? O1 C7 C6 120.43(19) . . ? O1 C7 C8 121.14(19) . . ? C6 C7 C8 118.42(18) . . ? C9 C8 C7 114.24(17) . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C14 119.04(19) . . ? C10 C9 C8 117.98(19) . . ? C14 C9 C8 122.98(19) . . ? C11 C10 C9 121.4(2) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C12 C11 C10 119.6(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 121.2(2) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C9 118.34(19) . . ? C13 C14 C15 122.1(2) . . ? C9 C14 C15 119.61(18) . . ? C16 C15 C14 131.3(2) . . ? C16 C15 H15 114.3 . . ? C14 C15 H15 114.3 . . ? C15 C16 C20 118.24(19) . . ? C15 C16 C17 132.7(2) . . ? C20 C16 C17 109.00(18) . . ? C16 C17 C18 106.08(18) . . ? C16 C17 H17A 110.5 . . ? C18 C17 H17A 110.5 . . ? C16 C17 H17B 110.5 . . ? C18 C17 H17B 110.5 . . ? H17A C17 H17B 108.7 . . ? C19 C18 C17 107.80(18) . . ? C19 C18 H18A 110.1 . . ? C17 C18 H18A 110.1 . . ? C19 C18 H18B 110.1 . . ? C17 C18 H18B 110.1 . . ? H18A C18 H18B 108.5 . . ? C20 C19 C18 106.34(18) . . ? C20 C19 H19A 110.5 . . ? C18 C19 H19A 110.5 . . ? C20 C19 H19B 110.5 . . ? C18 C19 H19B 110.5 . . ? H19A C19 H19B 108.7 . . ? O2 C20 C16 125.9(2) . . ? O2 C20 C19 124.7(2) . . ? C16 C20 C19 109.34(18) . . ? _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 1.0(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C2 C1 C6 C5 -1.0(3) . . . . ? C2 C1 C6 C7 177.8(2) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C4 C5 C6 C7 -178.5(2) . . . . ? C1 C6 C7 O1 -0.3(3) . . . . ? C5 C6 C7 O1 178.4(2) . . . . ? C1 C6 C7 C8 -179.19(19) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? O1 C7 C8 C9 9.3(3) . . . . ? C6 C7 C8 C9 -171.80(18) . . . . ? C7 C8 C9 C10 106.7(2) . . . . ? C7 C8 C9 C14 -73.9(3) . . . . ? C14 C9 C10 C11 2.0(3) . . . . ? C8 C9 C10 C11 -178.62(19) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C13 -2.0(3) . . . . ? C11 C12 C13 C14 1.1(3) . . . . ? C12 C13 C14 C9 1.4(3) . . . . ? C12 C13 C14 C15 -178.4(2) . . . . ? C10 C9 C14 C13 -2.8(3) . . . . ? C8 C9 C14 C13 177.78(18) . . . . ? C10 C9 C14 C15 176.92(19) . . . . ? C8 C9 C14 C15 -2.5(3) . . . . ? C13 C14 C15 C16 9.7(3) . . . . ? C9 C14 C15 C16 -170.0(2) . . . . ? C14 C15 C16 C20 178.5(2) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C15 C16 C17 C18 -177.5(2) . . . . ? C20 C16 C17 C18 3.7(2) . . . . ? C16 C17 C18 C19 -9.9(2) . . . . ? C17 C18 C19 C20 12.3(2) . . . . ? C15 C16 C20 O2 3.8(3) . . . . ? C17 C16 C20 O2 -177.2(2) . . . . ? C15 C16 C20 C19 -175.00(19) . . . . ? C17 C16 C20 C19 4.1(2) . . . . ? C18 C19 C20 O2 171.0(2) . . . . ? C18 C19 C20 C16 -10.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.183 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.048