Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Simon Jones' 'Harry Adams' 'Isaac Ojea-Jimenez' _publ_contact_author_name 'Simon Jones' _publ_contact_author_address ; Department of Chemistry University of Sheffield Dainton Building Sheffield S3 7HF UNITED KINGDOM ; _publ_contact_author_email SIMON.JONES@SHEFFIELD.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Highly Diastereoselective Diels-Alder Cycloadditions of 9R-(1-Methoxyethyl)anthracene with p-Benzoquinone ; # Attachment 'OSJ5M.CIF' data_osj5m _database_code_depnum_ccdc_archive 'CCDC 601816' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H42 Cl2 O6' _chemical_formula_weight 773.71 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 13.5591(16) _cell_length_b 9.7766(12) _cell_length_c 27.715(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.819(2) _cell_angle_gamma 90.00 _cell_volume 3639.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2831 _cell_measurement_theta_min 5.153 _cell_measurement_theta_max 52.862 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9292 _exptl_absorpt_correction_T_max 0.9420 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker smart' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12893 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.52 _reflns_number_total 4210 _reflns_number_gt 2849 _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^)+(0.0539P)^2^+1.6220P] 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 4210 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.12519(11) 0.81213(15) 0.50144(5) 0.0259(4) Uani 1 1 d . . . O2 O 0.31439(12) 0.36363(15) 0.55618(5) 0.0279(4) Uani 1 1 d . . . O3 O 0.16602(11) 0.99246(13) 0.59404(5) 0.0216(3) Uani 1 1 d . . . C1 C 0.25557(15) 0.8761(2) 0.69123(7) 0.0180(4) Uani 1 1 d . . . H1 H 0.2271 0.9631 0.6828 0.022 Uiso 1 1 calc R . . C2 C 0.32371(16) 0.8605(2) 0.73319(7) 0.0215(5) Uani 1 1 d . . . H2 H 0.3392 0.9366 0.7542 0.026 Uiso 1 1 calc R . . C3 C 0.36916(15) 0.7359(2) 0.74484(7) 0.0216(5) Uani 1 1 d . . . H3 H 0.4153 0.7270 0.7737 0.026 Uiso 1 1 calc R . . C4 C 0.34741(15) 0.6239(2) 0.71445(7) 0.0201(5) Uani 1 1 d . . . H4 H 0.3801 0.5389 0.7217 0.024 Uiso 1 1 calc R . . C5 C 0.08430(16) 0.3922(2) 0.63818(7) 0.0186(4) Uani 1 1 d . . . H5 H 0.1198 0.3096 0.6459 0.022 Uiso 1 1 calc R . . C6 C -0.01957(16) 0.3932(2) 0.63245(7) 0.0215(5) Uani 1 1 d . . . H6 H -0.0550 0.3117 0.6374 0.026 Uiso 1 1 calc R . . C7 C -0.07083(16) 0.5131(2) 0.61949(7) 0.0205(5) Uani 1 1 d . . . H7 H -0.1416 0.5130 0.6150 0.025 Uiso 1 1 calc R . . C8 C -0.01978(15) 0.6335(2) 0.61291(7) 0.0169(4) Uani 1 1 d . . . H8 H -0.0556 0.7146 0.6031 0.020 Uiso 1 1 calc R . . C9 C 0.15215(14) 0.75742(19) 0.61565(7) 0.0145(4) Uani 1 1 d . . . C10 C 0.24682(15) 0.5261(2) 0.63739(7) 0.0155(4) Uani 1 1 d . . . H10 H 0.2811 0.4378 0.6472 0.019 Uiso 1 1 calc R . . C11 C 0.22949(14) 0.7627(2) 0.66166(7) 0.0148(4) Uani 1 1 d . . . C12 C 0.27743(14) 0.6380(2) 0.67350(7) 0.0154(4) Uani 1 1 d . . . C13 C 0.13523(15) 0.5124(2) 0.63254(7) 0.0154(4) Uani 1 1 d . . . C14 C 0.08390(14) 0.6353(2) 0.62067(6) 0.0142(4) Uani 1 1 d . . . C15 C 0.21566(14) 0.7147(2) 0.57314(7) 0.0151(4) Uani 1 1 d . . . H15 H 0.2663 0.7880 0.5710 0.018 Uiso 1 1 calc R . . C16 C 0.27322(15) 0.57935(19) 0.58713(7) 0.0153(4) Uani 1 1 d . . . H16 H 0.3459 0.6017 0.5917 0.018 Uiso 1 1 calc R . . C17 C 0.15019(15) 0.7085(2) 0.52419(7) 0.0174(4) Uani 1 1 d . . . C18 C 0.25763(16) 0.4605(2) 0.55169(7) 0.0184(4) Uani 1 1 d . . . C19 C 0.11914(16) 0.5749(2) 0.50252(7) 0.0210(5) Uani 1 1 d . . . H19 H 0.0602 0.5702 0.4797 0.025 Uiso 1 1 calc R . . C20 C 0.17044(16) 0.4608(2) 0.51370(7) 0.0230(5) Uani 1 1 d . . . H20 H 0.1506 0.3784 0.4970 0.028 Uiso 1 1 calc R . . C21 C 0.09511(15) 0.89166(19) 0.60399(7) 0.0168(4) Uani 1 1 d . . . H21 H 0.0474 0.8774 0.5736 0.020 Uiso 1 1 calc R . . C22 C 0.03530(16) 0.9411(2) 0.64397(8) 0.0224(5) Uani 1 1 d . . . H22A H 0.0428 1.0403 0.6478 0.034 Uiso 1 1 calc R . . H22B H 0.0602 0.8958 0.6748 0.034 Uiso 1 1 calc R . . H22C H -0.0352 0.9186 0.6348 0.034 Uiso 1 1 calc R . . C23 C 0.12347(18) 1.0959(2) 0.56143(8) 0.0281(5) Uani 1 1 d . . . H23A H 0.0697 1.1418 0.5754 0.042 Uiso 1 1 calc R . . H23B H 0.0967 1.0542 0.5302 0.042 Uiso 1 1 calc R . . H23C H 0.1748 1.1629 0.5562 0.042 Uiso 1 1 calc R . . Cl1 Cl 0.10690(5) 0.72520(6) 0.76752(2) 0.03581(18) Uani 1 1 d . . . C1S C 0.0000 0.6254(3) 0.7500 0.0288(7) Uani 1 2 d S . . H1S1 H -0.0117 0.5657 0.7775 0.035 Uiso 0.50 1 calc PR . . H1S2 H 0.0117 0.5657 0.7225 0.035 Uiso 0.50 1 calc PR . . 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 0.0339(9) 0.0249(8) 0.0189(8) 0.0043(6) 0.0041(7) 0.0080(7) O2 0.0350(10) 0.0227(8) 0.0254(8) -0.0030(7) 0.0020(7) 0.0098(7) O3 0.0240(8) 0.0142(7) 0.0268(8) 0.0047(6) 0.0046(6) -0.0009(6) C1 0.0170(11) 0.0199(11) 0.0179(10) -0.0010(8) 0.0056(8) -0.0009(9) C2 0.0210(11) 0.0256(12) 0.0185(10) -0.0057(9) 0.0044(9) -0.0077(9) C3 0.0155(10) 0.0340(13) 0.0150(10) -0.0014(9) 0.0007(8) -0.0029(9) C4 0.0182(11) 0.0240(11) 0.0180(10) 0.0008(9) 0.0027(8) 0.0015(9) C5 0.0249(12) 0.0184(11) 0.0128(10) -0.0004(8) 0.0031(8) -0.0021(9) C6 0.0264(12) 0.0210(11) 0.0179(10) -0.0017(8) 0.0054(9) -0.0104(9) C7 0.0154(11) 0.0306(12) 0.0161(10) -0.0036(9) 0.0048(8) -0.0056(9) C8 0.0155(11) 0.0200(10) 0.0150(10) 0.0007(8) 0.0015(8) 0.0002(8) C9 0.0155(10) 0.0148(10) 0.0137(9) -0.0005(7) 0.0036(8) -0.0013(8) C10 0.0172(10) 0.0138(10) 0.0153(10) 0.0015(8) 0.0011(8) 0.0022(8) C11 0.0129(10) 0.0190(10) 0.0130(10) 0.0009(8) 0.0039(8) -0.0028(8) C12 0.0140(10) 0.0181(10) 0.0148(10) -0.0004(8) 0.0044(8) -0.0018(8) C13 0.0186(10) 0.0183(10) 0.0095(9) -0.0003(8) 0.0024(8) -0.0003(8) C14 0.0166(11) 0.0171(10) 0.0090(9) -0.0014(7) 0.0021(8) -0.0022(8) C15 0.0149(10) 0.0162(10) 0.0151(10) 0.0011(8) 0.0047(8) -0.0008(8) C16 0.0143(10) 0.0165(10) 0.0155(10) -0.0008(8) 0.0033(8) 0.0003(8) C17 0.0165(11) 0.0216(11) 0.0154(10) 0.0014(8) 0.0068(8) 0.0027(9) C18 0.0242(11) 0.0173(11) 0.0147(10) 0.0009(8) 0.0066(8) 0.0001(9) C19 0.0201(11) 0.0281(12) 0.0144(10) -0.0008(9) 0.0016(8) -0.0029(10) C20 0.0274(12) 0.0225(11) 0.0187(11) -0.0030(9) 0.0020(9) -0.0059(10) C21 0.0168(11) 0.0149(10) 0.0186(10) 0.0011(8) 0.0022(8) 0.0004(8) C22 0.0212(11) 0.0226(11) 0.0243(11) -0.0021(9) 0.0062(9) 0.0043(9) C23 0.0433(15) 0.0171(11) 0.0246(12) 0.0036(9) 0.0070(10) 0.0032(10) Cl1 0.0337(4) 0.0316(3) 0.0448(4) -0.0016(3) 0.0148(3) -0.0090(3) C1S 0.0338(19) 0.0199(16) 0.0323(18) 0.000 0.0032(15) 0.000 _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 C17 1.217(2) . ? O2 C18 1.216(2) . ? O3 C23 1.425(2) . ? O3 C21 1.430(2) . ? C1 C2 1.392(3) . ? C1 C11 1.395(3) . ? C1 H1 0.9500 . ? C2 C3 1.383(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C12 1.384(3) . ? C4 H4 0.9500 . ? C5 C13 1.382(3) . ? C5 C6 1.396(3) . ? C5 H5 0.9500 . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 C8 1.390(3) . ? C7 H7 0.9500 . ? C8 C14 1.393(3) . ? C8 H8 0.9500 . ? C9 C14 1.528(3) . ? C9 C21 1.535(3) . ? C9 C11 1.538(3) . ? C9 C15 1.606(3) . ? C10 C12 1.503(3) . ? C10 C13 1.507(3) . ? C10 C16 1.573(3) . ? C10 H10 1.0000 . ? C11 C12 1.399(3) . ? C13 C14 1.405(3) . ? C15 C17 1.518(3) . ? C15 C16 1.558(3) . ? C15 H15 1.0000 . ? C16 C18 1.518(3) . ? C16 H16 1.0000 . ? C17 C19 1.475(3) . ? C18 C20 1.472(3) . ? C19 C20 1.328(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.537(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 . ? Cl1 C1S 1.7600(19) . ? C1S Cl1 1.7600(18) 2_556 ? C1S H1S1 0.9900 . ? C1S H1S2 0.9900 . ? 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 C23 O3 C21 112.75(16) . . ? C2 C1 C11 119.35(19) . . ? C2 C1 H1 120.3 . . ? C11 C1 H1 120.3 . . ? C3 C2 C1 121.03(19) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.12(19) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C12 C4 C3 118.96(19) . . ? C12 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C13 C5 C6 119.6(2) . . ? C13 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 119.89(19) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.62(19) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C14 120.04(19) . . ? C7 C8 H8 120.0 . . ? C14 C8 H8 120.0 . . ? C14 C9 C21 113.13(16) . . ? C14 C9 C11 107.67(15) . . ? C21 C9 C11 114.41(16) . . ? C14 C9 C15 104.80(15) . . ? C21 C9 C15 111.89(15) . . ? C11 C9 C15 104.11(15) . . ? C12 C10 C13 107.87(16) . . ? C12 C10 C16 105.85(15) . . ? C13 C10 C16 107.28(15) . . ? C12 C10 H10 111.8 . . ? C13 C10 H10 111.8 . . ? C16 C10 H10 111.8 . . ? C1 C11 C12 118.81(18) . . ? C1 C11 C9 127.11(18) . . ? C12 C11 C9 114.08(16) . . ? C4 C12 C11 121.60(18) . . ? C4 C12 C10 124.76(18) . . ? C11 C12 C10 113.63(17) . . ? C5 C13 C14 120.94(19) . . ? C5 C13 C10 125.19(18) . . ? C14 C13 C10 113.86(17) . . ? C8 C14 C13 118.85(18) . . ? C8 C14 C9 127.36(18) . . ? C13 C14 C9 113.74(17) . . ? C17 C15 C16 113.62(16) . . ? C17 C15 C9 111.05(15) . . ? C16 C15 C9 109.79(15) . . ? C17 C15 H15 107.4 . . ? C16 C15 H15 107.4 . . ? C9 C15 H15 107.4 . . ? C18 C16 C15 117.92(16) . . ? C18 C16 C10 106.91(15) . . ? C15 C16 C10 109.57(15) . . ? C18 C16 H16 107.3 . . ? C15 C16 H16 107.3 . . ? C10 C16 H16 107.3 . . ? O1 C17 C19 118.84(18) . . ? O1 C17 C15 121.18(18) . . ? C19 C17 C15 119.94(17) . . ? O2 C18 C20 120.69(19) . . ? O2 C18 C16 119.98(18) . . ? C20 C18 C16 119.25(18) . . ? C20 C19 C17 122.48(19) . . ? C20 C19 H19 118.8 . . ? C17 C19 H19 118.8 . . ? C19 C20 C18 120.86(19) . . ? C19 C20 H20 119.6 . . ? C18 C20 H20 119.6 . . ? O3 C21 C9 107.28(15) . . ? O3 C21 C22 110.91(16) . . ? C9 C21 C22 114.64(16) . . ? O3 C21 H21 107.9 . . ? C9 C21 H21 107.9 . . ? C22 C21 H21 107.9 . . ? 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 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? Cl1 C1S Cl1 112.66(17) . 2_556 ? Cl1 C1S H1S1 109.1 . . ? Cl1 C1S H1S1 109.1 2_556 . ? Cl1 C1S H1S2 109.1 . . ? Cl1 C1S H1S2 109.1 2_556 . ? H1S1 C1S H1S2 107.8 . . ? 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 C11 C1 C2 C3 2.9(3) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C12 -2.2(3) . . . . ? C13 C5 C6 C7 2.3(3) . . . . ? C5 C6 C7 C8 -1.1(3) . . . . ? C6 C7 C8 C14 -1.8(3) . . . . ? C2 C1 C11 C12 -3.9(3) . . . . ? C2 C1 C11 C9 176.56(18) . . . . ? C14 C9 C11 C1 -130.4(2) . . . . ? C21 C9 C11 C1 -3.7(3) . . . . ? C15 C9 C11 C1 118.7(2) . . . . ? C14 C9 C11 C12 50.1(2) . . . . ? C21 C9 C11 C12 176.79(16) . . . . ? C15 C9 C11 C12 -60.8(2) . . . . ? C3 C4 C12 C11 1.1(3) . . . . ? C3 C4 C12 C10 179.77(18) . . . . ? C1 C11 C12 C4 2.0(3) . . . . ? C9 C11 C12 C4 -178.42(17) . . . . ? C1 C11 C12 C10 -176.84(17) . . . . ? C9 C11 C12 C10 2.7(2) . . . . ? C13 C10 C12 C4 125.8(2) . . . . ? C16 C10 C12 C4 -119.6(2) . . . . ? C13 C10 C12 C11 -55.4(2) . . . . ? C16 C10 C12 C11 59.2(2) . . . . ? C6 C5 C13 C14 -0.6(3) . . . . ? C6 C5 C13 C10 -179.64(18) . . . . ? C12 C10 C13 C5 -126.6(2) . . . . ? C16 C10 C13 C5 119.8(2) . . . . ? C12 C10 C13 C14 54.3(2) . . . . ? C16 C10 C13 C14 -59.3(2) . . . . ? C7 C8 C14 C13 3.4(3) . . . . ? C7 C8 C14 C9 -179.51(18) . . . . ? C5 C13 C14 C8 -2.3(3) . . . . ? C10 C13 C14 C8 176.88(16) . . . . ? C5 C13 C14 C9 -179.69(17) . . . . ? C10 C13 C14 C9 -0.6(2) . . . . ? C21 C9 C14 C8 4.3(3) . . . . ? C11 C9 C14 C8 131.74(19) . . . . ? C15 C9 C14 C8 -117.8(2) . . . . ? C21 C9 C14 C13 -178.50(16) . . . . ? C11 C9 C14 C13 -51.1(2) . . . . ? C15 C9 C14 C13 59.34(19) . . . . ? C14 C9 C15 C17 68.60(19) . . . . ? C21 C9 C15 C17 -54.4(2) . . . . ? C11 C9 C15 C17 -178.44(16) . . . . ? C14 C9 C15 C16 -57.90(19) . . . . ? C21 C9 C15 C16 179.14(15) . . . . ? C11 C9 C15 C16 55.07(19) . . . . ? C17 C15 C16 C18 -0.3(2) . . . . ? C9 C15 C16 C18 124.74(18) . . . . ? C17 C15 C16 C10 -122.83(17) . . . . ? C9 C15 C16 C10 2.2(2) . . . . ? C12 C10 C16 C18 171.67(16) . . . . ? C13 C10 C16 C18 -73.35(19) . . . . ? C12 C10 C16 C15 -59.47(19) . . . . ? C13 C10 C16 C15 55.5(2) . . . . ? C16 C15 C17 O1 -157.32(18) . . . . ? C9 C15 C17 O1 78.3(2) . . . . ? C16 C15 C17 C19 20.2(2) . . . . ? C9 C15 C17 C19 -104.2(2) . . . . ? C15 C16 C18 O2 165.63(18) . . . . ? C10 C16 C18 O2 -70.5(2) . . . . ? C15 C16 C18 C20 -17.5(3) . . . . ? C10 C16 C18 C20 106.32(19) . . . . ? O1 C17 C19 C20 153.4(2) . . . . ? C15 C17 C19 C20 -24.2(3) . . . . ? C17 C19 C20 C18 5.0(3) . . . . ? O2 C18 C20 C19 -167.2(2) . . . . ? C16 C18 C20 C19 16.0(3) . . . . ? C23 O3 C21 C9 151.55(16) . . . . ? C23 O3 C21 C22 -82.6(2) . . . . ? C14 C9 C21 O3 -172.59(14) . . . . ? C11 C9 C21 O3 63.6(2) . . . . ? C15 C9 C21 O3 -54.5(2) . . . . ? C14 C9 C21 C22 63.8(2) . . . . ? C11 C9 C21 C22 -60.0(2) . . . . ? C15 C9 C21 C22 -178.12(16) . . . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.340 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.063 # Attachment 'OSJ10M.CIF' data_osj10m _database_code_depnum_ccdc_archive 'CCDC 601817' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 O3' _chemical_formula_weight 344.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 16.221(8) _cell_length_b 7.386(4) _cell_length_c 28.003(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.388(8) _cell_angle_gamma 90.00 _cell_volume 3250(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3860 _cell_measurement_theta_min 5.185 _cell_measurement_theta_max 54.647 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9597 _exptl_absorpt_correction_T_max 0.9854 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker Smart 1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number ? _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 17536 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 27.65 _reflns_number_total 3733 _reflns_number_gt 2407 _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^)+(0.0752P)^2^+2.2345P] 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 3733 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1513 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.29548(10) 0.0045(2) 0.42404(6) 0.0319(4) Uani 1 1 d . . . O2 O -0.01242(10) 0.0262(2) 0.30089(6) 0.0308(4) Uani 1 1 d . . . O3 O 0.31400(9) 0.56548(19) 0.43490(5) 0.0210(4) Uani 1 1 d . . . C1 C 0.15162(13) 0.3974(3) 0.44999(8) 0.0181(5) Uani 1 1 d . . . H1 H 0.2041 0.4045 0.4743 0.022 Uiso 1 1 calc R . . C2 C 0.07499(14) 0.4006(3) 0.46381(8) 0.0222(5) Uani 1 1 d . . . H2 H 0.0753 0.4098 0.4977 0.027 Uiso 1 1 calc R . . C3 C -0.00142(14) 0.3906(3) 0.42879(9) 0.0240(5) Uani 1 1 d . . . H3 H -0.0534 0.3915 0.4387 0.029 Uiso 1 1 calc R . . C4 C -0.00267(14) 0.3792(3) 0.37919(9) 0.0206(5) Uani 1 1 d . . . H4 H -0.0553 0.3742 0.3550 0.025 Uiso 1 1 calc R . . C5 C 0.11976(14) 0.6044(3) 0.26160(8) 0.0186(5) Uani 1 1 d . . . H5 H 0.0659 0.5967 0.2385 0.022 Uiso 1 1 calc R . . C6 C 0.17873(14) 0.7341(3) 0.25568(8) 0.0220(5) Uani 1 1 d . . . H6 H 0.1656 0.8153 0.2285 0.026 Uiso 1 1 calc R . . C7 C 0.25621(14) 0.7433(3) 0.28951(8) 0.0217(5) Uani 1 1 d . . . H7 H 0.2966 0.8313 0.2853 0.026 Uiso 1 1 calc R . . C8 C 0.27689(13) 0.6270(3) 0.32976(8) 0.0184(5) Uani 1 1 d . . . H8 H 0.3305 0.6366 0.3529 0.022 Uiso 1 1 calc R . . C9 C 0.22836(12) 0.3609(3) 0.37885(8) 0.0151(4) Uani 1 1 d . . . C10 C 0.08162(13) 0.3455(3) 0.31352(8) 0.0163(4) Uani 1 1 d . . . H10 H 0.0248 0.3466 0.2892 0.020 Uiso 1 1 calc R . . C11 C 0.15103(12) 0.3839(3) 0.40048(8) 0.0149(4) Uani 1 1 d . . . C12 C 0.07350(13) 0.3751(3) 0.36521(8) 0.0158(4) Uani 1 1 d . . . C13 C 0.14012(13) 0.4863(3) 0.30151(7) 0.0156(4) Uani 1 1 d . . . C14 C 0.21834(12) 0.4960(3) 0.33593(7) 0.0148(4) Uani 1 1 d . . . C15 C 0.21419(13) 0.1648(3) 0.35375(8) 0.0166(4) Uani 1 1 d . . . H15 H 0.2583 0.1510 0.3346 0.020 Uiso 1 1 calc R . . C16 C 0.12571(13) 0.1578(3) 0.31534(8) 0.0171(4) Uani 1 1 d . . . H16 H 0.1364 0.1353 0.2822 0.021 Uiso 1 1 calc R . . C17 C 0.22971(13) 0.0129(3) 0.39185(8) 0.0192(5) Uani 1 1 d . . . C18 C 0.06185(13) 0.0162(3) 0.32329(8) 0.0190(5) Uani 1 1 d . . . C19 C 0.16636(14) -0.1307(3) 0.38985(9) 0.0222(5) Uani 1 1 d . . . H19 H 0.1807 -0.2290 0.4123 0.027 Uiso 1 1 calc R . . C20 C 0.09047(14) -0.1306(3) 0.35851(9) 0.0226(5) Uani 1 1 d . . . H20 H 0.0532 -0.2294 0.3589 0.027 Uiso 1 1 calc R . . C21 C 0.31328(13) 0.3817(3) 0.41820(8) 0.0187(5) Uani 1 1 d . . . H21 H 0.3114 0.3005 0.4465 0.022 Uiso 1 1 calc R . . C22 C 0.39315(14) 0.3360(3) 0.40136(9) 0.0251(5) Uani 1 1 d . . . H22A H 0.3921 0.4005 0.3706 0.038 Uiso 1 1 calc R . . H22B H 0.3952 0.2053 0.3958 0.038 Uiso 1 1 calc R . . H22C H 0.4435 0.3727 0.4268 0.038 Uiso 1 1 calc R . . C23 C 0.36526(16) 0.5916(3) 0.48340(9) 0.0288(5) Uani 1 1 d . . . H23A H 0.3493 0.5033 0.5056 0.043 Uiso 1 1 calc R . . H23B H 0.3566 0.7144 0.4945 0.043 Uiso 1 1 calc R . . H23C H 0.4253 0.5752 0.4836 0.043 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 0.0304(9) 0.0194(8) 0.0370(10) 0.0058(7) -0.0084(8) -0.0007(7) O2 0.0232(9) 0.0251(9) 0.0392(10) 0.0036(7) -0.0011(8) -0.0062(7) O3 0.0232(8) 0.0137(7) 0.0239(8) -0.0018(6) 0.0014(6) -0.0013(6) C1 0.0214(11) 0.0151(10) 0.0170(11) 0.0008(8) 0.0031(9) 0.0008(8) C2 0.0270(12) 0.0209(11) 0.0210(12) -0.0001(9) 0.0104(10) 0.0030(9) C3 0.0216(11) 0.0234(11) 0.0322(13) 0.0014(10) 0.0163(10) 0.0041(9) C4 0.0158(10) 0.0168(10) 0.0293(12) 0.0020(9) 0.0056(9) 0.0004(8) C5 0.0213(11) 0.0179(10) 0.0166(11) 0.0008(8) 0.0050(8) 0.0041(8) C6 0.0301(13) 0.0182(11) 0.0207(11) 0.0036(9) 0.0123(10) 0.0035(9) C7 0.0257(12) 0.0161(10) 0.0270(12) 0.0008(9) 0.0139(10) -0.0033(9) C8 0.0154(10) 0.0173(10) 0.0234(11) 0.0001(9) 0.0066(9) 0.0008(8) C9 0.0142(10) 0.0111(9) 0.0198(11) -0.0005(8) 0.0035(8) 0.0000(7) C10 0.0160(10) 0.0148(10) 0.0164(11) 0.0019(8) 0.0010(8) -0.0004(8) C11 0.0152(10) 0.0099(9) 0.0201(11) 0.0010(8) 0.0052(8) 0.0006(7) C12 0.0182(11) 0.0095(9) 0.0201(11) 0.0011(8) 0.0053(8) 0.0019(8) C13 0.0177(10) 0.0120(9) 0.0192(11) -0.0020(8) 0.0085(8) 0.0011(8) C14 0.0172(10) 0.0110(9) 0.0183(11) -0.0006(8) 0.0080(8) 0.0027(8) C15 0.0165(10) 0.0127(10) 0.0213(11) -0.0016(8) 0.0059(9) 0.0009(8) C16 0.0196(11) 0.0148(10) 0.0171(11) -0.0005(8) 0.0048(9) -0.0003(8) C17 0.0211(11) 0.0142(10) 0.0228(12) -0.0010(8) 0.0063(9) 0.0047(8) C18 0.0202(11) 0.0155(10) 0.0210(11) -0.0040(8) 0.0047(9) -0.0024(8) C19 0.0279(12) 0.0139(10) 0.0272(12) 0.0030(9) 0.0115(10) 0.0021(9) C20 0.0227(12) 0.0146(10) 0.0328(13) -0.0004(9) 0.0111(10) -0.0034(8) C21 0.0182(11) 0.0135(10) 0.0228(12) -0.0009(8) 0.0023(9) 0.0003(8) C22 0.0159(11) 0.0224(11) 0.0364(14) 0.0014(10) 0.0052(10) 0.0012(9) C23 0.0326(13) 0.0263(12) 0.0234(13) -0.0030(10) -0.0007(10) -0.0066(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C17 1.215(3) . ? O2 C18 1.214(3) . ? O3 C23 1.418(3) . ? O3 C21 1.435(3) . ? C1 C11 1.388(3) . ? C1 C2 1.391(3) . ? C1 H1 0.9500 . ? C2 C3 1.378(3) . ? C2 H2 0.9500 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C12 1.386(3) . ? C4 H4 0.9500 . ? C5 C13 1.391(3) . ? C5 C6 1.392(3) . ? C5 H5 0.9500 . ? C6 C7 1.375(3) . ? C6 H6 0.9500 . ? C7 C8 1.390(3) . ? C7 H7 0.9500 . ? C8 C14 1.396(3) . ? C8 H8 0.9500 . ? C9 C11 1.532(3) . ? C9 C14 1.539(3) . ? C9 C21 1.543(3) . ? C9 C15 1.602(3) . ? C10 C13 1.501(3) . ? C10 C12 1.502(3) . ? C10 C16 1.555(3) . ? C10 H10 1.0000 . ? C11 C12 1.394(3) . ? C13 C14 1.392(3) . ? C15 C17 1.525(3) . ? C15 C16 1.566(3) . ? C15 H15 1.0000 . ? C16 C18 1.527(3) . ? C16 H16 1.0000 . ? C17 C19 1.468(3) . ? C18 C20 1.462(3) . ? C19 C20 1.322(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.522(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 . ? 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 C23 O3 C21 113.34(16) . . ? C11 C1 C2 119.6(2) . . ? C11 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? C3 C2 C1 120.6(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C12 C4 C3 119.5(2) . . ? C12 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C13 C5 C6 119.6(2) . . ? C13 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 119.3(2) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 121.5(2) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C7 C8 C14 119.6(2) . . ? C7 C8 H8 120.2 . . ? C14 C8 H8 120.2 . . ? C11 C9 C14 107.40(16) . . ? C11 C9 C21 112.34(17) . . ? C14 C9 C21 113.30(17) . . ? C11 C9 C15 103.38(15) . . ? C14 C9 C15 105.54(16) . . ? C21 C9 C15 114.10(16) . . ? C13 C10 C12 109.06(16) . . ? C13 C10 C16 108.29(16) . . ? C12 C10 C16 104.37(16) . . ? C13 C10 H10 111.6 . . ? C12 C10 H10 111.6 . . ? C16 C10 H10 111.6 . . ? C1 C11 C12 119.47(19) . . ? C1 C11 C9 126.87(18) . . ? C12 C11 C9 113.45(18) . . ? C4 C12 C11 120.6(2) . . ? C4 C12 C10 124.98(19) . . ? C11 C12 C10 114.19(18) . . ? C5 C13 C14 121.17(19) . . ? C5 C13 C10 125.26(18) . . ? C14 C13 C10 113.51(17) . . ? C13 C14 C8 118.77(19) . . ? C13 C14 C9 114.11(17) . . ? C8 C14 C9 127.06(18) . . ? C17 C15 C16 114.82(17) . . ? C17 C15 C9 112.19(17) . . ? C16 C15 C9 109.78(16) . . ? C17 C15 H15 106.5 . . ? C16 C15 H15 106.5 . . ? C9 C15 H15 106.5 . . ? C18 C16 C10 106.99(17) . . ? C18 C16 C15 117.50(17) . . ? C10 C16 C15 109.18(16) . . ? C18 C16 H16 107.6 . . ? C10 C16 H16 107.6 . . ? C15 C16 H16 107.6 . . ? O1 C17 C19 117.93(19) . . ? O1 C17 C15 121.22(19) . . ? C19 C17 C15 120.83(18) . . ? O2 C18 C20 120.12(19) . . ? O2 C18 C16 120.32(19) . . ? C20 C18 C16 119.55(18) . . ? C20 C19 C17 123.5(2) . . ? C20 C19 H19 118.3 . . ? C17 C19 H19 118.3 . . ? C19 C20 C18 122.39(19) . . ? C19 C20 H20 118.8 . . ? C18 C20 H20 118.8 . . ? O3 C21 C22 111.85(17) . . ? O3 C21 C9 105.08(16) . . ? C22 C21 C9 115.74(18) . . ? O3 C21 H21 108.0 . . ? C22 C21 H21 108.0 . . ? C9 C21 H21 108.0 . . ? 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 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 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 C11 C1 C2 C3 0.0(3) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C2 C3 C4 C12 1.0(3) . . . . ? C13 C5 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C6 C7 C8 C14 0.7(3) . . . . ? C2 C1 C11 C12 0.5(3) . . . . ? C2 C1 C11 C9 -173.91(19) . . . . ? C14 C9 C11 C1 -133.7(2) . . . . ? C21 C9 C11 C1 -8.5(3) . . . . ? C15 C9 C11 C1 115.0(2) . . . . ? C14 C9 C11 C12 51.6(2) . . . . ? C21 C9 C11 C12 176.85(16) . . . . ? C15 C9 C11 C12 -59.7(2) . . . . ? C3 C4 C12 C11 -0.5(3) . . . . ? C3 C4 C12 C10 173.91(19) . . . . ? C1 C11 C12 C4 -0.2(3) . . . . ? C9 C11 C12 C4 174.92(18) . . . . ? C1 C11 C12 C10 -175.23(18) . . . . ? C9 C11 C12 C10 -0.1(2) . . . . ? C13 C10 C12 C4 132.0(2) . . . . ? C16 C10 C12 C4 -112.4(2) . . . . ? C13 C10 C12 C11 -53.2(2) . . . . ? C16 C10 C12 C11 62.3(2) . . . . ? C6 C5 C13 C14 0.5(3) . . . . ? C6 C5 C13 C10 177.40(19) . . . . ? C12 C10 C13 C5 -124.2(2) . . . . ? C16 C10 C13 C5 122.8(2) . . . . ? C12 C10 C13 C14 52.9(2) . . . . ? C16 C10 C13 C14 -60.1(2) . . . . ? C5 C13 C14 C8 -0.2(3) . . . . ? C10 C13 C14 C8 -177.48(17) . . . . ? C5 C13 C14 C9 177.32(18) . . . . ? C10 C13 C14 C9 0.0(2) . . . . ? C7 C8 C14 C13 -0.4(3) . . . . ? C7 C8 C14 C9 -177.54(19) . . . . ? C11 C9 C14 C13 -51.9(2) . . . . ? C21 C9 C14 C13 -176.53(17) . . . . ? C15 C9 C14 C13 57.9(2) . . . . ? C11 C9 C14 C8 125.4(2) . . . . ? C21 C9 C14 C8 0.7(3) . . . . ? C15 C9 C14 C8 -124.8(2) . . . . ? C11 C9 C15 C17 -72.3(2) . . . . ? C14 C9 C15 C17 175.02(16) . . . . ? C21 C9 C15 C17 50.0(2) . . . . ? C11 C9 C15 C16 56.6(2) . . . . ? C14 C9 C15 C16 -56.0(2) . . . . ? C21 C9 C15 C16 178.92(17) . . . . ? C13 C10 C16 C18 -175.33(16) . . . . ? C12 C10 C16 C18 68.58(19) . . . . ? C13 C10 C16 C15 56.5(2) . . . . ? C12 C10 C16 C15 -59.6(2) . . . . ? C17 C15 C16 C18 6.6(3) . . . . ? C9 C15 C16 C18 -120.83(19) . . . . ? C17 C15 C16 C10 128.65(19) . . . . ? C9 C15 C16 C10 1.2(2) . . . . ? C16 C15 C17 O1 -179.04(19) . . . . ? C9 C15 C17 O1 -52.8(3) . . . . ? C16 C15 C17 C19 2.7(3) . . . . ? C9 C15 C17 C19 128.9(2) . . . . ? C10 C16 C18 O2 42.6(3) . . . . ? C15 C16 C18 O2 165.70(19) . . . . ? C10 C16 C18 C20 -136.73(19) . . . . ? C15 C16 C18 C20 -13.6(3) . . . . ? O1 C17 C19 C20 175.7(2) . . . . ? C15 C17 C19 C20 -5.9(3) . . . . ? C17 C19 C20 C18 -1.3(3) . . . . ? O2 C18 C20 C19 -168.0(2) . . . . ? C16 C18 C20 C19 11.3(3) . . . . ? C23 O3 C21 C22 -79.0(2) . . . . ? C23 O3 C21 C9 154.64(18) . . . . ? C11 C9 C21 O3 -64.0(2) . . . . ? C14 C9 C21 O3 57.9(2) . . . . ? C15 C9 C21 O3 178.74(16) . . . . ? C11 C9 C21 C22 172.10(17) . . . . ? C14 C9 C21 C22 -66.0(2) . . . . ? C15 C9 C21 C22 54.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.65 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.383 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.063