Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2003 data_global _audit_creation_method SHELXL-97 # SUBMISSION DETAILS _publ_contact_author_name 'Dr Fumio Toda' _publ_contact_author_address ; Dr Fumio Toda Department of Chemistry Okayama University of Science Faculty of Science Ridai-cho 1-1 Okayama 700-0005 JAPAN ; _publ_contact_author_email TODA@CHEM.OUS.AC.JP _publ_contact_letter ; March 28, 2003 Please consider this CIF crystallographic data as a supplementary material for communication Ref.: B303060C ; _publ_requested_journal 'Organic & Biomolecular Chemistry' # PROCESSING SUMMARY (IUCr Office Use Only) _journal_coden_Cambridge 177 _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # TITLE AND AUTHOR LIST _publ_section_title ; Isolation of an inclusion complex of naphthol with its benzoate as an intermediate in solvent-free benzoylation reaction of naphthol ; loop_ _publ_author_name _publ_author_address 'Seiken Nakamatsu' ; Department of Chemistry Faculty of Science Okayama University of Science Ridaicho 1-1, Okayama 700-0005, Japan ; 'Kazuhiro Yoshizawa' ; Department of Chemistry Faculty of Science Okayama University of Science Ridaicho 1-1, Okayama 700-0005, Japan ; 'Sinji Toyota' ; Department of Chemistry Faculty of Science Okayama University of Science Ridaicho 1-1, Okayama 700-0005, Japan ; 'Fumio Toda' ; Department of Chemistry Faculty of Science Okayama University of Science Ridaicho 1-1, Okayama 700-0005, Japan ; 'Ivanka Matijasic' ; Laboratory of Organic Chemistry Faculty of Science University of Zagreb Strossmayerov trg 14 HR-10 000 Zagreb, Croatia ; data_compound(15) _database_code_CSD 207265 _chemical_name_systematic ; bisnaphthalene-2,3-diol 2,3-di(p-methylbenzoyloxy)naphthalene complex ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 O4, 2(C10 H8 O2)' _chemical_formula_sum 'C46 H36 O8' _chemical_formula_weight 716.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c n b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z' '-x-1/2, y, z-1/2' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.448(1) _cell_length_b 15.243(1) _cell_length_c 31.849(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3615.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3157 _cell_measurement_theta_min 2.209 _cell_measurement_theta_max 65.089 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.729 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graded mirror' _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5596 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 4.01 _diffrn_reflns_theta_max 65.10 _reflns_number_total 3062 _reflns_number_gt 2383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD Server Software (Nonius, 1997-2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0950P)^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 & dmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0036(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3062 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.52770(17) 0.08270(8) 0.46657(3) 0.0378(3) Uani 1 1 d . . . H100 H 0.584(3) 0.1363(16) 0.4695(7) 0.070(7) Uiso 1 1 d . . . O2 O 0.34666(18) -0.06506(8) 0.45219(4) 0.0429(4) Uani 1 1 d . . . H200 H 0.393(3) -0.0405(14) 0.4777(7) 0.064(6) Uiso 1 1 d . . . C1 C 0.5013(2) 0.06172(10) 0.42523(5) 0.0336(4) Uani 1 1 d . . . C2 C 0.4049(2) -0.01736(10) 0.41859(5) 0.0347(4) Uani 1 1 d . . . C3 C 0.3685(2) -0.04527(11) 0.37888(5) 0.0364(4) Uani 1 1 d . . . H3 H 0.3041 -0.0969 0.3749 0.0445(15) Uiso 1 1 calc R . . C4 C 0.4279(2) 0.00350(10) 0.34354(5) 0.0345(4) Uani 1 1 d . . . C5 C 0.3954(2) -0.02404(11) 0.30186(5) 0.0384(4) Uani 1 1 d . . . H5 H 0.3333 -0.0760 0.2971 0.0445(15) Uiso 1 1 calc R . . C6 C 0.4537(2) 0.02451(12) 0.26825(5) 0.0407(4) Uani 1 1 d . . . H6 H 0.4322 0.0050 0.2410 0.0445(15) Uiso 1 1 calc R . . C7 C 0.5461(2) 0.10380(12) 0.27490(5) 0.0411(4) Uani 1 1 d . . . H7 H 0.5837 0.1370 0.2521 0.0445(15) Uiso 1 1 calc R . . C8 C 0.5808(2) 0.13229(11) 0.31494(5) 0.0379(4) Uani 1 1 d . . . H8 H 0.6433 0.1844 0.3189 0.0445(15) Uiso 1 1 calc R . . C9 C 0.5230(2) 0.08366(10) 0.35029(5) 0.0338(4) Uani 1 1 d . . . C10 C 0.5583(2) 0.11117(11) 0.39207(5) 0.0349(4) Uani 1 1 d . . . H10 H 0.6206 0.1631 0.3969 0.0445(15) Uiso 1 1 calc R . . O3 O 0.07887(15) 0.16735(7) 0.45942(3) 0.0343(3) Uani 1 1 d . . . O4 O 0.29390(16) 0.26605(7) 0.47399(3) 0.0392(3) Uani 1 1 d . . . C11 C 0.0463(2) 0.20934(10) 0.42088(5) 0.0315(4) Uani 1 1 d . . . C12 C 0.0905(2) 0.16948(10) 0.38433(5) 0.0321(4) Uani 1 1 d . . . H12 H 0.1505 0.1160 0.3848 0.0445(15) Uiso 1 1 calc R . . C13 C 0.0457(2) 0.20896(10) 0.34541(5) 0.0322(4) Uani 1 1 d . . . C14 C 0.0903(2) 0.16945(10) 0.30653(5) 0.0356(4) Uani 1 1 d . . . H14 H 0.1503 0.1160 0.3062 0.0445(15) Uiso 1 1 calc R . . C15 C 0.0457(2) 0.20947(10) 0.26932(5) 0.0378(4) Uani 1 1 d . . . H15 H 0.0759 0.1830 0.2440 0.0445(15) Uiso 1 1 calc R . . C16 C 0.1977(2) 0.20723(10) 0.48596(5) 0.0332(4) Uani 1 1 d . . . C17 C 0.1881(2) 0.17198(10) 0.52891(5) 0.0340(4) Uani 1 1 d . . . C18 C 0.2633(3) 0.22020(12) 0.56133(6) 0.0448(5) Uani 1 1 d . . . H18 H 0.3253 0.2718 0.5556 0.0445(15) Uiso 1 1 calc R . . C19 C 0.2459(3) 0.19123(12) 0.60237(5) 0.0468(5) Uani 1 1 d . . . H19 H 0.2959 0.2242 0.6240 0.0445(15) Uiso 1 1 calc R . . C20 C 0.1556(2) 0.11420(12) 0.61188(5) 0.0398(4) Uani 1 1 d . . . C21 C 0.0849(3) 0.06622(12) 0.57910(6) 0.0475(5) Uani 1 1 d . . . H21 H 0.0268 0.0135 0.5847 0.0445(15) Uiso 1 1 calc R . . C22 C 0.0986(3) 0.09494(12) 0.53805(5) 0.0436(5) Uani 1 1 d . . . H22 H 0.0475 0.0622 0.5165 0.0445(15) Uiso 1 1 calc R . . C23 C 0.1310(3) 0.08440(13) 0.65693(6) 0.0508(5) Uani 1 1 d . . . H23A H 0.1872 0.1257 0.6755 0.165(9) Uiso 1 1 calc R . . H23B H 0.1850 0.0277 0.6606 0.165(9) Uiso 1 1 calc R . . H23C H 0.0052 0.0809 0.6633 0.165(9) 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 0.0462(8) 0.0352(7) 0.0320(6) -0.0002(5) -0.0052(5) -0.0073(6) O2 0.0545(9) 0.0378(7) 0.0364(6) 0.0065(5) -0.0109(6) -0.0138(6) C1 0.0337(9) 0.0341(8) 0.0330(8) -0.0012(7) -0.0059(7) 0.0002(8) C2 0.0360(10) 0.0332(8) 0.0348(8) 0.0031(7) -0.0038(7) -0.0013(7) C3 0.0370(10) 0.0310(8) 0.0414(9) 0.0004(7) -0.0071(8) 0.0002(7) C4 0.0316(9) 0.0349(9) 0.0370(9) -0.0030(7) -0.0026(7) 0.0036(7) C5 0.0366(10) 0.0379(9) 0.0407(9) -0.0061(7) -0.0050(8) 0.0043(8) C6 0.0393(11) 0.0479(10) 0.0349(9) -0.0072(7) -0.0004(8) 0.0068(8) C7 0.0393(11) 0.0490(10) 0.0351(9) 0.0016(7) 0.0045(8) 0.0029(9) C8 0.0335(10) 0.0409(9) 0.0394(9) 0.0005(7) 0.0004(8) -0.0024(8) C9 0.0286(9) 0.0368(9) 0.0359(9) -0.0014(7) -0.0015(7) 0.0027(7) C10 0.0331(10) 0.0343(8) 0.0372(9) -0.0013(7) -0.0025(7) -0.0028(7) O3 0.0367(7) 0.0329(6) 0.0333(6) 0.0025(4) -0.0033(5) -0.0049(5) O4 0.0372(7) 0.0371(7) 0.0433(7) 0.0056(5) -0.0011(6) -0.0075(6) C11 0.0282(9) 0.0334(8) 0.0329(8) 0.0041(7) -0.0013(7) -0.0051(7) C12 0.0284(9) 0.0296(8) 0.0384(9) -0.0001(6) -0.0004(7) -0.0003(7) C13 0.0286(9) 0.0320(8) 0.0359(9) -0.0008(6) 0.0006(7) -0.0024(7) C14 0.0347(10) 0.0329(9) 0.0393(9) 0.0000(7) 0.0016(7) -0.0012(7) C15 0.0384(10) 0.0398(9) 0.0352(8) -0.0046(7) 0.0025(7) -0.0029(8) C16 0.0311(9) 0.0309(8) 0.0377(8) -0.0006(7) -0.0007(7) 0.0006(7) C17 0.0329(10) 0.0322(9) 0.0369(9) 0.0016(7) 0.0004(7) 0.0018(7) C18 0.0525(12) 0.0378(9) 0.0440(10) 0.0038(7) -0.0098(9) -0.0092(9) C19 0.0582(13) 0.0445(10) 0.0378(9) 0.0003(8) -0.0118(9) -0.0025(9) C20 0.0357(10) 0.0458(10) 0.0379(9) 0.0037(7) -0.0010(8) 0.0067(8) C21 0.0523(12) 0.0464(10) 0.0438(10) 0.0076(8) 0.0025(9) -0.0123(9) C22 0.0500(12) 0.0418(10) 0.0390(9) 0.0004(7) -0.0019(9) -0.0114(9) C23 0.0501(13) 0.0639(12) 0.0384(10) 0.0103(9) 0.0029(9) 0.0071(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 C1 1.3692(19) . ? O1 H100 0.92(2) . ? O2 C2 1.3646(19) . ? O2 H200 0.96(2) . ? C1 C10 1.365(2) . ? C1 C2 1.419(2) . ? C2 C3 1.361(2) . ? C3 C4 1.420(2) . ? C3 H3 0.9300 . ? C4 C5 1.413(2) . ? C4 C9 1.429(2) . ? C5 C6 1.372(2) . ? C5 H5 0.9300 . ? C6 C7 1.407(2) . ? C6 H6 0.9300 . ? C7 C8 1.372(2) . ? C7 H7 0.9300 . ? C8 C9 1.415(2) . ? C8 H8 0.9300 . ? C9 C10 1.420(2) . ? C10 H10 0.9300 . ? O3 C16 1.3663(19) . ? O3 C11 1.4053(18) . ? O4 C16 1.2095(19) . ? C11 C12 1.354(2) . ? C11 C11 1.418(3) 2 ? C12 C13 1.418(2) . ? C12 H12 0.9300 . ? C13 C14 1.416(2) . ? C13 C13 1.424(3) 2 ? C14 C15 1.374(2) . ? C14 H14 0.9300 . ? C15 C15 1.410(3) 2 ? C15 H15 0.9300 . ? C16 C17 1.471(2) . ? C17 C22 1.381(2) . ? C17 C18 1.386(2) . ? C18 C19 1.386(2) . ? C18 H18 0.9300 . ? C19 C20 1.387(2) . ? C19 H19 0.9300 . ? C20 C21 1.379(3) . ? C20 C23 1.516(2) . ? C21 C22 1.382(2) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 C1 O1 H100 111.7(13) . . ? C2 O2 H200 109.9(13) . . ? C10 C1 O1 124.77(15) . . ? C10 C1 C2 120.74(15) . . ? O1 C1 C2 114.48(14) . . ? C3 C2 O2 119.92(15) . . ? C3 C2 C1 120.31(15) . . ? O2 C2 C1 119.77(14) . . ? C2 C3 C4 120.73(15) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C9 118.72(15) . . ? C5 C4 C3 122.40(16) . . ? C9 C4 C3 118.87(14) . . ? C6 C5 C4 121.21(16) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.06(16) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.28(16) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 121.10(16) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C4 119.05(14) . . ? C10 C9 C8 122.32(15) . . ? C4 C9 C8 118.62(14) . . ? C1 C10 C9 120.29(15) . . ? C1 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C16 O3 C11 116.71(12) . . ? C12 C11 O3 120.31(14) . . ? C12 C11 C11 120.69(9) . 2 ? O3 C11 C11 118.81(8) . 2 ? C11 C12 C13 120.27(15) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 121.91(15) . . ? C14 C13 C13 119.05(9) . 2 ? C12 C13 C13 119.04(9) . 2 ? C15 C14 C13 120.57(15) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C15 120.38(10) . 2 ? C14 C15 H15 119.8 . . ? C15 C15 H15 119.8 2 . ? O4 C16 O3 121.24(15) . . ? O4 C16 C17 126.32(16) . . ? O3 C16 C17 112.41(14) . . ? C22 C17 C18 119.27(16) . . ? C22 C17 C16 122.00(15) . . ? C18 C17 C16 118.65(15) . . ? C19 C18 C17 119.72(17) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C18 121.43(17) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 117.95(16) . . ? C21 C20 C23 120.77(17) . . ? C19 C20 C23 121.27(17) . . ? C22 C21 C20 121.32(17) . . ? C22 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? C17 C22 C21 120.28(17) . . ? C17 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 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 C10 C1 C2 C3 0.3(3) . . . . ? O1 C1 C2 C3 179.52(15) . . . . ? C10 C1 C2 O2 -178.95(15) . . . . ? O1 C1 C2 O2 0.3(2) . . . . ? O2 C2 C3 C4 179.95(15) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C5 178.95(16) . . . . ? C2 C3 C4 C9 -1.5(3) . . . . ? C9 C4 C5 C6 0.2(3) . . . . ? C3 C4 C5 C6 179.78(16) . . . . ? C4 C5 C6 C7 -0.7(3) . . . . ? C5 C6 C7 C8 1.0(3) . . . . ? C6 C7 C8 C9 -0.8(3) . . . . ? C5 C4 C9 C10 -179.15(16) . . . . ? C3 C4 C9 C10 1.2(2) . . . . ? C5 C4 C9 C8 0.0(2) . . . . ? C3 C4 C9 C8 -179.59(15) . . . . ? C7 C8 C9 C10 179.46(16) . . . . ? C7 C8 C9 C4 0.3(3) . . . . ? O1 C1 C10 C9 -179.64(15) . . . . ? C2 C1 C10 C9 -0.5(3) . . . . ? C4 C9 C10 C1 -0.3(3) . . . . ? C8 C9 C10 C1 -179.42(16) . . . . ? C16 O3 C11 C12 116.76(17) . . . . ? C16 O3 C11 C11 -68.2(2) . . . 2 ? O3 C11 C12 C13 175.35(14) . . . . ? C11 C11 C12 C13 0.4(3) 2 . . . ? C11 C12 C13 C14 179.74(15) . . . . ? C11 C12 C13 C13 0.2(3) . . . 2 ? C12 C13 C14 C15 -179.75(15) . . . . ? C13 C13 C14 C15 -0.2(3) 2 . . . ? C13 C14 C15 C15 -0.1(3) . . . 2 ? C11 O3 C16 O4 -13.2(2) . . . . ? C11 O3 C16 C17 165.23(13) . . . . ? O4 C16 C17 C22 -168.13(17) . . . . ? O3 C16 C17 C22 13.6(2) . . . . ? O4 C16 C17 C18 15.3(3) . . . . ? O3 C16 C17 C18 -163.04(15) . . . . ? C22 C17 C18 C19 -0.8(3) . . . . ? C16 C17 C18 C19 175.83(17) . . . . ? C17 C18 C19 C20 0.5(3) . . . . ? C18 C19 C20 C21 0.8(3) . . . . ? C18 C19 C20 C23 -177.77(18) . . . . ? C19 C20 C21 C22 -1.8(3) . . . . ? C23 C20 C21 C22 176.73(18) . . . . ? C18 C17 C22 C21 -0.2(3) . . . . ? C16 C17 C22 C21 -176.74(17) . . . . ? C20 C21 C22 C17 1.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 65.10 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.211 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.042