data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yoshitane Imai' _publ_contact_author_email Y-IMAI@APCH.KINDAI.AC.JP _publ_section_title ; Recovery and molecular recognition of bisphenol A and its derivatives using p-benzoquinone molecule ; loop_ _publ_author_name 'Yoshitane Imai' 'Noriaki Iwase' 'Takafumi Kinuta' 'Reiko Kuroda' 'Yoshio Matsubara' 'Tomohiro Sato' 'Nobuo Tajima' # Attachment 'IMAI917ver1.CIF' data_imai917_1 _database_code_depnum_ccdc_archive 'CCDC 759687' #TrackingRef 'IMAI917ver1.CIF' #data_im9174a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 O4' _chemical_formula_weight 336.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 22.0528(18) _cell_length_b 6.3612(5) _cell_length_c 24.693(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3463.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3389 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 27.90 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9528 _exptl_absorpt_correction_T_max 0.9782 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19949 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.90 _reflns_number_total 4068 _reflns_number_gt 3389 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0579P)^2^+1.0490P] 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 4068 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.13815(6) 0.18269(19) 0.70365(5) 0.0206(3) Uani 1 1 d . . . C2 C 0.19013(6) 0.1585(2) 0.67244(5) 0.0228(3) Uani 1 1 d . . . H2 H 0.2193 0.0559 0.6827 0.027 Uiso 1 1 calc R . . C3 C 0.20067(6) 0.2804(2) 0.62662(5) 0.0236(3) Uani 1 1 d . . . H3 H 0.2365 0.2600 0.6059 0.028 Uiso 1 1 calc R . . C4 C 0.15893(6) 0.4314(2) 0.61140(5) 0.0220(3) Uani 1 1 d . . . C5 C 0.10555(7) 0.4540(2) 0.64075(5) 0.0277(3) Uani 1 1 d . . . H5 H 0.0758 0.5529 0.6296 0.033 Uiso 1 1 calc R . . C6 C 0.09596(6) 0.3319(2) 0.68631(5) 0.0276(3) Uani 1 1 d . . . H6 H 0.0596 0.3501 0.7064 0.033 Uiso 1 1 calc R . . C7 C 0.12583(5) 0.0539(2) 0.75508(5) 0.0223(3) Uani 1 1 d . . . C8 C 0.07293(7) -0.0966(2) 0.74376(6) 0.0320(3) Uani 1 1 d . . . H8A H 0.0368 -0.0152 0.7341 0.048 Uiso 1 1 calc R . . H8B H 0.0646 -0.1805 0.7762 0.048 Uiso 1 1 calc R . . H8C H 0.0836 -0.1901 0.7137 0.048 Uiso 1 1 calc R . . C9 C 0.18128(7) -0.0781(2) 0.77111(6) 0.0340(3) Uani 1 1 d . . . H9A H 0.1887 -0.1852 0.7434 0.051 Uiso 1 1 calc R . . H9B H 0.1736 -0.1468 0.8060 0.051 Uiso 1 1 calc R . . H9C H 0.2169 0.0133 0.7742 0.051 Uiso 1 1 calc R . . C10 C 0.11171(6) 0.20587(19) 0.80167(5) 0.0203(3) Uani 1 1 d . . . C11 C 0.05604(6) 0.2151(2) 0.82790(5) 0.0253(3) Uani 1 1 d . . . H11 H 0.0251 0.1190 0.8178 0.030 Uiso 1 1 calc R . . C12 C 0.04436(6) 0.3614(2) 0.86856(6) 0.0287(3) Uani 1 1 d . . . H12 H 0.0057 0.3657 0.8855 0.034 Uiso 1 1 calc R . . C13 C 0.08934(6) 0.5002(2) 0.88419(5) 0.0246(3) Uani 1 1 d . . . C14 C 0.14610(6) 0.4897(2) 0.85997(5) 0.0261(3) Uani 1 1 d . . . H14 H 0.1778 0.5805 0.8716 0.031 Uiso 1 1 calc R . . C15 C 0.15624(6) 0.3464(2) 0.81887(5) 0.0258(3) Uani 1 1 d . . . H15 H 0.1948 0.3435 0.8018 0.031 Uiso 1 1 calc R . . O4 O 0.17195(4) 0.55414(15) 0.56716(4) 0.0269(2) Uani 1 1 d . . . H4 H 0.1463 0.6515 0.5648 0.040 Uiso 1 1 calc R . . O13 O 0.07623(5) 0.64292(16) 0.92418(4) 0.0320(2) Uani 1 1 d . . . H13 H 0.1044 0.7315 0.9263 0.048 Uiso 1 1 calc R . . C21 C 0.14345(6) 0.1188(2) 0.96240(5) 0.0244(3) Uani 1 1 d . . . C22 C 0.08166(6) 0.1369(2) 0.98463(5) 0.0276(3) Uani 1 1 d . . . H22 H 0.0524 0.0331 0.9756 0.033 Uiso 1 1 calc R . . C23 C 0.06575(6) 0.2950(2) 1.01705(6) 0.0277(3) Uani 1 1 d . . . H23 H 0.0260 0.2994 1.0318 0.033 Uiso 1 1 calc R . . C24 C 0.10924(6) 0.4627(2) 1.03015(5) 0.0259(3) Uani 1 1 d . . . C25 C 0.17111(6) 0.4458(2) 1.00806(5) 0.0253(3) Uani 1 1 d . . . H25 H 0.2004 0.5491 1.0173 0.030 Uiso 1 1 calc R . . C26 C 0.18667(6) 0.2882(2) 0.97539(5) 0.0251(3) Uani 1 1 d . . . H26 H 0.2262 0.2850 0.9602 0.030 Uiso 1 1 calc R . . O21 O 0.15904(5) -0.03246(15) 0.93491(4) 0.0320(2) Uani 1 1 d . . . O24 O 0.09377(5) 0.61388(16) 1.05790(4) 0.0345(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0236(6) 0.0187(6) 0.0196(6) -0.0013(5) -0.0001(5) 0.0011(5) C2 0.0226(6) 0.0233(6) 0.0227(6) -0.0009(5) -0.0013(5) 0.0048(5) C3 0.0212(6) 0.0280(7) 0.0216(6) -0.0018(5) 0.0022(5) 0.0014(5) C4 0.0292(7) 0.0192(6) 0.0176(6) -0.0008(5) -0.0010(5) -0.0031(5) C5 0.0309(7) 0.0255(7) 0.0265(7) 0.0030(5) 0.0016(5) 0.0105(6) C6 0.0261(7) 0.0300(7) 0.0267(7) 0.0029(5) 0.0067(5) 0.0088(5) C7 0.0244(7) 0.0194(6) 0.0233(6) 0.0016(5) 0.0029(5) 0.0019(5) C8 0.0393(8) 0.0239(7) 0.0329(7) -0.0055(6) 0.0064(6) -0.0071(6) C9 0.0387(8) 0.0299(7) 0.0335(8) 0.0120(6) 0.0050(6) 0.0123(6) C10 0.0231(6) 0.0194(6) 0.0183(6) 0.0037(5) -0.0011(5) -0.0005(5) C11 0.0207(6) 0.0279(7) 0.0272(7) -0.0035(5) -0.0014(5) -0.0036(5) C12 0.0222(7) 0.0343(8) 0.0296(7) -0.0060(6) 0.0028(5) 0.0004(6) C13 0.0317(7) 0.0211(6) 0.0209(6) 0.0007(5) -0.0022(5) 0.0013(5) C14 0.0303(7) 0.0237(7) 0.0244(6) 0.0027(5) -0.0019(5) -0.0089(5) C15 0.0239(7) 0.0289(7) 0.0245(6) 0.0028(5) 0.0036(5) -0.0048(5) O4 0.0325(5) 0.0243(5) 0.0241(5) 0.0043(4) 0.0016(4) -0.0006(4) O13 0.0374(6) 0.0268(5) 0.0317(5) -0.0089(4) 0.0010(4) -0.0017(4) C21 0.0303(7) 0.0214(6) 0.0215(6) -0.0018(5) -0.0013(5) 0.0017(5) C22 0.0285(7) 0.0229(7) 0.0313(7) -0.0041(5) -0.0019(6) -0.0054(5) C23 0.0243(7) 0.0262(7) 0.0324(7) -0.0034(6) 0.0029(5) -0.0023(5) C24 0.0320(7) 0.0219(6) 0.0239(6) -0.0036(5) 0.0007(5) -0.0006(5) C25 0.0266(7) 0.0240(7) 0.0253(6) -0.0014(5) -0.0013(5) -0.0053(5) C26 0.0245(7) 0.0259(7) 0.0248(6) 0.0008(5) 0.0008(5) -0.0002(5) O21 0.0400(6) 0.0254(5) 0.0306(5) -0.0080(4) 0.0033(4) 0.0017(4) O24 0.0400(6) 0.0274(5) 0.0362(6) -0.0124(4) 0.0062(5) -0.0017(4) _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 1.3899(18) . ? C1 C6 1.3964(18) . ? C1 C7 1.5354(17) . ? C2 C3 1.3913(18) . ? C3 C4 1.3825(18) . ? C4 O4 1.3730(15) . ? C4 C5 1.3898(19) . ? C5 C6 1.3832(18) . ? C7 C10 1.5343(17) . ? C7 C8 1.5348(18) . ? C7 C9 1.5355(18) . ? C10 C11 1.3894(18) . ? C10 C15 1.3940(18) . ? C11 C12 1.3927(18) . ? C12 C13 1.3831(19) . ? C13 O13 1.3720(15) . ? C13 C14 1.389(2) . ? C14 C15 1.3827(19) . ? C21 O21 1.2269(16) . ? C21 C22 1.474(2) . ? C21 C26 1.4741(19) . ? C22 C23 1.3325(19) . ? C23 C24 1.4702(19) . ? C24 O24 1.2294(16) . ? C24 C25 1.4735(19) . ? C25 C26 1.3313(19) . ? 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 117.05(12) . . ? C2 C1 C7 123.06(11) . . ? C6 C1 C7 119.89(11) . . ? C1 C2 C3 121.80(12) . . ? C4 C3 C2 119.82(12) . . ? O4 C4 C3 118.17(11) . . ? O4 C4 C5 122.23(12) . . ? C3 C4 C5 119.59(12) . . ? C6 C5 C4 119.72(12) . . ? C5 C6 C1 121.94(12) . . ? C10 C7 C8 112.04(10) . . ? C10 C7 C1 108.66(10) . . ? C8 C7 C1 108.45(11) . . ? C10 C7 C9 108.24(11) . . ? C8 C7 C9 108.12(12) . . ? C1 C7 C9 111.36(10) . . ? C11 C10 C15 116.94(12) . . ? C11 C10 C7 123.75(11) . . ? C15 C10 C7 119.30(11) . . ? C10 C11 C12 121.86(12) . . ? C13 C12 C11 119.67(13) . . ? O13 C13 C12 118.18(12) . . ? O13 C13 C14 122.11(12) . . ? C12 C13 C14 119.70(12) . . ? C15 C14 C13 119.57(12) . . ? C14 C15 C10 122.18(12) . . ? O21 C21 C22 121.77(13) . . ? O21 C21 C26 120.84(13) . . ? C22 C21 C26 117.38(11) . . ? C23 C22 C21 121.74(12) . . ? C22 C23 C24 120.53(13) . . ? O24 C24 C23 120.62(13) . . ? O24 C24 C25 121.36(13) . . ? C23 C24 C25 118.01(12) . . ? C26 C25 C24 121.18(12) . . ? C25 C26 C21 121.04(12) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.305 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.050 #===END data_imai917_2 _database_code_depnum_ccdc_archive 'CCDC 759688' #TrackingRef 'IMAI917ver1.CIF' #data_im9190a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 F6 O4' _chemical_formula_weight 444.32 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' F F 0.0171 0.0103 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.6512(5) _cell_length_b 23.5120(17) _cell_length_c 12.0859(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.6020(10) _cell_angle_gamma 90.00 _cell_volume 1881.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3423 _cell_measurement_theta_min 1.73 _cell_measurement_theta_max 27.87 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9370 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11676 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.87 _reflns_number_total 4265 _reflns_number_gt 3423 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0472P)^2^+0.4562P] 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 4265 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.002 _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 0.4469(2) 0.19881(6) 0.51906(12) 0.0167(3) Uani 1 1 d . . . C2 C 0.4793(2) 0.18646(7) 0.63224(13) 0.0196(3) Uani 1 1 d . . . H2 H 0.5694 0.2095 0.6787 0.023 Uiso 1 1 calc R . . C3 C 0.3834(2) 0.14155(7) 0.67809(13) 0.0208(3) Uani 1 1 d . . . H3 H 0.4083 0.1336 0.7553 0.025 Uiso 1 1 calc R . . C4 C 0.2507(2) 0.10807(6) 0.61126(13) 0.0193(3) Uani 1 1 d . . . C5 C 0.2184(2) 0.11921(7) 0.49860(13) 0.0195(3) Uani 1 1 d . . . H5 H 0.1283 0.0960 0.4524 0.023 Uiso 1 1 calc R . . C6 C 0.3170(2) 0.16406(7) 0.45276(13) 0.0177(3) Uani 1 1 d . . . H6 H 0.2953 0.1711 0.3751 0.021 Uiso 1 1 calc R . . C7 C 0.5607(2) 0.25008(7) 0.47631(12) 0.0166(3) Uani 1 1 d . . . C8 C 0.7800(2) 0.23057(7) 0.46800(13) 0.0219(3) Uani 1 1 d . . . F9 F 0.78681(14) 0.18069(4) 0.41543(8) 0.0274(2) Uani 1 1 d . . . F10 F 0.87951(13) 0.22363(4) 0.56864(8) 0.0251(2) Uani 1 1 d . . . F11 F 0.88734(13) 0.26740(4) 0.41304(8) 0.0286(2) Uani 1 1 d . . . C12 C 0.4736(2) 0.26946(7) 0.35955(13) 0.0201(3) Uani 1 1 d . . . F13 F 0.55127(14) 0.31905(4) 0.33068(8) 0.0266(2) Uani 1 1 d . . . F14 F 0.27379(13) 0.27725(4) 0.35566(7) 0.0237(2) Uani 1 1 d . . . F15 F 0.50612(14) 0.23212(4) 0.27966(7) 0.0263(2) Uani 1 1 d . . . C16 C 0.5453(2) 0.30151(6) 0.55385(12) 0.0171(3) Uani 1 1 d . . . C17 C 0.7029(2) 0.33869(7) 0.58498(13) 0.0192(3) Uani 1 1 d . . . H17 H 0.8310 0.3326 0.5585 0.023 Uiso 1 1 calc R . . C18 C 0.6764(2) 0.38451(7) 0.65387(13) 0.0195(3) Uani 1 1 d . . . H18 H 0.7866 0.4091 0.6757 0.023 Uiso 1 1 calc R . . C19 C 0.4888(2) 0.39458(6) 0.69104(12) 0.0182(3) Uani 1 1 d . . . C20 C 0.3293(2) 0.35837(7) 0.65974(13) 0.0199(3) Uani 1 1 d . . . H20 H 0.2004 0.3652 0.6846 0.024 Uiso 1 1 calc R . . C21 C 0.3577(2) 0.31238(7) 0.59246(13) 0.0189(3) Uani 1 1 d . . . H21 H 0.2476 0.2876 0.5719 0.023 Uiso 1 1 calc R . . O4 O 0.14744(17) 0.06379(5) 0.65275(10) 0.0265(3) Uani 1 1 d . . . H4 H 0.1824 0.0603 0.7211 0.040 Uiso 1 1 calc R . . O19 O 0.46947(17) 0.44075(5) 0.75789(9) 0.0239(3) Uani 1 1 d . . . H19 H 0.3497 0.4430 0.7740 0.036 Uiso 1 1 calc R . . C31 C 0.6504(2) 0.47659(7) 0.43711(13) 0.0222(3) Uani 1 1 d . . . C32 C 0.7047(2) 0.51610(7) 0.52943(14) 0.0241(4) Uani 1 1 d . . . H32 H 0.8426 0.5256 0.5482 0.029 Uiso 1 1 calc R . . C33 C 0.5645(2) 0.53871(7) 0.58712(14) 0.0234(3) Uani 1 1 d . . . H33 H 0.6032 0.5651 0.6448 0.028 Uiso 1 1 calc R . . O31 O 0.77900(17) 0.45755(5) 0.38131(10) 0.0284(3) Uani 1 1 d . . . C41 C 1.0384(2) 0.47431(7) 0.89751(14) 0.0219(3) Uani 1 1 d . . . C42 C 0.8542(2) 0.50803(7) 0.90673(14) 0.0234(4) Uani 1 1 d . . . H42 H 0.7581 0.5121 0.8437 0.028 Uiso 1 1 calc R . . C43 C 0.8205(2) 0.53277(7) 1.00212(14) 0.0238(4) Uani 1 1 d . . . H43 H 0.7030 0.5555 1.0054 0.029 Uiso 1 1 calc R . . O41 O 1.07341(17) 0.45382(5) 0.80841(10) 0.0295(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0143(7) 0.0201(8) 0.0159(7) -0.0007(6) 0.0025(6) 0.0020(6) C2 0.0186(7) 0.0236(8) 0.0159(8) -0.0031(6) -0.0017(6) 0.0010(6) C3 0.0229(8) 0.0245(9) 0.0147(8) 0.0011(6) 0.0015(6) 0.0040(7) C4 0.0176(7) 0.0172(8) 0.0235(8) -0.0003(6) 0.0047(6) 0.0028(6) C5 0.0165(7) 0.0193(8) 0.0221(8) -0.0035(6) -0.0005(6) 0.0007(6) C6 0.0169(7) 0.0227(8) 0.0133(7) -0.0019(6) 0.0003(6) 0.0036(6) C7 0.0135(7) 0.0226(8) 0.0135(7) -0.0010(6) 0.0009(6) 0.0003(6) C8 0.0179(7) 0.0286(9) 0.0192(8) -0.0039(7) 0.0020(6) 0.0000(7) F9 0.0216(5) 0.0332(6) 0.0272(5) -0.0123(4) 0.0016(4) 0.0045(4) F10 0.0175(4) 0.0348(6) 0.0219(5) -0.0046(4) -0.0041(4) 0.0050(4) F11 0.0178(5) 0.0400(6) 0.0291(5) -0.0016(4) 0.0083(4) -0.0035(4) C12 0.0168(7) 0.0268(8) 0.0171(8) 0.0000(6) 0.0032(6) -0.0023(6) F13 0.0266(5) 0.0313(6) 0.0222(5) 0.0070(4) 0.0035(4) -0.0053(4) F14 0.0166(4) 0.0342(5) 0.0198(5) 0.0044(4) -0.0013(4) 0.0013(4) F15 0.0283(5) 0.0364(6) 0.0142(5) -0.0032(4) 0.0027(4) -0.0006(4) C16 0.0187(7) 0.0188(8) 0.0137(7) 0.0010(6) 0.0006(6) 0.0012(6) C17 0.0148(7) 0.0234(8) 0.0192(8) 0.0039(6) 0.0014(6) 0.0010(6) C18 0.0170(7) 0.0206(8) 0.0202(8) 0.0018(6) -0.0020(6) -0.0028(6) C19 0.0239(8) 0.0169(8) 0.0136(8) 0.0022(6) 0.0003(6) 0.0020(6) C20 0.0174(7) 0.0238(8) 0.0192(8) 0.0019(6) 0.0051(6) 0.0008(6) C21 0.0159(7) 0.0215(8) 0.0192(8) -0.0003(6) 0.0022(6) -0.0025(6) O4 0.0301(6) 0.0245(6) 0.0250(6) 0.0045(5) 0.0038(5) -0.0038(5) O19 0.0243(6) 0.0232(6) 0.0244(6) -0.0058(5) 0.0030(5) 0.0005(5) C31 0.0229(8) 0.0234(9) 0.0200(8) 0.0035(7) 0.0019(6) 0.0042(7) C32 0.0205(8) 0.0282(9) 0.0237(9) 0.0006(7) 0.0021(7) 0.0004(7) C33 0.0254(8) 0.0238(8) 0.0207(8) -0.0007(7) 0.0007(7) 0.0001(7) O31 0.0259(6) 0.0344(7) 0.0258(6) -0.0016(5) 0.0074(5) 0.0074(5) C41 0.0216(8) 0.0201(8) 0.0245(9) -0.0031(6) 0.0050(7) -0.0061(6) C42 0.0192(8) 0.0253(9) 0.0254(9) 0.0002(7) 0.0001(7) -0.0014(7) C43 0.0182(8) 0.0229(8) 0.0305(9) -0.0007(7) 0.0029(7) 0.0011(6) O41 0.0277(6) 0.0351(7) 0.0270(7) -0.0119(5) 0.0084(5) -0.0064(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.386(2) . ? C1 C2 1.394(2) . ? C1 C7 1.539(2) . ? C2 C3 1.378(2) . ? C3 C4 1.383(2) . ? C4 O4 1.3688(19) . ? C4 C5 1.383(2) . ? C5 C6 1.386(2) . ? C7 C16 1.539(2) . ? C7 C12 1.541(2) . ? C7 C8 1.542(2) . ? C8 F10 1.3368(18) . ? C8 F9 1.3367(18) . ? C8 F11 1.3392(18) . ? C12 F13 1.3354(18) . ? C12 F15 1.3381(18) . ? C12 F14 1.3377(17) . ? C16 C17 1.388(2) . ? C16 C21 1.398(2) . ? C17 C18 1.383(2) . ? C18 C19 1.387(2) . ? C19 O19 1.3668(18) . ? C19 C20 1.384(2) . ? C20 C21 1.377(2) . ? C31 O31 1.2246(19) . ? C31 C32 1.470(2) . ? C31 C33 1.475(2) 3_666 ? C32 C33 1.329(2) . ? C33 C31 1.475(2) 3_666 ? C41 O41 1.2227(19) . ? C41 C43 1.469(2) 3_767 ? C41 C42 1.473(2) . ? C42 C43 1.330(2) . ? C43 C41 1.469(2) 3_767 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.18(14) . . ? C6 C1 C7 124.53(13) . . ? C2 C1 C7 117.29(13) . . ? C3 C2 C1 121.38(15) . . ? C2 C3 C4 119.72(15) . . ? O4 C4 C3 122.23(14) . . ? O4 C4 C5 118.01(14) . . ? C3 C4 C5 119.75(15) . . ? C4 C5 C6 120.26(14) . . ? C5 C6 C1 120.68(14) . . ? C1 C7 C16 110.29(12) . . ? C1 C7 C12 112.70(12) . . ? C16 C7 C12 106.50(12) . . ? C1 C7 C8 106.74(12) . . ? C16 C7 C8 113.13(12) . . ? C12 C7 C8 107.56(12) . . ? F10 C8 F9 106.78(13) . . ? F10 C8 F11 106.84(12) . . ? F9 C8 F11 106.68(12) . . ? F10 C8 C7 111.39(13) . . ? F9 C8 C7 111.60(12) . . ? F11 C8 C7 113.17(13) . . ? F13 C12 F15 106.88(12) . . ? F13 C12 F14 106.23(12) . . ? F15 C12 F14 107.13(12) . . ? F13 C12 C7 112.14(13) . . ? F15 C12 C7 113.21(13) . . ? F14 C12 C7 110.85(12) . . ? C17 C16 C21 117.99(14) . . ? C17 C16 C7 124.50(13) . . ? C21 C16 C7 117.48(13) . . ? C18 C17 C16 121.08(14) . . ? C17 C18 C19 119.96(14) . . ? O19 C19 C20 122.43(14) . . ? O19 C19 C18 117.82(14) . . ? C20 C19 C18 119.75(14) . . ? C21 C20 C19 119.93(14) . . ? C20 C21 C16 121.27(14) . . ? O31 C31 C32 121.07(15) . . ? O31 C31 C33 121.12(15) . 3_666 ? C32 C31 C33 117.81(14) . 3_666 ? C33 C32 C31 121.21(16) . . ? C32 C33 C31 120.95(16) . 3_666 ? O41 C41 C43 121.42(15) . 3_767 ? O41 C41 C42 120.68(16) . . ? C43 C41 C42 117.89(14) 3_767 . ? C43 C42 C41 120.86(16) . . ? C42 C43 C41 121.22(15) . 3_767 ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.394 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.052 #===END data_imai917_3 _database_code_depnum_ccdc_archive 'CCDC 759689' #TrackingRef 'IMAI917ver1.CIF' #data_im9195a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 O4' _chemical_formula_weight 308.32 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.4272(17) _cell_length_b 6.1401(5) _cell_length_c 11.1047(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.3840(10) _cell_angle_gamma 90.00 _cell_volume 1487.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 2802 _cell_measurement_theta_min 1.87 _cell_measurement_theta_max 28.02 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9625 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8761 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3395 _reflns_number_gt 2802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0519P)^2^+0.4916P] 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 3395 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.002 _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 0.20849(6) -0.4138(2) 0.54194(13) 0.0187(3) Uani 1 1 d . . . C2 C 0.20605(7) -0.6191(2) 0.59335(13) 0.0204(3) Uani 1 1 d . . . H2 H 0.2303 -0.7335 0.5722 0.025 Uiso 1 1 calc R . . C3 C 0.16884(7) -0.6606(2) 0.67521(14) 0.0219(3) Uani 1 1 d . . . H3 H 0.1675 -0.8022 0.7090 0.026 Uiso 1 1 calc R . . C4 C 0.13361(7) -0.4937(2) 0.70727(14) 0.0213(3) Uani 1 1 d . . . C5 C 0.13530(7) -0.2871(2) 0.65645(14) 0.0214(3) Uani 1 1 d . . . H5 H 0.1111 -0.1728 0.6776 0.026 Uiso 1 1 calc R . . C6 C 0.17242(6) -0.2489(2) 0.57502(14) 0.0210(3) Uani 1 1 d . . . H6 H 0.1734 -0.1075 0.5409 0.025 Uiso 1 1 calc R . . C7 C 0.24870(7) -0.3675(2) 0.45274(14) 0.0209(3) Uani 1 1 d . . . H7A H 0.2222 -0.3336 0.3705 0.025 Uiso 1 1 calc R . . H7B H 0.2722 -0.5007 0.4440 0.025 Uiso 1 1 calc R . . C8 C 0.29334(6) -0.1807(2) 0.49191(13) 0.0174(3) Uani 1 1 d . . . C9 C 0.30029(6) -0.0207(2) 0.40762(13) 0.0177(3) Uani 1 1 d . . . H9 H 0.2760 -0.0275 0.3254 0.021 Uiso 1 1 calc R . . C10 C 0.34205(6) 0.1493(2) 0.44081(13) 0.0171(3) Uani 1 1 d . . . H10 H 0.3464 0.2561 0.3815 0.021 Uiso 1 1 calc R . . C11 C 0.37721(6) 0.1614(2) 0.56111(13) 0.0169(3) Uani 1 1 d . . . C12 C 0.37088(6) 0.0030(2) 0.64696(13) 0.0184(3) Uani 1 1 d . . . H12 H 0.3950 0.0102 0.7293 0.022 Uiso 1 1 calc R . . C13 C 0.32925(6) -0.1654(2) 0.61211(13) 0.0190(3) Uani 1 1 d . . . H13 H 0.3251 -0.2725 0.6714 0.023 Uiso 1 1 calc R . . O4 O 0.09609(5) -0.52156(18) 0.78742(11) 0.0283(3) Uani 1 1 d . . . H4 H 0.0955 -0.6538 0.8066 0.042 Uiso 1 1 calc R . . O11 O 0.41960(5) 0.32194(16) 0.60070(9) 0.0211(2) Uani 1 1 d . . . H11 H 0.4175 0.4145 0.5442 0.032 Uiso 1 1 calc R . . C21 C 0.46132(6) 0.8130(2) 0.46887(13) 0.0165(3) Uani 1 1 d . . . C22 C 0.50055(6) 0.8406(2) 0.59415(12) 0.0167(3) Uani 1 1 d . . . H22 H 0.4999 0.7336 0.6556 0.020 Uiso 1 1 calc R . . C23 C 0.53704(6) 1.0139(2) 0.62249(12) 0.0165(3) Uani 1 1 d . . . H23 H 0.5626 1.0261 0.7034 0.020 Uiso 1 1 calc R . . O21 O 0.42888(5) 0.65092(17) 0.43970(9) 0.0209(2) Uani 1 1 d . . . C31 C 0.04015(7) 0.4681(2) 0.41898(14) 0.0210(3) Uani 1 1 d . . . C32 C 0.02728(7) 0.2903(2) 0.49831(14) 0.0216(3) Uani 1 1 d . . . H32 H 0.0467 0.1531 0.4967 0.026 Uiso 1 1 calc R . . C36 C 0.01117(7) 0.6814(2) 0.42774(13) 0.0215(3) Uani 1 1 d . . . H36 H 0.0200 0.8003 0.3800 0.026 Uiso 1 1 calc R . . O31 O 0.07262(5) 0.43975(19) 0.34528(10) 0.0286(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0150(7) 0.0208(7) 0.0203(7) -0.0039(6) 0.0041(5) -0.0040(5) C2 0.0181(7) 0.0191(7) 0.0243(7) -0.0041(6) 0.0054(6) -0.0010(6) C3 0.0227(8) 0.0175(7) 0.0256(8) -0.0011(6) 0.0061(6) -0.0045(6) C4 0.0192(7) 0.0235(8) 0.0233(7) -0.0066(6) 0.0092(6) -0.0071(6) C5 0.0181(7) 0.0196(7) 0.0275(8) -0.0068(6) 0.0070(6) -0.0017(6) C6 0.0192(7) 0.0173(7) 0.0270(8) -0.0022(6) 0.0060(6) -0.0032(6) C7 0.0199(7) 0.0218(7) 0.0231(7) -0.0028(6) 0.0093(6) -0.0034(6) C8 0.0143(7) 0.0183(7) 0.0209(7) -0.0015(6) 0.0072(5) 0.0011(5) C9 0.0151(7) 0.0222(7) 0.0161(7) 0.0000(6) 0.0040(5) 0.0040(5) C10 0.0186(7) 0.0169(7) 0.0181(7) 0.0036(5) 0.0087(5) 0.0027(5) C11 0.0151(7) 0.0163(7) 0.0210(7) -0.0020(6) 0.0078(5) 0.0003(5) C12 0.0167(7) 0.0240(8) 0.0148(7) 0.0006(6) 0.0046(5) 0.0010(5) C13 0.0186(7) 0.0201(7) 0.0203(7) 0.0049(6) 0.0086(6) 0.0015(5) O4 0.0329(6) 0.0248(6) 0.0339(6) -0.0045(5) 0.0213(5) -0.0074(5) O11 0.0248(6) 0.0185(5) 0.0200(5) 0.0002(4) 0.0052(4) -0.0049(4) C21 0.0147(7) 0.0168(7) 0.0196(7) -0.0021(5) 0.0073(5) 0.0001(5) C22 0.0182(7) 0.0172(7) 0.0158(7) 0.0029(5) 0.0064(5) 0.0020(5) C23 0.0160(7) 0.0200(7) 0.0138(6) -0.0008(5) 0.0041(5) 0.0005(5) O21 0.0230(5) 0.0184(5) 0.0221(5) -0.0025(4) 0.0070(4) -0.0050(4) C31 0.0191(7) 0.0228(8) 0.0223(7) -0.0048(6) 0.0070(6) -0.0045(6) C32 0.0201(7) 0.0196(7) 0.0261(8) -0.0027(6) 0.0071(6) -0.0009(6) C36 0.0232(8) 0.0200(7) 0.0223(7) -0.0007(6) 0.0075(6) -0.0036(6) O31 0.0302(6) 0.0290(6) 0.0325(6) -0.0039(5) 0.0191(5) -0.0015(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.390(2) . ? C1 C6 1.397(2) . ? C1 C7 1.5129(19) . ? C2 C3 1.392(2) . ? C3 C4 1.390(2) . ? C4 O4 1.3698(17) . ? C4 C5 1.393(2) . ? C5 C6 1.383(2) . ? C7 C8 1.5184(19) . ? C8 C9 1.390(2) . ? C8 C13 1.393(2) . ? C9 C10 1.394(2) . ? C10 C11 1.387(2) . ? C11 O11 1.3695(16) . ? C11 C12 1.392(2) . ? C12 C13 1.387(2) . ? C21 O21 1.2312(17) . ? C21 C22 1.4735(19) . ? C21 C23 1.4756(19) 3_676 ? C22 C23 1.3349(19) . ? C23 C21 1.4756(19) 3_676 ? C31 O31 1.2272(18) . ? C31 C32 1.473(2) . ? C31 C36 1.475(2) . ? C32 C36 1.333(2) 3_566 ? C36 C32 1.333(2) 3_566 ? 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 117.96(13) . . ? C2 C1 C7 121.69(13) . . ? C6 C1 C7 120.35(13) . . ? C1 C2 C3 121.37(14) . . ? C4 C3 C2 119.64(14) . . ? O4 C4 C3 123.07(14) . . ? O4 C4 C5 117.09(13) . . ? C3 C4 C5 119.84(13) . . ? C6 C5 C4 119.74(14) . . ? C5 C6 C1 121.45(14) . . ? C1 C7 C8 114.07(12) . . ? C9 C8 C13 117.86(13) . . ? C9 C8 C7 120.67(13) . . ? C13 C8 C7 121.46(13) . . ? C8 C9 C10 121.63(13) . . ? C11 C10 C9 119.46(13) . . ? O11 C11 C10 123.04(12) . . ? O11 C11 C12 117.15(12) . . ? C10 C11 C12 119.80(13) . . ? C13 C12 C11 119.91(13) . . ? C12 C13 C8 121.34(13) . . ? O21 C21 C22 121.91(13) . . ? O21 C21 C23 120.57(12) . 3_676 ? C22 C21 C23 117.51(12) . 3_676 ? C23 C22 C21 120.91(13) . . ? C22 C23 C21 121.57(12) . 3_676 ? O31 C31 C32 121.51(14) . . ? O31 C31 C36 120.55(14) . . ? C32 C31 C36 117.92(13) . . ? C36 C32 C31 121.07(14) 3_566 . ? C32 C36 C31 120.96(14) 3_566 . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.291 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.048