data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yoshitane Imaiy-imai@apch.kindai.ac.jp' _publ_contact_author_email y-imai@apch.kindai.ac.j loop_ _publ_author_name 'Noriaki Iwase' 'Yuhei Kobayashi' 'Takafumi Kinuta' 'Tomohiro Sato' 'Nobuo Tajima' 'Reiko Kuroda' 'Yoshio Matsubara' 'Yoshitane Imai' data_imai023_1 _database_code_depnum_ccdc_archive 'CCDC 803894' #TrackingRef 'IMAI023Ver-F.CIF' #data_im9192a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 O5' _chemical_formula_weight 418.47 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 23.7772(14) _cell_length_b 6.8025(4) _cell_length_c 13.4175(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.9070(10) _cell_angle_gamma 90.00 _cell_volume 2097.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _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 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9645 _exptl_absorpt_correction_T_max 0.9909 _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 17605 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.87 _reflns_number_total 4853 _reflns_number_gt 4171 _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. We confirmed that the highest residual electron density does not correspond to the presence of any kind of atoms. ; _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^)+(0.0943P)^2^+0.9587P] 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 4853 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1558 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.66667(6) 0.3095(2) 0.01918(11) 0.0139(3) Uani 1 1 d . . . C2 C 0.67499(6) 0.4956(2) -0.01932(12) 0.0144(3) Uani 1 1 d . . . H2 H 0.7069 0.5729 0.0174 0.017 Uiso 1 1 calc R . . C3 C 0.63865(7) 0.5719(2) -0.10881(12) 0.0148(3) Uani 1 1 d . . . C4 C 0.59171(7) 0.4563(2) -0.16253(11) 0.0149(3) Uani 1 1 d . . . C5 C 0.58150(7) 0.2733(2) -0.12490(12) 0.0145(3) Uani 1 1 d . . . H5 H 0.5492 0.1969 -0.1608 0.017 Uiso 1 1 calc R . . C6 C 0.61878(7) 0.2017(2) -0.03434(12) 0.0146(3) Uani 1 1 d . . . H6 H 0.6113 0.0769 -0.0088 0.018 Uiso 1 1 calc R . . C7 C 0.64863(7) 0.7691(2) -0.15088(13) 0.0183(3) Uani 1 1 d . . . H7A H 0.6814 0.8343 -0.1028 0.027 Uiso 1 1 calc R . . H7B H 0.6135 0.8497 -0.1596 0.027 Uiso 1 1 calc R . . H7C H 0.6575 0.7524 -0.2178 0.027 Uiso 1 1 calc R . . C8 C 0.71113(7) 0.2348(2) 0.11570(11) 0.0141(3) Uani 1 1 d . . . C9 C 0.71149(7) 0.3753(3) 0.20531(13) 0.0238(4) Uani 1 1 d . . . H9A H 0.7241 0.5060 0.1892 0.036 Uiso 1 1 calc R . . H9B H 0.7384 0.3257 0.2684 0.036 Uiso 1 1 calc R . . H9C H 0.6722 0.3838 0.2156 0.036 Uiso 1 1 calc R . . C10 C 0.69575(7) 0.0277(3) 0.14733(13) 0.0228(4) Uani 1 1 d . . . H10A H 0.7253 -0.0150 0.2089 0.034 Uiso 1 1 calc R . . H10B H 0.6946 -0.0646 0.0908 0.034 Uiso 1 1 calc R . . H10C H 0.6576 0.0311 0.1624 0.034 Uiso 1 1 calc R . . C11 C 0.77161(7) 0.2249(2) 0.09405(11) 0.0137(3) Uani 1 1 d . . . C12 C 0.82286(7) 0.2413(2) 0.17212(12) 0.0163(3) Uani 1 1 d . . . H12 H 0.8200 0.2586 0.2409 0.020 Uiso 1 1 calc R . . C13 C 0.87824(7) 0.2337(2) 0.15455(12) 0.0167(3) Uani 1 1 d . . . C14 C 0.88188(7) 0.2073(2) 0.05316(13) 0.0174(3) Uani 1 1 d . . . C15 C 0.83154(7) 0.1808(3) -0.02536(12) 0.0194(4) Uani 1 1 d . . . H15 H 0.8343 0.1566 -0.0937 0.023 Uiso 1 1 calc R . . C16 C 0.77730(7) 0.1893(3) -0.00524(12) 0.0183(3) Uani 1 1 d . . . H16 H 0.7434 0.1706 -0.0601 0.022 Uiso 1 1 calc R . . C17 C 0.93224(8) 0.2524(3) 0.24215(13) 0.0253(4) Uani 1 1 d . . . H17A H 0.9212 0.2635 0.3074 0.038 Uiso 1 1 calc R . . H17B H 0.9539 0.3699 0.2320 0.038 Uiso 1 1 calc R . . H17C H 0.9567 0.1358 0.2440 0.038 Uiso 1 1 calc R . . O4 O 0.55724(5) 0.53653(17) -0.25124(9) 0.0203(3) Uani 1 1 d . . . H4 H 0.5366 0.4480 -0.2863 0.030 Uiso 1 1 calc R . . O14 O 0.93327(5) 0.2041(2) 0.02498(9) 0.0237(3) Uani 1 1 d . . . H14 H 0.9609 0.2275 0.0767 0.036 Uiso 1 1 calc R . . C21 C 0.84088(7) 0.7077(3) 0.04177(13) 0.0199(4) Uani 1 1 d . . . C22 C 0.90445(7) 0.7226(3) 0.08654(13) 0.0209(4) Uani 1 1 d . . . H22 H 0.9194 0.7294 0.1593 0.025 Uiso 1 1 calc R . . C23 C 0.94112(8) 0.7266(3) 0.02617(13) 0.0216(4) Uani 1 1 d . . . H23 H 0.9818 0.7361 0.0567 0.026 Uiso 1 1 calc R . . C24 C 0.91977(7) 0.7166(3) -0.08711(13) 0.0206(4) Uani 1 1 d . . . C25 C 0.85669(8) 0.6936(3) -0.13212(13) 0.0236(4) Uani 1 1 d . . . H25 H 0.8420 0.6834 -0.2048 0.028 Uiso 1 1 calc R . . C26 C 0.82023(8) 0.6870(3) -0.07176(14) 0.0242(4) Uani 1 1 d . . . H26 H 0.7799 0.6686 -0.1023 0.029 Uiso 1 1 calc R . . O21 O 0.80689(5) 0.71412(19) 0.09645(10) 0.0246(3) Uani 1 1 d . . . O24 O 0.95336(6) 0.7290(2) -0.14285(10) 0.0298(3) Uani 1 1 d . . . C31 C 0.50736(7) 0.6814(2) -0.04873(12) 0.0163(3) Uani 1 1 d . . . C32 C 0.54561(7) 0.6282(2) 0.05297(12) 0.0175(3) Uani 1 1 d . . . H32 H 0.5754 0.7165 0.0868 0.021 Uiso 1 1 calc R . . C33 C 0.53899(7) 0.4585(2) 0.09794(12) 0.0173(3) Uani 1 1 d . . . H33 H 0.5645 0.4268 0.1629 0.021 Uiso 1 1 calc R . . O31 O 0.51401(5) 0.83729(17) -0.08982(9) 0.0212(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 0.0120(7) 0.0176(8) 0.0123(7) -0.0012(6) 0.0036(6) 0.0029(6) C2 0.0119(7) 0.0159(7) 0.0153(7) -0.0035(6) 0.0034(6) -0.0014(5) C3 0.0151(7) 0.0140(7) 0.0164(7) -0.0024(6) 0.0062(6) 0.0007(6) C4 0.0141(7) 0.0177(8) 0.0125(7) -0.0018(6) 0.0026(6) 0.0033(6) C5 0.0118(7) 0.0179(8) 0.0130(7) -0.0041(6) 0.0015(6) -0.0008(6) C6 0.0137(7) 0.0167(7) 0.0144(7) -0.0001(6) 0.0056(6) 0.0009(6) C7 0.0212(8) 0.0161(8) 0.0177(8) -0.0004(6) 0.0051(6) -0.0004(6) C8 0.0117(7) 0.0206(8) 0.0097(7) 0.0006(6) 0.0023(6) 0.0023(6) C9 0.0162(8) 0.0403(10) 0.0147(8) -0.0053(7) 0.0035(6) 0.0055(7) C10 0.0183(8) 0.0291(9) 0.0216(8) 0.0113(7) 0.0063(7) 0.0019(7) C11 0.0130(7) 0.0168(7) 0.0113(7) 0.0016(5) 0.0034(6) 0.0019(6) C12 0.0160(8) 0.0232(8) 0.0097(7) -0.0003(6) 0.0030(6) 0.0022(6) C13 0.0139(8) 0.0215(8) 0.0141(8) 0.0006(6) 0.0025(6) 0.0011(6) C14 0.0148(8) 0.0221(8) 0.0166(8) 0.0021(6) 0.0064(6) 0.0020(6) C15 0.0185(8) 0.0289(9) 0.0120(7) 0.0002(6) 0.0058(6) 0.0006(6) C16 0.0148(8) 0.0269(9) 0.0122(7) -0.0001(6) 0.0019(6) 0.0000(6) C17 0.0141(8) 0.0451(11) 0.0154(8) -0.0016(7) 0.0015(6) 0.0016(7) O4 0.0220(6) 0.0189(6) 0.0156(6) 0.0002(4) -0.0032(5) 0.0013(5) O14 0.0133(6) 0.0400(8) 0.0195(6) -0.0008(5) 0.0073(5) -0.0007(5) C21 0.0162(8) 0.0248(9) 0.0194(8) 0.0003(6) 0.0061(6) -0.0019(6) C22 0.0193(9) 0.0278(9) 0.0143(8) 0.0008(6) 0.0018(6) -0.0007(7) C23 0.0140(8) 0.0309(9) 0.0185(8) -0.0006(7) 0.0014(6) -0.0008(6) C24 0.0161(8) 0.0279(9) 0.0185(8) -0.0008(6) 0.0056(6) -0.0009(6) C25 0.0183(9) 0.0345(10) 0.0171(8) -0.0026(7) 0.0030(7) -0.0019(7) C26 0.0147(8) 0.0336(10) 0.0233(9) -0.0030(7) 0.0028(7) -0.0027(7) O21 0.0200(6) 0.0334(7) 0.0228(6) -0.0009(5) 0.0098(5) -0.0025(5) O24 0.0182(7) 0.0522(9) 0.0207(7) -0.0022(6) 0.0082(5) -0.0028(6) C31 0.0134(7) 0.0164(8) 0.0187(8) -0.0004(6) 0.0032(6) 0.0016(6) C32 0.0137(7) 0.0210(8) 0.0165(7) -0.0042(6) 0.0014(6) -0.0009(6) C33 0.0141(7) 0.0225(8) 0.0136(7) -0.0002(6) 0.0007(6) 0.0011(6) O31 0.0221(6) 0.0178(6) 0.0221(6) 0.0024(5) 0.0030(5) -0.0003(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 1.389(2) . ? C1 C2 1.400(2) . ? C1 C8 1.533(2) . ? C2 C3 1.387(2) . ? C3 C4 1.404(2) . ? C3 C7 1.498(2) . ? C4 O4 1.3728(19) . ? C4 C5 1.388(2) . ? C5 C6 1.395(2) . ? C8 C9 1.534(2) . ? C8 C11 1.540(2) . ? C8 C10 1.542(2) . ? C11 C12 1.392(2) . ? C11 C16 1.394(2) . ? C12 C13 1.397(2) . ? C13 C14 1.397(2) . ? C13 C17 1.507(2) . ? C14 O14 1.3690(19) . ? C14 C15 1.388(2) . ? C15 C16 1.385(2) . ? C21 O21 1.224(2) . ? C21 C22 1.480(2) . ? C21 C26 1.482(2) . ? C22 C23 1.334(2) . ? C23 C24 1.475(2) . ? C24 O24 1.230(2) . ? C24 C25 1.474(2) . ? C25 C26 1.331(2) . ? C31 O31 1.224(2) . ? C31 C32 1.477(2) . ? C31 C33 1.477(2) 3_665 ? C32 C33 1.331(2) . ? C33 C31 1.477(2) 3_665 ? 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 117.48(14) . . ? C6 C1 C8 123.87(14) . . ? C2 C1 C8 118.64(14) . . ? C3 C2 C1 122.81(14) . . ? C2 C3 C4 118.09(14) . . ? C2 C3 C7 122.52(14) . . ? C4 C3 C7 119.38(14) . . ? O4 C4 C5 123.42(14) . . ? O4 C4 C3 116.17(14) . . ? C5 C4 C3 120.41(14) . . ? C4 C5 C6 119.92(14) . . ? C1 C6 C5 121.25(14) . . ? C1 C8 C9 108.62(13) . . ? C1 C8 C11 109.26(12) . . ? C9 C8 C11 110.98(13) . . ? C1 C8 C10 112.00(13) . . ? C9 C8 C10 107.89(13) . . ? C11 C8 C10 108.11(12) . . ? C12 C11 C16 116.85(14) . . ? C12 C11 C8 122.25(13) . . ? C16 C11 C8 120.83(14) . . ? C11 C12 C13 123.41(14) . . ? C14 C13 C12 117.80(15) . . ? C14 C13 C17 121.11(15) . . ? C12 C13 C17 121.09(15) . . ? O14 C14 C15 116.43(14) . . ? O14 C14 C13 123.67(15) . . ? C15 C14 C13 119.90(15) . . ? C16 C15 C14 120.74(15) . . ? C15 C16 C11 121.16(15) . . ? O21 C21 C22 121.16(16) . . ? O21 C21 C26 121.62(16) . . ? C22 C21 C26 117.22(14) . . ? C23 C22 C21 120.92(16) . . ? C22 C23 C24 121.28(16) . . ? O24 C24 C25 120.66(16) . . ? O24 C24 C23 121.22(16) . . ? C25 C24 C23 118.12(15) . . ? C26 C25 C24 120.52(16) . . ? C25 C26 C21 121.80(16) . . ? O31 C31 C32 120.56(15) . . ? O31 C31 C33 121.66(15) . 3_665 ? C32 C31 C33 117.78(14) . 3_665 ? C33 C32 C31 121.01(15) . . ? C32 C33 C31 121.20(15) . 3_665 ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.784 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.084 #===END data_imai023_2 _database_code_depnum_ccdc_archive 'CCDC 803895' #TrackingRef 'IMAI023Ver-F.CIF' #data_im9193a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 O3' _chemical_formula_weight 324.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7120(7) _cell_length_b 10.1166(8) _cell_length_c 10.2478(8) _cell_angle_alpha 90.2410(10) _cell_angle_beta 107.1330(10) _cell_angle_gamma 92.4330(10) _cell_volume 862.21(12) _cell_formula_units_Z 2 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3350 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9640 _exptl_absorpt_correction_T_max 0.9838 _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 'Bruker APEX' _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 5378 _diffrn_reflns_av_R_equivalents 0.0118 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3768 _reflns_number_gt 3350 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0614P)^2^+0.3143P] 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 3768 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.003 _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 -0.27796(14) 0.64884(12) 0.05610(12) 0.0177(3) Uani 1 1 d . . . C2 C -0.27606(15) 0.59610(13) -0.06944(13) 0.0193(3) Uani 1 1 d . . . H2 H -0.2322 0.5120 -0.0713 0.023 Uiso 1 1 calc R . . C3 C -0.33584(15) 0.66178(13) -0.19229(13) 0.0188(3) Uani 1 1 d . . . C4 C -0.40423(14) 0.78257(12) -0.18783(12) 0.0176(3) Uani 1 1 d . . . C5 C -0.40993(15) 0.83682(12) -0.06505(13) 0.0199(3) Uani 1 1 d . . . H5 H -0.4583 0.9190 -0.0637 0.024 Uiso 1 1 calc R . . C6 C -0.34528(15) 0.77127(13) 0.05539(13) 0.0199(3) Uani 1 1 d . . . H6 H -0.3468 0.8105 0.1394 0.024 Uiso 1 1 calc R . . C7 C -0.32559(18) 0.60520(14) -0.32544(13) 0.0254(3) Uani 1 1 d . . . H7A H -0.4343 0.5886 -0.3876 0.038 Uiso 1 1 calc R . . H7B H -0.2699 0.5220 -0.3087 0.038 Uiso 1 1 calc R . . H7C H -0.2659 0.6683 -0.3667 0.038 Uiso 1 1 calc R . . C8 C -0.19858(15) 0.58376(12) 0.19312(13) 0.0195(3) Uani 1 1 d . . . C9 C -0.17382(18) 0.43589(13) 0.17412(14) 0.0259(3) Uani 1 1 d . . . H9A H -0.2776 0.3906 0.1284 0.039 Uiso 1 1 calc R . . H9B H -0.1273 0.3966 0.2636 0.039 Uiso 1 1 calc R . . H9C H -0.1008 0.4264 0.1183 0.039 Uiso 1 1 calc R . . C10 C -0.30753(17) 0.59361(15) 0.28683(14) 0.0256(3) Uani 1 1 d . . . H10A H -0.3116 0.6864 0.3130 0.038 Uiso 1 1 calc R . . H10B H -0.2640 0.5417 0.3690 0.038 Uiso 1 1 calc R . . H10C H -0.4162 0.5590 0.2381 0.038 Uiso 1 1 calc R . . C11 C -0.03258(15) 0.65218(12) 0.25795(12) 0.0175(3) Uani 1 1 d . . . C12 C 0.05497(15) 0.70799(13) 0.17598(12) 0.0191(3) Uani 1 1 d . . . H12 H 0.0059 0.7087 0.0800 0.023 Uiso 1 1 calc R . . C13 C 0.20968(15) 0.76235(13) 0.22771(13) 0.0199(3) Uani 1 1 d . . . C14 C 0.28237(15) 0.76068(12) 0.36845(13) 0.0194(3) Uani 1 1 d . . . C15 C 0.19805(16) 0.70719(12) 0.45326(13) 0.0196(3) Uani 1 1 d . . . H15 H 0.2472 0.7069 0.5492 0.024 Uiso 1 1 calc R . . C16 C 0.04254(16) 0.65420(12) 0.39847(12) 0.0192(3) Uani 1 1 d . . . H16 H -0.0138 0.6186 0.4578 0.023 Uiso 1 1 calc R . . C17 C 0.29840(17) 0.82189(16) 0.13546(14) 0.0301(3) Uani 1 1 d . . . H17A H 0.3695 0.7569 0.1162 0.045 Uiso 1 1 calc R . . H17B H 0.3626 0.9003 0.1802 0.045 Uiso 1 1 calc R . . H17C H 0.2211 0.8474 0.0497 0.045 Uiso 1 1 calc R . . O4 O -0.46126(11) 0.84905(9) -0.30872(9) 0.0223(2) Uani 1 1 d . . . H4 H -0.5212 0.9085 -0.2982 0.034 Uiso 1 1 calc R . . O14 O 0.43514(11) 0.81451(10) 0.41618(9) 0.0261(2) Uani 1 1 d . . . H14 H 0.4665 0.8106 0.5018 0.039 Uiso 1 1 calc R . . C21 C 0.14579(16) 0.99177(13) 0.60642(14) 0.0226(3) Uani 1 1 d . . . C22 C 0.14560(16) 1.03079(13) 0.46859(14) 0.0245(3) Uani 1 1 d . . . H22 H 0.2454 1.0517 0.4519 0.029 Uiso 1 1 calc R . . C23 C 0.01017(16) 1.03800(13) 0.36572(14) 0.0233(3) Uani 1 1 d . . . C24 C 0.00458(19) 1.07457(15) 0.22354(15) 0.0314(3) Uani 1 1 d . . . H24A H 0.1144 1.0900 0.2182 0.047 Uiso 1 1 calc R . . H24B H -0.0549 1.1553 0.1987 0.047 Uiso 1 1 calc R . . H24C H -0.0494 1.0024 0.1604 0.047 Uiso 1 1 calc R . . O21 O 0.27219(12) 0.98216(10) 0.69807(10) 0.0290(2) 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 0.0152(6) 0.0199(6) 0.0174(6) 0.0002(5) 0.0042(4) -0.0027(5) C2 0.0183(6) 0.0186(6) 0.0206(6) -0.0013(5) 0.0052(5) 0.0010(5) C3 0.0173(6) 0.0207(6) 0.0178(6) -0.0031(5) 0.0046(5) -0.0010(5) C4 0.0129(6) 0.0213(6) 0.0170(6) 0.0003(5) 0.0022(4) -0.0009(4) C5 0.0194(6) 0.0186(6) 0.0220(6) -0.0017(5) 0.0066(5) 0.0024(5) C6 0.0198(6) 0.0225(6) 0.0179(6) -0.0033(5) 0.0069(5) -0.0015(5) C7 0.0331(8) 0.0248(7) 0.0187(6) -0.0016(5) 0.0075(5) 0.0065(6) C8 0.0210(6) 0.0199(6) 0.0170(6) 0.0014(5) 0.0052(5) -0.0009(5) C9 0.0336(8) 0.0195(6) 0.0221(6) 0.0020(5) 0.0047(5) -0.0018(5) C10 0.0230(7) 0.0337(7) 0.0209(6) 0.0039(6) 0.0080(5) -0.0030(5) C11 0.0195(6) 0.0149(6) 0.0179(6) 0.0003(4) 0.0051(5) 0.0021(4) C12 0.0210(6) 0.0213(6) 0.0144(6) 0.0014(5) 0.0040(5) 0.0021(5) C13 0.0207(6) 0.0216(6) 0.0180(6) 0.0013(5) 0.0066(5) 0.0026(5) C14 0.0192(6) 0.0188(6) 0.0191(6) -0.0008(5) 0.0036(5) 0.0022(5) C15 0.0244(6) 0.0187(6) 0.0145(6) 0.0007(5) 0.0035(5) 0.0026(5) C16 0.0249(7) 0.0173(6) 0.0168(6) 0.0023(5) 0.0079(5) 0.0020(5) C17 0.0236(7) 0.0459(9) 0.0201(7) 0.0024(6) 0.0067(5) -0.0081(6) O4 0.0239(5) 0.0241(5) 0.0176(4) 0.0010(4) 0.0030(4) 0.0075(4) O14 0.0213(5) 0.0369(6) 0.0173(4) -0.0001(4) 0.0019(4) -0.0044(4) C21 0.0197(6) 0.0168(6) 0.0296(7) -0.0028(5) 0.0041(5) 0.0036(5) C22 0.0192(6) 0.0220(6) 0.0325(7) 0.0007(5) 0.0078(5) 0.0008(5) C23 0.0242(7) 0.0165(6) 0.0295(7) 0.0009(5) 0.0079(5) 0.0026(5) C24 0.0331(8) 0.0309(8) 0.0303(8) 0.0047(6) 0.0093(6) 0.0030(6) O21 0.0212(5) 0.0316(5) 0.0301(5) -0.0049(4) 0.0007(4) 0.0062(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.3918(18) . ? C1 C2 1.3955(17) . ? C1 C8 1.5355(17) . ? C2 C3 1.3956(18) . ? C3 C4 1.3884(18) . ? C3 C7 1.5056(17) . ? C4 O4 1.3808(15) . ? C4 C5 1.3857(17) . ? C5 C6 1.3818(18) . ? C8 C11 1.5352(17) . ? C8 C9 1.5401(18) . ? C8 C10 1.5418(18) . ? C11 C16 1.3949(17) . ? C11 C12 1.3969(17) . ? C12 C13 1.3834(18) . ? C13 C14 1.3944(17) . ? C13 C17 1.4999(18) . ? C14 O14 1.3638(16) . ? C14 C15 1.3907(18) . ? C15 C16 1.3877(18) . ? C21 O21 1.2267(16) . ? C21 C22 1.468(2) . ? C21 C23 1.4876(19) 2_576 ? C22 C23 1.3356(19) . ? C23 C21 1.4876(19) 2_576 ? C23 C24 1.492(2) . ? 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 117.30(11) . . ? C6 C1 C8 119.34(11) . . ? C2 C1 C8 123.18(11) . . ? C1 C2 C3 122.76(12) . . ? C4 C3 C2 117.71(11) . . ? C4 C3 C7 120.71(11) . . ? C2 C3 C7 121.58(11) . . ? O4 C4 C5 121.04(11) . . ? O4 C4 C3 117.98(11) . . ? C5 C4 C3 120.94(11) . . ? C6 C5 C4 119.97(12) . . ? C5 C6 C1 121.29(11) . . ? C11 C8 C1 108.85(10) . . ? C11 C8 C9 107.78(10) . . ? C1 C8 C9 111.57(10) . . ? C11 C8 C10 111.57(10) . . ? C1 C8 C10 109.65(10) . . ? C9 C8 C10 107.43(11) . . ? C16 C11 C12 116.85(12) . . ? C16 C11 C8 122.52(11) . . ? C12 C11 C8 120.49(11) . . ? C13 C12 C11 123.21(12) . . ? C12 C13 C14 118.49(12) . . ? C12 C13 C17 121.20(11) . . ? C14 C13 C17 120.31(12) . . ? O14 C14 C15 123.09(11) . . ? O14 C14 C13 117.07(11) . . ? C15 C14 C13 119.84(12) . . ? C16 C15 C14 120.36(11) . . ? C15 C16 C11 121.24(12) . . ? O21 C21 C22 121.05(13) . . ? O21 C21 C23 119.76(13) . 2_576 ? C22 C21 C23 119.18(12) . 2_576 ? C23 C22 C21 122.40(13) . . ? C22 C23 C21 118.41(13) . 2_576 ? C22 C23 C24 124.18(13) . . ? C21 C23 C24 117.41(12) 2_576 . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.349 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.047 #===END data_imai023_3 _database_code_depnum_ccdc_archive 'CCDC 803896' #TrackingRef 'IMAI023Ver-F.CIF' #data_im9191a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H18 F6 O4' _chemical_formula_weight 472.37 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 11.1508(7) _cell_length_b 7.3171(5) _cell_length_c 24.5176(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2000.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 2090 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9385 _exptl_absorpt_correction_T_max 0.9789 _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 'Bruker APEX' _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 11389 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.88 _reflns_number_total 2354 _reflns_number_gt 2090 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0534P)^2^+0.9102P] 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 2354 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.53545(11) 0.06864(17) 0.70040(5) 0.0150(3) Uani 1 1 d . . . C2 C 0.62673(11) 0.02105(18) 0.66423(5) 0.0178(3) Uani 1 1 d . . . H2 H 0.6726 -0.0861 0.6708 0.021 Uiso 1 1 calc R . . C3 C 0.65168(11) 0.12754(18) 0.61886(5) 0.0183(3) Uani 1 1 d . . . H3 H 0.7151 0.0941 0.5950 0.022 Uiso 1 1 calc R . . C4 C 0.58415(11) 0.28321(18) 0.60823(5) 0.0166(3) Uani 1 1 d . . . C5 C 0.49230(12) 0.33229(17) 0.64359(5) 0.0175(3) Uani 1 1 d . . . H5 H 0.4457 0.4384 0.6366 0.021 Uiso 1 1 calc R . . C6 C 0.46897(11) 0.22597(18) 0.68911(5) 0.0168(3) Uani 1 1 d . . . H6 H 0.4063 0.2608 0.7132 0.020 Uiso 1 1 calc R . . C7 C 0.5000 -0.0486(2) 0.7500 0.0156(4) Uani 1 2 d S . . C8 C 0.39601(12) -0.17328(19) 0.73113(6) 0.0208(3) Uani 1 1 d . . . O4 O 0.61094(9) 0.38144(14) 0.56232(4) 0.0211(2) Uani 1 1 d . . . H4 H 0.5724 0.4801 0.5626 0.032 Uiso 1 1 calc R . . F9 F 0.41857(8) -0.25198(12) 0.68306(3) 0.0269(2) Uani 1 1 d . . . F10 F 0.37173(8) -0.30912(11) 0.76607(4) 0.0287(2) Uani 1 1 d . . . F11 F 0.29509(7) -0.07636(12) 0.72479(3) 0.0251(2) Uani 1 1 d . . . C21 C 0.50638(12) 0.15233(18) 0.46416(5) 0.0178(3) Uani 1 1 d . . . C22 C 0.40197(12) 0.12323(19) 0.49940(6) 0.0197(3) Uani 1 1 d . . . H22 H 0.3365 0.2058 0.4968 0.024 Uiso 1 1 calc R . . C23 C 0.39491(11) -0.01459(18) 0.53515(5) 0.0178(3) Uani 1 1 d . . . C24 C 0.29406(12) -0.03857(19) 0.57453(6) 0.0224(3) Uani 1 1 d . . . H24A H 0.3154 0.0178 0.6095 0.034 Uiso 1 1 calc R . . H24B H 0.2789 -0.1692 0.5800 0.034 Uiso 1 1 calc R . . H24C H 0.2217 0.0199 0.5600 0.034 Uiso 1 1 calc R . . O21 O 0.51495(9) 0.28958(13) 0.43581(4) 0.0226(2) 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 0.0163(6) 0.0134(6) 0.0153(6) 0.0000(4) -0.0009(5) -0.0007(5) C2 0.0183(6) 0.0149(6) 0.0202(6) -0.0010(5) 0.0001(5) 0.0044(5) C3 0.0180(6) 0.0195(6) 0.0174(6) -0.0022(5) 0.0017(5) 0.0027(5) C4 0.0189(6) 0.0152(6) 0.0156(6) -0.0003(5) -0.0024(5) -0.0034(5) C5 0.0183(6) 0.0134(6) 0.0208(6) -0.0003(5) -0.0029(5) 0.0025(5) C6 0.0151(6) 0.0164(6) 0.0188(6) -0.0021(5) 0.0003(5) 0.0024(5) C7 0.0157(8) 0.0135(8) 0.0176(9) 0.000 0.0012(6) 0.000 C8 0.0247(7) 0.0164(6) 0.0214(7) -0.0034(5) 0.0019(5) -0.0033(5) O4 0.0255(5) 0.0186(5) 0.0193(5) 0.0036(4) 0.0016(4) 0.0001(4) F9 0.0345(5) 0.0222(4) 0.0242(4) -0.0101(3) 0.0027(3) -0.0050(3) F10 0.0387(5) 0.0177(4) 0.0297(5) -0.0011(3) 0.0054(4) -0.0119(4) F11 0.0175(4) 0.0277(5) 0.0301(5) -0.0073(3) -0.0022(3) -0.0037(3) C21 0.0235(6) 0.0141(6) 0.0157(6) -0.0007(5) -0.0032(5) -0.0013(5) C22 0.0204(6) 0.0175(6) 0.0213(6) -0.0004(5) -0.0015(5) 0.0023(5) C23 0.0199(6) 0.0152(6) 0.0183(6) -0.0028(5) -0.0014(5) -0.0019(5) C24 0.0247(6) 0.0173(7) 0.0253(7) 0.0011(5) 0.0050(5) 0.0000(5) O21 0.0302(5) 0.0163(5) 0.0214(5) 0.0047(4) 0.0001(4) 0.0009(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.3942(17) . ? C1 C6 1.3970(17) . ? C1 C7 1.5398(15) . ? C2 C3 1.3864(18) . ? C3 C4 1.3901(18) . ? C4 O4 1.3684(15) . ? C4 C5 1.3891(18) . ? C5 C6 1.3851(18) . ? C7 C1 1.5398(15) 4_656 ? C7 C8 1.5461(17) . ? C7 C8 1.5461(17) 4_656 ? C8 F9 1.3357(15) . ? C8 F11 1.3393(16) . ? C8 F10 1.3398(16) . ? C21 O21 1.2250(16) . ? C21 C22 1.4653(18) . ? C21 C23 1.4925(18) 5_656 ? C22 C23 1.3385(19) . ? C23 C21 1.4925(18) 5_656 ? C23 C24 1.4925(18) . ? 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 117.85(12) . . ? C2 C1 C7 123.41(11) . . ? C6 C1 C7 118.65(11) . . ? C3 C2 C1 121.10(12) . . ? C2 C3 C4 120.15(12) . . ? O4 C4 C5 122.58(12) . . ? O4 C4 C3 117.80(11) . . ? C5 C4 C3 119.62(12) . . ? C6 C5 C4 119.75(12) . . ? C5 C6 C1 121.53(12) . . ? C1 C7 C1 112.27(14) 4_656 . ? C1 C7 C8 111.87(7) 4_656 . ? C1 C7 C8 106.56(7) . . ? C1 C7 C8 106.56(7) 4_656 4_656 ? C1 C7 C8 111.87(7) . 4_656 ? C8 C7 C8 107.69(15) . 4_656 ? F9 C8 F11 106.49(11) . . ? F9 C8 F10 106.41(11) . . ? F11 C8 F10 107.30(11) . . ? F9 C8 C7 112.16(10) . . ? F11 C8 C7 110.64(11) . . ? F10 C8 C7 113.45(11) . . ? O21 C21 C22 121.04(12) . . ? O21 C21 C23 120.16(12) . 5_656 ? C22 C21 C23 118.76(11) . 5_656 ? C23 C22 C21 122.84(12) . . ? C22 C23 C21 118.21(12) . 5_656 ? C22 C23 C24 123.82(12) . . ? C21 C23 C24 117.97(12) 5_656 . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.433 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.052 #===END data_imai023_4 _database_code_depnum_ccdc_archive 'CCDC 803897' #TrackingRef 'IMAI023Ver-F.CIF' #data_im9196a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 Cl F6 O4' _chemical_formula_weight 492.79 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 11.2984(10) _cell_length_b 7.2275(6) _cell_length_c 24.573(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2006.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 2127 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 27.89 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8863 _exptl_absorpt_correction_T_max 0.9344 _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 'Bruker APEX' _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 11472 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.89 _reflns_number_total 2349 _reflns_number_gt 2127 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0412P)^2^+1.5228P] 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 2349 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.007 _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 0.03621(14) 0.0539(2) 0.20070(6) 0.0205(3) Uani 1 1 d . . . C2 C -0.02978(14) 0.2114(2) 0.18852(7) 0.0230(3) Uani 1 1 d . . . H2 H -0.0926 0.2467 0.2120 0.028 Uiso 1 1 calc R . . C3 C -0.00585(15) 0.3178(2) 0.14293(7) 0.0247(3) Uani 1 1 d . . . H3 H -0.0523 0.4242 0.1353 0.030 Uiso 1 1 calc R . . C4 C 0.08590(15) 0.2687(2) 0.10856(6) 0.0227(3) Uani 1 1 d . . . C5 C 0.15288(15) 0.1128(2) 0.11995(7) 0.0254(3) Uani 1 1 d . . . H5 H 0.2162 0.0789 0.0965 0.030 Uiso 1 1 calc R . . C6 C 0.12778(15) 0.0062(2) 0.16538(7) 0.0244(3) Uani 1 1 d . . . H6 H 0.1737 -0.1011 0.1726 0.029 Uiso 1 1 calc R . . C7 C 0.0000 -0.0647(3) 0.2500 0.0210(4) Uani 1 2 d S . . C8 C -0.10210(16) -0.1909(2) 0.23062(7) 0.0284(4) Uani 1 1 d . . . F9 F -0.07849(10) -0.27025(15) 0.18271(4) 0.0377(3) Uani 1 1 d . . . F10 F -0.12655(11) -0.32895(15) 0.26523(5) 0.0400(3) Uani 1 1 d . . . F11 F -0.20163(9) -0.09348(16) 0.22387(4) 0.0346(3) Uani 1 1 d . . . O21 O -0.01208(13) -0.29814(17) 0.06257(5) 0.0335(3) Uani 1 1 d . . . C21 C -0.00483(16) -0.1585(2) 0.03485(7) 0.0262(4) Uani 1 1 d . . . C22 C -0.10136(15) -0.0180(2) 0.03499(7) 0.0264(4) Uani 1 1 d . . . C23 C -0.09684(16) 0.1255(2) 0.00083(7) 0.0285(4) Uani 1 1 d . . . H23 H -0.1617 0.2090 -0.0004 0.034 Uiso 1 1 calc R . . O4 O 0.11302(12) 0.36664(18) 0.06239(5) 0.0295(3) Uani 1 1 d . . . H4 H 0.0738 0.4654 0.0619 0.044 Uiso 1 1 calc R . . Cl22 Cl -0.21408(12) -0.0540(2) 0.07591(6) 0.0349(4) Uiso 0.50 1 d P . . C22M C -0.1969(4) -0.0499(6) 0.08368(19) 0.0166(12) Uiso 0.50 1 d P . . H22A H -0.1654 0.0010 0.1177 0.025 Uiso 0.50 1 calc PR . . H22B H -0.2115 -0.1827 0.0882 0.025 Uiso 0.50 1 calc PR . . H22C H -0.2712 0.0127 0.0745 0.025 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 C1 0.0227(7) 0.0187(7) 0.0202(7) -0.0001(6) -0.0015(6) 0.0005(6) C2 0.0225(7) 0.0216(8) 0.0250(8) -0.0020(6) 0.0007(6) 0.0036(6) C3 0.0284(8) 0.0191(7) 0.0266(8) 0.0000(6) -0.0049(6) 0.0040(6) C4 0.0272(8) 0.0209(8) 0.0200(7) -0.0004(6) -0.0041(6) -0.0047(6) C5 0.0257(8) 0.0284(8) 0.0221(8) -0.0023(6) 0.0028(6) 0.0039(7) C6 0.0266(8) 0.0220(8) 0.0248(8) 0.0000(6) 0.0000(6) 0.0070(6) C7 0.0225(10) 0.0170(10) 0.0237(11) 0.000 0.0011(8) 0.000 C8 0.0327(9) 0.0231(8) 0.0293(9) -0.0055(7) 0.0027(7) -0.0050(7) F9 0.0474(7) 0.0321(6) 0.0338(6) -0.0148(5) 0.0037(5) -0.0072(5) F10 0.0535(7) 0.0255(6) 0.0411(6) -0.0020(5) 0.0065(5) -0.0167(5) F11 0.0254(5) 0.0395(6) 0.0390(6) -0.0109(5) -0.0029(4) -0.0055(4) O21 0.0476(8) 0.0239(6) 0.0289(6) 0.0070(5) -0.0003(6) 0.0013(6) C21 0.0368(9) 0.0205(8) 0.0212(8) -0.0002(6) -0.0058(7) -0.0013(7) C22 0.0317(8) 0.0237(8) 0.0238(8) -0.0015(6) -0.0032(7) -0.0023(7) C23 0.0320(9) 0.0245(8) 0.0289(8) 0.0014(7) -0.0023(7) 0.0040(7) O4 0.0369(7) 0.0271(6) 0.0247(6) 0.0045(5) 0.0004(5) -0.0022(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.393(2) . ? C1 C6 1.394(2) . ? C1 C7 1.5392(19) . ? C2 C3 1.385(2) . ? C3 C4 1.383(2) . ? C4 O4 1.3720(19) . ? C4 C5 1.386(2) . ? C5 C6 1.386(2) . ? C7 C1 1.5392(19) 4 ? C7 C8 1.546(2) . ? C7 C8 1.546(2) 4 ? C8 F9 1.3366(19) . ? C8 F11 1.337(2) . ? C8 F10 1.340(2) . ? O21 C21 1.221(2) . ? C21 C23 1.465(2) 5 ? C21 C22 1.490(2) . ? C22 C23 1.335(2) . ? C22 C22M 1.628(4) . ? C22 Cl22 1.643(2) . ? C23 C21 1.465(2) 5 ? 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 117.75(14) . . ? C2 C1 C7 118.80(14) . . ? C6 C1 C7 123.34(14) . . ? C3 C2 C1 121.51(15) . . ? C4 C3 C2 119.83(15) . . ? O4 C4 C3 122.66(15) . . ? O4 C4 C5 117.69(15) . . ? C3 C4 C5 119.64(15) . . ? C4 C5 C6 120.19(15) . . ? C5 C6 C1 121.07(15) . . ? C1 C7 C1 112.34(18) 4 . ? C1 C7 C8 111.88(9) 4 . ? C1 C7 C8 106.52(9) . . ? C1 C7 C8 106.52(9) 4 4 ? C1 C7 C8 111.88(9) . 4 ? C8 C7 C8 107.66(19) . 4 ? F9 C8 F11 106.52(14) . . ? F9 C8 F10 106.30(14) . . ? F11 C8 F10 107.31(14) . . ? F9 C8 C7 112.07(13) . . ? F11 C8 C7 110.80(14) . . ? F10 C8 C7 113.45(14) . . ? O21 C21 C23 121.42(16) . 5 ? O21 C21 C22 120.86(17) . . ? C23 C21 C22 117.69(15) 5 . ? C23 C22 C21 119.98(16) . . ? C23 C22 C22M 126.7(2) . . ? C21 C22 C22M 113.0(2) . . ? C23 C22 Cl22 122.49(15) . . ? C21 C22 Cl22 117.45(14) . . ? C22M C22 Cl22 9.60(18) . . ? C22 C23 C21 122.19(16) . 5 ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.404 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.053 #===END