# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Ru-Qiang Zou' 'Rui-Qin Zhong' 'Miao Du' 'Qiang Xu' T.Kiyobayashi _publ_contact_author_name 'Ruqiang Zou' _publ_contact_author_email ruqiang.zou@aist.go.jp data_1 _database_code_depnum_ccdc_archive 'CCDC 632140' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H6 F6 O8 Zn2' _chemical_formula_weight 606.98 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' F F 0.0171 0.0103 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.483(5) _cell_length_b 7.7834(16) _cell_length_c 10.488(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.73(3) _cell_angle_gamma 90.00 _cell_volume 1998.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.017 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 2.504 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; Refinement using reflections with F^2^ > -3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7365 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 25.19 _reflns_number_total 1786 _reflns_number_gt 1588 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Shelxtl _computing_publication_material Shelxtl _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1033P)^2^+32.2235P] 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 SHELXL _refine_ls_extinction_coef 0.0038(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1786 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1953 _refine_ls_wR_factor_gt 0.1893 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.170 _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 Zn1 Zn 0.23515(3) 0.06511(10) 0.61029(8) 0.0197(4) Uani 1 1 d . . . C1 C 0.3601(3) 0.0395(9) 0.3610(6) 0.0190(14) Uani 1 1 d . . . C2 C 0.3553(3) -0.1214(9) 0.2965(7) 0.0210(14) Uani 1 1 d . . . C3 C 0.3954(3) -0.1677(9) 0.2168(7) 0.0229(15) Uani 1 1 d . . . H3 H 0.3930 -0.2708 0.1724 0.027 Uiso 1 1 calc R . . C4 C 0.4409(3) -0.0611(8) 0.2006(7) 0.0197(15) Uani 1 1 d . . . H4 H 0.4677 -0.0942 0.1436 0.024 Uiso 1 1 calc R . . C5 C 0.4475(3) 0.0957(9) 0.2680(7) 0.0208(14) Uani 1 1 d . . . C6 C 0.4063(3) 0.1455(9) 0.3451(7) 0.0216(15) Uani 1 1 d . . . H6 H 0.4085 0.2502 0.3876 0.026 Uiso 1 1 calc R . . C7 C 0.3177(3) 0.0968(8) 0.4486(6) 0.0173(14) Uani 1 1 d . . . C8 C 0.3074(3) -0.2473(8) 0.3076(6) 0.0188(14) Uani 1 1 d . . . C9 C 0.5000 0.2091(12) 0.2500 0.0174(19) Uani 1 2 d S . . C10 C 0.4846(3) 0.3266(10) 0.1336(7) 0.0263(16) Uani 1 1 d . . . F1 F 0.4819(2) 0.2328(7) 0.0287(4) 0.0375(12) Uani 1 1 d . . . F2 F 0.5216(2) 0.4561(6) 0.1232(5) 0.0380(12) Uani 1 1 d . . . F3 F 0.4343(2) 0.4007(7) 0.1397(5) 0.0394(12) Uani 1 1 d . . . O1 O 0.3148(2) 0.2567(6) 0.4763(5) 0.0230(11) Uani 1 1 d . . . O2 O 0.2892(2) -0.0169(7) 0.4974(5) 0.0294(12) Uani 1 1 d . . . O3 O 0.3194(2) -0.3865(7) 0.3660(6) 0.0307(13) Uani 1 1 d . . . O4 O 0.2598(2) -0.2151(7) 0.2541(5) 0.0259(11) 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 Zn1 0.0205(6) 0.0150(5) 0.0237(5) -0.0002(3) 0.0075(3) 0.0005(3) C1 0.021(3) 0.020(3) 0.016(3) 0.004(3) 0.002(3) 0.001(3) C2 0.019(3) 0.019(3) 0.026(3) 0.004(3) 0.002(3) 0.002(3) C3 0.024(3) 0.018(3) 0.027(4) -0.005(3) 0.006(3) 0.001(3) C4 0.021(3) 0.019(4) 0.019(3) -0.002(3) 0.003(3) 0.000(3) C5 0.017(3) 0.021(3) 0.024(3) 0.000(3) 0.002(3) 0.000(3) C6 0.025(4) 0.013(3) 0.027(4) -0.002(3) 0.002(3) -0.001(3) C7 0.017(3) 0.018(3) 0.017(3) 0.003(3) -0.001(3) 0.006(3) C8 0.023(3) 0.015(3) 0.019(3) -0.001(2) 0.009(3) 0.000(3) C9 0.019(4) 0.017(5) 0.017(4) 0.000 0.007(4) 0.000 C10 0.026(4) 0.022(4) 0.030(4) 0.001(3) 0.003(3) 0.005(3) F1 0.047(3) 0.044(3) 0.021(2) 0.001(2) 0.010(2) 0.006(2) F2 0.042(3) 0.026(2) 0.047(3) 0.018(2) 0.014(2) -0.005(2) F3 0.032(3) 0.042(3) 0.044(3) 0.012(2) 0.011(2) 0.017(2) O1 0.023(2) 0.020(2) 0.026(3) -0.001(2) 0.004(2) 0.005(2) O2 0.029(3) 0.023(3) 0.037(3) -0.003(2) 0.019(2) 0.001(2) O3 0.025(3) 0.023(3) 0.045(3) 0.008(2) 0.008(2) -0.005(2) O4 0.022(2) 0.028(3) 0.028(3) 0.005(2) 0.003(2) -0.002(2) _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 Zn1 O2 1.897(5) . ? Zn1 O3 1.946(5) 7_546 ? Zn1 O4 1.995(5) 6_556 ? Zn1 O1 2.054(5) 7_556 ? C1 C6 1.412(10) . ? C1 C2 1.427(10) . ? C1 C7 1.465(10) . ? C2 C3 1.347(10) . ? C2 C8 1.534(9) . ? C3 C4 1.400(10) . ? C3 H3 0.9300 . ? C4 C5 1.419(10) . ? C4 H4 0.9300 . ? C5 C6 1.357(10) . ? C5 C9 1.573(9) . ? C6 H6 0.9300 . ? C7 O2 1.241(9) . ? C7 O1 1.280(8) . ? C8 O3 1.277(9) . ? C8 O4 1.309(9) . ? C9 C10 1.568(9) 2_655 ? C9 C10 1.568(9) . ? C9 C5 1.573(9) 2_655 ? C10 F1 1.321(9) . ? C10 F2 1.360(9) . ? C10 F3 1.362(9) . ? O1 Zn1 2.054(5) 7_556 ? O3 Zn1 1.946(5) 7_546 ? O4 Zn1 1.995(5) 6 ? 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 O2 Zn1 O3 109.0(2) . 7_546 ? O2 Zn1 O4 117.5(2) . 6_556 ? O3 Zn1 O4 121.5(2) 7_546 6_556 ? O2 Zn1 O1 111.6(2) . 7_556 ? O3 Zn1 O1 97.6(2) 7_546 7_556 ? O4 Zn1 O1 96.4(2) 6_556 7_556 ? C6 C1 C2 121.2(6) . . ? C6 C1 C7 118.1(6) . . ? C2 C1 C7 120.6(6) . . ? C3 C2 C1 118.2(6) . . ? C3 C2 C8 116.2(6) . . ? C1 C2 C8 125.6(6) . . ? C2 C3 C4 120.3(7) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 122.4(6) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C6 C5 C4 117.5(6) . . ? C6 C5 C9 121.8(6) . . ? C4 C5 C9 120.8(6) . . ? C5 C6 C1 120.4(6) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O2 C7 O1 124.5(6) . . ? O2 C7 C1 116.6(6) . . ? O1 C7 C1 118.7(6) . . ? O3 C8 O4 124.5(6) . . ? O3 C8 C2 113.9(6) . . ? O4 C8 C2 121.4(6) . . ? C10 C9 C10 108.6(8) 2_655 . ? C10 C9 C5 115.0(4) 2_655 . ? C10 C9 C5 103.4(4) . . ? C10 C9 C5 103.4(4) 2_655 2_655 ? C10 C9 C5 115.0(4) . 2_655 ? C5 C9 C5 111.7(8) . 2_655 ? F1 C10 F2 111.7(6) . . ? F1 C10 F3 103.8(6) . . ? F2 C10 F3 107.0(6) . . ? F1 C10 C9 109.6(6) . . ? F2 C10 C9 109.9(6) . . ? F3 C10 C9 114.8(5) . . ? C7 O1 Zn1 126.2(5) . 7_556 ? C7 O2 Zn1 114.7(5) . . ? C8 O3 Zn1 120.8(5) . 7_546 ? C8 O4 Zn1 134.0(4) . 6 ? 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 C6 C1 C2 C3 -1.9(10) . . . . ? C7 C1 C2 C3 179.9(7) . . . . ? C6 C1 C2 C8 179.4(6) . . . . ? C7 C1 C2 C8 1.2(11) . . . . ? C1 C2 C3 C4 1.2(11) . . . . ? C8 C2 C3 C4 -179.9(6) . . . . ? C2 C3 C4 C5 1.5(11) . . . . ? C3 C4 C5 C6 -3.7(11) . . . . ? C3 C4 C5 C9 178.2(6) . . . . ? C4 C5 C6 C1 3.0(10) . . . . ? C9 C5 C6 C1 -178.9(6) . . . . ? C2 C1 C6 C5 -0.3(11) . . . . ? C7 C1 C6 C5 178.0(6) . . . . ? C6 C1 C7 O2 -154.1(7) . . . . ? C2 C1 C7 O2 24.1(10) . . . . ? C6 C1 C7 O1 21.2(10) . . . . ? C2 C1 C7 O1 -160.5(6) . . . . ? C3 C2 C8 O3 70.4(8) . . . . ? C1 C2 C8 O3 -110.8(8) . . . . ? C3 C2 C8 O4 -105.7(8) . . . . ? C1 C2 C8 O4 73.1(9) . . . . ? C6 C5 C9 C10 28.2(9) . . . 2_655 ? C4 C5 C9 C10 -153.8(7) . . . 2_655 ? C6 C5 C9 C10 -90.1(7) . . . . ? C4 C5 C9 C10 87.9(8) . . . . ? C6 C5 C9 C5 145.6(8) . . . 2_655 ? C4 C5 C9 C5 -36.3(5) . . . 2_655 ? C10 C9 C10 F1 167.8(7) 2_655 . . . ? C5 C9 C10 F1 -69.6(6) . . . . ? C5 C9 C10 F1 52.5(8) 2_655 . . . ? C10 C9 C10 F2 44.7(4) 2_655 . . . ? C5 C9 C10 F2 167.3(6) . . . . ? C5 C9 C10 F2 -70.6(8) 2_655 . . . ? C10 C9 C10 F3 -75.9(6) 2_655 . . . ? C5 C9 C10 F3 46.7(8) . . . . ? C5 C9 C10 F3 168.8(6) 2_655 . . . ? O2 C7 O1 Zn1 -89.5(8) . . . 7_556 ? C1 C7 O1 Zn1 95.5(7) . . . 7_556 ? O1 C7 O2 Zn1 4.8(9) . . . . ? C1 C7 O2 Zn1 179.8(5) . . . . ? O3 Zn1 O2 C7 161.8(5) 7_546 . . . ? O4 Zn1 O2 C7 -54.8(6) 6_556 . . . ? O1 Zn1 O2 C7 55.2(6) 7_556 . . . ? O4 C8 O3 Zn1 -3.6(9) . . . 7_546 ? C2 C8 O3 Zn1 -179.5(4) . . . 7_546 ? O3 C8 O4 Zn1 -153.6(5) . . . 6 ? C2 C8 O4 Zn1 22.0(10) . . . 6 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 2.106 _refine_diff_density_min -0.981 _refine_diff_density_rms 0.186 # Attachment 'CCDC 632141.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 632141' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H10 Cd2 F6 O10' _chemical_formula_weight 737.07 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' F F 0.0171 0.0103 '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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.483(5) _cell_length_b 7.7834(16) _cell_length_c 10.488(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.73(3) _cell_angle_gamma 90.00 _cell_volume 1998.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 2.246 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.770 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; Refinement using reflections with F^2^ > -3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9339 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2274 _reflns_number_gt 2198 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Shelxtl _computing_publication_material Shelxtl _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+2.1735P] 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 SHELXL _refine_ls_extinction_coef 0.0046(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2274 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0909 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 Cd1 Cd 0.233834(7) 0.08993(2) 0.646733(17) 0.01711(14) Uani 1 1 d . . . C1 C 0.36462(9) 0.0143(3) 0.3755(2) 0.0156(4) Uani 1 1 d . . . C2 C 0.36364(10) -0.1423(3) 0.3098(2) 0.0166(4) Uani 1 1 d . . . C3 C 0.40268(10) -0.1731(3) 0.2183(2) 0.0230(5) Uani 1 1 d . . . H3 H 0.4008 -0.2731 0.1700 0.028 Uiso 1 1 calc R . . C4 C 0.44449(12) -0.0572(4) 0.1976(3) 0.0222(5) Uani 1 1 d . . . H4 H 0.4700 -0.0795 0.1348 0.027 Uiso 1 1 calc R . . C5 C 0.44873(10) 0.0931(3) 0.2703(3) 0.0152(5) Uani 1 1 d . . . C6 C 0.40726(10) 0.1318(3) 0.3544(2) 0.0157(4) Uani 1 1 d . . . H6 H 0.4076 0.2364 0.3973 0.019 Uiso 1 1 calc R . . C7 C 0.32102(10) 0.0626(3) 0.4676(2) 0.0172(5) Uani 1 1 d . . . C8 C 0.32279(10) -0.2833(3) 0.3307(2) 0.0167(4) Uani 1 1 d . . . C9 C 0.5000 0.2074(4) 0.2500 0.0146(6) Uani 1 2 d S . . C10 C 0.48766(10) 0.3238(3) 0.1335(2) 0.0211(5) Uani 1 1 d . . . F1 F 0.48455(7) 0.2307(2) 0.02723(14) 0.0335(4) Uani 1 1 d . . . F2 F 0.52579(8) 0.4442(3) 0.1167(2) 0.0331(4) Uani 1 1 d . . . F3 F 0.44007(8) 0.4053(2) 0.1446(2) 0.0322(5) Uani 1 1 d . . . O1 O 0.30948(8) 0.2188(3) 0.48253(19) 0.0224(4) Uani 1 1 d . . . O2 O 0.29672(9) -0.0547(3) 0.5287(2) 0.0300(5) Uani 1 1 d . . . O3 O 0.33600(9) -0.4042(2) 0.4025(2) 0.0264(5) Uani 1 1 d . . . O4 O 0.27892(8) -0.2858(2) 0.26625(19) 0.0226(4) Uani 1 1 d . . . O1W O 0.17900(10) 0.1408(4) 0.8237(2) 0.0403(6) Uani 1 1 d . . . H1WA H 0.1851 0.0545 0.8660 0.048 Uiso 1 1 d R . . H1WB H 0.1823 0.2274 0.8677 0.048 Uiso 1 1 d 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 Cd1 0.01847(18) 0.01269(17) 0.02030(18) -0.00170(5) 0.00539(11) -0.00101(5) C1 0.0177(11) 0.0116(11) 0.0177(10) 0.0002(8) 0.0067(8) 0.0010(8) C2 0.0184(11) 0.0125(11) 0.0189(11) 0.0007(9) 0.0049(9) -0.0022(9) C3 0.0244(12) 0.0160(11) 0.0289(12) -0.0096(10) 0.0092(10) -0.0025(9) C4 0.0204(12) 0.0221(12) 0.0245(13) -0.0081(11) 0.0143(10) -0.0018(11) C5 0.0143(11) 0.0126(12) 0.0189(12) -0.0006(7) 0.0070(10) -0.0009(7) C6 0.0180(11) 0.0118(10) 0.0176(11) -0.0018(9) 0.0081(9) 0.0000(9) C7 0.0140(11) 0.0191(11) 0.0187(11) -0.0005(9) 0.0060(9) -0.0015(9) C8 0.0189(11) 0.0123(10) 0.0190(10) -0.0010(8) 0.0078(9) -0.0007(8) C9 0.0144(14) 0.0121(14) 0.0175(14) 0.000 0.0110(12) 0.000 C10 0.0177(11) 0.0199(12) 0.0258(12) 0.0044(9) 0.0088(9) 0.0035(9) F1 0.0458(10) 0.0372(10) 0.0175(8) 0.0002(6) 0.0048(7) 0.0101(8) F2 0.0301(10) 0.0260(8) 0.0434(11) 0.0186(8) 0.0103(8) -0.0032(7) F3 0.0250(9) 0.0313(10) 0.0406(11) 0.0095(6) 0.0101(8) 0.0139(6) O1 0.0242(10) 0.0194(9) 0.0238(9) -0.0003(7) 0.0100(8) 0.0079(7) O2 0.0330(11) 0.0209(9) 0.0368(12) 0.0019(9) 0.0256(9) -0.0048(9) O3 0.0298(11) 0.0163(10) 0.0331(12) 0.0073(6) -0.0044(9) -0.0063(6) O4 0.0181(9) 0.0211(9) 0.0287(10) 0.0069(7) 0.0031(7) -0.0031(7) O1W 0.0399(13) 0.0501(14) 0.0313(12) -0.0121(11) 0.0183(10) -0.0119(11) _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 Cd1 O4 2.2533(19) 6_556 ? Cd1 O1 2.268(2) 7_556 ? Cd1 O2 2.284(2) . ? Cd1 O3 2.293(2) 7_546 ? Cd1 O1W 2.338(2) . ? Cd1 O4 2.5579(19) 7_546 ? C1 C2 1.400(3) . ? C1 C6 1.407(3) . ? C1 C7 1.497(3) . ? C2 C3 1.384(3) . ? C2 C8 1.503(3) . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 C5 1.399(3) . ? C4 H4 0.9300 . ? C5 C6 1.387(3) . ? C5 C9 1.555(3) . ? C6 H6 0.9300 . ? C7 O1 1.258(3) . ? C7 O2 1.268(3) . ? C8 O3 1.245(3) . ? C8 O4 1.262(3) . ? C9 C10 1.548(3) 2_655 ? C9 C10 1.548(3) . ? C9 C5 1.555(3) 2_655 ? C10 F1 1.331(3) . ? C10 F3 1.333(3) . ? C10 F2 1.336(3) . ? O1 Cd1 2.268(2) 7_556 ? O3 Cd1 2.293(2) 7_546 ? O4 Cd1 2.2533(19) 6 ? O4 Cd1 2.5579(19) 7_546 ? O1W H1WA 0.8172 . ? O1W H1WB 0.8207 . ? 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 O4 Cd1 O1 96.35(9) 6_556 7_556 ? O4 Cd1 O2 107.81(8) 6_556 . ? O1 Cd1 O2 108.24(8) 7_556 . ? O4 Cd1 O3 155.56(8) 6_556 7_546 ? O1 Cd1 O3 86.42(7) 7_556 7_546 ? O2 Cd1 O3 94.19(8) . 7_546 ? O4 Cd1 O1W 74.11(8) 6_556 . ? O1 Cd1 O1W 95.43(9) 7_556 . ? O2 Cd1 O1W 155.68(10) . . ? O3 Cd1 O1W 81.46(9) 7_546 . ? O4 Cd1 O4 119.26(3) 6_556 7_546 ? O1 Cd1 O4 139.70(8) 7_556 7_546 ? O2 Cd1 O4 79.83(7) . 7_546 ? O3 Cd1 O4 53.32(7) 7_546 7_546 ? O1W Cd1 O4 78.43(8) . 7_546 ? C2 C1 C6 119.8(2) . . ? C2 C1 C7 121.9(2) . . ? C6 C1 C7 118.3(2) . . ? C3 C2 C1 119.0(2) . . ? C3 C2 C8 116.2(2) . . ? C1 C2 C8 124.9(2) . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.6(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 118.6(2) . . ? C6 C5 C9 124.1(2) . . ? C4 C5 C9 117.3(2) . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O1 C7 O2 121.7(2) . . ? O1 C7 C1 119.1(2) . . ? O2 C7 C1 119.3(2) . . ? O3 C8 O4 121.7(2) . . ? O3 C8 C2 118.2(2) . . ? O4 C8 C2 119.8(2) . . ? C10 C9 C10 108.3(3) 2_655 . ? C10 C9 C5 107.04(13) 2_655 2_655 ? C10 C9 C5 112.14(13) . 2_655 ? C10 C9 C5 112.14(13) 2_655 . ? C10 C9 C5 107.04(13) . . ? C5 C9 C5 110.2(2) 2_655 . ? F1 C10 F3 106.9(2) . . ? F1 C10 F2 107.7(2) . . ? F3 C10 F2 106.9(2) . . ? F1 C10 C9 110.6(2) . . ? F3 C10 C9 111.82(18) . . ? F2 C10 C9 112.7(2) . . ? C7 O1 Cd1 131.60(18) . 7_556 ? C7 O2 Cd1 104.07(18) . . ? C8 O3 Cd1 98.80(17) . 7_546 ? C8 O4 Cd1 134.05(16) . 6 ? C8 O4 Cd1 85.98(14) . 7_546 ? Cd1 O4 Cd1 139.76(8) 6 7_546 ? Cd1 O1W H1WA 100.9 . . ? Cd1 O1W H1WB 122.2 . . ? H1WA O1W H1WB 110.7 . . ? 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 C6 C1 C2 C3 -4.7(4) . . . . ? C7 C1 C2 C3 174.7(2) . . . . ? C6 C1 C2 C8 175.4(2) . . . . ? C7 C1 C2 C8 -5.2(4) . . . . ? C1 C2 C3 C4 4.6(4) . . . . ? C8 C2 C3 C4 -175.4(2) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C3 C4 C5 C6 -6.3(4) . . . . ? C3 C4 C5 C9 174.2(2) . . . . ? C4 C5 C6 C1 6.2(4) . . . . ? C9 C5 C6 C1 -174.4(2) . . . . ? C2 C1 C6 C5 -0.8(4) . . . . ? C7 C1 C6 C5 179.8(2) . . . . ? C2 C1 C7 O1 -150.1(2) . . . . ? C6 C1 C7 O1 29.3(3) . . . . ? C2 C1 C7 O2 30.0(4) . . . . ? C6 C1 C7 O2 -150.6(3) . . . . ? C3 C2 C8 O3 83.0(3) . . . . ? C1 C2 C8 O3 -97.0(3) . . . . ? C3 C2 C8 O4 -89.8(3) . . . . ? C1 C2 C8 O4 90.2(3) . . . . ? C6 C5 C9 C10 23.4(3) . . . 2_655 ? C4 C5 C9 C10 -157.2(2) . . . 2_655 ? C6 C5 C9 C10 -95.3(3) . . . . ? C4 C5 C9 C10 84.1(3) . . . . ? C6 C5 C9 C5 142.5(3) . . . 2_655 ? C4 C5 C9 C5 -38.08(19) . . . 2_655 ? C10 C9 C10 F1 171.0(2) 2_655 . . . ? C5 C9 C10 F1 53.1(2) 2_655 . . . ? C5 C9 C10 F1 -67.8(2) . . . . ? C10 C9 C10 F3 -69.93(18) 2_655 . . . ? C5 C9 C10 F3 172.2(2) 2_655 . . . ? C5 C9 C10 F3 51.2(3) . . . . ? C10 C9 C10 F2 50.49(17) 2_655 . . . ? C5 C9 C10 F2 -67.4(3) 2_655 . . . ? C5 C9 C10 F2 171.6(2) . . . . ? O2 C7 O1 Cd1 -109.0(3) . . . 7_556 ? C1 C7 O1 Cd1 71.1(3) . . . 7_556 ? O1 C7 O2 Cd1 2.0(3) . . . . ? C1 C7 O2 Cd1 -178.07(18) . . . . ? O4 Cd1 O2 C7 -56.5(2) 6_556 . . . ? O1 Cd1 O2 C7 46.7(2) 7_556 . . . ? O3 Cd1 O2 C7 134.28(19) 7_546 . . . ? O1W Cd1 O2 C7 -147.2(2) . . . . ? O4 Cd1 O2 C7 -174.2(2) 7_546 . . . ? O4 C8 O3 Cd1 5.0(3) . . . 7_546 ? C2 C8 O3 Cd1 -167.65(17) . . . 7_546 ? O3 C8 O4 Cd1 170.88(19) . . . 6 ? C2 C8 O4 Cd1 -16.6(3) . . . 6 ? O3 C8 O4 Cd1 -4.5(2) . . . 7_546 ? C2 C8 O4 Cd1 168.1(2) . . . 7_546 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.216 _refine_diff_density_min -1.774 _refine_diff_density_rms 0.178