# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Guoqing Zhang' _publ_contact_author_email gzhang@ustc.edu.cn loop_ _publ_author_name 'Xingxing Sun' 'Xuepeng Zhang' 'Xinyang Li' 'Shiyong Liu' 'Guoqing Zhang' data_sxx-3 _database_code_depnum_ccdc_archive 'CCDC 880808' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 B F2 O4' _chemical_formula_weight 384.17 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' B B 0.0013 0.0007 '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 26.2572(17) _cell_length_b 7.2012(3) _cell_length_c 10.3231(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.870(5) _cell_angle_gamma 90.00 _cell_volume 1928.58(18) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1869 _cell_measurement_theta_min 2.9297 _cell_measurement_theta_max 29.2024 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9641 _exptl_absorpt_correction_T_max 0.9759 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8854 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1966 _reflns_number_gt 1186 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0657P)^2^+0.5425P] 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 1966 _refine_ls_number_parameters 128 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1550 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.065 _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 F1 F 1.03201(5) 0.54320(18) 0.19006(12) 0.0778(5) Uani 1 1 d . . . O2 O 0.96793(6) 0.31854(18) 0.15044(14) 0.0644(5) Uani 1 1 d . . . O1 O 0.83664(7) -0.1915(2) -0.26252(16) 0.0773(5) Uani 1 1 d . . . C11 C 1.0000 0.0446(4) 0.2500 0.0527(7) Uani 1 2 d S . . H11 H 1.0000 -0.0845 0.2500 0.063 Uiso 1 2 calc SR . . C1 C 0.93434(7) 0.0469(2) 0.04593(18) 0.0485(5) Uani 1 1 d . . . C10 C 0.96868(8) 0.1375(3) 0.15237(19) 0.0484(5) Uani 1 1 d . . . C4 C 0.86929(8) -0.1227(3) -0.1583(2) 0.0588(6) Uani 1 1 d . . . C3 C 0.89756(10) -0.2293(3) -0.0624(2) 0.0653(6) Uani 1 1 d . . . H3 H 0.8949 -0.3581 -0.0657 0.078 Uiso 1 1 calc R . . C5 C 0.87339(9) 0.0690(3) -0.1525(2) 0.0655(6) Uani 1 1 d . . . H5 H 0.8543 0.1415 -0.2170 0.079 Uiso 1 1 calc R . . C2 C 0.92969(9) -0.1450(3) 0.0384(2) 0.0607(6) Uani 1 1 d . . . H2 H 0.9487 -0.2180 0.1028 0.073 Uiso 1 1 calc R . . C6 C 0.90547(9) 0.1520(3) -0.0521(2) 0.0586(6) Uani 1 1 d . . . H6 H 0.9080 0.2808 -0.0493 0.070 Uiso 1 1 calc R . . B1 B 1.0000 0.4342(4) 0.2500 0.0566(9) Uani 1 2 d S . . C7 C 0.83361(11) -0.3888(4) -0.2800(3) 0.0841(8) Uani 1 1 d . . . H7A H 0.8216 -0.4472 -0.2056 0.101 Uiso 1 1 calc R . . H7B H 0.8672 -0.4392 -0.2884 0.101 Uiso 1 1 calc R . . C8 C 0.79681(13) -0.4230(5) -0.4010(3) 0.1104(11) Uani 1 1 d D . . H8 H 0.8021 -0.3566 -0.4751 0.132 Uiso 1 1 calc R . . C9 C 0.75951(15) -0.5315(6) -0.4141(4) 0.1488(16) Uani 1 1 d D . . H9A H 0.7526 -0.6012 -0.3429 0.179 Uiso 1 1 calc R . . H9B H 0.7385 -0.5429 -0.4949 0.179 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0866(10) 0.0612(9) 0.0854(10) 0.0134(6) 0.0125(8) -0.0157(7) O2 0.0868(11) 0.0324(8) 0.0689(10) 0.0018(6) -0.0041(9) 0.0013(7) O1 0.0812(12) 0.0678(11) 0.0766(11) -0.0100(8) -0.0075(9) -0.0055(8) C11 0.0636(18) 0.0312(15) 0.0618(18) 0.000 0.0052(15) 0.000 C1 0.0552(12) 0.0380(12) 0.0533(12) 0.0012(9) 0.0117(10) 0.0000(9) C10 0.0569(12) 0.0341(11) 0.0566(12) 0.0006(9) 0.0168(10) 0.0020(9) C4 0.0595(14) 0.0555(14) 0.0602(13) -0.0065(11) 0.0053(11) -0.0042(10) C3 0.0792(16) 0.0416(12) 0.0716(15) -0.0033(11) 0.0003(13) -0.0049(11) C5 0.0716(15) 0.0543(14) 0.0673(14) 0.0066(11) 0.0006(12) 0.0048(11) C2 0.0732(15) 0.0412(12) 0.0637(14) 0.0026(10) -0.0018(12) 0.0017(10) C6 0.0713(15) 0.0377(12) 0.0658(14) 0.0022(10) 0.0072(12) 0.0012(10) B1 0.069(2) 0.0320(17) 0.068(2) 0.000 0.0073(19) 0.000 C7 0.0810(18) 0.0716(18) 0.0950(19) -0.0214(15) -0.0017(16) -0.0076(14) C8 0.101(2) 0.106(3) 0.119(2) -0.035(2) 0.001(2) -0.017(2) C9 0.119(3) 0.137(3) 0.180(4) -0.030(3) -0.009(3) -0.041(3) _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 F1 B1 1.366(2) . ? O2 C10 1.304(2) . ? O2 B1 1.481(2) . ? O1 C4 1.361(2) . ? O1 C7 1.433(3) . ? C11 C10 1.372(2) 2_755 ? C11 C10 1.372(2) . ? C11 H11 0.9300 . ? C1 C2 1.389(3) . ? C1 C6 1.391(3) . ? C1 C10 1.463(3) . ? C4 C3 1.376(3) . ? C4 C5 1.385(3) . ? C3 C2 1.376(3) . ? C3 H3 0.9300 . ? C5 C6 1.368(3) . ? C5 H5 0.9300 . ? C2 H2 0.9300 . ? C6 H6 0.9300 . ? B1 F1 1.366(2) 2_755 ? B1 O2 1.481(2) 2_755 ? C7 C8 1.477(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.243(4) . ? C8 H8 0.9300 . ? C9 H9A 0.9300 . ? C9 H9B 0.9300 . ? 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 C10 O2 B1 123.11(17) . . ? C4 O1 C7 118.45(18) . . ? C10 C11 C10 121.7(2) 2_755 . ? C10 C11 H11 119.2 2_755 . ? C10 C11 H11 119.2 . . ? C2 C1 C6 117.85(19) . . ? C2 C1 C10 121.63(18) . . ? C6 C1 C10 120.52(17) . . ? O2 C10 C11 120.28(19) . . ? O2 C10 C1 115.34(17) . . ? C11 C10 C1 124.38(17) . . ? O1 C4 C3 124.7(2) . . ? O1 C4 C5 115.6(2) . . ? C3 C4 C5 119.7(2) . . ? C2 C3 C4 119.8(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C6 C5 C4 120.2(2) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C3 C2 C1 121.3(2) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C5 C6 C1 121.11(19) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? F1 B1 F1 109.9(2) 2_755 . ? F1 B1 O2 108.30(8) 2_755 . ? F1 B1 O2 109.42(8) . . ? F1 B1 O2 109.42(8) 2_755 2_755 ? F1 B1 O2 108.30(8) . 2_755 ? O2 B1 O2 111.5(2) . 2_755 ? O1 C7 C8 106.8(2) . . ? O1 C7 H7A 110.4 . . ? C8 C7 H7A 110.4 . . ? O1 C7 H7B 110.4 . . ? C8 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C9 C8 C7 126.7(4) . . ? C9 C8 H8 116.6 . . ? C7 C8 H8 116.6 . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? 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 B1 O2 C10 C11 0.3(2) . . . . ? B1 O2 C10 C1 179.97(13) . . . . ? C10 C11 C10 O2 -0.13(12) 2_755 . . . ? C10 C11 C10 C1 -179.8(2) 2_755 . . . ? C2 C1 C10 O2 -177.54(18) . . . . ? C6 C1 C10 O2 3.0(3) . . . . ? C2 C1 C10 C11 2.2(3) . . . . ? C6 C1 C10 C11 -177.32(16) . . . . ? C7 O1 C4 C3 -4.4(3) . . . . ? C7 O1 C4 C5 175.2(2) . . . . ? O1 C4 C3 C2 179.6(2) . . . . ? C5 C4 C3 C2 -0.1(3) . . . . ? O1 C4 C5 C6 -179.6(2) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C3 C2 C1 0.0(3) . . . . ? C6 C1 C2 C3 -0.1(3) . . . . ? C10 C1 C2 C3 -179.61(19) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? C10 C1 C6 C5 179.71(19) . . . . ? C10 O2 B1 F1 -120.6(2) . . . 2_755 ? C10 O2 B1 F1 119.7(2) . . . . ? C10 O2 B1 O2 -0.14(13) . . . 2_755 ? C4 O1 C7 C8 -178.5(2) . . . . ? O1 C7 C8 C9 -129.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.178 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036 # Attachment '2.cif' data_sxx-1 _database_code_depnum_ccdc_archive 'CCDC 880809' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 B F2 O4' _chemical_formula_weight 358.14 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P C' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 10.6842(7) _cell_length_b 7.2837(4) _cell_length_c 12.8423(7) _cell_angle_alpha 90.00 _cell_angle_beta 120.355(7) _cell_angle_gamma 90.00 _cell_volume 862.39(9) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1487 _cell_measurement_theta_min 3.9894 _cell_measurement_theta_max 62.7080 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.921 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7327 _exptl_absorpt_correction_T_max 0.8372 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3520 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.80 _diffrn_reflns_theta_max 62.78 _reflns_number_total 1740 _reflns_number_gt 1495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0847P)^2^+0.8025P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1740 _refine_ls_number_parameters 236 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0807 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.1899 _refine_ls_wR_factor_gt 0.1812 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.091 _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 F1 F 0.5710(7) 1.0544(8) 0.1680(5) 0.118(2) Uani 1 1 d . . . F2 F 0.3678(6) 1.0907(6) 0.1767(4) 0.1018(16) Uani 1 1 d . . . O1 O 0.5243(6) 0.8563(6) 0.2846(4) 0.0741(14) Uani 1 1 d . . . O2 O 0.3815(6) 0.8530(5) 0.0650(4) 0.0734(14) Uani 1 1 d . . . O3 O 0.0776(7) 0.3343(7) -0.3845(5) 0.0887(18) Uani 1 1 d . . . O4 O 0.8245(6) 0.3502(7) 0.7405(4) 0.0786(15) Uani 1 1 d . . . C1 C 0.5991(7) 0.5908(9) 0.4037(5) 0.0525(14) Uani 1 1 d . . . C2 C 0.6724(8) 0.7002(9) 0.5067(7) 0.068(2) Uani 1 1 d . . . H2 H 0.6710 0.8270 0.4980 0.082 Uiso 1 1 calc R . . C3 C 0.7465(9) 0.6255(9) 0.6207(6) 0.0697(19) Uani 1 1 d . . . H3 H 0.7915 0.7014 0.6880 0.084 Uiso 1 1 calc R . . C4 C 0.7537(7) 0.4386(8) 0.6342(6) 0.0583(15) Uani 1 1 d . . . C5 C 0.6809(8) 0.3289(10) 0.5312(7) 0.0664(19) Uani 1 1 d . . . H5 H 0.6846 0.2019 0.5399 0.080 Uiso 1 1 calc R . . C6 C 0.6053(8) 0.4018(10) 0.4193(6) 0.0622(17) Uani 1 1 d . . . H6 H 0.5573 0.3251 0.3526 0.075 Uiso 1 1 calc R . . C7 C 0.5252(7) 0.6784(9) 0.2854(6) 0.0556(15) Uani 1 1 d . . . C8 C 0.4523(9) 0.5822(7) 0.1775(7) 0.0583(13) Uani 1 1 d . . . H8 H 0.4504 0.4546 0.1791 0.070 Uiso 1 1 calc R . . C9 C 0.3829(7) 0.6718(8) 0.0681(6) 0.0558(15) Uani 1 1 d . . . C10 C 0.3035(7) 0.5818(10) -0.0477(6) 0.0569(16) Uani 1 1 d . . . C11 C 0.2430(8) 0.6807(10) -0.1560(6) 0.0671(19) Uani 1 1 d . . . H11 H 0.2529 0.8077 -0.1536 0.080 Uiso 1 1 calc R . . C12 C 0.1687(10) 0.5929(11) -0.2667(7) 0.078(2) Uani 1 1 d . . . H12 H 0.1305 0.6612 -0.3375 0.094 Uiso 1 1 calc R . . C13 C 0.1508(8) 0.4036(11) -0.2726(6) 0.0663(18) Uani 1 1 d . . . C14 C 0.2129(8) 0.3025(9) -0.1668(6) 0.0693(19) Uani 1 1 d . . . H14 H 0.2040 0.1754 -0.1693 0.083 Uiso 1 1 calc R . . C15 C 0.2878(8) 0.3920(10) -0.0581(6) 0.0653(18) Uani 1 1 d . . . H15 H 0.3303 0.3221 0.0121 0.078 Uiso 1 1 calc R . . C16 C 0.8972(9) 0.4580(12) 0.8490(6) 0.083(2) Uani 1 1 d . . . H16A H 0.9706 0.5319 0.8475 0.124 Uiso 1 1 calc R . . H16B H 0.9413 0.3780 0.9178 0.124 Uiso 1 1 calc R . . H16C H 0.8282 0.5362 0.8542 0.124 Uiso 1 1 calc R . . C17 C 0.0529(10) 0.1372(11) -0.3948(9) 0.097(2) Uani 1 1 d DU . . H17A H 0.1430 0.0713 -0.3677 0.117 Uiso 1 1 calc R . . H17B H 0.0106 0.0980 -0.3471 0.117 Uiso 1 1 calc R . . C18 C -0.0466(15) 0.1055(15) -0.5220(10) 0.130(3) Uani 1 1 d DU . . H18 H -0.1359 0.1647 -0.5576 0.156 Uiso 1 1 calc R . . B1 B 0.4635(13) 0.9642(9) 0.1738(9) 0.0706(19) Uani 1 1 d . . . C19 C -0.0187(17) -0.0027(18) -0.5914(12) 0.148(4) Uani 1 1 d DU . . H19A H 0.0697 -0.0639 -0.5587 0.178 Uiso 1 1 calc R . . H19B H -0.0875 -0.0171 -0.6727 0.178 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.130(4) 0.130(5) 0.079(3) 0.008(3) 0.042(3) -0.057(4) F2 0.137(4) 0.067(2) 0.075(3) -0.004(2) 0.034(3) 0.027(3) O1 0.105(4) 0.047(3) 0.053(3) -0.003(2) 0.028(3) -0.001(3) O2 0.106(4) 0.042(2) 0.057(3) -0.002(2) 0.030(3) 0.002(3) O3 0.121(5) 0.065(3) 0.053(3) -0.005(3) 0.024(3) -0.007(3) O4 0.097(4) 0.069(3) 0.051(3) 0.006(2) 0.023(3) 0.004(3) C1 0.070(4) 0.043(3) 0.045(3) 0.000(3) 0.029(3) 0.003(3) C2 0.090(5) 0.043(3) 0.064(5) -0.004(3) 0.034(4) 0.000(3) C3 0.088(5) 0.057(4) 0.049(4) -0.003(3) 0.023(4) 0.001(4) C4 0.063(4) 0.052(3) 0.053(3) 0.004(3) 0.023(3) 0.008(3) C5 0.080(5) 0.047(3) 0.063(4) 0.008(3) 0.030(4) 0.003(3) C6 0.073(4) 0.050(3) 0.055(4) -0.004(3) 0.026(3) -0.007(3) C7 0.067(4) 0.045(3) 0.057(4) -0.006(3) 0.033(3) -0.005(3) C8 0.074(3) 0.043(2) 0.052(3) 0.004(4) 0.027(3) 0.004(4) C9 0.064(3) 0.048(3) 0.057(4) -0.003(3) 0.031(3) -0.001(3) C10 0.065(4) 0.053(3) 0.053(4) -0.002(3) 0.030(3) -0.001(3) C11 0.091(5) 0.053(4) 0.054(4) 0.002(3) 0.034(4) 0.000(4) C12 0.104(6) 0.067(4) 0.055(4) 0.011(4) 0.034(4) 0.004(4) C13 0.080(4) 0.062(4) 0.054(4) 0.001(3) 0.033(4) -0.002(4) C14 0.086(5) 0.048(3) 0.063(5) 0.002(3) 0.030(4) -0.005(3) C15 0.081(5) 0.056(4) 0.054(4) 0.009(3) 0.030(4) 0.003(3) C16 0.081(5) 0.100(6) 0.047(4) -0.011(4) 0.017(3) 0.002(4) C17 0.099(4) 0.077(4) 0.103(3) 0.006(3) 0.042(3) -0.002(3) C18 0.154(6) 0.115(5) 0.104(4) -0.007(4) 0.054(3) -0.001(4) B1 0.098(5) 0.047(3) 0.058(4) -0.003(4) 0.032(4) -0.003(5) C19 0.179(7) 0.138(6) 0.126(5) -0.011(4) 0.077(5) 0.007(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 F1 B1 1.358(12) . ? F2 B1 1.391(11) . ? O1 C7 1.296(8) . ? O1 B1 1.459(10) . ? O2 C9 1.320(7) . ? O2 B1 1.463(10) . ? O3 C13 1.339(9) . ? O3 C17 1.453(9) . ? O4 C4 1.344(8) . ? O4 C16 1.438(8) . ? C1 C6 1.388(9) . ? C1 C2 1.397(9) . ? C1 C7 1.459(9) . ? C2 C3 1.376(10) . ? C2 H2 0.9300 . ? C3 C4 1.370(9) . ? C3 H3 0.9300 . ? C4 C5 1.398(10) . ? C5 C6 1.351(10) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.389(9) . ? C8 C9 1.377(9) . ? C8 H8 0.9300 . ? C9 C10 1.444(9) . ? C10 C15 1.391(9) . ? C10 C11 1.401(10) . ? C11 C12 1.385(11) . ? C11 H11 0.9300 . ? C12 C13 1.389(10) . ? C12 H12 0.9300 . ? C13 C14 1.385(10) . ? C14 C15 1.372(10) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.448(12) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.332(9) . ? C18 H18 0.9300 . ? C19 H19A 0.9300 . ? C19 H19B 0.9300 . ? 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 C7 O1 B1 123.0(6) . . ? C9 O2 B1 122.2(6) . . ? C13 O3 C17 116.8(7) . . ? C4 O4 C16 118.3(5) . . ? C6 C1 C2 117.8(6) . . ? C6 C1 C7 123.0(6) . . ? C2 C1 C7 119.1(6) . . ? C3 C2 C1 121.8(6) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C4 C3 C2 119.6(7) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? O4 C4 C3 124.8(6) . . ? O4 C4 C5 116.5(6) . . ? C3 C4 C5 118.6(6) . . ? C6 C5 C4 122.0(7) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C1 120.1(7) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O1 C7 C8 119.9(6) . . ? O1 C7 C1 116.4(6) . . ? C8 C7 C1 123.7(6) . . ? C9 C8 C7 121.4(5) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? O2 C9 C8 119.8(6) . . ? O2 C9 C10 115.5(6) . . ? C8 C9 C10 124.7(6) . . ? C15 C10 C11 116.2(6) . . ? C15 C10 C9 122.0(6) . . ? C11 C10 C9 121.7(6) . . ? C12 C11 C10 121.3(7) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 120.4(7) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? O3 C13 C14 125.6(7) . . ? O3 C13 C12 115.0(7) . . ? C14 C13 C12 119.3(7) . . ? C15 C14 C13 119.3(7) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C10 123.4(7) . . ? C14 C15 H15 118.3 . . ? C10 C15 H15 118.3 . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 O3 104.9(8) . . ? C18 C17 H17A 110.8 . . ? O3 C17 H17A 110.8 . . ? C18 C17 H17B 110.8 . . ? O3 C17 H17B 110.8 . . ? H17A C17 H17B 108.9 . . ? C19 C18 C17 124.4(13) . . ? C19 C18 H18 117.8 . . ? C17 C18 H18 117.8 . . ? F1 B1 F2 109.5(6) . . ? F1 B1 O1 110.0(8) . . ? F2 B1 O1 107.6(7) . . ? F1 B1 O2 109.3(8) . . ? F2 B1 O2 107.4(8) . . ? O1 B1 O2 113.0(5) . . ? C18 C19 H19A 120.0 . . ? C18 C19 H19B 120.0 . . ? H19A C19 H19B 120.0 . . ? 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 -1.2(11) . . . . ? C7 C1 C2 C3 -178.7(7) . . . . ? C1 C2 C3 C4 2.4(12) . . . . ? C16 O4 C4 C3 0.8(12) . . . . ? C16 O4 C4 C5 -178.2(6) . . . . ? C2 C3 C4 O4 179.0(7) . . . . ? C2 C3 C4 C5 -2.0(12) . . . . ? O4 C4 C5 C6 179.7(7) . . . . ? C3 C4 C5 C6 0.6(11) . . . . ? C4 C5 C6 C1 0.5(11) . . . . ? C2 C1 C6 C5 -0.3(11) . . . . ? C7 C1 C6 C5 177.1(7) . . . . ? B1 O1 C7 C8 -7.2(11) . . . . ? B1 O1 C7 C1 175.8(7) . . . . ? C6 C1 C7 O1 178.0(7) . . . . ? C2 C1 C7 O1 -4.7(10) . . . . ? C6 C1 C7 C8 1.0(11) . . . . ? C2 C1 C7 C8 178.4(6) . . . . ? O1 C7 C8 C9 2.5(12) . . . . ? C1 C7 C8 C9 179.3(6) . . . . ? B1 O2 C9 C8 6.0(11) . . . . ? B1 O2 C9 C10 -176.4(8) . . . . ? C7 C8 C9 O2 -1.9(12) . . . . ? C7 C8 C9 C10 -179.2(6) . . . . ? O2 C9 C10 C15 -176.0(7) . . . . ? C8 C9 C10 C15 1.5(11) . . . . ? O2 C9 C10 C11 6.6(10) . . . . ? C8 C9 C10 C11 -175.9(7) . . . . ? C15 C10 C11 C12 1.6(11) . . . . ? C9 C10 C11 C12 179.1(7) . . . . ? C10 C11 C12 C13 0.9(12) . . . . ? C17 O3 C13 C14 4.6(12) . . . . ? C17 O3 C13 C12 -178.3(8) . . . . ? C11 C12 C13 O3 -179.8(8) . . . . ? C11 C12 C13 C14 -2.5(12) . . . . ? O3 C13 C14 C15 178.5(8) . . . . ? C12 C13 C14 C15 1.6(11) . . . . ? C13 C14 C15 C10 1.0(11) . . . . ? C11 C10 C15 C14 -2.6(11) . . . . ? C9 C10 C15 C14 179.9(7) . . . . ? C13 O3 C17 C18 171.0(8) . . . . ? O3 C17 C18 C19 120.8(13) . . . . ? C7 O1 B1 F1 -112.0(8) . . . . ? C7 O1 B1 F2 128.7(7) . . . . ? C7 O1 B1 O2 10.4(13) . . . . ? C9 O2 B1 F1 113.1(8) . . . . ? C9 O2 B1 F2 -128.2(7) . . . . ? C9 O2 B1 O1 -9.7(12) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 62.78 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.550 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.056 # Attachment '3.cif' data_sxx02132 _database_code_depnum_ccdc_archive 'CCDC 880810' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 B F2 O4' _chemical_formula_weight 332.10 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/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 21.1856(12) _cell_length_b 7.1155(4) _cell_length_c 10.3692(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.363(5) _cell_angle_gamma 90.00 _cell_volume 1553.49(15) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1236 _cell_measurement_theta_min 3.0158 _cell_measurement_theta_max 28.8441 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9503 _exptl_absorpt_correction_T_max 0.9665 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4077 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 26.35 _reflns_number_total 1579 _reflns_number_gt 1172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0676P)^2^+0.1011P] 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 1579 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 F1 F 0.03891(5) 0.54564(14) 0.33201(9) 0.0613(4) Uani 1 1 d . . . O1 O 0.03994(6) 0.31785(15) 0.17364(10) 0.0528(4) Uani 1 1 d . . . O2 O 0.20116(6) -0.19734(18) -0.15193(12) 0.0674(4) Uani 1 1 d . . . C1 C 0.08155(7) 0.0435(2) 0.09187(13) 0.0388(4) Uani 1 1 d . . . C8 C 0.0000 0.0397(3) 0.2500 0.0423(5) Uani 1 2 d S . . H8 H 0.0000 -0.0910 0.2500 0.051 Uiso 1 2 calc SR . . C5 C 0.12622(8) -0.2360(2) 0.00582(16) 0.0498(4) Uani 1 1 d . . . H5 H 0.1291 -0.3663 0.0032 0.060 Uiso 1 1 calc R . . C7 C 0.03906(7) 0.1346(2) 0.17456(12) 0.0373(4) Uani 1 1 d . . . C4 C 0.16141(7) -0.1276(3) -0.06979(14) 0.0472(4) Uani 1 1 d . . . C6 C 0.08661(8) -0.1506(2) 0.08563(15) 0.0485(4) Uani 1 1 d . . . H6 H 0.0629 -0.2248 0.1362 0.058 Uiso 1 1 calc R . . C3 C 0.15674(8) 0.0662(3) -0.06472(17) 0.0561(5) Uani 1 1 d . . . H3 H 0.1804 0.1400 -0.1156 0.067 Uiso 1 1 calc R . . C2 C 0.11748(8) 0.1506(2) 0.01465(15) 0.0491(4) Uani 1 1 d . . . H2 H 0.1148 0.2810 0.0169 0.059 Uiso 1 1 calc R . . C9 C 0.20300(10) -0.3958(3) -0.1705(2) 0.0730(6) Uani 1 1 d . . . H9B H 0.2170 -0.4559 -0.0895 0.110 Uiso 1 1 calc R . . H9C H 0.2319 -0.4249 -0.2328 0.110 Uiso 1 1 calc R . . H9A H 0.1613 -0.4402 -0.2018 0.110 Uiso 1 1 calc R . . B1 B 0.0000 0.4344(3) 0.2500 0.0453(6) Uani 1 2 d S . . 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 F1 0.0641(7) 0.0527(7) 0.0674(7) -0.0124(4) 0.0085(5) -0.0093(5) O1 0.0679(8) 0.0284(6) 0.0673(8) 0.0011(5) 0.0297(6) -0.0009(5) O2 0.0668(8) 0.0658(9) 0.0765(9) -0.0038(6) 0.0383(6) 0.0072(7) C1 0.0414(8) 0.0367(9) 0.0386(8) 0.0018(6) 0.0057(6) -0.0002(7) C8 0.0508(13) 0.0302(12) 0.0476(12) 0.000 0.0128(9) 0.000 C5 0.0564(11) 0.0368(9) 0.0587(10) -0.0019(7) 0.0175(8) 0.0007(8) C7 0.0416(8) 0.0306(8) 0.0393(8) 0.0013(6) 0.0036(6) 0.0001(6) C4 0.0427(9) 0.0524(11) 0.0480(9) -0.0010(7) 0.0120(6) 0.0036(8) C6 0.0570(10) 0.0362(9) 0.0558(9) 0.0013(7) 0.0217(7) -0.0033(8) C3 0.0595(11) 0.0503(11) 0.0633(11) 0.0103(8) 0.0280(8) -0.0013(9) C2 0.0568(10) 0.0364(9) 0.0562(9) 0.0063(7) 0.0159(7) 0.0000(8) C9 0.0652(12) 0.0686(14) 0.0896(14) -0.0220(11) 0.0281(10) 0.0113(11) B1 0.0552(16) 0.0294(13) 0.0524(14) 0.000 0.0113(11) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 B1 1.3688(17) . ? O1 C7 1.3038(18) . ? O1 B1 1.4762(17) . ? O2 C4 1.3565(19) . ? O2 C9 1.426(2) . ? C1 C6 1.387(2) . ? C1 C2 1.391(2) . ? C1 C7 1.462(2) . ? C8 C7 1.3771(17) . ? C8 C7 1.3771(17) 2 ? C8 H8 0.9300 . ? C5 C4 1.377(2) . ? C5 C6 1.383(2) . ? C5 H5 0.9300 . ? C4 C3 1.384(2) . ? C6 H6 0.9300 . ? C3 C2 1.372(2) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C9 H9A 0.9600 . ? B1 F1 1.3688(17) 2 ? B1 O1 1.4762(17) 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 C7 O1 B1 123.25(12) . . ? C4 O2 C9 118.38(14) . . ? C6 C1 C2 117.92(14) . . ? C6 C1 C7 121.65(13) . . ? C2 C1 C7 120.42(14) . . ? C7 C8 C7 121.26(19) . 2 ? C7 C8 H8 119.4 . . ? C7 C8 H8 119.4 2 . ? C4 C5 C6 119.83(16) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? O1 C7 C8 120.30(13) . . ? O1 C7 C1 115.40(12) . . ? C8 C7 C1 124.30(14) . . ? O2 C4 C5 124.45(16) . . ? O2 C4 C3 116.13(14) . . ? C5 C4 C3 119.42(15) . . ? C5 C6 C1 121.36(15) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? C2 C3 C4 120.63(15) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C2 C1 120.83(15) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? O2 C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C9 H9A 109.5 . . ? H9B C9 H9A 109.5 . . ? H9C C9 H9A 109.5 . . ? F1 B1 F1 109.35(19) . 2 ? F1 B1 O1 109.46(6) . 2 ? F1 B1 O1 108.45(6) 2 2 ? F1 B1 O1 108.45(6) . . ? F1 B1 O1 109.46(6) 2 . ? O1 B1 O1 111.64(17) 2 . ? 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 B1 O1 C7 C8 -0.57(17) . . . . ? B1 O1 C7 C1 179.50(10) . . . . ? C7 C8 C7 O1 0.29(9) 2 . . . ? C7 C8 C7 C1 -179.79(14) 2 . . . ? C6 C1 C7 O1 178.48(13) . . . . ? C2 C1 C7 O1 -2.75(19) . . . . ? C6 C1 C7 C8 -1.4(2) . . . . ? C2 C1 C7 C8 177.33(11) . . . . ? C9 O2 C4 C5 5.7(3) . . . . ? C9 O2 C4 C3 -173.89(15) . . . . ? C6 C5 C4 O2 -179.42(14) . . . . ? C6 C5 C4 C3 0.1(2) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? C7 C1 C6 C5 179.07(14) . . . . ? O2 C4 C3 C2 179.55(16) . . . . ? C5 C4 C3 C2 0.0(3) . . . . ? C4 C3 C2 C1 0.1(3) . . . . ? C6 C1 C2 C3 -0.2(2) . . . . ? C7 C1 C2 C3 -178.99(15) . . . . ? C7 O1 B1 F1 120.97(15) . . . . ? C7 O1 B1 F1 -119.80(15) . . . 2 ? C7 O1 B1 O1 0.29(9) . . . 2 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.143 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.046