# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110621a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1i _chemical_melting_point 'not measured' _chemical_formula_moiety 'C15 H11 B F2 O4' _chemical_formula_sum 'C15 H11 B F2 O4' _chemical_formula_weight 304.05 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3288(7) _cell_length_b 19.338(2) _cell_length_c 10.3913(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.1170(10) _cell_angle_gamma 90.00 _cell_volume 1434.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4485 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.56 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9714 _exptl_absorpt_correction_T_max 0.9781 _exptl_absorpt_process_details 'Semi-empirical from equivalents' _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12312 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.61 _reflns_number_total 3329 _reflns_number_gt 2179 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0733P)^2^+0.3947P] 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 0.0074(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3329 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1722 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 B1 B 0.3000(5) 0.10469(14) 0.1235(3) 0.0819(8) Uani 1 1 d . . . C1 C 0.6222(4) -0.25251(13) 0.4081(3) 0.0911(8) Uani 1 1 d . . . H1 H 0.6221 -0.3002 0.3964 0.109 Uiso 1 1 calc R . . C2 C 0.6992(3) -0.22067(13) 0.5202(3) 0.0788(7) Uani 1 1 d . . . H2 H 0.7618 -0.2411 0.5989 0.095 Uiso 1 1 calc R . . C3 C 0.6671(3) -0.15008(11) 0.4963(2) 0.0665(5) Uani 1 1 d . . . H3 H 0.7042 -0.1144 0.5566 0.080 Uiso 1 1 calc R . . C4 C 0.5723(3) -0.14324(10) 0.36968(19) 0.0565(5) Uani 1 1 d . . . C5 C 0.4997(3) -0.08412(10) 0.29451(19) 0.0571(5) Uani 1 1 d . . . H5 H 0.5180 -0.0419 0.3384 0.069 Uiso 1 1 calc R . . C6 C 0.4076(3) -0.08218(10) 0.16720(19) 0.0575(5) Uani 1 1 d . . . H6 H 0.3901 -0.1231 0.1189 0.069 Uiso 1 1 calc R . . C7 C 0.3353(3) -0.01896(10) 0.10333(19) 0.0543(4) Uani 1 1 d . . . C8 C 0.2335(3) -0.01599(10) -0.02576(19) 0.0587(5) Uani 1 1 d . . . H8 H 0.2087 -0.0564 -0.0751 0.070 Uiso 1 1 calc R . . C9 C 0.1680(3) 0.04652(10) -0.08234(19) 0.0555(5) Uani 1 1 d . . . C10 C 0.0621(3) 0.05307(11) -0.21645(18) 0.0574(5) Uani 1 1 d . . . H10 H 0.0302 0.0134 -0.2672 0.069 Uiso 1 1 calc R . . C11 C 0.0080(3) 0.11488(11) -0.27022(19) 0.0586(5) Uani 1 1 d . . . H11 H 0.0423 0.1531 -0.2158 0.070 Uiso 1 1 calc R . . C12 C -0.0954(3) 0.12872(11) -0.40045(19) 0.0577(5) Uani 1 1 d . . . C13 C -0.1507(3) 0.18880(12) -0.4630(2) 0.0701(6) Uani 1 1 d . . . H13 H -0.1299 0.2329 -0.4271 0.084 Uiso 1 1 calc R . . C14 C -0.2455(3) 0.17235(14) -0.5924(2) 0.0770(7) Uani 1 1 d . . . H14 H -0.2992 0.2033 -0.6587 0.092 Uiso 1 1 calc R . . C15 C -0.2434(3) 0.10425(15) -0.6016(2) 0.0795(7) Uani 1 1 d . . . H15 H -0.2975 0.0795 -0.6774 0.095 Uiso 1 1 calc R . . F1 F 0.1753(4) 0.12499(13) 0.19404(16) 0.1769(13) Uani 1 1 d . . . F2 F 0.4476(3) 0.14707(9) 0.1353(2) 0.1757(13) Uani 1 1 d . . . O1 O 0.5434(2) -0.20673(8) 0.31202(15) 0.0784(5) Uani 1 1 d . . . O2 O 0.3706(2) 0.03723(7) 0.17428(14) 0.0718(4) Uani 1 1 d . . . O3 O 0.2008(2) 0.10377(7) -0.01499(14) 0.0732(4) Uani 1 1 d . . . O4 O -0.1516(2) 0.07502(8) -0.48551(14) 0.0730(4) 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 B1 0.108(2) 0.0598(15) 0.0612(15) -0.0067(12) -0.0166(14) 0.0152(14) C1 0.110(2) 0.0616(14) 0.0957(19) 0.0156(13) 0.0100(16) 0.0090(13) C2 0.0818(15) 0.0780(15) 0.0721(15) 0.0216(12) 0.0084(12) 0.0109(12) C3 0.0705(13) 0.0690(13) 0.0565(12) 0.0064(10) 0.0073(10) 0.0014(10) C4 0.0535(10) 0.0573(11) 0.0579(11) 0.0062(9) 0.0109(8) -0.0002(8) C5 0.0542(10) 0.0576(11) 0.0593(11) 0.0069(8) 0.0123(8) -0.0024(8) C6 0.0543(10) 0.0583(11) 0.0584(11) 0.0070(9) 0.0098(8) -0.0012(8) C7 0.0473(9) 0.0596(11) 0.0554(10) 0.0028(8) 0.0105(8) -0.0023(8) C8 0.0577(11) 0.0599(11) 0.0548(11) 0.0016(9) 0.0051(8) 0.0006(8) C9 0.0474(9) 0.0651(11) 0.0522(10) 0.0016(9) 0.0079(8) 0.0000(8) C10 0.0499(10) 0.0680(12) 0.0522(10) 0.0022(9) 0.0070(8) 0.0001(8) C11 0.0503(10) 0.0709(12) 0.0529(11) 0.0021(9) 0.0079(8) -0.0005(9) C12 0.0507(10) 0.0671(12) 0.0537(10) 0.0037(9) 0.0088(8) -0.0010(9) C13 0.0691(13) 0.0680(13) 0.0696(13) 0.0073(11) 0.0081(10) 0.0017(10) C14 0.0735(14) 0.0901(17) 0.0629(13) 0.0213(12) 0.0064(11) 0.0095(12) C15 0.0826(16) 0.0978(19) 0.0505(12) 0.0014(11) -0.0007(10) 0.0081(13) F1 0.245(3) 0.211(2) 0.0626(10) -0.0024(12) 0.0083(12) 0.157(2) F2 0.204(2) 0.0881(12) 0.1617(18) 0.0518(12) -0.1111(17) -0.0574(13) O1 0.0959(12) 0.0609(9) 0.0703(10) 0.0028(7) 0.0020(8) 0.0022(8) O2 0.0878(10) 0.0612(9) 0.0557(8) 0.0041(7) -0.0062(7) 0.0045(7) O3 0.0900(11) 0.0619(9) 0.0563(8) 0.0025(7) -0.0073(7) 0.0082(7) O4 0.0819(10) 0.0713(9) 0.0593(9) 0.0000(7) 0.0019(7) 0.0049(8) _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 B1 F2 1.341(4) . ? B1 F1 1.353(4) . ? B1 O3 1.458(3) . ? B1 O2 1.457(3) . ? C1 C2 1.326(4) . ? C1 O1 1.361(3) . ? C1 H1 0.9300 . ? C2 C3 1.398(3) . ? C2 H2 0.9300 . ? C3 C4 1.348(3) . ? C3 H3 0.9300 . ? C4 O1 1.362(2) . ? C4 C5 1.418(3) . ? C5 C6 1.342(3) . ? C5 H5 0.9300 . ? C6 C7 1.434(3) . ? C6 H6 0.9300 . ? C7 O2 1.305(2) . ? C7 C8 1.380(3) . ? C8 C9 1.382(3) . ? C8 H8 0.9300 . ? C9 O3 1.303(2) . ? C9 C10 1.439(3) . ? C10 C11 1.341(3) . ? C10 H10 0.9300 . ? C11 C12 1.418(3) . ? C11 H11 0.9300 . ? C12 C13 1.348(3) . ? C12 O4 1.365(2) . ? C13 C14 1.402(3) . ? C13 H13 0.9300 . ? C14 C15 1.321(4) . ? C14 H14 0.9300 . ? C15 O4 1.364(3) . ? C15 H15 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 F2 B1 F1 113.8(3) . . ? F2 B1 O3 108.0(2) . . ? F1 B1 O3 106.9(2) . . ? F2 B1 O2 107.6(2) . . ? F1 B1 O2 107.0(2) . . ? O3 B1 O2 113.76(19) . . ? C2 C1 O1 111.6(2) . . ? C2 C1 H1 124.2 . . ? O1 C1 H1 124.2 . . ? C1 C2 C3 106.0(2) . . ? C1 C2 H2 127.0 . . ? C3 C2 H2 127.0 . . ? C4 C3 C2 107.3(2) . . ? C4 C3 H3 126.3 . . ? C2 C3 H3 126.3 . . ? C3 C4 O1 109.59(17) . . ? C3 C4 C5 131.5(2) . . ? O1 C4 C5 118.89(17) . . ? C6 C5 C4 127.4(2) . . ? C6 C5 H5 116.3 . . ? C4 C5 H5 116.3 . . ? C5 C6 C7 122.02(19) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? O2 C7 C8 120.55(18) . . ? O2 C7 C6 116.31(17) . . ? C8 C7 C6 123.14(18) . . ? C7 C8 C9 120.59(19) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? O3 C9 C8 120.73(18) . . ? O3 C9 C10 116.03(17) . . ? C8 C9 C10 123.24(18) . . ? C11 C10 C9 121.71(19) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 C12 127.5(2) . . ? C10 C11 H11 116.2 . . ? C12 C11 H11 116.2 . . ? C13 C12 O4 109.25(18) . . ? C13 C12 C11 131.3(2) . . ? O4 C12 C11 119.44(18) . . ? C12 C13 C14 107.2(2) . . ? C12 C13 H13 126.4 . . ? C14 C13 H13 126.4 . . ? C15 C14 C13 106.5(2) . . ? C15 C14 H14 126.7 . . ? C13 C14 H14 126.7 . . ? C14 C15 O4 111.1(2) . . ? C14 C15 H15 124.4 . . ? O4 C15 H15 124.4 . . ? C1 O1 C4 105.44(18) . . ? C7 O2 B1 122.15(16) . . ? C9 O3 B1 122.05(17) . . ? C15 O4 C12 105.86(18) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.341 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 950204' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110610a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1j _chemical_melting_point 'not measured' _chemical_formula_moiety 'C23 H19 B F2 O2' _chemical_formula_sum 'C23 H19 B F2 O2' _chemical_formula_weight 376.19 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M '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 16.957(2) _cell_length_b 11.8082(16) _cell_length_c 9.9913(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.180(2) _cell_angle_gamma 90.00 _cell_volume 1992.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1892 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 26.04 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9751 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_process_details 'Semi-empirical from equivalents' _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8451 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.58 _reflns_number_total 2306 _reflns_number_gt 1119 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.1205P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2306 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1147 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.2196 _refine_ls_wR_factor_gt 0.1736 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 C6 C 0.31136(12) 0.9417(2) 0.77497(19) 0.0687(6) Uani 1 1 d . . . C2 C 0.41567(16) 0.9727(3) 0.6313(2) 0.0961(9) Uani 1 1 d . . . H2 H 0.4519 1.0213 0.5967 0.115 Uiso 1 1 calc R . . C1 C 0.36586(14) 1.0126(2) 0.7217(2) 0.0818(7) Uani 1 1 d . . . H1 H 0.3687 1.0883 0.7476 0.098 Uiso 1 1 calc R . . C5 C 0.30882(16) 0.8312(2) 0.7338(3) 0.0937(8) Uani 1 1 d . . . H5 H 0.2726 0.7819 0.7673 0.112 Uiso 1 1 calc R . . C3 C 0.41225(16) 0.8631(3) 0.5923(3) 0.0992(9) Uani 1 1 d . . . H3 H 0.4459 0.8362 0.5310 0.119 Uiso 1 1 calc R . . C4 C 0.3589(2) 0.7921(3) 0.6438(3) 0.1108(10) Uani 1 1 d . . . H4 H 0.3565 0.7165 0.6175 0.133 Uiso 1 1 calc R . . C8 C 0.20570(12) 0.9335(2) 0.9341(2) 0.0716(6) Uani 1 1 d . . . H8 H 0.1996 0.8559 0.9205 0.086 Uiso 1 1 calc R . . C10 C 0.10130(12) 0.9380(2) 1.08917(17) 0.0686(6) Uani 1 1 d . . . H10 H 0.0957 0.8599 1.0805 0.082 Uiso 1 1 calc R . . C9 C 0.15636(12) 0.9894(2) 1.02318(18) 0.0680(6) Uani 1 1 d . . . H9 H 0.1632 1.0669 1.0359 0.082 Uiso 1 1 calc R . . C7 C 0.25988(13) 0.9880(2) 0.8702(2) 0.0734(7) Uani 1 1 d . . . H7 H 0.2655 1.0650 0.8886 0.088 Uiso 1 1 calc R . . C12 C 0.0000 0.9394(3) 1.2500 0.0692(8) Uani 1 2 d S . . H12 H 0.0000 0.8606 1.2500 0.083 Uiso 1 2 calc SR . . O1 O 0.05256(8) 1.10657(14) 1.17352(14) 0.0778(5) Uani 1 1 d . . . C11 C 0.05021(11) 0.99731(19) 1.17300(18) 0.0621(6) Uani 1 1 d . . . B1 B 0.0000 1.1763(3) 1.2500 0.0737(10) Uani 1 2 d S . . F1 F -0.04585(9) 1.24176(12) 1.16120(14) 0.0988(6) 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 C6 0.0628(13) 0.0823(15) 0.0631(12) -0.0008(11) 0.0166(10) 0.0026(11) C2 0.0781(17) 0.128(3) 0.0870(17) -0.0064(16) 0.0349(14) -0.0094(16) C1 0.0756(15) 0.0900(16) 0.0834(14) -0.0076(13) 0.0265(12) -0.0107(12) C5 0.0993(18) 0.0834(18) 0.1048(18) -0.0043(15) 0.0438(15) -0.0032(15) C3 0.0892(18) 0.129(3) 0.0850(16) -0.0069(17) 0.0358(14) 0.0177(18) C4 0.128(2) 0.096(2) 0.116(2) -0.0194(16) 0.0486(19) 0.0100(18) C8 0.0678(13) 0.0847(15) 0.0648(12) 0.0018(11) 0.0194(11) 0.0044(11) C10 0.0742(14) 0.0715(14) 0.0637(12) 0.0004(10) 0.0255(11) 0.0012(11) C9 0.0669(14) 0.0758(14) 0.0629(12) 0.0014(10) 0.0156(11) 0.0050(10) C7 0.0657(13) 0.0811(15) 0.0759(13) -0.0043(11) 0.0208(11) -0.0006(11) C12 0.079(2) 0.0603(17) 0.0726(17) 0.000 0.0299(16) 0.000 O1 0.0789(11) 0.0642(10) 0.0956(11) 0.0047(7) 0.0375(9) 0.0008(7) C11 0.0627(13) 0.0652(13) 0.0600(11) 0.0003(10) 0.0135(10) 0.0027(10) B1 0.080(2) 0.058(2) 0.087(2) 0.000 0.028(2) 0.000 F1 0.1078(11) 0.0878(10) 0.1045(10) 0.0174(8) 0.0293(9) 0.0246(8) _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 C6 C5 1.367(3) . ? C6 C1 1.388(3) . ? C6 C7 1.455(3) . ? C2 C3 1.351(4) . ? C2 C1 1.375(3) . ? C5 C4 1.372(4) . ? C3 C4 1.368(4) . ? C8 C7 1.331(3) . ? C8 C9 1.437(3) . ? C10 C9 1.337(3) . ? C10 C11 1.440(3) . ? C12 C11 1.380(3) . ? C12 C11 1.380(3) 2_557 ? O1 C11 1.291(3) . ? O1 B1 1.476(2) . ? B1 F1 1.365(2) 2_557 ? B1 F1 1.365(2) . ? B1 O1 1.476(2) 2_557 ? 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 C5 C6 C1 117.6(2) . . ? C5 C6 C7 123.5(2) . . ? C1 C6 C7 118.9(2) . . ? C3 C2 C1 120.3(3) . . ? C2 C1 C6 121.0(2) . . ? C6 C5 C4 121.0(3) . . ? C2 C3 C4 119.4(2) . . ? C3 C4 C5 120.6(3) . . ? C7 C8 C9 122.7(2) . . ? C9 C10 C11 123.3(2) . . ? C10 C9 C8 124.7(2) . . ? C8 C7 C6 127.7(2) . . ? C11 C12 C11 120.5(3) . 2_557 ? C11 O1 B1 122.67(17) . . ? O1 C11 C12 120.9(2) . . ? O1 C11 C10 117.95(18) . . ? C12 C11 C10 121.1(2) . . ? F1 B1 F1 111.1(3) 2_557 . ? F1 B1 O1 108.32(8) 2_557 2_557 ? F1 B1 O1 108.49(8) . 2_557 ? F1 B1 O1 108.49(8) 2_557 . ? F1 B1 O1 108.32(8) . . ? O1 B1 O1 112.2(3) 2_557 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.503 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 950205'