data_cb48_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H9 Br0.05 F0.95 O2' _chemical_formula_weight 243.27 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' 'Br' 'Br' -0.2901 2.4595 '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 9.2885(14) _cell_length_b 3.7650(6) _cell_length_c 30.373(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.517(3) _cell_angle_gamma 90.00 _cell_volume 1053.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7082 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 30.45 _exptl_crystal_description 'thin needle frag.' _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 501 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8518 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21009 _diffrn_reflns_av_R_equivalents 0.0716 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 29.13 _reflns_number_total 2827 _reflns_number_gt 2134 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1105P)^2^+1.0684P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2827 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.2078 _refine_ls_wR_factor_gt 0.1910 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.5435(2) 0.8565(6) 0.13660(8) 0.0189(5) Uani 1 1 d . . . H1 H 0.4704 0.8148 0.1122 0.023 Uiso 1 1 calc R . . C2 C 0.5064(2) 0.9976(6) 0.17461(8) 0.0225(5) Uani 1 1 d . . . H2 H 0.4074 1.0516 0.1764 0.027 Uiso 1 1 calc R . . C3 C 0.6112(3) 1.0665(6) 0.21172(8) 0.0233(5) Uani 1 1 d . . . H3 H 0.5821 1.1639 0.2380 0.028 Uiso 1 1 calc R . . C4 C 0.7537(3) 0.9936(7) 0.20980(8) 0.0225(5) Uani 1 1 d . . . H4 H 0.8242 1.0424 0.2346 0.027 Uiso 1 1 calc R . . C4A C 0.7971(2) 0.8437(6) 0.17039(7) 0.0184(5) Uani 1 1 d . A . C5 C 1.1396(2) 0.5260(6) 0.12949(8) 0.0221(5) Uani 1 1 d . . . H5 H 1.2089 0.5765 0.1546 0.026 Uiso 1 1 calc R . . C6 C 1.1830(2) 0.3714(6) 0.09320(9) 0.0235(5) Uani 1 1 d . . . H6 H 1.2826 0.3161 0.0928 0.028 Uiso 1 1 calc R . . C7 C 1.0796(2) 0.2917(6) 0.05570(8) 0.0205(5) Uani 1 1 d . . . H7 H 1.1107 0.1801 0.0305 0.025 Uiso 1 1 calc R . . C8 C 0.9370(2) 0.3731(6) 0.05544(7) 0.0188(5) Uani 1 1 d . . . H8 H 0.8700 0.3164 0.0300 0.023 Uiso 1 1 calc R . . C8A C 0.8856(2) 0.5419(6) 0.09242(7) 0.0159(4) Uani 1 1 d . . . C9 C 0.7381(2) 0.6290(6) 0.09396(7) 0.0156(4) Uani 1 1 d . . . C9A C 0.6916(2) 0.7693(6) 0.13270(7) 0.0162(4) Uani 1 1 d . . . C10 C 0.9414(2) 0.7689(6) 0.16707(7) 0.0200(5) Uani 1 1 d . . . F1 F 1.0415(2) 0.8502(6) 0.20227(6) 0.0307(4) Uani 0.9495(14) 1 d P A 1 Br1 Br 1.0844(8) 0.959(2) 0.2093(2) 0.0307(4) Uani 0.0505(14) 1 d P A 2 C10A C 0.9904(2) 0.6137(6) 0.13032(7) 0.0181(4) Uani 1 1 d . A . C11 C 0.6315(2) 0.5764(6) 0.05348(7) 0.0168(4) Uani 1 1 d . . . O1 O 0.51676(16) 0.4123(5) 0.05386(5) 0.0205(4) Uani 1 1 d . . . O2 O 0.66809(17) 0.7237(5) 0.01746(5) 0.0208(4) Uani 1 1 d . . . H2O H 0.617(3) 0.669(9) -0.0051(10) 0.025 Uiso 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 0.0130(9) 0.0162(10) 0.0274(11) 0.0015(8) 0.0028(8) -0.0004(8) C2 0.0175(10) 0.0182(11) 0.0333(12) 0.0027(9) 0.0086(9) 0.0013(8) C3 0.0254(12) 0.0186(11) 0.0271(11) -0.0025(9) 0.0082(9) -0.0006(9) C4 0.0221(11) 0.0209(11) 0.0242(11) -0.0015(9) 0.0017(8) -0.0010(9) C4A 0.0153(10) 0.0171(10) 0.0225(10) 0.0021(8) 0.0011(8) -0.0021(8) C5 0.0097(9) 0.0194(11) 0.0361(12) 0.0038(9) -0.0006(8) -0.0007(8) C6 0.0106(9) 0.0191(11) 0.0411(13) 0.0027(10) 0.0045(9) 0.0003(8) C7 0.0159(10) 0.0142(10) 0.0328(11) 0.0021(9) 0.0083(8) 0.0024(8) C8 0.0138(10) 0.0161(10) 0.0269(10) 0.0010(8) 0.0038(8) -0.0010(8) C8A 0.0109(9) 0.0116(9) 0.0249(10) 0.0018(8) 0.0016(7) -0.0011(7) C9 0.0106(9) 0.0130(9) 0.0232(10) 0.0013(8) 0.0017(7) -0.0020(7) C9A 0.0119(9) 0.0128(9) 0.0238(10) 0.0019(8) 0.0022(7) 0.0001(7) C10 0.0143(10) 0.0203(11) 0.0239(10) 0.0000(9) -0.0031(8) -0.0028(8) F1 0.0202(10) 0.0403(12) 0.0290(9) 0.0002(8) -0.0063(7) 0.0035(8) Br1 0.0202(10) 0.0403(12) 0.0290(9) 0.0002(8) -0.0063(7) 0.0035(8) C10A 0.0101(9) 0.0153(10) 0.0284(11) 0.0030(8) 0.0013(8) -0.0002(8) C11 0.0099(9) 0.0151(10) 0.0252(10) -0.0005(8) 0.0017(7) 0.0030(7) O1 0.0100(7) 0.0253(9) 0.0259(8) 0.0009(6) 0.0017(5) -0.0041(6) O2 0.0133(7) 0.0260(9) 0.0225(8) 0.0015(7) 0.0005(6) -0.0037(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.356(3) . ? C1 C9A 1.434(3) . ? C1 H1 0.9500 . ? C2 C3 1.413(3) . ? C2 H2 0.9500 . ? C3 C4 1.360(3) . ? C3 H3 0.9500 . ? C4 C4A 1.428(3) . ? C4 H4 0.9500 . ? C4A C10 1.387(3) . ? C4A C9A 1.434(3) . ? C5 C6 1.354(3) . ? C5 C10A 1.428(3) . ? C5 H5 0.9500 . ? C6 C7 1.423(3) . ? C6 H6 0.9500 . ? C7 C8 1.358(3) . ? C7 H7 0.9500 . ? C8 C8A 1.426(3) . ? C8 H8 0.9500 . ? C8A C9 1.416(3) . ? C8A C10A 1.433(3) . ? C9 C9A 1.408(3) . ? C9 C11 1.487(3) . ? C10 F1 1.357(3) . ? C10 C10A 1.388(3) . ? C10 Br1 1.863(8) . ? C11 O1 1.234(3) . ? C11 O2 1.310(3) . ? O2 H2O 0.81(3) . ? 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 C9A 120.9(2) . . ? C2 C1 H1 119.6 . . ? C9A C1 H1 119.6 . . ? C1 C2 C3 121.7(2) . . ? C1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C4A 119.9(2) . . ? C3 C4 H4 120.1 . . ? C4A C4 H4 120.1 . . ? C10 C4A C4 121.5(2) . . ? C10 C4A C9A 118.0(2) . . ? C4 C4A C9A 120.52(19) . . ? C6 C5 C10A 120.5(2) . . ? C6 C5 H5 119.8 . . ? C10A C5 H5 119.8 . . ? C5 C6 C7 120.1(2) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.8(2) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C8A 121.5(2) . . ? C7 C8 H8 119.2 . . ? C8A C8 H8 119.2 . . ? C9 C8A C8 123.68(19) . . ? C9 C8A C10A 119.25(19) . . ? C8 C8A C10A 117.04(19) . . ? C9A C9 C8A 121.25(19) . . ? C9A C9 C11 119.79(18) . . ? C8A C9 C11 118.96(18) . . ? C9 C9A C1 123.88(19) . . ? C9 C9A C4A 119.19(18) . . ? C1 C9A C4A 116.89(19) . . ? F1 C10 C4A 117.8(2) . . ? F1 C10 C10A 117.8(2) . . ? C4A C10 C10A 124.4(2) . . ? F1 C10 Br1 11.0(3) . . ? C4A C10 Br1 118.7(3) . . ? C10A C10 Br1 115.8(3) . . ? C10 C10A C5 122.2(2) . . ? C10 C10A C8A 117.76(19) . . ? C5 C10A C8A 120.1(2) . . ? O1 C11 O2 122.6(2) . . ? O1 C11 C9 122.79(19) . . ? O2 C11 C9 114.63(18) . . ? C11 O2 H2O 114(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 C9A C1 C2 C3 0.4(4) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 C4A -0.7(4) . . . . ? C3 C4 C4A C10 179.4(2) . . . . ? C3 C4 C4A C9A 0.1(3) . . . . ? C10A C5 C6 C7 -0.7(4) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? C6 C7 C8 C8A 0.2(3) . . . . ? C7 C8 C8A C9 -179.4(2) . . . . ? C7 C8 C8A C10A -1.5(3) . . . . ? C8 C8A C9 C9A 174.8(2) . . . . ? C10A C8A C9 C9A -3.0(3) . . . . ? C8 C8A C9 C11 -6.3(3) . . . . ? C10A C8A C9 C11 175.92(19) . . . . ? C8A C9 C9A C1 -178.8(2) . . . . ? C11 C9 C9A C1 2.3(3) . . . . ? C8A C9 C9A C4A 3.6(3) . . . . ? C11 C9 C9A C4A -175.34(19) . . . . ? C2 C1 C9A C9 -178.6(2) . . . . ? C2 C1 C9A C4A -0.9(3) . . . . ? C10 C4A C9A C9 -0.8(3) . . . . ? C4 C4A C9A C9 178.6(2) . . . . ? C10 C4A C9A C1 -178.6(2) . . . . ? C4 C4A C9A C1 0.7(3) . . . . ? C4 C4A C10 F1 -1.4(3) . . . . ? C9A C4A C10 F1 177.9(2) . . . . ? C4 C4A C10 C10A 178.0(2) . . . . ? C9A C4A C10 C10A -2.7(4) . . . . ? C4 C4A C10 Br1 -13.8(4) . . . . ? C9A C4A C10 Br1 165.5(3) . . . . ? F1 C10 C10A C5 2.6(3) . . . . ? C4A C10 C10A C5 -176.8(2) . . . . ? Br1 C10 C10A C5 14.8(4) . . . . ? F1 C10 C10A C8A -177.4(2) . . . . ? C4A C10 C10A C8A 3.2(3) . . . . ? Br1 C10 C10A C8A -165.3(3) . . . . ? C6 C5 C10A C10 179.3(2) . . . . ? C6 C5 C10A C8A -0.7(3) . . . . ? C9 C8A C10A C10 -0.3(3) . . . . ? C8 C8A C10A C10 -178.2(2) . . . . ? C9 C8A C10A C5 179.7(2) . . . . ? C8 C8A C10A C5 1.7(3) . . . . ? C9A C9 C11 O1 -52.0(3) . . . . ? C8A C9 C11 O1 129.1(2) . . . . ? C9A C9 C11 O2 126.9(2) . . . . ? C8A C9 C11 O2 -52.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O1 0.81(3) 1.83(3) 2.632(2) 172(3) 3_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.617 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.094