# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email luxmsc@gmail.com loop_ _publ_author_name M.Ravikanth L.Vellanki data_mr017 _database_code_depnum_ccdc_archive 'CCDC 849331' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H11 B Br2 F2 N2 O' _chemical_formula_sum 'C16 H11 B Br2 F2 N2 O' _chemical_formula_weight 455.90 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' N N 0.0061 0.0033 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0532(4) _cell_length_b 9.4760(4) _cell_length_c 11.2338(5) _cell_angle_alpha 78.222(4) _cell_angle_beta 83.573(4) _cell_angle_gamma 67.746(4) _cell_volume 776.15(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5073 _cell_measurement_theta_min 3.1277 _cell_measurement_theta_max 32.4512 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.951 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 5.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3781 _exptl_absorpt_correction_T_max 0.5485 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5582 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2727 _reflns_number_gt 2330 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0377P)^2^] 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 2727 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0269 _refine_ls_R_factor_gt 0.0216 _refine_ls_wR_factor_ref 0.0593 _refine_ls_wR_factor_gt 0.0584 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 B1 B 0.3446(4) 0.4166(3) 0.1278(3) 0.0177(6) Uani 1 1 d . . . N1 N 0.2895(3) 0.5888(2) 0.14540(17) 0.0155(4) Uani 1 1 d . . . N2 N 0.5255(3) 0.3251(2) 0.19239(17) 0.0156(4) Uani 1 1 d . . . O1 O 0.9074(2) 0.80143(19) 0.50508(15) 0.0215(4) Uani 1 1 d . . . F1 F 0.3652(2) 0.40735(16) 0.00658(12) 0.0227(3) Uani 1 1 d . . . F2 F 0.21472(19) 0.35950(16) 0.18432(13) 0.0225(3) Uani 1 1 d . . . Br1 Br -0.00815(4) 0.70083(3) -0.00396(2) 0.02462(10) Uani 1 1 d . . . Br2 Br 0.56445(4) 0.03815(3) 0.13298(2) 0.02682(10) Uani 1 1 d . . . C1 C 0.1512(3) 0.7132(3) 0.0964(2) 0.0187(5) Uani 1 1 d . . . C2 C 0.1476(4) 0.8482(3) 0.1322(2) 0.0213(6) Uani 1 1 d . . . H2 H 0.0627 0.9502 0.1103 0.026 Uiso 1 1 calc R . . C3 C 0.2903(4) 0.8037(3) 0.2046(2) 0.0202(6) Uani 1 1 d . . . H3 H 0.3234 0.8701 0.2419 0.024 Uiso 1 1 calc R . . C4 C 0.3806(3) 0.6416(3) 0.2147(2) 0.0156(5) Uani 1 1 d . . . C5 C 0.5389(3) 0.5427(3) 0.2704(2) 0.0160(5) Uani 1 1 d . . . C6 C 0.6096(3) 0.3853(3) 0.2602(2) 0.0155(5) Uani 1 1 d . . . C7 C 0.7576(3) 0.2644(3) 0.3143(2) 0.0192(5) Uani 1 1 d . . . H7 H 0.8386 0.2728 0.3653 0.023 Uiso 1 1 calc R . . C8 C 0.7649(3) 0.1292(3) 0.2798(2) 0.0195(5) Uani 1 1 d . . . H8 H 0.8507 0.0278 0.3026 0.023 Uiso 1 1 calc R . . C9 C 0.6222(3) 0.1723(3) 0.2057(2) 0.0180(5) Uani 1 1 d . . . C10 C 0.6358(3) 0.6040(3) 0.3384(2) 0.0165(5) Uani 1 1 d . . . C11 C 0.8172(3) 0.5798(3) 0.3117(2) 0.0190(5) Uani 1 1 d . . . H11 H 0.8811 0.5175 0.2529 0.023 Uiso 1 1 calc R . . C12 C 0.9049(4) 0.6455(3) 0.3696(2) 0.0199(5) Uani 1 1 d . . . H12 H 1.0278 0.6296 0.3498 0.024 Uiso 1 1 calc R . . C13 C 0.8126(3) 0.7351(3) 0.4574(2) 0.0187(5) Uani 1 1 d . . . C14 C 0.6359(3) 0.7530(3) 0.4891(2) 0.0190(5) Uani 1 1 d . . . H14 H 0.5745 0.8093 0.5519 0.023 Uiso 1 1 calc R . . C15 C 0.5484(3) 0.6888(3) 0.4292(2) 0.0189(5) Uani 1 1 d . . . H15 H 0.4263 0.7031 0.4507 0.023 Uiso 1 1 calc R . . C16 C 0.8108(4) 0.9099(3) 0.5834(2) 0.0236(6) Uani 1 1 d . . . H16A H 0.6992 0.9828 0.5457 0.035 Uiso 1 1 calc R . . H16B H 0.8846 0.9669 0.5964 0.035 Uiso 1 1 calc R . . H16C H 0.7826 0.8543 0.6617 0.035 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 B1 0.0170(16) 0.0166(14) 0.0202(15) -0.0038(11) -0.0017(11) -0.0064(12) N1 0.0144(11) 0.0158(10) 0.0164(10) -0.0028(8) -0.0011(8) -0.0056(9) N2 0.0171(12) 0.0141(10) 0.0163(11) -0.0043(8) 0.0010(8) -0.0062(9) O1 0.0182(10) 0.0225(10) 0.0268(10) -0.0100(8) -0.0044(7) -0.0071(8) F1 0.0262(9) 0.0251(8) 0.0170(7) -0.0067(6) -0.0032(6) -0.0076(7) F2 0.0198(8) 0.0205(8) 0.0285(8) 0.0002(6) -0.0019(6) -0.0110(7) Br1 0.02438(17) 0.02120(15) 0.02764(16) -0.00103(11) -0.01076(11) -0.00660(12) Br2 0.03166(18) 0.02034(15) 0.03266(17) -0.00952(11) -0.00235(12) -0.01141(13) C1 0.0172(14) 0.0195(13) 0.0177(13) 0.0008(10) -0.0033(10) -0.0063(11) C2 0.0202(15) 0.0137(12) 0.0253(14) -0.0014(10) -0.0007(11) -0.0020(11) C3 0.0246(15) 0.0178(13) 0.0204(13) -0.0041(10) 0.0016(10) -0.0105(11) C4 0.0161(14) 0.0176(13) 0.0157(13) -0.0054(10) 0.0008(10) -0.0079(11) C5 0.0176(14) 0.0198(13) 0.0118(12) -0.0035(9) 0.0038(10) -0.0090(11) C6 0.0155(13) 0.0189(12) 0.0130(12) -0.0034(9) 0.0009(9) -0.0075(10) C7 0.0170(14) 0.0230(14) 0.0182(13) -0.0042(10) -0.0005(10) -0.0075(11) C8 0.0157(14) 0.0175(13) 0.0211(13) -0.0041(10) 0.0034(10) -0.0020(11) C9 0.0200(14) 0.0155(13) 0.0202(13) -0.0060(10) 0.0034(10) -0.0081(11) C10 0.0181(14) 0.0162(12) 0.0159(13) -0.0014(10) -0.0021(10) -0.0073(11) C11 0.0174(14) 0.0188(13) 0.0212(13) -0.0076(10) 0.0030(10) -0.0062(11) C12 0.0158(14) 0.0218(13) 0.0205(14) -0.0038(10) 0.0011(10) -0.0057(11) C13 0.0203(15) 0.0150(12) 0.0207(13) -0.0010(10) -0.0049(10) -0.0063(11) C14 0.0208(15) 0.0202(13) 0.0150(12) -0.0052(10) -0.0013(10) -0.0050(11) C15 0.0173(14) 0.0214(13) 0.0184(13) -0.0033(10) 0.0010(10) -0.0082(11) C16 0.0260(16) 0.0184(13) 0.0257(14) -0.0071(11) -0.0040(11) -0.0049(12) _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 F1 1.369(3) . ? B1 F2 1.389(3) . ? B1 N2 1.557(3) . ? B1 N1 1.569(3) . ? N1 C1 1.345(3) . ? N1 C4 1.400(3) . ? N2 C9 1.344(3) . ? N2 C6 1.396(3) . ? O1 C13 1.363(3) . ? O1 C16 1.430(3) . ? Br1 C1 1.850(3) . ? Br1 F2 3.0244(15) 2_565 ? Br1 F1 3.4033(15) 2_565 ? Br2 C9 1.860(2) . ? C1 C2 1.407(3) . ? C2 C3 1.365(4) . ? C2 H2 0.9500 . ? C3 C4 1.415(3) . ? C3 H3 0.9500 . ? C4 C5 1.389(3) . ? C5 C6 1.405(3) . ? C5 C10 1.479(3) . ? C6 C7 1.396(4) . ? C7 C8 1.391(3) . ? C7 H7 0.9500 . ? C8 C9 1.378(4) . ? C8 H8 0.9500 . ? C10 C15 1.388(3) . ? C10 C11 1.398(4) . ? C11 C12 1.382(4) . ? C11 H11 0.9500 . ? C12 C13 1.395(3) . ? C12 H12 0.9500 . ? C13 C14 1.382(4) . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 F1 B1 F2 110.9(2) . . ? F1 B1 N2 110.7(2) . . ? F2 B1 N2 109.5(2) . . ? F1 B1 N1 110.5(2) . . ? F2 B1 N1 109.1(2) . . ? N2 B1 N1 105.90(19) . . ? C1 N1 C4 106.97(19) . . ? C1 N1 B1 127.7(2) . . ? C4 N1 B1 125.4(2) . . ? C9 N2 C6 106.0(2) . . ? C9 N2 B1 128.1(2) . . ? C6 N2 B1 125.60(19) . . ? C13 O1 C16 117.15(19) . . ? C1 Br1 F2 170.47(8) . 2_565 ? C1 Br1 F1 143.66(8) . 2_565 ? F2 Br1 F1 40.88(3) 2_565 2_565 ? N1 C1 C2 110.8(2) . . ? N1 C1 Br1 122.82(18) . . ? C2 C1 Br1 126.4(2) . . ? C3 C2 C1 106.4(2) . . ? C3 C2 H2 126.8 . . ? C1 C2 H2 126.8 . . ? C2 C3 C4 108.3(2) . . ? C2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? C5 C4 N1 121.4(2) . . ? C5 C4 C3 130.9(2) . . ? N1 C4 C3 107.5(2) . . ? C4 C5 C6 120.3(2) . . ? C4 C5 C10 119.9(2) . . ? C6 C5 C10 119.8(2) . . ? C7 C6 N2 108.6(2) . . ? C7 C6 C5 130.1(2) . . ? N2 C6 C5 121.3(2) . . ? C8 C7 C6 107.4(2) . . ? C8 C7 H7 126.3 . . ? C6 C7 H7 126.3 . . ? C9 C8 C7 106.0(2) . . ? C9 C8 H8 127.0 . . ? C7 C8 H8 127.0 . . ? N2 C9 C8 112.0(2) . . ? N2 C9 Br2 122.92(19) . . ? C8 C9 Br2 125.06(18) . . ? C15 C10 C11 118.3(2) . . ? C15 C10 C5 120.9(2) . . ? C11 C10 C5 120.8(2) . . ? C12 C11 C10 120.9(2) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 119.8(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? O1 C13 C14 124.6(2) . . ? O1 C13 C12 115.6(2) . . ? C14 C13 C12 119.8(2) . . ? C13 C14 C15 119.9(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 121.2(2) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 F1 B1 N1 C1 53.6(3) . . . . ? F2 B1 N1 C1 -68.6(3) . . . . ? N2 B1 N1 C1 173.6(2) . . . . ? F1 B1 N1 C4 -124.8(2) . . . . ? F2 B1 N1 C4 112.9(2) . . . . ? N2 B1 N1 C4 -4.8(3) . . . . ? F1 B1 N2 C9 -62.8(3) . . . . ? F2 B1 N2 C9 59.9(3) . . . . ? N1 B1 N2 C9 177.4(2) . . . . ? F1 B1 N2 C6 124.7(2) . . . . ? F2 B1 N2 C6 -112.6(2) . . . . ? N1 B1 N2 C6 4.9(3) . . . . ? C4 N1 C1 C2 -0.3(3) . . . . ? B1 N1 C1 C2 -179.0(2) . . . . ? C4 N1 C1 Br1 179.68(17) . . . . ? B1 N1 C1 Br1 1.0(3) . . . . ? F2 Br1 C1 N1 -37.1(6) 2_565 . . . ? F1 Br1 C1 N1 76.0(2) 2_565 . . . ? F2 Br1 C1 C2 142.9(4) 2_565 . . . ? F1 Br1 C1 C2 -104.1(2) 2_565 . . . ? N1 C1 C2 C3 0.6(3) . . . . ? Br1 C1 C2 C3 -179.38(18) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C1 N1 C4 C5 -175.2(2) . . . . ? B1 N1 C4 C5 3.5(3) . . . . ? C1 N1 C4 C3 -0.1(3) . . . . ? B1 N1 C4 C3 178.6(2) . . . . ? C2 C3 C4 C5 174.9(3) . . . . ? C2 C3 C4 N1 0.5(3) . . . . ? N1 C4 C5 C6 -1.3(3) . . . . ? C3 C4 C5 C6 -175.1(2) . . . . ? N1 C4 C5 C10 177.3(2) . . . . ? C3 C4 C5 C10 3.5(4) . . . . ? C9 N2 C6 C7 -0.3(3) . . . . ? B1 N2 C6 C7 173.6(2) . . . . ? C9 N2 C6 C5 -177.4(2) . . . . ? B1 N2 C6 C5 -3.6(3) . . . . ? C4 C5 C6 C7 -175.2(2) . . . . ? C10 C5 C6 C7 6.2(4) . . . . ? C4 C5 C6 N2 1.3(3) . . . . ? C10 C5 C6 N2 -177.3(2) . . . . ? N2 C6 C7 C8 0.0(3) . . . . ? C5 C6 C7 C8 176.8(2) . . . . ? C6 C7 C8 C9 0.3(3) . . . . ? C6 N2 C9 C8 0.5(3) . . . . ? B1 N2 C9 C8 -173.2(2) . . . . ? C6 N2 C9 Br2 179.75(17) . . . . ? B1 N2 C9 Br2 6.1(3) . . . . ? C7 C8 C9 N2 -0.5(3) . . . . ? C7 C8 C9 Br2 -179.73(17) . . . . ? C4 C5 C10 C15 52.9(3) . . . . ? C6 C5 C10 C15 -128.5(3) . . . . ? C4 C5 C10 C11 -126.1(3) . . . . ? C6 C5 C10 C11 52.5(3) . . . . ? C15 C10 C11 C12 -3.3(4) . . . . ? C5 C10 C11 C12 175.8(2) . . . . ? C10 C11 C12 C13 1.0(4) . . . . ? C16 O1 C13 C14 -7.0(3) . . . . ? C16 O1 C13 C12 172.2(2) . . . . ? C11 C12 C13 O1 -176.8(2) . . . . ? C11 C12 C13 C14 2.4(4) . . . . ? O1 C13 C14 C15 175.8(2) . . . . ? C12 C13 C14 C15 -3.4(4) . . . . ? C13 C14 C15 C10 1.0(4) . . . . ? C11 C10 C15 C14 2.3(4) . . . . ? C5 C10 C15 C14 -176.7(2) . . . . ? 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 C7 H7 O1 0.95 2.44 3.349(3) 160.1 2_766 C16 H16C F2 0.98 2.38 3.306(3) 158.3 2_666 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.593 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.069 data_mr043a _database_code_depnum_ccdc_archive 'CCDC 849332' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H9 B Br4 F2 N2 O' _chemical_formula_weight 613.70 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' N N 0.0061 0.0033 '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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8922(4) _cell_length_b 11.1893(6) _cell_length_c 11.3508(5) _cell_angle_alpha 73.442(4) _cell_angle_beta 74.044(4) _cell_angle_gamma 84.062(4) _cell_volume 923.44(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4668 _cell_measurement_theta_min 3.6873 _cell_measurement_theta_max 32.7252 _exptl_crystal_description plate _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 8.744 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1605 _exptl_absorpt_correction_T_max 0.2611 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10011 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 32.80 _reflns_number_total 6014 _reflns_number_gt 4622 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0348P)^2^] 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 6014 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 B1 B 0.7511(4) 0.0046(3) 0.6953(4) 0.0209(7) Uani 1 1 d . . . Br1 Br 0.83020(5) 0.11311(3) 0.91808(3) 0.03386(10) Uani 1 1 d . . . Br2 Br 0.90625(5) 0.43872(3) 0.77205(4) 0.03204(10) Uani 1 1 d . . . Br3 Br 0.69920(4) -0.20837(3) 0.32831(4) 0.02844(9) Uani 1 1 d . . . Br4 Br 0.75454(4) -0.27080(3) 0.64063(4) 0.02917(9) Uani 1 1 d . . . F1 F 0.5941(2) -0.03271(16) 0.78029(18) 0.0267(4) Uani 1 1 d . . . F2 F 0.8904(2) -0.06378(16) 0.7347(2) 0.0279(4) Uani 1 1 d . . . N1 N 0.7786(3) 0.1461(2) 0.6732(2) 0.0195(5) Uani 1 1 d . . . N2 N 0.7521(3) -0.0083(2) 0.5611(3) 0.0187(5) Uani 1 1 d . . . O1 O 0.7166(3) 0.5938(2) 0.0149(2) 0.0327(6) Uani 1 1 d . . . C1 C 0.8167(4) 0.2002(3) 0.7553(3) 0.0213(6) Uani 1 1 d . . . C2 C 0.8414(4) 0.3280(3) 0.6981(3) 0.0212(6) Uani 1 1 d . . . C3 C 0.8160(4) 0.3535(3) 0.5781(3) 0.0191(6) Uani 1 1 d . . . H3 H 0.8246 0.4324 0.5171 0.023 Uiso 1 1 calc R . . C4 C 0.7750(4) 0.2407(3) 0.5629(3) 0.0178(6) Uani 1 1 d . . . C5 C 0.7476(4) 0.2137(3) 0.4563(3) 0.0178(6) Uani 1 1 d . . . C6 C 0.7328(4) 0.0897(3) 0.4574(3) 0.0183(6) Uani 1 1 d . . . C7 C 0.7066(4) 0.0400(3) 0.3626(3) 0.0207(6) Uani 1 1 d . . . H7 H 0.6883 0.0856 0.2824 0.025 Uiso 1 1 calc R . . C8 C 0.7130(4) -0.0881(3) 0.4100(3) 0.0226(6) Uani 1 1 d . . . C9 C 0.7395(4) -0.1139(3) 0.5314(3) 0.0208(6) Uani 1 1 d . . . C10 C 0.7382(4) 0.3157(3) 0.3430(3) 0.0169(6) Uani 1 1 d . . . C11 C 0.8405(4) 0.3101(3) 0.2229(3) 0.0200(6) Uani 1 1 d . . . H11 H 0.9185 0.2407 0.2145 0.024 Uiso 1 1 calc R . . C12 C 0.8291(4) 0.4042(3) 0.1165(3) 0.0234(6) Uani 1 1 d . . . H12 H 0.9002 0.3997 0.0354 0.028 Uiso 1 1 calc R . . C13 C 0.7140(4) 0.5063(3) 0.1266(3) 0.0225(6) Uani 1 1 d . . . C14 C 0.6121(4) 0.5132(3) 0.2443(3) 0.0206(6) Uani 1 1 d . . . H14 H 0.5332 0.5824 0.2516 0.025 Uiso 1 1 calc R . . C15 C 0.6242(4) 0.4191(3) 0.3526(3) 0.0193(6) Uani 1 1 d . . . H15 H 0.5546 0.4249 0.4337 0.023 Uiso 1 1 calc R . . C16 C 0.5955(6) 0.6983(4) 0.0193(4) 0.0491(11) Uani 1 1 d . . . H16A H 0.4744 0.6687 0.0513 0.074 Uiso 1 1 calc R . . H16B H 0.6109 0.7548 -0.0664 0.074 Uiso 1 1 calc R . . H16C H 0.6185 0.7428 0.0760 0.074 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 B1 0.0200(16) 0.0168(15) 0.024(2) -0.0004(13) -0.0078(15) 0.0000(12) Br1 0.0538(2) 0.02732(18) 0.02052(19) -0.00078(13) -0.01657(17) 0.00194(15) Br2 0.0545(2) 0.02134(16) 0.0273(2) -0.00631(13) -0.02142(18) -0.00251(14) Br3 0.02959(17) 0.02470(17) 0.0346(2) -0.01591(14) -0.00525(15) -0.00205(12) Br4 0.03553(19) 0.01487(15) 0.0363(2) -0.00187(12) -0.01269(16) -0.00176(12) F1 0.0281(10) 0.0251(10) 0.0209(11) -0.0001(7) -0.0014(8) -0.0052(7) F2 0.0303(10) 0.0202(9) 0.0363(12) -0.0050(8) -0.0193(9) 0.0078(7) N1 0.0224(13) 0.0191(12) 0.0162(14) -0.0038(10) -0.0048(11) -0.0001(10) N2 0.0193(12) 0.0141(11) 0.0207(14) -0.0026(9) -0.0037(11) -0.0013(9) O1 0.0461(15) 0.0260(12) 0.0164(13) 0.0015(9) -0.0039(11) 0.0100(10) C1 0.0245(15) 0.0227(15) 0.0150(15) -0.0023(11) -0.0059(13) 0.0019(11) C2 0.0290(16) 0.0172(14) 0.0201(16) -0.0071(11) -0.0080(13) -0.0014(11) C3 0.0219(14) 0.0167(13) 0.0173(16) -0.0016(11) -0.0057(12) -0.0006(11) C4 0.0193(14) 0.0165(13) 0.0154(15) -0.0011(11) -0.0043(12) 0.0000(10) C5 0.0156(13) 0.0164(13) 0.0184(16) -0.0013(11) -0.0031(12) -0.0009(10) C6 0.0186(14) 0.0173(13) 0.0164(15) -0.0025(11) -0.0026(12) -0.0006(10) C7 0.0222(15) 0.0201(14) 0.0204(17) -0.0062(11) -0.0050(13) -0.0017(11) C8 0.0200(14) 0.0193(14) 0.0298(19) -0.0101(12) -0.0038(13) -0.0036(11) C9 0.0177(14) 0.0165(14) 0.0250(18) -0.0029(11) -0.0025(13) -0.0017(11) C10 0.0207(14) 0.0150(13) 0.0154(15) -0.0027(10) -0.0064(12) -0.0012(10) C11 0.0212(15) 0.0193(14) 0.0195(16) -0.0057(11) -0.0055(13) 0.0021(11) C12 0.0276(16) 0.0268(16) 0.0132(16) -0.0046(12) -0.0026(13) 0.0008(12) C13 0.0279(16) 0.0172(14) 0.0195(17) 0.0011(11) -0.0075(14) -0.0011(12) C14 0.0245(15) 0.0152(13) 0.0210(17) -0.0043(11) -0.0055(13) 0.0015(11) C15 0.0237(15) 0.0163(13) 0.0179(16) -0.0047(11) -0.0052(13) -0.0003(11) C16 0.077(3) 0.032(2) 0.024(2) 0.0040(16) -0.011(2) 0.023(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 B1 F1 1.364(4) . ? B1 F2 1.377(4) . ? B1 N1 1.559(4) . ? B1 N2 1.568(5) . ? Br1 C1 1.853(3) . ? Br2 C2 1.861(3) . ? Br2 Br4 3.4112(5) 1_565 ? Br3 C8 1.865(3) . ? Br4 C9 1.852(3) . ? N1 C1 1.356(4) . ? N1 C4 1.395(4) . ? N2 C9 1.338(4) . ? N2 C6 1.393(4) . ? O1 C13 1.359(4) . ? O1 C16 1.435(4) . ? C1 C2 1.401(4) . ? C2 C3 1.376(4) . ? C3 C4 1.402(4) . ? C3 H3 0.9500 . ? C4 C5 1.402(4) . ? C5 C6 1.401(4) . ? C5 C10 1.470(4) . ? C6 C7 1.413(4) . ? C7 C8 1.381(4) . ? C7 H7 0.9500 . ? C8 C9 1.395(5) . ? C10 C11 1.395(4) . ? C10 C15 1.401(4) . ? C11 C12 1.375(4) . ? C11 H11 0.9500 . ? C12 C13 1.395(4) . ? C12 H12 0.9500 . ? C13 C14 1.376(5) . ? C14 C15 1.392(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 F1 B1 F2 111.4(3) . . ? F1 B1 N1 111.4(3) . . ? F2 B1 N1 109.4(2) . . ? F1 B1 N2 110.2(2) . . ? F2 B1 N2 109.6(3) . . ? N1 B1 N2 104.6(2) . . ? C2 Br2 Br4 107.85(9) . 1_565 ? C1 N1 C4 106.9(2) . . ? C1 N1 B1 126.8(3) . . ? C4 N1 B1 126.3(3) . . ? C9 N2 C6 106.8(3) . . ? C9 N2 B1 126.6(3) . . ? C6 N2 B1 125.6(2) . . ? C13 O1 C16 117.2(3) . . ? N1 C1 C2 109.7(3) . . ? N1 C1 Br1 123.3(2) . . ? C2 C1 Br1 127.0(2) . . ? C3 C2 C1 107.6(3) . . ? C3 C2 Br2 127.4(2) . . ? C1 C2 Br2 124.9(2) . . ? C2 C3 C4 107.0(3) . . ? C2 C3 H3 126.5 . . ? C4 C3 H3 126.5 . . ? N1 C4 C3 108.8(3) . . ? N1 C4 C5 120.9(3) . . ? C3 C4 C5 130.0(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 C10 120.3(3) . . ? C4 C5 C10 119.8(3) . . ? N2 C6 C5 120.9(3) . . ? N2 C6 C7 108.8(3) . . ? C5 C6 C7 130.2(3) . . ? C8 C7 C6 106.2(3) . . ? C8 C7 H7 126.9 . . ? C6 C7 H7 126.9 . . ? C7 C8 C9 107.4(3) . . ? C7 C8 Br3 127.8(3) . . ? C9 C8 Br3 124.8(2) . . ? N2 C9 C8 110.7(3) . . ? N2 C9 Br4 123.1(2) . . ? C8 C9 Br4 126.1(2) . . ? C11 C10 C15 118.6(3) . . ? C11 C10 C5 120.5(3) . . ? C15 C10 C5 120.9(3) . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? O1 C13 C14 125.4(3) . . ? O1 C13 C12 115.0(3) . . ? C14 C13 C12 119.6(3) . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C10 120.5(3) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 F1 B1 N1 C1 72.9(4) . . . . ? F2 B1 N1 C1 -50.7(4) . . . . ? N2 B1 N1 C1 -168.0(3) . . . . ? F1 B1 N1 C4 -109.6(3) . . . . ? F2 B1 N1 C4 126.8(3) . . . . ? N2 B1 N1 C4 9.4(4) . . . . ? F1 B1 N2 C9 -62.9(4) . . . . ? F2 B1 N2 C9 60.0(4) . . . . ? N1 B1 N2 C9 177.3(3) . . . . ? F1 B1 N2 C6 104.2(3) . . . . ? F2 B1 N2 C6 -132.9(3) . . . . ? N1 B1 N2 C6 -15.6(4) . . . . ? C4 N1 C1 C2 -1.3(3) . . . . ? B1 N1 C1 C2 176.6(3) . . . . ? C4 N1 C1 Br1 178.2(2) . . . . ? B1 N1 C1 Br1 -3.9(4) . . . . ? N1 C1 C2 C3 0.6(4) . . . . ? Br1 C1 C2 C3 -178.8(2) . . . . ? N1 C1 C2 Br2 -177.0(2) . . . . ? Br1 C1 C2 Br2 3.5(4) . . . . ? Br4 Br2 C2 C3 28.6(3) 1_565 . . . ? Br4 Br2 C2 C1 -154.2(3) 1_565 . . . ? C1 C2 C3 C4 0.3(3) . . . . ? Br2 C2 C3 C4 177.8(2) . . . . ? C1 N1 C4 C3 1.4(3) . . . . ? B1 N1 C4 C3 -176.5(3) . . . . ? C1 N1 C4 C5 176.7(3) . . . . ? B1 N1 C4 C5 -1.2(4) . . . . ? C2 C3 C4 N1 -1.1(3) . . . . ? C2 C3 C4 C5 -175.7(3) . . . . ? N1 C4 C5 C6 -3.3(4) . . . . ? C3 C4 C5 C6 170.8(3) . . . . ? N1 C4 C5 C10 177.9(3) . . . . ? C3 C4 C5 C10 -8.0(5) . . . . ? C9 N2 C6 C5 -177.1(3) . . . . ? B1 N2 C6 C5 13.7(4) . . . . ? C9 N2 C6 C7 0.4(3) . . . . ? B1 N2 C6 C7 -168.8(3) . . . . ? C4 C5 C6 N2 -2.7(4) . . . . ? C10 C5 C6 N2 176.1(3) . . . . ? C4 C5 C6 C7 -179.5(3) . . . . ? C10 C5 C6 C7 -0.8(5) . . . . ? N2 C6 C7 C8 -0.8(3) . . . . ? C5 C6 C7 C8 176.3(3) . . . . ? C6 C7 C8 C9 1.0(3) . . . . ? C6 C7 C8 Br3 -176.6(2) . . . . ? C6 N2 C9 C8 0.2(3) . . . . ? B1 N2 C9 C8 169.3(3) . . . . ? C6 N2 C9 Br4 -179.4(2) . . . . ? B1 N2 C9 Br4 -10.3(4) . . . . ? C7 C8 C9 N2 -0.8(4) . . . . ? Br3 C8 C9 N2 176.9(2) . . . . ? C7 C8 C9 Br4 178.8(2) . . . . ? Br3 C8 C9 Br4 -3.5(4) . . . . ? C6 C5 C10 C11 -49.4(4) . . . . ? C4 C5 C10 C11 129.4(3) . . . . ? C6 C5 C10 C15 129.3(3) . . . . ? C4 C5 C10 C15 -51.9(4) . . . . ? C15 C10 C11 C12 0.0(4) . . . . ? C5 C10 C11 C12 178.7(3) . . . . ? C10 C11 C12 C13 -0.6(5) . . . . ? C16 O1 C13 C14 -3.8(5) . . . . ? C16 O1 C13 C12 177.5(3) . . . . ? C11 C12 C13 O1 179.2(3) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? O1 C13 C14 C15 -178.3(3) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C13 C14 C15 C10 -0.9(4) . . . . ? C11 C10 C15 C14 0.7(4) . . . . ? C5 C10 C15 C14 -177.9(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 C11 H11 F2 0.95 2.40 3.307(3) 160.8 2_756 C12 H12 Br2 0.95 2.88 3.699(3) 144.8 1_554 _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.497 _refine_diff_density_min -1.225 _refine_diff_density_rms 0.138 data_mr044a _database_code_depnum_ccdc_archive 'CCDC 849333' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H8 B Br5 F2 N2 O' _chemical_formula_sum 'C16 H8 B Br5 F2 N2 O' _chemical_formula_weight 692.60 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' N N 0.0061 0.0033 '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' 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 8.9535(17) _cell_length_b 19.702(4) _cell_length_c 11.172(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.84(2) _cell_angle_gamma 90.00 _cell_volume 1970.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3242 _cell_measurement_theta_min 3.5512 _cell_measurement_theta_max 30.4395 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 10.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1619 _exptl_absorpt_correction_T_max 0.2605 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21069 _diffrn_reflns_av_R_equivalents 0.1355 _diffrn_reflns_av_sigmaI/netI 0.2301 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5993 _reflns_number_gt 2036 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0692P)^2^] 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 5993 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1842 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.1679 _refine_ls_wR_factor_gt 0.1528 _refine_ls_goodness_of_fit_ref 0.863 _refine_ls_restrained_S_all 0.863 _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 0.3131(13) 0.5701(5) 0.5077(10) 0.039(3) Uani 1 1 d . . . Br1 Br 0.86184(11) 0.70462(5) 0.50265(9) 0.0468(3) Uani 1 1 d . . . Br2 Br 0.07804(11) 0.47468(5) 0.34305(10) 0.0514(3) Uani 1 1 d . . . Br3 Br 0.21622(12) 0.48372(5) 0.03966(9) 0.0506(3) Uani 1 1 d . . . Br4 Br 0.72861(13) 0.69618(6) 0.80137(9) 0.0572(3) Uani 1 1 d . . . Br5 Br 0.38487(12) 0.60244(6) 0.79298(9) 0.0574(3) Uani 1 1 d . . . F1 F 0.1911(5) 0.6087(2) 0.5303(4) 0.0426(13) Uani 1 1 d . . . F2 F 0.3110(6) 0.5077(2) 0.5625(4) 0.0455(14) Uani 1 1 d . . . O1 O 0.9708(7) 0.7121(2) 0.0041(5) 0.0327(14) Uani 1 1 d . . . N1 N 0.4592(8) 0.6094(3) 0.5487(6) 0.0290(16) Uani 1 1 d . . . N2 N 0.3314(8) 0.5589(3) 0.3688(6) 0.0334(17) Uani 1 1 d . . . C1 C 0.5027(12) 0.6260(4) 0.6618(7) 0.043(3) Uani 1 1 d . . . C2 C 0.6341(10) 0.6623(4) 0.6643(7) 0.032(2) Uani 1 1 d . . . C3 C 0.6833(9) 0.6660(4) 0.5484(8) 0.033(2) Uani 1 1 d . . . C4 C 0.5713(10) 0.6328(4) 0.4741(8) 0.030(2) Uani 1 1 d . . . C5 C 0.5620(8) 0.6243(3) 0.3515(8) 0.0256(19) Uani 1 1 d . . . C6 C 0.4457(9) 0.5876(4) 0.2983(7) 0.0266(19) Uani 1 1 d . . . C7 C 0.4214(9) 0.5689(4) 0.1757(7) 0.030(2) Uani 1 1 d . . . H7 H 0.4792 0.5818 0.1088 0.036 Uiso 1 1 calc R . . C8 C 0.2987(10) 0.5289(4) 0.1755(7) 0.036(2) Uani 1 1 d . . . C9 C 0.2423(10) 0.5233(4) 0.2930(8) 0.038(2) Uani 1 1 d . . . C10 C 0.6755(9) 0.6495(4) 0.2685(7) 0.029(2) Uani 1 1 d . . . C11 C 0.6566(9) 0.7080(4) 0.2009(7) 0.0280(19) Uani 1 1 d . . . H11 H 0.5697 0.7347 0.2128 0.034 Uiso 1 1 calc R . . C12 C 0.7559(11) 0.7287(4) 0.1192(7) 0.034(2) Uani 1 1 d . . . H12 H 0.7397 0.7700 0.0771 0.041 Uiso 1 1 calc R . . C13 C 0.8842(10) 0.6894(4) 0.0955(8) 0.034(2) Uani 1 1 d . . . C14 C 0.9092(10) 0.6317(4) 0.1611(8) 0.035(2) Uani 1 1 d . . . H14 H 0.9968 0.6056 0.1488 0.042 Uiso 1 1 calc R . . C15 C 0.8055(9) 0.6112(4) 0.2464(8) 0.035(2) Uani 1 1 d . . . H15 H 0.8228 0.5706 0.2903 0.042 Uiso 1 1 calc R . . C16 C 1.0831(11) 0.6683(4) -0.0326(9) 0.048(3) Uani 1 1 d . . . H16A H 1.1611 0.6657 0.0297 0.072 Uiso 1 1 calc R . . H16B H 1.1263 0.6852 -0.1069 0.072 Uiso 1 1 calc R . . H16C H 1.0410 0.6230 -0.0464 0.072 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 B1 0.039(7) 0.043(6) 0.035(6) 0.004(5) 0.007(5) -0.002(6) Br1 0.0397(6) 0.0567(6) 0.0438(6) -0.0013(5) -0.0087(5) -0.0043(5) Br2 0.0380(6) 0.0478(6) 0.0686(8) 0.0039(5) 0.0048(5) -0.0011(5) Br3 0.0523(7) 0.0543(6) 0.0449(6) -0.0053(5) -0.0108(5) -0.0106(5) Br4 0.0689(8) 0.0739(7) 0.0283(5) -0.0088(5) -0.0134(5) 0.0071(6) Br5 0.0598(7) 0.0810(8) 0.0317(6) 0.0036(5) 0.0131(5) 0.0150(6) F1 0.024(3) 0.045(3) 0.059(4) -0.007(3) 0.015(2) 0.015(2) F2 0.059(4) 0.043(3) 0.036(3) 0.011(2) 0.014(3) 0.005(3) O1 0.038(4) 0.030(3) 0.030(3) 0.009(2) 0.006(3) -0.009(3) N1 0.035(4) 0.028(4) 0.024(4) -0.003(3) 0.003(3) 0.005(3) N2 0.030(4) 0.036(4) 0.035(4) -0.001(3) 0.002(3) -0.002(4) C1 0.072(8) 0.044(5) 0.014(4) 0.005(4) 0.017(5) 0.029(5) C2 0.028(5) 0.039(5) 0.029(5) -0.008(4) -0.005(4) 0.008(4) C3 0.028(5) 0.032(5) 0.039(6) -0.002(4) -0.001(4) 0.014(4) C4 0.034(5) 0.025(4) 0.031(5) -0.001(4) 0.000(4) 0.011(4) C5 0.019(5) 0.014(4) 0.043(6) 0.005(3) -0.001(4) 0.003(3) C6 0.028(5) 0.026(4) 0.027(5) 0.006(3) 0.008(4) 0.003(4) C7 0.023(5) 0.036(5) 0.030(5) 0.007(4) -0.003(4) -0.010(4) C8 0.034(6) 0.044(5) 0.030(5) -0.005(4) -0.008(4) 0.013(5) C9 0.040(6) 0.024(5) 0.049(6) -0.003(4) 0.005(5) 0.007(4) C10 0.023(5) 0.028(5) 0.036(5) -0.002(4) -0.012(4) -0.003(4) C11 0.029(5) 0.021(4) 0.034(5) 0.003(4) 0.002(4) 0.007(4) C12 0.060(7) 0.022(4) 0.020(5) 0.003(3) -0.003(4) 0.005(4) C13 0.043(6) 0.026(5) 0.034(5) -0.001(4) -0.006(4) -0.003(4) C14 0.031(5) 0.041(5) 0.033(5) 0.012(4) 0.011(4) 0.002(4) C15 0.033(5) 0.033(5) 0.039(6) 0.013(4) 0.005(4) 0.003(4) C16 0.044(6) 0.054(6) 0.047(7) 0.008(5) 0.012(5) -0.009(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 B1 F1 1.357(11) . ? B1 F2 1.375(11) . ? B1 N2 1.579(13) . ? B1 N1 1.582(12) . ? Br1 C3 1.849(9) . ? Br2 C9 1.848(9) . ? Br2 F1 3.257(5) 3_566 ? Br3 C8 1.899(8) . ? Br4 C2 1.862(8) . ? Br5 C1 1.876(9) . ? O1 C13 1.367(10) . ? O1 C16 1.392(10) . ? N1 C1 1.357(11) . ? N1 C4 1.392(10) . ? N2 C9 1.351(10) . ? N2 C6 1.418(10) . ? C1 C2 1.377(13) . ? C2 C3 1.376(11) . ? C3 C4 1.449(12) . ? C4 C5 1.381(11) . ? C5 C6 1.394(11) . ? C5 C10 1.472(11) . ? C6 C7 1.432(11) . ? C7 C8 1.353(11) . ? C7 H7 0.9500 . ? C8 C9 1.417(12) . ? C10 C11 1.387(10) . ? C10 C15 1.413(11) . ? C11 C12 1.347(11) . ? C11 H11 0.9500 . ? C12 C13 1.413(12) . ? C12 H12 0.9500 . ? C13 C14 1.369(11) . ? C14 C15 1.399(11) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 F1 B1 F2 113.7(8) . . ? F1 B1 N2 110.9(8) . . ? F2 B1 N2 108.3(7) . . ? F1 B1 N1 109.7(7) . . ? F2 B1 N1 109.0(8) . . ? N2 B1 N1 104.8(7) . . ? C9 Br2 F1 171.8(3) . 3_566 ? C13 O1 C16 115.9(6) . . ? C1 N1 C4 106.2(8) . . ? C1 N1 B1 127.8(8) . . ? C4 N1 B1 126.1(7) . . ? C9 N2 C6 106.5(7) . . ? C9 N2 B1 128.3(7) . . ? C6 N2 B1 125.2(7) . . ? N1 C1 C2 112.2(8) . . ? N1 C1 Br5 120.7(8) . . ? C2 C1 Br5 127.0(7) . . ? C3 C2 C1 107.1(7) . . ? C3 C2 Br4 127.3(7) . . ? C1 C2 Br4 125.5(7) . . ? C2 C3 C4 106.7(8) . . ? C2 C3 Br1 124.9(7) . . ? C4 C3 Br1 128.4(7) . . ? C5 C4 N1 121.4(8) . . ? C5 C4 C3 130.8(8) . . ? N1 C4 C3 107.8(7) . . ? C4 C5 C6 121.3(7) . . ? C4 C5 C10 123.5(7) . . ? C6 C5 C10 115.2(7) . . ? C5 C6 N2 120.7(7) . . ? C5 C6 C7 130.0(7) . . ? N2 C6 C7 109.1(7) . . ? C8 C7 C6 105.3(7) . . ? C8 C7 H7 127.4 . . ? C6 C7 H7 127.4 . . ? C7 C8 C9 110.1(7) . . ? C7 C8 Br3 125.5(7) . . ? C9 C8 Br3 124.3(7) . . ? N2 C9 C8 108.9(8) . . ? N2 C9 Br2 123.0(7) . . ? C8 C9 Br2 128.0(7) . . ? C11 C10 C15 116.3(8) . . ? C11 C10 C5 123.0(7) . . ? C15 C10 C5 120.5(7) . . ? C12 C11 C10 123.0(8) . . ? C12 C11 H11 118.5 . . ? C10 C11 H11 118.5 . . ? C11 C12 C13 120.5(7) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? O1 C13 C14 125.6(8) . . ? O1 C13 C12 115.5(7) . . ? C14 C13 C12 118.8(8) . . ? C13 C14 C15 119.9(8) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 121.4(8) . . ? C14 C15 H15 119.3 . . ? C10 C15 H15 119.3 . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 F1 B1 N1 C1 66.7(10) . . . . ? F2 B1 N1 C1 -58.3(11) . . . . ? N2 B1 N1 C1 -174.1(7) . . . . ? F1 B1 N1 C4 -114.6(9) . . . . ? F2 B1 N1 C4 120.3(8) . . . . ? N2 B1 N1 C4 4.5(10) . . . . ? F1 B1 N2 C9 -67.2(11) . . . . ? F2 B1 N2 C9 58.2(11) . . . . ? N1 B1 N2 C9 174.4(7) . . . . ? F1 B1 N2 C6 110.2(9) . . . . ? F2 B1 N2 C6 -124.4(8) . . . . ? N1 B1 N2 C6 -8.1(10) . . . . ? C4 N1 C1 C2 3.2(9) . . . . ? B1 N1 C1 C2 -177.9(8) . . . . ? C4 N1 C1 Br5 -178.9(5) . . . . ? B1 N1 C1 Br5 -0.1(11) . . . . ? N1 C1 C2 C3 -3.7(10) . . . . ? Br5 C1 C2 C3 178.6(6) . . . . ? N1 C1 C2 Br4 178.6(5) . . . . ? Br5 C1 C2 Br4 0.8(11) . . . . ? C1 C2 C3 C4 2.6(9) . . . . ? Br4 C2 C3 C4 -179.8(6) . . . . ? C1 C2 C3 Br1 -175.8(6) . . . . ? Br4 C2 C3 Br1 1.8(11) . . . . ? C1 N1 C4 C5 -179.7(7) . . . . ? B1 N1 C4 C5 1.4(11) . . . . ? C1 N1 C4 C3 -1.5(8) . . . . ? B1 N1 C4 C3 179.7(7) . . . . ? C2 C3 C4 C5 177.4(8) . . . . ? Br1 C3 C4 C5 -4.3(12) . . . . ? C2 C3 C4 N1 -0.7(8) . . . . ? Br1 C3 C4 N1 177.6(5) . . . . ? N1 C4 C5 C6 -4.8(11) . . . . ? C3 C4 C5 C6 177.3(7) . . . . ? N1 C4 C5 C10 178.4(7) . . . . ? C3 C4 C5 C10 0.6(13) . . . . ? C4 C5 C6 N2 1.2(11) . . . . ? C10 C5 C6 N2 178.2(7) . . . . ? C4 C5 C6 C7 -174.9(7) . . . . ? C10 C5 C6 C7 2.1(11) . . . . ? C9 N2 C6 C5 -176.0(7) . . . . ? B1 N2 C6 C5 6.1(11) . . . . ? C9 N2 C6 C7 0.9(8) . . . . ? B1 N2 C6 C7 -177.0(7) . . . . ? C5 C6 C7 C8 174.9(8) . . . . ? N2 C6 C7 C8 -1.6(9) . . . . ? C6 C7 C8 C9 1.6(9) . . . . ? C6 C7 C8 Br3 -176.3(6) . . . . ? C6 N2 C9 C8 0.2(8) . . . . ? B1 N2 C9 C8 178.0(8) . . . . ? C6 N2 C9 Br2 178.8(5) . . . . ? B1 N2 C9 Br2 -3.5(11) . . . . ? C7 C8 C9 N2 -1.2(9) . . . . ? Br3 C8 C9 N2 176.8(5) . . . . ? C7 C8 C9 Br2 -179.7(6) . . . . ? Br3 C8 C9 Br2 -1.7(11) . . . . ? F1 Br2 C9 N2 -15(2) 3_566 . . . ? F1 Br2 C9 C8 162.9(13) 3_566 . . . ? C4 C5 C10 C11 -101.9(10) . . . . ? C6 C5 C10 C11 81.1(9) . . . . ? C4 C5 C10 C15 83.7(10) . . . . ? C6 C5 C10 C15 -93.3(9) . . . . ? C15 C10 C11 C12 -0.8(12) . . . . ? C5 C10 C11 C12 -175.4(8) . . . . ? C10 C11 C12 C13 2.2(13) . . . . ? C16 O1 C13 C14 7.7(12) . . . . ? C16 O1 C13 C12 -170.0(7) . . . . ? C11 C12 C13 O1 174.8(7) . . . . ? C11 C12 C13 C14 -3.1(13) . . . . ? O1 C13 C14 C15 -175.0(8) . . . . ? C12 C13 C14 C15 2.6(13) . . . . ? C13 C14 C15 C10 -1.3(13) . . . . ? C11 C10 C15 C14 0.3(12) . . . . ? C5 C10 C15 C14 175.1(8) . . . . ? 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 C12 H12 F1 0.95 2.48 3.402(9) 162.5 4_675 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.201 _refine_diff_density_min -1.301 _refine_diff_density_rms 0.183 data_mr048 _database_code_depnum_ccdc_archive 'CCDC 849334' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 B Br3 F2 N2 O' _chemical_formula_weight 534.80 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' N N 0.0061 0.0033 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2231(10) _cell_length_b 10.6391(10) _cell_length_c 10.7273(6) _cell_angle_alpha 105.580(7) _cell_angle_beta 92.262(7) _cell_angle_gamma 106.758(9) _cell_volume 858.63(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3768 _cell_measurement_theta_min 3.4685 _cell_measurement_theta_max 32.3188 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.069 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 7.074 _exptl_absorpt_correction_T_min 0.2036 _exptl_absorpt_correction_T_max 0.3181 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(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 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6019 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3015 _reflns_number_gt 2253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0485P)^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 3015 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0777 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 Br1 Br -0.00903(7) 0.18946(4) -0.44284(4) 0.06122(16) Uani 1 1 d . . . Br2 Br 0.34174(6) -0.15593(4) 0.13177(4) 0.04999(15) Uani 1 1 d . . . Br3 Br 0.21448(6) -0.21091(4) -0.20472(4) 0.05090(15) Uani 1 1 d . . . F1 F 0.2593(3) 0.0589(2) -0.3090(2) 0.0434(5) Uani 1 1 d . . . F2 F -0.0164(3) -0.02025(19) -0.2720(2) 0.0435(5) Uani 1 1 d . . . O1 O 0.4180(4) 0.7026(2) 0.5255(2) 0.0492(7) Uani 1 1 d . . . N1 N 0.1320(4) 0.2232(3) -0.1882(3) 0.0338(7) Uani 1 1 d . . . N2 N 0.2048(4) 0.0584(3) -0.0906(3) 0.0324(7) Uani 1 1 d . . . B1 B 0.1420(5) 0.0739(4) -0.2217(4) 0.0351(10) Uani 1 1 d . . . C1 C 0.0717(5) 0.2813(4) -0.2689(4) 0.0410(9) Uani 1 1 d . . . C2 C 0.0799(5) 0.4152(4) -0.2041(4) 0.0477(10) Uani 1 1 d . . . H2 H 0.0455 0.4756 -0.2395 0.057 Uiso 1 1 calc R . . C3 C 0.1482(5) 0.4410(4) -0.0783(4) 0.0409(9) Uani 1 1 d . . . H3 H 0.1695 0.5230 -0.0122 0.049 Uiso 1 1 calc R . . C4 C 0.1810(4) 0.3214(3) -0.0663(3) 0.0331(8) Uani 1 1 d . . . C5 C 0.2415(4) 0.2926(3) 0.0424(3) 0.0310(8) Uani 1 1 d . . . C6 C 0.2515(4) 0.1596(3) 0.0299(3) 0.0319(8) Uani 1 1 d . . . C7 C 0.3095(5) 0.1067(4) 0.1225(4) 0.0360(8) Uani 1 1 d . . . H7 H 0.3492 0.1525 0.2101 0.043 Uiso 1 1 calc R . . C8 C 0.2960(4) -0.0276(3) 0.0576(4) 0.0358(9) Uani 1 1 d . . . C9 C 0.2350(4) -0.0539(3) -0.0712(4) 0.0356(9) Uani 1 1 d . . . C10 C 0.2949(4) 0.3989(3) 0.1701(3) 0.0331(8) Uani 1 1 d . . . C11 C 0.4030(5) 0.5299(4) 0.1786(4) 0.0364(9) Uani 1 1 d . . . H11 H 0.4441 0.5487 0.1038 0.044 Uiso 1 1 calc R . . C12 C 0.4499(5) 0.6322(3) 0.2965(3) 0.0359(9) Uani 1 1 d . . . H12 H 0.5247 0.7180 0.3010 0.043 Uiso 1 1 calc R . . C13 C 0.3861(5) 0.6074(3) 0.4071(4) 0.0368(9) Uani 1 1 d . . . C14 C 0.2833(5) 0.4757(4) 0.4003(4) 0.0427(10) Uani 1 1 d . . . H14 H 0.2441 0.4569 0.4755 0.051 Uiso 1 1 calc R . . C15 C 0.2394(5) 0.3739(4) 0.2844(4) 0.0387(9) Uani 1 1 d . . . H15 H 0.1712 0.2864 0.2819 0.046 Uiso 1 1 calc R . . C16 C 0.5047(6) 0.8416(4) 0.5298(4) 0.0581(12) Uani 1 1 d . . . H16A H 0.6223 0.8516 0.5176 0.087 Uiso 1 1 calc R . . H16B H 0.4991 0.9019 0.6129 0.087 Uiso 1 1 calc R . . H16C H 0.4507 0.8646 0.4618 0.087 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 Br1 0.0932(4) 0.0500(3) 0.0359(3) 0.0082(2) -0.0118(2) 0.0221(2) Br2 0.0620(3) 0.0427(2) 0.0527(3) 0.0206(2) 0.0027(2) 0.0218(2) Br3 0.0637(3) 0.0287(2) 0.0516(3) -0.00133(18) -0.0025(2) 0.01462(19) F1 0.0555(14) 0.0397(11) 0.0361(13) 0.0088(10) 0.0155(11) 0.0171(10) F2 0.0444(12) 0.0334(11) 0.0421(14) 0.0084(10) -0.0031(10) -0.0003(10) O1 0.081(2) 0.0311(14) 0.0245(15) -0.0004(12) 0.0035(14) 0.0097(14) N1 0.0406(17) 0.0261(15) 0.0314(18) 0.0060(13) 0.0027(14) 0.0077(13) N2 0.0388(17) 0.0253(15) 0.0310(18) 0.0083(13) 0.0043(14) 0.0071(13) B1 0.042(2) 0.029(2) 0.029(2) 0.0029(18) 0.0044(19) 0.0081(19) C1 0.049(2) 0.039(2) 0.034(2) 0.0107(18) 0.0022(18) 0.0127(18) C2 0.063(3) 0.034(2) 0.046(3) 0.0091(19) -0.002(2) 0.0183(19) C3 0.051(2) 0.030(2) 0.039(2) 0.0034(17) 0.0030(19) 0.0154(18) C4 0.038(2) 0.0309(19) 0.028(2) 0.0047(16) 0.0038(16) 0.0103(16) C5 0.0319(19) 0.0269(18) 0.031(2) 0.0050(15) 0.0065(16) 0.0068(15) C6 0.038(2) 0.0277(18) 0.027(2) 0.0055(16) 0.0058(16) 0.0080(16) C7 0.043(2) 0.0337(19) 0.028(2) 0.0046(16) 0.0041(17) 0.0112(17) C8 0.038(2) 0.0305(19) 0.042(2) 0.0160(17) 0.0043(17) 0.0116(17) C9 0.036(2) 0.0278(19) 0.041(2) 0.0092(17) 0.0072(17) 0.0080(16) C10 0.037(2) 0.0312(19) 0.031(2) 0.0045(16) 0.0072(16) 0.0136(16) C11 0.046(2) 0.0325(19) 0.031(2) 0.0097(16) 0.0096(17) 0.0105(17) C12 0.047(2) 0.0257(18) 0.029(2) 0.0057(16) 0.0041(17) 0.0053(16) C13 0.052(2) 0.0287(19) 0.027(2) 0.0050(16) 0.0029(17) 0.0113(17) C14 0.058(2) 0.040(2) 0.030(2) 0.0128(18) 0.0158(19) 0.012(2) C15 0.046(2) 0.0269(18) 0.040(2) 0.0077(17) 0.0091(18) 0.0085(17) C16 0.086(3) 0.033(2) 0.041(3) -0.0004(19) 0.000(2) 0.007(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 Br1 C1 1.851(4) . ? Br2 C8 1.869(3) . ? Br3 C9 1.844(4) . ? F1 B1 1.383(5) . ? F2 B1 1.376(5) . ? O1 C13 1.355(4) . ? O1 C16 1.432(4) . ? N1 C1 1.345(5) . ? N1 C4 1.395(4) . ? N1 B1 1.559(5) . ? N2 C9 1.354(4) . ? N2 C6 1.397(4) . ? N2 B1 1.545(5) . ? C1 C2 1.387(5) . ? C2 C3 1.366(6) . ? C2 H2 0.9300 . ? C3 C4 1.411(5) . ? C3 H3 0.9300 . ? C4 C5 1.391(5) . ? C5 C6 1.411(5) . ? C5 C10 1.477(5) . ? C6 C7 1.397(5) . ? C7 C8 1.380(5) . ? C7 H7 0.9300 . ? C8 C9 1.377(5) . ? C10 C15 1.389(5) . ? C10 C11 1.398(5) . ? C11 C12 1.383(5) . ? C11 H11 0.9300 . ? C12 C13 1.374(5) . ? C12 H12 0.9300 . ? C13 C14 1.393(5) . ? C14 C15 1.366(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C13 O1 C16 116.7(3) . . ? C1 N1 C4 106.8(3) . . ? C1 N1 B1 127.2(3) . . ? C4 N1 B1 126.0(3) . . ? C9 N2 C6 106.3(3) . . ? C9 N2 B1 126.7(3) . . ? C6 N2 B1 126.9(3) . . ? F2 B1 F1 110.8(3) . . ? F2 B1 N2 110.4(3) . . ? F1 B1 N2 110.3(3) . . ? F2 B1 N1 110.8(3) . . ? F1 B1 N1 109.4(3) . . ? N2 B1 N1 105.1(3) . . ? N1 C1 C2 111.0(4) . . ? N1 C1 Br1 122.6(3) . . ? C2 C1 Br1 126.3(3) . . ? C3 C2 C1 106.6(3) . . ? C3 C2 H2 126.7 . . ? C1 C2 H2 126.7 . . ? C2 C3 C4 108.0(3) . . ? C2 C3 H3 126.0 . . ? C4 C3 H3 126.0 . . ? C5 C4 N1 121.9(3) . . ? C5 C4 C3 130.6(3) . . ? N1 C4 C3 107.4(3) . . ? C4 C5 C6 119.2(3) . . ? C4 C5 C10 120.9(3) . . ? C6 C5 C10 119.8(3) . . ? C7 C6 N2 109.2(3) . . ? C7 C6 C5 130.0(3) . . ? N2 C6 C5 120.7(3) . . ? C8 C7 C6 106.0(3) . . ? C8 C7 H7 127.0 . . ? C6 C7 H7 127.0 . . ? C9 C8 C7 108.4(3) . . ? C9 C8 Br2 125.2(3) . . ? C7 C8 Br2 126.4(3) . . ? N2 C9 C8 110.1(3) . . ? N2 C9 Br3 123.2(3) . . ? C8 C9 Br3 126.5(3) . . ? C15 C10 C11 117.9(3) . . ? C15 C10 C5 122.1(3) . . ? C11 C10 C5 120.1(3) . . ? C12 C11 C10 121.0(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? O1 C13 C12 124.5(3) . . ? O1 C13 C14 116.4(3) . . ? C12 C13 C14 119.0(3) . . ? C15 C14 C13 120.8(3) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C10 121.0(3) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 C9 N2 B1 F2 61.4(5) . . . . ? C6 N2 B1 F2 -122.8(3) . . . . ? C9 N2 B1 F1 -61.3(4) . . . . ? C6 N2 B1 F1 114.5(4) . . . . ? C9 N2 B1 N1 -179.1(3) . . . . ? C6 N2 B1 N1 -3.3(5) . . . . ? C1 N1 B1 F2 -55.5(5) . . . . ? C4 N1 B1 F2 122.9(3) . . . . ? C1 N1 B1 F1 66.9(5) . . . . ? C4 N1 B1 F1 -114.7(4) . . . . ? C1 N1 B1 N2 -174.7(3) . . . . ? C4 N1 B1 N2 3.7(5) . . . . ? C4 N1 C1 C2 0.2(4) . . . . ? B1 N1 C1 C2 178.8(3) . . . . ? C4 N1 C1 Br1 180.0(3) . . . . ? B1 N1 C1 Br1 -1.4(5) . . . . ? N1 C1 C2 C3 0.1(5) . . . . ? Br1 C1 C2 C3 -179.7(3) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C1 N1 C4 C5 176.7(3) . . . . ? B1 N1 C4 C5 -2.0(5) . . . . ? C1 N1 C4 C3 -0.4(4) . . . . ? B1 N1 C4 C3 -179.1(3) . . . . ? C2 C3 C4 C5 -176.3(4) . . . . ? C2 C3 C4 N1 0.5(4) . . . . ? N1 C4 C5 C6 -0.9(5) . . . . ? C3 C4 C5 C6 175.4(4) . . . . ? N1 C4 C5 C10 179.2(3) . . . . ? C3 C4 C5 C10 -4.5(6) . . . . ? C9 N2 C6 C7 -0.3(4) . . . . ? B1 N2 C6 C7 -176.8(3) . . . . ? C9 N2 C6 C5 177.7(3) . . . . ? B1 N2 C6 C5 1.2(5) . . . . ? C4 C5 C6 C7 178.8(4) . . . . ? C10 C5 C6 C7 -1.3(6) . . . . ? C4 C5 C6 N2 1.3(5) . . . . ? C10 C5 C6 N2 -178.8(3) . . . . ? N2 C6 C7 C8 -0.6(4) . . . . ? C5 C6 C7 C8 -178.3(4) . . . . ? C6 C7 C8 C9 1.2(4) . . . . ? C6 C7 C8 Br2 -176.0(3) . . . . ? C6 N2 C9 C8 1.1(4) . . . . ? B1 N2 C9 C8 177.6(3) . . . . ? C6 N2 C9 Br3 -173.6(2) . . . . ? B1 N2 C9 Br3 2.9(5) . . . . ? C7 C8 C9 N2 -1.5(4) . . . . ? Br2 C8 C9 N2 175.8(2) . . . . ? C7 C8 C9 Br3 173.0(3) . . . . ? Br2 C8 C9 Br3 -9.7(5) . . . . ? C4 C5 C10 C15 131.7(4) . . . . ? C6 C5 C10 C15 -48.2(5) . . . . ? C4 C5 C10 C11 -47.6(5) . . . . ? C6 C5 C10 C11 132.5(4) . . . . ? C15 C10 C11 C12 -1.5(5) . . . . ? C5 C10 C11 C12 177.8(3) . . . . ? C10 C11 C12 C13 -2.0(6) . . . . ? C16 O1 C13 C12 8.8(6) . . . . ? C16 O1 C13 C14 -172.2(4) . . . . ? C11 C12 C13 O1 -176.8(3) . . . . ? C11 C12 C13 C14 4.2(6) . . . . ? O1 C13 C14 C15 177.9(3) . . . . ? C12 C13 C14 C15 -3.1(6) . . . . ? C13 C14 C15 C10 -0.4(6) . . . . ? C11 C10 C15 C14 2.7(5) . . . . ? C5 C10 C15 C14 -176.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.844 _refine_diff_density_min -0.631 _refine_diff_density_rms 0.078