# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Yong-Ming Wu' _publ_contact_author_email ymwu@mail.sioc.ac.cn _publ_contact_author_name 'Yong-Ming Wu' data_cd28214 _database_code_depnum_ccdc_archive 'CCDC 846077' #TrackingRef '- cd28214.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 Br F2 N2' _chemical_formula_weight 439.30 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' 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)/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 9.7632(9) _cell_length_b 21.4713(19) _cell_length_c 10.1143(9) _cell_angle_alpha 90.00 _cell_angle_beta 111.853(2) _cell_angle_gamma 90.00 _cell_volume 1967.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2385 _cell_measurement_theta_min 4.736 _cell_measurement_theta_max 43.637 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.486 _exptl_crystal_size_mid 0.411 _exptl_crystal_size_min 0.218 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 2.117 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.75713 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 10720 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.0847 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3871 _reflns_number_gt 2153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0789P)^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 3871 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_restrained_S_all 0.878 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.004 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 Br Br 0.09790(6) 0.23445(2) 0.75867(6) 0.0824(3) Uani 1 1 d . . . F1 F 0.1997(4) 0.17553(14) 1.0052(3) 0.1112(12) Uani 1 1 d . . . F2 F -0.0018(4) 0.13840(14) 0.8596(4) 0.1182(12) Uani 1 1 d . . . N1 N 0.1367(3) 0.07459(15) 0.7275(3) 0.0474(8) Uani 1 1 d . . . N2 N 0.3699(3) 0.11781(13) 0.8766(3) 0.0397(7) Uani 1 1 d . . . C1 C 0.2123(4) 0.11198(16) 0.8208(4) 0.0419(9) Uani 1 1 d . . . C2 C 0.1293(5) 0.15954(18) 0.8708(5) 0.0601(11) Uani 1 1 d . . . C3 C 0.4467(4) 0.14948(15) 0.8065(4) 0.0401(9) Uani 1 1 d . . . C4 C 0.4054(5) 0.16731(18) 0.6667(4) 0.0526(10) Uani 1 1 d . . . H4 H 0.3103 0.1601 0.6015 0.063 Uiso 1 1 calc R . . C5 C 0.5078(6) 0.1958(2) 0.6272(5) 0.0694(13) Uani 1 1 d . . . H5 H 0.4824 0.2080 0.5329 0.083 Uiso 1 1 calc R . . C6 C 0.6516(5) 0.2073(2) 0.7248(6) 0.0698(13) Uani 1 1 d . . . H6 H 0.7199 0.2265 0.6943 0.084 Uiso 1 1 calc R . . C7 C 0.6908(4) 0.19055(18) 0.8626(5) 0.0623(12) Uani 1 1 d . . . H7 H 0.7861 0.1983 0.9267 0.075 Uiso 1 1 calc R . . C8 C 0.5891(4) 0.16172(15) 0.9090(4) 0.0448(9) Uani 1 1 d . . . C9 C 0.5935(4) 0.13711(16) 1.0398(4) 0.0464(9) Uani 1 1 d . . . H9 H 0.6741 0.1386 1.1256 0.056 Uiso 1 1 calc R . . C10 C 0.4605(4) 0.11078(15) 1.0199(4) 0.0403(9) Uani 1 1 d . . . C11 C 0.4141(4) 0.07405(16) 1.1179(4) 0.0431(9) Uani 1 1 d . . . C12 C 0.4471(5) 0.0931(2) 1.2564(4) 0.0598(11) Uani 1 1 d . . . H12 H 0.4975 0.1304 1.2872 0.072 Uiso 1 1 calc R . . C13 C 0.4075(6) 0.0585(2) 1.3491(5) 0.0782(14) Uani 1 1 d . . . H13 H 0.4316 0.0720 1.4425 0.094 Uiso 1 1 calc R . . C14 C 0.3316(6) 0.0035(2) 1.3044(6) 0.0799(15) Uani 1 1 d . . . H14 H 0.3043 -0.0203 1.3673 0.096 Uiso 1 1 calc R . . C15 C 0.2966(5) -0.0159(2) 1.1666(5) 0.0673(13) Uani 1 1 d . . . H15 H 0.2440 -0.0526 1.1355 0.081 Uiso 1 1 calc R . . C16 C 0.3386(4) 0.01864(16) 1.0748(4) 0.0510(10) Uani 1 1 d . . . H16 H 0.3162 0.0047 0.9821 0.061 Uiso 1 1 calc R . . C17 C 0.2043(4) 0.02742(17) 0.6698(4) 0.0485(10) Uani 1 1 d . . . H17A H 0.3088 0.0249 0.7276 0.058 Uiso 1 1 calc R . . H17B H 0.1943 0.0391 0.5740 0.058 Uiso 1 1 calc R . . C18 C 0.1340(4) -0.03564(18) 0.6662(4) 0.0488(10) Uani 1 1 d . . . C19 C 0.0469(5) -0.0481(2) 0.7417(5) 0.0664(12) Uani 1 1 d . . . H19 H 0.0254 -0.0168 0.7946 0.080 Uiso 1 1 calc R . . C20 C -0.0101(6) -0.1081(3) 0.7395(6) 0.0895(17) Uani 1 1 d . . . H20 H -0.0673 -0.1173 0.7928 0.107 Uiso 1 1 calc R . . C21 C 0.0197(6) -0.1534(2) 0.6574(7) 0.096(2) Uani 1 1 d . . . H21 H -0.0187 -0.1933 0.6547 0.115 Uiso 1 1 calc R . . C22 C 0.1038(6) -0.1407(2) 0.5806(5) 0.0784(15) Uani 1 1 d . . . H22 H 0.1229 -0.1715 0.5252 0.094 Uiso 1 1 calc R . . C23 C 0.1601(5) -0.08249(18) 0.5850(4) 0.0591(12) Uani 1 1 d . . . H23 H 0.2179 -0.0740 0.5320 0.071 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 Br 0.0922(4) 0.0452(3) 0.1030(5) 0.0032(2) 0.0287(3) 0.0166(2) F1 0.137(3) 0.124(2) 0.0672(19) -0.0037(17) 0.0315(19) 0.078(2) F2 0.084(2) 0.080(2) 0.232(4) 0.010(2) 0.106(3) 0.0149(16) N1 0.0338(17) 0.0502(18) 0.0500(19) 0.0055(16) 0.0062(15) 0.0011(15) N2 0.0308(16) 0.0427(16) 0.0408(18) 0.0016(13) 0.0078(13) -0.0024(13) C1 0.036(2) 0.0387(19) 0.051(2) 0.0090(18) 0.0163(18) 0.0061(17) C2 0.050(3) 0.056(3) 0.070(3) 0.001(2) 0.018(2) 0.012(2) C3 0.040(2) 0.0336(18) 0.049(2) 0.0013(16) 0.0193(18) 0.0050(15) C4 0.051(3) 0.055(2) 0.054(3) 0.007(2) 0.022(2) 0.0063(19) C5 0.085(4) 0.064(3) 0.071(3) 0.017(2) 0.042(3) 0.012(3) C6 0.063(3) 0.062(3) 0.100(4) 0.023(3) 0.050(3) 0.007(2) C7 0.039(2) 0.047(2) 0.097(4) 0.002(2) 0.021(2) 0.0003(18) C8 0.036(2) 0.0338(18) 0.064(3) 0.0004(17) 0.0172(18) 0.0035(16) C9 0.033(2) 0.043(2) 0.053(2) -0.0030(18) 0.0038(17) -0.0016(16) C10 0.041(2) 0.0337(18) 0.041(2) -0.0004(16) 0.0084(17) 0.0060(16) C11 0.040(2) 0.042(2) 0.043(2) 0.0028(17) 0.0096(17) 0.0081(17) C12 0.064(3) 0.060(3) 0.050(3) 0.001(2) 0.013(2) 0.000(2) C13 0.098(4) 0.082(4) 0.054(3) 0.008(3) 0.028(3) 0.011(3) C14 0.094(4) 0.075(3) 0.087(4) 0.037(3) 0.052(3) 0.022(3) C15 0.075(3) 0.050(2) 0.080(4) 0.011(2) 0.033(3) 0.003(2) C16 0.056(3) 0.040(2) 0.052(2) 0.0059(18) 0.015(2) 0.0049(18) C17 0.043(2) 0.050(2) 0.046(2) -0.0034(18) 0.0085(18) -0.0070(18) C18 0.037(2) 0.050(2) 0.043(2) 0.0065(19) -0.0043(18) -0.0036(18) C19 0.053(3) 0.062(3) 0.077(3) 0.007(2) 0.016(2) -0.005(2) C20 0.055(3) 0.096(4) 0.104(4) 0.030(4) 0.014(3) -0.017(3) C21 0.072(4) 0.057(3) 0.107(5) 0.016(3) -0.025(3) -0.016(3) C22 0.084(4) 0.055(3) 0.067(3) -0.002(2) -0.006(3) -0.009(3) C23 0.062(3) 0.053(2) 0.045(2) 0.001(2) 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 Br C2 1.926(4) . ? F1 C2 1.320(5) . ? F2 C2 1.323(5) . ? N1 C1 1.249(4) . ? N1 C17 1.445(5) . ? N2 C3 1.387(4) . ? N2 C10 1.397(4) . ? N2 C1 1.434(4) . ? C1 C2 1.503(5) . ? C3 C4 1.372(5) . ? C3 C8 1.416(5) . ? C4 C5 1.353(6) . ? C4 H4 0.9300 . ? C5 C6 1.405(6) . ? C5 H5 0.9300 . ? C6 C7 1.349(6) . ? C6 H6 0.9300 . ? C7 C8 1.392(6) . ? C7 H7 0.9300 . ? C8 C9 1.410(5) . ? C9 C10 1.361(5) . ? C9 H9 0.9300 . ? C10 C11 1.465(5) . ? C11 C16 1.382(5) . ? C11 C12 1.378(5) . ? C12 C13 1.360(6) . ? C12 H12 0.9300 . ? C13 C14 1.378(7) . ? C13 H13 0.9300 . ? C14 C15 1.370(6) . ? C14 H14 0.9300 . ? C15 C16 1.364(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.512(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.365(6) . ? C18 C23 1.381(6) . ? C19 C20 1.400(7) . ? C19 H19 0.9300 . ? C20 C21 1.379(8) . ? C20 H20 0.9300 . ? C21 C22 1.351(8) . ? C21 H21 0.9300 . ? C22 C23 1.359(6) . ? C22 H22 0.9300 . ? C23 H23 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 C1 N1 C17 121.7(3) . . ? C3 N2 C10 109.2(3) . . ? C3 N2 C1 123.1(3) . . ? C10 N2 C1 124.9(3) . . ? N1 C1 N2 126.8(3) . . ? N1 C1 C2 116.7(3) . . ? N2 C1 C2 116.2(3) . . ? F1 C2 F2 107.1(4) . . ? F1 C2 C1 112.6(3) . . ? F2 C2 C1 111.3(3) . . ? F1 C2 Br 107.3(3) . . ? F2 C2 Br 107.4(3) . . ? C1 C2 Br 110.9(3) . . ? C4 C3 N2 131.0(3) . . ? C4 C3 C8 122.4(4) . . ? N2 C3 C8 106.7(3) . . ? C5 C4 C3 117.6(4) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? C4 C5 C6 121.8(4) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 120.3(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.2(4) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C9 135.0(4) . . ? C7 C8 C3 117.7(4) . . ? C9 C8 C3 107.2(3) . . ? C10 C9 C8 108.8(3) . . ? C10 C9 H9 125.6 . . ? C8 C9 H9 125.6 . . ? C9 C10 N2 108.0(3) . . ? C9 C10 C11 130.0(3) . . ? N2 C10 C11 121.6(3) . . ? C16 C11 C12 118.2(4) . . ? C16 C11 C10 120.9(3) . . ? C12 C11 C10 120.9(3) . . ? C13 C12 C11 121.3(4) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 119.9(5) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 119.6(5) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C16 C15 C14 120.2(4) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 120.9(4) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? N1 C17 C18 111.4(3) . . ? N1 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? N1 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C19 C18 C23 118.8(4) . . ? C19 C18 C17 122.3(4) . . ? C23 C18 C17 118.9(4) . . ? C18 C19 C20 119.9(5) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C21 C20 C19 119.2(5) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C22 C21 C20 120.8(5) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C23 119.5(5) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C18 121.8(5) . . ? C22 C23 H23 119.1 . . ? C18 C23 H23 119.1 . . ? 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 C17 N1 C1 N2 4.8(6) . . . . ? C17 N1 C1 C2 179.1(3) . . . . ? C3 N2 C1 N1 79.8(5) . . . . ? C10 N2 C1 N1 -121.1(4) . . . . ? C3 N2 C1 C2 -94.5(4) . . . . ? C10 N2 C1 C2 64.6(4) . . . . ? N1 C1 C2 F1 149.0(4) . . . . ? N2 C1 C2 F1 -36.1(5) . . . . ? N1 C1 C2 F2 28.7(5) . . . . ? N2 C1 C2 F2 -156.4(3) . . . . ? N1 C1 C2 Br -90.8(4) . . . . ? N2 C1 C2 Br 84.1(3) . . . . ? C10 N2 C3 C4 -180.0(4) . . . . ? C1 N2 C3 C4 -18.0(5) . . . . ? C10 N2 C3 C8 0.6(4) . . . . ? C1 N2 C3 C8 162.6(3) . . . . ? N2 C3 C4 C5 -177.2(4) . . . . ? C8 C3 C4 C5 2.1(5) . . . . ? C3 C4 C5 C6 -0.4(6) . . . . ? C4 C5 C6 C7 -0.7(7) . . . . ? C5 C6 C7 C8 0.0(7) . . . . ? C6 C7 C8 C9 177.7(4) . . . . ? C6 C7 C8 C3 1.6(6) . . . . ? C4 C3 C8 C7 -2.8(5) . . . . ? N2 C3 C8 C7 176.7(3) . . . . ? C4 C3 C8 C9 -179.9(3) . . . . ? N2 C3 C8 C9 -0.4(4) . . . . ? C7 C8 C9 C10 -176.3(4) . . . . ? C3 C8 C9 C10 0.0(4) . . . . ? C8 C9 C10 N2 0.4(4) . . . . ? C8 C9 C10 C11 173.3(3) . . . . ? C3 N2 C10 C9 -0.6(4) . . . . ? C1 N2 C10 C9 -162.2(3) . . . . ? C3 N2 C10 C11 -174.3(3) . . . . ? C1 N2 C10 C11 24.2(5) . . . . ? C9 C10 C11 C16 -132.2(4) . . . . ? N2 C10 C11 C16 39.9(5) . . . . ? C9 C10 C11 C12 46.4(6) . . . . ? N2 C10 C11 C12 -141.5(4) . . . . ? C16 C11 C12 C13 0.3(6) . . . . ? C10 C11 C12 C13 -178.4(4) . . . . ? C11 C12 C13 C14 -0.6(7) . . . . ? C12 C13 C14 C15 0.0(8) . . . . ? C13 C14 C15 C16 1.0(7) . . . . ? C14 C15 C16 C11 -1.4(6) . . . . ? C12 C11 C16 C15 0.7(6) . . . . ? C10 C11 C16 C15 179.4(4) . . . . ? C1 N1 C17 C18 132.7(4) . . . . ? N1 C17 C18 C19 -15.8(5) . . . . ? N1 C17 C18 C23 165.0(3) . . . . ? C23 C18 C19 C20 2.1(6) . . . . ? C17 C18 C19 C20 -177.1(4) . . . . ? C18 C19 C20 C21 -1.8(7) . . . . ? C19 C20 C21 C22 0.6(7) . . . . ? C20 C21 C22 C23 0.3(7) . . . . ? C21 C22 C23 C18 0.0(7) . . . . ? C19 C18 C23 C22 -1.2(6) . . . . ? C17 C18 C23 C22 178.0(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.082 _refine_diff_density_min -0.741 _refine_diff_density_rms 0.071 # Attachment '- cd29452.cif' data_cd29452 _database_code_depnum_ccdc_archive 'CCDC 846078' #TrackingRef '- cd29452.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 Br F2 N2' _chemical_formula_weight 439.30 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' 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 12.5433(14) _cell_length_b 13.5672(15) _cell_length_c 12.0025(14) _cell_angle_alpha 90.00 _cell_angle_beta 107.766(2) _cell_angle_gamma 90.00 _cell_volume 1945.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2842 _cell_measurement_theta_min 4.543 _cell_measurement_theta_max 49.119 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.438 _exptl_crystal_size_mid 0.402 _exptl_crystal_size_min 0.207 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 2.142 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3292 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _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 11187 _diffrn_reflns_av_R_equivalents 0.0822 _diffrn_reflns_av_sigmaI/netI 0.0890 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.99 _reflns_number_total 4229 _reflns_number_gt 2467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0474P)^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 4229 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 0.888 _refine_ls_restrained_S_all 0.888 _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 Br Br 0.59870(3) 0.20172(3) 1.06542(4) 0.06482(17) Uani 1 1 d . . . F1 F 0.43192(14) 0.33520(13) 1.00512(17) 0.0570(5) Uani 1 1 d . . . F2 F 0.50135(16) 0.29839(13) 0.86816(19) 0.0650(6) Uani 1 1 d . . . N1 N 0.30066(17) 0.16479(16) 0.9610(2) 0.0330(5) Uani 1 1 d . . . N2 N 0.38761(18) 0.13766(18) 0.8134(2) 0.0409(6) Uani 1 1 d . . . C1 C 0.3803(2) 0.1807(2) 0.9046(3) 0.0352(7) Uani 1 1 d . . . C2 C 0.2028(2) 0.11158(19) 0.8961(2) 0.0334(7) Uani 1 1 d . . . C3 C 0.2267(2) 0.0386(2) 0.8175(2) 0.0339(7) Uani 1 1 d . . . C4 C 0.3171(2) 0.0560(2) 0.7750(3) 0.0404(7) Uani 1 1 d . . . C5 C 0.3390(3) -0.0069(2) 0.6930(3) 0.0493(8) Uani 1 1 d . . . H5 H 0.3975 0.0066 0.6629 0.059 Uiso 1 1 calc R . . C6 C 0.2737(3) -0.0891(2) 0.6568(3) 0.0549(9) Uani 1 1 d . . . H6 H 0.2884 -0.1312 0.6021 0.066 Uiso 1 1 calc R . . C7 C 0.1863(3) -0.1098(2) 0.7008(3) 0.0493(9) Uani 1 1 d . . . H7 H 0.1437 -0.1665 0.6771 0.059 Uiso 1 1 calc R . . C8 C 0.1623(2) -0.0463(2) 0.7800(3) 0.0415(7) Uani 1 1 d . . . H8 H 0.1029 -0.0602 0.8087 0.050 Uiso 1 1 calc R . . C9 C 0.4684(2) 0.2596(2) 0.9528(3) 0.0433(8) Uani 1 1 d . . . C10 C 0.1004(2) 0.1280(2) 0.9052(2) 0.0357(7) Uani 1 1 d . . . H10 H 0.0462 0.0829 0.8658 0.043 Uiso 1 1 calc R . . C11 C 0.0604(2) 0.2050(2) 0.9664(3) 0.0364(7) Uani 1 1 d . . . C12 C -0.0295(2) 0.1852(2) 1.0098(3) 0.0460(8) Uani 1 1 d . . . H12 H -0.0633 0.1235 0.9976 0.055 Uiso 1 1 calc R . . C13 C -0.0678(3) 0.2556(3) 1.0699(3) 0.0588(9) Uani 1 1 d . . . H13 H -0.1262 0.2410 1.0998 0.071 Uiso 1 1 calc R . . C14 C -0.0198(3) 0.3483(3) 1.0861(3) 0.0568(9) Uani 1 1 d . . . H14 H -0.0446 0.3953 1.1289 0.068 Uiso 1 1 calc R . . C15 C 0.0635(3) 0.3708(2) 1.0399(3) 0.0507(9) Uani 1 1 d . . . H15 H 0.0939 0.4339 1.0488 0.061 Uiso 1 1 calc R . . C16 C 0.1028(2) 0.3003(2) 0.9799(3) 0.0417(7) Uani 1 1 d . . . H16 H 0.1590 0.3168 0.9476 0.050 Uiso 1 1 calc R . . C17 C 0.3223(2) 0.1821(2) 1.0879(2) 0.0383(7) Uani 1 1 d . . . H17A H 0.2773 0.2373 1.0986 0.046 Uiso 1 1 calc R . . H17B H 0.4004 0.1996 1.1227 0.046 Uiso 1 1 calc R . . C18 C 0.2960(2) 0.0934(2) 1.1500(2) 0.0359(7) Uani 1 1 d . . . C19 C 0.2249(3) 0.1032(2) 1.2175(3) 0.0473(8) Uani 1 1 d . . . H19 H 0.1909 0.1635 1.2214 0.057 Uiso 1 1 calc R . . C20 C 0.2039(3) 0.0224(3) 1.2800(3) 0.0652(10) Uani 1 1 d . . . H20 H 0.1562 0.0287 1.3257 0.078 Uiso 1 1 calc R . . C21 C 0.2536(4) -0.0655(3) 1.2733(4) 0.0753(12) Uani 1 1 d . . . H21 H 0.2388 -0.1197 1.3137 0.090 Uiso 1 1 calc R . . C22 C 0.3253(3) -0.0753(3) 1.2080(4) 0.0721(11) Uani 1 1 d . . . H22 H 0.3602 -0.1353 1.2055 0.087 Uiso 1 1 calc R . . C23 C 0.3454(3) 0.0040(2) 1.1462(3) 0.0517(8) Uani 1 1 d . . . H23 H 0.3933 -0.0032 1.1009 0.062 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 Br 0.03501(19) 0.0710(3) 0.0738(3) -0.0043(2) -0.00514(17) -0.00233(16) F1 0.0489(10) 0.0470(10) 0.0725(14) -0.0099(10) 0.0147(10) -0.0041(8) F2 0.0552(11) 0.0763(13) 0.0644(13) 0.0098(10) 0.0196(11) -0.0257(10) N1 0.0264(11) 0.0392(13) 0.0320(14) -0.0026(11) 0.0067(11) -0.0060(10) N2 0.0327(13) 0.0525(15) 0.0388(15) -0.0020(13) 0.0129(12) -0.0030(12) C1 0.0253(14) 0.0391(17) 0.0377(18) 0.0048(14) 0.0044(13) 0.0002(11) C2 0.0301(14) 0.0363(16) 0.0324(16) 0.0016(13) 0.0075(13) -0.0050(12) C3 0.0288(14) 0.0360(15) 0.0321(16) -0.0021(13) 0.0022(13) 0.0031(12) C4 0.0332(15) 0.0484(18) 0.0358(18) -0.0016(14) 0.0051(14) 0.0044(14) C5 0.0370(16) 0.065(2) 0.047(2) -0.0096(17) 0.0145(16) 0.0058(16) C6 0.0477(18) 0.059(2) 0.053(2) -0.0209(18) 0.0078(18) 0.0119(17) C7 0.0473(18) 0.0414(18) 0.049(2) -0.0092(15) 0.0003(17) 0.0025(15) C8 0.0365(15) 0.0446(17) 0.0414(19) -0.0004(15) 0.0087(14) -0.0006(14) C9 0.0337(16) 0.0485(19) 0.046(2) 0.0073(16) 0.0102(15) -0.0070(14) C10 0.0315(14) 0.0379(16) 0.0365(17) -0.0006(13) 0.0087(13) -0.0045(12) C11 0.0276(13) 0.0441(17) 0.0362(16) 0.0028(14) 0.0078(13) 0.0054(13) C12 0.0391(16) 0.0450(19) 0.058(2) 0.0075(15) 0.0207(17) 0.0047(14) C13 0.052(2) 0.072(2) 0.063(2) 0.015(2) 0.0340(19) 0.0184(19) C14 0.058(2) 0.061(2) 0.053(2) -0.0054(18) 0.0195(19) 0.0199(19) C15 0.0477(18) 0.0395(18) 0.058(2) -0.0022(16) 0.0060(17) 0.0075(15) C16 0.0369(15) 0.0416(17) 0.0472(19) 0.0024(15) 0.0138(15) -0.0012(14) C17 0.0325(15) 0.0482(18) 0.0337(17) -0.0056(13) 0.0092(14) -0.0056(13) C18 0.0305(14) 0.0427(17) 0.0302(16) 0.0005(13) 0.0027(13) -0.0016(13) C19 0.0504(18) 0.0459(19) 0.049(2) -0.0002(16) 0.0201(17) 0.0024(15) C20 0.072(2) 0.067(3) 0.071(3) 0.012(2) 0.044(2) 0.001(2) C21 0.098(3) 0.054(2) 0.091(3) 0.026(2) 0.055(3) 0.007(2) C22 0.090(3) 0.050(2) 0.085(3) 0.020(2) 0.040(3) 0.025(2) C23 0.0510(19) 0.057(2) 0.054(2) 0.0102(18) 0.0256(17) 0.0142(17) _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 Br C9 1.941(3) . ? F1 C9 1.353(4) . ? F2 C9 1.318(4) . ? N1 C1 1.384(4) . ? N1 C2 1.432(3) . ? N1 C17 1.482(4) . ? N2 C1 1.268(4) . ? N2 C4 1.405(4) . ? C1 C9 1.520(4) . ? C2 C10 1.340(4) . ? C2 C3 1.461(4) . ? C3 C4 1.398(4) . ? C3 C8 1.400(4) . ? C4 C5 1.392(4) . ? C5 C6 1.373(4) . ? C5 H5 0.9300 . ? C6 C7 1.383(5) . ? C6 H6 0.9300 . ? C7 C8 1.382(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C10 C11 1.452(4) . ? C10 H10 0.9300 . ? C11 C16 1.388(4) . ? C11 C12 1.404(4) . ? C12 C13 1.370(4) . ? C12 H12 0.9300 . ? C13 C14 1.382(5) . ? C13 H13 0.9300 . ? C14 C15 1.359(5) . ? C14 H14 0.9300 . ? C15 C16 1.377(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.504(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.369(4) . ? C18 C19 1.383(4) . ? C19 C20 1.398(4) . ? C19 H19 0.9300 . ? C20 C21 1.359(5) . ? C20 H20 0.9300 . ? C21 C22 1.367(5) . ? C21 H21 0.9300 . ? C22 C23 1.373(5) . ? C22 H22 0.9300 . ? C23 H23 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 C1 N1 C2 116.1(2) . . ? C1 N1 C17 123.0(2) . . ? C2 N1 C17 119.7(2) . . ? C1 N2 C4 116.2(3) . . ? N2 C1 N1 127.1(3) . . ? N2 C1 C9 114.7(3) . . ? N1 C1 C9 118.2(3) . . ? C10 C2 N1 123.8(3) . . ? C10 C2 C3 123.8(2) . . ? N1 C2 C3 112.4(2) . . ? C4 C3 C8 118.3(3) . . ? C4 C3 C2 118.1(3) . . ? C8 C3 C2 123.6(3) . . ? C5 C4 C3 120.8(3) . . ? C5 C4 N2 118.3(3) . . ? C3 C4 N2 120.8(3) . . ? C6 C5 C4 119.6(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 120.7(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.0(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C3 120.6(3) . . ? C7 C8 H8 119.7 . . ? C3 C8 H8 119.7 . . ? F2 C9 F1 106.6(2) . . ? F2 C9 C1 110.5(3) . . ? F1 C9 C1 113.7(2) . . ? F2 C9 Br 107.6(2) . . ? F1 C9 Br 108.42(19) . . ? C1 C9 Br 109.9(2) . . ? C2 C10 C11 130.4(3) . . ? C2 C10 H10 114.8 . . ? C11 C10 H10 114.8 . . ? C16 C11 C12 117.3(3) . . ? C16 C11 C10 123.3(3) . . ? C12 C11 C10 119.4(3) . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 121.5(3) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? N1 C17 C18 112.6(2) . . ? N1 C17 H17A 109.1 . . ? C18 C17 H17A 109.1 . . ? N1 C17 H17B 109.1 . . ? C18 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? C23 C18 C19 118.9(3) . . ? C23 C18 C17 121.5(3) . . ? C19 C18 C17 119.5(3) . . ? C18 C19 C20 120.0(3) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C21 C20 C19 119.4(3) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 120.8(3) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C21 C22 C23 119.7(3) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C18 C23 C22 121.1(3) . . ? C18 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? 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 C4 N2 C1 N1 -9.6(4) . . . . ? C4 N2 C1 C9 172.1(2) . . . . ? C2 N1 C1 N2 -15.3(4) . . . . ? C17 N1 C1 N2 152.4(3) . . . . ? C2 N1 C1 C9 163.0(2) . . . . ? C17 N1 C1 C9 -29.4(4) . . . . ? C1 N1 C2 C10 -146.4(3) . . . . ? C17 N1 C2 C10 45.5(4) . . . . ? C1 N1 C2 C3 32.6(3) . . . . ? C17 N1 C2 C3 -135.5(3) . . . . ? C10 C2 C3 C4 151.4(3) . . . . ? N1 C2 C3 C4 -27.6(3) . . . . ? C10 C2 C3 C8 -26.9(4) . . . . ? N1 C2 C3 C8 154.2(2) . . . . ? C8 C3 C4 C5 3.2(4) . . . . ? C2 C3 C4 C5 -175.1(3) . . . . ? C8 C3 C4 N2 -177.2(2) . . . . ? C2 C3 C4 N2 4.4(4) . . . . ? C1 N2 C4 C5 -165.5(3) . . . . ? C1 N2 C4 C3 14.9(4) . . . . ? C3 C4 C5 C6 -2.5(5) . . . . ? N2 C4 C5 C6 177.9(3) . . . . ? C4 C5 C6 C7 0.1(5) . . . . ? C5 C6 C7 C8 1.5(5) . . . . ? C6 C7 C8 C3 -0.8(4) . . . . ? C4 C3 C8 C7 -1.6(4) . . . . ? C2 C3 C8 C7 176.7(3) . . . . ? N2 C1 C9 F2 28.2(4) . . . . ? N1 C1 C9 F2 -150.3(2) . . . . ? N2 C1 C9 F1 147.9(3) . . . . ? N1 C1 C9 F1 -30.5(4) . . . . ? N2 C1 C9 Br -90.4(3) . . . . ? N1 C1 C9 Br 91.1(3) . . . . ? N1 C2 C10 C11 7.8(5) . . . . ? C3 C2 C10 C11 -171.0(3) . . . . ? C2 C10 C11 C16 32.9(5) . . . . ? C2 C10 C11 C12 -150.5(3) . . . . ? C16 C11 C12 C13 -4.4(4) . . . . ? C10 C11 C12 C13 178.8(3) . . . . ? C11 C12 C13 C14 1.5(5) . . . . ? C12 C13 C14 C15 1.8(5) . . . . ? C13 C14 C15 C16 -2.1(5) . . . . ? C14 C15 C16 C11 -0.9(5) . . . . ? C12 C11 C16 C15 4.1(4) . . . . ? C10 C11 C16 C15 -179.2(3) . . . . ? C1 N1 C17 C18 -126.3(3) . . . . ? C2 N1 C17 C18 40.9(3) . . . . ? N1 C17 C18 C23 56.7(3) . . . . ? N1 C17 C18 C19 -126.6(3) . . . . ? C23 C18 C19 C20 -0.3(4) . . . . ? C17 C18 C19 C20 -177.1(3) . . . . ? C18 C19 C20 C21 -0.2(5) . . . . ? C19 C20 C21 C22 1.1(6) . . . . ? C20 C21 C22 C23 -1.5(6) . . . . ? C19 C18 C23 C22 -0.1(5) . . . . ? C17 C18 C23 C22 176.6(3) . . . . ? C21 C22 C23 C18 1.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.032 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.067 # Attachment '- cd29561.cif' data_cd29561 _database_code_depnum_ccdc_archive 'CCDC 846079' #TrackingRef '- cd29561.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 F3 N2 O' _chemical_formula_weight 394.39 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' _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 9.670(2) _cell_length_b 9.854(2) _cell_length_c 11.723(3) _cell_angle_alpha 81.755(4) _cell_angle_beta 85.472(4) _cell_angle_gamma 62.643(4) _cell_volume 981.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 867 _cell_measurement_theta_min 4.689 _cell_measurement_theta_max 43.795 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.287 _exptl_crystal_size_min 0.139 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2567 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _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 5176 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0731 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3582 _reflns_number_gt 1740 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1035P)^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 3582 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1150 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1972 _refine_ls_wR_factor_gt 0.1634 _refine_ls_goodness_of_fit_ref 0.860 _refine_ls_restrained_S_all 0.860 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.8134(3) 0.7138(3) 0.3326(2) 0.1143(9) Uani 1 1 d . . . F2 F 0.7784(3) 0.5220(3) 0.41236(18) 0.1222(10) Uani 1 1 d . . . F3 F 1.0066(3) 0.4940(3) 0.36327(19) 0.1171(10) Uani 1 1 d . . . O1 O 0.1515(3) 0.9483(3) 0.3986(2) 0.0833(8) Uani 1 1 d . . . N1 N 0.6983(3) 0.5994(3) 0.1638(2) 0.0574(7) Uani 1 1 d . . . N2 N 0.9687(3) 0.4218(3) 0.1728(2) 0.0633(8) Uani 1 1 d . . . C1 C 0.8433(4) 0.5249(4) 0.2130(3) 0.0627(9) Uani 1 1 d . . . C2 C 0.6843(4) 0.5799(3) 0.0465(2) 0.0554(8) Uani 1 1 d . . . C3 C 0.8112(4) 0.4387(3) 0.0105(2) 0.0557(8) Uani 1 1 d . . . C4 C 0.9517(4) 0.3675(4) 0.0728(3) 0.0587(9) Uani 1 1 d . . . C5 C 1.0784(4) 0.2355(4) 0.0402(3) 0.0732(10) Uani 1 1 d . . . H5 H 1.1722 0.1932 0.0788 0.088 Uiso 1 1 calc R . . C6 C 1.0619(5) 0.1682(4) -0.0509(3) 0.0869(12) Uani 1 1 d . . . H6 H 1.1451 0.0797 -0.0734 0.104 Uiso 1 1 calc R . . C7 C 0.9211(5) 0.2327(4) -0.1084(3) 0.0801(12) Uani 1 1 d . . . H7 H 0.9104 0.1859 -0.1683 0.096 Uiso 1 1 calc R . . C8 C 0.7985(4) 0.3641(4) -0.0779(3) 0.0644(9) Uani 1 1 d . . . H8 H 0.7049 0.4046 -0.1166 0.077 Uiso 1 1 calc R . . C9 C 0.8602(5) 0.5657(5) 0.3308(3) 0.0852(12) Uani 1 1 d . . . C10 C 0.5603(4) 0.6865(4) -0.0149(3) 0.0603(9) Uani 1 1 d . . . H10 H 0.4837 0.7576 0.0286 0.072 Uiso 1 1 calc R . . C11 C 0.5239(4) 0.7111(3) -0.1378(3) 0.0546(8) Uani 1 1 d . . . C12 C 0.6369(4) 0.6806(4) -0.2252(3) 0.0634(9) Uani 1 1 d . . . H12 H 0.7416 0.6364 -0.2066 0.076 Uiso 1 1 calc R . . C13 C 0.5935(5) 0.7162(4) -0.3395(3) 0.0774(11) Uani 1 1 d . . . H13 H 0.6703 0.6909 -0.3969 0.093 Uiso 1 1 calc R . . C14 C 0.4425(6) 0.7865(5) -0.3698(3) 0.0889(13) Uani 1 1 d . . . H14 H 0.4157 0.8122 -0.4472 0.107 Uiso 1 1 calc R . . C15 C 0.3283(5) 0.8199(4) -0.2851(4) 0.0878(12) Uani 1 1 d . . . H15 H 0.2239 0.8670 -0.3051 0.105 Uiso 1 1 calc R . . C16 C 0.3698(4) 0.7826(4) -0.1692(3) 0.0725(10) Uani 1 1 d . . . H16 H 0.2923 0.8064 -0.1124 0.087 Uiso 1 1 calc R . . C17 C 0.5588(4) 0.6940(4) 0.2254(2) 0.0535(8) Uani 1 1 d . . . C18 C 0.4729(4) 0.6277(4) 0.2838(3) 0.0634(9) Uani 1 1 d . . . H18 H 0.5068 0.5225 0.2858 0.076 Uiso 1 1 calc R . . C19 C 0.3359(4) 0.7160(4) 0.3400(3) 0.0674(10) Uani 1 1 d . . . H19 H 0.2764 0.6710 0.3782 0.081 Uiso 1 1 calc R . . C20 C 0.2878(4) 0.8729(4) 0.3388(3) 0.0597(9) Uani 1 1 d . . . C21 C 0.3733(4) 0.9395(4) 0.2806(3) 0.0643(9) Uani 1 1 d . . . H21 H 0.3400 1.0446 0.2786 0.077 Uiso 1 1 calc R . . C22 C 0.5095(4) 0.8499(4) 0.2245(3) 0.0609(9) Uani 1 1 d . . . H22 H 0.5687 0.8949 0.1857 0.073 Uiso 1 1 calc R . . C23 C 0.1057(5) 1.1081(4) 0.4089(4) 0.1075(16) Uani 1 1 d . . . H23A H 0.1871 1.1155 0.4453 0.161 Uiso 1 1 calc R . . H23B H 0.0120 1.1489 0.4547 0.161 Uiso 1 1 calc R . . H23C H 0.0876 1.1658 0.3336 0.161 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.130(2) 0.1012(19) 0.1037(18) -0.0475(15) -0.0284(15) -0.0318(16) F2 0.135(2) 0.177(3) 0.0439(12) -0.0127(14) 0.0059(13) -0.063(2) F3 0.0897(18) 0.154(2) 0.0749(15) -0.0448(15) -0.0218(13) -0.0161(16) O1 0.0747(17) 0.0767(18) 0.0845(18) -0.0139(14) 0.0197(14) -0.0246(14) N1 0.0628(18) 0.0588(16) 0.0428(15) -0.0084(12) -0.0023(13) -0.0200(14) N2 0.0681(19) 0.0630(17) 0.0472(16) -0.0083(13) -0.0018(14) -0.0193(15) C1 0.080(3) 0.058(2) 0.0421(18) -0.0025(16) -0.0046(18) -0.0240(19) C2 0.073(2) 0.0507(19) 0.0418(17) -0.0043(14) -0.0022(16) -0.0277(18) C3 0.077(2) 0.0483(18) 0.0386(16) -0.0016(14) -0.0004(16) -0.0268(17) C4 0.076(2) 0.053(2) 0.0411(17) -0.0053(15) 0.0004(16) -0.0245(18) C5 0.080(3) 0.057(2) 0.066(2) -0.0068(18) -0.0020(19) -0.017(2) C6 0.100(3) 0.056(2) 0.077(3) -0.020(2) 0.000(2) -0.009(2) C7 0.108(3) 0.058(2) 0.065(2) -0.0160(19) -0.009(2) -0.026(2) C8 0.079(2) 0.056(2) 0.057(2) -0.0099(16) -0.0037(17) -0.0281(19) C9 0.085(3) 0.095(3) 0.060(2) -0.023(2) -0.007(2) -0.023(3) C10 0.070(2) 0.055(2) 0.0496(19) -0.0099(15) 0.0007(17) -0.0228(18) C11 0.065(2) 0.0423(17) 0.0523(19) -0.0063(14) -0.0022(17) -0.0209(16) C12 0.083(2) 0.060(2) 0.052(2) -0.0066(16) -0.0012(18) -0.0367(19) C13 0.115(3) 0.075(3) 0.048(2) 0.0004(18) -0.006(2) -0.050(2) C14 0.127(4) 0.080(3) 0.057(2) 0.005(2) -0.027(3) -0.045(3) C15 0.105(3) 0.071(3) 0.078(3) 0.001(2) -0.033(3) -0.030(2) C16 0.081(3) 0.054(2) 0.070(2) -0.0075(18) -0.008(2) -0.0183(19) C17 0.063(2) 0.053(2) 0.0431(17) -0.0073(14) 0.0045(15) -0.0258(17) C18 0.084(3) 0.053(2) 0.054(2) -0.0088(16) 0.0013(18) -0.0322(19) C19 0.087(3) 0.068(2) 0.055(2) -0.0063(17) 0.0063(18) -0.043(2) C20 0.066(2) 0.058(2) 0.0476(19) -0.0080(15) 0.0027(16) -0.0211(18) C21 0.078(2) 0.052(2) 0.059(2) -0.0053(16) 0.0074(18) -0.0274(19) C22 0.076(2) 0.057(2) 0.054(2) -0.0076(16) 0.0119(17) -0.0351(19) C23 0.109(4) 0.066(3) 0.107(3) -0.018(2) 0.037(3) -0.010(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 F1 C9 1.317(5) . ? F2 C9 1.342(5) . ? F3 C9 1.318(4) . ? O1 C20 1.372(4) . ? O1 C23 1.447(4) . ? N1 C1 1.377(4) . ? N1 C2 1.440(4) . ? N1 C17 1.447(4) . ? N2 C1 1.281(4) . ? N2 C4 1.406(4) . ? C1 C9 1.533(5) . ? C2 C10 1.349(4) . ? C2 C3 1.462(4) . ? C3 C8 1.397(4) . ? C3 C4 1.416(5) . ? C4 C5 1.394(4) . ? C5 C6 1.391(5) . ? C5 H5 0.9300 . ? C6 C7 1.392(5) . ? C6 H6 0.9300 . ? C7 C8 1.366(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C10 C11 1.470(4) . ? C10 H10 0.9300 . ? C11 C16 1.378(5) . ? C11 C12 1.394(4) . ? C12 C13 1.383(5) . ? C12 H12 0.9300 . ? C13 C14 1.348(5) . ? C13 H13 0.9300 . ? C14 C15 1.379(6) . ? C14 H14 0.9300 . ? C15 C16 1.396(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.366(4) . ? C17 C22 1.382(4) . ? C18 C19 1.383(4) . ? C18 H18 0.9300 . ? C19 C20 1.393(4) . ? C19 H19 0.9300 . ? C20 C21 1.364(4) . ? C21 C22 1.381(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 C20 O1 C23 115.9(3) . . ? C1 N1 C2 118.6(3) . . ? C1 N1 C17 122.9(3) . . ? C2 N1 C17 118.4(2) . . ? C1 N2 C4 115.5(3) . . ? N2 C1 N1 127.7(3) . . ? N2 C1 C9 114.5(3) . . ? N1 C1 C9 117.7(3) . . ? C10 C2 N1 119.0(3) . . ? C10 C2 C3 128.2(3) . . ? N1 C2 C3 112.8(3) . . ? C8 C3 C4 117.7(3) . . ? C8 C3 C2 123.5(3) . . ? C4 C3 C2 118.7(3) . . ? C5 C4 N2 116.6(3) . . ? C5 C4 C3 121.2(3) . . ? N2 C4 C3 122.1(3) . . ? C6 C5 C4 118.8(4) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C7 120.2(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.7(4) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C3 121.1(3) . . ? C7 C8 H8 119.4 . . ? C3 C8 H8 119.4 . . ? F1 C9 F3 106.8(4) . . ? F1 C9 F2 107.3(3) . . ? F3 C9 F2 106.8(3) . . ? F1 C9 C1 113.6(3) . . ? F3 C9 C1 111.0(3) . . ? F2 C9 C1 111.0(4) . . ? C2 C10 C11 131.9(3) . . ? C2 C10 H10 114.1 . . ? C11 C10 H10 114.1 . . ? C16 C11 C12 118.0(3) . . ? C16 C11 C10 118.5(3) . . ? C12 C11 C10 123.1(3) . . ? C13 C12 C11 120.1(4) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 121.6(4) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 119.5(4) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 119.8(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 121.0(4) . . ? C11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C18 C17 C22 119.6(3) . . ? C18 C17 N1 119.0(3) . . ? C22 C17 N1 121.4(3) . . ? C17 C18 C19 120.4(3) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C20 119.4(3) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C21 C20 O1 125.4(3) . . ? C21 C20 C19 120.2(3) . . ? O1 C20 C19 114.3(3) . . ? C20 C21 C22 119.6(3) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C21 C22 C17 120.7(3) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? O1 C23 H23A 109.5 . . ? O1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C4 N2 C1 N1 -7.2(5) . . . . ? C4 N2 C1 C9 171.7(3) . . . . ? C2 N1 C1 N2 -10.0(5) . . . . ? C17 N1 C1 N2 168.8(3) . . . . ? C2 N1 C1 C9 171.1(3) . . . . ? C17 N1 C1 C9 -10.1(5) . . . . ? C1 N1 C2 C10 -158.3(3) . . . . ? C17 N1 C2 C10 22.9(4) . . . . ? C1 N1 C2 C3 23.0(4) . . . . ? C17 N1 C2 C3 -155.9(3) . . . . ? C10 C2 C3 C8 -23.2(5) . . . . ? N1 C2 C3 C8 155.4(3) . . . . ? C10 C2 C3 C4 161.1(3) . . . . ? N1 C2 C3 C4 -20.3(4) . . . . ? C1 N2 C4 C5 -167.8(3) . . . . ? C1 N2 C4 C3 9.7(5) . . . . ? C8 C3 C4 C5 6.0(5) . . . . ? C2 C3 C4 C5 -178.0(3) . . . . ? C8 C3 C4 N2 -171.3(3) . . . . ? C2 C3 C4 N2 4.7(5) . . . . ? N2 C4 C5 C6 173.5(3) . . . . ? C3 C4 C5 C6 -4.0(5) . . . . ? C4 C5 C6 C7 0.3(6) . . . . ? C5 C6 C7 C8 1.2(6) . . . . ? C6 C7 C8 C3 1.0(6) . . . . ? C4 C3 C8 C7 -4.5(5) . . . . ? C2 C3 C8 C7 179.7(3) . . . . ? N2 C1 C9 F1 125.7(4) . . . . ? N1 C1 C9 F1 -55.3(5) . . . . ? N2 C1 C9 F3 5.3(5) . . . . ? N1 C1 C9 F3 -175.6(3) . . . . ? N2 C1 C9 F2 -113.3(4) . . . . ? N1 C1 C9 F2 65.8(4) . . . . ? N1 C2 C10 C11 170.3(3) . . . . ? C3 C2 C10 C11 -11.2(6) . . . . ? C2 C10 C11 C16 152.9(4) . . . . ? C2 C10 C11 C12 -34.2(6) . . . . ? C16 C11 C12 C13 -2.7(5) . . . . ? C10 C11 C12 C13 -175.6(3) . . . . ? C11 C12 C13 C14 2.9(5) . . . . ? C12 C13 C14 C15 -2.0(6) . . . . ? C13 C14 C15 C16 0.9(6) . . . . ? C12 C11 C16 C15 1.6(5) . . . . ? C10 C11 C16 C15 174.9(3) . . . . ? C14 C15 C16 C11 -0.8(6) . . . . ? C1 N1 C17 C18 -91.0(4) . . . . ? C2 N1 C17 C18 87.8(3) . . . . ? C1 N1 C17 C22 90.2(4) . . . . ? C2 N1 C17 C22 -91.0(4) . . . . ? C22 C17 C18 C19 1.2(5) . . . . ? N1 C17 C18 C19 -177.6(3) . . . . ? C17 C18 C19 C20 -1.5(5) . . . . ? C23 O1 C20 C21 -6.6(5) . . . . ? C23 O1 C20 C19 174.2(3) . . . . ? C18 C19 C20 C21 1.5(5) . . . . ? C18 C19 C20 O1 -179.2(3) . . . . ? O1 C20 C21 C22 179.5(3) . . . . ? C19 C20 C21 C22 -1.3(5) . . . . ? C20 C21 C22 C17 1.0(5) . . . . ? C18 C17 C22 C21 -1.0(5) . . . . ? N1 C17 C22 C21 177.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.211 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.049