# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email slyou@sioc.ac.cn _publ_contact_author_name 'Shuli You' _publ_author_name 'Shuli You' data_cd211246 _database_code_depnum_ccdc_archive 'CCDC 859342' #TrackingRef 'cd211246.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 Br F3 N O' _chemical_formula_weight 396.20 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.2256(14) _cell_length_b 11.0205(18) _cell_length_c 18.212(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1650.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3899 _cell_measurement_theta_min 4.473 _cell_measurement_theta_max 51.188 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.369 _exptl_crystal_size_mid 0.311 _exptl_crystal_size_min 0.257 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 2.525 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.57501 _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 8973 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3202 _reflns_number_gt 2721 _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^)+(0.0314P)^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 SHELXL _refine_ls_extinction_coef 0.0035(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.022(8) _chemical_absolute_configuration ad _refine_ls_number_reflns 3202 _refine_ls_number_parameters 218 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0751 _refine_ls_wR_factor_gt 0.0719 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.13184(4) -0.38707(2) 0.068711(18) 0.06625(14) Uani 1 1 d . . . F1 F 0.2121(3) 0.1599(2) -0.05560(11) 0.0912(7) Uani 1 1 d . . . F2 F 0.0060(3) 0.2679(2) -0.07884(11) 0.0890(7) Uani 1 1 d . . . F3 F -0.0247(3) 0.08588(18) -0.04396(9) 0.0727(5) Uani 1 1 d . . . N1 N 0.0480(3) 0.15615(18) 0.10015(11) 0.0454(5) Uani 1 1 d . . . O1 O 0.0759(3) 0.34247(18) 0.05025(13) 0.0764(7) Uani 1 1 d . . . C1 C 0.0642(4) 0.2339(2) 0.04433(14) 0.0487(7) Uani 1 1 d . . . C2 C 0.0644(4) 0.1841(3) -0.03382(15) 0.0540(7) Uani 1 1 d . . . C3 C 0.0712(4) 0.0272(2) 0.09391(13) 0.0421(6) Uani 1 1 d . . . C4 C 0.2214(4) -0.0192(2) 0.07973(16) 0.0504(7) Uani 1 1 d . . . H4 H 0.3102 0.0327 0.0755 0.060 Uiso 1 1 calc R . . C5 C 0.2427(4) -0.1431(3) 0.07162(17) 0.0546(7) Uani 1 1 d . . . H5 H 0.3443 -0.1755 0.0608 0.066 Uiso 1 1 calc R . . C6 C 0.1092(4) -0.2168(2) 0.08008(13) 0.0478(6) Uani 1 1 d . . . C7 C -0.0414(4) -0.1712(2) 0.09625(14) 0.0471(7) Uani 1 1 d . . . H7 H -0.1289 -0.2236 0.1027 0.056 Uiso 1 1 calc R . . C8 C -0.0637(4) -0.0469(2) 0.10304(14) 0.0433(6) Uani 1 1 d . . . C9 C -0.2285(4) 0.0057(3) 0.11688(16) 0.0537(7) Uani 1 1 d . . . H9A H -0.2603 0.0536 0.0746 0.064 Uiso 1 1 calc R . . H9B H -0.3060 -0.0602 0.1218 0.064 Uiso 1 1 calc R . . C10 C -0.2377(4) 0.0838(3) 0.18389(17) 0.0638(8) Uani 1 1 d . . . H10 H -0.3304 0.0735 0.2125 0.077 Uiso 1 1 calc R . . C11 C -0.1346(4) 0.1641(3) 0.20797(16) 0.0634(8) Uani 1 1 d . . . H11 H -0.1628 0.2004 0.2523 0.076 Uiso 1 1 calc R . . C12 C 0.0220(4) 0.2070(2) 0.17552(15) 0.0543(7) Uani 1 1 d . . . H12 H 0.0114 0.2950 0.1695 0.065 Uiso 1 1 calc R . . C13 C 0.1673(4) 0.1872(3) 0.22396(15) 0.0576(8) Uani 1 1 d . . . C14 C 0.1817(5) 0.0857(3) 0.26638(18) 0.0783(10) Uani 1 1 d U . . H14 H 0.1010 0.0267 0.2647 0.094 Uiso 1 1 calc R . . C15 C 0.3136(6) 0.0696(5) 0.3116(2) 0.1023(14) Uani 1 1 d U . . H15 H 0.3222 -0.0001 0.3401 0.123 Uiso 1 1 calc R . . C16 C 0.4322(6) 0.1563(6) 0.3146(3) 0.1085(17) Uani 1 1 d U . . H16 H 0.5217 0.1460 0.3452 0.130 Uiso 1 1 calc R . . C17 C 0.4184(5) 0.2569(5) 0.2729(3) 0.0983(14) Uani 1 1 d U . . H17 H 0.4989 0.3160 0.2752 0.118 Uiso 1 1 calc R . . C18 C 0.2887(5) 0.2736(4) 0.22743(18) 0.0751(10) Uani 1 1 d . . . H18 H 0.2819 0.3433 0.1987 0.090 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 0.0946(2) 0.03096(15) 0.0731(2) -0.00784(13) 0.00283(18) 0.01307(14) F1 0.0743(13) 0.1249(19) 0.0743(13) -0.0190(13) 0.0203(10) -0.0075(13) F2 0.1292(18) 0.0775(14) 0.0603(11) 0.0260(10) -0.0187(12) -0.0117(13) F3 0.1016(14) 0.0676(12) 0.0489(9) -0.0015(8) -0.0034(9) -0.0351(11) N1 0.0708(15) 0.0258(10) 0.0395(10) -0.0015(8) 0.0024(10) 0.0053(10) O1 0.122(2) 0.0316(11) 0.0754(15) 0.0049(10) 0.0001(13) -0.0120(12) C1 0.0576(17) 0.0344(15) 0.0541(15) 0.0026(11) -0.0007(12) -0.0064(12) C2 0.0625(18) 0.0505(17) 0.0490(15) 0.0078(13) 0.0029(14) -0.0106(14) C3 0.0634(18) 0.0266(12) 0.0362(12) -0.0014(9) 0.0048(11) 0.0057(12) C4 0.0577(18) 0.0382(14) 0.0552(17) -0.0040(12) 0.0048(14) -0.0032(12) C5 0.0575(17) 0.0438(15) 0.0626(17) -0.0017(14) 0.0106(15) 0.0105(12) C6 0.0716(19) 0.0273(12) 0.0446(13) 0.0003(10) 0.0030(14) 0.0089(12) C7 0.0633(19) 0.0319(14) 0.0460(14) 0.0027(10) 0.0070(12) -0.0013(12) C8 0.0562(17) 0.0362(14) 0.0375(12) 0.0029(10) 0.0055(11) 0.0055(11) C9 0.0578(18) 0.0452(15) 0.0581(17) 0.0015(13) 0.0065(14) 0.0090(13) C10 0.0631(19) 0.076(2) 0.0520(16) 0.0001(16) 0.0154(14) 0.0195(17) C11 0.077(2) 0.0670(18) 0.0466(15) -0.0124(14) 0.0042(16) 0.0237(19) C12 0.081(2) 0.0372(15) 0.0443(14) -0.0065(12) -0.0021(14) 0.0179(14) C13 0.079(2) 0.0513(17) 0.0423(14) -0.0135(12) 0.0002(14) 0.0116(15) C14 0.099(3) 0.074(2) 0.062(2) 0.0079(17) -0.0132(17) 0.013(2) C15 0.118(4) 0.114(4) 0.075(3) 0.009(2) -0.023(2) 0.041(3) C16 0.081(3) 0.165(5) 0.079(3) -0.038(3) -0.014(2) 0.045(3) C17 0.067(3) 0.135(4) 0.093(3) -0.052(3) 0.014(2) -0.002(3) C18 0.084(3) 0.084(2) 0.0580(19) -0.0251(17) 0.0059(18) -0.003(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 C6 1.897(2) . ? F1 C2 1.306(4) . ? F2 C2 1.325(4) . ? F3 C2 1.321(3) . ? N1 C1 1.337(3) . ? N1 C3 1.439(3) . ? N1 C12 1.498(3) . ? O1 C1 1.205(3) . ? C1 C2 1.525(4) . ? C3 C4 1.361(4) . ? C3 C8 1.388(4) . ? C4 C5 1.385(4) . ? C4 H4 0.9300 . ? C5 C6 1.374(4) . ? C5 H5 0.9300 . ? C6 C7 1.369(4) . ? C7 C8 1.387(3) . ? C7 H7 0.9300 . ? C8 C9 1.496(4) . ? C9 C10 1.495(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.302(5) . ? C10 H10 0.9300 . ? C11 C12 1.494(5) . ? C11 H11 0.9300 . ? C12 C13 1.502(5) . ? C12 H12 0.9800 . ? C13 C14 1.364(5) . ? C13 C18 1.381(5) . ? C14 C15 1.373(6) . ? C14 H14 0.9300 . ? C15 C16 1.367(7) . ? C15 H15 0.9300 . ? C16 C17 1.349(7) . ? C16 H16 0.9300 . ? C17 C18 1.362(6) . ? C17 H17 0.9300 . ? C18 H18 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 C3 124.1(2) . . ? C1 N1 C12 118.1(2) . . ? C3 N1 C12 117.5(2) . . ? O1 C1 N1 125.2(3) . . ? O1 C1 C2 116.1(3) . . ? N1 C1 C2 118.6(2) . . ? F1 C2 F3 107.8(3) . . ? F1 C2 F2 107.0(3) . . ? F3 C2 F2 106.4(2) . . ? F1 C2 C1 111.0(3) . . ? F3 C2 C1 115.1(2) . . ? F2 C2 C1 109.0(3) . . ? C4 C3 C8 121.8(2) . . ? C4 C3 N1 120.4(3) . . ? C8 C3 N1 117.8(2) . . ? C3 C4 C5 120.3(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 118.0(3) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? C7 C6 C5 122.0(2) . . ? C7 C6 Br1 118.4(2) . . ? C5 C6 Br1 119.6(2) . . ? C6 C7 C8 120.1(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C3 117.7(3) . . ? C7 C8 C9 121.2(3) . . ? C3 C8 C9 121.1(2) . . ? C10 C9 C8 114.0(3) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C9 129.3(3) . . ? C11 C10 H10 115.4 . . ? C9 C10 H10 115.4 . . ? C10 C11 C12 130.1(3) . . ? C10 C11 H11 115.0 . . ? C12 C11 H11 115.0 . . ? C11 C12 N1 111.5(2) . . ? C11 C12 C13 114.1(2) . . ? N1 C12 C13 111.7(2) . . ? C11 C12 H12 106.3 . . ? N1 C12 H12 106.3 . . ? C13 C12 H12 106.3 . . ? C14 C13 C18 118.5(3) . . ? C14 C13 C12 121.4(3) . . ? C18 C13 C12 120.1(3) . . ? C13 C14 C15 120.9(4) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.9(4) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 119.4(4) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 121.3(5) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C13 120.0(4) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C1 O1 -165.2(3) . . . . ? C12 N1 C1 O1 7.8(5) . . . . ? C3 N1 C1 C2 16.3(4) . . . . ? C12 N1 C1 C2 -170.7(3) . . . . ? O1 C1 C2 F1 89.9(4) . . . . ? N1 C1 C2 F1 -91.5(3) . . . . ? O1 C1 C2 F3 -147.3(3) . . . . ? N1 C1 C2 F3 31.4(4) . . . . ? O1 C1 C2 F2 -27.7(4) . . . . ? N1 C1 C2 F2 150.9(3) . . . . ? C1 N1 C3 C4 67.1(4) . . . . ? C12 N1 C3 C4 -105.9(3) . . . . ? C1 N1 C3 C8 -113.1(3) . . . . ? C12 N1 C3 C8 73.9(3) . . . . ? C8 C3 C4 C5 2.1(4) . . . . ? N1 C3 C4 C5 -178.1(3) . . . . ? C3 C4 C5 C6 -1.6(5) . . . . ? C4 C5 C6 C7 -0.2(4) . . . . ? C4 C5 C6 Br1 179.5(2) . . . . ? C5 C6 C7 C8 1.4(4) . . . . ? Br1 C6 C7 C8 -178.3(2) . . . . ? C6 C7 C8 C3 -0.9(4) . . . . ? C6 C7 C8 C9 176.9(2) . . . . ? C4 C3 C8 C7 -0.8(4) . . . . ? N1 C3 C8 C7 179.4(2) . . . . ? C4 C3 C8 C9 -178.6(3) . . . . ? N1 C3 C8 C9 1.6(3) . . . . ? C7 C8 C9 C10 124.0(3) . . . . ? C3 C8 C9 C10 -58.3(4) . . . . ? C8 C9 C10 C11 41.7(5) . . . . ? C9 C10 C11 C12 2.4(6) . . . . ? C10 C11 C12 N1 7.2(4) . . . . ? C10 C11 C12 C13 -120.6(4) . . . . ? C1 N1 C12 C11 120.5(3) . . . . ? C3 N1 C12 C11 -66.0(3) . . . . ? C1 N1 C12 C13 -110.4(3) . . . . ? C3 N1 C12 C13 63.0(4) . . . . ? C11 C12 C13 C14 37.2(4) . . . . ? N1 C12 C13 C14 -90.5(4) . . . . ? C11 C12 C13 C18 -141.6(3) . . . . ? N1 C12 C13 C18 90.8(3) . . . . ? C18 C13 C14 C15 0.0(5) . . . . ? C12 C13 C14 C15 -178.7(3) . . . . ? C13 C14 C15 C16 0.3(6) . . . . ? C14 C15 C16 C17 -0.1(7) . . . . ? C15 C16 C17 C18 -0.3(7) . . . . ? C16 C17 C18 C13 0.6(6) . . . . ? C14 C13 C18 C17 -0.5(5) . . . . ? C12 C13 C18 C17 178.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.389 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.051