# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 F N2' _chemical_formula_sum 'C18 H17 F N2' _chemical_formula_weight 280.34 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 17.924(7) _cell_length_b 14.035(6) _cell_length_c 5.888(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1481.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour white _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5087 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 23.47 _reflns_number_total 1837 _reflns_number_gt 1435 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0614P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2.4(18) _refine_ls_number_reflns 1837 _refine_ls_number_parameters 192 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.007 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 0.49182(13) 0.86459(16) -0.5968(5) 0.0923(9) Uani 1 1 d . . . N1 N 0.17195(14) 0.94477(19) 0.2583(5) 0.0448(7) Uani 1 1 d . . . N2 N 0.15477(15) 0.85083(18) 0.2346(6) 0.0481(8) Uani 1 1 d . . . C1 C 0.4330(2) 0.8720(3) -0.4523(8) 0.0612(12) Uani 1 1 d . . . C2 C 0.4421(2) 0.9197(3) -0.2514(9) 0.0612(11) Uani 1 1 d . . . H2 H 0.4876 0.9475 -0.2152 0.073 Uiso 1 1 calc R . . C3 C 0.38288(19) 0.9260(2) -0.1041(7) 0.0527(10) Uani 1 1 d . . . H3 H 0.3887 0.9582 0.0327 0.063 Uiso 1 1 calc R . . C4 C 0.31368(18) 0.8845(2) -0.1563(6) 0.0412(9) Uani 1 1 d . . . C5 C 0.25091(18) 0.8909(2) 0.0053(6) 0.0427(9) Uani 1 1 d . . . C6 C 0.22994(18) 0.9699(2) 0.1242(6) 0.0453(9) Uani 1 1 d . . . H6 H 0.2516 1.0300 0.1148 0.054 Uiso 1 1 calc R . . C7 C 0.12995(18) 1.0042(2) 0.4073(6) 0.0423(8) Uani 1 1 d . . . C8 C 0.11483(17) 1.0970(2) 0.3479(7) 0.0510(10) Uani 1 1 d . . . H8 H 0.1317 1.1215 0.2103 0.061 Uiso 1 1 calc R . . C9 C 0.0743(2) 1.1536(3) 0.4954(8) 0.0585(11) Uani 1 1 d . . . H9 H 0.0646 1.2166 0.4571 0.070 Uiso 1 1 calc R . . C10 C 0.04832(19) 1.1184(3) 0.6957(7) 0.0581(12) Uani 1 1 d . . . H10 H 0.0204 1.1570 0.7919 0.070 Uiso 1 1 calc R . . C11 C 0.3071(2) 0.8388(2) -0.3636(7) 0.0507(10) Uani 1 1 d . . . H11 H 0.2614 0.8124 -0.4038 0.061 Uiso 1 1 calc R . . C12 C 0.3664(2) 0.8314(2) -0.5129(7) 0.0563(10) Uani 1 1 d . . . H12 H 0.3612 0.7997 -0.6507 0.068 Uiso 1 1 calc R . . C13 C 0.20232(17) 0.8178(2) 0.0792(6) 0.0438(9) Uani 1 1 d . . . C14 C 0.06334(18) 1.0254(3) 0.7562(7) 0.0564(10) Uani 1 1 d . . . H14 H 0.0459 1.0013 0.8935 0.068 Uiso 1 1 calc R . . C15 C 0.10464(18) 0.9679(2) 0.6110(7) 0.0492(9) Uani 1 1 d . . . H15 H 0.1152 0.9052 0.6510 0.059 Uiso 1 1 calc R . . C16 C 0.20019(19) 0.7142(2) 0.0136(7) 0.0524(10) Uani 1 1 d . . . H16 H 0.2410 0.7028 -0.0938 0.063 Uiso 1 1 calc R . . C17 C 0.1276(2) 0.6897(3) -0.1058(10) 0.0892(15) Uani 1 1 d . . . H17A H 0.0864 0.7021 -0.0058 0.134 Uiso 1 1 calc R . . H17B H 0.1277 0.6235 -0.1468 0.134 Uiso 1 1 calc R . . H17C H 0.1227 0.7279 -0.2402 0.134 Uiso 1 1 calc R . . C18 C 0.2126(3) 0.6496(3) 0.2180(8) 0.0824(14) Uani 1 1 d . . . H18A H 0.2589 0.6661 0.2903 0.124 Uiso 1 1 calc R . . H18B H 0.2145 0.5845 0.1688 0.124 Uiso 1 1 calc R . . H18C H 0.1724 0.6576 0.3238 0.124 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 0.0749(15) 0.1002(17) 0.102(2) -0.0005(17) 0.0466(17) 0.0001(13) N1 0.0405(16) 0.0443(17) 0.0496(18) -0.0021(16) 0.0061(17) 0.0018(13) N2 0.0472(16) 0.0389(17) 0.058(2) -0.0009(15) 0.0047(18) 0.0000(14) C1 0.050(3) 0.064(3) 0.070(4) 0.008(3) 0.023(3) 0.008(2) C2 0.046(2) 0.060(2) 0.078(3) 0.001(2) 0.011(3) -0.0041(18) C3 0.051(2) 0.051(2) 0.057(3) 0.0008(19) 0.004(2) -0.0031(17) C4 0.041(2) 0.0389(17) 0.044(2) 0.0034(18) 0.0009(19) 0.0037(15) C5 0.0405(19) 0.043(2) 0.045(2) 0.0024(18) -0.0027(18) 0.0009(16) C6 0.0397(19) 0.049(2) 0.047(2) 0.006(2) 0.001(2) -0.0078(17) C7 0.0368(18) 0.041(2) 0.049(2) -0.0009(19) -0.0006(19) -0.0009(16) C8 0.048(2) 0.050(2) 0.055(2) 0.002(2) 0.003(2) -0.0058(17) C9 0.058(2) 0.047(2) 0.070(3) -0.006(2) 0.003(3) -0.0005(19) C10 0.044(2) 0.068(3) 0.062(3) -0.020(2) 0.008(2) -0.0019(19) C11 0.045(2) 0.055(2) 0.052(3) 0.005(2) 0.001(2) -0.0016(17) C12 0.064(3) 0.056(2) 0.049(2) 0.006(2) 0.006(2) 0.009(2) C13 0.0374(19) 0.045(2) 0.049(2) 0.0028(19) -0.001(2) -0.0002(16) C14 0.047(2) 0.071(3) 0.051(2) -0.008(2) 0.007(2) -0.0074(19) C15 0.047(2) 0.050(2) 0.051(2) 0.006(2) -0.006(2) -0.0014(17) C16 0.044(2) 0.046(2) 0.067(3) -0.0055(19) 0.007(2) -0.0037(16) C17 0.080(3) 0.069(3) 0.118(4) -0.028(3) -0.022(3) -0.008(2) C18 0.108(3) 0.050(2) 0.089(4) 0.011(2) 0.003(3) 0.000(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 C1 1.359(4) . ? N1 C6 1.352(4) . ? N1 N2 1.361(4) . ? N1 C7 1.425(4) . ? N2 C13 1.334(4) . ? C1 C12 1.369(5) . ? C1 C2 1.369(6) . ? C2 C3 1.373(5) . ? C2 H2 0.9300 . ? C3 C4 1.404(5) . ? C3 H3 0.9300 . ? C4 C11 1.384(5) . ? C4 C5 1.476(5) . ? C5 C6 1.365(4) . ? C5 C13 1.414(4) . ? C6 H6 0.9300 . ? C7 C8 1.376(4) . ? C7 C15 1.380(5) . ? C8 C9 1.383(5) . ? C8 H8 0.9300 . ? C9 C10 1.361(6) . ? C9 H9 0.9300 . ? C10 C14 1.379(5) . ? C10 H10 0.9300 . ? C11 C12 1.384(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C16 1.505(5) . ? C14 C15 1.390(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.519(5) . ? C16 C18 1.523(5) . ? C16 H16 0.9800 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C6 N1 N2 111.5(3) . . ? C6 N1 C7 127.8(3) . . ? N2 N1 C7 120.7(3) . . ? C13 N2 N1 105.2(3) . . ? F1 C1 C12 118.8(4) . . ? F1 C1 C2 119.1(4) . . ? C12 C1 C2 122.2(4) . . ? C3 C2 C1 119.0(4) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 121.2(4) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C11 C4 C3 117.4(3) . . ? C11 C4 C5 122.1(3) . . ? C3 C4 C5 120.5(3) . . ? C6 C5 C13 105.2(3) . . ? C6 C5 C4 126.2(3) . . ? C13 C5 C4 128.6(3) . . ? N1 C6 C5 107.4(3) . . ? N1 C6 H6 126.3 . . ? C5 C6 H6 126.3 . . ? C8 C7 C15 120.4(3) . . ? C8 C7 N1 120.1(3) . . ? C15 C7 N1 119.5(3) . . ? C7 C8 C9 119.2(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 121.1(4) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C14 120.0(4) . . ? C9 C10 H10 120.0 . . ? C14 C10 H10 120.0 . . ? C12 C11 C4 122.0(3) . . ? C12 C11 H11 119.0 . . ? C4 C11 H11 119.0 . . ? C1 C12 C11 118.2(4) . . ? C1 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? N2 C13 C5 110.7(3) . . ? N2 C13 C16 119.7(3) . . ? C5 C13 C16 129.6(3) . . ? C10 C14 C15 119.7(4) . . ? C10 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C7 C15 C14 119.7(3) . . ? C7 C15 H15 120.1 . . ? C14 C15 H15 120.2 . . ? C13 C16 C17 111.1(3) . . ? C13 C16 C18 111.6(3) . . ? C17 C16 C18 110.9(4) . . ? C13 C16 H16 107.7 . . ? C17 C16 H16 107.7 . . ? C18 C16 H16 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.116 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.035 _atom_sites_special_details ; The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual = -1, Ralpha = 0.069 ; _database_code_depnum_ccdc_archive 'CCDC 941068' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_gp100_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 Br N O' _chemical_formula_sum 'C15 H13 Br N O' _chemical_formula_weight 302.17 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' 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 C12/c1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.75(3) _cell_length_b 10.556(9) _cell_length_c 8.407(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.360(10) _cell_angle_gamma 90.00 _cell_volume 2644(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 3.097 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5782 _diffrn_reflns_av_R_equivalents 0.0865 _diffrn_reflns_av_sigmaI/netI 0.1131 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.27 _reflns_number_total 2248 _reflns_number_gt 983 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1465P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2248 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1844 _refine_ls_R_factor_gt 0.0868 _refine_ls_wR_factor_ref 0.2858 _refine_ls_wR_factor_gt 0.2361 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.092 _refine_ls_shift/su_mean 0.018 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 0.45157(4) 0.63026(15) 1.07082(17) 0.1081(8) Uani 1 1 d . . . O1 O 0.1957(2) 0.5168(7) 0.5043(9) 0.088(2) Uani 1 1 d . . . N1 N 0.2419(3) 0.5050(9) 0.5795(11) 0.083(3) Uani 1 1 d . . . C1 C 0.3899(3) 0.6220(10) 0.9537(12) 0.064(3) Uani 1 1 d . . . C2 C 0.3603(4) 0.7145(10) 0.9714(12) 0.070(3) Uani 1 1 d . . . H2 H 0.3701 0.7826 1.0412 0.084 Uiso 1 1 calc R . . C3 C 0.3154(3) 0.7063(9) 0.8844(12) 0.062(3) Uani 1 1 d . . . H3 H 0.2951 0.7684 0.8980 0.075 Uiso 1 1 calc R . . C4 C 0.3007(3) 0.6061(8) 0.7776(10) 0.049(2) Uani 1 1 d . . . C5 C 0.2545(4) 0.5975(8) 0.6830(12) 0.062(3) Uani 1 1 d . . . C6 C 0.2171(3) 0.6842(10) 0.6918(12) 0.064(3) Uani 1 1 d . . . H6A H 0.2258 0.7724 0.6895 0.077 Uiso 1 1 calc R . . H6B H 0.2062 0.6687 0.7890 0.077 Uiso 1 1 calc R . . C7 C 0.1818(4) 0.6461(10) 0.5325(13) 0.079(3) Uani 1 1 d . . . H7 H 0.1844 0.7012 0.4417 0.095 Uiso 1 1 calc R . . C8 C 0.1337(3) 0.6411(8) 0.5433(11) 0.055(2) Uani 1 1 d . . . C9 C 0.1028(4) 0.7233(10) 0.4514(13) 0.076(3) Uani 1 1 d . . . H9 H 0.1122 0.7823 0.3849 0.091 Uiso 1 1 calc R . . C10 C 0.0587(5) 0.7211(12) 0.4547(16) 0.098(4) Uani 1 1 d . . . H10 H 0.0385 0.7776 0.3908 0.118 Uiso 1 1 calc R . . C11 C 0.0440(4) 0.6345(13) 0.554(2) 0.103(5) Uani 1 1 d . . . H11 H 0.0140 0.6313 0.5556 0.124 Uiso 1 1 calc R . . C12 C 0.3329(3) 0.5131(9) 0.7654(11) 0.064(3) Uani 1 1 d . . . H12 H 0.3235 0.4436 0.6977 0.077 Uiso 1 1 calc R . . C13 C 0.3769(3) 0.5201(9) 0.8477(12) 0.067(3) Uani 1 1 d . . . H13 H 0.3974 0.4592 0.8336 0.080 Uiso 1 1 calc R . . C14 C 0.0738(4) 0.5554(12) 0.6461(15) 0.087(3) Uani 1 1 d . . . H14 H 0.0643 0.4975 0.7136 0.104 Uiso 1 1 calc R . . C15 C 0.1189(4) 0.5580(10) 0.6434(13) 0.079(3) Uani 1 1 d . . . H15 H 0.1391 0.5030 0.7101 0.095 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 0.0635(9) 0.1579(15) 0.0966(11) -0.0065(8) 0.0078(7) -0.0183(7) O1 0.075(5) 0.093(5) 0.089(5) -0.041(4) 0.007(4) 0.003(4) N1 0.072(6) 0.092(6) 0.086(7) -0.040(6) 0.019(5) -0.005(5) C1 0.053(6) 0.079(7) 0.059(6) 0.000(6) 0.011(5) -0.020(5) C2 0.091(9) 0.066(7) 0.058(6) -0.011(5) 0.026(6) -0.014(6) C3 0.077(8) 0.056(6) 0.054(6) 0.000(5) 0.017(5) 0.003(5) C4 0.049(6) 0.057(6) 0.042(5) -0.002(4) 0.015(4) -0.002(4) C5 0.088(8) 0.054(6) 0.055(6) -0.005(5) 0.039(6) -0.001(5) C6 0.056(6) 0.074(6) 0.061(6) -0.015(5) 0.008(5) 0.000(5) C7 0.087(9) 0.088(9) 0.060(7) 0.017(6) 0.016(6) -0.007(6) C8 0.054(6) 0.055(6) 0.046(5) 0.002(5) -0.006(5) 0.000(5) C9 0.083(8) 0.070(7) 0.072(7) 0.007(6) 0.012(6) 0.005(6) C10 0.114(12) 0.068(8) 0.096(10) 0.004(7) -0.006(9) 0.021(8) C11 0.066(8) 0.095(10) 0.150(14) -0.032(9) 0.030(9) 0.005(7) C12 0.080(8) 0.060(6) 0.056(6) -0.008(5) 0.024(6) -0.009(5) C13 0.054(6) 0.071(7) 0.078(7) -0.005(6) 0.021(6) -0.008(5) C14 0.072(8) 0.100(9) 0.085(9) 0.005(7) 0.013(7) 0.001(7) C15 0.087(9) 0.079(8) 0.065(7) 0.021(6) 0.006(6) 0.007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.908(10) . ? O1 N1 1.408(10) . ? O1 C7 1.467(12) . ? N1 C5 1.301(12) . ? C1 C2 1.368(14) . ? C1 C13 1.391(13) . ? C2 C3 1.397(13) . ? C2 H2 0.9300 . ? C3 C4 1.389(12) . ? C3 H3 0.9300 . ? C4 C12 1.414(12) . ? C4 C5 1.451(13) . ? C5 C6 1.486(13) . ? C6 C7 1.553(14) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.502(14) . ? C7 H7 0.9800 . ? C8 C15 1.370(14) . ? C8 C9 1.375(13) . ? C9 C10 1.364(16) . ? C9 H9 0.9300 . ? C10 C11 1.383(18) . ? C10 H10 0.9300 . ? C11 C14 1.338(17) . ? C11 H11 0.9300 . ? C12 C13 1.360(11) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.391(14) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 O1 C7 108.2(7) . . ? C5 N1 O1 109.5(8) . . ? C2 C1 C13 121.8(9) . . ? C2 C1 Br1 120.9(8) . . ? C13 C1 Br1 117.3(8) . . ? C1 C2 C3 119.9(9) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 120.3(9) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C12 117.1(9) . . ? C3 C4 C5 121.2(8) . . ? C12 C4 C5 121.7(8) . . ? N1 C5 C4 120.1(9) . . ? N1 C5 C6 112.9(9) . . ? C4 C5 C6 126.9(9) . . ? C5 C6 C7 100.5(8) . . ? C5 C6 H6A 111.7 . . ? C7 C6 H6A 111.7 . . ? C5 C6 H6B 111.7 . . ? C7 C6 H6B 111.7 . . ? H6A C6 H6B 109.5 . . ? O1 C7 C8 108.0(8) . . ? O1 C7 C6 102.2(8) . . ? C8 C7 C6 116.4(9) . . ? O1 C7 H7 110.0 . . ? C8 C7 H7 110.0 . . ? C6 C7 H7 110.0 . . ? C15 C8 C9 117.3(10) . . ? C15 C8 C7 122.8(9) . . ? C9 C8 C7 119.9(9) . . ? C10 C9 C8 122.1(11) . . ? C10 C9 H9 118.9 . . ? C8 C9 H9 118.9 . . ? C9 C10 C11 119.8(11) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C14 C11 C10 119.0(12) . . ? C14 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C13 C12 C4 123.4(9) . . ? C13 C12 H12 118.3 . . ? C4 C12 H12 118.3 . . ? C12 C13 C1 117.5(9) . . ? C12 C13 H13 121.3 . . ? C1 C13 H13 121.3 . . ? C11 C14 C15 121.3(12) . . ? C11 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C8 C15 C14 120.5(10) . . ? C8 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.27 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 1.136 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.110 _atom_sites_special_details ; The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.3, Nqual = 0, Ralpha = 0.044 ; _database_code_depnum_ccdc_archive 'CCDC 945312'