# 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_12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Br N O' _chemical_formula_weight 268.15 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 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 10.3914(12) _cell_length_b 11.2801(14) _cell_length_c 10.7843(13) _cell_angle_alpha 90.00 _cell_angle_beta 107.418(4) _cell_angle_gamma 90.00 _cell_volume 1206.1(3) _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 ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 3.382 _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 13973 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2901 _reflns_number_gt 1841 _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^)+(0.0653P)^2^+0.1334P] 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 2901 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 -0.14394(4) 0.20171(3) 0.91317(3) 0.04114(17) Uani 1 1 d . . . O1 O -0.3421(3) 0.2052(2) 0.6454(3) 0.0455(7) Uani 1 1 d . . . N1 N 0.0471(3) 0.4048(3) 0.8985(3) 0.0338(7) Uani 1 1 d . . . H1 H 0.0525 0.3539 0.9592 0.041 Uiso 1 1 calc R . . C6 C -0.2723(4) 0.3742(4) 0.5492(4) 0.0434(9) Uani 1 1 d . . . H1A H -0.3327 0.4373 0.5573 0.052 Uiso 1 1 calc R . . H1B H -0.3125 0.3351 0.4665 0.052 Uiso 1 1 calc R . . C1 C -0.2595(4) 0.2861(3) 0.6571(3) 0.0331(8) Uani 1 1 d . . . C2 C -0.1509(3) 0.3055(3) 0.7727(3) 0.0301(8) Uani 1 1 d . . . C3 C -0.0543(3) 0.3919(3) 0.7883(3) 0.0274(7) Uani 1 1 d . . . C7 C 0.1484(4) 0.4974(3) 0.9241(4) 0.0361(8) Uani 1 1 d . . . H5A H 0.1863 0.5059 1.0174 0.043 Uiso 1 1 calc R . . H5B H 0.1042 0.5716 0.8908 0.043 Uiso 1 1 calc R . . C8 C 0.2631(3) 0.4784(3) 0.8666(3) 0.0337(8) Uani 1 1 d . . . C13 C 0.3492(4) 0.5714(4) 0.8687(4) 0.0487(10) Uani 1 1 d . . . H7 H 0.3336 0.6442 0.9019 0.058 Uiso 1 1 calc R . . C12 C 0.4583(5) 0.5581(5) 0.8221(5) 0.0629(13) Uani 1 1 d . . . H8 H 0.5153 0.6219 0.8232 0.076 Uiso 1 1 calc R . . C11 C 0.4823(5) 0.4517(5) 0.7749(5) 0.0653(14) Uani 1 1 d . . . H9 H 0.5572 0.4420 0.7456 0.078 Uiso 1 1 calc R . . C5 C -0.1386(4) 0.4277(4) 0.5496(4) 0.0467(10) Uani 1 1 d . . . H10A H -0.0836 0.3672 0.5263 0.056 Uiso 1 1 calc R . . H10B H -0.1543 0.4899 0.4847 0.056 Uiso 1 1 calc R . . C4 C -0.0638(4) 0.4782(3) 0.6803(3) 0.0383(9) Uani 1 1 d . . . H11A H 0.0265 0.5005 0.6805 0.046 Uiso 1 1 calc R . . H11B H -0.1095 0.5493 0.6953 0.046 Uiso 1 1 calc R . . C10 C 0.3966(5) 0.3585(5) 0.7700(5) 0.0644(13) Uani 1 1 d . . . H12 H 0.4122 0.2861 0.7358 0.077 Uiso 1 1 calc R . . C9 C 0.2876(4) 0.3719(4) 0.8157(4) 0.0471(10) Uani 1 1 d . . . H13 H 0.2296 0.3083 0.8122 0.057 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 0.0451(3) 0.0370(2) 0.0386(2) 0.00641(16) 0.00829(17) -0.01039(18) O1 0.0448(16) 0.0457(17) 0.0392(15) -0.0019(12) 0.0021(12) -0.0120(13) N1 0.0322(16) 0.0337(16) 0.0376(16) -0.0006(13) 0.0138(14) -0.0070(13) C6 0.044(2) 0.049(2) 0.035(2) 0.0020(18) 0.0090(18) 0.0024(19) C1 0.0327(19) 0.035(2) 0.0328(19) -0.0011(15) 0.0114(16) 0.0064(17) C2 0.0309(19) 0.0295(18) 0.0295(18) 0.0059(14) 0.0083(15) 0.0023(15) C3 0.0273(18) 0.0292(18) 0.0306(18) 0.0022(14) 0.0163(15) 0.0068(15) C7 0.035(2) 0.0337(19) 0.043(2) -0.0072(16) 0.0178(17) -0.0081(16) C8 0.0305(19) 0.037(2) 0.0349(19) 0.0006(16) 0.0122(16) -0.0015(16) C13 0.049(3) 0.041(2) 0.062(3) 0.0029(19) 0.026(2) -0.0083(19) C12 0.052(3) 0.067(3) 0.080(3) 0.009(3) 0.035(3) -0.017(2) C11 0.051(3) 0.093(4) 0.067(3) 0.009(3) 0.040(2) 0.007(3) C5 0.055(3) 0.055(3) 0.036(2) 0.0122(18) 0.0213(19) 0.003(2) C4 0.037(2) 0.040(2) 0.041(2) 0.0096(17) 0.0149(17) -0.0010(17) C10 0.067(3) 0.064(3) 0.075(3) -0.012(3) 0.041(3) 0.004(3) C9 0.049(2) 0.043(2) 0.057(3) -0.010(2) 0.029(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 C2 1.899(3) . ? O1 C1 1.233(4) . ? N1 C3 1.339(4) . ? N1 C7 1.450(4) . ? N1 H1 0.8600 . ? C6 C1 1.505(5) . ? C6 C5 1.514(6) . ? C6 H1A 0.9700 . ? C6 H1B 0.9700 . ? C1 C2 1.426(5) . ? C2 C3 1.373(5) . ? C3 C4 1.498(5) . ? C7 C8 1.514(5) . ? C7 H5A 0.9700 . ? C7 H5B 0.9700 . ? C8 C13 1.374(5) . ? C8 C9 1.376(5) . ? C13 C12 1.379(6) . ? C13 H7 0.9300 . ? C12 C11 1.355(7) . ? C12 H8 0.9300 . ? C11 C10 1.369(7) . ? C11 H9 0.9300 . ? C5 C4 1.504(5) . ? C5 H10A 0.9700 . ? C5 H10B 0.9700 . ? C4 H11A 0.9700 . ? C4 H11B 0.9700 . ? C10 C9 1.372(6) . ? C10 H12 0.9300 . ? C9 H13 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 C3 N1 C7 125.5(3) . . ? C3 N1 H1 117.2 . . ? C7 N1 H1 117.2 . . ? C1 C6 C5 113.1(3) . . ? C1 C6 H1A 109.0 . . ? C5 C6 H1A 109.0 . . ? C1 C6 H1B 109.0 . . ? C5 C6 H1B 109.0 . . ? H1A C6 H1B 107.8 . . ? O1 C1 C2 123.1(3) . . ? O1 C1 C6 120.8(3) . . ? C2 C1 C6 116.0(3) . . ? C3 C2 C1 125.0(3) . . ? C3 C2 Br1 119.2(2) . . ? C1 C2 Br1 115.7(3) . . ? N1 C3 C2 122.6(3) . . ? N1 C3 C4 118.0(3) . . ? C2 C3 C4 119.4(3) . . ? N1 C7 C8 115.8(3) . . ? N1 C7 H5A 108.3 . . ? C8 C7 H5A 108.3 . . ? N1 C7 H5B 108.3 . . ? C8 C7 H5B 108.3 . . ? H5A C7 H5B 107.4 . . ? C13 C8 C9 118.5(4) . . ? C13 C8 C7 118.2(3) . . ? C9 C8 C7 123.3(3) . . ? C8 C13 C12 120.9(4) . . ? C8 C13 H7 119.6 . . ? C12 C13 H7 119.6 . . ? C11 C12 C13 119.8(4) . . ? C11 C12 H8 120.1 . . ? C13 C12 H8 120.1 . . ? C12 C11 C10 120.3(4) . . ? C12 C11 H9 119.9 . . ? C10 C11 H9 119.9 . . ? C4 C5 C6 111.7(3) . . ? C4 C5 H10A 109.3 . . ? C6 C5 H10A 109.3 . . ? C4 C5 H10B 109.3 . . ? C6 C5 H10B 109.3 . . ? H10A C5 H10B 107.9 . . ? C3 C4 C5 112.2(3) . . ? C3 C4 H11A 109.2 . . ? C5 C4 H11A 109.2 . . ? C3 C4 H11B 109.2 . . ? C5 C4 H11B 109.2 . . ? H11A C4 H11B 107.9 . . ? C11 C10 C9 119.9(4) . . ? C11 C10 H12 120.0 . . ? C9 C10 H12 120.0 . . ? C10 C9 C8 120.7(4) . . ? C10 C9 H13 119.7 . . ? C8 C9 H13 119.7 . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.483 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 962394' ####################################################################### # # 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_sp1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H Br N O2' _chemical_formula_weight 247.03 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 9.9209(13) _cell_length_b 9.2391(13) _cell_length_c 22.868(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2096.1(5) _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 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 3.893 _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 22611 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.41 _reflns_number_total 1930 _reflns_number_gt 1316 _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^)+(0.1018P)^2^+5.2254P] 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 1930 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 0.880 _refine_ls_restrained_S_all 0.880 _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 0.51301(6) 0.09803(7) 0.38810(3) 0.0696(3) Uani 1 1 d . . . C1 C 0.2151(5) 0.0837(7) 0.5229(2) 0.0602(15) Uani 1 1 d . . . H20A H 0.2218 0.1242 0.5614 0.090 Uiso 1 1 calc R . . H20B H 0.2050 -0.0194 0.5257 0.090 Uiso 1 1 calc R . . H20C H 0.1383 0.1241 0.5032 0.090 Uiso 1 1 calc R . . O1 O 0.4322(6) 0.1921(6) 0.5074(2) 0.0991(17) Uani 1 1 d . . . O2 O 0.2182(4) 0.2357(3) 0.38304(16) 0.0539(9) Uani 1 1 d . . . C8 C -0.1989(6) 0.0868(7) 0.2729(3) 0.0697(18) Uani 1 1 d . . . H1 H -0.2744 0.1054 0.2500 0.084 Uiso 1 1 calc R . . C9 C -0.1195(6) -0.0316(7) 0.2611(2) 0.0611(15) Uani 1 1 d . . . H2 H -0.1417 -0.0937 0.2306 0.073 Uiso 1 1 calc R . . C10 C -0.0069(5) -0.0577(6) 0.2947(2) 0.0496(12) Uani 1 1 d . . . H3 H 0.0472 -0.1375 0.2869 0.060 Uiso 1 1 calc R . . C5 C 0.0257(4) 0.0344(5) 0.34006(19) 0.0375(10) Uani 1 1 d . . . N1 N 0.1438(4) 0.0059(4) 0.37325(16) 0.0401(9) Uani 1 1 d . . . H5 H 0.1612 -0.0828 0.3817 0.048 Uiso 1 1 calc R . . C4 C 0.2292(5) 0.1059(5) 0.3921(2) 0.0415(11) Uani 1 1 d . . . C3 C 0.3477(5) 0.0510(5) 0.4292(2) 0.0468(12) Uani 1 1 d . . . H7 H 0.3408 -0.0544 0.4332 0.056 Uiso 1 1 calc R . . C2 C 0.3411(7) 0.1186(6) 0.4889(3) 0.0610(15) Uani 1 1 d . . . C7 C -0.1673(5) 0.1779(6) 0.3186(2) 0.0577(14) Uani 1 1 d . . . H9 H -0.2217 0.2574 0.3266 0.069 Uiso 1 1 calc R . . C6 C -0.0559(5) 0.1514(6) 0.3523(2) 0.0468(12) Uani 1 1 d . . . H10 H -0.0353 0.2124 0.3834 0.056 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 0.0462(4) 0.0849(5) 0.0776(5) 0.0086(3) -0.0033(3) 0.0005(3) C1 0.048(3) 0.090(4) 0.043(3) 0.000(3) 0.000(2) 0.020(3) O1 0.124(4) 0.104(4) 0.069(3) -0.017(3) -0.017(3) -0.048(3) O2 0.050(2) 0.0223(16) 0.090(3) 0.0055(15) -0.0160(18) -0.0014(14) C8 0.050(3) 0.091(5) 0.068(4) 0.024(3) -0.023(3) -0.020(3) C9 0.065(4) 0.070(4) 0.049(3) 0.000(3) -0.010(3) -0.026(3) C10 0.054(3) 0.047(3) 0.048(3) -0.002(2) 0.002(2) -0.013(2) C5 0.037(2) 0.036(2) 0.038(2) 0.0037(19) -0.0022(18) -0.0061(19) N1 0.041(2) 0.0266(18) 0.053(2) -0.0023(16) -0.0065(17) -0.0008(16) C4 0.036(2) 0.034(2) 0.054(3) -0.005(2) -0.003(2) 0.0005(19) C3 0.047(3) 0.028(2) 0.066(3) 0.000(2) -0.017(2) -0.002(2) C2 0.077(4) 0.049(3) 0.057(3) 0.001(3) -0.011(3) 0.005(3) C7 0.044(3) 0.066(3) 0.064(3) 0.009(3) -0.008(2) 0.004(3) C6 0.041(3) 0.045(3) 0.055(3) -0.006(2) -0.004(2) 0.004(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 C3 1.940(5) . ? C1 C2 1.507(8) . ? C1 H20A 0.9600 . ? C1 H20B 0.9600 . ? C1 H20C 0.9600 . ? O1 C2 1.207(7) . ? O2 C4 1.222(5) . ? C8 C9 1.374(9) . ? C8 C7 1.377(8) . ? C8 H1 0.9300 . ? C9 C10 1.377(7) . ? C9 H2 0.9300 . ? C10 C5 1.379(7) . ? C10 H3 0.9300 . ? C5 C6 1.380(7) . ? C5 N1 1.420(6) . ? N1 C4 1.326(6) . ? N1 H5 0.8600 . ? C4 C3 1.536(6) . ? C3 C2 1.502(8) . ? C3 H7 0.9800 . ? C7 C6 1.369(7) . ? C7 H9 0.9300 . ? C6 H10 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 C2 C1 H20A 109.5 . . ? C2 C1 H20B 109.5 . . ? H20A C1 H20B 109.5 . . ? C2 C1 H20C 109.5 . . ? H20A C1 H20C 109.5 . . ? H20B C1 H20C 109.5 . . ? C9 C8 C7 120.3(5) . . ? C9 C8 H1 119.8 . . ? C7 C8 H1 119.8 . . ? C8 C9 C10 119.6(5) . . ? C8 C9 H2 120.2 . . ? C10 C9 H2 120.2 . . ? C9 C10 C5 120.1(5) . . ? C9 C10 H3 119.9 . . ? C5 C10 H3 119.9 . . ? C10 C5 C6 119.8(4) . . ? C10 C5 N1 118.8(4) . . ? C6 C5 N1 121.4(4) . . ? C4 N1 C5 124.9(4) . . ? C4 N1 H5 117.5 . . ? C5 N1 H5 117.5 . . ? O2 C4 N1 124.8(4) . . ? O2 C4 C3 119.1(4) . . ? N1 C4 C3 116.0(4) . . ? C2 C3 C4 109.3(4) . . ? C2 C3 Br1 112.6(4) . . ? C4 C3 Br1 107.8(3) . . ? C2 C3 H7 109.0 . . ? C4 C3 H7 109.0 . . ? Br1 C3 H7 109.0 . . ? O1 C2 C3 121.3(6) . . ? O1 C2 C1 124.1(5) . . ? C3 C2 C1 114.6(5) . . ? C6 C7 C8 120.1(5) . . ? C6 C7 H9 120.0 . . ? C8 C7 H9 120.0 . . ? C7 C6 C5 120.0(5) . . ? C7 C6 H10 120.0 . . ? C5 C6 H10 120.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.41 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.744 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 962395'