# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_19fin _database_code_depnum_ccdc_archive 'CCDC 884937' #TrackingRef 'compound-3g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 Br N2 O3' _chemical_formula_weight 347.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 7.5775(7) _cell_length_b 11.0791(11) _cell_length_c 16.7543(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1406.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(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 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 4.099 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5419 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.79 _diffrn_reflns_theta_max 67.28 _reflns_number_total 2021 _reflns_number_gt 1815 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement ? _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^)+(0.0112P)^2^+7.7881P] 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 SHELXL _refine_ls_extinction_coef 0.0059(5) _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 0.04(5) _refine_ls_number_reflns 2021 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _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 0.10545(11) 0.13380(9) 0.47490(7) 0.0564(4) Uani 1 1 d . . . O1 O -0.4979(7) -0.1442(5) 0.5491(4) 0.0535(17) Uani 1 1 d . . . C1 C -0.5778(12) -0.0057(7) 0.7073(6) 0.049(2) Uani 1 1 d . . . H1 H -0.6770 -0.0525 0.6969 0.059 Uiso 1 1 calc R . . C2 C -0.5680(13) 0.0651(8) 0.7749(6) 0.053(3) Uani 1 1 d . . . H2 H -0.6617 0.0668 0.8107 0.064 Uiso 1 1 calc R . . C3 C -0.4175(12) 0.1341(8) 0.7894(6) 0.055(2) Uani 1 1 d . . . H3 H -0.4151 0.1822 0.8349 0.066 Uiso 1 1 calc R . . C4 C -0.2746(11) 0.1351(8) 0.7409(6) 0.048(2) Uani 1 1 d . . . H4 H -0.1744 0.1800 0.7530 0.057 Uiso 1 1 calc R . . C5 C -0.2859(10) 0.0642(6) 0.6708(5) 0.0325(17) Uani 1 1 d . . . N1 N -0.1589(9) 0.0489(6) 0.6124(5) 0.0452(19) Uani 1 1 d . . . H1A H -0.0531 0.0767 0.6151 0.054 Uiso 1 1 calc R . . C6 C -0.2297(9) -0.0216(6) 0.5450(5) 0.0330(18) Uani 1 1 d . . . C7 C -0.4078(11) -0.0679(6) 0.5808(5) 0.0392(18) Uani 1 1 d . . . C8 C -0.4359(10) -0.0049(7) 0.6556(6) 0.040(2) Uani 1 1 d . . . C9 C -0.2601(10) 0.0526(6) 0.4687(6) 0.0368(18) Uani 1 1 d . . . C10 C -0.4226(11) 0.0504(7) 0.4305(5) 0.042(2) Uani 1 1 d . . . H10 H -0.5137 0.0047 0.4523 0.051 Uiso 1 1 calc R . . C11 C -0.4532(13) 0.1153(9) 0.3596(6) 0.059(3) Uani 1 1 d . . . H11 H -0.5620 0.1109 0.3341 0.071 Uiso 1 1 calc R . . C12 C -0.3199(15) 0.1854(9) 0.3286(7) 0.063(3) Uani 1 1 d . . . H12 H -0.3398 0.2307 0.2828 0.075 Uiso 1 1 calc R . . C13 C -0.1580(13) 0.1888(8) 0.3649(6) 0.057(3) Uani 1 1 d . . . H13 H -0.0676 0.2353 0.3433 0.068 Uiso 1 1 calc R . . C14 C -0.1297(10) 0.1228(7) 0.4338(5) 0.0395(19) Uani 1 1 d . . . C15 C -0.1150(9) -0.1293(6) 0.5220(5) 0.0405(18) Uani 1 1 d . . . H15A H -0.1818 -0.1830 0.4877 0.049 Uiso 1 1 calc R . . H15B H -0.0131 -0.1012 0.4923 0.049 Uiso 1 1 calc R . . N2 N -0.0545(11) -0.1969(7) 0.5944(5) 0.054(2) Uani 1 1 d . . . O2 O -0.1608(12) -0.2576(8) 0.6294(5) 0.085(3) Uani 1 1 d . . . O3 O 0.0983(13) -0.1881(8) 0.6135(5) 0.093(3) Uani 1 1 d . . . 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 0.0338(5) 0.0576(6) 0.0777(7) -0.0011(5) 0.0084(5) -0.0143(4) O1 0.045(3) 0.048(3) 0.068(5) -0.015(3) 0.012(3) -0.023(3) C1 0.042(5) 0.038(4) 0.067(6) -0.002(4) 0.007(4) 0.002(4) C2 0.056(7) 0.047(5) 0.057(6) -0.007(4) 0.013(5) 0.013(4) C3 0.060(6) 0.044(4) 0.060(6) -0.011(5) -0.007(5) 0.013(5) C4 0.046(5) 0.034(4) 0.063(6) -0.017(5) -0.011(4) 0.003(4) C5 0.034(4) 0.026(3) 0.037(5) 0.001(3) 0.002(3) 0.005(3) N1 0.029(4) 0.040(4) 0.067(5) -0.014(4) -0.001(3) -0.007(3) C6 0.026(4) 0.024(3) 0.050(5) -0.004(3) 0.002(3) -0.003(3) C7 0.034(4) 0.029(4) 0.055(5) 0.003(4) 0.003(4) -0.008(4) C8 0.028(5) 0.027(4) 0.064(6) -0.010(4) 0.010(4) 0.002(3) C9 0.033(4) 0.026(3) 0.051(5) -0.002(4) 0.011(4) -0.001(3) C10 0.037(5) 0.040(4) 0.050(6) 0.000(4) -0.004(4) 0.000(4) C11 0.048(5) 0.067(6) 0.063(7) 0.010(6) -0.014(4) 0.011(5) C12 0.064(7) 0.065(6) 0.060(7) 0.012(5) 0.006(5) 0.013(5) C13 0.051(6) 0.047(5) 0.073(7) 0.016(5) 0.018(5) 0.003(4) C14 0.032(4) 0.033(4) 0.054(5) 0.000(4) 0.004(3) 0.005(4) C15 0.032(4) 0.027(3) 0.062(5) 0.005(4) 0.003(4) 0.001(4) N2 0.047(5) 0.042(4) 0.075(6) -0.003(4) -0.004(4) 0.013(3) O2 0.081(6) 0.097(6) 0.078(6) 0.036(5) 0.024(5) 0.004(5) O3 0.078(6) 0.101(6) 0.099(7) 0.023(5) -0.043(6) 0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C14 1.914(8) . ? O1 C7 1.210(9) . ? C1 C2 1.379(12) . ? C1 C8 1.380(12) . ? C1 H1 0.9300 . ? C2 C3 1.395(13) . ? C2 H2 0.9300 . ? C3 C4 1.353(13) . ? C3 H3 0.9300 . ? C4 C5 1.416(11) . ? C4 H4 0.9300 . ? C5 N1 1.383(10) . ? C5 C8 1.394(11) . ? N1 C6 1.474(10) . ? N1 H1A 0.8600 . ? C6 C15 1.525(9) . ? C6 C9 1.537(11) . ? C6 C7 1.564(10) . ? C7 C8 1.451(11) . ? C9 C14 1.386(10) . ? C9 C10 1.388(12) . ? C10 C11 1.408(12) . ? C10 H10 0.9300 . ? C11 C12 1.376(14) . ? C11 H11 0.9300 . ? C12 C13 1.369(15) . ? C12 H12 0.9300 . ? C13 C14 1.384(12) . ? C13 H13 0.9300 . ? C15 N2 1.497(11) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? N2 O2 1.202(10) . ? N2 O3 1.205(11) . ? 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 C8 118.0(9) . . ? C2 C1 H1 121.0 . . ? C8 C1 H1 121.0 . . ? C1 C2 C3 119.9(9) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 123.7(9) . . ? C4 C3 H3 118.2 . . ? C2 C3 H3 118.2 . . ? C3 C4 C5 116.4(8) . . ? C3 C4 H4 121.8 . . ? C5 C4 H4 121.8 . . ? N1 C5 C8 111.8(7) . . ? N1 C5 C4 127.8(7) . . ? C8 C5 C4 120.4(7) . . ? C5 N1 C6 110.8(6) . . ? C5 N1 H1A 124.6 . . ? C6 N1 H1A 124.6 . . ? N1 C6 C15 113.6(6) . . ? N1 C6 C9 114.1(6) . . ? C15 C6 C9 107.1(6) . . ? N1 C6 C7 101.1(6) . . ? C15 C6 C7 109.4(6) . . ? C9 C6 C7 111.4(6) . . ? O1 C7 C8 129.3(8) . . ? O1 C7 C6 123.2(8) . . ? C8 C7 C6 107.5(6) . . ? C1 C8 C5 121.6(8) . . ? C1 C8 C7 130.8(8) . . ? C5 C8 C7 107.6(7) . . ? C14 C9 C10 116.7(8) . . ? C14 C9 C6 122.9(7) . . ? C10 C9 C6 120.4(7) . . ? C9 C10 C11 121.7(8) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 119.1(9) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C13 C12 C11 120.4(10) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.6(9) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C9 122.5(8) . . ? C13 C14 Br1 114.3(6) . . ? C9 C14 Br1 123.2(6) . . ? N2 C15 C6 111.2(7) . . ? N2 C15 H15A 109.4 . . ? C6 C15 H15A 109.4 . . ? N2 C15 H15B 109.4 . . ? C6 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? O2 N2 O3 124.0(10) . . ? O2 N2 C15 118.0(8) . . ? O3 N2 C15 118.0(9) . . ? _diffrn_measured_fraction_theta_max 0.843 _diffrn_reflns_theta_full 67.28 _diffrn_measured_fraction_theta_full 0.843 _refine_diff_density_max 0.825 _refine_diff_density_min -1.749 _refine_diff_density_rms 0.139