data_090104cm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Br N O3' _chemical_formula_weight 346.18 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' 'O' 'O' 0.0106 0.0060 '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' '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.9944(11) _cell_length_b 6.2207(9) _cell_length_c 14.801(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.384(2) _cell_angle_gamma 90.00 _cell_volume 716.05(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2843 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 22.68 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 2.879 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.3922 _exptl_absorpt_correction_T_max 0.9447 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 7876 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3043 _reflns_number_gt 2466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0519P)^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 0.017(12) _refine_ls_number_reflns 3043 _refine_ls_number_parameters 193 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Br1 Br 0.09473(5) 1.00513(10) 0.45376(3) 0.07077(19) Uani 1 1 d . . . C1 C 0.2620(5) 0.8326(7) 0.4148(2) 0.0456(8) Uani 1 1 d . . . C2 C 0.4174(5) 0.9259(6) 0.4122(2) 0.0426(8) Uani 1 1 d . . . H2 H 0.4435 1.0649 0.4341 0.051 Uiso 1 1 calc R . . C3 C 0.5334(5) 0.8077(6) 0.3762(2) 0.0427(8) Uani 1 1 d . . . H3 H 0.6374 0.8693 0.3721 0.051 Uiso 1 1 calc R . . C4 C 0.4960(4) 0.5984(6) 0.3461(2) 0.0393(7) Uani 1 1 d . . . C5 C 0.3392(4) 0.5072(8) 0.3532(2) 0.0466(7) Uani 1 1 d . . . H5 H 0.3142 0.3655 0.3351 0.056 Uiso 1 1 calc R . . C6 C 0.2226(5) 0.6261(7) 0.3868(2) 0.0504(9) Uani 1 1 d . . . H6 H 0.1177 0.5666 0.3905 0.061 Uiso 1 1 calc R . . C7 C 0.6195(5) 0.4588(5) 0.3119(2) 0.0431(9) Uani 1 1 d . . . C8 C 0.7380(4) 0.5474(5) 0.2535(2) 0.0371(7) Uani 1 1 d . . . H8 H 0.8558 0.5533 0.2915 0.045 Uiso 1 1 calc R . . C9 C 0.6094(4) 0.7398(6) 0.1251(2) 0.0411(8) Uani 1 1 d . . . C10 C 0.7342(4) 0.4068(5) 0.1670(2) 0.0402(7) Uani 1 1 d . . . H10 H 0.6745 0.2716 0.1725 0.048 Uiso 1 1 calc R . . C11 C 0.9112(4) 0.3584(6) 0.1495(2) 0.0394(7) Uani 1 1 d . . . C12 C 0.9959(4) 0.5053(9) 0.1057(2) 0.0542(8) Uani 1 1 d . . . H12 H 0.9446 0.6366 0.0860 0.065 Uiso 1 1 calc R . . C13 C 1.1581(5) 0.4567(9) 0.0910(3) 0.0658(14) Uani 1 1 d . . . H13 H 1.2151 0.5549 0.0614 0.079 Uiso 1 1 calc R . . C14 C 1.2321(5) 0.2634(9) 0.1205(3) 0.0634(12) Uani 1 1 d . . . H14 H 1.3397 0.2300 0.1104 0.076 Uiso 1 1 calc R . . C15 C 1.1509(5) 0.1203(8) 0.1641(3) 0.0642(11) Uani 1 1 d . . . H15 H 1.2037 -0.0098 0.1845 0.077 Uiso 1 1 calc R . . C16 C 0.9888(5) 0.1662(7) 0.1787(3) 0.0536(10) Uani 1 1 d . . . H16 H 0.9331 0.0664 0.2082 0.064 Uiso 1 1 calc R . . N1 N 0.6269(3) 0.5406(5) 0.09704(17) 0.0454(7) Uani 1 1 d D . . H1 H 0.588(4) 0.518(8) 0.0389(10) 0.055 Uiso 1 1 d D . . O1 O 0.6312(5) 0.2693(5) 0.3292(2) 0.0766(10) Uani 1 1 d . . . O2 O 0.5385(4) 0.8943(5) 0.08310(17) 0.0590(7) Uani 1 1 d . . . O3 O 0.6873(3) 0.7582(4) 0.21778(14) 0.0417(5) 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 0.0633(3) 0.0798(3) 0.0805(3) 0.0043(3) 0.0397(2) 0.0193(3) C1 0.044(2) 0.057(2) 0.0408(17) 0.0011(15) 0.0202(15) 0.0046(17) C2 0.051(2) 0.0358(19) 0.0454(16) -0.0003(13) 0.0208(15) -0.0036(14) C3 0.048(2) 0.0401(19) 0.0439(17) 0.0035(14) 0.0188(15) -0.0045(15) C4 0.0456(18) 0.0383(18) 0.0366(14) 0.0032(13) 0.0146(13) -0.0015(15) C5 0.0531(19) 0.0414(18) 0.0456(15) 0.000(2) 0.0120(13) -0.012(2) C6 0.0415(19) 0.064(2) 0.0482(18) -0.0015(18) 0.0158(15) -0.0112(18) C7 0.058(2) 0.034(2) 0.0415(15) 0.0039(13) 0.0186(14) 0.0023(15) C8 0.0389(16) 0.034(2) 0.0386(14) 0.0019(13) 0.0090(12) 0.0006(13) C9 0.0392(19) 0.050(2) 0.0367(15) 0.0014(15) 0.0135(14) 0.0005(15) C10 0.0360(17) 0.0389(18) 0.0479(17) -0.0042(14) 0.0142(14) -0.0005(14) C11 0.0387(18) 0.0440(19) 0.0381(15) -0.0059(14) 0.0139(13) 0.0019(15) C12 0.0479(18) 0.060(2) 0.0587(18) 0.013(2) 0.0205(14) 0.005(2) C13 0.047(2) 0.092(4) 0.067(2) 0.005(2) 0.0299(18) -0.007(2) C14 0.039(2) 0.087(3) 0.065(2) -0.026(2) 0.0146(18) 0.010(2) C15 0.054(2) 0.057(3) 0.079(3) -0.017(2) 0.009(2) 0.012(2) C16 0.052(2) 0.044(2) 0.065(2) -0.0039(18) 0.0139(18) 0.0042(18) N1 0.0365(14) 0.057(2) 0.0397(12) -0.0102(14) 0.0017(11) 0.0060(14) O1 0.119(3) 0.0393(17) 0.093(2) 0.0191(15) 0.068(2) 0.0160(17) O2 0.0715(18) 0.0580(16) 0.0483(13) 0.0123(12) 0.0157(12) 0.0202(14) O3 0.0559(15) 0.0367(12) 0.0356(11) 0.0017(9) 0.0169(10) -0.0039(11) _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 1.905(4) . ? C1 C6 1.364(6) . ? C1 C2 1.379(5) . ? C2 C3 1.383(5) . ? C2 H2 0.9300 . ? C3 C4 1.386(5) . ? C3 H3 0.9300 . ? C4 C5 1.402(5) . ? C4 C7 1.489(5) . ? C5 C6 1.370(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.205(4) . ? C7 C8 1.525(5) . ? C8 O3 1.437(4) . ? C8 C10 1.545(4) . ? C8 H8 0.9800 . ? C9 O2 1.212(4) . ? C9 N1 1.324(5) . ? C9 O3 1.373(4) . ? C10 N1 1.446(4) . ? C10 C11 1.526(5) . ? C10 H10 0.9800 . ? C11 C16 1.370(5) . ? C11 C12 1.384(6) . ? C12 C13 1.397(5) . ? C12 H12 0.9300 . ? C13 C14 1.366(7) . ? C13 H13 0.9300 . ? C14 C15 1.350(7) . ? C14 H14 0.9300 . ? C15 C16 1.392(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N1 H1 0.857(10) . ? 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 C1 C2 122.3(4) . . ? C6 C1 Br1 119.5(3) . . ? C2 C1 Br1 118.1(3) . . ? C1 C2 C3 118.4(3) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.1(4) . . ? C3 C4 C7 123.1(3) . . ? C5 C4 C7 117.7(3) . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C1 C6 C5 119.3(4) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? O1 C7 C4 121.5(3) . . ? O1 C7 C8 116.5(3) . . ? C4 C7 C8 122.0(3) . . ? O3 C8 C7 112.3(3) . . ? O3 C8 C10 105.2(2) . . ? C7 C8 C10 111.7(3) . . ? O3 C8 H8 109.2 . . ? C7 C8 H8 109.2 . . ? C10 C8 H8 109.2 . . ? O2 C9 N1 130.7(3) . . ? O2 C9 O3 119.7(3) . . ? N1 C9 O3 109.6(3) . . ? N1 C10 C11 114.3(3) . . ? N1 C10 C8 99.3(2) . . ? C11 C10 C8 114.3(3) . . ? N1 C10 H10 109.5 . . ? C11 C10 H10 109.5 . . ? C8 C10 H10 109.5 . . ? C16 C11 C12 119.3(4) . . ? C16 C11 C10 119.2(3) . . ? C12 C11 C10 121.5(3) . . ? C11 C12 C13 120.1(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 119.3(4) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C15 C14 C13 120.8(4) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 120.4(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 120.0(4) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C9 N1 C10 113.7(3) . . ? C9 N1 H1 116(4) . . ? C10 N1 H1 130(3) . . ? C9 O3 C8 108.4(2) . . ? 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 C6 C1 C2 C3 2.8(5) . . . . ? Br1 C1 C2 C3 -174.3(2) . . . . ? C1 C2 C3 C4 -1.9(5) . . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? C2 C3 C4 C7 -176.3(3) . . . . ? C3 C4 C5 C6 2.0(5) . . . . ? C7 C4 C5 C6 178.1(3) . . . . ? C2 C1 C6 C5 -1.3(5) . . . . ? Br1 C1 C6 C5 175.8(3) . . . . ? C4 C5 C6 C1 -1.2(5) . . . . ? C3 C4 C7 O1 142.2(4) . . . . ? C5 C4 C7 O1 -33.7(5) . . . . ? C3 C4 C7 C8 -37.6(5) . . . . ? C5 C4 C7 C8 146.5(3) . . . . ? O1 C7 C8 O3 165.9(3) . . . . ? C4 C7 C8 O3 -14.3(4) . . . . ? O1 C7 C8 C10 48.0(4) . . . . ? C4 C7 C8 C10 -132.2(3) . . . . ? O3 C8 C10 N1 -18.8(3) . . . . ? C7 C8 C10 N1 103.3(3) . . . . ? O3 C8 C10 C11 103.3(3) . . . . ? C7 C8 C10 C11 -134.6(3) . . . . ? N1 C10 C11 C16 -148.4(3) . . . . ? C8 C10 C11 C16 98.0(4) . . . . ? N1 C10 C11 C12 32.3(4) . . . . ? C8 C10 C11 C12 -81.2(4) . . . . ? C16 C11 C12 C13 0.4(6) . . . . ? C10 C11 C12 C13 179.7(3) . . . . ? C11 C12 C13 C14 -0.2(6) . . . . ? C12 C13 C14 C15 -0.5(6) . . . . ? C13 C14 C15 C16 0.9(6) . . . . ? C12 C11 C16 C15 -0.1(5) . . . . ? C10 C11 C16 C15 -179.3(3) . . . . ? C14 C15 C16 C11 -0.6(6) . . . . ? O2 C9 N1 C10 174.9(4) . . . . ? O3 C9 N1 C10 -5.6(4) . . . . ? C11 C10 N1 C9 -106.8(3) . . . . ? C8 C10 N1 C9 15.3(4) . . . . ? O2 C9 O3 C8 171.5(3) . . . . ? N1 C9 O3 C8 -8.1(4) . . . . ? C7 C8 O3 C9 -104.4(3) . . . . ? C10 C8 O3 C9 17.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C3 H3 O1 0.93 2.57 3.097(5) 116.7 1_565 N1 H1 O2 0.857(10) 2.007(17) 2.838(3) 163(4) 2_645 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.565 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.062