data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H11 Br N2 O' _chemical_formula_sum 'C16 H11 Br N2 O' _chemical_formula_weight 327.18 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.3620(2) _cell_length_b 16.9968(7) _cell_length_c 12.6001(10) _cell_angle_alpha 90 _cell_angle_beta 105.892(5) _cell_angle_gamma 90 _cell_volume 1310.42(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9762 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 3.133 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.034 0 -1 0 0.148 1 0 0 0.076 -1 0 0 0.121 0 -1 1 0.118 0 0 -1 0.079 0 1 1 0.090 0 -1 -1 0.140 0 1 -1 0.042 1 0 -1 0.082 -1 0 1 0.163 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.559 _exptl_absorpt_correction_T_max 0.671 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 'Bruker Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9690 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.40 _reflns_number_total 2941 _reflns_number_gt 2246 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0137P)^2^+1.5617P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2941 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _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 1.36197(5) 0.58952(2) 0.09757(3) 0.03722(11) Uani 1 1 d . . . C11 C 1.0434(4) 0.44798(17) 0.3302(2) 0.0235(6) Uani 1 1 d . . . N1 N 0.9404(4) 0.40539(14) 0.39724(19) 0.0250(5) Uani 1 1 d . . . H1 H 0.8126 0.3874 0.3649 0.030 Uiso 1 1 d R . . N2 N 0.6771(4) 0.31877(14) 0.48198(19) 0.0226(5) Uani 1 1 d . . . O1 O 1.1941(3) 0.41055(14) 0.56582(17) 0.0349(5) Uani 1 1 d . . . C14 C 1.2305(5) 0.53124(17) 0.1908(3) 0.0268(6) Uani 1 1 d . . . C1 C 0.8646(4) 0.33971(16) 0.5512(2) 0.0224(6) Uani 1 1 d . . . C2 C 0.5417(4) 0.27191(16) 0.5224(2) 0.0226(6) Uani 1 1 d . . . C7 C 0.5988(4) 0.24565(17) 0.6332(2) 0.0236(6) Uani 1 1 d . . . C10 C 1.0178(5) 0.38945(17) 0.5067(3) 0.0255(6) Uani 1 1 d . . . C3 C 0.3392(5) 0.24829(17) 0.4499(3) 0.0259(6) Uani 1 1 d . . . H3 H 0.2995 0.2655 0.3770 0.031 Uiso 1 1 d R . . C6 C 0.4525(5) 0.19637(18) 0.6681(3) 0.0301(7) Uani 1 1 d . . . H6 H 0.4879 0.1791 0.7409 0.036 Uiso 1 1 d R . . C12 C 0.9184(4) 0.47039(17) 0.2257(3) 0.0262(6) Uani 1 1 d . . . H12 H 0.7710 0.4571 0.2028 0.031 Uiso 1 1 d R . . C5 C 0.2592(5) 0.17403(18) 0.5968(3) 0.0313(7) Uani 1 1 d . . . H5 H 0.1651 0.1410 0.6208 0.038 Uiso 1 1 d R . . C16 C 1.2653(4) 0.46742(18) 0.3636(3) 0.0276(7) Uani 1 1 d . . . H16 H 1.3510 0.4523 0.4329 0.033 Uiso 1 1 d R . . C8 C 0.8008(5) 0.27028(19) 0.7034(2) 0.0299(7) Uani 1 1 d . . . H8 H 0.8429 0.2545 0.7769 0.036 Uiso 1 1 d R . . C13 C 1.0098(5) 0.51232(18) 0.1556(3) 0.0285(7) Uani 1 1 d . . . H13 H 0.9251 0.5273 0.0861 0.034 Uiso 1 1 d R . . C15 C 1.3583(5) 0.50915(17) 0.2942(3) 0.0290(7) Uani 1 1 d . . . H15 H 1.5058 0.5223 0.3166 0.035 Uiso 1 1 d R . . C4 C 0.2029(5) 0.20060(18) 0.4869(3) 0.0293(7) Uani 1 1 d . . . H4 H 0.0703 0.1853 0.4389 0.035 Uiso 1 1 d R . . C9 C 0.9341(5) 0.31771(18) 0.6630(2) 0.0281(7) Uani 1 1 d . . . H9 H 1.0677 0.3349 0.7080 0.034 Uiso 1 1 d 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 0.03099(17) 0.03780(19) 0.0466(2) 0.00831(17) 0.01695(13) -0.00358(16) C11 0.0214(13) 0.0175(14) 0.0319(17) -0.0016(12) 0.0079(12) -0.0014(12) N1 0.0199(11) 0.0244(13) 0.0288(13) 0.0010(11) 0.0032(10) -0.0055(10) N2 0.0234(12) 0.0223(12) 0.0220(13) -0.0005(10) 0.0061(10) 0.0012(10) O1 0.0273(11) 0.0422(13) 0.0332(12) -0.0103(11) 0.0051(9) -0.0121(11) C14 0.0261(15) 0.0197(15) 0.0381(18) -0.0040(13) 0.0148(13) -0.0024(12) C1 0.0226(14) 0.0184(14) 0.0269(16) -0.0038(12) 0.0080(12) 0.0017(11) C2 0.0259(14) 0.0179(14) 0.0248(16) -0.0038(12) 0.0085(12) 0.0003(12) C7 0.0261(15) 0.0209(14) 0.0238(16) -0.0020(12) 0.0067(12) 0.0053(12) C10 0.0242(14) 0.0225(15) 0.0305(17) -0.0078(12) 0.0091(12) 0.0001(12) C3 0.0267(14) 0.0261(16) 0.0247(16) 0.0002(12) 0.0067(12) 0.0005(12) C6 0.0374(17) 0.0260(16) 0.0311(18) 0.0054(13) 0.0163(14) 0.0065(14) C12 0.0191(13) 0.0229(15) 0.0365(18) -0.0022(13) 0.0075(12) -0.0010(12) C5 0.0338(16) 0.0235(16) 0.0413(19) 0.0052(14) 0.0183(14) 0.0002(14) C16 0.0211(14) 0.0265(16) 0.0337(18) -0.0005(13) 0.0049(12) 0.0012(12) C8 0.0345(17) 0.0343(17) 0.0184(16) 0.0013(13) 0.0031(13) 0.0053(14) C13 0.0267(15) 0.0261(16) 0.0325(17) -0.0004(13) 0.0077(13) 0.0033(13) C15 0.0209(14) 0.0256(16) 0.0400(19) -0.0047(14) 0.0075(13) -0.0028(12) C4 0.0278(15) 0.0252(16) 0.0355(18) -0.0016(13) 0.0097(13) -0.0036(13) C9 0.0283(15) 0.0298(17) 0.0226(16) -0.0068(13) 0.0010(12) 0.0000(13) _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 1.897(3) . ? C11 C12 1.393(4) . ? C11 C16 1.398(4) . ? C11 N1 1.404(4) . ? N1 C10 1.359(4) . ? N1 H1 0.8599 . ? N2 C1 1.320(4) . ? N2 C2 1.370(4) . ? O1 C10 1.218(3) . ? C14 C15 1.385(4) . ? C14 C13 1.389(4) . ? C1 C9 1.406(4) . ? C1 C10 1.509(4) . ? C2 C7 1.415(4) . ? C2 C3 1.419(4) . ? C7 C6 1.409(4) . ? C7 C8 1.410(4) . ? C3 C4 1.359(4) . ? C3 H3 0.9300 . ? C6 C5 1.363(4) . ? C6 H6 0.9300 . ? C12 C13 1.381(4) . ? C12 H12 0.9301 . ? C5 C4 1.406(4) . ? C5 H5 0.9299 . ? C16 C15 1.379(4) . ? C16 H16 0.9300 . ? C8 C9 1.366(4) . ? C8 H8 0.9299 . ? C13 H13 0.9299 . ? C15 H15 0.9300 . ? C4 H4 0.9301 . ? C9 H9 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 C12 C11 C16 119.2(3) . . ? C12 C11 N1 118.0(2) . . ? C16 C11 N1 122.7(3) . . ? C10 N1 C11 127.9(2) . . ? C10 N1 H1 116.3 . . ? C11 N1 H1 115.8 . . ? C1 N2 C2 117.2(2) . . ? C15 C14 C13 121.3(3) . . ? C15 C14 Br1 118.6(2) . . ? C13 C14 Br1 120.1(2) . . ? N2 C1 C9 124.8(3) . . ? N2 C1 C10 117.6(3) . . ? C9 C1 C10 117.6(3) . . ? N2 C2 C7 122.2(3) . . ? N2 C2 C3 118.5(3) . . ? C7 C2 C3 119.2(3) . . ? C6 C7 C8 123.2(3) . . ? C6 C7 C2 118.9(3) . . ? C8 C7 C2 118.0(3) . . ? O1 C10 N1 125.4(3) . . ? O1 C10 C1 121.2(3) . . ? N1 C10 C1 113.4(2) . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C6 C7 120.9(3) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.5 . . ? C13 C12 C11 121.0(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 120.1 . . ? C15 C16 C11 120.3(3) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 120.1 . . ? C9 C8 C7 119.6(3) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C12 C13 C14 118.8(3) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.8 . . ? C16 C15 C14 119.5(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.3 . . ? C3 C4 C5 121.0(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.4 . . ? C8 C9 C1 118.3(3) . . ? C8 C9 H9 121.0 . . ? C1 C9 H9 120.8 . . ? 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 N1 H1 N2 0.86 2.23 2.663(3) 111.0 . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.324 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.083