data_hyj1380201 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Br N O' _chemical_formula_weight 264.12 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3861(14) _cell_length_b 8.3872(14) _cell_length_c 9.0080(16) _cell_angle_alpha 95.574(12) _cell_angle_beta 100.912(12) _cell_angle_gamma 112.227(11) _cell_volume 565.89(17) _cell_formula_units_Z 2 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 2397 _cell_measurement_theta_min 2.344 _cell_measurement_theta_max 24.377 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 3.604 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4319 _exptl_absorpt_correction_T_max 0.4912 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(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 'Bruker APEX-II CCD' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7697 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2793 _reflns_number_gt 2095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (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^)+(0.0382P)^2^+0.1997P] 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 2793 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.58452(4) 0.75665(4) 0.83209(3) 0.05583(13) Uani 1 1 d . . . O1 O 0.3245(3) 0.8696(2) 0.3890(2) 0.0548(5) Uani 1 1 d . . . N1 N 0.0468(3) -0.1840(3) 0.8519(3) 0.0497(6) Uani 1 1 d . . . C12 C 0.3079(5) 0.6798(4) 0.1689(3) 0.0590(8) Uani 1 1 d . . . H1A H 0.3317 0.7827 0.1235 0.089 Uiso 1 1 calc R . . H1B H 0.1960 0.5896 0.1119 0.089 Uiso 1 1 calc R . . H1C H 0.4006 0.6395 0.1667 0.089 Uiso 1 1 calc R . . C11 C 0.3006(3) 0.7228(3) 0.3325(3) 0.0408(6) Uani 1 1 d . . . C10 C 0.2577(3) 0.5742(3) 0.4166(3) 0.0397(5) Uani 1 1 d . . . H3 H 0.2009 0.4626 0.3562 0.048 Uiso 1 1 calc R . . C8 C 0.2911(3) 0.5819(3) 0.5692(3) 0.0336(5) Uani 1 1 d . . . C5 C 0.2371(3) 0.4168(3) 0.6317(3) 0.0332(5) Uani 1 1 d . . . C4 C 0.2528(3) 0.2689(3) 0.5609(3) 0.0382(5) Uani 1 1 d . . . H6 H 0.2983 0.2745 0.4741 0.046 Uiso 1 1 calc R . . C3 C 0.2019(3) 0.1155(3) 0.6176(3) 0.0387(5) Uani 1 1 d . . . H7 H 0.2129 0.0185 0.5691 0.046 Uiso 1 1 calc R . . C2 C 0.1342(3) 0.1056(3) 0.7473(3) 0.0358(5) Uani 1 1 d . . . C1 C 0.0837(3) -0.0549(3) 0.8068(3) 0.0396(6) Uani 1 1 d . . . C6 C 0.1689(3) 0.4040(3) 0.7623(3) 0.0399(6) Uani 1 1 d . . . H10 H 0.1582 0.5008 0.8115 0.048 Uiso 1 1 calc R . . C7 C 0.1171(3) 0.2506(3) 0.8194(3) 0.0403(6) Uani 1 1 d . . . H11 H 0.0710 0.2441 0.9058 0.048 Uiso 1 1 calc R . . C9 C 0.3805(3) 0.7515(3) 0.6828(3) 0.0402(6) Uani 1 1 d . . . H12A H 0.2959 0.7669 0.7365 0.048 Uiso 1 1 calc R . . H12B H 0.4193 0.8479 0.6282 0.048 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 0.05131(18) 0.0595(2) 0.04489(18) 0.00156(13) -0.00387(12) 0.01913(14) O1 0.0775(14) 0.0417(11) 0.0456(11) 0.0113(9) 0.0142(10) 0.0244(10) N1 0.0577(14) 0.0462(13) 0.0486(13) 0.0148(11) 0.0199(11) 0.0200(11) C12 0.084(2) 0.0627(19) 0.0415(16) 0.0186(14) 0.0222(15) 0.0358(17) C11 0.0416(13) 0.0438(14) 0.0367(14) 0.0103(11) 0.0074(11) 0.0172(11) C10 0.0430(13) 0.0338(12) 0.0372(13) 0.0076(10) 0.0072(11) 0.0111(11) C8 0.0328(11) 0.0358(12) 0.0339(12) 0.0065(10) 0.0095(10) 0.0149(10) C5 0.0305(11) 0.0370(12) 0.0306(12) 0.0062(9) 0.0063(9) 0.0129(10) C4 0.0441(13) 0.0428(14) 0.0326(12) 0.0086(10) 0.0163(11) 0.0193(11) C3 0.0455(13) 0.0365(13) 0.0378(13) 0.0069(10) 0.0123(11) 0.0198(11) C2 0.0337(12) 0.0396(13) 0.0344(12) 0.0101(10) 0.0087(10) 0.0143(10) C1 0.0379(13) 0.0439(15) 0.0388(14) 0.0090(11) 0.0124(11) 0.0170(11) C6 0.0477(14) 0.0419(14) 0.0363(13) 0.0060(11) 0.0153(11) 0.0227(12) C7 0.0451(14) 0.0489(15) 0.0349(13) 0.0129(11) 0.0187(11) 0.0223(12) C9 0.0458(14) 0.0392(13) 0.0372(13) 0.0069(10) 0.0090(11) 0.0196(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 C9 1.949(2) . ? O1 C11 1.212(3) . ? N1 C1 1.146(3) . ? C12 C11 1.501(4) . ? C12 H1A 0.9600 . ? C12 H1B 0.9600 . ? C12 H1C 0.9600 . ? C11 C10 1.484(4) . ? C10 C8 1.340(3) . ? C10 H3 0.9300 . ? C8 C5 1.487(3) . ? C8 C9 1.501(3) . ? C5 C6 1.398(3) . ? C5 C4 1.402(3) . ? C4 C3 1.376(3) . ? C4 H6 0.9300 . ? C3 C2 1.389(3) . ? C3 H7 0.9300 . ? C2 C7 1.391(3) . ? C2 C1 1.440(4) . ? C6 C7 1.377(3) . ? C6 H10 0.9300 . ? C7 H11 0.9300 . ? C9 H12A 0.9700 . ? C9 H12B 0.9700 . ? 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 C11 C12 H1A 109.5 . . ? C11 C12 H1B 109.5 . . ? H1A C12 H1B 109.5 . . ? C11 C12 H1C 109.5 . . ? H1A C12 H1C 109.5 . . ? H1B C12 H1C 109.5 . . ? O1 C11 C10 123.1(2) . . ? O1 C11 C12 121.1(2) . . ? C10 C11 C12 115.8(2) . . ? C8 C10 C11 127.7(2) . . ? C8 C10 H3 116.2 . . ? C11 C10 H3 116.2 . . ? C10 C8 C5 119.6(2) . . ? C10 C8 C9 122.9(2) . . ? C5 C8 C9 117.4(2) . . ? C6 C5 C4 117.9(2) . . ? C6 C5 C8 121.2(2) . . ? C4 C5 C8 120.8(2) . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H6 119.5 . . ? C5 C4 H6 119.5 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H7 120.0 . . ? C2 C3 H7 120.0 . . ? C3 C2 C7 119.9(2) . . ? C3 C2 C1 119.5(2) . . ? C7 C2 C1 120.6(2) . . ? N1 C1 C2 178.0(3) . . ? C7 C6 C5 121.3(2) . . ? C7 C6 H10 119.4 . . ? C5 C6 H10 119.4 . . ? C6 C7 C2 119.7(2) . . ? C6 C7 H11 120.1 . . ? C2 C7 H11 120.1 . . ? C8 C9 Br1 111.56(16) . . ? C8 C9 H12A 109.3 . . ? Br1 C9 H12A 109.3 . . ? C8 C9 H12B 109.3 . . ? Br1 C9 H12B 109.3 . . ? H12A C9 H12B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.382 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.060