#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/63/2226351.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226351
loop_
_publ_author_name
'Wang, Zhi-jian'
'Jia, Wei-min'
'Yao, Hong-guo'
'Qiu, Hong'
'Wang, Wei'
_publ_section_title
;
 2-(4-Bromophenyl)quinoxaline
;
_journal_coeditor_code           ZS2039
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1380
_journal_paper_doi               10.1107/S160053681001723X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H9 Br N2'
_chemical_formula_moiety         'C14 H9 Br N2'
_chemical_formula_sum            'C14 H9 Br N2'
_chemical_formula_weight         285.14
_chemical_melting_point          418
_chemical_name_systematic
;
2-(4-Bromophenyl)quinoxaline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 109.53(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.959(3)
_cell_length_b                   5.9031(12)
_cell_length_c                   14.497(3)
_cell_measurement_reflns_used    3221
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.886
_cell_measurement_theta_min      2.863
_cell_volume                     1125.8(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Model name? CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8910
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.626
_exptl_absorpt_correction_T_max  0.7132
_exptl_absorpt_correction_T_min  0.5308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.687
_refine_ls_extinction_coef       0.0540(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0337P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0745
_reflns_number_gt                1763
_reflns_number_total             2683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2039.cif
_cod_data_source_block           I
_cod_original_cell_volume        1125.9(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226351
_cod_database_fobs_code          2226351
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.460263(18) 1.10538(4) 0.33474(2) 0.03213(13) Uani d . 1 . .
N N1 -0.12149(15) 0.6560(3) 0.02060(15) 0.0218(5) Uani d . 1 . .
N N2 -0.05847(15) 1.0700(3) 0.12055(14) 0.0169(4) Uani d . 1 . .
C C1 0.00712(17) 0.9095(4) 0.11986(16) 0.0150(5) Uani d . 1 . .
C C2 -0.02653(17) 0.7012(4) 0.07034(17) 0.0210(6) Uani d . 1 . .
H H2 0.0229 0.5882 0.0736 0.025 Uiso calc R 1 . .
C C3 -0.19054(16) 0.8203(4) 0.02054(16) 0.0160(5) Uani d . 1 . .
C C4 -0.29514(17) 0.7808(4) -0.02863(17) 0.0204(6) Uani d . 1 . .
H H4 -0.3168 0.6436 -0.0636 0.024 Uiso calc R 1 . .
C C5 -0.36496(18) 0.9398(4) -0.02576(17) 0.0213(6) Uani d . 1 . .
H H5 -0.4352 0.9126 -0.0588 0.026 Uiso calc R 1 . .
C C6 -0.33379(19) 1.1438(4) 0.02573(18) 0.0229(6) Uani d . 1 . .
H H6 -0.3833 1.2523 0.0279 0.028 Uiso calc R 1 . .
C C7 -0.23291(17) 1.1877(4) 0.07274(17) 0.0176(5) Uani d . 1 . .
H H7 -0.2126 1.3275 0.1060 0.021 Uiso calc R 1 . .
C C8 -0.15888(16) 1.0252(4) 0.07190(15) 0.0150(5) Uani d . 1 . .
C C9 0.11683(17) 0.9532(4) 0.17107(16) 0.0157(5) Uani d . 1 . .
C C10 0.19145(17) 0.7987(4) 0.16884(17) 0.0186(5) Uani d . 1 . .
H H10 0.1721 0.6609 0.1337 0.022 Uiso calc R 1 . .
C C11 0.29343(17) 0.8427(4) 0.21702(18) 0.0206(6) Uani d . 1 . .
H H11 0.3437 0.7360 0.2152 0.025 Uiso calc R 1 . .
C C12 0.32117(17) 1.0434(4) 0.26773(17) 0.0186(5) Uani d . 1 . .
C C13 0.24914(17) 1.2017(4) 0.27042(17) 0.0196(5) Uani d . 1 . .
H H13 0.2692 1.3406 0.3045 0.023 Uiso calc R 1 . .
C C14 0.14782(18) 1.1554(4) 0.22297(16) 0.0186(5) Uani d . 1 . .
H H14 0.0980 1.2627 0.2255 0.022 Uiso calc R 1 . .
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
;
Br Br -0.2901 2.4595
; International Tables
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C3 . . 116.11(19) ?
C1 N2 C8 . . 116.82(18) ?
N2 C1 C2 . . 120.8(2) ?
N2 C1 C9 . . 118.30(19) ?
C2 C1 C9 . . 120.9(2) ?
N1 C2 C1 . . 123.9(2) ?
N1 C2 H2 . . 118.0 ?
C1 C2 H2 . . 118.0 ?
N1 C3 C8 . . 120.74(19) ?
N1 C3 C4 . . 119.5(2) ?
C8 C3 C4 . . 119.7(2) ?
C5 C4 C3 . . 119.9(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C7 C6 C5 . . 120.7(2) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 120.1(2) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
N2 C8 C3 . . 121.6(2) ?
N2 C8 C7 . . 119.4(2) ?
C3 C8 C7 . . 119.0(2) ?
C10 C9 C14 . . 118.1(2) ?
C10 C9 C1 . . 121.96(19) ?
C14 C9 C1 . . 119.9(2) ?
C11 C10 C9 . . 121.1(2) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C12 C11 C10 . . 119.2(2) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C11 C12 C13 . . 121.2(2) ?
C11 C12 Br1 . . 119.76(18) ?
C13 C12 Br1 . . 119.03(17) ?
C14 C13 C12 . . 119.1(2) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
C13 C14 C9 . . 121.3(2) ?
C13 C14 H14 . . 119.4 ?
C9 C14 H14 . . 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C12 . 1.894(2) ?
N1 C2 . 1.307(3) ?
N1 C3 . 1.367(3) ?
N2 C1 . 1.320(3) ?
N2 C8 . 1.368(3) ?
C1 C2 . 1.422(3) ?
C1 C9 . 1.484(3) ?
C2 H2 . 0.9500 ?
C3 C8 . 1.411(3) ?
C3 C4 . 1.414(3) ?
C4 C5 . 1.364(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.407(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.369(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.413(3) ?
C7 H7 . 0.9500 ?
C9 C10 . 1.393(3) ?
C9 C14 . 1.400(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.379(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.383(3) ?
C13 C14 . 1.378(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N2 C1 C2 . . . . 0.1(3) ?
C8 N2 C1 C9 . . . . 179.40(19) ?
C3 N1 C2 C1 . . . . -2.1(3) ?
N2 C1 C2 N1 . . . . 2.2(4) ?
C9 C1 C2 N1 . . . . -177.1(2) ?
C2 N1 C3 C8 . . . . 0.0(3) ?
C2 N1 C3 C4 . . . . -177.7(2) ?
N1 C3 C4 C5 . . . . 177.3(2) ?
C8 C3 C4 C5 . . . . -0.4(3) ?
C3 C4 C5 C6 . . . . 0.1(4) ?
C4 C5 C6 C7 . . . . 0.8(4) ?
C5 C6 C7 C8 . . . . -1.5(4) ?
C1 N2 C8 C3 . . . . -2.2(3) ?
C1 N2 C8 C7 . . . . 178.0(2) ?
N1 C3 C8 N2 . . . . 2.2(3) ?
C4 C3 C8 N2 . . . . 179.9(2) ?
N1 C3 C8 C7 . . . . -177.9(2) ?
C4 C3 C8 C7 . . . . -0.2(3) ?
C6 C7 C8 N2 . . . . -179.0(2) ?
C6 C7 C8 C3 . . . . 1.2(3) ?
N2 C1 C9 C10 . . . . -176.0(2) ?
C2 C1 C9 C10 . . . . 3.3(4) ?
N2 C1 C9 C14 . . . . 3.5(3) ?
C2 C1 C9 C14 . . . . -177.2(2) ?
C14 C9 C10 C11 . . . . 0.4(4) ?
C1 C9 C10 C11 . . . . 179.9(2) ?
C9 C10 C11 C12 . . . . -0.2(4) ?
C10 C11 C12 C13 . . . . -0.6(4) ?
C10 C11 C12 Br1 . . . . 179.59(19) ?
C11 C12 C13 C14 . . . . 1.2(4) ?
Br1 C12 C13 C14 . . . . -179.02(17) ?
C12 C13 C14 C9 . . . . -1.0(4) ?
C10 C9 C14 C13 . . . . 0.2(4) ?
C1 C9 C14 C13 . . . . -179.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 666286
