##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-05-04
_journal_date_accepted     2010-05-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1380
_journal_page_last     o1380
_journal_paper_category     QO
_journal_coeditor_code     ZS2039
_publ_contact_author_name     'Dr. Wei Wang'
_publ_contact_author_address
; School of Perfume and Aroma Technology,
  Shanghai Institute of Technology,
  Shanghai, 200235,
  People's Republic of China
;
_publ_contact_author_email     zhao_submit@yahoo.com.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
2-(4-Bromophenyl)quinoxaline
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhi-jian Wang'
;
  School of Perfume and Aroma Technology,
  Shanghai Institute of Technology,
  Shanghai 200235,
  People's Republic of China
;
    'Wei-min Jia'
;
  School of Perfume and Aroma Technology,
  Shanghai Institute of Technology,
  Shanghai 200235,
  People's Republic of China
;
    'Hong-guo Yao'
;
  School of Chemical Engineering,
  University of Science and Technology,
  Liaoning Anshan 114051,
  People's Republic of China
;
    'Hong Qiu'
;
  School of Chemical Engineering,
  University of Science and Technology,
  Liaoning Anshan 114051,
  People's Republic of China
;
    'Wei Wang'
;
  School of Perfume and Aroma Technology,
  Shanghai Institute of Technology,
  Shanghai 200235,
  People's Republic of China
;
data_I
_chemical_name_systematic
;
2-(4-Bromophenyl)quinoxaline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H9 Br N2'
_chemical_formula_sum     'C14 H9 Br N2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C14 H9 Br N2'
_chemical_formula_weight     285.14
_chemical_melting_point     418
_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     13.959(3)
_cell_length_b     5.9031(12)
_cell_length_c     14.497(3)
_cell_angle_alpha     90.00
_cell_angle_beta     109.53(3)
_cell_angle_gamma     90.00
_cell_volume     1125.9(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3221
_cell_measurement_theta_min     2.863
_cell_measurement_theta_max     27.886
_cell_measurement_temperature     153(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.682
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     3.626
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(REQAB; Jacobson, 1998)'
_exptl_absorpt_correction_T_min     0.5308
_exptl_absorpt_correction_T_max     0.7132
_exptl_special_details
;
;
_diffrn_ambient_temperature     153(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     'multilayer'
_diffrn_measurement_device_type
                                   'Rigaku Model name? CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     7.31
_diffrn_reflns_number     8910
_diffrn_reflns_av_R_equivalents     0.0518
_diffrn_reflns_av_sigmaI/netI     0.0666
_diffrn_reflns_theta_min     2.86
_diffrn_reflns_theta_max     27.88
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F² are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.
;
_reflns_number_total     2683
_reflns_number_gt     1763
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0498
_refine_ls_R_factor_gt     0.0322
_refine_ls_wR_factor_gt     0.0694
_refine_ls_wR_factor_ref     0.0745
_refine_ls_goodness_of_fit_ref     0.956
_refine_ls_restrained_S_all     0.956
_refine_ls_number_reflns     2683
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0337P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.763
_refine_diff_density_min     -0.687
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0540(17)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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
;
_computing_data_collection     'CrystalClear (Rigaku/MSC, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku/MSC, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Br1 0.01429(15) 0.0399(2) 0.03931(19) -0.00711(11) 0.00519(12) -0.00733(13)
    N1 0.0176(11) 0.0191(10) 0.0248(11) 0.0017(8) 0.0021(9) -0.0045(9)
    N2 0.0157(10) 0.0175(10) 0.0176(9) 0.0015(8) 0.0054(9) -0.0003(8)
    C1 0.0153(11) 0.0153(12) 0.0148(11) 0.0002(9) 0.0058(10) 0.0002(9)
    C2 0.0158(12) 0.0198(12) 0.0246(13) 0.0035(10) 0.0029(11) -0.0052(11)
    C3 0.0148(12) 0.0172(11) 0.0147(11) 0.0002(9) 0.0031(10) 0.0018(9)
    C4 0.0188(13) 0.0194(12) 0.0193(11) -0.0026(10) 0.0015(11) 0.0002(10)
    C5 0.0115(12) 0.0273(14) 0.0216(12) 0.0004(9) 0.0009(10) 0.0039(10)
    C6 0.0248(14) 0.0213(13) 0.0234(13) 0.0085(11) 0.0090(12) 0.0048(10)
    C7 0.0188(12) 0.0135(11) 0.0209(12) 0.0022(10) 0.0070(11) 0.0018(10)
    C8 0.0149(12) 0.0165(12) 0.0141(11) -0.0005(9) 0.0053(10) 0.0022(9)
    C9 0.0149(12) 0.0169(12) 0.0151(11) -0.0009(9) 0.0048(10) 0.0013(9)
    C10 0.0173(12) 0.0158(11) 0.0227(12) -0.0020(10) 0.0068(10) -0.0043(10)
    C11 0.0156(12) 0.0210(13) 0.0268(13) 0.0021(10) 0.0090(11) -0.0011(10)
    C12 0.0124(11) 0.0229(13) 0.0198(12) -0.0047(9) 0.0045(10) 0.0007(10)
    C13 0.0212(13) 0.0171(11) 0.0203(12) -0.0051(10) 0.0068(11) -0.0018(10)
    C14 0.0182(12) 0.0200(13) 0.0172(11) 0.0029(10) 0.0055(11) -0.0018(10)
_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_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_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_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) ?
