#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/30/2213089.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_2213089
loop_
_publ_author_name
'Hong-Bin Zhao'
'Zhi-Zhi Hu'
'Xing Chen'
'Cui-Ping Wang'
'Zhi-Qiang Zhang'
_publ_section_title
;
 2,3-Bis(4-chlorophenyl)quinoxaline
;
_journal_coeditor_code           AT2259
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2488
_journal_page_last               o2489
_journal_paper_doi               10.1107/S1600536807016972
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H12 Cl2 N2'
_chemical_formula_moiety         'C20 H12 Cl2 N2'
_chemical_formula_sum            'C20 H12 Cl2 N2'
_chemical_formula_weight         351.22
_chemical_melting_point          447
_chemical_name_systematic
;
2,3-Bis(4-chlorophenyl)quinoxaline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.764(7)
_cell_angle_beta                 92.259(7)
_cell_angle_gamma                95.778(7)
_cell_formula_units_Z            2
_cell_length_a                   5.9282(6)
_cell_length_b                   11.9737(12)
_cell_length_c                   12.0247(13)
_cell_measurement_temperature    298(2)
_cell_volume                     819.29(15)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4712
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.54
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.9426
_exptl_absorpt_correction_T_min  0.8898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0390
_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)+(0.0541P)²+0.034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                2268
_reflns_number_total             2788
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2259.cif
_cod_data_source_block           I
_cod_database_code               2213089
_cod_database_fobs_code          2213089
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl2 0.04010(11) 0.68907(5) 0.56180(5) 0.0732(2) Uani d . 1
Cl Cl1 0.74092(11) 1.18952(6) 1.13621(5) 0.0834(3) Uani d . 1
N N2 -0.2905(3) 1.21318(13) 0.67212(13) 0.0504(4) Uani d . 1
C C20 -0.0692(3) 1.06565(16) 0.69190(16) 0.0462(4) Uani d . 1
C C19 -0.1140(3) 1.18893(15) 0.72670(15) 0.0457(4) Uani d . 1
N N1 -0.0019(3) 1.38869(14) 0.82822(14) 0.0546(4) Uani d . 1
C C18 0.1669(3) 0.91929(17) 0.60506(16) 0.0529(5) Uani d . 1
H H18A 0.3021 0.8993 0.5729 0.063 Uiso calc R 1
C C17 0.0281(3) 1.27823(16) 0.81168(15) 0.0472(4) Uani d . 1
C C16 0.2077(3) 1.25170(17) 0.88776(15) 0.0491(5) Uani d . 1
C C15 0.1331(3) 1.03426(17) 0.64630(16) 0.0512(5) Uani d . 1
H H15A 0.2484 1.0920 0.6435 0.061 Uiso calc R 1
C C14 -0.2384(3) 0.97782(17) 0.69686(18) 0.0549(5) Uani d . 1
H H14A -0.3755 0.9972 0.7270 0.066 Uiso calc R 1
C C13 -0.3283(3) 1.32661(16) 0.69109(16) 0.0503(5) Uani d . 1
C C12 0.4028(3) 1.33050(18) 0.92393(16) 0.0531(5) Uani d . 1
H H12A 0.4214 1.3971 0.8974 0.064 Uiso calc R 1
C C11 0.5378(4) 1.2141(2) 1.03895(17) 0.0603(5) Uani d . 1
C C10 -0.0023(3) 0.83464(16) 0.61211(16) 0.0519(5) Uani d . 1
C C9 -0.5157(4) 1.35615(19) 0.63434(19) 0.0625(6) Uani d . 1
H H9A -0.6163 1.2981 0.5855 0.075 Uiso calc R 1
C C8 -0.1770(3) 1.41500(16) 0.76625(16) 0.0529(5) Uani d . 1
C C7 -0.2050(4) 0.86296(18) 0.65774(18) 0.0588(5) Uani d . 1
H H7A -0.3182 0.8048 0.6620 0.071 Uiso calc R 1
C C6 0.5685(4) 1.31111(19) 0.99834(17) 0.0599(5) Uani d . 1
H H6A 0.6994 1.3633 1.0207 0.072 Uiso calc R 1
C C5 0.1835(4) 1.15501(19) 0.93073(18) 0.0595(5) Uani d . 1
H H5A 0.0546 1.1015 0.9077 0.071 Uiso calc R 1
C C4 0.3454(4) 1.1358(2) 1.00679(18) 0.0633(6) Uani d . 1
H H4A 0.3252 1.0709 1.0360 0.076 Uiso calc R 1
C C3 -0.2162(4) 1.53197(18) 0.7815(2) 0.0694(6) Uani d . 1
H H3A -0.1180 1.5914 0.8301 0.083 Uiso calc R 1
C C2 -0.5504(5) 1.4692(2) 0.6505(2) 0.0708(6) Uani d . 1
H H2B -0.6746 1.4886 0.6126 0.085 Uiso calc R 1
C C1 -0.3990(5) 1.5571(2) 0.7243(2) 0.0751(7) Uani d . 1
H H1B -0.4243 1.6343 0.7344 0.090 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
;
Cl Cl 0.1484 0.1585
; International Tables
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C19 N2 C13 118.21(16) ?
C15 C20 C14 118.38(18) ?
C15 C20 C19 121.42(16) ?
C14 C20 C19 120.03(17) ?
N2 C19 C17 121.40(17) ?
N2 C19 C20 115.04(16) yes
C17 C19 C20 123.53(16) ?
C17 N1 C8 117.72(16) ?
C10 C18 C15 118.94(18) ?
C10 C18 H18A 120.5 ?
C15 C18 H18A 120.5 ?
N1 C17 C19 120.83(17) ?
N1 C17 C16 116.33(16) yes
C19 C17 C16 122.79(16) ?
C5 C16 C12 117.90(19) ?
C5 C16 C17 122.50(17) ?
C12 C16 C17 119.47(18) ?
C18 C15 C20 121.31(17) ?
C18 C15 H15A 119.3 ?
C20 C15 H15A 119.3 ?
C7 C14 C20 120.77(18) ?
C7 C14 H14A 119.6 ?
C20 C14 H14A 119.6 ?
N2 C13 C9 119.94(18) ?
N2 C13 C8 120.23(17) ?
C9 C13 C8 119.82(18) ?
C6 C12 C16 121.1(2) ?
C6 C12 H12A 119.5 ?
C16 C12 H12A 119.5 ?
C6 C11 C4 121.3(2) ?
C6 C11 Cl1 120.10(17) ?
C4 C11 Cl1 118.59(19) ?
C18 C10 C7 121.17(18) ?
C18 C10 Cl2 119.29(16) ?
C7 C10 Cl2 119.54(16) ?
C2 C9 C13 120.2(2) ?
C2 C9 H9A 119.9 ?
C13 C9 H9A 119.9 ?
N1 C8 C3 119.71(19) ?
N1 C8 C13 121.18(17) ?
C3 C8 C13 119.0(2) ?
C14 C7 C10 119.41(19) ?
C14 C7 H7A 120.3 ?
C10 C7 H7A 120.3 ?
C11 C6 C12 119.15(19) ?
C11 C6 H6A 120.4 ?
C12 C6 H6A 120.4 ?
C4 C5 C16 121.61(19) ?
C4 C5 H5A 119.2 ?
C16 C5 H5A 119.2 ?
C5 C4 C11 119.0(2) ?
C5 C4 H4A 120.5 ?
C11 C4 H4A 120.5 ?
C1 C3 C8 119.3(2) ?
C1 C3 H3A 120.3 ?
C8 C3 H3A 120.3 ?
C9 C2 C1 120.0(2) ?
C9 C2 H2B 120.0 ?
C1 C2 H2B 120.0 ?
C3 C1 C2 121.6(2) ?
C3 C1 H1B 119.2 ?
C2 C1 H1B 119.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl2 C10 1.7406(19) ?
Cl1 C11 1.744(2) ?
N2 C19 1.309(2) ?
N2 C13 1.362(2) ?
C20 C15 1.385(3) ?
C20 C14 1.393(3) ?
C20 C19 1.482(3) yes
C19 C17 1.446(3) ?
N1 C17 1.318(2) ?
N1 C8 1.362(3) ?
C18 C10 1.373(3) ?
C18 C15 1.377(3) ?
C18 H18A 0.9300 ?
C17 C16 1.487(3) yes
C16 C5 1.380(3) ?
C16 C12 1.396(3) ?
C15 H15A 0.9300 ?
C14 C7 1.373(3) ?
C14 H14A 0.9300 ?
C13 C9 1.403(3) ?
C13 C8 1.414(3) ?
C12 C6 1.379(3) ?
C12 H12A 0.9300 ?
C11 C6 1.369(3) ?
C11 C4 1.376(3) ?
C10 C7 1.378(3) ?
C9 C2 1.356(3) ?
C9 H9A 0.9300 ?
C8 C3 1.410(3) ?
C7 H7A 0.9300 ?
C6 H6A 0.9300 ?
C5 C4 1.376(3) ?
C5 H5A 0.9300 ?
C4 H4A 0.9300 ?
C3 C1 1.359(3) ?
C3 H3A 0.9300 ?
C2 C1 1.405(4) ?
C2 H2B 0.9300 ?
C1 H1B 0.9300 ?
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_publ_flag
C13 N2 C19 C17 4.7(3) ?
C13 N2 C19 C20 -173.40(15) yes
C15 C20 C19 N2 119.61(19) ?
C14 C20 C19 N2 -55.7(2) ?
C15 C20 C19 C17 -58.5(3) ?
C14 C20 C19 C17 126.2(2) ?
C8 N1 C17 C19 2.8(3) ?
C8 N1 C17 C16 -174.90(15) yes
N2 C19 C17 N1 -7.1(3) ?
C20 C19 C17 N1 170.92(17) ?
N2 C19 C17 C16 170.47(16) ?
C20 C19 C17 C16 -11.6(3) ?
N1 C17 C16 C5 141.9(2) ?
C19 C17 C16 C5 -35.7(3) ?
N1 C17 C16 C12 -33.9(2) ?
C19 C17 C16 C12 148.52(18) ?
C10 C18 C15 C20 -1.5(3) ?
C14 C20 C15 C18 0.9(3) ?
C19 C20 C15 C18 -174.46(17) ?
C15 C20 C14 C7 0.2(3) ?
C19 C20 C14 C7 175.62(18) ?
C19 N2 C13 C9 -179.94(18) ?
C19 N2 C13 C8 1.2(3) ?
C5 C16 C12 C6 1.3(3) ?
C17 C16 C12 C6 177.27(17) ?
C15 C18 C10 C7 1.1(3) ?
C15 C18 C10 Cl2 -179.23(14) ?
N2 C13 C9 C2 -178.15(19) ?
C8 C13 C9 C2 0.7(3) ?
C17 N1 C8 C3 179.72(17) ?
C17 N1 C8 C13 3.1(3) ?
N2 C13 C8 N1 -5.4(3) ?
C9 C13 C8 N1 175.75(17) ?
N2 C13 C8 C3 178.01(17) ?
C9 C13 C8 C3 -0.9(3) ?
C20 C14 C7 C10 -0.6(3) ?
C18 C10 C7 C14 0.0(3) ?
Cl2 C10 C7 C14 -179.70(16) ?
C4 C11 C6 C12 0.1(3) ?
Cl1 C11 C6 C12 -178.25(15) ?
C16 C12 C6 C11 -1.4(3) ?
C12 C16 C5 C4 0.0(3) ?
C17 C16 C5 C4 -175.84(19) ?
C16 C5 C4 C11 -1.2(3) ?
C6 C11 C4 C5 1.1(3) ?
Cl1 C11 C4 C5 179.54(16) ?
N1 C8 C3 C1 -176.2(2) ?
C13 C8 C3 C1 0.4(3) ?
C13 C9 C2 C1 -0.2(3) ?
C8 C3 C1 C2 0.1(3) ?
C9 C2 C1 C3 -0.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 281359
