#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/53/2215353.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_2215353
loop_
_publ_author_name
'Lei, Peng'
'Hu, Zhi-Zhi'
'Wang, Cui-Ping'
'Chen, Xing'
'Zhang, Zhi-Qiang'
_publ_section_title
;
 2,3-Bis(3-nitrophenyl)quinoxaline
;
_journal_coeditor_code           BH2119
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3969
_journal_page_last               o3969
_journal_paper_doi               10.1107/S1600536807042055
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H12 N4 O4'
_chemical_formula_moiety         'C20 H12 N4 O4'
_chemical_formula_sum            'C20 H12 N4 O4'
_chemical_formula_weight         372.34
_chemical_melting_point          484
_chemical_name_systematic
;
2,3-Bis(3-nitrophenyl)quinoxaline
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.807(3)
_cell_length_b                   7.6160(15)
_cell_length_c                   34.430(7)
_cell_measurement_reflns_used    2243
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      2.3
_cell_volume                     3358.2(12)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 1000'
_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  0.0829
_diffrn_reflns_av_sigmaI/netI    0.0641
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13448
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0892P)²+1.3718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1903
_reflns_number_gt                1533
_reflns_number_total             2948
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2119.cif
_cod_data_source_block           I
_cod_database_code               2215353
_cod_database_fobs_code          2215353
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O O1 0.7566(4) 1.1964(7) -0.02595(10) 0.1310(17) Uani d U 1
O O2 0.8690(3) 1.0826(5) 0.01110(10) 0.0870(11) Uani d . 1
O O3 0.2285(3) 0.8632(5) 0.18938(10) 0.0883(11) Uani d . 1
O O4 0.1405(3) 0.7078(6) 0.14923(13) 0.1201(16) Uani d . 1
N N1 0.7804(4) 1.1237(5) 0.00377(10) 0.0723(12) Uani d . 1
N N2 0.7785(2) 0.8778(4) 0.13906(8) 0.0410(8) Uani d . 1
N N3 0.6311(2) 0.7105(4) 0.18590(8) 0.0425(8) Uani d . 1
N N4 0.2227(3) 0.7670(6) 0.16106(13) 0.0711(11) Uani d . 1
C C1 0.7236(3) 0.9972(5) 0.06500(10) 0.0427(9) Uani d . 1
H H1 0.7902 0.9501 0.0677 0.051 Uiso calc R 1
C C2 0.6987(3) 1.0903(5) 0.03248(11) 0.0510(10) Uani d . 1
C C3 0.6010(4) 1.1591(5) 0.02666(13) 0.0622(12) Uani d . 1
H H3A 0.5843 1.2163 0.0036 0.075 Uiso calc R 1
C C4 0.5285(3) 1.1413(5) 0.05580(13) 0.0639(12) Uani d . 1
H H4A 0.4625 1.1908 0.0531 0.077 Uiso calc R 1
C C5 0.5536(3) 1.0506(5) 0.08894(12) 0.0532(11) Uani d . 1
H H5 0.5040 1.0413 0.1086 0.064 Uiso calc R 1
C C6 0.6500(3) 0.9724(5) 0.09413(10) 0.0414(9) Uani d . 1
C C7 0.6801(3) 0.8727(4) 0.12936(9) 0.0371(9) Uani d . 1
C C8 0.8071(3) 0.7959(5) 0.17225(10) 0.0410(9) Uani d . 1
C C9 0.9120(3) 0.7918(5) 0.18301(12) 0.0526(10) Uani d . 1
H H9 0.9621 0.8434 0.1671 0.063 Uiso calc R 1
C C10 0.9413(3) 0.7126(6) 0.21664(12) 0.0607(12) Uani d . 1
H H10 1.0115 0.7093 0.2235 0.073 Uiso calc R 1
C C11 0.8674(4) 0.6365(6) 0.24082(12) 0.0590(11) Uani d . 1
H H11 0.8884 0.5825 0.2637 0.071 Uiso calc R 1
C C12 0.7646(3) 0.6403(5) 0.23127(10) 0.0526(11) Uani d . 1
H H12 0.7156 0.5899 0.2478 0.063 Uiso calc R 1
C C13 0.7320(3) 0.7196(5) 0.19665(9) 0.0397(9) Uani d . 1
C C14 0.6066(3) 0.7777(5) 0.15223(10) 0.0402(9) Uani d . 1
C C15 0.5015(3) 0.7331(5) 0.13689(10) 0.0449(9) Uani d . 1
C C16 0.4938(3) 0.6437(5) 0.10190(11) 0.0560(11) Uani d . 1
H H16 0.5544 0.6162 0.0883 0.067 Uiso calc R 1
C C17 0.3983(4) 0.5947(6) 0.08668(12) 0.0633(12) Uani d . 1
H H17 0.3946 0.5342 0.0633 0.076 Uiso calc R 1
C C18 0.3105(4) 0.6358(6) 0.10632(13) 0.0610(12) Uani d . 1
H H18 0.2456 0.6047 0.0964 0.073 Uiso calc R 1
C C19 0.3170(3) 0.7230(5) 0.14073(12) 0.0514(10) Uani d . 1
C C20 0.4127(3) 0.7711(5) 0.15701(11) 0.0487(10) Uani d . 1
H H20 0.4158 0.8274 0.1809 0.058 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
;
O O 0.0106 0.0060
; 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
O1 N1 O2 122.5(4) ?
O1 N1 C2 118.3(4) ?
O2 N1 C2 119.2(4) ?
C7 N2 C8 117.7(3) ?
C14 N3 C13 117.0(3) ?
O4 N4 O3 122.9(4) ?
O4 N4 C19 118.6(5) ?
O3 N4 C19 118.5(4) ?
C2 C1 C6 120.3(4) ?
C2 C1 H1 119.8 ?
C6 C1 H1 119.8 ?
C1 C2 C3 122.2(4) ?
C1 C2 N1 118.6(4) ?
C3 C2 N1 119.2(4) ?
C2 C3 C4 118.2(4) ?
C2 C3 H3A 120.9 ?
C4 C3 H3A 120.9 ?
C5 C4 C3 120.0(4) ?
C5 C4 H4A 120.0 ?
C3 C4 H4A 120.0 ?
C4 C5 C6 122.2(4) ?
C4 C5 H5 118.9 ?
C6 C5 H5 118.9 ?
C5 C6 C1 117.0(3) ?
C5 C6 C7 124.0(3) ?
C1 C6 C7 119.0(3) ?
N2 C7 C14 120.8(3) ?
N2 C7 C6 116.4(3) yes
C14 C7 C6 122.8(3) ?
N2 C8 C9 119.8(3) ?
N2 C8 C13 120.7(3) ?
C9 C8 C13 119.5(3) ?
C10 C9 C8 120.2(4) ?
C10 C9 H9 119.9 ?
C8 C9 H9 119.9 ?
C9 C10 C11 120.6(4) ?
C9 C10 H10 119.7 ?
C11 C10 H10 119.7 ?
C12 C11 C10 120.5(4) ?
C12 C11 H11 119.7 ?
C10 C11 H11 119.7 ?
C11 C12 C13 120.3(4) ?
C11 C12 H12 119.8 ?
C13 C12 H12 119.8 ?
N3 C13 C12 119.9(3) ?
N3 C13 C8 121.0(3) ?
C12 C13 C8 118.9(4) ?
N3 C14 C7 122.1(3) ?
N3 C14 C15 116.4(3) yes
C7 C14 C15 121.2(3) ?
C20 C15 C16 119.1(4) ?
C20 C15 C14 121.8(3) ?
C16 C15 C14 119.1(3) ?
C17 C16 C15 121.7(4) ?
C17 C16 H16 119.2 ?
C15 C16 H16 119.2 ?
C18 C17 C16 119.0(4) ?
C18 C17 H17 120.5 ?
C16 C17 H17 120.5 ?
C17 C18 C19 119.9(4) ?
C17 C18 H18 120.0 ?
C19 C18 H18 120.0 ?
C18 C19 C20 122.1(4) ?
C18 C19 N4 119.1(4) ?
C20 C19 N4 118.8(4) ?
C15 C20 C19 118.2(4) ?
C15 C20 H20 120.9 ?
C19 C20 H20 120.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.202(4) ?
O2 N1 1.204(4) ?
O3 N4 1.222(5) ?
O4 N4 1.215(5) ?
N1 C2 1.462(5) ?
N2 C7 1.304(4) ?
N2 C8 1.353(4) ?
N3 C14 1.305(4) ?
N3 C13 1.346(4) ?
N4 C19 1.435(5) ?
C1 C2 1.363(5) ?
C1 C6 1.389(5) ?
C1 H1 0.9300 ?
C2 C3 1.372(5) ?
C3 C4 1.373(6) ?
C3 H3A 0.9300 ?
C4 C5 1.372(5) ?
C4 H4A 0.9300 ?
C5 C6 1.383(5) ?
C5 H5 0.9300 ?
C6 C7 1.482(5) yes
C7 C14 1.425(5) yes
C8 C9 1.394(5) ?
C8 C13 1.403(5) ?
C9 C10 1.358(5) ?
C9 H9 0.9300 ?
C10 C11 1.387(6) ?
C10 H10 0.9300 ?
C11 C12 1.357(5) ?
C11 H11 0.9300 ?
C12 C13 1.401(5) ?
C12 H12 0.9300 ?
C14 C15 1.485(5) yes
C15 C20 1.363(5) ?
C15 C16 1.387(5) ?
C16 C17 1.382(5) ?
C16 H16 0.9300 ?
C17 C18 1.349(5) ?
C17 H17 0.9300 ?
C18 C19 1.361(6) ?
C18 H18 0.9300 ?
C19 C20 1.397(5) ?
C20 H20 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
C6 C1 C2 C3 -1.5(6)
C6 C1 C2 N1 175.8(3)
O1 N1 C2 C1 175.5(4)
O2 N1 C2 C1 -6.6(6)
O1 N1 C2 C3 -7.2(6)
O2 N1 C2 C3 170.7(4)
C1 C2 C3 C4 3.8(6)
N1 C2 C3 C4 -173.5(4)
C2 C3 C4 C5 -2.5(6)
C3 C4 C5 C6 -1.0(6)
C4 C5 C6 C1 3.3(6)
C4 C5 C6 C7 -179.7(4)
C2 C1 C6 C5 -2.0(5)
C2 C1 C6 C7 -179.2(3)
C8 N2 C7 C14 -2.6(5)
C8 N2 C7 C6 176.5(3)
C5 C6 C7 N2 -148.7(3)
C1 C6 C7 N2 28.2(5)
C5 C6 C7 C14 30.3(5)
C1 C6 C7 C14 -152.8(3)
C7 N2 C8 C9 177.5(3)
C7 N2 C8 C13 -4.6(5)
N2 C8 C9 C10 178.8(3)
C13 C8 C9 C10 0.8(6)
C8 C9 C10 C11 -0.6(6)
C9 C10 C11 C12 -0.1(6)
C10 C11 C12 C13 0.6(6)
C14 N3 C13 C12 -176.0(3)
C14 N3 C13 C8 -1.0(5)
C11 C12 C13 N3 174.7(3)
C11 C12 C13 C8 -0.4(5)
N2 C8 C13 N3 6.7(5)
C9 C8 C13 N3 -175.4(3)
N2 C8 C13 C12 -178.3(3)
C9 C8 C13 C12 -0.3(5)
C13 N3 C14 C7 -6.3(5)
C13 N3 C14 C15 167.0(3)
N2 C7 C14 N3 8.5(5)
C6 C7 C14 N3 -170.5(3)
N2 C7 C14 C15 -164.5(3)
C6 C7 C14 C15 16.5(5)
N3 C14 C15 C20 58.2(5)
C7 C14 C15 C20 -128.4(4)
N3 C14 C15 C16 -119.1(4)
C7 C14 C15 C16 54.4(5)
C20 C15 C16 C17 1.0(6)
C14 C15 C16 C17 178.3(4)
C15 C16 C17 C18 0.4(6)
C16 C17 C18 C19 -0.6(6)
C17 C18 C19 C20 -0.6(6)
C17 C18 C19 N4 179.5(4)
O4 N4 C19 C18 8.2(6)
O3 N4 C19 C18 -171.3(4)
O4 N4 C19 C20 -171.6(4)
O3 N4 C19 C20 8.8(6)
C16 C15 C20 C19 -2.1(5)
C14 C15 C20 C19 -179.3(3)
C18 C19 C20 C15 2.0(6)
N4 C19 C20 C15 -178.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123480
