#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557321.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_1557321
loop_
_publ_author_name
'de Freitas, Jorge F.'
'Brown, Shayne'
'Oberndorfer, James S.'
'Crundwell, Guy'
_publ_section_title
;
 6-Nitro-2,3-bis(thiophen-2-yl)quinoxaline
;
_journal_coeditor_code           FF4034
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x200203
_journal_paper_doi               10.1107/S2414314620002035
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C16 H9 N3 O2 S2'
_chemical_formula_moiety         'C16 H9 N3 O2 S2'
_chemical_formula_sum            'C16 H9 N3 O2 S2'
_chemical_formula_weight         339.38
_chemical_melting_point          474
_chemical_name_common
;
6-Nitro-2,3-bis(thien-2-yl)quinoxaline
;
_chemical_name_systematic
;
6-Nitro-2,3-bis(thiophen-2-yl)quinoxaline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.610(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7649(4)
_cell_length_b                   5.3386(2)
_cell_length_c                   24.3536(8)
_cell_measurement_reflns_used    4982
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.6699
_cell_measurement_theta_min      4.1858
_cell_volume                     1473.18(9)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED  (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
OLEX2 (Bourhis et al.,  2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Sapphire3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            12501
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         34.74
_diffrn_reflns_theta_min         4.19
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.334
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         5931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0958P)²+0.3970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.1988
_reflns_number_gt                3620
_reflns_number_total             5931
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ff4034sup1.cif
_cod_data_source_block           I
_cod_database_code               1557321
_cod_database_fobs_code          1557321
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.16791(7) 0.82603(13) 0.52719(3) 0.0622(2) Uani d 1 . .
S S2 0.02258(6) 1.15002(14) 0.31003(3) 0.0592(2) Uani d 1 . .
O O1 0.30694(18) 0.1759(4) 0.20797(8) 0.0669(5) Uani d 1 . .
O O2 0.43910(18) -0.0612(4) 0.26181(9) 0.0663(5) Uani d 1 . .
N N2 0.20929(14) 0.7957(3) 0.33911(7) 0.0357(3) Uani d 1 . .
N N1 0.36211(14) 0.6752(3) 0.44590(7) 0.0369(3) Uani d 1 . .
N N3 0.37406(17) 0.1200(4) 0.25404(8) 0.0463(4) Uani d 1 . .
C C1 0.27918(15) 0.8444(4) 0.44089(8) 0.0328(4) Uani d 1 . .
C C2 0.20193(15) 0.9143(3) 0.38578(7) 0.0323(3) Uani d 1 . .
C C3 0.29042(16) 0.6090(3) 0.34485(8) 0.0322(3) Uani d 1 . .
C C4 0.29411(17) 0.4671(4) 0.29649(8) 0.0373(4) Uani d 1 . .
H H4 0.2428 0.5008 0.2609 0.045 Uiso calc 1 . .
C C5 0.37543(17) 0.2785(4) 0.30344(8) 0.0361(4) Uani d 1 . .
C C6 0.45704(19) 0.2266(4) 0.35510(9) 0.0445(5) Uani d 1 . .
H H6 0.5124 0.0998 0.3576 0.053 Uiso calc 1 . .
C C7 0.45498(19) 0.3639(4) 0.40225(9) 0.0442(5) Uani d 1 . .
H H7 0.5094 0.3318 0.4370 0.053 Uiso calc 1 . .
C C8 0.37005(16) 0.5542(4) 0.39796(8) 0.0343(4) Uani d 1 . .
C C9 0.26743(17) 0.9512(4) 0.49523(8) 0.0369(4) Uani d 1 . .
C C10 0.3322(2) 1.1441(5) 0.52755(8) 0.0452(5) Uani d 1 . .
H H10 0.3919 1.2336 0.5179 0.054 Uiso calc 1 . .
C C11 0.2935(2) 1.1845(5) 0.57763(9) 0.0529(6) Uani d 1 . .
H H11 0.3249 1.3084 0.6042 0.063 Uiso calc 1 . .
C C12 0.2088(2) 1.0296(5) 0.58287(10) 0.0567(6) Uani d 1 . .
H H12 0.1756 1.0320 0.6135 0.068 Uiso calc 1 . .
C C13 0.11360(16) 1.1131(4) 0.37766(8) 0.0351(4) Uani d 1 . .
C C14 0.08780(17) 1.2923(4) 0.41567(9) 0.0380(4) Uani d 1 . .
H H14 0.1266 1.3051 0.4542 0.046 Uiso calc 1 . .
C C15 -0.0063(2) 1.4494(5) 0.38591(12) 0.0545(6) Uani d 1 . .
H H15 -0.0363 1.5785 0.4035 0.065 Uiso calc 1 . .
C C16 -0.0479(2) 1.3957(5) 0.33041(13) 0.0607(7) Uani d 1 . .
H H16 -0.1089 1.4836 0.3057 0.073 Uiso calc 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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 S1 C9 . . 91.82(12) yes
C16 S2 C13 . . 92.06(12) yes
C2 N2 C3 . . 117.91(15) yes
C1 N1 C8 . . 117.97(16) yes
O1 N3 C5 . . 118.3(2) yes
O2 N3 O1 . . 124.1(2) yes
O2 N3 C5 . . 117.62(19) yes
N1 C1 C2 . . 121.85(17) yes
N1 C1 C9 . . 115.35(16) yes
C2 C1 C9 . . 122.76(16) yes
N2 C2 C1 . . 120.08(16) yes
N2 C2 C13 . . 116.08(16) yes
C1 C2 C13 . . 123.84(16) yes
N2 C3 C4 . . 119.05(16) yes
N2 C3 C8 . . 121.41(17) yes
C8 C3 C4 . . 119.54(17) yes
C3 C4 H4 . . 121.0 no
C5 C4 C3 . . 118.00(17) yes
C5 C4 H4 . . 121.0 no
C4 C5 N3 . . 118.04(18) yes
C4 C5 C6 . . 123.28(18) yes
C6 C5 N3 . . 118.66(19) yes
C5 C6 H6 . . 120.4 no
C7 C6 C5 . . 119.27(19) yes
C7 C6 H6 . . 120.4 no
C6 C7 H7 . . 120.1 no
C6 C7 C8 . . 119.78(19) yes
C8 C7 H7 . . 120.1 no
N1 C8 C3 . . 120.51(17) yes
N1 C8 C7 . . 119.36(16) yes
C3 C8 C7 . . 120.06(17) yes
C1 C9 S1 . . 119.81(15) yes
C10 C9 S1 . . 111.71(16) yes
C10 C9 C1 . . 128.42(19) yes
C9 C10 H10 . . 125.0 no
C9 C10 C11 . . 110.0(2) yes
C11 C10 H10 . . 125.0 no
C10 C11 H11 . . 122.9 no
C12 C11 C10 . . 114.1(2) yes
C12 C11 H11 . . 122.9 no
S1 C12 H12 . . 123.8 no
C11 C12 S1 . . 112.30(18) yes
C11 C12 H12 . . 123.8 no
C2 C13 S2 . . 116.76(14) yes
C14 C13 S2 . . 111.13(14) yes
C14 C13 C2 . . 132.09(17) yes
C13 C14 H14 . . 125.1 no
C13 C14 C15 . . 109.80(19) yes
C15 C14 H14 . . 125.1 no
C14 C15 H15 . . 122.8 no
C16 C15 C14 . . 114.3(2) yes
C16 C15 H15 . . 122.8 no
S2 C16 H16 . . 123.7 no
C15 C16 S2 . . 112.70(18) yes
C15 C16 H16 . . 123.7 no
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
S1 C9 . 1.707(2) yes
S1 C12 . 1.703(3) yes
S2 C13 . 1.7171(19) yes
S2 C16 . 1.696(3) yes
O1 N3 . 1.223(3) yes
O2 N3 . 1.216(3) yes
N2 C2 . 1.324(2) yes
N2 C3 . 1.361(2) yes
N1 C1 . 1.311(2) yes
N1 C8 . 1.359(2) yes
N3 C5 . 1.467(3) yes
C1 C2 . 1.453(2) yes
C1 C9 . 1.481(3) yes
C2 C13 . 1.461(3) yes
C3 C4 . 1.411(3) yes
C3 C8 . 1.408(2) yes
C4 H4 . 0.9300 no
C4 C5 . 1.368(3) yes
C5 C6 . 1.390(3) yes
C6 H6 . 0.9300 no
C6 C7 . 1.368(3) yes
C7 H7 . 0.9300 no
C7 C8 . 1.409(3) yes
C9 C10 . 1.392(3) yes
C10 H10 . 0.9300 no
C10 C11 . 1.428(3) yes
C11 H11 . 0.9300 no
C11 C12 . 1.327(4) yes
C12 H12 . 0.9300 no
C13 C14 . 1.420(3) yes
C14 H14 . 0.9300 no
C14 C15 . 1.422(3) yes
C15 H15 . 0.9300 no
C15 C16 . 1.339(4) yes
C16 H16 . 0.9300 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 146673765
