#------------------------------------------------------------------------------
#$Date: 2018-06-08 18:34:09 +0300 (Fri, 08 Jun 2018) $
#$Revision: 208214 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/25/2242522.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_2242522
loop_
_publ_author_name
'Chrysochos, Nicolas'
'Schulzke, Carola'
_publ_section_title
;
 Crystal structure of
 1-ethyl-3-(2-oxo-1,3-dithiol-4-yl)quinoxalin-2(1H)-one
;
_journal_coeditor_code           KQ2022
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              901
_journal_page_last               904
_journal_paper_doi               10.1107/S2056989018007892
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C13 H10 N2 O2 S2'
_chemical_formula_moiety         'C13 H10 N2 O2 S2'
_chemical_formula_sum            'C13 H10 N2 O2 S2'
_chemical_formula_weight         290.35
_chemical_name_systematic
;
1-Ethyl-3-(2-oxo-1,3-dithiol-4-yl)quinoxalin-2(1H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 107.81(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.531(6)
_cell_length_b                   4.8522(10)
_cell_length_c                   20.861(4)
_cell_measurement_reflns_used    10798
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.5
_cell_measurement_theta_min      3.4
_cell_volume                     2460.4(10)
_computing_cell_refinement
;
X-Area (Stoe & Cie, 2010)
;
_computing_data_collection
;
X-Area (Stoe & Cie, 2010)
;
_computing_data_reduction
;
X-Area (Stoe & Cie, 2010)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008) and Mercury  (Macrae et al., 2006)
;
_computing_publication_material
;
CIFTAB (Sheldrick, 2013) and Mercury  (Macrae et al.,, 2006)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR-92 (Altomare et al., 1994)
;
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS2T'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10078
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.734
_diffrn_reflns_theta_min         1.676
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.8872
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(X-Red32 and X-Shape; Stoe & Cie, 2010)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.482
_exptl_crystal_size_mid          0.463
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.436
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0430
_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)+(0.0557P)²+1.3022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                2052
_reflns_number_total             2599
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            kq2022sup1.cif
_cod_data_source_block           I
_cod_database_code               2242522
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.819
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S S1 0.06586(2) 1.17332(13) 0.38431(3) 0.02924(17) Uani d 1
S S2 0.16189(2) 0.80790(12) 0.43550(3) 0.02882(17) Uani d 1
O O1 0.14629(7) 1.1274(4) 0.32955(8) 0.0379(4) Uani d 1
O O2 0.04198(6) 0.7134(3) 0.56260(8) 0.0296(4) Uani d 1
N N1 0.09576(7) 0.3591(4) 0.61708(9) 0.0233(4) Uani d 1
N N2 0.16734(7) 0.4593(4) 0.54239(9) 0.0242(4) Uani d 1
C C1 0.12850(9) 1.0512(5) 0.37418(11) 0.0290(5) Uani d 1
C C2 0.06873(9) 0.9742(5) 0.45374(11) 0.0258(5) Uani d 1
C C3 0.11163(9) 0.8032(5) 0.47709(11) 0.0237(4) Uani d 1
C C4 0.12261(8) 0.6022(5) 0.53199(10) 0.0229(4) Uani d 1
C C5 0.08324(8) 0.5692(5) 0.57104(10) 0.0236(4) Uani d 1
C C6 0.14444(8) 0.2091(5) 0.63101(11) 0.0231(4) Uani d 1
C C7 0.15922(9) 0.0081(5) 0.68143(11) 0.0263(5) Uani d 1
H H7 0.135972 -0.028724 0.708326 0.032 Uiso calc 1
C C8 0.20757(9) -0.1364(5) 0.69197(11) 0.0278(5) Uani d 1
H H8 0.217320 -0.273223 0.726147 0.033 Uiso calc 1
C C9 0.24248(9) -0.0852(5) 0.65328(12) 0.0296(5) Uani d 1
H H9 0.275622 -0.187017 0.661099 0.036 Uiso calc 1
C C10 0.22885(9) 0.1124(5) 0.60399(11) 0.0273(5) Uani d 1
H H10 0.252595 0.147249 0.577626 0.033 Uiso calc 1
C C11 0.17997(9) 0.2633(5) 0.59235(11) 0.0237(4) Uani d 1
C C12 0.05590(9) 0.2972(5) 0.65349(12) 0.0269(5) Uani d 1
H H12A 0.054369 0.095209 0.659446 0.032 Uiso calc 1
H H12B 0.018905 0.359079 0.625995 0.032 Uiso calc 1
C C13 0.07039(10) 0.4352(6) 0.72202(12) 0.0353(6) Uani d 1
H H13A 0.108738 0.394349 0.747326 0.053 Uiso calc 1
H H13B 0.046176 0.365385 0.746832 0.053 Uiso calc 1
H H13C 0.065600 0.634974 0.716145 0.053 Uiso calc 1
H H2 0.0387(10) 0.987(5) 0.4716(12) 0.028(6) Uiso d 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
C2 S1 C1 96.00(11)
C3 S2 C1 95.93(11)
C5 N1 C6 122.51(18)
C5 N1 C12 117.57(17)
C6 N1 C12 119.91(18)
C4 N2 C11 119.18(18)
O1 C1 S2 123.50(19)
O1 C1 S1 123.48(19)
S2 C1 S1 113.02(13)
C3 C2 S1 118.16(17)
C3 C2 H2 124.3(15)
S1 C2 H2 117.4(15)
C2 C3 C4 129.5(2)
C2 C3 S2 116.86(17)
C4 C3 S2 113.64(15)
N2 C4 C3 115.80(19)
N2 C4 C5 124.1(2)
C3 C4 C5 120.11(19)
O2 C5 N1 121.94(19)
O2 C5 C4 123.6(2)
N1 C5 C4 114.42(18)
N1 C6 C7 122.65(19)
N1 C6 C11 118.2(2)
C7 C6 C11 119.16(19)
C8 C7 C6 119.8(2)
C8 C7 H7 120.1
C6 C7 H7 120.1
C7 C8 C9 121.1(2)
C7 C8 H8 119.4
C9 C8 H8 119.4
C10 C9 C8 119.9(2)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C11 120.2(2)
C9 C10 H10 119.9
C11 C10 H10 119.9
N2 C11 C10 118.85(19)
N2 C11 C6 121.32(19)
C10 C11 C6 119.8(2)
N1 C12 C13 112.79(18)
N1 C12 H12A 109.0
C13 C12 H12A 109.0
N1 C12 H12B 109.0
C13 C12 H12B 109.0
H12A C12 H12B 107.8
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.724(2)
S1 C1 1.778(2)
S2 C3 1.755(2)
S2 C1 1.758(2)
O1 C1 1.212(3)
O2 C5 1.232(3)
N1 C5 1.370(3)
N1 C6 1.392(3)
N1 C12 1.475(3)
N2 C4 1.296(3)
N2 C11 1.374(3)
C2 C3 1.341(3)
C2 H2 0.95(2)
C3 C4 1.465(3)
C4 C5 1.483(3)
C6 C7 1.399(3)
C6 C11 1.411(3)
C7 C8 1.378(3)
C7 H7 0.9500
C8 C9 1.395(3)
C8 H8 0.9500
C9 C10 1.371(3)
C9 H9 0.9500
C10 C11 1.403(3)
C10 H10 0.9500
C12 C13 1.519(3)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O2 . 0.95(2) 2.30(3) 2.859(3) 117.2(19)
C2 H2 O2 5_576 0.95(2) 2.44(2) 3.133(3) 129(2)
C7 H7 O1 6_566 0.95 2.51 3.272(3) 138
C9 H9 S2 7_556 0.95 2.99 3.652(3) 128
C12 H12A O2 1_545 0.99 2.69 3.367(3) 126
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
C3 S2 C1 O1 -178.3(2)
C3 S2 C1 S1 1.57(15)
C2 S1 C1 O1 179.1(2)
C2 S1 C1 S2 -0.82(15)
C1 S1 C2 C3 -0.6(2)
S1 C2 C3 C4 -176.09(18)
S1 C2 C3 S2 1.9(3)
C1 S2 C3 C2 -2.1(2)
C1 S2 C3 C4 176.21(16)
C11 N2 C4 C3 -178.92(19)
C11 N2 C4 C5 0.1(3)
C2 C3 C4 N2 178.4(2)
S2 C3 C4 N2 0.4(3)
C2 C3 C4 C5 -0.7(4)
S2 C3 C4 C5 -178.67(16)
C6 N1 C5 O2 -174.7(2)
C12 N1 C5 O2 4.1(3)
C6 N1 C5 C4 6.6(3)
C12 N1 C5 C4 -174.59(18)
N2 C4 C5 O2 177.0(2)
C3 C4 C5 O2 -4.0(3)
N2 C4 C5 N1 -4.3(3)
C3 C4 C5 N1 174.71(18)
C5 N1 C6 C7 175.2(2)
C12 N1 C6 C7 -3.6(3)
C5 N1 C6 C11 -4.9(3)
C12 N1 C6 C11 176.29(19)
N1 C6 C7 C8 178.9(2)
C11 C6 C7 C8 -0.9(3)
C6 C7 C8 C9 0.3(3)
C7 C8 C9 C10 0.2(4)
C8 C9 C10 C11 0.0(3)
C4 N2 C11 C10 -179.0(2)
C4 N2 C11 C6 1.9(3)
C9 C10 C11 N2 -179.8(2)
C9 C10 C11 C6 -0.7(3)
N1 C6 C11 N2 0.3(3)
C7 C6 C11 N2 -179.8(2)
N1 C6 C11 C10 -178.7(2)
C7 C6 C11 C10 1.2(3)
C5 N1 C12 C13 -96.3(2)
C6 N1 C12 C13 82.5(3)

_cod_database_fobs_code 2242522
