#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/73/2207364.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_2207364
loop_
_publ_author_name
'Ning-Ning Pan'
'Wei Wang'
'Bing Zhao'
_publ_section_title
;
 2,3-Bis(1-methyl-1H-imidazol-2-ylsulfanylmethyl)quinoxaline
;
_journal_coeditor_code           TK6275
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3939
_journal_page_last               o3940
_journal_paper_doi               10.1107/S1600536805033404
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H18 N6 S2'
_chemical_formula_moiety         'C18 H18 N6 S2'
_chemical_formula_sum            'C18 H18 N6 S2'
_chemical_formula_weight         382.50
_chemical_melting_point          374
_chemical_name_systematic
;
2,3-Bis(1-methyl-1H-imidazol-2-ylsulfanylmethyl)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                96.495(4)
_cell_angle_beta                 97.418(3)
_cell_angle_gamma                109.863(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8978(14)
_cell_length_b                   9.953(2)
_cell_length_c                   14.556(3)
_cell_measurement_reflns_used    1798
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.86
_cell_volume                     918.7(3)
_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      294(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.021
_diffrn_reflns_av_sigmaI/netI    0.041
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4713
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.4
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.062
_refine_ls_R_factor_gt           0.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.067P)²+0.146P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.107
_refine_ls_wR_factor_ref         0.122
_reflns_number_gt                2350
_reflns_number_total             3244
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6275.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Yes' changed to 'yes' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2207364
_cod_database_fobs_code          2207364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
S1 1.35146(10) 0.12202(7) 0.46720(5) 0.0503(2) Uani d . 1 S
S2 0.77718(12) 0.23331(7) 0.27469(5) 0.0572(2) Uani d . 1 S
N1 1.1229(3) -0.0871(2) 0.30655(14) 0.0425(5) Uani d . 1 N
N2 0.7135(3) -0.1509(2) 0.20914(14) 0.0429(5) Uani d . 1 N
N3 1.6020(3) 0.3723(2) 0.58181(14) 0.0464(5) Uani d . 1 N
N4 1.2665(3) 0.3184(2) 0.58856(16) 0.0566(6) Uani d . 1 N
N5 0.5893(3) 0.1870(2) 0.09107(15) 0.0467(5) Uani d . 1 N
N6 0.9146(3) 0.1882(2) 0.11143(18) 0.0586(6) Uani d . 1 N
C1 1.0296(4) -0.2055(2) 0.23596(17) 0.0409(6) Uani d . 1 C
C2 1.1400(4) -0.2976(3) 0.21369(19) 0.0507(7) Uani d . 1 C
H2 1.2760 -0.2766 0.2449 0.061 Uiso calc R 1 H
C3 1.0458(5) -0.4172(3) 0.1463(2) 0.0595(8) Uani d . 1 C
H3 1.1178 -0.4785 0.1320 0.071 Uiso calc R 1 H
C4 0.8436(5) -0.4492(3) 0.0984(2) 0.0614(8) Uani d . 1 C
H4 0.7824 -0.5313 0.0523 0.074 Uiso calc R 1 H
C5 0.7332(5) -0.3616(3) 0.11812(19) 0.0558(7) Uani d . 1 C
H5 0.5981 -0.3838 0.0855 0.067 Uiso calc R 1 H
C6 0.8260(4) -0.2377(3) 0.18814(17) 0.0419(6) Uani d . 1 C
C7 1.0119(4) -0.0083(2) 0.32687(16) 0.0386(5) Uani d . 1 C
C8 0.8033(3) -0.0407(2) 0.27681(16) 0.0375(5) Uani d . 1 C
C9 1.1045(4) 0.1174(3) 0.40570(19) 0.0535(7) Uani d . 1 C
H9A 1.0078 0.1105 0.4493 0.064 Uiso calc R 1 H
H9B 1.1253 0.2068 0.3809 0.064 Uiso calc R 1 H
C10 1.4038(4) 0.2785(3) 0.54957(16) 0.0410(6) Uani d . 1 C
C11 1.3839(5) 0.4449(3) 0.6483(2) 0.0597(8) Uani d . 1 C
H11 1.3291 0.4997 0.6858 0.072 Uiso calc R 1 H
C12 1.5877(5) 0.4794(3) 0.64540(19) 0.0572(7) Uani d . 1 C
H12 1.6976 0.5599 0.6797 0.069 Uiso calc R 1 H
C13 1.7926(4) 0.3652(4) 0.5518(2) 0.0762(10) Uani d . 1 C
H13A 1.8091 0.2764 0.5639 0.114 Uiso calc R 1 H
H13B 1.9112 0.4459 0.5861 0.114 Uiso calc R 1 H
H13C 1.7829 0.3684 0.4858 0.114 Uiso calc R 1 H
C14 0.6765(4) 0.0502(3) 0.30156(18) 0.0472(6) Uani d . 1 C
H14A 0.6722 0.0564 0.3682 0.057 Uiso calc R 1 H
H14B 0.5339 0.0019 0.2677 0.057 Uiso calc R 1 H
C15 0.7616(4) 0.1992(2) 0.15380(18) 0.0443(6) Uani d . 1 C
C16 0.8366(5) 0.1697(3) 0.0183(2) 0.0657(8) Uani d . 1 C
H16 0.9105 0.1596 -0.0295 0.079 Uiso calc R 1 H
C17 0.6391(5) 0.1680(3) 0.00393(19) 0.0574(7) Uani d . 1 C
H17 0.5538 0.1563 -0.0536 0.069 Uiso calc R 1 H
C18 0.3942(4) 0.1972(3) 0.1122(2) 0.0713(9) Uani d . 1 C
H18A 0.3528 0.1436 0.1617 0.107 Uiso calc R 1 H
H18B 0.2872 0.1576 0.0571 0.107 Uiso calc R 1 H
H18C 0.4135 0.2969 0.1318 0.107 Uiso calc R 1 H
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
;
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
_geom_angle_publ_flag
C10 S1 C9 96.95(11) ?
C15 S2 C14 101.70(11) ?
C7 N1 C1 117.0(2) ?
C8 N2 C6 117.0(2) ?
C10 N3 C12 106.3(2) ?
C10 N3 C13 127.1(2) ?
C12 N3 C13 126.6(2) ?
C10 N4 C11 104.5(2) ?
C15 N5 C17 106.2(2) ?
C15 N5 C18 127.1(2) ?
C17 N5 C18 126.6(2) ?
C15 N6 C16 104.4(2) ?
N1 C1 C6 120.9(2) ?
N1 C1 C2 119.3(2) ?
C6 C1 C2 119.7(2) ?
C3 C2 C1 119.5(3) ?
C3 C2 H2 120.3 ?
C1 C2 H2 120.3 ?
C2 C3 C4 120.9(3) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
C5 C4 C3 120.9(3) ?
C5 C4 H4 119.5 ?
C3 C4 H4 119.5 ?
C4 C5 C6 119.4(3) ?
C4 C5 H5 120.3 ?
C6 C5 H5 120.3 ?
N2 C6 C1 121.1(2) ?
N2 C6 C5 119.4(2) ?
C1 C6 C5 119.5(2) ?
N1 C7 C8 121.9(2) ?
N1 C7 C9 118.6(2) ?
C8 C7 C9 119.5(2) ?
N2 C8 C7 122.0(2) ?
N2 C8 C14 116.6(2) ?
C7 C8 C14 121.3(2) ?
C7 C9 S1 111.30(17) ?
C7 C9 H9A 109.4 ?
S1 C9 H9A 109.4 ?
C7 C9 H9B 109.4 ?
S1 C9 H9B 109.4 ?
H9A C9 H9B 108.0 ?
S1 C10 N3 121.20(18) yes
S1 C10 N4 126.74(19) yes
N3 C10 N4 112.0(2) yes
C12 C11 N4 111.0(2) ?
C12 C11 H11 124.5 ?
N4 C11 H11 124.5 ?
C11 C12 N3 106.1(2) ?
C11 C12 H12 126.9 ?
N3 C12 H12 126.9 ?
N3 C13 H13A 109.5 ?
N3 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
N3 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C8 C14 S2 114.05(17) ?
C8 C14 H14A 108.7 ?
S2 C14 H14A 108.7 ?
C8 C14 H14B 108.7 ?
S2 C14 H14B 108.7 ?
H14A C14 H14B 107.6 ?
S2 C15 N5 123.13(19) yes
S2 C15 N6 125.0(2) yes
N5 C15 N6 111.8(2) yes
C17 C16 N6 111.6(3) ?
C17 C16 H16 124.2 ?
N6 C16 H16 124.2 ?
C16 C17 N5 106.0(3) ?
C16 C17 H17 127.0 ?
N5 C17 H17 127.0 ?
N5 C18 H18A 109.5 ?
N5 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
N5 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C9 1.803(3) yes
S1 C10 1.754(2) yes
S2 C14 1.825(3) yes
S2 C15 1.736(3) yes
N1 C7 1.305(3) ?
N1 C1 1.378(3) ?
N2 C8 1.301(3) ?
N2 C6 1.378(3) ?
N3 C10 1.352(3) ?
N3 C12 1.369(3) ?
N3 C13 1.459(3) ?
N4 C10 1.311(3) ?
N4 C11 1.369(3) ?
N5 C15 1.362(3) ?
N5 C17 1.365(3) ?
N5 C18 1.452(3) ?
N6 C15 1.319(3) ?
N6 C16 1.360(4) ?
C1 C6 1.396(3) ?
C1 C2 1.413(3) ?
C2 C3 1.359(4) ?
C2 H2 0.9300 ?
C3 C4 1.389(4) ?
C3 H3 0.9300 ?
C4 C5 1.369(4) ?
C4 H4 0.9300 ?
C5 C6 1.408(3) ?
C5 H5 0.9300 ?
C7 C8 1.437(3) ?
C7 C9 1.494(3) ?
C8 C14 1.503(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C11 C12 1.336(4) ?
C11 H11 0.9300 ?
C12 H12 0.9300 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C16 C17 1.345(4) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
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
C7 N1 C1 C6 0.7(3)
C7 N1 C1 C2 -177.6(2)
N1 C1 C2 C3 177.8(2)
C6 C1 C2 C3 -0.5(4)
C1 C2 C3 C4 0.7(4)
C2 C3 C4 C5 -0.4(4)
C3 C4 C5 C6 -0.2(4)
C8 N2 C6 C1 -1.7(3)
C8 N2 C6 C5 177.5(2)
N1 C1 C6 N2 0.9(4)
C2 C1 C6 N2 179.2(2)
N1 C1 C6 C5 -178.3(2)
C2 C1 C6 C5 0.0(4)
C4 C5 C6 N2 -178.9(2)
C4 C5 C6 C1 0.4(4)
C1 N1 C7 C8 -1.4(3)
C1 N1 C7 C9 177.5(2)
C6 N2 C8 C7 1.0(3)
C6 N2 C8 C14 -177.9(2)
N1 C7 C8 N2 0.6(4)
C9 C7 C8 N2 -178.3(2)
N1 C7 C8 C14 179.4(2)
C9 C7 C8 C14 0.5(3)
N1 C7 C9 S1 -6.5(3)
C8 C7 C9 S1 172.42(18)
C10 S1 C9 C7 179.8(2)
C11 N4 C10 N3 0.5(3)
C11 N4 C10 S1 179.0(2)
C12 N3 C10 N4 -0.4(3)
C13 N3 C10 N4 -177.7(3)
C12 N3 C10 S1 -178.94(18)
C13 N3 C10 S1 3.8(4)
C9 S1 C10 N4 35.5(3)
C9 S1 C10 N3 -146.2(2)
C10 N4 C11 C12 -0.4(3)
N4 C11 C12 N3 0.2(3)
C10 N3 C12 C11 0.1(3)
C13 N3 C12 C11 177.4(3)
N2 C8 C14 S2 -113.0(2)
C7 C8 C14 S2 68.1(3)
C15 S2 C14 C8 61.0(2)
C16 N6 C15 N5 0.6(3)
C16 N6 C15 S2 -176.7(2)
C17 N5 C15 N6 -0.4(3)
C18 N5 C15 N6 -178.4(2)
C17 N5 C15 S2 176.96(18)
C18 N5 C15 S2 -1.1(4)
C14 S2 C15 N6 -92.9(2)
C14 S2 C15 N5 90.1(2)
C15 N6 C16 C17 -0.6(3)
N6 C16 C17 N5 0.4(3)
C15 N5 C17 C16 0.0(3)
C18 N5 C17 C16 178.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126994
2 PubChem 71405362
