#------------------------------------------------------------------------------
#$Date: 2023-08-30 04:47:45 +0300 (Wed, 30 Aug 2023) $
#$Revision: 285904 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/22/2312282.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_2312282
loop_
_publ_author_name
'Wzgarda-Raj, Kinga'
'Dominikowska, Justyna'
'Husik, Natallia'
'Rybarczyk-Pirek, Agnieszka J'
_publ_section_title
;
 2,2'-Dithiobispyrazine: about the disulfide bond.
;
_journal_coeditor_code           DG3042
_journal_issue                   9
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229623007416
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C8 H6 N4 S2'
_chemical_formula_moiety         'C8 H6 N4 S2'
_chemical_formula_sum            'C8 H6 N4 S2'
_chemical_formula_weight         222.29
_chemical_name_common
;
2,2'-Dithiobispyrazine
;
_chemical_name_systematic
;
2-(Pyrazin-2-yldisulfanyl)pyrazine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                91.524(2)
_cell_angle_beta                 95.245(2)
_cell_angle_gamma                106.024(2)
_cell_formula_units_Z            2
_cell_length_a                   5.68320(10)
_cell_length_b                   7.4639(2)
_cell_length_c                   11.7473(3)
_cell_measurement_reflns_used    6130
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.1730
_cell_measurement_theta_min      2.8330
_cell_volume                     476.24(2)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13219
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.052
_diffrn_reflns_theta_min         2.844
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       'cut plate'
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0324
_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)+(0.0388P)²+0.0599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                1990
_reflns_number_total             2551
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dg3042sup1.cif
_cod_data_source_block           I
_cod_database_code               2312282
_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.
;
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S12A 0.88777(8) 0.82515(5) 0.24527(3) 0.05535(14) Uani d 1 . .
S S12 0.51768(8) 0.75339(6) 0.21054(3) 0.05632(14) Uani d 1 . .
N N11A 1.1678(2) 0.85466(18) 0.43568(11) 0.0534(3) Uani d 1 . .
N N11 0.5985(2) 0.42008(18) 0.16399(12) 0.0542(3) Uani d 1 . .
N N14A 0.8155(3) 0.6392(2) 0.56361(12) 0.0586(3) Uani d 1 . .
N N14 0.1119(2) 0.2607(2) 0.07399(12) 0.0613(4) Uani d 1 . .
C C12 0.4351(3) 0.5157(2) 0.15903(11) 0.0416(3) Uani d 1 . .
C C12A 0.9380(3) 0.77714(18) 0.39184(12) 0.0435(3) Uani d 1 . .
C C13A 0.7614(3) 0.6697(2) 0.45469(13) 0.0512(4) Uani d 1 . .
H H13A 0.602192 0.618027 0.420052 0.061 Uiso calc 1 . .
C C15 0.2761(3) 0.1648(2) 0.07863(13) 0.0531(4) Uani d 1 . .
H H15 0.227497 0.040696 0.051216 0.064 Uiso calc 1 . .
C C13 0.1918(3) 0.4365(2) 0.11467(13) 0.0558(4) Uani d 1 . .
H H13 0.082179 0.508859 0.113540 0.067 Uiso calc 1 . .
C C16A 1.2209(3) 0.8212(2) 0.54463(15) 0.0591(4) Uani d 1 . .
H H16A 1.380639 0.871281 0.579086 0.071 Uiso calc 1 . .
C C16 0.5152(3) 0.2425(2) 0.12250(15) 0.0574(4) Uani d 1 . .
H H16 0.623987 0.169461 0.123587 0.069 Uiso calc 1 . .
C C15A 1.0470(3) 0.7152(2) 0.60712(14) 0.0589(4) Uani d 1 . .
H H15A 1.092551 0.695813 0.682846 0.071 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0270
0 0 -1 0.0281
0 -1 0 0.0534
-1 0 0 0.0992
1 0 0 0.1348
-4 4 -13 0.0675
4 -4 13 0.0675
-8 6 1 0.0944
8 -5 -5 0.1254
0 0 1 0.0059
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
C12A S12A S12 . . 104.70(5) y
C12 S12 S12A . . 104.87(5) y
C12A N11A C16A . . 115.79(13) y
C12 N11 C16 . . 115.54(13) y
C15A N14A C13A . . 116.19(14) y
C15 N14 C13 . . 116.23(13) y
N11 C12 S12 . . 120.89(11) y
N11 C12 C13 . . 122.03(14) y
C13 C12 S12 . . 117.08(11) y
N11A C12A S12A . . 112.32(10) y
N11A C12A C13A . . 122.57(13) y
C13A C12A S12A . . 125.10(11) y
N14A C13A C12A . . 121.17(14) y
N14A C13A H13A . . 119.4 ?
C12A C13A H13A . . 119.4 ?
N14 C15 H15 . . 119.0 ?
N14 C15 C16 . . 122.02(15) y
C16 C15 H15 . . 119.0 ?
N14 C13 C12 . . 121.76(15) y
N14 C13 H13 . . 119.1 ?
C12 C13 H13 . . 119.1 ?
N11A C16A H16A . . 119.1 ?
N11A C16A C15A . . 121.84(15) y
C15A C16A H16A . . 119.1 ?
N11 C16 C15 . . 122.42(15) y
N11 C16 H16 . . 118.8 ?
C15 C16 H16 . . 118.8 ?
N14A C15A C16A . . 122.42(15) y
N14A C15A H15A . . 118.8 ?
C16A C15A H15A . . 118.8 ?
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
S12A S12 . 2.0216(6) y
S12A C12A . 1.7816(14) y
S12 C12 . 1.7792(15) y
N11A C12A . 1.3227(19) y
N11A C16A . 1.334(2) y
N11 C12 . 1.3166(19) y
N11 C16 . 1.340(2) y
N14A C13A . 1.329(2) y
N14A C15A . 1.328(2) y
N14 C15 . 1.321(2) y
N14 C13 . 1.324(2) y
C12 C13 . 1.391(2) y
C12A C13A . 1.385(2) y
C13A H13A . 0.9300 ?
C15 H15 . 0.9300 ?
C15 C16 . 1.367(2) y
C13 H13 . 0.9300 ?
C16A H16A . 0.9300 ?
C16A C15A . 1.369(3) y
C16 H16 . 0.9300 ?
C15A H15A . 0.9300 ?
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
_geom_hbond_publ_flag
C13A H13A S12 . 0.93 2.74 3.2220(16) 113.4 yes
C13A H13A N14A 2_666 0.93 2.64 3.433(2) 144.2 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S12A S12 C12 N11 . . . . 8.43(12) ?
S12A S12 C12 C13 . . . . -172.07(10) ?
S12A C12A C13A N14A . . . . 179.24(12) ?
S12 S12A C12A N11A . . . . -165.73(10) ?
S12 S12A C12A C13A . . . . 15.01(14) ?
S12 C12 C13 N14 . . . . 179.87(13) ?
N11A C12A C13A N14A . . . . 0.0(2) ?
N11A C16A C15A N14A . . . . 0.1(3) ?
N11 C12 C13 N14 . . . . -0.6(2) ?
N14 C15 C16 N11 . . . . 0.3(3) ?
C12 N11 C16 C15 . . . . -0.5(2) ?
C12A N11A C16A C15A . . . . -0.8(2) ?
C13A N14A C15A C16A . . . . 0.8(3) ?
C15 N14 C13 C12 . . . . 0.4(2) ?
C13 N14 C15 C16 . . . . -0.2(2) ?
C16A N11A C12A S12A . . . . -178.51(11) ?
C16A N11A C12A C13A . . . . 0.8(2) ?
C16 N11 C12 S12 . . . . -179.90(12) ?
C16 N11 C12 C13 . . . . 0.6(2) ?
C15A N14A C13A C12A . . . . -0.8(2) ?

_cod_database_fobs_code 2312282
