#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018129.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_2018129
loop_
_publ_author_name
'Szczesio, Małgorzata'
'Olczak, Andrzej'
'Gołka, Jolanta'
'Gobis, Katarzyna'
'Foks, Henryk'
'Główka, Marek L.'
_publ_section_title
;
 Planarity of heteroaryldithiocarbazic acid derivatives showing
 tuberculostatic activity. III. Mono- and diesters of
 3-(pyrazin-2-ylcarbonyl)dithiocarbazic acid
;
_journal_coeditor_code           GD3386
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o235
_journal_page_last               o240
_journal_paper_doi               10.1107/S0108270111021767
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H10 N4 O S2'
_chemical_formula_moiety         'C8 H10 N4 O S2'
_chemical_formula_sum            'C8 H10 N4 O S2'
_chemical_formula_weight         242.32
_chemical_name_systematic
;
N'-[bis(methylsulfanyl)methylidene]pyrazine-2-carbohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.121(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8332(2)
_cell_length_b                   21.0883(4)
_cell_length_c                   7.3920(2)
_cell_measurement_reflns_used    8241
_cell_measurement_temperature    297
_cell_measurement_theta_max      28.5739
_cell_measurement_theta_min      2.8947
_cell_volume                     1096.36(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Kuma KM4 CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12975
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.464
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.198
_refine_ls_extinction_coef       0.0042(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0311
_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)+(0.0445P)²+0.2852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                1960
_reflns_number_total             2236
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3386.cif
_cod_data_source_block           F1
_cod_original_cell_volume        1096.36(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018129
_cod_database_fobs_code          2018129
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.0226(2) 0.61366(8) 0.7928(2) 0.0423(4) Uani d . 1 1 . .
C C01 1.3336(3) 0.61423(10) 0.7154(3) 0.0628(5) Uani d . 1 1 . .
H H01A 1.4011 0.6417 0.8281 0.075 Uiso calc R 1 1 . .
H H01B 1.2553 0.6392 0.5998 0.075 Uiso calc R 1 1 . .
H H01C 1.4230 0.5903 0.6867 0.075 Uiso calc R 1 1 . .
C C02 0.7790(3) 0.50863(9) 0.6980(3) 0.0624(5) Uani d . 1 1 . .
H H02A 0.8867 0.4810 0.7363 0.075 Uiso calc R 1 1 . .
H H02B 0.7338 0.5203 0.5590 0.075 Uiso calc R 1 1 . .
H H02C 0.6798 0.4872 0.7165 0.075 Uiso calc R 1 1 . .
C C4 0.8997(2) 0.77379(8) 0.7750(2) 0.0398(3) Uani d . 1 1 . .
C C41 0.7227(2) 0.80257(7) 0.7710(2) 0.0374(3) Uani d . 1 1 . .
C C43 0.4284(2) 0.78993(8) 0.7531(3) 0.0490(4) Uani d . 1 1 . .
H H43 0.3279 0.7644 0.7431 0.059 Uiso calc R 1 1 . .
C C44 0.4121(2) 0.85490(8) 0.7613(3) 0.0490(4) Uani d . 1 1 . .
H H44 0.3002 0.8716 0.7562 0.059 Uiso calc R 1 1 . .
C C46 0.7053(2) 0.86748(8) 0.7796(3) 0.0458(4) Uani d . 1 1 . .
H H46 0.8049 0.8933 0.7881 0.055 Uiso calc R 1 1 . .
N N2 1.03942(18) 0.67337(6) 0.7761(2) 0.0421(3) Uani d . 1 1 . .
N N3 0.89650(18) 0.71015(6) 0.7821(2) 0.0425(3) Uani d . 1 1 . .
H H3 0.8023 0.6918 0.7906 0.051 Uiso calc R 1 1 . .
N N42 0.58415(18) 0.76297(6) 0.7590(2) 0.0456(3) Uani d . 1 1 . .
N N45 0.5491(2) 0.89439(7) 0.7761(2) 0.0529(4) Uani d . 1 1 . .
O O5 1.02739(17) 0.80592(6) 0.7719(2) 0.0585(3) Uani d . 1 1 . .
S S1 1.18679(6) 0.56102(2) 0.77482(9) 0.05940(17) Uani d . 1 1 . .
S S2 0.84763(6) 0.57861(2) 0.85177(8) 0.05666(16) Uani d . 1 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
N2 C1 S1 . . 120.54(12) ?
N2 C1 S2 . . 123.95(12) ?
S1 C1 S2 . . 115.37(9) ?
S1 C01 H01A . . 109.5 ?
S1 C01 H01B . . 109.5 ?
H01A C01 H01B . . 109.5 ?
S1 C01 H01C . . 109.5 ?
H01A C01 H01C . . 109.5 ?
H01B C01 H01C . . 109.5 ?
S2 C02 H02A . . 109.5 ?
S2 C02 H02B . . 109.5 ?
H02A C02 H02B . . 109.5 ?
S2 C02 H02C . . 109.5 ?
H02A C02 H02C . . 109.5 ?
H02B C02 H02C . . 109.5 ?
O5 C4 N3 . . 125.92(14) ?
O5 C4 C41 . . 122.27(14) ?
N3 C4 C41 . . 111.81(13) ?
N42 C41 C46 . . 121.83(14) ?
N42 C41 C4 . . 117.57(14) ?
C46 C41 C4 . . 120.60(14) ?
N42 C43 C44 . . 121.67(16) ?
N42 C43 H43 . . 119.2 ?
C44 C43 H43 . . 119.2 ?
N45 C44 C43 . . 122.71(15) ?
N45 C44 H44 . . 118.6 ?
C43 C44 H44 . . 118.6 ?
N45 C46 C41 . . 121.85(15) ?
N45 C46 H46 . . 119.1 ?
C41 C46 H46 . . 119.1 ?
C1 N2 N3 . . 115.58(13) ?
C4 N3 N2 . . 122.10(13) ?
C4 N3 H3 . . 119.0 ?
N2 N3 H3 . . 119.0 ?
C43 N42 C41 . . 116.10(14) ?
C44 N45 C46 . . 115.82(14) ?
C1 S1 C01 . . 101.17(9) ?
C1 S2 C02 . . 103.63(9) ?
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
C1 N2 . 1.278(2) ?
C1 S1 . 1.7478(15) ?
C1 S2 . 1.7723(16) ?
C01 S1 . 1.794(2) ?
C01 H01A . 0.9600 ?
C01 H01B . 0.9600 ?
C01 H01C . 0.9600 ?
C02 S2 . 1.795(2) ?
C02 H02A . 0.9600 ?
C02 H02B . 0.9600 ?
C02 H02C . 0.9600 ?
C4 O5 . 1.2165(19) ?
C4 N3 . 1.344(2) ?
C4 C41 . 1.502(2) ?
C41 N42 . 1.3411(19) ?
C41 C46 . 1.380(2) ?
C43 N42 . 1.329(2) ?
C43 C44 . 1.380(2) ?
C43 H43 . 0.9300 ?
C44 N45 . 1.324(2) ?
C44 H44 . 0.9300 ?
C46 N45 . 1.339(2) ?
C46 H46 . 0.9300 ?
N2 N3 . 1.3785(17) ?
N3 H3 . 0.8600 ?
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
C44 H44 O5 1_455 0.93 2.59 3.219(2) 125
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
O5 C4 C41 N42 . . . . 174.91(15) ?
N3 C4 C41 N42 . . . . -5.0(2) ?
O5 C4 C41 C46 . . . . -5.2(2) ?
N3 C4 C41 C46 . . . . 174.88(15) ?
N42 C43 C44 N45 . . . . -0.2(3) ?
N42 C41 C46 N45 . . . . -0.1(3) ?
C4 C41 C46 N45 . . . . 179.96(14) ?
S1 C1 N2 N3 . . . . 176.70(11) ?
S2 C1 N2 N3 . . . . -7.8(2) ?
O5 C4 N3 N2 . . . . -3.4(3) ?
C41 C4 N3 N2 . . . . 176.49(12) ?
C1 N2 N3 C4 . . . . 177.07(15) ?
C44 C43 N42 C41 . . . . -0.8(3) ?
C46 C41 N42 C43 . . . . 0.9(2) ?
C4 C41 N42 C43 . . . . -179.16(14) ?
C43 C44 N45 C46 . . . . 1.0(3) ?
C41 C46 N45 C44 . . . . -0.8(3) ?
N2 C1 S1 C01 . . . . -4.05(17) ?
S2 C1 S1 C01 . . . . -179.90(10) ?
N2 C1 S2 C02 . . . . 141.69(15) ?
S1 C1 S2 C02 . . . . -42.62(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9370946
2 PubChem 11195877
