#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018130.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_2018130
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          'C9 H12 N4 O2 S2'
_chemical_formula_moiety         'C9 H12 N4 O2 S2'
_chemical_formula_sum            'C9 H12 N4 O2 S2'
_chemical_formula_weight         272.35
_chemical_name_systematic
;
N'-[bis(methylsulfanyl)methylidene]-6-methoxypyrazine-2-carbohydrazide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 115.430(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.111(2)
_cell_length_b                   7.5812(7)
_cell_length_c                   15.6547(14)
_cell_measurement_reflns_used    8658
_cell_measurement_temperature    270
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.70
_cell_volume                     2477.1(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2002)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_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      270
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27591
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisme
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.412
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0720P)²+1.1533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                2351
_reflns_number_total             3051
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3386.cif
_cod_data_source_block           F2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018130
_cod_database_fobs_code          2018130
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.32187(8) 0.0500(2) 0.93843(13) 0.0441(4) Uani d . 1 1 . .
C C01 0.30859(12) 0.0459(3) 1.10871(16) 0.0677(6) Uani d . 1 1 . .
H H01A 0.2641 0.0784 1.0808 0.081 Uiso calc R 1 1 . .
H H01B 0.3278 0.0790 1.1743 0.081 Uiso calc R 1 1 . .
H H01C 0.3124 -0.0793 1.1034 0.081 Uiso calc R 1 1 . .
C C02 0.23931(11) -0.1431(3) 0.78714(16) 0.0634(5) Uani d . 1 1 . .
H H02A 0.2379 -0.0503 0.7446 0.076 Uiso calc R 1 1 . .
H H02B 0.2007 -0.2115 0.7593 0.076 Uiso calc R 1 1 . .
H H02C 0.2755 -0.2177 0.7991 0.076 Uiso calc R 1 1 . .
C C4 0.44767(9) 0.1438(2) 0.87865(12) 0.0460(4) Uani d . 1 1 . .
C C11 0.56273(13) 0.3733(3) 1.20507(16) 0.0721(6) Uani d . 1 1 . .
H H11A 0.5205 0.4214 1.1714 0.086 Uiso calc R 1 1 . .
H H11B 0.5820 0.4214 1.2679 0.086 Uiso calc R 1 1 . .
H H11C 0.5600 0.2473 1.2085 0.086 Uiso calc R 1 1 . .
C C41 0.51134(8) 0.2302(2) 0.93364(12) 0.0431(4) Uani d . 1 1 . .
C C43 0.58091(9) 0.3626(2) 1.06730(14) 0.0513(4) Uani d . 1 1 . .
C C44 0.62150(10) 0.3955(3) 1.02402(17) 0.0635(6) Uani d . 1 1 . .
H H44 0.6592 0.4578 1.0573 0.076 Uiso calc R 1 1 . .
C C46 0.55275(9) 0.2544(3) 0.89284(14) 0.0552(5) Uani d . 1 1 . .
H H46 0.5422 0.2096 0.8327 0.066 Uiso calc R 1 1 . .
N N2 0.35298(7) 0.05000(19) 0.88799(10) 0.0447(3) Uani d . 1 1 . .
N N3 0.41252(7) 0.13022(19) 0.92788(10) 0.0434(3) Uani d . 1 1 . .
H H3 0.4271 0.1716 0.9844 0.052 Uiso calc R 1 1 . .
N N42 0.52559(7) 0.28252(19) 1.02262(10) 0.0438(3) Uani d . 1 1 . .
N N45 0.60835(9) 0.3418(3) 0.93820(15) 0.0655(5) Uani d . 1 1 . .
O O5 0.43033(8) 0.0961(2) 0.79736(10) 0.0717(5) Uani d . 1 1 . .
O O6 0.60084(8) 0.4175(2) 1.15676(11) 0.0686(4) Uani d . 1 1 . .
S S1 0.34869(3) 0.15723(7) 1.04845(4) 0.06153(19) Uani d . 1 1 . .
S S2 0.24630(2) -0.05000(7) 0.89574(4) 0.06069(18) 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 S2 . . 119.89(13) ?
N2 C1 S1 . . 123.41(13) ?
S2 C1 S1 . . 116.61(10) ?
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 . . 124.78(17) ?
O5 C4 C41 . . 122.21(16) ?
N3 C4 C41 . . 112.99(15) ?
O6 C11 H11A . . 109.5 ?
O6 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O6 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N42 C41 C46 . . 122.19(17) ?
N42 C41 C4 . . 117.81(15) ?
C46 C41 C4 . . 120.00(17) ?
N42 C43 O6 . . 121.31(18) ?
N42 C43 C44 . . 121.85(19) ?
O6 C43 C44 . . 116.84(18) ?
N45 C44 C43 . . 122.32(19) ?
N45 C44 H44 . . 118.8 ?
C43 C44 H44 . . 118.8 ?
N45 C46 C41 . . 121.27(19) ?
N45 C46 H46 . . 119.4 ?
C41 C46 H46 . . 119.4 ?
C1 N2 N3 . . 115.85(14) ?
C4 N3 N2 . . 120.27(14) ?
C4 N3 H3 . . 119.9 ?
N2 N3 H3 . . 119.9 ?
C43 N42 C41 . . 115.91(16) ?
C44 N45 C46 . . 116.32(18) ?
C43 O6 C11 . . 117.95(16) ?
C1 S1 C01 . . 104.67(10) ?
C1 S2 C02 . . 101.68(10) ?
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 . 1.276(2) ?
C1 S2 . 1.7519(17) ?
C1 S1 . 1.7592(18) ?
C01 S1 . 1.792(2) ?
C01 H01A . 0.9600 ?
C01 H01B . 0.9600 ?
C01 H01C . 0.9600 ?
C02 S2 . 1.783(2) ?
C02 H02A . 0.9600 ?
C02 H02B . 0.9600 ?
C02 H02C . 0.9600 ?
C4 O5 . 1.214(2) ?
C4 N3 . 1.342(2) ?
C4 C41 . 1.499(2) ?
C11 O6 . 1.425(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C41 N42 . 1.346(2) ?
C41 C46 . 1.372(3) ?
C43 N42 . 1.313(2) ?
C43 O6 . 1.339(3) ?
C43 C44 . 1.395(3) ?
C44 N45 . 1.308(3) ?
C44 H44 . 0.9300 ?
C46 N45 . 1.345(3) ?
C46 H46 . 0.9300 ?
N2 N3 . 1.3839(19) ?
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
C46 H46 O5 2_656 0.93 2.53 3.385(3) 153
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 . . . . 178.34(18) ?
N3 C4 C41 N42 . . . . 0.0(2) ?
O5 C4 C41 C46 . . . . -1.3(3) ?
N3 C4 C41 C46 . . . . -179.71(16) ?
N42 C43 C44 N45 . . . . -3.1(3) ?
O6 C43 C44 N45 . . . . 177.2(2) ?
N42 C41 C46 N45 . . . . -4.1(3) ?
C4 C41 C46 N45 . . . . 175.60(17) ?
S2 C1 N2 N3 . . . . -179.29(11) ?
S1 C1 N2 N3 . . . . 4.4(2) ?
O5 C4 N3 N2 . . . . 3.1(3) ?
C41 C4 N3 N2 . . . . -178.58(14) ?
C1 N2 N3 C4 . . . . -177.06(16) ?
O6 C43 N42 C41 . . . . -178.65(16) ?
C44 C43 N42 C41 . . . . 1.7(3) ?
C46 C41 N42 C43 . . . . 1.8(3) ?
C4 C41 N42 C43 . . . . -177.90(15) ?
C43 C44 N45 C46 . . . . 0.9(3) ?
C41 C46 N45 C44 . . . . 2.6(3) ?
N42 C43 O6 C11 . . . . 5.2(3) ?
C44 C43 O6 C11 . . . . -175.1(2) ?
N2 C1 S1 C01 . . . . -156.84(16) ?
S2 C1 S1 C01 . . . . 26.73(14) ?
N2 C1 S2 C02 . . . . 4.43(17) ?
S1 C1 S2 C02 . . . . -179.00(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654312
2 PubChem 93998445
