#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018131.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_2018131
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
;
methyl 1-methyl-2-(pyrazin-2-ylcarbonyl)hydrazinecarbodithioate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.151(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.0900(4)
_cell_length_b                   6.4482(6)
_cell_length_c                   20.7828(19)
_cell_measurement_reflns_used    8014
_cell_measurement_temperature    290
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      2.94
_cell_volume                     548.00(9)
_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  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12608
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.210
_refine_ls_abs_structure_details
'Flack (1983), with how many Friedel pairs?'
_refine_ls_abs_structure_Flack   0.18(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0460
_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)+(0.0713P)²+0.2203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                2523
_reflns_number_total             2642
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3386.cif
_cod_data_source_block           G1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2018131
_cod_database_fobs_code          2018131
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.0937(7) 0.8741(5) 0.85674(13) 0.0386(6) Uani d . 1 1 . .
C C01 1.4285(9) 0.5824(6) 0.93116(16) 0.0562(9) Uani d . 1 1 . .
H H01A 1.2695 0.6055 0.9638 0.067 Uiso calc R 1 1 . .
H H01B 1.6046 0.6797 0.9366 0.067 Uiso calc R 1 1 . .
H H01C 1.5123 0.4438 0.9349 0.067 Uiso calc R 1 1 . .
C C4 0.9719(7) 0.8113(5) 0.69513(14) 0.0388(6) Uani d . 1 1 . .
C C10 0.7799(9) 1.1372(6) 0.79370(16) 0.0524(7) Uani d . 1 1 . .
H H10A 0.9419 1.2346 0.7801 0.063 Uiso calc R 1 1 . .
H H10B 0.6903 1.1826 0.8337 0.063 Uiso calc R 1 1 . .
H H10C 0.6084 1.1282 0.7616 0.063 Uiso calc R 1 1 . .
C C41 0.8459(7) 0.6519(4) 0.64844(12) 0.0362(5) Uani d . 1 1 . .
C C43 0.5792(9) 0.3512(5) 0.62875(18) 0.0534(8) Uani d . 1 1 . .
H H43 0.4588 0.2380 0.6427 0.064 Uiso calc R 1 1 . .
C C44 0.6554(10) 0.3659(6) 0.56436(18) 0.0576(8) Uani d . 1 1 . .
H H44 0.5901 0.2599 0.5366 0.069 Uiso calc R 1 1 . .
C C46 0.9132(9) 0.6699(5) 0.58369(14) 0.0488(7) Uani d . 1 1 . .
H H46 1.0275 0.7854 0.5696 0.059 Uiso calc R 1 1 . .
N N2 0.9302(7) 0.9338(4) 0.80247(11) 0.0419(5) Uani d . 1 1 . .
N N3 0.8641(6) 0.7856(4) 0.75509(11) 0.0402(5) Uani d . 1 1 . .
H H3 0.7532 0.6767 0.7644 0.048 Uiso calc R 1 1 . .
N N42 0.6733(7) 0.4945(4) 0.67133(12) 0.0451(6) Uani d . 1 1 . .
N N45 0.8187(9) 0.5261(6) 0.54075(13) 0.0591(7) Uani d . 1 1 . .
O O5 1.1584(6) 0.9485(4) 0.67904(12) 0.0572(6) Uani d . 1 1 . .
S S1 1.23971(17) 0.61678(12) 0.85307(3) 0.04268(18) Uani d . 1 1 . .
S S2 1.1449(2) 1.03003(14) 0.91904(4) 0.0560(2) 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'
S S 0.1246 0.1234 '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'
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 . . 122.2(2) ?
N2 C1 S1 . . 113.1(2) ?
S2 C1 S1 . . 124.69(18) ?
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 ?
O5 C4 N3 . . 124.3(3) ?
O5 C4 C41 . . 121.9(3) ?
N3 C4 C41 . . 113.7(2) ?
N2 C10 H10A . . 109.5 ?
N2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N42 C41 C46 . . 121.9(3) ?
N42 C41 C4 . . 118.0(2) ?
C46 C41 C4 . . 120.0(3) ?
N42 C43 C44 . . 121.9(3) ?
N42 C43 H43 . . 119.1 ?
C44 C43 H43 . . 119.1 ?
N45 C44 C43 . . 122.3(3) ?
N45 C44 H44 . . 118.8 ?
C43 C44 H44 . . 118.8 ?
N45 C46 C41 . . 122.0(3) ?
N45 C46 H46 . . 119.0 ?
C41 C46 H46 . . 119.0 ?
C1 N2 N3 . . 118.6(3) ?
C1 N2 C10 . . 124.0(3) ?
N3 N2 C10 . . 116.9(2) ?
C4 N3 N2 . . 120.6(2) ?
C4 N3 H3 . . 119.7 ?
N2 N3 H3 . . 119.7 ?
C41 N42 C43 . . 116.1(3) ?
C44 N45 C46 . . 115.6(3) ?
C1 S1 C01 . . 102.50(16) ?
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 . 1.355(4) ?
C1 S2 . 1.649(3) ?
C1 S1 . 1.765(3) ?
C01 S1 . 1.797(3) ?
C01 H01A . 0.9600 ?
C01 H01B . 0.9600 ?
C01 H01C . 0.9600 ?
C4 O5 . 1.219(4) ?
C4 N3 . 1.341(4) ?
C4 C41 . 1.497(4) ?
C10 N2 . 1.458(4) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C41 N42 . 1.330(4) ?
C41 C46 . 1.384(4) ?
C43 N42 . 1.331(4) ?
C43 C44 . 1.383(5) ?
C43 H43 . 0.9300 ?
C44 N45 . 1.329(5) ?
C44 H44 . 0.9300 ?
C46 N45 . 1.338(4) ?
C46 H46 . 0.9300 ?
N2 N3 . 1.395(3) ?
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
N3 H3 S1 1_455 0.86 2.85 3.473(3) 131
C43 H43 O5 1_445 0.93 2.37 3.297(4) 179
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 . . . . 172.6(3) ?
N3 C4 C41 N42 . . . . -6.5(4) ?
O5 C4 C41 C46 . . . . -6.7(5) ?
N3 C4 C41 C46 . . . . 174.2(3) ?
N42 C43 C44 N45 . . . . -1.9(6) ?
N42 C41 C46 N45 . . . . -2.5(5) ?
C4 C41 C46 N45 . . . . 176.8(3) ?
S2 C1 N2 N3 . . . . -172.5(2) ?
S1 C1 N2 N3 . . . . 7.3(3) ?
S2 C1 N2 C10 . . . . -1.0(4) ?
S1 C1 N2 C10 . . . . 178.8(2) ?
O5 C4 N3 N2 . . . . 8.0(5) ?
C41 C4 N3 N2 . . . . -172.9(3) ?
C1 N2 N3 C4 . . . . -121.9(3) ?
C10 N2 N3 C4 . . . . 66.0(4) ?
C46 C41 N42 C43 . . . . 2.4(5) ?
C4 C41 N42 C43 . . . . -176.9(3) ?
C44 C43 N42 C41 . . . . -0.3(5) ?
C43 C44 N45 C46 . . . . 1.9(6) ?
C41 C46 N45 C44 . . . . 0.2(6) ?
N2 C1 S1 C01 . . . . -178.2(2) ?
S2 C1 S1 C01 . . . . 1.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654313
2 PubChem 93997332
