#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/79/2017954.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_2017954
loop_
_publ_author_name
'Olczak, Andrzej'
'Szczesio, Małgorzata'
'Gołka, Jolanta'
'Orlewska, Czesława'
'Gobis, Katarzyna'
'Foks, Henryk'
'Główka, Marek L.'
_publ_section_title
;
 Planarity of heteroaryldithiocarbazic acid derivatives showing
 tuberculostatic activity. II. Crystal structures of
 3-[amino(pyrazin-2-yl)methylidene]-2-methylcarbazic acid esters
;
_journal_coeditor_code           FG3209
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o37
_journal_page_last               o42
_journal_paper_doi               10.1107/S0108270110049905
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H19 N5 O4 S2'
_chemical_formula_moiety         'C14 H19 N5 O4 S2'
_chemical_formula_sum            'C14 H19 N5 O4 S2'
_chemical_formula_weight         385.46
_chemical_name_systematic
;
diethyl 2,2'-[({[amino(pyrazin-2-
yl)methylidene]hydrazinylidene}methylidene)bis(sulfanediyl)]diacetate
;
_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                 98.635(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.5249(14)
_cell_length_b                   8.0969(9)
_cell_length_c                   15.4717(6)
_cell_measurement_reflns_used    12369
_cell_measurement_temperature    291
_cell_measurement_theta_max      28.4615
_cell_measurement_theta_min      2.6598
_cell_volume                     3656.7(5)
_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., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      291
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kuma KM-4 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  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21104
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.304
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0292
_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)+(0.0593P)²+0.6854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                3064
_reflns_number_total             3722
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3209.cif
_cod_data_source_block           B1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2017954
_cod_database_fobs_code          2017954
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_disorder_assembly
_atom_site_disorder_group
C C1 0.15561(5) 0.35264(17) 0.12965(9) 0.0341(3) Uani d . 1 . .
C C4 0.10830(5) 0.23775(18) -0.07261(8) 0.0356(3) Uani d . 1 . .
C C11 0.20470(6) 0.20016(19) 0.27392(9) 0.0414(3) Uani d . 1 . .
H H11A 0.2337 0.2539 0.2700 0.050 Uiso calc R 1 . .
H H11B 0.1863 0.2746 0.3034 0.050 Uiso calc R 1 . .
C C12 0.21301(5) 0.04261(18) 0.32516(9) 0.0363(3) Uani d . 1 . .
C C14 0.24295(6) -0.05918(18) 0.46614(9) 0.0429(4) Uani d . 1 . .
H H14A 0.2609 -0.1406 0.4401 0.051 Uiso calc R 1 . .
H H14B 0.2153 -0.1118 0.4794 0.051 Uiso calc R 1 . .
C C15 0.26990(7) 0.0099(2) 0.54705(11) 0.0567(5) Uani d . 1 . .
H H15A 0.2516 0.0887 0.5726 0.068 Uiso calc R 1 . .
H H15B 0.2969 0.0633 0.5328 0.068 Uiso calc R 1 . .
H H15C 0.2787 -0.0778 0.5879 0.068 Uiso calc R 1 . .
C C21 0.13426(5) 0.67846(18) 0.13933(10) 0.0415(3) Uani d . 1 . .
H H21A 0.1418 0.7848 0.1667 0.050 Uiso calc R 1 . .
H H21B 0.1424 0.6824 0.0809 0.050 Uiso calc R 1 . .
C C22 0.08327(5) 0.65033(18) 0.13266(9) 0.0416(3) Uani d . 1 . .
C C24 0.01131(6) 0.7266(3) 0.05408(14) 0.0791(7) Uani d . 1 . .
H H24A -0.0015 0.8015 0.0930 0.095 Uiso calc R 1 . .
H H24B 0.0020 0.6151 0.0660 0.095 Uiso calc R 1 . .
C C25 -0.00556(8) 0.7709(4) -0.03911(16) 0.0989(9) Uani d . 1 . .
H H25A -0.0007 0.8866 -0.0478 0.119 Uiso calc R 1 . .
H H25B -0.0377 0.7464 -0.0525 0.119 Uiso calc R 1 . .
H H25C 0.0109 0.7081 -0.0769 0.119 Uiso calc R 1 . .
C C41 0.09896(5) 0.08074(18) -0.12173(9) 0.0372(3) Uani d . 1 . .
C C43 0.07013(8) -0.0511(3) -0.24623(12) 0.0694(6) Uani d . 1 . .
H H43 0.0557 -0.0490 -0.3039 0.083 Uiso calc R 1 . .
C C44 0.08200(7) -0.2004(2) -0.20854(12) 0.0604(5) Uani d . 1 . .
H H44 0.0751 -0.2961 -0.2410 0.072 Uiso calc R 1 . .
C C46 0.11129(6) -0.0708(2) -0.08432(11) 0.0483(4) Uani d . 1 . .
H H46 0.1259 -0.0735 -0.0268 0.058 Uiso calc R 1 . .
N N2 0.13292(4) 0.37312(15) 0.05315(7) 0.0392(3) Uani d . 1 . .
N N3 0.12640(4) 0.22133(15) 0.00863(7) 0.0400(3) Uani d . 1 . .
N N5 0.09644(5) 0.37870(17) -0.11533(8) 0.0498(3) Uani d . 1 . .
H H5A 0.1007 0.4717 -0.0885 0.060 Uiso calc R 1 . .
H H5B 0.0846 0.3762 -0.1696 0.060 Uiso calc R 1 . .
N N42 0.07829(5) 0.09141(18) -0.20412(9) 0.0581(4) Uani d . 1 . .
N N45 0.10316(6) -0.21282(18) -0.12694(10) 0.0586(4) Uani d . 1 . .
O O12 0.20462(4) -0.09417(14) 0.29774(7) 0.0523(3) Uani d . 1 . .
O O13 0.23145(4) 0.07862(12) 0.40646(7) 0.0462(3) Uani d . 1 . .
O O22 0.06498(4) 0.56275(15) 0.17990(7) 0.0532(3) Uani d . 1 . .
O O23 0.06124(4) 0.73868(17) 0.06809(8) 0.0621(4) Uani d . 1 . .
S S1 0.175323(13) 0.15511(4) 0.16549(2) 0.04032(13) Uani d . 1 . .
S S2 0.167798(13) 0.52195(5) 0.20082(2) 0.04149(13) Uani d . 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 . . 120.44(11) ?
N2 C1 S1 . . 120.70(11) ?
S2 C1 S1 . . 118.86(8) ?
N3 C4 N5 . . 127.24(14) ?
N3 C4 C41 . . 115.22(13) ?
N5 C4 C41 . . 117.53(12) ?
C12 C11 S1 . . 109.65(10) ?
C12 C11 H11A . . 109.7 ?
S1 C11 H11A . . 109.7 ?
C12 C11 H11B . . 109.7 ?
S1 C11 H11B . . 109.7 ?
H11A C11 H11B . . 108.2 ?
O12 C12 O13 . . 124.94(13) ?
O12 C12 C11 . . 126.08(13) ?
O13 C12 C11 . . 108.98(12) ?
O13 C14 C15 . . 106.86(12) ?
O13 C14 H14A . . 110.4 ?
C15 C14 H14A . . 110.4 ?
O13 C14 H14B . . 110.4 ?
C15 C14 H14B . . 110.4 ?
H14A C14 H14B . . 108.6 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C22 C21 S2 . . 113.29(10) ?
C22 C21 H21A . . 108.9 ?
S2 C21 H21A . . 108.9 ?
C22 C21 H21B . . 108.9 ?
S2 C21 H21B . . 108.9 ?
H21A C21 H21B . . 107.7 ?
O22 C22 O23 . . 124.39(15) ?
O22 C22 C21 . . 125.53(14) ?
O23 C22 C21 . . 110.07(13) ?
O23 C24 C25 . . 108.02(17) ?
O23 C24 H24A . . 110.1 ?
C25 C24 H24A . . 110.1 ?
O23 C24 H24B . . 110.1 ?
C25 C24 H24B . . 110.1 ?
H24A C24 H24B . . 108.4 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
N42 C41 C46 . . 120.87(14) ?
N42 C41 C4 . . 117.24(13) ?
C46 C41 C4 . . 121.90(13) ?
N42 C43 C44 . . 122.92(17) ?
N42 C43 H43 . . 118.5 ?
C44 C43 H43 . . 118.5 ?
N45 C44 C43 . . 121.89(17) ?
N45 C44 H44 . . 119.1 ?
C43 C44 H44 . . 119.1 ?
N45 C46 C41 . . 122.93(15) ?
N45 C46 H46 . . 118.5 ?
C41 C46 H46 . . 118.5 ?
C1 N2 N3 . . 110.69(12) ?
C4 N3 N2 . . 113.01(12) ?
C4 N5 H5A . . 120.0 ?
C4 N5 H5B . . 120.0 ?
H5A N5 H5B . . 120.0 ?
C43 N42 C41 . . 115.87(16) ?
C44 N45 C46 . . 115.52(16) ?
C12 O13 C14 . . 117.17(11) ?
C22 O23 C24 . . 116.63(14) ?
C1 S1 C11 . . 101.46(7) ?
C1 S2 C21 . . 100.01(7) ?
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 . 1.2803(17) ?
C1 S2 . 1.7613(14) ?
C1 S1 . 1.7628(14) ?
C4 N3 . 1.2966(17) ?
C4 N5 . 1.3389(19) ?
C4 C41 . 1.486(2) ?
C11 C12 . 1.5026(19) ?
C11 S1 . 1.8062(14) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 O12 . 1.1985(18) ?
C12 O13 . 1.3258(17) ?
C14 O13 . 1.4555(17) ?
C14 C15 . 1.488(2) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C21 C22 . 1.511(2) ?
C21 S2 . 1.7912(14) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C22 O22 . 1.2031(19) ?
C22 O23 . 1.3183(18) ?
C24 O23 . 1.461(2) ?
C24 C25 . 1.497(3) ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
C41 N42 . 1.3309(18) ?
C41 C46 . 1.382(2) ?
C43 N42 . 1.330(2) ?
C43 C44 . 1.365(3) ?
C43 H43 . 0.9300 ?
C44 N45 . 1.326(2) ?
C44 H44 . 0.9300 ?
C46 N45 . 1.330(2) ?
C46 H46 . 0.9300 ?
N2 N3 . 1.4079(17) ?
N5 H5A . 0.8600 ?
N5 H5B . 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
N5 H5A N45 1_565 0.86 2.63 3.320(2) 138.6
C44 H44 O22 6 0.93 2.48 3.403(2) 173.7
C11 H11A O12 4 0.97 2.55 3.473(2) 159.0
N5 H5B O22 6_565 0.86 2.37 3.2002(17) 163.7
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
S1 C11 C12 O12 . . . . 4.8(2) ?
S1 C11 C12 O13 . . . . -175.35(10) ?
S2 C21 C22 O22 . . . . 19.1(2) ?
S2 C21 C22 O23 . . . . -162.16(11) ?
N3 C4 C41 N42 . . . . 176.74(14) ?
N5 C4 C41 N42 . . . . -1.8(2) ?
N3 C4 C41 C46 . . . . -3.6(2) ?
N5 C4 C41 C46 . . . . 177.84(15) ?
N42 C43 C44 N45 . . . . -0.8(3) ?
N42 C41 C46 N45 . . . . -0.6(3) ?
C4 C41 C46 N45 . . . . 179.78(16) ?
S2 C1 N2 N3 . . . . -178.75(10) ?
S1 C1 N2 N3 . . . . 1.44(18) ?
N5 C4 N3 N2 . . . . 0.7(2) ?
C41 C4 N3 N2 . . . . -177.67(12) ?
C1 N2 N3 C4 . . . . -172.45(13) ?
C44 C43 N42 C41 . . . . -0.1(3) ?
C46 C41 N42 C43 . . . . 0.8(3) ?
C4 C41 N42 C43 . . . . -179.58(16) ?
C43 C44 N45 C46 . . . . 1.0(3) ?
C41 C46 N45 C44 . . . . -0.3(3) ?
O12 C12 O13 C14 . . . . 1.1(2) ?
C11 C12 O13 C14 . . . . -178.77(13) ?
C15 C14 O13 C12 . . . . 170.58(14) ?
O22 C22 O23 C24 . . . . -0.3(3) ?
C21 C22 O23 C24 . . . . -179.12(17) ?
C25 C24 O23 C22 . . . . -156.0(2) ?
N2 C1 S1 C11 . . . . 179.31(12) ?
S2 C1 S1 C11 . . . . -0.51(11) ?
C12 C11 S1 C1 . . . . 164.53(11) ?
N2 C1 S2 C21 . . . . 7.65(14) ?
S1 C1 S2 C21 . . . . -172.53(9) ?
C22 C21 S2 C1 . . . . 68.14(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654284
