#------------------------------------------------------------------------------
#$Date: 2018-02-28 09:18:30 +0200 (Wed, 28 Feb 2018) $
#$Revision: 206693 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/10/2021048.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_2021048
loop_
_publ_author_name
'Szczesio, Małgorzata'
'Gołka, Jolanta'
'Korona-Głowniak, Izabela'
'Orlewska, Czesława'
'Gobis, Katarzyna'
'Olczak, Andrzej'
_publ_section_title
;
 Planarity of heteroaryldithiocarbazic acid derivatives showing
 tuberculostatic activity: structure--activity relationships
;
_journal_coeditor_code           FN3253
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961800284X
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C9 H12 N4 S2'
_chemical_formula_moiety         'C9 H12 N4 S2'
_chemical_formula_sum            'C9 H12 N4 S2'
_chemical_formula_weight         240.35
_chemical_name_systematic
;
(Z)-Methyl
2-[amino(pyridin-2-yl)methylidene]-1-methylhydrazinecarbodithioate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                79.167(2)
_cell_angle_beta                 71.019(2)
_cell_angle_gamma                84.080(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3230(2)
_cell_length_b                   8.5983(2)
_cell_length_c                   10.0343(2)
_cell_measurement_reflns_used    21672
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7410
_cell_measurement_theta_min      4.7090
_cell_volume                     586.21(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24172
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.020
_diffrn_reflns_theta_min         4.724
_exptl_absorpt_coefficient_mu    3.906
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.176
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.300
_refine_ls_extinction_coef       0.0147(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0656P)²+0.3090P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                2393
_reflns_number_total             2417
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fn3253sup1.cif
_cod_data_source_block           S3
_cod_database_code               2021048
_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.
;
_shelxl_version_number           2.014
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
C C1 0.31630(19) 0.09177(17) 0.72264(15) 0.0122(3) Uani d 1
S S1 0.34397(5) 0.06346(4) 0.89411(4) 0.01573(15) Uani d 1
C C2 0.3910(2) 0.27722(18) 0.49557(16) 0.0171(3) Uani d 1
H H2A 0.4059 0.1910 0.4439 0.026 Uiso calc 1
H H2B 0.4892 0.3516 0.4443 0.026 Uiso calc 1
H H2C 0.2658 0.3291 0.5056 0.026 Uiso calc 1
N N2 0.40933(17) 0.21624(15) 0.63707(13) 0.0135(3) Uani d 1
S S2 0.18763(5) -0.02514(4) 0.67422(4) 0.01568(15) Uani d 1
N N3 0.47965(17) 0.32513(15) 0.69812(13) 0.0144(3) Uani d 1
C C4 0.6665(2) 0.30834(17) 0.67435(15) 0.0130(3) Uani d 1
N N5 0.7889(2) 0.20436(17) 0.60358(15) 0.0204(3) Uani d 1
H H5A 0.752(3) 0.133(3) 0.569(2) 0.024 Uiso d 1
H H5B 0.899(3) 0.199(3) 0.603(2) 0.024 Uiso d 1
C C11 0.2272(2) -0.11904(19) 0.97915(17) 0.0211(3) Uani d 1
H H11A 0.0966 -0.1093 0.9764 0.032 Uiso calc 1
H H11B 0.2264 -0.1420 1.0767 0.032 Uiso calc 1
H H11C 0.2960 -0.2034 0.9299 0.032 Uiso calc 1
C C41 0.7511(2) 0.41881(16) 0.73531(15) 0.0124(3) Uani d 1
N N42 0.94248(18) 0.40172(16) 0.70950(15) 0.0190(3) Uani d 1
C C43 1.0231(2) 0.4971(2) 0.76351(19) 0.0229(4) Uani d 1
H H43 1.1560 0.4864 0.7470 0.027 Uiso calc 1
C C44 0.9187(2) 0.6113(2) 0.84294(18) 0.0220(3) Uani d 1
H H44 0.9803 0.6756 0.8784 0.026 Uiso calc 1
C C45 0.7210(2) 0.6273(2) 0.86809(18) 0.0219(3) Uani d 1
H H45 0.6473 0.7030 0.9206 0.026 Uiso calc 1
C C46 0.6342(2) 0.52893(19) 0.81397(16) 0.0177(3) Uani d 1
H H46 0.5015 0.5365 0.8299 0.021 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N2 C1 S2 124.23(11)
N2 C1 S1 112.10(10)
S2 C1 S1 123.67(9)
C1 S1 C11 102.69(7)
N2 C2 H2A 109.5
N2 C2 H2B 109.5
H2A C2 H2B 109.5
N2 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C1 N2 N3 118.75(12)
C1 N2 C2 123.12(12)
N3 N2 C2 115.15(12)
C4 N3 N2 112.75(11)
N3 C4 N5 127.57(14)
N3 C4 C41 115.85(12)
N5 C4 C41 116.57(13)
C4 N5 H5A 122.6(14)
C4 N5 H5B 118.5(15)
H5A N5 H5B 118(2)
S1 C11 H11A 109.5
S1 C11 H11B 109.5
H11A C11 H11B 109.5
S1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N42 C41 C46 123.67(13)
N42 C41 C4 115.47(12)
C46 C41 C4 120.85(13)
C41 N42 C43 117.22(13)
N42 C43 C44 123.42(15)
N42 C43 H43 118.3
C44 C43 H43 118.3
C45 C44 C43 118.43(14)
C45 C44 H44 120.8
C43 C44 H44 120.8
C44 C45 C46 119.14(14)
C44 C45 H45 120.4
C46 C45 H45 120.4
C45 C46 C41 118.12(14)
C45 C46 H46 120.9
C41 C46 H46 120.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.331(2)
C1 S2 1.6767(14)
C1 S1 1.7663(14)
S1 C11 1.7947(16)
C2 N2 1.4626(19)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
N2 N3 1.4273(17)
N3 C4 1.3073(19)
C4 N5 1.3292(19)
C4 C41 1.4991(19)
N5 H5A 0.86(2)
N5 H5B 0.80(2)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C41 N42 1.3373(19)
C41 C46 1.388(2)
N42 C43 1.338(2)
C43 C44 1.388(2)
C43 H43 0.9300
C44 C45 1.383(2)
C44 H44 0.9300
C45 C46 1.387(2)
C45 H45 0.9300
C46 H46 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
N5 H5B S2 1_655 0.80(2) 2.88(2) 3.5431(14) 141.3(19)
N5 H5A S2 2_656 0.86(2) 2.66(2) 3.3798(14) 141.5(18)

_cod_database_fobs_code 2021048
