#------------------------------------------------------------------------------
#$Date: 2023-06-29 18:22:27 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284681 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/21/2312130.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_2312130
loop_
_publ_author_name
'Ziembicka, Dagmara'
'Olczak, Andrzej'
'Gobis, Katarzyna'
'Korona-Głowniak, Izabela'
'Pietrzak, Anna'
'Augustynowicz-Kopeć, Ewa'
'Głogowska, Agnieszka'
'Zaborowski, Marcin'
'Szczesio, Małgorzata'
_publ_section_title
;
 Synthesis, structure, ADME and biological activity of three
 2,6-disubstituted thiosemicarbazone derivatives.
;
_journal_coeditor_code           VP3029
_journal_issue                   7
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              283
_journal_page_last               291
_journal_paper_doi               10.1107/S2053229623005521
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C13 H20 N6 S'
_chemical_formula_moiety         'C13 H20 N6 S'
_chemical_formula_sum            'C13 H20 N6 S'
_chemical_formula_weight         292.41
_chemical_name_systematic
2-{Amino[6-(pyrrolidin-1-yl)pyridin-2-yl]methylidene}-N,N-dimethylhydrazine-1-carbothioamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.01.27 svn.rdd5efbe for OlexSys, GUI svn.r6708)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.202(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1032(2)
_cell_length_b                   10.90340(10)
_cell_length_c                   15.3748(2)
_cell_measurement_reflns_used    19769
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      78.4090
_cell_measurement_theta_min      5.0360
_cell_volume                     1457.78(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009),
ShelXle (Hübschle et al., 2011) and
Mercury program (Macrae et al., 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and OLEX2 (Dolomanov et al.,
2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.487
_diffrn_reflns_theta_min         5.052
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.973
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2022)
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.370
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0373
_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)+(0.0553P)²+0.6020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2716
_reflns_number_total             2926
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3029sup1.cif
_cod_data_source_block           4
_cod_database_code               2312130
_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.
;
_shelx_estimated_absorpt_t_min   0.356
_shelx_estimated_absorpt_t_max   0.874
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.04534(4) 0.75908(3) 0.37551(2) 0.01890(14) Uani d 1 . .
N N1 -0.18255(14) 0.65105(12) 0.24490(9) 0.0230(3) Uani d 1 . .
N N2 0.04897(14) 0.55753(11) 0.27110(8) 0.0201(3) Uani d 1 . .
N N3 0.20290(14) 0.56162(12) 0.31890(8) 0.0181(3) Uani d 1 . .
N N4 0.24591(17) 0.39043(12) 0.24336(9) 0.0219(3) Uani d 1 . .
N N22 0.50248(14) 0.59473(11) 0.40280(8) 0.0181(3) Uani d 1 . .
N N31 0.68835(14) 0.71376(12) 0.50042(9) 0.0215(3) Uani d 1 . .
C C1 -0.03178(16) 0.64798(13) 0.29379(10) 0.0177(3) Uani d 1 . .
C C4 0.29823(17) 0.48042(13) 0.30400(9) 0.0182(3) Uani d 1 . .
C C11 -0.29400(18) 0.73250(15) 0.26571(12) 0.0239(3) Uani d 1 . .
H H11A -0.323815 0.796436 0.218982 0.036 Uiso calc 1 . .
H H11B -0.248221 0.770578 0.325331 0.036 Uiso calc 1 . .
H H11C -0.385110 0.685409 0.266840 0.036 Uiso calc 1 . .
C C12 -0.2454(2) 0.56785(16) 0.16875(13) 0.0331(4) Uani d 1 . .
H H12A -0.317917 0.612407 0.118890 0.050 Uiso calc 1 . .
H H12B -0.298871 0.500177 0.188434 0.050 Uiso calc 1 . .
H H12C -0.161559 0.535029 0.147734 0.050 Uiso calc 1 . .
C C21 0.46085(17) 0.48744(13) 0.35892(9) 0.0177(3) Uani d 1 . .
C C23 0.64784(16) 0.60524(14) 0.45664(10) 0.0186(3) Uani d 1 . .
C C24 0.75565(17) 0.50775(15) 0.46824(10) 0.0211(3) Uani d 1 . .
H H24 0.857993 0.516959 0.506761 0.025 Uiso calc 1 . .
C C25 0.70829(18) 0.40031(15) 0.42252(10) 0.0242(3) Uani d 1 . .
H H25 0.778245 0.333809 0.429467 0.029 Uiso calc 1 . .
C C26 0.55768(18) 0.38779(15) 0.36568(10) 0.0223(3) Uani d 1 . .
H H26 0.523292 0.314057 0.333096 0.027 Uiso calc 1 . .
C C32 0.58185(17) 0.81708(14) 0.48718(11) 0.0230(3) Uani d 1 . .
H H32A 0.483389 0.792270 0.497055 0.028 Uiso calc 1 . .
H H32B 0.560985 0.852035 0.425281 0.028 Uiso calc 1 . .
C C33 0.66818(19) 0.90798(16) 0.55941(12) 0.0312(4) Uani d 1 . .
H H33A 0.640406 0.993467 0.539570 0.037 Uiso calc 1 . .
H H33B 0.645787 0.893661 0.617800 0.037 Uiso calc 1 . .
C C34 0.8362(2) 0.88260(16) 0.56860(13) 0.0327(4) Uani d 1 . .
H H34A 0.903150 0.909418 0.628810 0.039 Uiso calc 1 . .
H H34B 0.868387 0.925225 0.520377 0.039 Uiso calc 1 . .
C C35 0.84309(18) 0.74405(14) 0.55830(11) 0.0225(3) Uani d 1 . .
H H35A 0.921969 0.720686 0.528742 0.027 Uiso calc 1 . .
H H35B 0.865881 0.702534 0.618085 0.027 Uiso calc 1 . .
H H4A 0.311(3) 0.3524(19) 0.2181(15) 0.037(5) Uiso d 1 . .
H H4B 0.155(3) 0.3930(18) 0.2153(14) 0.030(5) Uiso d 1 . .
H H3 0.235(2) 0.6166(18) 0.3602(13) 0.025(5) Uiso 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 0.0181 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -2 0.0281
-1 0 2 0.0440
-3 6 -2 0.2931
3 -6 2 0.2653
3 6 1 0.2062
0 -7 0 0.3518
-5 0 -3 0.2571
5 -1 -7 0.0546
-5 1 7 0.0383
5 0 2 0.2042
-2 -1 -8 0.2723
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
C1 N1 C11 . . 123.43(13) ?
C1 N1 C12 . . 121.48(13) ?
C11 N1 C12 . . 115.05(13) ?
C1 N2 N3 . . 112.84(12) ?
N2 N3 H3 . . 119.4(13) ?
C4 N3 N2 . . 120.55(13) ?
C4 N3 H3 . . 120.0(13) ?
C4 N4 H4A . . 119.8(14) ?
C4 N4 H4B . . 116.1(14) ?
H4A N4 H4B . . 118.9(19) ?
C23 N22 C21 . . 117.57(12) ?
C23 N31 C32 . . 122.10(13) ?
C23 N31 C35 . . 124.72(12) ?
C32 N31 C35 . . 112.97(12) ?
N1 C1 S1 . . 120.66(11) ?
N2 C1 S1 . . 124.58(11) ?
N2 C1 N1 . . 114.71(13) ?
N3 C4 N4 . . 120.02(14) ?
N3 C4 C21 . . 118.11(13) ?
N4 C4 C21 . . 121.79(13) ?
N1 C11 H11A . . 109.5 ?
N1 C11 H11B . . 109.5 ?
N1 C11 H11C . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12B . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N22 C21 C4 . . 114.72(12) ?
N22 C21 C26 . . 124.44(14) ?
C26 C21 C4 . . 120.81(13) ?
N22 C23 N31 . . 117.00(13) ?
N22 C23 C24 . . 122.11(14) ?
N31 C23 C24 . . 120.88(14) ?
C23 C24 H24 . . 120.8 ?
C25 C24 C23 . . 118.34(14) ?
C25 C24 H24 . . 120.8 ?
C24 C25 H25 . . 119.8 ?
C24 C25 C26 . . 120.43(14) ?
C26 C25 H25 . . 119.8 ?
C21 C26 C25 . . 117.11(14) ?
C21 C26 H26 . . 121.4 ?
C25 C26 H26 . . 121.4 ?
N31 C32 H32A . . 111.2 ?
N31 C32 H32B . . 111.2 ?
N31 C32 C33 . . 102.85(12) ?
H32A C32 H32B . . 109.1 ?
C33 C32 H32A . . 111.2 ?
C33 C32 H32B . . 111.2 ?
C32 C33 H33A . . 111.0 ?
C32 C33 H33B . . 111.0 ?
H33A C33 H33B . . 109.0 ?
C34 C33 C32 . . 103.75(13) ?
C34 C33 H33A . . 111.0 ?
C34 C33 H33B . . 111.0 ?
C33 C34 H34A . . 111.0 ?
C33 C34 H34B . . 111.0 ?
C33 C34 C35 . . 104.03(13) ?
H34A C34 H34B . . 109.0 ?
C35 C34 H34A . . 111.0 ?
C35 C34 H34B . . 111.0 ?
N31 C35 C34 . . 103.03(12) ?
N31 C35 H35A . . 111.2 ?
N31 C35 H35B . . 111.2 ?
C34 C35 H35A . . 111.2 ?
C34 C35 H35B . . 111.2 ?
H35A C35 H35B . . 109.1 ?
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
S1 C1 . 1.7370(15) ?
N1 C1 . 1.356(2) ?
N1 C11 . 1.4534(19) ?
N1 C12 . 1.458(2) ?
N2 N3 . 1.3771(17) ?
N2 C1 . 1.3366(19) ?
N3 C4 . 1.3065(19) ?
N3 H3 . 0.86(2) ?
N4 C4 . 1.340(2) ?
N4 H4A . 0.90(2) ?
N4 H4B . 0.82(2) ?
N22 C21 . 1.3477(19) ?
N22 C23 . 1.3422(19) ?
N31 C23 . 1.357(2) ?
N31 C32 . 1.4608(19) ?
N31 C35 . 1.464(2) ?
C4 C21 . 1.473(2) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C21 C26 . 1.383(2) ?
C23 C24 . 1.422(2) ?
C24 H24 . 0.9500 ?
C24 C25 . 1.369(2) ?
C25 H25 . 0.9500 ?
C25 C26 . 1.398(2) ?
C26 H26 . 0.9500 ?
C32 H32A . 0.9900 ?
C32 H32B . 0.9900 ?
C32 C33 . 1.522(2) ?
C33 H33A . 0.9900 ?
C33 H33B . 0.9900 ?
C33 C34 . 1.519(2) ?
C34 H34A . 0.9900 ?
C34 H34B . 0.9900 ?
C34 C35 . 1.522(2) ?
C35 H35A . 0.9900 ?
C35 H35B . 0.9900 ?
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
_geom_hbond_publ_flag
C11 H11B S1 . 0.98 2.56 3.0646(17) 112.3 yes
C35 H35A S1 1_655 0.99 2.92 3.7915(16) 146.8 yes
N4 H4A S1 2_545 0.90(2) 2.44(2) 3.3250(14) 170.1(19) yes
N3 H3 S1 . 0.86(2) 2.388(19) 2.8616(13) 115.2(15) yes
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
N2 N3 C4 N4 . . . . -1.6(2) ?
N2 N3 C4 C21 . . . . -178.40(12) ?
N3 N2 C1 S1 . . . . -0.74(17) ?
N3 N2 C1 N1 . . . . 176.74(11) ?
N3 C4 C21 N22 . . . . -16.04(18) ?
N3 C4 C21 C26 . . . . 161.68(13) ?
N4 C4 C21 N22 . . . . 167.22(13) ?
N4 C4 C21 C26 . . . . -15.1(2) ?
N22 C21 C26 C25 . . . . 0.4(2) ?
N22 C23 C24 C25 . . . . 0.1(2) ?
N31 C23 C24 C25 . . . . 179.88(14) ?
N31 C32 C33 C34 . . . . 30.65(17) ?
C1 N2 N3 C4 . . . . -179.19(12) ?
C4 C21 C26 C25 . . . . -177.10(13) ?
C11 N1 C1 S1 . . . . -9.92(19) ?
C11 N1 C1 N2 . . . . 172.49(13) ?
C12 N1 C1 S1 . . . . 172.51(12) ?
C12 N1 C1 N2 . . . . -5.1(2) ?
C21 N22 C23 N31 . . . . 179.97(12) ?
C21 N22 C23 C24 . . . . -0.26(19) ?
C23 N22 C21 C4 . . . . 177.63(11) ?
C23 N22 C21 C26 . . . . 0.0(2) ?
C23 N31 C32 C33 . . . . 171.67(14) ?
C23 N31 C35 C34 . . . . 165.39(14) ?
C23 C24 C25 C26 . . . . 0.3(2) ?
C24 C25 C26 C21 . . . . -0.5(2) ?
C32 N31 C23 N22 . . . . -2.6(2) ?
C32 N31 C23 C24 . . . . 177.65(13) ?
C32 N31 C35 C34 . . . . -9.43(17) ?
C32 C33 C34 C35 . . . . -37.12(18) ?
C33 C34 C35 N31 . . . . 28.44(17) ?
C35 N31 C23 N22 . . . . -176.96(13) ?
C35 N31 C23 C24 . . . . 3.3(2) ?
C35 N31 C32 C33 . . . . -13.35(17) ?

_cod_database_fobs_code 2312130
