#------------------------------------------------------------------------------
#$Date: 2021-04-23 12:50:23 +0300 (Fri, 23 Apr 2021) $
#$Revision: 264471 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/23/2022359.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_2022359
loop_
_publ_author_name
'Szczesio, Małgorzata'
'Gobis, Katarzyna'
'Korona-Głowniak, Izabela'
'Mazerant-Politowicz, Ida'
'Ziembicka, Dagmara'
'Foks, Henryk'
'Główka, Marek'
'Olczak, Andrzej'
_publ_section_title
;
 Synthesis, structure and biological activity of four new
 picolinohydrazonamide derivatives
;
_journal_coeditor_code           FM3063
_journal_issue                   7
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              673
_journal_page_last               680
_journal_paper_doi               10.1107/S2053229620007822
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C12 H17 N5 O S'
_chemical_formula_moiety         'C12 H17 N5 O S'
_chemical_formula_sum            'C12 H17 N5 O S'
_chemical_formula_weight         279.36
_chemical_name_common
;
6-Methyl-N'-(morpholine-4-carbonothioyl)picolinohydrazonamide
;
_chemical_name_systematic
;
6-Methyl-N'-[(morpholin-4-yl)carbothioylamino]pyridine-2-carboximidamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 97.16
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0601(2)
_cell_length_b                   10.9903(2)
_cell_length_c                   8.7228(2)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.335
_cell_measurement_theta_min      3.170
_cell_volume                     1337.38(4)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD '
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13619
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.331
_diffrn_reflns_theta_min         3.168
_exptl_absorpt_coefficient_mu    2.162
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.986
_exptl_crystal_size_mid          0.464
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.258
_refine_ls_extinction_coef       0.0251(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0287
_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)+(0.0352P)²+0.8311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                2645
_reflns_number_total             2646
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fm3063sup1.cif
_cod_data_source_block           3
_cod_original_cell_volume        1337.39(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022359
_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   0.224
_shelx_estimated_absorpt_t_max   0.672
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C1 0.70600(8) 0.50211(11) 0.55778(13) 0.0107(2) Uani d 1 . .
C C4 0.76349(8) 0.19479(10) 0.56262(13) 0.0108(2) Uani d 1 . .
C C22 0.63554(9) 0.70582(11) 0.60357(15) 0.0168(3) Uani d 1 . .
H H22A 0.6633 0.7290 0.5115 0.020 Uiso calc 1 . .
H H22B 0.6689 0.7496 0.6907 0.020 Uiso calc 1 . .
C C23 0.52943(10) 0.73824(12) 0.58476(15) 0.0211(3) Uani d 1 . .
H H23A 0.5223 0.8256 0.5720 0.025 Uiso calc 1 . .
H H23B 0.4977 0.6995 0.4923 0.025 Uiso calc 1 . .
C C25 0.49318(9) 0.57149(11) 0.73240(15) 0.0158(3) Uani d 1 . .
H H25A 0.4608 0.5321 0.6409 0.019 Uiso calc 1 . .
H H25B 0.4620 0.5459 0.8202 0.019 Uiso calc 1 . .
C C26 0.59692(9) 0.53191(11) 0.75625(14) 0.0157(3) Uani d 1 . .
H H26A 0.6281 0.5645 0.8531 0.019 Uiso calc 1 . .
H H26B 0.6005 0.4438 0.7616 0.019 Uiso calc 1 . .
C C41 0.82391(8) 0.11208(11) 0.48227(13) 0.0104(2) Uani d 1 . .
C C42 0.81622(8) -0.01364(11) 0.49654(13) 0.0127(2) Uani d 1 . .
H H42 0.7771 -0.0478 0.5635 0.015 Uiso calc 1 . .
C C43 0.86884(9) -0.08646(11) 0.40775(14) 0.0155(3) Uani d 1 . .
H H43 0.8648 -0.1708 0.4127 0.019 Uiso calc 1 . .
C C44 0.92717(9) -0.03146(11) 0.31216(14) 0.0152(2) Uani d 1 . .
H H44 0.9621 -0.0785 0.2503 0.018 Uiso calc 1 . .
C C45 0.93350(8) 0.09563(11) 0.30889(13) 0.0130(2) Uani d 1 . .
C C451 1.00009(9) 0.15750(12) 0.21218(15) 0.0186(3) Uani d 1 . .
H H45A 0.9659 0.2196 0.1505 0.028 Uiso calc 1 . .
H H45B 1.0249 0.0988 0.1459 0.028 Uiso calc 1 . .
H H45C 1.0522 0.1937 0.2783 0.028 Uiso calc 1 . .
N N2 0.70501(7) 0.38672(9) 0.60249(11) 0.0116(2) Uani d 1 . .
N N3 0.76317(7) 0.31112(9) 0.53006(11) 0.0108(2) Uani d 1 . .
N N4 0.70523(7) 0.15231(10) 0.65970(12) 0.0133(2) Uani d 1 . .
N N21 0.64612(7) 0.57536(9) 0.62886(12) 0.0143(2) Uani d 1 . .
N N46 0.88191(7) 0.16668(9) 0.39188(11) 0.0114(2) Uani d 1 . .
O O24 0.48458(6) 0.70023(8) 0.71516(10) 0.0190(2) Uani d 1 . .
S S1 0.77346(2) 0.56026(2) 0.42180(3) 0.01303(12) Uani d 1 . .
H H4A 0.7184(12) 0.0856(17) 0.710(2) 0.025(4) Uiso d 1 . .
H H4B 0.6746(12) 0.2051(15) 0.7020(18) 0.019(4) Uiso d 1 . .
H H3 0.7968(12) 0.3385(15) 0.4673(19) 0.018(4) 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'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N2 C1 N21 . . 113.55(10)
N2 C1 S1 . . 125.51(9)
N21 C1 S1 . . 120.94(9)
N3 C4 N4 . . 119.58(11)
N3 C4 C41 . . 118.94(10)
N4 C4 C41 . . 121.34(10)
N21 C22 C23 . . 109.10(10)
N21 C22 H22A . . 109.9
C23 C22 H22A . . 109.9
N21 C22 H22B . . 109.9
C23 C22 H22B . . 109.9
H22A C22 H22B . . 108.3
O24 C23 C22 . . 111.66(10)
O24 C23 H23A . . 109.3
C22 C23 H23A . . 109.3
O24 C23 H23B . . 109.3
C22 C23 H23B . . 109.3
H23A C23 H23B . . 107.9
O24 C25 C26 . . 111.57(10)
O24 C25 H25A . . 109.3
C26 C25 H25A . . 109.3
O24 C25 H25B . . 109.3
C26 C25 H25B . . 109.3
H25A C25 H25B . . 108.0
N21 C26 C25 . . 109.98(10)
N21 C26 H26A . . 109.7
C25 C26 H26A . . 109.7
N21 C26 H26B . . 109.7
C25 C26 H26B . . 109.7
H26A C26 H26B . . 108.2
N46 C41 C42 . . 123.70(10)
N46 C41 C4 . . 115.45(10)
C42 C41 C4 . . 120.79(10)
C43 C42 C41 . . 117.97(11)
C43 C42 H42 . . 121.0
C41 C42 H42 . . 121.0
C44 C43 C42 . . 118.84(11)
C44 C43 H43 . . 120.6
C42 C43 H43 . . 120.6
C43 C44 C45 . . 119.56(11)
C43 C44 H44 . . 120.2
C45 C44 H44 . . 120.2
N46 C45 C44 . . 122.07(11)
N46 C45 C451 . . 117.29(11)
C44 C45 C451 . . 120.64(11)
C45 C451 H45A . . 109.5
C45 C451 H45B . . 109.5
H45A C451 H45B . . 109.5
C45 C451 H45C . . 109.5
H45A C451 H45C . . 109.5
H45B C451 H45C . . 109.5
C1 N2 N3 . . 114.47(9)
C4 N3 N2 . . 118.48(10)
C4 N3 H3 . . 121.0(11)
N2 N3 H3 . . 120.5(11)
C4 N4 H4A . . 120.6(12)
C4 N4 H4B . . 115.3(11)
H4A N4 H4B . . 117.2(15)
C1 N21 C22 . . 124.62(10)
C1 N21 C26 . . 121.95(10)
C22 N21 C26 . . 112.84(9)
C45 N46 C41 . . 117.79(10)
C25 O24 C23 . . 109.49(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N2 . 1.3274(16)
C1 N21 . 1.3679(15)
C1 S1 . 1.7307(12)
C4 N3 . 1.3096(15)
C4 N4 . 1.3338(15)
C4 C41 . 1.4790(16)
C22 N21 . 1.4555(15)
C22 C23 . 1.5227(18)
C22 H22A . 0.9700
C22 H22B . 0.9700
C23 O24 . 1.4299(15)
C23 H23A . 0.9700
C23 H23B . 0.9700
C25 O24 . 1.4264(15)
C25 C26 . 1.5115(16)
C25 H25A . 0.9700
C25 H25B . 0.9700
C26 N21 . 1.4604(15)
C26 H26A . 0.9700
C26 H26B . 0.9700
C41 N46 . 1.3443(15)
C41 C42 . 1.3927(16)
C42 C43 . 1.3894(17)
C42 H42 . 0.9300
C43 C44 . 1.3797(17)
C43 H43 . 0.9300
C44 C45 . 1.4002(17)
C44 H44 . 0.9300
C45 N46 . 1.3381(15)
C45 C451 . 1.4991(16)
C451 H45A . 0.9600
C451 H45B . 0.9600
C451 H45C . 0.9600
N2 N3 . 1.3736(14)
N3 H3 . 0.824(17)
N4 H4A . 0.862(19)
N4 H4B . 0.835(17)
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
N4 H4B O24 2_646 0.835(17) 2.437(17) 3.0523(14) 131.2(14)
N4 H4A S1 4_566 0.862(19) 2.496(19) 3.3255(11) 161.7(15)
N3 H3 S1 . 0.824(17) 2.484(16) 2.9059(10) 113.0(13)
N3 H3 N46 . 0.824(17) 2.373(16) 2.6947(14) 104.1(13)
