#------------------------------------------------------------------------------
#$Date: 2021-12-21 04:59:12 +0200 (Tue, 21 Dec 2021) $
#$Revision: 271558 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022488.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_2022488
loop_
_publ_author_name
'Lobana, Tarlok Singh'
'Kaushal, Mani'
'Bhatia, Robin'
'Bala, Ritu'
'Butcher, Ray J.'
'Jasinksi, Jerry P.'
_publ_section_title
;
 Crystal structures of 3/4-pyridyl-based thiosemicarbazones and related Cu
 and Ni coordination compounds
;
_journal_coeditor_code           YD3022
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322962101319X
_journal_volume                  78
_journal_year                    2022
_chemical_formula_moiety         'C15 H16 N4 S'
_chemical_formula_sum            'C15 H16 N4 S'
_chemical_formula_weight         284.38
_chemical_name_common
;
4-Benzoylpyridine 4-ethylthiosemicarbazone
;
_chemical_name_systematic
(E)-N-Ethyl-2-[phenyl(pyridin-4-yl)methylidene]hydrazine-1-carbothioamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
OLEX2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8897(3)
_cell_length_b                   10.9845(2)
_cell_length_c                   16.8393(3)
_cell_measurement_reflns_used    10170
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.3650
_cell_measurement_theta_min      3.9800
_cell_volume                     2939.14(9)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku OD Gemini Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36150
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.845
_diffrn_reflns_theta_min         3.307
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2019)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0403
_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)+(0.0522P)²+0.7060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                4133
_reflns_number_total             5181
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yd3022sup1.cif
_cod_data_source_block           2
_cod_database_code               2022488
_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   0.934
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.15876(2) 0.77991(3) 0.67701(2) 0.03544(9) Uani d 1 . .
N N1 0.32190(6) 0.72393(8) 0.66444(6) 0.02645(19) Uani d 1 . .
H H1 0.361902 0.683872 0.639466 0.032 Uiso calc 1 . .
N N2 0.23332(6) 0.64807(9) 0.56906(6) 0.0288(2) Uani d 1 . .
H H2 0.182345 0.637311 0.549863 0.035 Uiso calc 1 . .
N N3 0.30060(6) 0.59710(8) 0.53136(6) 0.02595(18) Uani d 1 . .
N N4 0.50794(6) 0.37951(10) 0.36409(6) 0.0329(2) Uani d 1 . .
C C1 0.24434(7) 0.71581(9) 0.63649(6) 0.0245(2) Uani d 1 . .
C C2 0.28598(6) 0.52459(9) 0.47264(6) 0.02316(19) Uani d 1 . .
C C3 0.36179(6) 0.47578(9) 0.43256(6) 0.02238(19) Uani d 1 . .
C C4 0.43464(7) 0.54479(10) 0.42607(6) 0.0272(2) Uani d 1 . .
H H4 0.435933 0.626335 0.444837 0.033 Uiso calc 1 . .
C C5 0.50532(7) 0.49327(11) 0.39193(7) 0.0312(2) Uani d 1 . .
H H5 0.554770 0.541505 0.388058 0.037 Uiso calc 1 . .
C C6 0.43704(7) 0.31490(11) 0.36882(7) 0.0329(2) Uani d 1 . .
H H6 0.437369 0.234220 0.348497 0.039 Uiso calc 1 . .
C C7 0.36292(7) 0.35843(10) 0.40161(7) 0.0282(2) Uani d 1 . .
H H7 0.313850 0.309069 0.402921 0.034 Uiso calc 1 . .
C C8 0.20158(6) 0.48579(9) 0.44413(6) 0.02224(19) Uani d 1 . .
C C9 0.17690(7) 0.50928(10) 0.36640(7) 0.0281(2) Uani d 1 . .
H H9 0.213599 0.551897 0.331600 0.034 Uiso calc 1 . .
C C10 0.09876(8) 0.47061(12) 0.33953(8) 0.0356(3) Uani d 1 . .
H H10 0.081909 0.487739 0.286565 0.043 Uiso calc 1 . .
C C11 0.04537(8) 0.40736(11) 0.38939(9) 0.0372(3) Uani d 1 . .
H H11 -0.007859 0.380379 0.370684 0.045 Uiso calc 1 . .
C C12 0.06965(8) 0.38353(11) 0.46643(8) 0.0368(3) Uani d 1 . .
H H12 0.032864 0.340268 0.500797 0.044 Uiso calc 1 . .
C C13 0.14732(7) 0.42220(10) 0.49415(7) 0.0296(2) Uani d 1 . .
H H13 0.163568 0.405321 0.547318 0.036 Uiso calc 1 . .
C C14 0.34520(8) 0.79516(10) 0.73407(6) 0.0289(2) Uani d 1 . .
H H14A 0.397390 0.761091 0.757239 0.035 Uiso calc 1 . .
H H14B 0.300134 0.788198 0.774412 0.035 Uiso calc 1 . .
C C15 0.35907(10) 0.92783(12) 0.71494(8) 0.0392(3) Uani d 1 . .
H H15A 0.404036 0.935383 0.675405 0.059 Uiso calc 1 . .
H H15B 0.375181 0.971505 0.763355 0.059 Uiso calc 1 . .
H H15C 0.307021 0.962791 0.693620 0.059 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 0.0033 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'
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 H1 . . 118.0 ?
C1 N1 C14 . . 124.01(9) ?
C14 N1 H1 . . 118.0 ?
N3 N2 H2 . . 119.7 ?
N3 N2 C1 . . 120.60(9) y
C1 N2 H2 . . 119.7 ?
C2 N3 N2 . . 117.96(9) y
C6 N4 C5 . . 116.78(10) ?
N1 C1 S1 . . 125.65(8) y
N1 C1 N2 . . 116.82(9) y
N2 C1 S1 . . 117.53(8) y
N3 C2 C3 . . 115.21(9) y
N3 C2 C8 . . 125.92(9) y
C3 C2 C8 . . 118.86(9) y
C4 C3 C2 . . 121.09(9) ?
C4 C3 C7 . . 117.77(10) ?
C7 C3 C2 . . 121.12(9) ?
C3 C4 H4 . . 120.4 ?
C5 C4 C3 . . 119.11(10) ?
C5 C4 H4 . . 120.4 ?
N4 C5 C4 . . 123.67(11) ?
N4 C5 H5 . . 118.2 ?
C4 C5 H5 . . 118.2 ?
N4 C6 H6 . . 118.0 ?
N4 C6 C7 . . 123.91(10) ?
C7 C6 H6 . . 118.0 ?
C3 C7 H7 . . 120.6 ?
C6 C7 C3 . . 118.70(10) ?
C6 C7 H7 . . 120.6 ?
C9 C8 C2 . . 120.34(9) ?
C9 C8 C13 . . 119.18(10) ?
C13 C8 C2 . . 120.45(10) ?
C8 C9 H9 . . 119.9 ?
C10 C9 C8 . . 120.15(11) ?
C10 C9 H9 . . 119.9 ?
C9 C10 H10 . . 119.8 ?
C11 C10 C9 . . 120.34(12) ?
C11 C10 H10 . . 119.8 ?
C10 C11 H11 . . 120.1 ?
C12 C11 C10 . . 119.72(11) ?
C12 C11 H11 . . 120.1 ?
C11 C12 H12 . . 119.7 ?
C11 C12 C13 . . 120.53(11) ?
C13 C12 H12 . . 119.7 ?
C8 C13 H13 . . 120.0 ?
C12 C13 C8 . . 120.07(11) ?
C12 C13 H13 . . 120.0 ?
N1 C14 H14A . . 109.1 ?
N1 C14 H14B . . 109.1 ?
N1 C14 C15 . . 112.58(9) ?
H14A C14 H14B . . 107.8 ?
C15 C14 H14A . . 109.1 ?
C15 C14 H14B . . 109.1 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15B . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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 . 1.6764(10) y
N1 H1 . 0.8800 ?
N1 C1 . 1.3222(14) y
N1 C14 . 1.4574(14) y
N2 H2 . 0.8800 ?
N2 N3 . 1.3636(12) y
N2 C1 . 1.3688(14) y
N3 C2 . 1.2909(13) y
N4 C5 . 1.3353(15) y
N4 C6 . 1.3339(16) ?
C2 C3 . 1.4812(14) y
C2 C8 . 1.4867(14) ?
C3 C4 . 1.3881(15) y
C3 C7 . 1.3905(14) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.3827(15) y
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C6 C7 . 1.3858(15) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.3907(15) ?
C8 C13 . 1.3931(15) ?
C9 H9 . 0.9500 ?
C9 C10 . 1.3881(16) ?
C10 H10 . 0.9500 ?
C10 C11 . 1.3811(19) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.378(2) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.3862(17) ?
C13 H13 . 0.9500 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C14 C15 . 1.5087(17) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
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
N1 H1 N4 5_666 0.88 2.18 2.9719(13) 149.0 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 C2 C3 . . . . 177.95(9) ?
N2 N3 C2 C8 . . . . -3.27(16) ?
N3 N2 C1 S1 . . . . 177.57(8) ?
N3 N2 C1 N1 . . . . -3.05(15) ?
N3 C2 C3 C4 . . . . -33.40(15) ?
N3 C2 C3 C7 . . . . 145.28(11) ?
N3 C2 C8 C9 . . . . 121.10(12) ?
N3 C2 C8 C13 . . . . -60.89(15) ?
N4 C6 C7 C3 . . . . -0.85(19) ?
C1 N1 C14 C15 . . . . -83.30(14) ?
C1 N2 N3 C2 . . . . 173.43(10) ?
C2 C3 C4 C5 . . . . 176.60(10) ?
C2 C3 C7 C6 . . . . -176.32(11) ?
C2 C8 C9 C10 . . . . 178.63(10) ?
C2 C8 C13 C12 . . . . -178.28(10) ?
C3 C2 C8 C9 . . . . -60.16(13) ?
C3 C2 C8 C13 . . . . 117.85(11) ?
C3 C4 C5 N4 . . . . 0.22(18) ?
C4 C3 C7 C6 . . . . 2.41(16) ?
C5 N4 C6 C7 . . . . -1.06(19) ?
C6 N4 C5 C4 . . . . 1.38(18) ?
C7 C3 C4 C5 . . . . -2.12(16) ?
C8 C2 C3 C4 . . . . 147.73(10) ?
C8 C2 C3 C7 . . . . -33.59(15) ?
C8 C9 C10 C11 . . . . -0.76(18) ?
C9 C8 C13 C12 . . . . -0.24(16) ?
C9 C10 C11 C12 . . . . 0.56(19) ?
C10 C11 C12 C13 . . . . -0.21(18) ?
C11 C12 C13 C8 . . . . 0.06(17) ?
C13 C8 C9 C10 . . . . 0.59(16) ?
C14 N1 C1 S1 . . . . -2.61(16) ?
C14 N1 C1 N2 . . . . 178.07(10) ?

_cod_database_fobs_code 2022488
