#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/73/2237383.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_2237383
loop_
_publ_author_name
'Low, May Lee'
'Ravoof, Thahira Begum S. A.'
'Tahir, Mohamed Ibrahim Mohamed'
'Crouse, Karen A.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 (Pyridin-4-yl)methyl
 N'-(3-phenylallylidene)hydrazinecarbodithioate
;
_journal_coeditor_code           QM2090
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o167
_journal_page_last               o168
_journal_paper_doi               10.1107/S1600536812051537
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H15 N3 S2'
_chemical_formula_moiety         'C16 H15 N3 S2'
_chemical_formula_sum            'C16 H15 N3 S2'
_chemical_formula_weight         313.43
_chemical_name_common
;
(Pyridin-4-yl)methyl
3-[(1E,2E)-3-Phenylprop-2-en-1-ylidene]dithiocarbazate
;
_chemical_name_systematic
;
(Pyridin-4-yl)methyl N'-(3-phenylallylidene)hydrazinecarbodithioate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.315(9)
_cell_angle_beta                 84.735(9)
_cell_angle_gamma                78.193(8)
_cell_formula_units_Z            2
_cell_length_a                   5.3784(5)
_cell_length_b                   10.1570(9)
_cell_length_c                   14.5488(17)
_cell_measurement_reflns_used    5833
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72
_cell_measurement_theta_min      3
_cell_volume                     758.06(14)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1952
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Oxford Diffraction Xcaliber Eos Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15664
_diffrn_reflns_theta_full        72.30
_diffrn_reflns_theta_max         72.30
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.141
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       thin-plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0416
_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)+(0.0669P)²+0.3038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                2469
_reflns_number_total             2918
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2090.cif
_cod_data_source_block           I
_cod_original_cell_volume        758.06(13)
_cod_database_code               2237383
_cod_database_fobs_code          2237383
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.36876(9) 0.53086(5) 0.18295(4) 0.02532(16) Uani d . 1 1
S S2 0.33320(10) 0.32045(5) 0.06781(4) 0.02701(17) Uani d . 1 1
N N1 0.6775(3) 0.29601(17) 0.19095(13) 0.0256(4) Uani d D 1 1
H H1n 0.749(4) 0.2148(14) 0.1794(18) 0.031 Uiso d D 1 1
N N2 0.7786(3) 0.34184(17) 0.25917(13) 0.0262(4) Uani d . 1 1
N N3 -0.1177(4) 1.01818(18) 0.16683(15) 0.0338(5) Uani d . 1 1
C C1 0.4717(4) 0.3730(2) 0.14713(15) 0.0233(4) Uani d . 1 1
C C2 0.9846(4) 0.2638(2) 0.29282(16) 0.0266(5) Uani d . 1 1
H H2 1.0579 0.1846 0.2682 0.032 Uiso calc R 1 1
C C3 1.1038(4) 0.2962(2) 0.36748(16) 0.0284(5) Uani d . 1 1
H H3 1.0295 0.3764 0.3909 0.034 Uiso calc R 1 1
C C4 1.3162(4) 0.2171(2) 0.40512(16) 0.0279(5) Uani d . 1 1
H H4 1.3893 0.1405 0.3776 0.033 Uiso calc R 1 1
C C5 1.4484(4) 0.2350(2) 0.48372(16) 0.0284(5) Uani d . 1 1
C C6 1.3649(5) 0.3430(2) 0.53137(18) 0.0370(6) Uani d . 1 1
H H6 1.2139 0.4074 0.5133 0.044 Uiso calc R 1 1
C C7 1.4982(5) 0.3574(3) 0.60420(19) 0.0393(6) Uani d . 1 1
H H7 1.4401 0.4323 0.6349 0.047 Uiso calc R 1 1
C C8 1.7160(5) 0.2633(3) 0.63253(18) 0.0368(6) Uani d . 1 1
H H8 1.8074 0.2733 0.6826 0.044 Uiso calc R 1 1
C C9 1.8000(4) 0.1543(3) 0.58746(18) 0.0359(5) Uani d . 1 1
H H9 1.9484 0.0889 0.6072 0.043 Uiso calc R 1 1
C C10 1.6683(4) 0.1405(2) 0.51347(17) 0.0312(5) Uani d . 1 1
H H10 1.7283 0.0659 0.4827 0.037 Uiso calc R 1 1
C C11 0.1118(4) 0.6125(2) 0.10459(17) 0.0269(5) Uani d . 1 1
H H11A 0.1725 0.6164 0.0379 0.032 Uiso calc R 1 1
H H11B -0.0298 0.5612 0.1181 0.032 Uiso calc R 1 1
C C12 0.0263(4) 0.7559(2) 0.12385(16) 0.0262(5) Uani d . 1 1
C C13 -0.1950(4) 0.7908(2) 0.17696(19) 0.0357(6) Uani d . 1 1
H H13 -0.3022 0.7258 0.1998 0.043 Uiso calc R 1 1
C C14 -0.2588(4) 0.9219(2) 0.1965(2) 0.0390(6) Uani d . 1 1
H H14 -0.4112 0.9441 0.2330 0.047 Uiso calc R 1 1
C C15 0.0961(5) 0.9839(2) 0.11574(18) 0.0345(5) Uani d . 1 1
H H15 0.1999 1.0508 0.0940 0.041 Uiso calc R 1 1
C C16 0.1742(4) 0.8555(2) 0.09283(17) 0.0314(5) Uani d . 1 1
H H16 0.3277 0.8361 0.0562 0.038 Uiso calc R 1 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
C1 S1 C11 101.51(10)
C1 N1 N2 119.67(17)
C1 N1 H1n 122.4(17)
N2 N1 H1n 117.9(17)
C2 N2 N1 114.56(18)
C14 N3 C15 116.84(19)
N1 C1 S2 121.98(16)
N1 C1 S1 113.13(16)
S2 C1 S1 124.88(12)
N2 C2 C3 120.4(2)
N2 C2 H2 119.8
C3 C2 H2 119.8
C4 C3 C2 122.2(2)
C4 C3 H3 118.9
C2 C3 H3 118.9
C3 C4 C5 127.5(2)
C3 C4 H4 116.3
C5 C4 H4 116.3
C10 C5 C6 117.9(2)
C10 C5 C4 119.1(2)
C6 C5 C4 123.0(2)
C7 C6 C5 121.1(2)
C7 C6 H6 119.4
C5 C6 H6 119.4
C6 C7 C8 120.2(2)
C6 C7 H7 119.9
C8 C7 H7 119.9
C7 C8 C9 119.7(2)
C7 C8 H8 120.2
C9 C8 H8 120.2
C8 C9 C10 120.2(2)
C8 C9 H9 119.9
C10 C9 H9 119.9
C9 C10 C5 120.9(2)
C9 C10 H10 119.6
C5 C10 H10 119.6
C12 C11 S1 105.44(14)
C12 C11 H11A 110.7
S1 C11 H11A 110.7
C12 C11 H11B 110.7
S1 C11 H11B 110.7
H11A C11 H11B 108.8
C13 C12 C16 117.4(2)
C13 C12 C11 121.6(2)
C16 C12 C11 121.0(2)
C12 C13 C14 119.3(2)
C12 C13 H13 120.3
C14 C13 H13 120.3
N3 C14 C13 123.6(2)
N3 C14 H14 118.2
C13 C14 H14 118.2
N3 C15 C16 123.4(2)
N3 C15 H15 118.3
C16 C15 H15 118.3
C12 C16 C15 119.4(2)
C12 C16 H16 120.3
C15 C16 H16 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.760(2)
S1 C11 1.817(2)
S2 C1 1.662(2)
N1 C1 1.342(3)
N1 N2 1.379(3)
N1 H1n 0.880(10)
N2 C2 1.290(3)
N3 C14 1.332(3)
N3 C15 1.337(3)
C2 C3 1.439(3)
C2 H2 0.9500
C3 C4 1.340(3)
C3 H3 0.9500
C4 C5 1.463(3)
C4 H4 0.9500
C5 C10 1.398(3)
C5 C6 1.400(3)
C6 C7 1.382(3)
C6 H6 0.9500
C7 C8 1.383(3)
C7 H7 0.9500
C8 C9 1.385(4)
C8 H8 0.9500
C9 C10 1.389(3)
C9 H9 0.9500
C10 H10 0.9500
C11 C12 1.514(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.385(3)
C12 C16 1.386(3)
C13 C14 1.391(3)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.389(3)
C15 H15 0.9500
C16 H16 0.9500
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
N1 H1n N3 1_645 0.881(16) 2.021(15) 2.897(3) 172(2)
C8 H8 Cg1 2_766 0.95 2.92 3.701(3) 141
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
C1 N1 N2 C2 -176.15(19)
N2 N1 C1 S2 -177.22(15)
N2 N1 C1 S1 2.5(2)
C11 S1 C1 N1 175.41(16)
C11 S1 C1 S2 -4.84(16)
N1 N2 C2 C3 -177.19(18)
N2 C2 C3 C4 179.2(2)
C2 C3 C4 C5 -176.9(2)
C3 C4 C5 C10 179.6(2)
C3 C4 C5 C6 -0.2(4)
C10 C5 C6 C7 1.3(4)
C4 C5 C6 C7 -178.8(2)
C5 C6 C7 C8 -1.1(4)
C6 C7 C8 C9 0.1(4)
C7 C8 C9 C10 0.8(4)
C8 C9 C10 C5 -0.5(4)
C6 C5 C10 C9 -0.5(3)
C4 C5 C10 C9 179.6(2)
C1 S1 C11 C12 -174.77(15)
S1 C11 C12 C13 -103.5(2)
S1 C11 C12 C16 73.2(2)
C16 C12 C13 C14 0.1(4)
C11 C12 C13 C14 176.9(2)
C15 N3 C14 C13 -0.1(4)
C12 C13 C14 N3 0.0(4)
C14 N3 C15 C16 0.2(4)
C13 C12 C16 C15 0.0(3)
C11 C12 C16 C15 -176.9(2)
N3 C15 C16 C12 -0.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658319
2 PubChem 139085199
