#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/45/1564549.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_1564549
loop_
_publ_author_name
'Guo, Hui'
'Du, Wenli'
'Zhou, Haoyu'
_publ_section_title
;
 (E)-Benzyl
 2-{4-[ethyl(2-hydroxyethyl)amino]benzylidene}hydrazinecarbodithioate
;
_journal_coeditor_code           HB4387
_journal_issue                   9
_journal_name_full               IUCrData
_journal_page_first              x210901
_journal_paper_doi               10.1107/S2414314621009019
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C19 H23 N3 O S2'
_chemical_formula_moiety         'C19 H23 N3 O S2'
_chemical_formula_sum            'C19 H23 N3 O S2'
_chemical_formula_weight         373.52
_chemical_name_systematic
;
(E)-Benzyl
2-{4-[ethyl(2-hydroxyethyl)amino]benzylidene}hydrazinecarbodithioate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                101.78(3)
_cell_angle_beta                 107.81(3)
_cell_angle_gamma                93.57(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1794(18)
_cell_length_b                   9.4642(19)
_cell_length_c                   11.665(2)
_cell_measurement_reflns_used    8567
_cell_measurement_temperature    120
_cell_measurement_theta_max      4.295
_cell_measurement_theta_min      69.767
_cell_volume                     936.0(4)
_computing_cell_refinement
;
X-Area Recipe (Stoe, 2018)
;
_computing_data_collection
;
X-Area Pilatus3_SV (Stoe, 2018)
;
_computing_data_reduction
;
X-Area Integrate (Stoe, 2018)
X-Area LANA (Stoe, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Stoe X-Area CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8565
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.627
_diffrn_reflns_theta_min         1.886
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.8077
_exptl_absorpt_correction_T_min  0.3420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-Red32; Stoe, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0388
_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)+(0.0568P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                2508
_reflns_number_total             3419
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4387sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        936.1(4)
_cod_database_code               1564549
_cod_database_fobs_code          1564549
#BEGIN Tags that were not found in dictionaries:
_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   0.965
_shelx_estimated_absorpt_t_max   0.971
#END Tags that were not found in dictionaries
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.15987(6) 0.04410(6) 0.90983(5) 0.02333(15) Uani d 1 . .
S S2 1.05575(6) 0.31931(6) 0.83421(5) 0.02330(15) Uani d 1 . .
O O1 0.22245(18) 0.21535(18) 0.18795(14) 0.0262(4) Uani d 1 . .
H H1 0.223336 0.181675 0.115767 0.039 Uiso calc 1 . .
N N1 0.8765(2) 0.0761(2) 0.79056(16) 0.0233(4) Uani d 1 . .
H H1A 0.850789 -0.013576 0.794332 0.028 Uiso calc 1 . .
N N2 0.7650(2) 0.1512(2) 0.73042(16) 0.0228(4) Uani d 1 . .
N N3 0.1089(2) 0.2823(2) 0.39125(16) 0.0224(4) Uani d 1 . .
C C1 1.0235(2) 0.1382(2) 0.84322(19) 0.0223(5) Uani d 1 . .
C C2 1.2647(3) 0.3598(3) 0.9062(2) 0.0290(5) Uani d 1 . .
H H2A 1.294123 0.355290 0.994245 0.035 Uiso calc 1 . .
H H2B 1.315757 0.287256 0.863582 0.035 Uiso calc 1 . .
C C3 1.3150(2) 0.5093(3) 0.8965(2) 0.0238(5) Uani d 1 . .
C C4 1.3139(3) 0.6313(3) 0.9856(2) 0.0273(5) Uani d 1 . .
H H4 1.276995 0.620316 1.051407 0.033 Uiso calc 1 . .
C C5 1.3663(3) 0.7686(3) 0.9790(2) 0.0308(6) Uani d 1 . .
H H5 1.365720 0.851217 1.040672 0.037 Uiso calc 1 . .
C C6 1.4193(3) 0.7867(3) 0.8836(2) 0.0320(6) Uani d 1 . .
H H6 1.455293 0.881218 0.879535 0.038 Uiso calc 1 . .
C C7 1.4196(3) 0.6659(3) 0.7939(2) 0.0335(6) Uani d 1 . .
H H7 1.455863 0.677709 0.728000 0.040 Uiso calc 1 . .
C C8 1.3675(3) 0.5285(3) 0.7997(2) 0.0298(5) Uani d 1 . .
H H8 1.367371 0.446318 0.737304 0.036 Uiso calc 1 . .
C C9 0.6253(2) 0.0890(2) 0.6989(2) 0.0228(5) Uani d 1 . .
H H9 0.606910 0.001568 0.723393 0.027 Uiso calc 1 . .
C C10 0.4956(2) 0.1479(2) 0.6275(2) 0.0220(5) Uani d 1 . .
C C11 0.5133(3) 0.2530(2) 0.5624(2) 0.0231(5) Uani d 1 . .
H H11 0.614400 0.293822 0.571093 0.028 Uiso calc 1 . .
C C12 0.3883(2) 0.2988(2) 0.4861(2) 0.0231(5) Uani d 1 . .
H H12 0.405089 0.369235 0.442312 0.028 Uiso calc 1 . .
C C13 0.2348(2) 0.2430(2) 0.47130(19) 0.0208(5) Uani d 1 . .
C C14 0.2178(3) 0.1427(2) 0.5421(2) 0.0240(5) Uani d 1 . .
H H14 0.117263 0.107096 0.539112 0.029 Uiso calc 1 . .
C C15 0.3445(3) 0.0952(3) 0.6157(2) 0.0255(5) Uani d 1 . .
H H15 0.328834 0.024729 0.659759 0.031 Uiso calc 1 . .
C C16 0.1209(3) 0.3845(2) 0.3153(2) 0.0243(5) Uani d 1 . .
H H16A 0.221483 0.447682 0.354456 0.029 Uiso calc 1 . .
H H16B 0.038555 0.447687 0.313128 0.029 Uiso calc 1 . .
C C17 0.1074(3) 0.3110(2) 0.1842(2) 0.0243(5) Uani d 1 . .
H H17A 0.003408 0.255098 0.140883 0.029 Uiso calc 1 . .
H H17B 0.122681 0.385034 0.138467 0.029 Uiso calc 1 . .
C C18 -0.0480(2) 0.2184(3) 0.3739(2) 0.0244(5) Uani d 1 . .
H H18A -0.047229 0.114806 0.377521 0.029 Uiso calc 1 . .
H H18B -0.116034 0.221695 0.290540 0.029 Uiso calc 1 . .
C C19 -0.1142(3) 0.2960(3) 0.4705(2) 0.0324(6) Uani d 1 . .
H H19A -0.216151 0.244927 0.457563 0.049 Uiso calc 1 . .
H H19B -0.123843 0.396399 0.462546 0.049 Uiso calc 1 . .
H H19C -0.045187 0.296706 0.553457 0.049 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'
O O 0.0106 0.0060 '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 S2 C2 . . 101.28(11) ?
C17 O1 H1 . . 109.5 ?
N2 N1 H1A . . 119.7 ?
C1 N1 H1A . . 119.7 ?
C1 N1 N2 . . 120.63(18) ?
C9 N2 N1 . . 114.97(19) ?
C13 N3 C16 . . 123.26(18) ?
C13 N3 C18 . . 121.00(18) ?
C16 N3 C18 . . 115.70(18) ?
S1 C1 S2 . . 124.96(13) ?
N1 C1 S1 . . 120.51(17) ?
N1 C1 S2 . . 114.53(17) ?
S2 C2 H2A . . 110.0 ?
S2 C2 H2B . . 110.0 ?
H2A C2 H2B . . 108.4 ?
C3 C2 S2 . . 108.51(16) ?
C3 C2 H2A . . 110.0 ?
C3 C2 H2B . . 110.0 ?
C4 C3 C2 . . 120.6(2) ?
C4 C3 C8 . . 118.8(2) ?
C8 C3 C2 . . 120.6(2) ?
C3 C4 H4 . . 119.8 ?
C5 C4 C3 . . 120.4(2) ?
C5 C4 H4 . . 119.8 ?
C4 C5 H5 . . 119.7 ?
C6 C5 C4 . . 120.6(2) ?
C6 C5 H5 . . 119.7 ?
C5 C6 H6 . . 120.3 ?
C5 C6 C7 . . 119.4(2) ?
C7 C6 H6 . . 120.3 ?
C6 C7 H7 . . 119.8 ?
C8 C7 C6 . . 120.4(2) ?
C8 C7 H7 . . 119.8 ?
C3 C8 H8 . . 119.8 ?
C7 C8 C3 . . 120.4(2) ?
C7 C8 H8 . . 119.8 ?
N2 C9 H9 . . 119.0 ?
N2 C9 C10 . . 122.0(2) ?
C10 C9 H9 . . 119.0 ?
C11 C10 C9 . . 122.4(2) ?
C11 C10 C15 . . 117.1(2) ?
C15 C10 C9 . . 120.5(2) ?
C10 C11 H11 . . 119.1 ?
C12 C11 C10 . . 121.8(2) ?
C12 C11 H11 . . 119.1 ?
C11 C12 H12 . . 119.3 ?
C11 C12 C13 . . 121.4(2) ?
C13 C12 H12 . . 119.3 ?
N3 C13 C12 . . 122.15(19) ?
N3 C13 C14 . . 121.34(19) ?
C14 C13 C12 . . 116.5(2) ?
C13 C14 H14 . . 119.4 ?
C15 C14 C13 . . 121.2(2) ?
C15 C14 H14 . . 119.4 ?
C10 C15 H15 . . 119.0 ?
C14 C15 C10 . . 121.9(2) ?
C14 C15 H15 . . 119.0 ?
N3 C16 H16A . . 108.9 ?
N3 C16 H16B . . 108.9 ?
N3 C16 C17 . . 113.41(19) ?
H16A C16 H16B . . 107.7 ?
C17 C16 H16A . . 108.9 ?
C17 C16 H16B . . 108.9 ?
O1 C17 C16 . . 108.64(18) ?
O1 C17 H17A . . 110.0 ?
O1 C17 H17B . . 110.0 ?
C16 C17 H17A . . 110.0 ?
C16 C17 H17B . . 110.0 ?
H17A C17 H17B . . 108.3 ?
N3 C18 H18A . . 109.0 ?
N3 C18 H18B . . 109.0 ?
N3 C18 C19 . . 113.08(19) ?
H18A C18 H18B . . 107.8 ?
C19 C18 H18A . . 109.0 ?
C19 C18 H18B . . 109.0 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19B . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 . 1.670(2) ?
S2 C1 . 1.751(2) ?
S2 C2 . 1.823(2) ?
O1 H1 . 0.8400 ?
O1 C17 . 1.429(3) ?
N1 H1A . 0.8800 ?
N1 N2 . 1.379(3) ?
N1 C1 . 1.338(3) ?
N2 C9 . 1.286(3) ?
N3 C13 . 1.371(3) ?
N3 C16 . 1.459(3) ?
N3 C18 . 1.464(3) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C2 C3 . 1.498(3) ?
C3 C4 . 1.390(3) ?
C3 C8 . 1.395(3) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.382(3) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.379(3) ?
C6 H6 . 0.9500 ?
C6 C7 . 1.384(4) ?
C7 H7 . 0.9500 ?
C7 C8 . 1.379(4) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C9 C10 . 1.445(3) ?
C10 C11 . 1.398(3) ?
C10 C15 . 1.400(3) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.375(3) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.420(3) ?
C13 C14 . 1.411(3) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.380(3) ?
C15 H15 . 0.9500 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C16 C17 . 1.509(3) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C18 C19 . 1.521(3) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 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 H1A O1 2_656 0.88 2.06 2.933(3) 175 yes
O1 H1 S1 1_454 0.84 2.36 3.1749(19) 163 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
S2 C2 C3 C4 . . . . 86.2(2) ?
S2 C2 C3 C8 . . . . -95.4(2) ?
N1 N2 C9 C10 . . . . -175.48(19) ?
N2 N1 C1 S1 . . . . -176.94(15) ?
N2 N1 C1 S2 . . . . 2.7(3) ?
N2 C9 C10 C11 . . . . 16.2(3) ?
N2 C9 C10 C15 . . . . -167.2(2) ?
N3 C13 C14 C15 . . . . 175.2(2) ?
N3 C16 C17 O1 . . . . -56.2(2) ?
C1 S2 C2 C3 . . . . 175.21(17) ?
C1 N1 N2 C9 . . . . -170.6(2) ?
C2 S2 C1 S1 . . . . 2.66(17) ?
C2 S2 C1 N1 . . . . -176.95(17) ?
C2 C3 C4 C5 . . . . 177.4(2) ?
C2 C3 C8 C7 . . . . -177.4(2) ?
C3 C4 C5 C6 . . . . 0.5(3) ?
C4 C3 C8 C7 . . . . 1.1(3) ?
C4 C5 C6 C7 . . . . 0.1(4) ?
C5 C6 C7 C8 . . . . -0.1(3) ?
C6 C7 C8 C3 . . . . -0.5(4) ?
C8 C3 C4 C5 . . . . -1.0(3) ?
C9 C10 C11 C12 . . . . 174.2(2) ?
C9 C10 C15 C14 . . . . -176.0(2) ?
C10 C11 C12 C13 . . . . 1.0(3) ?
C11 C10 C15 C14 . . . . 0.8(3) ?
C11 C12 C13 N3 . . . . -176.9(2) ?
C11 C12 C13 C14 . . . . 2.2(3) ?
C12 C13 C14 C15 . . . . -3.9(3) ?
C13 N3 C16 C17 . . . . 98.0(2) ?
C13 N3 C18 C19 . . . . 84.7(3) ?
C13 C14 C15 C10 . . . . 2.4(4) ?
C15 C10 C11 C12 . . . . -2.6(3) ?
C16 N3 C13 C12 . . . . -0.4(3) ?
C16 N3 C13 C14 . . . . -179.4(2) ?
C16 N3 C18 C19 . . . . -97.4(2) ?
C18 N3 C13 C12 . . . . 177.3(2) ?
C18 N3 C13 C14 . . . . -1.7(3) ?
C18 N3 C16 C17 . . . . -79.8(2) ?
