#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/98/1569865.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_1569865
loop_
_publ_author_name
'Abdul Manan, Mohd Abdul Fatah'
'Cordes, David B.'
'McKay, Aidan P.'
'Mohammat, Mohd Fazli'
'Mohd Aluwi, Mohd Fadhlizil Fasihi'
'Jumali, Nor Saliyana'
_publ_section_title
;
 (Z)-Benzyl 2-(5-methyl-2-oxoindolin-3-ylidene)hydrazinecarbodithioate
;
_journal_coeditor_code           HB4449
_journal_issue                   9
_journal_name_full               IUCrData
_journal_page_first              x230782
_journal_paper_doi               10.1107/S2414314623007824
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          'C17 H15 N3 O S2'
_chemical_formula_moiety         'C17 H15 N3 O S2'
_chemical_formula_sum            'C17 H15 N3 O S2'
_chemical_formula_weight         341.44
_chemical_name_common
;
Benzyl (Z)-2-(2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate
;
_chemical_name_systematic
;
(Z)-Benzyl 2-(5-methyl-2-oxoindolin-3-ylidene)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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                95.442(2)
_cell_angle_beta                 99.527(2)
_cell_angle_gamma                90.360(2)
_cell_formula_units_Z            2
_cell_length_a                   6.5733(2)
_cell_length_b                   8.0601(2)
_cell_length_c                   15.8280(4)
_cell_measurement_reflns_used    8603
_cell_measurement_temperature    173
_cell_measurement_theta_max      65.9910
_cell_measurement_theta_min      2.8440
_cell_volume                     823.09(4)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14207
_diffrn_reflns_theta_full        66.465
_diffrn_reflns_theta_max         66.465
_diffrn_reflns_theta_min         2.844
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    2.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2876
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0626P)²+0.1676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                2623
_reflns_number_total             2876
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4449.cif
_cod_data_source_block           I
_cod_database_code               1569865
#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   0.716
_shelx_estimated_absorpt_t_max   0.943
#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 S11 0.21331(6) 0.33788(5) 0.21855(2) 0.03493(14) Uani d 1 . .
S S10 0.58661(6) 0.23720(6) 0.13457(3) 0.04020(15) Uani d 1 . .
O O1 0.86838(18) 0.08666(16) 0.40267(8) 0.0398(3) Uani d 1 . .
N N3 0.5546(2) 0.22521(17) 0.29604(9) 0.0341(3) Uani d 1 . .
N N2 0.4614(2) 0.26067(17) 0.36534(9) 0.0326(3) Uani d 1 . .
N N9 0.7901(2) 0.11126(18) 0.54096(9) 0.0358(3) Uani d 1 . .
C C12 0.1188(3) 0.5709(2) 0.10260(10) 0.0337(3) Uani d 1 . .
C C1 0.7576(2) 0.1314(2) 0.45642(11) 0.0335(3) Uani d 1 . .
C C2 0.5567(2) 0.22039(19) 0.43850(10) 0.0325(3) Uani d 1 . .
C C10 0.4621(2) 0.26451(19) 0.21733(10) 0.0319(3) Uani d 1 . .
C C8 0.6299(2) 0.1807(2) 0.58149(11) 0.0340(3) Uani d 1 . .
C C3 0.4846(2) 0.24993(19) 0.52025(10) 0.0324(3) Uani d 1 . .
C C5 0.2894(3) 0.3413(2) 0.63055(11) 0.0378(4) Uani d 1 . .
C C11 0.1296(3) 0.3858(2) 0.10785(10) 0.0359(4) Uani d 1 . .
H H11A 0.227507 0.338283 0.071281 0.043 Uiso calc 1 . .
H H11B -0.007988 0.333708 0.085640 0.043 Uiso calc 1 . .
C C4 0.3146(3) 0.3301(2) 0.54485(11) 0.0365(4) Uani d 1 . .
H H4 0.216108 0.376892 0.503346 0.044 Uiso calc 1 . .
C C7 0.6075(3) 0.1888(2) 0.66702(11) 0.0394(4) Uani d 1 . .
H H7 0.705150 0.140761 0.708391 0.047 Uiso calc 1 . .
C C6 0.4357(3) 0.2702(2) 0.69000(11) 0.0415(4) Uani d 1 . .
H H6 0.417242 0.277589 0.748510 0.050 Uiso calc 1 . .
C C17 -0.0561(3) 0.6540(2) 0.11867(12) 0.0452(4) Uani d 1 . .
H H17 -0.169973 0.593731 0.131545 0.054 Uiso calc 1 . .
C C13 0.2833(3) 0.6589(3) 0.08239(12) 0.0478(5) Uani d 1 . .
H H13 0.403301 0.602050 0.070803 0.057 Uiso calc 1 . .
C C9 0.1083(3) 0.4309(3) 0.65976(12) 0.0474(4) Uani d 1 . .
H H9A 0.023698 0.475703 0.610469 0.071 Uiso calc 1 . .
H H9B 0.158867 0.522536 0.703588 0.071 Uiso calc 1 . .
H H9C 0.024801 0.352666 0.684170 0.071 Uiso calc 1 . .
C C16 -0.0654(5) 0.8257(3) 0.11601(14) 0.0685(7) Uani d 1 . .
H H16 -0.184886 0.883158 0.127739 0.082 Uiso calc 1 . .
C C14 0.2728(5) 0.8293(3) 0.07910(14) 0.0690(8) Uani d 1 . .
H H14 0.385349 0.889230 0.064934 0.083 Uiso calc 1 . .
C C15 0.1000(6) 0.9125(3) 0.09623(15) 0.0803(10) Uani d 1 . .
H H15 0.094106 1.029931 0.094482 0.096 Uiso calc 1 . .
H H3 0.680(3) 0.177(3) 0.3057(14) 0.052(6) Uiso d 1 . .
H H9 0.901(3) 0.053(3) 0.5684(14) 0.057(6) 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
_geom_angle_publ_flag
C10 S11 C11 . . 103.16(8) ?
N2 N3 C10 . . 119.92(14) ?
N2 N3 H3 . . 116.6(14) ?
C10 N3 H3 . . 123.4(14) ?
C2 N2 N3 . . 117.17(14) ?
C1 N9 C8 . . 111.27(14) ?
C1 N9 H9 . . 123.9(15) ?
C8 N9 H9 . . 124.7(15) ?
C17 C12 C11 . . 119.66(16) ?
C17 C12 C13 . . 119.77(17) ?
C13 C12 C11 . . 120.57(16) ?
O1 C1 N9 . . 127.80(15) ?
O1 C1 C2 . . 125.75(15) ?
N9 C1 C2 . . 106.46(14) ?
N2 C2 C1 . . 128.01(15) ?
N2 C2 C3 . . 125.68(15) ?
C3 C2 C1 . . 106.30(13) ?
S10 C10 S11 . . 128.14(10) ?
N3 C10 S11 . . 112.22(12) ?
N3 C10 S10 . . 119.64(13) ?
C3 C8 N9 . . 109.25(14) ?
C7 C8 N9 . . 129.31(15) ?
C7 C8 C3 . . 121.43(16) ?
C8 C3 C2 . . 106.70(14) ?
C4 C3 C2 . . 133.05(15) ?
C4 C3 C8 . . 120.24(16) ?
C4 C5 C6 . . 118.99(16) ?
C4 C5 C9 . . 120.83(16) ?
C6 C5 C9 . . 120.18(16) ?
S11 C11 H11A . . 109.4 ?
S11 C11 H11B . . 109.4 ?
C12 C11 S11 . . 111.12(11) ?
C12 C11 H11A . . 109.4 ?
C12 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
C3 C4 C5 . . 119.52(16) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C8 C7 H7 . . 121.4 ?
C8 C7 C6 . . 117.16(16) ?
C6 C7 H7 . . 121.4 ?
C5 C6 H6 . . 118.7 ?
C7 C6 C5 . . 122.66(16) ?
C7 C6 H6 . . 118.7 ?
C12 C17 H17 . . 120.0 ?
C12 C17 C16 . . 120.0(2) ?
C16 C17 H17 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C14 C13 C12 . . 120.0(2) ?
C14 C13 H13 . . 120.0 ?
C5 C9 H9A . . 109.5 ?
C5 C9 H9B . . 109.5 ?
C5 C9 H9C . . 109.5 ?
H9A C9 H9B . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C17 C16 H16 . . 120.1 ?
C15 C16 C17 . . 119.8(2) ?
C15 C16 H16 . . 120.1 ?
C13 C14 H14 . . 119.9 ?
C15 C14 C13 . . 120.3(2) ?
C15 C14 H14 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C14 C15 C16 . . 120.1(2) ?
C14 C15 H15 . . 119.9 ?
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
S11 C10 . 1.7449(16) ?
S11 C11 . 1.8260(16) ?
S10 C10 . 1.6544(16) ?
O1 C1 . 1.239(2) ?
N3 N2 . 1.3509(19) ?
N3 C10 . 1.360(2) ?
N3 H3 . 0.912(16) ?
N2 C2 . 1.293(2) ?
N9 C1 . 1.345(2) ?
N9 C8 . 1.413(2) ?
N9 H9 . 0.938(16) ?
C12 C11 . 1.503(2) ?
C12 C17 . 1.381(3) ?
C12 C13 . 1.387(2) ?
C1 C2 . 1.505(2) ?
C2 C3 . 1.449(2) ?
C8 C3 . 1.402(2) ?
C8 C7 . 1.381(2) ?
C3 C4 . 1.387(2) ?
C5 C4 . 1.388(2) ?
C5 C6 . 1.396(3) ?
C5 C9 . 1.510(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C4 H4 . 0.9500 ?
C7 H7 . 0.9500 ?
C7 C6 . 1.392(3) ?
C6 H6 . 0.9500 ?
C17 H17 . 0.9500 ?
C17 C16 . 1.390(3) ?
C13 H13 . 0.9500 ?
C13 C14 . 1.381(3) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C16 H16 . 0.9500 ?
C16 C15 . 1.384(4) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.375(4) ?
C15 H15 . 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
_geom_hbond_publ_flag
N3 H3 O1 . 0.912(16) 2.002(19) 2.7539(17) 138.6(19) yes
N9 H9 O1 2_756 0.938(16) 1.914(17) 2.8341(18) 166(2) 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
O1 C1 C2 N2 . . . . 2.5(3) ?
O1 C1 C2 C3 . . . . -178.95(16) ?
N3 N2 C2 C1 . . . . -2.7(2) ?
N3 N2 C2 C3 . . . . 178.99(14) ?
N2 N3 C10 S11 . . . . -6.67(19) ?
N2 N3 C10 S10 . . . . 174.23(11) ?
N2 C2 C3 C8 . . . . 177.57(15) ?
N2 C2 C3 C4 . . . . -3.7(3) ?
N9 C1 C2 N2 . . . . -177.48(15) ?
N9 C1 C2 C3 . . . . 1.09(17) ?
N9 C8 C3 C2 . . . . 0.65(18) ?
N9 C8 C3 C4 . . . . -178.28(14) ?
N9 C8 C7 C6 . . . . 177.93(16) ?
C12 C17 C16 C15 . . . . 0.8(3) ?
C12 C13 C14 C15 . . . . 0.3(3) ?
C1 N9 C8 C3 . . . . 0.07(19) ?
C1 N9 C8 C7 . . . . -178.72(17) ?
C1 C2 C3 C8 . . . . -1.05(17) ?
C1 C2 C3 C4 . . . . 177.68(17) ?
C2 C3 C4 C5 . . . . -178.56(16) ?
C10 S11 C11 C12 . . . . -109.04(13) ?
C10 N3 N2 C2 . . . . 179.99(14) ?
C8 N9 C1 O1 . . . . 179.33(16) ?
C8 N9 C1 C2 . . . . -0.72(18) ?
C8 C3 C4 C5 . . . . 0.0(2) ?
C8 C7 C6 C5 . . . . 0.2(3) ?
C3 C8 C7 C6 . . . . -0.7(3) ?
C11 S11 C10 S10 . . . . -2.51(13) ?
C11 S11 C10 N3 . . . . 178.48(11) ?
C11 C12 C17 C16 . . . . 178.43(17) ?
C11 C12 C13 C14 . . . . -178.98(16) ?
C4 C5 C6 C7 . . . . 0.4(3) ?
C7 C8 C3 C2 . . . . 179.54(15) ?
C7 C8 C3 C4 . . . . 0.6(2) ?
C6 C5 C4 C3 . . . . -0.5(3) ?
C17 C12 C11 S11 . . . . -84.17(17) ?
C17 C12 C13 C14 . . . . 0.5(3) ?
C17 C16 C15 C14 . . . . 0.1(3) ?
C13 C12 C11 S11 . . . . 95.35(16) ?
C13 C12 C17 C16 . . . . -1.1(3) ?
C13 C14 C15 C16 . . . . -0.7(3) ?
C9 C5 C4 C3 . . . . 178.71(16) ?
C9 C5 C6 C7 . . . . -178.83(16) ?
