#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/28/1552865.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_1552865
loop_
_publ_author_name
'Omar Ali, Nur Halilatul Sadiqin'
'Sheikh Abdul Hamid, Malai Haniti'
'Mirza, Aminul Huq'
'Usman, Anwar'
_publ_section_title
;
 2-[1-(1,3-Dioxo-1,3-dihydro-2H-inden-2-ylidene)ethyl]hydrazinecarbothioamide
;
_journal_coeditor_code           IS5524
_journal_issue                   11
_journal_name_full               IUCrData
_journal_page_first              x191501
_journal_paper_doi               10.1107/S2414314619015013
_journal_volume                  4
_journal_year                    2019
_chemical_formula_iupac          'C12 H11 N3 O2 S'
_chemical_formula_moiety         'C12 H11 N3 O2 S'
_chemical_formula_sum            'C12 H11 N3 O2 S'
_chemical_formula_weight         261.30
_chemical_name_systematic
2-[1-(1,3-Dioxo-1,3-dihydro-2H-inden-2-ylidene)ethyl]hydrazinecarbothioamide
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.0751(6)
_cell_length_b                   7.6891(4)
_cell_length_c                   20.7891(9)
_cell_measurement_reflns_used    6090
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      29.571
_cell_measurement_theta_min      2.380
_cell_volume                     2409.75(19)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      99(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18247
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.571
_diffrn_reflns_theta_min         2.380
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.756
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.248
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.996
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0628
_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)+(0.1170P)²+0.3104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1728
_reflns_number_gt                2712
_reflns_number_total             3382
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5524sup1.cif
_cod_data_source_block           I
_cod_database_code               1552865
_cod_database_fobs_code          1552865
_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   0.824
_shelx_estimated_absorpt_t_max   0.937
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
S S1 0.43388(3) 0.69858(6) 0.75750(2) 0.01816(17) Uani d 1
O O1 0.86124(9) 0.5148(2) 0.58244(8) 0.0294(4) Uani d 1
O O2 0.58261(8) 0.40510(17) 0.48472(6) 0.0202(3) Uani d 1
N N1 0.50396(12) 0.8510(2) 0.65405(8) 0.0213(4) Uani d 1
H HN1 0.4960(17) 0.948(4) 0.6726(15) 0.043(8) Uiso d 1
H HN2 0.5428(16) 0.853(3) 0.6251(14) 0.025(6) Uiso d 1
N N2 0.52093(10) 0.5557(2) 0.66273(7) 0.0162(3) Uani d 1
H HN3 0.5202(14) 0.465(3) 0.6853(13) 0.024(6) Uiso d 1
N N3 0.57075(10) 0.5469(2) 0.60634(7) 0.0150(3) Uani d 1
H HN4 0.5434(15) 0.516(3) 0.5700(14) 0.027(6) Uiso d 1
C C1 0.49117(11) 0.7065(2) 0.68685(8) 0.0152(4) Uani d 1
C C2 0.66012(11) 0.5365(2) 0.60836(8) 0.0141(3) Uani d 1
C C3 0.70518(11) 0.4833(2) 0.55397(8) 0.0151(3) Uani d 1
C C4 0.80153(11) 0.4714(2) 0.54558(10) 0.0191(4) Uani d 1
C C5 0.81627(12) 0.3939(2) 0.48089(10) 0.0209(4) Uani d 1
C C6 0.89580(14) 0.3553(3) 0.45015(12) 0.0308(5) Uani d 1
H H6 0.951321 0.377395 0.470159 0.037 Uiso calc 1
C C7 0.89078(15) 0.2830(3) 0.38902(12) 0.0366(6) Uani d 1
H H7 0.944060 0.256797 0.366630 0.044 Uiso calc 1
C C8 0.81003(16) 0.2482(3) 0.35982(11) 0.0349(5) Uani d 1
H H8 0.809265 0.197883 0.318095 0.042 Uiso calc 1
C C9 0.72982(15) 0.2855(3) 0.39040(10) 0.0268(5) Uani d 1
H H9 0.674394 0.261752 0.370510 0.032 Uiso calc 1
C C10 0.73498(12) 0.3592(2) 0.45145(8) 0.0177(4) Uani d 1
C C11 0.66251(11) 0.4159(2) 0.49572(8) 0.0149(3) Uani d 1
C C12 0.70463(12) 0.5863(3) 0.67010(9) 0.0215(4) Uani d 1
H H12A 0.684628 0.702208 0.683240 0.026 Uiso calc 1
H H12B 0.769069 0.587450 0.663875 0.026 Uiso calc 1
H H12C 0.689323 0.501675 0.703566 0.026 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'
O O 0.0106 0.0060 '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 N1 HN1 119(2)
C1 N1 HN2 119.0(17)
HN1 N1 HN2 114(2)
C1 N2 N3 122.48(15)
C1 N2 HN3 120.3(17)
N3 N2 HN3 115.8(16)
C2 N3 N2 120.94(15)
C2 N3 HN4 118.1(15)
N2 N3 HN4 118.4(15)
N1 C1 N2 119.14(16)
N1 C1 S1 123.34(14)
N2 C1 S1 117.46(13)
N3 C2 C3 118.86(15)
N3 C2 C12 117.30(15)
C3 C2 C12 123.84(16)
C2 C3 C11 124.43(15)
C2 C3 C4 127.10(16)
C11 C3 C4 108.34(15)
O1 C4 C3 129.43(19)
O1 C4 C5 124.29(17)
C3 C4 C5 106.28(16)
C6 C5 C10 121.0(2)
C6 C5 C4 129.0(2)
C10 C5 C4 109.99(15)
C7 C6 C5 117.3(2)
C7 C6 H6 121.3
C5 C6 H6 121.3
C8 C7 C6 121.71(18)
C8 C7 H7 119.1
C6 C7 H7 119.1
C7 C8 C9 121.4(2)
C7 C8 H8 119.3
C9 C8 H8 119.3
C10 C9 C8 116.8(2)
C10 C9 H9 121.6
C8 C9 H9 121.6
C9 C10 C5 121.78(17)
C9 C10 C11 129.77(18)
C5 C10 C11 108.44(16)
O2 C11 C3 127.43(15)
O2 C11 C10 125.64(16)
C3 C11 C10 106.93(14)
C2 C12 H12A 109.5
C2 C12 H12B 109.5
H12A C12 H12B 109.5
C2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7050(18)
O1 C4 1.228(2)
O2 C11 1.229(2)
N1 C1 1.318(2)
N1 HN1 0.85(3)
N1 HN2 0.84(3)
N2 C1 1.340(2)
N2 N3 1.394(2)
N2 HN3 0.84(2)
N3 C2 1.350(2)
N3 HN4 0.89(3)
C2 C3 1.381(2)
C2 C12 1.498(2)
C3 C11 1.466(2)
C3 C4 1.466(2)
C4 C5 1.488(3)
C5 C6 1.391(3)
C5 C10 1.395(3)
C6 C7 1.389(4)
C6 H6 0.9500
C7 C8 1.386(4)
C7 H7 0.9500
C8 C9 1.396(3)
C8 H8 0.9500
C9 C10 1.392(3)
C9 H9 0.9500
C10 C11 1.493(2)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 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
C12 H12B O1 . 0.98 2.26 3.033(3) 135 yes
N2 HN3 S1 3_646 0.84(2) 2.47(2) 3.2796(16) 163(2) yes
N1 HN1 S1 3_656 0.85(3) 2.63(3) 3.3764(19) 147(2) yes
N1 HN2 O1 8_765 0.84(3) 2.11(3) 2.816(2) 142(2) yes
N3 HN4 O2 . 0.89(3) 2.05(3) 2.7592(19) 135(2) yes
N3 HN4 O2 5_666 0.89(3) 2.30(2) 3.0107(19) 137(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
C1 N2 N3 C2 97.7(2)
N3 N2 C1 N1 4.8(3)
N3 N2 C1 S1 -178.07(12)
N2 N3 C2 C3 163.37(16)
N2 N3 C2 C12 -17.4(2)
N3 C2 C3 C11 -7.9(3)
C12 C2 C3 C11 172.90(16)
N3 C2 C3 C4 176.93(16)
C12 C2 C3 C4 -2.3(3)
C2 C3 C4 O1 -4.8(3)
C11 C3 C4 O1 179.40(19)
C2 C3 C4 C5 175.41(17)
C11 C3 C4 C5 -0.42(19)
O1 C4 C5 C6 0.3(3)
C3 C4 C5 C6 -179.83(19)
O1 C4 C5 C10 179.86(18)
C3 C4 C5 C10 -0.3(2)
C10 C5 C6 C7 0.7(3)
C4 C5 C6 C7 -179.82(18)
C5 C6 C7 C8 -0.9(3)
C6 C7 C8 C9 0.5(3)
C7 C8 C9 C10 0.0(3)
C8 C9 C10 C5 -0.2(3)
C8 C9 C10 C11 179.00(18)
C6 C5 C10 C9 -0.2(3)
C4 C5 C10 C9 -179.77(17)
C6 C5 C10 C11 -179.53(16)
C4 C5 C10 C11 0.9(2)
C2 C3 C11 O2 4.2(3)
C4 C3 C11 O2 -179.82(17)
C2 C3 C11 C10 -175.02(16)
C4 C3 C11 C10 0.94(19)
C9 C10 C11 O2 0.3(3)
C5 C10 C11 O2 179.61(16)
C9 C10 C11 C3 179.59(18)
C5 C10 C11 C3 -1.14(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 135761128
