##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-2018/3
_chemical_name_systematic
;\
2-{3-Methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}\
hydrazinecarbothioamide
;
_chemical_name_common     'cis-jasmone thiosemicarbazone'
_chemical_formula_moiety     'C12 H19 N3 S'
_chemical_formula_sum     'C12 H19 N3 S'
_chemical_formula_iupac     'C12 H19 N3 S'
_chemical_formula_weight     237.36
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.0159(7)
_cell_length_b     8.0595(3)
_cell_length_c     10.8243(5)
_cell_angle_alpha     90
_cell_angle_beta     94.372(3)
_cell_angle_gamma     90
_cell_volume     1306.15(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     60208
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.485
_cell_measurement_temperature     123
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.174
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.054
_exptl_crystal_density_diffrn     1.207
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     0.227
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(Blessing, 1995)
;
_exptl_absorpt_correction_T_min     0.9215
_exptl_absorpt_correction_T_max     0.9983
_diffrn_ambient_temperature     123
_diffrn_source     'sealed X-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'horizontally mounted graphite crystal'
_diffrn_measurement_device_type     'Enraf--Nonius FR590 Kappa CCD'
_diffrn_measurement_method     'CCD rotation images, thick slices, κ-goniostat'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     24176
_diffrn_reflns_av_R_equivalents     0.0826
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_theta_min     3.155
_diffrn_reflns_theta_max     27.570
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     14
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     3002
_reflns_number_gt     2241
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0798
_refine_ls_R_factor_gt     0.0540
_refine_ls_wR_factor_gt     0.1297
_refine_ls_wR_factor_ref     0.1427
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_restrained_S_all     1.086
_refine_ls_number_reflns     3002
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0690P)²+0.7307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.592
_refine_diff_density_min     -0.449
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
COLLECT (Nonius, 1998)
;
_computing_cell_refinement
;
HKL, Scalepack (Otwinowski & Minor, 1997)
;
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor, 1997)
;
_computing_structure_solution
;
SIR-92 (Altomare et al.,  1994)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006), CrystalExplorer (Wolff et al.,
2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and
enCIFer (Allen et al.,
2004)
;
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 0.49279(4) -0.38063(6) 0.29692(5) 0.02576(19) Uani d 1 . .
    N N1 0.35988(12) -0.5052(2) -0.01509(16) 0.0239(4) Uani d 1 . .
    N N2 0.40985(12) -0.5194(2) 0.09773(17) 0.0235(4) Uani d 1 . .
    H H1 0.4271(17) -0.617(3) 0.133(2) 0.030(7) Uiso d 1 . .
    N N3 0.42480(14) -0.2376(2) 0.09074(19) 0.0275(5) Uani d 1 . .
    H H2 0.3988(18) -0.242(4) 0.016(3) 0.039(5) Uiso d 1 . .
    H H3 0.4455(19) -0.149(4) 0.126(3) 0.039(5) Uiso d 1 . .
    C C1 0.32864(14) -0.6392(3) -0.0662(2) 0.0224(5) Uani d 1 . .
    C C2 0.33976(16) -0.8181(3) -0.0266(2) 0.0251(5) Uani d 1 . .
    H H2A 0.3276(15) -0.833(3) 0.065(2) 0.024(4) Uiso d 1 . .
    H H2B 0.4031(17) -0.853(3) -0.036(2) 0.024(4) Uiso d 1 . .
    C C3 0.27458(17) -0.9129(3) -0.1170(2) 0.0295(5) Uani d 1 . .
    H H3A 0.3041(16) -1.002(4) -0.156(2) 0.035(5) Uiso d 1 . .
    H H3B 0.2234(17) -0.961(3) -0.074(2) 0.035(5) Uiso d 1 . .
    C C4 0.24066(15) -0.7858(3) -0.2109(2) 0.0269(5) Uani d 1 . .
    C C5 0.27121(15) -0.6322(3) -0.1810(2) 0.0253(5) Uani d 1 . .
    C C6 0.25021(17) -0.4704(3) -0.2465(2) 0.0299(5) Uani d 1 . .
    H H6A 0.3013(19) -0.413(4) -0.246(3) 0.039(5) Uiso d 1 . .
    H H6B 0.2284(17) -0.490(3) -0.337(3) 0.039(5) Uiso d 1 . .
    C C7 0.18173(18) -0.3701(3) -0.1851(2) 0.0349(6) Uani d 1 . .
    H H7 0.1977(18) -0.347(3) -0.097(3) 0.041(8) Uiso d 1 . .
    C C8 0.1055(2) -0.3144(4) -0.2354(3) 0.0520(8) Uani d 1 . .
    H H8A 0.077777 -0.233393 -0.190673 0.062 Uiso calc 0.590(14) A 1
    H H8B 0.059808 -0.292155 -0.184493 0.062 Uiso calc 0.410(14) A 2
    C C9A 0.0569(4) -0.3651(9) -0.3570(6) 0.0381(17) Uani d 0.590(14) A 1
    H H9A1 0.014033 -0.451696 -0.342863 0.046 Uiso calc 0.590(14) A 1
    H H9A2 0.099214 -0.408217 -0.412357 0.046 Uiso calc 0.590(14) A 1
    C C10A 0.0088(6) -0.2146(8) -0.4159(9) 0.0420(18) Uani d 0.590(14) A 1
    H H10A -0.034413 -0.174691 -0.362002 0.063 Uiso calc 0.590(14) A 1
    H H10B -0.020921 -0.245795 -0.494084 0.063 Uiso calc 0.590(14) A 1
    H H10C 0.051400 -0.128624 -0.428493 0.063 Uiso calc 0.590(14) A 1
    C C11 0.17972(19) -0.8356(4) -0.3194(3) 0.0371(6) Uani d 1 . .
    H H11A 0.161(2) -0.743(4) -0.376(3) 0.051(5) Uiso d 1 . .
    H H11B 0.125(2) -0.877(4) -0.291(3) 0.051(5) Uiso d 1 . .
    H H11C 0.206(2) -0.916(4) -0.370(3) 0.051(5) Uiso d 1 . .
    C C12 0.43977(14) -0.3783(2) 0.1527(2) 0.0221(4) Uani d 1 . .
    C C9B 0.0882(7) -0.2831(15) -0.3810(7) 0.043(3) Uani d 0.410(14) A 2
    H H9B1 0.108084 -0.172234 -0.400126 0.052 Uiso d 0.410(14) A 2
    H H9B2 0.120614 -0.362544 -0.427766 0.052 Uiso d 0.410(14) A 2
    C C10B -0.0104(10) -0.290(3) -0.4108(15) 0.090(6) Uani d 0.410(14) A 2
    H H10D -0.034871 -0.381309 -0.367063 0.135 Uiso calc 0.410(14) A 2
    H H10E -0.022841 -0.306245 -0.498360 0.135 Uiso calc 0.410(14) A 2
    H H10F -0.037061 -0.188515 -0.386266 0.135 Uiso calc 0.410(14) A 2
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C12 . 1.698(2) ?
    N1 C1 . 1.285(3) ?
    N1 N2 . 1.388(2) ?
    N2 C12 . 1.345(3) ?
    N2 H1 . 0.90(3) ?
    N3 C12 . 1.328(3) ?
    N3 H2 . 0.87(3) ?
    N3 H3 . 0.85(3) ?
    C1 C5 . 1.458(3) ?
    C1 C2 . 1.510(3) ?
    C2 C3 . 1.534(3) ?
    C2 H2A . 1.03(2) ?
    C2 H2B . 1.00(2) ?
    C3 C4 . 1.504(3) ?
    C3 H3A . 0.96(3) ?
    C3 H3B . 1.00(3) ?
    C4 C5 . 1.351(3) ?
    C4 C11 . 1.489(3) ?
    C5 C6 . 1.506(3) ?
    C6 C7 . 1.502(4) ?
    C6 H6A . 0.90(3) ?
    C6 H6B . 1.02(3) ?
    C7 C8 . 1.308(4) ?
    C7 H7 . 0.98(3) ?
    C8 C9A . 1.512(6) ?
    C8 C9B . 1.598(8) ?
    C8 H8A . 0.9300 ?
    C8 H8B . 0.9300 ?
    C9A C10A . 1.526(10) ?
    C9A H9A1 . 0.9700 ?
    C9A H9A2 . 0.9700 ?
    C10A H10A . 0.9600 ?
    C10A H10B . 0.9600 ?
    C10A H10C . 0.9600 ?
    C11 H11A . 1.00(3) ?
    C11 H11B . 0.96(3) ?
    C11 H11C . 0.95(3) ?
    C9B C10B . 1.49(2) ?
    C9B H9B1 . 0.9700 ?
    C9B H9B2 . 0.9700 ?
    C10B H10D . 0.9600 ?
    C10B H10E . 0.9600 ?
    C10B H10F . 0.9600 ?
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 N2 . . 117.67(18) ?
    C12 N2 N1 . . 117.32(18) ?
    C12 N2 H1 . . 118.2(16) ?
    N1 N2 H1 . . 124.3(16) ?
    C12 N3 H2 . . 118.8(19) ?
    C12 N3 H3 . . 116.3(19) ?
    H2 N3 H3 . . 125(3) ?
    N1 C1 C5 . . 120.47(19) ?
    N1 C1 C2 . . 130.6(2) ?
    C5 C1 C2 . . 108.90(18) ?
    C1 C2 C3 . . 104.07(18) ?
    C1 C2 H2A . . 111.4(14) ?
    C3 C2 H2A . . 113.8(13) ?
    C1 C2 H2B . . 108.9(13) ?
    C3 C2 H2B . . 111.0(13) ?
    H2A C2 H2B . . 107.6(19) ?
    C4 C3 C2 . . 105.00(19) ?
    C4 C3 H3A . . 110.8(15) ?
    C2 C3 H3A . . 111.1(15) ?
    C4 C3 H3B . . 110.1(15) ?
    C2 C3 H3B . . 111.7(14) ?
    H3A C3 H3B . . 108(2) ?
    C5 C4 C11 . . 127.8(2) ?
    C5 C4 C3 . . 111.8(2) ?
    C11 C4 C3 . . 120.4(2) ?
    C4 C5 C1 . . 109.67(19) ?
    C4 C5 C6 . . 128.7(2) ?
    C1 C5 C6 . . 121.56(19) ?
    C7 C6 C5 . . 112.6(2) ?
    C7 C6 H6A . . 109.3(18) ?
    C5 C6 H6A . . 107.2(18) ?
    C7 C6 H6B . . 109.0(15) ?
    C5 C6 H6B . . 111.1(16) ?
    H6A C6 H6B . . 108(2) ?
    C8 C7 C6 . . 127.4(2) ?
    C8 C7 H7 . . 118.7(16) ?
    C6 C7 H7 . . 113.9(16) ?
    C7 C8 C9A . . 128.2(3) ?
    C7 C8 C9B . . 122.4(4) ?
    C7 C8 H8A . . 115.9 ?
    C9A C8 H8A . . 115.9 ?
    C7 C8 H8B . . 118.8 ?
    C9B C8 H8B . . 118.8 ?
    C8 C9A C10A . . 109.3(5) ?
    C8 C9A H9A1 . . 109.8 ?
    C10A C9A H9A1 . . 109.8 ?
    C8 C9A H9A2 . . 109.8 ?
    C10A C9A H9A2 . . 109.8 ?
    H9A1 C9A H9A2 . . 108.3 ?
    C9A C10A H10A . . 109.5 ?
    C9A C10A H10B . . 109.5 ?
    H10A C10A H10B . . 109.5 ?
    C9A C10A H10C . . 109.5 ?
    H10A C10A H10C . . 109.5 ?
    H10B C10A H10C . . 109.5 ?
    C4 C11 H11A . . 114.3(18) ?
    C4 C11 H11B . . 109.3(18) ?
    H11A C11 H11B . . 104(2) ?
    C4 C11 H11C . . 112.3(18) ?
    H11A C11 H11C . . 105(3) ?
    H11B C11 H11C . . 111(3) ?
    N3 C12 N2 . . 117.47(19) ?
    N3 C12 S1 . . 121.54(17) ?
    N2 C12 S1 . . 120.98(16) ?
    C10B C9B C8 . . 107.0(10) ?
    C10B C9B H9B1 . . 107.9 ?
    C8 C9B H9B1 . . 109.0 ?
    C10B C9B H9B2 . . 113.0 ?
    C8 C9B H9B2 . . 111.1 ?
    H9B1 C9B H9B2 . . 108.7 ?
    C9B C10B H10D . . 109.5 ?
    C9B C10B H10E . . 109.5 ?
    H10D C10B H10E . . 109.5 ?
    C9B C10B H10F . . 109.5 ?
    H10D C10B H10F . . 109.5 ?
    H10E C10B H10F . . 109.5 ?
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
    C1 N1 N2 C12 . . . . -177.82(19) ?
    N2 N1 C1 C5 . . . . 176.34(19) ?
    N2 N1 C1 C2 . . . . -2.8(4) ?
    N1 C1 C2 C3 . . . . 171.8(2) ?
    C5 C1 C2 C3 . . . . -7.4(2) ?
    C1 C2 C3 C4 . . . . 7.3(3) ?
    C2 C3 C4 C5 . . . . -5.1(3) ?
    C2 C3 C4 C11 . . . . 175.9(2) ?
    C11 C4 C5 C1 . . . . 179.4(2) ?
    C3 C4 C5 C1 . . . . 0.5(3) ?
    C11 C4 C5 C6 . . . . 1.9(4) ?
    C3 C4 C5 C6 . . . . -177.1(2) ?
    N1 C1 C5 C4 . . . . -174.7(2) ?
    C2 C1 C5 C4 . . . . 4.5(3) ?
    N1 C1 C5 C6 . . . . 3.0(3) ?
    C2 C1 C5 C6 . . . . -177.7(2) ?
    C4 C5 C6 C7 . . . . 100.2(3) ?
    C1 C5 C6 C7 . . . . -77.0(3) ?
    C5 C6 C7 C8 . . . . -123.5(3) ?
    C6 C7 C8 C9A . . . . 14.5(7) ?
    C6 C7 C8 C9B . . . . -24.3(7) ?
    C7 C8 C9A C10A . . . . -145.8(5) ?
    N1 N2 C12 N3 . . . . -4.8(3) ?
    N1 N2 C12 S1 . . . . 174.04(15) ?
    C7 C8 C9B C10B . . . . 156.7(12) ?
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
    N2 H1 S1 2_645 0.90(3) 2.53(3) 3.4142(19) 166(2) yes
    N3 H3 S1 2_655 0.85(3) 2.48(3) 3.325(2) 173(3) yes
    C2 H2B S1 2_645 1.00(2) 2.93(2) 3.436(2) 112.2(16) yes
_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     ?
_shelx_estimated_absorpt_T_max     ?
data_publication_text
_journal_date_recd_electronic     2023-11-21
_journal_date_accepted     2023-11-24
_journal_name_full     'IUCrData'
_journal_year     2023
_journal_volume     8
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314623010180
_journal_coeditor_code     BT4143
_publ_contact_author_name     'Adriano Bof de Oliveira'
_publ_contact_author_address
;Departamento de Química
Universidade Federal de Sergipe
Av. Marcelo Deda Chagas s/n, Campus Universitário
49107-230 São Cristóvão-SE, Brazil
;
_publ_contact_author_email     adriano@daad-alumni.de
_publ_section_title
;\
A second crystalline modification of
2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}\
hydrazinecarbothioamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Oliveira, Adriano Bof de '
;Departamento de Química
Universidade Federal de Sergipe
Av. Marcelo Deda Chagas s/n, Campus Universitário
49107-230 São Cristóvão-SE, Brazil
;
    'Bresolin, Leandro'
;Escola de Química e Alimentos
Universidade Federal do Rio Grande
Av. Itália km 08, Campus Carreiros
96203-900 Rio Grande-RS, Brazil
;
    'Gervini, Vanessa Carratu'
;Escola de Química e Alimentos
Universidade Federal do Rio Grande
Av. Itália km 08, Campus Carreiros
96203-900 Rio Grande-RS, Brazil
;
    'Beck, Johannes'
;Institut für Anorganische Chemie
Rheinische Friedrich-Wilhelms-Universität Bonn
Gerhard-Domagk-Strasse 1
D-53121 Bonn, Germany
;
    'Daniels, Jörg'
;Institut für Anorganische Chemie
Rheinische Friedrich-Wilhelms-Universität Bonn
Gerhard-Domagk-Strasse 1
D-53121 Bonn, Germany
;
_publ_section_synopsis
;
The crystal structure and Hirshfeld analysis of a second crystalline
modification of the cis-jasmone thiosemicarbazone is reported. The
molecular structure matches the asymmetric unit and the molecules are linked
into mono-periodic hydrogen-bonded ribbons along [010].
;
