#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/96/2239683.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_2239683
loop_
_publ_author_name
'Rocha, Fillipe Vieira'
'de Godoy Netto, Adelino Vieira'
'Beck, Johannes'
'Daniels, Jörg'
'de Oliveira, Adriano Bof'
_publ_section_title
;
 N-Methyl-2-(1-methyl-3-phenylprop-2-en-1-ylidene)hydrazinecarbothioamide
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o800
_journal_paper_doi               10.1107/S1600536814013889
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H15 N3 S'
_chemical_formula_moiety         'C12 H15 N3 S'
_chemical_formula_sum            'C12 H15 N3 S'
_chemical_formula_weight         233.33
_chemical_name_systematic
;
N-Methyl-2-(1-methyl-3-phenylprop-2-en-1-ylidene)hydrazinecarbothioamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.5832(2)
_cell_length_b                   7.9509(2)
_cell_length_c                   28.9259(5)
_cell_measurement_reflns_used    31577
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_volume                     2434.00(9)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            26770
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9552
_exptl_absorpt_correction_T_min  0.9035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.266
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0349P)²+1.1303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                2414
_reflns_number_total             2783
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bx2460sup1.cif
_cod_data_source_block           I
_cod_database_code               2239683
_cod_database_fobs_code          2239683
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
S S1 0.55474(3) 0.22917(4) -0.026590(10) 0.02121(10) Uani d 1 1
N N1 0.46643(10) 0.21163(13) 0.10454(3) 0.0194(2) Uani d 1 1
N N2 0.46052(10) 0.18678(14) 0.05748(4) 0.0197(2) Uani d 1 1
N N3 0.62048(10) 0.37903(13) 0.05248(4) 0.0209(2) Uani d 1 1
C C1 0.35320(12) 0.12835(15) 0.26361(4) 0.0198(3) Uani d 1 1
C C2 0.46266(13) 0.20581(18) 0.28079(5) 0.0238(3) Uani d 1 1
C C3 0.47782(14) 0.23114(18) 0.32807(5) 0.0265(3) Uani d 1 1
C C4 0.38429(14) 0.18207(18) 0.35891(5) 0.0283(3) Uani d 1 1
C C5 0.27620(14) 0.10384(19) 0.34236(5) 0.0292(3) Uani d 1 1
C C6 0.26153(13) 0.07566(18) 0.29525(4) 0.0248(3) Uani d 1 1
C C7 0.33153(12) 0.10103(16) 0.21392(4) 0.0203(3) Uani d 1 1
C C8 0.39960(12) 0.16857(16) 0.17955(4) 0.0203(3) Uani d 1 1
C C9 0.38228(11) 0.13760(15) 0.13014(4) 0.0183(2) Uani d 1 1
C C10 0.54759(11) 0.26906(15) 0.03065(4) 0.0174(2) Uani d 1 1
C C11 0.71582(13) 0.48111(18) 0.02979(5) 0.0252(3) Uani d 1 1
C C12 0.27638(12) 0.03234(18) 0.11160(4) 0.0213(3) Uani d 1 1
H HN2 0.4267(16) 0.097(2) 0.0461(6) 0.035(5) Uiso d 1 1
H HN3 0.6058(15) 0.390(2) 0.0823(6) 0.031(4) Uiso d 1 1
H H2 0.5277(16) 0.240(2) 0.2603(6) 0.034(4) Uiso d 1 1
H H3 0.5538(15) 0.286(2) 0.3389(6) 0.033(4) Uiso d 1 1
H H4 0.3962(15) 0.201(2) 0.3915(6) 0.032(4) Uiso d 1 1
H H5 0.2119(16) 0.071(2) 0.3634(6) 0.040(5) Uiso d 1 1
H H6 0.1862(15) 0.020(2) 0.2843(5) 0.034(4) Uiso d 1 1
H H7 0.2640(15) 0.026(2) 0.2072(5) 0.026(4) Uiso d 1 1
H H8 0.4663(14) 0.245(2) 0.1856(6) 0.026(4) Uiso d 1 1
H H11A 0.6826(18) 0.530(3) 0.0021(7) 0.059(6) Uiso d 1 1
H H11B 0.7862(19) 0.419(3) 0.0221(7) 0.052(6) Uiso d 1 1
H H11C 0.738(2) 0.572(3) 0.0489(7) 0.061(6) Uiso d 1 1
H H12A 0.2344(17) 0.088(2) 0.0863(6) 0.038(5) Uiso d 1 1
H H12B 0.3056(16) -0.073(2) 0.0991(6) 0.036(5) Uiso d 1 1
H H12C 0.2155(15) 0.005(2) 0.1358(6) 0.033(4) Uiso d 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 N2 117.87(10)
C10 N2 N1 117.43(10)
C10 N2 HN2 117.2(11)
N1 N2 HN2 121.0(11)
C10 N3 C11 123.89(11)
C10 N3 HN3 115.2(11)
C11 N3 HN3 120.8(11)
C6 C1 C2 118.21(12)
C6 C1 C7 119.15(11)
C2 C1 C7 122.64(11)
C3 C2 C1 120.46(12)
C3 C2 H2 119.3(10)
C1 C2 H2 120.3(10)
C4 C3 C2 120.56(13)
C4 C3 H3 120.8(10)
C2 C3 H3 118.7(10)
C5 C4 C3 119.49(12)
C5 C4 H4 121.0(10)
C3 C4 H4 119.5(10)
C4 C5 C6 120.18(13)
C4 C5 H5 119.6(11)
C6 C5 H5 120.2(11)
C5 C6 C1 121.07(13)
C5 C6 H6 119.2(10)
C1 C6 H6 119.7(10)
C8 C7 C1 125.58(12)
C8 C7 H7 120.2(9)
C1 C7 H7 114.3(9)
C7 C8 C9 126.19(12)
C7 C8 H8 121.4(10)
C9 C8 H8 112.4(10)
N1 C9 C8 113.27(11)
N1 C9 C12 124.17(11)
C8 C9 C12 122.55(11)
N3 C10 N2 115.86(11)
N3 C10 S1 124.41(9)
N2 C10 S1 119.73(9)
N3 C11 H11A 110.6(12)
N3 C11 H11B 111.8(13)
H11A C11 H11B 108.3(17)
N3 C11 H11C 109.8(13)
H11A C11 H11C 105.7(18)
H11B C11 H11C 110.4(18)
C9 C12 H12A 111.0(10)
C9 C12 H12B 112.4(10)
H12A C12 H12B 105.3(14)
C9 C12 H12C 111.2(10)
H12A C12 H12C 110.1(14)
H12B C12 H12C 106.6(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.6875(12)
N1 C9 1.2994(16)
N1 N2 1.3769(14)
N2 C10 1.3708(15)
N2 HN2 0.862(18)
N3 C10 1.3261(16)
N3 C11 1.4518(16)
N3 HN3 0.879(17)
C1 C6 1.3980(18)
C1 C2 1.4029(18)
C1 C7 1.4716(17)
C2 C3 1.3917(18)
C2 H2 0.949(18)
C3 C4 1.388(2)
C3 H3 0.965(17)
C4 C5 1.387(2)
C4 H4 0.964(17)
C5 C6 1.3896(19)
C5 H5 0.950(18)
C6 H6 0.967(17)
C7 C8 1.3402(18)
C7 H7 0.950(16)
C8 C9 1.4616(16)
C8 H8 0.948(16)
C9 C12 1.4981(17)
C11 H11A 0.96(2)
C11 H11B 0.92(2)
C11 H11C 0.94(2)
C12 H12A 0.965(18)
C12 H12B 0.964(18)
C12 H12C 0.977(17)
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
N3 HN3 N1 1 0.879(17) 2.143(16) 2.5877(15) 110.7(13)
N2 HN2 S1 5_655 0.862(18) 2.663(18) 3.4296(12) 148.7(15)
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_4
_geom_torsion
N1 N1 N2 C10 1 . 0.00(9)
C9 N1 N2 C10 . . 178.27(11)
C9 N1 N2 N1 . 1 0E1(10)
C6 C1 C2 C3 . . -0.9(2)
C7 C1 C2 C3 . . 178.99(13)
C1 C2 C3 C4 . . -0.8(2)
C2 C3 C4 C5 . . 1.4(2)
C3 C4 C5 C6 . . -0.3(2)
C4 C5 C6 C1 . . -1.4(2)
C2 C1 C6 C5 . . 2.0(2)
C7 C1 C6 C5 . . -177.89(13)
C6 C1 C7 C8 . . 168.26(13)
C2 C1 C7 C8 . . -11.7(2)
C1 C7 C8 C9 . . 177.50(12)
N2 N1 C9 N1 . 1 0E1(10)
N1 N1 C9 C8 1 . 0.00(7)
N2 N1 C9 C8 . . 178.31(10)
N1 N1 C9 C12 1 . 0.000(19)
N2 N1 C9 C12 . . -2.44(18)
C7 C8 C9 N1 . 1 -176.06(12)
C7 C8 C9 N1 . . -176.06(12)
C7 C8 C9 C12 . . 4.7(2)
C11 N3 C10 N2 . . -178.42(12)
C11 N3 C10 S1 . . 0.53(18)
N1 N2 C10 N3 1 . -7.04(16)
N1 N2 C10 N3 . . -7.04(16)
N1 N2 C10 S1 1 . 173.96(9)
N1 N2 C10 S1 . . 173.96(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 54602184
