#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:00:13 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301809 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/12/2311230.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_2311230
loop_
_publ_author_name
'Mague, Joel T.'
'Mohamed, Shaaban K.'
'Akkurt, Mehmet'
'Hassan, Alaa A.'
'Albayati, Mustafa R.'
_publ_section_title
;
 1-{[(Z)-Cyclo-pentyl-idene]amino}-3-phenyl-thio-urea.
;
_journal_coeditor_code           SJ5395
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica. Section E, Structure reports online'
_journal_page_first              o515
_journal_paper_doi               10.1107/S1600536814007028
_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
;
1-{[(Z)-Cyclopentylidene]amino}-3-phenylthiourea
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                93.0220(9)
_cell_angle_beta                 105.4530(9)
_cell_angle_gamma                104.7070(8)
_cell_formula_units_Z            2
_cell_length_a                   7.3997(2)
_cell_length_b                   7.57900(10)
_cell_length_c                   11.4657(2)
_cell_measurement_reflns_used    8773
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.0159
_cell_measurement_theta_min      4.0340
_cell_volume                     594.45(2)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction
;
SAINT  (Bruker, 2013) and CELL_NOW (Sheldrick, 2008a)
;
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008a)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008a)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008a)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11363
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         70.010
_diffrn_reflns_theta_min         4.034
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         11360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0395
_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)+(0.0390P)²+0.1956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                9454
_reflns_number_total             11360
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5395sup1.cif
_cod_data_source_block           I
_cod_database_code               2311230
_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   0.654
_shelx_estimated_absorpt_t_max   0.917
_shelxl_version_number           .2013
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
S S1 0.89113(8) 1.01459(7) 0.81488(4) 0.02372(18) Uani d 1
N N1 0.7313(2) 0.5215(2) 0.90890(15) 0.0216(4) Uani d 1
N N2 0.8223(3) 0.7082(2) 0.91604(15) 0.0213(4) Uani d 1
H H2 0.8859 0.7824 0.9880 0.026 Uiso d 1
N N3 0.7179(2) 0.6693(2) 0.70759(14) 0.0226(4) Uani d 1
H H3 0.6668 0.5483 0.7126 0.027 Uiso d 1
C C1 0.7350(3) 0.4552(3) 1.01002(18) 0.0201(5) Uani d 1
C C2 0.8303(3) 0.5512(3) 1.13816(17) 0.0221(5) Uani d 1
H H2A 0.7989 0.6695 1.1480 0.027 Uiso calc 1
H H2B 0.9739 0.5749 1.1600 0.027 Uiso calc 1
C C3 0.7435(3) 0.4160(3) 1.21708(19) 0.0274(5) Uani d 1
H H3A 0.8400 0.4244 1.2973 0.033 Uiso calc 1
H H3B 0.6258 0.4424 1.2306 0.033 Uiso calc 1
C C4 0.6913(3) 0.2257(3) 1.14529(19) 0.0280(5) Uani d 1
H H4A 0.5820 0.1399 1.1656 0.034 Uiso calc 1
H H4B 0.8049 0.1748 1.1635 0.034 Uiso calc 1
C C5 0.6317(3) 0.2559(3) 1.01077(19) 0.0242(5) Uani d 1
H H5A 0.6742 0.1736 0.9604 0.029 Uiso calc 1
H H5B 0.4885 0.2326 0.9791 0.029 Uiso calc 1
C C6 0.8052(3) 0.7858(3) 0.81110(18) 0.0201(5) Uani d 1
C C7 0.6780(3) 0.7262(3) 0.58782(18) 0.0240(5) Uani d 1
C C8 0.8249(4) 0.7674(3) 0.5318(2) 0.0358(6) Uani d 1
H H8 0.9527 0.7619 0.5729 0.043 Uiso calc 1
C C9 0.7831(5) 0.8171(4) 0.4146(2) 0.0453(7) Uani d 1
H H9 0.8827 0.8458 0.3751 0.054 Uiso calc 1
C C10 0.5971(5) 0.8248(3) 0.3557(2) 0.0448(7) Uani d 1
H H10 0.5690 0.8582 0.2755 0.054 Uiso calc 1
C C11 0.4526(4) 0.7845(3) 0.4123(2) 0.0410(7) Uani d 1
H H11 0.3249 0.7906 0.3714 0.049 Uiso calc 1
C C12 0.4930(4) 0.7346(3) 0.5295(2) 0.0309(5) Uani d 1
H H12 0.3933 0.7066 0.5690 0.037 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 0.0181 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'
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
C1 N1 N2 117.12(17)
C6 N2 N1 118.43(17)
C6 N2 H2 118.3
N1 N2 H2 123.1
C6 N3 C7 123.96(16)
C6 N3 H3 118.7
C7 N3 H3 116.9
N1 C1 C2 128.72(18)
N1 C1 C5 120.66(18)
C2 C1 C5 110.61(16)
C1 C2 C3 104.01(17)
C1 C2 H2A 111.0
C3 C2 H2A 111.0
C1 C2 H2B 111.0
C3 C2 H2B 111.0
H2A C2 H2B 109.0
C4 C3 C2 105.41(17)
C4 C3 H3A 110.7
C2 C3 H3A 110.7
C4 C3 H3B 110.7
C2 C3 H3B 110.7
H3A C3 H3B 108.8
C3 C4 C5 105.07(16)
C3 C4 H4A 110.7
C5 C4 H4A 110.7
C3 C4 H4B 110.7
C5 C4 H4B 110.7
H4A C4 H4B 108.8
C1 C5 C4 104.55(17)
C1 C5 H5A 110.8
C4 C5 H5A 110.8
C1 C5 H5B 110.8
C4 C5 H5B 110.8
H5A C5 H5B 108.9
N3 C6 N2 115.83(18)
N3 C6 S1 123.58(14)
N2 C6 S1 120.59(16)
C12 C7 C8 120.89(19)
C12 C7 N3 119.41(19)
C8 C7 N3 119.68(19)
C7 C8 C9 119.1(2)
C7 C8 H8 120.4
C9 C8 H8 120.4
C10 C9 C8 120.0(3)
C10 C9 H9 120.0
C8 C9 H9 120.0
C11 C10 C9 120.4(2)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 120.0(2)
C10 C11 H11 120.0
C12 C11 H11 120.0
C7 C12 C11 119.6(2)
C7 C12 H12 120.2
C11 C12 H12 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C6 1.682(2)
N1 C1 1.284(2)
N1 N2 1.392(2)
N2 C6 1.357(2)
N2 H2 0.9098
N3 C6 1.341(3)
N3 C7 1.439(2)
N3 H3 0.9098
C1 C2 1.503(3)
C1 C5 1.512(3)
C2 C3 1.535(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.526(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.533(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C7 C12 1.373(3)
C7 C8 1.382(3)
C8 C9 1.391(3)
C8 H8 0.9500
C9 C10 1.379(4)
C9 H9 0.9500
C10 C11 1.373(4)
C10 H10 0.9500
C11 C12 1.391(3)
C11 H11 0.9500
C12 H12 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
N2 H2 S1 2_777 0.91 2.56 3.4636(18) 172
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 N1 N2 C6 -173.97(17)
N2 N1 C1 C2 -1.9(3)
N2 N1 C1 C5 177.10(17)
N1 C1 C2 C3 166.7(2)
C5 C1 C2 C3 -12.4(2)
C1 C2 C3 C4 27.7(2)
C2 C3 C4 C5 -32.9(2)
N1 C1 C5 C4 173.24(18)
C2 C1 C5 C4 -7.6(2)
C3 C4 C5 C1 24.8(2)
C7 N3 C6 N2 176.88(18)
C7 N3 C6 S1 -3.4(3)
N1 N2 C6 N3 -6.8(3)
N1 N2 C6 S1 173.42(14)
C6 N3 C7 C12 -100.6(2)
C6 N3 C7 C8 80.9(3)
C12 C7 C8 C9 -0.3(3)
N3 C7 C8 C9 178.2(2)
C7 C8 C9 C10 0.0(4)
C8 C9 C10 C11 0.3(4)
C9 C10 C11 C12 -0.3(4)
C8 C7 C12 C11 0.3(3)
N3 C7 C12 C11 -178.16(19)
C10 C11 C12 C7 0.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 909360
