#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/96/2229686.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_2229686
loop_
_publ_author_name
'Salam, Md. Abdus'
'Affan, Md. Abu'
'Ahmad, Fasihuddin B.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 1-Cyclohexyl-3-{(E)-[1-(pyridin-2-yl)ethylidene]amino}thiourea
;
_journal_coeditor_code           HG5008
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o955
_journal_paper_doi               10.1107/S1600536811009317
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H20 N4 S'
_chemical_formula_moiety         'C14 H20 N4 S'
_chemical_formula_sum            'C14 H20 N4 S'
_chemical_formula_weight         276.40
_chemical_name_systematic
;
1-Cyclohexyl-3-{(E)-[1-(pyridin-2-yl)ethylidene]amino}thiourea
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.718(8)
_cell_angle_beta                 90.427(9)
_cell_angle_gamma                90.979(8)
_cell_formula_units_Z            2
_cell_length_a                   5.8824(6)
_cell_length_b                   10.2410(9)
_cell_length_c                   12.3902(14)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.3
_cell_measurement_theta_min      2.5
_cell_volume                     743.74(13)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent Technologies, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent Technologies, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type
;
Agilent Supernova Dual diffractometer with an Atlas detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5817
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent Technologies, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.2389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                2355
_reflns_number_total             3292
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5008.cif
_cod_data_source_block           I
_cod_database_code               2229686
_cod_database_fobs_code          2229686
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.98373(10) 0.38035(6) 0.62998(5) 0.0566(2) Uani d . 1 . .
N N1 0.6028(3) 0.4301(2) 0.73985(16) 0.0516(5) Uani d D 1 . .
N N2 0.6780(3) 0.56047(19) 0.60354(16) 0.0473(5) Uani d D 1 . .
N N3 0.4954(3) 0.63316(18) 0.63973(15) 0.0443(4) Uani d . 1 . .
N N4 0.2260(4) 0.9312(2) 0.61127(19) 0.0655(6) Uani d . 1 . .
C C1 0.6423(4) 0.3310(2) 0.81548(18) 0.0509(6) Uani d . 1 . .
H H1A 0.7317 0.2612 0.7785 0.061 Uiso calc R 1 . .
C C2 0.7750(5) 0.3871(3) 0.9131(2) 0.0774(9) Uani d . 1 . .
H H2A 0.6945 0.4610 0.9476 0.093 Uiso calc R 1 . .
H H2B 0.9219 0.4189 0.8903 0.093 Uiso calc R 1 . .
C C3 0.8102(6) 0.2857(4) 0.9947(3) 0.1056(13) Uani d . 1 . .
H H3A 0.9038 0.2159 0.9627 0.127 Uiso calc R 1 . .
H H3B 0.8898 0.3264 1.0579 0.127 Uiso calc R 1 . .
C C4 0.5863(6) 0.2288(4) 1.0287(2) 0.0850(10) Uani d . 1 . .
H H4A 0.6135 0.1614 1.0776 0.102 Uiso calc R 1 . .
H H4B 0.4981 0.2969 1.0668 0.102 Uiso calc R 1 . .
C C5 0.4558(5) 0.1713(3) 0.9314(3) 0.0797(9) Uani d . 1 . .
H H5A 0.3094 0.1388 0.9542 0.096 Uiso calc R 1 . .
H H5B 0.5380 0.0976 0.8977 0.096 Uiso calc R 1 . .
C C6 0.4189(5) 0.2718(3) 0.8486(2) 0.0746(8) Uani d . 1 . .
H H6A 0.3421 0.2296 0.7851 0.090 Uiso calc R 1 . .
H H6B 0.3222 0.3407 0.8796 0.090 Uiso calc R 1 . .
C C7 0.7428(4) 0.4599(2) 0.66113(17) 0.0436(5) Uani d . 1 . .
C C8 0.4457(4) 0.7360(2) 0.59286(18) 0.0433(5) Uani d . 1 . .
C C9 0.5690(4) 0.7871(2) 0.4999(2) 0.0575(6) Uani d . 1 . .
H H9A 0.5857 0.7177 0.4437 0.086 Uiso calc R 1 . .
H H9B 0.7165 0.8197 0.5238 0.086 Uiso calc R 1 . .
H H9C 0.4842 0.8567 0.4725 0.086 Uiso calc R 1 . .
C C10 0.2493(4) 0.8097(2) 0.64002(17) 0.0438(5) Uani d . 1 . .
C C11 0.1000(4) 0.7543(2) 0.70977(19) 0.0516(6) Uani d . 1 . .
H H11 0.1192 0.6689 0.7279 0.062 Uiso calc R 1 . .
C C12 -0.0774(4) 0.8277(3) 0.7519(2) 0.0627(7) Uani d . 1 . .
H H12 -0.1794 0.7929 0.7993 0.075 Uiso calc R 1 . .
C C13 -0.1011(5) 0.9530(3) 0.7227(2) 0.0702(8) Uani d . 1 . .
H H13 -0.2191 1.0048 0.7500 0.084 Uiso calc R 1 . .
C C14 0.0518(5) 1.0001(3) 0.6527(3) 0.0768(9) Uani d . 1 . .
H H14 0.0339 1.0850 0.6327 0.092 Uiso calc R 1 . .
H H1 0.478(3) 0.474(2) 0.743(2) 0.065(8) Uiso d D 1 . .
H H2 0.768(4) 0.579(3) 0.5503(14) 0.065(8) Uiso d 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 125.56(19) ?
C7 N1 H1 . . 114.1(18) ?
C1 N1 H1 . . 120.3(18) ?
C7 N2 N3 . . 118.18(18) ?
C7 N2 H2 . . 115.9(18) ?
N3 N2 H2 . . 125.6(18) ?
C8 N3 N2 . . 119.02(18) ?
C10 N4 C14 . . 117.7(2) ?
N1 C1 C2 . . 111.2(2) ?
N1 C1 C6 . . 110.3(2) ?
C2 C1 C6 . . 110.8(2) ?
N1 C1 H1A . . 108.1 ?
C2 C1 H1A . . 108.1 ?
C6 C1 H1A . . 108.1 ?
C1 C2 C3 . . 111.7(3) ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2B . . 109.3 ?
C3 C2 H2B . . 109.3 ?
H2A C2 H2B . . 107.9 ?
C4 C3 C2 . . 111.2(3) ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3B . . 109.4 ?
C2 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C5 C4 C3 . . 110.2(3) ?
C5 C4 H4A . . 109.6 ?
C3 C4 H4A . . 109.6 ?
C5 C4 H4B . . 109.6 ?
C3 C4 H4B . . 109.6 ?
H4A C4 H4B . . 108.1 ?
C4 C5 C6 . . 111.9(3) ?
C4 C5 H5A . . 109.2 ?
C6 C5 H5A . . 109.2 ?
C4 C5 H5B . . 109.2 ?
C6 C5 H5B . . 109.2 ?
H5A C5 H5B . . 107.9 ?
C1 C6 C5 . . 111.2(2) ?
C1 C6 H6A . . 109.4 ?
C5 C6 H6A . . 109.4 ?
C1 C6 H6B . . 109.4 ?
C5 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
N1 C7 N2 . . 115.73(19) ?
N1 C7 S1 . . 124.18(17) ?
N2 C7 S1 . . 120.08(16) ?
N3 C8 C10 . . 114.81(19) ?
N3 C8 C9 . . 126.0(2) ?
C10 C8 C9 . . 119.19(19) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N4 C10 C11 . . 122.2(2) ?
N4 C10 C8 . . 116.23(19) ?
C11 C10 C8 . . 121.5(2) ?
C12 C11 C10 . . 119.0(2) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C13 C12 C11 . . 118.8(2) ?
C13 C12 H12 . . 120.6 ?
C11 C12 H12 . . 120.6 ?
C12 C13 C14 . . 118.7(3) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
N4 C14 C13 . . 123.6(3) ?
N4 C14 H14 . . 118.2 ?
C13 C14 H14 . . 118.2 ?
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 C7 . 1.678(2) ?
N1 C7 . 1.332(3) ?
N1 C1 . 1.457(3) ?
N1 H1 . 0.870(10) ?
N2 C7 . 1.359(3) ?
N2 N3 . 1.374(2) ?
N2 H2 . 0.878(10) ?
N3 C8 . 1.281(3) ?
N4 C10 . 1.331(3) ?
N4 C14 . 1.336(3) ?
C1 C2 . 1.503(4) ?
C1 C6 . 1.512(3) ?
C1 H1A . 0.9800 ?
C2 C3 . 1.523(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.508(5) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.498(5) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.529(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C8 C10 . 1.488(3) ?
C8 C9 . 1.491(3) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.384(3) ?
C11 C12 . 1.377(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.370(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.364(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
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
N1 H1 N3 . 0.867(19) 2.16(2) 2.592(3) 110.8(17)
C9 H9C N4 . 0.96 2.39 2.822(3) 107
N2 H2 S1 2_766 0.88(2) 2.73(2) 3.610(2) 174(2)
C9 H9B Cg1 1_655 0.96 2.89 3.776(3) 155
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
C7 N2 N3 C8 . . . . 173.2(2) ?
C7 N1 C1 C2 . . . . 87.7(3) ?
C7 N1 C1 C6 . . . . -149.0(2) ?
N1 C1 C2 C3 . . . . 178.0(3) ?
C6 C1 C2 C3 . . . . 54.9(3) ?
C1 C2 C3 C4 . . . . -56.3(4) ?
C2 C3 C4 C5 . . . . 56.3(4) ?
C3 C4 C5 C6 . . . . -56.3(4) ?
N1 C1 C6 C5 . . . . -177.8(2) ?
C2 C1 C6 C5 . . . . -54.2(3) ?
C4 C5 C6 C1 . . . . 55.7(4) ?
C1 N1 C7 N2 . . . . -176.6(2) ?
C1 N1 C7 S1 . . . . 4.3(3) ?
N3 N2 C7 N1 . . . . 8.8(3) ?
N3 N2 C7 S1 . . . . -172.17(15) ?
N2 N3 C8 C10 . . . . -178.40(18) ?
N2 N3 C8 C9 . . . . 0.0(3) ?
C14 N4 C10 C11 . . . . 0.3(4) ?
C14 N4 C10 C8 . . . . -179.7(2) ?
N3 C8 C10 N4 . . . . 164.7(2) ?
C9 C8 C10 N4 . . . . -13.9(3) ?
N3 C8 C10 C11 . . . . -15.3(3) ?
C9 C8 C10 C11 . . . . 166.1(2) ?
N4 C10 C11 C12 . . . . -0.7(4) ?
C8 C10 C11 C12 . . . . 179.3(2) ?
C10 C11 C12 C13 . . . . 0.4(4) ?
C11 C12 C13 C14 . . . . 0.2(4) ?
C10 N4 C14 C13 . . . . 0.3(5) ?
C12 C13 C14 N4 . . . . -0.6(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4521786
