#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/13/2211388.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_2211388
loop_
_publ_author_name
'Kai-huang Zou'
'Li-Xue Zhang'
'Jian-Yu Jin'
'Hong-Ping Xiao'
'Kang Zhang'
_publ_section_title
4-[(4-Chlorobenzylidene)amino]-3-(3-hydroxypropyl)-1,2,4-triazole-5(4H)-thione
_journal_coeditor_code           FL2069
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5773
_journal_page_last               o5774
_journal_paper_doi               10.1107/S1600536806048057
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H13 Cl N4 O S'
_chemical_formula_moiety         'C12 H13 Cl N4 O S'
_chemical_formula_sum            'C12 H13 Cl N4 O S'
_chemical_formula_weight         296.77
_chemical_name_systematic
;
4-[(4-Chlorobenzylidene)amino]-3-(3-hydroxypropyl)-1,2,4-triazole-5-thione
;
_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           SHELXL97
_cell_angle_alpha                91.610(2)
_cell_angle_beta                 97.999(2)
_cell_angle_gamma                95.695(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1880(6)
_cell_length_b                   7.5476(7)
_cell_length_c                   14.6378(14)
_cell_measurement_reflns_used    1694
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.72
_cell_volume                     673.05(11)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3560
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.9296
_exptl_absorpt_correction_T_min  0.8914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0475
_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)+(0.048P)²+0.3229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                2117
_reflns_number_total             2342
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2069.cif
_cod_data_source_block           I
_cod_database_code               2211388
_cod_database_fobs_code          2211388
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
Cl Cl1 1.35634(14) 0.19177(12) 0.51723(6) 0.0727(3) Uani d . 1
S S1 0.51393(11) 0.92889(8) 0.73662(5) 0.0479(2) Uani d . 1
O O1 -0.0045(3) 0.0319(2) 0.86319(14) 0.0490(5) Uani d . 1
H H1 -0.1233 0.0110 0.8302 0.073 Uiso calc R 1
N N1 0.6302(3) 0.4951(3) 0.76705(14) 0.0387(5) Uani d . 1
N N2 0.4879(3) 0.5903(2) 0.80949(13) 0.0325(4) Uani d . 1
N N3 0.2706(3) 0.7641(3) 0.85390(14) 0.0402(5) Uani d . 1
H H3 0.2035 0.8567 0.8618 0.048 Uiso calc R 1
N N4 0.2248(3) 0.6064(3) 0.89565(14) 0.0395(5) Uani d . 1
C C1 1.1893(4) 0.3036(4) 0.58016(18) 0.0458(6) Uani d . 1
C C2 1.0308(5) 0.2069(4) 0.6205(2) 0.0549(7) Uani d . 1
H H2 1.0171 0.0830 0.6165 0.066 Uiso calc R 1
C C3 0.8929(4) 0.2953(3) 0.66695(19) 0.0477(7) Uani d . 1
H H3A 0.7843 0.2303 0.6938 0.057 Uiso calc R 1
C C4 0.9129(4) 0.4801(3) 0.67451(16) 0.0361(5) Uani d . 1
C C5 1.0753(4) 0.5738(3) 0.63276(17) 0.0401(6) Uani d . 1
H H5 1.0900 0.6977 0.6364 0.048 Uiso calc R 1
C C6 1.2141(4) 0.4863(4) 0.58631(18) 0.0446(6) Uani d . 1
H H6 1.3234 0.5501 0.5594 0.053 Uiso calc R 1
C C7 0.7669(4) 0.5773(3) 0.72240(17) 0.0399(6) Uani d . 1
H H7 0.7743 0.7008 0.7201 0.048 Uiso calc R 1
C C8 0.4281(4) 0.7615(3) 0.80015(16) 0.0356(5) Uani d . 1
C C9 0.3582(4) 0.5026(3) 0.86723(16) 0.0335(5) Uani d . 1
C C10 0.3824(4) 0.3163(3) 0.89429(18) 0.0395(6) Uani d . 1
H H10A 0.5326 0.3089 0.9223 0.047 Uiso calc R 1
H H10B 0.3541 0.2383 0.8392 0.047 Uiso calc R 1
C C11 0.2277(4) 0.2507(3) 0.96198(17) 0.0425(6) Uani d . 1
H H11A 0.2869 0.1518 0.9943 0.051 Uiso calc R 1
H H11B 0.2239 0.3458 1.0075 0.051 Uiso calc R 1
C C12 -0.0036(4) 0.1913(3) 0.91758(18) 0.0419(6) Uani d . 1
H H12A -0.0975 0.1702 0.9648 0.050 Uiso calc R 1
H H12B -0.0595 0.2836 0.8789 0.050 Uiso calc R 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
C12 O1 H1 109.5
C7 N1 N2 119.4(2)
C9 N2 C8 108.29(18)
C9 N2 N1 118.71(18)
C8 N2 N1 132.70(19)
C8 N3 N4 114.36(19)
C8 N3 H3 122.8
N4 N3 H3 122.8
C9 N4 N3 104.09(18)
C6 C1 C2 121.3(2)
C6 C1 Cl1 119.5(2)
C2 C1 Cl1 119.2(2)
C3 C2 C1 119.2(2)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 121.1(2)
C2 C3 H3A 119.5
C4 C3 H3A 119.5
C3 C4 C5 118.2(2)
C3 C4 C7 122.2(2)
C5 C4 C7 119.6(2)
C6 C5 C4 121.1(2)
C6 C5 H5 119.5
C4 C5 H5 119.5
C1 C6 C5 119.1(2)
C1 C6 H6 120.4
C5 C6 H6 120.4
N1 C7 C4 120.5(2)
N1 C7 H7 119.7
C4 C7 H7 119.7
N3 C8 N2 102.42(19)
N3 C8 S1 125.93(18)
N2 C8 S1 131.62(18)
N4 C9 N2 110.8(2)
N4 C9 C10 126.4(2)
N2 C9 C10 122.7(2)
C9 C10 C11 113.2(2)
C9 C10 H10A 108.9
C11 C10 H10A 108.9
C9 C10 H10B 108.9
C11 C10 H10B 108.9
H10A C10 H10B 107.8
C12 C11 C10 114.3(2)
C12 C11 H11A 108.7
C10 C11 H11A 108.7
C12 C11 H11B 108.7
C10 C11 H11B 108.7
H11A C11 H11B 107.6
O1 C12 C11 109.1(2)
O1 C12 H12A 109.9
C11 C12 H12A 109.9
O1 C12 H12B 109.9
C11 C12 H12B 109.9
H12A C12 H12B 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.739(3)
S1 C8 1.677(2)
O1 C12 1.423(3)
O1 H1 0.8200
N1 C7 1.265(3)
N1 N2 1.389(3)
N2 C9 1.383(3)
N2 C8 1.385(3)
N3 C8 1.336(3)
N3 N4 1.376(3)
N3 H3 0.8600
N4 C9 1.294(3)
C1 C6 1.371(4)
C1 C2 1.374(4)
C2 C3 1.373(4)
C2 H2 0.9300
C3 C4 1.388(3)
C3 H3A 0.9300
C4 C5 1.392(3)
C4 C7 1.458(3)
C5 C6 1.373(3)
C5 H5 0.9300
C6 H6 0.9300
C7 H7 0.9300
C9 C10 1.487(3)
C10 C11 1.530(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.506(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9700
C12 H12B 0.9700
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 H3 O1 1_565 0.86 1.94 2.780(3) 166.8
O1 H1 S1 1_445 0.82 2.47 3.2922(19) 176.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655109
