#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/55/2205503.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_2205503
loop_
_publ_author_name
'Fang, Xiao-Niu'
'Zhong, Fan'
'Dai, Mei-Zhen'
'Hu, Rong-Hua'
_publ_section_title
;3-(2,4-Dichlorophenyl)-4-[(1E)-(2,4-dichlorophenyl)methyleneamino]-4,5-dihydro-1H-1,2,4-triazole-5-thione
 dimethylformamide solvate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o863
_journal_page_last               o865
_journal_paper_doi               10.1107/S1600536805006240
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H8 Cl4 N4 S, C3 H7 N O'
_chemical_formula_moiety         'C15 H8 Cl4 N4 S, C3 H7 N O'
_chemical_formula_sum            'C18 H15 Cl4 N5 O S'
_chemical_formula_weight         491.21
_chemical_melting_point          .491E-305
_chemical_name_systematic
;
3-(2,4-Dichlorophenyl)-4-[(1E)-(2,4-dichlorophenyl)methyleneamino]-
4,5-dihydro-1H-1,2,4-triazole-5-thione dimethylformamide solvate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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            4
_cell_length_a                   11.3496(19)
_cell_length_b                   18.016(3)
_cell_length_c                   10.9165(18)
_cell_measurement_reflns_used    2025
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      20.2742
_cell_measurement_theta_min      4.2444
_cell_volume                     2232.1(6)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    APEX2
_computing_publication_material  APEX2
_computing_structure_refinement  APEX2
_computing_structure_solution    APEX2
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD 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  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0765
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9843
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         4.27
_diffrn_standards_number         'no decay'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.150
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.821
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.821
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0311
_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)+(0.0165P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0371
_refine_ls_wR_factor_ref         0.0388
_reflns_number_gt                1956
_reflns_number_total             3377
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6143.cif
_cod_data_source_block           I
_cod_original_cell_volume        2232.2(6)
_cod_original_sg_symbol_Hall     'p 2c -2ac'
_cod_database_code               2205503
_cod_database_fobs_code          2205503
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_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_type_symbol
S1 0.00511(8) 0.13674(5) 0.09675(7) 0.0666(2) Uani d . 1 S
Cl1 -0.27397(9) 0.36750(5) 0.74596(7) 0.0881(3) Uani d . 1 Cl
Cl2 -0.20235(9) 0.14720(5) 0.42729(8) 0.0995(3) Uani d . 1 Cl
Cl3 0.22577(10) 0.41118(5) 0.15381(8) 0.0980(3) Uani d . 1 Cl
Cl4 0.56605(9) 0.46671(5) 0.48244(9) 0.0998(3) Uani d . 1 Cl
N1 0.1006(3) 0.26706(14) 0.3018(2) 0.0551(7) Uani d . 1 N
N2 0.1659(3) 0.23067(13) 0.2115(2) 0.0489(7) Uani d . 1 N
N3 0.2378(3) 0.16563(13) 0.0686(2) 0.0646(8) Uani d . 1 N
H3 0.2453 0.1341 0.0099 0.077 Uiso calc R 1 H
N4 0.3297(2) 0.20839(15) 0.1100(2) 0.0604(7) Uani d . 1 N
C1 -0.1561(3) 0.23127(15) 0.4887(3) 0.0517(8) Uani d . 1 C
C2 -0.2236(3) 0.26120(18) 0.5818(3) 0.0580(9) Uani d . 1 C
H2 -0.2892 0.2361 0.6118 0.070 Uiso calc R 1 H
C3 -0.1913(3) 0.32934(19) 0.6294(2) 0.0563(9) Uani d . 1 C
C4 -0.0967(3) 0.36713(18) 0.5825(3) 0.0584(8) Uani d . 1 C
H4 -0.0774 0.4138 0.6128 0.070 Uiso calc R 1 H
C5 -0.0304(3) 0.33594(17) 0.4905(3) 0.0555(8) Uani d . 1 C
H5 0.0343 0.3617 0.4600 0.067 Uiso calc R 1 H
C6 -0.0582(3) 0.26644(17) 0.4420(2) 0.0455(8) Uani d . 1 C
C7 0.0142(3) 0.23342(18) 0.3463(2) 0.0544(9) Uani d . 1 C
H7 -0.0042 0.1862 0.3176 0.065 Uiso calc R 1 H
C8 0.4330(3) 0.27936(18) 0.3519(3) 0.0625(9) Uani d . 1 C
H8 0.4464 0.2288 0.3621 0.075 Uiso calc R 1 H
C9 0.4981(3) 0.3292(2) 0.4178(3) 0.0671(9) Uani d . 1 C
H9 0.5551 0.3125 0.4725 0.080 Uiso calc R 1 H
C10 0.4790(3) 0.4044(2) 0.4029(3) 0.0637(9) Uani d . 1 C
C11 0.3949(3) 0.4297(2) 0.3243(3) 0.0684(10) Uani d . 1 C
H11 0.3821 0.4804 0.3152 0.082 Uiso calc R 1 H
C12 0.3284(3) 0.37882(18) 0.2577(3) 0.0570(8) Uani d . 1 C
C13 0.3470(3) 0.30292(17) 0.2700(3) 0.0478(8) Uani d . 1 C
C14 0.2825(3) 0.24782(17) 0.1956(3) 0.0513(9) Uani d . 1 C
C15 0.1341(3) 0.17703(16) 0.1276(3) 0.0514(8) Uani d . 1 C
C16 0.6339(6) -0.0243(3) 0.3608(4) 0.128(2) Uani d . 1 C
H16 0.5713 -0.0235 0.4157 0.154 Uiso calc R 1 H
C17 0.5406(4) 0.0734(2) 0.2456(4) 0.1180(15) Uani d . 1 C
H17A 0.4770 0.0675 0.3027 0.177 Uiso calc R 1 H
H17B 0.5123 0.0646 0.1639 0.177 Uiso calc R 1 H
H17C 0.5712 0.1230 0.2512 0.177 Uiso calc R 1 H
C18 0.7274(4) 0.0194(2) 0.1837(4) 0.1153(14) Uani d . 1 C
H18A 0.7895 -0.0125 0.2120 0.173 Uiso calc R 1 H
H18B 0.7576 0.0687 0.1722 0.173 Uiso calc R 1 H
H18C 0.6975 0.0010 0.1072 0.173 Uiso calc R 1 H
N5 0.6328(3) 0.02090(18) 0.2740(3) 0.0728(8) Uani d . 1 N
O2 0.7162(3) -0.07169(16) 0.3788(3) 0.1423(15) Uani d . 1 O
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
_geom_angle_publ_flag
C7 N1 N2 117.5(3) yes
C14 N2 C15 109.1(3) yes
C14 N2 N1 119.8(3) yes
C15 N2 N1 131.2(3) yes
C15 N3 N4 114.7(2) yes
C15 N3 H3 122.6 ?
N4 N3 H3 122.6 ?
C14 N4 N3 103.4(3) yes
C6 C1 C2 122.7(3) ?
C6 C1 Cl2 120.1(2) ?
C2 C1 Cl2 117.2(3) ?
C3 C2 C1 118.4(3) ?
C3 C2 H2 120.8 ?
C1 C2 H2 120.8 ?
C4 C3 C2 120.6(3) ?
C4 C3 Cl1 120.3(3) ?
C2 C3 Cl1 119.1(3) ?
C3 C4 C5 119.9(3) ?
C3 C4 H4 120.0 ?
C5 C4 H4 120.0 ?
C4 C5 C6 121.3(3) ?
C4 C5 H5 119.3 ?
C6 C5 H5 119.3 ?
C1 C6 C5 117.0(3) ?
C1 C6 C7 122.2(3) ?
C5 C6 C7 120.7(3) ?
N1 C7 C6 121.5(3) yes
N1 C7 H7 119.2 ?
C6 C7 H7 119.2 ?
C9 C8 C13 121.2(3) ?
C9 C8 H8 119.4 ?
C13 C8 H8 119.4 ?
C8 C9 C10 119.8(3) ?
C8 C9 H9 120.1 ?
C10 C9 H9 120.1 ?
C11 C10 C9 120.8(3) ?
C11 C10 Cl4 120.0(3) ?
C9 C10 Cl4 119.2(3) ?
C10 C11 C12 119.2(3) ?
C10 C11 H11 120.4 ?
C12 C11 H11 120.4 ?
C13 C12 C11 121.0(3) ?
C13 C12 Cl3 119.8(3) ?
C11 C12 Cl3 119.1(3) ?
C12 C13 C8 118.0(3) ?
C12 C13 C14 122.2(3) ?
C8 C13 C14 119.8(3) ?
N4 C14 N2 111.7(3) yes
N4 C14 C13 124.2(3) ?
N2 C14 C13 124.1(3) ?
N3 C15 N2 101.2(3) yes
N3 C15 S1 126.8(3) yes
N2 C15 S1 132.0(3) yes
N5 C16 O2 123.9(6) yes
N5 C16 H16 118.0 ?
O2 C16 H16 118.0 ?
N5 C17 H17A 109.5 ?
N5 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
N5 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
N5 C18 H18A 109.5 ?
N5 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
N5 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C16 N5 C17 126.6(5) ?
C16 N5 C18 119.5(4) ?
C17 N5 C18 113.6(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C15 1.668(3) yes
Cl1 C3 1.724(3) ?
Cl2 C1 1.738(3) ?
Cl3 C12 1.727(3) ?
Cl4 C10 1.729(3) ?
N1 C7 1.251(3) ?
N1 N2 1.397(3) yes
N2 C14 1.369(4) yes
N2 C15 1.380(3) yes
N3 C15 1.357(3) yes
N3 N4 1.374(3) yes
N3 H3 0.8600 ?
N4 C14 1.291(3) yes
C1 C6 1.378(3) ?
C1 C2 1.383(4) ?
C2 C3 1.382(4) ?
C2 H2 0.9300 ?
C3 C4 1.370(4) ?
C4 C5 1.375(4) ?
C4 H4 0.9300 ?
C5 C6 1.396(3) ?
C5 H5 0.9300 ?
C6 C7 1.456(4) ?
C7 H7 0.9300 ?
C8 C9 1.367(4) ?
C8 C13 1.390(4) ?
C8 H8 0.9300 ?
C9 C10 1.382(4) ?
C9 H9 0.9300 ?
C10 C11 1.362(4) ?
C11 C12 1.392(4) ?
C11 H11 0.9300 ?
C12 C13 1.390(4) ?
C13 C14 1.476(4) ?
C16 N5 1.250(4) yes
C16 O2 1.280(6) yes
C16 H16 0.9300 ?
C17 N5 1.445(4) yes
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C18 N5 1.458(4) ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
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
N3 H3 O2 2_654 0.86 1.87 2.726(2) 172 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173491
