#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/96/2229685.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_2229685
loop_
_publ_author_name
'Yu, Peng'
'Wang, Peng'
'Zhang, Jian-Qiang'
'He, Qiu'
'Wan, Rong'
_publ_section_title
;
 (E)-N-(4-Chlorobenzylidene)-5-(4-methylphenyl)-1,3,4-thiadiazol-2-amine
;
_journal_coeditor_code           HG5007
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o861
_journal_paper_doi               10.1107/S1600536811008841
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H12 Cl N3 S'
_chemical_formula_moiety         'C16 H12 Cl N3 S'
_chemical_formula_sum            'C16 H12 Cl N3 S'
_chemical_formula_weight         313.80
_chemical_melting_point_gt       415
_chemical_melting_point_lt       416
_chemical_name_systematic
;
(E)-N-(4-Chlorobenzylidene)-5-(4-methylphenyl)-1,3,4-
thiadiazol-2-amine
;
_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                98.64(3)
_cell_angle_beta                 90.66(3)
_cell_angle_gamma                99.45(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7940(12)
_cell_length_b                   8.7510(18)
_cell_length_c                   14.965(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     739.5(3)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3001
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.38
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  0.9616
_exptl_absorpt_correction_T_min  0.8907
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0576
_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)+(0.0970P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1790
_reflns_number_gt                1816
_reflns_number_total             2708
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg5007.cif
_cod_data_source_block           I
_cod_database_code               2229685
_cod_database_fobs_code          2229685
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 S 0.23283(16) 0.39838(13) 0.35972(7) 0.0476(3) Uani d . 1 . .
Cl Cl -0.1368(3) -0.07874(15) 0.83792(8) 0.0817(5) Uani d . 1 . .
N N1 0.6673(6) 0.4295(4) 0.3257(2) 0.0519(9) Uani d . 1 . .
C C1 0.3679(10) 0.7600(6) -0.0164(3) 0.0755(15) Uani d . 1 . .
H H1B 0.2081 0.7357 -0.0388 0.113 Uiso calc R 1 . .
H H1C 0.4673 0.7212 -0.0622 0.113 Uiso calc R 1 . .
H H1D 0.4125 0.8715 -0.0008 0.113 Uiso calc R 1 . .
N N2 0.6450(6) 0.3517(4) 0.3990(2) 0.0541(9) Uani d . 1 . .
C C2 0.3925(8) 0.6843(5) 0.0659(3) 0.0514(10) Uani d . 1 . .
N N3 0.3694(6) 0.2419(4) 0.4943(2) 0.0453(8) Uani d . 1 . .
C C3 0.6064(8) 0.7020(5) 0.1130(3) 0.0549(11) Uani d . 1 . .
H H3B 0.7361 0.7632 0.0927 0.066 Uiso calc R 1 . .
C C4 0.6334(7) 0.6324(5) 0.1885(3) 0.0509(10) Uani d . 1 . .
H H4A 0.7784 0.6480 0.2188 0.061 Uiso calc R 1 . .
C C5 0.4413(6) 0.5384(4) 0.2189(2) 0.0411(9) Uani d . 1 . .
C C6 0.2262(7) 0.5216(5) 0.1734(3) 0.0484(10) Uani d . 1 . .
H H6A 0.0957 0.4613 0.1937 0.058 Uiso calc R 1 . .
C C7 0.2041(7) 0.5928(5) 0.0990(3) 0.0527(10) Uani d . 1 . .
H H7A 0.0580 0.5794 0.0698 0.063 Uiso calc R 1 . .
C C8 0.4687(6) 0.4610(4) 0.2982(2) 0.0393(8) Uani d . 1 . .
C C9 0.4290(7) 0.3246(4) 0.4246(3) 0.0431(9) Uani d . 1 . .
C C10 0.1634(7) 0.2334(4) 0.5231(3) 0.0453(9) Uani d . 1 . .
H H10A 0.0582 0.2843 0.4964 0.054 Uiso calc R 1 . .
C C11 0.0852(7) 0.1474(4) 0.5959(2) 0.0433(9) Uani d . 1 . .
C C12 0.2161(7) 0.0438(4) 0.6275(3) 0.0455(9) Uani d . 1 . .
H H12A 0.3516 0.0236 0.5986 0.055 Uiso calc R 1 . .
C C13 0.1470(8) -0.0277(5) 0.7001(3) 0.0536(10) Uani d . 1 . .
H H13A 0.2334 -0.0969 0.7207 0.064 Uiso calc R 1 . .
C C14 -0.0557(8) 0.0053(5) 0.7428(3) 0.0513(10) Uani d . 1 . .
C C15 -0.1919(7) 0.1018(5) 0.7109(3) 0.0529(10) Uani d . 1 . .
H H15A -0.3294 0.1195 0.7391 0.063 Uiso calc R 1 . .
C C16 -0.1227(7) 0.1715(5) 0.6373(3) 0.0481(10) Uani d . 1 . .
H H16A -0.2153 0.2354 0.6148 0.058 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S C9 . . 86.66(18) ?
C8 N1 N2 . . 112.6(3) ?
C2 C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C9 N2 N1 . . 112.7(3) ?
C7 C2 C3 . . 116.6(4) ?
C7 C2 C1 . . 121.8(4) ?
C3 C2 C1 . . 121.6(4) ?
C10 N3 C9 . . 119.0(3) ?
C4 C3 C2 . . 122.5(4) ?
C4 C3 H3B . . 118.7 ?
C2 C3 H3B . . 118.7 ?
C3 C4 C5 . . 119.5(4) ?
C3 C4 H4A . . 120.3 ?
C5 C4 H4A . . 120.3 ?
C6 C5 C4 . . 118.5(4) ?
C6 C5 C8 . . 121.4(3) ?
C4 C5 C8 . . 120.0(3) ?
C7 C6 C5 . . 120.8(4) ?
C7 C6 H6A . . 119.6 ?
C5 C6 H6A . . 119.6 ?
C6 C7 C2 . . 122.1(4) ?
C6 C7 H7A . . 119.0 ?
C2 C7 H7A . . 119.0 ?
N1 C8 C5 . . 123.9(3) ?
N1 C8 S . . 114.6(3) ?
C5 C8 S . . 121.4(3) ?
N2 C9 N3 . . 121.5(3) ?
N2 C9 S . . 113.3(3) ?
N3 C9 S . . 125.2(3) ?
N3 C10 C11 . . 122.6(4) ?
N3 C10 H10A . . 118.7 ?
C11 C10 H10A . . 118.7 ?
C16 C11 C12 . . 119.0(4) ?
C16 C11 C10 . . 119.1(4) ?
C12 C11 C10 . . 121.9(3) ?
C13 C12 C11 . . 120.8(4) ?
C13 C12 H12A . . 119.6 ?
C11 C12 H12A . . 119.6 ?
C12 C13 C14 . . 118.6(4) ?
C12 C13 H13A . . 120.7 ?
C14 C13 H13A . . 120.7 ?
C15 C14 C13 . . 121.6(4) ?
C15 C14 Cl . . 119.7(3) ?
C13 C14 Cl . . 118.7(3) ?
C16 C15 C14 . . 119.3(4) ?
C16 C15 H15A . . 120.4 ?
C14 C15 H15A . . 120.4 ?
C15 C16 C11 . . 120.5(4) ?
C15 C16 H16A . . 119.7 ?
C11 C16 H16A . . 119.7 ?
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
S C8 . 1.718(4) ?
S C9 . 1.748(4) ?
Cl C14 . 1.734(4) ?
N1 C8 . 1.303(5) ?
N1 N2 . 1.371(4) ?
C1 C2 . 1.500(6) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
N2 C9 . 1.308(5) ?
C2 C7 . 1.386(6) ?
C2 C3 . 1.392(6) ?
N3 C10 . 1.268(5) ?
N3 C9 . 1.372(5) ?
C3 C4 . 1.381(5) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.395(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.389(5) ?
C5 C8 . 1.471(5) ?
C6 C7 . 1.369(5) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
C10 C11 . 1.451(5) ?
C10 H10A . 0.9300 ?
C11 C16 . 1.393(5) ?
C11 C12 . 1.402(5) ?
C12 C13 . 1.366(5) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.394(6) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.376(6) ?
C15 C16 . 1.371(5) ?
C15 H15A . 0.9300 ?
C16 H16A . 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
_geom_hbond_publ_flag
C6 H6A S . 0.93 2.76 3.139(5) 106 yes
C10 H10A S . 0.93 2.56 3.019(4) 111 yes
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
C8 N1 N2 C9 . . . . 0.7(5) ?
C7 C2 C3 C4 . . . . 0.4(6) ?
C1 C2 C3 C4 . . . . -179.5(4) ?
C2 C3 C4 C5 . . . . 0.9(6) ?
C3 C4 C5 C6 . . . . -1.8(6) ?
C3 C4 C5 C8 . . . . 178.8(3) ?
C4 C5 C6 C7 . . . . 1.5(6) ?
C8 C5 C6 C7 . . . . -179.2(3) ?
C5 C6 C7 C2 . . . . -0.1(6) ?
C3 C2 C7 C6 . . . . -0.8(6) ?
C1 C2 C7 C6 . . . . 179.1(4) ?
N2 N1 C8 C5 . . . . -177.7(3) ?
N2 N1 C8 S . . . . 0.1(4) ?
C6 C5 C8 N1 . . . . 157.1(4) ?
C4 C5 C8 N1 . . . . -23.5(6) ?
C6 C5 C8 S . . . . -20.5(5) ?
C4 C5 C8 S . . . . 158.9(3) ?
C9 S C8 N1 . . . . -0.6(3) ?
C9 S C8 C5 . . . . 177.2(3) ?
N1 N2 C9 N3 . . . . 177.1(3) ?
N1 N2 C9 S . . . . -1.2(5) ?
C10 N3 C9 N2 . . . . 172.4(4) ?
C10 N3 C9 S . . . . -9.6(5) ?
C8 S C9 N2 . . . . 1.0(3) ?
C8 S C9 N3 . . . . -177.2(3) ?
C9 N3 C10 C11 . . . . 179.5(3) ?
N3 C10 C11 C16 . . . . 165.7(4) ?
N3 C10 C11 C12 . . . . -12.5(6) ?
C16 C11 C12 C13 . . . . -2.7(6) ?
C10 C11 C12 C13 . . . . 175.5(4) ?
C11 C12 C13 C14 . . . . -0.5(6) ?
C12 C13 C14 C15 . . . . 3.0(6) ?
C12 C13 C14 Cl . . . . -177.2(3) ?
C13 C14 C15 C16 . . . . -2.2(6) ?
Cl C14 C15 C16 . . . . 178.0(3) ?
C14 C15 C16 C11 . . . . -1.1(6) ?
C12 C11 C16 C15 . . . . 3.5(6) ?
C10 C11 C16 C15 . . . . -174.7(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656582
