#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224875.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_2224875
loop_
_publ_author_name
'Hu, Jun'
'Ji, Jin-xiu'
'Zhou, Ying'
'Wang, Ji-kui'
'Xu, Yan-hua'
_publ_section_title
(E)-5-(3,5-Dimethylphenyl)-N-[4-(methylsulfanyl)benzylidene]-1,3,4-thiadiazol-2-amine
_journal_coeditor_code           BT5165
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o410
_journal_paper_doi               10.1107/S1600536810001558
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H17 N3 S2'
_chemical_formula_moiety         'C18 H17 N3 S2'
_chemical_formula_sum            'C18 H17 N3 S2'
_chemical_formula_weight         339.47
_chemical_melting_point          408
_chemical_name_systematic
;
(E)-5-(3,5-Dimethylphenyl)-N-[4-(methylsulfanyl)benzylidene]-
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                90.98(3)
_cell_angle_beta                 110.03(3)
_cell_angle_gamma                99.66(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5640(17)
_cell_length_b                   9.3370(19)
_cell_length_c                   11.570(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     854.1(3)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3324
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.9117
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.456
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0650
_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)+(0.1000P)²+1.5500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.2079
_reflns_number_gt                2286
_reflns_number_total             3098
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5165.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224875
_cod_database_fobs_code          2224875
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 0.62029(16) 1.18993(14) -0.40284(12) 0.0614(4) Uani d . 1 . .
S S2 0.10286(13) 0.70508(13) 0.07048(10) 0.0522(4) Uani d . 1 . .
N N1 0.0950(5) 0.8908(4) -0.1158(3) 0.0502(9) Uani d . 1 . .
N N2 -0.1485(5) 0.8040(5) -0.0728(4) 0.0692(12) Uani d . 1 . .
N N3 -0.2085(5) 0.7183(5) 0.0023(4) 0.0685(12) Uani d . 1 . .
C C1 0.7907(6) 1.0978(6) -0.3883(5) 0.0723(15) Uani d . 1 . .
H H1B 0.8553 1.1424 -0.4359 0.108 Uiso calc R 1 . .
H H1C 0.7470 0.9974 -0.4181 0.108 Uiso calc R 1 . .
H H1D 0.8620 1.1039 -0.3031 0.108 Uiso calc R 1 . .
C C2 0.5192(5) 1.0955(4) -0.3116(4) 0.0445(9) Uani d . 1 . .
C C3 0.3640(6) 1.1315(5) -0.3168(4) 0.0533(11) Uani d . 1 . .
H H3B 0.3206 1.2023 -0.3674 0.064 Uiso calc R 1 . .
C C4 0.2770(5) 1.0636(5) -0.2484(4) 0.0524(11) Uani d . 1 . .
H H4A 0.1754 1.0897 -0.2519 0.063 Uiso calc R 1 . .
C C5 0.3370(5) 0.9560(4) -0.1734(4) 0.0442(9) Uani d . 1 . .
C C6 0.4919(5) 0.9225(5) -0.1672(4) 0.0487(10) Uani d . 1 . .
H H6A 0.5357 0.8527 -0.1155 0.058 Uiso calc R 1 . .
C C7 0.5814(5) 0.9899(4) -0.2356(4) 0.0473(10) Uani d . 1 . .
H H7A 0.6838 0.9646 -0.2309 0.057 Uiso calc R 1 . .
C C8 0.2444(5) 0.8767(5) -0.1040(4) 0.0480(10) Uani d . 1 . .
H H8A 0.2960 0.8130 -0.0488 0.058 Uiso calc R 1 . .
C C9 0.0130(5) 0.8098(4) -0.0484(4) 0.0447(9) Uani d . 1 . .
C C10 -0.0942(5) 0.6600(4) 0.0806(4) 0.0453(10) Uani d . 1 . .
C C11 -0.1302(5) 0.5649(4) 0.1713(4) 0.0443(9) Uani d . 1 . .
C C12 -0.2857(5) 0.5491(5) 0.1857(4) 0.0491(10) Uani d . 1 . .
H H12A -0.3676 0.5975 0.1361 0.059 Uiso calc R 1 . .
C C13 -0.3218(6) 0.4629(5) 0.2724(4) 0.0543(11) Uani d . 1 . .
C C14 -0.2009(6) 0.3892(5) 0.3429(4) 0.0580(12) Uani d . 1 . .
H H14A -0.2254 0.3293 0.4003 0.070 Uiso calc R 1 . .
C C15 -0.0418(6) 0.4016(5) 0.3309(4) 0.0521(11) Uani d . 1 . .
C C16 -0.0071(5) 0.4910(5) 0.2446(4) 0.0484(10) Uani d . 1 . .
H H16A 0.0979 0.5018 0.2356 0.058 Uiso calc R 1 . .
C C17 -0.4903(7) 0.4480(6) 0.2888(6) 0.0737(15) Uani d . 1 . .
H H17A -0.4931 0.3842 0.3525 0.111 Uiso calc R 1 . .
H H17B -0.5785 0.4083 0.2128 0.111 Uiso calc R 1 . .
H H17C -0.5070 0.5421 0.3116 0.111 Uiso calc R 1 . .
C C18 0.0868(7) 0.3170(6) 0.4057(5) 0.0736(15) Uani d . 1 . .
H H18A 0.1873 0.3396 0.3853 0.110 Uiso calc R 1 . .
H H18B 0.0416 0.2146 0.3877 0.110 Uiso calc R 1 . .
H H18C 0.1137 0.3426 0.4919 0.110 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'
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
C2 S1 C1 . . 103.0(2) ?
C10 S2 C9 . . 86.66(19) ?
C8 N1 C9 . . 119.2(4) ?
C9 N2 N3 . . 112.4(4) ?
C10 N3 N2 . . 113.2(4) ?
S1 C1 H1B . . 109.5 ?
S1 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
S1 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C7 C2 C3 . . 118.8(4) ?
C7 C2 S1 . . 124.6(3) ?
C3 C2 S1 . . 116.6(3) ?
C4 C3 C2 . . 120.5(4) ?
C4 C3 H3B . . 119.8 ?
C2 C3 H3B . . 119.8 ?
C3 C4 C5 . . 121.1(4) ?
C3 C4 H4A . . 119.4 ?
C5 C4 H4A . . 119.4 ?
C4 C5 C6 . . 118.1(4) ?
C4 C5 C8 . . 122.7(4) ?
C6 C5 C8 . . 119.2(4) ?
C7 C6 C5 . . 121.5(4) ?
C7 C6 H6A . . 119.2 ?
C5 C6 H6A . . 119.2 ?
C6 C7 C2 . . 120.0(4) ?
C6 C7 H7A . . 120.0 ?
C2 C7 H7A . . 120.0 ?
N1 C8 C5 . . 122.3(4) ?
N1 C8 H8A . . 118.9 ?
C5 C8 H8A . . 118.9 ?
N2 C9 N1 . . 120.4(4) ?
N2 C9 S2 . . 113.3(3) ?
N1 C9 S2 . . 126.2(3) ?
N3 C10 C11 . . 122.6(4) ?
N3 C10 S2 . . 114.3(3) ?
C11 C10 S2 . . 123.1(3) ?
C12 C11 C16 . . 119.6(4) ?
C12 C11 C10 . . 120.0(4) ?
C16 C11 C10 . . 120.3(4) ?
C13 C12 C11 . . 121.3(4) ?
C13 C12 H12A . . 119.4 ?
C11 C12 H12A . . 119.4 ?
C14 C13 C12 . . 118.7(4) ?
C14 C13 C17 . . 120.4(4) ?
C12 C13 C17 . . 120.9(4) ?
C13 C14 C15 . . 121.9(4) ?
C13 C14 H14A . . 119.1 ?
C15 C14 H14A . . 119.1 ?
C16 C15 C14 . . 118.5(4) ?
C16 C15 C18 . . 120.2(4) ?
C14 C15 C18 . . 121.3(4) ?
C15 C16 C11 . . 120.0(4) ?
C15 C16 H16A . . 120.0 ?
C11 C16 H16A . . 120.0 ?
C13 C17 H17A . . 109.5 ?
C13 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C13 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
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 C2 . 1.745(4) ?
S1 C1 . 1.777(5) ?
S2 C10 . 1.714(4) ?
S2 C9 . 1.736(4) ?
N1 C8 . 1.269(5) ?
N1 C9 . 1.376(5) ?
N2 C9 . 1.305(5) ?
N2 N3 . 1.360(5) ?
N3 C10 . 1.290(5) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C2 C7 . 1.384(6) ?
C2 C3 . 1.407(6) ?
C3 C4 . 1.358(6) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.387(6) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.392(5) ?
C5 C8 . 1.442(5) ?
C6 C7 . 1.371(6) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
C8 H8A . 0.9300 ?
C10 C11 . 1.465(6) ?
C11 C12 . 1.382(6) ?
C11 C16 . 1.399(6) ?
C12 C13 . 1.380(6) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.375(6) ?
C13 C17 . 1.503(6) ?
C14 C15 . 1.403(6) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.389(6) ?
C15 C18 . 1.500(6) ?
C16 H16A . 0.9300 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
C7 H7A N2 1_655 0.93 2.58 3.223(6) 126.00 yes
C8 H8A S2 . 0.93 2.59 3.041(5) 110.00 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
C9 N2 N3 C10 . . . . -0.7(7) ?
C1 S1 C2 C7 . . . . 8.1(5) ?
C1 S1 C2 C3 . . . . -172.1(4) ?
C7 C2 C3 C4 . . . . 0.0(7) ?
S1 C2 C3 C4 . . . . -179.8(4) ?
C2 C3 C4 C5 . . . . -1.0(7) ?
C3 C4 C5 C6 . . . . 1.9(7) ?
C3 C4 C5 C8 . . . . -177.0(4) ?
C4 C5 C6 C7 . . . . -1.9(7) ?
C8 C5 C6 C7 . . . . 177.0(4) ?
C5 C6 C7 C2 . . . . 1.0(7) ?
C3 C2 C7 C6 . . . . 0.0(7) ?
S1 C2 C7 C6 . . . . 179.8(3) ?
C9 N1 C8 C5 . . . . 178.8(4) ?
C4 C5 C8 N1 . . . . 6.6(7) ?
C6 C5 C8 N1 . . . . -172.3(4) ?
N3 N2 C9 N1 . . . . 179.6(4) ?
N3 N2 C9 S2 . . . . 0.9(6) ?
C8 N1 C9 N2 . . . . -168.9(4) ?
C8 N1 C9 S2 . . . . 9.7(6) ?
C10 S2 C9 N2 . . . . -0.7(4) ?
C10 S2 C9 N1 . . . . -179.3(4) ?
N2 N3 C10 C11 . . . . 179.3(4) ?
N2 N3 C10 S2 . . . . 0.1(6) ?
C9 S2 C10 N3 . . . . 0.3(4) ?
C9 S2 C10 C11 . . . . -178.9(4) ?
N3 C10 C11 C12 . . . . -8.1(7) ?
S2 C10 C11 C12 . . . . 171.1(3) ?
N3 C10 C11 C16 . . . . 172.7(4) ?
S2 C10 C11 C16 . . . . -8.2(6) ?
C16 C11 C12 C13 . . . . 0.8(7) ?
C10 C11 C12 C13 . . . . -178.5(4) ?
C11 C12 C13 C14 . . . . -1.6(7) ?
C11 C12 C13 C17 . . . . 179.1(4) ?
C12 C13 C14 C15 . . . . 1.3(7) ?
C17 C13 C14 C15 . . . . -179.4(4) ?
C13 C14 C15 C16 . . . . -0.2(7) ?
C13 C14 C15 C18 . . . . -178.1(5) ?
C14 C15 C16 C11 . . . . -0.7(7) ?
C18 C15 C16 C11 . . . . 177.2(4) ?
C12 C11 C16 C15 . . . . 0.4(6) ?
C10 C11 C16 C15 . . . . 179.7(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744303
