#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/60/2216058.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_2216058
loop_
_publ_author_name
'Wang, Pin-Liang'
'Zeng, Hai-Shu'
'Kang, Si-Shun'
'Li, Hai-Ling'
'Wang, Hai-Bo'
_publ_section_title
2-Methyl-5-{3-[4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-ylmethylsulfanyl}-1,3,4-thiadiazole
_journal_coeditor_code           LW2039
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4356
_journal_page_last               o4356
_journal_paper_doi               10.1107/S1600536807050313
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H12 N4 O3 S3'
_chemical_formula_moiety         'C13 H12 N4 O3 S3'
_chemical_formula_sum            'C13 H12 N4 O3 S3'
_chemical_formula_weight         368.45
_chemical_name_systematic
;
2-Methyl-5-{3-[4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-ylmethylsulfanyl}-
1,3,4-thiadiazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.26(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.365(3)
_cell_length_b                   15.956(3)
_cell_length_c                   8.2400(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1543.9(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3239
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.9067
_exptl_absorpt_correction_T_min  0.8251
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.574
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0510
_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)+(0.08P)²+0.5P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                2349
_reflns_number_total             3019
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lw2039.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216058
_cod_database_fobs_code          2216058
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S S1 0.72521(7) 0.34658(5) 0.36586(11) 0.0417(2) Uani d . 1
O O1 0.4584(2) 0.04592(14) 0.1689(3) 0.0481(6) Uani d . 1
N N1 0.7921(2) 0.19730(17) 0.4507(4) 0.0441(7) Uani d . 1
C C1 0.9215(3) 0.3017(2) 0.6335(5) 0.0467(8) Uani d . 1
H H1B 0.9637 0.2532 0.6874 0.070 Uiso calc R 1
H H1C 0.8978 0.3329 0.7159 0.070 Uiso calc R 1
H H1D 0.9690 0.3363 0.5886 0.070 Uiso calc R 1
S S2 0.52374(7) 0.27954(6) 0.09389(12) 0.0481(3) Uani d . 1
O O2 0.1594(2) 0.01484(14) 0.9643(3) 0.0488(6) Uani d . 1
N N2 0.6927(2) 0.18906(16) 0.3141(4) 0.0450(7) Uani d . 1
C C2 0.8194(3) 0.27461(18) 0.4915(4) 0.0372(7) Uani d . 1
S S3 0.10797(6) 0.07761(4) 0.83848(10) 0.0334(2) Uani d . 1
O O3 0.1006(2) 0.16209(13) 0.8943(3) 0.0482(6) Uani d . 1
N N3 0.3686(2) 0.15372(15) 0.2358(3) 0.0376(6) Uani d . 1
C C3 0.6486(3) 0.26122(18) 0.2582(4) 0.0363(7) Uani d . 1
N N4 0.4067(2) 0.01607(16) 0.2870(4) 0.0433(6) Uani d . 1
C C4 0.4766(3) 0.1743(2) 0.0265(4) 0.0487(9) Uani d . 1
H H4B 0.4181 0.1771 -0.0840 0.058 Uiso calc R 1
H H4C 0.5401 0.1430 0.0120 0.058 Uiso calc R 1
C C5 0.4305(3) 0.1279(2) 0.1470(4) 0.0399(7) Uani d . 1
C C6 0.3552(2) 0.08168(17) 0.3201(4) 0.0338(6) Uani d . 1
C C7 0.2925(2) 0.07993(17) 0.4449(4) 0.0340(7) Uani d . 1
C C8 0.2290(3) 0.14939(19) 0.4627(4) 0.0426(8) Uani d . 1
H H8A 0.2247 0.1960 0.3933 0.051 Uiso calc R 1
C C9 0.1727(3) 0.14945(18) 0.5821(4) 0.0394(7) Uani d . 1
H H9A 0.1297 0.1956 0.5938 0.047 Uiso calc R 1
C C10 0.1810(2) 0.07929(17) 0.6852(4) 0.0323(6) Uani d . 1
C C11 0.2437(3) 0.00997(18) 0.6702(4) 0.0374(7) Uani d . 1
H H11A 0.2484 -0.0363 0.7407 0.045 Uiso calc R 1
C C13 -0.0297(3) 0.0440(2) 0.7251(4) 0.0442(8) Uani d . 1
H H13A -0.0750 0.0415 0.8008 0.066 Uiso calc R 1
H H13B -0.0262 -0.0106 0.6782 0.066 Uiso calc R 1
H H13C -0.0636 0.0827 0.6342 0.066 Uiso calc R 1
C C12 0.2993(2) 0.01041(18) 0.5485(4) 0.0376(7) Uani d . 1
H H12A 0.3414 -0.0361 0.5361 0.045 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 S1 C3 86.69(15)
C5 O1 N4 105.6(2)
C2 N1 N2 113.1(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
C3 S2 C4 101.93(16)
C3 N2 N1 111.8(3)
N1 C2 C1 124.5(3)
N1 C2 S1 113.9(3)
C1 C2 S1 121.6(2)
O3 S3 O2 118.73(15)
O3 S3 C13 108.04(16)
O2 S3 C13 107.96(16)
O3 S3 C10 108.20(14)
O2 S3 C10 108.40(13)
C13 S3 C10 104.63(15)
C5 N3 C6 102.0(3)
N2 C3 S2 127.0(3)
N2 C3 S1 114.5(3)
S2 C3 S1 118.54(17)
C6 N4 O1 103.4(2)
C5 C4 S2 114.3(2)
C5 C4 H4B 108.7
S2 C4 H4B 108.7
C5 C4 H4C 108.7
S2 C4 H4C 108.7
H4B C4 H4C 107.6
N3 C5 O1 114.1(3)
N3 C5 C4 130.0(3)
O1 C5 C4 115.9(3)
N4 C6 N3 114.9(3)
N4 C6 C7 122.2(3)
N3 C6 C7 122.8(2)
C12 C7 C8 119.9(3)
C12 C7 C6 120.2(3)
C8 C7 C6 119.8(3)
C9 C8 C7 120.4(3)
C9 C8 H8A 119.8
C7 C8 H8A 119.8
C8 C9 C10 118.7(3)
C8 C9 H9A 120.6
C10 C9 H9A 120.6
C11 C10 C9 121.9(3)
C11 C10 S3 118.6(2)
C9 C10 S3 119.5(2)
C10 C11 C12 118.9(3)
C10 C11 H11A 120.6
C12 C11 H11A 120.6
S3 C13 H13A 109.5
S3 C13 H13B 109.5
H13A C13 H13B 109.5
S3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 C12 C7 120.2(3)
C11 C12 H12A 119.9
C7 C12 H12A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.729(3)
S1 C3 1.736(3)
O1 C5 1.350(4)
O1 N4 1.405(3)
N1 C2 1.295(4)
N1 N2 1.389(4)
C1 C2 1.492(5)
C1 H1B 0.9600
C1 H1C 0.9600
C1 H1D 0.9600
S2 C3 1.730(3)
S2 C4 1.807(4)
O2 S3 1.439(2)
N2 C3 1.295(4)
S3 O3 1.436(2)
S3 C13 1.750(3)
S3 C10 1.768(3)
N3 C5 1.281(4)
N3 C6 1.380(4)
N4 C6 1.298(4)
C4 C5 1.488(4)
C4 H4B 0.9700
C4 H4C 0.9700
C6 C7 1.468(4)
C7 C12 1.386(4)
C7 C8 1.393(4)
C8 C9 1.372(4)
C8 H8A 0.9300
C9 C10 1.389(4)
C9 H9A 0.9300
C10 C11 1.378(4)
C11 C12 1.383(4)
C11 H11A 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C12 H12A 0.9300
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
C2 N1 N2 C3 -0.3(4)
N2 N1 C2 C1 179.7(3)
N2 N1 C2 S1 0.0(3)
C3 S1 C2 N1 0.3(2)
C3 S1 C2 C1 -179.5(3)
N1 N2 C3 S2 -178.4(2)
N1 N2 C3 S1 0.6(3)
C4 S2 C3 N2 -0.4(3)
C4 S2 C3 S1 -179.38(17)
C2 S1 C3 N2 -0.5(2)
C2 S1 C3 S2 178.59(19)
C5 O1 N4 C6 0.3(3)
C3 S2 C4 C5 73.2(3)
C6 N3 C5 O1 -0.6(4)
C6 N3 C5 C4 -179.9(3)
N4 O1 C5 N3 0.2(4)
N4 O1 C5 C4 179.7(3)
S2 C4 C5 N3 38.5(5)
S2 C4 C5 O1 -140.8(3)
O1 N4 C6 N3 -0.6(4)
O1 N4 C6 C7 -177.6(3)
C5 N3 C6 N4 0.8(4)
C5 N3 C6 C7 177.7(3)
N4 C6 C7 C12 8.7(4)
N3 C6 C7 C12 -168.0(3)
N4 C6 C7 C8 -173.3(3)
N3 C6 C7 C8 10.0(4)
C12 C7 C8 C9 -0.1(5)
C6 C7 C8 C9 -178.2(3)
C7 C8 C9 C10 0.4(5)
C8 C9 C10 C11 -0.2(5)
C8 C9 C10 S3 -179.4(3)
O3 S3 C10 C11 150.6(2)
O2 S3 C10 C11 20.6(3)
C13 S3 C10 C11 -94.4(3)
O3 S3 C10 C9 -30.3(3)
O2 S3 C10 C9 -160.3(2)
C13 S3 C10 C9 84.7(3)
C9 C10 C11 C12 -0.2(5)
S3 C10 C11 C12 178.9(2)
C10 C11 C12 C7 0.5(5)
C8 C7 C12 C11 -0.4(5)
C6 C7 C12 C11 177.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21121206
2 PubChem 139073450
