#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/35/2233535.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_2233535
loop_
_publ_author_name
'Kang, Sung Kwon'
'Cho, Nam Sook'
'Jang, Siyoung'
_publ_section_title
;
 5-Ethoxy-1,3,4-thiadiazole-2(3H)-thione
;
_journal_coeditor_code           IS5053
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o503
_journal_paper_doi               10.1107/S1600536812002024
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C4 H6 N2 O S2'
_chemical_formula_moiety         'C4 H6 N2 O S2'
_chemical_formula_sum            'C4 H6 N2 O S2'
_chemical_formula_weight         162.23
_chemical_name_systematic
;
5-Ethoxy-1,3,4-thiadiazole-2(3H)-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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                116.55(4)
_cell_angle_beta                 93.70(3)
_cell_angle_gamma                106.10(3)
_cell_formula_units_Z            2
_cell_length_a                   6.0308(12)
_cell_length_b                   8.1171(16)
_cell_length_c                   8.7616(18)
_cell_measurement_reflns_used    3632
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.56
_cell_measurement_theta_min      2.88
_cell_volume                     359.7(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10973
_diffrn_reflns_theta_full        25.4
_diffrn_reflns_theta_max         25.4
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0692P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.106
_reflns_number_gt                1020
_reflns_number_total             1329
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL [C4H6N2OS2] compound in P-1
CELL 0.71073   6.0308   8.1171   8.7616 116.546  93.703 106.103
ZERR    2   0.0012   0.0016   0.0018   0.042   0.030   0.031
LATT  1
SFAC C H N O S
UNIT 8 12 4 2 4
HTAB
EQIV $1  -x, -y+1, -z+1
HTAB N3 S6_$1
ACTA
L.S. 5
BOND $H
FMAP 2
PLAN -5
mpla 6 S1 > S6
mpla 3 O7 > C9
WGHT    0.069200
FVAR       0.38287
MOLE   1
S1    5    0.580722    0.694662    0.868514    11.00000    0.06191    0.04591 =
         0.06793    0.01509   -0.00964    0.02553
C2    1    0.325688    0.637934    0.723306    11.00000    0.04719    0.04991 =
         0.05211    0.02601    0.01008    0.02292
N3    3    0.266029    0.451044    0.603886    11.00000    0.04758    0.04983 =
         0.05601    0.02153   -0.00110    0.02207
H3    2    0.158378    0.407576    0.531226    11.00000    0.05469
N4    3    0.398072    0.340514    0.612954    11.00000    0.05255    0.04447 =
         0.05923    0.02163    0.00252    0.02415
C5    1    0.570396    0.453745    0.748666    11.00000    0.04803    0.04527 =
         0.05931    0.02493    0.00416    0.02227
S6    5    0.188840    0.794688    0.736973    11.00000    0.05972    0.05306 =
         0.06678    0.02475    0.00591    0.03191
O7    4    0.734350    0.400955    0.803082    11.00000    0.05833    0.04581 =
         0.07387    0.02138   -0.01018    0.02406
C8    1    0.708046    0.195485    0.705113    11.00000    0.06203    0.04705 =
         0.06339    0.02429    0.00474    0.02625
AFIX  23
H8A   2    0.721794    0.160670    0.585725    11.00000   -1.20000
H8B   2    0.554352    0.114159    0.702695    11.00000   -1.20000
AFIX   0
C9    1    0.901394    0.165565    0.795570    11.00000    0.08033    0.06727 =
         0.07986    0.03825    0.00908    0.04292
AFIX  33
H9A   2    0.890027    0.030582    0.733814    11.00000   -1.50000
H9B   2    0.885337    0.199887    0.913275    11.00000   -1.50000
H9C   2    1.052380    0.247106    0.797429    11.00000   -1.50000
HKLF 4
REM  [C4H6N2OS2] compound in P-1
REM R1 =  0.0347 for   1020 Fo > 4sig(Fo)  and  0.0464 for all   1329 data
REM     86 parameters refined using      0 restraints
END
WGHT      0.0692      0.0000
REM Highest difference peak  0.336,  deepest hole -0.246,  1-sigma level  0.058
Q1    1   0.0325  0.6918  0.6559  11.00000  0.05    0.34
Q2    1   0.4380  0.6215  0.9133  11.00000  0.05    0.32
Q3    1   0.0296  0.7058  0.7553  11.00000  0.05    0.30
Q4    1   0.3221  0.9026  0.8414  11.00000  0.05    0.27
Q5    1   0.3036  0.8336  0.6467  11.00000  0.05    0.27
;
_cod_data_source_file            is5053.cif
_cod_data_source_block           I
_cod_database_code               2233535
_cod_database_fobs_code          2233535
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
S S1 0.58072(11) 0.69466(8) 0.86851(8) 0.0633(3) Uani d . 1
C C2 0.3257(4) 0.6379(3) 0.7233(3) 0.0478(5) Uani d . 1
N N3 0.2660(4) 0.4510(3) 0.6039(3) 0.0522(5) Uani d . 1
H H3 0.158(4) 0.408(4) 0.531(3) 0.055(8) Uiso d . 1
N N4 0.3981(3) 0.3405(3) 0.6130(3) 0.0523(5) Uani d . 1
C C5 0.5704(4) 0.4537(3) 0.7487(3) 0.0500(6) Uani d . 1
S S6 0.18884(11) 0.79469(9) 0.73697(8) 0.0591(3) Uani d . 1
O O7 0.7344(3) 0.4010(2) 0.8031(2) 0.0623(5) Uani d . 1
C C8 0.7080(5) 0.1955(3) 0.7051(3) 0.0572(6) Uani d . 1
H H8A 0.7218 0.1607 0.5857 0.069 Uiso calc R 1
H H8B 0.5544 0.1142 0.7027 0.069 Uiso calc R 1
C C9 0.9014(5) 0.1656(4) 0.7956(4) 0.0711(7) Uani d . 1
H H9A 0.89 0.0306 0.7338 0.107 Uiso calc R 1
H H9B 0.8853 0.1999 0.9133 0.107 Uiso calc R 1
H H9C 1.0524 0.2471 0.7974 0.107 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0619(4) 0.0459(4) 0.0679(4) 0.0255(3) -0.0096(3) 0.0151(3)
C2 0.0472(12) 0.0499(13) 0.0521(12) 0.0229(10) 0.0101(10) 0.0260(10)
N3 0.0476(11) 0.0498(11) 0.0560(12) 0.0221(9) -0.0011(10) 0.0215(9)
N4 0.0525(11) 0.0445(10) 0.0592(11) 0.0241(9) 0.0025(9) 0.0216(9)
C5 0.0480(13) 0.0453(12) 0.0593(14) 0.0223(10) 0.0042(11) 0.0249(11)
S6 0.0597(4) 0.0531(4) 0.0668(4) 0.0319(3) 0.0059(3) 0.0248(3)
O7 0.0583(10) 0.0458(9) 0.0739(11) 0.0241(8) -0.0102(8) 0.0214(8)
C8 0.0620(15) 0.0471(13) 0.0634(14) 0.0263(11) 0.0047(11) 0.0243(11)
C9 0.0803(19) 0.0673(17) 0.0799(18) 0.0429(14) 0.0091(14) 0.0382(14)
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 0 '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 0.006 '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
C5 S1 C2 89.00(11)
N3 C2 S6 127.91(18)
N3 C2 S1 107.12(17)
S6 C2 S1 124.97(15)
C2 N3 N4 120.52(19)
C2 N3 H3 118(2)
N4 N3 H3 121(2)
C5 N4 N3 107.33(18)
N4 C5 O7 125.7(2)
N4 C5 S1 116.01(17)
O7 C5 S1 118.33(16)
C5 O7 C8 115.95(17)
O7 C8 C9 107.07(19)
O7 C8 H8A 110.3
C9 C8 H8A 110.3
O7 C8 H8B 110.3
C9 C8 H8B 110.3
H8A C8 H8B 108.6
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.738(2)
S1 C2 1.740(2)
C2 N3 1.325(3)
C2 S6 1.665(2)
N3 N4 1.377(3)
N3 H3 0.76(2)
N4 C5 1.293(3)
C5 O7 1.321(2)
O7 C8 1.449(3)
C8 C9 1.502(3)
C8 H8A 0.97
C8 H8B 0.97
C9 H9A 0.96
C9 H9B 0.96
C9 H9C 0.96
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 S6 2_566 0.76(2) 2.57(2) 3.317(3) 170(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14539688
2 PubChem 14996766
