#------------------------------------------------------------------------------
#$Date: 2022-09-20 11:32:02 +0300 (Tue, 20 Sep 2022) $
#$Revision: 277994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/29/1552921.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_1552921
loop_
_publ_author_name
'Razzoqova, Surayyo Razzoqovna'
'Kadirova, Shaxnoza'
'Ashurov, Jamshid Mengnorovich'
'Rakhmonova, Dilnoza Salamovna'
'Ziyaev, Abdukhakim'
'Parpiev, Nusrat Agzamovich'
_publ_section_title
;
 5-(3-Hydroxyphenyl)-1,3,4-oxadiazole-2(3H)-thione hemihydrate
;
_journal_coeditor_code           WM4116
_journal_issue                   11
_journal_name_full               IUCrData
_journal_page_first              x191532
_journal_paper_doi               10.1107/S2414314619015323
_journal_volume                  4
_journal_year                    2019
_chemical_formula_iupac          'C8 H6 N2 O2 S, 0.5(H2 O)'
_chemical_formula_moiety         'C8 H6 N2 O2 S, 0.5(H2 O)'
_chemical_formula_sum            'C8 H7 N2 O2.5 S'
_chemical_formula_weight         203.21
_chemical_name_systematic
;
5-(3-Hydroxyphenyl)-1,3,4-oxadiazole-2(3H)-thione hemihydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 97.512(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3881(12)
_cell_length_b                   4.6912(3)
_cell_length_c                   22.4928(18)
_cell_measurement_reflns_used    1053
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1790
_cell_measurement_theta_min      5.4340
_cell_volume                     1714.4(2)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.2576
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku Xcalibur Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5850
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.063
_diffrn_reflns_theta_min         3.965
_exptl_absorpt_coefficient_mu    3.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0512P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                1256
_reflns_number_total             1767
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm4116sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2022-09-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C16 H14 N4 O5 S2'
_cod_original_formula_weight         406.43
_cod_original_formula_moiety         '2(C8 H6 N2 O2 S), H2 O'
_cod_original_formula_iupac          '2C8 H6 N2 O2 S, H2 O'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               1552921
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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_occupancy
S S1 0.67502(4) 1.34393(15) 0.35767(3) 0.0449(2) Uani d 1
O O1 0.55444(11) 0.9588(4) 0.35221(8) 0.0373(4) Uani d 1
O O2 0.32072(15) 0.0756(5) 0.42672(10) 0.0555(6) Uani d 1
H H2 0.290571 -0.045956 0.409275 0.083 Uiso calc 1
O O1W 0.750000 1.3852(8) 0.500000 0.0597(9) Uani d 1
N N1 0.60967(15) 1.0310(5) 0.44201(11) 0.0447(6) Uani d 1
H H1 0.640309 1.100099 0.472576 0.054 Uiso calc 1
N N0AA 0.55104(15) 0.8229(5) 0.44618(11) 0.0452(6) Uani d 1
C C2 0.51961(16) 0.7884(6) 0.39152(11) 0.0361(6) Uani d 1
C C3 0.45590(16) 0.5862(5) 0.36792(12) 0.0365(6) Uani d 1
C C8 0.41731(17) 0.4239(6) 0.40779(13) 0.0392(6) Uani d 1
H H8 0.431399 0.446199 0.448938 0.047 Uiso calc 1
C C1 0.61390(16) 1.1129(6) 0.38633(12) 0.0380(6) Uani d 1
C C7 0.35775(17) 0.2289(6) 0.38559(13) 0.0401(6) Uani d 1
C C4 0.43517(18) 0.5516(6) 0.30612(13) 0.0435(7) Uani d 1
H H4 0.461017 0.659969 0.279433 0.052 Uiso calc 1
C C6 0.33699(18) 0.1922(6) 0.32463(13) 0.0447(7) Uani d 1
H H6 0.297161 0.059244 0.310210 0.054 Uiso calc 1
C C5 0.37544(19) 0.3532(7) 0.28508(13) 0.0480(7) Uani d 1
H H5 0.361217 0.328550 0.244007 0.058 Uiso calc 1
H H1W 0.742(3) 1.497(8) 0.4702(18) 0.086(14) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_3
_geom_angle
C1 O1 C2 . 105.8(2)
C7 O2 H2 . 109.5
H1W O1W H1W 2_656 104(6)
C1 N1 N0AA . 113.2(2)
C1 N1 H1 . 123.4
N0AA N1 H1 . 123.4
C2 N0AA N1 . 102.7(2)
N0AA C2 O1 . 113.4(2)
N0AA C2 C3 . 127.7(2)
O1 C2 C3 . 118.9(2)
C8 C3 C4 . 120.4(3)
C8 C3 C2 . 119.1(2)
C4 C3 C2 . 120.5(2)
C7 C8 C3 . 119.2(3)
C7 C8 H8 . 120.4
C3 C8 H8 . 120.4
N1 C1 O1 . 104.9(2)
N1 C1 S1 . 131.8(2)
O1 C1 S1 . 123.3(2)
O2 C7 C6 . 122.0(3)
O2 C7 C8 . 117.1(3)
C6 C7 C8 . 120.8(3)
C5 C4 C3 . 119.1(3)
C5 C4 H4 . 120.5
C3 C4 H4 . 120.5
C7 C6 C5 . 119.9(3)
C7 C6 H6 . 120.1
C5 C6 H6 . 120.1
C6 C5 C4 . 120.5(3)
C6 C5 H5 . 119.7
C4 C5 H5 . 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C1 . 1.662(3)
O1 C1 . 1.366(3)
O1 C2 . 1.371(3)
O2 C7 . 1.374(3)
O2 H2 . 0.8200
O1W H1W . 0.85(4)
O1W H1W 2_656 0.85(4)
N1 C1 . 1.321(4)
N1 N0AA . 1.381(3)
N1 H1 . 0.8600
N0AA C2 . 1.280(4)
C2 C3 . 1.458(4)
C3 C8 . 1.390(4)
C3 C4 . 1.396(4)
C8 C7 . 1.382(4)
C8 H8 . 0.9300
C7 C6 . 1.380(4)
C4 C5 . 1.388(4)
C4 H4 . 0.9300
C6 C5 . 1.380(4)
C6 H6 . 0.9300
C5 H5 . 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
N1 H1 O1W . 0.86 2.26 2.995(3) 143.3 yes
N1 H1 O2 5_666 0.86 2.42 3.064(3) 132.5 yes
O1W H1W S1 . 0.85(4) 2.72(4) 3.2814(9) 125(3) yes
O2 H2 S1 6_565 0.82 2.51 3.319(2) 168.1 yes

_cod_database_fobs_code 1552921
