Access to 4-(pyridin-2-yloxy)-1,2,4-thiadiazol-5(4<i>H</i>)-ones <i>via</i> an amidoxime O-heteroarylation/cyclization reaction sequence.
Solodyankina, Olga V.; Baykova, Svetlana O.; Baykov, Sergey V.; Togyzbayeva, Nurila; Zhussupova, Leilya; Novikov, Mikhail S.; Turmanov, Rakhymzhan; Boyarskiy, Vadim P.; Organic & biomolecular chemistry 23 (2025) 10398–10407; doi:10.1039/d5ob01387a

data_7160819
_publ_section_title
;
 Access to 4-(pyridin-2-yloxy)-1,2,4-thiadiazol-5(4<i>H</i>)-ones
 <i>via</i> an amidoxime O-heteroarylation/cyclization reaction sequence.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10398
_journal_page_last               10407
_journal_paper_doi               10.1039/d5ob01387a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C13 H8 Cl N3 O2 S'
_chemical_formula_sum            'C13 H8 Cl N3 O2 S'
_chemical_formula_weight         305.73
_chemical_name_systematic
3-(3-chlorophenyl)-4-(pyridin-2-yloxy)-1,2,4-thiadiazol-5(4H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-07-21 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.245(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.1298(12)
_cell_length_b                   6.4573(2)
_cell_length_c                   8.0989(3)
_cell_measurement_reflns_used    6586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.3360
_cell_measurement_theta_min      3.5690
_cell_volume                     1293.67(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -23.00  24.00   1.00    2.00    --  -47.14  52.00 142.00   47
  2  \w    -95.00 -44.00   1.00    2.00    --  -47.14 -52.00  -2.00   51
  3  \w     17.00  52.00   1.00    2.00    --   47.14 -52.00  -2.00   35
  4  \w     36.00 119.00   1.00    2.00    --   47.14  52.00 142.00   83
  5  \w   -176.00 -93.00   1.00    8.00    -- -106.00 -52.00  -2.00   83
  6  \w    -59.00 -34.00   1.00    8.00    -- -106.00  52.00 142.00   25
  7  \w    115.00 140.00   1.00    8.00    --  113.25  52.00 142.00   25
  8  \w    -40.00  26.00   1.00    2.00    --  -47.14  37.00 -60.00   66
  9  \w    -25.00  23.00   1.00    2.00    --  -47.14  19.00 -60.00   48
 10  \w     60.00  85.00   1.00    2.00    --   47.14  19.00   0.00   25
 11  \w    -26.00  13.00   1.00    2.00    --   47.14 -19.00   0.00   39
 12  \w    -70.00 -34.00   1.00    8.00    -- -106.00  61.00 -90.00   36
 13  \w    -92.00 -41.00   1.00    8.00    -- -106.00  77.00  60.00   51
 14  \w    -71.00 -35.00   1.00    8.00    -- -106.00  77.00-180.00   36
 15  \w   -149.00 -95.00   1.00    8.00    -- -106.00 -45.00 -90.00   54
 16  \w    -63.00 -36.00   1.00    8.00    -- -106.00  61.00 -30.00   27
 17  \w    -69.00 -36.00   1.00    8.00    -- -106.00  61.00-120.00   33
 18  \w    -69.00 -41.00   1.00    8.00    -- -106.00  61.00 120.00   28
 19  \w    -63.00 -37.00   1.00    8.00    -- -106.00  61.00 -60.00   26
 20  \w   -176.00 -92.00   1.00    8.00    -- -106.00 -61.00  90.00   84
 21  \w    -71.00 -46.00   1.00    8.00    -- -106.00  61.00-180.00   25
 22  \w    102.00 163.00   1.00    8.00    --  113.25  30.00-180.00   61
 23  \w     43.00  94.00   1.00    8.00    --  113.25 -77.00-120.00   51
 24  \w     42.00  67.00   1.00    8.00    --  113.25 -61.00  30.00   25
 25  \w     45.00  70.00   1.00    8.00    --  113.25 -61.00 -30.00   25
 26  \w     43.00  68.00   1.00    8.00    --  113.25 -61.00-120.00   25
 27  \w     44.00 107.00   1.00    8.00    --  113.25-125.00-180.00   63
 28  \w    104.00 165.00   1.00    8.00    --  113.25  30.00  90.00   61
 29  \w    111.00 136.00   1.00    8.00    --  113.25  45.00-120.00   25
 30  \w    102.00 162.00   1.00    8.00    --  113.25  77.00-180.00   60
 31  \w     42.00  67.00   1.00    8.00    --  113.25 -61.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0566526000
_diffrn_orient_matrix_UB_12      0.0530830000
_diffrn_orient_matrix_UB_13      -0.0113020000
_diffrn_orient_matrix_UB_21      -0.0098287000
_diffrn_orient_matrix_UB_22      0.1419185000
_diffrn_orient_matrix_UB_23      -0.1634463000
_diffrn_orient_matrix_UB_31      -0.0239157000
_diffrn_orient_matrix_UB_32      -0.1842933000
_diffrn_orient_matrix_UB_33      -0.1291718000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10275
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.402
_diffrn_reflns_theta_min         3.574
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2716
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0513
_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/[\s^2^(Fo^2^)+(0.0692P)^2^+1.9717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2537
_reflns_number_total             2716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01387a3.cif
_cod_data_source_block           105-003_end-088
_cod_depositor_comments
'Adding full bibliography for 7160818--7160821.cif.'
_cod_database_code               7160819
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H10ClN3O
_shelx_estimated_absorpt_t_max   0.634
_shelx_estimated_absorpt_t_min   0.489
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Restrained distances
 C8A-C7A = C6A-C7A
 1.384 with sigma of 0.02
 C6A-C7A
 1.384 with sigma of 0.002
 C7A-C8A
 1.384 with sigma of 0.02
 C5-C6A
 1.384 with sigma of 0.002
 C6-C5
 1.384 with sigma of 0.001
 C3-C8A
 1.384 with sigma of 0.001
 C8-C3
 1.384 with sigma of 0.001
 C6-C7 = C7-C8
 1.384 with sigma of 0.001
 C8A-C7A
 1.384 with sigma of 0.001
2. Others
 Sof(C6)=Sof(H6)=Sof(C8)=Sof(H8)=Sof(C7)=Sof(H7)=1-FVAR(1)
 Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(H6A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C4(H4), C6(H6), C8(H8), C7(H7), C8A(H8A), C7A(H7A),
 C6A(H6A)
;
_shelx_res_checksum              97161
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.508
_oxdiff_exptl_absorpt_empirical_full_min 0.438