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_7160818
_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         'C12 H10 Cl N3 O'
_chemical_formula_sum            'C12 H10 Cl N3 O'
_chemical_formula_weight         247.68
_chemical_name_systematic        2-chloro-N'-(pyridin-2-yloxy)benzimidamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_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                 113.892(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6695(2)
_cell_length_b                   9.7859(2)
_cell_length_c                   11.9081(3)
_cell_measurement_reflns_used    4692
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7750
_cell_measurement_theta_min      4.5250
_cell_volume                     1136.79(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_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            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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    -24.00  32.00   0.50    0.70    --   41.10 -88.00 -94.00  112
  2  \w     42.00  67.00   0.50    0.70    --   41.10 -88.00 -94.00   50
  3  \w     38.00  63.00   0.50    2.30    --  100.00 -88.00 -94.00   50
  4  \w     89.00 127.00   0.50    2.30    --  100.00 -88.00 -94.00   76
  5  \w    -48.00   2.00   0.50    0.70    --  -41.10  54.00 -30.00  100
  6  \w   -105.00 -72.00   0.50    0.70    --  -41.10 -32.00 -30.00   66
  7  \w    -16.00  17.00   0.50    0.70    --  -41.10  88.00  22.00   66
  8  \w    -50.00  21.00   0.50    0.70    --  -41.10  32.00 150.00  142
  9  \w    -65.00 -34.00   0.50    0.70    --  -41.10 -32.00 -30.00   62
 10  \w    -50.00 -25.00   0.50    0.70    --  -41.10  88.00  22.00   50
 11  \w    -11.00  37.00   0.50    0.70    --   41.10 -54.00 -30.00   96
 12  \w     60.00  99.00   0.50    0.70    --   41.10  54.00  90.00   78
 13  \w     71.00 103.00   0.50    0.70    --   41.10  43.00 -30.00   64
 14  \w     31.00  68.00   0.50    0.70    --   41.10  43.00 -30.00   74
 15  \w     68.00  97.00   0.50    0.70    --   41.10  32.00-120.00   58
 16  \w     33.00  58.00   0.50    0.70    --   41.10  32.00-180.00   50
 17  \w     87.00 157.00   0.50    2.30    --  100.00  42.00  60.00  140
 18  \w     34.00  59.00   0.50    2.30    --  100.00 -87.00  30.00   50
 19  \w    102.00 128.00   0.50    2.30    --  100.00  93.00  60.00   52
 20  \w     50.00  76.00   0.50    2.30    --  100.00 -59.00 -90.00   52
 21  \w     95.00 121.00   0.50    2.30    --  100.00 -68.00-180.00   52
 22  \w     56.00  90.00   0.50    2.30    --  100.00 -68.00-180.00   68
 23  \w     52.00  94.00   0.50    2.30    --  100.00-133.00 120.00   84
 24  \w     90.00 118.00   0.50    2.30    --  100.00 -59.00 -60.00   56
 25  \w     48.00  82.00   0.50    2.30    --  100.00 -59.00 -60.00   68
 26  \w     82.00 148.00   0.50    2.30    --  100.00  59.00-180.00  132
 27  \w     98.00 152.00   0.50    2.30    --  100.00  25.00 -60.00  108
 28  \w    101.00 148.00   0.50    2.30    --  100.00  42.00 120.00   94
 29  \w     44.00  69.00   0.50    2.30    --  100.00 -77.00   0.00   50
 30  \w     83.00 109.00   0.50    2.30    --  100.00  59.00  90.00   52
 31  \w     87.00 155.00   0.50    2.30    --  100.00  68.00 150.00  136
 32  \w     87.00 125.00   0.50    2.30    --  100.00 -87.00  30.00   76
 33  \w    100.00 125.00   0.50    2.30    --  100.00  42.00 -60.00   50
 34  \w     66.00 103.00   0.50    2.30    --  100.00-111.00 -60.00   74
 35  \w     80.00 155.00   0.50    2.30    --  100.00  68.00 -60.00  150
 36  \w     84.00 139.00   0.50    2.30    --  100.00  59.00 -30.00  110
 37  \w    122.00 155.00   0.50    2.30    --  100.00  88.00  22.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1064503000
_diffrn_orient_matrix_UB_12      0.1145222000
_diffrn_orient_matrix_UB_13      0.0553404000
_diffrn_orient_matrix_UB_21      0.0684105000
_diffrn_orient_matrix_UB_22      -0.0836221000
_diffrn_orient_matrix_UB_23      0.1190282000
_diffrn_orient_matrix_UB_31      0.0944984000
_diffrn_orient_matrix_UB_32      -0.0684464000
_diffrn_orient_matrix_UB_33      -0.0527430000
_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  0.0279
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.635
_diffrn_reflns_theta_min         4.533
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
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    1.447
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.6312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1997
_reflns_number_total             2212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01387a3.cif
_cod_data_source_block           cob-58
_cod_depositor_comments
'Adding full bibliography for 7160818--7160821.cif.'
_cod_database_code               7160818
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H10 Cl N3 O'
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.782
_reflns_odcompleteness_completeness 94.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C7(H7), C4(H4), C10(H10), C6(H6), C11(H11), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_shelx_res_checksum              49830
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.643