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_7160820
_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         'C17 H14 N4 O'
_chemical_formula_sum            'C17 H14 N4 O'
_chemical_formula_weight         290.32
_chemical_name_systematic        N'-([2,2'-bipyridin]-6-yloxy)benzimidamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                 93.6270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.1399(3)
_cell_length_b                   6.21410(10)
_cell_length_c                   21.7378(3)
_cell_measurement_reflns_used    6886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6700
_cell_measurement_theta_min      2.0460
_cell_volume                     2849.88(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  43.00   0.50    0.20    --   41.10 -86.00  97.00  134
  2  \w    103.00 128.00   0.50    0.80    --  100.00 -86.00  97.00   50
  3  \w     87.00 157.00   0.50    0.80    --  100.00  86.00-145.00  140
  4  \w     37.00  73.00   0.50    0.80    --  100.00 -86.00  97.00   72
  5  \w    -68.00 -36.00   0.50    0.20    --  -41.10  86.00-145.00   64
  6  \w    -11.00  14.00   0.50    0.20    --  -41.10  86.00-145.00   50
  7  \w    -92.00 -22.00   0.50    0.20    --  -41.10 -65.00  90.00  140
  8  \w    -14.00  22.00   0.50    0.20    --  -41.10  54.00 -60.00   72
  9  \w    -54.00 -18.00   0.50    0.20    --  -41.10  54.00 -60.00   72
 10  \w    -11.00  25.00   0.50    0.20    --  -41.10  32.00   0.00   72
 11  \w    -48.00 -16.00   0.50    0.20    --  -41.10  32.00   0.00   64
 12  \w     33.00 107.00   0.50    0.20    --   41.10  32.00-120.00  148
 13  \w     18.00  46.00   0.50    0.20    --   41.10 -65.00 150.00   56
 14  \w    -21.00   4.00   0.50    0.20    --   41.10 -65.00 150.00   50
 15  \w     37.00  62.00   0.50    0.20    --   41.10  11.00 -30.00   50
 16  \w     22.00  48.00   0.50    0.20    --   41.10 -21.00  90.00   52
 17  \w    -11.00  31.00   0.50    0.20    --   41.10 -43.00  90.00   84
 18  \w     68.00  93.00   0.50    0.20    --   41.10  11.00 -30.00   50
 19  \w    -17.00   8.00   0.50    0.20    --   41.10 -21.00  90.00   50
 20  \w     87.00 130.00   0.50    0.80    --  100.00  93.00 150.00   86
 21  \w     87.00 136.00   0.50    0.80    --  100.00   8.00   0.00   98
 22  \w     37.00  83.00   0.50    0.80    --  100.00 -59.00 -60.00   92
 23  \w     31.00  69.00   0.50    0.80    --  100.00 -93.00-180.00   76
 24  \w    104.00 155.00   0.50    0.80    --  100.00 111.00 150.00  102
 25  \w     82.00 108.00   0.50    0.80    --  100.00 -42.00  60.00   52
 26  \w     84.00 143.00   0.50    0.80    --  100.00  50.00 150.00  118
 27  \w    132.00 157.00   0.50    0.80    --  100.00  68.00-150.00   50
 28  \w    108.00 157.00   0.50    0.80    --  100.00  77.00-120.00   98
 29  \w     80.00 107.00   0.50    0.80    --  100.00  68.00-150.00   54
 30  \w     38.00 103.00   0.50    0.80    --  100.00-133.00 -90.00  130
 31  \w    126.00 152.00   0.50    0.80    --  100.00  77.00   0.00   52
 32  \w     38.00  67.00   0.50    0.80    --  100.00 -42.00  60.00   58
 33  \w     74.00 108.00   0.50    0.80    --  100.00 -54.00  49.58   68
 34  \w     29.00 113.00   0.50    0.80    --  100.00 -17.00-120.00  168
 35  \w     76.00 102.00   0.50    0.80    --  100.00-111.00-180.00   52
 36  \w    112.00 137.00   0.50    0.80    --  100.00  33.00 120.00   50
 37  \w     39.00  97.00   0.50    0.80    --  100.00-133.00-180.00  116
 38  \w    101.00 126.00   0.50    0.80    --  100.00  33.00-120.00   50
 39  \w     83.00 157.00   0.50    0.80    --  100.00  77.00-180.00  148
;
_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      0.0319247000
_diffrn_orient_matrix_UB_12      -0.2021459000
_diffrn_orient_matrix_UB_13      -0.0249247000
_diffrn_orient_matrix_UB_21      0.0654970000
_diffrn_orient_matrix_UB_22      0.0901155000
_diffrn_orient_matrix_UB_23      0.0219437000
_diffrn_orient_matrix_UB_31      -0.0050075000
_diffrn_orient_matrix_UB_32      -0.1115715000
_diffrn_orient_matrix_UB_33      0.0627689000
_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  0.0396
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8402
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.816
_diffrn_reflns_theta_min         4.076
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73726
_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    1.353
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0659P)^2^+1.8283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2602
_reflns_number_total             2791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01387a3.cif
_cod_data_source_block           syn-549
_cod_depositor_comments
'Adding full bibliography for 7160818--7160821.cif.'
_cod_database_code               7160820
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H14 N4 O'
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.859
_reflns_odcompleteness_completeness 94.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C10(H10), C4(H4), C11(H11), C9(H9), C17(H17), C15(H15),
 C16(H16), C6(H6), C14(H14), C5(H5)
;
_shelx_res_checksum              12583
_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 1.931
_oxdiff_exptl_absorpt_empirical_full_min 0.626