Investigation of the photochemical behavior of allomaltol-containing 2-aminothiazole derivatives.
Migulin, Alexander V.; Milyutin, Constantine V.; Lichitsky, Boris V.; Korobkov, Stepan M.; Komogortsev, Andrey N.; Organic & biomolecular chemistry 23 (2025) 4172–4185; doi:10.1039/d5ob00264h

data_7160481
_publ_section_title
;
 Investigation of the photochemical behavior of allomaltol-containing
 2-aminothiazole derivatives.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4172
_journal_page_last               4185
_journal_paper_doi               10.1039/d5ob00264h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C22 H18 Cl N4 O S, I, 2(H2 O)'
_chemical_formula_sum            'C22 H22 Cl I N4 O3 S'
_chemical_formula_weight         584.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-29 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                97.8836(4)
_cell_angle_beta                 99.1687(5)
_cell_angle_gamma                97.7247(5)
_cell_formula_units_Z            2
_cell_length_a                   8.18997(5)
_cell_length_b                   8.95782(5)
_cell_length_c                   17.13924(9)
_cell_measurement_reflns_used    22999
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.6090
_cell_measurement_theta_min      5.0260
_cell_volume                     1213.809(12)
_computing_cell_refinement       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -26.00  41.00   0.50    0.32    --  -41.40  19.00 -43.00  134
  2  \w    -21.00 123.00   0.50    0.32    --   41.40  19.00 -43.00  288
  3  \w    -21.00 123.00   0.50    0.32    --   41.40  19.00 -43.00  288
  4  \w    -43.00  27.00   0.50    0.32    --   41.40 -19.00 148.00  140
  5  \w   -177.00 -40.00   0.50    0.32    -- -100.00 -19.00 148.00  274
  6  \w   -177.00 -40.00   0.50    0.32    -- -100.00 -19.00 148.00  274
  7  \w     59.00 178.00   0.50    0.32    --  121.50  19.00 -43.00  238
  8  \w     -1.00  44.00   0.50    0.80    --    0.00 -99.00  90.00   90
  9  \w    -26.00  83.00   0.50    0.80    --    0.00  19.00 -43.00  218
 10  \w   -126.00  19.00   0.50    0.32    --  -41.40 -19.00 148.00  290
 11  \w    -43.00  27.00   0.50    0.32    --   41.40 -19.00   0.00  140
 12  \w     34.00  99.00   0.50    0.32    --   41.40-125.00-150.00  130
 13  \w     -1.00  86.00   0.50    0.32    --   41.40 -99.00  30.00  174
 14  \w     -1.00  86.00   0.50    0.32    --   41.40 -99.00 150.00  174
 15  \w     -1.00  86.00   0.50    0.32    --   41.40 -99.00  30.00  174
 16  \w     34.00  99.00   0.50    0.32    --   41.40-125.00  30.00  130
 17  \w     -1.00  28.00   0.50    0.32    --   41.40  97.00 -38.04   58
 18  \w    -71.00 -24.00   0.50    0.32    -- -100.00  61.00-180.00   94
 19  \w    -82.00 -23.00   0.50    0.32    -- -100.00 111.00  30.00  118
 20  \w    -51.00 -21.00   0.50    0.32    -- -100.00  45.00 150.00   60
 21  \w    -51.00 -21.00   0.50    0.32    -- -100.00  45.00 120.00   60
 22  \w   -105.00 -24.00   0.50    0.32    -- -100.00  77.00 -30.00  162
 23  \w   -105.00 -24.00   0.50    0.32    -- -100.00  77.00 -30.00  162
 24  \w     61.00 151.00   0.50    0.32    --  121.50-178.00  60.00  180
 25  \w     61.00 151.00   0.50    0.32    --  121.50-178.00  60.00  180
 26  \w     45.00 108.00   0.50    0.32    --  121.50-111.00 120.00  126
 27  \w     45.00 108.00   0.50    0.32    --  121.50-111.00  60.00  126
 28  \w     92.00 178.00   0.50    0.32    --  121.50  45.00 120.00  172
 29  \w     41.00 106.00   0.50    0.32    --  121.50 -95.00   0.00  130
 30  \w     45.00 108.00   0.50    0.32    --  121.50-111.00-120.00  126
 31  \w     92.00 178.00   0.50    0.32    --  121.50  61.00 120.00  172
 32  \w     61.00 151.00   0.50    0.32    --  121.50-178.00  90.00  180
 33  \w     45.00 108.00   0.50    0.32    --  121.50-111.00-150.00  126
 34  \w     92.00 178.00   0.50    0.32    --  121.50  61.00-120.00  172
 35  \w     41.00 106.00   0.50    0.32    --  121.50 -95.00  90.00  130
 36  \w     41.00 106.00   0.50    0.32    --  121.50 -95.00 -30.00  130
 37  \w    103.00 178.00   0.50    0.32    --  121.50 111.00   0.00  150
 38  \w     87.00 178.00   0.50    0.32    --  121.50  77.00-180.00  182
 39  \w     92.00 178.00   0.50    0.32    --  121.50  61.00-150.00  172
 40  \w     92.00 178.00   0.50    0.32    --  121.50  61.00-150.00  172
 41  \w     45.00 108.00   0.50    0.32    --  121.50-111.00-180.00  126
 42  \w     92.00 178.00   0.50    0.32    --  121.50  45.00-180.00  172
 43  \w     63.00 146.00   0.50    0.32    --  121.50 178.00  30.00  166
 44  \w     92.00 178.00   0.50    0.32    --  121.50  45.00  30.00  172
 45  \w     45.00 108.00   0.50    0.32    --  121.50-111.00   0.00  126
 46  \w     45.00 108.00   0.50    0.32    --  121.50-111.00 -60.00  126
 47  \w     47.00 105.00   0.50    0.32    --  121.50 -77.00  90.00  116
 48  \w     45.00 108.00   0.50    0.32    --  121.50-111.00  90.00  126
 49  \w     45.00 108.00   0.50    0.32    --  121.50-111.00  90.00  126
 50  \w     47.00 105.00   0.50    0.32    --  121.50 -77.00  30.00  116
 51  \w     42.00 178.00   0.50    0.32    --  121.50  15.00  60.00  272
 52  \w     41.00 106.00   0.50    0.32    --  121.50 -95.00 -60.00  130
 53  \w     92.00 178.00   0.50    0.32    --  121.50  45.00 120.00  172
 54  \w     84.00 178.00   0.50    0.32    --  121.50  30.00-180.00  188
 55  \w     42.00 178.00   0.50    0.32    --  121.50  15.00  60.00  272
 56  \w     47.00 105.00   0.50    0.32    --  121.50 -77.00 -60.00  116
 57  \w     47.00 105.00   0.50    0.32    --  121.50 -77.00   0.00  116
 58  \w     45.00 158.00   0.50    0.32    --  121.50 -81.00 153.57  226
 59  \w     87.00 178.00   0.50    0.32    --  121.50  77.00-120.00  182
 60  \w     51.00  98.00   0.50    0.32    --  121.50 -79.00-174.39   94
 61  \w    129.00 154.00   0.50    0.32    --  121.50 -79.00-174.39   50
 62  \w     76.00 107.00   0.50    0.32    --  121.50-111.00  30.00   62
 63  \w     80.00 106.00   0.50    0.32    --  121.50 -95.00-150.00   52
 64  \w     71.00  97.00   0.50    0.32    --  121.50 -95.00  60.00   52
 65  \w     52.00 103.00   0.50    0.32    --  121.50 -95.00 150.00  102
 66  \w    103.00 137.00   0.50    0.32    --  121.50 111.00-120.00   68
 67  \w    141.00 167.00   0.50    0.32    --  121.50 111.00 -90.00   52
 68  \w     42.00  76.00   0.50    0.32    --  121.50 -95.00  30.00   68
 69  \w    151.00 177.00   0.50    0.32    --  121.50  61.00  90.00   52
 70  \w    128.00 157.00   0.50    0.32    --  121.50 -79.00 132.03   58
 71  \w     49.00  75.00   0.50    0.32    --  121.50 -79.00 132.03   52
 72  \w     96.00 149.00   0.50    0.32    --  121.50-178.00   0.00  106
 73  \w     88.00 166.00   0.50    0.32    --  121.50  30.00   0.00  156
 74  \w     92.00 144.00   0.50    0.32    --  121.50  45.00-120.00  104
 75  \w    132.00 158.00   0.50    0.32    --  121.50 -81.00 153.57   52
 76  \w    119.00 145.00   0.50    0.32    --  121.50 -81.00 107.62   52
 77  \w    130.00 160.00   0.50    0.32    --  121.50 -85.00 -78.72   60
 78  \w    120.00 178.00   0.50    0.32    --  121.50  45.00  90.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1606401000
_diffrn_orient_matrix_UB_12      -0.0957605000
_diffrn_orient_matrix_UB_13      0.0137594000
_diffrn_orient_matrix_UB_21      0.0990875000
_diffrn_orient_matrix_UB_22      -0.1293924000
_diffrn_orient_matrix_UB_23      0.0184238000
_diffrn_orient_matrix_UB_31      0.0404039000
_diffrn_orient_matrix_UB_32      0.0708631000
_diffrn_orient_matrix_UB_33      0.0893575000
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32044
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.264
_diffrn_reflns_theta_min         2.646
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.047
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.00058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5288
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0242
_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^)+(0.0321P)^2^+1.5310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5247
_reflns_number_total             5288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00264h2.cif
_cod_data_source_block           am-161
_cod_depositor_comments
'Adding full bibliography for 7160480--7160482.cif.'
_cod_database_code               7160481
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C22H18ClN4OSI
_chemical_oxdiff_usercomment     AM-161
_shelx_estimated_absorpt_t_max   0.780
_shelx_estimated_absorpt_t_min   0.592
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H4B-N4
 0.87 with sigma of 0.02
 H4A-N4
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C21(H21),
 C22(H22)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              89982
_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 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.802