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_7160482
_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 H20 Cl N3 O4 S'
_chemical_formula_sum            'C22 H20 Cl N3 O4 S'
_chemical_formula_weight         457.92
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2024-11-29 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2370(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.1807(2)
_cell_length_b                   10.98210(10)
_cell_length_c                   13.83250(10)
_cell_measurement_reflns_used    42503
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.9920
_cell_measurement_theta_min      2.6620
_cell_volume                     5036.64(7)
_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 1.5 (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 0.998
_diffrn_measured_fraction_theta_max 0.994
_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    -32.00  80.00   0.40    0.30    --    0.00  48.00 173.00  280
  2  \w    -32.00  80.00   0.40    0.30    --    0.00  48.00 173.00  280
  3  \w    -54.00  18.00   0.40    3.00    --  -61.62  48.00 173.00  180
  4  \w     30.00 140.00   0.40    3.00    --   61.62  48.00 173.00  275
  5  \w    -18.00  54.00   0.40    3.00    --   61.62 -48.00  24.00  180
  6  \w    -54.00 -22.00   0.40    6.00    -- -101.75  48.00 173.00   80
  7  \w   -177.00 -71.00   0.40    6.00    -- -101.75 -48.00  24.00  265
  8  \w     91.00 177.00   0.40    6.00    --  123.25  48.00 173.00  215
  9  \w     91.00 177.00   0.40    6.00    --  123.25  48.00 173.00  215
 10  \w     -1.00  45.00   0.40    0.30    --    0.00 -99.00  30.00  115
 11  \w    -79.00  31.00   0.40    0.30    --    0.00 -48.00  24.00  275
 12  \w   -143.00 -87.00   0.40    3.00    --  -61.62 -99.00 150.00  140
 13  \w   -141.00 -31.00   0.40    3.00    --  -61.62 -48.00  24.00  275
 14  \w   -143.00 -87.00   0.40    3.00    --  -61.62 -99.00-180.00  140
 15  \w     33.00 137.00   0.40    3.00    --   61.62  57.00 -60.00  260
 16  \w     25.00 137.00   0.40    3.00    --   61.62  77.00-120.00  280
 17  \w     33.00 137.00   0.40    3.00    --   61.62  57.00-120.00  260
 18  \w     25.00 137.00   0.40    3.00    --   61.62  77.00-120.00  280
 19  \w   -177.00 -69.00   0.40    6.00    -- -101.75 -71.00-108.10  270
 20  \w   -177.00 -65.00   0.40    6.00    -- -101.75 -77.00 -60.00  280
 21  \w   -177.00 -71.00   0.40    6.00    -- -101.75 -51.00 -58.65  265
 22  \w   -177.00 -65.00   0.40    6.00    -- -101.75 -77.00 -90.00  280
 23  \w   -177.00 -67.00   0.40    6.00    -- -101.75 -73.00 -73.65  275
 24  \w   -177.00 -71.00   0.40    6.00    -- -101.75 -60.00-139.17  265
 25  \w   -177.00 -69.00   0.40    6.00    -- -101.75 -71.00-108.10  270
 26  \w    -71.00 -27.00   0.40    6.00    -- -101.75  61.00 -60.00  110
 27  \w    -51.00 -21.00   0.40    6.00    -- -101.75  45.00   0.00   75
 28  \w    -51.00 -21.00   0.40    6.00    -- -101.75  45.00 -60.00   75
 29  \w   -177.00 -65.00   0.40    6.00    -- -101.75 -77.00 -90.00  280
 30  \w    -51.00 -21.00   0.40    6.00    -- -101.75  45.00 150.00   75
 31  \w   -177.00 -69.00   0.40    6.00    -- -101.75 -68.00 -96.56  270
 32  \w   -177.00 -71.00   0.40    6.00    -- -101.75 -51.00 -58.65  265
 33  \w     91.00 177.00   0.40    6.00    --  123.25  45.00 -60.00  215
 34  \w     87.00 177.00   0.40    6.00    --  123.25  77.00 -30.00  225
 35  \w     91.00 177.00   0.40    6.00    --  123.25  45.00 -60.00  215
 36  \w     79.00 177.00   0.40    6.00    --  123.25  30.00-120.00  245
 37  \w     63.00 145.00   0.40    6.00    --  123.25 178.00  90.00  205
 38  \w     87.00 177.00   0.40    6.00    --  123.25  77.00 -90.00  225
 39  \w     87.00 177.00   0.40    6.00    --  123.25  77.00 -90.00  225
 40  \w    151.00 176.20   0.40    6.00    --  123.25 111.00  60.00   63
 41  \w    152.80 178.00   0.40    6.00    --  123.25   0.00  30.00   63
 42  \w    111.00 147.00   0.40    6.00    --  123.25 111.00  60.00   90
 43  \w     36.00  70.00   0.40    6.00    --  123.25   0.00  30.00   85
 44  \w     94.00 146.00   0.40    6.00    --  123.25  61.00 -30.00  130
 45  \w    135.00 163.00   0.40    6.00    --  123.25  77.00  60.00   70
 46  \w     99.00 174.20   0.40    6.00    --  123.25  61.00-120.00  188
 47  \w     73.00  99.00   0.40    6.00    --  123.25 -77.00 -30.00   65
 48  \w     41.00  92.20   0.40    6.00    --  123.25 -95.00 120.00  128
 49  \w    108.00 133.20   0.40    6.00    --  123.25  45.00 -30.00   63
 50  \w     62.00 111.20   0.40    6.00    --  123.25-178.00 -90.00  123
 51  \w    124.00 161.20   0.40    6.00    --  123.25 -81.00  98.31   93
 52  \w    117.00 161.00   0.40    6.00    --  123.25 -80.00 -24.05  110
 53  \w     96.00 173.20   0.40    6.00    --  123.25  61.00 -90.00  193
 54  \w    105.00 131.00   0.40    6.00    --  123.25  30.00 -60.00   65
 55  \w     87.00 113.00   0.40    6.00    --  123.25  77.00  60.00   65
 56  \w    106.00 151.20   0.40    6.00    --  123.25  45.00-120.00  113
 57  \w     93.00 126.20   0.40    6.00    --  123.25  61.00  60.00   83
 58  \w    137.00 165.00   0.40    6.00    --  123.25  45.00  30.00   70
 59  \w     89.00 116.20   0.40    6.00    --  123.25   0.00  30.00   68
 60  \w    105.00 131.00   0.40    6.00    --  123.25  45.00  30.00   65
 61  \w     71.00 101.00   0.40    6.00    --  123.25 178.00   0.00   75
 62  \w    102.00 136.00   0.40    6.00    --  123.25  61.00  30.00   85
 63  \w    100.00 126.00   0.40    6.00    --  123.25 178.00 -60.00   65
 64  \w     45.00  92.20   0.40    6.00    --  123.25 -80.00  84.53  118
 65  \w    107.00 153.00   0.40    6.00    --  123.25 -80.00  84.53  115
 66  \w     87.00 177.00   0.40    6.00    --  123.25  77.00 -60.00  225
 67  \w     45.00  70.20   0.40    6.00    --  123.25-111.00 -30.00   63
 68  \w    133.00 169.00   0.40    6.00    --  123.25 111.00-120.00   90
 69  \w    117.00 152.20   0.40    6.00    --  123.25 111.00 -90.00   88
 70  \w     64.00  97.20   0.40    6.00    --  123.25 178.00  60.00   83
 71  \w    118.00 159.20   0.40    6.00    --  123.25  61.00-150.00  103
 72  \w     87.00 112.20   0.40    6.00    --  123.25  77.00-120.00   63
 73  \w     60.00  86.00   0.40    6.00    --  123.25 -77.00 -90.00   65
 74  \w    125.00 156.20   0.40    6.00    --  123.25 -81.00  42.01   78
 75  \w    125.00 151.00   0.40    6.00    --  123.25 111.00  30.00   65
 76  \w     45.00  76.20   0.40    6.00    --  123.25 -81.00  42.01   78
 77  \w    111.80 161.00   0.40    6.00    --  123.25 -80.00 127.57  123
 78  \w    128.00 175.20   0.40    6.00    --  123.25  77.00-150.00  118
 79  \w     49.00  84.20   0.40    6.00    --  123.25-111.00 -60.00   88
 80  \w     63.00  89.00   0.40    6.00    --  123.25 -80.00 127.57   65
 81  \w     71.00  97.00   0.40    6.00    --  123.25-111.00 -30.00   65
 82  \w     42.00 104.00   0.40    6.00    --  123.25 -95.00 -30.00  155
 83  \w     41.00 105.00   0.40    6.00    --  123.25 -95.00  30.00  160
 84  \w     47.00  73.00   0.40    6.00    --  123.25 -95.00 150.00   65
 85  \w    104.00 147.20   0.40    6.00    --  123.25 111.00-180.00  108
 86  \w     93.00 142.20   0.40    6.00    --  123.25 178.00 150.00  123
 87  \w     96.00 126.00   0.40    6.00    --  123.25  61.00 -60.00   75
 88  \w    107.00 151.00   0.40    6.00    --  123.25-178.00-120.00  110
 89  \w     92.00 117.20   0.40    6.00    --  123.25  77.00-150.00   63
 90  \w    143.00 177.00   0.40    6.00    --  123.25  45.00  90.00   85
 91  \w     66.00  98.00   0.40    6.00    --  123.25  24.00 -45.12   80
 92  \w     49.00  94.20   0.40    6.00    --  123.25-111.00  30.00  113
 93  \w     71.80 105.00   0.40    6.00    --  123.25 -95.00  90.00   83
 94  \w     71.00  97.00   0.40    6.00    --  123.25  -2.00  19.80   65
 95  \w    152.00 177.20   0.40    6.00    --  123.25  30.00-120.00   63
;
_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      0.0062394000
_diffrn_orient_matrix_UB_12      -0.0129304000
_diffrn_orient_matrix_UB_13      -0.1092831000
_diffrn_orient_matrix_UB_21      0.0377027000
_diffrn_orient_matrix_UB_22      0.0815651000
_diffrn_orient_matrix_UB_23      0.0097749000
_diffrn_orient_matrix_UB_31      0.0264492000
_diffrn_orient_matrix_UB_32      -0.1133583000
_diffrn_orient_matrix_UB_33      0.0196190000
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            64615
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.310
_diffrn_reflns_theta_min         2.665
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.372
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5469
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0448P)^2^+9.6079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5313
_reflns_number_total             5469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00264h2.cif
_cod_data_source_block           am-117
_cod_depositor_comments
'Adding full bibliography for 7160480--7160482.cif.'
_cod_database_code               7160482
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C22H16ClN4OSI
_chemical_oxdiff_usercomment     AM-117
_shelx_estimated_absorpt_t_max   0.732
_shelx_estimated_absorpt_t_min   0.611
_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
 C15-C16A \\sim C15-C16B
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(C16A) = Uanis(C16B)
4. Others
 Sof(C16B)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C11(H11)
5.b Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C16B(H16D,H16E,H16F), C19(H19A,H19B,H19C), C20(H20A,
 H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              8919
_shelx_fab_checksum              61285
_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 1.752
_oxdiff_exptl_absorpt_empirical_full_min 0.788