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_7160480
_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         'C21 H20 N2 O4 S'
_chemical_formula_sum            'C21 H20 N2 O4 S'
_chemical_formula_weight         396.45
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-02-29
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2024-09-19 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.8020(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2397(3)
_cell_length_b                   19.0851(4)
_cell_length_c                   6.99979(12)
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      79.0890
_cell_measurement_theta_min      4.0880
_cell_volume                     1764.82(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_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    -80.00  34.00   0.50    4.50    --  -40.36  92.00 -83.00  228
  2  \w     -8.00  27.00   0.50    4.50    --   40.36 -92.00 163.00   70
  3  \w     31.00  80.00   0.50    4.50    --   40.36 -92.00 163.00   98
  4  \w   -152.00-127.00   0.50   14.00    --  -98.00 -92.00 163.00   50
  5  \w    106.00 168.00   0.50   14.00    --  119.50  92.00 -83.00  124
  6  \w     51.00  76.00   0.50   14.00    --  119.50 -92.00 163.00   50
  7  \w    -27.00  32.00   0.50    4.50    --  -40.36  19.00 -90.00  118
  8  \w    -27.00  38.00   0.50    4.50    --  -40.36  19.00  30.00  130
  9  \w    -45.00  37.00   0.50    4.50    --  -40.36  92.00 -83.00  164
 10  \w     71.00 119.00   0.50    4.50    --   40.36 178.00-150.00   96
 11  \w    -51.00 -26.00   0.50   14.00    --  -98.00  45.00 120.00   50
 12  \w    -50.00 -21.00   0.50   14.00    --  -98.00  45.00 -60.00   58
 13  \w    -74.00 -48.00   0.50   14.00    --  -98.00  92.00 -83.00   52
 14  \w    -50.00 -25.00   0.50   14.00    --  -98.00  45.00 150.00   50
 15  \w    -50.00 -21.00   0.50   14.00    --  -98.00  45.00  90.00   58
 16  \w     82.00 107.00   0.50   14.00    --  119.50-111.00  90.00   50
 17  \w     47.00  73.00   0.50   14.00    --  119.50 -95.00 120.00   52
 18  \w    103.00 129.00   0.50   14.00    --  119.50  45.00  30.00   52
 19  \w     74.00 100.00   0.50   14.00    --  119.50 -95.00 120.00   52
 20  \w     69.00 100.00   0.50   14.00    --  119.50 -80.00 -13.44   62
 21  \w     71.00 102.00   0.50   14.00    --  119.50-111.00 -30.00   62
 22  \w     46.00  74.00   0.50   14.00    --  119.50-111.00  90.00   56
 23  \w    126.00 152.00   0.50   14.00    --  119.50 111.00-150.00   52
 24  \w     55.00  96.00   0.50   14.00    --  119.50 -77.00   0.00   82
 25  \w    151.00 177.00   0.50   14.00    --  119.50 111.00-180.00   52
 26  \w     68.00 108.00   0.50   14.00    --  119.50-111.00 120.00   80
 27  \w     94.00 137.00   0.50   14.00    --  119.50  61.00 120.00   86
 28  \w    145.00 170.00   0.50   14.00    --  119.50  61.00 120.00   50
 29  \w     87.00 135.00   0.50   14.00    --  119.50  77.00 -60.00   96
 30  \w     93.00 141.00   0.50   14.00    --  119.50  61.00  60.00   96
 31  \w     47.00  98.00   0.50   14.00    --  119.50-111.00-120.00  102
 32  \w     89.00 141.00   0.50   14.00    --  119.50  77.00-120.00  104
 33  \w    144.00 170.00   0.50   14.00    --  119.50  77.00-120.00   52
 34  \w    139.00 177.00   0.50   14.00    --  119.50 111.00 150.00   76
 35  \w     80.00 105.00   0.50   14.00    --  119.50 -77.00-180.00   50
 36  \w    129.00 154.00   0.50   14.00    --  119.50 -80.00 -13.44   50
 37  \w     80.00 105.00   0.50   14.00    --  119.50 -95.00-180.00   50
 38  \w    124.00 165.00   0.50   14.00    --  119.50 111.00 -60.00   82
 39  \w     42.00  74.00   0.50   14.00    --  119.50 -95.00-180.00   64
 40  \w    104.00 143.00   0.50   14.00    --  119.50 178.00  60.00   78
 41  \w    128.00 157.00   0.50   14.00    --  119.50 -87.00  85.58   58
 42  \w     64.00 146.00   0.50   14.00    --  119.50 178.00-180.00  164
 43  \w     76.00 102.00   0.50   14.00    --  119.50 -87.00  85.58   52
 44  \w    103.00 131.00   0.50   14.00    --  119.50 111.00-180.00   56
 45  \w     90.00 163.00   0.50   14.00    --  119.50  30.00  90.00  146
 46  \w    104.00 152.00   0.50   14.00    --  119.50 -88.00  81.03   96
 47  \w    104.00 177.00   0.50   14.00    --  119.50  61.00   0.00  146
 48  \w     65.00  91.00   0.50   14.00    --  119.50 -82.00 157.04   52
 49  \w    119.00 155.00   0.50   14.00    --  119.50 -82.00 157.04   72
 50  \w     73.00  98.00   0.50   14.00    --  119.50 -84.00-138.26   50
 51  \w     95.00 155.00   0.50   14.00    --  119.50  61.00-120.00  120
 52  \w     95.00 133.00   0.50   14.00    --  119.50  45.00 -30.00   76
 53  \w     49.00  85.00   0.50   14.00    --  119.50 -77.00-120.00   72
 54  \w     53.00 104.00   0.50   14.00    --  119.50 -95.00 -30.00  102
 55  \w    145.00 177.00   0.50   14.00    --  119.50  77.00 -60.00   64
 56  \w    115.00 141.00   0.50   14.00    --  119.50  30.00-180.00   52
 57  \w     44.00  73.00   0.50   14.00    --  119.50 -84.00 107.59   58
 58  \w    115.00 153.00   0.50   14.00    --  119.50 -84.00 107.59   76
 59  \w     63.00  89.00   0.50   14.00    --  119.50 -88.00 -20.02   52
 60  \w     48.00  75.00   0.50   14.00    --  119.50 -95.00-120.00   54
;
_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      -0.0828535000
_diffrn_orient_matrix_UB_12      0.0565793000
_diffrn_orient_matrix_UB_13      0.0044966000
_diffrn_orient_matrix_UB_21      0.0740304000
_diffrn_orient_matrix_UB_22      0.0481004000
_diffrn_orient_matrix_UB_23      0.1174682000
_diffrn_orient_matrix_UB_31      0.0353974000
_diffrn_orient_matrix_UB_32      0.0316866000
_diffrn_orient_matrix_UB_33      -0.1865850000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6297
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.968
_diffrn_reflns_theta_min         3.345
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.911
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0822P)^2^+1.2035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5856
_reflns_number_total             6297
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9773\% 
around [1.00 0.01 -0.00] (reciprocal) or [0.99 0.00 0.12] (direct)
;
_cod_data_source_file            d5ob00264h2.cif
_cod_data_source_block           AM14
_cod_depositor_comments
'Adding full bibliography for 7160480--7160482.cif.'
_cod_database_code               7160480
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H20N2O4S
_chemical_oxdiff_usercomment     AM14
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4532(14)
 0.5468(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C13(H13)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              78091
_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 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.604
_oxdiff_exptl_absorpt_spherical_max 0.869
_oxdiff_exptl_absorpt_spherical_min 0.869
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2