Anionic photochemical rearrangement of 3-hydroxypyran-4-ones bearing oxazol-2-one fragment
Komogortsev, Andrey N.; Melekhina, Valeriya G.; Lichitskii, Boris V.; Organic & Biomolecular Chemistry 22 (2024) 1686–1692; doi:10.1039/D3OB01957H

data_7159776
_publ_section_title
;
 Anionic photochemical rearrangement of 3-hydroxypyran-4-ones bearing
 oxazol-2-one fragment
;
_journal_issue                   8
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1686
_journal_page_last               1692
_journal_paper_doi               10.1039/D3OB01957H
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C24 H21 N O6, 0.5(C6 H6)'
_chemical_formula_sum            'C27 H24 N O6'
_chemical_formula_weight         458.47
_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             2023-03-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-10-27 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2259(2)
_cell_length_b                   19.8037(2)
_cell_length_c                   7.83380(10)
_cell_measurement_reflns_used    17124
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      75.3130
_cell_measurement_theta_min      3.4640
_cell_volume                     2665.47(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_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    'XT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_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 0.989
_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   -122.00  35.00   0.50    4.03    --  -43.17  -2.00-156.00  314
  2  \w    -36.00 121.00   0.50    4.03    --   43.17  -2.00-156.00  314
  3  \w   -168.00 -11.00   0.50   17.12    --  -90.25   2.00  21.00  314
  4  \w     34.00 178.00   0.50   17.12    --  111.75   2.00  21.00  288
  5  \w     33.00 151.00   0.50   17.12    --  111.75  -2.00-156.00  236
  6  \w    -83.00 -14.00   0.50    4.03    --  -43.17 125.00-180.00  138
  7  \w    -29.00  43.00   0.50    4.03    --   43.17 -38.00 -90.00  144
  8  \w     40.00  80.00   0.50    4.03    --   43.17 -99.00-180.00   80
  9  \w     19.00  44.00   0.50    4.03    --   43.17   2.00  21.00   50
 10  \w   -115.00 -90.00   0.50   17.12    --  -90.25  -2.00-156.00   50
 11  \w     38.00  69.00   0.50   17.12    --  111.75 -61.00-120.00   62
 12  \w     65.00  91.00   0.50   17.12    --  111.75 -95.00  30.00   52
 13  \w     64.00  89.00   0.50   17.12    --  111.75 -77.00  60.00   50
 14  \w     45.00  75.00   0.50   17.12    --  111.75 -95.00 -30.00   60
 15  \w    140.00 166.00   0.50   17.12    --  111.75  45.00-150.00   52
 16  \w     39.00  90.00   0.50   17.12    --  111.75 -77.00 120.00  102
 17  \w    107.00 178.00   0.50   17.12    --  111.75 101.00  41.65  142
 18  \w     43.00  70.00   0.50   17.12    --  111.75 -61.00  30.00   54
 19  \w     54.00 108.00   0.50   17.12    --  111.75-112.00-157.16  108
 20  \w     37.00  64.00   0.50   17.12    --  111.75 -95.00  30.00   54
 21  \w     62.00 160.00   0.50   17.12    --  111.75  15.00  60.00  196
 22  \w     82.00 107.00   0.50   17.12    --  111.75-110.00 108.23   50
 23  \w     98.00 136.00   0.50   17.12    --  111.75  45.00-150.00   76
 24  \w     41.00 107.00   0.50   17.12    --  111.75-125.00  90.00  132
 25  \w     47.00  83.00   0.50   17.12    --  111.75-148.00-155.12   72
 26  \w     99.00 128.00   0.50   17.12    --  111.75-148.00-155.12   58
 27  \w     52.00  77.00   0.50   17.12    --  111.75-110.00 108.23   50
 28  \w     40.00 103.00   0.50   17.12    --  111.75 -95.00 120.00  126
 29  \w     56.00  91.00   0.50   17.12    --  111.75 -77.00-120.00   70
 30  \w     91.00 149.00   0.50   17.12    --  111.75  45.00-120.00  116
 31  \w    114.00 161.00   0.50   17.12    --  111.75  30.00-180.00   94
 32  \w     90.00 140.00   0.50   17.12    --  111.75  30.00 150.00  100
 33  \w     62.00  88.00   0.50   17.12    --  111.75 -77.00-180.00   52
 34  \w     87.00 112.00   0.50   17.12    --  111.75-125.00-150.00   50
 35  \w    111.00 144.00   0.50   17.12    --  111.75 -87.00  89.68   66
 36  \w     38.00  83.00   0.50   17.12    --  111.75 -95.00-180.00   90
 37  \w     39.00  71.00   0.50   17.12    --  111.75 -61.00   0.00   64
 38  \w     71.00 105.00   0.50   17.12    --  111.75 -95.00-120.00   68
 39  \w    116.00 142.00   0.50   17.12    --  111.75  80.00  53.47   52
 40  \w     91.00 177.00   0.50   17.12    --  111.75  61.00 -60.00  172
 41  \w     75.00 127.00   0.50   17.12    --  111.75   5.00 159.62  104
 42  \w     39.00  64.00   0.50   17.12    --  111.75 -77.00 -30.00   50
;
_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      -0.0855761000
_diffrn_orient_matrix_UB_12      -0.0008867000
_diffrn_orient_matrix_UB_13      -0.0722617000
_diffrn_orient_matrix_UB_21      -0.0268639000
_diffrn_orient_matrix_UB_22      0.0018931000
_diffrn_orient_matrix_UB_23      0.1833932000
_diffrn_orient_matrix_UB_31      -0.0002415000
_diffrn_orient_matrix_UB_32      0.0777264000
_diffrn_orient_matrix_UB_33      -0.0053084000
_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  0.0342
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            33501
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.064
_diffrn_reflns_theta_min         2.572
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00104(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         5572
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0700P)^2^+0.8706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4965
_reflns_number_total             5572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01957h2.cif
_cod_data_source_block           oxaz-136
_cod_depositor_comments          'Adding full bibliography for 7159776.cif.'
_cod_database_code               7159776
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C24H21NO6
_chemical_oxdiff_usercomment     OXAZ-136
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.895
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25-C26 \\sim C26-C27 \\sim C25-C27_$2
 with sigma of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5A), C6(H6), C8(H8), C9(H9), C14(H14), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              62057
_shelx_fab_checksum              76901
_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 1.559
_oxdiff_exptl_absorpt_empirical_full_min 0.461