1,1'-Carbonyldiimidazole-mediated transformation of allomaltol containing hydrazides into substituted 3-acetyltetronic acids.
Komogortsev, Andrey N.; Lichitskii, Boris V.; Melekhina, Valeriya G.; Organic & biomolecular chemistry 21 (2023) 7224–7230; doi:10.1039/d3ob01136d

data_7159544
_publ_section_title
;
 1,1'-Carbonyldiimidazole-mediated transformation of allomaltol containing
 hydrazides into substituted 3-acetyltetronic acids.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7224
_journal_page_last               7230
_journal_paper_doi               10.1039/d3ob01136d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-10-30
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.4030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.80840(10)
_cell_length_b                   14.35350(10)
_cell_length_c                   12.24630(10)
_cell_measurement_reflns_used    29081
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5720
_cell_measurement_theta_min      3.0730
_cell_volume                     1635.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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    '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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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     21.00  84.00   0.45    0.30    --   48.57-108.00 -40.00  140
  2  \w    -82.00 -18.10   0.45    0.80    --  -86.25 108.00  56.00  142
  3  \w   -155.00 -83.00   0.45    0.80    --  -86.25-108.00 -40.00  160
  4  \w    104.00 176.00   0.45    0.80    --  107.75 108.00  56.00  160
  5  \w     39.00 106.05   0.45    0.80    --  107.75-108.00 -40.00  149
  6  \w   -118.00 -73.00   0.45    0.30    --  -48.57-125.00 120.00  100
  7  \w   -120.00 -27.75   0.45    0.30    --  -48.57 -77.00 -90.00  205
  8  \w    -82.00  -1.00   0.45    0.30    --  -48.57 108.00  56.00  180
  9  \w   -118.00 -73.00   0.45    0.30    --  -48.57-125.00  60.00  100
 10  \w   -118.00 -73.00   0.45    0.30    --  -48.57-125.00  90.00  100
 11  \w    -26.00  24.85   0.45    0.30    --  -48.57  19.00 150.00  113
 12  \w    -22.00  62.15   0.45    0.30    --   48.57 -57.00   0.00  187
 13  \w    -25.00  25.40   0.45    0.30    --   48.57 -19.00 -60.00  112
 14  \w     34.00  92.05   0.45    0.30    --   48.57-125.00  60.00  129
 15  \w    -51.00 -15.00   0.45    0.80    --  -86.25  45.00   0.00   80
 16  \w     36.00 104.40   0.45    0.80    --  107.75 -95.00 -90.00  152
 17  \w     97.00 178.00   0.45    0.80    --  107.75  45.00 120.00  180
 18  \w     36.00 104.40   0.45    0.80    --  107.75 -77.00  30.00  152
 19  \w     95.00 176.00   0.45    0.80    --  107.75 125.00 150.00  180
 20  \w     38.00 105.05   0.45    0.80    --  107.75 -98.00 -35.04  149
 21  \w     39.00 111.00   0.45    0.80    --  107.75-125.00 -90.00  160
 22  \w     36.00  70.20   0.45    0.80    --  107.75 -61.00 150.00   76
 23  \w     36.00 104.40   0.45    0.80    --  107.75 -77.00  90.00  152
 24  \w     95.00 176.00   0.45    0.80    --  107.75 125.00-120.00  180
 25  \w     39.00 106.05   0.45    0.80    --  107.75-106.00  64.29  149
 26  \w     39.00 111.00   0.45    0.80    --  107.75-125.00-180.00  160
 27  \w     97.00 178.00   0.45    0.80    --  107.75  45.00  60.00  180
 28  \w     39.00 111.00   0.45    0.80    --  107.75-125.00 -60.00  160
 29  \w     86.00 176.90   0.45    0.80    --  107.75  77.00-180.00  202
 30  \w     36.00 104.40   0.45    0.80    --  107.75 -95.00-150.00  152
 31  \w     97.00 178.00   0.45    0.80    --  107.75  45.00 -30.00  180
 32  \w     39.00 111.00   0.45    0.80    --  107.75-125.00 120.00  160
 33  \w     86.00 176.90   0.45    0.80    --  107.75  77.00-120.00  202
 34  \w     97.00 178.00   0.45    0.80    --  107.75  15.00 -60.00  180
 35  \w     36.00 104.40   0.45    0.80    --  107.75 -95.00  30.00  152
 36  \w     39.00 111.00   0.45    0.80    --  107.75-125.00-120.00  160
 37  \w     97.00 175.75   0.45    0.80    --  107.75 122.00 -63.41  175
 38  \w     95.00 176.00   0.45    0.80    --  107.75 125.00  90.00  180
 39  \w     39.00 106.05   0.45    0.80    --  107.75-108.00  11.04  149
 40  \w     36.00 104.40   0.45    0.80    --  107.75 -95.00 -30.00  152
 41  \w     95.00 176.00   0.45    0.80    --  107.75 125.00   0.00  180
 42  \w     51.00 109.05   0.45    0.80    --  107.75-125.00 -30.00  129
 43  \w    116.00 140.75   0.45    0.80    --  107.75  30.00-150.00   55
 44  \w    151.00 178.00   0.45    0.80    --  107.75  30.00-150.00   60
 45  \w     77.00 105.35   0.45    0.80    --  107.75 -99.00-127.76   63
 46  \w     36.00  70.20   0.45    0.80    --  107.75 -77.00  60.00   76
 47  \w     44.00  70.10   0.45    0.80    --  107.75 -95.00 120.00   58
 48  \w     41.00  67.10   0.45    0.80    --  107.75-125.00  30.00   58
 49  \w    127.00 158.05   0.45    0.80    --  107.75 125.00-150.00   69
 50  \w     36.00  62.10   0.45    0.80    --  107.75 -77.00 -60.00   58
 51  \w     54.00  80.10   0.45    0.80    --  107.75 -77.00 -30.00   58
 52  \w     43.00  69.10   0.45    0.80    --  107.75 -77.00   0.00   58
 53  \w     39.00  65.10   0.45    0.80    --  107.75-125.00   0.00   58
 54  \w    106.00 177.10   0.45    0.80    --  107.75  61.00 150.00  158
 55  \w     44.00  70.10   0.45    0.80    --  107.75 -95.00   0.00   58
 56  \w     43.00  69.10   0.45    0.80    --  107.75 -95.00  90.00   58
 57  \w     36.00  62.10   0.45    0.80    --  107.75 -94.00-153.03   58
 58  \w     78.00 104.10   0.45    0.80    --  107.75 -95.00  90.00   58
 59  \w     40.00 106.15   0.45    0.80    --  107.75-106.00 177.56  147
 60  \w    122.00 164.30   0.45    0.80    --  107.75 125.00 -30.00   94
 61  \w    134.00 159.65   0.45    0.80    --  107.75 125.00 120.00   57
 62  \w    123.00 147.75   0.45    0.80    --  107.75  30.00 -30.00   55
 63  \w    124.00 164.05   0.45    0.80    --  107.75  15.00-150.00   89
 64  \w    120.00 145.65   0.45    0.80    --  107.75  77.00  30.00   57
 65  \w     92.00 122.15   0.45    0.80    --  107.75 -87.00  65.56   67
 66  \w     37.00 107.20   0.45    0.80    --  107.75  -1.00 124.00  156
 67  \w    125.00 149.75   0.45    0.80    --  107.75  45.00 150.00   55
;
_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      -0.0394849000
_diffrn_orient_matrix_UB_12      0.1034400000
_diffrn_orient_matrix_UB_13      0.0044170000
_diffrn_orient_matrix_UB_21      0.0114013000
_diffrn_orient_matrix_UB_22      0.0144607000
_diffrn_orient_matrix_UB_23      -0.1214929000
_diffrn_orient_matrix_UB_31      -0.1604055000
_diffrn_orient_matrix_UB_32      -0.0244532000
_diffrn_orient_matrix_UB_33      -0.0530212000
_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  0.0322
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41248
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.731
_diffrn_reflns_theta_min         4.751
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0433P)^2^+0.7451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3382
_reflns_number_total             3480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01136d2.cif
_cod_data_source_block           tet-acid
_cod_depositor_comments
'Adding full bibliography for 7159539--7159545.cif.'
_cod_database_code               7159544
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H22N2O5
_chemical_oxdiff_usercomment     TET-Acid
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_shelx_res_checksum              42375
_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.736