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_7159545
_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         'C23 H24 N4 O6, C7 H8'
_chemical_formula_sum            'C30 H32 N4 O6'
_chemical_formula_weight         544.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-11-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.0334(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3210(2)
_cell_length_b                   7.16745(8)
_cell_length_c                   20.9490(3)
_cell_measurement_reflns_used    15608
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      77.3470
_cell_measurement_theta_min      3.8160
_cell_volume                     2725.53(6)
_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_temperature      100.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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    -46.00  23.00   0.50    5.50    --  -48.67  41.00-132.00  138
  2  \w   -120.00 -38.00   0.50    5.50    --  -48.67 -41.00  74.00  164
  3  \w     11.00  36.00   0.50    5.50    --   48.67 -41.00  74.00   50
  4  \w     52.00  80.00   0.50    5.50    --   48.67  41.00-132.00   56
  5  \w    -46.00 -21.00   0.50   22.00    --  -86.25  41.00-132.00   50
  6  \w   -126.00 -90.00   0.50   22.00    --  -86.25 -41.00  74.00   72
  7  \w     99.00 142.00   0.50   22.00    --  107.75  41.00-132.00   86
  8  \w    -14.00  26.00   0.50    5.50    --  -48.67  19.00   0.00   80
  9  \w   -105.00 -74.00   0.50    5.50    --  -48.67-125.00-150.00   62
 10  \w    -21.00  25.00   0.50    5.50    --   48.67 -19.00 -30.00   92
 11  \w    -44.00 -19.00   0.50   22.00    --  -86.25  45.00  60.00   50
 12  \w    120.00 163.00   0.50   22.00    --  107.75  15.00 -30.00   86
 13  \w     38.00  63.00   0.50   22.00    --  107.75 -77.00-120.00   50
 14  \w     39.00  64.00   0.50   22.00    --  107.75 -61.00 -30.00   50
 15  \w    126.00 156.00   0.50   22.00    --  107.75  30.00-180.00   60
 16  \w     40.00  71.00   0.50   22.00    --  107.75 -61.00-180.00   62
 17  \w     47.00  73.00   0.50   22.00    --  107.75-125.00   0.00   52
 18  \w    110.00 137.00   0.50   22.00    --  107.75  45.00-120.00   54
 19  \w    144.00 175.00   0.50   22.00    --  107.75  45.00-120.00   62
 20  \w     39.00  98.00   0.50   22.00    --  107.75 -98.00  35.98  118
 21  \w     40.00 105.00   0.50   22.00    --  107.75 -77.00 120.00  130
 22  \w    117.00 143.00   0.50   22.00    --  107.75 107.00-170.22   52
 23  \w     97.00 125.00   0.50   22.00    --  107.75  30.00   0.00   56
 24  \w     91.00 127.00   0.50   22.00    --  107.75  77.00  30.00   72
 25  \w    133.00 159.00   0.50   22.00    --  107.75  30.00   0.00   52
 26  \w     41.00 102.00   0.50   22.00    --  107.75 -95.00 120.00  122
 27  \w     57.00 105.00   0.50   22.00    --  107.75-103.00  84.50   96
 28  \w    101.00 127.00   0.50   22.00    --  107.75  61.00-150.00   52
 29  \w    139.00 165.00   0.50   22.00    --  107.75  61.00-150.00   52
 30  \w     54.00  80.00   0.50   22.00    --  107.75-125.00 120.00   52
 31  \w     68.00 104.00   0.50   22.00    --  107.75-125.00 -90.00   72
 32  \w    146.00 171.00   0.50   22.00    --  107.75  61.00-180.00   50
 33  \w     36.00  61.00   0.50   22.00    --  107.75 -61.00 120.00   50
 34  \w     42.00  72.00   0.50   22.00    --  107.75-125.00  30.00   60
 35  \w     82.00 107.00   0.50   22.00    --  107.75-125.00  30.00   50
 36  \w    103.00 132.00   0.50   22.00    --  107.75  30.00  60.00   58
 37  \w    142.00 168.00   0.50   22.00    --  107.75  30.00  60.00   52
 38  \w     93.00 119.00   0.50   22.00    --  107.75  61.00-180.00   52
 39  \w     67.00 114.00   0.50   22.00    --  107.75-143.00 -28.98   94
 40  \w     69.00  98.00   0.50   22.00    --  107.75 -77.00-120.00   58
 41  \w    138.00 164.00   0.50   22.00    --  107.75  77.00  30.00   52
 42  \w     95.00 134.00   0.50   22.00    --  107.75  61.00 150.00   78
 43  \w     98.00 136.00   0.50   22.00    --  107.75  15.00   0.00   76
 44  \w    145.00 178.00   0.50   22.00    --  107.75  15.00   0.00   66
 45  \w     39.00  94.00   0.50   22.00    --  107.75 -77.00 -60.00  110
 46  \w     37.00  62.00   0.50   22.00    --  107.75 -77.00  90.00   50
 47  \w     37.00  62.00   0.50   22.00    --  107.75 -77.00   0.00   50
 48  \w     78.00 104.00   0.50   22.00    --  107.75 -77.00   0.00   52
 49  \w     49.00  74.00   0.50   22.00    --  107.75 -95.00-180.00   50
 50  \w     40.00  80.00   0.50   22.00    --  107.75 -95.00 150.00   80
 51  \w    115.00 141.00   0.50   22.00    --  107.75 122.00-133.21   52
 52  \w    117.00 143.00   0.50   22.00    --  107.75  45.00-150.00   52
 53  \w    135.00 178.00   0.50   22.00    --  107.75  30.00 -90.00   86
 54  \w    139.00 175.00   0.50   22.00    --  107.75 125.00   0.00   72
 55  \w     95.00 121.00   0.50   22.00    --  107.75 -88.00 -74.45   52
 56  \w     37.00  68.00   0.50   22.00    --  107.75 -61.00 -60.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33634
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.833
_diffrn_reflns_theta_min         2.687
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66569
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0513P)^2^+1.3167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4980
_reflns_number_total             5757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01136d2.cif
_cod_data_source_block           kjoket5m
_cod_depositor_comments
'Adding full bibliography for 7159539--7159545.cif.'
_cod_database_code               7159545
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.887
_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.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              40020
_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
;