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_7159540
_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         'C21 H22 N2 O5'
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.40
_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             2022-11-08
_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                 97.3170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.69260(10)
_cell_length_b                   11.74390(10)
_cell_length_c                   13.59140(10)
_cell_measurement_reflns_used    14884
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.3330
_cell_measurement_theta_min      3.7740
_cell_volume                     1851.13(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      99.99(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 0.995
_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    -64.00 -39.00   0.50    0.40    --  -48.70 116.00 -18.00   50
  2  \w   -106.00 -79.00   0.50    0.40    --  -48.70-167.00 107.00   54
  3  \w     44.00  76.00   0.50    0.40    --   48.70-116.00-106.00   64
  4  \w     72.00 121.00   0.50    0.40    --   48.70-167.00 107.00   98
  5  \w   -141.00-115.00   0.50    2.00    --  -86.25-116.00-106.00   52
  6  \w    -86.00 -61.00   0.50    2.00    --  -86.25 167.00 128.00   50
  7  \w     74.00  99.00   0.50    2.00    --  107.75-167.00 107.00   50
  8  \w    101.00 148.00   0.50    2.00    --  107.75 167.00 128.00   94
  9  \w    119.00 146.00   0.50    2.00    --  107.75 116.00 -18.00   54
 10  \w     74.00 109.00   0.50    2.00    --  107.75-116.00-106.00   70
 11  \w    -24.00  25.00   0.50    0.40    --  -48.70  19.00  60.00   98
 12  \w   -119.00 -28.00   0.50    0.40    --  -48.70 -77.00 -90.00  182
 13  \w   -117.00 -79.00   0.50    0.40    --  -48.70-125.00  60.00   76
 14  \w   -117.00 -75.00   0.50    0.40    --  -48.70-125.00 -60.00   84
 15  \w     38.00  79.00   0.50    2.00    --  107.75-100.00 -49.59   82
 16  \w     36.00  61.00   0.50    2.00    --  107.75 -61.00 150.00   50
 17  \w     97.00 175.00   0.50    2.00    --  107.75  15.00  90.00  156
 18  \w    142.00 176.00   0.50    2.00    --  107.75  52.00-111.36   68
 19  \w     45.00  73.00   0.50    2.00    --  107.75-125.00   0.00   56
 20  \w     52.00 105.00   0.50    2.00    --  107.75 -95.00-120.00  106
 21  \w     36.00  70.00   0.50    2.00    --  107.75 -61.00 -30.00   68
 22  \w     79.00 110.00   0.50    2.00    --  107.75-125.00  30.00   62
 23  \w    113.00 139.00   0.50    2.00    --  107.75  30.00 -60.00   52
 24  \w    151.00 178.00   0.50    2.00    --  107.75  30.00 -60.00   54
 25  \w     51.00 102.00   0.50    2.00    --  107.75 -77.00   0.00  102
 26  \w    133.00 168.00   0.50    2.00    --  107.75 125.00-180.00   70
 27  \w     38.00  63.00   0.50    2.00    --  107.75 -77.00  90.00   50
 28  \w    104.00 129.00   0.50    2.00    --  107.75  52.00-111.36   50
 29  \w     79.00 104.00   0.50    2.00    --  107.75 -77.00 120.00   50
 30  \w     65.00 108.00   0.50    2.00    --  107.75-111.00 -20.51   86
 31  \w    106.00 163.00   0.50    2.00    --  107.75  98.00  12.93  114
 32  \w    105.00 152.00   0.50    2.00    --  107.75  15.00-150.00   94
 33  \w     97.00 164.00   0.50    2.00    --  107.75  77.00   0.00  134
 34  \w     40.00 102.00   0.50    2.00    --  107.75 -95.00 120.00  124
 35  \w     97.00 126.00   0.50    2.00    --  107.75  45.00-180.00   58
 36  \w    105.00 151.00   0.50    2.00    --  107.75  30.00 -30.00   92
 37  \w     43.00  71.00   0.50    2.00    --  107.75 -61.00 -60.00   56
 38  \w     79.00 105.00   0.50    2.00    --  107.75 -97.00-121.25   52
 39  \w     47.00  88.00   0.50    2.00    --  107.75 -77.00-180.00   82
 40  \w     50.00  75.00   0.50    2.00    --  107.75 -77.00 120.00   50
 41  \w     36.00  62.00   0.50    2.00    --  107.75 -77.00-120.00   52
 42  \w     44.00  96.00   0.50    2.00    --  107.75 -95.00 150.00  104
 43  \w     82.00 108.00   0.50    2.00    --  107.75-115.00  35.28   52
 44  \w     60.00 106.00   0.50    2.00    --  107.75 -92.00 -96.34   92
 45  \w     76.00 111.00   0.50    2.00    --  107.75-125.00 -30.00   70
 46  \w     74.00 111.00   0.50    2.00    --  107.75 -85.00 -68.22   74
 47  \w     36.00  62.00   0.50    2.00    --  107.75 -61.00  90.00   52
;
_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      -0.0356478000
_diffrn_orient_matrix_UB_12      0.0600752000
_diffrn_orient_matrix_UB_13      0.0921076000
_diffrn_orient_matrix_UB_21      -0.0404301000
_diffrn_orient_matrix_UB_22      -0.1147645000
_diffrn_orient_matrix_UB_23      0.0382806000
_diffrn_orient_matrix_UB_31      0.1214894000
_diffrn_orient_matrix_UB_32      -0.0206331000
_diffrn_orient_matrix_UB_33      0.0556518000
_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  0.0539
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22156
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.762
_diffrn_reflns_theta_min         3.811
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78483
_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    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0536P)^2^+0.7635P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3707
_reflns_number_total             3929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01136d2.cif
_cod_data_source_block           tet-acid-2
_cod_depositor_comments
'Adding full bibliography for 7159539--7159545.cif.'
_cod_database_code               7159540
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H10N2O2
_chemical_oxdiff_usercomment     TET-Acid-2
_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 Secondary CH2 refined with riding coordinates:
 C2(H2B,H2C), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              6910
_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 2.673
_oxdiff_exptl_absorpt_empirical_full_min 0.415