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_7159539
_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         'C22 H20 N4 O4, H2 O'
_chemical_formula_sum            'C22 H22 N4 O5'
_chemical_formula_weight         422.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-01-10
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                66.2311(15)
_cell_angle_beta                 74.6710(13)
_cell_angle_gamma                76.7962(14)
_cell_formula_units_Z            2
_cell_length_a                   8.26940(12)
_cell_length_b                   11.01204(19)
_cell_length_c                   12.41759(17)
_cell_measurement_reflns_used    31007
_cell_measurement_temperature    99.95(16)
_cell_measurement_theta_max      77.4960
_cell_measurement_theta_min      3.9340
_cell_volume                     988.49(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_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   -121.00 -39.00   0.50    0.41    --  -48.70 -38.00 156.00  164
  2  \w     39.00 121.00   0.50    0.41    --   48.70  38.00 -48.00  164
  3  \w    -23.00  43.00   0.50    0.41    --   48.70 -38.00 156.00  132
  4  \w    -43.00 -14.00   0.50    1.64    --  -86.25  38.00 -48.00   58
  5  \w   -158.00 -75.00   0.50    1.64    --  -86.25 -38.00 156.00  166
  6  \w     97.00 178.00   0.50    1.64    --  107.75  38.00 -48.00  162
  7  \w    -42.00 -12.00   0.50    0.41    --    2.00 124.00 151.79   60
  8  \w     -9.00  43.00   0.50    0.41    --   18.00  89.00  -0.29  104
  9  \w     -1.00  43.00   0.50    0.41    --   26.00  89.00  52.07   88
 10  \w      4.00  31.00   0.50    0.41    --   34.00  95.00 177.27   54
 11  \w    -86.00 -13.00   0.50    0.41    --  -48.70 125.00 120.00  146
 12  \w    -43.00  24.00   0.50    0.41    --  -48.70  38.00 -48.00  134
 13  \w     27.00 120.00   0.50    0.41    --   48.70  77.00 -90.00  186
 14  \w     27.00 120.00   0.50    0.41    --   48.70  77.00-150.00  186
 15  \w    -25.00  26.00   0.50    0.41    --   48.70 -19.00 -90.00  102
 16  \w     34.00  93.00   0.50    0.41    --   48.70-125.00   0.00  118
 17  \w     27.00 120.00   0.50    0.41    --   48.70  77.00 -30.00  186
 18  \w   -121.00 -28.00   0.50    0.41    --  -50.00 -77.00  86.49  186
 19  \w     28.00 121.00   0.50    0.41    --   50.00  77.00  33.52  186
 20  \w     30.00 121.00   0.50    0.41    --   50.00  74.00 -46.99  182
 21  \w   -125.00 -33.00   0.50    0.41    --  -54.00 -75.00 154.79  184
 22  \w     34.00 125.00   0.50    0.41    --   54.00  74.00  90.54  182
 23  \w     34.00 125.00   0.50    0.41    --   54.00  74.00  66.38  182
 24  \w     37.00 130.00   0.50    0.41    --   58.00  75.00 177.03  186
 25  \w     38.00 130.00   0.50    0.41    --   58.00  72.00-129.06  184
 26  \w     38.00 130.00   0.50    0.41    --   58.00  74.00 138.39  184
 27  \w     42.00 134.00   0.50    0.41    --   62.00  72.00  10.39  184
 28  \w     41.00 134.00   0.50    0.41    --   62.00  76.00 179.68  186
 29  \w     42.00 134.00   0.50    0.41    --   62.00  73.00 -19.59  184
 30  \w   -138.00 -49.00   0.50    0.41    --  -66.00 -66.00  85.25  178
 31  \w   -138.00 -47.00   0.50    0.41    --  -66.00 -70.00-129.58  182
 32  \w     45.00 138.00   0.50    0.41    --   66.00  75.00  33.40  186
 33  \w     44.00 138.00   0.50    0.41    --   66.00  77.00-129.29  188
 34  \w   -142.00 -53.00   0.50    1.64    --  -70.00 -65.00 -78.08  178
 35  \w     49.00 142.00   0.50    0.41    --   70.00  76.00  68.97  186
 36  \w   -142.00 -53.00   0.50    1.64    --  -70.00 -66.00-114.72  178
 37  \w   -142.00 -52.00   0.50    1.64    --  -70.00 -67.00 -54.21  180
 38  \w   -145.00 -57.00   0.50    1.64    --  -74.00 -66.00 -96.54  176
 39  \w   -145.00 -57.00   0.50    1.64    --  -74.00 -66.00 -84.06  176
 40  \w   -145.00 -57.00   0.50    1.64    --  -74.00 -66.00 104.97  176
 41  \w     53.00  84.00   0.50    0.41    --   74.00  75.00-141.43   62
 42  \w    105.00 131.00   0.50    0.41    --   74.00  75.00-141.43   52
 43  \w     52.00  77.00   0.50    0.41    --   74.00  77.00 175.49   50
 44  \w    -87.00 -61.00   0.50    1.64    --  -78.00 -64.00 -37.44   52
 45  \w    -94.00 -58.00   0.50    1.64    --  -78.00 -73.00  34.95   72
 46  \w    -90.00 -64.00   0.50    1.64    --  -86.25 -77.00 150.00   52
 47  \w    -91.00 -65.00   0.50    1.64    --  -86.25 -77.00  90.00   52
 48  \w   -102.00 -66.00   0.50    1.64    --  -86.25 -72.00 121.89   72
 49  \w    -98.00 -70.00   0.50    1.64    --  -86.25 -63.00 -96.10   56
 50  \w    -89.00 -64.00   0.50    1.64    --  -86.25 -77.00-150.00   50
 51  \w   -109.00 -69.00   0.50    1.64    --  -86.25 -71.00 165.50   80
 52  \w    -92.00 -65.00   0.50    1.64    --  -86.25 -75.00  47.49   54
 53  \w    -99.00 -66.00   0.50    1.64    --  -86.25 -77.00  30.00   66
 54  \w   -101.00 -64.00   0.50    1.64    --  -86.25 -77.00 -30.00   74
 55  \w   -141.00-115.00   0.50    1.64    --  -86.25 -77.00 -90.00   52
 56  \w    -89.00 -64.00   0.50    1.64    --  -86.25 -77.00 -90.00   50
 57  \w    -89.00 -64.00   0.50    1.64    --  -86.25 -77.00-180.00   50
 58  \w    -93.00 -67.00   0.50    1.64    --  -86.25 -72.00-108.85   52
 59  \w    -95.00 -66.00   0.50    1.64    --  -86.25 -77.00-120.00   58
 60  \w   -112.00 -67.00   0.50    1.64    --  -86.25 -75.00  11.02   90
 61  \w   -101.00 -69.00   0.50    1.64    --  -86.25 -71.00-177.00   64
 62  \w    -95.00 -69.00   0.50    1.64    --  -86.25 -70.00  67.22   52
 63  \w    -93.00 -66.00   0.50    1.64    --  -86.25 -74.00-134.94   54
 64  \w   -115.00 -68.00   0.50    1.64    --  -86.25 -72.00 105.60   94
 65  \w    -84.00 -59.00   0.50    1.64    --  -86.25 125.00   0.00   50
 66  \w    -93.00 -67.00   0.50    1.64    --  -86.25 -76.00 -45.58   52
 67  \w    123.00 177.00   0.50    1.64    --  107.75  30.00  60.00  108
 68  \w     83.00 111.00   0.50    1.64    --  107.75-125.00 -90.00   56
 69  \w     39.00  98.00   0.50    1.64    --  107.75 -95.00 120.00  118
 70  \w     42.00  68.00   0.50    1.64    --  107.75 -77.00 -30.00   52
 71  \w     43.00  68.00   0.50    1.64    --  107.75-125.00 -90.00   50
 72  \w    124.00 177.00   0.50    1.64    --  107.75  45.00 -90.00  106
 73  \w     88.00 173.00   0.50    1.64    --  107.75  77.00 150.00  170
 74  \w     72.00 111.00   0.50    1.64    --  107.75-125.00-150.00   78
 75  \w     37.00  87.00   0.50    1.64    --  107.75 -77.00 -60.00  100
 76  \w    129.00 155.00   0.50    1.64    --  107.75  61.00 150.00   52
 77  \w     95.00 121.00   0.50    1.64    --  107.75  61.00 150.00   52
 78  \w     95.00 125.00   0.50    1.64    --  107.75  61.00 -60.00   60
 79  \w    124.00 178.00   0.50    1.64    --  107.75  77.00 -30.00  108
 80  \w    123.00 159.00   0.50    1.64    --  107.75  30.00-150.00   72
 81  \w     89.00 116.00   0.50    1.64    --  107.75  77.00 -30.00   54
 82  \w    145.00 176.00   0.50    1.64    --  107.75  77.00-120.00   62
 83  \w     79.00 105.00   0.50    1.64    --  107.75 -95.00-120.00   52
 84  \w     88.00 128.00   0.50    1.64    --  107.75  77.00-120.00   80
 85  \w     80.00 109.00   0.50    1.64    --  107.75-125.00 -60.00   58
 86  \w     41.00  95.00   0.50    1.64    --  107.75 -77.00  90.00  108
 87  \w     70.00  96.00   0.50    1.64    --  107.75 -77.00-180.00   52
 88  \w     88.00 176.00   0.50    1.64    --  107.75  77.00 120.00  176
 89  \w     37.00  63.00   0.50    1.64    --  107.75 -61.00   0.00   52
 90  \w     92.00 124.00   0.50    1.64    --  107.75  77.00 -60.00   64
 91  \w     69.00  96.00   0.50    1.64    --  107.75 -95.00 -90.00   54
 92  \w    147.00 174.00   0.50    1.64    --  107.75  77.00   0.00   54
 93  \w     40.00  66.00   0.50    1.64    --  107.75-125.00 -60.00   52
 94  \w     36.00  71.00   0.50    1.64    --  107.75 -95.00 -60.00   70
 95  \w     38.00  64.00   0.50    1.64    --  107.75 -95.00 -90.00   52
 96  \w     94.00 140.00   0.50    1.64    --  107.75  61.00  60.00   92
 97  \w     94.00 124.00   0.50    1.64    --  107.75  61.00 -90.00   60
 98  \w     86.00 127.00   0.50    1.64    --  107.75  77.00   0.00   82
 99  \w    148.00 174.00   0.50    1.64    --  107.75  61.00-120.00   52
100  \w     93.00 127.00   0.50    1.64    --  107.75  61.00-120.00   68
101  \w     74.00 111.00   0.50    1.64    --  107.75-125.00 120.00   74
102  \w     36.00  63.00   0.50    1.64    --  107.75 -77.00-180.00   54
103  \w     40.00  65.00   0.50    1.64    --  107.75-125.00 120.00   50
104  \w     41.00  66.00   0.50    1.64    --  107.75 -77.00  30.00   50
105  \w    133.00 177.00   0.50    1.64    --  107.75  77.00-150.00   88
106  \w     43.00  69.00   0.50    1.64    --  107.75 -95.00-120.00   52
107  \w    138.00 163.00   0.50    1.64    --  107.75  45.00  90.00   50
108  \w     80.00 105.00   0.50    1.64    --  107.75 -95.00  90.00   50
109  \w     81.00 110.00   0.50    1.64    --  107.75-125.00   0.00   58
110  \w    133.00 176.00   0.50    1.64    --  107.75  45.00 -60.00   86
111  \w     39.00  69.00   0.50    1.64    --  107.75-125.00   0.00   60
112  \w    142.00 170.00   0.50    1.64    --  107.75  30.00  30.00   56
113  \w    104.00 130.00   0.50    1.64    --  107.75 125.00 120.00   52
114  \w    147.00 176.00   0.50    1.64    --  107.75 125.00 120.00   58
115  \w     88.00 129.00   0.50    1.64    --  107.75  77.00-150.00   82
116  \w     94.00 168.00   0.50    1.64    --  107.75  61.00  90.00  148
117  \w     96.00 125.00   0.50    1.64    --  107.75  61.00   0.00   58
118  \w    124.00 165.00   0.50    1.64    --  107.75  45.00 -30.00   82
119  \w     99.00 129.00   0.50    1.64    --  107.75  45.00  90.00   60
120  \w     40.00 105.00   0.50    1.64    --  107.75-125.00-180.00  130
121  \w     94.00 126.00   0.50    1.64    --  107.75  61.00 -30.00   64
122  \w     95.00 154.00   0.50    1.64    --  107.75  61.00-180.00  118
123  \w    137.00 163.00   0.50    1.64    --  107.75  77.00 -90.00   52
124  \w     40.00  66.00   0.50    1.64    --  107.75 -77.00 120.00   52
125  \w     86.00 156.00   0.50    1.64    --  107.75  77.00-180.00  140
126  \w    125.00 165.00   0.50    1.64    --  107.75 125.00-180.00   80
127  \w     45.00  70.00   0.50    1.64    --  107.75 -61.00-120.00   50
128  \w     37.00  64.00   0.50    1.64    --  107.75 -77.00-150.00   54
129  \w     86.00 126.00   0.50    1.64    --  107.75  77.00 -90.00   80
130  \w     47.00  95.00   0.50    1.64    --  107.75 -98.00  -1.50   96
131  \w     86.00 145.00   0.50    1.64    --  107.75  77.00  90.00  118
132  \w    138.00 172.00   0.50    1.64    --  107.75  77.00  30.00   68
133  \w     97.00 173.00   0.50    1.64    --  107.75  45.00   0.00  152
134  \w     72.00  98.00   0.50    1.64    --  107.75 -77.00 150.00   52
135  \w     42.00  68.00   0.50    1.64    --  107.75 -77.00 150.00   52
136  \w    136.00 162.00   0.50    1.64    --  107.75  77.00  60.00   52
137  \w     89.00 131.00   0.50    1.64    --  107.75  77.00  30.00   84
138  \w     96.00 160.00   0.50    1.64    --  107.75  61.00 120.00  128
139  \w     86.00 111.00   0.50    1.64    --  107.75  77.00  60.00   50
140  \w     97.00 155.00   0.50    1.64    --  107.75  61.00-150.00  116
141  \w     39.00 111.00   0.50    1.64    --  107.75-125.00  90.00  144
142  \w     43.00 106.00   0.50    1.64    --  107.75-108.00  37.72  126
143  \w     36.00  70.00   0.50    1.64    --  107.75 -61.00 150.00   68
144  \w     74.00 105.00   0.50    1.64    --  107.75 -95.00 -60.00   62
;
_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      -0.0294230000
_diffrn_orient_matrix_UB_12      -0.1462218000
_diffrn_orient_matrix_UB_13      0.0392173000
_diffrn_orient_matrix_UB_21      0.1608722000
_diffrn_orient_matrix_UB_22      -0.0491269000
_diffrn_orient_matrix_UB_23      0.0545402000
_diffrn_orient_matrix_UB_31      -0.1062724000
_diffrn_orient_matrix_UB_32      0.0052265000
_diffrn_orient_matrix_UB_33      0.1207401000
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            47219
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.859
_diffrn_reflns_theta_min         3.965
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0463P)^2^+0.3690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3886
_reflns_number_total             4157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01136d2.cif
_cod_data_source_block           C6BMTT
_cod_depositor_comments
'Adding full bibliography for 7159539--7159545.cif.'
_cod_database_code               7159539
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C22H20N4O4
_chemical_oxdiff_usercomment     C6BMTT
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.835
_reflns_odcompleteness_completeness 97.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_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:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C17(H17), C22(H22)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_res_checksum              5262
_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.825