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_7159541
_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         'C13 H15 N O5, 2(C3 H4 N2)'
_chemical_formula_sum            'C19 H23 N5 O5'
_chemical_formula_weight         401.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-03-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.9400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.5566(2)
_cell_length_b                   9.65170(10)
_cell_length_c                   21.0321(2)
_cell_measurement_reflns_used    20854
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6830
_cell_measurement_theta_min      4.2270
_cell_volume                     3948.59(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (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 0.999
_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    -75.00  24.00   0.50    0.40    --  -48.70  87.00  59.00  198
  2  \w    -21.00  75.00   0.50    0.40    --   48.70 -87.00 -58.00  192
  3  \w   -112.00 -14.00   0.50    1.60    --  -86.25  87.00  59.00  196
  4  \w     36.00 134.00   0.50    1.60    --  107.75 -87.00 -58.00  196
  5  \w    101.00 178.00   0.50    1.60    --  107.75  87.00  59.00  154
  6  \w   -118.00 -73.00   0.50    0.40    --  -48.70-125.00   0.00   90
  7  \w   -118.00 -73.00   0.50    0.40    --  -48.70-125.00  30.00   90
  8  \w    -26.00  26.00   0.50    0.40    --  -48.70  19.00-180.00  104
  9  \w    -25.00  26.00   0.50    0.40    --   48.70 -19.00-150.00  102
 10  \w   -158.00 -79.00   0.50    1.60    --  -86.25 -87.00 -58.00  158
 11  \w    -51.00 -14.00   0.50    1.60    --  -86.25  45.00-120.00   74
 12  \w    101.00 176.00   0.50    1.60    --  107.75 116.00 -74.79  150
 13  \w     45.00  71.00   0.50    1.60    --  107.75 -61.00 -60.00   52
 14  \w    102.00 150.00   0.50    1.60    --  107.75  30.00 -30.00   96
 15  \w    142.00 173.00   0.50    1.60    --  107.75 125.00-120.00   62
 16  \w     63.00 105.00   0.50    1.60    --  107.75-105.00  13.72   84
 17  \w     41.00  67.00   0.50    1.60    --  107.75 -61.00 120.00   52
 18  \w     46.00  72.00   0.50    1.60    --  107.75 -77.00 -30.00   52
 19  \w     95.00 136.00   0.50    1.60    --  107.75 125.00-120.00   82
 20  \w     37.00  70.00   0.50    1.60    --  107.75 -61.00-150.00   66
 21  \w     50.00  76.00   0.50    1.60    --  107.75-125.00-150.00   52
 22  \w    131.00 177.00   0.50    1.60    --  107.75 125.00-180.00   92
 23  \w     40.00 117.00   0.50    1.60    --  107.75-135.00 151.77  154
 24  \w     60.00 105.00   0.50    1.60    --  107.75 -95.00 -90.00   90
 25  \w    114.00 140.00   0.50    1.60    --  107.75  45.00   0.00   52
 26  \w    143.00 168.00   0.50    1.60    --  107.75  45.00   0.00   50
 27  \w     84.00 111.00   0.50    1.60    --  107.75-125.00-180.00   54
 28  \w     37.00  65.00   0.50    1.60    --  107.75 -57.00-107.27   56
 29  \w     98.00 135.00   0.50    1.60    --  107.75  30.00  30.00   74
 30  \w     44.00  84.00   0.50    1.60    --  107.75 -95.00  90.00   80
 31  \w     95.00 121.00   0.50    1.60    --  107.75 125.00-180.00   52
 32  \w     76.00 101.00   0.50    1.60    --  107.75 -77.00-120.00   50
 33  \w     42.00 106.00   0.50    1.60    --  107.75-105.00  55.78  128
 34  \w     98.00 126.00   0.50    1.60    --  107.75  30.00 150.00   56
 35  \w    131.00 176.00   0.50    1.60    --  107.75  30.00 150.00   90
 36  \w     48.00  81.00   0.50    1.60    --  107.75 -77.00   0.00   66
 37  \w     57.00  83.00   0.50    1.60    --  107.75 -95.00  30.00   52
 38  \w     36.00  63.00   0.50    1.60    --  107.75 -61.00-120.00   54
 39  \w     74.00 104.00   0.50    1.60    --  107.75 -77.00-180.00   60
 40  \w     38.00  71.00   0.50    1.60    --  107.75 -95.00   0.00   66
 41  \w     43.00  77.00   0.50    1.60    --  107.75-125.00-180.00   68
 42  \w    111.00 136.00   0.50    1.60    --  107.75  73.00  49.59   50
 43  \w    134.00 160.00   0.50    1.60    --  107.75  30.00-180.00   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      -0.0143988000
_diffrn_orient_matrix_UB_12      -0.1429129000
_diffrn_orient_matrix_UB_13      -0.0310499000
_diffrn_orient_matrix_UB_21      -0.0719710000
_diffrn_orient_matrix_UB_22      -0.0007380000
_diffrn_orient_matrix_UB_23      0.0238004000
_diffrn_orient_matrix_UB_31      -0.0299406000
_diffrn_orient_matrix_UB_32      0.0705734000
_diffrn_orient_matrix_UB_33      -0.0624379000
_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  0.0258
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26476
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.853
_diffrn_reflns_theta_min         4.227
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.283
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0108P)^2^+10.2680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4091
_reflns_number_total             4156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01136d2.cif
_cod_data_source_block           kjnoim
_cod_depositor_comments
'Adding full bibliography for 7159539--7159545.cif.'
_cod_database_code               7159541
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C187  H170  N17  O17  '
_chemical_oxdiff_usercomment     KJMOIM
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.892
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O5-N1 \\sim O5A-N1A
 with sigma of 0.02
 N3-C15 \\sim N3A-C15A
 with sigma of 0.02
 N5-C17 \\sim N5A-C17A
 with sigma of 0.02
 N3A-N3 \\sim C16-C16A
 with sigma of 0.03
 N5-C19 \\sim N5A-C19A
 with sigma of 0.02
 N3-C16 \\sim N3A-C16A
 with sigma of 0.02
 N5-C18 \\sim N5A-C18A
 with sigma of 0.04
 N3-N2 \\sim N3A-N2A
 with sigma of 0.04
 N3-C14 \\sim N3A-C14A
 with sigma of 0.04
 N4A-N5 \\sim N5A-N4
 with sigma of 0.03
 N3A-C15A \\sim C15-N3
 with sigma of 0.03
 N4-C19 \\sim C19A-N5A
 with sigma of 0.03
 N5-N4 \\sim N5A-N4A
 with sigma of 0.03
 O5-C11 \\sim O5A-C11
 with sigma of 0.04
 C18A-N4A \\sim C17-N5
 with sigma of 0.03
 N5-C19 \\sim C19A-N4A
 with sigma of 0.03
 C17A-N5A \\sim C18-N4
 with sigma of 0.03
 N1-O5 \\sim N1A-O5A
 with sigma of 0.03
 N1-C11 \\sim N1A-C11
 with sigma of 0.02
 C11-N1 \\sim N1-N1A
 with sigma of 0.03
 C15A-C14A \\sim C14-C15
 with sigma of 0.03
 N2-C16 \\sim N2A-C16A
 with sigma of 0.02
 N2-C14 \\sim N2A-C14A
 with sigma of 0.02
 C16A-N2 \\sim N2A-C16
 with sigma of 0.03
 C15-C16 \\sim C15A-C16A
 with sigma of 0.04
 C16-C14 \\sim C16A-C14A
 with sigma of 0.04
 C14-C14A \\sim N2A-N2
 with sigma of 0.03
 N2-N2A \\sim C16A-C16
 with sigma of 0.03
 C15-C14 \\sim C15A-C14A
 with sigma of 0.02
 N2-C15 \\sim N2A-C15A
 with sigma of 0.04
 N4-C19 \\sim N4A-C19A
 with sigma of 0.02
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 N4-C18 \\sim N4A-C18A
 with sigma of 0.02
 N4-C17 \\sim N4A-C17A
 with sigma of 0.04
 C18A-C17A \\sim C17-C18
 with sigma of 0.03
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C19-C18 \\sim C19A-C18A
 with sigma of 0.04
 C18-C19 \\sim C19A-C17A
 with sigma of 0.03
3. Uiso/Uaniso restraints and constraints
Uanis(N3A) = Uanis(N3)
Uanis(N4) = Uanis(N5)
Uanis(N5) = Uanis(N4A)
Uanis(N4A) = Uanis(N5A)
Uanis(O5A) = Uanis(O5)
Uanis(N5A) = Uanis(N4)
Uanis(N1) = Uanis(N1A)
Uanis(C16A) = Uanis(C16)
Uanis(N2A) = Uanis(N2)
Uanis(C15) = Uanis(C15A)
Uanis(C14) = Uanis(C14A)
Uanis(C17) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C17A) = Uanis(C18)
4. Others
 Sof(O5A)=Sof(H5A)=Sof(N1A)=1-FVAR(1)
 Sof(O5)=Sof(H5)=Sof(N1)=FVAR(1)
 Sof(N2A)=Sof(N3A)=Sof(H3E)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=1-FVAR(2)
 Sof(N2)=Sof(N3)=Sof(H3)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=
 FVAR(2)
 Sof(N4A)=Sof(N5A)=Sof(H5K)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(H19A)=1-FVAR(3)
 Sof(N4)=Sof(N5)=Sof(H5D)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5B,H5C), C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), N3(H3), C14(H14), C15(H15), C16(H16), N3A(H3E), C14A(H14A),
 C15A(H15A), C16A(H16A), C17(H17), C18(H18), C19(H19), C17A(H17A), C18A(H18A),
 C19A(H19A)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
5.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O5A(H5A)
;
_shelx_res_checksum              35627
_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 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.797