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_7159542
_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 H23 N3 O4 S, C2 H6 O'
_chemical_formula_sum            'C24 H29 N3 O5 S'
_chemical_formula_weight         471.56
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-11-03
_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                70.4960(10)
_cell_angle_beta                 89.3540(10)
_cell_angle_gamma                79.0940(10)
_cell_formula_units_Z            2
_cell_length_a                   10.03440(10)
_cell_length_b                   10.70520(10)
_cell_length_c                   11.26660(10)
_cell_measurement_reflns_used    30944
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      77.5900
_cell_measurement_theta_min      4.1280
_cell_volume                     1118.45(2)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(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 0.992
_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    -82.00  -4.00   0.50    0.15    --  -48.79 113.00 -43.00  156
  2  \w     26.00  86.00   0.50    0.15    --   48.79-113.00-135.00  120
  3  \w    -83.00 -18.00   0.50    0.60    --  -86.25 113.00 -43.00  130
  4  \w   -154.00 -81.00   0.50    0.60    --  -86.25-113.00-135.00  146
  5  \w     40.00 108.00   0.50    0.60    --  107.75-113.00-135.00  136
  6  \w    102.00 176.00   0.50    0.60    --  107.75 113.00 -43.00  148
  7  \w    -26.00  26.00   0.50    0.15    --  -48.79  19.00-150.00  104
  8  \w    -26.00  26.00   0.50    0.15    --  -48.79  19.00 -60.00  104
  9  \w    -43.00  23.00   0.50    0.15    --  -48.79  38.00  60.00  132
 10  \w   -118.00 -73.00   0.50    0.15    --  -48.79-125.00  30.00   90
 11  \w    -63.00  23.00   0.50    0.15    --  -48.79  57.00 -90.00  172
 12  \w     35.00 120.00   0.50    0.15    --   48.79  57.00 -30.00  170
 13  \w   -158.00 -71.00   0.50    0.60    --  -86.25 -61.00 -70.69  174
 14  \w     36.00  71.00   0.50    0.60    --  107.75 -61.00 120.00   70
 15  \w     97.00 178.00   0.50    0.60    --  107.75  45.00 150.00  162
 16  \w     36.00 105.00   0.50    0.60    --  107.75 -77.00 -90.00  138
 17  \w     97.00 178.00   0.50    0.60    --  107.75  45.00-120.00  162
 18  \w     95.00 177.00   0.50    0.60    --  107.75 125.00 -30.00  164
 19  \w     95.00 177.00   0.50    0.60    --  107.75 125.00 -60.00  164
 20  \w     39.00 111.00   0.50    0.60    --  107.75-125.00  90.00  144
 21  \w     36.00  71.00   0.50    0.60    --  107.75 -61.00 150.00   70
 22  \w     36.00 105.00   0.50    0.60    --  107.75 -77.00   0.00  138
 23  \w     39.00 111.00   0.50    0.60    --  107.75-125.00  60.00  144
 24  \w     97.00 178.00   0.50    0.60    --  107.75  15.00-120.00  162
 25  \w     36.00 166.00   0.50    0.60    --  107.75   0.00-150.00  260
 26  \w     36.00 105.00   0.50    0.60    --  107.75 -77.00 -30.00  138
 27  \w     97.00 178.00   0.50    0.60    --  107.75  30.00 120.00  162
 28  \w     36.00 105.00   0.50    0.60    --  107.75 -77.00  60.00  138
 29  \w     36.00  71.00   0.50    0.60    --  107.75 -61.00  30.00   70
 30  \w     38.00 107.00   0.50    0.60    --  107.75-102.00 -22.98  138
 31  \w     39.00 111.00   0.50    0.60    --  107.75-125.00-120.00  144
 32  \w     97.00 178.00   0.50    0.60    --  107.75  30.00 -60.00  162
 33  \w     39.00 111.00   0.50    0.60    --  107.75-125.00 120.00  144
 34  \w     36.00 105.00   0.50    0.60    --  107.75 -77.00-150.00  138
 35  \w     39.00 111.00   0.50    0.60    --  107.75-125.00 -60.00  144
 36  \w     39.00 111.00   0.50    0.60    --  107.75-125.00 150.00  144
 37  \w     97.00 178.00   0.50    0.60    --  107.75  30.00  60.00  162
 38  \w     36.00 105.00   0.50    0.60    --  107.75 -95.00  90.00  138
 39  \w     39.00 111.00   0.50    0.60    --  107.75-125.00-180.00  144
 40  \w     36.00 105.00   0.50    0.60    --  107.75 -95.00-180.00  138
 41  \w     36.00 105.00   0.50    0.60    --  107.75 -95.00 -60.00  138
 42  \w     36.00  71.00   0.50    0.60    --  107.75 -61.00 -60.00   70
 43  \w     95.00 177.00   0.50    0.60    --  107.75 125.00  30.00  164
 44  \w     86.00 178.00   0.50    0.60    --  107.75  77.00  90.00  184
 45  \w     36.00  71.00   0.50    0.60    --  107.75 -61.00-150.00   70
 46  \w     97.00 178.00   0.50    0.60    --  107.75  15.00 -60.00  162
 47  \w     95.00 177.00   0.50    0.60    --  107.75 125.00 150.00  164
 48  \w     86.00 178.00   0.50    0.60    --  107.75  77.00 120.00  184
 49  \w     36.00 105.00   0.50    0.60    --  107.75 -77.00 150.00  138
 50  \w     36.00 105.00   0.50    0.60    --  107.75 -95.00 -90.00  138
 51  \w     36.00 105.00   0.50    0.60    --  107.75 -95.00 -30.00  138
 52  \w     36.00 105.00   0.50    0.60    --  107.75 -95.00   0.00  138
 53  \w     36.00 105.00   0.50    0.60    --  107.75 -95.00  60.00  138
 54  \w     39.00 108.00   0.50    0.60    --  107.75-110.00 106.96  138
 55  \w     36.00 106.00   0.50    0.60    --  107.75 -90.00-110.08  140
 56  \w     36.00 105.00   0.50    0.60    --  107.75 -95.00 150.00  138
 57  \w     99.00 137.00   0.50    0.60    --  107.75  45.00 -30.00   76
 58  \w     43.00  73.00   0.50    0.60    --  107.75-125.00  30.00   60
 59  \w     38.00 106.00   0.50    0.60    --  107.75-101.00 -98.92  136
 60  \w    108.00 134.00   0.50    0.60    --  107.75  15.00 -30.00   52
 61  \w    101.00 128.00   0.50    0.60    --  107.75  15.00 150.00   54
 62  \w    103.00 178.00   0.50    0.60    --  107.75  42.00 169.94  150
 63  \w    138.00 164.00   0.50    0.60    --  107.75 125.00  90.00   52
 64  \w     36.00  67.00   0.50    0.60    --  107.75 -61.00   0.00   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      -0.0372054000
_diffrn_orient_matrix_UB_12      0.1470165000
_diffrn_orient_matrix_UB_13      -0.0017978000
_diffrn_orient_matrix_UB_21      -0.0202877000
_diffrn_orient_matrix_UB_22      -0.0512461000
_diffrn_orient_matrix_UB_23      0.1427055000
_diffrn_orient_matrix_UB_31      0.1507546000
_diffrn_orient_matrix_UB_32      -0.0024341000
_diffrn_orient_matrix_UB_33      0.0272216000
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34127
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.920
_diffrn_reflns_theta_min         4.169
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74689
_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            Colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0502P)^2^+0.4790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4689
_reflns_number_total             4730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01136d2.cif
_cod_data_source_block           c6t2tt
_cod_depositor_comments
'Adding full bibliography for 7159539--7159545.cif.'
_cod_database_code               7159542
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H21N3O3S
_chemical_oxdiff_usercomment     C6T2TT
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.735
_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. Restrained distances
 C5-O1A \\sim C5-O1B
 with sigma of 0.03
 O1A-C8A \\sim O1B-C8B
 with sigma of 0.03
3. Uiso/Uaniso restraints and constraints
Uanis(C8A) = Uanis(C8B)
Uanis(O1A) = Uanis(O1B)
4. Others
 Sof(O1B)=Sof(C8B)=Sof(H8BA)=Sof(H8BB)=Sof(H8BC)=1-FVAR(1)
 Sof(O1A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C23(H23A,H23B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C20(H20)
5.c Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C8B(H8BA,H8BB,H8BC), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              666
_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 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.572