Electrochemical oxidation–cyclocondensation of chitin-derived 3-acetamido-5-acetylfuran (3A5AF) for the synthesis of 3-acetyl-4-acetamidopyrrolin-2-ones
Arteaga Giraldo, Juan J.; Söhnel, Tilo; Kilmartin, Paul A.; Sperry, Jonathan; Green Chemistry 27 (2025) 4259–4266; doi:10.1039/D4GC06067A

data_7250160
_publ_section_title
;
 Electrochemical oxidation--cyclocondensation of chitin-derived
 3-acetamido-5-acetylfuran (3A5AF) for the synthesis of
 3-acetyl-4-acetamidopyrrolin-2-ones
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              4259
_journal_page_last               4266
_journal_paper_doi               10.1039/D4GC06067A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C19 H21 N3 O4'
_chemical_formula_sum            'C19 H21 N3 O4'
_chemical_formula_weight         355.39
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-11-06 deposited with the CCDC.	2025-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.436(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5658(8)
_cell_length_b                   8.2756(5)
_cell_length_c                   22.671(2)
_cell_measurement_reflns_used    2538
_cell_measurement_temperature    120.0(4)
_cell_measurement_theta_max      70.8920
_cell_measurement_theta_min      4.7040
_cell_volume                     1770.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_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     17.00  47.00   0.50    4.46    --   46.23 -42.00 -27.00   60
  2  \w     19.00  44.00   0.50   17.84    --   97.33 -42.00 -27.00   50
  3  \w     20.00  46.00   0.50   17.84    --   97.33 -45.00   0.00   52
  4  \w     38.00  66.00   0.50   17.84    --   97.33 -61.00  30.00   56
  5  \w     23.00  49.00   0.50   17.84    --   97.33 -45.00  60.00   52
  6  \w     20.00  47.00   0.50   17.84    --   97.33 -45.00  30.00   54
  7  \w     66.00 117.00   0.50   17.84    --   97.33  15.00   0.00  102
  8  \w    133.00 176.00   0.50   17.84    --   97.33  15.00   0.00   86
  9  \w    117.00 147.00   0.50   17.84    --   97.33  42.00 125.00   60
 10  \w     48.00  78.00   0.50    4.46    --   46.23  42.00 125.00   60
 11  \w    -16.00  16.00   0.50    4.46    --   46.23 -42.00 -27.00   64
 12  \w     31.00  59.00   0.50   17.84    --   97.33 -61.00-120.00   56
 13  \w     20.00  51.00   0.50   17.84    --   97.33 -45.00-120.00   62
 14  \w     78.00 118.00   0.50   17.84    --   97.33  45.00-150.00   80
 15  \w    142.00 175.00   0.50   17.84    --   97.33  45.00-150.00   66
 16  \w     71.00 123.00   0.50   17.84    --   97.33 178.00 -60.00  104
 17  \w     29.00  77.00   0.50    4.46    --   46.23  57.00-180.00   96
 18  \w    -68.00 -36.00   0.50   17.84    --  -90.25  61.00 -90.00   64
 19  \w    -50.00 -12.00   0.50   17.84    --  -90.25  45.00 -90.00   76
 20  \w    -51.00 -26.00   0.50   17.84    --  -90.25  45.00-150.00   50
 21  \w    -71.00 -23.00   0.50   17.84    --  -90.25  61.00 -60.00   96
 22  \w    -71.00 -21.00   0.50   17.84    --  -90.25  61.00-120.00  100
 23  \w    -93.00 -65.00   0.50    4.46    --  -46.23 -42.00 -27.00   56
 24  \w    -31.00  -6.00   0.50    4.46    --  -46.23  42.00 125.00   50
 25  \w    -47.00 -22.00   0.50   17.84    --  -90.25  42.00 125.00   50
 26  \w    -50.00 -15.00   0.50   17.84    --  -90.25  45.00 150.00   70
 27  \w    -71.00 -45.00   0.50   17.84    --  -90.25  61.00 150.00   52
 28  \w   -102.00 -76.00   0.50   17.84    --  -90.25 -42.00 -27.00   52
 29  \w   -102.00 -75.00   0.50   17.84    --  -90.25 -77.00 -30.00   54
 30  \w   -123.00 -73.00   0.50    4.46    --  -46.23-125.00 -90.00  100
 31  \w   -122.00 -74.00   0.50    4.46    --  -46.23-125.00 -60.00   96
 32  \w   -119.00 -82.00   0.50    4.46    --  -46.23-125.00  60.00   74
 33  \w   -163.00-126.00   0.50   17.84    --  -90.25 -77.00 -30.00   74
 34  \w   -173.00 -62.00   0.50   17.84    --  -90.25 -15.00   0.00  222
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0999552000
_diffrn_orient_matrix_UB_12      -0.0636442000
_diffrn_orient_matrix_UB_13      0.0553535000
_diffrn_orient_matrix_UB_21      0.0965352000
_diffrn_orient_matrix_UB_22      -0.0748459000
_diffrn_orient_matrix_UB_23      -0.0407294000
_diffrn_orient_matrix_UB_31      0.0860340000
_diffrn_orient_matrix_UB_32      0.1582330000
_diffrn_orient_matrix_UB_33      0.0029367000
_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     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10105
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        65.088
_diffrn_reflns_theta_max         65.088
_diffrn_reflns_theta_min         5.617
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_preparation       'solvents of acetone & pentane'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0823
_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^)+(0.0275P)^2^+5.4492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.1980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2299
_reflns_number_total             2943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc06067a2.cif
_cod_data_source_block           ja_92_11_1
_cod_depositor_comments          'Adding full bibliography for 7250160.cif.'
_cod_original_cell_volume        1770.4(3)
_cod_database_code               7250160
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C19H21N3O3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.912
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C3(H3A), C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              14307
_shelx_hkl_checksum              75429
_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 1.854
_oxdiff_exptl_absorpt_empirical_full_min 0.368