PIDA-mediated synthesis of kynurenine derivatives by oxidative fragmentation of the tryptophan scaffold.
Jena, Chinmay K.; Patnaik, Aurobindo; Nayak, Sushree S.; Kumari, Supriya; Panda, Ankita; Dixit, Manjusha; Sharma, Nagendra K.; Organic & biomolecular chemistry 23 (2025) 3208–3223; doi:10.1039/d5ob00057b

data_7160391
_publ_section_title
;
 PIDA-mediated synthesis of kynurenine derivatives by oxidative
 fragmentation of the tryptophan scaffold.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3208
_journal_page_last               3223
_journal_paper_doi               10.1039/d5ob00057b
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration s
_chemical_formula_moiety         'C20 H27 N3 O7'
_chemical_formula_sum            'C20 H27 N3 O7'
_chemical_formula_weight         421.44
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-03-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-10-01 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                82.934(3)
_cell_angle_beta                 85.650(3)
_cell_angle_gamma                73.874(3)
_cell_formula_units_Z            1
_cell_length_a                   5.03333(16)
_cell_length_b                   8.5410(3)
_cell_length_c                   13.3951(4)
_cell_measurement_reflns_used    5956
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      77.4870
_cell_measurement_theta_min      5.3900
_cell_volume                     548.47(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_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     31.00 112.00   0.50    0.11    --   49.06  71.00 117.00  162
  2  \w    -14.00  68.00   0.50    0.11    --   49.06 -71.00 -13.00  164
  3  \w     44.00 125.00   0.50    0.59    --  106.83 -71.00 -13.00  162
  4  \w     88.00 170.00   0.50    0.59    --  106.83  71.00 117.00  164
  5  \w   -102.00 -20.00   0.50    0.11    --  -38.50 -71.00 -13.00  164
  6  \w    -50.00  24.00   0.50    0.11    --  -38.50  57.00-180.00  148
  7  \w    -57.00  25.00   0.50    0.11    --  -38.50  71.00 117.00  164
  8  \w   -101.00 -27.00   0.50    0.11    --  -38.50 -57.00-120.00  148
  9  \w    -86.00  -6.00   0.50    0.11    --  -38.50 125.00  60.00  160
 10  \w     44.00 112.00   0.50    0.59    --  106.83-125.00 -30.00  136
 11  \w     42.00 111.00   0.50    0.59    --  106.83 -45.00 -60.00  138
 12  \w     98.00 170.00   0.50    0.59    --  106.83  54.00  43.93  144
 13  \w     39.00 106.00   0.50    0.59    --  106.83 -94.00  30.00  134
 14  \w     43.00 130.00   0.50    0.59    --  106.83 -77.00 150.00  174
 15  \w    104.00 175.00   0.50    0.59    --  106.83  30.00  90.00  142
 16  \w     42.00 111.00   0.50    0.59    --  106.83 -45.00 120.00  138
 17  \w     44.00 120.00   0.50    0.59    --  106.83 -61.00-150.00  152
 18  \w     39.00 106.00   0.50    0.59    --  106.83 -94.00 120.00  134
 19  \w     39.00 106.00   0.50    0.59    --  106.83 -94.00 -30.00  134
 20  \w     44.00 120.00   0.50    0.59    --  106.83 -61.00  30.00  152
 21  \w     99.00 175.00   0.50    0.59    --  106.83  15.00-150.00  152
 22  \w     43.00 130.00   0.50    0.59    --  106.83 -77.00 120.00  174
 23  \w    102.00 171.00   0.50    0.59    --  106.83  45.00 -60.00  138
 24  \w     44.00 112.00   0.50    0.59    --  106.83-125.00   0.00  136
 25  \w    103.00 171.00   0.50    0.59    --  106.83  77.00-120.00  136
 26  \w     39.00 115.00   0.50    0.59    --  106.83 -15.00  90.00  152
 27  \w     41.00 108.00   0.50    0.59    --  106.83-107.00 141.95  134
 28  \w   -102.00 -38.00   0.50    0.11    --  -38.50 -71.00-156.54  128
 29  \w     38.00 112.00   0.50    0.11    --   49.06  57.00  90.00  148
 30  \w     38.00 112.00   0.50    0.11    --   49.06  57.00 -30.00  148
 31  \w     38.00 112.00   0.50    0.11    --   49.06  57.00-120.00  148
 32  \w     38.00 112.00   0.50    0.11    --   49.06  57.00-180.00  148
 33  \w     38.00 112.00   0.50    0.11    --   49.06  57.00  30.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8615
_diffrn_reflns_point_group_measured_fraction_full 0.787
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.774
_diffrn_reflns_theta_min         3.328
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1038 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0592P)^2^+0.1059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.532
_reflns_Friedel_fraction_full    0.578
_reflns_Friedel_fraction_max     0.519
_reflns_number_gt                3280
_reflns_number_total             3497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00057b2.cif
_cod_data_source_block           nks-b-alakyn_auto
_cod_depositor_comments
'Adding full bibliography for 7160390--7160394.cif.'
_cod_original_cell_volume        548.46(3)
_cod_database_code               7160391
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.992
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C8(H8A,H8B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C3(H3A), C5(H5), C6(H6), C4(H4)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C11(H11A,H11B,
 H11C)
;
_shelx_res_checksum              97468
_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
;