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_7160393
_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_formula_moiety         'C19 H16 N2 O4'
_chemical_formula_sum            'C19 H14 N2 O4'
_chemical_formula_weight         334.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-09-30 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.295(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6051(10)
_cell_length_b                   9.8026(6)
_cell_length_c                   21.1562(13)
_cell_measurement_reflns_used    5135
_cell_measurement_temperature    243(60)
_cell_measurement_theta_max      29.9410
_cell_measurement_theta_min      3.9140
_cell_volume                     3202.4(3)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      243(60)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.828
_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     -9.00  38.00   0.50   37.71    --   -2.33  53.00 -66.00   94
  2  \w    -64.00   0.00   0.50   37.71    --   -2.33 -53.00 149.00  128
  3  \w    -59.00   2.00   0.50   37.71    --    1.54 -19.00-150.00  122
  4  \w    -42.00  18.00   0.50   37.71    --   -2.33 -77.00  90.00  120
  5  \w    -10.00  15.00   0.50   37.71    --   -2.33 -99.00   0.00   50
  6  \w    -21.00   6.00   0.50   37.71    --   -2.33  77.00  90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0432308000
_diffrn_orient_matrix_UB_12      -0.0050965000
_diffrn_orient_matrix_UB_13      -0.0156942000
_diffrn_orient_matrix_UB_21      0.0041901000
_diffrn_orient_matrix_UB_22      0.0643737000
_diffrn_orient_matrix_UB_23      -0.0145703000
_diffrn_orient_matrix_UB_31      0.0149599000
_diffrn_orient_matrix_UB_32      -0.0326309000
_diffrn_orient_matrix_UB_33      -0.0262452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15065
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.232
_diffrn_reflns_theta_min         3.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58974
_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            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0889P)^2^+3.0274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1841
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3103
_reflns_number_total             3943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00057b2.cif
_cod_data_source_block           nks-ckj-453
_cod_depositor_comments
'Adding full bibliography for 7160390--7160394.cif.'
_cod_database_code               7160393
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C152 H128 N16 O32 '
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.999
_diffrn_oxdiff_digest_frames
;
0118d07eea0a4bab33e831aa2f29f1b96a00025d058
;
_diffrn_oxdiff_digest_hkl
;
019ec82a3cf15463555f6c033ac152612d0d42
;
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C19(H19), C18(H18), C16(H16), C17(H17), C5(H5), C2(H2A),
 C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              27267
_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 1.568
_oxdiff_exptl_absorpt_empirical_full_min 0.691