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_7160392
_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         'C16 H18 N2 O5'
_chemical_formula_sum            'C16 H18 N2 O5'
_chemical_formula_weight         318.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
;
2024-09-30 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6238(3)
_cell_length_b                   14.8768(8)
_cell_length_c                   19.4102(10)
_cell_measurement_reflns_used    6749
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.6880
_cell_measurement_theta_min      4.5690
_cell_volume                     1623.94(15)
_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 0.999
_diffrn_measured_fraction_theta_max 0.960
_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    -42.00  27.00   0.50    0.25    --  -38.50  40.00 170.00  138
  2  \w   -104.00 -35.00   0.50    0.25    --  -38.50 -40.00  16.00  138
  3  \w    -16.00  53.00   0.50    0.25    --   49.31 -40.00  16.00  138
  4  \w     46.00 115.00   0.50    0.25    --   49.31  40.00 170.00  138
  5  \w     42.00 111.00   0.50    0.97    --  107.46 -40.00  16.00  138
  6  \w    104.00 173.00   0.50    0.97    --  107.46  40.00 170.00  138
  7  \w     28.00  98.00   0.50    0.25    --   49.31-125.00  30.00  140
  8  \w     46.00  99.00   0.50    0.25    --   49.31  37.00-120.00  106
  9  \w     82.00 108.00   0.50    0.97    --  107.46 -30.00-180.00   52
 10  \w     99.00 133.00   0.50    0.97    --  107.46 125.00  30.00   68
 11  \w    141.00 168.00   0.50    0.97    --  107.46 125.00  30.00   54
 12  \w     52.00  78.00   0.50    0.97    --  107.46-125.00  60.00   52
 13  \w     63.00 111.00   0.50    0.97    --  107.46-125.00-180.00   96
 14  \w     40.00  75.00   0.50    0.97    --  107.46 -30.00-180.00   70
 15  \w    118.00 152.00   0.50    0.97    --  107.46 125.00  90.00   68
;
_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  0.0436
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7534
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.905
_diffrn_reflns_theta_min         3.744
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76053
_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 whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.002
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1116 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0756P)^2^+0.2678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.603
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                3016
_reflns_number_total             3118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00057b2.cif
_cod_data_source_block           nks-ckj-boc-w-spiro_auto
_cod_depositor_comments
'Adding full bibliography for 7160390--7160394.cif.'
_cod_database_code               7160392
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.984
_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:
 C00D(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), C00H(H00H), C00L(H00N), C00M(H00O), C00N(H00P)
2.d Idealised Me refined as rotating group:
 C00G(H00C,H00E,H00F), C00J(H00G,H00I,H00J), C00K(H00K,H00L,H00M)
;
_shelx_res_checksum              57075
_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
;