Harnessing the reactivity of captodative radicals: photocatalytic α-pyridination of glycyl derivatives through reversible radical coupling.
Yamazaki, Ken; Akimoto, Shuta; Miura, Tomoya; Organic & biomolecular chemistry 23 (2025) 9936–9941; doi:10.1039/d5ob00675a

data_7160589
_publ_section_title
;
 Harnessing the reactivity of captodative radicals: photocatalytic
 &#x3b1;-pyridination of glycyl derivatives through reversible radical
 coupling.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9936
_journal_page_last               9941
_journal_paper_doi               10.1039/d5ob00675a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H18 N2 O3'
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
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_atom_sites_solution_primary     iterative
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;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-03 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                84.851(4)
_cell_angle_beta                 69.482(5)
_cell_angle_gamma                67.945(5)
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_cell_length_c                   10.8014(5)
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_cell_measurement_temperature    173.15
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_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
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CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
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CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
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_diffrn_ambient_temperature      173.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.995
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_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9424
_diffrn_reflns_point_group_measured_fraction_full 0.995
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_diffrn_source                   'Rotating Anode'
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_diffrn_source_power             1.2
_diffrn_source_target            Mo
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_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.090
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_description       block
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_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.39
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_refine_diff_density_max         0.300
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0474P)^2^+0.1979P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2982
_reflns_number_total             3513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00675a2.cif
_cod_data_source_block           ov_akimoto-byproduct_autored
_cod_depositor_comments
'Adding full bibliography for 7160589--7160590.cif.'
_cod_database_code               7160589
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.930
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C6(H6), C5(H5), C17(H17), C3(H3), C2(H2), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              84693
_olex2_submission_special_instructions 'No special instructions were received'