Nickel catalysed SET-induced oxygenation of (aryl)(N-heteroaryl)methanes with molecular oxygen.
Chauhan, Shivani Singh; Kakadiya, Harikrushn Ghanashyambhai; Singh, Anupam Kumar; Ghosh, Eliza; Paine, Tapan Kanti; Bhadra, Sukalyan; Organic & biomolecular chemistry 24 (2026) 1474–1480; doi:10.1039/d5ob01658d

data_7160996
_publ_section_title
;
 Nickel catalysed SET-induced oxygenation of (aryl)(N-heteroaryl)methanes
 with molecular oxygen.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1474
_journal_page_last               1480
_journal_paper_doi               10.1039/d5ob01658d
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C18 H11 N O2'
_chemical_formula_sum            'C18 H11 N O2'
_chemical_formula_weight         273.28
_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
_audit_creation_date             2025-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-05-07 deposited with the CCDC.	2026-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.751(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3789(9)
_cell_length_b                   12.2013(8)
_cell_length_c                   8.2874(5)
_cell_measurement_reflns_used    9363
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.079
_cell_measurement_theta_min      3.051
_cell_volume                     1302.04(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            70789
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.662
_diffrn_reflns_theta_min         2.300
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1184 before and 0.0849 after correction. The Ratio of minimum to maximum transmission is 0.8425. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0728P)^2^+0.2420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1797
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2329
_reflns_number_total             4013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01658d2.cif
_cod_data_source_block           sc_780_0ma_a
_cod_database_code               7160996
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              52229
_olex2_submission_special_instructions 'No special instructions were received'