Electrochemical oxidation-induced benzylic C(sp3)–H functionalization towards the atom-economic synthesis of oxazole heterocycles
Yang, Na; Li, Anni; Gao, Hui; Liao, Li-Mei; Yang, Yu-Ping; Wang, Pei-Long; Li, Hongji; Green Chemistry 25 (2023) 5128–5133; doi:10.1039/D2GC04782A

data_7246830
_publ_section_title
;
 Electrochemical oxidation-induced benzylic C(sp3)--H functionalization
 towards the atom-economic synthesis of oxazole heterocycles
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              5128
_journal_page_last               5133
_journal_paper_doi               10.1039/D2GC04782A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C24 H19 N O3'
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.40
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-03-09
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-03-09 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.647(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.998(3)
_cell_length_b                   13.804(4)
_cell_length_c                   14.731(4)
_cell_measurement_reflns_used    464
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      3.09
_cell_volume                     1827.8(9)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            100316
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.654
_diffrn_reflns_theta_min         2.768
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0605 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.9753.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.4734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3453
_reflns_number_total             4241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04782a2.cif
_cod_data_source_block           2
_cod_depositor_comments          'Adding full bibliography for 7246830.cif.'
_cod_original_cell_volume        1827.9(9)
_cod_database_code               7246830
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              78414
_olex2_submission_special_instructions 'No special instructions were received'