N-heterocyclic carbene and photocatalyst-catalyzed rapid access to indole ketones via radical C(sp3)–H acylation
Nie, Guihua; Tu, Ting; Liao, Tianhui; Liu, Donghan; Ye, Wenjun; Ren, Shi-Chao; Green Chemistry 26 (2024) 5397–5408; doi:10.1039/D4GC00653D

data_7248336
_publ_section_title
;
 N-heterocyclic carbene and photocatalyst-catalyzed rapid access to indole
 ketones via radical C(sp3)--H acylation
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              5397
_journal_page_last               5408
_journal_paper_doi               10.1039/D4GC00653D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-20 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                83.474(2)
_cell_angle_beta                 89.157(2)
_cell_angle_gamma                70.718(2)
_cell_formula_units_Z            4
_cell_length_a                   9.6651(6)
_cell_length_b                   10.0573(7)
_cell_length_c                   18.1252(12)
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.684
_cell_measurement_theta_min      4.079
_cell_volume                     1651.76(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32984
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.901
_diffrn_reflns_theta_min         2.135
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1695 before and 0.0955 after correction.
The Ratio of minimum to maximum transmission is 0.8610.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         7473
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0723
_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^)+(0.1015P)^2^+0.9051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1966
_refine_ls_wR_factor_ref         0.2090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5563
_reflns_number_total             7473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc00653d2.cif
_cod_data_source_block           230909_ngh_c069_3a_zlj_0m
_cod_depositor_comments
'Adding full bibliography for 7248336--7248338.cif.'
_cod_database_code               7248336
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.941
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C33-C32 \\sim C33-C32A
 with sigma of 0.02
 C31-C32 \\sim C31-C32A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C32A \\sim C33: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
4. Others
 Sof(H33C)=Sof(H33D)=Sof(H31C)=Sof(H31D)=Sof(C32A)=Sof(H32C)=Sof(H32D)=1-FVAR(1)
 Sof(H33A)=Sof(H33B)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C30(H30), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C33(H33C,H33D), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,
 H12B), C31(H31A,H31B), C31(H31C,H31D), C32(H32A,H32B), C32A(H32C,H32D)
5.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C19(H19), C37(H37), C17(H17), C16(H16), C22(H22), C38(H38),
 C25(H25), C41(H41), C2(H2), C40(H40), C1(H1), C23(H23), C4(H4), C24(H24),
 C3(H3)
5.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C42(H42A,H42B,
 H42C)
;
_shelx_res_checksum              42948
_shelx_hkl_checksum              64663
_olex2_submission_special_instructions 'No special instructions were received'