Mechanism-controlled switchable regioselective O- and N-cyclization alkenylation of alkenylbenzamides via dual photoredox and cobalt catalysis
Rao, Feiyang; Hu, Kui; He, Yuanxiang; Zuo, Ziyi; Lv, Shiming; Geng, Shu; Pan, Li; Wang, Hongmei; Huang, Feng; Green Chemistry 27 (2025) 14328–14337; doi:10.1039/D5GC04510J

data_7251124
_publ_section_title
;
 Mechanism-controlled switchable regioselective O- and N-cyclization
 alkenylation of alkenylbenzamides via dual photoredox and cobalt
 catalysis
;
_journal_issue                   44
_journal_name_full               'Green Chemistry'
_journal_page_first              14328
_journal_page_last               14337
_journal_paper_doi               10.1039/D5GC04510J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C17 H15 N O'
_chemical_formula_sum            'C17 H15 N O'
_chemical_formula_weight         249.30
_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             2023-08-04
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-18 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                82.150(2)
_cell_angle_beta                 86.291(2)
_cell_angle_gamma                82.644(2)
_cell_formula_units_Z            2
_cell_length_a                   6.24510(10)
_cell_length_b                   9.7295(2)
_cell_length_c                   11.3595(2)
_cell_measurement_reflns_used    4763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.1120
_cell_measurement_theta_min      3.9290
_cell_volume                     677.34(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.964
_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     -9.00  82.00   0.50    0.50    --   42.00   1.00  -8.00  182
  2  \w    -44.00 -18.00   0.50    0.50    --   42.00  -1.00 169.00   52
  3  \w    155.00 180.00   0.50    0.50    --   93.70   1.00  -8.00   50
  4  \w     92.00 136.00   0.50    0.50    --   93.70   1.00  -8.00   88
  5  \w     18.00  50.00   0.50    0.50    --   42.00 -77.00  90.00   64
  6  \w    -46.00  32.00   0.50    0.50    --   42.00 -82.00-180.00  156
  7  \w    -21.00   4.00   0.50    0.50    --   42.00 -54.00 -90.00   50
  8  \w     37.00  68.00   0.50    0.50    --   42.00 -82.00-150.00   62
  9  \w     80.00 130.00   0.50    0.50    --   42.00  65.00-180.00  100
 10  \w     23.00  65.00   0.50    0.50    --   42.00 -65.00 -30.00   84
 11  \w    -44.00  14.00   0.50    0.50    --   42.00 -65.00 -30.00  116
 12  \w     16.00  46.00   0.50    0.50    --   42.00 -54.00 -90.00   60
 13  \w    -43.00   1.00   0.50    0.50    --   42.00 -77.00  90.00   88
 14  \w    -42.00  19.00   0.50    0.50    --   42.00 -82.00-150.00  122
 15  \w     12.00  71.00   0.50    0.50    --   42.00 -43.00-180.00  118
 16  \w     36.00  63.00   0.50    0.50    --   42.00 -82.00-180.00   54
 17  \w    -16.00  68.00   0.50    0.50    --   42.00 -82.00  30.00  168
 18  \w     70.00 115.00   0.50    0.50    --   93.70 -82.00   0.00   90
 19  \w      4.00  65.00   0.50    0.50    --   93.70 -82.00   0.00  122
 20  \w     82.00 176.00   0.50    0.50    --   93.70  50.00 -90.00  188
 21  \w    142.00 183.00   0.50    0.50    --   93.70  50.00-150.00   82
 22  \w      4.00 121.00   0.50    0.50    --   93.70 -82.00 -60.00  234
 23  \w     60.00 117.00   0.50    0.50    --   93.70 -68.00  60.00  114
 24  \w     96.00 124.00   0.50    0.50    --   93.70 -33.00 -90.00   56
 25  \w     10.00  49.00   0.50    0.50    --   93.70 -33.00 -90.00   78
 26  \w     75.00 114.00   0.50    0.50    --   93.70  50.00-150.00   78
 27  \w     39.00  84.00   0.50    0.50    --   93.70 -82.00  90.00   90
 28  \w      5.00  93.00   0.50    0.50    --   93.70 -82.00-150.00  176
 29  \w     65.00  90.00   0.50    0.50    --   93.70 -82.00-180.00   50
 30  \w     33.00  74.00   0.50    0.50    --   93.70 -82.00 -30.00   82
 31  \w     79.00 104.00   0.50    0.50    --   93.70 -82.00  60.00   50
 32  \w     62.00  88.00   0.50    0.50    --   93.70 -82.00-120.00   52
 33  \w     80.00 174.00   0.50    0.50    --   93.70  68.00 150.00  188
 34  \w      5.00  60.00   0.50    0.50    --   93.70 -82.00-120.00  110
 35  \w     70.00 102.00   0.50    0.50    --   93.70  68.00  60.00   64
 36  \w     48.00  75.00   0.50    0.50    --   93.70 -82.00  60.00   54
 37  \w     32.00  60.00   0.50    0.50    --   93.70 -82.00-180.00   56
 38  \w      4.00  88.00   0.50    0.50    --   93.70 -82.00 -90.00  168
 39  \w     14.00  40.00   0.50    0.50    --   93.70 -68.00  60.00   52
 40  \w      5.00  99.00   0.50    0.50    --   93.70 -82.00 120.00  188
 41  \w      4.00  69.00   0.50    0.50    --   93.70  -1.00 169.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1955202000
_diffrn_orient_matrix_UB_12      0.0818238000
_diffrn_orient_matrix_UB_13      -0.0000822000
_diffrn_orient_matrix_UB_21      0.1538191000
_diffrn_orient_matrix_UB_22      -0.1369818000
_diffrn_orient_matrix_UB_23      -0.0007618000
_diffrn_orient_matrix_UB_31      0.0109926000
_diffrn_orient_matrix_UB_32      0.0215851000
_diffrn_orient_matrix_UB_33      -0.1370581000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5735
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.050
_diffrn_reflns_theta_min         3.933
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.124(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0768P)^2^+0.0825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2217
_reflns_number_total             2384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04510j2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7251123--7251124.cif.'
_cod_database_code               7251124
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.911
_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 Ternary CH refined with riding coordinates:
 C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C2(H2), C6(H6), C10(H10), C11(H11), C3(H3), C4(H4), C5(H5)
2.c X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              82037
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 7.163
_oxdiff_exptl_absorpt_empirical_full_min 0.504