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_7251123
_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         'C15 H13 N O S'
_chemical_formula_sum            'C15 H13 N O S'
_chemical_formula_weight         255.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-03-29
_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                90
_cell_angle_beta                 92.4620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.22690(10)
_cell_length_b                   13.1586(3)
_cell_length_c                   15.0552(4)
_cell_measurement_reflns_used    6926
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.681
_cell_measurement_theta_min      4.465
_cell_volume                     1232.44(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10964
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.672
_diffrn_reflns_theta_min         4.464
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.208
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1407 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.0963.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2515
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0801
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1783P)^2^+0.4592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2429
_refine_ls_wR_factor_ref         0.2459
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2399
_reflns_number_total             2515
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04510j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7251123--7251124.cif.'
_cod_database_code               7251123
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.679
_shelx_estimated_absorpt_t_min   0.587
_olex2_refinement_description
;
1. Rigid bond restraints
 S1, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C3, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4), C10(H10), C3(H3), C1(H1), C8(H8), C11(H11)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              30015
_olex2_submission_special_instructions 'No special instructions were received'