Silyl Radical-Mediated Carbocyclization of Acrylamide-/Vinyl Sulfonamide-Attached Alkylidenecyclopropanes via Photoredox Catalysis with a Catalytic Amount of Silane Reagent
Zhang, Xiao-Yu; Wu, Xiao-Yun; Zhang, Bo; Wei, Yin; Shi, Min; ACS Catalysis  (2021) 4372–4380; doi:10.1021/acscatal.1c00240

data_4518582
_publ_section_title
;
 Silyl Radical-Mediated Carbocyclization of Acrylamide-/Vinyl
 Sulfonamide-Attached Alkylidenecyclopropanes via Photoredox Catalysis
 with a Catalytic Amount of Silane Reagent
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              4372
_journal_page_last               4380
_journal_paper_doi               10.1021/acscatal.1c00240
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_sum            'C21 H21 N O'
_chemical_formula_weight         303.39
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4865(2)
_cell_length_b                   7.4865(2)
_cell_length_c                   59.2740(19)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.683
_cell_measurement_theta_min      4.810
_cell_volume                     3322.17(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       73
_diffrn_reflns_limit_l_min       -72
_diffrn_reflns_number            29434
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.806
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0(6)
_refine_ls_extinction_coef       0.031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0684
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+2.2655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1823
_reflns_Friedel_coverage         0.577
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2766
_reflns_number_total             3253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c00240_si_002.cif
_cod_data_source_block           mo_d8v19724_0m
_cod_original_cell_volume        3322.2(2)
_cod_database_code               4518582
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-4
_shelx_res_checksum              23945
_shelx_hkl_checksum              76911