Photoredox Asymmetric Nucleophilic Dearomatization of Indoles with Neutral Radicals
Zhang, Yueteng; Ji, Peng; Gao, Feng; Huang, He; Zeng, Fanxun; Wang, Wei; ACS Catalysis 11 (2021) 998–1007; doi:10.1021/acscatal.0c04696

data_4518470
_publ_section_title
;
 Photoredox Asymmetric Nucleophilic Dearomatization of Indoles with
 Neutral Radicals
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              998
_journal_page_last               1007
_journal_paper_doi               10.1021/acscatal.0c04696
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H28 N2 O5 S'
_chemical_formula_sum            'C27 H28 N2 O5 S'
_chemical_formula_weight         492.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.610(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.7379(12)
_cell_length_b                   7.3689(4)
_cell_length_c                   14.3911(7)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.25
_cell_volume                     2410.3(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23129
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         1.416
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0524 before and 0.0455 after correction. The Ratio of minimum to maximum transmission is 0.9186. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4583
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0461P)^2^+0.6736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4373
_reflns_number_total             4583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04696_si_002.cif
_cod_data_source_block           mo_yz13168c_0m
_cod_database_code               4518470
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.957
_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:
 C18(H18), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C20(H20A,H20B), C7(H7A,H7B), C23(H23A,H23B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C15(H15), C13(H13), C3(H3), C5(H5), C2(H2), C14(H14),
 C6(H6), C1(H1)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              95246
_shelx_hkl_checksum              7713
_olex2_submission_special_instructions 'No special instructions were received'