Enantioselective dicarbofunctionalization of (<i>E</i>)-alkenyloxindoles with pyridinium salts by chiral Lewis acid/photo relay catalysis.
Zhang, Dong; Dong, Shunxi; He, Qianwen; Luo, Yao; Liu, Yun; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 56 (2020) 12757–12760; doi:10.1039/d0cc05621a

data_7127242
_publ_section_title
;
 Enantioselective dicarbofunctionalization of (<i>E</i>)-alkenyloxindoles
 with pyridinium salts by chiral Lewis acid/photo relay catalysis.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12757
_journal_page_last               12760
_journal_paper_doi               10.1039/d0cc05621a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C27 H25 Br N2 O4'
_chemical_formula_sum            'C27 H25 Br N2 O4'
_chemical_formula_weight         521.40
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-06-12 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.3160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2371(4)
_cell_length_b                   16.5924(5)
_cell_length_c                   11.5023(3)
_cell_measurement_reflns_used    9778
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      72.36
_cell_measurement_theta_min      3.48
_cell_volume                     2424.57(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44480
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.401
_diffrn_reflns_theta_min         3.479
_exptl_absorpt_coefficient_mu    2.608
_exptl_absorpt_correction_T_max  0.8894
_exptl_absorpt_correction_T_min  0.7382
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc, PE'
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.074
_refine_diff_density_max         1.302
_refine_diff_density_min         -1.217
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4773
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0399P)^2^+2.6960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4508
_reflns_number_total             4773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05621a2.cif
_cod_data_source_block           zhd019
_cod_depositor_comments
'Adding full bibliography for 7127240--7127244.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7127242
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.686
_shelx_estimated_absorpt_t_max   0.830
_shelx_res_checksum              71679
_shelx_hkl_checksum              16410