Photoredox-Catalyzed Reductive Dimerization of Isatins and Isatin-Derived Ketimines: Diastereoselective Construction of 3,3'-Disubstituted Bisoxindoles.
Wang, Chao-Ming; Xia, Peng-Ju; Xiao, Jun-An; Li, Jun; Xiang, Hao-Yue; Chen, Xiao-Qing; Yang, Hua; The Journal of organic chemistry 82 (2017) 3895–3900; doi:10.1021/acs.joc.6b03056

data_4032408
_publ_section_title
;
 Photoredox-Catalyzed Reductive Dimerization of Isatins and Isatin-Derived
 Ketimines: Diastereoselective Construction of 3,3'-Disubstituted
 Bisoxindoles.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3895
_journal_page_last               3900
_journal_paper_doi               10.1021/acs.joc.6b03056
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C28 H32 Br2 N4 O6'
_chemical_formula_weight         680.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.074(6)
_cell_angle_beta                 70.491(6)
_cell_angle_gamma                81.465(6)
_cell_formula_units_Z            2
_cell_length_a                   11.800(2)
_cell_length_b                   12.630(3)
_cell_length_c                   13.630(3)
_cell_measurement_reflns_used    1.83
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      6223
_cell_measurement_theta_min      25.03
_cell_volume                     1775.6(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19007
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    2.322
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         6223
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0734P)^2^+0.3770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                4559
_reflns_number_total             6223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b03056_si_004.cif
_cod_data_source_block           ja1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032408--4032410.cif.

2020-10-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1775.5(6)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C1.56 H1.78 Br0.11 N0.22 O0.33'
_cod_original_formula_units_Z    36
_cod_original_formula_weight     37.80
_cod_database_code               4032408