Photoredox-catalyzed direct aminoalkylation of isatins: diastereoselective access to 3-hydroxy-3-aminoalkylindolin-2-ones analogues
Wang, Chao-Ming; Song, Dan; Xia, Peng-Ju; Ye, Zhi-Peng; Xiao, Jun-An; Xiang, Hao-Yue; Chen, Xiao-Qing; Yang, Hua; Organic Chemistry Frontiers 5 (2018) 1608–; doi:10.1039/C8QO00201K

data_1554289
_publ_section_title
;
 Photoredox-catalyzed direct aminoalkylation of isatins:
 diastereoselective access to 3-hydroxy-3-aminoalkylindolin-2-ones
 analogues
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1608
_journal_paper_doi               10.1039/C8QO00201K
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C30 H25 Br N2 O2'
_chemical_formula_weight         525.45
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-03-16 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.135(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.3150(15)
_cell_length_b                   11.3915(7)
_cell_length_c                   18.4957(12)
_cell_measurement_reflns_used    9260
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      0.87
_cell_volume                     4905.0(5)
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28580
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         0.87
_exptl_absorpt_coefficient_mu    1.707
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.372
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         9260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+8.6257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                6988
_reflns_number_total             9260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00201k2.cif
_cod_data_source_block           ja
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C3.93 H3.28 Br0.13 N0.26 O0.26'
_cod_original_formula_weight         68.91
_cod_original_formula_units_Z            61
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1554289