Photoredox Asymmetric Catalytic Enantioconvergent Substitution of 3-Chlorooxindoles
Zeng, Guangkuo; Li, Yunqiang; Qiao, Baokun; Zhao, Xiaowei; Jiang, Zhiyong; Chemical Communications  (2019) –; doi:10.1039/C9CC05304B

data_7124071
_publ_section_title
;
 Photoredox Asymmetric Catalytic Enantioconvergent Substitution of
 3-Chlorooxindoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05304B
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H20 Br F3 N2 O2, 0.5(H2 O)'
_chemical_formula_sum            'C24 H21 Br F3 N2 O2.5'
_chemical_formula_weight         514.33
_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'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-11 deposited with the CCDC.    2019-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.467(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.455(2)
_cell_length_b                   6.3246(2)
_cell_length_c                   14.0068(9)
_cell_measurement_reflns_used    2141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.7970
_cell_measurement_theta_min      5.6200
_cell_volume                     2209.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega -104.00  -11.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  -30.0000 186

  2 omega  -68.00  -41.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 54

  3 omega  -99.00  -25.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   90.0000 148

  4 omega   50.00   75.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  150.0000 50

  5 omega   58.00   85.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -126.0000   76.0000 54

  6 omega   79.00  109.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 60

  7 omega   -1.00   65.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 132

  8 omega   57.00   92.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 70

  9 omega   43.00  101.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  120.0000 116

 10 omega    2.00   38.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  150.0000 72

 11 omega   38.00   73.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

 12 omega  111.00  167.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 112

 13 omega   43.00  108.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 130

 14 omega   42.00   86.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 88

 15 omega   38.00   90.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 104

 16 omega   48.00   90.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 84

 17 omega   94.00  156.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 124

 18 omega   47.00   85.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 76

 19 omega   61.00  109.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 96

 20 omega  104.00  177.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 146

 21 omega  -65.00  -39.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 52

 22 omega  -60.00  -26.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 68

 23 omega   23.00   49.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 52

 24 omega   73.00   99.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 52

 25 omega   -8.00   -7.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  106.0000   68.0072 2
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0254781000
_diffrn_orient_matrix_UB_12      -0.0131809000
_diffrn_orient_matrix_UB_13      -0.0840061000
_diffrn_orient_matrix_UB_21      -0.0559431000
_diffrn_orient_matrix_UB_22      0.0173970000
_diffrn_orient_matrix_UB_23      -0.0808803000
_diffrn_orient_matrix_UB_31      0.0052995000
_diffrn_orient_matrix_UB_32      0.2427336000
_diffrn_orient_matrix_UB_33      0.0011786000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5109
_diffrn_reflns_point_group_measured_fraction_full 0.737
_diffrn_reflns_point_group_measured_fraction_max 0.718
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.764
_diffrn_reflns_theta_min         3.347
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       needle
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 627 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0620P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.334
_reflns_Friedel_fraction_full    0.417
_reflns_Friedel_fraction_max     0.398
_reflns_number_gt                2726
_reflns_number_total             3058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05304b2.cif
_cod_data_source_block           zgk22075a
_cod_depositor_comments
;

2025-03-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C24 H20 Br F3 N2 O2), H2 O'
_cod_original_formula_sum        'C48 H42 Br2 F6 N4 O5'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1028.67
_cod_database_code               7124071
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2F3Br1
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.679
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.02
3.a Free rotating group:
 O3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C21(H21)
3.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'