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_7124070
_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         'C23 H21 F N2 O4 S'
_chemical_formula_sum            'C23 H21 F N2 O4 S'
_chemical_formula_weight         440.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2019-05-11 deposited with the CCDC.    2019-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.17133(16)
_cell_length_b                   14.8909(5)
_cell_length_c                   22.8926(7)
_cell_measurement_reflns_used    2453
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9230
_cell_measurement_theta_min      3.8810
_cell_volume                     2103.75(11)
_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 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega -102.00  -15.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -180.0000 174

  2 omega -105.00  -73.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 64

  3 omega    7.00   33.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 52

  4 omega  -52.00  -21.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 62

  5 omega   26.00   74.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 96

  6 omega   -4.00   22.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 52

  7 omega  -32.00   12.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -60.0000 88

  8 omega   20.00  107.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  120.0000 174

  9 omega   57.00   82.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 50

 10 omega   60.00  106.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 92

 11 omega   38.00   68.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 60

 12 omega   48.00   84.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 72

 13 omega   46.00   92.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 92

 14 omega  118.00  175.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 114

 15 omega   38.00  138.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 200

 16 omega   42.00   84.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 84

 17 omega   41.00  101.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 120

 18 omega   53.00   80.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0088367000
_diffrn_orient_matrix_UB_12      -0.0553560000
_diffrn_orient_matrix_UB_13      -0.0567952000
_diffrn_orient_matrix_UB_21      -0.0120171000
_diffrn_orient_matrix_UB_22      0.0873764000
_diffrn_orient_matrix_UB_23      -0.0359004000
_diffrn_orient_matrix_UB_31      0.2491678000
_diffrn_orient_matrix_UB_32      0.0022761000
_diffrn_orient_matrix_UB_33      -0.0037911000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7878
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.958
_diffrn_reflns_theta_min         3.541
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73612
_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    1.391
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0386P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3123
_reflns_number_total             3984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05304b2.cif
_cod_data_source_block           201805262
_cod_original_cell_volume        2103.76(11)
_cod_database_code               7124070
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N3S1
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.781
_reflns_odcompleteness_completeness 99.86
_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
2. Restrained distances
 C12A-C11A
 1.38 with sigma of 0.02
 C13A-C12A
 1.38 with sigma of 0.02
 C11-S1
 1.6 with sigma of 0.02
 N2-H2A
 0.87 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C14) \\sim Ueq, Uanis(C14A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(F1) = Uanis(F1A)
Uanis(C11) = Uanis(C11A)
4. Others
 Sof(C14A)=Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(C16A)=
 Sof(H16A)=Sof(C15A)=Sof(H15A)=Sof(F1A)=1-FVAR(1)
 Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=Sof(H15)=
 Sof(C16)=Sof(H16)=Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C13A(H13A), C12A(H12A),
 C16A(H16A), C15A(H15A), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21),
 C22(H22)
5.c Fitted hexagon refined as free rotating group:
 C14A(C13A,C12A,C11A,C16A,C15A)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'