Palladium-catalyzed asymmetric allylic alkylation of 3-aminooxindoles to access chiral homoallylic aminooxindoles.
Zhang, Chao; Wu, You-Cai; Cui, Bao-Dong; Li, Lian; Han, Wen-Yong; Wan, Nan-Wei; Chen, Yong-Zheng; Organic & biomolecular chemistry 19 (2021) 4720–4725; doi:10.1039/d1ob00550b

data_7158052
_publ_section_title
;
 Palladium-catalyzed asymmetric allylic alkylation of 3-aminooxindoles to
 access chiral homoallylic aminooxindoles.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4720
_journal_page_last               4725
_journal_paper_doi               10.1039/d1ob00550b
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H29 F N2 O3'
_chemical_formula_sum            'C29 H29 F N2 O3'
_chemical_formula_weight         472.54
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-06
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.6850(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.4371(5)
_cell_length_b                   6.95612(16)
_cell_length_c                   15.3764(2)
_cell_measurement_reflns_used    6502
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5800
_cell_measurement_theta_min      2.9060
_cell_volume                     2681.98(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -62.00 -35.00   1.00    1.00    --  -40.98 -57.00   0.00   27
  2  \w     23.00  71.00   1.00    1.00    --   40.98  57.00   0.00   48
  3  \w      9.00 117.00   1.00    1.00    --   40.98  77.00 -90.00  108
  4  \w     50.00  77.00   1.00    1.00    --   40.98  37.00   0.00   27
  5  \w    -35.00  37.00   1.00    1.00    --   40.98 -77.00  60.00   72
  6  \w     81.00 114.00   1.00    1.00    --   40.98  37.00   0.00   33
  7  \w     40.00  67.00   1.00    1.00    --   40.98  77.00-150.00   27
  8  \w     30.00  87.00   1.00    1.00    --   40.98  37.00-120.00   57
  9  \w      1.00  79.00   1.00    1.00    --   40.98 -99.00 150.00   78
 10  \w     75.00 100.00   1.00    2.00    --  106.95  77.00 -30.00   25
 11  \w    109.00 178.00   1.00    2.00    --  106.95  77.00-120.00   69
 12  \w     75.00 100.00   1.00    1.50    --  106.95  77.00-120.00   25
 13  \w     74.00 101.00   1.00    1.50    --  106.95  77.00   0.00   27
 14  \w     74.00 100.00   1.00    1.50    --  106.95  77.00 -60.00   26
 15  \w     34.00  87.00   1.00    1.50    --  106.95-124.00-180.00   53
 16  \w     74.00 101.00   1.00    1.50    --  106.95  77.00-150.00   27
 17  \w     24.00 106.00   1.00    1.50    --  106.95 -94.00-180.00   82
 18  \w     78.00 104.00   1.00    1.50    --  106.95  61.00 -90.00   26
 19  \w     78.00 104.00   1.00    1.50    --  106.95  61.00   0.00   26
 20  \w     79.00 140.00   1.00    1.50    --  106.95  61.00 -60.00   61
 21  \w     79.00 104.00   1.00    1.50    --  106.95  61.00 -30.00   25
 22  \w     82.00 109.00   1.00    1.50    --  106.95  61.00-150.00   27
 23  \w     82.00 145.00   1.00    1.50    --  106.95  45.00 -30.00   63
 24  \w     79.00 104.00   1.00    1.50    --  106.95  61.00-120.00   25
 25  \w     82.00 149.00   1.00    1.50    --  106.95  45.00-120.00   67
 26  \w     81.00 108.00   1.00    1.50    --  106.95  45.00 -60.00   27
 27  \w     81.00 178.00   1.00    1.50    --  106.95  45.00   0.00   97
 28  \w     24.00  69.00   1.00    1.50    --  106.95 -94.00 -90.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0078301000
_diffrn_orient_matrix_UB_12      0.0120649000
_diffrn_orient_matrix_UB_13      -0.0970437000
_diffrn_orient_matrix_UB_21      -0.0605189000
_diffrn_orient_matrix_UB_22      -0.0245871000
_diffrn_orient_matrix_UB_23      -0.0301519000
_diffrn_orient_matrix_UB_31      -0.0072132000
_diffrn_orient_matrix_UB_32      0.2197350000
_diffrn_orient_matrix_UB_33      0.0019726000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10381
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.708
_diffrn_reflns_theta_min         2.915
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.170
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 1690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_coef       0.00110(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0499P)^2^+0.3009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                4489
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00550b2.cif
_cod_data_source_block           zc-2-2
_cod_depositor_comments
'Adding full bibliography for 7158051--7158052.cif.'
_cod_database_code               7158052
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              38638
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.347
_oxdiff_exptl_absorpt_empirical_full_min 0.656