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_7158051
_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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-27
_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                 106.0020(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.32490(16)
_cell_length_b                   10.11966(12)
_cell_length_c                   11.47015(15)
_cell_measurement_reflns_used    6888
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3460
_cell_measurement_theta_min      3.9860
_cell_volume                     1263.59(3)
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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    -85.00  -5.00   1.00    1.00    --  -40.98 124.00 -30.00   80
  2  \w   -112.00  -6.00   1.00    1.00    --  -40.98 -19.00-120.00  106
  3  \w     44.00  88.00   1.00    1.00    --   40.98-124.00-120.00   44
  4  \w     35.00 134.00   1.00    1.50    --  106.95 -61.00-180.00   99
  5  \w     64.00 121.00   1.00    1.50    --  106.95-124.00-150.00   57
  6  \w     54.00 130.00   1.00    1.50    --  106.95 -45.00 -90.00   76
  7  \w     82.00 174.00   1.00    1.50    --  106.95  45.00   0.00   92
  8  \w    153.00 178.00   1.00    1.50    --  106.95 124.00  30.00   25
  9  \w     94.00 177.00   1.00    1.50    --  106.95  61.00-120.00   83
 10  \w    145.00 172.00   1.00    1.50    --  106.95 124.00-180.00   27
 11  \w    100.00 130.00   1.00    1.50    --  106.95 124.00-180.00   30
 12  \w     90.00 176.00   1.00    1.50    --  106.95  45.00 -60.00   86
 13  \w     56.00 127.00   1.00    1.50    --  106.95 -45.00  60.00   71
 14  \w     29.00  91.00   1.00    1.50    --  106.95 -94.00  90.00   62
 15  \w     28.00 109.00   1.00    1.50    --  106.95 -94.00 -30.00   81
 16  \w     23.00  53.00   1.00    1.00    --   40.98-124.00 150.00   30
 17  \w   -114.00 -34.00   1.00    1.00    --  -40.98 -37.00-180.00   80
;
_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      0.0539667000
_diffrn_orient_matrix_UB_12      -0.0436533000
_diffrn_orient_matrix_UB_13      0.1326146000
_diffrn_orient_matrix_UB_21      -0.1232179000
_diffrn_orient_matrix_UB_22      0.0312684000
_diffrn_orient_matrix_UB_23      0.0263444000
_diffrn_orient_matrix_UB_31      -0.0439243000
_diffrn_orient_matrix_UB_32      -0.1425201000
_diffrn_orient_matrix_UB_33      -0.0350617000
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8662
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.716
_diffrn_reflns_theta_min         4.009
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61642
_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    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_coef       0.0050(5)
_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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0268
_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^)+(0.0405P)^2^+0.0948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.750
_reflns_Friedel_fraction_max     0.715
_reflns_number_gt                4295
_reflns_number_total             4383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00550b2.cif
_cod_data_source_block           zc-3
_cod_depositor_comments
'Adding full bibliography for 7158051--7158052.cif.'
_cod_database_code               7158051
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_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), C11(H11), C12(H12), 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:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              61591
_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.669