Asymmetric amination of 2-substituted indolin-3-ones catalyzed by natural cinchona alkaloids
Guo, Jing; Lin, Zi-Hui; Chen, Kai-Bin; Xie, Ying; Chan, Albert S. C.; Weng, Jiang; Lu, Gui; Organic Chemistry Frontiers 4 (2017) 1400–; doi:10.1039/C7QO00129K

data_1553750
_publ_section_title
;
 Asymmetric amination of 2-substituted indolin-3-ones catalyzed by natural
 cinchona alkaloids
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1400
_journal_paper_doi               10.1039/C7QO00129K
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H31 N3 O6'
_chemical_formula_sum            'C26 H31 N3 O6'
_chemical_formula_weight         481.55
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_Int_Tables_number      1
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-27 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                109.875(3)
_cell_angle_beta                 108.593(3)
_cell_angle_gamma                107.103(3)
_cell_formula_units_Z            1
_cell_length_a                   9.0047(3)
_cell_length_b                   9.2247(3)
_cell_length_c                   9.4826(3)
_cell_measurement_reflns_used    18387
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.2790
_cell_measurement_theta_min      5.6930
_cell_volume                     626.45(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9929
_diffrn_measured_fraction_theta_max 0.9915
_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   -126.00 -79.00   1.00    3.00    --  -44.40 -99.00   0.00   47
  2  \w   -126.00 -79.00   1.00    3.00    --  -44.40 -99.00 -60.00   47
  3  \w   -118.00 -73.00   1.00    3.00    --  -44.40-125.00   0.00   45
  4  \w   -118.00 -73.00   1.00    3.00    --  -44.40-125.00 120.00   45
  5  \w     73.00 118.00   1.00    3.00    --   44.40 125.00-150.00   45
  6  \w     19.00 114.00   1.00    3.00    --   44.40  57.00  30.00   95
  7  \w     19.00 114.00   1.00    3.00    --   44.40  57.00 120.00   95
  8  \w   -164.00 -58.00   1.00    5.00    --  -90.00 -77.00  60.00  106
  9  \w   -160.00 -63.00   1.00    5.00    --  -90.00 -61.00  60.00   97
 10  \w   -160.00 -63.00   1.00    5.00    --  -90.00 -61.00  90.00   97
 11  \w   -173.00 -80.00   1.00    5.00    --  -90.00 -94.00 -60.00   93
 12  \w   -160.00 -66.00   1.00    5.00    --  -90.00 -51.00  62.15   94
 13  \w     26.00 121.00   1.00    5.00    --  100.00-125.00 -30.00   95
 14  \w     29.00 124.00   1.00    5.00    --  100.00 -45.00 150.00   95
 15  \w     29.00 124.00   1.00    5.00    --  100.00 -45.00  60.00   95
 16  \w     68.00 174.00   1.00    5.00    --  100.00  77.00   0.00  106
 17  \w     68.00 174.00   1.00    5.00    --  100.00  77.00  30.00  106
 18  \w     21.00 139.00   1.00    5.00    --  100.00 -15.00  60.00  118
 19  \w     26.00 121.00   1.00    5.00    --  100.00-125.00 -60.00   95
 20  \w     68.00 174.00   1.00    5.00    --  100.00  77.00  90.00  106
 21  \w     30.00 127.00   1.00    5.00    --  100.00 -61.00  30.00   97
 22  \w     68.00 174.00   1.00    5.00    --  100.00  77.00  60.00  106
 23  \w     73.00 170.00   1.00    5.00    --  100.00  61.00  90.00   97
 24  \w     76.00 171.00   1.00    5.00    --  100.00  41.00 -36.00   95
 25  \w     76.00 171.00   1.00    5.00    --  100.00  45.00   0.00   95
 26  \w     73.00 174.00   1.00    5.00    --  100.00 125.00 150.00  101
 27  \w     73.00 174.00   1.00    5.00    --  100.00 125.00-180.00  101
 28  \w     73.00 174.00   1.00    5.00    --  100.00 125.00  60.00  101
 29  \w     30.00  56.00   1.00    5.00    --  100.00 -45.00   0.00   26
 30  \w     95.00 122.00   1.00    5.00    --  100.00  45.00  60.00   27
 31  \w     70.00  96.00   1.00    5.00    --  100.00  77.00 120.00   26
 32  \w    123.00 150.00   1.00    5.00    --  100.00  61.00 -60.00   27
 33  \w      7.00  32.00   1.00    3.00    --   42.00  89.00  44.78   25
 34  \w     22.00  49.00   1.00    3.00    --   44.40  40.00 -39.00   27
 35  \w     21.00  48.00   1.00    3.00    --   44.40  57.00-150.00   27
 36  \w     26.00  98.00   1.00    3.00    --   44.40-125.00 -90.00   72
 37  \w     26.00  53.00   1.00    3.00    --   44.40  37.00 120.00   27
 38  \w     13.00  38.00   1.00    3.00    --   46.00  82.00 -91.78   25
 39  \w     17.00  42.00   1.00    3.00    --   50.00  82.00 158.77   25
 40  \w     22.00  47.00   1.00    3.00    --   54.00  78.00 -25.99   25
 41  \w     22.00  47.00   1.00    3.00    --   54.00  78.00 104.26   25
 42  \w     36.00  62.00   1.00    3.00    --   62.00  75.00 159.72   26
 43  \w     37.00  63.00   1.00    3.00    --   62.00  75.00-109.23   26
 44  \w     31.00  63.00   1.00    3.00    --   62.00  75.00-157.17   32
 45  \w     36.00  62.00   1.00    3.00    --   62.00  75.00 -15.42   26
 46  \w     31.00  57.00   1.00    3.00    --   62.00  76.00  49.39   26
 47  \w     84.00 135.00   1.00    3.00    --   62.00  75.00 159.72   51
 48  \w    109.00 135.00   1.00    3.00    --   62.00  75.00-157.17   26
 49  \w     96.00 122.00   1.00    3.00    --   66.00  77.00 108.59   26
 50  \w     40.00  66.00   1.00    3.00    --   66.00  77.00 108.59   26
 51  \w     34.00  60.00   1.00    3.00    --   66.00  77.00  -2.46   26
 52  \w     40.00  67.00   1.00    3.00    --   70.00  76.00 -86.71   27
 53  \w    118.00 144.00   1.00    5.00    --   74.00  76.00-149.34   26
 54  \w     44.00  70.00   1.00    5.00    --   74.00  76.00-149.34   26
 55  \w     43.00  69.00   1.00    5.00    --   74.00  75.00  60.18   26
 56  \w    -87.00 -61.00   1.00    5.00    --  -90.00 -71.00 -91.95   26
 57  \w    -84.00 -58.00   1.00    5.00    --  -90.00 -77.00-120.00   26
 58  \w    -84.00 -58.00   1.00    5.00    --  -90.00 -77.00   0.00   26
 59  \w    -87.00 -61.00   1.00    5.00    --  -90.00 -75.00-100.77   26
 60  \w    -86.00 -60.00   1.00    5.00    --  -90.00 -72.00  36.58   26
 61  \w    -84.00 -58.00   1.00    5.00    --  -90.00 -77.00  90.00   26
 62  \w    -86.00 -60.00   1.00    5.00    --  -90.00 -76.00 139.48   26
 63  \w    -88.00 -62.00   1.00    5.00    --  -90.00 -73.00-166.18   26
 64  \w    -87.00 -61.00   1.00    5.00    --  -90.00 -70.00  62.16   26
 65  \w    -88.00 -62.00   1.00    5.00    --  -90.00 -67.00 -34.27   26
 66  \w    -83.00 -58.00   1.00    5.00    --  -90.00 -77.00 -60.00   25
 67  \w    -86.00 -60.00   1.00    5.00    --  -90.00 -76.00 131.47   26
 68  \w    -89.00 -63.00   1.00    5.00    --  -90.00 -61.00  -3.60   26
 69  \w    -83.00 -58.00   1.00    5.00    --  -90.00 -77.00-150.00   25
 70  \w    -83.00 -58.00   1.00    5.00    --  -90.00 -77.00 165.49   25
 71  \w     68.00  99.00   1.00    5.00    --  100.00  77.00 120.00   31
 72  \w     73.00  99.00   1.00    5.00    --  100.00  61.00 -30.00   26
 73  \w    109.00 139.00   1.00    5.00    --  100.00  45.00-180.00   30
 74  \w     74.00 100.00   1.00    5.00    --  100.00 -94.00-120.00   26
 75  \w     89.00 115.00   1.00    5.00    --  100.00-125.00-150.00   26
 76  \w     62.00  88.00   1.00    5.00    --  100.00-125.00  60.00   26
 77  \w     33.00  59.00   1.00    5.00    --  100.00-125.00  60.00   26
 78  \w     38.00  67.00   1.00    5.00    --  100.00 -94.00   0.00   29
 79  \w     79.00 108.00   1.00    5.00    --  100.00  77.00-150.00   29
 80  \w     81.00 132.00   1.00    5.00    --  100.00  61.00   0.00   51
 81  \w     65.00  91.00   1.00    5.00    --  100.00 -61.00 -90.00   26
 82  \w     32.00  58.00   1.00    5.00    --  100.00 -61.00 -90.00   26
 83  \w     98.00 149.00   1.00    5.00    --  100.00  77.00-120.00   51
 84  \w     68.00  94.00   1.00    5.00    --  100.00  77.00-120.00   26
 85  \w     72.00 103.00   1.00    5.00    --  100.00 -94.00   0.00   31
 86  \w     70.00 104.00   1.00    5.00    --  100.00-125.00   0.00   34
 87  \w     41.00  67.00   1.00    5.00    --  100.00-125.00   0.00   26
 88  \w     58.00 104.00   1.00    5.00    --  100.00 -94.00-180.00   46
 89  \w     92.00 117.00   1.00    5.00    --  100.00-125.00 120.00   25
 90  \w     77.00 106.00   1.00    5.00    --  100.00  45.00-180.00   29
 91  \w     28.00  54.00   1.00    5.00    --  100.00-125.00 120.00   26
 92  \w     99.00 125.00   1.00    5.00    --  100.00  77.00 -90.00   26
 93  \w     68.00  96.00   1.00    5.00    --  100.00  77.00 -90.00   28
 94  \w    115.00 152.00   1.00    5.00    --  100.00  77.00 120.00   37
 95  \w     69.00 102.00   1.00    5.00    --  100.00  77.00-180.00   33
 96  \w    105.00 134.00   1.00    5.00    --  100.00 125.00 120.00   29
 97  \w      7.00  33.00   1.00    3.00    --   42.00  89.00  44.78   26
 98  \w   -118.00 -73.00   1.00    3.00    --  -44.40-125.00 -60.00   45
 99  \w      2.00  98.00   1.00    3.00    --   44.40-125.00   0.00   96
100  \w     17.00  45.00   1.00    3.00    --   50.00  82.00 158.77   28
101  \w     17.00  45.00   1.00    3.00    --   50.00  82.00 117.02   28
102  \w     17.00  46.00   1.00    3.00    --   50.00  81.00  37.67   29
103  \w     18.00  46.00   1.00    3.00    --   50.00  80.00-127.11   28
104  \w     22.00  49.00   1.00    3.00    --   54.00  78.00 -25.99   27
105  \w     27.00 131.00   1.00    3.00    --   58.00  75.00 -79.72  104
106  \w     31.00 136.00   1.00    3.00    --   62.00  76.00  49.39  105
107  \w     31.00 135.00   1.00    3.00    --   62.00  75.00 -15.42  104
108  \w     34.00 140.00   1.00    3.00    --   66.00  77.00 108.59  106
109  \w     39.00 104.00   1.00    3.00    --   70.00  76.00 -86.71   65
110  \w    135.00 162.00   1.00    5.00    --  100.00  61.00-180.00   27
111  \w    106.00 132.00   1.00    5.00    --  100.00  61.00-150.00   26
112  \w    102.00 128.00   1.00    5.00    --  100.00  61.00 -90.00   26
113  \w     54.00  80.00   1.00    5.00    --  100.00 -94.00  90.00   26
114  \w    129.00 155.00   1.00    5.00    --  100.00  55.00 132.00   26
115  \w     75.00 101.00   1.00    5.00    --  100.00  61.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1227838000
_diffrn_orient_matrix_UB_12      -0.1120657000
_diffrn_orient_matrix_UB_13      0.0436672000
_diffrn_orient_matrix_UB_21      0.1482329000
_diffrn_orient_matrix_UB_22      -0.0374569000
_diffrn_orient_matrix_UB_23      0.0898614000
_diffrn_orient_matrix_UB_31      0.0622785000
_diffrn_orient_matrix_UB_32      0.1601575000
_diffrn_orient_matrix_UB_33      0.1677448000
_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  0.0757
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24247
_diffrn_reflns_theta_full        72.3189
_diffrn_reflns_theta_max         72.32
_diffrn_reflns_theta_min         5.72
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.2764
_exptl_crystal_description       block
_exptl_crystal_F_000             256.8698
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.1923
_refine_diff_density_min         -0.1768
_refine_diff_density_rms         0.0376
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.10(13)
_refine_ls_d_res_high            0.8091
_refine_ls_d_res_low             7.7405
_refine_ls_goodness_of_fit_ref   1.0608
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0608
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0876P)^2^+0.0895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.895
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                4625
_reflns_number_total             4674
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7qo00129k2.cif
_cod_data_source_block           gj_160918
_cod_original_sg_symbol_Hall     ' P 1'
_cod_database_code               1553750
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C24(H24), C13(H13), C14(H14), C23(H23), C25(H25), C31(H31),
 C21(H21), C20(H20), N7(H7)
2.b Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C22(H22a,H22b,H22c), C28(H28a,H28b,H28c), C32(H32a,H32b,
 H32c), C33(H33a,H33b,H33c), C34(H34a,H34b,H34c), C35(H35a,H35b,H35c)
;
_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 3.499
_oxdiff_exptl_absorpt_empirical_full_min 0.414