Chiral Bifunctional Bisphosphine Enabled Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Ynones
Zhang, Junliang; Cong, Tiantian; Wang, Huamin; Li, Xiuzheng; Wu, Hai-Hong; Chemical Communications  (2019) –; doi:10.1039/C9CC04357H

data_7123769
_publ_section_title
;
 Chiral Bifunctional Bisphosphine Enabled Enantioselective Tandem Michael
 Addition of Tryptamine-Derived Oxindoles to Ynones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04357H
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H28 N2 O6 S'
_chemical_formula_sum            'C25 H28 N2 O6 S'
_chemical_formula_weight         484.55
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-17 deposited with the CCDC.    2019-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.4750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.45040(10)
_cell_length_b                   8.50540(10)
_cell_length_c                   12.26270(10)
_cell_measurement_reflns_used    22588
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1880
_cell_measurement_theta_min      3.8020
_cell_volume                     1181.23(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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      3.00  29.00   1.00    1.00    --    0.00 -82.00 145.00   26
  2  \w    -14.00  68.00   1.00    1.00    --    0.00  82.00 -93.00   82
  3  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -93.00   25
  4  \w     42.00 127.00   1.00    1.00    --   95.80 -82.00 145.00   85
  5  \w    -22.00  12.00   1.00    1.00    --    0.00  57.00-180.00   34
  6  \w     46.00  88.00   1.00    1.00    --    0.00  57.00 -30.00   42
  7  \w     19.00  44.00   1.00    1.00    --    0.00  77.00  60.00   25
  8  \w     28.00  54.00   1.00    1.00    --    0.00  57.00-180.00   26
  9  \w    -18.00  25.00   1.00    1.00    --    0.00  38.00  60.00   43
 10  \w    -15.00  89.00   1.00    1.00    --    0.00  38.00-120.00  104
 11  \w    -23.00  13.00   1.00    1.00    --    0.00  57.00 -30.00   36
 12  \w     35.00  88.00   1.00    1.00    --    0.00  38.00  60.00   53
 13  \w    -26.00  23.00   1.00    1.00    --    0.00 -57.00 -90.00   49
 14  \w    -81.00 -15.00   1.00    1.00    --    0.00 -77.00 -90.00   66
 15  \w    -88.00 -63.00   1.00    1.00    --    0.00 -57.00 -90.00   25
 16  \w     63.00  89.00   1.00    1.00    --    0.00  77.00  60.00   26
 17  \w    -18.00  14.00   1.00    1.00    --    0.00  77.00  60.00   32
 18  \w     96.00 184.00   1.00    1.00    --   95.80  77.00 150.00   88
 19  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 20  \w     51.00 125.00   1.00    1.00    --   95.80 -77.00 -30.00   74
 21  \w    129.00 161.00   1.00    1.00    --   95.80  79.00  67.36   32
 22  \w     64.00  94.00   1.00    1.00    --   95.80  79.00  67.36   30
 23  \w     10.00  47.00   1.00    1.00    --   95.80 -77.00 -30.00   37
 24  \w    147.00 173.00   1.00    1.00    --   95.80  66.00-168.49   26
 25  \w    105.00 181.00   1.00    1.00    --   95.80  82.00  90.00   76
 26  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 27  \w     68.00 119.00   1.00    1.00    --   95.80  68.00 -57.63   51
 28  \w    160.00 185.00   1.00    1.00    --   95.80  82.00   0.00   25
 29  \w     67.00 125.00   1.00    1.00    --   95.80 -82.00  60.00   58
 30  \w     66.00  91.00   1.00    1.00    --   95.80  77.00  60.00   25
 31  \w    147.00 173.00   1.00    1.00    --   95.80  77.00  60.00   26
 32  \w     72.00  97.00   1.00    1.00    --   95.80  61.00-180.00   25
 33  \w    107.00 139.00   1.00    1.00    --   95.80  61.00-180.00   32
 34  \w     69.00 103.00   1.00    1.00    --   95.80  65.00  38.04   34
 35  \w     88.00 127.00   1.00    1.00    --   95.80 -82.00-150.00   39
 36  \w     51.00  76.00   1.00    1.00    --   95.80 -82.00-150.00   25
 37  \w     64.00  89.00   1.00    1.00    --   95.80  82.00   0.00   25
 38  \w    123.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   62
 39  \w    108.00 134.00   1.00    1.00    --   95.80  77.00 -30.00   26
 40  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 41  \w    117.00 185.00   1.00    1.00    --   95.80  82.00 120.00   68
 42  \w     73.00 183.00   1.00    1.00    --   95.80  54.00-130.83  110
 43  \w    133.00 159.00   1.00    1.00    --   95.80  45.00 120.00   26
 44  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 45  \w     78.00 135.00   1.00    1.00    --   95.80  45.00  90.00   57
 46  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 -60.00   26
 47  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 -60.00   26
 48  \w     71.00  96.00   1.00    1.00    --   95.80  61.00   0.00   25
 49  \w    157.00 182.00   1.00    1.00    --   95.80  61.00   0.00   25
 50  \w     71.00  96.00   1.00    1.00    --   95.80  61.00 150.00   25
 51  \w     11.00 120.00   1.00    1.00    --   95.80 -61.00  30.00  109
 52  \w    157.00 183.00   1.00    1.00    --   95.80  77.00-150.00   26
 53  \w     75.00 102.00   1.00    1.00    --   95.80  45.00 120.00   27
 54  \w     73.00  99.00   1.00    1.00    --   95.80  61.00  60.00   26
 55  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-120.00   25
 56  \w    127.00 152.00   1.00    1.00    --   95.80  77.00-120.00   25
 57  \w     64.00  90.00   1.00    1.00    --   95.80  82.00-150.00   26
 58  \w     75.00 127.00   1.00    1.00    --   95.80  45.00 -90.00   52
 59  \w    146.00 185.00   1.00    1.00    --   95.80  45.00 -90.00   39
 60  \w     75.00 156.00   1.00    1.00    --   95.80  45.00 -60.00   81
 61  \w     75.00 172.00   1.00    1.00    --   95.80  45.00   0.00   97
 62  \w      8.00  33.00   1.00    1.00    --   95.80 -77.00-180.00   25
 63  \w     57.00 121.00   1.00    1.00    --   95.80 -77.00-180.00   64
 64  \w     75.00 108.00   1.00    1.00    --   95.80  45.00  30.00   33
 65  \w    113.00 139.00   1.00    1.00    --   95.80  45.00  30.00   26
 66  \w    147.00 174.00   1.00    1.00    --   95.80  45.00  30.00   27
 67  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 68  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 69  \w    123.00 176.00   1.00    1.00    --   95.80  65.00  38.04   53
 70  \w     65.00  90.00   1.00    1.00    --   95.80  82.00-120.00   25
 71  \w     66.00  92.00   1.00    1.00    --   95.80  77.00-150.00   26
 72  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 73  \w     65.00  91.00   1.00    1.00    --   95.80  82.00 -60.00   26
 74  \w     69.00 126.00   1.00    1.00    --   95.80  66.00-168.49   57
 75  \w     70.00 109.00   1.00    1.00    --   95.80  65.00 123.88   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0758717000
_diffrn_orient_matrix_UB_12      0.0789097000
_diffrn_orient_matrix_UB_13      -0.0991229000
_diffrn_orient_matrix_UB_21      0.1125773000
_diffrn_orient_matrix_UB_22      0.0426102000
_diffrn_orient_matrix_UB_23      -0.0484660000
_diffrn_orient_matrix_UB_31      -0.0075881000
_diffrn_orient_matrix_UB_32      -0.1574639000
_diffrn_orient_matrix_UB_33      -0.0629038000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27083
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.568
_diffrn_reflns_theta_min         3.903
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.593
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 2105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(13)
_refine_ls_extinction_coef       0.0063(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0726P)^2^+0.1518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                4700
_reflns_number_total             4750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04357h2.cif
_cod_data_source_block           exp_483
_cod_database_code               7123769
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.96
_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.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C17(H17), C4(H4), C16(H16), C18(H18), C19(H19),
 C15(H15)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_shelx_res_checksum              32493
_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 4.350
_oxdiff_exptl_absorpt_empirical_full_min 0.324