Asymmetric Synthesis of Oxindole-Derived Vicinal Tetrasubstituted Acyclic Amino Acid Derivatives by Mannich-Type Reaction.
Hou, Ke-Qiang; Zhou, Feng; Chen, Xue-Ping; Ge, Yang; Chan, Albert Sun Chi; Xiong, Xiao-Feng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00981

data_4038568
_publ_section_title
;
 Asymmetric Synthesis of Oxindole-Derived Vicinal Tetrasubstituted Acyclic
 Amino Acid Derivatives by Mannich-Type Reaction.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00981
_journal_year                    2020
_chemical_formula_moiety         'C27 H28 N2 O6 S'
_chemical_formula_sum            'C27 H28 N2 O6 S'
_chemical_formula_weight         508.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                102.2448(11)
_cell_angle_beta                 101.3852(12)
_cell_angle_gamma                115.8420(17)
_cell_formula_units_Z            2
_cell_length_a                   9.98869(17)
_cell_length_b                   11.08896(19)
_cell_length_c                   13.18431(11)
_cell_measurement_reflns_used    31957
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9630
_cell_measurement_theta_min      3.6380
_cell_volume                     1212.66(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_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   -118.00 -46.00   0.50    0.05    --  -46.37-163.00 151.00  144
  2  \w   -119.00 -30.00   0.50    0.05    --  -46.37 163.00 176.00  178
  3  \w    -91.00  -5.00   0.50    0.05    --  -46.37 117.00  27.00  172
  4  \w     51.00 118.00   0.50    0.05    --   46.37 163.00 176.00  134
  5  \w     34.00 119.00   0.50    0.05    --   46.37-163.00 151.00  170
  6  \w      9.00  91.00   0.50    0.05    --   46.37-117.00 -59.00  164
  7  \w   -113.00 -27.00   0.50    0.30    -- -100.00 117.00  27.00  172
  8  \w   -161.00 -46.00   0.50    0.30    -- -100.00-163.00 151.00  230
  9  \w   -173.00 -76.00   0.50    0.30    -- -100.00-117.00 -59.00  194
 10  \w     34.00 113.00   0.50    0.30    --  107.00-117.00 -59.00  158
 11  \w     51.00 161.00   0.50    0.30    --  107.00 163.00 176.00  220
 12  \w     34.00 143.00   0.50    0.30    --  107.00-163.00 151.00  218
 13  \w     81.00 178.00   0.50    0.30    --  107.00 117.00  27.00  194
 14  \w     -9.00  30.00   0.50    0.05    --   24.00  97.00 -73.83   78
 15  \w      4.00  36.00   0.50    0.05    --   36.00  94.00-131.84   64
 16  \w     14.00  45.00   0.50    0.05    --   44.00  90.00 -62.09   62
 17  \w     13.00  43.00   0.50    0.05    --   44.00  92.00  23.32   60
 18  \w   -120.00 -32.00   0.50    0.05    --  -46.37 -38.00-180.00  176
 19  \w   -122.00 -31.00   0.50    0.05    --  -46.37 -19.00-120.00  182
 20  \w   -120.00 -32.00   0.50    0.05    --  -46.37 -38.00  90.00  176
 21  \w   -118.00 -30.00   0.50    0.05    --  -46.37 -57.00  90.00  176
 22  \w   -120.00 -32.00   0.50    0.05    --  -46.37 -38.00  90.00  176
 23  \w     25.00  52.00   0.50    0.05    --   46.37  77.00 150.00   54
 24  \w     26.00  52.00   0.50    0.05    --   46.37  77.00  90.00   52
 25  \w     19.00  44.00   0.50    0.05    --   48.00  88.00  58.41   50
 26  \w     18.00  43.00   0.50    0.05    --   48.00  90.00-165.73   50
 27  \w     33.00  58.00   0.50    0.05    --   52.00  71.00-116.22   50
 28  \w    -82.00 -31.00   0.50    0.05    --  -56.00 -82.00 -76.42  102
 29  \w     30.00  67.00   0.50    0.05    --   56.00  83.00 -89.63   74
 30  \w     31.00  56.00   0.50    0.05    --   56.00  80.00  85.13   50
 31  \w     31.00  57.00   0.50    0.05    --   56.00  80.00 157.03   52
 32  \w    -91.00 -37.00   0.50    0.05    --  -60.00 -80.00  48.39  108
 33  \w    -59.00 -34.00   0.50    0.05    --  -60.00 -81.00 -43.97   50
 34  \w   -117.00 -92.00   0.50    0.05    --  -60.00 -81.00 -43.97   50
 35  \w    -64.00 -38.00   0.50    0.05    --  -64.00 -82.00  -8.77   52
 36  \w    -79.00 -45.00   0.50    0.05    --  -68.00 -74.00  28.80   68
 37  \w    -98.00 -49.00   0.50    0.05    --  -68.00 -69.00 -41.42   98
 38  \w    -70.00 -45.00   0.50    0.05    --  -68.00 -75.00 115.46   50
 39  \w    -80.00 -54.00   0.50    0.05    --  -72.00 -64.00-159.43   52
 40  \w    -78.00 -45.00   0.50    0.05    --  -72.00 -83.00 -52.65   66
 41  \w    -73.00 -47.00   0.50    0.05    --  -72.00 -82.00 172.84   52
 42  \w    -79.00 -51.00   0.50    0.05    --  -72.00 -69.00   7.25   56
 43  \w   -112.00 -86.00   0.50    0.05    --  -72.00 -69.00   7.25   52
 44  \w    -86.00 -53.00   0.50    0.05    --  -72.00 -67.00  90.33   66
 45  \w    -86.00 -54.00   0.50    0.05    --  -72.00 -68.00  71.05   64
 46  \w   -145.00-116.00   0.50    0.05    --  -72.00 -69.00   7.25   58
 47  \w    -81.00 -55.00   0.50    0.30    --  -76.00 -72.00-161.61   52
 48  \w    -81.00 -55.00   0.50    0.30    --  -76.00 -69.00 177.94   52
 49  \w    -75.00 -49.00   0.50    0.30    --  -76.00 -83.00 -80.74   52
 50  \w    -84.00 -57.00   0.50    0.30    --  -80.00 -74.00 152.33   54
 51  \w    -89.00 -61.00   0.50    0.30    --  -80.00 -65.00  42.17   56
 52  \w   -130.00 -93.00   0.50    0.30    --  -80.00 -65.00  42.17   74
 53  \w    -87.00 -61.00   0.50    0.30    --  -80.00 -64.00-160.64   52
 54  \w    -87.00 -54.00   0.50    0.30    --  -80.00 -83.00-100.10   66
 55  \w    -85.00 -59.00   0.50    0.30    --  -80.00 -70.00 -79.99   52
 56  \w    -82.00 -55.00   0.50    0.30    --  -80.00 -82.00  11.89   54
 57  \w    -85.00 -59.00   0.50    0.30    --  -84.00 -81.00 119.35   52
 58  \w    -96.00 -67.00   0.50    0.30    --  -84.00 -60.00 -44.87   58
 59  \w    -98.00 -65.00   0.50    0.30    --  -88.00 -74.00  84.10   66
 60  \w    -95.00 -69.00   0.50    0.30    --  -88.00 -65.00 127.56   52
 61  \w    -96.00 -67.00   0.50    0.30    --  -88.00 -72.00  20.86   58
 62  \w    -92.00 -67.00   0.50    0.30    --  -88.00 -71.00 -12.40   50
 63  \w   -103.00 -69.00   0.50    0.30    --  -96.00 -83.00  66.97   68
 64  \w   -167.00-141.00   0.50    0.30    --  -96.00 -83.00  66.97   52
 65  \w   -110.00 -72.00   0.50    0.30    --  -96.00 -82.00-156.34   76
 66  \w   -172.00 -80.00   0.50    0.30    -- -100.00 -70.00 -54.43  184
 67  \w   -112.00 -81.00   0.50    0.30    -- -100.00 -69.00  43.71   62
 68  \w   -172.00-125.00   0.50    0.30    -- -100.00 -69.00  43.71   94
 69  \w   -104.00 -76.00   0.50    0.30    -- -100.00 -78.00  81.71   56
 70  \w   -107.00 -76.00   0.50    0.30    -- -100.00 -77.00 -30.00   62
 71  \w   -144.00 -82.00   0.50    0.30    -- -100.00 -77.00 -90.00  124
 72  \w   -171.00-145.00   0.50    0.30    -- -100.00 -77.00 178.70   52
 73  \w   -172.00-128.00   0.50    0.30    -- -100.00 -78.00  81.71   88
 74  \w   -129.00 -91.00   0.50    0.30    -- -100.00 -30.00   0.00   76
 75  \w   -107.00 -77.00   0.50    0.30    -- -100.00 -77.00   0.00   60
 76  \w   -173.00-111.00   0.50    0.30    -- -100.00 -77.00   0.00  124
 77  \w   -129.00 -77.00   0.50    0.30    -- -100.00 -77.00 -60.00  104
 78  \w   -169.00-132.00   0.50    0.30    -- -100.00 -77.00 -60.00   74
 79  \w   -104.00 -76.00   0.50    0.30    -- -100.00 -77.00 125.75   56
 80  \w   -119.00 -81.00   0.50    0.30    -- -100.00 -66.00   6.29   76
 81  \w   -173.00-125.00   0.50    0.30    -- -100.00 -77.00 125.75   96
 82  \w   -146.00 -77.00   0.50    0.30    -- -100.00 -77.00-120.00  138
 83  \w   -111.00 -75.00   0.50    0.30    -- -100.00 -80.00 144.46   72
 84  \w   -172.00 -76.00   0.50    0.30    -- -100.00 -78.00-107.49  192
 85  \w   -105.00 -76.00   0.50    0.30    -- -100.00 -77.00  30.00   58
 86  \w   -117.00 -80.00   0.50    0.30    -- -100.00 -67.00 174.10   74
 87  \w   -170.00-144.00   0.50    0.30    -- -100.00 -67.00 174.10   52
 88  \w   -104.00 -78.00   0.50    0.30    -- -100.00 -74.00 100.82   52
 89  \w   -173.00-121.00   0.50    0.30    -- -100.00 -80.00 144.46  104
 90  \w   -154.00 -85.00   0.50    0.30    -- -100.00 -61.00 -30.00  138
 91  \w   -100.00 -75.00   0.50    0.30    -- -100.00 -80.00 -79.16   50
 92  \w   -137.00-110.00   0.50    0.30    -- -100.00 -80.00 -79.16   54
 93  \w   -109.00 -80.00   0.50    0.30    -- -100.00 -74.00-140.17   58
 94  \w   -170.00-139.00   0.50    0.30    -- -100.00 -74.00-140.17   62
 95  \w   -111.00 -86.00   0.50    0.30    -- -100.00 163.00 176.00   50
 96  \w   -104.00 -78.00   0.50    0.30    -- -100.00 -77.00 178.70   52
 97  \w   -172.00 -76.00   0.50    0.30    -- -100.00 -77.00-151.65  192
 98  \w   -165.00-138.00   0.50    0.30    -- -100.00 -30.00   0.00   54
 99  \w     83.00 176.00   0.50    0.30    --  107.00  77.00 150.00  186
100  \w     40.00  82.00   0.50    0.30    --  107.00 -94.00 120.00   84
101  \w    138.00 178.00   0.50    0.30    --  107.00  77.00   0.00   80
102  \w     34.00 108.00   0.50    0.30    --  107.00 -94.00 -30.00  148
103  \w    104.00 130.00   0.50    0.30    --  107.00  77.00   0.00   52
104  \w    100.00 175.00   0.50    0.30    --  107.00  45.00 120.00  150
105  \w    124.00 150.00   0.50    0.30    --  107.00  45.00-150.00   52
106  \w     51.00 117.00   0.50    0.30    --  107.00-125.00 -60.00  132
107  \w     76.00 102.00   0.50    0.30    --  107.00 -94.00  90.00   52
108  \w     86.00 121.00   0.50    0.30    --  107.00  77.00  30.00   70
109  \w     34.00 131.00   0.50    0.30    --  107.00 -77.00 -30.00  194
110  \w     90.00 148.00   0.50    0.30    --  107.00  61.00 120.00  116
111  \w     52.00 117.00   0.50    0.30    --  107.00-125.00  90.00  130
112  \w     38.00  95.00   0.50    0.30    --  107.00-125.00-180.00  114
113  \w     38.00 114.00   0.50    0.30    --  107.00-125.00-150.00  152
114  \w     36.00 117.00   0.50    0.30    --  107.00-125.00-120.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0359286000
_diffrn_orient_matrix_UB_12      -0.0835096000
_diffrn_orient_matrix_UB_13      -0.1205539000
_diffrn_orient_matrix_UB_21      0.1485961000
_diffrn_orient_matrix_UB_22      -0.0128453000
_diffrn_orient_matrix_UB_23      0.0340619000
_diffrn_orient_matrix_UB_31      -0.0978429000
_diffrn_orient_matrix_UB_32      -0.1405736000
_diffrn_orient_matrix_UB_33      0.0185748000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            47070
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.090
_diffrn_reflns_theta_min         3.634
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
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    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.4781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4634
_reflns_number_total             4996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00981_si_002.cif
_cod_data_source_block           houkq_190619
_cod_database_code               4038568
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.743
_diffrn_oxdiff_digest_frames
;
01dc80baabeed0865f72c0144c8ea5644400130b46e
;
_diffrn_oxdiff_digest_hkl
;
01299f73bc259e61782a4825c2e939157e3cb9
;
_reflns_odcompleteness_completeness 99.96
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
 C26(H26), C28(H28), C30(H30), C31(H31), C32(H32), C35(H35)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              41275
_shelx_hkl_checksum              50699
_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 1.707
_oxdiff_exptl_absorpt_empirical_full_min 0.695