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_4038567
_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         'C34 H33 N3 O6 S'
_chemical_formula_sum            'C34 H33 N3 O6 S'
_chemical_formula_weight         611.69
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.5878(4)
_cell_length_b                   11.8658(2)
_cell_length_c                   23.2836(3)
_cell_measurement_reflns_used    13432
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.5130
_cell_measurement_theta_min      3.7870
_cell_volume                     5964.25(17)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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     13.00  60.00   0.50    0.05    --   46.12 -21.00 -24.00   94
  2  \w   -173.00 -78.00   0.50    0.05    -- -100.00-120.00 130.00  190
  3  \w    113.00 178.00   0.50    0.05    --  105.44  21.00 141.00  130
  4  \w    -55.00   4.00   0.50    0.05    --  -46.12  57.00-180.00  118
  5  \w   -112.00 -72.00   0.50    0.05    --  -46.12-125.00  90.00   80
  6  \w      6.00  62.00   0.50    0.05    --   46.12 -57.00 -90.00  112
  7  \w     91.00 166.00   0.50    0.05    --  105.44  45.00-150.00  150
  8  \w     40.00  84.00   0.50    0.05    --  105.44 -94.00-180.00   88
  9  \w     47.00  83.00   0.50    0.05    --  105.44 -94.00-120.00   72
 10  \w     34.00  70.00   0.50    0.05    --  105.44 -94.00 -30.00   72
 11  \w     83.00 124.00   0.50    0.50    --  107.00 151.00  14.00   82
 12  \w   -104.00 -78.00   0.50    0.05    --  -46.37-125.00  30.00   52
 13  \w     24.00  87.00   0.50    0.05    --   46.37-125.00  60.00  126
 14  \w   -106.00 -75.00   0.50    0.50    -- -100.00  45.00 120.00   62
 15  \w   -114.00 -85.00   0.50    0.50    -- -100.00 -30.00 -60.00   58
 16  \w   -171.00-144.00   0.50    0.50    -- -100.00 -30.00 -60.00   54
 17  \w    100.00 125.00   0.50    0.50    --  107.00 -15.00 -60.00   50
 18  \w    100.00 128.00   0.50    0.50    --  107.00 -77.00 -90.00   56
 19  \w     44.00  83.00   0.50    0.50    --  107.00 -77.00 -90.00   78
 20  \w    135.00 162.00   0.50    0.50    --  107.00 125.00-180.00   54
 21  \w     44.00  96.00   0.50    0.50    --  107.00 -15.00 -60.00  104
 22  \w     89.00 131.00   0.50    0.50    --  107.00 125.00-180.00   84
 23  \w     77.00 104.00   0.50    0.50    --  107.00 -94.00 -60.00   54
 24  \w     45.00 102.00   0.50    0.50    --  107.00 -94.00  30.00  114
 25  \w    131.00 161.00   0.50    0.50    --  107.00 151.00  14.00   60
 26  \w   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00 -30.00  190
 27  \w   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00-150.00  190
 28  \w   -118.00 -30.00   0.50    0.05    --  -46.37 -57.00   0.00  176
 29  \w   -118.00 -82.00   0.50    0.05    --  -46.37 -57.00 120.00   72
 30  \w   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00  90.00  190
 31  \w   -100.00 -75.00   0.50    0.05    --  -46.37 -20.00 -22.00   50
;
_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      -0.0156297000
_diffrn_orient_matrix_UB_12      0.0704763000
_diffrn_orient_matrix_UB_13      0.0067713000
_diffrn_orient_matrix_UB_21      -0.0304892000
_diffrn_orient_matrix_UB_22      -0.0091934000
_diffrn_orient_matrix_UB_23      0.0637452000
_diffrn_orient_matrix_UB_31      0.1251991000
_diffrn_orient_matrix_UB_32      0.0065981000
_diffrn_orient_matrix_UB_33      0.0163871000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            55316
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.257
_diffrn_reflns_theta_min         3.797
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71671
_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    1.362
_exptl_crystal_description       needle
_exptl_crystal_F_000             2576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.00035(6)
_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   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0858P)^2^+3.6745P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5041
_reflns_number_total             6165
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00981_si_003.cif
_cod_data_source_block           houkq_191128_2
_cod_database_code               4038567
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.768
_diffrn_oxdiff_digest_frames
;
017dc4805e1b91bbc4cf8dceba10ba842b0110648bc
;
_diffrn_oxdiff_digest_hkl
;
01eaeb4b8b4ee875160d6fefcaae9a1cbb3222
;
_reflns_odcompleteness_completeness 99.85
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 N17(H17), C5(H5), C44(H44), C8(H8), C7(H7), C12(H12), C40(H40), C6(H6),
 C37(H37), C16(H16), C43(H43), C15(H15), C42(H42), C41(H41), C14(H14), C33(H33),
  C13(H13), C36(H36), C34(H34)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C38(H38A,H38B,H38C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              31393
_shelx_hkl_checksum              13953
_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 2.102
_oxdiff_exptl_absorpt_empirical_full_min 0.548