A zinc/PyBisulidine catalyzed asymmetric Mannich reaction of N-tosyl imines with 3-acyloxy-2-oxindoles
Yang, Zinan; He, Huakang; Tian, Rui; Wu, Ruoran; Hu, Sheng; Wu, Yue; Zhou, Hui; Organic & Biomolecular Chemistry 19 (2021) 7460–7469; doi:10.1039/D1OB01328A

data_7158236
_publ_section_title
;
 A zinc/PyBisulidine catalyzed asymmetric Mannich reaction of N-tosyl
 imines with 3-acyloxy-2-oxindoles
;
_journal_issue                   34
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              7460
_journal_page_last               7469
_journal_paper_doi               10.1039/D1OB01328A
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 N2 O5 S'
_chemical_formula_sum            'C24 H22 N2 O5 S'
_chemical_formula_weight         450.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-24 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.42743(15)
_cell_length_b                   9.8509(2)
_cell_length_c                   24.0927(4)
_cell_measurement_reflns_used    3593
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8640
_cell_measurement_theta_min      4.8390
_cell_volume                     2237.46(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -102.00 -36.00   1.00    2.00    --  -33.50 -57.00  90.00   66
  2  \w     59.00 109.00   1.00    2.00    --   36.47 178.00 150.00   50
  3  \w    -30.00  58.00   1.00    2.00    --   36.47 -77.00 -30.00   88
  4  \w     44.00  99.00   1.00    2.00    --   36.47  37.00 150.00   55
  5  \w     69.00  99.00   1.00    2.00    --   36.47 178.00   0.00   30
  6  \w     66.00  95.00   1.00    2.00    --   36.47 178.00-150.00   29
  7  \w     57.00  83.00   1.00    2.00    --   36.47 178.00-120.00   26
  8  \w     63.00 108.00   1.00   13.00    --  108.00  15.00  30.00   45
  9  \w     39.00 137.00   1.00   13.00    --  108.00 -77.00 150.00   98
 10  \w     42.00  92.00   1.00   13.00    --  108.00-111.00 -90.00   50
 11  \w     67.00 106.00   1.00   13.00    --  108.00 -94.00  60.00   39
 12  \w     98.00 134.00   1.00   13.00    --  108.00 -30.00 -30.00   36
 13  \w     38.00  66.00   1.00   13.00    --  108.00 -30.00 -30.00   28
 14  \w    134.00 178.00   1.00   13.00    --  108.00  15.00  30.00   44
 15  \w     42.00 133.00   1.00   13.00    --  108.00 -77.00 -60.00   91
 16  \w     45.00 111.00   1.00   13.00    --  108.00 -30.00  90.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1055754000
_diffrn_orient_matrix_UB_12      -0.0270960000
_diffrn_orient_matrix_UB_13      0.0475442000
_diffrn_orient_matrix_UB_21      -0.0588329000
_diffrn_orient_matrix_UB_22      0.1233701000
_diffrn_orient_matrix_UB_23      0.0318016000
_diffrn_orient_matrix_UB_31      -0.1100144000
_diffrn_orient_matrix_UB_32      -0.0921275000
_diffrn_orient_matrix_UB_33      0.0286080000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8071
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.058
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         3.669
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (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    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1285 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0719P)^2^+0.1825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3538
_reflns_number_total             3985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01328a2.cif
_cod_data_source_block           202009189
_cod_depositor_comments          'Adding full bibliography for 7158236.cif.'
_cod_database_code               7158236
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H30O2N2S1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.806
_reflns_odcompleteness_completeness 99.87
_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 N(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:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.903