ArPNO-catalyzed acylative kinetic resolution of tertiary alcohols: access to 3-hydroxy-3-substituted oxindoles
Yang, Min; Gao, Yu-Lin; Xie, Ming-Sheng; Guo, Hai-Ming; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01205G

data_7158798
_publ_section_title
;
 ArPNO-catalyzed acylative kinetic resolution of tertiary alcohols: access
 to 3-hydroxy-3-substituted oxindoles
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01205G
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H17 N O3'
_chemical_formula_sum            'C22 H17 N O3'
_chemical_formula_weight         343.39
_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'
_symmetry_Int_Tables_number      19
_audit_creation_date             2022-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-23 deposited with the CCDC.	2022-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.30180(10)
_cell_length_b                   10.53570(10)
_cell_length_c                   20.17220(10)
_cell_measurement_reflns_used    18161
_cell_measurement_temperature    189.99(10)
_cell_measurement_theta_max      71.4240
_cell_measurement_theta_min      4.1650
_cell_volume                     1764.37(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      189.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9910
_diffrn_measured_fraction_theta_max 0.9910
_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    -53.00  31.00   1.00    1.00    --  -35.62  59.00  54.00   84
  2  \w      4.00  76.00   1.00    1.00    --   35.62-101.00-176.00   72
  3  \w     41.00 129.00   1.00    1.00    --  107.12 -68.00  64.00   88
  4  \w     37.00 110.00   1.00    1.00    --  107.12-101.00-176.00   73
  5  \w     90.00 174.00   1.00    1.00    --  107.12  59.00  54.00   84
  6  \w    -76.00  18.00   1.00    1.00    --  -35.62 101.00 -72.00   94
  7  \w    -32.00  52.00   1.00    1.00    --   35.62 -57.00-180.00   84
  8  \w     57.00 108.00   1.00    1.00    --   35.62 178.00-180.00   51
  9  \w    100.00 177.00   1.00    1.00    --  107.12 111.00-120.00   77
 10  \w     38.00 110.00   1.00    1.00    --  107.12 -95.00 -60.00   72
 11  \w     89.00 174.00   1.00    1.00    --  107.12  61.00   0.00   85
 12  \w    100.00 177.00   1.00    1.00    --  107.12 111.00-180.00   77
 13  \w     86.00 177.00   1.00    1.00    --  107.12  30.00 150.00   91
 14  \w     40.00 125.00   1.00    1.00    --  107.12 -59.00 -85.00   85
 15  \w   -103.00  -9.00   1.00    1.00    --  -35.62 -77.00 150.00   94
 16  \w   -103.00  -9.00   1.00    1.00    --  -35.62 -77.00  90.00   94
 17  \w   -103.00 -18.00   1.00    1.00    --  -35.62 -59.00 -85.00   85
 18  \w   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00 -30.00   84
 19  \w   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00-180.00   84
 20  \w      9.00 103.00   1.00    1.00    --   35.62  77.00  30.00   94
 21  \w    -34.00  55.00   1.00    1.00    --   35.62 -38.00  60.00   89
 22  \w     38.00 110.00   1.00    1.00    --  107.12 -95.00-120.00   72
 23  \w     89.00 174.00   1.00    1.00    --  107.12  61.00  30.00   85
 24  \w     90.00 176.00   1.00    1.00    --  107.12  45.00-180.00   86
 25  \w     80.00 175.00   1.00    1.00    --  107.12  77.00 -30.00   95
 26  \w     89.00 174.00   1.00    1.00    --  107.12  61.00  90.00   85
 27  \w     86.00 177.00   1.00    1.00    --  107.12  30.00-120.00   91
 28  \w     86.00 177.00   1.00    1.00    --  107.12  30.00 -60.00   91
 29  \w   -108.00 -35.00   1.00    1.00    --  -35.62-178.00-180.00   73
 30  \w      9.00 103.00   1.00    1.00    --   35.62  77.00 -30.00   94
 31  \w      9.00 103.00   1.00    1.00    --   35.62  77.00  60.00   94
 32  \w     17.00 105.00   1.00    1.00    --   35.62  38.00-120.00   88
 33  \w      6.00 107.00   1.00    1.00    --   35.62  19.00-150.00  101
 34  \w     17.00 105.00   1.00    1.00    --   35.62  38.00   0.00   88
 35  \w      9.00 103.00   1.00    1.00    --   35.62  77.00 -90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1248051000
_diffrn_orient_matrix_UB_12      0.0739606000
_diffrn_orient_matrix_UB_13      -0.0412943000
_diffrn_orient_matrix_UB_21      -0.0357374000
_diffrn_orient_matrix_UB_22      -0.0856647000
_diffrn_orient_matrix_UB_23      -0.0601233000
_diffrn_orient_matrix_UB_31      -0.1325704000
_diffrn_orient_matrix_UB_32      0.0926268000
_diffrn_orient_matrix_UB_33      -0.0226246000
_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  0.0336
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22801
_diffrn_reflns_theta_full        71.5658
_diffrn_reflns_theta_max         71.57
_diffrn_reflns_theta_min         4.38
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
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    1.2926
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             722.3477
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.1332
_refine_diff_density_min         -0.2621
_refine_diff_density_rms         0.0564
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.14(13)
_refine_ls_d_res_high            0.8126
_refine_ls_d_res_low             10.0861
_refine_ls_goodness_of_fit_ref   1.1026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1026
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.2195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.985
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              24
_reflns_limit_l_min              -24
_reflns_number_gt                3357
_reflns_number_total             3414
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2ob01205g2.cif
_cod_data_source_block           YM-20220411
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7158798
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_diffrn_oxdiff_digest_frames
;
01170c10c53c267baaf6b4f9f307dfcf7c031005882
;
_diffrn_oxdiff_digest_hkl
;
013bf4e3b972a9c44d7826cbc21495a22db361
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C17(H17), C13(H13), C15(H15), C14(H14), C7(H7), C21(H21),
 C20(H20), C11(H11), C19(H19), C6(H6), C18(H18), C12(H12)
2.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c)
;
_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.594