Enantioselective and regioselective aza-Friedel-Crafts reaction of electron-rich phenols with isatin-derived ketimines.
Cai, Liu; Liu, Xiangshuai; Wang, Jie; Chen, Li; Li, Xin; Cheng, Jin-Pei; Chemical communications (Cambridge, England) 56 (2020) 10361–10364; doi:10.1039/d0cc04966b

data_7126993
_publ_section_title
;
 Enantioselective and regioselective aza-Friedel-Crafts reaction of
 electron-rich phenols with isatin-derived ketimines.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10361
_journal_page_last               10364
_journal_paper_doi               10.1039/d0cc04966b
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H30 N2 O6'
_chemical_formula_sum            'C28 H30 N2 O6'
_chemical_formula_weight         490.54
_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     dual
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-06-24 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.51250(10)
_cell_length_b                   16.33800(10)
_cell_length_c                   17.88090(10)
_cell_measurement_reflns_used    12725
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      79.1240
_cell_measurement_theta_min      5.3940
_cell_volume                     2486.83(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.995
_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   -199.00 -21.00   0.50    2.00    -- -110.00  12.00  77.00  356
  2  \w    -24.00  94.00   0.50    0.50    --    5.00  57.00 -60.00  236
  3  \w    -78.00  39.00   0.50    0.50    --  -50.10  57.00  90.00  234
  4  \w    -51.00 -21.00   0.50    0.50    --  -50.10 -12.00 -95.00   60
  5  \w   -140.00 -52.00   0.50    2.00    -- -110.00  38.00  60.00  176
  6  \w   -199.00 -76.00   0.50    2.00    -- -110.00 -32.00 -51.43  246
  7  \w   -139.00 -23.00   0.50    2.00    -- -110.00  72.00-150.00  232
  8  \w   -177.00-132.00   0.50    2.00    -- -110.00 -57.00-120.00   90
  9  \w   -114.00 -89.00   0.50    2.00    -- -110.00  72.00-180.00   50
 10  \w   -124.00 -98.00   0.50    2.00    -- -110.00  72.00-120.00   52
 11  \w   -139.00 -21.00   0.50    2.00    -- -110.00  57.00-150.00  236
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0289376000
_diffrn_orient_matrix_UB_12      0.0931267000
_diffrn_orient_matrix_UB_13      0.0005897000
_diffrn_orient_matrix_UB_21      0.0046872000
_diffrn_orient_matrix_UB_22      -0.0002772000
_diffrn_orient_matrix_UB_23      0.0861178000
_diffrn_orient_matrix_UB_31      0.1785290000
_diffrn_orient_matrix_UB_32      0.0150477000
_diffrn_orient_matrix_UB_33      -0.0021060000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16130
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.495
_diffrn_reflns_theta_min         3.665
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.310
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1986 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_coef       0.0022(3)
_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   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0427P)^2^+0.1958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                4799
_reflns_number_total             4929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04966b2.cif
_cod_data_source_block           p20190306b
_cod_depositor_comments          'Adding full bibliography for 7126993.cif.'
_cod_database_code               7126993
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C27H24N2O6
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.772
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C13(H13), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              35640
_shelx_hkl_checksum              28297
_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.532