An enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived <i>N</i>-Boc ketimines.
Liu, Hui; Yan, Yingkun; Li, Min; Zhang, Xiaomei; Organic & biomolecular chemistry 19 (2021) 3820–3824; doi:10.1039/d1ob00374g

data_7158005
_publ_section_title
;
 An enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with
 isatin-derived <i>N</i>-Boc ketimines.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3820
_journal_page_last               3824
_journal_paper_doi               10.1039/d1ob00374g
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H29 Cl N4 O4'
_chemical_formula_sum            'C26 H29 Cl N4 O4'
_chemical_formula_weight         496.98
_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             2020-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-20 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2734(2)
_cell_length_b                   12.5056(3)
_cell_length_c                   22.5981(7)
_cell_measurement_reflns_used    3111
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4880
_cell_measurement_theta_min      4.0220
_cell_volume                     2620.69(12)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -56.00  37.00   1.00    1.50    --  -33.50  37.00 -90.00   93
  2  \w     63.00  89.00   1.00    1.50    --   36.47  57.00  60.00   26
  3  \w     71.00 110.00   1.00    1.50    --   36.47 178.00 120.00   39
  4  \w     19.00  52.00   1.00    1.50    --   36.47  57.00  60.00   33
  5  \w    -32.00  40.00   1.00    1.50    --   36.47 -77.00 -90.00   72
  6  \w     79.00 105.00   1.00    1.50    --   36.47 178.00-150.00   26
  7  \w     35.00  61.00   1.00    1.50    --   36.47 -99.00   0.00   26
  8  \w     35.00 105.00   1.00    1.50    --   36.47  57.00   0.00   70
  9  \w     -1.00  30.00   1.00    1.50    --   36.47 -99.00   0.00   31
 10  \w     37.00 105.00   1.00    7.50    --  108.00-111.00 120.00   68
 11  \w     84.00 110.00   1.00    7.50    --  108.00 -45.00 150.00   26
 12  \w     39.00  72.00   1.00    7.50    --  108.00 -45.00 150.00   33
 13  \w     48.00 112.00   1.00    7.50    --  108.00 -30.00  60.00   64
 14  \w     53.00  86.00   1.00    7.50    --  108.00 -94.00 -30.00   33
 15  \w    105.00 174.00   1.00    7.50    --  108.00  61.00-120.00   69
 16  \w    107.00 155.00   1.00    7.50    --  108.00 111.00 120.00   48
 17  \w     41.00 133.00   1.00    7.50    --  108.00 -77.00 120.00   92
;
_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      0.0304382000
_diffrn_orient_matrix_UB_12      -0.0194394000
_diffrn_orient_matrix_UB_13      0.0661702000
_diffrn_orient_matrix_UB_21      0.1171182000
_diffrn_orient_matrix_UB_22      -0.0820944000
_diffrn_orient_matrix_UB_23      -0.0164734000
_diffrn_orient_matrix_UB_31      0.1138305000
_diffrn_orient_matrix_UB_32      0.0897073000
_diffrn_orient_matrix_UB_33      -0.0007331000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9257
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.016
_diffrn_reflns_theta_max         67.016
_diffrn_reflns_theta_min         3.912
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95096
_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    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(14)
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.2617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4029
_reflns_number_total             4660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00374g2.cif
_cod_data_source_block           202012299_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7158004--7158005.cif.'
_cod_database_code               7158005
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.795
_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
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups
2.a Riding coordinates:
 C26(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4A), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              86854
_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 1.122
_oxdiff_exptl_absorpt_empirical_full_min 0.912
_cod_duplicate_entry 7158004