Asymmetric dearomatization of 2-nitrobenzofurans by organocatalyzed one-step Michael addition to access 3,3'-disubstituted oxindoles.
Ge, Zhen-Zhen; Yang, Lei; You, Yong; Wang, Zhen-Hua; Xie, Ke-Xin; Zhou, Ming-Qiang; Zhao, Jian-Qiang; Yuan, Wei-Cheng; Chemical communications (Cambridge, England) 56 (2020) 2586–2589; doi:10.1039/c9cc09939e

data_7125877
_publ_section_title
;
 Asymmetric dearomatization of 2-nitrobenzofurans by organocatalyzed
 one-step Michael addition to access 3,3'-disubstituted oxindoles.
;
_journal_issue                   17
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2586
_journal_page_last               2589
_journal_paper_doi               10.1039/c9cc09939e
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H16 Cl N3 O4'
_chemical_formula_sum            'C21 H16 Cl N3 O4'
_chemical_formula_weight         409.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-28 deposited with the CCDC.	2020-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.306(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3140(4)
_cell_length_b                   21.8053(13)
_cell_length_c                   9.5831(5)
_cell_measurement_reflns_used    6023
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.1370
_cell_measurement_theta_min      4.0510
_cell_volume                     1940.78(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
  1 omega  -48.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 84

  2 omega  -41.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   60.0000 26

  3 omega  -82.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000   90.0000 70

  4 omega  -31.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -150.0000 68

  5 omega   62.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 26

  6 omega   24.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 25

  7 omega   10.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 25

  8 omega   28.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 27

  9 omega   56.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 37

 10 omega   16.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000    0.0000 40

 11 omega   15.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 32

 12 omega   -1.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -30.0000 62

 13 omega  -32.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  -30.0000 93

 14 omega   26.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   90.0000 25

 15 omega   10.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   30.0000 25

 16 omega   10.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   60.0000 62

 17 omega   63.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 26

 18 omega    9.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   90.0000 38

 19 omega   20.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000    0.0000 31

 20 omega   80.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 25

 21 omega   -8.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  106.0000   61.5941 25

 22 omega   57.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 50

 23 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 26

 24 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 25 omega  100.00  149.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 49

 26 omega   94.00  120.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 26

 27 omega   88.00  165.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 77

 28 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 26

 29 omega   52.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 57

 30 omega   89.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 26

 31 omega   83.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 32

 32 omega   88.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 25

 33 omega   80.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   76.0000    4.6736 97

 34 omega   80.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 35 omega   88.00  147.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 59

 36 omega   88.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 26

 37 omega   82.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 26

 38 omega   88.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 25

 39 omega   44.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 35

 40 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 41 omega  100.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 78

 42 omega   90.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 86

 43 omega   82.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 33

 44 omega   88.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 25

 45 omega  126.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 51

 46 omega   82.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 26

 47 omega   83.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 32

 48 omega  119.00  155.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 36

 49 omega   88.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 26

 50 omega  124.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 52

 51 omega   88.00  141.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 53

 52 omega   92.00  118.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 26

 53 omega   79.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 25

 54 omega   72.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 27

 55 omega   83.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   70.0000  -27.9358 25

 56 omega   79.00  128.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   26.0000   20.6541 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1431246000
_diffrn_orient_matrix_UB_12      -0.0162833000
_diffrn_orient_matrix_UB_13      0.0828157000
_diffrn_orient_matrix_UB_21      -0.0789084000
_diffrn_orient_matrix_UB_22      -0.0049754000
_diffrn_orient_matrix_UB_23      0.1351742000
_diffrn_orient_matrix_UB_31      -0.0282101000
_diffrn_orient_matrix_UB_32      -0.0685756000
_diffrn_orient_matrix_UB_33      -0.0293581000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0402
_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       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18941
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.055
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.403
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2111 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         6342
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0674P)^2^+0.1208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.822
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                5658
_reflns_number_total             6342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09939e2.cif
_cod_data_source_block           201811452
_cod_depositor_comments          'Adding full bibliography for 7125877.cif.'
_cod_original_cell_volume        1940.77(17)
_cod_database_code               7125877
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N1Cl1
_shelx_estimated_absorpt_t_max   0.822
_shelx_estimated_absorpt_t_min   0.750
_reflns_odcompleteness_completeness 99.97
_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 Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C10'(H10'), C11'(H11')
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C5'(H5'), C6'(H6'), C7'(H7'), C8'(H8'),
 C14'(H14'), C15'(H15'), C17'(H17'), C18'(H18'), C19'(H19'), C20'(H20'),
 C21'(H21')
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9'(H9'A,H9'B,H9'C)
;
_olex2_submission_special_instructions 'No special instructions were received'