A base-catalyzed domino reaction between isoindigos and α-alkylidene succinimides-convenient preparation of highly steric bispirooxindoles.
Li, Chen-Yi; Xiang, Min; Song, Xiang-Jia; Zou, Ying; Huang, Zhi-Cheng; Li, Xia; Tian, Fang; Wang, Li-Xin; Organic & biomolecular chemistry 18 (2020) 9511–9515; doi:10.1039/d0ob01858a

data_7157772
_publ_section_title
;
 A base-catalyzed domino reaction between isoindigos and \a-alkylidene
 succinimides-convenient preparation of highly steric bispirooxindoles.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9511
_journal_page_last               9515
_journal_paper_doi               10.1039/d0ob01858a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C43 H39 N3 O8'
_chemical_formula_sum            'C43 H39 N3 O8'
_chemical_formula_weight         725.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-26 deposited with the CCDC.	2020-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 134.872(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   41.0905(9)
_cell_length_b                   12.16370(11)
_cell_length_c                   21.1598(5)
_cell_measurement_reflns_used    12436
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8230
_cell_measurement_theta_min      3.9140
_cell_volume                     7495.0(6)
_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  -80.00  -54.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000 -180.0000 52

  2 omega  -53.00   15.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000 -180.0000 136

  3 omega  -13.00   35.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   30.0000 96

  4 omega   75.00  101.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 52

  5 omega   26.00   52.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 52

  6 omega  -26.00   65.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 182

  7 omega   12.00   52.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -30.0000 80

  8 omega   -3.00   28.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 62

  9 omega   75.00  100.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -180.0000 50

 10 omega   75.00  101.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 52

 11 omega   -4.00   22.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 52

 12 omega  -30.00   16.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 92

 13 omega   72.00   98.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 52

 14 omega   67.00   93.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 52

 15 omega   71.00  110.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 78

 16 omega  -32.00    5.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -30.0000 74

 17 omega   25.00   60.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -135.0000  -82.0000 70

 18 omega   63.00  102.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 78

 19 omega   40.00   75.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 70

 20 omega   12.00   40.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 56

 21 omega   29.00   57.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -180.0000 56

 22 omega   14.00  105.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  120.0000 182

 23 omega   67.00   93.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -135.0000  -82.0000 52

 24 omega   60.00  104.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  120.0000 88

 25 omega   68.00  113.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 90

 26 omega   60.00  152.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -150.0000 184

 27 omega   37.00   71.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 68

 28 omega   48.00  106.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 116

 29 omega  135.00  167.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 64

 30 omega   38.00   91.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 106

 31 omega   38.00   79.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 82

 32 omega   40.00   82.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 84

 33 omega   91.00  117.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 52

 34 omega   64.00   97.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 66

 35 omega   57.00   98.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 82

 36 omega   38.00  109.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 142

 37 omega   47.00   73.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 52

 38 omega   50.00   76.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 52

 39 omega   62.00  106.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 88

 40 omega   44.00   70.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 52

 41 omega   40.00  127.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 174

 42 omega   65.00  177.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 224

 43 omega  118.00  144.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 52

 44 omega   52.00  110.00   0.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0044512500
_diffrn_orient_matrix_UB_12      0.0942292500
_diffrn_orient_matrix_UB_13      -0.0421760000
_diffrn_orient_matrix_UB_21      -0.0242678500
_diffrn_orient_matrix_UB_22      0.0784867500
_diffrn_orient_matrix_UB_23      0.0131446000
_diffrn_orient_matrix_UB_31      0.0467816000
_diffrn_orient_matrix_UB_32      0.0316971000
_diffrn_orient_matrix_UB_33      0.0927260000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28879
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         3.938
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80668
_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    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             3056
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         6699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0681P)^2^+3.5524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5785
_reflns_number_total             6699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01858a2.cif
_cod_data_source_block           201907191
_cod_depositor_comments          'Adding full bibliography for 7157772.cif.'
_cod_original_cell_volume        7495.0(4)
_cod_database_code               7157772
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C21H22N3O3
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.892
_reflns_odcompleteness_completeness 99.96
_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:
 C2(H2), C3(H3), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C22(H22), C23(H23), C24(H24), C25(H25), C35(H35), C36(H36),
  C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C41(H41A,H41B,
 H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C)
;
_olex2_submission_special_instructions 'No special instructions were received'