Base Catalyzed Abnormal [3 + 2]-Cycloaddition between Isatin N,N'-Cyclic Azomethine Imine 1,3-Dipole and 3-Methyleneoxindole for the One-step Construction of Tetracyclic Bispirooxindoles.
Song, Xiang-Jia; Ren, Hong-Xia; Xiang, Min; Li, Chen-Yi; Tian, Fang; Wang, Li-Xin; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03050

data_4037869
_publ_section_title
;
 Base Catalyzed Abnormal [3 + 2]-Cycloaddition between Isatin N,N'-Cyclic
 Azomethine Imine 1,3-Dipole and 3-Methyleneoxindole for the One-step
 Construction of Tetracyclic Bispirooxindoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03050
_journal_year                    2020
_chemical_formula_moiety         'C37 H30 Br Cl N4 O5'
_chemical_formula_sum            'C37 H30 Br Cl N4 O5'
_chemical_formula_weight         726.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_audit_creation_date             2019-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7459(8)
_cell_length_b                   10.4802(4)
_cell_length_c                   20.5472(7)
_cell_measurement_reflns_used    4017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8810
_cell_measurement_theta_min      4.4490
_cell_volume                     3267.3(2)
_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
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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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -47.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000    0.0000 76

  2 omega -101.00  -61.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 40

  3 omega   17.00   54.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -30.0000 37

  4 omega   58.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 29

  5 omega   44.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   60.0000 57

  6 omega   53.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   30.0000 53

  7 omega   81.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   90.0000 25

  8 omega  -32.00    1.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -30.0000 33

  9 omega   81.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 29

 10 omega   57.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 51

 11 omega   38.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   90.0000 27

 12 omega   11.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   60.0000 26

 13 omega   38.00   99.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 61

 14 omega   37.00   82.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 45

 15 omega   78.00  114.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 36

 16 omega   37.00   75.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 38

 17 omega   63.00  108.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 45

 18 omega  114.00  139.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 25

 19 omega   68.00   94.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 26

 20 omega   40.00   66.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 26

 21 omega  103.00  172.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 69

 22 omega   37.00   80.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 43

 23 omega   38.00   83.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 45

 24 omega   72.00  127.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
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_diffrn_orient_matrix_UB_11      0.0117806000
_diffrn_orient_matrix_UB_12      -0.0178559000
_diffrn_orient_matrix_UB_13      -0.0714787000
_diffrn_orient_matrix_UB_21      0.0999937000
_diffrn_orient_matrix_UB_22      -0.0163404000
_diffrn_orient_matrix_UB_23      0.0302568000
_diffrn_orient_matrix_UB_31      -0.0127036000
_diffrn_orient_matrix_UB_32      -0.1449389000
_diffrn_orient_matrix_UB_33      0.0053493000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13018
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.116
_diffrn_reflns_theta_max         67.116
_diffrn_reflns_theta_min         4.466
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51947
_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    1.476
_exptl_crystal_description       prism
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         5837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0484P)^2^+0.8651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                4546
_reflns_number_total             5837
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03050_si_002.cif
_cod_data_source_block           201905133
_cod_database_code               4037869
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4Cl1Br1
_shelx_estimated_absorpt_t_max   0.742
_shelx_estimated_absorpt_t_min   0.639
_reflns_odcompleteness_completeness 99.71
_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
2.a Ternary CH refined with riding coordinates:
 C33(H33), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C24(H24A,H24B), C32(H32A,H32B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_olex2_submission_special_instructions 'No special instructions were received'