Exploration of a KI-catalyzed oxidation system for direct construction of bispyrrolidino[2,3-b]indolines and the total synthesis of (+)-WIN 64821.
Chen, Si-Kai; Yang, Ju-Song; Dai, Kun-Long; Zhang, Fu-Min; Zhang, Xiao-Ming; Tu, Yong-Qiang; Chemical communications (Cambridge, England) 56 (2020) 121–124; doi:10.1039/c9cc08646c

data_7125427
_publ_section_title
;
 Exploration of a KI-catalyzed oxidation system for direct construction of
 bispyrrolidino[2,3-b]indolines and the total synthesis of (+)-WIN 64821.
;
_journal_issue                   1
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              121
_journal_page_last               124
_journal_paper_doi               10.1039/c9cc08646c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C36 H38 N4 O4 S2'
_chemical_formula_sum            'C38 H38 N2 O4 S2'
_chemical_formula_weight         650.82
_chemical_name_common            6a
_chemical_name_systematic        product
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-13 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.596(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4849(8)
_cell_length_b                   10.3567(3)
_cell_length_c                   19.7384(8)
_cell_measurement_reflns_used    2196
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9630
_cell_measurement_theta_min      4.0040
_cell_volume                     3332.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -41.00   42.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 83

  2 omega  -23.00   39.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000 -180.0000 62

  3 omega  -40.00   54.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000  -60.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0122682000
_diffrn_orient_matrix_UB_12      -0.0420652000
_diffrn_orient_matrix_UB_13      0.0249424000
_diffrn_orient_matrix_UB_21      0.0315110000
_diffrn_orient_matrix_UB_22      0.0251890000
_diffrn_orient_matrix_UB_23      0.0249108000
_diffrn_orient_matrix_UB_31      -0.0274025000
_diffrn_orient_matrix_UB_32      0.0478108000
_diffrn_orient_matrix_UB_33      0.0088320000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13247
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_min         3.459
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0601P)^2^+1.6529P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3838
_reflns_number_total             6550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08646c2.cif
_cod_data_source_block           yangjs_0320
_cod_depositor_comments          'Adding full bibliography for 7125427.cif.'
_cod_original_cell_volume        3332.0(2)
_cod_database_code               7125427
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C9(H9), C4AA(H4AA)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C12(H12A,H12B), C22(H22A,H22B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C26(H26), C15(H15), C3(H3), C25(H25), C28(H28), C6(H6), C32(H32),
 C4(H4), C16(H16), C17(H17), C36(H36), C5(H5), C18(H18), C35(H35), C33(H33)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C10(H10A,H10B,H10C), C23(H23A,H23B,H23C), C37(H37A,H37B,
 H37C)
;
_shelx_res_checksum              86974
_olex2_date_sample_data_collection 2019-03-20
_olex2_submission_special_instructions 'No special instructions were received'