Se-catalyzed enantioselective lactamization enabled by a <i>N</i>-fluorosulfonyl group: total synthesis of diaporisoindole A.
Yamamoto, Daiki; Yamasaki, Shun; Hashimoto, Takuya; Chemical science 17 (2026) 3313–3319; doi:10.1039/d5sc08502k

data_1576484
_publ_section_title
;
 Se-catalyzed enantioselective lactamization enabled by a
 <i>N</i>-fluorosulfonyl group: total synthesis of diaporisoindole A.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              3313
_journal_page_last               3319
_journal_paper_doi               10.1039/d5sc08502k
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         '2(C10 H9 F I N O3 S)'
_chemical_formula_sum            'C20 H18 F2 I2 N2 O6 S2'
_chemical_formula_weight         738.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-03
_audit_creation_method
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2025-09-03 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                74.713(3)
_cell_angle_beta                 77.550(3)
_cell_angle_gamma                77.289(3)
_cell_formula_units_Z            1
_cell_length_a                   7.6473(2)
_cell_length_b                   7.7662(3)
_cell_length_c                   10.9617(4)
_cell_measurement_reflns_used    4193
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      75.3630
_cell_measurement_theta_min      4.2400
_cell_volume                     603.94(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.921
_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     50.00  76.00   0.50    0.05    --   46.62-142.00 119.00   52
  2  \w     76.00 123.00   0.50    0.08    --  105.44-142.00 119.00   94
  3  \w     85.00 111.00   0.50    0.08    --  105.44-125.00   0.00   52
  4  \w     51.00  76.00   0.50    0.08    --  105.44-125.00   0.00   50
  5  \w     35.00  64.00   0.50    0.08    --  105.44 -94.00   0.00   58
  6  \w     69.00 101.00   0.50    0.08    --  105.44 -94.00   0.00   64
  7  \w     80.00 106.00   0.50    0.08    --  105.44-128.00 -69.00   52
  8  \w     50.00 106.00   0.50    0.08    --  105.44-125.00-120.00  112
  9  \w     42.00  67.00   0.50    0.05    --   46.62-128.00 -69.00   50
 10  \w     11.00  38.00   0.50    0.05    --   46.62 -38.00-180.00   54
 11  \w    -27.00   8.00   0.50    0.05    --   46.62 -38.00-180.00   70
 12  \w     40.00  65.00   0.50    0.08    --  105.44 -61.00 -90.00   50
 13  \w     39.00  72.00   0.50    0.08    --  105.44 -61.00  60.00   66
 14  \w     35.00  66.00   0.50    0.08    --  105.44 -61.00  90.00   62
 15  \w     45.00  71.00   0.50    0.08    --  105.44 -61.00 150.00   52
 16  \w     51.00 120.00   0.50    0.05    --   46.62  77.00 -60.00  138
 17  \w    142.00 174.00   0.50    0.08    --  105.44  30.00 -60.00   64
 18  \w     97.00 136.00   0.50    0.08    --  105.44  30.00 -60.00   78
 19  \w    145.00 170.00   0.50    0.08    --  105.44 125.00  60.00   50
 20  \w     84.00 121.00   0.50    0.08    --  105.44 142.00 175.00   74
 21  \w    107.00 133.00   0.50    0.08    --  105.44 125.00  60.00   52
 22  \w    115.00 144.00   0.50    0.08    --  105.44 128.00   4.00   58
 23  \w    -17.00  27.00   0.50    0.05    --  -46.62  19.00 -60.00   88
 24  \w    -71.00 -19.00   0.50    0.08    --  -91.75  61.00-180.00  104
 25  \w   -103.00 -54.00   0.50    0.08    --  -91.75  77.00-180.00   98
 26  \w    -45.00 -19.00   0.50    0.08    --  -91.75  45.00-120.00   52
 27  \w    -48.00 -23.00   0.50    0.08    --  -91.75  45.00 -60.00   50
 28  \w    -12.00  14.00   0.50    0.05    --  -46.62  19.00-150.00   52
 29  \w    -45.00 -20.00   0.50    0.08    --  -91.75  45.00   0.00   50
 30  \w    -49.00 -19.00   0.50    0.08    --  -91.75  45.00  30.00   60
 31  \w    -50.00 -20.00   0.50    0.08    --  -91.75  45.00  60.00   60
 32  \w   -106.00 -80.00   0.50    0.08    --  -91.75 -15.00 150.00   52
 33  \w    -91.00 -61.00   0.50    0.05    --  -46.62 142.00 175.00   60
 34  \w    -57.00 -15.00   0.50    0.05    --  -46.62 128.00   4.00   84
 35  \w   -142.00-117.00   0.50    0.08    --  -91.75 -15.00 150.00   50
 36  \w   -163.00 -81.00   0.50    0.08    --  -91.75 -30.00  90.00  164
 37  \w   -109.00 -63.00   0.50    0.05    --  -46.62-142.00 119.00   92
 38  \w   -149.00 -78.00   0.50    0.08    --  -91.75-142.00 119.00  142
 39  \w   -154.00-111.00   0.50    0.08    --  -91.75-128.00 -69.00   86
 40  \w   -109.00 -74.00   0.50    0.08    --  -91.75-125.00-120.00   70
 41  \w   -153.00-126.00   0.50    0.08    --  -91.75-125.00-120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0073430000
_diffrn_orient_matrix_UB_12      -0.1486278000
_diffrn_orient_matrix_UB_13      0.1245622000
_diffrn_orient_matrix_UB_21      0.0572017000
_diffrn_orient_matrix_UB_22      -0.1463550000
_diffrn_orient_matrix_UB_23      -0.0791394000
_diffrn_orient_matrix_UB_31      0.2013749000
_diffrn_orient_matrix_UB_32      0.0093638000
_diffrn_orient_matrix_UB_33      -0.0078041000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6299
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.206
_diffrn_reflns_theta_min         4.241
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    22.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
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    2.030
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.946
_refine_diff_density_min         -1.395
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.787
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.787
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0361
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             2327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08502k2.cif
_cod_data_source_block           exp_399_auto
_cod_database_code               1576484
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.211
_shelx_estimated_absorpt_t_min   0.071
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H)
;
_shelx_res_checksum              74868
_shelx_hkl_checksum              81836
_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 3.126
_oxdiff_exptl_absorpt_empirical_full_min 0.575