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_1576481
_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         'C11 H11 F I N O3 S'
_chemical_formula_sum            'C11 H11 F I N O3 S'
_chemical_formula_weight         383.17
_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             2025-04-04
_audit_creation_method
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2025-08-25 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                81.7530(10)
_cell_angle_beta                 75.2280(10)
_cell_angle_gamma                78.6440(10)
_cell_formula_units_Z            2
_cell_length_a                   7.32110(10)
_cell_length_b                   8.01260(10)
_cell_length_c                   11.50270(10)
_cell_measurement_reflns_used    13065
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      75.9320
_cell_measurement_theta_min      3.9670
_cell_volume                     636.584(13)
_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 0.999
_diffrn_measured_fraction_theta_max 0.942
_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     -1.00  25.00   0.50    0.50    --  -46.62  60.00-172.00   52
  2  \w    -41.00 -15.00   0.50    0.50    --  -46.62  60.00-172.00   52
  3  \w    -24.00  29.00   0.50    0.50    --  -46.62  19.00-180.00  106
  4  \w    -26.00   9.00   0.50    0.50    --  -46.62  19.00 -30.00   70
  5  \w    -26.00  28.00   0.50    0.50    --  -46.62  19.00  90.00  108
  6  \w     24.00  69.00   0.50    0.50    --   46.62  77.00  90.00   90
  7  \w     90.00 120.00   0.50    0.50    --   46.62  77.00 150.00   60
  8  \w     95.00 120.00   0.50    0.50    --   46.62  77.00 -30.00   50
  9  \w     85.00 118.00   0.50    0.50    --   46.62  77.00 -90.00   66
 10  \w     24.00  67.00   0.50    0.50    --   46.62  77.00-150.00   86
 11  \w     30.00  61.00   0.50    0.50    --   46.62  60.00-172.00   62
 12  \w     23.00  65.00   0.50    0.50    --   46.62  77.00 -90.00   84
 13  \w     39.00  83.00   0.50    0.50    --   46.62  38.00-120.00   88
 14  \w     24.00  50.00   0.50    0.50    --   46.62  77.00 -30.00   52
 15  \w     35.00  85.00   0.50    0.50    --   46.62  38.00   0.00  100
 16  \w     34.00  96.00   0.50    0.50    --   46.62  57.00  60.00  124
 17  \w     24.00  50.00   0.50    0.50    --   46.62  77.00 150.00   52
 18  \w     41.00  79.00   0.50    0.50    --   46.62  38.00 150.00   76
 19  \w     86.00 113.00   0.50    0.50    --   46.62  38.00 150.00   54
 20  \w     80.00 105.00   0.50    0.50    --  105.44 -77.00 150.00   50
 21  \w     34.00  65.00   0.50    0.50    --  105.44 -77.00 150.00   62
 22  \w     35.00  64.00   0.50    0.50    --  105.44 -60.00  48.00   58
 23  \w     42.00  68.00   0.50    0.50    --  105.44 -61.00   0.00   52
 24  \w     45.00 103.00   0.50    0.50    --  105.44 -77.00 -30.00  116
 25  \w     45.00  72.00   0.50    0.50    --  105.44 -61.00-180.00   54
 26  \w     70.00 104.00   0.50    0.50    --  105.44 -94.00-180.00   68
 27  \w     56.00 108.00   0.50    0.50    --  105.44-125.00 -60.00  104
 28  \w     77.00 104.00   0.50    0.50    --  105.44 -94.00 -30.00   54
 29  \w     67.00 104.00   0.50    0.50    --  105.44 -94.00 -90.00   74
 30  \w     35.00  65.00   0.50    0.50    --  105.44 -94.00 -30.00   60
 31  \w     34.00  85.00   0.50    0.50    --   46.62-125.00 -30.00  102
 32  \w     63.00 103.00   0.50    0.50    --  105.44 -94.00  60.00   80
 33  \w     81.00 106.00   0.50    0.50    --  105.44-125.00 120.00   50
 34  \w     36.00  66.00   0.50    0.50    --  105.44-125.00 120.00   60
 35  \w     39.00 100.00   0.50    0.50    --  105.44 -94.00 150.00  122
 36  \w     95.00 174.00   0.50    0.50    --  105.44  45.00 -90.00  158
 37  \w     91.00 173.00   0.50    0.50    --  105.44  60.00-172.00  164
 38  \w     25.00  63.00   0.50    0.50    --   46.62 -60.00  48.00   76
 39  \w    -11.00  15.00   0.50    0.50    --   46.62 -60.00  48.00   52
 40  \w    -52.00 -20.00   0.50    0.50    --  -91.75  61.00 120.00   64
 41  \w    -48.00 -22.00   0.50    0.50    --  -91.75  45.00  60.00   52
 42  \w    -44.00 -19.00   0.50    0.50    --  -91.75  45.00  30.00   50
 43  \w    -50.00 -22.00   0.50    0.50    --  -91.75  45.00 -90.00   56
 44  \w    -56.00 -21.00   0.50    0.50    --  -91.75  60.00-172.00   70
 45  \w   -167.00 -77.00   0.50    0.50    --  -91.75 -15.00 -60.00  180
 46  \w   -164.00-121.00   0.50    0.50    --  -91.75 -77.00  60.00   86
 47  \w   -101.00 -69.00   0.50    0.50    --  -91.75 -77.00  60.00   64
 48  \w    -95.00 -69.00   0.50    0.50    --  -91.75 -77.00  30.00   52
 49  \w    -95.00 -69.00   0.50    0.50    --  -91.75 -77.00 -30.00   52
 50  \w    -96.00 -70.00   0.50    0.50    --  -91.75 -77.00 -60.00   52
 51  \w   -105.00 -69.00   0.50    0.50    --  -91.75 -77.00-120.00   72
 52  \w    -94.00 -68.00   0.50    0.50    --  -91.75 -77.00-180.00   52
 53  \w    -99.00 -68.00   0.50    0.50    --  -91.75 -76.00-141.38   62
 54  \w   -158.00-128.00   0.50    0.50    --  -91.75 -77.00-120.00   60
 55  \w    -94.00 -68.00   0.50    0.50    --  -91.75 -77.00   0.00   52
 56  \w   -104.00 -69.00   0.50    0.50    --  -91.75 -73.00  66.26   70
 57  \w    -95.00 -69.00   0.50    0.50    --  -91.75 -75.00 125.53   52
 58  \w    -95.00 -69.00   0.50    0.50    --  -91.75 -77.00 150.00   52
 59  \w   -105.00 -69.00   0.50    0.50    --  -91.75 -74.00 106.36   72
 60  \w   -142.00-116.00   0.50    0.50    --  -91.75 -74.00 106.36   52
 61  \w   -137.00-111.00   0.50    0.50    --  -91.75 -73.00  66.26   52
 62  \w   -156.00-117.00   0.50    0.50    --  -91.75 -66.00 154.81   78
 63  \w   -134.00 -70.00   0.50    0.50    --  -91.75 -71.00  88.18  128
 64  \w   -100.00 -74.00   0.50    0.50    --  -91.75 -66.00 154.81   52
 65  \w    -97.00 -71.00   0.50    0.50    --  -91.75 -72.00   5.05   52
 66  \w   -150.00 -74.00   0.50    0.50    --  -91.75 -63.00 111.54  152
 67  \w   -105.00 -74.00   0.50    0.50    --  -91.75 -65.00  19.92   62
 68  \w   -137.00 -74.00   0.50    0.50    --  -91.75 -61.00 -90.00  126
 69  \w   -100.00 -73.00   0.50    0.50    --  -91.75 -64.00-118.49   54
 70  \w    -98.00 -73.00   0.50    0.50    --  -91.75 -63.00-106.32   50
 71  \w   -110.00 -73.00   0.50    0.50    --  -91.75 -70.00-167.76   74
 72  \w   -164.00-119.00   0.50    0.50    --  -91.75 -70.00-167.76   90
 73  \w   -104.00 -76.00   0.50    0.50    --  -91.75 -61.00 -64.65   56
 74  \w   -100.00 -75.00   0.50    0.50    --  -91.75 -61.00 -30.00   50
 75  \w   -129.00-102.00   0.50    0.50    --  -91.75 -60.00  48.00   54
 76  \w   -159.00-133.00   0.50    0.50    --  -91.75 -60.00  48.00   52
 77  \w   -154.00-119.00   0.50    0.50    --  -91.75 -45.00   0.00   70
 78  \w   -113.00 -77.00   0.50    0.50    --  -91.75 -45.00   0.00   72
 79  \w   -146.00-120.00   0.50    0.50    --  -91.75 -58.00 139.73   52
 80  \w   -115.00 -77.00   0.50    0.50    --  -91.75 -58.00 139.73   76
 81  \w   -112.00 -86.00   0.50    0.50    --  -46.62 -60.00  48.00   52
 82  \w    -79.00 -33.00   0.50    0.50    --  -91.75 125.00-120.00   92
 83  \w    -58.00 -22.00   0.50    0.50    --  -91.75 125.00-150.00   72
 84  \w    -79.00 -45.00   0.50    0.50    --  -46.62 -60.00  48.00   68
 85  \w    -50.00 -24.00   0.50    0.50    --  -46.62 -77.00   0.00   52
 86  \w    -49.00 -23.00   0.50    0.50    --  -46.62 -77.00 -30.00   52
 87  \w    -96.00 -70.00   0.50    0.50    --  -46.62 -77.00 -30.00   52
;
_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      0.0919773000
_diffrn_orient_matrix_UB_12      0.1262439000
_diffrn_orient_matrix_UB_13      0.0466758000
_diffrn_orient_matrix_UB_21      -0.0769091000
_diffrn_orient_matrix_UB_22      0.1454807000
_diffrn_orient_matrix_UB_23      -0.0870806000
_diffrn_orient_matrix_UB_31      -0.1853411000
_diffrn_orient_matrix_UB_32      0.0416045000
_diffrn_orient_matrix_UB_33      0.0980320000
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.097
_diffrn_reflns_theta_min         3.994
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    21.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41310
_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    1.999
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.510
_refine_diff_density_min         -1.487
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0261
_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^)+(0.0345P)^2^+1.1984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2473
_reflns_number_total             2498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08502k2.cif
_cod_data_source_block           exp_371_auto
_cod_original_cell_volume        636.584(14)
_cod_database_code               1576481
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H11 F1 I1 N1 O3 S1'
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00D), C00E(H00E,H00F), C00F(H00G,H00H)
1.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00G(H00I), C00H(H00J), C00I(H00K)
;
_shelx_res_checksum              86731
_shelx_hkl_checksum              82906
_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 2.083
_oxdiff_exptl_absorpt_empirical_full_min 0.629