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_1576483
_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         'C5 H7 F I N O3 S'
_chemical_formula_sum            'C5 H7 F I N O3 S'
_chemical_formula_weight         307.08
_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     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                90
_cell_angle_beta                 105.905(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3378(5)
_cell_length_b                   5.8654(2)
_cell_length_c                   21.9011(8)
_cell_measurement_reflns_used    3046
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.3370
_cell_measurement_theta_min      4.2040
_cell_volume                     1771.31(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.907
_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 -25.00   0.50    0.32    --  -91.75  45.00-173.00   50
  2  \w    -66.00 -25.00   0.50    0.32    --  -91.75  61.00 -90.00   82
  3  \w    -44.00 -19.00   0.50    0.32    --  -91.75  45.00 -60.00   50
  4  \w    -47.00  26.00   0.50    0.08    --  -46.62  45.00-173.00  146
  5  \w    -45.00 -19.00   0.50    0.32    --  -91.75  45.00-120.00   52
  6  \w    -46.00 -21.00   0.50    0.32    --  -91.75  45.00-150.00   50
  7  \w    -47.00 -21.00   0.50    0.32    --  -91.75  45.00 -30.00   52
  8  \w    -50.00 -24.00   0.50    0.32    --  -91.75  45.00   0.00   52
  9  \w    -44.00 -19.00   0.50    0.32    --  -91.75  45.00  30.00   50
 10  \w    -49.00 -21.00   0.50    0.32    --  -91.75  45.00 120.00   56
 11  \w    -17.00  23.00   0.50    0.08    --  -46.62  19.00 -30.00   80
 12  \w    -89.00 -35.00   0.50    0.08    --  -46.62 -45.00  37.00  108
 13  \w   -119.00 -93.00   0.50    0.08    --  -46.62 -45.00  37.00   52
 14  \w   -134.00 -89.00   0.50    0.32    --  -91.75 -45.00 120.00   90
 15  \w   -155.00 -80.00   0.50    0.32    --  -91.75 -45.00  37.00  150
 16  \w     64.00  92.00   0.50    0.08    --   46.62  45.00-173.00   56
 17  \w     97.00 122.00   0.50    0.32    --  105.44  45.00-173.00   50
 18  \w     42.00  67.00   0.50    0.32    --  105.44 -61.00-120.00   50
 19  \w     12.00  42.00   0.50    0.08    --   46.62 -45.00  37.00   60
 20  \w     35.00  61.00   0.50    0.32    --  105.44 -94.00  90.00   52
 21  \w     71.00  98.00   0.50    0.32    --  105.44 -94.00  90.00   54
 22  \w     49.00 103.00   0.50    0.32    --  105.44 -94.00  30.00  108
 23  \w     61.00 110.00   0.50    0.32    --  105.44-125.00-120.00   98
;
_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      -0.0208725000
_diffrn_orient_matrix_UB_12      0.0558600000
_diffrn_orient_matrix_UB_13      0.0637010000
_diffrn_orient_matrix_UB_21      0.0901916000
_diffrn_orient_matrix_UB_22      -0.1377249000
_diffrn_orient_matrix_UB_23      0.0354611000
_diffrn_orient_matrix_UB_31      0.0626482000
_diffrn_orient_matrix_UB_32      0.2164022000
_diffrn_orient_matrix_UB_33      0.0060211000
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4945
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.587
_diffrn_reflns_theta_min         4.198
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    30.580
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.303
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.042
_refine_diff_density_max         1.247
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0462P)^2^+2.0911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1555
_reflns_number_total             1680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08502k2.cif
_cod_data_source_block           exp_368_autored
_cod_database_code               1576483
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C5 H7 F1 I1 N1 O3 S1'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 I7-C6 \\sim I7A-C6A
 with sigma of 0.02
 C4-C6 \\sim C4-C6A
 with sigma of 0.02
 I7-C4 \\sim I7A-C4
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C6A) = Uanis(C6)
Uanis(I7A) = Uanis(I7)
4. Others
 Sof(H4B)=Sof(I7A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=1-FVAR(1)
 Sof(I7)=Sof(H4A)=Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4A), C4(H4B)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C6A(H6AA,H6AB)
;
_shelx_res_checksum              69334
_shelx_hkl_checksum              83129
_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 2.087
_oxdiff_exptl_absorpt_empirical_full_min 0.687