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_1576482
_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_absolute_configuration ad
_chemical_formula_moiety         'C10 H8 F N O3 S'
_chemical_formula_sum            'C10 H8 F N O3 S'
_chemical_formula_weight         241.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-25
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-08-25 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.895(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4669(6)
_cell_length_b                   7.9789(5)
_cell_length_c                   9.3340(8)
_cell_measurement_reflns_used    2823
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      29.6530
_cell_measurement_theta_min      3.8330
_cell_volume                     522.91(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (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 1.000
_diffrn_measured_fraction_theta_max 0.806
_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    -20.00  37.00   0.50    3.89    --    4.95 -99.00 -30.00  114
  2  \w    -16.00  25.00   0.50    3.89    --   -5.34 -99.00-120.00   82
  3  \w    -35.00  -8.00   0.50    3.89    --    4.95 -19.00-120.00   54
  4  \w    -65.00  -2.00   0.50    3.89    --   -5.34 -22.00 -58.00  126
  5  \w    -17.00  70.00   0.50    3.89    --   -5.34  22.00 107.00  174
;
_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      0.0762867000
_diffrn_orient_matrix_UB_12      0.0236197000
_diffrn_orient_matrix_UB_13      -0.0247330000
_diffrn_orient_matrix_UB_21      0.0596483000
_diffrn_orient_matrix_UB_22      0.0105778000
_diffrn_orient_matrix_UB_23      0.0769061000
_diffrn_orient_matrix_UB_31      0.0287017000
_diffrn_orient_matrix_UB_32      -0.0850508000
_diffrn_orient_matrix_UB_33      0.0027730000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.806
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4923
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.734
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         2.320
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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    1.532
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 795 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2356
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0399P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0821
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.653
_reflns_number_gt                2118
_reflns_number_total             2356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08502k2.cif
_cod_data_source_block           exp_121_auto
_cod_original_cell_volume        522.91(7)
_cod_database_code               1576482
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C10 H8 F1 N1 O3 S1'
_diffrn_oxdiff_digest_hkl
;
01eef1118f59071092aa772e8516f5cbc848d4
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C8(H8), C5(H5), C4(H4), C3(H3), C9(H9)
;
_shelx_res_checksum              91450
_shelx_hkl_checksum              7111
_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 1.127
_oxdiff_exptl_absorpt_empirical_full_min 0.798