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_1576485
_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         'C22 H24 F N O7 S'
_chemical_formula_sum            'C22 H24 F N O7 S'
_chemical_formula_weight         465.48
_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     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                 91.9460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.91650(10)
_cell_length_b                   16.1273(2)
_cell_length_c                   12.29690(10)
_cell_measurement_reflns_used    10600
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      75.2840
_cell_measurement_theta_min      4.0550
_cell_volume                     2163.67(4)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_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 0.962
_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 -17.00   0.50    0.49    --  -88.50  45.00  60.00   66
  2  \w    -45.00 -19.00   0.50    0.49    --  -88.50  45.00   0.00   52
  3  \w    -44.00 -17.00   0.50    0.49    --  -88.50  45.00 -60.00   54
  4  \w    -24.00  17.00   0.50    0.12    --  -46.62  19.00 -60.00   82
  5  \w    -42.00  23.00   0.50    0.12    --  -46.62  38.00 -30.00  130
  6  \w    -26.00  29.00   0.50    0.12    --  -46.62  19.00  30.00  110
  7  \w    -26.00  28.00   0.50    0.12    --  -46.62  19.00 150.00  108
  8  \w   -102.00 -77.00   0.50    0.12    --  -46.62 172.00 -14.00   50
  9  \w    -75.00 -50.00   0.50    0.49    --  -88.50 114.00-155.00   50
 10  \w    -58.00  -6.00   0.50    0.12    --  -46.62 114.00-155.00  104
 11  \w     38.00  69.00   0.50    0.12    --   46.62-114.00 114.00   62
 12  \w     90.00 146.00   0.50    0.49    --  106.06-172.00 -26.00  112
 13  \w     58.00  84.00   0.50    0.49    --  106.06-172.00 -26.00   52
 14  \w     72.00  97.00   0.50    0.49    --  106.06-114.00 114.00   50
 15  \w     35.00 106.00   0.50    0.49    --  106.06 -94.00 120.00  142
 16  \w     36.00 105.00   0.50    0.49    --  106.06 -77.00 120.00  138
 17  \w     38.00  69.00   0.50    0.49    --  106.06 -61.00 150.00   62
 18  \w     38.00  63.00   0.50    0.49    --  106.06 -77.00 -30.00   50
 19  \w     34.00  60.00   0.50    0.49    --  106.06 -61.00   0.00   52
 20  \w     44.00  70.00   0.50    0.49    --  106.06 -61.00 -30.00   52
 21  \w     33.00  58.00   0.50    0.49    --  106.06 -61.00 -60.00   50
 22  \w     40.00  65.00   0.50    0.49    --  106.06 -61.00 -90.00   50
 23  \w     94.00 172.00   0.50    0.49    --  106.06  30.00 -60.00  156
 24  \w     83.00 108.00   0.50    0.49    --  106.06 172.00 -14.00   50
 25  \w    104.00 164.00   0.50    0.49    --  106.06 114.00-155.00  120
 26  \w   -109.00 -74.00   0.50    0.49    --  -88.50-125.00  90.00   70
 27  \w   -157.00-115.00   0.50    0.49    --  -88.50-125.00  90.00   84
 28  \w   -119.00 -86.00   0.50    0.49    --  -88.50-114.00 114.00   66
 29  \w    -86.00 -55.00   0.50    0.12    --  -46.62-172.00 -26.00   62
 30  \w   -112.00 -87.00   0.50    0.49    --  -88.50-172.00 -26.00   50
;
_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      -0.0438171000
_diffrn_orient_matrix_UB_12      -0.0882151000
_diffrn_orient_matrix_UB_13      -0.0294204000
_diffrn_orient_matrix_UB_21      -0.0586948000
_diffrn_orient_matrix_UB_22      0.0328094000
_diffrn_orient_matrix_UB_23      -0.1073063000
_diffrn_orient_matrix_UB_31      0.1206807000
_diffrn_orient_matrix_UB_32      -0.0161357000
_diffrn_orient_matrix_UB_33      -0.0578930000
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17330
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.242
_diffrn_reflns_theta_min         4.052
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87371
_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    1.429
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00122(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0337P)^2^+0.8883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3895
_reflns_number_total             4360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08502k2.cif
_cod_data_source_block           exp_174_auto
_cod_database_code               1576485
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H24 F1 N1 O7 S1'
_diffrn_oxdiff_digest_hkl
;
01e01f0bdab3328cf0417b869b8a0b6b0fdbe5
;
_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:
 C17(H17), C12(H12), C18(H18), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28a,H28b), C4(H4a,H4b), C5(H5a,H5b)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C14(H14), C10(H10), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C25(H25a,H25b,H25c), C32(H32a,H32b,H32c)
;
_shelx_res_checksum              24706
_shelx_hkl_checksum              21794
_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 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.790