Catalyst-free coupling of peroxypyrroloindolenines with amines to afford stable peroxyindolenines.
Zheng, Xiaoshan; Wang, Menghan; Sun, Xianbin; Gao, Yu; Chen, Haijun; Organic & biomolecular chemistry 23 (2025) 1215–1218; doi:10.1039/d4ob01736f

data_7160296
_publ_section_title
;
 Catalyst-free coupling of peroxypyrroloindolenines with amines to afford
 stable peroxyindolenines.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1215
_journal_page_last               1218
_journal_paper_doi               10.1039/d4ob01736f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C28 H33 N3 O4 S'
_chemical_formula_sum            'C28 H33 N3 O4 S'
_chemical_formula_weight         507.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-18
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-19 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.326(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9075(2)
_cell_length_b                   9.8706(2)
_cell_length_c                   21.4050(4)
_cell_measurement_reflns_used    10501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2040
_cell_measurement_theta_min      3.8580
_cell_volume                     2719.33(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_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 0.995
_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    -67.00 -42.00   0.50    0.29    -- -106.00  61.00  90.00   50
  2  \w    -42.00  27.00   0.50    0.07    --  -46.60  38.00   0.00  138
  3  \w    -70.00 -42.00   0.50    0.29    -- -106.00  61.00-150.00   56
  4  \w    -70.00 -40.00   0.50    0.29    -- -106.00  61.00-120.00   60
  5  \w   -107.00 -82.00   0.50    0.29    -- -106.00  84.00-107.00   50
  6  \w    -71.00 -19.00   0.50    0.07    --  -46.60  84.00-107.00  104
  7  \w     -2.00  24.00   0.50    0.07    --  -46.60  84.00-107.00   52
  8  \w   -176.00 -88.00   0.50    0.29    -- -106.00 -61.00  90.00  176
  9  \w   -152.00-127.00   0.50    0.29    -- -106.00 -84.00 132.00   50
 10  \w    -21.00  36.00   0.50    0.07    --   46.60 -84.00 132.00  114
 11  \w     40.00  68.00   0.50    0.07    --   46.60 -84.00 132.00   56
 12  \w     45.00 104.00   0.50    0.29    --  108.09 -95.00  60.00  118
 13  \w     35.00  90.00   0.50    0.29    --  108.09 -95.00   0.00  110
 14  \w     60.00 134.00   0.50    0.29    --  108.09 -84.00 132.00  148
 15  \w     37.00  72.00   0.50    0.29    --  108.09 -77.00 150.00   70
 16  \w     -4.00  26.00   0.50    0.07    --   46.60 -19.00 120.00   60
 17  \w     37.00  70.00   0.50    0.29    --  108.09 -61.00 -30.00   66
 18  \w     56.00  97.00   0.50    0.29    --  108.09 -77.00 -90.00   82
 19  \w     35.00  60.00   0.50    0.29    --  108.09 -61.00 -90.00   50
 20  \w     35.00  69.00   0.50    0.29    --  108.09 -61.00-150.00   68
 21  \w    140.00 165.00   0.50    0.29    --  108.09  30.00 -30.00   50
 22  \w    107.00 133.00   0.50    0.29    --  108.09  30.00 -30.00   52
 23  \w    107.00 156.00   0.50    0.29    --  108.09  45.00-180.00   98
 24  \w     81.00 178.00   0.50    0.29    --  108.09  84.00-107.00  194
 25  \w     42.00 118.00   0.50    0.07    --   46.60 178.00  60.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0558309000
_diffrn_orient_matrix_UB_12      -0.1325155000
_diffrn_orient_matrix_UB_13      -0.0153512000
_diffrn_orient_matrix_UB_21      0.0165092000
_diffrn_orient_matrix_UB_22      -0.0325421000
_diffrn_orient_matrix_UB_23      0.0704273000
_diffrn_orient_matrix_UB_31      -0.1045861000
_diffrn_orient_matrix_UB_32      -0.0758501000
_diffrn_orient_matrix_UB_33      -0.0033078000
_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  0.0399
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17962
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.575
_diffrn_reflns_theta_max         66.575
_diffrn_reflns_theta_min         3.874
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4786
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0693
_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^)+(0.1248P)^2^+1.5310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2039
_refine_ls_wR_factor_ref         0.2169
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3919
_reflns_number_total             4786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01736f2.cif
_cod_data_source_block           1282_auto
_cod_depositor_comments          'Adding full bibliography for 7160296.cif.'
_cod_database_code               7160296
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.822
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C14, C15
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.004
 C25, C27
 with sigma for 1-2 distances of 0.0008 and sigma for 1-3 distances of 0.0004
 C25, C26
 with sigma for 1-2 distances of 0.0008 and sigma for 1-3 distances of 0.0004
 C25, C28
 with sigma for 1-2 distances of 0.0008 and sigma for 1-3 distances of 0.0004
3. Uiso/Uaniso restraints and constraints
C25 \\sim C27 \\sim C26 \\sim C28 \\sim O4: within 3.8A with sigma of 0.002 and
sigma for terminal atoms of 0.004 within 3.8A
Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C8(H8), C17(H17), C24(H24), C5(H5), C23(H23), C7(H7), C6(H6),
 C19(H19), C16(H16), C13(H13), C20(H20), C15(H15), C14(H14)
4.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C22(H22A,H22B,H22C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_shelx_res_checksum              44663
_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 1.550
_oxdiff_exptl_absorpt_empirical_full_min 0.476