FeCl<sub>3</sub>-catalyzed oxidative diselenylation of pyrrole-tethered indoles.
Zhou, Jing; Sheng, Xue; Jiang, Man; Cui, Hai-Lei; Organic & biomolecular chemistry 23 (2025) 2254–2262; doi:10.1039/d4ob01929f

data_7160342
_publ_section_title
;
 FeCl<sub>3</sub>-catalyzed oxidative diselenylation of pyrrole-tethered
 indoles.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2254
_journal_page_last               2262
_journal_paper_doi               10.1039/d4ob01929f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C35 H29 Cl N2 O Se2'
_chemical_formula_sum            'C35 H29 Cl N2 O Se2'
_chemical_formula_weight         686.97
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-07-29
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-07-29 deposited with the CCDC.	2025-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.36591(11)
_cell_length_b                   16.76936(19)
_cell_length_c                   21.6439(2)
_cell_measurement_reflns_used    16017
_cell_measurement_temperature    200.03(10)
_cell_measurement_theta_max      72.9960
_cell_measurement_theta_min      3.3400
_cell_volume                     3762.35(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.03(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_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     27.00  52.00   0.50    0.43    --   99.00 -45.00-180.00   50
  2  \w     48.00  73.00   0.50    0.43    --   99.00 -61.00-180.00   50
  3  \w     27.00  52.00   0.50    0.43    --   99.00 -45.00-120.00   50
  4  \w     27.00  52.00   0.50    0.43    --   99.00 -45.00-150.00   50
  5  \w     27.00  52.00   0.50    0.43    --   99.00 -45.00 -30.00   50
  6  \w     27.00  53.00   0.50    0.43    --   99.00 -45.00  30.00   52
  7  \w     28.00  53.00   0.50    0.43    --   99.00 -45.00 120.00   50
  8  \w     26.00  52.00   0.50    0.43    --   99.00 -61.00 150.00   52
  9  \w    -22.00  44.00   0.50    0.11    --   45.87 -37.00 120.00  132
 10  \w    -24.00  73.00   0.50    0.11    --   45.87 -88.00 105.00  194
 11  \w     52.00  87.00   0.50    0.43    --   99.00 -88.00 105.00   70
 12  \w     93.00 126.00   0.50    0.43    --   99.00 -88.00 105.00   66
 13  \w    102.00 133.00   0.50    0.43    --   99.00  53.00 112.00   62
 14  \w     80.00 123.00   0.50    0.43    --   99.00 125.00   0.00   86
 15  \w    142.00 169.00   0.50    0.43    --   99.00 125.00   0.00   54
 16  \w     85.00 156.00   0.50    0.43    --   99.00  83.00 -30.00  142
 17  \w     86.00 151.00   0.50    0.43    --   99.00  45.00 -60.00  130
 18  \w     85.00 168.00   0.50    0.43    --   99.00  88.00-137.00  166
 19  \w    -22.00  18.00   0.50    0.11    --  -45.87  19.00 -60.00   80
 20  \w     -9.00  24.00   0.50    0.11    --  -45.87  19.00-120.00   66
 21  \w    -70.00 -28.00   0.50    0.43    --  -99.00  61.00 -60.00   84
 22  \w    -71.00 -43.00   0.50    0.43    --  -99.00  77.00  60.00   56
 23  \w    -70.00 -29.00   0.50    0.43    --  -99.00 125.00 -30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024109000
_diffrn_orient_matrix_UB_12      -0.0796908000
_diffrn_orient_matrix_UB_13      0.0354120000
_diffrn_orient_matrix_UB_21      -0.1303231000
_diffrn_orient_matrix_UB_22      0.0231809000
_diffrn_orient_matrix_UB_23      0.0291909000
_diffrn_orient_matrix_UB_31      -0.0714657000
_diffrn_orient_matrix_UB_32      -0.0394171000
_diffrn_orient_matrix_UB_33      -0.0543747000
_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  0.0486
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24632
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.382
_diffrn_reflns_theta_min         4.085
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2745 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         7343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0350P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                6744
_reflns_number_total             7343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01929f2.cif
_cod_data_source_block           jm2407016
_cod_depositor_comments
'Adding full bibliography for 7160342--7160343.cif.'
_cod_original_cell_volume        3762.36(7)
_cod_database_code               7160342
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O  N Se Cl'
_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.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
  C30(H30), C31(H31), C33(H33)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C35(H35A,H35B,H35C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              1493
_shelx_fab_checksum              58317
_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 1.608
_oxdiff_exptl_absorpt_empirical_full_min 0.772