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_7160343
_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_absolute_configuration ad
_chemical_formula_moiety         'C29 H26 N2 O2 Se'
_chemical_formula_sum            'C29 H26 N2 O2 Se'
_chemical_formula_weight         513.48
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-12-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-12-20 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            8
_cell_length_a                   9.7120(3)
_cell_length_b                   9.7120(3)
_cell_length_c                   50.789(3)
_cell_measurement_reflns_used    4561
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      67.365
_cell_measurement_theta_min      3.481
_cell_volume                     4790.6(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_temperature      153.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_number            4449
_diffrn_reflns_point_group_measured_fraction_full 0.506
_diffrn_reflns_point_group_measured_fraction_max 0.504
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.439
_diffrn_reflns_theta_min         3.481
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.351
_exptl_absorpt_correction_T_max  0.753056
_exptl_absorpt_correction_T_min  0.453975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1475 before and 0.1214 after correction.
 The Ratio of minimum to maximum transmission is 0.60.

Final HKLF 4 output contains 68473 reflections, Rint = 0.1490
 (19786 with I > 3sig(I), Rint = 0.0772)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.276
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.13(6)
_refine_ls_extinction_coef       0.00187(10)
_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   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     618
_refine_ls_number_reflns         4449
_refine_ls_number_restraints     268
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0947
_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^)+(0.0923P)^2^+32.6904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2311
_refine_ls_wR_factor_ref         0.2391
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                3986
_reflns_number_total             4449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01929f2.cif
_cod_data_source_block           1207_5
_cod_depositor_comments
'Adding full bibliography for 7160342--7160343.cif.'
_cod_database_code               7160343
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.834
_shelx_estimated_absorpt_t_min   0.719
_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 body (RIGU) restrains
 Se1, O1, O2, N1, H1, N2, C00X, C1, C2, H2, C3, H3, C4, H4, C5, H5, C6, C7, H7,
  C8, C9, H9A, H9B, C10, H10A, H10B, C11, H11A, H11B, H11C, C12, C13, C14, C15,
 C16, C17, H17, C18, H18, C19, H19, C20, H20, C21, H21, C22, C23, H23, C24, H24,
  C25, H25, C26, H26, C27, H27, C28, H28A, H28B, H28C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.008
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C37(H37A,H37B), C38(H38A,H38B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), N3(H3A),
 C29(H29), C32(H32), C33(H33), C34(H34), C35(H35), C45(H45), C46(H46), C47(H47),
  C48(H48), C49(H49), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C28(H28A,H28B,H28C), C39(H39A,H39B,H39C), C57(H57A,H57B,
 H57C)
;
_shelx_res_checksum              29687
_olex2_submission_special_instructions 'No special instructions were received'