Stable radical cations based on indolo[3,2,1-<i>jk</i>]carbazole: synthesis, characterization, and theoretical calculation.
Yang, Jiayao; Yang, Linlin; Li, Tao; Zhao, Wanxiang; Chemical communications (Cambridge, England) 62 (2026) 5536–5539; doi:10.1039/d6cc00498a

data_7135409
_publ_section_title
;
 Stable radical cations based on indolo[3,2,1-<i>jk</i>]carbazole:
 synthesis, characterization, and theoretical calculation.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5536
_journal_page_last               5539
_journal_paper_doi               10.1039/d6cc00498a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C16 Al F36 O4, 2(C46 H48 N2)'
_chemical_formula_sum            'C108 H96 Al F36 N4 O4'
_chemical_formula_weight         2224.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2026-01-01 deposited with the CCDC.	2026-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 124.3540(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   48.7724(13)
_cell_length_b                   13.9285(4)
_cell_length_c                   39.1474(9)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      68.395
_cell_measurement_theta_min      2.195
_cell_volume                     21955.0(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            111881
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.425
_diffrn_reflns_theta_min         2.194
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.160
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.8020.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             9128
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1729
_refine_ls_number_reflns         20120
_refine_ls_number_restraints     1846
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0940
_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^)+(0.1459P)^2^+72.7572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2660
_refine_ls_wR_factor_ref         0.2803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15121
_reflns_number_total             20120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00498a2.cif
_cod_data_source_block           cu_2024112001_0m_a
_cod_depositor_comments
'Adding full bibliography for 7135408--7135409.cif.'
_cod_database_code               7135409
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.784
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F22A-C1B = F24A-C1B = F23A-C1B = F22-C103 = F23-C103 = F24-C103 = F20A-C1A =
 F21A-C1A = F19A-C1A = F19-C102 = F21-C102 = F20-C102 = F27A-C109 = F27-C104 =
 F26-C104 = F26A-C109 = F25-C104 = F25A-C109
 1.35 with sigma of 0.01
 F23A-F22A = F24A-F22A = F24A-F23A
 2.3 with sigma of 0.01
 F2-C94 = F3-C94 = F1-C94 = F8A-C96A = F7A-C96A = F9A-C96A = F7-C96 = F8-C96 =
 F9-C96 = F6A-C95A = F5A-C95A = F4A-C95A = F6-C95 = F5-C95 = F4-C95 = F2A-C94A =
  F3A-C94A = F1A-C94A
 1.35 with sigma of 0.01
 F36-C108 = F34-C108 = F34A-C1D = F36A-C1D = F35-C108 = F35A-C1D = F33-C107 =
 F33A-C1C = F32-C107 = F32A-C1C = F31A-C1C = F31-C107 = F29-C106 = F29A-C110 =
 F28A-C110 = F28-C106 = F30-C106 = F30A-C110
 1.35 with sigma of 0.01
 C105-F28A
 2.3 with sigma of 0.01
 C103-C101 \\sim C1B-C101 \\sim C104-C101 \\sim C109-C101 \\sim C102-C101 \\sim
C1A-C101
 with sigma of 0.02
 F24A-F22A \\sim F24A-F23A \\sim F23A-F22A
 with sigma of 0.02
 F22A-C101 \\sim F24A-C101 \\sim F23A-C101
 with sigma of 0.02
 C94-C93 \\sim C94A-C93 \\sim C95-C93 \\sim C95A-C93 \\sim C96-C93 \\sim
C96A-C93
 with sigma of 0.02
 C107-C105 \\sim C1C-C105 \\sim C106-C105 \\sim C110-C105 \\sim C108-C105 \\sim
C1D-C105
 with sigma of 0.02
 F32A-F31A \\sim F33A-F31A \\sim F33A-F32A
 with sigma of 0.02
 F30A-F29A \\sim F29A-F28A \\sim F30A-F28A
 with sigma of 0.02
 C1C-C110 \\sim C1D-C110 \\sim C1D-C1C
 with sigma of 0.02
 C95A-C94A \\sim C96A-C95A \\sim C96A-C94A
 with sigma of 0.02
 F9A-F8A \\sim F9A-F7A \\sim F8A-F7A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F25 \\sim F27 \\sim F23 \\sim F26 \\sim F20 \\sim F19 \\sim C101 \\sim F22
\\sim F21 \\sim C104 \\sim C102 \\sim C103 \\sim F24 \\sim F25A \\sim F27A
\\sim F23A \\sim F26A \\sim F20A \\sim F19A \\sim F21A \\sim C109 \\sim C1A
\\sim C1B \\sim F24A \\sim F22A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
F1 \\sim F4 \\sim F6 \\sim F3 \\sim F5 \\sim F9 \\sim F2 \\sim F7 \\sim C93
\\sim F8 \\sim C94 \\sim C95 \\sim C96 \\sim F6A \\sim F3A \\sim F5A \\sim F9A
\\sim F2A \\sim F7A \\sim F8A \\sim C94A \\sim C95A \\sim C96A \\sim F4A \\sim
F1A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F30 \\sim F29 \\sim F31 \\sim F32 \\sim F33 \\sim F28 \\sim C106 \\sim C105
\\sim C107 \\sim F36 \\sim F34 \\sim F35 \\sim C108 \\sim F30A \\sim F29A \\sim
F28A \\sim C110 \\sim C1C \\sim F36A \\sim F34A \\sim F35A \\sim C1D \\sim F31A
\\sim F32A \\sim F33A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(F35A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 F25, F27, F23, F26, F20, F19, C101, F22, F21, C104, C102, C103, F24, F25A,
 F27A, F23A, F26A, F20A, F19A, F21A, C109, C1A, C1B, F24A, F22A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F1, F4, F6, F3, F5, F9, F2, F7, C93, F8, C94, C95, C96, F6A, F3A, F5A, F9A,
 F2A, F7A, F8A, C94A, C95A, C96A, F4A, F1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F29, F31, F28, C106, C107, F36, F34, F35, C108, F29A, F28A, C110, C1C, F36A,
 F34A, F35A, C1D, F31A, F30, F32, F33, F32A, F33A, C105, F30A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(F25A)=Sof(F27A)=Sof(F23A)=Sof(F26A)=Sof(F20A)=Sof(F19A)=Sof(F21A)=
 Sof(C109)=Sof(C1A)=Sof(C1B)=Sof(F24A)=Sof(F22A)=1-FVAR(1)
 Sof(F25)=Sof(F27)=Sof(F23)=Sof(F26)=Sof(F20)=Sof(F19)=Sof(F22)=Sof(F21)=
 Sof(C104)=Sof(C102)=Sof(C103)=Sof(F24)=FVAR(1)
 Sof(F6A)=Sof(F3A)=Sof(F5A)=Sof(F9A)=Sof(F2A)=Sof(F7A)=Sof(F8A)=Sof(C94A)=
 Sof(C95A)=Sof(C96A)=Sof(F4A)=Sof(F1A)=1-FVAR(2)
 Sof(F1)=Sof(F4)=Sof(F6)=Sof(F3)=Sof(F5)=Sof(F9)=Sof(F2)=Sof(F7)=Sof(F8)=
 Sof(C94)=Sof(C95)=Sof(C96)=FVAR(2)
 Sof(F30A)=Sof(F29A)=Sof(F28A)=Sof(C110)=Sof(C1C)=Sof(F36A)=Sof(F34A)=
 Sof(F35A)=Sof(C1D)=Sof(F31A)=Sof(F32A)=Sof(F33A)=1-FVAR(3)
 Sof(F30)=Sof(F29)=Sof(F31)=Sof(F32)=Sof(F33)=Sof(F28)=Sof(C106)=Sof(C107)=
 Sof(F36)=Sof(F34)=Sof(F35)=Sof(C108)=FVAR(3)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C4(H4), C63(H63), C29(H29), C20(H20), C8(H8), C27(H27),
 C73(H73), C61(H61), C9(H9), C17(H17), C23(H23), C15(H15), C50(H50), C21(H21),
 C66(H66), C67(H67), C47(H47), C54(H54), C75(H75), C69(H69), C57(H57), C55(H55)
6.b Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C82(H82A,H82B,H82C), C42(H42A,H42B,H42C), C83(H83A,H83B,
 H83C), C37(H37A,H37B,H37C), C46(H46A,H46B,H46C), C33(H33A,H33B,H33C), C84(H84A,
 H84B,H84C), C34(H34A,H34B,H34C), C32(H32A,H32B,H32C), C86(H86A,H86B,H86C),
 C40(H40A,H40B,H40C), C44(H44A,H44B,H44C), C88(H88A,H88B,H88C), C92(H92A,H92B,
 H92C), C36(H36A,H36B,H36C), C87(H87A,H87B,H87C), C45(H45A,H45B,H45C), C91(H91A,
 H91B,H91C), C90(H90A,H90B,H90C), C41(H41A,H41B,H41C), C80(H80A,H80B,H80C),
 C78(H78A,H78B,H78C), C79(H79A,H79B,H79C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 524 electrons were 
found in a volume of 3196\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1.57[CH2Cl2] per Asymmetric Unit 
which account for 528 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              91195
_shelx_hkl_checksum              21691
_shelx_fab_checksum              2632
_olex2_submission_special_instructions 'No special instructions were received'