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_7135408
_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, C46 H48 N2'
_chemical_formula_sum            'C62 H48 Al F36 N2 O4'
_chemical_formula_weight         1596.00
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-05
_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                106.1860(10)
_cell_angle_beta                 100.0950(10)
_cell_angle_gamma                96.1510(10)
_cell_formula_units_Z            2
_cell_length_a                   11.5239(3)
_cell_length_b                   15.1374(3)
_cell_length_c                   19.9082(4)
_cell_measurement_reflns_used    9802
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      68.207
_cell_measurement_theta_min      3.082
_cell_volume                     3238.53(13)
_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      150.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            61861
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.265
_diffrn_reflns_theta_min         2.366
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1154 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.7988.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_modifier   green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description       block
_exptl_crystal_F_000             1606
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1414
_refine_ls_number_reflns         11808
_refine_ls_number_restraints     2444
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0634P)^2^+2.4541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10613
_reflns_number_total             11808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00498a2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7135408--7135409.cif.'
_cod_original_cell_volume        3238.52(13)
_cod_database_code               7135408
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.668
_shelx_estimated_absorpt_t_min   0.632
_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
 F12A-C52A = F12-C52 = F11A-C52A = F11-C52 = F10-C52 = F10A-C52A = F14A-C53A =
 F14-C53 = F15-C53 = F15A-C53A = F13A-C53A = F13-C53 = F16-C54 = F16A-C54A =
 F18A-C54A = F18-C54 = F17-C54 = F17A-C54A
 1.35 with sigma of 0.01
 C57-C55 = C58-C55 = C56-C55 = C56A-C55 = C57A-C55
 1.54 with sigma of 0.01
 F23A-C57A = F23-C57 = F24A-C57A = F24-C57 = F22A-C57A = F22-C57 = F27A-C58 =
 F27-C58 = F26A-C58 = F26-C58 = F25-C58 = F25A-C58 = F21-C56 = F21A-C56A = F20-
 C56 = F20A-C56A = F19A-C56A = F19-C56
 1.35 with sigma of 0.01
 C48-C47 = C48A-C47 = C50A-C47 = C50-C47 = C49A-C47 = C49-C47
 1.54 with sigma of 0.01
 F3-C48 = F3A-C48A = F2-C48 = F2A-C48A = F1-C48 = F1A-C48A = F7-C50 = F7A-C50A
 = F8-C50 = F8A-C50A = F9-C50 = F9A-C50A = F6-C49 = F6A-C49A = F5-C49 = F5A-
 C49A = F4-C49 = F4A-C49A
 1.35 with sigma of 0.01
 F29-C60 = F29A-C60A = F28-C60 = F30A-C60A = F30-C60 = F28A-C60A = F35A-C62A =
 F35-C62 = F34-C62 = F34A-C62A = F36-C62 = F36A-C62A = F32A-C61A = F32-C61 =
 F31-C61 = F31A-C61A = F33A-C61A = F33-C61
 1.35 with sigma of 0.01
 C60A-C59 = C60-C59 = C61-C59 = C61A-C59 = C62-C59 = C62A-C59
 1.54 with sigma of 0.01
 C52A-C51 \\sim C52-C51 \\sim C53-C51 \\sim C53A-C51 \\sim C54-C51 \\sim
C54A-C51
 with sigma of 0.02
 F14A-F13A \\sim F15A-F14A \\sim F15A-F13A
 with sigma of 0.02
 C54A-C53A \\sim C54A-C52A \\sim C53A-C52A
 with sigma of 0.02
 F18A-F16A \\sim F17A-F16A \\sim F18A-F17A
 with sigma of 0.02
 C45A-C43 \\sim C45-C43 \\sim C46-C43 \\sim C46A-C43 \\sim C44A-C43 \\sim
C44-C43
 with sigma of 0.02
 F32A-F31A \\sim F33A-F32A \\sim F33A-F31A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F13 \\sim F14 \\sim F17 \\sim F10 \\sim F16 \\sim F11 \\sim C51 \\sim F12 \\sim
F18 \\sim F15 \\sim C53 \\sim C54 \\sim C52 \\sim F13A \\sim F14A \\sim F17A
\\sim F10A \\sim F16A \\sim F11A \\sim F12A \\sim F18A \\sim F15A \\sim C53A
\\sim C54A \\sim C52A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C43 \\sim C45 \\sim C44 \\sim C46 \\sim C46A \\sim C45A \\sim C44A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F26 \\sim F20 \\sim F27 \\sim F25 \\sim F19 \\sim F22 \\sim C55 \\sim F23 \\sim
F21 \\sim F24 \\sim C58 \\sim C56 \\sim C57 \\sim F22A \\sim F23A \\sim F24A
\\sim C57A \\sim F20A \\sim F27A \\sim F21A \\sim C56A \\sim F26A \\sim F25A
\\sim F19A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
F7 \\sim F9 \\sim F8 \\sim F1 \\sim F2 \\sim F6 \\sim F3 \\sim C47 \\sim F5
\\sim F4 \\sim C50 \\sim C48 \\sim C49 \\sim F7A \\sim F9A \\sim F8A \\sim F1A
\\sim F2A \\sim F6A \\sim F3A \\sim F5A \\sim F4A \\sim C50A \\sim C48A \\sim
C49A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
F33 \\sim F31 \\sim F35 \\sim F32 \\sim F28 \\sim F34 \\sim C59 \\sim F29 \\sim
F36 \\sim F30 \\sim C61 \\sim C60 \\sim C62 \\sim F33A \\sim F31A \\sim F35A
\\sim F32A \\sim F28A \\sim F34A \\sim F29A \\sim F36A \\sim F30A \\sim C61A
\\sim C60A \\sim C62A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 F13, F14, F17, F10, F16, F11, C51, F12, F18, F15, C53, C54, C52, F13A, F14A,
 F17A, F10A, F16A, F11A, F12A, F18A, F15A, C53A, C54A, C52A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C43, C45, C44, C46, C46A, C45A, C44A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F26, F20, F27, F25, F19, F22, C55, F23, F21, F24, C58, C56, C57, F22A, F23A,
 F24A, C57A, F20A, F27A, F21A, C56A, F26A, F25A, F19A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F7, F9, F8, F1, F2, F6, F3, C47, F5, F4, C50, C48, C49, F7A, F9A, F8A, F1A,
 F2A, F6A, F3A, F5A, F4A, C50A, C48A, C49A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 F33, F31, F35, F32, F28, F34, C59, F29, F36, F30, C61, C60, C62, F33A, F31A,
 F35A, F32A, F28A, F34A, F29A, F36A, F30A, C61A, C60A, C62A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(F13A)=Sof(F14A)=Sof(F17A)=Sof(F10A)=Sof(F16A)=Sof(F11A)=Sof(F12A)=
 Sof(F18A)=Sof(F15A)=Sof(C53A)=Sof(C54A)=Sof(C52A)=1-FVAR(1)
 Sof(F13)=Sof(F14)=Sof(F17)=Sof(F10)=Sof(F16)=Sof(F11)=Sof(F12)=Sof(F18)=
 Sof(F15)=Sof(C53)=Sof(C54)=Sof(C52)=FVAR(1)
 Sof(C46A)=Sof(H46D)=Sof(H46E)=Sof(H46F)=Sof(C45A)=Sof(H45D)=Sof(H45E)=
 Sof(H45F)=Sof(C44A)=Sof(H44D)=Sof(H44E)=Sof(H44F)=1-FVAR(2)
 Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=
 Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=FVAR(2)
 Sof(F22A)=Sof(F23A)=Sof(F24A)=Sof(C57A)=Sof(F20A)=Sof(F27A)=Sof(F21A)=
 Sof(C56A)=Sof(F26A)=Sof(F25A)=Sof(F19A)=1-FVAR(3)
 Sof(F26)=Sof(F20)=Sof(F27)=Sof(F25)=Sof(F19)=Sof(F22)=Sof(F23)=Sof(F21)=
 Sof(F24)=Sof(C56)=Sof(C57)=FVAR(3)
 Sof(F7A)=Sof(F9A)=Sof(F8A)=Sof(F1A)=Sof(F2A)=Sof(F6A)=Sof(F3A)=Sof(F5A)=
 Sof(F4A)=Sof(C50A)=Sof(C48A)=Sof(C49A)=1-FVAR(4)
 Sof(F7)=Sof(F9)=Sof(F8)=Sof(F1)=Sof(F2)=Sof(F6)=Sof(F3)=Sof(F5)=Sof(F4)=
 Sof(C50)=Sof(C48)=Sof(C49)=FVAR(4)
 Sof(F33A)=Sof(F31A)=Sof(F35A)=Sof(F32A)=Sof(F28A)=Sof(F34A)=Sof(F29A)=
 Sof(F36A)=Sof(F30A)=Sof(C61A)=Sof(C60A)=Sof(C62A)=1-FVAR(5)
 Sof(F33)=Sof(F31)=Sof(F35)=Sof(F32)=Sof(F28)=Sof(F34)=Sof(F29)=Sof(F36)=
 Sof(F30)=Sof(C61)=Sof(C60)=Sof(C62)=FVAR(5)
 Fixed Y: F14A(0.78123)
 Fixed Z: F14A(1.016489)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C21(H21), C1(H1), C29(H29), C9(H9), C14(H14), C23(H23), C17(H17),
 C11(H11), C15(H15), C26(H26), C27(H27)
6.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C32(H32A,H32B,H32C), C38(H38A,H38B,H38C), C36(H36A,H36B,
 H36C), C41(H41A,H41B,H41C), C34(H34A,H34B,H34C), C42(H42A,H42B,H42C), C40(H40A,
 H40B,H40C), C33(H33A,H33B,H33C), C45(H45A,H45B,H45C), C44(H44A,H44B,H44C),
 C46(H46A,H46B,H46C), C46A(H46D,H46E,H46F), C45A(H45D,H45E,H45F), C44A(H44D,
 H44E,H44F)
;
_shelx_res_checksum              26059
_shelx_hkl_checksum              81469
_olex2_submission_special_instructions 'No special instructions were received'