π-Stacked dimerization of an antiaromatic homoHPHAC monocation.
Wada, Kaito; Tanioka, Yuma; Mori, Shigeki; Uno, Hidemitsu; Takase, Masayoshi; Chemical communications (Cambridge, England) 62 (2026) 6716–6720; doi:10.1039/d5cc07392h

data_7135560
_publ_section_title
;
 &#x3c0;-Stacked dimerization of an antiaromatic homoHPHAC monocation.
;
_journal_issue                   25
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6716
_journal_page_last               6720
_journal_paper_doi               10.1039/d5cc07392h
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C51 H53 N6, 1(F6 Sb)'
_chemical_formula_sum            'C51 H53 F6 N6 Sb'
_chemical_formula_weight         985.74
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2026-02-12
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-02-13 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                98.437(2)
_cell_angle_beta                 93.659(3)
_cell_angle_gamma                92.019(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0231(5)
_cell_length_b                   12.6110(4)
_cell_length_c                   15.2281(4)
_cell_measurement_reflns_used    25029
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.7580
_cell_measurement_theta_min      1.9640
_cell_volume                     2087.58(13)
_computing_cell_refinement       'CrysAlisPro 1.171.44.85 (Rigaku OD, 2024)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.44.85 (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 7.111
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.898
_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   -105.00  75.00   0.50    1.00    --  -15.00  45.00   0.00  360
  2  \w   -105.00  75.00   0.50    1.00    --  -15.00  45.00  90.00  360
  3  \w   -105.00  75.00   0.50    1.00    --  -15.00  45.00 180.00  360
  4  \w   -105.00  75.00   0.50    1.00    --  -15.00  45.00 270.00  360
;
_diffrn_measurement_device       'AFC11 SATURN724+ Right'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0106540000
_diffrn_orient_matrix_UB_12      -0.0536698000
_diffrn_orient_matrix_UB_13      0.0074075000
_diffrn_orient_matrix_UB_21      -0.0135756000
_diffrn_orient_matrix_UB_22      0.0187978000
_diffrn_orient_matrix_UB_23      0.0443488000
_diffrn_orient_matrix_UB_31      -0.0621940000
_diffrn_orient_matrix_UB_32      0.0024226000
_diffrn_orient_matrix_UB_33      -0.0143675000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            44460
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.899
_diffrn_reflns_theta_min         1.634
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'MicroMax 007'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.85 (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.786
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0173(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2025/1 (Sheldrick 2025)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     786
_refine_ls_number_reflns         11821
_refine_ls_number_restraints     1081
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+1.5181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8838
_reflns_number_total             11821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc07392h2.cif
_cod_data_source_block           wada_autored
_cod_depositor_comments          'Adding full bibliography for 7135560.cif.'
_cod_database_code               7135560
_shelx_shelxl_version_number     2025/1
_chemical_oxdiff_formula         Sb1F6N6C51H53
_cell_oxdiff_angle_alpha         98.437(2)
_cell_oxdiff_angle_beta          93.659(3)
_cell_oxdiff_angle_gamma         92.019(3)
_cell_oxdiff_length_a            11.0231(4)
_cell_oxdiff_length_b            12.6110(4)
_cell_oxdiff_length_c            15.2281(4)
_cell_oxdiff_measurement_reflns_used 25029
_cell_oxdiff_volume              2087.59(12)
_diffrn_oxdiff_digest_od_ed
;

;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Sb1-F1 \\sim Sb1-F2 \\sim Sb1-F3 \\sim Sb1-F4 \\sim Sb1-F5 \\sim Sb1-F6
 with sigma of 0.02
 Sb21-F201 \\sim Sb21-F202 \\sim Sb21-F203 \\sim Sb21-F204 \\sim Sb21-F205
\\sim Sb21-F206
 with sigma of 0.02
 C36-C37 \\sim C136-C137
 with sigma of 0.02
 C16-C36 \\sim C116-C136
 with sigma of 0.02
 Sb11-F101 \\sim Sb11-F102 \\sim Sb11-F103 \\sim Sb11-F104 \\sim Sb11-F105
\\sim Sb11-F106
 with sigma of 0.02
 C16-C37 \\sim C116-C137
 with sigma of 0.04
 C17-C38 \\sim C117-C138
 with sigma of 0.02
 C38-C39 \\sim C138-C139
 with sigma of 0.02
 C17-C39 \\sim C117-C139
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Sb1 \\sim F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim Sb21 \\sim F201
\\sim F202 \\sim F203 \\sim F204 \\sim F205 \\sim F206 \\sim Sb11 \\sim F101
\\sim F102 \\sim F103 \\sim F104 \\sim F105 \\sim F106: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C16 \\sim C17 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C116 \\sim C117
\\sim C136 \\sim C137 \\sim C138 \\sim C139: within 2A with sigma of 0.003 and
sigma for terminal atoms of 0.006 within 2A
Uanis(Sb1) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim
Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(Sb11)
\\sim Ueq, Uanis(F101) \\sim Ueq, Uanis(F102) \\sim Ueq, Uanis(F103) \\sim Ueq,
Uanis(F104) \\sim Ueq, Uanis(F105) \\sim Ueq, Uanis(F106) \\sim Ueq,
Uanis(Sb21) \\sim Ueq, Uanis(F201) \\sim Ueq, Uanis(F202) \\sim Ueq,
Uanis(F203) \\sim Ueq, Uanis(F204) \\sim Ueq, Uanis(F205) \\sim Ueq,
Uanis(F206) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37)
\\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C116) \\sim Ueq,
Uanis(C117) \\sim Ueq, Uanis(C136) \\sim Ueq, Uanis(C137) \\sim Ueq,
Uanis(C138) \\sim Ueq, Uanis(C139) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
4. Rigid body (RIGU) restrains
 Sb1, F1, F2, F3, F4, F5, F6, Sb21, F201, F202, F203, F204, F205, F206, Sb11,
 F101, F102, F103, F104, F105, F106
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, C17, C36, C37, C38, C39, C116, C117, C136, C137, C138, C139
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 1*[Sof(Sb1)+Sof(F1)+Sof(F2)+Sof(F3)+Sof(F4)+Sof(F5)+Sof(F6)]+1*[Sof(Sb11)+
 Sof(F101)+Sof(F102)+Sof(F103)+Sof(F104)+Sof(F105)+Sof(F106)]+1*[Sof(Sb21)+
 Sof(F201)+Sof(F202)+Sof(F203)+Sof(F204)+Sof(F205)+Sof(F206)]=1 with esd of
 0.00001
 Sof(Sb1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(Sb11)=Sof(F101)=Sof(F102)=Sof(F103)=Sof(F104)=Sof(F105)=Sof(F106)=FVAR(2)
 Sof(Sb21)=Sof(F201)=Sof(F202)=Sof(F203)=Sof(F204)=Sof(F205)=Sof(F206)=FVAR(3)
 Sof(C116)=Sof(C117)=Sof(C136)=Sof(H13A)=Sof(H13B)=Sof(C137)=Sof(H13C)=
 Sof(H13D)=Sof(H13E)=Sof(C138)=Sof(H13F)=Sof(H13G)=Sof(C139)=Sof(H13H)=
 Sof(H13I)=Sof(H13J)=1-FVAR(4)
 Sof(C16)=Sof(C17)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=
 Sof(H37C)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=
 FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C34(H34A,H34B), C40(H40A,H40B), C42(H42A,H42B), C44(H44A,
 H44B), C50(H50A,H50B), C36(H36A,H36B), C38(H38A,H38B), C136(H13A,H13B),
 C138(H13F,H13G)
6.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C31(H31)
6.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C41(H41A,H41B,H41C), C43(H43A,H43B,
 H43C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C49(H49A,H49B,H49C), C51(H51A,
 H51B,H51C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C137(H13C,H13D,H13E),
 C139(H13H,H13I,H13J)
;
_shelx_res_checksum              58515
_shelx_hkl_checksum              56128
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.650