Ladderization of polycyclic aromatic hydrocarbons enhances electrical conductivity through additional coherent channels
Wang, Qing; Huang, Na; zhang, Ruiying; Chen, Li-Chuan; Yan, Jian-Feng; Chen, Zhong-Ning; Li, Yuanming; Zhang, Qian-Chong; Physical Chemistry Chemical Physics  (2026) –; doi:10.1039/D6CP00672H

data_7251853
_publ_section_title
;
 Ladderization of polycyclic aromatic hydrocarbons enhances electrical
 conductivity through additional coherent channels.
;
_journal_issue                   21
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              12812
_journal_page_last               12816
_journal_paper_doi               10.1039/d6cp00672h
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C48 H46 S2, C7 H8'
_chemical_formula_sum            'C55 H54 S2'
_chemical_formula_weight         779.10
_chemical_name_systematic
'((1,8-bis(4-(tert-butyl)phenyl)phenanthrene-2,7-diyl)bis(4,1-phenylene))bis(methylsulfane) compound with toluene (1:1)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2026-01-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2026-01-22 deposited with the CCDC.	2026-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.8700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.53820(10)
_cell_length_b                   22.3478(3)
_cell_length_c                   22.2413(3)
_cell_measurement_reflns_used    17715
_cell_measurement_temperature    100.4(9)
_cell_measurement_theta_max      55.3630
_cell_measurement_theta_min      2.4330
_cell_volume                     4243.37(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.131a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.131a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.131a (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 2025/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.4(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_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     76.00 101.00   0.50    0.30    --   62.14 145.00 -92.00   50
  2  \w     81.00 106.00   0.50    0.30    --   62.14 125.00 100.00   50
  3  \w     47.00 135.00   0.50    0.30    --   62.14  57.00  90.00  176
  4  \w    -14.00  32.00   0.50    0.07    --   -1.25  57.00  30.00   92
  5  \w    -14.00  20.00   0.50    0.07    --   -1.25  57.00 120.00   68
  6  \w     27.00  62.00   0.50    0.07    --   -1.25  57.00 120.00   70
  7  \w    -87.00   7.00   0.50    0.30    --  -64.64  77.00  90.00  188
  8  \w    -23.00   8.00   0.50    0.30    --  -64.64  19.00  90.00   62
  9  \w    -24.00  11.00   0.50    0.30    --  -64.64  19.00  60.00   70
 10  \w    -26.00  11.00   0.50    0.30    --  -64.64  19.00  30.00   74
 11  \w    -39.00 -13.00   0.50    0.30    --  -64.64  38.00 -30.00   52
 12  \w    -42.00 -16.00   0.50    0.30    --  -64.64  57.00 -60.00   52
 13  \w   -112.00 -47.00   0.50    0.30    --  -64.64 145.00 -92.00  130
 14  \w   -102.00 -33.00   0.50    0.30    --  -64.64 125.00 100.00  138
 15  \w   -105.00 -80.00   0.50    0.30    --  -64.64-125.00  23.00   50
 16  \w   -101.00 -76.00   0.50    0.30    --  -64.64-145.00-143.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0646056000
_diffrn_orient_matrix_UB_12      -0.0279487000
_diffrn_orient_matrix_UB_13      -0.0467707000
_diffrn_orient_matrix_UB_21      -0.0449083000
_diffrn_orient_matrix_UB_22      -0.0528517000
_diffrn_orient_matrix_UB_23      0.0222676000
_diffrn_orient_matrix_UB_31      -0.1357525000
_diffrn_orient_matrix_UB_32      0.0041933000
_diffrn_orient_matrix_UB_33      -0.0306627000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            28383
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         55.374
_diffrn_reflns_theta_min         2.437
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.131a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       needle
_exptl_crystal_F_000             1664
_exptl_crystal_recrystallization_method
'The crystals were growth by means of evaporation of a mixture of methanol and toluene at RT.'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         8062
_refine_ls_number_restraints     399
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0542P)^2^+1.5180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6782
_reflns_number_total             8062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cp00672h2.cif
_cod_data_source_block           WQ-SM-2
_cod_depositor_comments          'Adding full bibliography for 7251853.cif.'
_cod_database_code               7251853
_shelx_shelxl_version_number     2025/1
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.830
_exptl_crystal_mounting_method
;
 Crystals were removed from the crystallisation vial and immediately coated
 with PDMS (polydimethylsiloxane/Dimethicone, CAS: 9006-65-9 on a glass slide.
 A suitable single crystal was selected and mounted on a glass fiber using
 vacuum silicone grease as adhesive. The glass fiber with single crystal was
 mounted on copper pin with solid paraffin. Operator: DJ_Tokyo.
;
_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. Uiso/Uaniso restraints and constraints
C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim
C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim
C44 \\sim C45 \\sim C46 \\sim C49 \\sim C50 \\sim C29A \\sim C30A \\sim C31A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C57 \\sim C51A
\\sim C52A \\sim C53A \\sim C54A \\sim C55A \\sim C56A \\sim C57A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Same fragment restrains
{C28, C29A, C30A, C31A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C28, C29, C30, C31}
{C51A, C52A, C53A, C54A, C55A, C56A, C57A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C51, C52, C53, C54, C55, C56, C57}
4. Others
 Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=Sof(C30A)=Sof(H30D)=Sof(H30E)=
 Sof(H30F)=Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(1)
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=FVAR(1)
 Sof(C51A)=Sof(C52A)=Sof(H52A)=Sof(C53A)=Sof(H53A)=Sof(C54A)=Sof(H54A)=
 Sof(C55A)=Sof(H55A)=Sof(C56A)=Sof(H56A)=Sof(C57A)=Sof(H57D)=Sof(H57E)=
 Sof(H57F)=1-FVAR(2)
 Sof(C51)=Sof(C52)=Sof(H52)=Sof(C53)=Sof(H53)=Sof(C54)=Sof(H54)=Sof(C55)=
 Sof(H55)=Sof(C56)=Sof(H56)=Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(H57C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18),
 C20(H20), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C37(H37), C38(H38),
  C40(H40), C41(H41), C42(H42), C43(H43), C45(H45), C46(H46), C52(H52),
 C53(H53), C54(H54), C55(H55), C56(H56), C52A(H52A), C53A(H53A), C54A(H54A),
 C55A(H55A), C56A(H56A)
5.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,
 H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C49(H49A,H49B,H49C), C50(H50A,
 H50B,H50C), C29A(H29D,H29E,H29F), C30A(H30D,H30E,H30F), C31A(H31D,H31E,H31F),
 C57(H57A,H57B,H57C), C57A(H57D,H57E,H57F)
;
_shelx_res_checksum              10043
_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 2.129
_oxdiff_exptl_absorpt_empirical_full_min 0.520