Regioselective late-stage functionalization of tetraphenylenes: rapid construction of double helical architectures and potential hole transport materials.
Xu, Xiang; Ma, Hao-Ran; Cui, Jian-Fang; Peng, Xiao-Shui; Wong, Henry N. C.; Chemical science 16 (2025) 4342–4351; doi:10.1039/d4sc07803a

data_1573779
_publ_section_title
;
 Regioselective late-stage functionalization of tetraphenylenes: rapid
 construction of double helical architectures and potential hole transport
 materials.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              4342
_journal_page_last               4351
_journal_paper_doi               10.1039/d4sc07803a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C64 H60 O2'
_chemical_formula_sum            'C64 H60 O2'
_chemical_formula_weight         861.12
_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             2021-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-09-03 deposited with the CCDC.	2025-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.354(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8746(12)
_cell_length_b                   19.1113(14)
_cell_length_c                   17.1888(14)
_cell_measurement_reflns_used    7967
_cell_measurement_temperature    297
_cell_measurement_theta_max      23.637
_cell_measurement_theta_min      2.443
_cell_volume                     5171.9(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31660
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.780
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   multi-scan
_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    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0035(4)
_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   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+7.7987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1765
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2848
_reflns_number_total             4678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07803a2.cif
_cod_data_source_block           sam1-1
_cod_depositor_comments          'Adding full bibliography for 1573779.cif.'
_cod_database_code               1573779
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.975
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C14(H14), C16(H16),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              72988
_olex2_submission_special_instructions 'No special instructions were received'