Synthesis, Crystal Structure, and Inherent Chirality in Hexa(tertbutylphenyl)-Substituted [6]Cycloparaphenylene
Zhang, Xiaoyu; Zhang, Xingyu; Lu, Dapeng; Huang, Qiang; Du, Pingwu; Chemical Communications  (2026) –; doi:10.1039/D6CC02109C

data_7135742
_publ_section_title
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 Synthesis, crystal structure, and inherent chirality in
 hexa(<i>tert</i>-butylphenyl)-substituted [6]cycloparaphenylene.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9277
_journal_page_last               9280
_journal_paper_doi               10.1039/d6cc02109c
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         '1.063(C96 H96), 2.6[CH3OH]'
_chemical_formula_sum            'C104.6 H112.4 O2.6'
_chemical_formula_weight         1411.14
_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
_audit_creation_date             2025-10-16
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-07 deposited with the CCDC.	2026-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                108.502(3)
_cell_angle_beta                 95.339(4)
_cell_angle_gamma                113.214(3)
_cell_formula_units_Z            2
_cell_length_a                   14.1436(12)
_cell_length_b                   17.1687(15)
_cell_length_c                   20.6678(17)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      45.594
_cell_measurement_theta_min      2.635
_cell_volume                     4234.8(6)
_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  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1356
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            70325
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        46.151
_diffrn_reflns_theta_max         46.151
_diffrn_reflns_theta_min         2.026
_diffrn_source_current           3.57
_diffrn_source_power             0.24989999999999998
_diffrn_source_voltage           70.0
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.6023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1392 before and 0.0699 after correction.
The Ratio of minimum to maximum transmission is 0.8025.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       plate
_exptl_crystal_F_000             1522
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1023
_refine_ls_number_reflns         10913
_refine_ls_number_restraints     231
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0866P)^2^+0.9496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1712
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6883
_reflns_number_total             10913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc02109c2.cif
_cod_data_source_block           zz_20251013_dpw_xyz1_a
_cod_depositor_comments          'Adding full bibliography for 7135742.cif.'
_cod_original_formula_sum        'C104.60 H112.40 O2.60'
_cod_database_code               7135742
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.972
_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
 C54-C55 \\sim C54-C55A
 with sigma of 0.02
 C54-C57 \\sim C54-C57A
 with sigma of 0.02
 C54-C56 \\sim C54-C56A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C108 \\sim C101 \\sim C107 \\sim C100 \\sim C106 \\sim C99 \\sim C105 \\sim C98
\\sim C104 \\sim C97 \\sim C103 \\sim C102: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C56A \\sim C56 \\sim C57A \\sim C57 \\sim C55A \\sim C55: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C107)=Sof(H107)=Sof(C106)=Sof(H106)=Sof(C105)=Sof(H105)=Sof(C104)=
 Sof(H104)=Sof(C103)=Sof(H103)=Sof(C108)=Sof(H108)=1-FVAR(1)
 Sof(C98)=Sof(H98)=Sof(C99)=Sof(H99)=Sof(C101)=Sof(H101)=Sof(C97)=Sof(H97)=
 Sof(C100)=Sof(H100)=Sof(C102)=Sof(H102)=FVAR(1)
 Sof(C56A)=Sof(H56D)=Sof(H56E)=Sof(H56F)=Sof(C55A)=Sof(H55D)=Sof(H55E)=
 Sof(H55F)=Sof(C57A)=Sof(H57D)=Sof(H57E)=Sof(H57F)=1-FVAR(2)
 Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(H57C)=
 Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C31(H31), C45(H45), C64(H64), C24(H24), C63(H63), C1(H1), C21(H21), C25(H25),
 C65(H65), C78(H78), C32(H32), C49(H49), C58(H58), C36(H36), C19(H19), C18(H18),
  C50(H50), C28(H28), C62(H62), C88(H88), C66(H66), C61(H61), C96(H96),
 C16(H16), C89(H89), C95(H95), C37(H37), C7(H7), C79(H79), C40(H40), C68(H68),
 C82(H82), C72(H72), C69(H69), C8(H8), C53(H53), C11(H11), C39(H39), C52(H52),
 C71(H71), C81(H81), C10(H10), C98(H98), C99(H99), C101(H101), C97(H97),
 C100(H100), C102(H102), C107(H107), C106(H106), C105(H105), C104(H104),
 C103(H103), C108(H108)
5.b Idealised Me refined as rotating group:
 C92(H92A,H92B,H92C), C94(H94A,H94B,H94C), C42(H42A,H42B,H42C), C13(H13A,H13B,
 H13C), C93(H93A,H93B,H93C), C74(H74A,H74B,H74C), C84(H84A,H84B,H84C), C44(H44A,
 H44B,H44C), C86(H86A,H86B,H86C), C85(H85A,H85B,H85C), C76(H76A,H76B,H76C),
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C75(H75A,H75B,H75C), C55(H55A,H55B,
 H55C), C57(H57A,H57B,H57C), C43(H43A,H43B,H43C), C56(H56A,H56B,H56C),
 C56A(H56D,H56E,H56F), C55A(H55D,H55E,H55F), C57A(H57D,H57E,H57F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              10441
_shelx_hkl_checksum              23309
_shelx_fab_checksum              86092
_olex2_submission_special_instructions 'No special instructions were received'