A bow-like axially chiral cycloparaphenylene with simultaneously enhanced photoluminescence quantum yield and dissymmetry factor
Yu, Meng-Xue; Feng, Chao; Guo, Wei-Chen; Chen, Chuan-Feng; Chemical Science  (2025) –; doi:10.1039/D5SC07321A

data_1576237
_publ_section_title
;
 A bow-like axially chiral cycloparaphenylene with simultaneously enhanced
 photoluminescence quantum yield and dissymmetry factor
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC07321A
_journal_year                    2025
_chemical_formula_moiety
'0.087(C Cl3), 0.087(C111 N9), 0.174(C2 N), 0.087[], 0.043[], 0.043[], 0.087[], 0.043[]'
_chemical_formula_sum            'C119 H97 Cl3 N8'
_chemical_formula_weight         1745.39
_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     iterative
_audit_creation_date             2025-02-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-07 deposited with the CCDC.	2025-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                93.438(4)
_cell_angle_beta                 106.677(6)
_cell_angle_gamma                100.910(5)
_cell_formula_units_Z            2
_cell_length_a                   14.8285(11)
_cell_length_b                   15.6780(9)
_cell_length_c                   24.1104(11)
_cell_measurement_reflns_used    3823
_cell_measurement_temperature    170.2(9)
_cell_measurement_theta_max      64.3700
_cell_measurement_theta_min      2.0370
_cell_volume                     5233.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.114a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 42.96a 64-bit (release 27-07-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.114a (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, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.2(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    -24.00   6.00   0.50    0.77    --  -46.51 103.00-110.00   60
  2  \w    -82.00 -43.00   0.50    0.77    --  -46.51 103.00-110.00   78
  3  \w      9.00  82.00   0.50    0.77    --   46.51-103.00 147.00  146
  4  \w    -94.00 -68.00   0.50    3.06    -- -104.50 103.00-110.00   52
  5  \w     35.00  90.00   0.50    3.06    --  105.35-103.00 147.00  110
  6  \w    125.00 151.00   0.50    3.06    --  105.35 103.00-110.00   52
  7  \w    -23.00  29.00   0.50    0.77    --  -46.51  19.00 -30.00  104
  8  \w    -84.00 -51.00   0.50    0.77    --  -46.51 125.00 -90.00   66
  9  \w    -44.00 -17.00   0.50    0.77    --  -46.51 125.00 -90.00   54
 10  \w    -22.00  27.00   0.50    0.77    --  -46.51  38.00  30.00   98
 11  \w    -31.00  21.00   0.50    0.77    --  -46.51  38.00   0.00  104
 12  \w    -18.00  19.00   0.50    0.77    --  -46.51  19.00 -90.00   74
 13  \w     25.00  87.00   0.50    0.77    --   46.51-125.00 120.00  124
 14  \w     23.00 116.00   0.50    0.77    --   46.51  77.00-120.00  186
 15  \w   -108.00 -80.00   0.50    3.06    -- -104.50 125.00  30.00   56
 16  \w   -111.00 -37.00   0.50    3.06    -- -104.50 125.00 -90.00  148
 17  \w   -110.00 -83.00   0.50    3.06    -- -104.50 125.00 -30.00   54
 18  \w   -173.00 -92.00   0.50    3.06    -- -104.50 -30.00  30.00  162
 19  \w   -123.00 -85.00   0.50    3.06    -- -104.50 141.00-175.75   76
 20  \w   -126.00 -83.00   0.50    3.06    -- -104.50 -70.00   2.18   86
 21  \w   -161.00-135.00   0.50    3.06    -- -104.50 -70.00   2.18   52
 22  \w   -172.00 -85.00   0.50    3.06    -- -104.50-103.00 147.00  174
 23  \w   -101.00 -31.00   0.50    3.06    -- -104.50  77.00 -90.00  140
 24  \w   -121.00 -87.00   0.50    3.06    -- -104.50 139.00 125.19   68
 25  \w   -111.00 -54.00   0.50    3.06    -- -104.50 125.00   0.00  114
 26  \w    -92.00 -60.00   0.50    3.06    -- -104.50 125.00 150.00   64
 27  \w   -102.00 -56.00   0.50    3.06    -- -104.50  77.00 150.00   92
 28  \w   -108.00 -82.00   0.50    3.06    -- -104.50 116.00-108.58   52
 29  \w   -148.00 -90.00   0.50    3.06    -- -104.50 -51.00  52.77  116
 30  \w    -74.00 -47.00   0.50    3.06    -- -104.50 125.00 -30.00   54
 31  \w   -171.00 -92.00   0.50    3.06    -- -104.50 -30.00-180.00  158
 32  \w   -171.00-109.00   0.50    3.06    -- -104.50 -53.00-128.16  124
 33  \w     97.00 178.00   0.50    3.06    --  105.35  30.00 -60.00  162
 34  \w     40.00  74.00   0.50    3.06    --  105.35 -61.00 120.00   68
 35  \w     58.00  92.00   0.50    3.06    --  105.35 -94.00 -60.00   68
 36  \w     33.00  74.00   0.50    3.06    --  105.35 -61.00 -30.00   82
 37  \w     92.00 173.00   0.50    3.06    --  105.35  30.00 -90.00  162
 38  \w     36.00 100.00   0.50    3.06    --  105.35 -94.00  90.00  128
 39  \w     34.00  82.00   0.50    3.06    --  105.35 -94.00 -30.00   96
 40  \w     35.00  72.00   0.50    3.06    --  105.35 -61.00  30.00   74
 41  \w     33.00  75.00   0.50    3.06    --  105.35 -61.00 150.00   84
 42  \w     83.00 177.00   0.50    3.06    --  105.35  77.00-150.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0671790000
_diffrn_orient_matrix_UB_12      0.0401069000
_diffrn_orient_matrix_UB_13      0.0612067000
_diffrn_orient_matrix_UB_21      -0.0884486000
_diffrn_orient_matrix_UB_22      0.0042791000
_diffrn_orient_matrix_UB_23      0.0205707000
_diffrn_orient_matrix_UB_31      -0.0011058000
_diffrn_orient_matrix_UB_32      -0.0923983000
_diffrn_orient_matrix_UB_33      0.0186113000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1854
_diffrn_reflns_av_unetI/netI     0.1560
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            65888
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.996
_diffrn_reflns_theta_min         1.927
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.114a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_description       needle
_exptl_crystal_F_000             1836
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1227
_refine_ls_number_reflns         18937
_refine_ls_number_restraints     142
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.2147
_refine_ls_R_factor_gt           0.1424
_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^)+(0.0114P)^2^+30.4308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2634
_refine_ls_wR_factor_ref         0.2976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10326
_reflns_number_total             18937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07321a2.cif
_cod_data_source_block           tx16744c_autored_sq
_cod_database_code               1576237
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     CHON
_olex2_refinement_description
;
1. Restrained distances
 C97-C100 \\sim C97-C101
 with sigma of 0.02
 C97-C99 \\sim C97-C98
 with sigma of 0.02
 C97-C103 \\sim C97-C102
 with sigma of 0.02
 C99-C102 \\sim C98-C102
 with sigma of 0.02
 C103-C101 \\sim C102-C101
 with sigma of 0.02
 C121-Cl2 \\sim C121-Cl2A
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
C97 \\sim C99 \\sim C100 \\sim C103 \\sim C98 \\sim C101 \\sim C102: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C121: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 1.7A
Cl2 \\sim Cl2A \\sim Cl3 \\sim Cl1: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 1.7A
Uanis(C97) \\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(C103) \\sim Ueq, Uanis(C99)
\\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(C98) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C121) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl2) \\sim Ueq, Uanis(Cl2A) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl3)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(C101)=Sof(H10G)=Sof(H10H)=Sof(H10I)=1-FVAR(1)
 Sof(C100)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
 Sof(C102)=Sof(H10J)=Sof(H10K)=Sof(H10L)=1-FVAR(2)
 Sof(C103)=Sof(H10D)=Sof(H10E)=Sof(H10F)=FVAR(2)
 Sof(C98)=Sof(H98A)=Sof(H98B)=Sof(H98C)=1-FVAR(3)
 Sof(C99)=Sof(H99A)=Sof(H99B)=Sof(H99C)=FVAR(3)
 Sof(H12D)=Sof(Cl2A)=1-FVAR(4)
 Sof(H121)=Sof(Cl2)=FVAR(4)
4.a Riding coordinates:
 C98(H98A,H98B,H98C)
4.b Ternary CH refined with riding coordinates:
 C121(H121), C121(H12D)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27),
  C28(H28), C29(H29), C32(H32), C33(H33), C34(H34), C36(H36), C38(H38),
 C39(H39), C40(H40), C42(H42), C44(H44), C45(H45), C47(H47), C48(H48), C50(H50),
  C53(H53), C54(H54), C57(H57), C58(H58), C59(H59), C60(H60), C68(H68),
 C69(H69), C70(H70), C75(H75), C77(H77), C78(H78), C86(H86), C87(H87), C88(H88),
  C93(H93), C94(H94), C96(H96), C105(H105), C106(H106), C113(H113), C115(H115)
4.d Idealised Me refined as rotating group:
 C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C65(H65A,H65B,
 H65C), C79(H79A,H79B,H79C), C80(H80A,H80B,H80C), C81(H81A,H81B,H81C),
 C118(H11A,H11B,H11C), C119(H11D,H11E,H11F), C120(H12A,H12B,H12C), C99(H99A,
 H99B,H99C), C100(H10A,H10B,H10C), C103(H10D,H10E,H10F), C101(H10G,H10H,H10I),
 C102(H10J,H10K,H10L), C83(H83A,H83B,H83C)
;
_shelx_res_checksum              11686
_shelx_fab_checksum              29256
_platon_squeeze_void_probe_radius 1.20
_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 2.422
_oxdiff_exptl_absorpt_empirical_full_min 0.386