Chiral carbon nanorings with strong chiral luminescent and second harmonic generation properties
Yu, Qi; Zhao, Jinghan; Xiao, Zuo; Wang, Yu; Jin, Ke; Huang, Kaige; Zuo, Chuantian; Zhu, Lingyun; Du, Wenna; Yue, Shizhong; Wang, Zhijie; Liu, Xinfeng; Ding, Liming; Chemical Communications  (2026) –; doi:10.1039/D6CC00720A

data_7135670
_publ_section_title
;
 Chiral carbon nanorings with strong chiral luminescence and
 second-harmonic generation properties.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8003
_journal_page_last               8007
_journal_paper_doi               10.1039/d6cc00720a
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C174 H192 N6 O6'
_chemical_formula_sum            'C174 H192 N6 O6'
_chemical_formula_weight         2463.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2026-03-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2026-03-13 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   29.2518(13)
_cell_length_b                   14.1018(6)
_cell_length_c                   26.9540(12)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      53.838
_cell_measurement_theta_min      2.990
_cell_volume                     11118.6(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            90876
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.013
_diffrn_reflns_theta_min         3.788
_diffrn_source_current           3.57
_diffrn_source_power             0.249543
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.6005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1365 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.8000.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.736
_exptl_crystal_description       block
_exptl_crystal_F_000             2652
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 7422 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.64(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     868
_refine_ls_number_reflns         20069
_refine_ls_number_restraints     1969
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0659
_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^)+(0.1617P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.1960
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                17953
_reflns_number_total             20069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00720a2.cif
_cod_data_source_block           250712_20250621
_cod_depositor_comments
'Adding full bibliography for 7135669--7135670.cif.'
_cod_database_code               7135670
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C58-C64
 1.53 with sigma of 0.01
 C80B-C64 = C80A-C64 = C86A-C80A
 1.53 with sigma of 0.01
 C86B-C80B
 1.53 with sigma of 0.01
 C85-C74
 1.53 with sigma of 0.01
 C85A-C74
 1.53 with sigma of 0.01
 C81-C75
 1.53 with sigma of 0.01
 C81A-C75
 1.53 with sigma of 0.01
 C78-C83 \\sim C78-C83A
 with sigma of 0.02
 C74-C85 \\sim C74-C85A
 with sigma of 0.02
 C75-C81 \\sim C75-C81A
 with sigma of 0.02
3. Rigid bond restraints
 C69, C76
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within -3A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within -3A
C80A \\sim C86A: within 1.8A with sigma of 0.001 and sigma for terminal atoms
of 0.002 within 1.8A
C80B: within 2.1A with sigma of 0.005 and sigma for terminal atoms of 0.01
within 2.1A
Uanis(C80B) = Uanis(C80A)
Uanis(C80A) = Uanis(C86A)
Uanis(C86A) = Uanis(C86B)
5. Others
 Sof(H78C)=Sof(H78D)=Sof(C83A)=Sof(H83D)=Sof(H83E)=Sof(H83F)=1-FVAR(1)
 Sof(H78A)=Sof(H78B)=Sof(C83)=Sof(H83A)=Sof(H83B)=Sof(H83C)=FVAR(1)
 Sof(H75C)=Sof(H75D)=Sof(C81A)=Sof(H81D)=Sof(H81E)=Sof(H81F)=1-FVAR(2)
 Sof(H75A)=Sof(H75B)=Sof(C81)=Sof(H81A)=Sof(H81B)=Sof(H81C)=FVAR(2)
 Fixed Sof: H64C(0.5) H64D(0.5) H64A(0.5) H64B(0.5) H74B(0.5) H74A(0.5)
 H74D(0.5) H74C(0.5) C80B(0.5) H80A(0.5) H80B(0.5) C85(0.5) H85A(0.5) H85B(0.5)
 H85C(0.5) C85A(0.5) H85D(0.5) H85E(0.5) H85F(0.5) C86A(0.5) H86A(0.5)
 H86B(0.5) H86C(0.5) C80A(0.5) H80C(0.5) H80D(0.5) C86B(0.5) H86D(0.5)
 H86E(0.5) H86F(0.5)
6.a Riding coordinates:
 C80B(H80A,H80B), C80A(H80C,H80D), C86B(H86D,H86E,H86F)
6.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C31(H31A,H31B), C37(H37A,H37B), C42(H42A,H42B), C47(H47A,
 H47B), C50(H50A,H50B), C51(H51A,H51B), C54(H54A,H54B), C56(H56A,H56B),
 C58(H58A,H58B), C60(H60A,H60B), C62(H62A,H62B), C63(H63A,H63B), C64(H64C,H64D),
  C64(H64A,H64B), C65(H65A,H65B), C66(H66A,H66B), C67(H67A,H67B), C68(H68A,
 H68B), C69(H69A,H69B), C70(H70A,H70B), C71(H71A,H71B), C72(H72A,H72B),
 C73(H73A,H73B), C74(H74B,H74A), C74(H74D,H74C), C75(H75A,H75B), C75(H75C,H75D),
  C76(H76A,H76B), C77(H77A,H77B), C78(H78A,H78B), C78(H78C,H78D), C82(H82A,H82B)
6.c Me refined with riding coordinates:
 C79(H79A,H79B,H79C), C84(H84A,H84B,H84C), C81(H81A,H81B,H81C), C83(H83A,H83B,
 H83C), C85(H85A,H85B,H85C), C81A(H81D,H81E,H81F), C83A(H83D,H83E,H83F),
 C85A(H85D,H85E,H85F)
6.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C21(H21), C23(H23), C24(H24), C28(H28), C29(H29),
 C32(H32), C35(H35), C41(H41), C44(H44), C48(H48), C49(H49), C52(H52), C53(H53),
  C55(H55), C57(H57), C61(H61)
6.e Idealised Me refined as rotating group:
 C86A(H86A,H86B,H86C)
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_smtbx_masks_special_details
;
A solvent mask was calculated and 1833 electrons were 
found in a volume of 5331\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
16[CH2Cl2], 12[CH3CN] per Asymmetric Unit 
which account for 1872 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              37082
_shelx_hkl_checksum              76610
_shelx_fab_checksum              41581
_olex2_submission_special_instructions 'No special instructions were received'