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_7135669
_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_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2025-12-25 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                   30.6017(9)
_cell_length_b                   13.4372(4)
_cell_length_c                   27.6470(8)
_cell_measurement_reflns_used    9024
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      43.36
_cell_measurement_theta_min      2.87
_cell_volume                     11368.5(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            111061
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        48.328
_diffrn_reflns_theta_max         48.328
_diffrn_reflns_theta_min         1.390
_diffrn_source_current           2.86
_diffrn_source_power             0.200057
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.720
_exptl_crystal_description       block
_exptl_crystal_F_000             2652
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     785
_refine_ls_number_reflns         16147
_refine_ls_number_restraints     1335
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.1037
_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^)+(0.1000P)^2^+12.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2638
_refine_ls_wR_factor_ref         0.2794
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                10879
_reflns_number_total             16147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00720a2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7135669--7135670.cif.'
_cod_database_code               7135669
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: -0.2(6)
 1.2(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C50-C28
 1.57 with sigma of 0.01
 C50-C077
 2.3 with sigma of 0.01
 C077-C062 = C082-C077 = C50-C082 = C50-C28 = C073-C062 = C084-C073 = C58-C084
 = C58-C18 = C9-C17 = C9-C074 = C083-C074 = C083-C046 = C061-C046 = C066-C061 =
 C088-C066 = C110-C088 = C039-C032 = C068-C039 = C079-C068 = C063-C038 = C038-
 C032 = C072-C063 = C085-C072
 1.54 with sigma of 0.01
 C077-C073
 2.35 with sigma of 0.01
 C28-C082
 2.35 with sigma of 0.01
 C78-C079
 1.57 with sigma of 0.01
 H075-H034
 2.15 with sigma of 0.01
 C053-C003 \\sim C065-C053 \\sim C065-C055 \\sim C092-C064 \\sim C092-C089
\\sim C089-C078 \\sim C095-
 C078 \\sim C095-C060 \\sim C081-C060 \\sim C081-C071
 with sigma of 0.01
4. Rigid bond restraints
 C079, C78
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within -2.5A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within -2.5A
6.a Secondary CH2 refined with riding coordinates:
 C003(H00A,H00B), C038(H03A,H03B), C039(H03C,H03D), C053(H05A,H05B), C055(H05C,
 H05D), C060(H06A,H06B), C061(H06C,H06D), C063(H06E,H06F), C064(H06G,H06H),
 C065(H06I,H06J), C066(H06K,H06L), C068(H06M,H06N), C071(H07B,H07A), C072(H07C,
 H07D), C073(H07F,H07E), C074(H07G,H07H), C077(H07I,H07J), C078(H07K,H07L),
 C079(H07M,H07N), C081(H08A,H08B), C082(H08C,H08D), C083(H08E,H08F), C084(H08G,
 H08H), C088(H08L,H08M), C089(H08N,H08O), C092(H09A,H09B), C095(H09C,H09D),
 C58(H58A,H58B), C9(H9A,H9B), C50(H50A,H50B)
6.b Aromatic/amide H refined with riding coordinates:
 C075(H075), C069(H069), C033(H033), C058(H058), C052(H052), C067(H067),
 C059(H059), C034(H034), C014(H014), C016(H016), C041(H041), C054(H054),
 C036(H036), C024(H024), C045(H045), C051(H051), C070(H070), C076(H076)
6.c Fitted hexagon refined as free rotating group:
 C004(C075,C069,C010,C015,C033), C008(C030,C050,C058,C052,C018), C009(C067,
 C059,C044,C037,C034), C012(C014,C007,C027,C016,C041), C013(C035,C021,C054,C036,
 C020)
6.d Idealised Me refined as rotating group:
 C085(H08I,H08J,H08K), C110(H11A,H11B,H11C), C17(H17A,H17B,H17C), C18(H18A,
 H18B,H18C), C28(H28A,H28B,H28C), C78(H78A,H78B,H78C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'