Chiral tether-guided selective synthesis of <i>D</i> <sub><i>n</i></sub> -symmetric chiral conjugated nanorings.
An, Tai; Yao, Jiayao; Xiao, Zuo; Yu, Qi; Wang, Yu; Gao, Yueyue; Song, Yixiao; Huang, Zuoxin; Ding, Zheng; Zhang, Xinyue; Xie, Yuanpeng; Lv, Menglan; Zuo, Chuantian; Ding, Junqiao; Ding, Liming; Chemical science 16 (2025) 21404–21415; doi:10.1039/d5sc06445g

data_1576039
_publ_section_title
;
 Chiral tether-guided selective synthesis of <i>D</i> <sub><i>n</i></sub>
 -symmetric chiral conjugated nanorings.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              21404
_journal_page_last               21415
_journal_paper_doi               10.1039/d5sc06445g
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2.333(C H Cl3), 0.333(C Cl3), C78 H72 N6'
_chemical_formula_sum            'C80.67 H74.33 Cl8 N6'
_chemical_formula_weight         1411.35
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-04-03 deposited with the CCDC.	2025-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   34.900(3)
_cell_length_b                   34.900(3)
_cell_length_c                   14.8617(15)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      45.384
_cell_measurement_theta_min      2.882
_cell_volume                     15677(2)
_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  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0740
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            97418
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.063
_diffrn_reflns_theta_min         3.629
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    2.216
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1110 before and 0.0833 after correction.
The Ratio of minimum to maximum transmission is 0.8038.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       needle
_exptl_crystal_F_000             6627
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.949
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 4188 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.053(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     897
_refine_ls_number_reflns         14145
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0794
_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^)+(0.1786P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2107
_refine_ls_wR_factor_ref         0.2337
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                10474
_reflns_number_total             14145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06445g2.cif
_cod_data_source_block           241110_1107_01_zwj
_cod_depositor_comments
'Adding full bibliography for 1576037--1576039.cif.'
_cod_original_cell_volume        15676(3)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               1576039
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.809
_shelx_estimated_absorpt_t_min   0.630
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1A
Cl12 \\sim Cl8 \\sim Cl10 \\sim C4 \\sim Cl3 \\sim Cl7 \\sim Cl2 \\sim C6:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C6) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl7) \\sim Ueq, Uanis(Cl2)
\\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(Cl12) \\sim Ueq, Uanis(Cl8) \\sim Ueq,
Uanis(Cl10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: Cl8(0.33333) Cl10(0.33333) C4(0.33333) Cl12(0.33333) C6(0.333)
 H6(0.333) Cl3(0.333) Cl7(0.333) Cl2(0.333)
4.a :
 C4(Cl12), C6(Cl3,Cl7,Cl2)
4.b Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C8(H8)
4.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C32(H32A,H32B), C36(H36A,H36B), C44(H44A,H44B), C48(H48A,
 H48B), C52(H52A,H52B), C68(H68A,H68B), C72(H72A,H72B), C76(H76A,H76B),
 C80(H80A,H80B), C41(H41A,H41B), C43(H43A,H43B), C45(H45A,H45B), C49(H49A,H49B),
  C25(H25A,H25B), C55(H55A,H55B), C15(H15A,H15B), C61(H61A,H61B), C65(H65A,
 H65B), C33(H33A,H33B), C67(H67A,H67B), C69(H69A,H69B), C71(H71A,H71B),
 C39(H39A,H39B)
4.d Aromatic/amide H refined with riding coordinates:
 C20(H20), C24(H24), C30(H30), C38(H38), C50(H50), C54(H54), C60(H60),
 C64(H64), C78(H78), C21(H21), C23(H23), C51(H51), C13(H13), C53(H53), C57(H57),
  C63(H63), C2(H2), C35(H35), C9(H9), C73(H73), C75(H75), C19(H19), C77(H77),
 C79(H79)
;
_olex2_submission_special_instructions 'No special instructions were received'