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_1576038
_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_formula_moiety         'C84 H72 N6 O6'
_chemical_formula_sum            'C84 H72 N6 O6'
_chemical_formula_weight         1261.47
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2025-04-03 deposited with the CCDC.	2025-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                65.980(5)
_cell_angle_beta                 81.665(6)
_cell_angle_gamma                77.601(6)
_cell_formula_units_Z            2
_cell_length_a                   17.728(2)
_cell_length_b                   17.892(2)
_cell_length_c                   19.632(2)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      42.57
_cell_measurement_theta_min      2.22
_cell_volume                     5543.6(11)
_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 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.1665
_diffrn_reflns_av_unetI/netI     0.1868
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            101204
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        42.573
_diffrn_reflns_theta_max         42.573
_diffrn_reflns_theta_min         2.970
_diffrn_source_current           2.86
_diffrn_source_power             0.200057
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.756
_exptl_crystal_description       plate
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_coef       0.0030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1737
_refine_ls_number_reflns         23091
_refine_ls_number_restraints     2466
_refine_ls_restrained_S_all      30.262
_refine_ls_R_factor_all          0.1830
_refine_ls_R_factor_gt           0.0897
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1421P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2333
_refine_ls_wR_factor_ref         0.2860
_reflns_Friedel_coverage         0.981
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                9386
_reflns_number_total             23091
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06445g2.cif
_cod_data_source_block           250304d_wenjing_r_m_3_0m
_cod_depositor_comments
'Adding full bibliography for 1576037--1576039.cif.'
_cod_original_cell_volume        5543.4(11)
_cod_database_code               1576038
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5(6)
 0.5(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
3. Restrained distances
 C088-C081
 1.56 with sigma of 0.01
 C103-C108
 1.56 with sigma of 0.01
 C070-C147
 1.56 with sigma of 0.01
 C020-C034
 1.56 with sigma of 0.01
 C116-C146
 1.55 with sigma of 0.01
 C036-C066
 1.55 with sigma of 0.01
 C117-C122
 1.55 with sigma of 0.01
 C039-C061
 1.55 with sigma of 0.01
 C024-C025
 1.55 with sigma of 0.008
 C139-C150
 1.55 with sigma of 0.008
 C011-C013
 1.55 with sigma of 0.008
 C064-C114
 1.55 with sigma of 0.005
 C081-C088
 1.55 with sigma of 0.005
 C025-C024
 1.39 with sigma of 0.01
 C034-C020
 1.54 with sigma of 0.01
 C129-C070
 1.39 with sigma of 0.01
 C108-C103
 1.39 with sigma of 0.01
 H19C_$1-H16N
 2.15 with sigma of 0.01
 C013-C011
 1.54 with sigma of 0.005
 C146-C116
 1.39 with sigma of 0.01
 C063-C048
 1.39 with sigma of 0.01
 C196-C187
 2.3 with sigma of 0.01
 C150-C139
 1.54 with sigma of 0.01
 C182-C170 \\sim C186-C182 \\sim C182-C178 \\sim C186-C163 \\sim C178-C163
\\sim C163-C110 \\sim C191-
 C170 \\sim C199-C170 \\sim C199-C158 \\sim C191-C158 \\sim C158-C124 \\sim
C192-C157 \\sim C203-C192 ~
 C203-C194 \\sim C196-C194 \\sim C30-C196 \\sim C30-C187 \\sim C187-C152 \\sim
C138-C055 \\sim C138-
 C111 \\sim C125-C111 \\sim C168-C125 \\sim C177-C168 \\sim C177-C173 \\sim
C173-C112 \\sim C166-C159 ~
 C181-C166 \\sim C181-C174 \\sim C180-C174 \\sim C180-C176 \\sim C189-C176
\\sim C189-C135 \\sim C161-
 C120 \\sim C161-C160 \\sim C160-C130 \\sim C145-C130 \\sim C164-C145 \\sim
C164-C149 \\sim C149-C115 ~
 C183-C052 \\sim C193-C183 \\sim C193-C188 \\sim C188-C179 \\sim C179-C175
\\sim C175-C155 \\sim C155-
 C151
 with sigma of 0.01
4. Rigid bond restraints
 C152, C187
 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 -2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within -2A
6. Others
 Fixed Sof: H15G(0.5) H15H(0.5) H15E(0.5) H15F(0.5) H16A(0.5) H16B(0.5)
 H16C(0.5) H16D(0.5) H17C(0.5) H17D(0.5) H17A(0.5) H17B(0.5) C178(0.5)
 H17I(0.5) H17J(0.5) H18A(0.5) H18B(0.5) H18C(0.5) H18D(0.5) C186(0.5)
 H18E(0.5) H18F(0.5) C191(0.5) H19A(0.5) H19B(0.5) C199(0.5) H19I(0.5) H19J(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C052(H05C,H05D), C055(H05A,H05B), C110(H11A,H11B), C111(H11C,H11D), C112(H11E,
 H11F), C115(H11G,H11H), C120(H12E,H12F), C124(H12A,H12B), C125(H12C,H12D),
 C130(H13C,H13D), C135(H13E,H13F), C138(H13A,H13B), C145(H14A,H14B), C149(H14C,
 H14D), C151(H15I,H15J), C152(H15A,H15B), C155(H15K,H15L), C157(H15C,H15D),
 C158(H15G,H15H), C158(H15E,H15F), C159(H15M,H15N), C160(H16G,H16H), C161(H16I,
 H16J), C163(H16A,H16B), C163(H16C,H16D), C164(H16K,H16L), C166(H16M,H16N),
 C168(H16E,H16F), C170(H17C,H17D), C170(H17A,H17B), C173(H17E,H17F), C174(H17K,
 H17L), C175(H17M,H17N), C176(H17O,H17P), C177(H17G,H17H), C178(H17I,H17J),
 C179(H17Q,H17R), C180(H18I,H18J), C181(H18K,H18L), C182(H18A,H18B), C182(H18C,
 H18D), C183(H18M,H18N), C186(H18E,H18F), C187(H18G,H18H), C188(H18O,H18P),
 C189(H18Q,H18R), C191(H19A,H19B), C192(H19C,H19D), C193(H19K,H19L), C194(H19E,
 H19F), C196(H19G,H19H), C199(H19I,H19J), C203(H20A,H20B), C30(H30A,H30B)
7.b Aromatic/amide H refined with riding coordinates:
 C014(H014), C017(H017), C038(H038), C044(H044), C046(H046), C049(H049),
 C054(H054), C060(H060), C147(H147), C117(H117), C122(H122), C073(H073),
 C075(H075), C078(H078), C080(H080), C083(H083), C086(H086), C090(H090),
 C093(H093), C095(H095), C096(H096), C097(H097), C098(H098), C101(H101),
 C109(H109), C113(H113), C114(H114), C118(H118), C119(H119), C123(H123),
 C126(H126), C127(H127), C128(H128), C132(H132), C133(H133), C136(H136),
 C140(H140), C141(H141), C142(H142), C143(H143), C144(H144), C148(H148),
 C153(H153), C156(H156), C165(H165), C167(H167), C169(H169), C171(H171)
7.c Fitted hexagon refined as free rotating group:
 C070(C147,C104,C117,C122,C072)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'