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_1576037
_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         '3(C H2 Cl2), 2(C84 H72 N6 O6), C6 H14'
_chemical_formula_sum            'C177 H164 Cl6 N12 O12'
_chemical_formula_weight         2863.89
_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             2024-12-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-04-03 deposited with the CCDC.	2025-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                68.118(3)
_cell_angle_beta                 83.583(3)
_cell_angle_gamma                74.293(3)
_cell_formula_units_Z            1
_cell_length_a                   17.3955(11)
_cell_length_b                   17.9852(12)
_cell_length_c                   19.2333(13)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      37.64
_cell_measurement_theta_min      3.13
_cell_volume                     5374.9(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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_av_unetI/netI     0.1341
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            155285
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.216
_diffrn_source_current           3.58
_diffrn_source_power             0.250421
_diffrn_source_voltage           69.95
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    0.885
_exptl_crystal_description       block
_exptl_crystal_F_000             1508
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 6143 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.46(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1686
_refine_ls_number_reflns         36283
_refine_ls_number_restraints     4911
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.1592
_refine_ls_R_factor_gt           0.0848
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1601P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2221
_refine_ls_wR_factor_ref         0.2654
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.832
_reflns_number_gt                17090
_reflns_number_total             36283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06445g2.cif
_cod_data_source_block           241203b_wenjing_0m
_cod_depositor_comments
'Adding full bibliography for 1576037--1576039.cif.'
_cod_database_code               1576037
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. 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
2. Restrained distances
 C04C-C38
 2.54 with sigma of 0.01
 C01R-C010
 1.55 with sigma of 0.001
 C04Q-C03Y
 1.55 with sigma of 0.001
 C00T-C00R
 1.55 with sigma of 0.001
 C011-C00Z
 1.55 with sigma of 0.001
 C024-C012
 1.55 with sigma of 0.001
 C02E-C02A
 1.55 with sigma of 0.001
 C03Q-C02W
 1.55 with sigma of 0.001
 C061-C04S
 2.65 with sigma of 0.01
 C05R-C05W
 2.58 with sigma of 0.01
 C046-C019
 1.55 with sigma of 0.001
 C04K-C02Y \\sim C04K-C02G \\sim C041-C02G \\sim C04Y-C041 \\sim C057-C04Y
\\sim C057-C04V \\sim C04V-
 C00Y \\sim C04L-C02X \\sim C04M-C04L \\sim C04M-C03P \\sim C03P-C02R \\sim
C04B-C02R \\sim C04U-C04B ~
 C04U-C04A \\sim C056-C04I \\sim C056-C052 \\sim C05L-C052 \\sim C05L-C059
\\sim C05B-C059 \\sim C05F-
 C05B \\sim C05F-C050
 with sigma of 0.008
 C05W-C038 \\sim C05W-C05I \\sim C05R-C05I \\sim C05R-C04Z \\sim C38-C04Z \\sim
C38-C05D \\sim C05D-
 C04C \\sim C03R-C015 \\sim C04X-C03R \\sim C04X-C04T \\sim C05K-C04T \\sim
C061-C05K \\sim C061-C05Y ~
 C05Y-C04S \\sim C05O-C02S \\sim C05O-C05H \\sim C29-C05H \\sim C29-C05P \\sim
C05P-C04D \\sim C05S-
 C04D \\sim C05S-C051
 with sigma of 0.008
 Cl6-C50 \\sim Cl5-C50 \\sim Cl3-C05A \\sim Cl4-C05A \\sim Cl1-C14 \\sim Cl2-C14
 with sigma of 0.008
 C26-C22 \\sim C25-C22 \\sim C25-C12 \\sim C17-C12 \\sim C7-C17
 with sigma of 0.008
3. 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
4.a Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C015(H01B,H01D), C02G(H02A,H02B), C02R(H02C,H02D), C02S(H02P,
 H02Q), C02X(H02E,H02F), C02Y(H02G,H02H), C038(H03E,H03F), C03P(H03A,H03C),
 C03R(H03G,H03J), C041(H04A,H04B), C04A(H04C,H04D), C04B(H04E,H04I), C04C(H04Z,
 H), C04D(H04,HA), C04I(H04J,H04K), C04K(H04L,H04M), C04L(H04N,H04O), C04M(H04P,
 H04Q), C04S(H2,HB), C04T(H3,HC), C04U(H04R,H04S), C04V(H04T,H04U), C04X(H4,HD),
  C04Y(H04V,H04W), C04Z(H5,HE), C050(H05A,H05B), C051(H05Q,H05R), C052(H05C,
 H05D), C056(H05E,H05F), C057(H05G,H05H), C059(H05I,H05J), C05A(H10,HF),
 C05B(H05K,H05L), C05D(H05S,H05T), C05F(H05M,H05N), C05H(H05U,H05V), C05I(H05W,
 H05X), C05K(H05Y,HG), C05L(H05O,H05P), C05O(H05Z,HH), C05P(H05,HI), C05R(H6,
 HJ), C05S(H7,HK), C05W(H8,HL), C05Y(H9,HM), C061(H06A,H06B), C29(H29A,H29B),
 C38(H38A,H38B), C12(H12A,H12B), C14(H14A,H14B), C17(H17A,H17B), C22(H22A,H22B),
  C25(H25A,H25B), C50(H50A,H50B)
4.b Aromatic/amide H refined with riding coordinates:
 C00U(H00U), C034(H034), C01L(H01L), C02B(H02J), C04J(H04X), C040(H040),
 C02O(H02O), C04N(H04Y), C026(H026), C01C(H01C), C047(H047), C016(H016),
 C014(H014), C01I(H01I), C03U(H03U), C03O(H03O), C018(H018), C02Z(H02Z),
 C04F(H04F), C02L(H02L), C01A(H01A), C031(H031), C01E(H01E), C029(H029),
 C03H(H03H), C04H(H04H), C02M(H02M), C03V(H03V), C01H(H01H), C01K(H01K),
 C02D(H02K), C01O(H01O), C03I(H03I), C03K(H03K), C01T(H01T), C01U(H01U),
 C039(H039), C03B(H03B), C030(H030), C03A(H03D), C03X(H03X), C01Y(H01Y),
 C02V(H02V), C04G(H04G), C02I(H02I), C02J(H02N), C04E(H1), C03W(H03W)
4.c Fitted hexagon refined as free rotating group:
 C00U(C02K,C04O,C034,C02W,C01L), C00Z(C02B,C02U,C044,C04J,C040), C011(C02O,
 C04N,C04Q,C03Z,C026), C012(C01C,C03F,C048,C047,C016), C017(C01I,C01R,C01N,C03U,
 C03O), C019(C02Z,C04F,C02E,C02L,C022), C01A(C023,C046,C031,C02P,C033),
 C01E(C029,C03N,C036,C03H,C02H), C01F(C03E,C04H,C024,C02M,C03V), C01K(C02T,C027,
 C02D,C035,C01X), C01P(C01O,C03I,C03J,C03K,C02N), C01U(C039,C02A,C03B,C01J,
 C03M), C01V(C021,C030,C03Q,C03A,C03X), C02F(C02V,C01G,C00W,C04G,C01W),
 C04E(C03G,C049,C03W,C01D,C03Y)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C26(H26A,H26B,H26C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'