A self-assembled macrocycle with a non-closed structure for hierarchically upgraded self-assembly
Cao, Ze; Ge, Chenqi; Wu, Guangcheng; Tang, Hua; Wu, Yating; Kuang, Yueyan; Lu, Yuyang; Liu, Jiyong; Li, Hao; Chemical Science  (2025) –; doi:10.1039/D5SC06544E

data_1576238
_publ_section_title
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 A self-assembled macrocycle with a non-closed structure for
 hierarchically upgraded self-assembly
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC06544E
_journal_year                    2025
_chemical_formula_moiety         '8(C H Cl3), 3(C5 H12 O), C132 H146 N20'
_chemical_formula_sum            'C155 H190 Cl24 N20 O3'
_chemical_formula_weight         3232.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2025-10-06
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-10-07 deposited with the CCDC.	2025-10-28 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 96.835(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0151(11)
_cell_length_b                   28.0832(15)
_cell_length_c                   28.4875(15)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      37.430
_cell_measurement_theta_min      3.043
_cell_volume                     16693.0(15)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III M28'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON III'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1602
_diffrn_reflns_av_unetI/netI     0.1766
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            102816
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        48.435
_diffrn_reflns_theta_max         48.435
_diffrn_reflns_theta_min         1.929
_diffrn_source                   'liquid Metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_type              'Bruker Excillum Metaljet D2+'
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    2.722
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_correction_T_min  0.5996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1219 before and 0.0881 after correction.
The Ratio of minimum to maximum transmission is 0.8000.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       needle
_exptl_crystal_F_000             6768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1837
_refine_ls_number_reflns         24037
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.2148
_refine_ls_R_factor_gt           0.1060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1979P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2687
_refine_ls_wR_factor_ref         0.3458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10785
_reflns_number_total             24037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06544e2.cif
_cod_data_source_block           250423_cz_mzr
_cod_database_code               1576238
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.640
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1A
 0.89 with sigma of 0.001
 C150-O3
 1.53 with sigma of 0.01
 N1-H1B
 0.89 with sigma of 0.001
 N20-H20B
 0.89 with sigma of 0.001
 N20-H20A
 0.89 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
O1 \\sim C133 \\sim C136 \\sim C138 \\sim C141 \\sim C144 \\sim O2 \\sim C147
\\sim C151 \\sim C152 \\sim C153 \\sim C154 \\sim O3 \\sim C140 \\sim C146
\\sim C148 \\sim C149 \\sim C150: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4.a Everything fixed:
 H20A, H20B
4.b Ternary CH refined with riding coordinates:
 C135(H135), C143(H143), C142(H142), C134(H134), C155(H155), C139(H139),
 C137(H137), C145(H145), C1(H1), C6(H6), C15(H15), C16(H16), C29(H29), C30(H30),
  C43(H43), C44(H44), C57(H57), C58(H58), C71(H71), C72(H72), C85(H85),
 C86(H86), C105(H105), C106(H106), C119(H119), C120(H120), C127(H127),
 C128(H128)
4.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B), C20(H20C,H20D), C31(H31A,H31B), C32(H32A,H32B),
 C33(H33A,H33B), C34(H34A,H34B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B),
  C48(H48A,H48B), C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B), C62(H62A,
 H62B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B), C76(H76A,H76B),
 C87(H87A,H87B), C88(H88A,H88B), C89(H89A,H89B), C90(H90A,H90B), C107(H10A,
 H10B), C108(H10C,H10D), C109(H10E,H10F), C110(H11A,H11B), C121(H12A,H12B),
 C122(H12C,H12D), C123(H12E,H12F), C124(H12G,H12H), C129(H12I,H12J), C130(H13A,
 H13B), C131(H13C,H13D), C132(H13E,H13F)
4.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C13(H13), C14(H14), C21(H21), C23(H23), C25(H25), C27(H27),
 C28(H28), C35(H35), C37(H37), C39(H39), C41(H41), C42(H42), C49(H49), C51(H51),
  C54(H54), C56(H56), C63(H63), C65(H65), C67(H67), C69(H69), C70(H70),
 C77(H77), C79(H79), C81(H81), C83(H83), C84(H84), C91(H91), C93(H93), C96(H96),
  C99(H99), C101(H101), C103(H103), C104(H104), C111(H111), C113(H113),
 C115(H115), C117(H117), C118(H118), C125(H125), C126(H126)
4.e Idealised Me refined as rotating group:
 C136(H13G,H13H,H13I), C138(H13J,H13K,H13L), C141(H14A,H14B,H14C), C144(H14D,
 H14E,H14F), C151(H15A,H15B,H15C), C152(H15D,H15E,H15F), C153(H15G,H15H,H15I),
 C154(H15J,H15K,H15L), C140(H14G,H14H,H14I), C146(H14J,H14K,H14L), C148(H14M,
 H14N,H14O), C150(H15M,H15N,H15O)
;
_shelx_res_checksum              46039
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'