Crown ether-cycloparaphenylene hybrid multimacrocycles: insights into supramolecular gas sensing and biological potential.
Hu, Yaning; Li, Tong; Su, Taotao; Shi, Wudi; Yu, Yabing; Li, Beibei; Li, Meng-Hua; Zhang, Sheng; Xu, Yuan-Qing; Liu, Qi; Wu, Di; Xu, Youzhi; Chemical science 16 (2025) 13115–13121; doi:10.1039/d5sc03476k

data_1574889
_publ_section_title
;
 Crown ether-cycloparaphenylene hybrid multimacrocycles: insights into
 supramolecular gas sensing and biological potential.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              13115
_journal_page_last               13121
_journal_paper_doi               10.1039/d5sc03476k
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety
'C66 H57 K O8, C66 H59 K O8, 2(F6 P), 4(C H Cl3)'
_chemical_formula_sum            'C136 H120 Cl12 F12 K2 O16 P2'
_chemical_formula_weight         2803.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2lbmbx
_audit_creation_date             2024-04-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-10-24 deposited with the CCDC.	2025-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.914(16)
_cell_length_b                   23.096(14)
_cell_length_c                   25.886(18)
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      53.161
_cell_measurement_theta_min      3.219
_cell_volume                     13699(16)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            68112
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        54.582
_diffrn_reflns_theta_max         54.582
_diffrn_reflns_theta_min         2.716
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    3.638
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             5776
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.943
_refine_diff_density_min         -1.334
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.36(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1617
_refine_ls_number_reflns         15727
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0755
_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^)+(0.1671P)^2^+6.2429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2215
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                12764
_reflns_number_total             15727
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03476k2.cif
_cod_data_source_block           m13104_0m_a
_cod_depositor_comments
'Adding full bibliography for 1574889--1574890.cif.'
_cod_database_code               1574889
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.712
_shelx_estimated_absorpt_t_min   0.611
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.64(2)
 0.36(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C256(H256), C266(H266), C274(H274), C272(H272)
3.b Secondary CH2 refined with riding coordinates:
 C68(H68A,H68B), C77(H77A,H77B), C108(H10A,H10B), C148(H14A,H14B), C165(H16C,
 H16D), C182(H18A,H18B), C205(H20C,H20D), C208(H20E,H20F), C223(H22A,H22B),
 C234(H23E,H23F), C251(H25E,H25F), C112(H11A,H11B), C122(H12A,H12B), C138(H13A,
 H13B), C156(H15A,H15B), C169(H16A,H16B), C202(H20A,H20B), C237(H23A,H23B),
 C239(H23C,H23D), C242(H24A,H24B), C248(H24C,H24D), C258(H25A,H25B), C259(H25C,
 H25D), C268(H26A,H26B)
3.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C26(H26), C27(H27), C39(H39), C59(H59), C62(H62),
 C65(H65), C66(H66), C74(H74), C80(H80), C93(H93), C96(H96), C103(H103),
 C116(H116), C125(H125), C127(H127), C134(H134), C137(H137), C149(H149),
 C163(H163), C188(H188), C189(H189), C191(H191), C193(H193), C194(H194),
 C198(H198), C201(H201), C206(H206), C207(H207), C217(H217), C220(H220),
 C225(H225), C241(H241), C255(H255), C10(H10), C17(H17), C33(H33), C37(H37),
 C40(H40), C64(H64), C99(H99), C100(H100), C115(H115), C117(H117), C121(H121),
 C132(H132), C141(H141), C166(H166), C179(H179), C180(H180), C184(H184),
 C186(H186), C200(H200), C209(H209), C211(H211), C212(H212), C213(H213),
 C215(H215), C224(H224), C226(H226), C228(H228), C230(H230), C233(H233),
 C246(H246), C261(H261), C264(H264), C273(H273)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              85186
_shelx_fab_checksum              17925
_olex2_submission_special_instructions 'No special instructions were received'