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_1574890
_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_formula_moiety         '1(C66 H58 O8), 0.5(C7 H7), 1.5(C7 H8)'
_chemical_formula_sum            'C80 H73.5 O8'
_chemical_formula_weight         1162.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2lbmcy
_audit_creation_date             2024-03-04
_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                 106.434(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.9739(14)
_cell_length_b                   21.8794(13)
_cell_length_c                   27.0805(16)
_cell_measurement_reflns_used    12422
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      65.285
_cell_measurement_theta_min      2.096
_cell_volume                     12487.7(13)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.1008
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            112251
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        65.285
_diffrn_reflns_theta_max         65.285
_diffrn_reflns_theta_min         2.096
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.1621
_exptl_absorpt_correction_T_min  0.0635
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             4940
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1597
_refine_ls_number_reflns         21290
_refine_ls_number_restraints     170
_refine_ls_restrained_S_all      1.277
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.1140
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3217
_refine_ls_wR_factor_ref         0.3659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12422
_reflns_number_total             21290
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03476k2.cif
_cod_data_source_block           m13194_0m
_cod_depositor_comments
'Adding full bibliography for 1574889--1574890.cif.'
_cod_original_formula_sum        'C80 H73.50 O8'
_cod_database_code               1574890
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.876
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O00G-C04G \\sim O00G-C3
 with sigma of 0.02
 C03M-C04G \\sim C03M-C3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C04A \\sim C049 \\sim C04B \\sim C03W \\sim C03I \\sim C044 \\sim C2: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C2) \\sim Ueq, Uanis(C049) \\sim Ueq, Uanis(C044) \\sim Ueq, Uanis(C03I)
\\sim Ueq, Uanis(C03W) \\sim Ueq, Uanis(C04B) \\sim Ueq, Uanis(C04A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C04I) \\sim Ueq, Uanis(C04Q) \\sim Ueq, Uanis(C04U) \\sim Ueq,
Uanis(C04O) \\sim Ueq, Uanis(C04M) \\sim Ueq, Uanis(C04H) \\sim Ueq,
Uanis(C04V) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C04P) \\sim Ueq, Uanis(C04K) \\sim Ueq, Uanis(C04R) \\sim Ueq,
Uanis(C04T) \\sim Ueq, Uanis(C04S) \\sim Ueq, Uanis(C04L) \\sim Ueq,
Uanis(C04N) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H03F)=Sof(H03G)=Sof(C3)=Sof(H3A)=Sof(H3B)=1-FVAR(1)
 Sof(H03C)=Sof(H03D)=Sof(C04G)=Sof(H04M)=Sof(H04N)=FVAR(1)
 Fixed Sof: C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C1(0.5) H1A(0.5) H1B(0.5)
 H1C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C02B(H02G,H02H), C02G(H02I,H02J), C02S(H02L,H02N), C02Z(H02B,H02D), C03A(H03A,
 H03B), C03B(H03M,H03N), C03C(H03O,H03P), C03G(H03T,H03U), C03J(H03V,H03W),
 C03K(H03X,H03Y), C03M(H03C,H03D), C03M(H03F,H03G), C03O(H03I,H03J), C03R(H2,H),
  C03Y(H4,HA), C03Z(H03K,H03L), C042(H04A,H04B), C045(H04C,H04D), C046(H04O,
 H04P), C048(H04E,H04F), C04C(H04G,H04H), C04D(H04Q,H04R), C04E(H04I,H04J),
 C04F(H04K,H04L), C04G(H04M,H04N), C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00J(H00J), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00U(H00U), C00X(H00X), C010(H010), C012(H012), C015(H015), C016(H016),
 C017(H017), C01A(H01A), C01E(H01E), C01F(H01F), C01H(H01H), C01J(H01J),
 C01K(H01K), C01M(H01M), C01O(H01O), C01P(H01P), C01R(H01R), C01S(H01S),
 C01T(H01T), C01U(H01U), C01X(H01X), C01Y(H01Y), C021(H021), C022(H022),
 C023(H023), C024(H024), C026(H026), C028(H028), C02A(H02A), C02C(H02C),
 C02E(H02E), C02F(H02F), C02H(H02K), C02M(H02M), C02P(H02P), C02Q(H02Q),
 C02R(H02R), C02T(H02T), C02U(H02U), C02V(H02V), C02W(H02W), C02X(H02X),
 C02Y(H02Y), C030(H030), C031(H031), C032(H032), C033(H033), C034(H034),
 C035(H035), C037(H037), C038(H038), C039(H039), C03D(H03Q), C03E(H03E),
 C03F(H03R), C03H(H03H), C03I(H5), C03L(H03Z), C03N(H03), C03P(H1), C03S(H03S),
 C03T(H3), C03V(H7), C03W(H6), C03X(H8), C040(H040), C041(H041), C043(H043),
 C044(H044), C047(H047), C04B(H04S), C04H(H04W), C04M(H04X), C04O(H04Y),
 C04U(H04Z), C04Q(H04), C04L(H10), C04N(H11), C04R(H13), C04S(H14), C04T(H15)
5.c Fitted hexagon refined as free rotating group:
 C04I(C04H,C04M,C04O,C04U,C04Q)
5.d Idealised Me refined as rotating group:
 C04J(H04T,H04U,H04V), C04P(H12,HB,HC), C04V(H9,HD,HE), C2(H2A,H2B,H2C),
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              16800
_olex2_submission_special_instructions 'No special instructions were received'