Observation of shuttling on the one-second timescale in a [10]cycloparaphenylene/C<sub>60</sub> [2]catenane.
Steudel, Fabian M.; Sabrià, Clara; Piane, Massimo Delle; Feixas, Ferran; Ribas, Xavi; Pavan, Giovanni M.; von Delius, Max; Chemical science 16 (2025) 21908–21916; doi:10.1039/d5sc05734e

data_1575927
_publ_section_title
;
 Observation of shuttling on the one-second timescale in a
 [10]cycloparaphenylene/C<sub>60</sub> [2]catenane.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              21908
_journal_page_last               21916
_journal_paper_doi               10.1039/d5sc05734e
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C85.88 H16.907 O8, C60 H40'
_chemical_formula_sum            'C149.83 H60.86 Cl11.85 O8'
_chemical_formula_weight         2408.88
_chemical_name_systematic
'Co-crystal of [10]cycloparaphenylene and in,in-trans-3 bis(methyl (4-ethynylbenzyl) malonato)-C60'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2025-04-03
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-05-02 deposited with the CCDC.	2025-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.963(5)
_cell_angle_beta                 94.519(5)
_cell_angle_gamma                97.050(5)
_cell_formula_units_Z            2
_cell_length_a                   15.9594(12)
_cell_length_b                   16.2718(12)
_cell_length_c                   20.8553(15)
_cell_measurement_reflns_used    8725
_cell_measurement_temperature    161.00
_cell_measurement_theta_max      66.492
_cell_measurement_theta_min      2.737
_cell_volume                     5356.3(7)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      161.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2425
_diffrn_reflns_av_unetI/netI     0.1141
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            164702
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.790
_diffrn_reflns_theta_max         66.790
_diffrn_reflns_theta_min         2.126
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    3.356
_exptl_absorpt_correction_T_max  0.7472
_exptl_absorpt_correction_T_min  0.6787
_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 dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             2451
_exptl_crystal_preparation
'A 2:1 mixture of the fullerene bis-adduct and [10]cycloparaphenylene was dissolved in CDCl3, and 1,2,4,5-tetramethylbenzene was added as an internal standard for NMR analysis.'
_exptl_crystal_recrystallization_method 'slow evaporation from NMR tube'
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.00154(14)
_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   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1456
_refine_ls_number_reflns         18955
_refine_ls_number_restraints     3542
_refine_ls_restrained_S_all      0.858
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0816
_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^)+(0.1330P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2119
_refine_ls_wR_factor_ref         0.2590
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8654
_reflns_number_total             18955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05734e3.cif
_cod_data_source_block           2024s032_fst_b1_230_sm_tmb
_cod_depositor_comments
'Adding full bibliography for 1575925--1575927.cif.'
_cod_database_code               1575927
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.845
_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
 O02F-C02Q \\sim O02G-C02Q
 with sigma of 0.02
 C02Q-O03O \\sim C02Q-O03P
 with sigma of 0.02
 O03O-C6 \\sim O03P-C6A
 with sigma of 0.02
 C02Q-C6 \\sim C02Q-C6A
 with sigma of 0.04
 C01W-C1 \\sim C01W-C1A
 with sigma of 0.02
 C1-O2 \\sim C1A-O2A
 with sigma of 0.02
 C1-O3 \\sim C1A-O3A
 with sigma of 0.02
 O3-C4 \\sim O3A-C4A
 with sigma of 0.02
 C01W-O2 \\sim C01W-O2A
 with sigma of 0.04
 C01W-O3 \\sim C01W-O3A
 with sigma of 0.04
 C1-C4 \\sim C1A-C4A
 with sigma of 0.04
 O2-O3 \\sim O2A-O3A
 with sigma of 0.04
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(O03P)=Sof(O02G)=1-FVAR(1)
 Sof(O02F)=Sof(O03O)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=FVAR(1)
 Sof(C02G)=Sof(H02A)=Sof(H02B)=Sof(C03D)=Sof(H03D)=Sof(C03E)=Sof(C042)=
 Sof(H042)=Sof(C043)=Sof(H043)=Sof(C04A)=Sof(C04B)=Sof(H04B)=Sof(C04K)=
 Sof(C04N)=Sof(H04N)=FVAR(2)
 Sof(O2A)=Sof(C1A)=Sof(O3A)=Sof(C4A)=1-FVAR(3)
 Sof(C1)=Sof(O2)=Sof(O3)=Sof(C4)=FVAR(3)
7.a Secondary CH2 refined with riding coordinates:
 C02G(H02A,H02B), C02X(H02C,H02D)
7.b Aromatic/amide H refined with riding coordinates:
 C023(H023), C024(H024), C026(H026), C029(H029), C02C(H02E), C02E(H02F),
 C02H(H02H), C02I(H02I), C02J(H02J), C02K(H02K), C02N(H02N), C02O(H02O),
 C02P(H02P), C02R(H02R), C02S(H02S), C02V(H02V), C02Y(H02Y), C02Z(H02Z),
 C031(H031), C032(H032), C036(H036), C038(H038), C03A(H03A), C03B(H03B),
 C03C(H03C), C03D(H03D), C03G(H03G), C03H(H03H), C03J(H03J), C03L(H03L),
 C03M(H03M), C03P(H03P), C03R(H03R), C03S(H03S), C03T(H03T), C03U(H03U),
 C03W(H03W), C03Z(H03Z), C041(H041), C042(H042), C043(H043), C044(H044),
 C045(H045), C046(H046), C047(H047), C048(H048), C04B(H04B), C04C(H04C)
7.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC)
7.d :
 C04I(H04I), C04N(H04N)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              55651
_shelx_fab_checksum              82038
_olex2_date_sample_data_collection 2024-12-11
_olex2_date_sample_submission    2024-12-10
_olex2_exptl_crystal_mounting_method
'The crystal was mounted in inert oil and transferred to the cold nitrogen gas stream of the diffractometer.'
_olex2_submission_original_sample_id 2024S032_FSt_B1_230_SM_TMB
_olex2_submission_special_instructions 'No special instructions were received'