A translationally active ligand based on a [2]rotaxane molecular shuttle with a 2,2'-bipyridyl core.
Dhara, Ayan; Dmitrienko, Anton; Hussein, Rahaf N.; Sotomayor, Ariel; Wilson, Benjamin H.; Loeb, Stephen J.; Chemical science 14 (2023) 7215–7220; doi:10.1039/d3sc01346d

data_1569451
_publ_section_title
;
 A translationally active ligand based on a [2]rotaxane molecular shuttle
 with a 2,2'-bipyridyl core.
;
_journal_issue                   26
_journal_name_full               'Chemical science'
_journal_page_first              7215
_journal_page_last               7220
_journal_paper_doi               10.1039/d3sc01346d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C16 H32 O8, C64 H64 N6'
_chemical_formula_sum            'C80 H96 N6 O8'
_chemical_formula_weight         1269.62
_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
_audit_creation_date             2023-02-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                86.179(2)
_cell_angle_beta                 74.935(2)
_cell_angle_gamma                80.127(2)
_cell_formula_units_Z            2
_cell_length_a                   14.9954(6)
_cell_length_b                   16.1533(7)
_cell_length_c                   20.1627(9)
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.428
_cell_volume                     4645.0(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            254110
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         1.834
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.7434
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0936 before and 0.0775 after correction. The Ratio of minimum to maximum transmission is 0.9416. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.908
_exptl_crystal_description       block
_exptl_crystal_F_000             1364
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene - diethyl ether'
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     884
_refine_ls_number_reflns         22158
_refine_ls_number_restraints     872
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.1078
_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^)+(0.1215P)^2^+5.0706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2715
_refine_ls_wR_factor_ref         0.2815
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17534
_reflns_number_total             22158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01346d2.cif
_cod_data_source_block           ayan_2_0m
_cod_depositor_comments
'Adding full bibliography for 1569451--1569452.cif.'
_cod_database_code               1569451
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.985
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C71-C72
 2.36 with sigma of 0.02
 C71B-C72B
 2.36 with sigma of 0.001
 C72B-O3B
 0.001 with sigma of 1.4
 C72-C71
 2.285 with sigma of 0.02
 C72B-O3 \\sim O3-C71
 with sigma of 0.001
 C70-C71 \\sim C70-C71B
 with sigma of 0.02
 O3-C72B \\sim O3B-C72B
 with sigma of 0.02
 C70-O3 \\sim C70-O3B
 with sigma of 0.04
 C72B-C71 \\sim C72B-C71B
 with sigma of 0.04
 C71B-C70 \\sim C70-C71
 with sigma of 0.001
 C30-C31 \\sim C30-C32B
 with sigma of 0.02
 C30-C33 \\sim C30-C31B
 with sigma of 0.02
 C30-C32 \\sim C30-C33B
 with sigma of 0.02
 O2-C70 \\sim O2B-C70
 with sigma of 0.02
 O2-C69 \\sim O2B-C69B
 with sigma of 0.02
 C68-C69 \\sim C68-C69B
 with sigma of 0.02
 O2-C68 \\sim O2B-C68
 with sigma of 0.04
 C70-C69 \\sim C70-C69B
 with sigma of 0.04
 O2B-C70 \\sim C70-O2
 with sigma of 0.001
 C69-O2 \\sim C69B-O2B
 with sigma of 0.001
 C73-C72B \\sim C73-C72
 with sigma of 0.02
 O3-C72B \\sim O3-C72
 with sigma of 0.02
 C72B-O3B \\sim C72-O3B
 with sigma of 0.02
 O3B-C72B \\sim O3-C72
 with sigma of 0.001
 C72B-C73 \\sim C73-C72
 with sigma of 0.001
 O7-C79 \\sim O7B-C79
 with sigma of 0.02
 O7-C80 \\sim O7B-C80B
 with sigma of 0.02
 C81-C80 \\sim C81-C80B
 with sigma of 0.02
 O7-C81 \\sim O7B-C81
 with sigma of 0.04
 C79-C80 \\sim C79-C80B
 with sigma of 0.04
 C80-C81 \\sim C81-C80B
 with sigma of 0.001
 O7B-C79 \\sim C79-O7
 with sigma of 0.001
 C72-O3 \\sim O3-C71
 with sigma of 0.001
 O3-C71 \\sim O3B-C71B
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C71B) = Uanis(C71)
Uanis(O3) = Uanis(O3B)
Uanis(C31) = Uanis(C32B) = Uanis(C32) = Uanis(C33B) = Uanis(C33) = Uanis(C31B)
Uanis(C69) = Uanis(C69B)
Uanis(O2) = Uanis(O2B)
Uanis(C72) = Uanis(C72B)
Uanis(O7) = Uanis(O7B)
Uanis(C80B) = Uanis(C80)
Uanis(C80) = Uanis(C80B)
4. 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
5. Others
 Sof(H73C)=Sof(H73D)=Sof(O3B)=Sof(C71B)=Sof(H71C)=Sof(H71D)=Sof(C72B)=
 Sof(H72C)=Sof(H72D)=1-FVAR(1)
 Sof(H73A)=Sof(H73B)=Sof(O3)=Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(C72)=Sof(H72A)=
 Sof(H72B)=FVAR(1)
 Sof(C31B)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C32B)=Sof(H32D)=Sof(H32E)=
 Sof(H32F)=Sof(C33B)=Sof(H33D)=Sof(H33E)=Sof(H33F)=1-FVAR(2)
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=
 Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(2)
 Sof(H68C)=Sof(H68D)=Sof(H70D)=Sof(H70C)=Sof(O2B)=Sof(C69B)=Sof(H69C)=
 Sof(H69D)=1-FVAR(3)
 Sof(H68A)=Sof(H68B)=Sof(H70B)=Sof(H70A)=Sof(O2)=Sof(C69)=Sof(H69A)=Sof(H69B)=
 FVAR(3)
 Sof(H79C)=Sof(H79D)=Sof(H81C)=Sof(H81D)=Sof(O7B)=Sof(C80B)=Sof(H80C)=
 Sof(H80D)=1-FVAR(4)
 Sof(H79A)=Sof(H79B)=Sof(H81A)=Sof(H81B)=Sof(O7)=Sof(C80)=Sof(H80A)=Sof(H80B)=
 FVAR(4)
 Fixed Sof: H5(0.5) H6(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C66(H66A,H66B), C67(H67A,H67B), C68(H68A,H68B), C68(H68C,H68D), C70(H70B,
 H70A), C70(H70D,H70C), C73(H73A,H73B), C73(H73C,H73D), C74(H74A,H74B),
 C75(H75A,H75B), C76(H76A,H76B), C77(H77A,H77B), C78(H78A,H78B), C79(H79A,H79B),
  C79(H79C,H79D), C81(H81A,H81B), C81(H81C,H81D), C69(H69A,H69B), C71(H71A,
 H71B), C72(H72A,H72B), C80(H80A,H80B), C69B(H69C,H69D), C71B(H71C,H71D),
 C72B(H72C,H72D), C80B(H80C,H80D)
6.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), N6(H6), C2(H2A), C3(H3), C5(H5A), C10(H10), C11(H11),
 C14(H14), C15(H15), C17(H17), C18(H18), C25(H25), C26(H26), C28(H28), C29(H29),
  C35(H35), C36(H36), C38(H38), C43(H43), C44(H44), C47(H47), C48(H48),
 C50(H50), C51(H51), C57(H57), C58(H58), C60(H60), C61(H61)
6.c Idealised Me refined as rotating group:
 C01U(H01A,H01B,H01C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C64(H64A,
 H64B,H64C), C65(H65A,H65B,H65C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C),
 C33(H33A,H33B,H33C), C31B(H31D,H31E,H31F), C32B(H32D,H32E,H32F), C33B(H33D,
 H33E,H33F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              95288
_shelx_fab_checksum              68578
_olex2_exptl_crystal_mounting_method
'on a glass microloop covered with perfluoroether oil.'
_olex2_submission_special_instructions 'No special instructions were received'