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_1569452
_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         'C131 H137 N13 O2 Zn, 2(C16 H32 O8)'
_chemical_formula_sum            'C163 H201 N13 O18 Zn'
_chemical_formula_weight         2695.73
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-16
_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                69.998(2)
_cell_angle_beta                 78.914(2)
_cell_angle_gamma                81.231(2)
_cell_formula_units_Z            2
_cell_length_a                   19.9646(12)
_cell_length_b                   21.9566(14)
_cell_length_c                   22.5133(15)
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      22.989
_cell_measurement_theta_min      2.167
_cell_volume                     9060.2(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.0(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1240
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            368177
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.879
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0751 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.9512.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.988
_exptl_crystal_description       block
_exptl_crystal_F_000             2888
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMF - isopropyl ether'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.098
_refine_diff_density_max         1.126
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1766
_refine_ls_number_reflns         31970
_refine_ls_number_restraints     225
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.1795
_refine_ls_R_factor_gt           0.1115
_refine_ls_shift/su_max          3.005
_refine_ls_shift/su_mean         0.050
_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          0.3123
_refine_ls_wR_factor_ref         0.3687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16346
_reflns_number_total             31970
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01346d2.cif
_cod_data_source_block           mo_lzn_ntf2_170_0m
_cod_depositor_comments
'Adding full bibliography for 1569451--1569452.cif.'
_cod_database_code               1569452
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.977
_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, All O(H,H) groups
2. Restrained distances
 C97-C98A
 2.391 with sigma of 0.001
 C126-C1E
 2.39 with sigma of 0.02
 C64-C61 \\sim C61-C62
 with sigma of 0.02
 C64-C61 \\sim C61-C63
 with sigma of 0.02
 C62-C61 \\sim C61-C63
 with sigma of 0.02
 C62-C64 \\sim C64-C63
 with sigma of 0.02
 C64-C63 \\sim C63-C62
 with sigma of 0.02
 C128-C127 \\sim C126-C125 \\sim C124-C123 \\sim C122-C121 \\sim C120-C119
\\sim C118-C117 \\sim C116-
 C115 \\sim C114-C113
 with sigma of 0.02
 C125-O15 \\sim O15-C124
 with sigma of 0.02
 C121-O13 \\sim O13-C120
 with sigma of 0.02
 C119-O12 \\sim O12-C118
 with sigma of 0.02
 C117-O11 \\sim O11-C116
 with sigma of 0.02
 C127-O16 \\sim O16-C126
 with sigma of 0.02
 C115-O18 \\sim O18-C114
 with sigma of 0.02
 C123-O14 \\sim O14-C122
 with sigma of 0.02
 C113-O17 \\sim O17-C128
 with sigma of 0.02
 C61-C62 \\sim C61-C62A
 with sigma of 0.02
 C61-C63 \\sim C61-C63A
 with sigma of 0.02
 C61-C64 \\sim C61-C64A
 with sigma of 0.02
 C108-O6 \\sim O6-C107
 with sigma of 0.02
 C104-O4 \\sim O4-C103
 with sigma of 0.02
 C106-O5 \\sim O5-C105
 with sigma of 0.02
 C102-O3 \\sim O3-C101
 with sigma of 0.02
 C112-O8 \\sim O8-C111
 with sigma of 0.02
 C100-C101 \\sim C102-C103 \\sim C104-C105 \\sim C106-C107 \\sim C108-C109
\\sim C110-C111 \\sim C112-
 C97
 with sigma of 0.02
 C110-O7 \\sim O7-C109
 with sigma of 0.02
 O10-C98 \\sim O10-C98A
 with sigma of 0.04
 O9-C98 \\sim O9-C98A
 with sigma of 0.02
 C98A-C99 \\sim C100-C101 \\sim C102-C103 \\sim C104-C105 \\sim C106-C107 \\sim
C108-C109 \\sim C110-
 C111 \\sim C112-C97
 with sigma of 0.01
 C98-O9 \\sim O9-C98A
 with sigma of 0.001
 O9-C98 \\sim O10-C100 \\sim O3-C102 \\sim O4-C104 \\sim O5-C106 \\sim O6-C108
\\sim O7-C110 \\sim O8-C112
 with sigma of 0.001
 C141-C146 \\sim C141-C1B
 with sigma of 0.02
 C141-C145 \\sim C141-C1A
 with sigma of 0.04
 C144-C142 \\sim C144-C1C
 with sigma of 0.04
 C141-C143 \\sim C141-C1D
 with sigma of 0.04
 C144-C146 \\sim C144-C1B
 with sigma of 0.04
 C143-C142 \\sim C1D-C1C
 with sigma of 0.02
 C141-C142 \\sim C141-C1C
 with sigma of 0.02
 C144-C143 \\sim C144-C1D
 with sigma of 0.02
 C144-C145 \\sim C144-C1A
 with sigma of 0.02
 C146-C145 \\sim C1B-C1A
 with sigma of 0.02
 C127-C128 \\sim C1E-C1F
 with sigma of 0.02
 O16-C127 \\sim O16-C1E
 with sigma of 0.02
 O17-C127 \\sim O17-C1E
 with sigma of 0.04
 O16-C128 \\sim O16-C1F
 with sigma of 0.04
 O17-C128 \\sim O17-C1F
 with sigma of 0.02
 C22-C20 \\sim C20-C21
 with sigma of 0.0001
 C20-C21 \\sim C21-C22
 with sigma of 0.0001
 C162-N13 \\sim N13-C163
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C126) \\sim Ueq, Uanis(C125) \\sim Ueq: with sigma of 0.0001 and sigma
for terminal atoms of 0.0002
Uanis(C64) = Uanis(C62A) = Uanis(C62) = Uanis(C63A) = Uanis(C63) = Uanis(C64A)
Uanis(C98) = Uanis(C98A)
Uanis(C146) = Uanis(C1B)
Uanis(C1C) = Uanis(C142)
Uanis(C145) = Uanis(C1A)
Uanis(C143) = Uanis(C1D)
Uanis(C127) = Uanis(C1E) = Uanis(C128) = Uanis(C1F)
Uanis(C86) = Uanis(C84) = Uanis(C85)
Uanis(C21) = Uanis(C20) = Uanis(C22)
Uanis(C95) = Uanis(C96) = Uanis(C94)
4. Rigid body (RIGU) restrains
 C19, C20, C21, C22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N13, C161, C162, C163
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C62A)=Sof(H62D)=Sof(H62E)=Sof(H62F)=Sof(C63A)=Sof(H63D)=Sof(H63E)=
 Sof(H63F)=Sof(C64A)=Sof(H64D)=Sof(H64E)=Sof(H64F)=1-FVAR(1)
 Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(H63C)=
 Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=FVAR(1)
 Sof(H99C)=Sof(H99D)=Sof(C98A)=Sof(H98C)=Sof(H98D)=1-FVAR(2)
 Sof(H99A)=Sof(H99B)=Sof(C98)=Sof(H98A)=Sof(H98B)=FVAR(2)
 Sof(C1A)=Sof(H1AA)=Sof(C1B)=Sof(H1BA)=Sof(C1C)=Sof(H1C)=Sof(C1D)=Sof(H1D)=1-
 FVAR(3)
 Sof(C142)=Sof(H142)=Sof(C143)=Sof(H143)=Sof(C145)=Sof(H145)=Sof(C146)=
 Sof(H146)=FVAR(3)
 Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(C1F)=Sof(H1FA)=Sof(H1FB)=1-FVAR(4)
 Sof(C127)=Sof(H12O)=Sof(H12P)=Sof(C128)=Sof(H12Q)=Sof(H12R)=FVAR(4)
 Fixed Sof: H3(0.5) H4(0.5) H9(0.5) H10(0.5)
6.a Rotating group:
 O1(H1A,H1B)
6.b Secondary CH2 refined with riding coordinates:
 C97(H97A,H97B), C99(H99A,H99B), C99(H99C,H99D), C100(H10B,H10C), C101(H10D,
 H10E), C102(H10F,H10G), C103(H10H,H10I), C104(H10J,H10K), C105(H10L,H10M),
 C106(H10N,H10O), C107(H10P,H10Q), C108(H10R,H10S), C109(H10T,H10U), C110(H11O,
 H11P), C111(H11Q,H11R), C112(H11S,H11T), C98(H98A,H98B), C98A(H98C,H98D),
 C113(H11A,H11B), C114(H11C,H11D), C115(H11E,H11F), C116(H11G,H11H), C117(H11I,
 H11J), C118(H11K,H11L), C119(H11M,H11N), C120(H12A,H12B), C121(H12C,H12D),
 C122(H12E,H12F), C123(H12G,H12H), C124(H12I,H12J), C125(H12K,H12L), C126(H12M,
 H12N), C127(H12O,H12P), C128(H12Q,H12R), C1E(H1EA,H1EB), C1F(H1FA,H1FB)
6.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), N5(H5), N9(H9), N10(H10), N12(H12), C2(H2), C3(H3A), C5(H5A),
 C10(H10A), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18), C24(H24),
 C25(H25), C27(H27), C28(H28), C34(H34), C35(H35), C37(H37), C42(H42), C43(H43),
  C46(H46), C47(H47), C49(H49), C50(H50), C56(H56), C57(H57), C59(H59),
 C60(H60), C66(H66), C67(H67), C69(H69), C73(H73), C74(H74), C78(H78), C79(H79),
  C81(H81), C82(H82), C88(H88), C89(H89), C91(H91), C92(H92), C130(H130),
 C131(H131), C133(H133), C138(H138), C139(H139), C152(H152), C153(H153),
 C155(H155), C156(H156), C161(H161), C142(H142), C143(H143), C145(H145),
 C146(H146), C1A(H1AA), C1B(H1BA), C1C(H1C), C1D(H1D)
6.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C52(H52A,H52B,H52C), C53(H53A,
 H53B,H53C), C54(H54A,H54B,H54C), C84(H84A,H84B,H84C), C85(H85A,H85B,H85C),
 C86(H86A,H86B,H86C), C94(H94A,H94B,H94C), C95(H95A,H95B,H95C), C96(H96A,H96B,
 H96C), C148(H14A,H14B,H14C), C149(H14D,H14E,H14F), C150(H15A,H15B,H15C),
 C158(H15D,H15E,H15F), C159(H15G,H15H,H15I), C160(H16A,H16B,H16C), C162(H16D,
 H16E,H16F), C163(H16G,H16H,H16I), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C),
 C64(H64A,H64B,H64C), C62A(H62D,H62E,H62F), C63A(H63D,H63E,H63F), C64A(H64D,
 H64E,H64F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              84001
_shelx_fab_checksum              4437
_olex2_exptl_crystal_mounting_method
'on a glass microloop covered with perfluoroether oil.'
_olex2_submission_special_instructions 'No special instructions were received'