A thermally driven rotaxane-catenane interconversion with a dynamic bis(hindered amino) disulfide.
Takashima, Rikito; Aoki, Daisuke; Takahashi, Akira; Otsuka, Hideyuki; Organic & biomolecular chemistry 22 (2024) 927–931; doi:10.1039/d3ob01693e

data_7159663
_publ_section_title
;
 A thermally driven rotaxane-catenane interconversion with a dynamic
 bis(hindered amino) disulfide.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              927
_journal_page_last               931
_journal_paper_doi               10.1039/d3ob01693e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C72 H114 N10 O6 S4, 2(C32 H33 N2 O2)'
_chemical_formula_sum            'C136 H180 N14 O10 S4'
_chemical_formula_weight         2299.17
_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_block_doi                 10.5517/ccdc.csd.cc2gyn7b
_audit_creation_date             2023-04-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-09-04 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                83.5207(15)
_cell_angle_beta                 73.4507(16)
_cell_angle_gamma                69.2324(18)
_cell_formula_units_Z            1
_cell_length_a                   13.7131(3)
_cell_length_b                   15.4192(3)
_cell_length_c                   18.7176(3)
_cell_measurement_reflns_used    17344
_cell_measurement_temperature    90
_cell_measurement_theta_max      75.5110
_cell_measurement_theta_min      2.4510
_cell_volume                     3546.99(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -118.00 -18.00   0.50    5.00    --  -41.30 -40.00  13.00  200
  2  \w      6.00  51.00   0.50    5.00    --   41.30 -40.00  13.00   90
  3  \w     21.00 118.00   0.50    5.00    --   41.30  40.00 167.00  194
  4  \w    -31.00  -5.00   0.50    5.00    --   41.30 -40.00  13.00   52
  5  \w   -175.00 -95.00   0.50   15.00    -- -104.00 -40.00  13.00  160
  6  \w    100.00 125.00   0.50   15.00    --  108.75  40.00 167.00   50
  7  \w   -115.00 -59.00   0.50    5.00    --  -41.30 -57.00  60.00  112
  8  \w    -45.00 -19.00   0.50    5.00    --  -41.30 -57.00  60.00   52
  9  \w    -28.00  36.00   0.50    5.00    --  -41.30  40.00 167.00  128
 10  \w    -87.00 -15.00   0.50    5.00    --  -41.30 125.00 -90.00  144
 11  \w     22.00  62.00   0.50    5.00    --   41.30 -57.00-180.00   80
 12  \w      5.00  31.00   0.50    5.00    --   41.30 -19.00-150.00   52
 13  \w     33.00  93.00   0.50    5.00    --   41.30-125.00 -60.00  120
 14  \w    -78.00 -32.00   0.50   15.00    -- -104.00  77.00 -30.00   92
 15  \w    -73.00 -32.00   0.50   15.00    -- -104.00 125.00 -60.00   82
 16  \w   -115.00 -89.00   0.50   15.00    -- -104.00 -94.00 120.00   52
 17  \w   -111.00 -85.00   0.50   15.00    -- -104.00 125.00 -60.00   52
 18  \w   -174.00-118.00   0.50   15.00    -- -104.00 -94.00 120.00  112
 19  \w    -68.00 -38.00   0.50   15.00    -- -104.00 125.00   0.00   60
 20  \w    -66.00 -30.00   0.50   15.00    -- -104.00  61.00  90.00   72
 21  \w    -59.00 -34.00   0.50   15.00    -- -104.00  61.00  30.00   50
 22  \w     40.00  73.00   0.50   15.00    --  108.75 -97.00 -39.41   66
 23  \w     81.00 106.00   0.50   15.00    --  108.75 -94.00 120.00   50
 24  \w     89.00 176.00   0.50   15.00    --  108.75  77.00 -90.00  174
 25  \w     35.00  77.00   0.50   15.00    --  108.75 -94.00 120.00   84
 26  \w     85.00 170.00   0.50   15.00    --  108.75  30.00 120.00  170
 27  \w     35.00  84.00   0.50   15.00    --  108.75 -94.00-150.00   98
 28  \w     52.00 107.00   0.50   15.00    --  108.75-106.00 110.55  110
 29  \w     37.00 100.00   0.50   15.00    --  108.75 -77.00 120.00  126
 30  \w     41.00  88.00   0.50   15.00    --  108.75 -94.00  30.00   94
 31  \w     46.00  85.00   0.50   15.00    --  108.75-142.00 -32.16   78
 32  \w     94.00 125.00   0.50   15.00    --  108.75-142.00 -32.16   62
 33  \w     91.00 117.00   0.50   15.00    --  108.75  61.00-180.00   52
 34  \w    121.00 168.00   0.50   15.00    --  108.75  61.00-180.00   94
 35  \w     88.00 176.00   0.50   15.00    --  108.75  45.00-120.00  176
 36  \w     37.00 101.00   0.50   15.00    --  108.75 -94.00   0.00  128
 37  \w     62.00 103.00   0.50   15.00    --  108.75 -94.00-120.00   82
 38  \w     78.00 106.00   0.50   15.00    --  108.75 -94.00-180.00   56
 39  \w    118.00 171.00   0.50   15.00    --  108.75  30.00 -60.00  106
 40  \w     38.00  72.00   0.50   15.00    --  108.75 -61.00-180.00   68
 41  \w     81.00 106.00   0.50   15.00    --  108.75 -98.00 108.10   50
 42  \w     62.00  95.00   0.50   15.00    --  108.75-101.00  72.22   66
 43  \w     85.00 178.00   0.50   15.00    --  108.75  30.00-150.00  186
 44  \w     78.00 105.00   0.50   15.00    --  108.75 -97.00 -39.41   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0712190000
_diffrn_orient_matrix_UB_12      -0.1028497000
_diffrn_orient_matrix_UB_13      0.0007306000
_diffrn_orient_matrix_UB_21      0.1001203000
_diffrn_orient_matrix_UB_22      0.0252373000
_diffrn_orient_matrix_UB_23      -0.0437375000
_diffrn_orient_matrix_UB_31      0.0204150000
_diffrn_orient_matrix_UB_32      0.0143138000
_diffrn_orient_matrix_UB_33      0.0738930000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            45289
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.778
_diffrn_reflns_theta_min         2.463
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_description       block
_exptl_crystal_F_000             1238
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     747
_refine_ls_number_reflns         14453
_refine_ls_number_restraints     1026
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0727
_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^)+(0.1528P)^2^+0.5852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2382
_refine_ls_wR_factor_ref         0.2579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9822
_reflns_number_total             14453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01693e2.cif
_cod_data_source_block           2catenane_auto
_cod_depositor_comments          'Adding full bibliography for 7159663.cif.'
_cod_original_cell_volume        3547.00(12)
_cod_database_code               7159663
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.835
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C15(H15), C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C84(H84A,H84B), C83(H83A,H83B), C80(H80A,H80B), C87(H87A,
 H87B), C6(H6A,H6B), C35(H35A,H35B), C67(H67A,H67B), C81(H81A,H81B), C56(H56A,
 H56B), C82(H82A,H82B), C22(H22A,H22B), C29(H29A,H29B), C65(H65A,H65B),
 C53(H53A,H53B), C51(H51A,H51B), C28(H28A,H28B), C24(H24A,H24B), C23(H23A,H23B),
  C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
3.c Aromatic/amide H refined with riding coordinates:
 C73(H73), C37(H37), C61(H61), C40(H40), C32(H32), C60(H60), C72(H72),
 C64(H64), C38(H38), C71(H71), C54(H54), C63(H63), C77(H77), C75(H75), C57(H57),
  C49(H49), C55(H55), C76(H76), C41(H41), C58(H58)
3.d Idealised Me refined as rotating group:
 C88(H88A,H88B,H88C), C10(H10A,H10B,H10C), C44(H44A,H44B,H44C), C46(H46A,H46B,
 H46C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C45(H45A,
 H45B,H45C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              30425
_shelx_hkl_checksum              70804
_shelx_fab_checksum              22416
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.669