Modulating the shuttling motion of [2]rotaxanes built of <i>p</i>-xylylenediamine units through permethylation at the benzylic positions of the ring.
Puigcerver, Julio; Alajarin, Mateo; Martinez-Cuezva, Alberto; Berna, Jose; Organic & biomolecular chemistry 21 (2023) 9070–9075; doi:10.1039/d3ob01611k

data_7159626
_publ_section_title
;
 Modulating the shuttling motion of [2]rotaxanes built of
 <i>p</i>-xylylenediamine units through permethylation at the benzylic
 positions of the ring.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9070
_journal_page_last               9075
_journal_paper_doi               10.1039/d3ob01611k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         '4(C H2 Cl2), 2(C16 H15 N O), 2(C20 H22 N2 O2)'
_chemical_formula_sum            'C76 H82 Cl8 N6 O6'
_chemical_formula_weight         1459.07
_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             2023-05-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-05 deposited with the CCDC.	2023-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                85.290(2)
_cell_angle_beta                 82.032(2)
_cell_angle_gamma                87.045(2)
_cell_formula_units_Z            2
_cell_length_a                   14.7489(8)
_cell_length_b                   15.2963(9)
_cell_length_c                   16.4862(9)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.00
_cell_measurement_theta_min      2.71
_cell_volume                     3668.0(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc.)'
_computing_data_collection       'APEX3 2017.3 (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc.)'
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w-scans and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            120345
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.424
_diffrn_reflns_theta_min         2.714
_exptl_absorpt_coefficient_mu    3.253
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       prism
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.891
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     982
_refine_ls_number_reflns         13442
_refine_ls_number_restraints     116
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+3.6923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11728
_reflns_number_total             13442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01611k2.cif
_cod_data_source_block           jpa27_2_0msp_a
_cod_depositor_comments          'Adding full bibliography for 7159626.cif.'
_cod_database_code               7159626
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.804
_shelx_estimated_absorpt_t_min   0.535
_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,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-C6 = C8-C9 = C9-C10
 1.37 with sigma of 0.02
 C5-C10
 1.38 with sigma of 0.02
 C6-C7 = C7-C8
 1.36 with sigma of 0.02
 C5-C9
 2.38 with sigma of 0.04
 C6-C8
 2.36 with sigma of 0.04
 C5-C7 = C7-C9 = C8-C10
 2.37 with sigma of 0.04
 C5-C6 \\sim C6-C7 \\sim C7-C8 \\sim C8-C9 \\sim C9-C10 \\sim C10-C5
 with sigma of 0.02
 C5-C9 \\sim C5-C7 \\sim C9-C7 \\sim C8-C6 \\sim C8-C10 \\sim C10-C6
 with sigma of 0.04
3. Restrained planarity
 C5, C6, C7, C8, C9, C10
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(Cl3')=Sof(Cl4')=Sof(Cl5')=Sof(Cl6')=Sof(H1'A)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(C4)=Sof(H4)=Sof(C5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=
 Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(H38C)=Sof(H38D)=Sof(H39C)=Sof(H39D)=1-
 FVAR(1)
 Sof(Cl3)=Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=Sof(H1')=Sof(C3')=Sof(H3'A)=Sof(H3'B)=
 Sof(C4')=Sof(H4')=Sof(C5')=Sof(C6')=Sof(H6')=Sof(C7')=Sof(H7')=Sof(C8')=
 Sof(H8')=Sof(C9')=Sof(H9')=Sof(C10')=Sof(H10')=Sof(H38A)=Sof(H38B)=Sof(H39A)=
 Sof(H39B)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C4(H4), C4'(H4'), C42(H42)
7.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3'(H3'A,H3'B), C37(H37A,H37B), C38(H38A,H38B), C38(H38C,H38D),
 C39(H39A,H39B), C39(H39C,H39D), C40(H40A,H40B), C41(H41A,H41B)
7.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N1'(H1'), N1'(H1'A), N2(H2), N2'(H2'), N3(H3), N3'(H3'), C1(H1A),
 C1'(H1'B), C6(H6), C6'(H6'), C7(H7), C7'(H7'), C8(H8), C8'(H8'), C9(H9),
 C9'(H9'), C10(H10), C10'(H10'), C12(H12), C12'(H12'), C13(H13), C13'(H13'),
 C14(H14), C14'(H14'), C15(H15), C15'(H15'), C16(H16), C16'(H16'), C18(H18),
 C18'(H18'), C19(H19), C19'(H19'), C21(H21), C21'(H21'), C22(H22), C22'(H22'),
 C28(H28), C28'(H28'), C29(H29), C29'(H29'), C30(H30), C30'(H30'), C32(H32),
 C32'(H32'), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
7.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C24'(H24D,H24E,H24F), C25(H25A,H25B,H25C), C25'(H25D,
 H25E,H25F), C35(H35A,H35B,H35C), C35'(H35D,H35E,H35F), C36(H36A,H36B,H36C),
 C36'(H36D,H36E,H36F)
;
_shelx_res_checksum              78288
_olex2_submission_special_instructions 'No special instructions were received'