Sliding-Ring Catenanes.
Fernando, Isurika R.; Frasconi, Marco; Wu, Yilei; Liu, Wei-Guang; Wasielewski, Michael R.; Goddard, 3rd, William A; Stoddart, J. Fraser; Journal of the American Chemical Society 138 (2016) 10214–10225; doi:10.1021/jacs.6b04982

data_4130593
_publ_section_title
;
 Sliding-Ring Catenanes.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10214
_journal_page_last               10225
_journal_paper_doi               10.1021/jacs.6b04982
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C36 H32 N4, C36 H44 O10, 2(C2 H3 N)'
_chemical_formula_sum            'C76 H82 N6 O10'
_chemical_formula_weight         1239.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.11 svn.r2872 for OlexSys, GUI svn.r4767)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.934(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9493(8)
_cell_length_b                   48.567(3)
_cell_length_c                   10.9451(5)
_cell_measurement_reflns_used    6501
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.474
_cell_measurement_theta_min      3.640
_cell_volume                     6828.9(7)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.796
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_Laue_measured_fraction_full 0.796
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       55
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20417
_diffrn_reflns_point_group_measured_fraction_full 0.796
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         61.164
_diffrn_reflns_theta_min         1.819
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0914 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.7893.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       plate
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     913
_refine_ls_number_reflns         9824
_refine_ls_number_restraints     681
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.1095
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+24.8607P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2433
_refine_ls_wR_factor_ref         0.2595
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6648
_reflns_number_total             9824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04982_si_002.cif
_cod_data_source_block           n3303
_cod_original_cell_volume        6829.0(6)
_cod_database_code               4130593
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.868
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6-C60 \\sim O7-C66 \\sim O7-C67 \\sim O8-C68 \\sim O8-C69 \\sim O9-C70 \\sim
O9-C71 \\sim O10-C72 \\sim O10-
 C37 \\sim O1-C42 \\sim O1-C47 \\sim O2-C48 \\sim O2-C49 \\sim O3-C50 \\sim
O3-C51 \\sim O4-C52 \\sim O4-C53 ~
 O5-C54 \\sim O5-C55 \\sim O7A-C66 \\sim O7A-C67A \\sim O8A-C68A \\sim O8A-C69A
\\sim O9-C70A
 with sigma of 0.02
 C66-C65 \\sim C67-C68 \\sim C69-C70 \\sim C71-C72 \\sim C48-C47 \\sim C50-C49
\\sim C51-C52 \\sim C53-C54
 \\sim C68A-C67A \\sim C70A-C69A
 with sigma of 0.02
 C71-C70 \\sim C69-C68 \\sim C67-C66 \\sim C65-C60 \\sim C72-C37 \\sim C55-C54
\\sim C53-C52 \\sim C51-C50
 \\sim C49-C48 \\sim C47-C42 \\sim C70A-C71 \\sim C69A-C68A \\sim C67A-C66
 with sigma of 0.02
3. Rigid bond restraints
 O7, O8, C67, C68, C69, C70, O7A, C67A, C68A, O8A, C69A, C70A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O7 \\sim O8 \\sim C67 \\sim C68 \\sim C69 \\sim C70 \\sim O7A \\sim C67A \\sim
C68A \\sim O8A \\sim C69A \\sim C70A: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.01
C76 \\sim C76A \\sim C75 \\sim C75A \\sim N6A \\sim N6: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
Uanis(O7) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C68)
\\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(O7A) \\sim Ueq,
Uanis(C67A) \\sim Ueq, Uanis(C68A) \\sim Ueq, Uanis(O8A) \\sim Ueq, Uanis(C69A)
\\sim Ueq, Uanis(C70A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Others
 Sof(O7A)=Sof(O8A)=Sof(H66C)=Sof(H66D)=Sof(C67A)=Sof(H67C)=Sof(H67D)=Sof(C68A)=
 Sof(H68C)=Sof(H68D)=Sof(C69A)=Sof(H69C)=Sof(H69D)=Sof(C70A)=Sof(H70C)=
 Sof(H70D)=1-FVAR(1)
 Sof(O7)=Sof(O8)=Sof(H66A)=Sof(H66B)=Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(C68)=
 Sof(H68A)=Sof(H68B)=Sof(C69)=Sof(H69A)=Sof(H69B)=Sof(C70)=Sof(H70A)=Sof(H70B)=
 FVAR(1)
 Sof(N6A)=Sof(C75A)=Sof(C76A)=Sof(H76D)=Sof(H76E)=Sof(H76F)=1-FVAR(2)
 Sof(N6)=Sof(C75)=Sof(C76)=Sof(H76A)=Sof(H76B)=Sof(H76C)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C19(H19A,H19B), C30(H30A,H30B), C47(H47A,H47B),
 C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B),
  C53(H53A,H53B), C54(H54A,H54B), C65(H65A,H65B), C66(H66A,H66B), C66(H66C,
 H66D), C67(H67A,H67B), C67A(H67C,H67D), C68(H68A,H68B), C68A(H68C,H68D),
 C69(H69A,H69B), C69A(H69C,H69D), C70(H70A,H70B), C70A(H70C,H70D), C71(H71A,
 H71B), C72(H72A,H72B)
6.b Me refined with riding coordinates:
 C74(H74A,H74B,H74C), C76(H76A,H76B,H76C)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26),
  C27(H27), C28(H28), C29(H29), C32(H32), C33(H33), C35(H35), C36(H36),
 C38(H38), C39(H39), C40(H40), C43(H43), C44(H44), C45(H45), C56(H56), C57(H57),
  C58(H58), C61(H61), C62(H62), C63(H63)
6.d Idealised Me refined as rotating group:
 C76A(H76D,H76E,H76F)
;
_smtbx_masks_special_details
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 347.0 Ang^3^ [5.1%]
Total electron count / cell = 92.6
;
_shelx_res_checksum              18954
_shelx_hkl_checksum              75180
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'