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_4130591
_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
'4(C28 H40 O10), 4(C36 H32 N4), 6(C7 H8), H2 O'
_chemical_formula_sum            'C298 H338 N16 O41'
_chemical_formula_weight         4799.82
_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     direct
_audit_creation_date             2014-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                87.674(3)
_cell_angle_beta                 69.262(2)
_cell_angle_gamma                78.983(3)
_cell_formula_units_Z            2
_cell_length_a                   20.1201(9)
_cell_length_b                   26.1627(12)
_cell_length_c                   26.4880(12)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.106
_cell_measurement_theta_min      2.670
_cell_volume                     12793.9(10)
_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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.983
_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  0.0368
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            83250
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.250
_diffrn_reflns_theta_min         2.391
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0979 before and 0.0446 after correction.
The Ratio of minimum to maximum transmission is 0.8787.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       plate
_exptl_crystal_F_000             5132
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.021
_refine_diff_density_max         1.470
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3323
_refine_ls_number_reflns         43042
_refine_ls_number_restraints     522
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0849
_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^)+(0.1396P)^2^+10.4260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2244
_refine_ls_wR_factor_ref         0.2608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                27965
_reflns_number_total             43042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04982_si_003.cif
_cod_data_source_block           n3513
_cod_database_code               4130591
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.860
_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, All O(H,H) groups
2. Restrained distances
 O3D-C47D \\sim O3B-C47B \\sim O3D-C46D \\sim O3B-C46B \\sim O2B-C45B \\sim
O2B-C45D \\sim O4B-C48B ~
 O2C-C44C \\sim O2E-C44C \\sim O2E-C45E \\sim O2C-C45C \\sim O3C-C46E \\sim
O3C-C46C
 with sigma of 0.01
 C48B-C47B \\sim C48B-C47D \\sim C46B-C45B \\sim C46D-C45D \\sim C50B-C49B
\\sim C44B-C43B \\sim C46E-
 C45E \\sim C46C-C45C
 with sigma of 0.01
 C47B-C46B \\sim C46D-C47D \\sim C48B-C49B \\sim C45D-C44B \\sim C44C-C45E
\\sim C46E-C47C \\sim C46C-
 C47C \\sim C45C-C44C
 with sigma of 0.01
3. Rigid bond restraints
 C47B, C47D, C46D, C46B, C45D, C45B, O3D, O3B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2E, O2C, C45E, C45C, C46C, C46E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C32S, C29S, C34S, C35S, C30S, C33S, C31S, C33T, C29T, C34T, C30T, C31T, C32T,
 C35T
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C47B \\sim C47D \\sim C46D \\sim C46B \\sim C45D \\sim C45B \\sim O3D \\sim
O3B: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
O2E \\sim O2C \\sim C45E \\sim C45C \\sim C46C \\sim C46E: within 1.7A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C32S \\sim C29S \\sim C34S \\sim C35S \\sim C30S \\sim C33S \\sim C31S \\sim
C33T \\sim C29T \\sim C34T \\sim C30T \\sim C31T \\sim C32T \\sim C35T: within
1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C29T)=Sof(H29T)=Sof(C30T)=Sof(C31T)=Sof(H31T)=Sof(C32T)=Sof(H32T)=
 Sof(C33T)=Sof(H33T)=Sof(C34T)=Sof(H34T)=Sof(C35T)=Sof(H35G)=Sof(H35H)=
 Sof(H35I)=Sof(O12)=Sof(H12A)=Sof(H12B)=1-FVAR(1)
 Sof(C29S)=Sof(C30S)=Sof(H30S)=Sof(C31S)=Sof(H31S)=Sof(C32S)=Sof(H32S)=
 Sof(C33S)=Sof(H33S)=Sof(C34S)=Sof(H34S)=Sof(C35S)=Sof(H35D)=Sof(H35E)=
 Sof(H35F)=Sof(O11)=Sof(H11I)=Sof(H11J)=FVAR(1)
 Sof(H48C)=Sof(H48D)=Sof(O3D)=Sof(C45D)=Sof(H45C)=Sof(H45D)=Sof(C46D)=
 Sof(H46C)=Sof(H46D)=Sof(C47D)=Sof(H47C)=Sof(H47D)=1-FVAR(2)
 Sof(O3B)=Sof(C45B)=Sof(H45A)=Sof(H45B)=Sof(C46B)=Sof(H46A)=Sof(H46B)=
 Sof(C47B)=Sof(H47A)=Sof(H47B)=Sof(H48A)=Sof(H48B)=FVAR(2)
 Sof(H44E)=Sof(H44F)=Sof(O2E)=Sof(C45E)=Sof(H45G)=Sof(H45H)=Sof(C46E)=
 Sof(H46G)=Sof(H46H)=1-FVAR(3)
 Sof(O2C)=Sof(H44C)=Sof(H44D)=Sof(C45C)=Sof(H45E)=Sof(H45F)=Sof(C46C)=
 Sof(H46E)=Sof(H46F)=FVAR(3)
6.a Free rotating group:
 O11(H11I,H11J), O12(H12A,H12B)
6.b Secondary CH2 refined with riding coordinates:
 C43(H43E,H43F), C44(H44G,H44H), C45(H45I,H45J), C46(H46I,H46J), C47(H47G,
 H47H), C48(H48G,H48H), C49(H49E,H49F), C50(H50E,H50F), C57(H57E,H57F),
 C58(H58E,H58F), C59(H59E,H59F), C60(H60E,H60F), C61(H61E,H61F), C62(H62E,H62F),
  C63(H63E,H63F), C64(H64E,H64F), C43A(H43G,H43H), C44A(H44I,H44J), C45A(H45K,
 H45L), C46A(H46K,H46L), C47A(H47I,H47J), C48A(H48I,H48J), C49A(H49G,H49H),
 C50A(H50G,H50H), C57A(H57G,H57H), C58A(H58G,H58H), C59A(H59G,H59H), C60A(H60G,
 H60H), C61A(H61G,H61H), C62A(H62G,H62H), C63A(H63G,H63H), C64A(H64G,H64H),
 C43B(H43A,H43B), C44B(H44A,H44B), C45B(H45A,H45B), C46B(H46A,H46B), C47B(H47A,
 H47B), C48B(H48A,H48B), C48B(H48C,H48D), C49B(H49A,H49B), C50B(H50A,H50B),
 C57B(H57A,H57B), C58B(H58A,H58B), C59B(H59A,H59B), C60B(H60A,H60B), C61B(H61A,
 H61B), C62B(H62A,H62B), C63B(H63A,H63B), C64B(H64A,H64B), C43C(H43C,H43D),
 C44C(H44C,H44D), C44C(H44E,H44F), C45C(H45E,H45F), C46C(H46E,H46F), C47C(H47E,
 H47F), C48C(H48E,H48F), C49C(H49C,H49D), C50C(H50C,H50D), C57C(H57C,H57D),
 C58C(H58C,H58D), C59C(H59C,H59D), C60C(H60C,H60D), C61C(H61C,H61D), C62C(H62C,
 H62D), C63C(H63C,H63D), C64C(H64C,H64D), C11(H11A,H11B), C18(H18A,H18B),
 C29(H29A,H29B), C36(H36A,H36B), C11A(H11C,H11D), C18A(H18C,H18D), C29A(H29C,
 H29D), C36A(H36C,H36D), C11B(H11E,H11F), C18B(H18E,H18F), C29B(H29E,H29F),
 C36B(H36E,H36F), C11C(H11G,H11H), C18C(H18G,H18H), C29C(H29G,H29H), C36C(H36G,
 H36H), C45D(H45C,H45D), C46D(H46C,H46D), C47D(H47C,H47D), C45E(H45G,H45H),
 C46E(H46G,H46H)
6.c Aromatic/amide H refined with riding coordinates:
 C38(H38), C39(H39), C41(H41), C42(H42), C52(H52), C53(H53), C55(H55),
 C56(H56), C38A(H38A), C39A(H39A), C41A(H41A), C42A(H42A), C52A(H52A),
 C53A(H53A), C55A(H55A), C56A(H56A), C38B(H38B), C39B(H39B), C41B(H41B),
 C42B(H42B), C52B(H52B), C53B(H53B), C55B(H55B), C56B(H56B), C38C(H38C),
 C39C(H39C), C41C(H41C), C42C(H42C), C52C(H52C), C53C(H53C), C55C(H55C),
 C56C(H56C), C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32), C34(H34),
 C35(H35), C1A(H1A), C2A(H2A), C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C9A(H9A),
  C10A(H10A), C13A(H13A), C14A(H14A), C16A(H16A), C17A(H17A), C19A(H19A),
 C20A(H20A), C22A(H22A), C23A(H23A), C25A(H25A), C26A(H26A), C27A(H27A),
 C28A(H28A), C31A(H31A), C32A(H32A), C34A(H34A), C35A(H35A), C1B(H1B), C2B(H2B),
  C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B), C13B(H13B),
 C14B(H14B), C16B(H16B), C17B(H17B), C19B(H19B), C20B(H20B), C22B(H22B),
 C23B(H23B), C25B(H25B), C26B(H26B), C27B(H27B), C28B(H28B), C31B(H31B),
 C32B(H32B), C34B(H34B), C35B(H35B), C1C(H1C), C2C(H2C), C4C(H4C), C5C(H5C),
 C7C(H7C), C8C(H8C), C9C(H9C), C10C(H10C), C13C(H13C), C14C(H14C), C16C(H16C),
 C17C(H17C), C19C(H19C), C20C(H20C), C22C(H22C), C23C(H23C), C25C(H25C),
 C26C(H26C), C27C(H27C), C28C(H28C), C31C(H31C), C32C(H32C), C34C(H34C),
 C35C(H35C), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S), C6S(H6S), C23S(H23S),
 C24S(H24S), C25S(H25S), C26S(H26S), C27S(H27S), C9S(H9S), C10S(H10S),
 C11S(H11S), C12S(H12S), C13S(H13S), C30S(H30S), C31S(H31S), C32S(H32S),
 C33S(H33S), C34S(H34S), C29T(H29T), C31T(H31T), C32T(H32T), C33T(H33T),
 C34T(H34T), C08W(H08W), C08Y(H08Y), C090(H090), C095(H095), C096(H096),
 C16S(H16S), C17S(H17S), C18S(H18S), C19S(H19S), C20S(H20S)
6.d Fitted hexagon refined as free rotating group:
 C29S(C30S,C31S,C32S,C33S,C34S), C29T(C30T,C31T,C32T,C33T,C34T)
6.e Idealised Me refined as rotating group:
 C7S(H7SA,H7SB,H7SC), C28S(H28D,H28E,H28F), C14S(H14D,H14E,H14F), C35S(H35D,
 H35E,H35F), C35T(H35G,H35H,H35I), C09U(H09A,H09B,H09C), C21S(H21A,H21B,H21C)
;
_shelx_res_checksum              60268
_shelx_hkl_checksum              73674