Formation of a hetero[3]rotaxane by a dynamic component-swapping strategy
Eleanor A. Wilson; Nicolaas A. Vermeulen; Paul R. McGonigal; Alyssa-Jennifer Avestro; Amy A. Sarjeant; Charlotte L. Stern; J. Fraser Stoddart; Chem.Commun. 50 (2014) 9665–; doi:10.1039/C4cc03612C

data_7115478
_publ_section_title
;
 Formation of a hetero[3]rotaxane by a dynamic component-swapping strategy
;
_journal_name_full               Chem.Commun.
_journal_page_first              9665
_journal_paper_doi               10.1039/C4cc03612C
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety
'2(C34 H35 N3 O6), C33 H56 N2, 2(F6 P), 0.5(C6 H14 O), C2 H3 N'
_chemical_formula_sum            'C106 H136 F12 N9 O12.5 P2'
_chemical_formula_weight         2026.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-05-21
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                91.402(10)
_cell_angle_beta                 95.326(7)
_cell_angle_gamma                115.533(8)
_cell_formula_units_Z            4
_cell_length_a                   20.542(2)
_cell_length_b                   23.791(3)
_cell_length_c                   24.599(2)
_cell_measurement_reflns_used    3189
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.02
_cell_measurement_theta_min      2.39
_cell_volume                     10773(2)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.03
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.516
_diffrn_measured_fraction_theta_max 0.892
_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  0.0996
_diffrn_reflns_av_unetI/netI     0.2536
_diffrn_reflns_Laue_measured_fraction_full 0.516
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            44374
_diffrn_reflns_point_group_measured_fraction_full 0.516
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         58.93
_diffrn_reflns_theta_min         1.81
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.066
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1150 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.7645.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       needle
_exptl_crystal_F_000             4292
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2635
_refine_ls_number_reflns         20131
_refine_ls_number_restraints     2733
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.2874
_refine_ls_R_factor_gt           0.1475
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1839P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3687
_refine_ls_wR_factor_ref         0.4305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6275
_reflns_number_total             20131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc03612c2.cif
_cod_data_source_block           n2757
_cod_original_formula_sum        'C106 H136 F12 N9 O12.50 P2'
_cod_database_code               7115478
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1A-C16A \\sim N2A-C19A
 with sigma of 0.02
 C17A-C16A \\sim C17A-C18A
 with sigma of 0.02
 C55B-C54A \\sim C55A-C54A \\sim C57A-C56A \\sim C57A-C56B
 with sigma of 0.02
 O3A-C55A \\sim O3B-C55B \\sim O3B-C56B \\sim O3A-C56A \\sim O4A-C57A \\sim O4A-C58A \\sim O2A-C54A ~
 O2A-C53A
 with sigma of 0.02
 O8A-C86A \\sim O8A-C87A \\sim O9A-C88A \\sim O9A-C89A \\sim O10A-C90A \\sim O10A-C91A \\sim O11A-C92A
 \\sim O11A-C93A \\sim O12A-C94A \\sim O12A-C95A
 with sigma of 0.02
 C88A-C87A \\sim C90A-C89A \\sim C92A-C91A \\sim C94A-C93A
 with sigma of 0.02
 O5B-C59A \\sim O5A-C59A \\sim O5A-C60A \\sim O5B-C60B \\sim O6A-C61A \\sim O6A-C61B
 with sigma of 0.02
 C61B-C60B \\sim C61A-C60A
 with sigma of 0.02
 C63A-C62A \\sim C64A-C63A \\sim C65A-C64A \\sim C66A-C65A \\sim C67A-C66A \\sim C67A-C62A
 with sigma of 0.01
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C22) \\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C89A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(H54C)=Sof(H54D)=Sof(H57C)=Sof(H57D)=Sof(C56B)=Sof(H56C)=Sof(H56D)=
 Sof(O3B)=Sof(C55B)=Sof(H55C)=Sof(H55D)=1-FVAR(1)
 Sof(O3A)=Sof(H54A)=Sof(H54B)=Sof(C55A)=Sof(H55A)=Sof(H55B)=Sof(C56A)=
 Sof(H56A)=Sof(H56B)=Sof(H57A)=Sof(H57B)=FVAR(1)
 Sof(H59C)=Sof(H59D)=Sof(C61B)=Sof(H61C)=Sof(H61D)=Sof(C60B)=Sof(H60C)=
 Sof(H60D)=Sof(O5B)=1-FVAR(2)
 Sof(O5A)=Sof(H59A)=Sof(H59B)=Sof(C60A)=Sof(H60A)=Sof(H60B)=Sof(C61A)=
 Sof(H61A)=Sof(H61B)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C102(H102), C105(H105)
6.b Secondary CH2 refined with riding coordinates:
 C54(H54E,H54F), C55(H55E,H55F), C56(H56E,H56F), C57(H57E,H57F), C58(H58C,
 H58D), C59(H59E,H59F), C60(H60E,H60F), C61(H61E,H61F), C54A(H54A,H54B),
 C54A(H54C,H54D), C55A(H55A,H55B), C56A(H56A,H56B), C57A(H57A,H57B), C57A(H57C,
 H57D), C58A(H58A,H58B), C59A(H59A,H59B), C59A(H59C,H59D), C60A(H60A,H60B),
 C61A(H61A,H61B), C88(H88A,H88B), C89(H89A,H89B), C90(H90A,H90B), C91(H91A,
 H91B), C92(H92A,H92B), C93(H93A,H93B), C94(H94A,H94B), C95(H95A,H95B),
 C87A(H87A,H87B), C88A(H88C,H88D), C89A(H89C,H89D), C90A(H90C,H90D), C91A(H91C,
 H91D), C92A(H92C,H92D), C93A(H93C,H93D), C94A(H94C,H94D), N1(H1A,H1B), N2(H2A,
 H2B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C1A(H1AA,
 H1AB), N1A(H1AC,H1AD), N2A(H2AA,H2AB), C15A(H15D,H15E), C16A(H16C,H16D),
 C17A(H17C,H17D), C18A(H18C,H18D), C19A(H19C,H19D), C56B(H56C,H56D), C55B(H55C,
 H55D), C61B(H61C,H61D), C60B(H60C,H60D)
6.c Me refined with riding coordinates:
 C8A(H8AA,H8AB,H8AC), C10A(H10D,H10E,H10F), C103(H10G,H10H,H10I)
6.d Aromatic/amide H refined with riding coordinates:
 C34(H34), C36(H36), C38(H38), C41(H41), C42(H42), C44(H44), C45(H45),
 C47(H47), C49(H49), C50(H50), C51(H51), C52(H52), C63(H63), C64(H64), C65(H65),
  C66(H66), C34A(H34A), C36A(H36A), C38A(H38A), C41A(H41A), C42A(H42A),
 C44A(H44A), C45A(H45A), C47A(H47A), C49A(H49A), C50A(H50A), C51A(H51A),
 C52A(H52A), C63A(H63A), C64A(H64A), C65A(H65A), C66A(H66A), C68(H68), C70(H70),
  C72(H72), C75(H75), C76(H76), C78(H78), C79(H79), C81(H81), C83(H83),
 C84(H84), C85(H85), C86(H86), C97(H97), C98(H98), C99(H99), C100(H100),
 C69A(H69A), C71A(H71A), C74A(H74A), C75A(H75A), C77A(H77A), C78A(H78A),
 C80A(H80D), C82A(H82A), C83A(H83A), C84A(H84A), C85A(H85A), C96A(H96A),
 C97A(H97A), C98A(H98A), C99A(H99A), C01A(H01A), C3(H3), C5(H5), C7(H7),
 C21(H21), C23(H23), C25(H25), C2A(H2AC), C4A(H4A), C6A(H6A), C21A(H21A),
 C23A(H23A), C25A(H25A)
6.e Idealised Me refined as rotating group:
 C46(H46D,H46E,H46F), C46A(H46A,H46B,H46C), C80(H80A,H80B,H80C), C79A(H79A,
 H79B,H79C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C33(H33A,H33B,H33C), C9A(H9AA,H9AB,H9AC), C12A(H12A,H12B,H12C),
 C13A(H13D,H13E,H13F), C14A(H14D,H14E,H14F), C27A(H27D,H27E,H27F), C28A(H28D,
 H28E,H28F), C29A(H29D,H29E,H29F), C31A(H31D,H31E,H31F), C32A(H32D,H32E,H32F),
 C33A(H33D,H33E,H33F), C104(H10J,H10K,H10L), C106(H10M,H10N,H10O), C107(H10P,
 H10Q,H10R), C109(H10S,H10T,H10U), C111(H11D,H11E,H11F)
;
_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 = 586.2 Ang^3^ [5.4%]
Total electron count / cell = 56.4
;
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.730
_shelx_res_checksum              1479
_shelxl_version_number           2012-9