Efficient syntheses of pillar[6]arene-based hetero[4]rotaxanes using a cooperative capture strategy
Xisen Hou; Chenfeng Ke; Chuyang Cheng; Nan Song; Anthea K. Blackburn; Amy A. Sarjeant; Youssry Y. Botros; Ying-Wei Yang; J. Fraser; Chem.Commun. 50 (2014) 6196–; doi:10.1039/C4CC00733f

data_7113936
_publ_section_title
;
 Efficient syntheses of pillar[6]arene-based hetero[4]rotaxanes using a
 cooperative capture strategy
;
_journal_name_full               Chem.Commun.
_journal_page_first              6196
_journal_paper_doi               10.1039/C4CC00733f
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety
'2(C36 H36 N24 O12), C44 H52 N10 O4, C42 H36 O12, 5(C H3 N O2), 4(F6 P)'
_chemical_formula_sum            'C163 H175 F24 N63 O50 P4'
_chemical_formula_weight         4396.53
_chemical_name_systematic
;
 ?
;
_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     dual
_audit_creation_date             2013-08-05
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                91.6273(18)
_cell_angle_beta                 94.4694(18)
_cell_angle_gamma                90.902(2)
_cell_formula_units_Z            2
_cell_length_a                   16.0511(5)
_cell_length_b                   25.4637(9)
_cell_length_c                   30.2922(10)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.13
_cell_measurement_theta_min      3.02
_cell_volume                     12336.4(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
;
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
;
SHELXD, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            41702
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        54.235
_diffrn_reflns_theta_max         54.23
_diffrn_reflns_theta_min         1.46
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.108
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0820 before and 0.0373 after correction.
The Ratio of minimum to maximum transmission is 0.8375.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       plate
_exptl_crystal_F_000             4540
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.546
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2765
_refine_ls_number_reflns         29486
_refine_ls_number_restraints     3239
_refine_ls_restrained_S_all      1.617
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.1284
_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^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3725
_refine_ls_wR_factor_ref         0.3931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20325
_reflns_number_total             29486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc00733f2.cif
_cod_data_source_block           n2881a
_cod_database_code               7113936
_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, All O(H) groups
2. Restrained distances
 F19A-F20A \\sim F19A-F22A \\sim F19A-F23A \\sim F19A-F24A \\sim F20A-F21A 
 \\sim F20A-F23A \\sim F20A-
 F24A \\sim F21A-F22A \\sim F21A-F23A \\sim F21A-F24A \\sim F22A-F23A \\sim 
 F22A-F24A
 with sigma of 0.04
 P4A-F19A \\sim P4A-F20A \\sim P4A-F21A \\sim P4A-F22A \\sim P4A-F23A \\sim 
 P4A-F24A
 with sigma of 0.02
 F19-F20 \\sim F19-F22 \\sim F19-F23 \\sim F19-F24 \\sim F20-F21 \\sim F20-F23 
 \\sim F20-F24 \\sim F21-F22
 \\sim F21-F23 \\sim F21-F24 \\sim F22-F23 \\sim F22-F24
 with sigma of 0.04
 P4-F19 \\sim P4-F20 \\sim P4-F21 \\sim P4-F22 \\sim P4-F23 \\sim P4-F24
 with sigma of 0.02
 O12S-N6S \\sim O11S-N6S \\sim O4S-N2S \\sim O3S-N2S \\sim O1S-N1S 
 \\sim O2S-N1S \\sim O8S-N4S \\sim O7S-
 N4S \\sim O6S-N3S \\sim O5S-N3S
 with sigma of 0.02
 O1S-O2S \\sim O3S-O4S \\sim O5S-O6S \\sim O7S-O8S \\sim O11S-O12S
 with sigma of 0.02
 N4S-C4S \\sim N1S-C1S \\sim N2S-C2S \\sim N6S-C6S \\sim N3S-C3S
 with sigma of 0.02
 C25-C20 \\sim C25A-C20 \\sim C25-C24 \\sim C25A-C24A \\sim C24-C23 
 \\sim C24A-C23 \\sim C23-C22A -
 C23-C22 \\sim C22A-C21A \\sim C22-C21 \\sim C21A-C20 \\sim C21-C20
 with sigma of 0.02
 N3-N2 \\sim N4-N3
 with sigma of 0.02
 N4-C12 \\sim N2-C11
 with sigma of 0.02
 N1-C9 \\sim N1A-C9 \\sim N1-C10 \\sim N1A-C10A
 with sigma of 0.02
 C11-C10A \\sim C11-C10
 with sigma of 0.02
 C12A-C11 \\sim C12-C11 \\sim N4-C12 \\sim N4-C12A \\sim N4-N3 \\sim N4-N3A 
 \\sim N3A-N2A \\sim N3-N2 \\sim N2-
 C11 \\sim N2A-C11
 with sigma of 0.02
 N4-C13A \\sim N4-C13
 with sigma of 0.02
 C14-C13A \\sim C14-C13
 with sigma of 0.02
 C12A-N2A \\sim C12-N3 \\sim C12A-N3A \\sim C12-N2
 with sigma of 0.02
3. Restrained planarity
 C21A, C20, C25A, C24A, C23, C22A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(C10) = Uanis(C12) = Uanis(N1A) = Uanis(C10A) = Uanis(N2A) = 
Uanis(N3A) = Uanis(C12A) = Uanis(C13) = Uanis(N3) = Uanis(N2) = Uanis(C13A)
5. Others
 Sof(P4A)=Sof(F19A)=Sof(F20A)=Sof(F21A)=Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(1)
 Sof(P4)=Sof(F19)=Sof(F20)=Sof(F21)=Sof(F22)=Sof(F23)=Sof(F24)=FVAR(1)
 Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(H21A)=Sof(C25A)=Sof(H25A)=Sof(C24A)=
 Sof(H24A)=1-FVAR(2)
 Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=FVAR(2)
 Sof(H9BC)=Sof(H9BD)=Sof(N1A)=Sof(H1AA)=Sof(H1AB)=Sof(C10A)=Sof(H10E)=
 Sof(H10F)=Sof(N2A)=Sof(N3A)=Sof(C12A)=Sof(H12A)=1-FVAR(3)
 Sof(N1)=Sof(H1A)=Sof(H1B)=Sof(H9AA)=Sof(H9AB)=Sof(C10)=Sof(H10C)=Sof(H10D)=
 Sof(N3)=Sof(N2)=Sof(C12)=Sof(H12)=FVAR(3)
 Sof(H14C)=Sof(H14D)=Sof(C13A)=Sof(H13C)=Sof(H13D)=1-FVAR(4)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H14A)=Sof(H14B)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C82(H82), C84(H84), C88(H88), C90(H90), C94(H94), C96(H96), C100(H100),
 C102(H102), C106(H106), C108(H108), C112(H112), C114(H114), C46(H46), 
 C48(H48),
  C52(H52), C54(H54), C58(H58), C60(H60), C64(H64), C66(H66), C70(H70),
 C72(H72), C76(H76), C78(H78)
6.b Secondary CH2 refined with riding coordinates:
 C85(H85A,H85B), C86(H86A,H86B), C91(H91A,H91B), C92(H92A,H92B), C97(H97A,
 H97B), C98(H98A,H98B), C103(H10G,H10H), C104(H10I,H10J), C109(H10K,H10L),
 C110(H11A,H11B), C115(H11C,H11D), C116(H11E,H11F), C49(H49A,H49B), C50(H50A,
 H50B), C55(H55A,H55B), C56(H56A,H56B), C61(H61A,H61B), C62(H62A,H62B),
 C67(H67A,H67B), C68(H68A,H68B), C73(H73A,H73B), C74(H74A,H74B), 
 C79(H79A,H79B),
  C80(H80A,H80B), N1(H1A,H1B), N10(H10A,H10B), C9(H9AA,H9AB), C9(H9BC,H9BD),
 C10(H10C,H10D), C13(H13A,H13B), C14(H14A,H14B), C14(H14C,H14D), 
 C31(H31A,H31B),
  C32(H32A,H32B), C35(H35A,H35B), C36(H36A,H36B), C123(H12B,H12C), C130(H13E,
 H13F), C137(H13G,H13H), C144(H14E,H14F), C151(H15A,H15B), C158(H15C,H15D),
 N1A(H1AA,H1AB), C10A(H10E,H10F), C13A(H13C,H13D)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21),
 C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), 
 C33(H33),
  C38(H38), C40(H40), C42(H42), C118(H118), C121(H121), C126(H126), 
  C129(H129),
 C132(H132), C135(H135), C140(H140), C143(H143), C146(H146), C149(H149),
 C154(H154), C157(H157), C22A(H22A), C21A(H21A), C25A(H25A), C24A(H24A),
 C12(H12), C12A(H12A)
6.d Fitted hexagon refined as free rotating group:
 C119(C118,C117,C122,C121,C120), C127(C126,C125,C124,C129,C128), C133(C132,
 C131,C136,C135,C134), C141(C140,C139,C138,C143,C142), C148(C147,C146,C145,
 C150,
 C149), C152(C153,C154,C155,C156,C157)
6.e Tetrahedral OH refined with riding coordinates:
 O29(H29A), O30(H30A), O31(H31), O32(H32), O33(H33A), O34(H34), O35(H35),
 O36(H36), O37(H37), O38(H38A), O39(H39), O40(H40A)
6.f Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C),
 C1S(H1SA,H1SB,H1SC), C6S(H6SA,H6SB,H6SC), C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,
 H3SC), C4S(H4SA,H4SB,H4SC)
;
_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 = 4014.2 Ang^3^ [32.5%]
Total electron count / cell = 1130.1
;
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.558
_shelxl_version_number           2012-9