Formation of ring-in-ring complexes between crown ethers and rigid TVBox(8+).
Sun, Junling; Frasconi, Marco; Liu, Zhichang; Barnes, Jonathan C.; Wang, Yuping; Chen, Dongyang; Stern, Charlotte L.; Fraser Stoddart, J.; Chemical communications (Cambridge, England) 51 (2015) 1432–1435; doi:10.1039/c4cc08053j

data_7116222
_publ_section_title
;
 Formation of ring-in-ring complexes between crown ethers and rigid
 TVBox(8+).
;
_journal_issue                   8
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1432
_journal_page_last               1435
_journal_paper_doi               10.1039/c4cc08053j
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         '2(C68 H56 N8), 16(F6 P), C2 H3 N'
_chemical_formula_sum            'C138 H115 F96 N17 P16'
_chemical_formula_weight         4330.98
_chemical_name_systematic        TVBox
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-08-28 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.888(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   53.047(3)
_cell_length_b                   13.8933(7)
_cell_length_c                   23.3837(11)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.457
_cell_measurement_theta_min      5.141
_cell_volume                     16400.6(15)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.09
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.912
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            71652
_diffrn_reflns_point_group_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.464
_diffrn_reflns_theta_min         3.973
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    3.056
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.5722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0950 before and 0.0575 after correction. The Ratio of minimum to maximum transmission is 0.7604. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_description       plate
_exptl_crystal_F_000             8664
_exptl_crystal_recrystallization_method
'slow vapor diffusion of diisopropyl ether into the sample solution in acetonitrile'
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.014
_refine_diff_density_max         1.479
_refine_diff_density_min         -1.422
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1462
_refine_ls_number_reflns         13549
_refine_ls_number_restraints     878
_refine_ls_restrained_S_all      1.563
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0980P)^2^+102.7148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.1964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10261
_reflns_number_total             13549
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc08053j2.cif
_cod_data_source_block           n3213
_cod_depositor_comments
'Adding full bibliography for 7116222--7116224.cif.'
_cod_original_cell_volume        16400.7(14)
_cod_database_code               7116222
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.299
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 P8-F42 \\sim P8-F45 \\sim P8-F44 \\sim P8-F42 \\sim P8-F47 \\sim P8-F43 \\sim
P8-F46 \\sim P8-F45 \\sim P8-
 F43 \\sim P8-F46 \\sim P8-F44 \\sim P8-F47
 with sigma of 0.02
 F42A-F45A \\sim F46A-F47A \\sim F44A-F43A \\sim F45-F44 \\sim F43-F46 \\sim
F42-F47
 with sigma of 0.01
 F9-F7 \\sim F12-F11 \\sim F8-F10 \\sim F25-F28 \\sim F26-F30 \\sim F27-F29
\\sim F40-F37 \\sim F39-F38
 with sigma of 0.01
 P7-F1A \\sim P7-F41 \\sim P7-F38 \\sim P7-F40 \\sim P7-F37 \\sim P7-F39
 with sigma of 0.01
 F1A-F41 \\sim F37-F39 \\sim F40-F38 \\sim F41-F40 \\sim F39-F37 \\sim F1A-F38
 with sigma of 0.01
 P5-F27A \\sim P5-F26 \\sim P5-F26A \\sim P5-F30 \\sim P5-F30A \\sim P5-F25
\\sim P5-F25A \\sim P5-F27
 with sigma of 0.01
 F11-F10 \\sim F9-F7 \\sim F12-F8
 with sigma of 0.01
 F11-F7A \\sim F10A-F9 \\sim F8A-F12A
 with sigma of 0.01
 P2-F8A \\sim P2-F11 \\sim P2-F7A \\sim P2-F10A \\sim P2-F9 \\sim P2-F12A
 with sigma of 0.01
 F11-F8A \\sim F10A-F9 \\sim F7A-F12A \\sim F42-F47 \\sim F43-F46 \\sim F45-F44
\\sim F42-F46 \\sim F45-
 F43 \\sim F44-F47 \\sim F47A-F46A \\sim F45A-F42A \\sim F43A-F44A \\sim
F47A-F43A \\sim F46A-F45A ~
 F42A-F44A
 with sigma of 0.01
 P8-F43 \\sim P8-F45A \\sim P8-F46A \\sim P8-F45 \\sim P8-F42A \\sim P8-F47
\\sim P8-F44 \\sim P8-F43A ~
 P8-F46 \\sim P8-F47A \\sim P8-F42
 with sigma of 0.01
 C34A-C29 \\sim C34A-C33A \\sim C33A-C32 \\sim C32-C31A \\sim C31A-C30A \\sim
C30A-C29
 with sigma of 0.02
 C29-C32 \\sim C33A-C30A \\sim C31A-C34A
 with sigma of 0.02
 C29-C33A \\sim C34A-C32 \\sim C33A-C31A \\sim C32-C30A \\sim C31A-C29
 with sigma of 0.02
 C65A-C66 \\sim C65A-C64A \\sim C64A-C63 \\sim C63-C68A
 with sigma of 0.01
 P7-F41 \\sim P7-F40A \\sim P7-F37 \\sim P7-F37A \\sim P7-F40 \\sim P7-F39A
\\sim P7-F38 \\sim P7-F39 \\sim P7-
 F1B \\sim P7-F38A \\sim P7-F1A \\sim P7-F41A
 with sigma of 0.01
 F41-F40 \\sim F38-F39 \\sim F1A-F37 \\sim F41A-F40A \\sim F38A-F1B \\sim
F37A-F39A \\sim F39A-F1B ~
 F38A-F40A \\sim F37A-F41A
 with sigma of 0.01
3. Rigid bond restraints
 F43, F42, F45, F44, F47, F47, F46, F45, F43, F44, F42, F46
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F11, F7A, F7, F9, F12, F10A, F12A, F8, F8A, F10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F25A, F26, F25, F26A, F27A, F27, F30, F30A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F46, F43, F45, F42A, F42, F47, F46A, F43A, F44, F44A, F47A, F45A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C30, C31, C33, C34, C30A, C31A, C33A, C34A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F39, F38, F1A, F41, F40, F37
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F38A, F41, F37, F39, F1B, F1A, F40, F40A, F39A, F41A, F37A, F38
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F43 \\sim F42 \\sim F45 \\sim F44 \\sim F47 \\sim F47 \\sim F46 \\sim F45 \\sim
F43 \\sim F44 \\sim F42 \\sim F46: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
F11 \\sim F7A \\sim F7 \\sim F9 \\sim F12 \\sim F10A \\sim F12A \\sim F8 \\sim
F8A \\sim F10: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
F25A \\sim F26 \\sim F25 \\sim F26A \\sim F27A \\sim F27 \\sim F30 \\sim F30A:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
F46 \\sim F43 \\sim F45 \\sim F42A \\sim F42 \\sim F47 \\sim F46A \\sim F43A
\\sim F44 \\sim F44A \\sim F47A \\sim F45A: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.02
C30 \\sim C31 \\sim C33 \\sim C34 \\sim C30A \\sim C31A \\sim C33A \\sim C34A:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
F39 \\sim F38 \\sim F1A \\sim F41 \\sim F40 \\sim F37: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02
F38A \\sim F41 \\sim F37 \\sim F39 \\sim F1B \\sim F1A \\sim F40 \\sim F40A
\\sim F39A \\sim F41A \\sim F37A \\sim F38: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.02
5. Others
 Sof(F42A)=Sof(F43A)=Sof(F44A)=Sof(F45A)=Sof(F46A)=Sof(F47A)=1-FVAR(1)
 Sof(F42)=Sof(F43)=Sof(F44)=Sof(F45)=Sof(F46)=Sof(F47)=FVAR(1)
 Sof(F7A)=Sof(F8A)=Sof(F10A)=Sof(F12A)=1-FVAR(2)
 Sof(F7)=Sof(F8)=Sof(F10)=Sof(F12)=FVAR(2)
 Sof(F25A)=Sof(F26A)=Sof(F27A)=Sof(F30A)=1-FVAR(3)
 Sof(F25)=Sof(F26)=Sof(F27)=Sof(F30)=FVAR(3)
 Sof(F1B)=Sof(F37A)=Sof(F38A)=Sof(F39A)=Sof(F40A)=Sof(F41A)=1-FVAR(4)
 Sof(F1A)=Sof(F37)=Sof(F38)=Sof(F39)=Sof(F40)=Sof(F41)=FVAR(4)
 Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=
 Sof(H34A)=1-FVAR(5)
 Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=FVAR(5)
 Sof(C64A)=Sof(H64A)=Sof(C65A)=Sof(H65A)=Sof(C67A)=Sof(H67A)=Sof(C68A)=
 Sof(H68A)=1-FVAR(6)
 Sof(C64)=Sof(H64)=Sof(C65)=Sof(H65)=Sof(C67)=Sof(H67)=Sof(C68)=Sof(H68)=FVAR(6)
 Fixed Sof: N9(0.5) C69(0.5) C70(0.5) H70A(0.5) H70B(0.5) H70C(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C45(H45A,H45B), C52(H52A,H52B)
6.b Me refined with riding coordinates:
 C70(H70A,H70B,H70C)
6.c Aromatic/amide H refined with riding coordinates:
 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), C30(H30), C31(H31), C33(H33), C34(H34),
 C30A(H30A), C31A(H31A), C33A(H33A), C34A(H34A), C35(H35), C36(H36), C38(H38),
 C39(H39), C41(H41), C42(H42), C43(H43), C44(H44), C47(H47), C48(H48), C50(H50),
  C51(H51), C53(H53), C54(H54), C56(H56), C57(H57), C59(H59), C60(H60),
 C61(H61), C62(H62), C64(H64), C64A(H64A), C65(H65), C65A(H65A), C67(H67),
 C67A(H67A), C68(H68), C68A(H68A)
6.d Fitted hexagon refined as free rotating group:
 C29(C30,C31,C32,C33,C34)
;
_shelx_res_checksum              30559