Ex2Box: Interdependent Modes of Binding in a Two-Nanometer-Long Synthetic Receptor
Michal Juríček; Jonathan C. Barnes; Edward J. Dale; Wei-Guang Liu; Nathan L. Strutt; Carson J. Bruns; Nicolaas A. Vermeulen; Kala C. Ghooray; Amy A. Sarjeant; Charlotte L. Stern; Youssry Y. Botros; William A. Goddard; J. Fraser Stoddart; Journal of the American Chemical Society 135 (2013) 12736–12746; doi:10.1021/ja4052763

data_4120373
_publ_section_title
;
 Ex2Box: Interdependent Modes of Binding in a Two-Nanometer-Long Synthetic
 Receptor
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12736
_journal_page_last               12746
_journal_paper_doi               10.1021/ja4052763
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C60 H48 N4, 2(C18 H12), 4(F6 P), 4(C2 H3 N)'
_chemical_formula_sum            'C104 H84 F24 N8 P4'
_chemical_formula_weight         2025.67
_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             2013-01-24
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                80.251(3)
_cell_angle_beta                 86.771(3)
_cell_angle_gamma                64.519(2)
_cell_formula_units_Z            1
_cell_length_a                   10.4803(4)
_cell_length_b                   11.3488(5)
_cell_length_c                   21.4424(9)
_cell_measurement_reflns_used    6722
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.51
_cell_measurement_theta_min      4.37
_cell_volume                     2268.62(17)
_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      100.12
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14871
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.694
_diffrn_reflns_theta_min         4.373
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0411 before and 0.0331 after correction.
The Ratio of minimum to maximum transmission is 0.9003.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     959
_refine_ls_number_reflns         7507
_refine_ls_number_restraints     1765
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0649P)^2^+1.4714P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5915
_reflns_number_total             7507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4052763_si_006.cif
_cod_data_source_block           n2392
_cod_original_cell_volume        2268.63(17)
_cod_database_code               4120373
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H42A of C42A, H40A of C40A, H39A of C39A, H36A of C36A, H35A of C35A, H34A
  of C34A, H45A of C45A, H44A of C44A, H43A of C43A, H56 of C56, H25 of C25, H5
  of C5, H24 of C24, H6 of C6, H8 of C8, H9 of C9, H10 of C10, H11 of C11,
  {H12A,H12B} of C12, H14 of C14, H15 of C15, H17 of C17, H18 of C18, {H19A,
  H19B} of C19, H21 of C21, H22 of C22, H3 of C3, H2 of C2, H51 of C51, H52 of
  C52, H49A of C49A, H48A of C48A, H27 of C27, H28 of C28, H30 of C30, H31 of
  C31, H33 of C33, H34 of C34, H35 of C35, H36 of C36, H38 of C38, H57 of C57,
  H54 of C54, H53 of C53, H33A of C33A, H48 of C48, H47 of C47, H45 of C45, H44
  of C44, H43 of C43, H42 of C42, H39 of C39, H50A of C50A, H51A of C51A, H52A
  of C52A, H53A of C53A, H57A of C57A, H58A of C58A
 At 1.5 times of:
  {H60A,H60B,H60C} of C60, {H62A,H62B,H62C} of C62
2. Restrained distances
 C39-C38 ~ C37-C38 ~ C37-C36 ~ C36-C35 ~ C35-C34 ~ C34-C33 ~ C33-C32 ~ C37-C32
 ~ C49-C32 ~ C49-C40 ~ C39-C40 ~ C41-C40 ~ C41-C46 ~ C47-C46 ~ C48-C47 ~ C49-
 C48 ~ C42-C41 ~ C43-C42 ~ C43-C44 ~ C44-C45 ~ C45-C46
 with sigma of 0.02
 C49-C38 ~ C36-C33 ~ C37-C34 ~ C41-C48 ~ C40-C47 ~ C46-C43 ~ C42-C45 ~ C47-C40
 ~ C41-C48 ~ C49-C46
 with sigma of 0.02
 C40A-C41A ~ C39A-C40A ~ C38A-C39A ~ C38A-C37A ~ C36A-C37A ~ C35A-C36A ~ C34A-
 C35A ~ C33A-C34A ~ C32A-C33A ~ C32A-C37A ~ C32A-C49A ~ C49A-C48A ~ C48A-C47A ~
 C38A-C47A ~ C47A-C46A ~ C46A-C41A ~ C46A-C45A ~ C45A-C44A ~ C43A-C44A ~ C43A-
 C42A ~ C42A-C41A
 with sigma of 0.02
 C33A-C36A ~ C34A-C37A ~ C32A-C35A ~ C38A-C49A ~ C47A-C40A ~ C39A-C46A ~ C41A-
 C44A ~ C42A-C45A
 with sigma of 0.02
3. Restrained planarity
 C42, C47, C48, C46, C49, C41, C45, C32, C40, C44, C33, C37, C39, C43, C34,
 C36, C38, C35
 with sigma of 0.1
 C42A, C45A, C46A, C44A, C41A, C47A, C43A, C40A, C38A, C48A, C39A, C37A, C49A,
 C36A, C32A, C35A, C33A, C34A
 with sigma of 0.1
 C43, C47, C48, C46, C49, C41, C45, C32, C40, C42, C44, C33, C37, C39, C34,
 C36, C38, C35
 with sigma of 0.1
4. Rigid bond restraints
 C48, C47, H47, C46, H48, C49, C41, C45, C32, C40, C42, H45, C44, C33, C37,
 C39, H42, C43, H44, H33, C34, C36, C38, H39, H43, H34, C35, H36, H38, H35,
 C37A, C45A, H45A, C46A, C44A, C41A, C47A, C43A, H44A, C40A, C42A, C38A, C48A,
 H43A, H40A, C39A, H42A, H48A, C49A, H39A, C36A, C32A, H49A, H36A, C35A, C33A,
 H35A, C34A, H33A, H34A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C48 ~ C47 ~ H47 ~ C46 ~ H48 ~ C49 ~ C41 ~ C45 ~ C32 ~ C40 ~ C42 ~ H45 ~ C44 
~ C33 ~ C37 ~ C39 ~ H42 ~ C43 ~ H44 ~ H33 ~ C34 ~ C36 ~ C38 ~ H39 ~ H43 ~ H34 
~ C35 ~ H36 ~ H38 ~ H35 ~ C47A ~ C45A ~ H45A ~ C46A ~ C44A ~ C41A ~ C43A 
~ H44A ~ C40A ~ C42A ~ C38A ~ C48A ~ H43A ~ H40A ~ C39A ~ H42A ~ C37A ~ H48A 
~ C49A ~ H39A ~ C36A ~ C32A ~ H49A ~ H36A ~ C35A ~ C33A ~ H35A ~ C34A ~ H33A 
~ H34A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
6. others
 Sof(C50)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52)=Sof(C53)=Sof(H53)=Sof(C54)=
 Sof(H54)=Sof(C55)=Sof(C56)=Sof(H56)=Sof(C57)=Sof(H57)=Sof(C58)=1-Sof(C51)=1-
 Sof(C51)=1-Sof(C51)=1-Sof(C51)=1-Sof(C51)=1-Sof(C51)=1-Sof(C51)=1-Sof(C51)=1-
 Sof(C51)=1-Sof(C51)=1-Sof(C51)=1-Sof(C51)=1-Sof(C51)=1-Sof(C51)=1-Sof(C51)
 Sof(C32)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=
 Sof(H36)=Sof(C37)=Sof(C38)=Sof(H38)=Sof(C39)=Sof(H39)=Sof(C40)=Sof(C41)=
 Sof(C42)=Sof(H42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=
 Sof(C46)=Sof(C47)=Sof(H47)=Sof(C48)=Sof(H48)=Sof(C49)=1-Sof(C33)=1-Sof(C33)=1-
 Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-
 Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-
 Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-
 Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)=1-Sof(C33)
7.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B)
7.b 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), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27),
  C28(H28), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36),
 C38(H38), C39(H39), C42(H42), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48),
  C33A(H33A), C34A(H34A), C35A(H35A), C36A(H36A), C39A(H39A), C40A(H40A),
 C42A(H42A), C43A(H43A), C44A(H44A), C45A(H45A), C48A(H48A), C49A(H49A),
 C51(H51), C52(H52), C53(H53), C54(H54), C56(H56), C57(H57), C50A(H50A),
 C51A(H51A), C52A(H52A), C53A(H53A), C57A(H57A), C58A(H58A)
7.c Idealised Me refined as rotating group:
 C60(H60A,H60B,H60C), C62(H62A,H62B,H62C)
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.738
_shelx_res_checksum              88801
_shelxl_version_number           2012-9