# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Warmuth, Ralf'
_publ_contact_author_email       warmuth@rutchem.rutgers.edu

_publ_section_title              
;
Templated dynamic cryptophane formation in water
;
loop_
_publ_author_name
R.Warmuth
'Junling Sun.'
C.Givelet
'Di Xu.'
T.Emge
A.Dhokte

# Attachment '- cryptophane.cif'

data_cryptophane
_database_code_depnum_ccdc_archive 'CCDC 809740'
#TrackingRef '- cryptophane.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'N6 O6 C60 H60, 6(C H2 CL2)'
_chemical_formula_sum            'C66 H72 Cl12 N6 O6'
_chemical_formula_weight         1470.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Rhombohedral
_symmetry_space_group_name_H-M   R32
_symmetry_space_group_name_Hall  'R 3 2"'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'

_cell_length_a                   16.2073(7)
_cell_length_b                   16.2073(7)
_cell_length_c                   23.4757(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5340.4(5)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3391
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      30.47

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2286
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7840
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         30.54
_reflns_number_total             3444
_reflns_number_gt                2666
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+11.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_number_reflns         3444
_refine_ls_number_parameters     163
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.35417(16) 0.03540(16) 0.05979(10) 0.0335(5) Uani 1 1 d . . .
O1 O 0.32745(13) 0.26870(13) 0.06791(8) 0.0368(4) Uani 1 1 d . . .
C1 C 0.26253(17) 0.19313(17) 0.09972(10) 0.0293(5) Uani 1 1 d . . .
C2 C 0.26862(17) 0.10958(17) 0.09745(11) 0.0285(5) Uani 1 1 d . . .
C3 C 0.20547(17) 0.03282(17) 0.13028(11) 0.0285(5) Uani 1 1 d . . .
H3 H 0.2096 -0.0236 0.1292 0.034 Uiso 1 1 calc R . .
C4 C 0.13632(17) 0.03408(17) 0.16475(11) 0.0256(5) Uani 1 1 d . . .
C5 C 0.12975(16) 0.11667(17) 0.16576(10) 0.0262(5) Uani 1 1 d . . .
C6 C 0.19381(17) 0.19591(17) 0.13380(11) 0.0279(5) Uani 1 1 d . . .
H6 H 0.1903 0.2526 0.1354 0.033 Uiso 1 1 calc R . .
C7 C 0.3230(2) 0.35381(19) 0.07152(14) 0.0443(7) Uani 1 1 d . . .
H7A H 0.3722 0.4026 0.0470 0.066 Uiso 1 1 calc R . .
H7B H 0.3337 0.3763 0.1110 0.066 Uiso 1 1 calc R . .
H7C H 0.2601 0.3413 0.0590 0.066 Uiso 1 1 calc R . .
C8 C 0.34051(17) 0.10631(19) 0.06069(11) 0.0314(5) Uani 1 1 d . . .
H8 H 0.3782 0.1592 0.0367 0.038 Uiso 1 1 calc R . .
C9 C 0.42671(18) 0.0422(2) 0.02020(13) 0.0380(6) Uani 1 1 d . . .
H9A H 0.4799 0.0435 0.0418 0.046 Uiso 1 1 calc R . .
H9B H 0.4524 0.1021 -0.0019 0.046 Uiso 1 1 calc R . .
C10 C 0.05473(18) 0.12653(18) 0.19945(10) 0.0278(5) Uani 1 1 d . . .
H10A H 0.0360 0.0840 0.2331 0.033 Uiso 1 1 calc R . .
H10B H 0.0831 0.1928 0.2135 0.033 Uiso 1 1 calc R . .
C11 C 0.0993(2) 0.4326(2) 0.1667 0.0425(10) Uani 1 2 d S . .
H11 H 0.0590 0.4011 0.2004 0.051 Uiso 0.50 1 calc PR . .
H12 H 0.0677 0.3923 0.1329 0.051 Uiso 0.50 1 calc PR . .
Cl1 Cl 0.10939(9) 0.54361(7) 0.15733(6) 0.0822(4) Uani 1 1 d . . .
C20 C 0.3333 0.6667 0.0639(3) 0.078(2) Uiso 1 3 d S . .
H21 H 0.3237 0.6042 0.0457 0.094 Uiso 0.33333 1 d P . .
H22 H 0.3333 0.6667 0.0963 0.094 Uiso 1 3 d S . .
Cl21 Cl 0.4362(5) 0.7614(4) 0.0248(4) 0.0626(18) Uani 0.33333 1 d P . .
Cl22 Cl 0.2515(5) 0.6924(5) 0.0258(4) 0.070(2) Uani 0.33333 1 d P . .
C30 C 0.0000 0.0000 0.0319(5) 0.051(3) Uiso 0.50 3 d SP . .
H31 H -0.0276 -0.0553 0.0568 0.061 Uiso 0.16667 1 d P . .
H32 H 0.0276 0.0553 0.0568 0.061 Uiso 0.16667 1 d P . .
Cl31 Cl -0.0756(6) 0.0229(8) -0.0069(5) 0.075(3) Uani 0.16667 1 d P . .
Cl32 Cl 0.0989(5) 0.0232(6) -0.0024(5) 0.077(3) Uani 0.16667 1 d PU . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0280(10) 0.0366(11) 0.0380(13) -0.0115(10) -0.0046(9) 0.0177(9)
O1 0.0358(10) 0.0278(9) 0.0451(11) 0.0011(7) 0.0088(8) 0.0146(8)
C1 0.0261(11) 0.0262(11) 0.0323(13) -0.0037(10) -0.0006(10) 0.0105(9)
C2 0.0247(11) 0.0312(12) 0.0308(13) -0.0070(10) -0.0048(10) 0.0150(10)
C3 0.0282(11) 0.0291(11) 0.0315(13) -0.0060(9) -0.0070(10) 0.0169(10)
C4 0.0240(11) 0.0273(11) 0.0245(12) -0.0035(9) -0.0070(9) 0.0121(9)
C5 0.0241(10) 0.0283(11) 0.0254(12) -0.0076(9) -0.0048(9) 0.0126(9)
C6 0.0276(11) 0.0245(10) 0.0309(14) -0.0069(9) -0.0038(10) 0.0126(9)
C7 0.0501(17) 0.0268(13) 0.0481(18) 0.0000(12) 0.0144(13) 0.0134(12)
C8 0.0238(11) 0.0327(12) 0.0353(14) -0.0059(11) -0.0023(10) 0.0123(10)
C9 0.0251(11) 0.0457(15) 0.0463(16) -0.0175(13) -0.0078(11) 0.0201(11)
C10 0.0301(11) 0.0285(12) 0.0245(12) -0.0059(9) -0.0003(10) 0.0145(9)
C11 0.0290(13) 0.0290(13) 0.071(3) 0.0048(9) -0.0048(9) 0.0159(15)
Cl1 0.0818(7) 0.0468(5) 0.1389(10) 0.0057(6) 0.0064(7) 0.0479(5)
Cl21 0.074(4) 0.0329(14) 0.068(3) 0.0022(16) -0.006(3) 0.0170(19)
Cl22 0.119(6) 0.066(3) 0.061(3) 0.017(2) 0.018(3) 0.073(4)
Cl31 0.066(5) 0.110(12) 0.070(7) 0.008(6) -0.014(5) 0.059(8)
Cl32 0.058(3) 0.088(6) 0.092(4) 0.007(4) 0.011(3) 0.041(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.275(3) . ?
N1 C9 1.459(3) . ?
O1 C1 1.370(3) . ?
O1 C7 1.419(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.407(3) . ?
C2 C3 1.384(4) . ?
C2 C8 1.472(3) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 C10 1.524(3) 3 ?
C5 C6 1.399(3) . ?
C5 C10 1.524(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C9 C9 1.517(5) 5 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C4 1.524(3) 2 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 Cl1 1.737(2) 10_455 ?
C11 Cl1 1.737(2) . ?
C11 H11 0.9900 . ?
C11 H12 0.9900 . ?
C20 Cl22 1.813(8) . ?
C20 Cl21 1.850(8) . ?
C20 H21 1.037(3) . ?
C20 H22 0.760(8) . ?
C30 Cl32 1.660(10) . ?
C30 Cl31 1.711(9) . ?
C30 H31 0.971(7) . ?
C30 H32 0.971(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 116.1(2) . . ?
C1 O1 C7 116.5(2) . . ?
O1 C1 C6 123.7(2) . . ?
O1 C1 C2 116.6(2) . . ?
C6 C1 C2 119.7(2) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 C8 122.5(2) . . ?
C1 C2 C8 119.6(2) . . ?
C2 C3 C4 123.4(2) . . ?
C2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C10 118.3(2) . 3 ?
C5 C4 C10 123.5(2) . 3 ?
C4 C5 C6 119.6(2) . . ?
C4 C5 C10 123.8(2) . . ?
C6 C5 C10 116.5(2) . . ?
C1 C6 C5 121.2(2) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C2 122.7(3) . . ?
N1 C8 H8 118.7 . . ?
C2 C8 H8 118.7 . . ?
N1 C9 C9 110.3(2) . 5 ?
N1 C9 H9A 109.6 . . ?
C9 C9 H9A 109.6 5 . ?
N1 C9 H9B 109.6 . . ?
C9 C9 H9B 109.6 5 . ?
H9A C9 H9B 108.1 . . ?
C4 C10 C5 113.28(18) 2 . ?
C4 C10 H10A 108.9 2 . ?
C5 C10 H10A 108.9 . . ?
C4 C10 H10B 108.9 2 . ?
C5 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
Cl1 C11 Cl1 111.2(2) 10_455 . ?
Cl1 C11 H11 109.4 10_455 . ?
Cl1 C11 H11 109.4 . . ?
Cl1 C11 H12 109.4 10_455 . ?
Cl1 C11 H12 109.4 . . ?
H11 C11 H12 108.0 . . ?
Cl22 C20 Cl21 91.4(4) . . ?
Cl22 C20 H21 104.5(5) . . ?
Cl21 C20 H21 103.9(5) . . ?
Cl22 C20 H22 119.5(4) . . ?
Cl21 C20 H22 119.8(4) . . ?
H21 C20 H22 114.4(4) . . ?
Cl32 C30 Cl31 114.0(8) . . ?
Cl32 C30 H31 116.6(3) . . ?
Cl31 C30 H31 118.1(3) . . ?
Cl32 C30 H32 97.8(4) . . ?
Cl31 C30 H32 99.8(5) . . ?
H31 C30 H32 106.0(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 C1 C6 0.8(4) . . . . ?
C7 O1 C1 C2 -178.2(2) . . . . ?
O1 C1 C2 C3 178.4(2) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
O1 C1 C2 C8 -1.8(3) . . . . ?
C6 C1 C2 C8 179.1(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C8 C2 C3 C4 -179.2(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C2 C3 C4 C10 -179.2(2) . . . 3 ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C10 C4 C5 C6 178.1(2) 3 . . . ?
C3 C4 C5 C10 177.2(2) . . . . ?
C10 C4 C5 C10 -2.9(4) 3 . . . ?
O1 C1 C6 C5 -179.5(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C4 C5 C6 C1 1.8(4) . . . . ?
C10 C5 C6 C1 -177.3(2) . . . . ?
C9 N1 C8 C2 178.8(2) . . . . ?
C3 C2 C8 N1 -5.3(4) . . . . ?
C1 C2 C8 N1 174.9(2) . . . . ?
C8 N1 C9 C9 -123.7(3) . . . 5 ?
C4 C5 C10 C4 -92.9(3) . . . 2 ?
C6 C5 C10 C4 86.2(3) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        30.54
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.057