# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cavitand

_audit_creation_date             2014-09-18T10:14:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C112 H96 N8 O8, (C H3 N O)'
_chemical_formula_sum            'C113 H99 N9 O10'
_chemical_formula_weight         1743.01

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 4/n n c'
_symmetry_space_group_name_Hall  '-P 4a 2bc'
_symmetry_Int_Tables_number      126
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, -y+1/2, z'
'-x+1/2, y, -z+1/2'
'y, x, -z+1/2'
'y, -x+1/2, z'
'-y+1/2, x, z'
'-y+1/2, -x+1/2, -z+1/2'
'-x, -y, -z'
'-x, y-1/2, z-1/2'
'x-1/2, y-1/2, -z'
'x-1/2, -y, z-1/2'
'-y, -x, z-1/2'
'-y, x-1/2, -z'
'y-1/2, -x, -z'
'y-1/2, x-1/2, z-1/2'

_cell_length_a                   19.221(3)
_cell_length_b                   19.221(3)
_cell_length_c                   26.996(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9974(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      23.26

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_F_000             3680
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.989

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_probe          X-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bluker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_number            81727
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.119
_diffrn_reflns_theta_max         24.154
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.882
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3995
_reflns_number_gt                3440
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1467P)²+15.4790P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3995
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0984
_refine_ls_wR_factor_ref         0.2863
_refine_ls_wR_factor_gt          0.2778
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11876(16) 0.28905(18) 0.53925(12) 0.0415(8) Uani 1 1 d . . . . .
H1 H 0.142 0.2822 0.5699 0.05 Uiso 1 1 calc R U . . .
C2 C 0.08409(16) 0.23308(18) 0.51787(12) 0.0417(8) Uani 1 1 d . . . . .
C3 C 0.05143(17) 0.2446(2) 0.47272(13) 0.0477(9) Uani 1 1 d . . . . .
C4 C 0.05309(18) 0.3086(2) 0.44831(13) 0.0495(10) Uani 1 1 d . . . . .
C5 C 0.08833(18) 0.3631(2) 0.47131(13) 0.0482(9) Uani 1 1 d . . . . .
C6 C 0.12081(17) 0.35467(18) 0.51749(12) 0.0429(8) Uani 1 1 d . . . . .
C7 C 0.08501(18) 0.1605(2) 0.54023(13) 0.0473(9) Uani 1 1 d . . . . .
H7 H 0.0415 0.1368 0.5288 0.057 Uiso 1 1 calc R U . . .
C8 C 0.0833(2) 0.1597(2) 0.59726(14) 0.0547(10) Uani 1 1 d . . . . .
H8A H 0.1263 0.182 0.6097 0.066 Uiso 1 1 calc R U . . .
H8B H 0.0435 0.1883 0.6086 0.066 Uiso 1 1 calc R U . . .
C9 C 0.0772(3) 0.0873(3) 0.62040(15) 0.0712(13) Uani 1 1 d . . . . .
H9 H 0.1193 0.0599 0.6108 0.085 Uiso 1 1 calc R U . . .
C10 C 0.0129(3) 0.0479(3) 0.6023(3) 0.113(2) Uani 1 1 d . . . . .
H10A H -0.0287 0.0764 0.6079 0.169 Uiso 1 1 calc R U . . .
H10B H 0.0085 0.0041 0.6205 0.169 Uiso 1 1 calc R U . . .
H10C H 0.0176 0.0381 0.5668 0.169 Uiso 1 1 calc R U . . .
C11 C 0.0762(5) 0.0935(4) 0.67680(19) 0.130(3) Uani 1 1 d . . . . .
H11A H 0.1214 0.1106 0.6884 0.196 Uiso 1 1 calc R U . . .
H11B H 0.067 0.0477 0.6914 0.196 Uiso 1 1 calc R U . . .
H11C H 0.0397 0.1261 0.6868 0.196 Uiso 1 1 calc R U . . .
C12 C 0.01806(19) 0.3180(2) 0.39912(13) 0.0528(10) Uani 1 1 d . . . . .
C13 C 0.0558(2) 0.3319(3) 0.35677(16) 0.0757(15) Uani 1 1 d . . . . .
H13 H 0.1051 0.3343 0.3587 0.091 Uiso 1 1 calc R U . . .
C14 C 0.0236(2) 0.3423(3) 0.31166(16) 0.0797(15) Uani 1 1 d . . . . .
H14 H 0.051 0.3522 0.2832 0.096 Uiso 1 1 calc R U . . .
C15 C -0.0484(2) 0.3385(2) 0.30736(14) 0.0593(11) Uani 1 1 d . . . . .
C16 C -0.0856(2) 0.3238(3) 0.34963(14) 0.0626(12) Uani 1 1 d . . . . .
H16 H -0.1348 0.3209 0.3479 0.075 Uiso 1 1 calc R U . . .
C17 C -0.0527(2) 0.3131(3) 0.39468(15) 0.0619(11) Uani 1 1 d . . . . .
H17 H -0.0798 0.3021 0.423 0.074 Uiso 1 1 calc R U . . .
C18 C 0.0503(2) 0.1442(2) 0.42177(14) 0.0578(11) Uani 1 1 d . . . . .
H18A H 0.0916 0.1682 0.4081 0.069 Uiso 1 1 calc R U . . .
H18B H 0.0211 0.129 0.3936 0.069 Uiso 1 1 calc R U . . .
O1 O 0.01208(13) 0.19129(15) 0.45122(10) 0.0576(8) Uani 1 1 d . . . . .
O2 O 0.08508(14) 0.42782(14) 0.44883(9) 0.0552(7) Uani 1 1 d . . . . .
C29 C 0.25 0.25 0.4475(3) 0.0503(17) Uani 1 4 d S T P . .
H29A H 0.2966 0.2617 0.4596 0.075 Uiso 0.25 1 calc R U P . .
H29B H 0.2368 0.2038 0.4596 0.075 Uiso 0.25 1 calc R U P . .
H29C H 0.2165 0.2845 0.4596 0.075 Uiso 0.25 1 calc R U P . .
N3 N 0.25 0.25 0.3923(2) 0.0492(15) Uani 1 4 d S T P . .
O3 O 0.1974(3) 0.2359(5) 0.3710(2) 0.0822(19) Uani 0.5 1 d . . P . .
C19A C -0.0518(3) 0.3845(4) 0.2251(3) 0.068(4) Uani 0.460(5) 1 d G . P A 1
H19A H -0.0095 0.4078 0.2323 0.081 Uiso 0.460(5) 1 calc R U P A 1
N1A N -0.0828(4) 0.3923(4) 0.1789(3) 0.066(3) Uani 0.460(5) 1 d G . P A 1
C21A C -0.1448(3) 0.3582(4) 0.16835(17) 0.040(3) Uani 0.460(5) 1 d G . P A 1
C22A C -0.1759(2) 0.3163(4) 0.20402(17) 0.054(2) Uani 0.460(5) 1 d G . P A 1
H22A H -0.2183 0.293 0.1968 0.064 Uiso 0.460(5) 1 calc R U P A 1
C23A C -0.1449(3) 0.3085(4) 0.25022(17) 0.050(2) Uani 0.460(5) 1 d G . P A 1
H23A H -0.1662 0.2799 0.2746 0.06 Uiso 0.460(5) 1 calc R U P A 1
C20A C -0.0829(3) 0.3426(4) 0.2608(2) 0.046(3) Uani 0.460(5) 1 d G . P A 1
C24A C -0.1750(5) 0.3624(7) 0.1222(3) 0.133(3) Uani 0.460(5) 1 d G . P A 1
C25A C -0.1496(6) 0.4119(6) 0.0893(4) 0.133(3) Uani 0.460(5) 1 d G . P A 1
H25A H -0.1117 0.4407 0.0986 0.16 Uiso 0.460(5) 1 calc R U P A 1
C26A C -0.1797(6) 0.4191(6) 0.0428(3) 0.133(3) Uani 0.460(5) 1 d G . P A 1
H26A H -0.1624 0.453 0.0203 0.16 Uiso 0.460(5) 1 calc R U P A 1
C27A C -0.2353(6) 0.3769(6) 0.0292(2) 0.133(3) Uani 0.460(5) 1 d G . P A 1
H27A H -0.2559 0.3819 -0.0026 0.16 Uiso 0.460(5) 1 calc R U P A 1
C28A C -0.2607(5) 0.3274(6) 0.0621(3) 0.133(3) Uani 0.460(5) 1 d G . P A 1
H28A H -0.2986 0.2986 0.0528 0.16 Uiso 0.460(5) 1 calc R U P A 1
N2A N -0.2305(5) 0.3202(6) 0.1086(3) 0.133(3) Uani 0.460(5) 1 d G . P A 1
C19B C -0.0473(3) 0.3525(5) 0.2137(3) 0.061(3) Uani 0.540(5) 1 d G . P A 2
H19B H 0.0005 0.34 0.2145 0.074 Uiso 0.540(5) 1 calc R U P A 2
N1B N -0.0803(4) 0.3636(4) 0.1686(2) 0.064(3) Uani 0.540(5) 1 d G . P A 2
C21B C -0.1502(4) 0.3818(5) 0.16744(17) 0.071(4) Uani 0.540(5) 1 d G . P A 2
C22B C -0.1872(3) 0.3889(5) 0.2114(2) 0.095(4) Uani 0.540(5) 1 d G . P A 2
H22B H -0.235 0.4014 0.2106 0.114 Uiso 0.540(5) 1 calc R U P A 2
C23B C -0.1542(3) 0.3778(5) 0.25653(17) 0.100(4) Uani 0.540(5) 1 d G . P A 2
H23B H -0.1795 0.3826 0.2866 0.12 Uiso 0.540(5) 1 calc R U P A 2
C20B C -0.0842(3) 0.3595(5) 0.2577(2) 0.067(4) Uani 0.540(5) 1 d G . P A 2
C24B C -0.1758(2) 0.3875(3) 0.11956(12) 0.0580(11) Uani 0.540(5) 1 d G . P A 2
C25B C -0.13728(16) 0.3944(3) 0.07624(16) 0.0580(11) Uani 0.540(5) 1 d G . P A
2
H25B H -0.0879 0.3935 0.0775 0.07 Uiso 0.540(5) 1 calc R U P A 2
C26B C -0.1711(2) 0.4025(3) 0.03108(13) 0.0580(11) Uani 0.540(5) 1 d G . P A 2
H26B H -0.1447 0.4072 0.0015 0.07 Uiso 0.540(5) 1 calc R U P A 2
C27B C -0.2433(2) 0.4038(3) 0.02924(11) 0.0580(11) Uani 0.540(5) 1 d G . P A 2
H27B H -0.2664 0.4093 -0.0016 0.07 Uiso 0.540(5) 1 calc R U P A 2
C28B C -0.28180(17) 0.3970(3) 0.07256(14) 0.0580(11) Uani 0.540(5) 1 d G . P A
2
H28B H -0.3312 0.3978 0.0713 0.07 Uiso 0.540(5) 1 calc R U P A 2
N2B N -0.2480(2) 0.3888(3) 0.11772(11) 0.0580(11) Uani 0.540(5) 1 d G . P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.391(5) . ?
C1 C6 1.392(5) . ?
C1 H1 0.95 . ?
C2 C3 1.389(5) . ?
C2 C7 1.520(5) . ?
C3 C4 1.396(6) . ?
C3 O1 1.399(4) . ?
C4 C5 1.395(5) . ?
C4 C12 1.500(5) . ?
C5 O2 1.385(5) . ?
C5 C6 1.404(5) . ?
C6 C7 1.518(5) 6 ?
C7 C6 1.518(5) 7 ?
C7 C8 1.540(5) . ?
C7 H7 1 . ?
C8 C9 1.531(6) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C11 1.527(6) . ?
C9 C10 1.530(7) . ?
C9 H9 1 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 C17 1.368(5) . ?
C12 C13 1.380(6) . ?
C13 C14 1.380(6) . ?
C13 H13 0.95 . ?
C14 C15 1.392(6) . ?
C14 H14 0.95 . ?
C15 C16 1.376(6) . ?
C15 C20A 1.424(6) . ?
C15 C20B 1.560(7) . ?
C16 C17 1.386(5) . ?
C16 H16 0.95 . ?
C17 H17 0.95 . ?
C18 O1 1.411(5) . ?
C18 O2 1.415(5) 7 ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
O2 C18 1.415(5) 6 ?
C29 N3 1.489(9) . ?
C29 H29A 0.98 . ?
C29 H29B 0.98 . ?
C29 H29C 0.98 . ?
N3 O3 1.194(6) 7 ?
N3 O3 1.194(6) 3 ?
N3 O3 1.194(6) 6 ?
N3 O3 1.194(6) . ?
O3 O3 1.480(9) 7 ?
O3 O3 1.480(9) 6 ?
C19A N1A 1.39 . ?
C19A C20A 1.39 . ?
C19A H19A 0.95 . ?
N1A C21A 1.39 . ?
C21A C24A 1.376(7) . ?
C21A C22A 1.39 . ?
C22A C23A 1.39 . ?
C22A H22A 0.95 . ?
C23A C20A 1.39 . ?
C23A H23A 0.95 . ?
C24A C25A 1.39 . ?
C24A N2A 1.39 . ?
C25A C26A 1.39 . ?
C25A H25A 0.95 . ?
C26A C27A 1.39 . ?
C26A H26A 0.95 . ?
C27A C28A 1.39 . ?
C27A H27A 0.95 . ?
C28A N2A 1.39 . ?
C28A H28A 0.95 . ?
C19B N1B 1.39 . ?
C19B C20B 1.39 . ?
C19B H19B 0.95 . ?
N1B C21B 1.39 . ?
C21B C24B 1.387(5) . ?
C21B C22B 1.39 . ?
C22B C23B 1.39 . ?
C22B H22B 0.95 . ?
C23B C20B 1.39 . ?
C23B H23B 0.95 . ?
C24B C25B 1.39 . ?
C24B N2B 1.39 . ?
C25B C26B 1.39 . ?
C25B H25B 0.95 . ?
C26B C27B 1.39 . ?
C26B H26B 0.95 . ?
C27B C28B 1.39 . ?
C27B H27B 0.95 . ?
C28B N2B 1.39 . ?
C28B H28B 0.95 . ?

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
C2 C1 C6 122.6(3) . . ?
C2 C1 H1 118.7 . . ?
C6 C1 H1 118.7 . . ?
C3 C2 C1 117.3(3) . . ?
C3 C2 C7 120.0(3) . . ?
C1 C2 C7 122.6(3) . . ?
C2 C3 C4 123.0(3) . . ?
C2 C3 O1 119.5(4) . . ?
C4 C3 O1 117.5(3) . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 C12 121.4(4) . . ?
C3 C4 C12 121.0(3) . . ?
O2 C5 C4 117.3(3) . . ?
O2 C5 C6 120.9(3) . . ?
C4 C5 C6 121.6(4) . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 C7 122.4(3) . 6 ?
C5 C6 C7 119.6(3) . 6 ?
C6 C7 C2 108.0(3) 7 . ?
C6 C7 C8 114.5(3) 7 . ?
C2 C7 C8 113.9(3) . . ?
C6 C7 H7 106.6 7 . ?
C2 C7 H7 106.6 . . ?
C8 C7 H7 106.6 . . ?
C9 C8 C7 114.7(3) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C11 C9 C10 110.3(5) . . ?
C11 C9 C8 109.7(4) . . ?
C10 C9 C8 112.4(5) . . ?
C11 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 117.6(4) . . ?
C17 C12 C4 121.0(4) . . ?
C13 C12 C4 121.4(3) . . ?
C12 C13 C14 121.6(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 117.2(4) . . ?
C16 C15 C20A 120.2(4) . . ?
C14 C15 C20A 122.3(5) . . ?
C16 C15 C20B 122.5(4) . . ?
C14 C15 C20B 119.8(5) . . ?
C15 C16 C17 121.4(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C12 C17 C16 121.3(4) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
O1 C18 O2 112.3(3) . 7 ?
O1 C18 H18A 109.1 . . ?
O2 C18 H18A 109.1 7 . ?
O1 C18 H18B 109.1 . . ?
O2 C18 H18B 109.1 7 . ?
H18A C18 H18B 107.9 . . ?
C3 O1 C18 115.0(3) . . ?
C5 O2 C18 117.2(3) . 6 ?
N3 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O3 N3 O3 76.6(3) 7 3 ?
O3 N3 O3 122.4(8) 7 6 ?
O3 N3 O3 76.6(3) 3 6 ?
O3 N3 O3 76.6(3) 7 . ?
O3 N3 O3 122.4(8) 3 . ?
O3 N3 O3 76.6(3) 6 . ?
O3 N3 C29 118.8(4) 7 . ?
O3 N3 C29 118.8(4) 3 . ?
O3 N3 C29 118.8(4) 6 . ?
O3 N3 C29 118.8(4) . . ?
N3 O3 O3 51.72(17) . 7 ?
N3 O3 O3 51.72(17) . 6 ?
O3 O3 O3 90.003(2) 7 6 ?
N1A C19A C20A 120 . . ?
N1A C19A H19A 120 . . ?
C20A C19A H19A 120 . . ?
C21A N1A C19A 120 . . ?
C24A C21A N1A 121.3(6) . . ?
C24A C21A C22A 118.7(6) . . ?
N1A C21A C22A 120 . . ?
C21A C22A C23A 120 . . ?
C21A C22A H22A 120 . . ?
C23A C22A H22A 120 . . ?
C20A C23A C22A 120 . . ?
C20A C23A H23A 120 . . ?
C22A C23A H23A 120 . . ?
C23A C20A C19A 120 . . ?
C23A C20A C15 123.6(5) . . ?
C19A C20A C15 116.4(5) . . ?
C21A C24A C25A 118.1(7) . . ?
C21A C24A N2A 121.9(7) . . ?
C25A C24A N2A 120 . . ?
C26A C25A C24A 120 . . ?
C26A C25A H25A 120 . . ?
C24A C25A H25A 120 . . ?
C25A C26A C27A 120 . . ?
C25A C26A H26A 120 . . ?
C27A C26A H26A 120 . . ?
C28A C27A C26A 120 . . ?
C28A C27A H27A 120 . . ?
C26A C27A H27A 120 . . ?
N2A C28A C27A 120 . . ?
N2A C28A H28A 120 . . ?
C27A C28A H28A 120 . . ?
C28A N2A C24A 120 . . ?
N1B C19B C20B 120 . . ?
N1B C19B H19B 120 . . ?
C20B C19B H19B 120 . . ?
C21B N1B C19B 120 . . ?
C24B C21B C22B 127.4(5) . . ?
C24B C21B N1B 112.5(5) . . ?
C22B C21B N1B 120 . . ?
C21B C22B C23B 120 . . ?
C21B C22B H22B 120 . . ?
C23B C22B H22B 120 . . ?
C20B C23B C22B 120 . . ?
C20B C23B H23B 120 . . ?
C22B C23B H23B 120 . . ?
C23B C20B C19B 120 . . ?
C23B C20B C15 120.7(4) . . ?
C19B C20B C15 118.9(4) . . ?
C21B C24B C25B 127.1(4) . . ?
C21B C24B N2B 112.8(4) . . ?
C25B C24B N2B 120 . . ?
C24B C25B C26B 120 . . ?
C24B C25B H25B 120 . . ?
C26B C25B H25B 120 . . ?
C27B C26B C25B 120 . . ?
C27B C26B H26B 120 . . ?
C25B C26B H26B 120 . . ?
C26B C27B C28B 120 . . ?
C26B C27B H27B 120 . . ?
C28B C27B H27B 120 . . ?
N2B C28B C27B 120 . . ?
N2B C28B H28B 120 . . ?
C27B C28B H28B 120 . . ?
C28B N2B C24B 120 . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1024890'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_iodocavitand

_audit_creation_date             2014-09-18T10:27:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C48 H52 I4 O8'
_chemical_formula_sum            'C48 H52 I4 O8'
_chemical_formula_weight         1264.5

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/m'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_Int_Tables_number      12
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   25.752(6)
_cell_length_b                   14.426(3)
_cell_length_c                   19.859(5)
_cell_angle_alpha                90
_cell_angle_beta                 123.395(2)
_cell_angle_gamma                90
_cell_volume                     6159(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.99

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             2464
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.063
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.627
_shelx_estimated_absorpt_T_max   0.886

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_probe          X-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bluker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_number            17086
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.7
_diffrn_reflns_theta_max         28.992
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.912
_reflns_number_total             7751
_reflns_number_gt                6324
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0625P)²+65.2260P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7751
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.738
_refine_diff_density_min         -1.313
_refine_diff_density_rms         0.171

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C26 C 0.6103(5) 0.1577(5) 0.6776(5) 0.063(2) Uani 1 1 d . . . . .
H26A H 0.5666 0.1537 0.6327 0.094 Uiso 1 1 calc R U . . .
H26B H 0.6244 0.0968 0.7033 0.094 Uiso 1 1 calc R U . . .
H26C H 0.6356 0.1774 0.6573 0.094 Uiso 1 1 calc R U . . .
I1 I 0.32580(2) 0.5 0.36893(3) 0.02667(13) Uani 1 2 d S T P . .
I2 I 0.31030(2) 0.14741(3) 0.59689(2) 0.03144(11) Uani 1 1 d . . . . .
I3 I 0.28523(3) 0.5 0.83286(4) 0.03926(15) Uani 1 2 d S T P . .
O3 O 0.38211(16) 0.2174(2) 0.7788(2) 0.0228(7) Uani 1 1 d . . . . .
O2 O 0.41217(17) 0.3341(2) 0.47771(19) 0.0216(7) Uani 1 1 d . . . . .
O4 O 0.37321(17) 0.3337(2) 0.8549(2) 0.0223(7) Uani 1 1 d . . . . .
C9 C 0.5175(3) 0.5 0.6356(4) 0.0174(12) Uani 1 2 d S T P . .
H9 H 0.554 0.5 0.6887 0.021 Uiso 1 2 calc R U P . .
C10 C 0.4374(2) 0.4161(3) 0.5208(3) 0.0194(9) Uani 1 1 d . . . . .
C2 C 0.4150(2) 0.2455(3) 0.7457(3) 0.0194(9) Uani 1 1 d . . . . .
O1 O 0.40619(17) 0.2160(2) 0.5560(2) 0.0240(7) Uani 1 1 d . . . . .
C13 C 0.3727(3) 0.5 0.8519(4) 0.0198(12) Uani 1 2 d S T P . .
C4 C 0.5031(2) 0.3187(3) 0.7578(3) 0.0186(8) Uani 1 1 d . . . . .
H4 H 0.5403 0.3539 0.7885 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4275(2) 0.2453(3) 0.6337(3) 0.0222(9) Uani 1 1 d . . . . .
C18 C 0.4930(2) 0.3224(3) 0.8789(3) 0.0180(8) Uani 1 1 d . . . . .
H18 H 0.4765 0.2754 0.8996 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4027(2) 0.4168(3) 0.8588(3) 0.0183(8) Uani 1 1 d . . . . .
C5 C 0.4829(2) 0.2936(3) 0.6789(3) 0.0188(9) Uani 1 1 d . . . . .
C19 C 0.5891(2) 0.3210(4) 0.7004(3) 0.0231(9) Uani 1 1 d . . . . .
H19A H 0.6088 0.3421 0.6721 0.028 Uiso 1 1 calc R U . . .
H19B H 0.6002 0.3662 0.7439 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4915(3) 0.5 0.8815(4) 0.0179(12) Uani 1 2 d S T P . .
H16 H 0.532 0.5 0.8913 0.021 Uiso 1 2 calc R U P . .
C22 C 0.5643(2) 0.3231(3) 0.9370(3) 0.0221(9) Uani 1 1 d . . . . .
H22A H 0.5815 0.3685 0.9169 0.027 Uiso 1 1 calc R U . . .
H22B H 0.5748 0.3451 0.9904 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4917(2) 0.4150(3) 0.5981(3) 0.0171(8) Uani 1 1 d . . . . .
C7 C 0.5180(2) 0.3230(3) 0.6401(3) 0.0193(9) Uani 1 1 d . . . . .
H7 H 0.5079 0.2765 0.5972 0.023 Uiso 1 1 calc R U . . .
C20 C 0.6167(3) 0.2276(4) 0.7389(3) 0.0309(11) Uani 1 1 d . . . . .
H20 H 0.5935 0.2033 0.7623 0.037 Uiso 1 1 calc R U . . .
C15 C 0.4629(2) 0.4151(3) 0.8746(3) 0.0194(9) Uani 1 1 d . . . . .
C17 C 0.3427(2) 0.2841(3) 0.7810(3) 0.0230(9) Uani 1 1 d . . . . .
H17A H 0.3057 0.2524 0.7735 0.028 Uiso 1 1 calc R U . . .
H17B H 0.3282 0.3282 0.7359 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4710(2) 0.2942(3) 0.7929(3) 0.0179(8) Uani 1 1 d . . . . .
C1 C 0.3930(2) 0.2208(3) 0.6667(3) 0.0226(9) Uani 1 1 d . . . . .
C23 C 0.5961(3) 0.2302(4) 0.9483(3) 0.0311(11) Uani 1 1 d . . . . .
H23 H 0.5859 0.2092 0.8943 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3726(3) 0.2827(4) 0.4931(3) 0.0270(10) Uani 1 1 d . . . . .
H12A H 0.3407 0.2504 0.4431 0.032 Uiso 1 1 calc R U . . .
H12B H 0.351 0.326 0.5084 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4098(3) 0.5 0.4825(4) 0.0212(13) Uani 1 2 d S T P . .
C24 C 0.5731(3) 0.1560(4) 0.9810(5) 0.0460(16) Uani 1 1 d . . . . .
H24A H 0.5825 0.1751 1.0339 0.069 Uiso 1 1 calc R U . . .
H24B H 0.5941 0.0971 0.9862 0.069 Uiso 1 1 calc R U . . .
H24C H 0.5281 0.1481 0.9437 0.069 Uiso 1 1 calc R U . . .
C21 C 0.6844(4) 0.2390(6) 0.8071(5) 0.064(2) Uani 1 1 d . . . . .
H21A H 0.7014 0.1788 0.8327 0.096 Uiso 1 1 calc R U . . .
H21B H 0.6874 0.2825 0.8471 0.096 Uiso 1 1 calc R U . . .
H21C H 0.708 0.2633 0.7856 0.096 Uiso 1 1 calc R U . . .
C25 C 0.6661(3) 0.2408(5) 1.0031(4) 0.0481(16) Uani 1 1 d . . . . .
H25A H 0.6772 0.2622 1.0564 0.072 Uiso 1 1 calc R U . . .
H25B H 0.6803 0.2861 0.9799 0.072 Uiso 1 1 calc R U . . .
H25C H 0.686 0.1808 1.0086 0.072 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C26 C20 1.518(8) . ?
I1 C11 2.097(7) . ?
I2 C1 2.081(5) . ?
I3 C13 2.070(6) . ?
O3 C2 1.387(5) . ?
O3 C17 1.417(6) . ?
O2 C10 1.394(5) . ?
O2 C12 1.422(6) . ?
O4 C14 1.398(5) . ?
O4 C17 1.419(6) . ?
C9 C8 1.399(5) 6_565 ?
C9 C8 1.399(5) . ?
C10 C8 1.396(6) . ?
C10 C11 1.397(6) . ?
C2 C1 1.390(6) . ?
C2 C3 1.403(7) . ?
O1 C6 1.389(5) . ?
O1 C12 1.431(6) . ?
C13 C14 1.393(5) . ?
C13 C14 1.393(5) 6_565 ?
C4 C3 1.390(6) . ?
C4 C5 1.399(6) . ?
C6 C5 1.385(7) . ?
C6 C1 1.406(6) . ?
C18 C15 1.525(6) . ?
C18 C3 1.529(6) . ?
C18 C22 1.539(7) . ?
C14 C15 1.402(6) . ?
C5 C7 1.535(6) . ?
C19 C20 1.520(7) . ?
C19 C7 1.540(7) . ?
C16 C15 1.396(6) . ?
C16 C15 1.396(6) 6_565 ?
C22 C23 1.523(7) . ?
C8 C7 1.515(6) . ?
C20 C21 1.516(10) . ?
C23 C25 1.515(9) . ?
C23 C24 1.530(9) . ?
C11 C10 1.397(6) 6_565 ?

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
C2 O3 C17 116.8(4) . . ?
C10 O2 C12 117.2(3) . . ?
C14 O4 C17 117.7(3) . . ?
C8 C9 C8 122.5(6) 6_565 . ?
O2 C10 C8 120.8(4) . . ?
O2 C10 C11 118.4(4) . . ?
C8 C10 C11 120.6(4) . . ?
O3 C2 C1 119.0(4) . . ?
O3 C2 C3 120.0(4) . . ?
C1 C2 C3 120.9(4) . . ?
C6 O1 C12 116.4(4) . . ?
C14 C13 C14 119.1(6) . 6_565 ?
C14 C13 I3 120.5(3) . . ?
C14 C13 I3 120.5(3) 6_565 . ?
C3 C4 C5 122.6(4) . . ?
C5 C6 O1 120.5(4) . . ?
C5 C6 C1 121.0(4) . . ?
O1 C6 C1 118.4(4) . . ?
C15 C18 C3 107.8(4) . . ?
C15 C18 C22 113.3(4) . . ?
C3 C18 C22 113.3(4) . . ?
C13 C14 O4 118.6(4) . . ?
C13 C14 C15 121.4(4) . . ?
O4 C14 C15 119.9(4) . . ?
C6 C5 C4 118.1(4) . . ?
C6 C5 C7 119.8(4) . . ?
C4 C5 C7 122.1(4) . . ?
C20 C19 C7 115.8(4) . . ?
C15 C16 C15 122.6(6) . 6_565 ?
C23 C22 C18 115.3(4) . . ?
C10 C8 C9 118.1(4) . . ?
C10 C8 C7 119.4(4) . . ?
C9 C8 C7 122.4(4) . . ?
C8 C7 C5 108.0(4) . . ?
C8 C7 C19 115.2(4) . . ?
C5 C7 C19 112.4(4) . . ?
C21 C20 C26 110.7(6) . . ?
C21 C20 C19 110.0(5) . . ?
C26 C20 C19 111.8(5) . . ?
C16 C15 C14 117.7(4) . . ?
C16 C15 C18 122.7(4) . . ?
C14 C15 C18 119.5(4) . . ?
O3 C17 O4 112.1(4) . . ?
C4 C3 C2 117.9(4) . . ?
C4 C3 C18 122.5(4) . . ?
C2 C3 C18 119.5(4) . . ?
C2 C1 C6 119.5(4) . . ?
C2 C1 I2 120.9(3) . . ?
C6 C1 I2 119.7(3) . . ?
C25 C23 C22 110.4(5) . . ?
C25 C23 C24 110.5(5) . . ?
C22 C23 C24 112.1(4) . . ?
O2 C12 O1 112.2(4) . . ?
C10 C11 C10 120.0(6) 6_565 . ?
C10 C11 I1 120.0(3) 6_565 . ?
C10 C11 I1 120.0(3) . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1024891'
