# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Hasell, Thomas'
'Schmidtmann, Marc'
'Smith, Martin'
'Stone, Corinne'
'Cooper, Andrew'

_publ_contact_author_name        'Cooper, Andrew'
_publ_contact_author_email       aicooper@liv.ac.uk

_publ_section_title              
;
Reversible water uptake by an imine-based porous organic cage
;

# Attachment '- H2O_CC3.cif'

data_H2O_CC3
_database_code_depnum_ccdc_archive 'CCDC 869701'
#TrackingRef '- H2O_CC3.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C72 H108 N12 O12'
_chemical_formula_weight         1333.70

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'

_symmetry_cell_setting           cubic
_symmetry_space_group_name_H-M   F4(1)32

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'
'z, x, y'
'z+1/2, -x, -y+1/2'
'-z, -x+1/2, y+1/2'
'-z+1/2, x+1/2, -y'
'y, z, x'
'-y+1/2, z+1/2, -x'
'y+1/2, -z, -x+1/2'
'-y, -z+1/2, x+1/2'
'y+3/4, x+1/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'y+1/4, -x+3/4, z+3/4'
'-y+3/4, x+3/4, z+1/4'
'x+3/4, z+1/4, -y+3/4'
'-x+3/4, z+3/4, y+1/4'
'-x+1/4, -z+1/4, -y+1/4'
'x+1/4, -z+3/4, y+3/4'
'z+3/4, y+1/4, -x+3/4'
'z+1/4, -y+3/4, x+3/4'
'-z+3/4, y+3/4, x+1/4'
'-z+1/4, -y+1/4, -x+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1, z+1'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z+1'
'z, x+1/2, y+1/2'
'z+1/2, -x+1/2, -y+1'
'-z, -x+1, y+1'
'-z+1/2, x+1, -y+1/2'
'y, z+1/2, x+1/2'
'-y+1/2, z+1, -x+1/2'
'y+1/2, -z+1/2, -x+1'
'-y, -z+1, x+1'
'y+3/4, x+3/4, -z+5/4'
'-y+1/4, -x+3/4, -z+3/4'
'y+1/4, -x+5/4, z+5/4'
'-y+3/4, x+5/4, z+3/4'
'x+3/4, z+3/4, -y+5/4'
'-x+3/4, z+5/4, y+3/4'
'-x+1/4, -z+3/4, -y+3/4'
'x+1/4, -z+5/4, y+5/4'
'z+3/4, y+3/4, -x+5/4'
'z+1/4, -y+5/4, x+5/4'
'-z+3/4, y+5/4, x+3/4'
'-z+1/4, -y+3/4, -x+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y+1/2, z+1'
'-x+1, y+1/2, -z+1/2'
'x+1, -y, -z+1'
'z+1/2, x, y+1/2'
'z+1, -x, -y+1'
'-z+1/2, -x+1/2, y+1'
'-z+1, x+1/2, -y+1/2'
'y+1/2, z, x+1/2'
'-y+1, z+1/2, -x+1/2'
'y+1, -z, -x+1'
'-y+1/2, -z+1/2, x+1'
'y+5/4, x+1/4, -z+5/4'
'-y+3/4, -x+1/4, -z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-y+5/4, x+3/4, z+3/4'
'x+5/4, z+1/4, -y+5/4'
'-x+5/4, z+3/4, y+3/4'
'-x+3/4, -z+1/4, -y+3/4'
'x+3/4, -z+3/4, y+5/4'
'z+5/4, y+1/4, -x+5/4'
'z+3/4, -y+3/4, x+5/4'
'-z+5/4, y+3/4, x+3/4'
'-z+3/4, -y+1/4, -x+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1, y+1, -z'
'x+1, -y+1/2, -z+1/2'
'z+1/2, x+1/2, y'
'z+1, -x+1/2, -y+1/2'
'-z+1/2, -x+1, y+1/2'
'-z+1, x+1, -y'
'y+1/2, z+1/2, x'
'-y+1, z+1, -x'
'y+1, -z+1/2, -x+1/2'
'-y+1/2, -z+1, x+1/2'
'y+5/4, x+3/4, -z+3/4'
'-y+3/4, -x+3/4, -z+1/4'
'y+3/4, -x+5/4, z+3/4'
'-y+5/4, x+5/4, z+1/4'
'x+5/4, z+3/4, -y+3/4'
'-x+5/4, z+5/4, y+1/4'
'-x+3/4, -z+3/4, -y+1/4'
'x+3/4, -z+5/4, y+3/4'
'z+5/4, y+3/4, -x+3/4'
'z+3/4, -y+5/4, x+3/4'
'-z+5/4, y+5/4, x+1/4'
'-z+3/4, -y+3/4, -x+1/4'

_cell_length_a                   25.1381(7)
_cell_length_b                   25.1381(7)
_cell_length_c                   25.1381(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     15885.4(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9814
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      19.98

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5760
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7291
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2008/1 (Sheldrick, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            73441
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         23.25
_reflns_number_total             975
_reflns_number_gt                914
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2011)'
_computing_cell_refinement       'Bruker AXS SAINT V7.68A'
_computing_data_reduction        'Bruker AXS SAINT V7.68A'
_computing_structure_solution    'SHELXD (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.1000P)^2^+18.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_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(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         975
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0881
_refine_ls_wR_factor_ref         0.2570
_refine_ls_wR_factor_gt          0.2553
_refine_ls_goodness_of_fit_ref   1.278
_refine_ls_restrained_S_all      1.278
_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 0.29549(16) 0.21503(19) 0.02911(16) 0.1134(13) Uani 1 1 d . . .
C1 C 0.3053(2) 0.1210(2) 0.1379(2) 0.1167(16) Uani 1 1 d . . .
H1 H 0.2762 0.1002 0.1285 0.140 Uiso 1 1 calc R . .
C2 C 0.3179(2) 0.1653(2) 0.10696(19) 0.1112(15) Uani 1 1 d . . .
C3 C 0.2843(2) 0.1779(2) 0.0610(2) 0.1227(18) Uani 1 1 d . . .
H3 H 0.2538 0.1578 0.0551 0.147 Uiso 1 1 calc R . .
C4 C 0.26155(19) 0.2221(2) -0.01731(17) 0.1129(15) Uani 1 1 d . . .
H4 H 0.2322 0.1965 -0.0153 0.135 Uiso 1 1 calc R . .
C5 C 0.2924(3) 0.2119(4) -0.0673(2) 0.171(3) Uani 1 1 d . . .
H5A H 0.3037 0.1750 -0.0678 0.206 Uiso 1 1 calc R . .
H5B H 0.3240 0.2339 -0.0674 0.206 Uiso 1 1 calc R . .
C6 C 0.2604(5) 0.2232(3) -0.1170(2) 0.208(5) Uani 1 1 d . . .
H6A H 0.2828 0.2182 -0.1480 0.249 Uiso 1 1 calc R . .
H6B H 0.2311 0.1982 -0.1193 0.249 Uiso 1 1 calc R . .
O1 O 0.3750 0.2982(4) 0.0482(4) 0.306(6) Uani 1 2 d S . .
O2 O 0.3551(7) 0.3551(7) 0.1449(7) 0.39(2) Uani 0.50 3 d SP . .
O3 O 0.2982(9) 0.2982(9) 0.2018(9) 0.64(3) Uani 1 3 d S . .

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 0.108(3) 0.132(3) 0.101(3) -0.010(2) 0.003(2) -0.009(2)
C1 0.122(4) 0.110(3) 0.118(4) 0.002(3) -0.003(3) -0.005(3)
C2 0.122(4) 0.109(3) 0.102(3) -0.007(3) 0.000(3) 0.001(3)
C3 0.145(4) 0.113(4) 0.111(4) -0.002(3) -0.012(3) -0.017(3)
C4 0.122(4) 0.130(4) 0.087(3) -0.008(2) 0.003(2) -0.021(3)
C5 0.176(6) 0.235(8) 0.104(4) -0.040(5) 0.033(4) -0.023(5)
C6 0.241(10) 0.293(14) 0.089(3) -0.050(5) 0.028(5) -0.058(11)
O1 0.321(14) 0.299(8) 0.299(8) 0.085(10) 0.045(7) -0.045(7)
O2 0.39(2) 0.39(2) 0.39(2) 0.085(17) 0.085(17) -0.085(17)
O3 0.64(3) 0.64(3) 0.64(3) -0.19(3) -0.19(3) 0.19(3)

_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 C3 1.262(6) . ?
N1 C4 1.457(6) . ?
C1 C2 1.379(6) 34_545 ?
C1 C2 1.396(6) . ?
C1 H1 0.9300 . ?
C2 C1 1.379(6) 55_554 ?
C2 C3 1.465(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.499(6) . ?
C4 C4 1.516(10) 50_554 ?
C4 H4 0.9800 . ?
C5 C6 1.513(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C6 1.444(17) 50_554 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O2 O2 1.74(6) 86 ?

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
C3 N1 C4 118.0(4) . . ?
C2 C1 C2 122.1(6) 34_545 . ?
C2 C1 H1 118.9 34_545 . ?
C2 C1 H1 118.9 . . ?
C1 C2 C1 117.8(6) 55_554 . ?
C1 C2 C3 123.3(5) 55_554 . ?
C1 C2 C3 118.8(5) . . ?
N1 C3 C2 122.2(5) . . ?
N1 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
N1 C4 C5 110.3(5) . . ?
N1 C4 C4 109.7(3) . 50_554 ?
C5 C4 C4 111.0(4) . 50_554 ?
N1 C4 H4 108.6 . . ?
C5 C4 H4 108.6 . . ?
C4 C4 H4 108.6 50_554 . ?
C4 C5 C6 112.6(6) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C6 C6 C5 111.6(7) 50_554 . ?
C6 C6 H6A 109.3 50_554 . ?
C5 C6 H6A 109.3 . . ?
C6 C6 H6B 109.3 50_554 . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037