# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cage6_squeezed
_database_code_depnum_ccdc_archive 'CCDC 1477553'
_audit_update_record             
;
2016-05-01 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C72 H80 N12 O4'
_chemical_formula_sum            'C72 H80 N12 O4'
_chemical_formula_weight         1177.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           210
_space_group_name_H-M_alt        'F 41 3 2'
_space_group_name_Hall           'F 4d 2 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   24.8942(5)
_cell_length_b                   24.8942(5)
_cell_length_c                   24.8942(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     15427.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3810
_cell_measurement_theta_min      3.075
_cell_measurement_theta_max      66.734

_exptl_crystal_description       tetrahedral
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.014
_exptl_crystal_F_000             5024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.509
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_reflns_number            14070
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         53.396
_diffrn_reflns_theta_full        53.396
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             772
_reflns_number_gt                748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.526
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         772
_refine_ls_number_parameters     73
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.1104
_refine_ls_wR_factor_ref         0.2918
_refine_ls_wR_factor_gt          0.2882
_refine_ls_goodness_of_fit_ref   1.431
_refine_ls_restrained_S_all      1.436
_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_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 0.7402(8) 0.2778(5) 0.3795(3) 0.232(11) Uani 1 1 d D . . . .
H1B H 0.7181 0.2843 0.3471 0.278 Uiso 1 1 calc R U . . .
H1A H 0.7710 0.3029 0.3789 0.278 Uiso 1 1 calc R U . . .
C2 C 0.7065(4) 0.2874(5) 0.4298(3) 0.164(4) Uani 1 1 d D . . . .
H2B H 0.6932 0.3249 0.4298 0.197 Uiso 1 1 calc R U . . .
H2A H 0.6750 0.2632 0.4294 0.197 Uiso 1 1 calc R U . . .
C3 C 0.7389(2) 0.2775(3) 0.48055(19) 0.1000(19) Uani 1 1 d . . . . .
H3 H 0.7693 0.3037 0.4818 0.120 Uiso 1 1 calc R U . . .
N1 N 0.7051(2) 0.2862(2) 0.52627(18) 0.1023(18) Uani 1 1 d . . . . .
C4 C 0.7150(3) 0.3240(3) 0.5586(2) 0.107(2) Uani 1 1 d . . . . .
H4 H 0.7465 0.3446 0.5529 0.129 Uiso 1 1 calc R U . . .
C5 C 0.6810(2) 0.3381(2) 0.6044(2) 0.103(2) Uani 1 1 d . . . . .
C6 C 0.6361(2) 0.3055(3) 0.6170(2) 0.103(2) Uani 1 1 d . . . . .
H6 H 0.6277 0.2747 0.5955 0.124 Uiso 0.3333 1 d R U P . .
O1 O 0.6235(4) 0.2638(6) 0.5857(5) 0.107(3) Uani 0.3333 1 d . . P . .
H1 H 0.6453 0.2620 0.5599 0.128 Uiso 0.3333 1 d R U P . .


_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 C1 1.47(2) 75_655 ?
C1 C2 1.527(16) . ?
C1 H1B 0.9900 . ?
C1 H1A 0.9900 . ?
C2 C3 1.518(8) . ?
C2 H2B 0.9900 . ?
C2 H2A 0.9900 . ?
C3 N1 1.432(7) . ?
C3 C3 1.476(13) 75_655 ?
C3 H3 1.0000 . ?
N1 C4 1.263(7) . ?
C4 C5 1.461(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.409(8) 13_665 ?
C5 C6 1.416(9) . ?
C6 O1 1.336(14) . ?
C6 C5 1.409(8) 14_566 ?
C6 H6 0.9597 . ?
O1 H6 0.3792 . ?
O1 H1 0.8401 . ?

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
C1 C1 C2 109.3(11) 75_655 . ?
C1 C1 H1B 109.8 75_655 . ?
C2 C1 H1B 109.8 . . ?
C1 C1 H1A 109.8 75_655 . ?
C2 C1 H1A 109.8 . . ?
H1B C1 H1A 108.3 . . ?
C3 C2 C1 111.5(9) . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
H2B C2 H2A 108.0 . . ?
N1 C3 C3 111.2(4) . 75_655 ?
N1 C3 C2 108.9(6) . . ?
C3 C3 C2 110.5(6) 75_655 . ?
N1 C3 H3 108.7 . . ?
C3 C3 H3 108.7 75_655 . ?
C2 C3 H3 108.7 . . ?
C4 N1 C3 120.4(6) . . ?
N1 C4 C5 124.3(6) . . ?
N1 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C6 C5 C6 121.2(6) 13_665 . ?
C6 C5 C4 119.3(5) 13_665 . ?
C6 C5 C4 119.5(6) . . ?
O1 C6 C5 121.2(7) . 14_566 ?
O1 C6 C5 120.0(7) . . ?
C5 C6 C5 118.8(6) 14_566 . ?
C5 C6 H6 120.7 14_566 . ?
C5 C6 H6 120.5 . . ?
C6 O1 H1 109.7 . . ?
H6 O1 H1 111.0 . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.007 -0.002 0.001 2467 248 ' '
2 0.000 0.000 0.500 13 8 ' '
3 0.000 0.500 0.000 13 8 ' '
4 0.125 0.125 0.625 6 4 ' '
5 0.125 0.375 0.875 6 3 ' '
6 0.125 0.625 0.125 6 4 ' '
7 0.125 0.875 0.375 6 3 ' '
8 0.250 0.250 0.750 13 8 ' '
9 0.250 0.750 0.250 13 8 ' '
10 0.375 0.125 0.875 6 3 ' '
11 0.375 0.375 0.625 6 3 ' '
12 0.375 0.625 0.375 6 3 ' '
13 0.375 0.875 0.125 6 3 ' '
14 0.500 0.000 0.000 13 8 ' '
15 0.500 0.500 0.500 13 8 ' '
16 0.625 0.125 0.125 6 4 ' '
17 0.625 0.375 0.375 6 3 ' '
18 0.625 0.625 0.625 6 4 ' '
19 0.625 0.875 0.875 6 3 ' '
20 0.750 0.250 0.250 13 8 ' '
21 0.750 0.750 0.750 13 8 ' '
22 0.875 0.125 0.375 6 3 ' '
23 0.875 0.375 0.125 6 3 ' '
24 0.875 0.625 0.875 6 3 ' '
25 0.875 0.875 0.625 6 3 ' '
_platon_squeeze_details          
;
Approx. four molecules of xylene have been sqeezed
;

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.098


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'commercial xylene mixture'
