# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1494828'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2016-11-20 downloaded from the CCDC.
;
_audit_creation_date             2016-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C192 H96 Eu24 N96 O128)'
_chemical_formula_sum            'C96 H48 Eu12 N48 O64'
_chemical_formula_weight         4721.34
_chemical_melting_point          ?
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'
Eu Eu -0.1578 3.6682 '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'

_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.
;
_space_group_crystal_system      cubic
_space_group_IT_number           225
_space_group_name_H-M_alt        'F m -3 m'
_space_group_name_Hall           '-F 4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x, -z, y'
'x, -y, -z'
'x, z, -y'
'z, y, -x'
'-x, y, -z'
'-z, y, x'
'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, x, -z'
'-y, -x, -z'
'-x, z, y'
'-x, -z, -y'
'z, -y, x'
'-z, -y, -x'
'x, y+1/2, z+1/2'
'-y, x+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'y, -x+1/2, z+1/2'
'x, -z+1/2, y+1/2'
'x, -y+1/2, -z+1/2'
'x, z+1/2, -y+1/2'
'z, y+1/2, -x+1/2'
'-x, y+1/2, -z+1/2'
'-z, y+1/2, x+1/2'
'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, x+1/2, -z+1/2'
'-y, -x+1/2, -z+1/2'
'-x, z+1/2, y+1/2'
'-x, -z+1/2, -y+1/2'
'z, -y+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'x+1/2, y, z+1/2'
'-y+1/2, x, z+1/2'
'-x+1/2, -y, z+1/2'
'y+1/2, -x, z+1/2'
'x+1/2, -z, y+1/2'
'x+1/2, -y, -z+1/2'
'x+1/2, z, -y+1/2'
'z+1/2, y, -x+1/2'
'-x+1/2, y, -z+1/2'
'-z+1/2, y, x+1/2'
'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+1/2, x, -z+1/2'
'-y+1/2, -x, -z+1/2'
'-x+1/2, z, y+1/2'
'-x+1/2, -z, -y+1/2'
'z+1/2, -y, x+1/2'
'-z+1/2, -y, -x+1/2'
'x+1/2, y+1/2, z'
'-y+1/2, x+1/2, z'
'-x+1/2, -y+1/2, z'
'y+1/2, -x+1/2, z'
'x+1/2, -z+1/2, y'
'x+1/2, -y+1/2, -z'
'x+1/2, z+1/2, -y'
'z+1/2, y+1/2, -x'
'-x+1/2, y+1/2, -z'
'-z+1/2, y+1/2, x'
'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+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'-x+1/2, z+1/2, y'
'-x+1/2, -z+1/2, -y'
'z+1/2, -y+1/2, x'
'-z+1/2, -y+1/2, -x'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x, z, -y'
'-x, y, z'
'-x, -z, y'
'-z, -y, x'
'x, -y, z'
'z, -y, -x'
'-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, -x, z'
'y, x, z'
'x, -z, -y'
'x, z, y'
'-z, y, -x'
'z, y, x'
'-x, -y+1/2, -z+1/2'
'y, -x+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'-y, x+1/2, -z+1/2'
'-x, z+1/2, -y+1/2'
'-x, y+1/2, z+1/2'
'-x, -z+1/2, y+1/2'
'-z, -y+1/2, x+1/2'
'x, -y+1/2, z+1/2'
'z, -y+1/2, -x+1/2'
'-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, -x+1/2, z+1/2'
'y, x+1/2, z+1/2'
'x, -z+1/2, -y+1/2'
'x, z+1/2, y+1/2'
'-z, y+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'-x+1/2, -y, -z+1/2'
'y+1/2, -x, -z+1/2'
'x+1/2, y, -z+1/2'
'-y+1/2, x, -z+1/2'
'-x+1/2, z, -y+1/2'
'-x+1/2, y, z+1/2'
'-x+1/2, -z, y+1/2'
'-z+1/2, -y, x+1/2'
'x+1/2, -y, z+1/2'
'z+1/2, -y, -x+1/2'
'-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+1/2, -x, z+1/2'
'y+1/2, x, z+1/2'
'x+1/2, -z, -y+1/2'
'x+1/2, z, y+1/2'
'-z+1/2, y, -x+1/2'
'z+1/2, y, x+1/2'
'-x+1/2, -y+1/2, -z'
'y+1/2, -x+1/2, -z'
'x+1/2, y+1/2, -z'
'-y+1/2, x+1/2, -z'
'-x+1/2, z+1/2, -y'
'-x+1/2, y+1/2, z'
'-x+1/2, -z+1/2, y'
'-z+1/2, -y+1/2, x'
'x+1/2, -y+1/2, z'
'z+1/2, -y+1/2, -x'
'-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+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
'x+1/2, -z+1/2, -y'
'x+1/2, z+1/2, y'
'-z+1/2, y+1/2, -x'
'z+1/2, y+1/2, x'

_cell_length_a                   21.713(3)
_cell_length_b                   21.713(3)
_cell_length_c                   21.713(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10237(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1695
_cell_measurement_temperature    282(1)
_cell_measurement_theta_max      73.0890
_cell_measurement_theta_min      4.0530
_shelx_estimated_absorpt_T_max   1.00000
_shelx_estimated_absorpt_T_min   0.70297
_exptl_absorpt_coefficient_mu    3.692
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             4456
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   0.478
_exptl_transmission_factor_min   0.448
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            ?
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.104
_diffrn_reflns_theta_min         1.624
_diffrn_ambient_temperature      282(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                467
_reflns_number_total             515
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXL (Sheldrick, 2015)'
_refine_diff_density_max         1.578
_refine_diff_density_min         -3.013
_refine_diff_density_rms         0.306
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     34
_refine_ls_number_reflns         515
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.272
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1232P)²+104.5891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.1763
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Restrained distances
 N1-O2
 2.01 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim C2 \\sim C3: within 3.8A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(N1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: H1(0.5)
5.a Rotating group:
 N1(H1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Eu1 Eu 0.0000 0.0000 0.12945(2) 0.01987(13) Uani 1 8 d S T P . .
O1 O 0.05889(11) 0.05889(11) 0.05889(11) 0.0049(9) Uani 1 6 d S T P . .
O2 O 0.0000 -0.09919(18) 0.17422(14) 0.0437(11) Uani 1 2 d DS T P . .
N1 N 0.0000 -0.1274(4) 0.2625(2) 0.154(3) Uani 1 2 d DS TU P . .
H1 H -0.0415 -0.0829 0.2545 0.185 Uiso 0.5 1 d GR . . . .
C1 C 0.0000 -0.1551(3) 0.1551(3) 0.046(2) Uani 1 4 d S T P . .
C2 C 0.0000 -0.2042(4) 0.2042(4) 0.087(2) Uani 1 4 d S TU P . .
C3 C 0.0000 -0.1898(4) 0.2653(4) 0.0955(19) Uani 1 2 d S TU 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
Eu1 Eu1 3.9749(8) 8 ?
Eu1 Eu1 3.9749(8) 104 ?
Eu1 Eu1 3.9749(8) 101 ?
Eu1 Eu1 3.9749(8) 5 ?
Eu1 O1 2.3701(11) 3 ?
Eu1 O1 2.3701(11) 2 ?
Eu1 O1 2.3701(11) 4 ?
Eu1 O1 2.3701(11) . ?
Eu1 O2 2.363(4) . ?
Eu1 O2 2.363(4) 4 ?
Eu1 O2 2.363(4) 2 ?
Eu1 O2 2.363(4) 3 ?
O1 Eu1 2.3700(11) 8 ?
O1 Eu1 2.3700(11) 101 ?
O2 C1 1.283(5) . ?
N1 C3 1.358(11) . ?
C1 O2 1.283(5) 117 ?
C1 C2 1.506(14) . ?
C2 C3 1.363(11) . ?
C2 C3 1.363(11) 117 ?
C3 C3 1.378(18) 45_545 ?

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
Eu1 Eu1 Eu1 60.0 101 8 ?
Eu1 Eu1 Eu1 60.0 104 101 ?
Eu1 Eu1 Eu1 90.0 5 101 ?
Eu1 Eu1 Eu1 90.0 104 8 ?
Eu1 Eu1 Eu1 60.0 5 8 ?
Eu1 Eu1 Eu1 60.0 5 104 ?
O1 Eu1 Eu1 85.67(9) 3 8 ?
O1 Eu1 Eu1 33.01(4) 2 104 ?
O1 Eu1 Eu1 33.01(4) . 8 ?
O1 Eu1 Eu1 33.01(4) . 101 ?
O1 Eu1 Eu1 33.01(4) 4 5 ?
O1 Eu1 Eu1 33.01(4) 4 8 ?
O1 Eu1 Eu1 85.67(9) 2 5 ?
O1 Eu1 Eu1 85.67(9) . 5 ?
O1 Eu1 Eu1 85.67(9) . 104 ?
O1 Eu1 Eu1 85.67(9) 2 8 ?
O1 Eu1 Eu1 33.01(4) 3 104 ?
O1 Eu1 Eu1 33.01(4) 2 101 ?
O1 Eu1 Eu1 85.67(9) 4 104 ?
O1 Eu1 Eu1 33.01(4) 3 5 ?
O1 Eu1 Eu1 85.67(9) 3 101 ?
O1 Eu1 Eu1 85.67(9) 4 101 ?
O1 Eu1 O1 65.30(11) 3 4 ?
O1 Eu1 O1 99.5(2) 4 2 ?
O1 Eu1 O1 65.30(11) . 2 ?
O1 Eu1 O1 99.5(2) . 3 ?
O1 Eu1 O1 65.30(11) . 4 ?
O1 Eu1 O1 65.30(11) 3 2 ?
O2 Eu1 Eu1 106.91(5) . 8 ?
O2 Eu1 Eu1 106.91(5) . 104 ?
O2 Eu1 Eu1 106.91(5) 2 101 ?
O2 Eu1 Eu1 69.29(8) 4 104 ?
O2 Eu1 Eu1 106.91(5) 3 104 ?
O2 Eu1 Eu1 159.29(8) 3 5 ?
O2 Eu1 Eu1 69.29(8) 3 101 ?
O2 Eu1 Eu1 106.91(5) 4 5 ?
O2 Eu1 Eu1 106.91(5) 3 8 ?
O2 Eu1 Eu1 159.29(8) 2 104 ?
O2 Eu1 Eu1 159.29(8) 4 8 ?
O2 Eu1 Eu1 106.91(5) 2 5 ?
O2 Eu1 Eu1 106.91(5) 4 101 ?
O2 Eu1 Eu1 69.30(8) . 5 ?
O2 Eu1 Eu1 159.29(8) . 101 ?
O2 Eu1 Eu1 69.29(8) 2 8 ?
O2 Eu1 O1 76.95(10) 3 2 ?
O2 Eu1 O1 139.26(5) 2 3 ?
O2 Eu1 O1 139.26(5) 4 . ?
O2 Eu1 O1 139.26(5) 3 3 ?
O2 Eu1 O1 76.95(10) 2 . ?
O2 Eu1 O1 139.26(5) 3 4 ?
O2 Eu1 O1 76.95(10) 2 4 ?
O2 Eu1 O1 139.26(5) 2 2 ?
O2 Eu1 O1 76.95(10) 3 . ?
O2 Eu1 O1 76.95(10) 4 3 ?
O2 Eu1 O1 139.26(5) 4 4 ?
O2 Eu1 O1 76.95(10) 4 2 ?
O2 Eu1 O1 139.26(5) . . ?
O2 Eu1 O1 76.95(10) . 4 ?
O2 Eu1 O1 139.26(5) . 2 ?
O2 Eu1 O1 76.95(10) . 3 ?
O2 Eu1 O2 80.25(6) 4 . ?
O2 Eu1 O2 80.26(6) 3 4 ?
O2 Eu1 O2 131.41(16) 3 . ?
O2 Eu1 O2 80.25(6) 2 . ?
O2 Eu1 O2 131.41(16) 2 4 ?
O2 Eu1 O2 80.26(6) 3 2 ?
Eu1 O1 Eu1 113.98(8) 8 . ?
Eu1 O1 Eu1 113.98(8) 8 101 ?
Eu1 O1 Eu1 113.98(8) 101 . ?
C1 O2 Eu1 136.9(4) . . ?
O2 C1 O2 127.7(7) 117 . ?
O2 C1 C2 116.2(4) . . ?
O2 C1 C2 116.2(4) 117 . ?
C3 C2 C1 121.8(5) 117 . ?
C3 C2 C1 121.8(5) . . ?
C3 C2 C3 116.4(11) . 117 ?
N1 C3 C2 100.6(7) . . ?
N1 C3 C3 137.6(5) . 45_545 ?
C2 C3 C3 121.8(5) . 45_545 ?

_olex2_submission_special_instructions 'No special instructions were received'

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 -0.004 0.441 4852 985 ' '
_platon_squeeze_details          
;
;
