# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_s
_database_code_depnum_ccdc_archive 'CCDC 1883718'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C104 H94 Eu2 N4 O16'
_chemical_formula_weight         1959.75

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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Fddd

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

_cell_length_a                   21.821(4)
_cell_length_b                   25.478(5)
_cell_length_c                   40.301(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     22406(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3785
_cell_measurement_theta_min      3.1766
_cell_measurement_theta_max      29.1285

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             8000
_exptl_absorpt_coefficient_mu    1.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12532
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4918
_reflns_number_gt                3128
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1314P)²+1.6736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4918
_refine_ls_number_parameters     286
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2282
_refine_ls_wR_factor_gt          0.2067
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.170
_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
Eu1 Eu 0.3750 0.3750 0.023179(13) 0.0679(3) Uani 1 2 d S . .
N1 N 0.4310(3) 0.5210(3) -0.02195(17) 0.0770(18) Uani 1 1 d . . .
O1 O 0.4033(3) 0.4616(2) 0.03056(13) 0.0773(14) Uani 1 1 d . . .
O2 O 0.4411(3) 0.3617(2) 0.07015(13) 0.0743(14) Uani 1 1 d . . .
O3 O 0.2815(3) 0.4134(2) 0.00585(14) 0.0880(17) Uani 1 1 d . . .
O4 O 0.3970(4) 0.4138(2) -0.03290(15) 0.109(2) Uani 1 1 d . . .
C1 C 0.4929(6) 0.3545(5) 0.1684(3) 0.125(4) Uani 1 1 d . . .
H1 H 0.4778 0.3792 0.1833 0.150 Uiso 1 1 calc R . .
C2 C 0.1489(6) 0.4955(6) 0.0014(4) 0.153(6) Uani 1 1 d . . .
H2 H 0.1325 0.4938 0.0227 0.183 Uiso 1 1 calc R . .
C3 C 0.3750 0.3750 -0.0855(4) 0.191(12) Uani 1 2 d S . .
C4 C 0.4019(7) 0.5432(5) 0.1018(3) 0.144(3) Uani 1 1 d U . .
H4 H 0.3841 0.5444 0.1227 0.173 Uiso 1 1 calc R . .
C5 C 0.1175(7) 0.5195(10) -0.0243(5) 0.201(11) Uani 1 1 d . . .
H5 H 0.0782 0.5320 -0.0199 0.242 Uiso 1 1 calc R . .
C6 C 0.5276(6) 0.2786(6) 0.1246(3) 0.140(3) Uani 1 1 d U . .
H6 H 0.5407 0.2532 0.1097 0.168 Uiso 1 1 calc R . .
C7 C 0.1386(8) 0.5259(7) -0.0536(5) 0.169(7) Uani 1 1 d . . .
H7 H 0.1147 0.5418 -0.0698 0.203 Uiso 1 1 calc R . .
C8 C 0.5304(7) 0.3150(7) 0.1786(4) 0.167(4) Uani 1 1 d U . .
H8 H 0.5522 0.3189 0.1982 0.201 Uiso 1 1 calc R . .
C9 C 0.4374(7) 0.5907(5) 0.0871(3) 0.157(3) Uani 1 1 d U . .
H9 H 0.4534 0.6169 0.1007 0.189 Uiso 1 1 calc R . .
C10 C 0.5371(7) 0.2690(7) 0.1606(4) 0.176(4) Uani 1 1 d U . .
H10 H 0.5463 0.2365 0.1698 0.211 Uiso 1 1 calc R . .
C11 C 0.4065(5) 0.5025(3) 0.0486(2) 0.096(2) Uani 1 1 d U . .
C12 C 0.3750 0.3750 -0.0477(3) 0.117(6) Uani 1 2 d S . .
C13 C 0.2431(4) 0.4427(3) 0.0191(2) 0.072(2) Uani 1 1 d . . .
C14 C 0.4284(6) 0.5488(3) 0.0333(2) 0.111(4) Uani 1 1 d . . .
C15 C 0.2059(4) 0.4739(3) -0.0059(3) 0.087(2) Uani 1 1 d . . .
C16 C 0.4435(5) 0.5298(4) -0.0564(2) 0.099(3) Uani 1 1 d . . .
H16A H 0.4687 0.5013 -0.0647 0.118 Uiso 1 1 calc R . .
H16B H 0.4667 0.5620 -0.0588 0.118 Uiso 1 1 calc R . .
C17 C 0.4031(4) 0.5338(4) -0.1146(2) 0.088(2) Uani 1 1 d . . .
H17A H 0.4272 0.5648 -0.1196 0.106 Uiso 1 1 calc R . .
H17B H 0.4276 0.5032 -0.1199 0.106 Uiso 1 1 calc R . .
C18 C 0.3983(6) 0.5005(4) 0.0825(2) 0.117(3) Uani 1 1 d U . .
H18 H 0.3899 0.4683 0.0924 0.140 Uiso 1 1 calc R . .
C19 C 0.4783(5) 0.3567(5) 0.1352(3) 0.103(2) Uani 1 1 d U . .
H19 H 0.4513 0.3829 0.1286 0.123 Uiso 1 1 calc R . .
C20 C 0.4844(4) 0.3312(4) 0.0762(2) 0.090(2) Uani 1 1 d U . .
C21 C 0.3869(4) 0.5334(4) -0.0767(2) 0.093(3) Uani 1 1 d . . .
H21A H 0.3649 0.5652 -0.0711 0.111 Uiso 1 1 calc R . .
H21B H 0.3606 0.5037 -0.0719 0.111 Uiso 1 1 calc R . .
C22 C 0.4385(6) 0.5549(4) 0.0001(3) 0.116(4) Uani 1 1 d . . .
H22 H 0.4522 0.5877 -0.0069 0.139 Uiso 1 1 calc R . .
C23 C 0.2343(4) 0.4471(4) 0.0523(2) 0.093(3) Uani 1 1 d . . .
H23 H 0.2051 0.4710 0.0595 0.112 Uiso 1 1 calc R . .
C24 C 0.2277(5) 0.4812(4) -0.0370(2) 0.092(3) Uani 1 1 d . . .
H24 H 0.2655 0.4666 -0.0423 0.111 Uiso 1 1 calc R . .
C25 C 0.4443(8) 0.5925(5) 0.0530(3) 0.157(3) Uani 1 1 d U . .
H25 H 0.4595 0.6227 0.0430 0.189 Uiso 1 1 calc R . .
C26 C 0.1972(6) 0.5088(5) -0.0612(3) 0.130(4) Uani 1 1 d . . .
H26 H 0.2152 0.5157 -0.0817 0.157 Uiso 1 1 calc R . .
C27 C 0.4996(4) 0.3246(4) 0.1119(3) 0.098(2) Uani 1 1 d U . .


_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 O1 2.309(5) 2 ?
Eu1 O1 2.309(5) . ?
Eu1 O3 2.369(6) . ?
Eu1 O3 2.369(6) 2 ?
Eu1 O2 2.404(5) 2 ?
Eu1 O2 2.404(5) . ?
Eu1 O4 2.513(6) . ?
Eu1 O4 2.513(6) 2 ?
Eu1 C12 2.855(13) . ?
N1 C22 1.249(11) . ?
N1 C16 1.431(10) . ?
O1 C11 1.274(9) . ?
O2 C20 1.248(10) . ?
O3 C13 1.241(9) . ?
O4 C12 1.249(9) . ?
C1 C8 1.361(18) . ?
C1 C19 1.375(15) . ?
C2 C15 1.392(16) . ?
C2 C5 1.385(19) . ?
C3 C12 1.526(19) . ?
C4 C18 1.338(13) . ?
C4 C9 1.553(16) . ?
C5 C7 1.280(18) . ?
C6 C27 1.416(16) . ?
C6 C10 1.484(16) . ?
C7 C26 1.385(17) . ?
C8 C10 1.385(19) . ?
C9 C25 1.383(15) . ?
C11 C18 1.378(13) . ?
C11 C14 1.415(12) . ?
C12 O4 1.249(9) 2 ?
C13 C23 1.356(11) . ?
C13 C15 1.519(12) . ?
C14 C22 1.368(13) . ?
C14 C25 1.411(13) . ?
C15 C24 1.352(13) . ?
C16 C21 1.485(12) . ?
C17 C17 1.483(17) 3_554 ?
C17 C21 1.567(12) . ?
C19 C27 1.331(14) . ?
C20 C23 1.383(13) 2 ?
C20 C27 1.487(13) . ?
C23 C20 1.383(13) 2 ?
C24 C26 1.374(13) . ?

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
O1 Eu1 O1 165.2(3) 2 . ?
O1 Eu1 O3 101.7(2) 2 . ?
O1 Eu1 O3 82.7(2) . . ?
O1 Eu1 O3 82.7(2) 2 2 ?
O1 Eu1 O3 101.7(2) . 2 ?
O3 Eu1 O3 145.7(3) . 2 ?
O1 Eu1 O2 82.74(19) 2 2 ?
O1 Eu1 O2 85.62(18) . 2 ?
O3 Eu1 O2 69.93(19) . 2 ?
O3 Eu1 O2 143.85(18) 2 2 ?
O1 Eu1 O2 85.62(18) 2 . ?
O1 Eu1 O2 82.74(19) . . ?
O3 Eu1 O2 143.85(18) . . ?
O3 Eu1 O2 69.93(19) 2 . ?
O2 Eu1 O2 76.1(3) 2 . ?
O1 Eu1 O4 122.83(18) 2 . ?
O1 Eu1 O4 71.91(19) . . ?
O3 Eu1 O4 74.8(2) . . ?
O3 Eu1 O4 74.5(2) 2 . ?
O2 Eu1 O4 140.1(2) 2 . ?
O2 Eu1 O4 130.5(2) . . ?
O1 Eu1 O4 71.91(19) 2 2 ?
O1 Eu1 O4 122.83(18) . 2 ?
O3 Eu1 O4 74.5(2) . 2 ?
O3 Eu1 O4 74.8(2) 2 2 ?
O2 Eu1 O4 130.5(2) 2 2 ?
O2 Eu1 O4 140.1(2) . 2 ?
O4 Eu1 O4 51.8(3) . 2 ?
O1 Eu1 C12 97.40(13) 2 . ?
O1 Eu1 C12 97.40(13) . . ?
O3 Eu1 C12 72.85(14) . . ?
O3 Eu1 C12 72.85(14) 2 . ?
O2 Eu1 C12 141.95(13) 2 . ?
O2 Eu1 C12 141.95(13) . . ?
O4 Eu1 C12 25.91(14) . . ?
O4 Eu1 C12 25.91(14) 2 . ?
C22 N1 C16 123.8(8) . . ?
C11 O1 Eu1 150.5(5) . . ?
C20 O2 Eu1 134.1(6) . . ?
C13 O3 Eu1 134.6(5) . . ?
C12 O4 Eu1 92.5(6) . . ?
C8 C1 C19 117.5(13) . . ?
C15 C2 C5 117.2(14) . . ?
C18 C4 C9 116.3(11) . . ?
C7 C5 C2 124.7(15) . . ?
C27 C6 C10 123.4(13) . . ?
C5 C7 C26 119.7(14) . . ?
C1 C8 C10 122.1(14) . . ?
C25 C9 C4 117.1(11) . . ?
C8 C10 C6 110.9(15) . . ?
O1 C11 C18 122.0(8) . . ?
O1 C11 C14 116.9(8) . . ?
C18 C11 C14 120.4(8) . . ?
O4 C12 O4 123.1(12) 2 . ?
O4 C12 C3 118.4(6) 2 . ?
O4 C12 C3 118.4(6) . . ?
O4 C12 Eu1 61.6(6) 2 . ?
O4 C12 Eu1 61.6(6) . . ?
C3 C12 Eu1 180.0 . . ?
O3 C13 C23 124.7(8) . . ?
O3 C13 C15 113.0(8) . . ?
C23 C13 C15 122.3(8) . . ?
C22 C14 C11 125.3(8) . . ?
C22 C14 C25 115.0(9) . . ?
C11 C14 C25 119.7(9) . . ?
C24 C15 C2 117.3(10) . . ?
C24 C15 C13 119.8(8) . . ?
C2 C15 C13 122.9(10) . . ?
N1 C16 C21 112.8(8) . . ?
C17 C17 C21 111.4(10) 3_554 . ?
C4 C18 C11 122.5(10) . . ?
C27 C19 C1 125.5(12) . . ?
O2 C20 C23 124.2(9) . 2 ?
O2 C20 C27 115.3(9) . . ?
C23 C20 C27 120.4(9) 2 . ?
C16 C21 C17 110.6(8) . . ?
N1 C22 C14 126.6(8) . . ?
C13 C23 C20 125.0(9) . 2 ?
C15 C24 C26 123.8(11) . . ?
C9 C25 C14 120.5(11) . . ?
C7 C26 C24 116.9(12) . . ?
C19 C27 C6 113.8(11) . . ?
C19 C27 C20 122.4(10) . . ?
C6 C27 C20 122.7(10) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.028
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.105

# 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 -0.125 0.375 -0.125 650 69 ' '
2 0.125 0.625 0.125 650 69 ' '
3 -0.125 0.875 0.375 650 69 ' '
4 0.125 0.125 0.625 650 69 ' '
5 0.375 0.875 -0.125 650 69 ' '
6 0.375 0.375 0.375 650 69 ' '
7 0.625 0.125 0.125 650 69 ' '
8 0.625 0.625 0.625 650 69 ' '
_platon_squeeze_details          
;
;
