# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_CNA-3
_database_code_depnum_ccdc_archive 'CCDC 1992588'
_audit_update_record             
;
2020-03-25 deposited with the CCDC.	2020-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H12 Eu3 N12 O19'
_chemical_formula_weight         1300.40

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'

_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'

_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, x, z'
'-x, -y, z'
'y, -x, z'
'x, -y, -z'
'y, x, -z'
'-x, y, -z'
'-y, -x, -z'
'z, x, y'
'-x, z, y'
'-z, -x, y'
'x, -z, y'
'z, -x, -y'
'x, z, -y'
'-z, x, -y'
'-x, -z, -y'
'y, z, x'
'-z, -y, -x'
'-z, y, x'
'z, y, -x'
'z, -y, x'
'y, -z, -x'
'-y, -z, x'
'-y, z, -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, -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'
'z, x+1/2, y+1/2'
'-x, z+1/2, y+1/2'
'-z, -x+1/2, y+1/2'
'x, -z+1/2, y+1/2'
'z, -x+1/2, -y+1/2'
'x, z+1/2, -y+1/2'
'-z, x+1/2, -y+1/2'
'-x, -z+1/2, -y+1/2'
'y, z+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'-z, y+1/2, x+1/2'
'z, y+1/2, -x+1/2'
'z, -y+1/2, x+1/2'
'y, -z+1/2, -x+1/2'
'-y, -z+1/2, x+1/2'
'-y, z+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, -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'
'z+1/2, x, y+1/2'
'-x+1/2, z, y+1/2'
'-z+1/2, -x, y+1/2'
'x+1/2, -z, y+1/2'
'z+1/2, -x, -y+1/2'
'x+1/2, z, -y+1/2'
'-z+1/2, x, -y+1/2'
'-x+1/2, -z, -y+1/2'
'y+1/2, z, x+1/2'
'-z+1/2, -y, -x+1/2'
'-z+1/2, y, x+1/2'
'z+1/2, y, -x+1/2'
'z+1/2, -y, x+1/2'
'y+1/2, -z, -x+1/2'
'-y+1/2, -z, x+1/2'
'-y+1/2, z, -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, -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'
'z+1/2, x+1/2, y'
'-x+1/2, z+1/2, y'
'-z+1/2, -x+1/2, y'
'x+1/2, -z+1/2, y'
'z+1/2, -x+1/2, -y'
'x+1/2, z+1/2, -y'
'-z+1/2, x+1/2, -y'
'-x+1/2, -z+1/2, -y'
'y+1/2, z+1/2, x'
'-z+1/2, -y+1/2, -x'
'-z+1/2, y+1/2, x'
'z+1/2, y+1/2, -x'
'z+1/2, -y+1/2, x'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z+1/2, x'
'-y+1/2, z+1/2, -x'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x, y, z'
'-y, -x, z'
'x, -y, z'
'y, x, z'
'-z, -x, -y'
'x, -z, -y'
'z, x, -y'
'-x, z, -y'
'-z, x, y'
'-x, -z, y'
'z, -x, y'
'x, z, y'
'-y, -z, -x'
'z, y, x'
'z, -y, -x'
'-z, -y, x'
'-z, y, -x'
'-y, z, x'
'y, z, -x'
'y, -z, 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, 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'
'-z, -x+1/2, -y+1/2'
'x, -z+1/2, -y+1/2'
'z, x+1/2, -y+1/2'
'-x, z+1/2, -y+1/2'
'-z, x+1/2, y+1/2'
'-x, -z+1/2, y+1/2'
'z, -x+1/2, y+1/2'
'x, z+1/2, y+1/2'
'-y, -z+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'z, -y+1/2, -x+1/2'
'-z, -y+1/2, x+1/2'
'-z, y+1/2, -x+1/2'
'-y, z+1/2, x+1/2'
'y, z+1/2, -x+1/2'
'y, -z+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, 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'
'-z+1/2, -x, -y+1/2'
'x+1/2, -z, -y+1/2'
'z+1/2, x, -y+1/2'
'-x+1/2, z, -y+1/2'
'-z+1/2, x, y+1/2'
'-x+1/2, -z, y+1/2'
'z+1/2, -x, y+1/2'
'x+1/2, z, y+1/2'
'-y+1/2, -z, -x+1/2'
'z+1/2, y, x+1/2'
'z+1/2, -y, -x+1/2'
'-z+1/2, -y, x+1/2'
'-z+1/2, y, -x+1/2'
'-y+1/2, z, x+1/2'
'y+1/2, z, -x+1/2'
'y+1/2, -z, 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, 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'
'-z+1/2, -x+1/2, -y'
'x+1/2, -z+1/2, -y'
'z+1/2, x+1/2, -y'
'-x+1/2, z+1/2, -y'
'-z+1/2, x+1/2, y'
'-x+1/2, -z+1/2, y'
'z+1/2, -x+1/2, y'
'x+1/2, z+1/2, y'
'-y+1/2, -z+1/2, -x'
'z+1/2, y+1/2, x'
'z+1/2, -y+1/2, -x'
'-z+1/2, -y+1/2, x'
'-z+1/2, y+1/2, -x'
'-y+1/2, z+1/2, x'
'y+1/2, z+1/2, -x'
'y+1/2, -z+1/2, x'

_cell_length_a                   27.6237(8)
_cell_length_b                   27.6237(8)
_cell_length_c                   27.6237(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     21078.8(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.820
_exptl_crystal_F_000             4936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.799
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52011
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.1374
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.277
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1097
_reflns_number_gt                815
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2013 (Sheldrick, 2013)'
_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)+(0.1477P)²+295.0619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1097
_refine_ls_number_parameters     40
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2591
_refine_ls_wR_factor_gt          0.2001
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_restrained_S_all      1.257
_refine_ls_shift/su_max          0.002
_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
Eu1 Eu 0.0000 0.39841(4) 0.0000 0.0304(5) Uani 1 8 d S T P . .
O1 O 0.0464(2) 0.4536(2) 0.0464(2) 0.019(2) Uani 1 6 d S T P . .
O2A O 0.0000 0.3625(4) 0.0784(4) 0.065(3) Uani 1 2 d S T P . .
O2 O 0.0000 0.3031(16) 0.0000 0.24(3) Uani 1 8 d S T P . .
N7 N 0.0000 0.2562(9) 0.1834(9) 0.28(2) Uani 1 2 d S T P . .
C4 C 0.0000 0.3788(6) 0.1212(6) 0.079(8) Uani 1 4 d S T P . .
C3 C 0.0000 0.2700(7) 0.2300(7) 0.24(4) Uani 1 4 d S T P . .
C5 C 0.0000 0.3391(6) 0.1609(6) 0.127(14) Uani 1 4 d S T P . .
C6 C 0.0000 0.2917(8) 0.1503(9) 0.188(18) Uani 1 2 d S T P . .
H6 H 0.0000 0.2829 0.1178 0.226 Uiso 1 2 calc 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
Eu1 O1 2.369(3) 76_455 ?
Eu1 O1 2.369(3) 99 ?
Eu1 O1 2.369(3) 170_455 ?
Eu1 O1 2.369(3) . ?
Eu1 O2A 2.381(10) 19 ?
Eu1 O2A 2.381(10) 99 ?
Eu1 O2A 2.381(10) 114 ?
Eu1 O2A 2.381(10) . ?
Eu1 O2 2.63(4) . ?
Eu1 Eu1 3.9688(15) 129 ?
Eu1 Eu1 3.9688(15) 74 ?
Eu1 Eu1 3.9688(15) 170_455 ?
O1 Eu1 2.369(3) 129 ?
O1 Eu1 2.369(3) 74 ?
O2A C4 1.266(14) . ?
N7 C6 1.34(3) . ?
N7 C3 1.34(3) . ?
C4 O2A 1.266(14) 130 ?
C4 C5 1.55(3) . ?
C3 N7 1.34(3) 130 ?
C3 C3 1.56(6) 121 ?
C5 C6 1.34(3) 130 ?
C5 C6 1.34(3) . ?
C6 H6 0.9300 . ?

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 99.9(5) 76_455 99 ?
O1 Eu1 O1 65.6(3) 76_455 170_455 ?
O1 Eu1 O1 65.6(3) 99 170_455 ?
O1 Eu1 O1 65.6(3) 76_455 . ?
O1 Eu1 O1 65.6(3) 99 . ?
O1 Eu1 O1 99.9(5) 170_455 . ?
O1 Eu1 O2A 77.1(3) 76_455 19 ?
O1 Eu1 O2A 139.49(16) 99 19 ?
O1 Eu1 O2A 77.1(3) 170_455 19 ?
O1 Eu1 O2A 139.49(16) . 19 ?
O1 Eu1 O2A 139.49(16) 76_455 99 ?
O1 Eu1 O2A 77.1(3) 99 99 ?
O1 Eu1 O2A 77.1(3) 170_455 99 ?
O1 Eu1 O2A 139.49(16) . 99 ?
O2A Eu1 O2A 80.0(2) 19 99 ?
O1 Eu1 O2A 139.49(16) 76_455 114 ?
O1 Eu1 O2A 77.1(3) 99 114 ?
O1 Eu1 O2A 139.49(16) 170_455 114 ?
O1 Eu1 O2A 77.1(3) . 114 ?
O2A Eu1 O2A 130.7(6) 19 114 ?
O2A Eu1 O2A 80.0(2) 99 114 ?
O1 Eu1 O2A 77.1(3) 76_455 . ?
O1 Eu1 O2A 139.49(16) 99 . ?
O1 Eu1 O2A 139.49(16) 170_455 . ?
O1 Eu1 O2A 77.1(3) . . ?
O2A Eu1 O2A 80.0(2) 19 . ?
O2A Eu1 O2A 130.7(6) 99 . ?
O2A Eu1 O2A 80.0(2) 114 . ?
O1 Eu1 O2 130.0(2) 76_455 . ?
O1 Eu1 O2 130.0(2) 99 . ?
O1 Eu1 O2 130.0(2) 170_455 . ?
O1 Eu1 O2 130.0(2) . . ?
O2A Eu1 O2 65.4(3) 19 . ?
O2A Eu1 O2 65.4(3) 99 . ?
O2A Eu1 O2 65.4(3) 114 . ?
O2A Eu1 O2 65.4(3) . . ?
O1 Eu1 Eu1 33.11(10) 76_455 129 ?
O1 Eu1 Eu1 85.9(2) 99 129 ?
O1 Eu1 Eu1 85.9(2) 170_455 129 ?
O1 Eu1 Eu1 33.11(10) . 129 ?
O2A Eu1 Eu1 107.14(19) 19 129 ?
O2A Eu1 Eu1 159.6(3) 99 129 ?
O2A Eu1 Eu1 107.14(19) 114 129 ?
O2A Eu1 Eu1 69.6(3) . 129 ?
O2 Eu1 Eu1 135.0 . 129 ?
O1 Eu1 Eu1 85.9(2) 76_455 74 ?
O1 Eu1 Eu1 33.11(10) 99 74 ?
O1 Eu1 Eu1 85.9(2) 170_455 74 ?
O1 Eu1 Eu1 33.11(10) . 74 ?
O2A Eu1 Eu1 159.6(3) 19 74 ?
O2A Eu1 Eu1 107.14(19) 99 74 ?
O2A Eu1 Eu1 69.6(3) 114 74 ?
O2A Eu1 Eu1 107.14(19) . 74 ?
O2 Eu1 Eu1 135.000(1) . 74 ?
Eu1 Eu1 Eu1 60.0 129 74 ?
O1 Eu1 Eu1 33.11(10) 76_455 170_455 ?
O1 Eu1 Eu1 85.9(2) 99 170_455 ?
O1 Eu1 Eu1 33.11(10) 170_455 170_455 ?
O1 Eu1 Eu1 85.9(2) . 170_455 ?
O2A Eu1 Eu1 69.6(3) 19 170_455 ?
O2A Eu1 Eu1 107.14(19) 99 170_455 ?
O2A Eu1 Eu1 159.6(3) 114 170_455 ?
O2A Eu1 Eu1 107.14(19) . 170_455 ?
O2 Eu1 Eu1 135.000(1) . 170_455 ?
Eu1 Eu1 Eu1 60.0 129 170_455 ?
Eu1 Eu1 Eu1 90.0 74 170_455 ?
Eu1 O1 Eu1 113.8(2) 129 74 ?
Eu1 O1 Eu1 113.8(2) 129 . ?
Eu1 O1 Eu1 113.8(2) 74 . ?
C4 O2A Eu1 134.4(12) . . ?
C6 N7 C3 117(3) . . ?
O2A C4 O2A 132(2) . 130 ?
O2A C4 C5 114.1(11) . . ?
O2A C4 C5 114.1(11) 130 . ?
N7 C3 N7 123(3) . 130 ?
N7 C3 C3 118.5(15) . 121 ?
N7 C3 C3 118.5(15) 130 121 ?
C6 C5 C6 115(3) 130 . ?
C6 C5 C4 122.3(14) 130 . ?
C6 C5 C4 122.3(14) . . ?
N7 C6 C5 124(3) . . ?
N7 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Eu1 O2A C4 O2A 0.000(5) . . . 130 ?
Eu1 O2A C4 C5 180.000(2) . . . . ?
C6 N7 C3 N7 0.000(3) . . . 130 ?
C6 N7 C3 C3 180.000(3) . . . 121 ?
O2A C4 C5 C6 180.000(4) . . . 130 ?
O2A C4 C5 C6 0.000(4) 130 . . 130 ?
O2A C4 C5 C6 0.000(4) . . . . ?
O2A C4 C5 C6 180.000(3) 130 . . . ?
C3 N7 C6 C5 0.000(4) . . . . ?
C6 C5 C6 N7 0.000(4) 130 . . . ?
C4 C5 C6 N7 180.000(4) . . . . ?

_refine_diff_density_max         3.278
_refine_diff_density_min         -1.705
_refine_diff_density_rms         0.399

_shelxl_version_number           2013-4



