# 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 2018

####################################################################### 
# 
# 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_t_sq_d
_database_code_depnum_ccdc_archive 'CCDC 1845244'
_audit_update_record             
;
2018-05-25 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H9 Eu N0 O8'
_chemical_formula_weight         481.19

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   I41/a

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

_cell_length_a                   21.534(3)
_cell_length_b                   21.534(3)
_cell_length_c                   15.908(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7377(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    32891
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3712
_exptl_absorpt_coefficient_mu    3.438
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Brucker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32891
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4211
_reflns_number_gt                3827
_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)+(0.0241P)²+45.7954P] 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         4211
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_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 0.199691(8) 0.923409(8) 0.168239(10) 0.02044(6) Uani 1 1 d . . .
O1 O 0.24322(13) 0.88189(12) 0.29128(15) 0.0296(6) Uani 1 1 d . . .
O2 O 0.13656(18) 0.82838(17) 0.1832(3) 0.0773(14) Uani 1 1 d . . .
O3 O 0.24446(16) 0.66021(13) 0.3902(2) 0.0461(8) Uani 1 1 d . . .
O5 O 0.21759(15) 0.95507(13) 0.3815(2) 0.0405(7) Uani 1 1 d . . .
O6 O 0.14936(14) 0.93271(15) 1.03991(16) 0.0379(7) Uani 1 1 d . . .
O7 O 0.19270(18) 0.64143(14) 0.5081(2) 0.0522(9) Uani 1 1 d . . .
O8 O 0.22052(14) 0.94331(17) 0.9414(2) 0.0472(8) Uani 1 1 d . . .
O9 O 0.12543(13) 0.84941(17) 0.68063(17) 0.0431(8) Uani 1 1 d . . .
C1 C 0.21765(19) 0.67686(17) 0.4564(2) 0.0311(8) Uani 1 1 d . . .
C2 C 0.0445(2) 0.8593(2) 0.7772(3) 0.0454(12) Uani 1 1 d . . .
H2 H 0.0175 0.8457 0.7355 0.055 Uiso 1 1 calc R . .
C3 C 0.22731(16) 0.89970(16) 0.3639(2) 0.0234(7) Uani 1 1 d . . .
C4 C 0.22085(16) 0.85171(17) 0.4311(2) 0.0228(7) Uani 1 1 d . . .
C5 C 0.22394(18) 0.78881(17) 0.4124(2) 0.0263(7) Uani 1 1 d . . .
H5 H 0.2320 0.7760 0.3577 0.032 Uiso 1 1 calc R . .
C6 C 0.21499(17) 0.74481(17) 0.4755(2) 0.0258(8) Uani 1 1 d . . .
C7 C 0.21007(17) 0.87055(17) 0.5135(2) 0.0266(8) Uani 1 1 d . . .
H7 H 0.2083 0.9127 0.5260 0.032 Uiso 1 1 calc R . .
C8 C 0.20195(18) 0.82765(19) 0.5770(2) 0.0294(8) Uani 1 1 d . . .
C9 C 0.19088(19) 0.8494(2) 0.6652(2) 0.0340(9) Uani 1 1 d . . .
H9A H 0.2116 0.8219 0.7046 0.041 Uiso 1 1 calc R . .
H9B H 0.2075 0.8909 0.6725 0.041 Uiso 1 1 calc R . .
C11 C 0.10662(18) 0.86622(19) 0.7602(2) 0.0304(8) Uani 1 1 d . . .
C12 C 0.16807(17) 0.92707(17) 0.9656(2) 0.0256(7) Uani 1 1 d . . .
C13 C 0.12394(17) 0.90189(17) 0.9011(2) 0.0244(7) Uani 1 1 d . . .
C14 C 0.14659(18) 0.88855(17) 0.8209(2) 0.0262(8) Uani 1 1 d . . .
H14 H 0.1883 0.8947 0.8085 0.031 Uiso 1 1 calc R . .
C15 C 0.0615(2) 0.8928(2) 0.9188(3) 0.0420(11) Uani 1 1 d . . .
H15 H 0.0463 0.9004 0.9725 0.050 Uiso 1 1 calc R . .
C16 C 0.20368(19) 0.76479(19) 0.5576(2) 0.0314(8) Uani 1 1 d . . .
H16 H 0.1972 0.7356 0.5998 0.038 Uiso 1 1 calc R . .
C17 C 0.0224(2) 0.8727(3) 0.8564(3) 0.0530(14) Uani 1 1 d . . .
H17 H -0.0197 0.8679 0.8677 0.064 Uiso 1 1 calc R . .


_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 O8 2.318(3) 8_353 ?
Eu1 O6 2.320(3) 1_554 ?
Eu1 O7 2.323(3) 16_666 ?
Eu1 O5 2.335(3) 6_554 ?
Eu1 O1 2.347(3) . ?
Eu1 O3 2.357(3) 13_565 ?
Eu1 O2 2.468(3) . ?
O1 C3 1.264(4) . ?
O3 C1 1.253(5) . ?
O3 Eu1 2.356(3) 13_565 ?
O5 C3 1.243(4) . ?
O5 Eu1 2.335(3) 8_354 ?
O6 C12 1.256(4) . ?
O6 Eu1 2.320(3) 1_556 ?
O7 C1 1.244(5) . ?
O7 Eu1 2.323(3) 10_566 ?
O8 C12 1.243(5) . ?
O8 Eu1 2.318(3) 6 ?
O9 C11 1.378(4) . ?
O9 C9 1.431(5) . ?
C1 C6 1.496(5) . ?
C2 C11 1.372(6) . ?
C2 C17 1.376(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.493(5) . ?
C4 C5 1.388(5) . ?
C4 C7 1.392(5) . ?
C5 C6 1.394(5) . ?
C5 H5 0.9300 . ?
C6 C16 1.396(5) . ?
C7 C8 1.380(5) . ?
C7 H7 0.9300 . ?
C8 C16 1.389(6) . ?
C8 C9 1.498(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C14 1.380(5) . ?
C12 C13 1.499(5) . ?
C13 C15 1.387(5) . ?
C13 C14 1.396(5) . ?
C14 H14 0.9300 . ?
C15 C17 1.372(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17 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
O8 Eu1 O6 91.56(11) 8_353 1_554 ?
O8 Eu1 O7 72.15(13) 8_353 16_666 ?
O6 Eu1 O7 91.95(11) 1_554 16_666 ?
O8 Eu1 O5 71.96(12) 8_353 6_554 ?
O6 Eu1 O5 98.91(11) 1_554 6_554 ?
O7 Eu1 O5 142.67(12) 16_666 6_554 ?
O8 Eu1 O1 105.46(10) 8_353 . ?
O6 Eu1 O1 162.41(10) 1_554 . ?
O7 Eu1 O1 89.12(11) 16_666 . ?
O5 Eu1 O1 90.76(10) 6_554 . ?
O8 Eu1 O3 147.79(12) 8_353 13_565 ?
O6 Eu1 O3 87.55(11) 1_554 13_565 ?
O7 Eu1 O3 140.07(12) 16_666 13_565 ?
O5 Eu1 O3 76.37(11) 6_554 13_565 ?
O1 Eu1 O3 80.45(11) . 13_565 ?
O8 Eu1 O2 140.27(14) 8_353 . ?
O6 Eu1 O2 84.20(14) 1_554 . ?
O7 Eu1 O2 68.56(14) 16_666 . ?
O5 Eu1 O2 147.74(13) 6_554 . ?
O1 Eu1 O2 79.85(13) . . ?
O3 Eu1 O2 71.67(13) 13_565 . ?
C3 O1 Eu1 122.5(2) . . ?
C1 O3 Eu1 141.7(3) . 13_565 ?
C3 O5 Eu1 165.4(3) . 8_354 ?
C12 O6 Eu1 132.1(3) . 1_556 ?
C1 O7 Eu1 158.3(3) . 10_566 ?
C12 O8 Eu1 164.0(3) . 6 ?
C11 O9 C9 116.6(3) . . ?
O7 C1 O3 125.4(4) . . ?
O7 C1 C6 116.7(3) . . ?
O3 C1 C6 118.0(3) . . ?
C11 C2 C17 119.7(4) . . ?
C11 C2 H2 120.2 . . ?
C17 C2 H2 120.2 . . ?
O5 C3 O1 122.9(3) . . ?
O5 C3 C4 119.2(3) . . ?
O1 C3 C4 118.0(3) . . ?
C5 C4 C7 119.6(3) . . ?
C5 C4 C3 121.2(3) . . ?
C7 C4 C3 119.2(3) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C16 119.2(3) . . ?
C5 C6 C1 120.9(3) . . ?
C16 C6 C1 119.9(3) . . ?
C8 C7 C4 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C4 C7 H7 119.5 . . ?
C7 C8 C16 119.1(3) . . ?
C7 C8 C9 119.8(4) . . ?
C16 C8 C9 121.1(4) . . ?
O9 C9 C8 108.5(3) . . ?
O9 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
O9 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C2 C11 O9 116.1(3) . . ?
C2 C11 C14 120.5(3) . . ?
O9 C11 C14 123.5(3) . . ?
O8 C12 O6 123.7(4) . . ?
O8 C12 C13 117.8(3) . . ?
O6 C12 C13 118.4(3) . . ?
C15 C13 C14 119.6(3) . . ?
C15 C13 C12 121.8(3) . . ?
C14 C13 C12 118.5(3) . . ?
C11 C14 C13 119.6(3) . . ?
C11 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C17 C15 C13 119.5(4) . . ?
C17 C15 H15 120.2 . . ?
C13 C15 H15 120.2 . . ?
C8 C16 C6 120.9(3) . . ?
C8 C16 H16 119.6 . . ?
C6 C16 H16 119.6 . . ?
C15 C17 C2 121.0(4) . . ?
C15 C17 H17 119.5 . . ?
C2 C17 H17 119.5 . . ?

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
O8 Eu1 O1 C3 42.0(3) 8_353 . . . ?
O6 Eu1 O1 C3 -122.9(4) 1_554 . . . ?
O7 Eu1 O1 C3 -29.2(3) 16_666 . . . ?
O5 Eu1 O1 C3 113.5(3) 6_554 . . . ?
O3 Eu1 O1 C3 -170.5(3) 13_565 . . . ?
O2 Eu1 O1 C3 -97.6(3) . . . . ?
Eu1 O7 C1 O3 25.1(13) 10_566 . . . ?
Eu1 O7 C1 C6 -155.0(7) 10_566 . . . ?
Eu1 O3 C1 O7 -28.9(8) 13_565 . . . ?
Eu1 O3 C1 C6 151.2(3) 13_565 . . . ?
Eu1 O5 C3 O1 112.3(10) 8_354 . . . ?
Eu1 O5 C3 C4 -68.5(12) 8_354 . . . ?
Eu1 O1 C3 O5 -40.7(5) . . . . ?
Eu1 O1 C3 C4 140.1(3) . . . . ?
O5 C3 C4 C5 172.3(4) . . . . ?
O1 C3 C4 C5 -8.5(5) . . . . ?
O5 C3 C4 C7 -6.2(5) . . . . ?
O1 C3 C4 C7 173.0(3) . . . . ?
C7 C4 C5 C6 1.4(6) . . . . ?
C3 C4 C5 C6 -177.1(3) . . . . ?
C4 C5 C6 C16 -0.8(6) . . . . ?
C4 C5 C6 C1 179.5(4) . . . . ?
O7 C1 C6 C5 -160.4(4) . . . . ?
O3 C1 C6 C5 19.5(6) . . . . ?
O7 C1 C6 C16 19.9(6) . . . . ?
O3 C1 C6 C16 -160.2(4) . . . . ?
C5 C4 C7 C8 -0.5(6) . . . . ?
C3 C4 C7 C8 178.0(3) . . . . ?
C4 C7 C8 C16 -1.0(6) . . . . ?
C4 C7 C8 C9 179.6(4) . . . . ?
C11 O9 C9 C8 177.8(4) . . . . ?
C7 C8 C9 O9 96.4(4) . . . . ?
C16 C8 C9 O9 -83.0(5) . . . . ?
C17 C2 C11 O9 177.4(5) . . . . ?
C17 C2 C11 C14 -2.4(8) . . . . ?
C9 O9 C11 C2 -172.9(4) . . . . ?
C9 O9 C11 C14 6.9(6) . . . . ?
Eu1 O8 C12 O6 71.3(11) 6 . . . ?
Eu1 O8 C12 C13 -111.4(9) 6 . . . ?
Eu1 O6 C12 O8 -35.7(6) 1_556 . . . ?
Eu1 O6 C12 C13 147.0(3) 1_556 . . . ?
O8 C12 C13 C15 -168.5(4) . . . . ?
O6 C12 C13 C15 8.9(6) . . . . ?
O8 C12 C13 C14 10.2(5) . . . . ?
O6 C12 C13 C14 -172.4(3) . . . . ?
C2 C11 C14 C13 2.5(6) . . . . ?
O9 C11 C14 C13 -177.2(4) . . . . ?
C15 C13 C14 C11 -0.3(6) . . . . ?
C12 C13 C14 C11 -179.0(3) . . . . ?
C14 C13 C15 C17 -2.0(7) . . . . ?
C12 C13 C15 C17 176.7(4) . . . . ?
C7 C8 C16 C6 1.6(6) . . . . ?
C9 C8 C16 C6 -179.0(4) . . . . ?
C5 C6 C16 C8 -0.7(6) . . . . ?
C1 C6 C16 C8 179.0(4) . . . . ?
C13 C15 C17 C2 2.1(9) . . . . ?
C11 C2 C17 C15 0.0(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.688
_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 0.500 0.250 -0.125 370 73 ' '
2 0.500 0.750 0.125 370 73 ' '
3 0.000 0.750 0.375 370 73 ' '
4 0.000 0.250 0.625 370 73 ' '
_platon_squeeze_details          ?
