# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# 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_js009
_database_code_depnum_ccdc_archive 'CCDC 1572387'
_audit_update_record             
;
2017-09-04 deposited with the CCDC.
2017-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H24 Eu N9 O9'
_chemical_formula_weight         854.58

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   12.5871(3)
_cell_length_b                   15.7676(3)
_cell_length_c                   17.0644(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.021(2)
_cell_angle_gamma                90
_cell_volume                     3312.48(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    26275
_cell_measurement_theta_min      2.248
_cell_measurement_theta_max      28.005

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.965
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5247
_exptl_absorpt_correction_T_max  0.8046
_exptl_absorpt_process_details   'X-Red and X-Shape (STOE)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  IPDS-2
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26275
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         28.005
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4013
_reflns_number_gt                3748
_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       'X-Area (STOE, 2008)'
_computing_cell_refinement       'X-Area (STOE, 2008)'
_computing_data_reduction        'X-Area (STOE, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_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)+(0.0590P)²+2.5819P] 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     SHELXL
_refine_ls_extinction_coef       0.00129(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4013
_refine_ls_number_parameters     266
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.082
_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 0.5000 0.40249(2) 0.7500 0.03136(9) Uani 1 2 d S T P . .
N1 N 0.7348(2) 0.43802(18) 0.79003(16) 0.0428(6) Uani 1 1 d . . . . .
O1 O 0.67325(19) 0.45055(15) 0.83936(13) 0.0450(5) Uani 1 1 d . . . . .
O2 O 0.6890(2) 0.41291(14) 0.72059(15) 0.0450(5) Uani 1 1 d . . . . .
O3 O 0.8327(2) 0.4493(2) 0.80804(17) 0.0605(7) Uani 1 1 d . . . . .
N2 N 0.5000 0.5880(2) 0.7500 0.0412(8) Uani 1 2 d S T P . .
O4 O 0.46302(19) 0.54530(14) 0.80158(12) 0.0421(5) Uani 1 1 d . . . . .
O5 O 0.5000 0.6645(2) 0.7500 0.0650(11) Uani 1 2 d S T P . .
N11 N 0.3904(2) 0.26686(16) 0.70476(14) 0.0391(5) Uani 1 1 d . . . . .
N12 N 0.4985(2) 0.35450(15) 0.60798(14) 0.0367(5) Uani 1 1 d . . . . .
C11 C 0.3402(3) 0.2232(2) 0.7530(2) 0.0462(7) Uani 1 1 d . . . . .
H11 H 0.3438 0.2437 0.8058 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2823(3) 0.1486(2) 0.7298(2) 0.0536(8) Uani 1 1 d . . . . .
H12 H 0.2491 0.1184 0.7665 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2744(3) 0.1198(2) 0.6532(3) 0.0532(8) Uani 1 1 d . . . . .
H13 H 0.2345 0.0697 0.6359 0.064 Uiso 1 1 calc R U . . .
C14 C 0.3256(3) 0.1647(2) 0.5999(2) 0.0451(7) Uani 1 1 d . . . . .
C15 C 0.3170(3) 0.1411(2) 0.5174(2) 0.0514(8) Uani 1 1 d . . . . .
H15 H 0.2762 0.0922 0.4972 0.062 Uiso 1 1 calc R U . . .
C16 C 0.3652(3) 0.1866(2) 0.4688(2) 0.0513(8) Uani 1 1 d . . . . .
H16 H 0.3580 0.1693 0.4146 0.062 Uiso 1 1 calc R U . . .
C17 C 0.4279(3) 0.2611(2) 0.49645(18) 0.0430(7) Uani 1 1 d . . . . .
C18 C 0.4779(3) 0.3117(2) 0.44728(18) 0.0483(8) Uani 1 1 d . . . . .
H18 H 0.4707 0.2979 0.3922 0.058 Uiso 1 1 calc R U . . .
C19 C 0.5371(3) 0.3808(2) 0.47838(19) 0.0459(7) Uani 1 1 d . . . . .
H19 H 0.5712 0.4156 0.4454 0.055 Uiso 1 1 calc R U . . .
C20 C 0.5467(3) 0.39970(19) 0.5594(2) 0.0416(7) Uani 1 1 d . . . . .
H20 H 0.5896 0.4471 0.5810 0.050 Uiso 1 1 calc R U . . .
C21 C 0.4386(2) 0.28554(19) 0.57715(17) 0.0373(6) Uani 1 1 d . . . . .
C22 C 0.3845(2) 0.23778(18) 0.62889(17) 0.0375(6) Uani 1 1 d . . . . .
N31 N 0.6966(4) 0.1644(3) 0.5512(3) 0.0546(10) Uani 0.75 1 d D . P A 1
C31 C 0.7176(6) 0.2110(5) 0.4912(6) 0.0481(15) Uani 0.75 1 d D . P A 1
C32 C 0.6789(4) 0.1893(4) 0.4102(3) 0.0555(12) Uani 0.75 1 d D . P A 1
H32 H 0.6954 0.2243 0.3690 0.067 Uiso 0.75 1 calc R U P A 1
C33 C 0.6164(7) 0.1167(6) 0.3906(4) 0.0632(16) Uani 0.75 1 d D . P A 1
H33 H 0.5888 0.1013 0.3363 0.076 Uiso 0.75 1 calc R U P A 1
C34 C 0.5965(6) 0.0686(5) 0.4519(5) 0.0614(16) Uani 0.75 1 d D . P A 1
H34 H 0.5552 0.0179 0.4411 0.074 Uiso 0.75 1 calc R U P A 1
C35 C 0.6367(5) 0.0937(3) 0.5306(5) 0.0639(15) Uani 0.75 1 d D . P A 1
H35 H 0.6211 0.0591 0.5724 0.077 Uiso 0.75 1 calc R U P A 1
N31' N 0.6898(16) 0.2256(11) 0.3941(10) 0.077(5) Uiso 0.25 1 d D . P B 2
C31' C 0.714(3) 0.2147(16) 0.4722(12) 0.050(8) Uiso 0.25 1 d D . P B 2
C32' C 0.6847(18) 0.1471(13) 0.5171(11) 0.066(6) Uiso 0.25 1 d D . P B 2
H32' H 0.7083 0.1444 0.5737 0.079 Uiso 0.25 1 calc R U P B 2
C33' C 0.619(2) 0.0839(15) 0.4737(15) 0.068(8) Uiso 0.25 1 d D . P B 2
H33' H 0.5927 0.0370 0.4990 0.081 Uiso 0.25 1 calc R U P B 2
C34' C 0.596(3) 0.0944(19) 0.3929(17) 0.090(13) Uiso 0.25 1 d D . P B 2
H34' H 0.5518 0.0528 0.3612 0.108 Uiso 0.25 1 calc R U P B 2
C35' C 0.6318(19) 0.1620(14) 0.3538(13) 0.089(6) Uiso 0.25 1 d D . P B 2
H35' H 0.6152 0.1634 0.2969 0.107 Uiso 0.25 1 calc R U P B 2


_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 O4 2.496(2) 2_656 ?
Eu1 O4 2.496(2) . ?
Eu1 O1 2.504(2) . ?
Eu1 O1 2.504(2) 2_656 ?
Eu1 N12 2.535(2) . ?
Eu1 N12 2.535(2) 2_656 ?
Eu1 O2 2.537(3) 2_656 ?
Eu1 O2 2.537(3) . ?
Eu1 N11 2.575(2) 2_656 ?
Eu1 N11 2.575(3) . ?
Eu1 N2 2.926(3) . ?
Eu1 N1 2.945(3) . ?
N1 O3 1.219(4) . ?
N1 O2 1.268(4) . ?
N1 O1 1.273(4) . ?
N2 O5 1.206(5) . ?
N2 O4 1.271(3) . ?
N2 O4 1.271(3) 2_656 ?
N11 C11 1.329(4) . ?
N11 C22 1.361(4) . ?
N12 C20 1.331(4) . ?
N12 C21 1.364(4) . ?
C11 C12 1.397(5) . ?
C12 C13 1.367(6) . ?
C13 C14 1.410(6) . ?
C14 C22 1.403(4) . ?
C14 C15 1.438(5) . ?
C15 C16 1.335(6) . ?
C16 C17 1.438(5) . ?
C17 C18 1.399(5) . ?
C17 C21 1.409(4) . ?
C18 C19 1.364(5) . ?
C19 C20 1.395(5) . ?
C21 C22 1.436(4) . ?
N31 C31 1.332(11) . ?
N31 C35 1.350(7) . ?
C31 C32 1.408(10) . ?
C31 C31 1.471(13) 7_656 ?
C32 C33 1.391(11) . ?
C33 C34 1.358(10) . ?
C34 C35 1.391(10) . ?
N31' C31' 1.315(19) . ?
N31' C35' 1.343(17) . ?
C31' C32' 1.405(19) . ?
C31' C31' 1.62(4) 7_656 ?
C32' C33' 1.405(19) . ?
C33' C34' 1.359(19) . ?
C34' C35' 1.383(19) . ?

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
O4 Eu1 O4 51.17(10) 2_656 . ?
O4 Eu1 O1 74.88(7) 2_656 . ?
O4 Eu1 O1 73.44(8) . . ?
O4 Eu1 O1 73.44(8) 2_656 2_656 ?
O4 Eu1 O1 74.88(7) . 2_656 ?
O1 Eu1 O1 144.77(11) . 2_656 ?
O4 Eu1 N12 84.09(7) 2_656 . ?
O4 Eu1 N12 129.90(7) . . ?
O1 Eu1 N12 120.32(8) . . ?
O1 Eu1 N12 71.09(7) 2_656 . ?
O4 Eu1 N12 129.90(7) 2_656 2_656 ?
O4 Eu1 N12 84.09(7) . 2_656 ?
O1 Eu1 N12 71.09(7) . 2_656 ?
O1 Eu1 N12 120.32(8) 2_656 2_656 ?
N12 Eu1 N12 145.26(11) . 2_656 ?
O4 Eu1 O2 105.23(7) 2_656 2_656 ?
O4 Eu1 O2 67.69(7) . 2_656 ?
O1 Eu1 O2 126.41(8) . 2_656 ?
O1 Eu1 O2 50.74(8) 2_656 2_656 ?
N12 Eu1 O2 112.81(8) . 2_656 ?
N12 Eu1 O2 69.57(8) 2_656 2_656 ?
O4 Eu1 O2 67.69(7) 2_656 . ?
O4 Eu1 O2 105.23(7) . . ?
O1 Eu1 O2 50.75(8) . . ?
O1 Eu1 O2 126.41(8) 2_656 . ?
N12 Eu1 O2 69.57(8) . . ?
N12 Eu1 O2 112.81(8) 2_656 . ?
O2 Eu1 O2 172.57(10) 2_656 . ?
O4 Eu1 N11 136.66(8) 2_656 2_656 ?
O4 Eu1 N11 140.45(7) . 2_656 ?
O1 Eu1 N11 74.01(8) . 2_656 ?
O1 Eu1 N11 141.10(8) 2_656 2_656 ?
N12 Eu1 N11 86.31(8) . 2_656 ?
N12 Eu1 N11 64.44(8) 2_656 2_656 ?
O2 Eu1 N11 117.42(8) 2_656 2_656 ?
O2 Eu1 N11 69.34(8) . 2_656 ?
O4 Eu1 N11 140.45(7) 2_656 . ?
O4 Eu1 N11 136.66(8) . . ?
O1 Eu1 N11 141.10(8) . . ?
O1 Eu1 N11 74.01(8) 2_656 . ?
N12 Eu1 N11 64.44(8) . . ?
N12 Eu1 N11 86.31(8) 2_656 . ?
O2 Eu1 N11 69.34(8) 2_656 . ?
O2 Eu1 N11 117.42(8) . . ?
N11 Eu1 N11 67.67(11) 2_656 . ?
O4 Eu1 N2 25.58(5) 2_656 . ?
O4 Eu1 N2 25.58(5) . . ?
O1 Eu1 N2 72.38(5) . . ?
O1 Eu1 N2 72.38(5) 2_656 . ?
N12 Eu1 N2 107.37(5) . . ?
N12 Eu1 N2 107.37(5) 2_656 . ?
O2 Eu1 N2 86.29(5) 2_656 . ?
O2 Eu1 N2 86.29(5) . . ?
N11 Eu1 N2 146.16(6) 2_656 . ?
N11 Eu1 N2 146.16(6) . . ?
O4 Eu1 N1 70.03(8) 2_656 . ?
O4 Eu1 N1 89.91(8) . . ?
O1 Eu1 N1 25.39(8) . . ?
O1 Eu1 N1 142.02(8) 2_656 . ?
N12 Eu1 N1 94.93(8) . . ?
N12 Eu1 N1 91.58(8) 2_656 . ?
O2 Eu1 N1 151.51(8) 2_656 . ?
O2 Eu1 N1 25.38(8) . . ?
N11 Eu1 N1 68.86(8) 2_656 . ?
N11 Eu1 N1 132.58(8) . . ?
N2 Eu1 N1 79.04(6) . . ?
O3 N1 O2 121.3(3) . . ?
O3 N1 O1 122.2(3) . . ?
O2 N1 O1 116.5(3) . . ?
O3 N1 Eu1 177.2(2) . . ?
O2 N1 Eu1 59.02(16) . . ?
O1 N1 Eu1 57.53(14) . . ?
N1 O1 Eu1 97.07(16) . . ?
N1 O2 Eu1 95.61(19) . . ?
O5 N2 O4 122.01(16) . . ?
O5 N2 O4 122.01(16) . 2_656 ?
O4 N2 O4 116.0(3) . 2_656 ?
O5 N2 Eu1 180.0 . . ?
O4 N2 Eu1 57.99(16) . . ?
O4 N2 Eu1 57.99(16) 2_656 . ?
N2 O4 Eu1 96.43(17) . . ?
C11 N11 C22 118.4(3) . . ?
C11 N11 Eu1 122.6(2) . . ?
C22 N11 Eu1 119.01(19) . . ?
C20 N12 C21 118.3(3) . . ?
C20 N12 Eu1 121.4(2) . . ?
C21 N12 Eu1 120.02(19) . . ?
N11 C11 C12 123.2(3) . . ?
C13 C12 C11 118.7(3) . . ?
C12 C13 C14 119.9(3) . . ?
C22 C14 C13 117.6(3) . . ?
C22 C14 C15 118.9(3) . . ?
C13 C14 C15 123.4(3) . . ?
C16 C15 C14 121.2(3) . . ?
C15 C16 C17 121.6(3) . . ?
C18 C17 C21 117.8(3) . . ?
C18 C17 C16 123.6(3) . . ?
C21 C17 C16 118.6(3) . . ?
C19 C18 C17 120.0(3) . . ?
C18 C19 C20 118.9(3) . . ?
N12 C20 C19 123.1(3) . . ?
N12 C21 C17 121.9(3) . . ?
N12 C21 C22 118.4(2) . . ?
C17 C21 C22 119.7(3) . . ?
N11 C22 C14 122.2(3) . . ?
N11 C22 C21 118.0(3) . . ?
C14 C22 C21 119.8(3) . . ?
C31 N31 C35 116.4(6) . . ?
N31 C31 C32 122.5(6) . . ?
N31 C31 C31 119.6(11) . 7_656 ?
C32 C31 C31 117.9(11) . 7_656 ?
C33 C32 C31 119.9(6) . . ?
C34 C33 C32 117.4(7) . . ?
C33 C34 C35 119.8(7) . . ?
N31 C35 C34 123.9(6) . . ?
C31' N31' C35' 113.9(17) . . ?
N31' C31' C32' 128.5(18) . . ?
N31' C31' C31' 119(2) . 7_656 ?
C32' C31' C31' 112(2) . 7_656 ?
C31' C32' C33' 116.2(17) . . ?
C34' C33' C32' 115.4(19) . . ?
C33' C34' C35' 124(2) . . ?
N31' C35' C34' 121.8(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H19 O4 0.95 2.62 3.187(4) 118.7 6_565
C35 H35 O3 0.95 2.65 3.531(7) 155.2 4_646

_refine_diff_density_max         0.977
_refine_diff_density_min         -1.171
_refine_diff_density_rms         0.095

_shelxl_version_number           2014-3

