# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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. 
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data_exp_8539
_database_code_depnum_ccdc_archive 'CCDC 1827828'
_audit_update_record             
;
2018-05-21 deposited with the CCDC.
2018-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23.50 Eu N2.50 O13'
_chemical_formula_weight         706.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -8.9294 11.1857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.8233(8)
_cell_length_b                   11.1006(13)
_cell_length_c                   13.2788(12)
_cell_angle_alpha                67.740(10)
_cell_angle_beta                 78.409(8)
_cell_angle_gamma                70.095(9)
_cell_volume                     1255.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1585
_cell_measurement_theta_min      3.6320
_cell_measurement_theta_max      70.6820

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    18.564
_shelx_estimated_absorpt_T_min   0.318
_shelx_estimated_absorpt_T_max   0.356
_exptl_absorpt_correction_T_min  0.19368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7709
_diffrn_reflns_av_unetI/netI     0.1534
_diffrn_reflns_av_R_equivalents  0.0975
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.609
_diffrn_reflns_theta_max         67.246
_diffrn_reflns_theta_full        67.246
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4480
_reflns_number_gt                3353
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1342P)²+1.1748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4480
_refine_ls_number_parameters     391
_refine_ls_number_restraints     1008
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0855
_refine_ls_wR_factor_ref         0.2450
_refine_ls_wR_factor_gt          0.2135
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      0.983
_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_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 0.71979(7) 0.51820(7) 0.49211(5) 0.0179(3) Uani 1 1 d . U . . .
N1 N 0.712(2) 0.953(2) 0.4603(19) 0.099(4) Uani 1 1 d . U . . .
N2 N 1.1174(11) 0.3209(12) -0.0489(9) 0.0292(19) Uani 1 1 d . U . . .
O1 O 0.7227(10) 0.4263(10) 0.3550(7) 0.0313(17) Uani 1 1 d . U . . .
O2 O 0.4903(9) 0.4251(10) 0.3968(7) 0.0315(17) Uani 1 1 d . U . . .
O3 O 0.2599(13) 0.2811(15) 0.1717(10) 0.059(3) Uani 1 1 d . U . . .
O4 O 0.3606(12) 0.3021(14) 0.0047(9) 0.047(3) Uani 1 1 d . U . . .
H4 H 0.2818 0.2987 -0.0038 0.071 Uiso 1 1 calc R U . . .
O5 O 0.8413(9) 0.4628(11) -0.3506(7) 0.0323(19) Uani 1 1 d . U . . .
O6 O 1.0816(10) 0.4149(11) -0.3759(7) 0.0338(19) Uani 1 1 d . U . . .
O7 O 0.5659(10) 0.6968(11) 0.3546(8) 0.0348(17) Uani 1 1 d . U . . .
O8 O 0.3376(10) 0.6835(10) 0.4036(8) 0.0344(18) Uani 1 1 d . U . . .
O9 O 0.9439(12) 0.3145(13) 0.4998(10) 0.054(3) Uani 1 1 d . U . . .
H9B H 0.9183 0.2420 0.5272 0.065 Uiso 1 1 d R U . . .
H9A H 1.0033 0.3124 0.5394 0.081 Uiso 1 1 d R U . . .
O10 O 0.7198(13) 0.7340(13) 0.4999(10) 0.054(2) Uani 1 1 d . U . . .
O14 O 0.024(2) 0.214(2) 0.3196(14) 0.119(6) Uani 1 1 d . U . . .
H14C H 0.0001 0.2863 0.3348 0.142 Uiso 1 1 d R U . . .
H14D H 0.0972 0.2138 0.2733 0.142 Uiso 1 1 d R U . . .
O15 O 0.978(2) 0.968(2) 0.3569(16) 0.132(5) Uani 1 1 d . U . . .
H15C H 0.9898 1.0439 0.3474 0.159 Uiso 1 1 d R U . . .
H15B H 0.9856 0.9571 0.2958 0.159 Uiso 1 1 d R U . . .
C1 C 0.6082(14) 0.4104(15) 0.3393(11) 0.031(2) Uani 1 1 d . U . . .
C2 C 0.6093(14) 0.3755(15) 0.2376(11) 0.029(2) Uani 1 1 d . U . . .
C3 C 0.4906(14) 0.3505(15) 0.2190(11) 0.0274(19) Uani 1 1 d . U . . .
H3 H 0.4092 0.3532 0.2688 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4922(14) 0.3210(15) 0.1252(11) 0.028(2) Uani 1 1 d . U . . .
C5 C 0.6128(14) 0.3181(15) 0.0503(11) 0.0285(19) Uani 1 1 d . U . . .
H5 H 0.6145 0.2973 -0.0116 0.034 Uiso 1 1 calc R U . . .
C6 C 0.7347(14) 0.3472(15) 0.0688(11) 0.0275(19) Uani 1 1 d . U . . .
C7 C 0.7299(14) 0.3743(15) 0.1645(11) 0.0290(19) Uani 1 1 d . U . . .
H7 H 0.8090 0.3917 0.1786 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3601(15) 0.2987(16) 0.1046(12) 0.034(2) Uani 1 1 d . U . . .
C9 C 0.8623(14) 0.3480(15) -0.0115(11) 0.029(2) Uani 1 1 d . U . . .
C10 C 0.8519(14) 0.3854(15) -0.1235(10) 0.0279(19) Uani 1 1 d . U . . .
H10 H 0.7620 0.4083 -0.1495 0.033 Uiso 1 1 calc R U . . .
C11 C 0.9740(13) 0.3883(15) -0.1956(10) 0.028(2) Uani 1 1 d . U . . .
C12 C 1.1047(14) 0.3600(15) -0.1564(11) 0.030(2) Uani 1 1 d . U . . .
H12 H 1.1861 0.3681 -0.2053 0.036 Uiso 1 1 calc R U . . .
C13 C 0.9976(14) 0.3161(15) 0.0200(11) 0.028(2) Uani 1 1 d . U . . .
H13 H 1.0075 0.2892 0.0942 0.033 Uiso 1 1 calc R U . . .
C14 C 0.9665(14) 0.4258(15) -0.3172(11) 0.029(2) Uani 1 1 d . U . . .
C15 C 0.4366(14) 0.7246(15) 0.3377(11) 0.030(2) Uani 1 1 d . U . . .
C16 C 0.3923(14) 0.8242(15) 0.2254(11) 0.029(2) Uani 1 1 d . U . . .
C17 C 0.4870(14) 0.8847(14) 0.1475(11) 0.028(2) Uani 1 1 d . U . . .
H17 H 0.5802 0.8681 0.1650 0.034 Uiso 1 1 d R U . . .
C18 C 0.4485(13) 0.9702(15) 0.0407(11) 0.026(2) Uani 1 1 d . U . . .
C19 C 0.3082(14) 0.9889(14) 0.0191(11) 0.031(2) Uani 1 1 d . U . . .
H19 H 0.2816 1.0396 -0.0516 0.038 Uiso 1 1 d R U . A .
C20 C 0.204(7) 0.943(8) 0.096(8) 0.030(3) Uani 0.5 1 d . U P A 1
C22 C 0.057(3) 0.970(3) 0.067(2) 0.032(3) Uani 0.5 1 d . U P A 1
O11 O -0.040(2) 0.940(2) 0.1336(16) 0.036(3) Uani 0.5 1 d . U P A 1
O12 O 0.049(2) 1.017(2) -0.0373(16) 0.037(3) Uani 0.5 1 d . U P A 1
H12A H -0.0359 1.0615 -0.0497 0.056 Uiso 0.5 1 d R U P A 1
N3 N 0.215(6) 0.931(6) 0.094(6) 0.030(3) Uani 0.5 1 d . U P A 2
C21 C 0.2529(14) 0.8532(15) 0.1981(11) 0.0284(19) Uani 1 1 d . U . . .
H21 H 0.1860 0.8164 0.2503 0.034 Uiso 1 1 d R U . A .
C23 C 0.702(2) 0.832(2) 0.525(2) 0.079(4) Uani 1 1 d . U . . .
H23 H 0.6791 0.8206 0.5985 0.095 Uiso 1 1 calc R U . . .
C24 C 0.700(3) 1.066(3) 0.500(2) 0.113(6) Uani 1 1 d . U . . .
H24A H 0.6408 1.0560 0.5676 0.169 Uiso 1 1 calc R U . . .
H24B H 0.6570 1.1518 0.4466 0.169 Uiso 1 1 calc R U . . .
H24C H 0.7953 1.0630 0.5106 0.169 Uiso 1 1 calc R U . . .
C25 C 0.709(3) 0.981(3) 0.329(2) 0.115(6) Uani 1 1 d . U . . .
H25A H 0.7858 0.9121 0.3082 0.172 Uiso 1 1 calc R U . . .
H25B H 0.7230 1.0688 0.2872 0.172 Uiso 1 1 calc R U . . .
H25C H 0.6173 0.9796 0.3167 0.172 Uiso 1 1 calc R 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 O2 2.330(9) 2_666 ?
Eu1 O8 2.334(10) 2_666 ?
Eu1 O6 2.376(9) 2_765 ?
Eu1 O5 2.387(9) 1_556 ?
Eu1 O1 2.393(10) . ?
Eu1 O7 2.424(9) . ?
Eu1 O10 2.436(13) . ?
Eu1 O9 2.549(12) . ?
Eu1 Eu1 4.4288(13) 2_666 ?
N1 C23 1.32(3) . ?
N1 C24 1.49(4) . ?
N1 C25 1.65(3) . ?
N2 C13 1.341(16) . ?
N2 C12 1.345(17) . ?
O1 C1 1.263(16) . ?
O2 C1 1.250(15) . ?
O2 Eu1 2.330(9) 2_666 ?
O3 C8 1.203(17) . ?
O4 C8 1.312(17) . ?
O5 C14 1.270(15) . ?
O5 Eu1 2.387(9) 1_554 ?
O6 C14 1.235(15) . ?
O6 Eu1 2.376(9) 2_765 ?
O7 C15 1.247(16) . ?
O8 C15 1.256(15) . ?
O8 Eu1 2.334(10) 2_666 ?
O10 C23 1.20(3) . ?
C1 C2 1.54(2) . ?
C2 C7 1.372(18) . ?
C2 C3 1.373(18) . ?
C3 C4 1.399(18) . ?
C4 C5 1.385(18) . ?
C4 C8 1.494(18) . ?
C5 C6 1.428(18) . ?
C6 C7 1.402(19) . ?
C6 C9 1.473(18) . ?
C9 C13 1.362(18) . ?
C9 C10 1.401(18) . ?
C10 C11 1.377(17) . ?
C11 C12 1.373(18) . ?
C11 C14 1.519(18) . ?
C15 C16 1.524(18) . ?
C16 C17 1.378(18) . ?
C16 C21 1.386(17) . ?
C17 C18 1.416(18) . ?
C18 C19 1.393(18) . ?
C18 C18 1.45(3) 2_675 ?
C19 N3 1.35(7) . ?
C19 C20 1.37(9) . ?
C20 C21 1.41(9) . ?
C20 C22 1.46(8) . ?
C22 O12 1.13(3) 2_575 ?
C22 O11 1.20(3) . ?
C22 O12 1.30(3) . ?
O11 O12 1.19(3) 2_575 ?
O12 C22 1.13(3) 2_575 ?
O12 O11 1.19(3) 2_575 ?
O12 O12 1.27(4) 2_575 ?
N3 C21 1.37(8) . ?

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
O2 Eu1 O8 73.0(4) 2_666 2_666 ?
O2 Eu1 O6 147.6(4) 2_666 2_765 ?
O8 Eu1 O6 137.9(4) 2_666 2_765 ?
O2 Eu1 O5 84.2(3) 2_666 1_556 ?
O8 Eu1 O5 81.7(3) 2_666 1_556 ?
O6 Eu1 O5 90.6(3) 2_765 1_556 ?
O2 Eu1 O1 121.4(3) 2_666 . ?
O8 Eu1 O1 78.2(3) 2_666 . ?
O6 Eu1 O1 81.9(3) 2_765 . ?
O5 Eu1 O1 139.9(4) 1_556 . ?
O2 Eu1 O7 80.4(3) 2_666 . ?
O8 Eu1 O7 121.7(3) 2_666 . ?
O6 Eu1 O7 86.5(3) 2_765 . ?
O5 Eu1 O7 145.9(4) 1_556 . ?
O1 Eu1 O7 73.1(3) . . ?
O2 Eu1 O10 76.8(4) 2_666 . ?
O8 Eu1 O10 142.7(4) 2_666 . ?
O6 Eu1 O10 71.0(4) 2_765 . ?
O5 Eu1 O10 73.9(4) 1_556 . ?
O1 Eu1 O10 137.5(4) . . ?
O7 Eu1 O10 73.1(4) . . ?
O2 Eu1 O9 137.6(4) 2_666 . ?
O8 Eu1 O9 69.9(4) 2_666 . ?
O6 Eu1 O9 68.5(4) 2_765 . ?
O5 Eu1 O9 70.9(4) 1_556 . ?
O1 Eu1 O9 69.7(4) . . ?
O7 Eu1 O9 137.4(4) . . ?
O10 Eu1 O9 125.0(4) . . ?
O2 Eu1 Eu1 48.9(2) 2_666 2_666 ?
O8 Eu1 Eu1 58.6(2) 2_666 2_666 ?
O6 Eu1 Eu1 145.7(2) 2_765 2_666 ?
O5 Eu1 Eu1 123.7(2) 1_556 2_666 ?
O1 Eu1 Eu1 72.5(2) . 2_666 ?
O7 Eu1 Eu1 64.7(2) . 2_666 ?
O10 Eu1 Eu1 114.0(3) . 2_666 ?
O9 Eu1 Eu1 120.6(3) . 2_666 ?
C23 N1 C24 124(3) . . ?
C23 N1 C25 114(2) . . ?
C24 N1 C25 121(2) . . ?
C13 N2 C12 118.5(11) . . ?
C1 O1 Eu1 120.4(9) . . ?
C1 O2 Eu1 170.4(10) . 2_666 ?
C14 O5 Eu1 142.8(9) . 1_554 ?
C14 O6 Eu1 157.9(10) . 2_765 ?
C15 O7 Eu1 133.4(9) . . ?
C15 O8 Eu1 140.5(10) . 2_666 ?
C23 O10 Eu1 165.8(14) . . ?
O2 C1 O1 126.3(14) . . ?
O2 C1 C2 115.7(12) . . ?
O1 C1 C2 117.9(11) . . ?
C7 C2 C3 121.1(13) . . ?
C7 C2 C1 118.2(12) . . ?
C3 C2 C1 120.6(12) . . ?
C2 C3 C4 120.0(12) . . ?
C5 C4 C3 120.2(12) . . ?
C5 C4 C8 120.6(12) . . ?
C3 C4 C8 119.2(12) . . ?
C4 C5 C6 119.6(13) . . ?
C7 C6 C5 118.5(12) . . ?
C7 C6 C9 121.2(12) . . ?
C5 C6 C9 120.2(12) . . ?
C2 C7 C6 120.5(12) . . ?
O3 C8 O4 121.9(14) . . ?
O3 C8 C4 124.2(14) . . ?
O4 C8 C4 113.9(12) . . ?
C13 C9 C10 116.3(12) . . ?
C13 C9 C6 121.0(12) . . ?
C10 C9 C6 122.6(12) . . ?
C11 C10 C9 120.3(12) . . ?
C12 C11 C10 119.0(12) . . ?
C12 C11 C14 119.5(11) . . ?
C10 C11 C14 121.5(12) . . ?
N2 C12 C11 121.4(12) . . ?
N2 C13 C9 124.3(12) . . ?
O6 C14 O5 124.8(13) . . ?
O6 C14 C11 118.1(12) . . ?
O5 C14 C11 117.1(11) . . ?
O7 C15 O8 127.6(13) . . ?
O7 C15 C16 116.2(11) . . ?
O8 C15 C16 116.2(11) . . ?
C17 C16 C21 118.0(12) . . ?
C17 C16 C15 122.6(12) . . ?
C21 C16 C15 119.4(12) . . ?
C16 C17 C18 122.4(12) . . ?
C19 C18 C17 115.6(12) . . ?
C19 C18 C18 123.1(15) . 2_675 ?
C17 C18 C18 121.3(14) . 2_675 ?
N3 C19 C18 123(3) . . ?
C20 C19 C18 125(4) . . ?
C19 C20 C21 115(5) . . ?
C19 C20 C22 122(7) . . ?
C21 C20 C22 122(6) . . ?
O12 C22 O11 61.3(18) 2_575 . ?
O12 C22 O12 63(2) 2_575 . ?
O11 C22 O12 124(3) . . ?
O12 C22 C20 172(5) 2_575 . ?
O11 C22 C20 124(4) . . ?
O12 C22 C20 112(4) . . ?
O12 O11 C22 56.4(18) 2_575 . ?
C22 O12 O11 62(2) 2_575 2_575 ?
C22 O12 O12 65(2) 2_575 2_575 ?
O11 O12 O12 127(3) 2_575 2_575 ?
C22 O12 C22 117(2) 2_575 . ?
O11 O12 C22 180(3) 2_575 . ?
O12 O12 C22 52.4(18) 2_575 . ?
C19 N3 C21 120(5) . . ?
N3 C21 C16 121(3) . . ?
C16 C21 C20 123(4) . . ?
O10 C23 N1 128(2) . . ?

_refine_diff_density_max         1.752
_refine_diff_density_min         -2.134
_refine_diff_density_rms         0.235

