# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1430315'
_audit_update_record             
;
2016-06-10 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C10 H12 Eu O13), 3(H2 O), C5 H7 N2'
_chemical_formula_sum            'C15 H25 Eu N2 O16'
_chemical_formula_weight         641.33

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           Monoclinic
_space_group_name_Hall           '-C 2yc'
_symmetry_space_group_name_H-M   'C2/c   '

loop_
_symmetry_equiv_pos_as_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                   13.0689(8)
_cell_length_b                   11.2535(6)
_cell_length_c                   15.4306(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.9080(10)
_cell_angle_gamma                90.00
_cell_volume                     2182.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2898
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      29

_exptl_crystal_description       blcok
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    2.959
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6179
_exptl_absorpt_correction_T_max  0.6652
_exptl_absorpt_process_details   'Higashi (1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 'Bruker SMART CCD area'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none'
_diffrn_reflns_number            8077
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         29.00
_reflns_number_total             2898
_reflns_number_gt                2760
_reflns_threshold_expression     >2sigma(I)

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

_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. 

1. Shared sites
{C13, N13}
2. Others
 Fixed Sof: H2A(0.5) H2B(0.5) N2(0.5) H131(0.5) C13(0.5) N13(0.5)
 O9(0.5) H9A(0.5) H9B(0.5) O7(0.5) H77a(0.5)
3.a Riding coordinates:
 C7(H7), C6(H6), C13(H131)
3.b Free rotating group:
 O8(H8A,H8B), O9(H9A,H9B)
3.c Rotating group:
 O5(H5A,H5B), O6(H66A,H66B), O7(H77A)
3.d Aromatic/amide H refined with riding coordinates:
 C3(H3)
3.e X=CH2 refined with riding coordinates:
 N2(H2a,H2b)

;

_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)+(0.0251P)²+2.3288P] 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         2898
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0532
_refine_ls_wR_factor_gt          0.0522
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.0000 0.118634(12) 0.2500 0.01741(6) Uani 1 2 d S . .
O1 O -0.08928(13) 0.24921(14) 0.11500(11) 0.0220(3) Uani 1 1 d . . .
O2 O 0.07543(13) 0.28897(14) 0.18877(11) 0.0248(3) Uani 1 1 d . . .
O3 O -0.00624(15) 0.17647(14) -0.03764(12) 0.0289(4) Uani 1 1 d . . .
O4 O -0.1141(2) 0.26014(17) -0.15732(14) 0.0574(7) Uani 1 1 d . . .
O5 O 0.03159(17) 0.04014(14) 0.11475(11) 0.0323(4) Uani 1 1 d . . .
H5A H 0.0159 -0.0304 0.1101 0.039 Uiso 1 1 d R . .
H5B H 0.0276 0.0784 0.0767 0.039 Uiso 1 1 d R . .
O6 O 0.18974(16) 0.07880(17) 0.29984(13) 0.0341(4) Uani 1 1 d . . .
H66A H 0.1993 0.0314 0.2654 0.041 Uiso 1 1 d R . .
H66B H 0.2303 0.1300 0.3125 0.041 Uiso 1 1 d R . .
O7 O 0.0000 -0.1032(2) 0.2500 0.0480(9) Uani 1 2 d S . .
H77A H 0.0215 -0.1449 0.2097 0.058 Uiso 1 1 d R . .
C1 C -0.00066(17) 0.40404(18) 0.05722(14) 0.0159(4) Uani 1 1 d . . .
C2 C -0.02849(17) 0.38586(16) -0.03576(15) 0.0165(4) Uani 1 1 d . . .
C3 C 0.02755(18) 0.51726(18) 0.09181(14) 0.0183(4) Uani 1 1 d . . .
H3 H 0.0462 0.5286 0.1539 0.022 Uiso 1 1 calc R . .
C4 C -0.00561(17) 0.30746(17) 0.12342(14) 0.0163(4) Uani 1 1 d . . .
C5 C -0.0525(2) 0.26452(19) -0.07929(15) 0.0227(5) Uani 1 1 d . . .
O8 O 0.23193(19) 0.4282(2) 0.29753(15) 0.0531(6) Uani 1 1 d . . .
H8A H 0.2945 0.3904 0.3215 0.064 Uiso 1 1 d R . .
H8B H 0.1844 0.3889 0.2549 0.064 Uiso 1 1 d R . .
C7 C 0.2653(3) 1.1946(3) 1.0817(2) 0.0513(8) Uani 1 1 d . A -1
C6 C 0.23019(15) 1.18565(19) 0.92333(16) 0.0500(8) Uani 1 1 d . A -1
H6 H 0.2166 1.1393 0.8691 0.060 Uiso 1 1 d R A -1
H7 H 0.2773 1.1560 1.1402 0.060 Uiso 1 1 d R A -1
C13 C 0.24493(15) 1.13009(19) 1.00343(16) 0.0457(7) Uani 0.50 1 d PR A -1
O9 O 0.23889(15) 0.87573(19) 1.00410(16) 0.0612(16) Uani 0.50 1 d PR A 1
H9A H 0.2629 0.8511 0.9600 0.073 Uiso 0.50 1 d PR A 1
H9B H 0.2091 0.8065 1.0166 0.073 Uiso 0.50 1 d PR A 1
N2 N 0.2387(4) 1.0120(5) 1.0102(4) 0.0459(12) Uani 0.50 1 d P A -1
H2A H 0.2474 0.9791 1.0616 0.055 Uiso 0.50 1 d PR A -1
H2B H 0.2273 0.9697 0.9620 0.055 Uiso 0.50 1 d PR A -1
N13 N 0.24493(15) 1.13009(19) 1.00343(16) 0.0457(7) Uani 0.50 1 d P A -1
H131 H 0.2281 1.0703 1.0073 0.055 Uiso 0.50 1 d PR A -1


_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 O5 2.4039(17) . ?
Eu1 O5 2.4039(17) 2 ?
Eu1 O6 2.4282(19) 2 ?
Eu1 O6 2.4282(19) . ?
Eu1 O2 2.4596(16) . ?
Eu1 O2 2.4596(16) 2 ?
Eu1 O7 2.496(2) . ?
Eu1 O1 2.5550(16) 2 ?
Eu1 O1 2.5550(16) . ?
Eu1 C4 2.874(2) 2 ?
Eu1 H5A 2.7857 . ?
Eu1 H66A 2.7326 . ?
O1 C4 1.251(3) . ?
O2 C4 1.264(3) . ?
O3 C5 1.244(3) . ?
O4 C5 1.253(3) . ?
O5 H5A 0.8179 . ?
O5 H5B 0.7181 . ?
O6 H66A 0.7866 . ?
O6 H66B 0.7709 . ?
O7 H77A 0.8838 . ?
C1 C3 1.392(3) . ?
C1 C2 1.395(3) . ?
C1 C4 1.505(3) . ?
C2 C3 1.394(3) 5_565 ?
C2 C5 1.516(3) . ?
C3 C2 1.394(3) 5_565 ?
C3 H3 0.9300 . ?
O8 H8A 0.9063 . ?
O8 H8B 0.8890 . ?
C7 C13 1.372(4) . ?
C7 H7 0.9742 . ?
C6 C13 1.3511 . ?
C6 H6 0.9600 . ?
C13 N2 1.338(6) . ?
C13 H131 0.7149 . ?
O9 N2 1.536(5) . ?
O9 H9A 0.8695 . ?
O9 H9B 0.9150 . ?
O9 H2A 1.4485 . ?
O9 H2B 1.2284 . ?
N2 H2A 0.8551 . ?
N2 H2B 0.8600 . ?
N2 H131 0.6702 . ?

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
O5 Eu1 O5 136.88(8) . 2 ?
O5 Eu1 O6 93.48(7) . 2 ?
O5 Eu1 O6 78.68(7) 2 2 ?
O5 Eu1 O6 78.68(7) . . ?
O5 Eu1 O6 93.48(7) 2 . ?
O6 Eu1 O6 158.72(9) 2 . ?
O5 Eu1 O2 76.74(6) . . ?
O5 Eu1 O2 143.34(6) 2 . ?
O6 Eu1 O2 120.28(6) 2 . ?
O6 Eu1 O2 77.50(6) . . ?
O5 Eu1 O2 143.34(6) . 2 ?
O5 Eu1 O2 76.74(6) 2 2 ?
O6 Eu1 O2 77.50(6) 2 2 ?
O6 Eu1 O2 120.28(6) . 2 ?
O2 Eu1 O2 77.60(8) . 2 ?
O5 Eu1 O7 68.44(4) . . ?
O5 Eu1 O7 68.44(4) 2 . ?
O6 Eu1 O7 79.36(5) 2 . ?
O6 Eu1 O7 79.36(5) . . ?
O2 Eu1 O7 141.20(4) . . ?
O2 Eu1 O7 141.20(4) 2 . ?
O5 Eu1 O1 140.40(6) . 2 ?
O5 Eu1 O1 69.65(6) 2 2 ?
O6 Eu1 O1 124.26(6) 2 2 ?
O6 Eu1 O1 69.48(6) . 2 ?
O2 Eu1 O1 73.94(5) . 2 ?
O2 Eu1 O1 51.69(5) 2 2 ?
O7 Eu1 O1 125.11(4) . 2 ?
O5 Eu1 O1 69.65(6) . . ?
O5 Eu1 O1 140.40(6) 2 . ?
O6 Eu1 O1 69.48(6) 2 . ?
O6 Eu1 O1 124.26(6) . . ?
O2 Eu1 O1 51.69(5) . . ?
O2 Eu1 O1 73.94(5) 2 . ?
O7 Eu1 O1 125.11(4) . . ?
O1 Eu1 O1 109.78(7) 2 . ?
O5 Eu1 C4 152.06(6) . 2 ?
O5 Eu1 C4 70.13(6) 2 2 ?
O6 Eu1 C4 100.68(6) 2 2 ?
O6 Eu1 C4 95.03(6) . 2 ?
O2 Eu1 C4 75.32(6) . 2 ?
O2 Eu1 C4 25.95(6) 2 2 ?
O7 Eu1 C4 137.69(4) . 2 ?
O1 Eu1 C4 25.79(6) 2 2 ?
O1 Eu1 C4 92.85(5) . 2 ?
O5 Eu1 H5A 16.1 . . ?
O5 Eu1 H5A 121.2 2 . ?
O6 Eu1 H5A 86.0 2 . ?
O6 Eu1 H5A 81.2 . . ?
O2 Eu1 H5A 92.8 . . ?
O2 Eu1 H5A 152.8 2 . ?
O7 Eu1 H5A 53.0 . . ?
O1 Eu1 H5A 149.7 2 . ?
O1 Eu1 H5A 80.1 . . ?
C4 Eu1 H5A 168.1 2 . ?
O5 Eu1 H66A 63.7 . . ?
O5 Eu1 H66A 100.3 2 . ?
O6 Eu1 H66A 145.9 2 . ?
O6 Eu1 H66A 16.2 . . ?
O2 Eu1 H66A 80.8 . . ?
O2 Eu1 H66A 136.0 2 . ?
O7 Eu1 H66A 68.9 . . ?
O1 Eu1 H66A 85.6 2 . ?
O1 Eu1 H66A 119.3 . . ?
C4 Eu1 H66A 111.1 2 . ?
H5A Eu1 H66A 65.1 . . ?
C4 O1 Eu1 91.48(13) . . ?
C4 O2 Eu1 95.65(13) . . ?
Eu1 O5 H5A 109.5 . . ?
Eu1 O5 H5B 119.9 . . ?
H5A O5 H5B 123.3 . . ?
Eu1 O6 H66A 104.4 . . ?
Eu1 O6 H66B 120.9 . . ?
H66A O6 H66B 116.9 . . ?
Eu1 O7 H77A 122.1 . . ?
C3 C1 C2 119.71(18) . . ?
C3 C1 C4 117.20(19) . . ?
C2 C1 C4 122.99(18) . . ?
C3 C2 C1 118.63(18) 5_565 . ?
C3 C2 C5 117.75(19) 5_565 . ?
C1 C2 C5 123.48(18) . . ?
C1 C3 C2 121.7(2) . 5_565 ?
C1 C3 H3 119.2 . . ?
C2 C3 H3 119.2 5_565 . ?
O1 C4 O2 120.95(19) . . ?
O1 C4 C1 120.46(19) . . ?
O2 C4 C1 118.56(19) . . ?
O3 C5 O4 123.9(2) . . ?
O3 C5 C2 118.5(2) . . ?
O4 C5 C2 117.5(2) . . ?
H8A O8 H8B 116.0 . . ?
C13 C7 H7 121.5 . . ?
C13 C6 H6 119.5 . . ?
N2 C13 C6 122.3(3) . . ?
N2 C13 C7 117.3(4) . . ?
C6 C13 C7 120.35(19) . . ?
N2 C13 H131 14.6 . . ?
C6 C13 H131 122.8 . . ?
C7 C13 H131 114.5 . . ?
N2 O9 H9A 111.9 . . ?
N2 O9 H9B 146.1 . . ?
H9A O9 H9B 99.1 . . ?
N2 O9 H2A 33.1 . . ?
H9A O9 H2A 138.8 . . ?
H9B O9 H2A 121.4 . . ?
N2 O9 H2B 34.0 . . ?
H9A O9 H2B 83.1 . . ?
H9B O9 H2B 147.9 . . ?
H2A O9 H2B 67.1 . . ?
C13 N2 O9 170.5(5) . . ?
C13 N2 H2A 120.5 . . ?
O9 N2 H2A 67.8 . . ?
C13 N2 H2B 118.9 . . ?
O9 N2 H2B 53.0 . . ?
H2A N2 H2B 120.7 . . ?
C13 N2 H131 15.6 . . ?
O9 N2 H131 167.9 . . ?
H2A N2 H131 117.3 . . ?
H2B N2 H131 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.129
