# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_EuL

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Eu N5 O10'
_chemical_formula_weight         666.39

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5509(5)
_cell_length_b                   11.2004(5)
_cell_length_c                   12.8518(6)
_cell_angle_alpha                66.2700(10)
_cell_angle_beta                 76.4140(10)
_cell_angle_gamma                80.5810(10)
_cell_volume                     1219.66(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.76
_cell_measurement_theta_max      26.17

_exptl_crystal_description       brick
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    2.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5783
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sheldrick, G. M. (2008). SADABS'

_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  ?
_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            7804
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.17
_reflns_number_total             4848
_reflns_number_gt                4389
_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)+(0.0288P)²+0.1274P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4848
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0588
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.495220(18) 0.254243(14) 0.449299(12) 0.02087(6) Uani 1 1 d . . .
N1 N 1.0379(4) 0.9476(3) -0.3376(3) 0.0411(8) Uani 1 1 d . . .
N2 N 0.8225(4) 1.0823(3) -0.3193(2) 0.0369(8) Uani 1 1 d . . .
N3 N -0.0704(3) -0.3098(3) 1.2880(2) 0.0390(8) Uani 1 1 d . . .
N4 N 0.1504(4) -0.3931(3) 1.3558(2) 0.0358(7) Uani 1 1 d . . .
N5 N 0.2179(4) 0.3114(3) 0.3681(3) 0.0361(7) Uani 1 1 d . . .
C1 C 0.6352(4) 0.4595(3) 0.2597(3) 0.0262(7) Uani 1 1 d . . .
C2 C 0.6922(4) 0.5666(3) 0.1485(3) 0.0263(7) Uani 1 1 d . . .
C3 C 0.7799(4) 0.5354(3) 0.0586(3) 0.0357(9) Uani 1 1 d . . .
H3A H 0.8044 0.4482 0.0685 0.043 Uiso 1 1 calc R . .
C4 C 0.8311(5) 0.6332(3) -0.0456(3) 0.0386(9) Uani 1 1 d . . .
H4A H 0.8907 0.6111 -0.1047 0.046 Uiso 1 1 calc R . .
C5 C 0.7942(4) 0.7638(3) -0.0622(3) 0.0285(8) Uani 1 1 d . . .
C6 C 0.7052(4) 0.7947(3) 0.0273(3) 0.0293(8) Uani 1 1 d . . .
H6A H 0.6796 0.8820 0.0170 0.035 Uiso 1 1 calc R . .
C7 C 0.6540(4) 0.6970(3) 0.1319(3) 0.0286(8) Uani 1 1 d . . .
H7A H 0.5940 0.7190 0.1909 0.034 Uiso 1 1 calc R . .
C8 C 0.8506(4) 0.8684(3) -0.1728(3) 0.0292(8) Uani 1 1 d . . .
C9 C 0.9857(4) 0.8549(4) -0.2376(3) 0.0380(9) Uani 1 1 d . . .
H9A H 1.0429 0.7775 -0.2099 0.046 Uiso 1 1 calc R . .
C10 C 0.9540(4) 1.0568(4) -0.3727(3) 0.0382(9) Uani 1 1 d . . .
H10A H 0.9908 1.1224 -0.4417 0.046 Uiso 1 1 calc R . .
C11 C 0.7720(4) 0.9857(3) -0.2190(3) 0.0319(8) Uani 1 1 d . . .
H11A H 0.6799 0.9988 -0.1791 0.038 Uiso 1 1 calc R . .
C12 C 0.4573(4) -0.0366(3) 0.6829(3) 0.0241(7) Uani 1 1 d . . .
C13 C 0.3820(4) -0.1001(3) 0.8061(3) 0.0227(7) Uani 1 1 d . . .
C14 C 0.2617(4) -0.0352(3) 0.8501(3) 0.0350(9) Uani 1 1 d . . .
H14A H 0.2297 0.0484 0.8041 0.042 Uiso 1 1 calc R . .
C15 C 0.1890(4) -0.0948(4) 0.9624(3) 0.0385(9) Uani 1 1 d . . .
H15A H 0.1076 -0.0510 0.9910 0.046 Uiso 1 1 calc R . .
C16 C 0.2357(4) -0.2193(3) 1.0333(3) 0.0251(7) Uani 1 1 d . . .
C17 C 0.3575(4) -0.2828(3) 0.9895(3) 0.0270(7) Uani 1 1 d . . .
H17A H 0.3908 -0.3655 1.0361 0.032 Uiso 1 1 calc R . .
C18 C 0.4307(4) -0.2239(3) 0.8759(3) 0.0262(7) Uani 1 1 d . . .
H18A H 0.5119 -0.2676 0.8470 0.031 Uiso 1 1 calc R . .
C19 C 0.1540(4) -0.2791(3) 1.1534(3) 0.0271(7) Uani 1 1 d . . .
C20 C 0.0056(4) -0.2648(4) 1.1796(3) 0.0363(9) Uani 1 1 d . . .
H20A H -0.0446 -0.2217 1.1191 0.044 Uiso 1 1 calc R . .
C21 C 0.0086(4) -0.3688(4) 1.3698(3) 0.0381(9) Uani 1 1 d . . .
H21A H -0.0417 -0.3962 1.4457 0.046 Uiso 1 1 calc R . .
C22 C 0.2218(4) -0.3476(3) 1.2472(3) 0.0300(8) Uani 1 1 d . . .
H22A H 0.3219 -0.3624 1.2336 0.036 Uiso 1 1 calc R . .
O1 O 0.5497(3) 0.4891(2) 0.33909(18) 0.0295(5) Uani 1 1 d . . .
O1W O 0.6573(3) 0.3003(2) 0.5470(2) 0.0420(7) Uani 1 1 d . . .
H1WA H 0.7334 0.2487 0.5482 0.063 Uiso 1 1 d R . .
H1WB H 0.6797 0.3789 0.5102 0.063 Uiso 1 1 d R . .
O2 O 0.6694(3) 0.3422(2) 0.27070(19) 0.0329(6) Uani 1 1 d . . .
O2W O 0.6994(3) 0.0914(2) 0.4705(2) 0.0326(6) Uani 1 1 d . . .
H2WB H 0.6703 0.0168 0.5157 0.049 Uiso 1 1 d R . .
H2WA H 0.7391 0.0891 0.4047 0.049 Uiso 1 1 d R . .
O3 O 0.4328(3) 0.0847(2) 0.63421(18) 0.0318(6) Uani 1 1 d . . .
O3W O 0.3496(3) 0.3725(2) 0.56559(19) 0.0312(5) Uani 1 1 d . . .
H3WA H 0.3996 0.3783 0.6098 0.047 Uiso 1 1 d R . .
H3WB H 0.2758 0.3313 0.6062 0.047 Uiso 1 1 d R . .
O4 O 0.5396(3) -0.1080(2) 0.63624(18) 0.0279(5) Uani 1 1 d . . .
O5 O 0.2312(3) 0.2325(2) 0.4705(2) 0.0372(6) Uani 1 1 d . . .
O6 O 0.3289(3) 0.3685(2) 0.3040(2) 0.0361(6) Uani 1 1 d . . .
O7 O 0.1023(4) 0.3316(3) 0.3360(3) 0.0642(9) Uani 1 1 d . . .


_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 O3 2.384(2) . ?
Eu1 O4 2.409(2) 2_656 ?
Eu1 O2W 2.427(2) . ?
Eu1 O2 2.435(2) . ?
Eu1 O1W 2.436(2) . ?
Eu1 O3W 2.436(2) . ?
Eu1 O1 2.510(2) . ?
Eu1 O5 2.513(3) . ?
Eu1 O6 2.540(3) . ?
Eu1 C1 2.824(3) . ?
Eu1 N5 2.953(3) . ?
N1 C10 1.321(5) . ?
N1 C9 1.332(4) . ?
N2 C10 1.329(5) . ?
N2 C11 1.350(4) . ?
N3 C21 1.327(5) . ?
N3 C20 1.342(4) . ?
N4 C21 1.321(5) . ?
N4 C22 1.329(4) . ?
N5 O7 1.223(4) . ?
N5 O6 1.264(4) . ?
N5 O5 1.279(4) . ?
C1 O2 1.259(4) . ?
C1 O1 1.269(4) . ?
C1 C2 1.499(4) . ?
C2 C7 1.386(5) . ?
C2 C3 1.390(5) . ?
C3 C4 1.385(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.389(5) . ?
C5 C8 1.481(4) . ?
C6 C7 1.388(4) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C11 1.378(5) . ?
C8 C9 1.383(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O3 1.254(4) . ?
C12 O4 1.255(4) . ?
C12 C13 1.502(4) . ?
C13 C14 1.386(5) . ?
C13 C18 1.388(4) . ?
C14 C15 1.385(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.393(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.385(5) . ?
C16 C19 1.488(4) . ?
C17 C18 1.397(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.376(5) . ?
C19 C22 1.386(5) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8500 . ?
O2W H2WB 0.8500 . ?
O2W H2WA 0.8501 . ?
O3W H3WA 0.8500 . ?
O3W H3WB 0.8500 . ?
O4 Eu1 2.409(2) 2_656 ?

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
O3 Eu1 O4 87.98(7) . 2_656 ?
O3 Eu1 O2W 73.76(8) . . ?
O4 Eu1 O2W 72.88(8) 2_656 . ?
O3 Eu1 O2 149.18(9) . . ?
O4 Eu1 O2 83.31(8) 2_656 . ?
O2W Eu1 O2 75.42(8) . . ?
O3 Eu1 O1W 82.38(9) . . ?
O4 Eu1 O1W 143.82(9) 2_656 . ?
O2W Eu1 O1W 70.95(9) . . ?
O2 Eu1 O1W 87.38(9) . . ?
O3 Eu1 O3W 76.99(8) . . ?
O4 Eu1 O3W 138.26(8) 2_656 . ?
O2W Eu1 O3W 135.81(8) . . ?
O2 Eu1 O3W 127.35(8) . . ?
O1W Eu1 O3W 72.98(9) . . ?
O3 Eu1 O1 146.74(8) . . ?
O4 Eu1 O1 124.94(7) 2_656 . ?
O2W Eu1 O1 117.09(8) . . ?
O2 Eu1 O1 52.94(7) . . ?
O1W Eu1 O1 73.18(8) . . ?
O3W Eu1 O1 74.53(7) . . ?
O3 Eu1 O5 75.15(9) . . ?
O4 Eu1 O5 68.85(8) 2_656 . ?
O2W Eu1 O5 130.80(8) . . ?
O2 Eu1 O5 127.61(8) . . ?
O1W Eu1 O5 139.75(9) . . ?
O3W Eu1 O5 69.70(8) . . ?
O1 Eu1 O5 109.89(8) . . ?
O3 Eu1 O6 125.62(9) . . ?
O4 Eu1 O6 70.32(8) 2_656 . ?
O2W Eu1 O6 136.93(8) . . ?
O2 Eu1 O6 78.81(8) . . ?
O1W Eu1 O6 141.47(8) . . ?
O3W Eu1 O6 87.18(8) . . ?
O1 Eu1 O6 69.78(8) . . ?
O5 Eu1 O6 50.66(8) . . ?
O3 Eu1 C1 163.20(9) . . ?
O4 Eu1 C1 103.44(8) 2_656 . ?
O2W Eu1 C1 97.60(9) . . ?
O2 Eu1 C1 26.38(9) . . ?
O1W Eu1 C1 81.16(9) . . ?
O3W Eu1 C1 101.23(9) . . ?
O1 Eu1 C1 26.70(8) . . ?
O5 Eu1 C1 120.27(9) . . ?
O6 Eu1 C1 70.53(9) . . ?
O3 Eu1 N5 100.46(9) . . ?
O4 Eu1 N5 66.62(8) 2_656 . ?
O2W Eu1 N5 139.30(8) . . ?
O2 Eu1 N5 103.01(9) . . ?
O1W Eu1 N5 149.44(8) . . ?
O3W Eu1 N5 78.03(8) . . ?
O1 Eu1 N5 90.13(8) . . ?
O5 Eu1 N5 25.47(8) . . ?
O6 Eu1 N5 25.21(8) . . ?
C1 Eu1 N5 95.42(10) . . ?
C10 N1 C9 116.4(3) . . ?
C10 N2 C11 115.5(3) . . ?
C21 N3 C20 114.9(3) . . ?
C21 N4 C22 115.7(3) . . ?
O7 N5 O6 122.5(3) . . ?
O7 N5 O5 121.0(3) . . ?
O6 N5 O5 116.5(3) . . ?
O7 N5 Eu1 178.3(3) . . ?
O6 N5 Eu1 58.83(18) . . ?
O5 N5 Eu1 57.68(17) . . ?
O2 C1 O1 121.5(3) . . ?
O2 C1 C2 119.2(3) . . ?
O1 C1 C2 119.2(3) . . ?
O2 C1 Eu1 59.29(16) . . ?
O1 C1 Eu1 62.72(15) . . ?
C2 C1 Eu1 170.6(2) . . ?
C7 C2 C3 119.2(3) . . ?
C7 C2 C1 121.0(3) . . ?
C3 C2 C1 119.8(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 C8 120.5(3) . . ?
C6 C5 C8 120.6(3) . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C2 C7 C6 120.1(3) . . ?
C2 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C11 C8 C9 115.3(3) . . ?
C11 C8 C5 122.4(3) . . ?
C9 C8 C5 122.3(3) . . ?
N1 C9 C8 123.1(4) . . ?
N1 C9 H9A 118.4 . . ?
C8 C9 H9A 118.4 . . ?
N1 C10 N2 126.6(3) . . ?
N1 C10 H10A 116.7 . . ?
N2 C10 H10A 116.7 . . ?
N2 C11 C8 123.1(3) . . ?
N2 C11 H11A 118.5 . . ?
C8 C11 H11A 118.5 . . ?
O3 C12 O4 124.8(3) . . ?
O3 C12 C13 117.1(3) . . ?
O4 C12 C13 118.1(3) . . ?
C14 C13 C18 119.7(3) . . ?
C14 C13 C12 119.7(3) . . ?
C18 C13 C12 120.6(3) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 C19 122.4(3) . . ?
C15 C16 C19 119.0(3) . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C13 C18 C17 119.9(3) . . ?
C13 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C20 C19 C22 115.3(3) . . ?
C20 C19 C16 122.1(3) . . ?
C22 C19 C16 122.5(3) . . ?
N3 C20 C19 123.4(3) . . ?
N3 C20 H20A 118.3 . . ?
C19 C20 H20A 118.3 . . ?
N4 C21 N3 127.5(3) . . ?
N4 C21 H21A 116.2 . . ?
N3 C21 H21A 116.2 . . ?
N4 C22 C19 123.0(3) . . ?
N4 C22 H22A 118.5 . . ?
C19 C22 H22A 118.5 . . ?
C1 O1 Eu1 90.58(18) . . ?
Eu1 O1W H1WA 109.5 . . ?
Eu1 O1W H1WB 108.9 . . ?
H1WA O1W H1WB 109.5 . . ?
C1 O2 Eu1 94.33(19) . . ?
Eu1 O2W H2WB 109.5 . . ?
Eu1 O2W H2WA 109.6 . . ?
H2WB O2W H2WA 109.5 . . ?
C12 O3 Eu1 138.9(2) . . ?
Eu1 O3W H3WA 109.3 . . ?
Eu1 O3W H3WB 109.3 . . ?
H3WA O3W H3WB 109.5 . . ?
C12 O4 Eu1 134.9(2) . 2_656 ?
N5 O5 Eu1 96.9(2) . . ?
N5 O6 Eu1 96.0(2) . . ?

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
O3 Eu1 N5 O7 -34(9) . . . . ?
O4 Eu1 N5 O7 50(9) 2_656 . . . ?
O2W Eu1 N5 O7 44(9) . . . . ?
O2 Eu1 N5 O7 126(9) . . . . ?
O1W Eu1 N5 O7 -126(9) . . . . ?
O3W Eu1 N5 O7 -108(9) . . . . ?
O1 Eu1 N5 O7 178(100) . . . . ?
O5 Eu1 N5 O7 -40(9) . . . . ?
O6 Eu1 N5 O7 143(9) . . . . ?
C1 Eu1 N5 O7 152(9) . . . . ?
O3 Eu1 N5 O6 -176.43(18) . . . . ?
O4 Eu1 N5 O6 -93.26(19) 2_656 . . . ?
O2W Eu1 N5 O6 -99.2(2) . . . . ?
O2 Eu1 N5 O6 -16.6(2) . . . . ?
O1W Eu1 N5 O6 90.8(2) . . . . ?
O3W Eu1 N5 O6 109.42(19) . . . . ?
O1 Eu1 N5 O6 35.27(19) . . . . ?
O5 Eu1 N5 O6 177.1(3) . . . . ?
C1 Eu1 N5 O6 9.1(2) . . . . ?
O3 Eu1 N5 O5 6.46(19) . . . . ?
O4 Eu1 N5 O5 89.63(19) 2_656 . . . ?
O2W Eu1 N5 O5 83.7(2) . . . . ?
O2 Eu1 N5 O5 166.33(18) . . . . ?
O1W Eu1 N5 O5 -86.3(2) . . . . ?
O3W Eu1 N5 O5 -67.69(19) . . . . ?
O1 Eu1 N5 O5 -141.84(19) . . . . ?
O6 Eu1 N5 O5 -177.1(3) . . . . ?
C1 Eu1 N5 O5 -168.05(19) . . . . ?
O3 Eu1 C1 O2 90.5(3) . . . . ?
O4 Eu1 C1 O2 -41.3(2) 2_656 . . . ?
O2W Eu1 C1 O2 32.8(2) . . . . ?
O1W Eu1 C1 O2 102.1(2) . . . . ?
O3W Eu1 C1 O2 172.7(2) . . . . ?
O1 Eu1 C1 O2 172.1(3) . . . . ?
O5 Eu1 C1 O2 -114.4(2) . . . . ?
O6 Eu1 C1 O2 -104.4(2) . . . . ?
N5 Eu1 C1 O2 -108.5(2) . . . . ?
O3 Eu1 C1 O1 -81.6(4) . . . . ?
O4 Eu1 C1 O1 146.64(19) 2_656 . . . ?
O2W Eu1 C1 O1 -139.24(19) . . . . ?
O2 Eu1 C1 O1 -172.1(3) . . . . ?
O1W Eu1 C1 O1 -69.97(19) . . . . ?
O3W Eu1 C1 O1 0.6(2) . . . . ?
O5 Eu1 C1 O1 73.5(2) . . . . ?
O6 Eu1 C1 O1 83.5(2) . . . . ?
N5 Eu1 C1 O1 79.4(2) . . . . ?
O3 Eu1 C1 C2 174.0(14) . . . . ?
O4 Eu1 C1 C2 42.2(15) 2_656 . . . ?
O2W Eu1 C1 C2 116.3(15) . . . . ?
O2 Eu1 C1 C2 83.4(15) . . . . ?
O1W Eu1 C1 C2 -174.5(15) . . . . ?
O3W Eu1 C1 C2 -103.9(15) . . . . ?
O1 Eu1 C1 C2 -104.5(16) . . . . ?
O5 Eu1 C1 C2 -31.0(15) . . . . ?
O6 Eu1 C1 C2 -21.0(15) . . . . ?
N5 Eu1 C1 C2 -25.1(15) . . . . ?
O2 C1 C2 C7 178.3(3) . . . . ?
O1 C1 C2 C7 0.7(5) . . . . ?
Eu1 C1 C2 C7 100.2(15) . . . . ?
O2 C1 C2 C3 0.9(5) . . . . ?
O1 C1 C2 C3 -176.7(3) . . . . ?
Eu1 C1 C2 C3 -77.1(16) . . . . ?
C7 C2 C3 C4 1.3(6) . . . . ?
C1 C2 C3 C4 178.7(4) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C3 C4 C5 C8 179.1(4) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C8 C5 C6 C7 -178.9(3) . . . . ?
C3 C2 C7 C6 -1.1(5) . . . . ?
C1 C2 C7 C6 -178.5(3) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C4 C5 C8 C11 146.7(4) . . . . ?
C6 C5 C8 C11 -34.3(5) . . . . ?
C4 C5 C8 C9 -33.0(6) . . . . ?
C6 C5 C8 C9 146.0(4) . . . . ?
C10 N1 C9 C8 1.1(6) . . . . ?
C11 C8 C9 N1 -0.1(6) . . . . ?
C5 C8 C9 N1 179.6(3) . . . . ?
C9 N1 C10 N2 -1.2(6) . . . . ?
C11 N2 C10 N1 0.3(6) . . . . ?
C10 N2 C11 C8 0.8(5) . . . . ?
C9 C8 C11 N2 -0.9(5) . . . . ?
C5 C8 C11 N2 179.4(3) . . . . ?
O3 C12 C13 C14 18.4(5) . . . . ?
O4 C12 C13 C14 -161.6(3) . . . . ?
O3 C12 C13 C18 -162.4(3) . . . . ?
O4 C12 C13 C18 17.5(5) . . . . ?
C18 C13 C14 C15 -1.2(6) . . . . ?
C12 C13 C14 C15 177.9(3) . . . . ?
C13 C14 C15 C16 0.7(6) . . . . ?
C14 C15 C16 C17 0.3(6) . . . . ?
C14 C15 C16 C19 179.9(4) . . . . ?
C15 C16 C17 C18 -0.9(5) . . . . ?
C19 C16 C17 C18 179.5(3) . . . . ?
C14 C13 C18 C17 0.6(5) . . . . ?
C12 C13 C18 C17 -178.5(3) . . . . ?
C16 C17 C18 C13 0.5(5) . . . . ?
C17 C16 C19 C20 -141.5(4) . . . . ?
C15 C16 C19 C20 38.9(5) . . . . ?
C17 C16 C19 C22 41.6(5) . . . . ?
C15 C16 C19 C22 -138.0(4) . . . . ?
C21 N3 C20 C19 0.8(6) . . . . ?
C22 C19 C20 N3 1.8(6) . . . . ?
C16 C19 C20 N3 -175.3(3) . . . . ?
C22 N4 C21 N3 3.3(6) . . . . ?
C20 N3 C21 N4 -3.6(6) . . . . ?
C21 N4 C22 C19 -0.2(5) . . . . ?
C20 C19 C22 N4 -2.2(5) . . . . ?
C16 C19 C22 N4 174.9(3) . . . . ?
O2 C1 O1 Eu1 -8.0(3) . . . . ?
C2 C1 O1 Eu1 169.6(3) . . . . ?
O3 Eu1 O1 C1 148.6(2) . . . . ?
O4 Eu1 O1 C1 -40.7(2) 2_656 . . . ?
O2W Eu1 O1 C1 46.6(2) . . . . ?
O2 Eu1 O1 C1 4.41(19) . . . . ?
O1W Eu1 O1 C1 104.1(2) . . . . ?
O3W Eu1 O1 C1 -179.4(2) . . . . ?
O5 Eu1 O1 C1 -118.3(2) . . . . ?
O6 Eu1 O1 C1 -86.7(2) . . . . ?
N5 Eu1 O1 C1 -101.9(2) . . . . ?
O1 C1 O2 Eu1 8.3(3) . . . . ?
C2 C1 O2 Eu1 -169.3(3) . . . . ?
O3 Eu1 O2 C1 -145.7(2) . . . . ?
O4 Eu1 O2 C1 139.7(2) 2_656 . . . ?
O2W Eu1 O2 C1 -146.3(2) . . . . ?
O1W Eu1 O2 C1 -75.3(2) . . . . ?
O3W Eu1 O2 C1 -9.1(2) . . . . ?
O1 Eu1 O2 C1 -4.46(19) . . . . ?
O5 Eu1 O2 C1 83.0(2) . . . . ?
O6 Eu1 O2 C1 68.6(2) . . . . ?
N5 Eu1 O2 C1 75.7(2) . . . . ?
O4 C12 O3 Eu1 2.8(6) . . . . ?
C13 C12 O3 Eu1 -177.3(2) . . . . ?
O4 Eu1 O3 C12 42.2(3) 2_656 . . . ?
O2W Eu1 O3 C12 -30.6(3) . . . . ?
O2 Eu1 O3 C12 -31.2(4) . . . . ?
O1W Eu1 O3 C12 -102.9(4) . . . . ?
O3W Eu1 O3 C12 -177.1(4) . . . . ?
O1 Eu1 O3 C12 -145.5(3) . . . . ?
O5 Eu1 O3 C12 110.8(4) . . . . ?
O6 Eu1 O3 C12 106.1(3) . . . . ?
C1 Eu1 O3 C12 -91.3(5) . . . . ?
N5 Eu1 O3 C12 107.9(3) . . . . ?
O3 C12 O4 Eu1 -101.0(4) . . . 2_656 ?
C13 C12 O4 Eu1 79.1(4) . . . 2_656 ?
O7 N5 O5 Eu1 178.7(3) . . . . ?
O6 N5 O5 Eu1 -2.8(3) . . . . ?
O3 Eu1 O5 N5 -173.4(2) . . . . ?
O4 Eu1 O5 N5 -79.79(18) 2_656 . . . ?
O2W Eu1 O5 N5 -121.11(18) . . . . ?
O2 Eu1 O5 N5 -16.9(2) . . . . ?
O1W Eu1 O5 N5 128.27(18) . . . . ?
O3W Eu1 O5 N5 105.21(19) . . . . ?
O1 Eu1 O5 N5 41.1(2) . . . . ?
O6 Eu1 O5 N5 1.59(17) . . . . ?
C1 Eu1 O5 N5 13.8(2) . . . . ?
O7 N5 O6 Eu1 -178.8(3) . . . . ?
O5 N5 O6 Eu1 2.7(3) . . . . ?
O3 Eu1 O6 N5 4.3(2) . . . . ?
O4 Eu1 O6 N5 76.72(19) 2_656 . . . ?
O2W Eu1 O6 N5 109.52(19) . . . . ?
O2 Eu1 O6 N5 163.55(19) . . . . ?
O1W Eu1 O6 N5 -125.3(2) . . . . ?
O3W Eu1 O6 N5 -67.47(19) . . . . ?
O1 Eu1 O6 N5 -142.0(2) . . . . ?
O5 Eu1 O6 N5 -1.61(17) . . . . ?
C1 Eu1 O6 N5 -170.4(2) . . . . ?

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
O1W H1WA N2 0.85 2.17 2.836(4) 135.1 1_546
O2W H2WB O4 0.85 1.96 2.759(3) 156.8 .
O2W H2WA N1 0.85 2.14 2.763(4) 129.7 2_765
O3W H3WA O1 0.85 2.01 2.720(3) 140.4 2_666
O3W H3WB N3 0.85 2.10 2.887(4) 154.7 2_557

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.17
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 1005405'
