# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1505423'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Eu N4 O10 S2'
_chemical_formula_weight         677.45

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.4989(19)
_cell_length_b                   7.0047(13)
_cell_length_c                   30.274(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.088(3)
_cell_angle_gamma                90.00
_cell_volume                     2213.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5527
_cell_measurement_theta_min      3.2074
_cell_measurement_theta_max      27.4758

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.037
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    3.089
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   'Sphere (Rigaku CrystalClear)'

_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  CCD_Profile_fitting
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16145
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5028
_reflns_number_gt                4547
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0839P)²+0.8366P] 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         5028
_refine_ls_number_parameters     349
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.004
_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 -0.475890(17) 1.47430(3) 0.939567(6) 0.01546(10) Uani 1 1 d . . .
O8 O -0.4263(3) 1.6444(4) 1.00302(9) 0.0209(6) Uani 1 1 d . . .
H8A H -0.3724 1.7501 1.0052 0.025 Uiso 1 1 calc R . .
O7 O -0.2728(3) 1.6099(6) 0.92215(13) 0.0342(8) Uani 1 1 d . . .
N2 N -0.5097(3) 1.4603(5) 0.85337(13) 0.0213(7) Uani 1 1 d . . .
O9 O -0.2904(3) 1.2757(5) 0.96957(12) 0.0263(7) Uani 1 1 d . . .
N1 N -0.7084(3) 1.4841(5) 0.90396(13) 0.0183(7) Uani 1 1 d . . .
N3 N -0.9965(3) 1.5226(5) 0.76465(12) 0.0213(7) Uani 1 1 d . . .
C5 C -0.8832(4) 1.5033(6) 0.79134(15) 0.0203(8) Uani 1 1 d . . .
C4 C -0.8628(4) 1.5092(6) 0.83897(15) 0.0185(8) Uani 1 1 d . . .
C11 C -0.7357(4) 1.4881(5) 0.85896(13) 0.0160(7) Uani 1 1 d . . .
S2 S -0.88728(10) 1.55044(16) 0.62052(4) 0.0247(2) Uani 1 1 d . . .
O6 O -0.8134(3) 1.3794(5) 0.63430(11) 0.0327(7) Uani 1 1 d . . .
O5 O -0.8348(3) 1.7184(5) 0.64236(13) 0.0395(8) Uani 1 1 d . . .
C15 C -1.0420(4) 1.5165(6) 0.63937(15) 0.0207(8) Uani 1 1 d . . .
O4 O -0.9089(3) 1.5689(6) 0.57243(11) 0.0409(9) Uani 1 1 d . . .
N4 N -0.8365(4) 1.4680(5) 0.72312(13) 0.0259(8) Uani 1 1 d . . .
H4A H -0.7975 1.4477 0.7000 0.031 Uiso 1 1 calc R . .
C1 C -0.8048(4) 1.5013(6) 0.92877(15) 0.0229(9) Uani 1 1 d . . .
H1A H -0.7862 1.4965 0.9595 0.027 Uiso 1 1 calc R . .
C14 C -1.0611(4) 1.5023(6) 0.68457(14) 0.0202(8) Uani 1 1 d . . .
C6 C -0.7827(4) 1.4718(6) 0.76589(15) 0.0223(8) Uani 1 1 d . . .
C12 C -0.6302(4) 1.4675(5) 0.83183(14) 0.0183(8) Uani 1 1 d . . .
C2 C -0.9322(4) 1.5262(6) 0.91149(16) 0.0250(9) Uani 1 1 d . . .
H2A H -0.9962 1.5404 0.9303 0.030 Uiso 1 1 calc R . .
C19 C -1.1878(4) 1.4867(6) 0.69534(15) 0.0262(9) Uani 1 1 d . . .
H19A H -1.2027 1.4810 0.7251 0.031 Uiso 1 1 calc R . .
C7 C -0.6528(4) 1.4517(6) 0.78518(15) 0.0219(8) Uani 1 1 d . . .
C13 C -0.9636(4) 1.5022(6) 0.72384(14) 0.0212(8) Uani 1 1 d . . .
C10 C -0.4125(4) 1.4326(7) 0.82932(15) 0.0276(9) Uani 1 1 d . . .
H10A H -0.3298 1.4302 0.8438 0.033 Uiso 1 1 calc R . .
C8 C -0.5487(4) 1.4201(8) 0.76089(15) 0.0348(11) Uani 1 1 d . . .
H8B H -0.5605 1.4081 0.7301 0.042 Uiso 1 1 calc R . .
C3 C -0.9614(4) 1.5292(6) 0.86612(15) 0.0233(9) Uani 1 1 d . . .
H3B H -1.0457 1.5445 0.8537 0.028 Uiso 1 1 calc R . .
S1 S -1.40179(10) 1.47599(13) 0.57722(3) 0.0185(2) Uani 1 1 d . . .
O1 O -1.4696(3) 1.3008(4) 0.58594(10) 0.0271(7) Uani 1 1 d . . .
O3 O -1.3492(3) 1.4784(4) 0.53476(11) 0.0278(7) Uani 1 1 d . . .
C17 C -1.2692(4) 1.4876(5) 0.61845(15) 0.0193(8) Uani 1 1 d . . .
C18 C -1.1459(4) 1.5083(6) 0.60665(14) 0.0205(8) Uani 1 1 d . . .
H18A H -1.1325 1.5168 0.5768 0.025 Uiso 1 1 calc R . .
C16 C -1.2907(4) 1.4796(7) 0.66294(15) 0.0263(10) Uani 1 1 d . . .
H16A H -1.3737 1.4696 0.6708 0.032 Uiso 1 1 calc R . .
O2 O -1.4790(3) 1.6421(4) 0.58453(10) 0.0232(6) Uani 1 1 d . . .
C9 C -0.4287(5) 1.4072(10) 0.78351(17) 0.0439(14) Uani 1 1 d . . .
H9B H -0.3583 1.3814 0.7682 0.053 Uiso 1 1 calc R . .
O10 O -0.0897(7) 1.7656(9) 0.99018(19) 0.0793(16) Uani 1 1 d D . .
H5 H -0.067(14) 1.877(10) 0.982(5) 0.18(6) Uiso 1 1 d D . .
H3 H -0.303(5) 1.207(8) 0.990(2) 0.037(16) Uiso 1 1 d . . .
H4 H -0.243(5) 1.224(9) 0.956(2) 0.037(17) Uiso 1 1 d . . .
H6 H -0.020(9) 1.79(3) 1.008(5) 0.26(10) Uiso 1 1 d D . .
H1 H -0.262(5) 1.681(8) 0.9077(18) 0.026(15) Uiso 1 1 d . . .
H2 H -0.218(7) 1.667(12) 0.946(3) 0.09(3) Uiso 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 O8 2.268(3) 3_487 ?
Eu1 O8 2.274(3) . ?
Eu1 O7 2.442(3) . ?
Eu1 O1 2.462(3) 2_356 ?
Eu1 O2 2.469(3) 2_346 ?
Eu1 O9 2.485(3) . ?
Eu1 N1 2.562(4) . ?
Eu1 N2 2.598(4) . ?
Eu1 Eu1 3.7641(8) 3_487 ?
O8 Eu1 2.268(3) 3_487 ?
O8 H8A 0.9300 . ?
O7 H1 0.68(6) . ?
O7 H2 0.97(8) . ?
N2 C10 1.330(6) . ?
N2 C12 1.361(5) . ?
O9 H3 0.82(6) . ?
O9 H4 0.78(6) . ?
N1 C1 1.329(6) . ?
N1 C11 1.363(5) . ?
N3 C13 1.325(6) . ?
N3 C5 1.372(6) . ?
C5 C6 1.389(6) . ?
C5 C4 1.436(6) . ?
C4 C3 1.395(6) . ?
C4 C11 1.413(6) . ?
C11 C12 1.455(6) . ?
S2 O5 1.431(4) . ?
S2 O4 1.455(4) . ?
S2 O6 1.464(4) . ?
S2 C15 1.794(5) . ?
C15 C18 1.395(6) . ?
C15 C14 1.407(6) . ?
N4 C6 1.357(6) . ?
N4 C13 1.358(6) . ?
N4 H4A 0.8600 . ?
C1 C2 1.395(6) . ?
C1 H1A 0.9300 . ?
C14 C19 1.408(6) . ?
C14 C13 1.484(6) . ?
C6 C7 1.432(6) . ?
C12 C7 1.411(6) . ?
C2 C3 1.375(7) . ?
C2 H2A 0.9300 . ?
C19 C16 1.381(6) . ?
C19 H19A 0.9300 . ?
C7 C8 1.398(6) . ?
C10 C9 1.391(7) . ?
C10 H10A 0.9300 . ?
C8 C9 1.372(6) . ?
C8 H8B 0.9300 . ?
C3 H3B 0.9300 . ?
S1 O2 1.448(3) . ?
S1 O3 1.452(4) . ?
S1 O1 1.457(3) . ?
S1 C17 1.770(4) . ?
O1 Eu1 2.462(3) 2_346 ?
C17 C18 1.386(6) . ?
C17 C16 1.390(6) . ?
C18 H18A 0.9300 . ?
C16 H16A 0.9300 . ?
O2 Eu1 2.469(3) 2_356 ?
C9 H9B 0.9300 . ?
O10 H5 0.86(2) . ?
O10 H6 0.86(2) . ?

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 O8 68.06(12) 3_487 . ?
O8 Eu1 O7 141.67(11) 3_487 . ?
O8 Eu1 O7 81.47(12) . . ?
O8 Eu1 O1 118.16(11) 3_487 2_356 ?
O8 Eu1 O1 78.63(10) . 2_356 ?
O7 Eu1 O1 75.53(12) . 2_356 ?
O8 Eu1 O2 78.03(10) 3_487 2_346 ?
O8 Eu1 O2 139.74(10) . 2_346 ?
O7 Eu1 O2 116.57(12) . 2_346 ?
O1 Eu1 O2 138.74(10) 2_356 2_346 ?
O8 Eu1 O9 85.15(11) 3_487 . ?
O8 Eu1 O9 83.36(11) . . ?
O7 Eu1 O9 68.19(12) . . ?
O1 Eu1 O9 141.42(11) 2_356 . ?
O2 Eu1 O9 72.48(10) 2_346 . ?
O8 Eu1 N1 81.02(11) 3_487 . ?
O8 Eu1 N1 117.63(11) . . ?
O7 Eu1 N1 135.50(12) . . ?
O1 Eu1 N1 70.35(10) 2_356 . ?
O2 Eu1 N1 75.91(10) 2_346 . ?
O9 Eu1 N1 147.48(11) . . ?
O8 Eu1 N2 136.98(11) 3_487 . ?
O8 Eu1 N2 149.67(11) . . ?
O7 Eu1 N2 80.06(12) . . ?
O1 Eu1 N2 73.58(10) 2_356 . ?
O2 Eu1 N2 70.50(10) 2_346 . ?
O9 Eu1 N2 111.38(11) . . ?
N1 Eu1 N2 63.62(12) . . ?
O8 Eu1 Eu1 34.07(7) 3_487 3_487 ?
O8 Eu1 Eu1 33.99(7) . 3_487 ?
O7 Eu1 Eu1 112.53(10) . 3_487 ?
O1 Eu1 Eu1 99.52(8) 2_356 3_487 ?
O2 Eu1 Eu1 109.63(7) 2_346 3_487 ?
O9 Eu1 Eu1 83.06(8) . 3_487 ?
N1 Eu1 Eu1 100.72(9) . 3_487 ?
N2 Eu1 Eu1 164.14(8) . 3_487 ?
Eu1 O8 Eu1 111.94(11) 3_487 . ?
Eu1 O8 H8A 124.0 3_487 . ?
Eu1 O8 H8A 124.0 . . ?
Eu1 O7 H1 130(5) . . ?
Eu1 O7 H2 118(5) . . ?
H1 O7 H2 93(6) . . ?
C10 N2 C12 118.1(4) . . ?
C10 N2 Eu1 121.6(3) . . ?
C12 N2 Eu1 120.1(3) . . ?
Eu1 O9 H3 115(4) . . ?
Eu1 O9 H4 126(4) . . ?
H3 O9 H4 108(6) . . ?
C1 N1 C11 118.1(4) . . ?
C1 N1 Eu1 120.9(3) . . ?
C11 N1 Eu1 120.8(3) . . ?
C13 N3 C5 104.1(4) . . ?
N3 C5 C6 110.6(4) . . ?
N3 C5 C4 128.1(4) . . ?
C6 C5 C4 121.4(4) . . ?
C3 C4 C11 118.9(4) . . ?
C3 C4 C5 123.6(4) . . ?
C11 C4 C5 117.4(4) . . ?
N1 C11 C4 121.3(4) . . ?
N1 C11 C12 118.0(4) . . ?
C4 C11 C12 120.6(4) . . ?
O5 S2 O4 113.6(2) . . ?
O5 S2 O6 112.0(2) . . ?
O4 S2 O6 112.3(2) . . ?
O5 S2 C15 106.2(2) . . ?
O4 S2 C15 106.2(2) . . ?
O6 S2 C15 105.7(2) . . ?
C18 C15 C14 120.4(4) . . ?
C18 C15 S2 116.5(3) . . ?
C14 C15 S2 123.1(3) . . ?
C6 N4 C13 107.0(4) . . ?
C6 N4 H4A 126.5 . . ?
C13 N4 H4A 126.5 . . ?
N1 C1 C2 123.9(4) . . ?
N1 C1 H1A 118.1 . . ?
C2 C1 H1A 118.1 . . ?
C15 C14 C19 117.8(4) . . ?
C15 C14 C13 128.4(4) . . ?
C19 C14 C13 113.8(4) . . ?
N4 C6 C5 105.6(4) . . ?
N4 C6 C7 132.0(4) . . ?
C5 C6 C7 122.4(4) . . ?
N2 C12 C7 121.7(4) . . ?
N2 C12 C11 117.2(4) . . ?
C7 C12 C11 121.0(4) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C16 C19 C14 121.7(4) . . ?
C16 C19 H19A 119.1 . . ?
C14 C19 H19A 119.1 . . ?
C8 C7 C12 118.7(4) . . ?
C8 C7 C6 124.4(4) . . ?
C12 C7 C6 116.9(4) . . ?
N3 C13 N4 112.8(4) . . ?
N3 C13 C14 121.4(4) . . ?
N4 C13 C14 125.6(4) . . ?
N2 C10 C9 123.0(4) . . ?
N2 C10 H10A 118.5 . . ?
C9 C10 H10A 118.5 . . ?
C9 C8 C7 118.4(4) . . ?
C9 C8 H8B 120.8 . . ?
C7 C8 H8B 120.8 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3B 120.5 . . ?
C4 C3 H3B 120.5 . . ?
O2 S1 O3 113.41(18) . . ?
O2 S1 O1 110.9(2) . . ?
O3 S1 O1 114.16(19) . . ?
O2 S1 C17 105.44(18) . . ?
O3 S1 C17 106.2(2) . . ?
O1 S1 C17 105.88(18) . . ?
S1 O1 Eu1 145.8(2) . 2_346 ?
C18 C17 C16 120.4(4) . . ?
C18 C17 S1 120.6(3) . . ?
C16 C17 S1 119.0(3) . . ?
C17 C18 C15 120.2(4) . . ?
C17 C18 H18A 119.9 . . ?
C15 C18 H18A 119.9 . . ?
C19 C16 C17 119.5(4) . . ?
C19 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
S1 O2 Eu1 143.59(19) . 2_356 ?
C8 C9 C10 119.9(4) . . ?
C8 C9 H9B 120.1 . . ?
C10 C9 H9B 120.1 . . ?
H5 O10 H6 78(10) . . ?

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 O8 Eu1 0.0 3_487 . . 3_487 ?
O7 Eu1 O8 Eu1 -156.28(15) . . . 3_487 ?
O1 Eu1 O8 Eu1 126.87(14) 2_356 . . 3_487 ?
O2 Eu1 O8 Eu1 -34.8(2) 2_346 . . 3_487 ?
O9 Eu1 O8 Eu1 -87.42(13) . . . 3_487 ?
N1 Eu1 O8 Eu1 66.37(15) . . . 3_487 ?
N2 Eu1 O8 Eu1 150.73(16) . . . 3_487 ?
O8 Eu1 N2 C10 -136.1(3) 3_487 . . . ?
O8 Eu1 N2 C10 85.5(4) . . . . ?
O7 Eu1 N2 C10 32.2(4) . . . . ?
O1 Eu1 N2 C10 109.9(4) 2_356 . . . ?
O2 Eu1 N2 C10 -90.7(4) 2_346 . . . ?
O9 Eu1 N2 C10 -29.5(4) . . . . ?
N1 Eu1 N2 C10 -174.2(4) . . . . ?
Eu1 Eu1 N2 C10 176.0(3) 3_487 . . . ?
O8 Eu1 N2 C12 39.0(4) 3_487 . . . ?
O8 Eu1 N2 C12 -99.3(3) . . . . ?
O7 Eu1 N2 C12 -152.6(3) . . . . ?
O1 Eu1 N2 C12 -74.9(3) 2_356 . . . ?
O2 Eu1 N2 C12 84.4(3) 2_346 . . . ?
O9 Eu1 N2 C12 145.7(3) . . . . ?
N1 Eu1 N2 C12 0.9(3) . . . . ?
Eu1 Eu1 N2 C12 -8.9(5) 3_487 . . . ?
O8 Eu1 N1 C1 27.2(3) 3_487 . . . ?
O8 Eu1 N1 C1 -32.1(3) . . . . ?
O7 Eu1 N1 C1 -139.2(3) . . . . ?
O1 Eu1 N1 C1 -97.1(3) 2_356 . . . ?
O2 Eu1 N1 C1 107.0(3) 2_346 . . . ?
O9 Eu1 N1 C1 93.2(4) . . . . ?
N2 Eu1 N1 C1 -178.0(3) . . . . ?
Eu1 Eu1 N1 C1 -0.7(3) 3_487 . . . ?
O8 Eu1 N1 C11 -158.4(3) 3_487 . . . ?
O8 Eu1 N1 C11 142.2(3) . . . . ?
O7 Eu1 N1 C11 35.1(4) . . . . ?
O1 Eu1 N1 C11 77.3(3) 2_356 . . . ?
O2 Eu1 N1 C11 -78.6(3) 2_346 . . . ?
O9 Eu1 N1 C11 -92.4(3) . . . . ?
N2 Eu1 N1 C11 -3.6(3) . . . . ?
Eu1 Eu1 N1 C11 173.6(3) 3_487 . . . ?
C13 N3 C5 C6 0.2(5) . . . . ?
C13 N3 C5 C4 -178.7(4) . . . . ?
N3 C5 C4 C3 2.6(7) . . . . ?
C6 C5 C4 C3 -176.1(4) . . . . ?
N3 C5 C4 C11 -179.1(4) . . . . ?
C6 C5 C4 C11 2.1(6) . . . . ?
C1 N1 C11 C4 -0.3(5) . . . . ?
Eu1 N1 C11 C4 -174.8(3) . . . . ?
C1 N1 C11 C12 -179.5(3) . . . . ?
Eu1 N1 C11 C12 6.0(4) . . . . ?
C3 C4 C11 N1 1.1(6) . . . . ?
C5 C4 C11 N1 -177.3(4) . . . . ?
C3 C4 C11 C12 -179.8(4) . . . . ?
C5 C4 C11 C12 1.9(6) . . . . ?
O5 S2 C15 C18 123.2(3) . . . . ?
O4 S2 C15 C18 1.9(4) . . . . ?
O6 S2 C15 C18 -117.6(3) . . . . ?
O5 S2 C15 C14 -55.5(4) . . . . ?
O4 S2 C15 C14 -176.7(4) . . . . ?
O6 S2 C15 C14 63.7(4) . . . . ?
C11 N1 C1 C2 -1.0(6) . . . . ?
Eu1 N1 C1 C2 173.5(3) . . . . ?
C18 C15 C14 C19 -2.2(6) . . . . ?
S2 C15 C14 C19 176.4(3) . . . . ?
C18 C15 C14 C13 178.1(4) . . . . ?
S2 C15 C14 C13 -3.3(6) . . . . ?
C13 N4 C6 C5 1.8(5) . . . . ?
C13 N4 C6 C7 -177.6(4) . . . . ?
N3 C5 C6 N4 -1.3(5) . . . . ?
C4 C5 C6 N4 177.7(4) . . . . ?
N3 C5 C6 C7 178.2(4) . . . . ?
C4 C5 C6 C7 -2.8(7) . . . . ?
C10 N2 C12 C7 -1.8(6) . . . . ?
Eu1 N2 C12 C7 -177.1(3) . . . . ?
C10 N2 C12 C11 176.9(4) . . . . ?
Eu1 N2 C12 C11 1.6(5) . . . . ?
N1 C11 C12 N2 -4.9(5) . . . . ?
C4 C11 C12 N2 175.9(3) . . . . ?
N1 C11 C12 C7 173.8(4) . . . . ?
C4 C11 C12 C7 -5.4(6) . . . . ?
N1 C1 C2 C3 1.4(7) . . . . ?
C15 C14 C19 C16 1.9(6) . . . . ?
C13 C14 C19 C16 -178.3(4) . . . . ?
N2 C12 C7 C8 2.7(6) . . . . ?
C11 C12 C7 C8 -176.0(4) . . . . ?
N2 C12 C7 C6 -176.7(4) . . . . ?
C11 C12 C7 C6 4.7(6) . . . . ?
N4 C6 C7 C8 -0.6(8) . . . . ?
C5 C6 C7 C8 -179.9(5) . . . . ?
N4 C6 C7 C12 178.7(4) . . . . ?
C5 C6 C7 C12 -0.7(6) . . . . ?
C5 N3 C13 N4 1.0(5) . . . . ?
C5 N3 C13 C14 176.4(4) . . . . ?
C6 N4 C13 N3 -1.9(5) . . . . ?
C6 N4 C13 C14 -177.0(4) . . . . ?
C15 C14 C13 N3 167.6(4) . . . . ?
C19 C14 C13 N3 -12.1(6) . . . . ?
C15 C14 C13 N4 -17.7(7) . . . . ?
C19 C14 C13 N4 162.6(4) . . . . ?
C12 N2 C10 C9 -1.3(7) . . . . ?
Eu1 N2 C10 C9 174.0(4) . . . . ?
C12 C7 C8 C9 -0.5(8) . . . . ?
C6 C7 C8 C9 178.8(5) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C11 C4 C3 C2 -0.6(6) . . . . ?
C5 C4 C3 C2 177.6(4) . . . . ?
O2 S1 O1 Eu1 137.0(3) . . . 2_346 ?
O3 S1 O1 Eu1 7.4(4) . . . 2_346 ?
C17 S1 O1 Eu1 -109.1(3) . . . 2_346 ?
O2 S1 C17 C18 -116.7(3) . . . . ?
O3 S1 C17 C18 3.9(4) . . . . ?
O1 S1 C17 C18 125.7(3) . . . . ?
O2 S1 C17 C16 62.0(4) . . . . ?
O3 S1 C17 C16 -177.4(3) . . . . ?
O1 S1 C17 C16 -55.6(4) . . . . ?
C16 C17 C18 C15 1.6(6) . . . . ?
S1 C17 C18 C15 -179.7(3) . . . . ?
C14 C15 C18 C17 0.5(6) . . . . ?
S2 C15 C18 C17 -178.2(3) . . . . ?
C14 C19 C16 C17 0.1(7) . . . . ?
C18 C17 C16 C19 -1.9(7) . . . . ?
S1 C17 C16 C19 179.4(3) . . . . ?
O3 S1 O2 Eu1 -19.5(4) . . . 2_356 ?
O1 S1 O2 Eu1 -149.5(2) . . . 2_356 ?
C17 S1 O2 Eu1 96.3(3) . . . 2_356 ?
C7 C8 C9 C10 -2.4(9) . . . . ?
N2 C10 C9 C8 3.4(9) . . . . ?

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
O8 H8A O3 0.93 2.10 2.897(4) 142.3 4_696
N4 H4A O6 0.86 2.03 2.795(5) 147.0 .
O10 H5 O4 0.86(2) 2.12(9) 2.846(8) 142(13) 2_456
O9 H3 O3 0.82(6) 1.96(6) 2.776(5) 172(5) 4_686
O9 H4 O4 0.78(6) 2.18(6) 2.943(5) 170(6) 2_446
O7 H1 O6 0.68(6) 2.09(6) 2.762(5) 168(6) 2_456
O7 H2 O10 0.97(8) 1.92(8) 2.879(7) 172(7) .

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.117
_refine_diff_density_min         -1.404
_refine_diff_density_rms         0.332
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1505425'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Eu N4 O11 S2'
_chemical_formula_weight         704.45

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'
S S 0.1246 0.1234 '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'

_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                   9.912(8)
_cell_length_b                   10.882(9)
_cell_length_c                   11.977(9)
_cell_angle_alpha                97.866(8)
_cell_angle_beta                 91.933(3)
_cell_angle_gamma                115.337(14)
_cell_volume                     1150.4(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3642
_cell_measurement_theta_min      2.1004
_cell_measurement_theta_max      27.5087

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.038
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.034
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             694
_exptl_absorpt_coefficient_mu    2.980
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   'Sphere (Rigaku CrystalClear)'

_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  CCD_Profile_fitting
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8853
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4878
_reflns_number_gt                4358
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0312P)²+0.0000P] 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         4878
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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
Eu Eu 0.04534(2) 0.745942(19) 0.396222(17) 0.00791(7) Uani 1 1 d . . .
S1 S 0.74792(10) 0.43444(9) -0.50885(9) 0.0083(2) Uani 1 1 d . . .
S2 S 0.27986(10) 0.22910(10) -0.26778(9) 0.0089(2) Uani 1 1 d . . .
O1 O 0.8224(3) 0.5608(3) -0.5562(2) 0.0103(6) Uani 1 1 d . . .
O2 O 0.8589(3) 0.4028(3) -0.4504(2) 0.0111(6) Uani 1 1 d . . .
O3 O 0.6445(3) 0.3182(3) -0.5904(2) 0.0137(6) Uani 1 1 d . . .
O4 O 0.1548(3) 0.2658(3) -0.2779(2) 0.0115(6) Uani 1 1 d . . .
O5 O 0.3014(3) 0.2051(3) -0.1535(2) 0.0107(6) Uani 1 1 d . . .
O7 O -0.0479(3) 0.8430(3) 0.5462(2) 0.0122(6) Uani 1 1 d . . .
O8 O -0.0965(3) 1.0198(3) 0.6147(2) 0.0092(6) Uani 1 1 d . . .
O9 O 0.2681(3) 0.8822(3) 0.5297(3) 0.0166(7) Uani 1 1 d . . .
N1 N 0.2431(4) 0.8274(3) 0.2574(3) 0.0100(7) Uani 1 1 d . . .
N2 N 0.0222(3) 0.5659(3) 0.2254(3) 0.0092(7) Uani 1 1 d . . .
N3 N 0.4626(4) 0.6768(3) -0.0691(3) 0.0095(7) Uani 1 1 d . . .
N4 N 0.3089(4) 0.4557(3) -0.0686(3) 0.0105(7) Uani 1 1 d . . .
H4B H 0.2682 0.3673 -0.0866 0.013 Uiso 1 1 calc R . .
C1 C 0.3452(4) 0.9586(4) 0.2682(4) 0.0130(9) Uani 1 1 d . . .
H1B H 0.3412 1.0223 0.3267 0.016 Uiso 1 1 calc R . .
C2 C 0.4579(4) 1.0048(4) 0.1959(4) 0.0131(9) Uani 1 1 d . . .
H2B H 0.5246 1.0978 0.2050 0.016 Uiso 1 1 calc R . .
C3 C 0.4694(4) 0.9129(4) 0.1120(4) 0.0116(9) Uani 1 1 d . . .
H3C H 0.5452 0.9418 0.0644 0.014 Uiso 1 1 calc R . .
C4 C 0.3647(4) 0.7732(4) 0.0986(4) 0.0091(8) Uani 1 1 d . . .
C5 C 0.3704(4) 0.6668(4) 0.0150(3) 0.0094(8) Uani 1 1 d . . .
C6 C 0.2722(4) 0.5305(4) 0.0160(4) 0.0098(9) Uani 1 1 d . . .
C7 C 0.1506(4) 0.4877(4) 0.0844(3) 0.0104(9) Uani 1 1 d . . .
C8 C 0.0383(4) 0.3524(4) 0.0756(4) 0.0135(9) Uani 1 1 d . . .
H8A H 0.0438 0.2808 0.0268 0.016 Uiso 1 1 calc R . .
C9 C -0.0798(5) 0.3270(4) 0.1397(4) 0.0141(9) Uani 1 1 d . . .
H9B H -0.1560 0.2381 0.1345 0.017 Uiso 1 1 calc R . .
C10 C -0.0839(4) 0.4365(4) 0.2130(4) 0.0118(9) Uani 1 1 d . . .
H10A H -0.1651 0.4181 0.2555 0.014 Uiso 1 1 calc R . .
C11 C 0.2526(4) 0.7356(4) 0.1723(3) 0.0086(8) Uani 1 1 d . . .
C12 C 0.1393(4) 0.5918(4) 0.1605(3) 0.0080(8) Uani 1 1 d . . .
C13 C 0.4219(4) 0.5470(4) -0.1190(3) 0.0096(9) Uani 1 1 d . . .
C14 C 0.4921(4) 0.5101(4) -0.2166(3) 0.0081(8) Uani 1 1 d . . .
C15 C 0.6200(4) 0.6181(4) -0.2452(4) 0.0129(9) Uani 1 1 d . . .
H15A H 0.6541 0.7056 -0.2022 0.015 Uiso 1 1 calc R . .
C16 C 0.6973(4) 0.5992(4) -0.3352(4) 0.0122(9) Uani 1 1 d . . .
H16A H 0.7824 0.6725 -0.3515 0.015 Uiso 1 1 calc R . .
C18 C 0.5183(4) 0.3598(4) -0.3765(4) 0.0110(9) Uani 1 1 d . . .
H18A H 0.4840 0.2733 -0.4213 0.013 Uiso 1 1 calc R . .
C19 C 0.4421(4) 0.3793(4) -0.2859(4) 0.0091(8) Uani 1 1 d . . .
C20 C -0.0418(4) 0.9604(4) 0.5465(3) 0.0094(9) Uani 1 1 d . . .
O6 O 0.2677(3) 0.1189(3) -0.3565(3) 0.0122(6) Uani 1 1 d . . .
C17 C 0.6456(4) 0.4693(4) -0.4004(3) 0.0091(8) Uani 1 1 d . . .
O1W O -0.1733(4) 0.0183(3) 0.0375(3) 0.0238(8) Uani 1 1 d . . .
O2W O 0.9018(4) 0.9285(3) -0.1655(3) 0.0282(8) Uani 1 1 d . . .
H1 H 0.2456 0.9316 0.5804 0.056(9) Uiso 1 1 d R . .
H6 H 0.9339 0.9558 -0.2268 0.056(9) Uiso 1 1 d R . .
H5 H 0.9920 0.9427 -0.1497 0.056(9) Uiso 1 1 d R . .
H2 H 0.2956 0.8411 0.5746 0.056(9) Uiso 1 1 d R . .
H4 H -0.1477 -0.0087 -0.0251 0.056(9) Uiso 1 1 d R . .
H3 H -0.231(7) -0.060(6) 0.057(5) 0.056(9) Uiso 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
Eu O4 2.346(3) 2_565 ?
Eu O2 2.346(3) 2_665 ?
Eu O7 2.372(3) . ?
Eu O8 2.400(3) 2_576 ?
Eu O1 2.420(3) 1_456 ?
Eu O9 2.437(3) . ?
Eu N1 2.555(4) . ?
Eu N2 2.562(4) . ?
Eu C20 3.180(5) . ?
Eu C20 3.191(5) 2_576 ?
Eu H1 2.8176 . ?
S1 O3 1.445(3) . ?
S1 O1 1.460(3) . ?
S1 O2 1.468(3) . ?
S1 C17 1.773(4) . ?
S2 O6 1.449(3) . ?
S2 O5 1.453(3) . ?
S2 O4 1.463(3) . ?
S2 C19 1.782(4) . ?
O1 Eu 2.420(3) 1_654 ?
O2 Eu 2.346(3) 2_665 ?
O4 Eu 2.346(3) 2_565 ?
O7 C20 1.252(5) . ?
O8 C20 1.251(5) . ?
O8 Eu 2.400(3) 2_576 ?
O9 H1 0.8535 . ?
O9 H2 0.8511 . ?
N1 C1 1.336(5) . ?
N1 C11 1.361(5) . ?
N2 C10 1.333(5) . ?
N2 C12 1.368(5) . ?
N3 C13 1.335(5) . ?
N3 C5 1.367(5) . ?
N4 C13 1.365(5) . ?
N4 C6 1.369(5) . ?
N4 H4B 0.8600 . ?
C1 C2 1.398(6) . ?
C1 H1B 0.9300 . ?
C2 C3 1.361(6) . ?
C2 H2B 0.9300 . ?
C3 C4 1.409(5) . ?
C3 H3C 0.9300 . ?
C4 C11 1.400(6) . ?
C4 C5 1.445(6) . ?
C5 C6 1.384(5) . ?
C6 C7 1.425(6) . ?
C7 C8 1.402(5) . ?
C7 C12 1.400(6) . ?
C8 C9 1.370(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.396(6) . ?
C9 H9B 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.467(5) . ?
C13 C14 1.476(6) . ?
C14 C15 1.404(5) . ?
C14 C19 1.416(5) . ?
C15 C16 1.386(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.386(6) . ?
C16 H16A 0.9300 . ?
C18 C19 1.387(6) . ?
C18 C17 1.388(5) . ?
C18 H18A 0.9300 . ?
C20 C20 1.544(8) 2_576 ?
C20 Eu 3.191(5) 2_576 ?
O1W H4 0.8545 . ?
O1W H3 0.87(6) . ?
O2W H6 0.8500 . ?
O2W H5 0.8500 . ?

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 Eu O2 138.64(9) 2_565 2_665 ?
O4 Eu O7 86.80(11) 2_565 . ?
O2 Eu O7 113.57(11) 2_665 . ?
O4 Eu O8 74.00(9) 2_565 2_576 ?
O2 Eu O8 146.15(9) 2_665 2_576 ?
O7 Eu O8 68.07(10) . 2_576 ?
O4 Eu O1 74.11(11) 2_565 1_456 ?
O2 Eu O1 78.24(11) 2_665 1_456 ?
O7 Eu O1 72.72(11) . 1_456 ?
O8 Eu O1 130.05(10) 2_576 1_456 ?
O4 Eu O9 149.53(10) 2_565 . ?
O2 Eu O9 71.83(11) 2_665 . ?
O7 Eu O9 76.95(12) . . ?
O8 Eu O9 76.05(10) 2_576 . ?
O1 Eu O9 123.41(11) 1_456 . ?
O4 Eu N1 96.32(12) 2_565 . ?
O2 Eu N1 90.88(11) 2_665 . ?
O7 Eu N1 138.61(10) . . ?
O8 Eu N1 73.20(10) 2_576 . ?
O1 Eu N1 147.68(10) 1_456 . ?
O9 Eu N1 80.17(12) . . ?
O4 Eu N2 76.86(11) 2_565 . ?
O2 Eu N2 70.01(11) 2_665 . ?
O7 Eu N2 154.33(10) . . ?
O8 Eu N2 124.18(11) 2_576 . ?
O1 Eu N2 83.73(11) 1_456 . ?
O9 Eu N2 126.07(11) . . ?
N1 Eu N2 63.97(11) . . ?
O4 Eu C20 79.49(11) 2_565 . ?
O2 Eu C20 130.29(11) 2_665 . ?
O7 Eu C20 20.06(9) . . ?
O8 Eu C20 48.16(10) 2_576 . ?
O1 Eu C20 88.81(11) 1_456 . ?
O9 Eu C20 76.50(11) . . ?
N1 Eu C20 120.32(11) . . ?
N2 Eu C20 156.32(10) . . ?
O4 Eu C20 73.92(10) 2_565 2_576 ?
O2 Eu C20 146.42(10) 2_665 2_576 ?
O7 Eu C20 48.05(9) . 2_576 ?
O8 Eu C20 20.17(10) 2_576 2_576 ?
O1 Eu C20 112.76(11) 1_456 2_576 ?
O9 Eu C20 76.06(10) . 2_576 ?
N1 Eu C20 93.15(11) . 2_576 ?
N2 Eu C20 140.31(10) . 2_576 ?
C20 Eu C20 28.04(14) . 2_576 ?
O4 Eu H1 136.9 2_565 . ?
O2 Eu H1 83.1 2_665 . ?
O7 Eu H1 60.5 . . ?
O8 Eu H1 68.3 2_576 . ?
O1 Eu H1 116.1 1_456 . ?
O9 Eu H1 16.8 . . ?
N1 Eu H1 92.2 . . ?
N2 Eu H1 142.8 . . ?
C20 Eu H1 60.0 . . ?
C20 Eu H1 63.5 2_576 . ?
O3 S1 O1 113.73(18) . . ?
O3 S1 O2 112.02(17) . . ?
O1 S1 O2 110.52(16) . . ?
O3 S1 C17 108.32(18) . . ?
O1 S1 C17 106.92(18) . . ?
O2 S1 C17 104.78(19) . . ?
O6 S2 O5 114.40(17) . . ?
O6 S2 O4 112.88(17) . . ?
O5 S2 O4 110.10(17) . . ?
O6 S2 C19 107.02(19) . . ?
O5 S2 C19 106.50(17) . . ?
O4 S2 C19 105.25(18) . . ?
S1 O1 Eu 151.65(17) . 1_654 ?
S1 O2 Eu 153.99(17) . 2_665 ?
S2 O4 Eu 146.43(18) . 2_565 ?
C20 O7 Eu 119.4(3) . . ?
C20 O8 Eu 118.4(2) . 2_576 ?
Eu O9 H1 107.8 . . ?
Eu O9 H2 118.3 . . ?
H1 O9 H2 96.6 . . ?
C1 N1 C11 117.4(4) . . ?
C1 N1 Eu 122.0(3) . . ?
C11 N1 Eu 120.5(2) . . ?
C10 N2 C12 117.5(4) . . ?
C10 N2 Eu 121.3(3) . . ?
C12 N2 Eu 119.4(2) . . ?
C13 N3 C5 104.9(3) . . ?
C13 N4 C6 107.5(3) . . ?
C13 N4 H4B 126.3 . . ?
C6 N4 H4B 126.3 . . ?
N1 C1 C2 123.2(4) . . ?
N1 C1 H1B 118.4 . . ?
C2 C1 H1B 118.4 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2B 120.2 . . ?
C1 C2 H2B 120.2 . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 H3C 120.5 . . ?
C4 C3 H3C 120.5 . . ?
C11 C4 C3 118.1(4) . . ?
C11 C4 C5 118.6(3) . . ?
C3 C4 C5 123.3(4) . . ?
N3 C5 C6 110.9(4) . . ?
N3 C5 C4 130.1(4) . . ?
C6 C5 C4 119.0(4) . . ?
N4 C6 C5 105.2(4) . . ?
N4 C6 C7 130.3(4) . . ?
C5 C6 C7 124.2(4) . . ?
C8 C7 C12 118.5(4) . . ?
C8 C7 C6 125.0(4) . . ?
C12 C7 C6 116.4(4) . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 H9B 120.5 . . ?
C10 C9 H9B 120.5 . . ?
N2 C10 C9 123.6(4) . . ?
N2 C10 H10A 118.2 . . ?
C9 C10 H10A 118.2 . . ?
N1 C11 C4 122.8(4) . . ?
N1 C11 C12 117.1(4) . . ?
C4 C11 C12 120.2(4) . . ?
N2 C12 C7 122.2(4) . . ?
N2 C12 C11 116.8(4) . . ?
C7 C12 C11 120.9(4) . . ?
N3 C13 N4 111.5(4) . . ?
N3 C13 C14 123.1(3) . . ?
N4 C13 C14 125.4(4) . . ?
C15 C14 C19 116.9(4) . . ?
C15 C14 C13 115.9(4) . . ?
C19 C14 C13 127.2(3) . . ?
C16 C15 C14 122.5(4) . . ?
C16 C15 H15A 118.8 . . ?
C14 C15 H15A 118.8 . . ?
C15 C16 C17 119.0(4) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?
C18 C19 C14 121.0(3) . . ?
C18 C19 S2 114.4(3) . . ?
C14 C19 S2 124.6(3) . . ?
O8 C20 O7 126.5(4) . . ?
O8 C20 C20 116.9(4) . 2_576 ?
O7 C20 C20 116.7(5) . 2_576 ?
O8 C20 Eu 166.3(3) . . ?
O7 C20 Eu 40.5(2) . . ?
C20 C20 Eu 76.4(3) 2_576 . ?
O8 C20 Eu 41.42(18) . 2_576 ?
O7 C20 Eu 167.2(3) . 2_576 ?
C20 C20 Eu 75.6(3) 2_576 2_576 ?
Eu C20 Eu 151.96(14) . 2_576 ?
C18 C17 C16 120.7(4) . . ?
C18 C17 S1 117.8(3) . . ?
C16 C17 S1 121.3(3) . . ?
H4 O1W H3 101.4 . . ?
H6 O2W H5 83.3 . . ?

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 S1 O1 Eu -118.0(4) . . . 1_654 ?
O2 S1 O1 Eu 9.0(4) . . . 1_654 ?
C17 S1 O1 Eu 122.5(4) . . . 1_654 ?
O3 S1 O2 Eu -14.0(5) . . . 2_665 ?
O1 S1 O2 Eu -141.9(4) . . . 2_665 ?
C17 S1 O2 Eu 103.2(4) . . . 2_665 ?
O6 S2 O4 Eu -18.0(4) . . . 2_565 ?
O5 S2 O4 Eu -147.2(3) . . . 2_565 ?
C19 S2 O4 Eu 98.4(3) . . . 2_565 ?
O4 Eu O7 C20 -67.7(3) 2_565 . . . ?
O2 Eu O7 C20 149.6(3) 2_665 . . . ?
O8 Eu O7 C20 6.3(3) 2_576 . . . ?
O1 Eu O7 C20 -142.1(3) 1_456 . . . ?
O9 Eu O7 C20 86.3(3) . . . . ?
N1 Eu O7 C20 28.2(3) . . . . ?
N2 Eu O7 C20 -117.8(3) . . . . ?
C20 Eu O7 C20 3.5(3) 2_576 . . . ?
O4 Eu N1 C1 102.9(3) 2_565 . . . ?
O2 Eu N1 C1 -117.9(3) 2_665 . . . ?
O7 Eu N1 C1 10.5(4) . . . . ?
O8 Eu N1 C1 31.7(3) 2_576 . . . ?
O1 Eu N1 C1 173.0(3) 1_456 . . . ?
O9 Eu N1 C1 -46.6(3) . . . . ?
N2 Eu N1 C1 174.9(3) . . . . ?
C20 Eu N1 C1 21.4(3) . . . . ?
C20 Eu N1 C1 28.7(3) 2_576 . . . ?
O4 Eu N1 C11 -80.6(3) 2_565 . . . ?
O2 Eu N1 C11 58.6(3) 2_665 . . . ?
O7 Eu N1 C11 -173.0(2) . . . . ?
O8 Eu N1 C11 -151.8(3) 2_576 . . . ?
O1 Eu N1 C11 -10.5(4) 1_456 . . . ?
O9 Eu N1 C11 130.0(3) . . . . ?
N2 Eu N1 C11 -8.6(3) . . . . ?
C20 Eu N1 C11 -162.1(3) . . . . ?
C20 Eu N1 C11 -154.8(3) 2_576 . . . ?
O4 Eu N2 C10 -78.5(3) 2_565 . . . ?
O2 Eu N2 C10 76.3(3) 2_665 . . . ?
O7 Eu N2 C10 -26.7(4) . . . . ?
O8 Eu N2 C10 -138.5(3) 2_576 . . . ?
O1 Eu N2 C10 -3.4(3) 1_456 . . . ?
O9 Eu N2 C10 123.8(3) . . . . ?
N1 Eu N2 C10 177.6(3) . . . . ?
C20 Eu N2 C10 -75.8(4) . . . . ?
C20 Eu N2 C10 -121.9(3) 2_576 . . . ?
O4 Eu N2 C12 117.2(3) 2_565 . . . ?
O2 Eu N2 C12 -87.9(3) 2_665 . . . ?
O7 Eu N2 C12 169.0(2) . . . . ?
O8 Eu N2 C12 57.3(3) 2_576 . . . ?
O1 Eu N2 C12 -167.7(3) 1_456 . . . ?
O9 Eu N2 C12 -40.4(3) . . . . ?
N1 Eu N2 C12 13.3(3) . . . . ?
C20 Eu N2 C12 119.9(3) . . . . ?
C20 Eu N2 C12 73.8(3) 2_576 . . . ?
C11 N1 C1 C2 1.0(6) . . . . ?
Eu N1 C1 C2 177.6(3) . . . . ?
N1 C1 C2 C3 -2.2(6) . . . . ?
C1 C2 C3 C4 1.4(6) . . . . ?
C2 C3 C4 C11 0.3(6) . . . . ?
C2 C3 C4 C5 -177.7(4) . . . . ?
C13 N3 C5 C6 -0.5(4) . . . . ?
C13 N3 C5 C4 178.3(4) . . . . ?
C11 C4 C5 N3 176.5(4) . . . . ?
C3 C4 C5 N3 -5.4(6) . . . . ?
C11 C4 C5 C6 -4.8(5) . . . . ?
C3 C4 C5 C6 173.3(4) . . . . ?
C13 N4 C6 C5 -1.8(4) . . . . ?
C13 N4 C6 C7 171.1(4) . . . . ?
N3 C5 C6 N4 1.4(4) . . . . ?
C4 C5 C6 N4 -177.5(3) . . . . ?
N3 C5 C6 C7 -172.0(3) . . . . ?
C4 C5 C6 C7 9.0(6) . . . . ?
N4 C6 C7 C8 -0.9(7) . . . . ?
C5 C6 C7 C8 170.8(4) . . . . ?
N4 C6 C7 C12 -176.6(4) . . . . ?
C5 C6 C7 C12 -4.8(6) . . . . ?
C12 C7 C8 C9 1.2(6) . . . . ?
C6 C7 C8 C9 -174.4(4) . . . . ?
C7 C8 C9 C10 -0.7(6) . . . . ?
C12 N2 C10 C9 1.4(6) . . . . ?
Eu N2 C10 C9 -163.2(3) . . . . ?
C8 C9 C10 N2 -0.7(6) . . . . ?
C1 N1 C11 C4 0.9(6) . . . . ?
Eu N1 C11 C4 -175.7(3) . . . . ?
C1 N1 C11 C12 -179.5(3) . . . . ?
Eu N1 C11 C12 3.8(4) . . . . ?
C3 C4 C11 N1 -1.6(6) . . . . ?
C5 C4 C11 N1 176.6(3) . . . . ?
C3 C4 C11 C12 178.9(3) . . . . ?
C5 C4 C11 C12 -3.0(5) . . . . ?
C10 N2 C12 C7 -0.8(5) . . . . ?
Eu N2 C12 C7 164.1(3) . . . . ?
C10 N2 C12 C11 178.0(3) . . . . ?
Eu N2 C12 C11 -17.1(4) . . . . ?
C8 C7 C12 N2 -0.5(6) . . . . ?
C6 C7 C12 N2 175.5(3) . . . . ?
C8 C7 C12 C11 -179.3(3) . . . . ?
C6 C7 C12 C11 -3.3(5) . . . . ?
N1 C11 C12 N2 8.8(5) . . . . ?
C4 C11 C12 N2 -171.7(3) . . . . ?
N1 C11 C12 C7 -172.4(3) . . . . ?
C4 C11 C12 C7 7.2(6) . . . . ?
C5 N3 C13 N4 -0.7(4) . . . . ?
C5 N3 C13 C14 179.0(3) . . . . ?
C6 N4 C13 N3 1.7(4) . . . . ?
C6 N4 C13 C14 -178.1(4) . . . . ?
N3 C13 C14 C15 8.7(5) . . . . ?
N4 C13 C14 C15 -171.5(4) . . . . ?
N3 C13 C14 C19 -169.3(4) . . . . ?
N4 C13 C14 C19 10.4(6) . . . . ?
C19 C14 C15 C16 -1.4(6) . . . . ?
C13 C14 C15 C16 -179.6(4) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C17 C18 C19 C14 0.1(6) . . . . ?
C17 C18 C19 S2 179.3(3) . . . . ?
C15 C14 C19 C18 0.9(5) . . . . ?
C13 C14 C19 C18 178.9(4) . . . . ?
C15 C14 C19 S2 -178.2(3) . . . . ?
C13 C14 C19 S2 -0.2(6) . . . . ?
O6 S2 C19 C18 0.1(3) . . . . ?
O5 S2 C19 C18 122.9(3) . . . . ?
O4 S2 C19 C18 -120.2(3) . . . . ?
O6 S2 C19 C14 179.2(3) . . . . ?
O5 S2 C19 C14 -58.0(4) . . . . ?
O4 S2 C19 C14 58.9(4) . . . . ?
Eu O8 C20 O7 174.2(3) 2_576 . . . ?
Eu O8 C20 C20 -5.6(5) 2_576 . . 2_576 ?
Eu O8 C20 Eu -169.6(10) 2_576 . . . ?
Eu O7 C20 O8 174.2(3) . . . . ?
Eu O7 C20 C20 -6.0(5) . . . 2_576 ?
Eu O7 C20 Eu -168.3(10) . . . 2_576 ?
O4 Eu C20 O8 89.9(11) 2_565 . . . ?
O2 Eu C20 O8 -57.6(11) 2_665 . . . ?
O7 Eu C20 O8 -20.2(10) . . . . ?
O8 Eu C20 O8 167.7(11) 2_576 . . . ?
O1 Eu C20 O8 15.8(11) 1_456 . . . ?
O9 Eu C20 O8 -109.0(11) . . . . ?
N1 Eu C20 O8 -178.9(11) . . . . ?
N2 Eu C20 O8 87.2(11) . . . . ?
C20 Eu C20 O8 165.3(13) 2_576 . . . ?
O4 Eu C20 O7 110.0(3) 2_565 . . . ?
O2 Eu C20 O7 -37.5(3) 2_665 . . . ?
O8 Eu C20 O7 -172.1(3) 2_576 . . . ?
O1 Eu C20 O7 36.0(3) 1_456 . . . ?
O9 Eu C20 O7 -88.9(3) . . . . ?
N1 Eu C20 O7 -158.8(3) . . . . ?
N2 Eu C20 O7 107.3(3) . . . . ?
C20 Eu C20 O7 -174.5(5) 2_576 . . . ?
O4 Eu C20 C20 -75.5(3) 2_565 . . 2_576 ?
O2 Eu C20 C20 137.0(2) 2_665 . . 2_576 ?
O7 Eu C20 C20 174.5(5) . . . 2_576 ?
O8 Eu C20 C20 2.4(2) 2_576 . . 2_576 ?
O1 Eu C20 C20 -149.5(3) 1_456 . . 2_576 ?
O9 Eu C20 C20 85.6(3) . . . 2_576 ?
N1 Eu C20 C20 15.8(3) . . . 2_576 ?
N2 Eu C20 C20 -78.1(4) . . . 2_576 ?
O4 Eu C20 Eu -75.5(3) 2_565 . . 2_576 ?
O2 Eu C20 Eu 137.0(2) 2_665 . . 2_576 ?
O7 Eu C20 Eu 174.5(5) . . . 2_576 ?
O8 Eu C20 Eu 2.4(2) 2_576 . . 2_576 ?
O1 Eu C20 Eu -149.5(3) 1_456 . . 2_576 ?
O9 Eu C20 Eu 85.6(3) . . . 2_576 ?
N1 Eu C20 Eu 15.7(3) . . . 2_576 ?
N2 Eu C20 Eu -78.1(4) . . . 2_576 ?
C20 Eu C20 Eu 0.0 2_576 . . 2_576 ?
C19 C18 C17 C16 -0.7(6) . . . . ?
C19 C18 C17 S1 174.2(3) . . . . ?
C15 C16 C17 C18 0.2(6) . . . . ?
C15 C16 C17 S1 -174.5(3) . . . . ?
O3 S1 C17 C18 29.3(4) . . . . ?
O1 S1 C17 C18 152.2(3) . . . . ?
O2 S1 C17 C18 -90.5(3) . . . . ?
O3 S1 C17 C16 -155.9(3) . . . . ?
O1 S1 C17 C16 -32.9(4) . . . . ?
O2 S1 C17 C16 84.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.922
_refine_diff_density_max         1.188
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.152
