# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Nd
_database_code_depnum_ccdc_archive 'CCDC 1404007'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            'C21 H16 N3 Nd2 O15.50'
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 N3 Nd2 O15.50'
_chemical_formula_sum            'C21 H16 N3 Nd2 O15.50'
_chemical_formula_weight         846.85

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'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.9748(2)
_cell_length_b                   17.4692(2)
_cell_length_c                   13.3874(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.2300(10)
_cell_angle_gamma                90
_cell_volume                     2517.50(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6776
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.234
_exptl_crystal_F_000             1628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.219
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_max          0.274
_exptl_absorpt_coefficient_mu    4.165
_shelx_estimated_absorpt_T_min   0.399
_shelx_estimated_absorpt_T_max   0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3947
_exptl_absorpt_correction_T_max  0.4622
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22732
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.892
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5160
_reflns_number_gt                4391
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0180P)²+1.7188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5160
_refine_ls_number_parameters     393
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0485
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.67184(2) 0.04253(2) 0.59031(2) 0.01402(6) Uani 1 1 d . . . . .
Nd2 Nd 1.15705(2) 0.25813(2) 0.59362(2) 0.01298(6) Uani 1 1 d . . . . .
N2 N 0.6262(3) 0.12023(15) 0.7428(2) 0.0178(7) Uani 1 1 d . . . . .
N3 N 1.1438(3) 0.12972(15) 0.6840(2) 0.0178(7) Uani 1 1 d . . . . .
N1 N 0.7106(3) 0.12096(15) 0.4327(2) 0.0172(7) Uani 1 1 d . . . . .
O1 O 0.5462(2) 0.00970(13) 0.41427(18) 0.0204(6) Uani 1 1 d . . . . .
O9 O 1.1727(3) 0.26167(14) 0.77952(18) 0.0263(6) Uani 1 1 d . . . . .
O2 O 0.4930(3) 0.02688(17) 0.2469(2) 0.0422(8) Uani 1 1 d . . . . .
O6 O 0.8577(3) 0.03200(15) 0.9250(2) 0.0335(7) Uani 1 1 d . . . . .
C6 C 0.8005(3) 0.17361(19) 0.4456(3) 0.0200(8) Uani 1 1 d . . . . .
C7 C 0.8600(3) 0.1874(2) 0.5558(3) 0.0212(8) Uani 1 1 d . . . . .
C2 C 0.6530(3) 0.1046(2) 0.3378(3) 0.0188(8) Uani 1 1 d . . . . .
C1 C 0.5567(3) 0.0420(2) 0.3301(3) 0.0219(8) Uani 1 1 d . . . . .
C4 C 0.7729(4) 0.1956(2) 0.2677(3) 0.0357(11) Uani 1 1 d . . . . .
H4 H 0.7928 0.2212 0.2121 0.043 Uiso 1 1 calc R U . . .
C5 C 0.8353(4) 0.2118(2) 0.3642(3) 0.0302(10) Uani 1 1 d . . . . .
H5 H 0.8995 0.2475 0.3752 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6805(4) 0.1411(2) 0.2536(3) 0.0286(9) Uani 1 1 d . . . . .
H3 H 0.6375 0.1292 0.1885 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7898(3) 0.04550(19) 0.8412(3) 0.0211(8) Uani 1 1 d . . . . .
C9 C 0.6895(4) 0.10552(19) 0.8368(3) 0.0211(8) Uani 1 1 d . . . . .
C12 C 0.4948(4) 0.2049(2) 0.8132(3) 0.0307(10) Uani 1 1 d . . . . .
H12 H 0.4275 0.2383 0.8035 0.037 Uiso 1 1 calc R U . . .
C13 C 0.5297(3) 0.16895(19) 0.7315(3) 0.0190(8) Uani 1 1 d . . . . .
C11 C 0.5615(4) 0.1904(2) 0.9093(3) 0.0401(11) Uani 1 1 d . . . . .
H11 H 0.5401 0.2140 0.9657 0.048 Uiso 1 1 calc R U . . .
C16 C 1.1427(3) 0.1284(2) 0.7833(3) 0.0195(8) Uani 1 1 d . . . . .
C15 C 1.1639(3) 0.2047(2) 0.8344(3) 0.0222(9) Uani 1 1 d . . . . .
C19 C 1.1015(3) -0.0039(2) 0.6751(3) 0.0230(9) Uani 1 1 d . . . . .
H19 H 1.0875 -0.0485 0.6366 0.028 Uiso 1 1 calc R U . . .
C20 C 1.1253(3) 0.06395(19) 0.6312(3) 0.0183(8) Uani 1 1 d . . . . .
C21 C 0.8647(3) -0.0722(2) 0.4789(3) 0.0185(8) Uani 1 1 d . . . . .
O13 O 0.6673(2) -0.10333(14) 0.60874(19) 0.0235(6) Uani 1 1 d G . . . .
H13A H 0.5980 -0.1282 0.5646 0.028 Uiso 1 1 d G U . . .
H13B H 0.7429 -0.1286 0.5991 0.028 Uiso 1 1 d G U . . .
O7 O 0.5153(2) 0.15009(13) 0.55456(18) 0.0209(6) Uani 1 1 d . . . . .
O12 O 0.8460(2) -0.01255(13) 0.52590(18) 0.0205(6) Uani 1 1 d . . . . .
O14 O 1.0424(2) 0.38510(13) 0.5726(2) 0.0263(6) Uani 1 1 d G . . . .
H14A H 1.0880 0.4330 0.5815 0.032 Uiso 1 1 d G U . . .
H14B H 0.9626 0.3953 0.5290 0.032 Uiso 1 1 d G U . . .
O8 O 0.3641(3) 0.21398(16) 0.6057(2) 0.0365(7) Uani 1 1 d . . . . .
O10 O 1.1730(3) 0.29418(15) 0.42900(19) 0.0383(8) Uani 1 1 d . . . . .
O15 O 1.2977(4) 0.36471(19) 0.6619(3) 0.0464(9) Uani 1 1 d D . . . .
C18 C 1.0988(4) -0.0047(2) 0.7776(3) 0.0320(10) Uani 1 1 d . . . . .
H18 H 1.0815 -0.0499 0.8089 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6609(4) 0.1403(2) 0.9212(3) 0.0331(10) Uani 1 1 d . . . . .
H10 H 0.7078 0.1304 0.9856 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4647(3) 0.17851(19) 0.6221(3) 0.0216(8) Uani 1 1 d . . . . .
O16 O 0.4364(13) 0.0560(6) 0.0329(10) 0.158(6) Uani 0.5 1 d . . P . .
H15B H 1.351(6) 0.389(5) 0.638(7) 0.20(5) Uiso 1 1 d D . . . .
H15A H 1.280(6) 0.390(3) 0.707(4) 0.10(3) Uiso 1 1 d D . . . .
O4 O 0.9419(2) 0.23941(14) 0.5733(2) 0.0282(6) Uani 1 1 d . . . . .
O3 O 0.8238(2) 0.14850(14) 0.62152(19) 0.0250(6) Uani 1 1 d . . . . .
O5 O 0.7940(2) 0.01171(14) 0.75861(19) 0.0254(6) Uani 1 1 d . . . . .
C17 C 1.1218(4) 0.0619(2) 0.8337(3) 0.0320(10) Uani 1 1 d . . . . .
H17 H 1.1232 0.0621 0.9034 0.038 Uiso 1 1 calc R U . . .
O11 O 1.1285(2) 0.13910(13) 0.48610(18) 0.0244(6) 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
Nd1 O12 2.442(2) . ?
Nd1 O5 2.447(2) . ?
Nd1 O3 2.472(2) . ?
Nd1 O7 2.528(2) . ?
Nd1 O1 2.551(2) 3_656 ?
Nd1 O1 2.553(2) . ?
Nd1 O13 2.561(2) . ?
Nd1 N2 2.581(3) . ?
Nd1 N1 2.619(3) . ?
Nd2 O10 2.331(3) . ?
Nd2 O4 2.346(3) . ?
Nd2 O8 2.375(3) 1_655 ?
Nd2 O9 2.462(2) . ?
Nd2 O15 2.477(3) . ?
Nd2 O11 2.514(2) . ?
Nd2 O14 2.539(2) . ?
Nd2 N3 2.567(3) . ?
N2 C9 1.338(4) . ?
N2 C13 1.344(4) . ?
N3 C16 1.332(4) . ?
N3 C20 1.344(4) . ?
N1 C2 1.335(4) . ?
N1 C6 1.335(4) . ?
O1 C1 1.285(4) . ?
O1 Nd1 2.551(2) 3_656 ?
O9 C15 1.252(4) . ?
O2 C1 1.223(4) . ?
O6 C8 1.242(4) . ?
C6 C5 1.394(5) . ?
C6 C7 1.512(5) . ?
C7 O3 1.236(4) . ?
C7 O4 1.268(4) . ?
C2 C3 1.379(5) . ?
C2 C1 1.510(5) . ?
C4 C5 1.369(6) . ?
C4 C3 1.377(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C8 O5 1.263(4) . ?
C8 C9 1.513(5) . ?
C9 C10 1.372(5) . ?
C12 C11 1.375(6) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.508(5) . ?
C11 C10 1.383(6) . ?
C11 H11 0.9300 . ?
C16 C17 1.384(5) . ?
C16 C15 1.495(5) . ?
C15 O10 1.251(4) 4_566 ?
C19 C20 1.371(5) . ?
C19 C18 1.379(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.506(5) 3_756 ?
C21 O12 1.254(4) . ?
C21 O11 1.256(4) 3_756 ?
C21 C20 1.506(5) 3_756 ?
O13 H13A 0.9700 . ?
O13 H13B 0.9701 . ?
O7 C14 1.253(4) . ?
O14 H14A 0.9701 . ?
O14 H14B 0.9700 . ?
O8 C14 1.248(4) . ?
O8 Nd2 2.375(3) 1_455 ?
O10 C15 1.251(4) 4_565 ?
O15 H15B 0.83(2) . ?
O15 H15A 0.81(2) . ?
C18 C17 1.382(5) . ?
C18 H18 0.9300 . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
O11 C21 1.256(4) 3_756 ?

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
O12 Nd1 O5 84.97(8) . . ?
O12 Nd1 O3 78.81(8) . . ?
O5 Nd1 O3 77.20(9) . . ?
O12 Nd1 O7 140.87(8) . . ?
O5 Nd1 O7 124.62(8) . . ?
O3 Nd1 O7 83.49(8) . . ?
O12 Nd1 O1 130.22(8) . 3_656 ?
O5 Nd1 O1 106.65(8) . 3_656 ?
O3 Nd1 O1 150.56(8) . 3_656 ?
O7 Nd1 O1 70.22(8) . 3_656 ?
O12 Nd1 O1 84.53(8) . . ?
O5 Nd1 O1 154.31(8) . . ?
O3 Nd1 O1 123.33(8) . . ?
O7 Nd1 O1 76.55(8) . . ?
O1 Nd1 O1 64.03(9) 3_656 . ?
O12 Nd1 O13 70.94(8) . . ?
O5 Nd1 O13 73.14(8) . . ?
O3 Nd1 O13 138.92(8) . . ?
O7 Nd1 O13 137.09(8) . . ?
O1 Nd1 O13 67.09(8) 3_656 . ?
O1 Nd1 O13 81.28(8) . . ?
O12 Nd1 N2 140.57(8) . . ?
O5 Nd1 N2 62.81(8) . . ?
O3 Nd1 N2 72.61(9) . . ?
O7 Nd1 N2 61.93(8) . . ?
O1 Nd1 N2 83.18(8) 3_656 . ?
O1 Nd1 N2 134.05(8) . . ?
O13 Nd1 N2 115.88(8) . . ?
O12 Nd1 N1 70.16(8) . . ?
O5 Nd1 N1 135.32(9) . . ?
O3 Nd1 N1 62.25(8) . . ?
O7 Nd1 N1 70.71(8) . . ?
O1 Nd1 N1 117.82(8) 3_656 . ?
O1 Nd1 N1 61.12(8) . . ?
O13 Nd1 N1 127.39(8) . . ?
N2 Nd1 N1 116.70(9) . . ?
O10 Nd2 O4 100.79(11) . . ?
O10 Nd2 O8 84.54(10) . 1_655 ?
O4 Nd2 O8 152.91(9) . 1_655 ?
O10 Nd2 O9 161.01(9) . . ?
O4 Nd2 O9 89.51(9) . . ?
O8 Nd2 O9 93.55(10) 1_655 . ?
O10 Nd2 O15 89.40(13) . . ?
O4 Nd2 O15 133.50(11) . . ?
O8 Nd2 O15 72.53(12) 1_655 . ?
O9 Nd2 O15 72.07(12) . . ?
O10 Nd2 O11 72.90(8) . . ?
O4 Nd2 O11 78.92(9) . . ?
O8 Nd2 O11 77.35(9) 1_655 . ?
O9 Nd2 O11 125.17(8) . . ?
O15 Nd2 O11 146.34(12) . . ?
O10 Nd2 O14 77.66(9) . . ?
O4 Nd2 O14 69.08(8) . . ?
O8 Nd2 O14 137.60(9) 1_655 . ?
O9 Nd2 O14 91.46(9) . . ?
O15 Nd2 O14 69.15(10) . . ?
O11 Nd2 O14 130.96(8) . . ?
O10 Nd2 N3 134.71(9) . . ?
O4 Nd2 N3 77.57(9) . . ?
O8 Nd2 N3 79.94(10) 1_655 . ?
O9 Nd2 N3 62.90(8) . . ?
O15 Nd2 N3 124.84(11) . . ?
O11 Nd2 N3 62.28(8) . . ?
O14 Nd2 N3 138.03(9) . . ?
C9 N2 C13 118.8(3) . . ?
C9 N2 Nd1 119.8(2) . . ?
C13 N2 Nd1 120.9(2) . . ?
C16 N3 C20 118.7(3) . . ?
C16 N3 Nd2 119.9(2) . . ?
C20 N3 Nd2 121.1(2) . . ?
C2 N1 C6 118.1(3) . . ?
C2 N1 Nd1 122.3(2) . . ?
C6 N1 Nd1 119.2(2) . . ?
C1 O1 Nd1 112.3(2) . 3_656 ?
C1 O1 Nd1 125.9(2) . . ?
Nd1 O1 Nd1 115.97(9) 3_656 . ?
C15 O9 Nd2 125.1(2) . . ?
N1 C6 C5 122.5(4) . . ?
N1 C6 C7 113.8(3) . . ?
C5 C6 C7 123.7(3) . . ?
O3 C7 O4 125.3(4) . . ?
O3 C7 C6 118.0(3) . . ?
O4 C7 C6 116.7(3) . . ?
N1 C2 C3 122.7(3) . . ?
N1 C2 C1 114.5(3) . . ?
C3 C2 C1 122.7(3) . . ?
O2 C1 O1 124.8(3) . . ?
O2 C1 C2 119.2(3) . . ?
O1 C1 C2 116.0(3) . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
O6 C8 O5 125.7(4) . . ?
O6 C8 C9 118.1(3) . . ?
O5 C8 C9 116.1(3) . . ?
N2 C9 C10 121.9(4) . . ?
N2 C9 C8 114.3(3) . . ?
C10 C9 C8 123.8(3) . . ?
C11 C12 C13 118.6(4) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
N2 C13 C12 122.3(3) . . ?
N2 C13 C14 113.2(3) . . ?
C12 C13 C14 124.6(3) . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
N3 C16 C17 122.4(3) . . ?
N3 C16 C15 114.2(3) . . ?
C17 C16 C15 123.4(3) . . ?
O10 C15 O9 125.5(3) 4_566 . ?
O10 C15 C16 116.9(3) 4_566 . ?
O9 C15 C16 117.6(3) . . ?
C20 C19 C18 118.5(3) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
N3 C20 C19 122.4(3) . . ?
N3 C20 C21 113.6(3) . 3_756 ?
C19 C20 C21 123.9(3) . 3_756 ?
O12 C21 O11 126.1(3) . 3_756 ?
O12 C21 C20 117.5(3) . 3_756 ?
O11 C21 C20 116.3(3) 3_756 3_756 ?
Nd1 O13 H13A 114.5 . . ?
Nd1 O13 H13B 114.0 . . ?
H13A O13 H13B 107.7 . . ?
C14 O7 Nd1 122.6(2) . . ?
C21 O12 Nd1 136.0(2) . . ?
Nd2 O14 H14A 120.4 . . ?
Nd2 O14 H14B 126.7 . . ?
H14A O14 H14B 107.4 . . ?
C14 O8 Nd2 167.2(3) . 1_455 ?
C15 O10 Nd2 162.8(3) 4_565 . ?
Nd2 O15 H15B 132(7) . . ?
Nd2 O15 H15A 118(5) . . ?
H15B O15 H15A 107(7) . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C9 C10 C11 119.1(4) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
O8 C14 O7 124.8(4) . . ?
O8 C14 C13 117.5(4) . . ?
O7 C14 C13 117.7(3) . . ?
C7 O4 Nd2 141.5(2) . . ?
C7 O3 Nd1 126.2(2) . . ?
C8 O5 Nd1 126.7(2) . . ?
C18 C17 C16 118.1(4) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C21 O11 Nd2 124.4(2) 3_756 . ?

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
C2 N1 C6 C5 0.2(5) . . . . ?
Nd1 N1 C6 C5 173.1(3) . . . . ?
C2 N1 C6 C7 -179.7(3) . . . . ?
Nd1 N1 C6 C7 -6.8(4) . . . . ?
N1 C6 C7 O3 2.0(5) . . . . ?
C5 C6 C7 O3 -177.9(4) . . . . ?
N1 C6 C7 O4 -176.7(3) . . . . ?
C5 C6 C7 O4 3.4(5) . . . . ?
C6 N1 C2 C3 -1.6(5) . . . . ?
Nd1 N1 C2 C3 -174.2(3) . . . . ?
C6 N1 C2 C1 177.4(3) . . . . ?
Nd1 N1 C2 C1 4.8(4) . . . . ?
Nd1 O1 C1 O2 -26.0(5) 3_656 . . . ?
Nd1 O1 C1 O2 -177.7(3) . . . . ?
Nd1 O1 C1 C2 152.1(2) 3_656 . . . ?
Nd1 O1 C1 C2 0.3(4) . . . . ?
N1 C2 C1 O2 174.9(3) . . . . ?
C3 C2 C1 O2 -6.1(6) . . . . ?
N1 C2 C1 O1 -3.3(5) . . . . ?
C3 C2 C1 O1 175.7(3) . . . . ?
C3 C4 C5 C6 -1.7(6) . . . . ?
N1 C6 C5 C4 1.4(6) . . . . ?
C7 C6 C5 C4 -178.7(4) . . . . ?
C5 C4 C3 C2 0.4(6) . . . . ?
N1 C2 C3 C4 1.3(6) . . . . ?
C1 C2 C3 C4 -177.6(4) . . . . ?
C13 N2 C9 C10 -1.9(5) . . . . ?
Nd1 N2 C9 C10 -174.0(3) . . . . ?
C13 N2 C9 C8 175.6(3) . . . . ?
Nd1 N2 C9 C8 3.5(4) . . . . ?
O6 C8 C9 N2 175.7(3) . . . . ?
O5 C8 C9 N2 -6.4(5) . . . . ?
O6 C8 C9 C10 -6.9(6) . . . . ?
O5 C8 C9 C10 171.0(4) . . . . ?
C9 N2 C13 C12 0.8(5) . . . . ?
Nd1 N2 C13 C12 172.8(3) . . . . ?
C9 N2 C13 C14 -178.4(3) . . . . ?
Nd1 N2 C13 C14 -6.4(4) . . . . ?
C11 C12 C13 N2 0.2(6) . . . . ?
C11 C12 C13 C14 179.3(4) . . . . ?
C13 C12 C11 C10 -0.1(7) . . . . ?
C20 N3 C16 C17 -0.7(6) . . . . ?
Nd2 N3 C16 C17 172.6(3) . . . . ?
C20 N3 C16 C15 -179.9(3) . . . . ?
Nd2 N3 C16 C15 -6.5(4) . . . . ?
Nd2 O9 C15 O10 179.2(3) . . . 4_566 ?
Nd2 O9 C15 C16 0.3(5) . . . . ?
N3 C16 C15 O10 -174.8(3) . . . 4_566 ?
C17 C16 C15 O10 6.1(6) . . . 4_566 ?
N3 C16 C15 O9 4.2(5) . . . . ?
C17 C16 C15 O9 -174.9(4) . . . . ?
C16 N3 C20 C19 2.1(5) . . . . ?
Nd2 N3 C20 C19 -171.2(3) . . . . ?
C16 N3 C20 C21 -177.0(3) . . . 3_756 ?
Nd2 N3 C20 C21 9.7(4) . . . 3_756 ?
C18 C19 C20 N3 -1.2(6) . . . . ?
C18 C19 C20 C21 177.8(3) . . . 3_756 ?
O11 C21 O12 Nd1 -69.6(5) 3_756 . . . ?
C20 C21 O12 Nd1 107.6(4) 3_756 . . . ?
C20 C19 C18 C17 -1.0(6) . . . . ?
N2 C9 C10 C11 1.9(6) . . . . ?
C8 C9 C10 C11 -175.3(4) . . . . ?
C12 C11 C10 C9 -0.9(7) . . . . ?
Nd2 O8 C14 O7 114.7(12) 1_455 . . . ?
Nd2 O8 C14 C13 -65.0(13) 1_455 . . . ?
Nd1 O7 C14 O8 -157.8(3) . . . . ?
Nd1 O7 C14 C13 21.9(4) . . . . ?
N2 C13 C14 O8 170.1(3) . . . . ?
C12 C13 C14 O8 -9.0(5) . . . . ?
N2 C13 C14 O7 -9.6(5) . . . . ?
C12 C13 C14 O7 171.2(4) . . . . ?
O3 C7 O4 Nd2 89.7(5) . . . . ?
C6 C7 O4 Nd2 -91.7(4) . . . . ?
O4 C7 O3 Nd1 -176.9(2) . . . . ?
C6 C7 O3 Nd1 4.6(5) . . . . ?
O6 C8 O5 Nd1 -175.4(3) . . . . ?
C9 C8 O5 Nd1 6.8(5) . . . . ?
C19 C18 C17 C16 2.3(6) . . . . ?
N3 C16 C17 C18 -1.4(6) . . . . ?
C15 C16 C17 C18 177.6(4) . . . . ?

_refine_diff_density_max         0.587
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.116

####################################################################### 
# 
# 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_Eu
_database_code_depnum_ccdc_archive 'CCDC 1404008'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            'C21 H16 Eu2 N3 O15.50'
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 Eu2 N3 O15.50'
_chemical_formula_sum            'C21 H16 Eu2 N3 O15.50'
_chemical_formula_weight         862.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.9763(2)
_cell_length_b                   17.4706(4)
_cell_length_c                   13.3915(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.2370(10)
_cell_angle_gamma                90
_cell_volume                     2518.76(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8185
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.274
_exptl_crystal_F_000             1652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.131
_exptl_absorpt_coefficient_mu    5.021
_shelx_estimated_absorpt_T_min   0.272
_shelx_estimated_absorpt_T_max   0.561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2723
_exptl_absorpt_correction_T_max  0.5591
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26378
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.892
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5151
_reflns_number_gt                4347
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0305P)²+6.8152P] 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         5151
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.32822(2) 0.04256(2) 0.90966(2) 0.01515(8) Uani 1 1 d . . . . .
Eu2 Eu -0.15700(2) 0.25812(2) 0.90651(2) 0.01399(8) Uani 1 1 d . . . . .
O13 O 0.3327(3) -0.10330(18) 0.8915(2) 0.0194(7) Uani 1 1 d G . . . .
H13A H 0.3967 -0.1280 0.9412 0.023 Uiso 1 1 d G U . . .
H13B H 0.2582 -0.1343 0.8841 0.023 Uiso 1 1 d G U . . .
O1 O 0.1763(3) 0.14859(18) 0.8785(3) 0.0212(8) Uani 1 1 d . . . . .
O7 O 0.4847(3) 0.15008(18) 0.9455(2) 0.0174(7) Uani 1 1 d . . . . .
O14 O -0.0423(3) 0.38509(18) 0.9275(3) 0.0216(8) Uani 1 1 d G . . . .
H14A H -0.0822 0.4348 0.9179 0.026 Uiso 1 1 d G U . . .
H14B H 0.0371 0.3927 0.9730 0.026 Uiso 1 1 d G U . . .
N2 N 0.3744(3) 0.1205(2) 0.7572(3) 0.0148(8) Uani 1 1 d . . . . .
O3 O 0.4537(3) 0.00970(17) 1.0857(2) 0.0157(7) Uani 1 1 d . . . . .
O11 O 0.1541(3) -0.01271(18) 0.9740(2) 0.0164(7) Uani 1 1 d . . . . .
O5 O 0.2067(3) 0.01191(19) 0.7414(3) 0.0218(8) Uani 1 1 d . . . . .
O2 O 0.0581(3) 0.23951(19) 0.9264(3) 0.0247(8) Uani 1 1 d . . . . .
N1 N 0.2885(3) 0.1207(2) 1.0668(3) 0.0132(8) Uani 1 1 d . . . . .
O12 O -0.1282(3) 0.13898(18) 1.0141(2) 0.0214(8) Uani 1 1 d . . . . .
O8 O -0.3643(3) 0.2142(2) 0.8943(3) 0.0326(9) Uani 1 1 d . . . . .
O9 O -0.1732(4) 0.2943(2) 1.0712(3) 0.0338(10) Uani 1 1 d . . . . .
O15 O -0.2968(4) 0.3645(2) 0.8373(3) 0.0390(10) Uani 1 1 d G . . . .
H15A H -0.2801 0.3996 0.7855 0.047 Uiso 1 1 d G U . . .
H15B H -0.3574 0.3884 0.8713 0.047 Uiso 1 1 d G U . . .
C1 C 0.1401(4) 0.1867(3) 0.9444(4) 0.0180(11) Uani 1 1 d . . . . .
C13 C 0.4694(4) 0.1689(3) 0.7688(4) 0.0186(10) Uani 1 1 d . . . . .
C6 C 0.3472(4) 0.1044(3) 1.1616(3) 0.0154(10) Uani 1 1 d . . . . .
C9 C 0.3103(4) 0.1061(3) 0.6635(4) 0.0168(10) Uani 1 1 d . . . . .
C8 C 0.2103(4) 0.0458(3) 0.6591(4) 0.0181(11) Uani 1 1 d . . . . .
C4 C 0.2266(5) 0.1953(3) 1.2326(4) 0.0313(13) Uani 1 1 d . . . . .
H4 H 0.2058 0.2205 1.2881 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1652(5) 0.2116(3) 1.1352(4) 0.0265(12) Uani 1 1 d . . . . .
H3 H 0.1016 0.2476 1.1239 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5354(4) 0.1784(2) 0.8781(4) 0.0170(10) Uani 1 1 d . . . . .
C5 C 0.3198(5) 0.1409(3) 1.2464(4) 0.0245(12) Uani 1 1 d . . . . .
H5 H 0.3632 0.1291 1.3113 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3399(5) 0.1405(3) 0.5787(4) 0.0288(12) Uani 1 1 d . . . . .
H10 H 0.2941 0.1300 0.5142 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5055(5) 0.2050(3) 0.6877(4) 0.0274(12) Uani 1 1 d . . . . .
H12 H 0.5732 0.2381 0.6977 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4383(5) 0.1904(3) 0.5911(4) 0.0364(14) Uani 1 1 d . . . . .
H11 H 0.4595 0.2144 0.5349 0.044 Uiso 1 1 calc R U . . .
C16 C -0.1425(4) 0.3719(3) 1.2168(4) 0.0168(10) Uani 1 1 d . . . . .
C15 C -0.1650(4) 0.2954(3) 1.1663(4) 0.0197(11) Uani 1 1 d . . . . .
C17 C -0.1208(5) 0.4381(3) 1.1670(4) 0.0271(12) Uani 1 1 d . . . . .
H17 H -0.1213 0.4379 1.0975 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1992(4) 0.1736(2) 1.0544(4) 0.0154(10) Uani 1 1 d . . . . .
O10 O -0.1729(3) 0.23853(18) 1.2209(2) 0.0230(8) Uani 1 1 d . . . . .
O4 O 0.5065(4) 0.0266(2) 1.2530(3) 0.0384(10) Uani 1 1 d . . . . .
C7 C 0.4429(4) 0.0418(3) 1.1700(4) 0.0181(11) Uani 1 1 d . . . . .
O6 O 0.1429(3) 0.0316(2) 0.5754(3) 0.0312(9) Uani 1 1 d . . . . .
N3 N -0.1436(3) 0.3702(2) 1.3163(3) 0.0139(8) Uani 1 1 d . . . . .
C20 C -0.1257(4) 0.4359(3) 1.3685(3) 0.0139(10) Uani 1 1 d . . . . .
C19 C -0.1011(4) 0.5040(3) 1.3248(4) 0.0190(11) Uani 1 1 d . . . . .
H19 H -0.0867 0.5485 1.3634 0.023 Uiso 1 1 calc R U . . .
C18 C -0.0985(5) 0.5045(3) 1.2228(4) 0.0285(13) Uani 1 1 d . . . . .
H18 H -0.0816 0.5497 1.1914 0.034 Uiso 1 1 calc R U . . .
C21 C -0.1352(4) 0.4279(3) 1.4786(3) 0.0141(10) Uani 1 1 d . . . . .
O16 O 0.5643(17) 0.4429(8) 0.9646(13) 0.136(7) Uani 0.5 1 d . . P . .


_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 O11 2.443(3) . ?
Eu1 O5 2.444(3) . ?
Eu1 O1 2.473(3) . ?
Eu1 O7 2.528(3) . ?
Eu1 O3 2.551(3) 3_657 ?
Eu1 O3 2.554(3) . ?
Eu1 O13 2.561(3) . ?
Eu1 N2 2.585(4) . ?
Eu1 N1 2.615(4) . ?
Eu1 C7 3.266(5) 3_657 ?
Eu1 Eu1 4.3278(5) 3_657 ?
Eu2 O9 2.334(3) . ?
Eu2 O2 2.347(3) . ?
Eu2 O8 2.377(3) . ?
Eu2 O10 2.458(3) 4_565 ?
Eu2 O15 2.473(4) . ?
Eu2 O12 2.516(3) . ?
Eu2 O14 2.539(3) . ?
Eu2 N3 2.564(4) 4_565 ?
O13 H13A 0.9700 . ?
O13 H13B 0.9700 . ?
O1 C1 1.232(6) . ?
O7 C14 1.251(5) . ?
O14 H14A 0.9700 . ?
O14 H14B 0.9700 . ?
N2 C13 1.329(6) . ?
N2 C9 1.337(6) . ?
O3 C7 1.286(6) . ?
O3 Eu1 2.551(3) 3_657 ?
O11 C21 1.254(5) 2_547 ?
O5 C8 1.258(6) . ?
O2 C1 1.278(5) . ?
N1 C2 1.334(5) . ?
N1 C6 1.338(6) . ?
O12 C21 1.259(5) 4_565 ?
O8 C14 1.247(5) 1_455 ?
O9 C15 1.260(6) . ?
O15 H15A 0.9700 . ?
O15 H15B 0.9700 . ?
C1 C2 1.507(7) . ?
C13 C12 1.378(7) . ?
C13 C14 1.511(7) . ?
C6 C5 1.385(6) . ?
C6 C7 1.506(6) . ?
C9 C10 1.377(7) . ?
C9 C8 1.515(6) . ?
C8 O6 1.242(6) . ?
C4 C3 1.376(8) . ?
C4 C5 1.382(7) . ?
C4 H4 0.9300 . ?
C3 C2 1.381(7) . ?
C3 H3 0.9300 . ?
C14 O8 1.247(5) 1_655 ?
C5 H5 0.9300 . ?
C10 C11 1.373(8) . ?
C10 H10 0.9300 . ?
C12 C11 1.382(8) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C16 N3 1.336(6) . ?
C16 C17 1.379(7) . ?
C16 C15 1.496(7) . ?
C15 O10 1.247(6) . ?
C17 C18 1.375(7) . ?
C17 H17 0.9300 . ?
O10 Eu2 2.458(3) 4_566 ?
O4 C7 1.222(6) . ?
C7 Eu1 3.266(5) 3_657 ?
N3 C20 1.338(6) . ?
N3 Eu2 2.564(4) 4_566 ?
C20 C19 1.375(6) . ?
C20 C21 1.505(6) . ?
C19 C18 1.372(7) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C21 O11 1.254(5) 2_557 ?
C21 O12 1.259(5) 4_566 ?

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
O11 Eu1 O5 85.10(11) . . ?
O11 Eu1 O1 78.90(10) . . ?
O5 Eu1 O1 77.28(11) . . ?
O11 Eu1 O7 140.92(10) . . ?
O5 Eu1 O7 124.51(10) . . ?
O1 Eu1 O7 83.46(11) . . ?
O11 Eu1 O3 130.15(10) . 3_657 ?
O5 Eu1 O3 106.54(10) . 3_657 ?
O1 Eu1 O3 150.54(10) . 3_657 ?
O7 Eu1 O3 70.22(10) . 3_657 ?
O11 Eu1 O3 84.50(10) . . ?
O5 Eu1 O3 154.35(11) . . ?
O1 Eu1 O3 123.29(10) . . ?
O7 Eu1 O3 76.54(10) . . ?
O3 Eu1 O3 64.04(11) 3_657 . ?
O11 Eu1 O13 70.82(10) . . ?
O5 Eu1 O13 73.23(11) . . ?
O1 Eu1 O13 138.96(11) . . ?
O7 Eu1 O13 137.09(10) . . ?
O3 Eu1 O13 67.09(10) 3_657 . ?
O3 Eu1 O13 81.21(10) . . ?
O11 Eu1 N2 140.70(11) . . ?
O5 Eu1 N2 62.79(11) . . ?
O1 Eu1 N2 72.65(11) . . ?
O7 Eu1 N2 61.84(11) . . ?
O3 Eu1 N2 83.11(10) 3_657 . ?
O3 Eu1 N2 133.96(11) . . ?
O13 Eu1 N2 115.99(11) . . ?
O11 Eu1 N1 70.01(11) . . ?
O5 Eu1 N1 135.21(11) . . ?
O1 Eu1 N1 62.09(11) . . ?
O7 Eu1 N1 70.92(10) . . ?
O3 Eu1 N1 118.04(10) 3_657 . ?
O3 Eu1 N1 61.25(10) . . ?
O13 Eu1 N1 127.25(11) . . ?
N2 Eu1 N1 116.73(12) . . ?
O11 Eu1 C7 129.89(11) . 3_657 ?
O5 Eu1 C7 85.19(12) . 3_657 ?
O1 Eu1 C7 145.01(11) . 3_657 ?
O7 Eu1 C7 81.94(11) . 3_657 ?
O3 Eu1 C7 21.35(11) 3_657 3_657 ?
O3 Eu1 C7 83.64(11) . 3_657 ?
O13 Eu1 C7 59.30(11) . 3_657 ?
N2 Eu1 C7 72.41(11) . 3_657 ?
N1 Eu1 C7 139.28(12) . 3_657 ?
O11 Eu1 Eu1 108.87(7) . 3_657 ?
O5 Eu1 Eu1 134.40(8) . 3_657 ?
O1 Eu1 Eu1 146.84(8) . 3_657 ?
O7 Eu1 Eu1 70.32(7) . 3_657 ?
O3 Eu1 Eu1 32.04(7) 3_657 3_657 ?
O3 Eu1 Eu1 32.00(6) . 3_657 ?
O13 Eu1 Eu1 71.36(7) . 3_657 ?
N2 Eu1 Eu1 109.81(8) . 3_657 ?
N1 Eu1 Eu1 89.62(8) . 3_657 ?
C7 Eu1 Eu1 52.09(9) 3_657 3_657 ?
O9 Eu2 O2 100.99(14) . . ?
O9 Eu2 O8 84.52(14) . . ?
O2 Eu2 O8 153.08(13) . . ?
O9 Eu2 O10 160.98(12) . 4_565 ?
O2 Eu2 O10 89.40(12) . 4_565 ?
O8 Eu2 O10 93.42(12) . 4_565 ?
O9 Eu2 O15 89.67(14) . . ?
O2 Eu2 O15 133.15(12) . . ?
O8 Eu2 O15 72.61(13) . . ?
O10 Eu2 O15 71.74(13) 4_565 . ?
O9 Eu2 O12 72.98(11) . . ?
O2 Eu2 O12 78.98(11) . . ?
O8 Eu2 O12 77.53(12) . . ?
O10 Eu2 O12 125.10(10) 4_565 . ?
O15 Eu2 O12 146.72(12) . . ?
O9 Eu2 O14 77.65(12) . . ?
O2 Eu2 O14 69.03(11) . . ?
O8 Eu2 O14 137.51(12) . . ?
O10 Eu2 O14 91.56(11) 4_565 . ?
O15 Eu2 O14 69.08(12) . . ?
O12 Eu2 O14 130.90(11) . . ?
O9 Eu2 N3 134.73(12) . 4_565 ?
O2 Eu2 N3 77.51(12) . 4_565 ?
O8 Eu2 N3 80.03(12) . 4_565 ?
O10 Eu2 N3 62.87(11) 4_565 4_565 ?
O15 Eu2 N3 124.69(13) . 4_565 ?
O12 Eu2 N3 62.23(11) . 4_565 ?
O14 Eu2 N3 138.02(11) . 4_565 ?
Eu1 O13 H13A 113.7 . . ?
Eu1 O13 H13B 122.2 . . ?
H13A O13 H13B 107.8 . . ?
C1 O1 Eu1 125.9(3) . . ?
C14 O7 Eu1 122.6(3) . . ?
Eu2 O14 H14A 124.5 . . ?
Eu2 O14 H14B 123.6 . . ?
H14A O14 H14B 106.8 . . ?
C13 N2 C9 119.0(4) . . ?
C13 N2 Eu1 120.9(3) . . ?
C9 N2 Eu1 119.7(3) . . ?
C7 O3 Eu1 112.4(3) . 3_657 ?
C7 O3 Eu1 125.9(3) . . ?
Eu1 O3 Eu1 115.95(11) 3_657 . ?
C21 O11 Eu1 136.3(3) 2_547 . ?
C8 O5 Eu1 126.8(3) . . ?
C1 O2 Eu2 141.0(3) . . ?
C2 N1 C6 118.2(4) . . ?
C2 N1 Eu1 119.7(3) . . ?
C6 N1 Eu1 121.8(3) . . ?
C21 O12 Eu2 124.1(3) 4_565 . ?
C14 O8 Eu2 167.0(3) 1_455 . ?
C15 O9 Eu2 162.9(3) . . ?
Eu2 O15 H15A 123.5 . . ?
Eu2 O15 H15B 125.4 . . ?
H15A O15 H15B 107.9 . . ?
O1 C1 O2 124.7(5) . . ?
O1 C1 C2 118.7(4) . . ?
O2 C1 C2 116.6(4) . . ?
N2 C13 C12 122.6(5) . . ?
N2 C13 C14 113.6(4) . . ?
C12 C13 C14 123.8(4) . . ?
N1 C6 C5 122.5(4) . . ?
N1 C6 C7 115.2(4) . . ?
C5 C6 C7 122.3(4) . . ?
N2 C9 C10 121.8(4) . . ?
N2 C9 C8 114.3(4) . . ?
C10 C9 C8 123.8(4) . . ?
O6 C8 O5 125.5(4) . . ?
O6 C8 C9 118.3(4) . . ?
O5 C8 C9 116.1(4) . . ?
C3 C4 C5 118.8(5) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C3 C2 119.1(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
O8 C14 O7 125.1(5) 1_655 . ?
O8 C14 C13 117.6(4) 1_655 . ?
O7 C14 C13 117.3(4) . . ?
C4 C5 C6 118.7(5) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C13 C12 C11 118.1(5) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C10 C11 C12 119.6(5) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N3 C16 C17 122.4(4) . . ?
N3 C16 C15 113.5(4) . . ?
C17 C16 C15 124.1(4) . . ?
O10 C15 O9 125.6(4) . . ?
O10 C15 C16 118.1(4) . . ?
O9 C15 C16 116.3(4) . . ?
C18 C17 C16 118.3(5) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
N1 C2 C3 122.7(5) . . ?
N1 C2 C1 113.2(4) . . ?
C3 C2 C1 124.2(4) . . ?
C15 O10 Eu2 125.1(3) . 4_566 ?
O4 C7 O3 124.7(4) . . ?
O4 C7 C6 119.5(4) . . ?
O3 C7 C6 115.7(4) . . ?
O4 C7 Eu1 81.9(3) . 3_657 ?
O3 C7 Eu1 46.2(2) . 3_657 ?
C6 C7 Eu1 150.9(3) . 3_657 ?
C16 N3 C20 118.2(4) . . ?
C16 N3 Eu2 120.1(3) . 4_566 ?
C20 N3 Eu2 121.4(3) . 4_566 ?
N3 C20 C19 122.8(4) . . ?
N3 C20 C21 113.6(4) . . ?
C19 C20 C21 123.6(4) . . ?
C18 C19 C20 118.2(4) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C19 C18 C17 120.0(5) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
O11 C21 O12 125.5(4) 2_557 4_566 ?
O11 C21 C20 118.0(4) 2_557 . ?
O12 C21 C20 116.4(4) 4_566 . ?

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
Eu1 O1 C1 O2 -177.4(3) . . . . ?
Eu1 O1 C1 C2 5.5(6) . . . . ?
Eu2 O2 C1 O1 91.1(6) . . . . ?
Eu2 O2 C1 C2 -91.7(6) . . . . ?
C9 N2 C13 C12 -0.4(7) . . . . ?
Eu1 N2 C13 C12 172.5(4) . . . . ?
C9 N2 C13 C14 -178.6(4) . . . . ?
Eu1 N2 C13 C14 -5.7(5) . . . . ?
C2 N1 C6 C5 -0.9(7) . . . . ?
Eu1 N1 C6 C5 -174.5(3) . . . . ?
C2 N1 C6 C7 177.5(4) . . . . ?
Eu1 N1 C6 C7 3.9(5) . . . . ?
C13 N2 C9 C10 -0.2(7) . . . . ?
Eu1 N2 C9 C10 -173.3(4) . . . . ?
C13 N2 C9 C8 175.8(4) . . . . ?
Eu1 N2 C9 C8 2.7(5) . . . . ?
Eu1 O5 C8 O6 -176.0(4) . . . . ?
Eu1 O5 C8 C9 7.1(6) . . . . ?
N2 C9 C8 O6 176.8(4) . . . . ?
C10 C9 C8 O6 -7.3(7) . . . . ?
N2 C9 C8 O5 -6.1(6) . . . . ?
C10 C9 C8 O5 169.9(5) . . . . ?
C5 C4 C3 C2 -0.6(8) . . . . ?
Eu1 O7 C14 O8 -158.1(4) . . . 1_655 ?
Eu1 O7 C14 C13 22.3(5) . . . . ?
N2 C13 C14 O8 170.1(4) . . . 1_655 ?
C12 C13 C14 O8 -8.1(7) . . . 1_655 ?
N2 C13 C14 O7 -10.3(6) . . . . ?
C12 C13 C14 O7 171.5(4) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
N1 C6 C5 C4 1.2(7) . . . . ?
C7 C6 C5 C4 -177.0(5) . . . . ?
N2 C9 C10 C11 0.3(8) . . . . ?
C8 C9 C10 C11 -175.3(5) . . . . ?
N2 C13 C12 C11 1.0(8) . . . . ?
C14 C13 C12 C11 179.0(5) . . . . ?
C9 C10 C11 C12 0.3(8) . . . . ?
C13 C12 C11 C10 -0.9(8) . . . . ?
Eu2 O9 C15 O10 -36.7(15) . . . . ?
Eu2 O9 C15 C16 142.6(10) . . . . ?
N3 C16 C15 O10 -5.2(6) . . . . ?
C17 C16 C15 O10 174.0(5) . . . . ?
N3 C16 C15 O9 175.4(4) . . . . ?
C17 C16 C15 O9 -5.4(7) . . . . ?
N3 C16 C17 C18 0.6(8) . . . . ?
C15 C16 C17 C18 -178.5(5) . . . . ?
C6 N1 C2 C3 -0.2(6) . . . . ?
Eu1 N1 C2 C3 173.5(4) . . . . ?
C6 N1 C2 C1 -179.9(4) . . . . ?
Eu1 N1 C2 C1 -6.1(5) . . . . ?
C4 C3 C2 N1 1.0(7) . . . . ?
C4 C3 C2 C1 -179.4(5) . . . . ?
O1 C1 C2 N1 0.9(6) . . . . ?
O2 C1 C2 N1 -176.5(4) . . . . ?
O1 C1 C2 C3 -178.8(4) . . . . ?
O2 C1 C2 C3 3.9(7) . . . . ?
O9 C15 O10 Eu2 -179.9(4) . . . 4_566 ?
C16 C15 O10 Eu2 0.8(6) . . . 4_566 ?
Eu1 O3 C7 O4 -25.7(6) 3_657 . . . ?
Eu1 O3 C7 O4 -177.8(4) . . . . ?
Eu1 O3 C7 C6 151.8(3) 3_657 . . . ?
Eu1 O3 C7 C6 -0.2(5) . . . . ?
Eu1 O3 C7 Eu1 -152.1(4) . . . 3_657 ?
N1 C6 C7 O4 175.3(4) . . . . ?
C5 C6 C7 O4 -6.3(7) . . . . ?
N1 C6 C7 O3 -2.4(6) . . . . ?
C5 C6 C7 O3 176.0(4) . . . . ?
N1 C6 C7 Eu1 42.1(8) . . . 3_657 ?
C5 C6 C7 Eu1 -139.5(5) . . . 3_657 ?
C17 C16 N3 C20 1.5(7) . . . . ?
C15 C16 N3 C20 -179.3(4) . . . . ?
C17 C16 N3 Eu2 -172.2(4) . . . 4_566 ?
C15 C16 N3 Eu2 7.0(5) . . . 4_566 ?
C16 N3 C20 C19 -2.7(7) . . . . ?
Eu2 N3 C20 C19 170.8(3) 4_566 . . . ?
C16 N3 C20 C21 177.1(4) . . . . ?
Eu2 N3 C20 C21 -9.3(5) 4_566 . . . ?
N3 C20 C19 C18 1.8(7) . . . . ?
C21 C20 C19 C18 -178.0(4) . . . . ?
C20 C19 C18 C17 0.4(8) . . . . ?
C16 C17 C18 C19 -1.6(8) . . . . ?
N3 C20 C21 O11 -160.7(4) . . . 2_557 ?
C19 C20 C21 O11 19.2(6) . . . 2_557 ?
N3 C20 C21 O12 16.7(6) . . . 4_566 ?
C19 C20 C21 O12 -163.5(4) . . . 4_566 ?

_refine_diff_density_max         0.698
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.149

