# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_d14176_a
_database_code_depnum_ccdc_archive 'CCDC 1436006'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H13 Eu2 N3 O20, 2(H2 O)'
_chemical_formula_sum            'C24 H17 Eu2 N3 O22'
_chemical_formula_weight         1003.32

# start Validation Reply Form
_vrf_PLAT220_d14176_a            
;
PROBLEM: Large Non-Solvent  O     Ueq(max)/Ueq(min) Range        6.2 Ratio 
RESPONSE: One of the nitro group O atoms has a larger the normal
anisotropic displacement parameter. Neither the boned N atom nor 
the other O atom of the same group have large or elongated ellipsoids
(which may have indicated rotational disorder about the C6---N1 bond) 
therefore it is difficult to create a disorder model.  
;
_vrf_PLAT430_d14176_a            
;
PROBLEM: Short Inter D...A Contact  O3     ..  O8      ..       2.84 Ang.  
RESPONSE: None of the carbonyl groups are protontated as required
by the stoiciometry. 
;
# end Validation Reply Form

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   16.7909(8)
_cell_length_b                   11.3883(6)
_cell_length_c                   15.3276(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.119(1)
_cell_angle_gamma                90
_cell_volume                     2930.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.49

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.274
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    4.348
_shelx_estimated_absorpt_T_min   0.275
_shelx_estimated_absorpt_T_max   0.462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5374
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20642
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.161
_diffrn_reflns_theta_max         27.507
_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             3362
_reflns_number_gt                3163
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0142P)²+8.0268P] 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         3362
_refine_ls_number_parameters     246
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0167
_refine_ls_R_factor_gt           0.0147
_refine_ls_wR_factor_ref         0.0364
_refine_ls_wR_factor_gt          0.0354
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.154
_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 0.53512(2) 0.35312(2) 0.37480(2) 0.00593(4) Uani 1 1 d . . . . .
O1 O 0.43403(9) 0.35056(13) 0.47698(10) 0.0137(3) Uani 1 1 d . . . . .
O2 O 0.39424(9) 0.52365(13) 0.52957(9) 0.0108(3) Uani 1 1 d . . . . .
O3 O 0.08139(9) 0.15509(13) 0.71294(10) 0.0118(3) Uani 1 1 d . . . . .
O4 O 0.17204(9) 0.17181(14) 0.81522(10) 0.0135(3) Uani 1 1 d . . . . .
O5 O 0.21426(11) -0.00284(15) 0.67146(12) 0.0245(4) Uani 1 1 d . U . . .
O6 O 0.31448(16) -0.00685(19) 0.5859(2) 0.0670(9) Uani 1 1 d . U . . .
O7 O 0.51882(9) 0.54497(13) 0.32027(10) 0.0137(3) Uani 1 1 d . . . . .
O8 O 0.52610(10) 1.15649(13) 0.31769(10) 0.0156(3) Uani 1 1 d . . . . .
O11 O 0.59855(10) 0.21972(14) 0.47404(10) 0.0199(4) Uani 1 1 d . . . . .
H1O H 0.6112 0.1553 0.4540 0.030 Uiso 1 1 d R U . . .
H2O H 0.6279 0.2283 0.5134 0.030 Uiso 1 1 d R U . . .
N1 N 0.26549(11) 0.04569(17) 0.62836(14) 0.0184(4) Uani 1 1 d . U . . .
C1 C 0.38909(12) 0.41389(18) 0.52295(13) 0.0093(4) Uani 1 1 d . . . . .
C2 C 0.32467(12) 0.35140(18) 0.57354(13) 0.0097(4) Uani 1 1 d . . . . .
C3 C 0.26727(13) 0.41484(19) 0.61877(15) 0.0146(4) Uani 1 1 d . . . . .
H3A H 0.2670 0.4981 0.6156 0.018 Uiso 1 1 calc R U . . .
C4 C 0.21025(14) 0.3571(2) 0.66857(16) 0.0168(5) Uani 1 1 d . . . . .
H4A H 0.1713 0.4015 0.6991 0.020 Uiso 1 1 calc R U . . .
C5 C 0.20949(12) 0.23553(19) 0.67425(13) 0.0103(4) Uani 1 1 d . . . . .
C6 C 0.26632(12) 0.17444(19) 0.62620(14) 0.0111(4) Uani 1 1 d . . . . .
C7 C 0.32344(12) 0.22958(19) 0.57614(13) 0.0114(4) Uani 1 1 d . . . . .
H7A H 0.3612 0.1850 0.5441 0.014 Uiso 1 1 calc R U . . .
C8 C 0.15131(12) 0.18051(19) 0.73683(14) 0.0106(4) Uani 1 1 d . . . . .
C9 C 0.5000 0.5957(3) 0.2500 0.0106(6) Uani 1 2 d S T P . .
C10 C 0.5000 0.7280(3) 0.2500 0.0121(6) Uani 1 2 d S T P . .
C11 C 0.49769(13) 0.78901(19) 0.32828(14) 0.0142(4) Uani 1 1 d . . . . .
H11A H 0.4971 0.7476 0.3821 0.017 Uiso 1 1 calc R U . A 1
O9 O 0.5302(2) 0.9525(3) 0.4709(2) 0.0253(8) Uani 0.5 1 d . . P B 1
O10 O 0.4182(2) 1.0235(3) 0.4246(2) 0.0262(8) Uani 0.5 1 d . . P B 1
N2 N 0.4796(2) 0.9668(3) 0.4144(2) 0.0151(8) Uani 0.5 1 d . . P B 1
C12 C 0.49633(15) 0.91068(19) 0.32756(14) 0.0162(5) Uani 0.5 1 d . . P B 1
C13 C 0.5000 0.9745(3) 0.2500 0.0165(6) Uani 0.5 2 d S T P B 1
C14 C 0.5000 1.1069(3) 0.2500 0.0136(6) Uani 0.5 2 d S T P B 1
C12A C 0.49633(15) 0.91068(19) 0.32756(14) 0.0162(5) Uani 0.5 1 d . . P B 2
H12A H 0.4928 0.9517 0.3814 0.019 Uiso 0.5 1 calc R U P B 2
C13A C 0.5000 0.9745(3) 0.2500 0.0165(6) Uani 0.5 2 d S T P B 2
C14A C 0.5000 1.1069(3) 0.2500 0.0136(6) Uani 0.5 2 d S T P B 2
O1W O 0.68432(12) 0.25738(18) 0.61584(14) 0.0367(5) Uani 1 1 d . . . . .
H1WA H 0.6832 0.3337 0.6326 0.055 Uiso 1 1 d R U . . .
H1WB H 0.7332 0.2191 0.6381 0.055 Uiso 1 1 d R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O1 2.3122(15) . ?
Eu1 O2 2.3490(14) 5_666 ?
Eu1 O7 2.3550(15) . ?
Eu1 O3 2.3735(15) 7_556 ?
Eu1 O11 2.3978(16) . ?
Eu1 O8 2.4089(15) 1_545 ?
Eu1 O4 2.4918(15) 8 ?
Eu1 O3 2.6028(15) 8 ?
Eu1 C8 2.905(2) 8 ?
Eu1 Eu1 4.0009(3) 2_655 ?
O1 C1 1.260(3) . ?
O2 C1 1.257(3) . ?
O2 Eu1 2.3490(14) 5_666 ?
O3 C8 1.263(3) . ?
O3 Eu1 2.3734(15) 7_556 ?
O3 Eu1 2.6028(15) 8_456 ?
O4 C8 1.254(3) . ?
O4 Eu1 2.4918(15) 8_456 ?
O5 N1 1.218(3) . ?
O6 N1 1.208(3) . ?
O7 C9 1.262(2) . ?
O8 C14A 1.259(2) . ?
O8 C14 1.259(2) . ?
O8 Eu1 2.4089(15) 1_565 ?
O11 H1O 0.8238 . ?
O11 H2O 0.7844 . ?
N1 C6 1.467(3) . ?
C1 C2 1.510(3) . ?
C2 C7 1.388(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.391(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(3) . ?
C5 C8 1.507(3) . ?
C6 C7 1.381(3) . ?
C7 H7A 0.9500 . ?
C8 Eu1 2.905(2) 8_456 ?
C9 O7 1.262(2) 2_655 ?
C9 C10 1.506(4) . ?
C10 C11 1.387(3) . ?
C10 C11 1.387(3) 2_655 ?
C11 C12A 1.386(3) . ?
C11 C12 1.386(3) . ?
C11 H11A 0.9500 . ?
O9 N2 1.222(5) . ?
O9 O9 1.730(7) 5_676 ?
O10 N2 1.227(5) . ?
N2 C12 1.503(4) . ?
C12 C13 1.395(3) . ?
C13 C12 1.395(3) 2_655 ?
C13 C14 1.508(4) . ?
C14 O8 1.259(2) 2_655 ?
C12A C13A 1.395(3) . ?
C12A H12A 0.9500 . ?
C13A C12A 1.395(3) 2_655 ?
C13A C14A 1.508(4) . ?
C14A O8 1.259(2) 2_655 ?
O1W H1WA 0.9066 . ?
O1W H1WB 0.9893 . ?

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
O1 Eu1 O2 87.44(5) . 5_666 ?
O1 Eu1 O7 99.63(5) . . ?
O2 Eu1 O7 74.06(5) 5_666 . ?
O1 Eu1 O3 77.17(5) . 7_556 ?
O2 Eu1 O3 142.34(5) 5_666 7_556 ?
O7 Eu1 O3 74.96(5) . 7_556 ?
O1 Eu1 O11 83.57(6) . . ?
O2 Eu1 O11 76.09(5) 5_666 . ?
O7 Eu1 O11 149.77(5) . . ?
O3 Eu1 O11 134.35(5) 7_556 . ?
O1 Eu1 O8 100.88(5) . 1_545 ?
O2 Eu1 O8 144.43(5) 5_666 1_545 ?
O7 Eu1 O8 136.58(5) . 1_545 ?
O3 Eu1 O8 72.93(5) 7_556 1_545 ?
O11 Eu1 O8 70.68(5) . 1_545 ?
O1 Eu1 O4 157.82(5) . 8 ?
O2 Eu1 O4 80.31(5) 5_666 8 ?
O7 Eu1 O4 94.72(5) . 8 ?
O3 Eu1 O4 123.22(5) 7_556 8 ?
O11 Eu1 O4 75.60(5) . 8 ?
O8 Eu1 O4 79.53(5) 1_545 8 ?
O1 Eu1 O3 150.02(5) . 8 ?
O2 Eu1 O3 117.70(5) 5_666 8 ?
O7 Eu1 O3 74.32(5) . 8 ?
O3 Eu1 O3 72.89(5) 7_556 8 ?
O11 Eu1 O3 116.67(5) . 8 ?
O8 Eu1 O3 68.83(5) 1_545 8 ?
O4 Eu1 O3 50.89(5) 8 8 ?
O1 Eu1 C8 170.52(6) . 8 ?
O2 Eu1 C8 101.18(6) 5_666 8 ?
O7 Eu1 C8 86.66(6) . 8 ?
O3 Eu1 C8 97.83(6) 7_556 8 ?
O11 Eu1 C8 94.60(6) . 8 ?
O8 Eu1 C8 69.80(6) 1_545 8 ?
O4 Eu1 C8 25.42(5) 8 8 ?
O3 Eu1 C8 25.76(5) 8 8 ?
O1 Eu1 Eu1 115.62(4) . 2_655 ?
O2 Eu1 Eu1 138.08(4) 5_666 2_655 ?
O7 Eu1 Eu1 68.09(4) . 2_655 ?
O3 Eu1 Eu1 38.49(4) 7_556 2_655 ?
O11 Eu1 Eu1 137.41(4) . 2_655 ?
O8 Eu1 Eu1 68.55(4) 1_545 2_655 ?
O4 Eu1 Eu1 85.41(3) 8 2_655 ?
O3 Eu1 Eu1 34.58(3) 8 2_655 ?
C8 Eu1 Eu1 60.07(4) 8 2_655 ?
C1 O1 Eu1 144.36(14) . . ?
C1 O2 Eu1 132.77(13) . 5_666 ?
C8 O3 Eu1 159.73(14) . 7_556 ?
C8 O3 Eu1 90.63(12) . 8_456 ?
Eu1 O3 Eu1 106.94(5) 7_556 8_456 ?
C8 O4 Eu1 96.06(12) . 8_456 ?
C9 O7 Eu1 139.15(15) . . ?
C14A O8 Eu1 137.54(16) . 1_565 ?
C14 O8 Eu1 137.54(16) . 1_565 ?
Eu1 O11 H1O 116.3 . . ?
Eu1 O11 H2O 133.4 . . ?
H1O O11 H2O 103.6 . . ?
O6 N1 O5 123.3(2) . . ?
O6 N1 C6 118.5(2) . . ?
O5 N1 C6 118.19(19) . . ?
O2 C1 O1 124.97(19) . . ?
O2 C1 C2 118.44(18) . . ?
O1 C1 C2 116.59(18) . . ?
C7 C2 C3 119.64(19) . . ?
C7 C2 C1 119.76(19) . . ?
C3 C2 C1 120.59(19) . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 117.31(19) . . ?
C4 C5 C8 117.45(19) . . ?
C6 C5 C8 125.08(19) . . ?
C7 C6 C5 123.0(2) . . ?
C7 C6 N1 118.29(19) . . ?
C5 C6 N1 118.74(19) . . ?
C6 C7 C2 118.7(2) . . ?
C6 C7 H7A 120.6 . . ?
C2 C7 H7A 120.6 . . ?
O4 C8 O3 121.05(19) . . ?
O4 C8 C5 117.62(18) . . ?
O3 C8 C5 120.95(19) . . ?
O4 C8 Eu1 58.52(11) . 8_456 ?
O3 C8 Eu1 63.61(11) . 8_456 ?
C5 C8 Eu1 162.79(14) . 8_456 ?
O7 C9 O7 125.5(3) . 2_655 ?
O7 C9 C10 117.25(13) . . ?
O7 C9 C10 117.26(13) 2_655 . ?
C11 C10 C11 119.9(3) . 2_655 ?
C11 C10 C9 120.07(14) . . ?
C11 C10 C9 120.07(14) 2_655 . ?
C12A C11 C10 119.6(2) . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
N2 O9 O9 82.9(3) . 5_676 ?
O9 N2 O10 124.2(4) . . ?
O9 N2 C12 116.1(3) . . ?
O10 N2 C12 119.7(3) . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 N2 114.9(2) . . ?
C13 C12 N2 122.8(2) . . ?
C12 C13 C12 117.2(3) 2_655 . ?
C12 C13 C14 121.41(14) 2_655 . ?
C12 C13 C14 121.41(14) . . ?
O8 C14 O8 126.7(3) 2_655 . ?
O8 C14 C13 116.64(14) 2_655 . ?
O8 C14 C13 116.64(14) . . ?
C11 C12A C13A 121.8(2) . . ?
C11 C12A H12A 119.1 . . ?
C13A C12A H12A 119.1 . . ?
C12A C13A C12A 117.2(3) 2_655 . ?
C12A C13A C14A 121.41(14) 2_655 . ?
C12A C13A C14A 121.41(14) . . ?
O8 C14A O8 126.7(3) 2_655 . ?
O8 C14A C13A 116.64(14) 2_655 . ?
O8 C14A C13A 116.64(14) . . ?
H1WA O1W H1WB 110.0 . . ?

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 O2 C1 O1 -90.0(2) 5_666 . . . ?
Eu1 O2 C1 C2 89.9(2) 5_666 . . . ?
Eu1 O1 C1 O2 -6.8(4) . . . . ?
Eu1 O1 C1 C2 173.29(16) . . . . ?
O2 C1 C2 C7 -172.14(19) . . . . ?
O1 C1 C2 C7 7.7(3) . . . . ?
O2 C1 C2 C3 6.8(3) . . . . ?
O1 C1 C2 C3 -173.32(19) . . . . ?
C7 C2 C3 C4 1.9(3) . . . . ?
C1 C2 C3 C4 -177.0(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -1.9(3) . . . . ?
C3 C4 C5 C8 173.8(2) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
C8 C5 C6 C7 -173.5(2) . . . . ?
C4 C5 C6 N1 -177.9(2) . . . . ?
C8 C5 C6 N1 6.8(3) . . . . ?
O6 N1 C6 C7 -0.4(4) . . . . ?
O5 N1 C6 C7 -178.9(2) . . . . ?
O6 N1 C6 C5 179.4(3) . . . . ?
O5 N1 C6 C5 0.9(3) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
N1 C6 C7 C2 179.90(19) . . . . ?
C3 C2 C7 C6 -2.0(3) . . . . ?
C1 C2 C7 C6 176.91(18) . . . . ?
Eu1 O4 C8 O3 -12.3(2) 8_456 . . . ?
Eu1 O4 C8 C5 160.69(16) 8_456 . . . ?
Eu1 O3 C8 O4 162.3(3) 7_556 . . . ?
Eu1 O3 C8 O4 11.7(2) 8_456 . . . ?
Eu1 O3 C8 C5 -10.5(5) 7_556 . . . ?
Eu1 O3 C8 C5 -161.06(18) 8_456 . . . ?
Eu1 O3 C8 Eu1 150.6(4) 7_556 . . 8_456 ?
C4 C5 C8 O4 -84.4(3) . . . . ?
C6 C5 C8 O4 90.9(3) . . . . ?
C4 C5 C8 O3 88.7(3) . . . . ?
C6 C5 C8 O3 -96.1(3) . . . . ?
C4 C5 C8 Eu1 -12.0(6) . . . 8_456 ?
C6 C5 C8 Eu1 163.3(4) . . . 8_456 ?
Eu1 O7 C9 O7 1.01(10) . . . 2_655 ?
Eu1 O7 C9 C10 -178.99(11) . . . . ?
O7 C9 C10 C11 -18.21(13) . . . . ?
O7 C9 C10 C11 161.79(13) 2_655 . . . ?
O7 C9 C10 C11 161.79(13) . . . 2_655 ?
O7 C9 C10 C11 -18.21(13) 2_655 . . 2_655 ?
C11 C10 C11 C12A 1.10(16) 2_655 . . . ?
C9 C10 C11 C12A -178.89(16) . . . . ?
C11 C10 C11 C12 1.10(16) 2_655 . . . ?
C9 C10 C11 C12 -178.89(16) . . . . ?
O9 O9 N2 O10 -4.8(5) 5_676 . . . ?
O9 O9 N2 C12 174.7(3) 5_676 . . . ?
C10 C11 C12 C13 -2.3(3) . . . . ?
C10 C11 C12 N2 169.9(2) . . . . ?
O9 N2 C12 C11 65.6(4) . . . . ?
O10 N2 C12 C11 -114.8(4) . . . . ?
O9 N2 C12 C13 -122.3(3) . . . . ?
O10 N2 C12 C13 57.3(5) . . . . ?
C11 C12 C13 C12 1.14(16) . . . 2_655 ?
N2 C12 C13 C12 -170.4(3) . . . 2_655 ?
C11 C12 C13 C14 -178.86(16) . . . . ?
N2 C12 C13 C14 9.6(3) . . . . ?
Eu1 O8 C14 O8 7.11(11) 1_565 . . 2_655 ?
Eu1 O8 C14 C13 -172.89(11) 1_565 . . . ?
C12 C13 C14 O8 25.88(15) 2_655 . . 2_655 ?
C12 C13 C14 O8 -154.12(15) . . . 2_655 ?
C12 C13 C14 O8 -154.11(15) 2_655 . . . ?
C12 C13 C14 O8 25.89(15) . . . . ?
C10 C11 C12A C13A -2.3(3) . . . . ?
C11 C12A C13A C12A 1.14(16) . . . 2_655 ?
C11 C12A C13A C14A -178.86(16) . . . . ?
Eu1 O8 C14A O8 7.11(11) 1_565 . . 2_655 ?
Eu1 O8 C14A C13A -172.89(11) 1_565 . . . ?
C12A C13A C14A O8 25.88(15) 2_655 . . 2_655 ?
C12A C13A C14A O8 -154.12(15) . . . 2_655 ?
C12A C13A C14A O8 -154.11(15) 2_655 . . . ?
C12A C13A C14A O8 25.89(15) . . . . ?

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
O11 H1O O6 0.82 2.19 2.977(3) 160.1 5_656
O11 H2O O1W 0.78 1.86 2.640(3) 171.3 .
O1W H1WA O5 0.91 2.02 2.904(3) 163.8 3
O1W H1WB O4 0.99 1.82 2.806(2) 170.9 2_656

_refine_diff_density_max         0.657
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_d14178_a
_database_code_depnum_ccdc_archive 'CCDC 1436007'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H13 N3 O20 Tb2, 2(H2 O)'
_chemical_formula_sum            'C24 H17 N3 O22 Tb2'
_chemical_formula_weight         1017.24

# start Validation Reply Form
_vrf_PLAT220_d14178_a            
;
PROBLEM: Large Non-Solvent  O     Ueq(max)/Ueq(min) Range        6.2 Ratio 
RESPONSE: One of the nitro group O atoms has a larger the normal
anisotropic displacement parameter. Neither the boned N atom nor 
the other O atom of the same group have large or elongated ellipsoids
(which may have indicated rotational disorder about the C6---N1 bond) 
therefore it is difficult to create a disorder model. 
This is similar to the Eu analogue.
;
_vrf_PLAT430_d14178_a            
;
PROBLEM: Short Inter D...A Contact  O3     ..  O8      ..       2.82 Ang.  
RESPONSE: None of the carbonyl groups are protontated as required
by the stoiciometry. These contacts alao appear in the Eu analogue.
;
# end Validation Reply Form

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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   16.7322(9)
_cell_length_b                   11.3501(9)
_cell_length_c                   15.2871(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.040(2)
_cell_angle_gamma                90
_cell_volume                     2903.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.55

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.327
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.941
_shelx_estimated_absorpt_T_min   0.319
_shelx_estimated_absorpt_T_max   0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5288
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38478
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         27.559
_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             3353
_reflns_number_gt                3121
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0110P)²+9.6832P] 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         3353
_refine_ls_number_parameters     246
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0162
_refine_ls_R_factor_gt           0.0136
_refine_ls_wR_factor_ref         0.0328
_refine_ls_wR_factor_gt          0.0316
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.003
_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
Tb1 Tb 0.53481(2) 0.35324(2) 0.62586(2) 0.00617(3) Uani 1 1 d . . . . .
O1 O 0.43437(9) 0.35200(13) 0.52451(10) 0.0138(3) Uani 1 1 d . . . . .
O2 O 0.39566(9) 0.52536(13) 0.46980(9) 0.0110(3) Uani 1 1 d . . . . .
O3 O 0.08059(9) 0.15490(13) 0.28707(10) 0.0121(3) Uani 1 1 d . . . . .
O4 O 0.17093(9) 0.17218(14) 0.18427(10) 0.0139(3) Uani 1 1 d . . . . .
O5 O 0.21389(11) -0.00329(15) 0.32902(12) 0.0249(4) Uani 1 1 d . U . . .
O6 O 0.31521(16) -0.00723(18) 0.4138(2) 0.0682(9) Uani 1 1 d . U . . .
O7 O 0.51858(9) 0.54368(13) 0.67935(10) 0.0135(3) Uani 1 1 d . . . . .
O8 O 0.52566(10) 1.15745(13) 0.68178(10) 0.0159(3) Uani 1 1 d . . . . .
O11 O 0.59701(10) 0.22112(14) 0.52709(10) 0.0192(3) Uani 1 1 d . . . . .
H1O H 0.6112 0.1554 0.5460 0.029 Uiso 1 1 d R U . . .
H2O H 0.6279 0.2284 0.4866 0.029 Uiso 1 1 d R U . . .
N1 N 0.26553(12) 0.04568(17) 0.37187(14) 0.0186(4) Uani 1 1 d . U . . .
C1 C 0.38999(12) 0.41522(18) 0.47728(13) 0.0089(4) Uani 1 1 d . . . . .
C2 C 0.32532(12) 0.35238(18) 0.42671(13) 0.0099(4) Uani 1 1 d . . . . .
C3 C 0.26755(13) 0.41587(19) 0.38110(15) 0.0151(4) Uani 1 1 d . . . . .
H3A H 0.2674 0.4995 0.3840 0.018 Uiso 1 1 calc R U . . .
C4 C 0.21010(14) 0.35815(19) 0.33137(15) 0.0166(4) Uani 1 1 d . . . . .
H4A H 0.1710 0.4027 0.3008 0.020 Uiso 1 1 calc R U . . .
C5 C 0.20920(12) 0.23586(19) 0.32591(13) 0.0106(4) Uani 1 1 d . . . . .
C6 C 0.26635(13) 0.17477(18) 0.37384(14) 0.0115(4) Uani 1 1 d . . . . .
C7 C 0.32394(12) 0.22993(19) 0.42423(14) 0.0116(4) Uani 1 1 d . . . . .
H7A H 0.3618 0.1851 0.4565 0.014 Uiso 1 1 calc R U . . .
C8 C 0.15055(12) 0.18089(18) 0.26304(14) 0.0105(4) Uani 1 1 d . . . . .
C9 C 0.5000 0.5949(3) 0.7500 0.0104(6) Uani 1 2 d S T P . .
C10 C 0.5000 0.7269(3) 0.7500 0.0125(6) Uani 1 2 d S T P . .
C11 C 0.49733(14) 0.78851(19) 0.67134(14) 0.0147(4) Uani 1 1 d . . . . .
H11 H 0.4964 0.7471 0.6174 0.018 Uiso 1 1 calc R U . A 1
O9 O 0.4174(2) 1.0233(3) 0.5746(2) 0.0270(8) Uani 0.5 1 d . . P B 1
O10 O 0.5302(2) 0.9533(3) 0.5287(2) 0.0256(8) Uani 0.5 1 d . . P B 1
N2 N 0.4791(2) 0.9676(3) 0.5850(2) 0.0158(8) Uani 0.5 1 d . . P B 1
C12 C 0.49605(15) 0.91057(19) 0.67207(14) 0.0162(5) Uani 0.5 1 d . . P B 1
C13 C 0.5000 0.9747(3) 0.7500 0.0167(6) Uani 0.5 2 d S T P B 1
C14 C 0.5000 1.1079(3) 0.7500 0.0132(6) Uani 0.5 2 d S T P B 1
C12A C 0.49605(15) 0.91057(19) 0.67207(14) 0.0162(5) Uani 0.5 1 d . . P B 2
H12A H 0.4924 0.9518 0.6181 0.019 Uiso 0.5 1 calc R U P B 2
C13A C 0.5000 0.9747(3) 0.7500 0.0167(6) Uani 0.5 2 d S T P B 2
C14A C 0.5000 1.1079(3) 0.7500 0.0132(6) Uani 0.5 2 d S T P B 2
O1W O 0.68507(13) 0.25712(18) 0.38627(15) 0.0403(5) Uani 1 1 d . . . . .
H1WA H 0.6833 0.3337 0.3678 0.060 Uiso 1 1 d R U . . .
H1WB H 0.7333 0.2191 0.3623 0.060 Uiso 1 1 d R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.2850(14) . ?
Tb1 O2 2.3222(14) 5_666 ?
Tb1 O7 2.3269(14) . ?
Tb1 O3 2.3479(15) 7_556 ?
Tb1 O11 2.3693(16) . ?
Tb1 O8 2.3860(15) 1_545 ?
Tb1 O4 2.4627(15) 8_556 ?
Tb1 O3 2.5819(15) 8_556 ?
Tb1 C8 2.880(2) 8_556 ?
Tb1 Tb1 3.9712(3) 2_656 ?
O1 C1 1.260(2) . ?
O2 C1 1.259(2) . ?
O2 Tb1 2.3222(14) 5_666 ?
O3 C8 1.262(3) . ?
O3 Tb1 2.3479(15) 7_556 ?
O3 Tb1 2.5819(15) 8_455 ?
O4 C8 1.256(3) . ?
O4 Tb1 2.4627(15) 8_455 ?
O5 N1 1.218(2) . ?
O6 N1 1.209(3) . ?
O7 C9 1.266(2) . ?
O8 C14A 1.261(2) . ?
O8 C14 1.261(2) . ?
O8 Tb1 2.3860(15) 1_565 ?
O11 H1O 0.8342 . ?
O11 H2O 0.8107 . ?
N1 C6 1.466(3) . ?
C1 C2 1.509(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.389(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.390(3) . ?
C5 C8 1.508(3) . ?
C6 C7 1.383(3) . ?
C7 H7A 0.9500 . ?
C8 Tb1 2.880(2) 8_455 ?
C9 O7 1.266(2) 2_656 ?
C9 C10 1.498(4) . ?
C10 C11 1.392(3) . ?
C10 C11 1.392(3) 2_656 ?
C11 C12A 1.386(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
O9 N2 1.220(5) . ?
O10 N2 1.225(5) . ?
O10 O10 1.707(7) 5_676 ?
N2 C12 1.507(4) . ?
C12 C13 1.398(3) . ?
C13 C12 1.398(3) 2_656 ?
C13 C14 1.511(4) . ?
C14 O8 1.261(2) 2_656 ?
C12A C13A 1.398(3) . ?
C12A H12A 0.9500 . ?
C13A C12A 1.398(3) 2_656 ?
C13A C14A 1.511(4) . ?
C14A O8 1.261(2) 2_656 ?
O1W H1WA 0.9151 . ?
O1W H1WB 0.9855 . ?

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
O1 Tb1 O2 86.86(5) . 5_666 ?
O1 Tb1 O7 99.09(5) . . ?
O2 Tb1 O7 74.26(5) 5_666 . ?
O1 Tb1 O3 77.25(5) . 7_556 ?
O2 Tb1 O3 142.46(5) 5_666 7_556 ?
O7 Tb1 O3 75.00(5) . 7_556 ?
O1 Tb1 O11 83.52(6) . . ?
O2 Tb1 O11 75.75(5) 5_666 . ?
O7 Tb1 O11 149.69(5) . . ?
O3 Tb1 O11 134.28(6) 7_556 . ?
O1 Tb1 O8 100.95(5) . 1_545 ?
O2 Tb1 O8 144.15(5) 5_666 1_545 ?
O7 Tb1 O8 137.03(5) . 1_545 ?
O3 Tb1 O8 72.97(5) 7_556 1_545 ?
O11 Tb1 O8 70.56(5) . 1_545 ?
O1 Tb1 O4 157.62(5) . 8_556 ?
O2 Tb1 O4 80.46(5) 5_666 8_556 ?
O7 Tb1 O4 95.14(5) . 8_556 ?
O3 Tb1 O4 123.40(5) 7_556 8_556 ?
O11 Tb1 O4 75.55(5) . 8_556 ?
O8 Tb1 O4 79.66(5) 1_545 8_556 ?
O1 Tb1 O3 149.83(5) . 8_556 ?
O2 Tb1 O3 118.29(5) 5_666 8_556 ?
O7 Tb1 O3 74.48(5) . 8_556 ?
O3 Tb1 O3 72.60(5) 7_556 8_556 ?
O11 Tb1 O3 117.10(5) . 8_556 ?
O8 Tb1 O3 69.13(5) 1_545 8_556 ?
O4 Tb1 O3 51.39(5) 8_556 8_556 ?
O1 Tb1 C8 170.70(6) . 8_556 ?
O2 Tb1 C8 101.63(6) 5_666 8_556 ?
O7 Tb1 C8 87.00(6) . 8_556 ?
O3 Tb1 C8 97.74(6) 7_556 8_556 ?
O11 Tb1 C8 94.79(6) . 8_556 ?
O8 Tb1 C8 69.94(6) 1_545 8_556 ?
O4 Tb1 C8 25.70(5) 8_556 8_556 ?
O3 Tb1 C8 25.99(5) 8_556 8_556 ?
O1 Tb1 Tb1 115.59(4) . 2_656 ?
O2 Tb1 Tb1 138.53(4) 5_666 2_656 ?
O7 Tb1 Tb1 68.27(4) . 2_656 ?
O3 Tb1 Tb1 38.39(4) 7_556 2_656 ?
O11 Tb1 Tb1 137.59(4) . 2_656 ?
O8 Tb1 Tb1 68.81(4) 1_545 2_656 ?
O4 Tb1 Tb1 85.71(4) 8_556 2_656 ?
O3 Tb1 Tb1 34.38(3) 8_556 2_656 ?
C8 Tb1 Tb1 60.10(4) 8_556 2_656 ?
C1 O1 Tb1 144.89(14) . . ?
C1 O2 Tb1 133.18(13) . 5_666 ?
C8 O3 Tb1 159.64(14) . 7_556 ?
C8 O3 Tb1 90.30(12) . 8_455 ?
Tb1 O3 Tb1 107.23(5) 7_556 8_455 ?
C8 O4 Tb1 96.05(12) . 8_455 ?
C9 O7 Tb1 139.06(15) . . ?
C14A O8 Tb1 137.23(16) . 1_565 ?
C14 O8 Tb1 137.23(16) . 1_565 ?
Tb1 O11 H1O 118.0 . . ?
Tb1 O11 H2O 134.6 . . ?
H1O O11 H2O 100.1 . . ?
O6 N1 O5 123.1(2) . . ?
O6 N1 C6 118.64(19) . . ?
O5 N1 C6 118.28(18) . . ?
O2 C1 O1 124.98(19) . . ?
O2 C1 C2 118.49(18) . . ?
O1 C1 C2 116.53(18) . . ?
C7 C2 C3 119.48(19) . . ?
C7 C2 C1 119.89(19) . . ?
C3 C2 C1 120.62(19) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 117.32(19) . . ?
C6 C5 C8 125.23(19) . . ?
C4 C5 C8 117.27(19) . . ?
C7 C6 C5 123.15(19) . . ?
C7 C6 N1 118.06(19) . . ?
C5 C6 N1 118.79(18) . . ?
C6 C7 C2 118.63(19) . . ?
C6 C7 H7A 120.7 . . ?
C2 C7 H7A 120.7 . . ?
O4 C8 O3 120.88(19) . . ?
O4 C8 C5 117.82(18) . . ?
O3 C8 C5 120.97(19) . . ?
O4 C8 Tb1 58.26(10) . 8_455 ?
O3 C8 Tb1 63.71(11) . 8_455 ?
C5 C8 Tb1 163.07(14) . 8_455 ?
O7 C9 O7 125.3(3) 2_656 . ?
O7 C9 C10 117.34(13) 2_656 . ?
O7 C9 C10 117.34(13) . . ?
C11 C10 C11 119.7(3) . 2_656 ?
C11 C10 C9 120.16(14) . . ?
C11 C10 C9 120.16(14) 2_656 . ?
C12A C11 C10 119.7(2) . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N2 O10 O10 82.2(3) . 5_676 ?
O9 N2 O10 124.6(4) . . ?
O9 N2 C12 119.7(3) . . ?
O10 N2 C12 115.6(3) . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 N2 115.2(2) . . ?
C13 C12 N2 122.5(2) . . ?
C12 C13 C12 117.2(3) . 2_656 ?
C12 C13 C14 121.39(14) . . ?
C12 C13 C14 121.39(14) 2_656 . ?
O8 C14 O8 127.0(3) . 2_656 ?
O8 C14 C13 116.51(14) . . ?
O8 C14 C13 116.51(14) 2_656 . ?
C11 C12A C13A 121.8(2) . . ?
C11 C12A H12A 119.1 . . ?
C13A C12A H12A 119.1 . . ?
C12A C13A C12A 117.2(3) . 2_656 ?
C12A C13A C14A 121.39(14) . . ?
C12A C13A C14A 121.39(14) 2_656 . ?
O8 C14A O8 127.0(3) . 2_656 ?
O8 C14A C13A 116.51(14) . . ?
O8 C14A C13A 116.51(14) 2_656 . ?
H1WA O1W H1WB 109.1 . . ?

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
Tb1 O2 C1 O1 91.1(2) 5_666 . . . ?
Tb1 O2 C1 C2 -89.2(2) 5_666 . . . ?
Tb1 O1 C1 O2 5.6(4) . . . . ?
Tb1 O1 C1 C2 -174.12(16) . . . . ?
O2 C1 C2 C7 171.47(19) . . . . ?
O1 C1 C2 C7 -8.8(3) . . . . ?
O2 C1 C2 C3 -7.4(3) . . . . ?
O1 C1 C2 C3 172.3(2) . . . . ?
C7 C2 C3 C4 -1.8(3) . . . . ?
C1 C2 C3 C4 177.1(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C3 C4 C5 C8 -173.6(2) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C8 C5 C6 C7 173.5(2) . . . . ?
C4 C5 C6 N1 178.0(2) . . . . ?
C8 C5 C6 N1 -7.0(3) . . . . ?
O6 N1 C6 C7 -0.4(4) . . . . ?
O5 N1 C6 C7 178.5(2) . . . . ?
O6 N1 C6 C5 -179.8(3) . . . . ?
O5 N1 C6 C5 -1.0(3) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
N1 C6 C7 C2 -179.96(19) . . . . ?
C3 C2 C7 C6 2.1(3) . . . . ?
C1 C2 C7 C6 -176.84(19) . . . . ?
Tb1 O4 C8 O3 12.4(2) 8_455 . . . ?
Tb1 O4 C8 C5 -161.00(16) 8_455 . . . ?
Tb1 O3 C8 O4 -161.7(3) 7_556 . . . ?
Tb1 O3 C8 O4 -11.7(2) 8_455 . . . ?
Tb1 O3 C8 C5 11.5(5) 7_556 . . . ?
Tb1 O3 C8 C5 161.43(18) 8_455 . . . ?
Tb1 O3 C8 Tb1 -149.9(4) 7_556 . . 8_455 ?
C6 C5 C8 O4 -90.8(3) . . . . ?
C4 C5 C8 O4 84.1(3) . . . . ?
C6 C5 C8 O3 95.8(3) . . . . ?
C4 C5 C8 O3 -89.3(3) . . . . ?
C6 C5 C8 Tb1 -162.8(4) . . . 8_455 ?
C4 C5 C8 Tb1 12.1(6) . . . 8_455 ?
Tb1 O7 C9 O7 -1.31(10) . . . 2_656 ?
Tb1 O7 C9 C10 178.69(10) . . . . ?
O7 C9 C10 C11 -161.82(13) 2_656 . . . ?
O7 C9 C10 C11 18.18(13) . . . . ?
O7 C9 C10 C11 18.18(13) 2_656 . . 2_656 ?
O7 C9 C10 C11 -161.82(13) . . . 2_656 ?
C11 C10 C11 C12A -1.04(16) 2_656 . . . ?
C9 C10 C11 C12A 178.96(16) . . . . ?
C11 C10 C11 C12 -1.04(16) 2_656 . . . ?
C9 C10 C11 C12 178.96(16) . . . . ?
O10 O10 N2 O9 5.1(5) 5_676 . . . ?
O10 O10 N2 C12 -175.1(3) 5_676 . . . ?
C10 C11 C12 C13 2.1(3) . . . . ?
C10 C11 C12 N2 -170.0(2) . . . . ?
O9 N2 C12 C11 113.9(4) . . . . ?
O10 N2 C12 C11 -65.9(4) . . . . ?
O9 N2 C12 C13 -58.2(5) . . . . ?
O10 N2 C12 C13 122.0(3) . . . . ?
C11 C12 C13 C12 -1.07(17) . . . 2_656 ?
N2 C12 C13 C12 170.5(3) . . . 2_656 ?
C11 C12 C13 C14 178.93(17) . . . . ?
N2 C12 C13 C14 -9.5(3) . . . . ?
Tb1 O8 C14 O8 -6.51(11) 1_565 . . 2_656 ?
Tb1 O8 C14 C13 173.48(11) 1_565 . . . ?
C12 C13 C14 O8 -25.55(14) . . . . ?
C12 C13 C14 O8 154.46(15) 2_656 . . . ?
C12 C13 C14 O8 154.45(15) . . . 2_656 ?
C12 C13 C14 O8 -25.55(15) 2_656 . . 2_656 ?
C10 C11 C12A C13A 2.1(3) . . . . ?
C11 C12A C13A C12A -1.07(17) . . . 2_656 ?
C11 C12A C13A C14A 178.93(17) . . . . ?
Tb1 O8 C14A O8 -6.51(11) 1_565 . . 2_656 ?
Tb1 O8 C14A C13A 173.48(11) 1_565 . . . ?
C12A C13A C14A O8 -25.55(14) . . . . ?
C12A C13A C14A O8 154.46(15) 2_656 . . . ?
C12A C13A C14A O8 154.45(15) . . . 2_656 ?
C12A C13A C14A O8 -25.55(15) 2_656 . . 2_656 ?

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
O11 H1O O6 0.83 2.17 2.978(3) 162.0 5_656
O11 H2O O1W 0.81 1.84 2.641(3) 171.0 .
O1W H1WA O5 0.92 2.01 2.897(3) 163.3 3
O1W H1WB O4 0.99 1.83 2.811(3) 171.0 2_655

_refine_diff_density_max         0.618
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_d14180
_database_code_depnum_ccdc_archive 'CCDC 1436008'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H13 Er2 N3 O20, 2(H2 O)'
_chemical_formula_sum            'C24 H17 Er2 N3 O22'
_chemical_formula_weight         1033.92

# start Validation Reply Form 
_vrf_PLAT220_d14180              
; 
PROBLEM: Large Non-Solvent  O     Ueq(max)/Ueq(min) Range   6.9 Ratio 
RESPONSE: One of the nitro group O atoms has a larger the normal 
anisotropic displacement parameter. Neither the bonded N atom nor 
the other O atom of the same group have large or elongated ellipsoids 
(which may have indicated rotational disorder about the C6---N1 bond) 
therefore it is difficult to create a disorder model. 
This is similar to the Eu and Tb analogues. 
;
# end Validation Reply Form 

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'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   16.6713(7)
_cell_length_b                   11.2905(5)
_cell_length_c                   15.2129(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.2242(12)
_cell_angle_gamma                90
_cell_volume                     2863.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.51

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.398
_exptl_crystal_F_000             1976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.931
_shelx_estimated_absorpt_T_min   0.330
_shelx_estimated_absorpt_T_max   0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6352
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18247
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.179
_diffrn_reflns_theta_max         27.507
_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             3294
_reflns_number_gt                2954
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0131P)²+7.2869P] 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         3294
_refine_ls_number_parameters     246
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0194
_refine_ls_R_factor_gt           0.0147
_refine_ls_wR_factor_ref         0.0335
_refine_ls_wR_factor_gt          0.0320
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.107
_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_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
Er1 Er 0.53440(2) 0.35428(2) 0.62675(2) 0.00656(4) Uani 1 1 d . . . . .
O1 O 0.43485(10) 0.35245(14) 0.52649(11) 0.0131(3) Uani 1 1 d . . . . .
O2 O 0.39763(9) 0.52615(14) 0.46910(10) 0.0105(3) Uani 1 1 d . . . . .
O3 O 0.07957(10) 0.15380(14) 0.28695(11) 0.0121(3) Uani 1 1 d . . . . .
O4 O 0.16935(10) 0.17165(15) 0.18364(11) 0.0142(4) Uani 1 1 d . . . . .
O5 O 0.21323(12) -0.00464(16) 0.32907(13) 0.0257(4) Uani 1 1 d . U . . .
O6 O 0.31584(18) -0.0087(2) 0.4131(2) 0.0724(10) Uani 1 1 d . U . . .
O7 O 0.51888(10) 0.54317(14) 0.67927(10) 0.0128(3) Uani 1 1 d . . . . .
O8 O 0.52499(11) 1.15971(14) 0.68122(11) 0.0145(4) Uani 1 1 d . . . . .
O11 O 0.59439(11) 0.22352(15) 0.52820(11) 0.0185(4) Uani 1 1 d . . . . .
H1O H 0.6106 0.1559 0.5462 0.028 Uiso 1 1 d R U . . .
H2O H 0.6273 0.2289 0.4868 0.028 Uiso 1 1 d R U . . .
N1 N 0.26551(13) 0.04450(18) 0.37192(15) 0.0200(5) Uani 1 1 d . U . . .
C1 C 0.39097(13) 0.4158(2) 0.47774(14) 0.0094(4) Uani 1 1 d . . . . .
C2 C 0.32601(14) 0.3524(2) 0.42695(15) 0.0105(4) Uani 1 1 d . . . . .
C3 C 0.26772(15) 0.4163(2) 0.38136(16) 0.0160(5) Uani 1 1 d . . . . .
H3A H 0.2675 0.5004 0.3844 0.019 Uiso 1 1 calc R U . . .
C4 C 0.20990(16) 0.3582(2) 0.33143(17) 0.0179(5) Uani 1 1 d . . . . .
H4A H 0.1706 0.4031 0.3008 0.022 Uiso 1 1 calc R U . . .
C5 C 0.20873(14) 0.2357(2) 0.32563(15) 0.0113(5) Uani 1 1 d . . . . .
C6 C 0.26660(15) 0.1741(2) 0.37393(16) 0.0124(5) Uani 1 1 d . . . . .
C7 C 0.32426(14) 0.2296(2) 0.42439(15) 0.0117(5) Uani 1 1 d . . . . .
H7A H 0.3622 0.1845 0.4569 0.014 Uiso 1 1 calc R U . . .
C8 C 0.14958(14) 0.1801(2) 0.26315(15) 0.0112(5) Uani 1 1 d . . . . .
C9 C 0.5000 0.5940(3) 0.7500 0.0108(6) Uani 1 2 d S T P . .
C10 C 0.5000 0.7272(3) 0.7500 0.0118(6) Uani 1 2 d S T P . .
C11 C 0.49711(15) 0.7893(2) 0.67102(16) 0.0142(5) Uani 1 1 d . . . . .
H11 H 0.4961 0.7478 0.6167 0.017 Uiso 1 1 calc R U . A 1
O9 O 0.4164(2) 1.0239(3) 0.5736(3) 0.0262(9) Uani 0.5 1 d . . P B 1
O10 O 0.5304(2) 0.9555(3) 0.5284(2) 0.0261(9) Uani 0.5 1 d . . P B 1
N2 N 0.4793(3) 0.9688(3) 0.5847(3) 0.0149(9) Uani 0.5 1 d . . P B 1
C12 C 0.49576(16) 0.9116(2) 0.67200(15) 0.0158(5) Uani 0.5 1 d . . P B 1
C13 C 0.5000 0.9761(3) 0.7500 0.0159(7) Uani 0.5 2 d S T P B 1
C14 C 0.5000 1.1097(3) 0.7500 0.0125(7) Uani 0.5 2 d S T P B 1
C12A C 0.49576(16) 0.9116(2) 0.67200(15) 0.0158(5) Uani 0.5 1 d . . P B 2
H12A H 0.4918 0.9531 0.6178 0.019 Uiso 0.5 1 calc R U P B 2
C13A C 0.5000 0.9761(3) 0.7500 0.0159(7) Uani 0.5 2 d S T P B 2
C14A C 0.5000 1.1097(3) 0.7500 0.0125(7) Uani 0.5 2 d S T P B 2
O1W O 0.68589(14) 0.2565(2) 0.38857(16) 0.0420(6) Uani 1 1 d . . . . .
H1WA H 0.7330 0.2188 0.3629 0.063 Uiso 1 1 d R U . . .
H1WB H 0.6830 0.3334 0.3684 0.063 Uiso 1 1 d R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er1 O1 2.2499(16) . ?
Er1 O2 2.2904(16) 5_666 ?
Er1 O7 2.2925(15) . ?
Er1 O3 2.3155(16) 7_556 ?
Er1 O11 2.3322(17) . ?
Er1 O8 2.3532(15) 1_545 ?
Er1 O4 2.4250(17) 8_556 ?
Er1 O3 2.5495(16) 8_556 ?
Er1 C8 2.848(2) 8_556 ?
Er1 Er1 3.9257(3) 2_656 ?
O1 C1 1.262(3) . ?
O2 C1 1.258(3) . ?
O2 Er1 2.2903(16) 5_666 ?
O3 C8 1.259(3) . ?
O3 Er1 2.3156(16) 7_556 ?
O3 Er1 2.5495(16) 8_455 ?
O4 C8 1.258(3) . ?
O4 Er1 2.4249(17) 8_455 ?
O5 N1 1.220(3) . ?
O6 N1 1.206(3) . ?
O7 C9 1.260(2) . ?
O8 C14A 1.261(2) . ?
O8 C14 1.261(2) . ?
O8 Er1 2.3533(15) 1_565 ?
O11 H1O 0.8549 . ?
O11 H2O 0.8394 . ?
N1 C6 1.463(3) . ?
C1 C2 1.508(3) . ?
C2 C7 1.387(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.390(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.396(3) . ?
C5 C8 1.504(3) . ?
C6 C7 1.379(3) . ?
C7 H7A 0.9500 . ?
C8 Er1 2.848(2) 8_455 ?
C9 O7 1.260(2) 2_656 ?
C9 C10 1.504(4) . ?
C10 C11 1.392(3) 2_656 ?
C10 C11 1.392(3) . ?
C11 C12A 1.381(3) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
O9 N2 1.231(5) . ?
O9 O10 1.805(5) 5_676 ?
O10 N2 1.220(5) . ?
O10 O10 1.667(8) 5_676 ?
O10 O9 1.805(5) 5_676 ?
N2 C12 1.501(5) . ?
C12 C13 1.394(3) . ?
C13 C12 1.394(3) 2_656 ?
C13 C14 1.509(5) . ?
C14 O8 1.261(2) 2_656 ?
C12A C13A 1.394(3) . ?
C12A H12A 0.9500 . ?
C13A C12A 1.394(3) 2_656 ?
C13A C14A 1.509(5) . ?
C14A O8 1.261(2) 2_656 ?
O1W H1WA 0.9764 . ?
O1W H1WB 0.9220 . ?

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
O1 Er1 O2 86.52(6) . 5_666 ?
O1 Er1 O7 99.25(6) . . ?
O2 Er1 O7 74.36(6) 5_666 . ?
O1 Er1 O3 77.24(6) . 7_556 ?
O2 Er1 O3 142.49(6) 5_666 7_556 ?
O7 Er1 O3 75.23(6) . 7_556 ?
O1 Er1 O11 82.84(6) . . ?
O2 Er1 O11 75.49(6) 5_666 . ?
O7 Er1 O11 149.57(6) . . ?
O3 Er1 O11 133.98(6) 7_556 . ?
O1 Er1 O8 100.38(6) . 1_545 ?
O2 Er1 O8 143.92(6) 5_666 1_545 ?
O7 Er1 O8 137.55(6) . 1_545 ?
O3 Er1 O8 73.00(6) 7_556 1_545 ?
O11 Er1 O8 70.42(6) . 1_545 ?
O1 Er1 O4 157.18(6) . 8_556 ?
O2 Er1 O4 80.66(6) 5_666 8_556 ?
O7 Er1 O4 95.38(6) . 8_556 ?
O3 Er1 O4 123.72(6) 7_556 8_556 ?
O11 Er1 O4 75.73(6) . 8_556 ?
O8 Er1 O4 79.90(6) 1_545 8_556 ?
O1 Er1 O3 149.54(6) . 8_556 ?
O2 Er1 O3 118.99(5) 5_666 8_556 ?
O7 Er1 O3 74.54(5) . 8_556 ?
O3 Er1 O3 72.33(6) 7_556 8_556 ?
O11 Er1 O3 117.78(6) . 8_556 ?
O8 Er1 O3 69.50(5) 1_545 8_556 ?
O4 Er1 O3 52.01(5) 8_556 8_556 ?
O1 Er1 C8 170.44(6) . 8_556 ?
O2 Er1 C8 102.14(6) 5_666 8_556 ?
O7 Er1 C8 87.11(6) . 8_556 ?
O3 Er1 C8 97.70(6) 7_556 8_556 ?
O11 Er1 C8 95.31(6) . 8_556 ?
O8 Er1 C8 70.24(6) 1_545 8_556 ?
O4 Er1 C8 26.06(6) 8_556 8_556 ?
O3 Er1 C8 26.23(6) 8_556 8_556 ?
O1 Er1 Er1 115.47(4) . 2_656 ?
O2 Er1 Er1 139.05(4) 5_666 2_656 ?
O7 Er1 Er1 68.48(4) . 2_656 ?
O3 Er1 Er1 38.27(4) 7_556 2_656 ?
O11 Er1 Er1 137.88(4) . 2_656 ?
O8 Er1 Er1 69.12(4) 1_545 2_656 ?
O4 Er1 Er1 86.17(4) 8_556 2_656 ?
O3 Er1 Er1 34.23(4) 8_556 2_656 ?
C8 Er1 Er1 60.19(5) 8_556 2_656 ?
C1 O1 Er1 144.85(15) . . ?
C1 O2 Er1 133.98(14) . 5_666 ?
C8 O3 Er1 159.41(16) . 7_556 ?
C8 O3 Er1 90.24(13) . 8_455 ?
Er1 O3 Er1 107.49(6) 7_556 8_455 ?
C8 O4 Er1 96.09(14) . 8_455 ?
C9 O7 Er1 138.58(17) . . ?
C14A O8 Er1 137.12(17) . 1_565 ?
C14 O8 Er1 137.12(17) . 1_565 ?
Er1 O11 H1O 119.7 . . ?
Er1 O11 H2O 136.1 . . ?
H1O O11 H2O 95.6 . . ?
O6 N1 O5 123.1(2) . . ?
O6 N1 C6 118.6(2) . . ?
O5 N1 C6 118.3(2) . . ?
O2 C1 O1 124.9(2) . . ?
O2 C1 C2 118.7(2) . . ?
O1 C1 C2 116.5(2) . . ?
C7 C2 C3 119.3(2) . . ?
C7 C2 C1 120.2(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 117.0(2) . . ?
C4 C5 C8 117.7(2) . . ?
C6 C5 C8 125.1(2) . . ?
C7 C6 C5 123.1(2) . . ?
C7 C6 N1 118.4(2) . . ?
C5 C6 N1 118.6(2) . . ?
C6 C7 C2 119.0(2) . . ?
C6 C7 H7A 120.5 . . ?
C2 C7 H7A 120.5 . . ?
O4 C8 O3 120.3(2) . . ?
O4 C8 C5 117.7(2) . . ?
O3 C8 C5 121.5(2) . . ?
O4 C8 Er1 57.85(12) . 8_455 ?
O3 C8 Er1 63.53(12) . 8_455 ?
C5 C8 Er1 162.89(16) . 8_455 ?
O7 C9 O7 125.8(3) 2_656 . ?
O7 C9 C10 117.08(15) 2_656 . ?
O7 C9 C10 117.08(15) . . ?
C11 C10 C11 119.5(3) 2_656 . ?
C11 C10 C9 120.23(15) 2_656 . ?
C11 C10 C9 120.23(15) . . ?
C12A C11 C10 119.6(2) . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
N2 O9 O10 76.3(3) . 5_676 ?
N2 O10 O10 82.2(4) . 5_676 ?
N2 O10 O9 159.1(4) . 5_676 ?
O10 O10 O9 77.1(3) 5_676 5_676 ?
O10 N2 O9 124.2(4) . . ?
O10 N2 C12 116.3(4) . . ?
O9 N2 C12 119.5(4) . . ?
C11 C12 C13 122.1(2) . . ?
C11 C12 N2 115.1(2) . . ?
C13 C12 N2 122.5(3) . . ?
C12 C13 C12 117.0(3) 2_656 . ?
C12 C13 C14 121.50(15) 2_656 . ?
C12 C13 C14 121.50(15) . . ?
O8 C14 O8 126.8(3) . 2_656 ?
O8 C14 C13 116.60(15) . . ?
O8 C14 C13 116.60(15) 2_656 . ?
C11 C12A C13A 122.1(2) . . ?
C11 C12A H12A 119.0 . . ?
C13A C12A H12A 119.0 . . ?
C12A C13A C12A 117.0(3) 2_656 . ?
C12A C13A C14A 121.50(15) 2_656 . ?
C12A C13A C14A 121.50(15) . . ?
O8 C14A O8 126.8(3) . 2_656 ?
O8 C14A C13A 116.60(15) . . ?
O8 C14A C13A 116.60(15) 2_656 . ?
H1WA O1W H1WB 108.6 . . ?

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
Er1 O2 C1 O1 92.4(3) 5_666 . . . ?
Er1 O2 C1 C2 -87.8(2) 5_666 . . . ?
Er1 O1 C1 O2 4.7(4) . . . . ?
Er1 O1 C1 C2 -175.15(18) . . . . ?
O2 C1 C2 C7 170.3(2) . . . . ?
O1 C1 C2 C7 -9.8(3) . . . . ?
O2 C1 C2 C3 -8.9(3) . . . . ?
O1 C1 C2 C3 170.9(2) . . . . ?
C7 C2 C3 C4 -2.1(4) . . . . ?
C1 C2 C3 C4 177.2(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 1.7(4) . . . . ?
C3 C4 C5 C8 -173.9(2) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C8 C5 C6 C7 174.0(2) . . . . ?
C4 C5 C6 N1 177.9(2) . . . . ?
C8 C5 C6 N1 -6.8(4) . . . . ?
O6 N1 C6 C7 -1.3(4) . . . . ?
O5 N1 C6 C7 178.2(2) . . . . ?
O6 N1 C6 C5 179.5(3) . . . . ?
O5 N1 C6 C5 -1.1(4) . . . . ?
C5 C6 C7 C2 -0.8(4) . . . . ?
N1 C6 C7 C2 -180.0(2) . . . . ?
C3 C2 C7 C6 2.5(4) . . . . ?
C1 C2 C7 C6 -176.8(2) . . . . ?
Er1 O4 C8 O3 12.0(2) 8_455 . . . ?
Er1 O4 C8 C5 -160.89(18) 8_455 . . . ?
Er1 O3 C8 O4 -161.4(3) 7_556 . . . ?
Er1 O3 C8 O4 -11.4(2) 8_455 . . . ?
Er1 O3 C8 C5 11.3(6) 7_556 . . . ?
Er1 O3 C8 C5 161.3(2) 8_455 . . . ?
Er1 O3 C8 Er1 -150.0(4) 7_556 . . 8_455 ?
C4 C5 C8 O4 83.9(3) . . . . ?
C6 C5 C8 O4 -91.4(3) . . . . ?
C4 C5 C8 O3 -89.0(3) . . . . ?
C6 C5 C8 O3 95.8(3) . . . . ?
C4 C5 C8 Er1 13.5(7) . . . 8_455 ?
C6 C5 C8 Er1 -161.8(4) . . . 8_455 ?
Er1 O7 C9 O7 -0.91(11) . . . 2_656 ?
Er1 O7 C9 C10 179.09(11) . . . . ?
O7 C9 C10 C11 18.58(15) 2_656 . . 2_656 ?
O7 C9 C10 C11 -161.42(15) . . . 2_656 ?
O7 C9 C10 C11 -161.41(15) 2_656 . . . ?
O7 C9 C10 C11 18.58(15) . . . . ?
C11 C10 C11 C12A -1.10(18) 2_656 . . . ?
C9 C10 C11 C12A 178.90(17) . . . . ?
C11 C10 C11 C12 -1.10(18) 2_656 . . . ?
C9 C10 C11 C12 178.90(17) . . . . ?
O10 O10 N2 O9 4.5(6) 5_676 . . . ?
O9 O10 N2 O9 11.6(15) 5_676 . . . ?
O10 O10 N2 C12 -176.4(3) 5_676 . . . ?
O9 O10 N2 C12 -169.3(9) 5_676 . . . ?
O10 O9 N2 O10 -4.2(5) 5_676 . . . ?
O10 O9 N2 C12 176.7(4) 5_676 . . . ?
C10 C11 C12 C13 2.3(4) . . . . ?
C10 C11 C12 N2 -170.6(2) . . . . ?
O10 N2 C12 C11 -66.0(5) . . . . ?
O9 N2 C12 C11 113.1(4) . . . . ?
O10 N2 C12 C13 121.2(4) . . . . ?
O9 N2 C12 C13 -59.7(5) . . . . ?
C11 C12 C13 C12 -1.14(18) . . . 2_656 ?
N2 C12 C13 C12 171.2(3) . . . 2_656 ?
C11 C12 C13 C14 178.85(18) . . . . ?
N2 C12 C13 C14 -8.8(3) . . . . ?
Er1 O8 C14 O8 -5.74(11) 1_565 . . 2_656 ?
Er1 O8 C14 C13 174.25(11) 1_565 . . . ?
C12 C13 C14 O8 154.91(16) 2_656 . . . ?
C12 C13 C14 O8 -25.09(16) . . . . ?
C12 C13 C14 O8 -25.09(16) 2_656 . . 2_656 ?
C12 C13 C14 O8 154.91(16) . . . 2_656 ?
C10 C11 C12A C13A 2.3(4) . . . . ?
C11 C12A C13A C12A -1.14(18) . . . 2_656 ?
C11 C12A C13A C14A 178.85(18) . . . . ?
Er1 O8 C14A O8 -5.74(11) 1_565 . . 2_656 ?
Er1 O8 C14A C13A 174.25(11) 1_565 . . . ?
C12A C13A C14A O8 154.91(16) 2_656 . . . ?
C12A C13A C14A O8 -25.09(16) . . . . ?
C12A C13A C14A O8 -25.09(16) 2_656 . . 2_656 ?
C12A C13A C14A O8 154.91(16) . . . 2_656 ?

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
O11 H1O O6 0.85 2.15 2.985(3) 163.8 5_656
O11 H2O O1W 0.84 1.82 2.646(3) 170.3 .
O1W H1WA O4 0.98 1.86 2.823(3) 170.4 2_655
O1W H1WB O5 0.92 1.99 2.882(3) 162.3 3

_refine_diff_density_max         0.621
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_d1534
_database_code_depnum_ccdc_archive 'CCDC 1436009'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 La2 N3 O24'
_chemical_formula_sum            'C24 H20 La2 N3 O24'
_chemical_formula_weight         1012.25

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'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3712(5)
_cell_length_b                   9.8819(6)
_cell_length_c                   10.2680(6)
_cell_angle_alpha                105.245(2)
_cell_angle_beta                 105.311(2)
_cell_angle_gamma                93.668(2)
_cell_volume                     782.26(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.149
_exptl_crystal_F_000             491
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    2.803
_shelx_estimated_absorpt_T_min   0.458
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5928
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24707
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.149
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3588
_reflns_number_gt                3396
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0092P)²+1.3134P] 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         3588
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0421
_refine_ls_wR_factor_gt          0.0414
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_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
La1 La 1.01132(2) 0.23145(2) 1.02238(2) 0.00784(4) Uani 1 1 d . . . . .
O1 O 0.8828(2) 0.30594(19) 0.81087(18) 0.0175(4) Uani 1 1 d . . . . .
O2 O 0.8305(2) 0.52992(18) 0.86017(19) 0.0175(4) Uani 1 1 d . . . . .
O3 O 0.2974(2) 0.19454(18) 0.14895(17) 0.0124(3) Uani 1 1 d . . . . .
O4 O 0.5144(2) 0.2867(2) 0.09724(18) 0.0193(4) Uani 1 1 d . . . . .
O5 O 0.2895(2) 0.3192(2) 0.6379(2) 0.0266(5) Uani 1 1 d . . . . .
O6 O 0.5226(3) 0.3380(3) 0.7996(2) 0.0356(6) Uani 1 1 d . . . . .
O7 O 1.0049(2) 0.00883(17) 1.14038(17) 0.0136(3) Uani 1 1 d . . . . .
O8 O 0.9848(2) 0.22199(18) 1.26568(19) 0.0182(4) Uani 1 1 d . . . . .
O9 O 0.6659(5) 0.0361(4) 1.2143(4) 0.0223(8) Uani 0.5 1 d . . P A 1
O10 O 0.5586(5) 0.0104(5) 1.3796(5) 0.0322(10) Uani 0.5 1 d . . P A 1
N2 N 0.6794(5) 0.0238(5) 1.3328(5) 0.0181(9) Uani 0.5 1 d . . P A 1
O11 O 0.7132(2) 0.1025(2) 0.9492(2) 0.0207(4) Uani 1 1 d . . . . .
H1O H 0.6909 0.0158 0.9048 0.075(15) Uiso 1 1 d R . . . .
H2O H 0.6304 0.1352 0.9709 0.058(13) Uiso 1 1 d R . . . .
O12 O 1.2212(2) 0.2711(2) 0.8899(2) 0.0235(4) Uani 1 1 d . . . . .
H3O H 1.2165 0.2936 0.8158 0.045(11) Uiso 1 1 d R . . . .
H4O H 1.3194 0.2655 0.9340 0.047(11) Uiso 1 1 d R . . . .
O13 O 0.8139(2) 0.40819(18) 1.09451(18) 0.0149(4) Uani 1 1 d . . . . .
H5O H 0.7254 0.3753 1.1062 0.040(10) Uiso 1 1 d R . . . .
H6O H 0.7996 0.4705 1.0522 0.038(10) Uiso 1 1 d R . . . .
N1 N 0.4441(3) 0.3325(2) 0.6791(2) 0.0186(5) Uani 1 1 d . . . . .
C1 C 0.8145(3) 0.4068(2) 0.7785(2) 0.0107(5) Uani 1 1 d . . . . .
C2 C 0.7116(3) 0.3784(2) 0.6275(2) 0.0114(5) Uani 1 1 d . . . . .
C3 C 0.5380(3) 0.3411(3) 0.5789(3) 0.0142(5) Uani 1 1 d . . . . .
C4 C 0.4488(3) 0.3075(3) 0.4368(3) 0.0147(5) Uani 1 1 d . . . . .
H4A H 0.3309 0.2804 0.4068 0.018 Uiso 1 1 calc R U . . .
C5 C 0.5351(3) 0.3140(2) 0.3392(2) 0.0113(5) Uani 1 1 d . . . . .
C6 C 0.7077(3) 0.3588(3) 0.3872(3) 0.0154(5) Uani 1 1 d . . . . .
H6A H 0.7665 0.3685 0.3219 0.018 Uiso 1 1 calc R U . . .
C7 C 0.7943(3) 0.3892(3) 0.5295(3) 0.0164(5) Uani 1 1 d . . . . .
H7A H 0.9120 0.4177 0.5600 0.020 Uiso 1 1 calc R U . . .
C8 C 0.4438(3) 0.2632(2) 0.1838(3) 0.0115(5) Uani 1 1 d . . . . .
C9 C 0.9901(3) 0.0931(3) 1.2522(2) 0.0117(5) Uani 1 1 d . . . . .
C10 C 0.9904(3) 0.0394(2) 1.3764(3) 0.0133(5) Uani 1 1 d . . . . .
C11 C 0.8509(3) 0.0268(3) 1.4236(3) 0.0177(5) Uani 0.5 1 d . . P A 1
C12 C 1.1411(3) 0.0108(3) 1.4535(3) 0.0169(5) Uani 0.5 1 d . . P A 1
H12 H 1.2380 0.0168 1.4225 0.020 Uiso 0.5 1 calc R U P A 1
C12A C 0.8509(3) 0.0268(3) 1.4236(3) 0.0177(5) Uani 0.5 1 d . . P A 2
H12A H 0.7469 0.0442 1.3706 0.021 Uiso 0.5 1 calc R U P A 2
C11A C 1.1411(3) 0.0108(3) 1.4535(3) 0.0169(5) Uani 0.5 1 d . . P A 2


_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
La1 O2 2.4557(17) 2_767 ?
La1 O1 2.4746(17) . ?
La1 O7 2.4902(17) 2_757 ?
La1 O3 2.5047(16) 1_656 ?
La1 O11 2.5529(18) . ?
La1 O12 2.5579(18) . ?
La1 O13 2.5817(17) . ?
La1 O8 2.5907(17) . ?
La1 O7 2.7806(16) . ?
La1 C9 3.059(2) . ?
O1 C1 1.256(3) . ?
O2 C1 1.259(3) . ?
O2 La1 2.4557(17) 2_767 ?
O3 C8 1.275(3) . ?
O3 La1 2.5047(16) 1_454 ?
O4 C8 1.250(3) . ?
O5 N1 1.237(3) . ?
O6 N1 1.224(3) . ?
O7 C9 1.270(3) . ?
O7 La1 2.4902(17) 2_757 ?
O8 C9 1.249(3) . ?
O9 N2 1.231(6) . ?
O10 N2 1.242(6) . ?
N2 C11 1.485(5) . ?
O11 H1O 0.8400 . ?
O11 H2O 0.8399 . ?
O12 H3O 0.8400 . ?
O12 H4O 0.8400 . ?
O13 H5O 0.8400 . ?
O13 H6O 0.8400 . ?
N1 C3 1.466(3) . ?
C1 C2 1.504(3) . ?
C2 C7 1.384(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.393(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.398(3) . ?
C5 C8 1.506(3) . ?
C6 C7 1.390(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C9 C10 1.503(3) . ?
C10 C12A 1.389(4) . ?
C10 C11 1.389(4) . ?
C10 C11A 1.391(4) . ?
C10 C12 1.391(4) . ?
C11 C12 1.393(3) 2_758 ?
C12 C11 1.393(3) 2_758 ?
C12 H12 0.9500 . ?
C12A C11A 1.393(3) 2_758 ?
C12A H12A 0.9500 . ?
C11A C12A 1.393(3) 2_758 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 La1 O1 89.93(6) 2_767 . ?
O2 La1 O7 147.47(6) 2_767 2_757 ?
O1 La1 O7 87.34(6) . 2_757 ?
O2 La1 O3 74.53(6) 2_767 1_656 ?
O1 La1 O3 136.85(6) . 1_656 ?
O7 La1 O3 85.55(6) 2_757 1_656 ?
O2 La1 O11 140.03(6) 2_767 . ?
O1 La1 O11 79.23(6) . . ?
O7 La1 O11 70.98(6) 2_757 . ?
O3 La1 O11 136.73(6) 1_656 . ?
O2 La1 O12 71.95(6) 2_767 . ?
O1 La1 O12 67.68(6) . . ?
O7 La1 O12 77.08(6) 2_757 . ?
O3 La1 O12 69.24(6) 1_656 . ?
O11 La1 O12 134.58(6) . . ?
O2 La1 O13 69.90(6) 2_767 . ?
O1 La1 O13 73.92(6) . . ?
O7 La1 O13 139.23(6) 2_757 . ?
O3 La1 O13 132.45(6) 1_656 . ?
O11 La1 O13 70.13(6) . . ?
O12 La1 O13 124.82(6) . . ?
O2 La1 O8 88.04(6) 2_767 . ?
O1 La1 O8 144.30(6) . . ?
O7 La1 O8 112.29(5) 2_757 . ?
O3 La1 O8 76.39(6) 1_656 . ?
O11 La1 O8 79.68(6) . . ?
O12 La1 O8 143.64(6) . . ?
O13 La1 O8 71.94(5) . . ?
O2 La1 O7 126.52(5) 2_767 . ?
O1 La1 O7 143.34(6) . . ?
O7 La1 O7 64.44(6) 2_757 . ?
O3 La1 O7 67.15(5) 1_656 . ?
O11 La1 O7 69.97(6) . . ?
O12 La1 O7 122.75(6) . . ?
O13 La1 O7 111.85(5) . . ?
O8 La1 O7 48.28(5) . . ?
O2 La1 C9 107.57(6) 2_767 . ?
O1 La1 C9 152.19(6) . . ?
O7 La1 C9 88.76(6) 2_757 . ?
O3 La1 C9 70.10(6) 1_656 . ?
O11 La1 C9 73.48(6) . . ?
O12 La1 C9 137.72(6) . . ?
O13 La1 C9 91.62(6) . . ?
O8 La1 C9 23.74(6) . . ?
O7 La1 C9 24.54(6) . . ?
C1 O1 La1 139.89(16) . . ?
C1 O2 La1 150.57(16) . 2_767 ?
C8 O3 La1 134.36(15) . 1_454 ?
C9 O7 La1 153.16(15) . 2_757 ?
C9 O7 La1 90.10(14) . . ?
La1 O7 La1 115.56(6) 2_757 . ?
C9 O8 La1 99.65(14) . . ?
O9 N2 O10 123.7(5) . . ?
O9 N2 C11 117.2(4) . . ?
O10 N2 C11 119.2(4) . . ?
La1 O11 H1O 120.5 . . ?
La1 O11 H2O 127.1 . . ?
H1O O11 H2O 112.2 . . ?
La1 O12 H3O 135.3 . . ?
La1 O12 H4O 112.2 . . ?
H3O O12 H4O 112.3 . . ?
La1 O13 H5O 117.4 . . ?
La1 O13 H6O 115.8 . . ?
H5O O13 H6O 112.9 . . ?
O6 N1 O5 123.1(2) . . ?
O6 N1 C3 118.3(2) . . ?
O5 N1 C3 118.7(2) . . ?
O1 C1 O2 125.5(2) . . ?
O1 C1 C2 116.6(2) . . ?
O2 C1 C2 117.8(2) . . ?
C7 C2 C3 117.6(2) . . ?
C7 C2 C1 118.0(2) . . ?
C3 C2 C1 124.4(2) . . ?
C4 C3 C2 122.5(2) . . ?
C4 C3 N1 117.7(2) . . ?
C2 C3 N1 119.7(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 C8 119.7(2) . . ?
C6 C5 C8 121.0(2) . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C2 C7 C6 121.0(2) . . ?
C2 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
O4 C8 O3 123.9(2) . . ?
O4 C8 C5 119.6(2) . . ?
O3 C8 C5 116.4(2) . . ?
O8 C9 O7 122.0(2) . . ?
O8 C9 C10 118.4(2) . . ?
O7 C9 C10 119.5(2) . . ?
O8 C9 La1 56.61(12) . . ?
O7 C9 La1 65.36(12) . . ?
C10 C9 La1 173.90(16) . . ?
C12A C10 C11A 118.4(2) . . ?
C11 C10 C12 118.4(2) . . ?
C12A C10 C9 123.3(2) . . ?
C11 C10 C9 123.3(2) . . ?
C11A C10 C9 118.1(2) . . ?
C12 C10 C9 118.1(2) . . ?
C10 C11 C12 121.9(2) . 2_758 ?
C10 C11 N2 121.7(3) . . ?
C12 C11 N2 115.2(3) 2_758 . ?
C10 C12 C11 119.6(2) . 2_758 ?
C10 C12 H12 120.2 . . ?
C11 C12 H12 120.2 2_758 . ?
C10 C12A C11A 121.9(2) . 2_758 ?
C10 C12A H12A 119.0 . . ?
C11A C12A H12A 119.0 2_758 . ?
C10 C11A C12A 119.6(2) . 2_758 ?

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
La1 O1 C1 O2 20.7(4) . . . . ?
La1 O1 C1 C2 -162.23(17) . . . . ?
La1 O2 C1 O1 81.7(4) 2_767 . . . ?
La1 O2 C1 C2 -95.4(3) 2_767 . . . ?
O1 C1 C2 C7 -82.5(3) . . . . ?
O2 C1 C2 C7 94.8(3) . . . . ?
O1 C1 C2 C3 97.1(3) . . . . ?
O2 C1 C2 C3 -85.6(3) . . . . ?
C7 C2 C3 C4 3.6(4) . . . . ?
C1 C2 C3 C4 -176.0(2) . . . . ?
C7 C2 C3 N1 -178.2(2) . . . . ?
C1 C2 C3 N1 2.3(4) . . . . ?
O6 N1 C3 C4 167.8(2) . . . . ?
O5 N1 C3 C4 -11.8(3) . . . . ?
O6 N1 C3 C2 -10.6(4) . . . . ?
O5 N1 C3 C2 169.8(2) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
N1 C3 C4 C5 -179.7(2) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C3 C4 C5 C8 173.5(2) . . . . ?
C4 C5 C6 C7 3.5(4) . . . . ?
C8 C5 C6 C7 -172.2(2) . . . . ?
C3 C2 C7 C6 -2.2(4) . . . . ?
C1 C2 C7 C6 177.4(2) . . . . ?
C5 C6 C7 C2 -1.2(4) . . . . ?
La1 O3 C8 O4 -62.0(3) 1_454 . . . ?
La1 O3 C8 C5 119.7(2) 1_454 . . . ?
C4 C5 C8 O4 170.2(2) . . . . ?
C6 C5 C8 O4 -14.2(3) . . . . ?
C4 C5 C8 O3 -11.4(3) . . . . ?
C6 C5 C8 O3 164.2(2) . . . . ?
La1 O8 C9 O7 0.0(3) . . . . ?
La1 O8 C9 C10 175.85(18) . . . . ?
La1 O7 C9 O8 -163.6(2) 2_757 . . . ?
La1 O7 C9 O8 0.0(2) . . . . ?
La1 O7 C9 C10 20.6(5) 2_757 . . . ?
La1 O7 C9 C10 -175.8(2) . . . . ?
La1 O7 C9 La1 -163.6(4) 2_757 . . . ?
O8 C9 C10 C12A 71.8(3) . . . . ?
O7 C9 C10 C12A -112.2(3) . . . . ?
O8 C9 C10 C11 71.8(3) . . . . ?
O7 C9 C10 C11 -112.2(3) . . . . ?
O8 C9 C10 C11A -103.4(3) . . . . ?
O7 C9 C10 C11A 72.6(3) . . . . ?
O8 C9 C10 C12 -103.4(3) . . . . ?
O7 C9 C10 C12 72.6(3) . . . . ?
C12 C10 C11 C12 1.3(4) . . . 2_758 ?
C9 C10 C11 C12 -174.0(2) . . . 2_758 ?
C12 C10 C11 N2 -166.2(3) . . . . ?
C9 C10 C11 N2 18.6(4) . . . . ?
O9 N2 C11 C10 -1.6(6) . . . . ?
O10 N2 C11 C10 179.1(4) . . . . ?
O9 N2 C11 C12 -169.8(4) . . . 2_758 ?
O10 N2 C11 C12 10.8(5) . . . 2_758 ?
C11 C10 C12 C11 -1.2(4) . . . 2_758 ?
C9 C10 C12 C11 174.2(2) . . . 2_758 ?
C11A C10 C12A C11A 1.3(4) . . . 2_758 ?
C9 C10 C12A C11A -174.0(2) . . . 2_758 ?
C12A C10 C11A C12A -1.2(4) . . . 2_758 ?
C9 C10 C11A C12A 174.2(2) . . . 2_758 ?

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
O11 H1O O3 0.84 2.02 2.829(3) 161.0 2_656
O11 H2O O4 0.84 2.17 2.943(3) 153.4 1_556
O12 H3O O5 0.84 2.14 2.940(3) 158.8 1_655
O12 H4O O4 0.84 1.96 2.756(3) 157.7 1_656
O13 H5O O4 0.84 1.89 2.720(2) 169.7 1_556
O13 H6O O2 0.84 2.27 2.989(2) 143.6 .
O13 H6O O12 0.84 2.49 3.168(3) 138.0 2_767

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_Compound_1
_database_code_depnum_ccdc_archive 'CCDC 1436823'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 N2 Nd O14'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless

_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         598.50

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7240(6)
_cell_length_b                   11.3159(8)
_cell_length_c                   12.3944(9)
_cell_angle_alpha                109.997(7)
_cell_angle_beta                 95.760(6)
_cell_angle_gamma                110.131(7)
_cell_volume                     1046.07(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13569
_cell_measurement_theta_min      5.132
_cell_measurement_theta_max      54.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.559
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6525
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 2015)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13569
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.804
_diffrn_reflns_theta_max         27.256
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4673
_reflns_number_gt                4393
_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       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'WINGX (Farrugia, 2012)'
_computing_publication_material  'Crystal Maker (Palmer, 2009)'

_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)+(0.0777P)²+13.0691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4673
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.23162(4) 0.07357(3) 0.60515(3) 0.00785(13) Uani 1 1 d . . . . .
O3 O 0.3730(6) 0.3356(5) 0.6768(4) 0.0155(9) Uani 1 1 d . . . . .
C2 C -0.1677(8) -0.3037(7) 0.5994(6) 0.0144(13) Uani 1 1 d . . . . .
C5 C 0.5943(8) 0.4583(6) 0.6064(6) 0.0111(11) Uani 1 1 d . . . . .
C1 C -0.0332(8) -0.1749(7) 0.6003(6) 0.0156(13) Uani 1 1 d . . . . .
C6 C 0.6186(9) 0.5878(7) 0.6864(7) 0.0183(14) Uani 1 1 d . . . . .
H6 H 0.5554 0.5962 0.7425 0.022 Uiso 1 1 calc R U . . .
C3 C -0.1987(9) -0.4355(7) 0.5171(6) 0.0177(13) Uani 1 1 d . . . . .
C8 C 0.4722(8) 0.3294(6) 0.6093(6) 0.0111(11) Uani 1 1 d . . . . .
O2 O 0.0705(5) 0.1218(4) 0.4673(4) 0.0116(8) Uani 1 1 d . . . . .
O8 O 0.2115(6) -0.0828(5) 0.4024(4) 0.0163(9) Uani 1 1 d . . . . .
C13 C 0.2311(8) -0.4263(7) 0.0276(6) 0.0160(13) Uani 1 1 d . . . . .
O4 O 0.4693(6) 0.2153(5) 0.5437(4) 0.0159(9) Uani 1 1 d . . . . .
O7 O 0.0506(5) 0.1655(5) 0.7103(4) 0.0129(9) Uani 1 1 d . . . . .
C10 C 0.1440(8) -0.2497(6) 0.2078(6) 0.0130(12) Uani 1 1 d . . . . .
C14 C 0.2202(14) -0.4431(11) 0.1312(7) 0.039(2) Uani 1 1 d . . . . .
H14 H 0.2397 -0.5146 0.1421 0.046 Uiso 1 1 calc R U . . .
O1 O 0.1077(7) -0.1232(6) 0.6691(6) 0.0390(17) Uani 1 1 d . . . . .
C7 C -0.2623(9) -0.2944(7) 0.6828(7) 0.0210(14) Uani 1 1 d . . . . .
H7 H -0.2463 -0.2082 0.7375 0.025 Uiso 1 1 calc R U . . .
O9 O 0.3159(7) -0.6104(6) -0.0467(5) 0.0255(12) Uani 1 1 d . . . . .
C16 C 0.2840(8) -0.5204(7) -0.0627(6) 0.0166(13) Uani 1 1 d . . . . .
N1 N -0.1016(11) -0.4544(9) 0.4269(8) 0.0415(19) Uani 1 1 d . . . . .
O10 O 0.2949(7) -0.4943(6) -0.1581(5) 0.0256(12) Uani 1 1 d . . . . .
O6 O -0.1391(11) -0.5721(8) 0.3501(8) 0.057(2) Uani 1 1 d . . . . .
OW2 O 0.3776(7) 0.1725(5) 0.8142(4) 0.0221(11) Uani 1 1 d . . . . .
OW1 O 0.4493(7) -0.0178(6) 0.6229(5) 0.0267(12) Uani 1 1 d . . . . .
C4 C 0.6863(8) 0.4465(7) 0.5199(6) 0.0143(12) Uani 1 1 d . . . . .
H4 H 0.6702 0.3604 0.4651 0.017 Uiso 1 1 calc R U . . .
C9 C 0.0977(8) -0.1566(6) 0.3080(5) 0.0114(11) Uani 1 1 d . . . . .
O11 O 0.1183(17) -0.0317(10) 0.1522(10) 0.087(4) Uani 1 1 d . . . . .
C11 C 0.1498(15) -0.2387(9) 0.1016(8) 0.040(2) Uani 1 1 d . . . . .
O12 O 0.000(3) -0.1785(17) -0.0319(10) 0.178(10) Uani 1 1 d . . . . .
C12 C 0.1930(15) -0.3249(9) 0.0112(8) 0.041(2) Uani 1 1 d . . . . .
H12 H 0.1959 -0.3138 -0.0597 0.049 Uiso 1 1 calc R U . . .
C15 C 0.1799(15) -0.3526(11) 0.2206(8) 0.041(2) Uani 1 1 d . . . . .
H15 H 0.1775 -0.3632 0.2917 0.049 Uiso 1 1 calc R U . . .
O5 O 0.0235(11) -0.3511(8) 0.4256(10) 0.073(3) Uani 1 1 d . . . . .
N2 N 0.082(2) -0.1458(12) 0.0698(10) 0.081(4) 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 O2 2.424(4) . ?
Nd1 O7 2.427(4) . ?
Nd1 OW2 2.442(5) . ?
Nd1 O8 2.476(5) . ?
Nd1 OW1 2.479(5) . ?
Nd1 O4 2.513(5) . ?
Nd1 O1 2.545(5) . ?
Nd1 O3 2.562(5) . ?
Nd1 O2 2.607(4) 2_556 ?
Nd1 C8 2.912(6) . ?
Nd1 C1 2.938(6) . ?
O3 C8 1.266(8) . ?
C2 C7 1.385(10) . ?
C2 C3 1.402(10) . ?
C2 C1 1.520(8) . ?
C5 C6 1.387(9) . ?
C5 C4 1.400(9) . ?
C5 C8 1.496(8) . ?
C1 O1 1.239(9) . ?
C1 O2 1.262(8) 2_556 ?
C6 C7 1.398(9) 1_665 ?
C3 C4 1.381(9) 1_445 ?
C3 N1 1.471(11) . ?
C8 O4 1.259(8) . ?
O2 C1 1.262(8) 2_556 ?
O2 Nd1 2.607(4) 2_556 ?
O8 C9 1.257(8) . ?
C13 C14 1.369(11) . ?
C13 C12 1.370(11) . ?
C13 C16 1.491(9) . ?
O7 C9 1.254(8) 2_556 ?
C10 C15 1.359(11) . ?
C10 C11 1.368(11) . ?
C10 C9 1.521(8) . ?
C14 C15 1.397(11) . ?
C7 C6 1.398(9) 1_445 ?
O9 C16 1.215(9) . ?
C16 O10 1.319(9) . ?
N1 O6 1.248(12) . ?
N1 O5 1.303(12) . ?
C4 C3 1.381(9) 1_665 ?
C9 O7 1.254(8) 2_556 ?
O11 N2 1.249(14) . ?
C11 C12 1.393(11) . ?
C11 N2 1.510(14) . ?
O12 N2 1.246(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Nd1 O7 73.84(15) . . ?
O2 Nd1 OW2 140.24(16) . . ?
O7 Nd1 OW2 75.28(16) . . ?
O2 Nd1 O8 72.53(15) . . ?
O7 Nd1 O8 137.48(15) . . ?
OW2 Nd1 O8 145.37(16) . . ?
O2 Nd1 OW1 142.30(17) . . ?
O7 Nd1 OW1 143.86(17) . . ?
OW2 Nd1 OW1 72.07(18) . . ?
O8 Nd1 OW1 73.30(17) . . ?
O2 Nd1 O4 80.78(15) . . ?
O7 Nd1 O4 122.82(15) . . ?
OW2 Nd1 O4 95.72(18) . . ?
O8 Nd1 O4 76.05(16) . . ?
OW1 Nd1 O4 75.96(18) . . ?
O2 Nd1 O1 123.97(16) . . ?
O7 Nd1 O1 84.6(2) . . ?
OW2 Nd1 O1 76.72(19) . . ?
O8 Nd1 O1 93.2(2) . . ?
OW1 Nd1 O1 73.3(2) . . ?
O4 Nd1 O1 149.17(19) . . ?
O2 Nd1 O3 76.28(15) . . ?
O7 Nd1 O3 73.10(15) . . ?
OW2 Nd1 O3 71.21(17) . . ?
O8 Nd1 O3 121.90(16) . . ?
OW1 Nd1 O3 109.62(18) . . ?
O4 Nd1 O3 51.22(15) . . ?
O1 Nd1 O3 144.6(2) . . ?
O2 Nd1 O2 73.87(16) . 2_556 ?
O7 Nd1 O2 72.13(14) . 2_556 ?
OW2 Nd1 O2 118.85(17) . 2_556 ?
O8 Nd1 O2 74.11(15) . 2_556 ?
OW1 Nd1 O2 111.15(17) . 2_556 ?
O4 Nd1 O2 145.38(15) . 2_556 ?
O1 Nd1 O2 50.23(16) . 2_556 ?
O3 Nd1 O2 139.07(14) . 2_556 ?
O2 Nd1 C8 76.93(16) . . ?
O7 Nd1 C8 98.05(17) . . ?
OW2 Nd1 C8 83.28(18) . . ?
O8 Nd1 C8 98.91(17) . . ?
OW1 Nd1 C8 93.15(19) . . ?
O4 Nd1 C8 25.49(17) . . ?
O1 Nd1 C8 158.46(18) . . ?
O3 Nd1 C8 25.73(17) . . ?
O2 Nd1 C8 150.75(15) 2_556 . ?
O2 Nd1 C1 99.26(17) . . ?
O7 Nd1 C1 77.76(17) . . ?
OW2 Nd1 C1 98.02(19) . . ?
O8 Nd1 C1 82.75(18) . . ?
OW1 Nd1 C1 91.77(19) . . ?
O4 Nd1 C1 157.78(18) . . ?
O1 Nd1 C1 24.82(18) . . ?
O3 Nd1 C1 150.63(17) . . ?
O2 Nd1 C1 25.42(16) 2_556 . ?
C8 Nd1 C1 175.08(17) . . ?
O2 Nd1 Nd1 38.51(10) . 2_556 ?
O7 Nd1 Nd1 68.50(11) . 2_556 ?
OW2 Nd1 Nd1 140.88(13) . 2_556 ?
O8 Nd1 Nd1 69.00(11) . 2_556 ?
OW1 Nd1 Nd1 135.28(13) . 2_556 ?
O4 Nd1 Nd1 115.91(12) . 2_556 ?
O1 Nd1 Nd1 85.53(12) . 2_556 ?
O3 Nd1 Nd1 110.29(11) . 2_556 ?
O2 Nd1 Nd1 35.36(10) 2_556 2_556 ?
C8 Nd1 Nd1 115.42(12) . 2_556 ?
C1 Nd1 Nd1 60.76(13) . 2_556 ?
C8 O3 Nd1 92.8(4) . . ?
C7 C2 C3 117.4(6) . . ?
C7 C2 C1 120.5(6) . . ?
C3 C2 C1 122.0(6) . . ?
C6 C5 C4 119.5(6) . . ?
C6 C5 C8 122.1(6) . . ?
C4 C5 C8 118.4(6) . . ?
O1 C1 O2 122.0(6) . 2_556 ?
O1 C1 C2 119.3(6) . . ?
O2 C1 C2 118.7(6) 2_556 . ?
O1 C1 Nd1 59.6(4) . . ?
O2 C1 Nd1 62.5(3) 2_556 . ?
C2 C1 Nd1 178.9(5) . . ?
C5 C6 C7 120.2(6) . 1_665 ?
C4 C3 C2 122.5(6) 1_445 . ?
C4 C3 N1 116.6(7) 1_445 . ?
C2 C3 N1 120.8(6) . . ?
O4 C8 O3 120.7(6) . . ?
O4 C8 C5 119.2(6) . . ?
O3 C8 C5 120.1(6) . . ?
O4 C8 Nd1 59.2(3) . . ?
O3 C8 Nd1 61.5(3) . . ?
C5 C8 Nd1 177.8(4) . . ?
C1 O2 Nd1 161.5(4) 2_556 . ?
C1 O2 Nd1 92.1(4) 2_556 2_556 ?
Nd1 O2 Nd1 106.13(16) . 2_556 ?
C9 O8 Nd1 136.0(4) . . ?
C14 C13 C12 119.0(7) . . ?
C14 C13 C16 118.0(7) . . ?
C12 C13 C16 123.1(7) . . ?
C8 O4 Nd1 95.3(4) . . ?
C9 O7 Nd1 139.4(4) 2_556 . ?
C15 C10 C11 116.2(7) . . ?
C15 C10 C9 119.7(6) . . ?
C11 C10 C9 124.0(6) . . ?
C13 C14 C15 119.8(8) . . ?
C1 O1 Nd1 95.6(4) . . ?
C2 C7 C6 121.2(7) . 1_445 ?
O9 C16 O10 124.4(6) . . ?
O9 C16 C13 122.0(6) . . ?
O10 C16 C13 113.6(6) . . ?
O6 N1 O5 119.0(9) . . ?
O6 N1 C3 119.4(8) . . ?
O5 N1 C3 121.5(9) . . ?
C3 C4 C5 119.1(6) 1_665 . ?
O7 C9 O8 127.0(6) 2_556 . ?
O7 C9 C10 117.0(5) 2_556 . ?
O8 C9 C10 115.9(5) . . ?
C10 C11 C12 123.0(8) . . ?
C10 C11 N2 120.2(7) . . ?
C12 C11 N2 116.1(8) . . ?
C13 C12 C11 119.4(8) . . ?
C10 C15 C14 122.5(8) . . ?
O11 N2 O12 122.4(12) . . ?
O11 N2 C11 114.9(12) . . ?
O12 N2 C11 122.6(11) . . ?

_refine_diff_density_max         3.891
_refine_diff_density_min         -1.562
_refine_diff_density_rms         0.267

_shelxl_version_number           2014-1

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 1436824'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H8 N2 Nd2 O24'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         996.80

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   6.9070(7)
_cell_length_b                   21.897(2)
_cell_length_c                   23.151(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3501.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    34472
_cell_measurement_theta_min      5.121
_cell_measurement_theta_max      53.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_F_000             1912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.027
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6692
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 2015)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31991
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.759
_diffrn_reflns_theta_max         27.228
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3900
_reflns_number_gt                3006
_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       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'WINGX (Farrugia, 2012)'
_computing_publication_material  'Crystal Maker (Palmer, 2009)'
_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)+(0.0326P)²+22.8885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3900
_refine_ls_number_parameters     263
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.249
_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_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 0.57830(4) 0.26843(2) 0.44936(2) 0.00639(9) Uani 1 1 d . . . . .
O1 O 0.6006(6) 0.31026(17) 0.34950(15) 0.0173(8) Uani 1 1 d . . . . .
O2 O 0.5664(6) 0.21088(17) 0.35873(15) 0.0158(8) Uani 1 1 d . . . . .
O3 O 0.7982(6) 0.35142(17) 0.46075(16) 0.0186(9) Uani 1 1 d . . . . .
O5 O 0.9150(5) 0.22452(16) 0.44759(14) 0.0103(7) Uani 1 1 d . . . . .
O6 O 0.2284(5) 0.23946(16) 0.44851(14) 0.0111(7) Uani 1 1 d . . . . .
O4 O 0.5494(5) 0.16375(16) 0.47969(15) 0.0115(7) Uani 1 1 d . . . . .
C1 C 0.5824(7) 0.2577(2) 0.3274(2) 0.0116(10) Uani 1 1 d . . . . .
C2 C 0.5795(7) 0.2497(2) 0.2634(2) 0.0091(10) Uani 1 1 d . . . . .
C3 C 0.5707(9) 0.1918(2) 0.2398(2) 0.0193(12) Uani 1 1 d . . . . .
H3 H 0.5646 0.1576 0.2636 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5868(9) 0.3002(2) 0.2271(2) 0.0177(12) Uani 1 1 d . . . . .
H4 H 0.5928 0.3392 0.2429 0.021 Uiso 1 1 calc R U . . .
C11 C 0.5730(7) 0.2685(2) 0.5785(2) 0.0077(9) Uani 1 1 d . U . . .
C12 C 0.5765(7) 0.2653(2) 0.6438(2) 0.0076(9) Uani 1 1 d . . . . .
O7 O 0.3846(6) 0.36281(18) 0.45478(18) 0.0233(9) Uani 1 1 d . . . . .
C5 C 0.5853(9) 0.2931(3) 0.1675(2) 0.0178(12) Uani 1 1 d . U . . .
H5 H 0.5901 0.3271 0.1436 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5710(10) 0.1854(2) 0.1804(2) 0.0206(13) Uani 1 1 d . . . . .
OW1 O 0.9023(7) 0.5497(2) 0.6917(2) 0.0334(11) Uani 1 1 d . . . . .
OW2 O 0.3114(6) 0.56836(19) 0.68471(18) 0.0249(10) Uani 1 1 d . . . . .
O10 O 0.6021(11) 0.1170(2) 0.1050(2) 0.0638(19) Uani 1 1 d . U . . .
O11 O 0.535(2) 0.0826(3) 0.1887(3) 0.138(3) Uani 1 1 d . U . . .
N2 N 0.5683(16) 0.1239(3) 0.1562(3) 0.073(3) Uani 1 1 d . U . . .
OW3 O 0.3841(7) 0.46956(19) 0.39006(19) 0.0262(10) Uani 1 1 d . . . . .
N1 N 0.0976(18) 0.0692(5) 0.0995(5) 0.035(3) Uani 0.5 1 d . U P A -1
O9 O -0.039(2) 0.0863(6) 0.1297(6) 0.070(4) Uani 0.5 1 d . U P A -1
O8 O 0.263(3) 0.0755(8) 0.1107(7) 0.096(5) Uani 0.5 1 d . U P A -1
C7 C 0.9313(8) 0.3697(2) 0.4932(2) 0.0125(10) Uani 1 1 d . . . B -1
C10 C 0.8980(8) 0.4750(3) 0.4534(2) 0.0186(12) Uani 1 1 d . . . B -1
C9 C 1.0628(9) 0.4627(3) 0.5441(2) 0.0197(12) Uani 1 1 d . . . B -1
C8 C 0.9641(7) 0.4374(2) 0.4980(2) 0.0134(11) Uani 1 1 d . . . B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O3 2.383(4) . ?
Nd1 O4 2.406(3) . ?
Nd1 O2 2.449(4) . ?
Nd1 O7 2.465(4) . ?
Nd1 O1 2.492(4) . ?
Nd1 O6 2.499(4) . ?
Nd1 O5 2.517(3) . ?
Nd1 O6 2.588(3) 4_556 ?
Nd1 O5 2.644(3) 4_456 ?
Nd1 C1 2.834(5) . ?
Nd1 C11 2.990(5) . ?
O1 C1 1.266(6) . ?
O2 C1 1.261(6) . ?
O3 C7 1.253(6) . ?
O5 C11 1.256(6) 4_556 ?
O5 Nd1 2.644(3) 4_556 ?
O6 C11 1.255(6) 4_456 ?
O6 Nd1 2.588(3) 4_456 ?
C1 C2 1.492(7) . ?
C2 C3 1.382(7) . ?
C2 C4 1.389(7) . ?
C3 C6 1.382(7) . ?
C4 C5 1.389(7) . ?
C11 O6 1.255(6) 4_556 ?
C11 O5 1.256(6) 4_456 ?
C11 C12 1.514(7) . ?
C12 C6 1.372(7) 7_566 ?
C12 C5 1.393(7) 7_566 ?
C5 C12 1.393(7) 7_565 ?
C6 C12 1.372(7) 7_565 ?
C6 N2 1.458(8) . ?
O10 N2 1.218(8) . ?
O11 N2 1.200(9) . ?
N1 O8 1.18(2) . ?
N1 O9 1.232(17) . ?
C7 C8 1.502(7) . ?
C10 C8 1.399(7) . ?
C9 C8 1.383(7) . ?

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 Nd1 O4 138.34(12) . . ?
O3 Nd1 O2 120.57(13) . . ?
O4 Nd1 O2 75.94(12) . . ?
O3 Nd1 O7 72.60(14) . . ?
O4 Nd1 O7 137.64(13) . . ?
O2 Nd1 O7 117.18(14) . . ?
O3 Nd1 O1 77.46(12) . . ?
O4 Nd1 O1 128.78(12) . . ?
O2 Nd1 O1 52.86(12) . . ?
O7 Nd1 O1 76.86(13) . . ?
O3 Nd1 O6 144.19(13) . . ?
O4 Nd1 O6 71.35(12) . . ?
O2 Nd1 O6 80.22(12) . . ?
O7 Nd1 O6 71.83(13) . . ?
O1 Nd1 O6 98.39(12) . . ?
O3 Nd1 O5 72.79(12) . . ?
O4 Nd1 O5 73.58(11) . . ?
O2 Nd1 O5 79.66(12) . . ?
O7 Nd1 O5 145.35(13) . . ?
O1 Nd1 O5 93.91(12) . . ?
O6 Nd1 O5 142.81(11) . . ?
O3 Nd1 O6 72.20(12) . 4_556 ?
O4 Nd1 O6 72.72(11) . 4_556 ?
O2 Nd1 O6 139.64(12) . 4_556 ?
O7 Nd1 O6 103.11(13) . 4_556 ?
O1 Nd1 O6 147.95(12) . 4_556 ?
O6 Nd1 O6 112.20(8) . 4_556 ?
O5 Nd1 O6 67.61(11) . 4_556 ?
O3 Nd1 O5 97.33(12) . 4_456 ?
O4 Nd1 O5 75.92(11) . 4_456 ?
O2 Nd1 O5 142.09(12) . 4_456 ?
O7 Nd1 O5 70.94(12) . 4_456 ?
O1 Nd1 O5 147.39(12) . 4_456 ?
O6 Nd1 O5 67.00(11) . 4_456 ?
O5 Nd1 O5 115.55(8) . 4_456 ?
O6 Nd1 O5 49.47(11) 4_556 4_456 ?
O3 Nd1 C1 99.62(14) . . ?
O4 Nd1 C1 102.28(14) . . ?
O2 Nd1 C1 26.34(14) . . ?
O7 Nd1 C1 97.23(14) . . ?
O1 Nd1 C1 26.52(14) . . ?
O6 Nd1 C1 88.90(13) . . ?
O5 Nd1 C1 86.72(12) . . ?
O6 Nd1 C1 154.29(13) 4_556 . ?
O5 Nd1 C1 155.30(12) 4_456 . ?
O3 Nd1 C11 84.07(13) . . ?
O4 Nd1 C11 73.00(12) . . ?
O2 Nd1 C11 148.94(12) . . ?
O7 Nd1 C11 86.66(13) . . ?
O1 Nd1 C11 158.18(12) . . ?
O6 Nd1 C11 89.77(12) . . ?
O5 Nd1 C11 91.60(12) . . ?
O6 Nd1 C11 24.67(12) 4_556 . ?
O5 Nd1 C11 24.80(12) 4_456 . ?
C1 Nd1 C11 175.27(14) . . ?
C1 O1 Nd1 92.0(3) . . ?
C1 O2 Nd1 94.1(3) . . ?
C7 O3 Nd1 141.1(3) . . ?
C11 O5 Nd1 139.8(3) 4_556 . ?
C11 O5 Nd1 93.2(3) 4_556 4_556 ?
Nd1 O5 Nd1 110.93(12) . 4_556 ?
C11 O6 Nd1 150.1(3) 4_456 . ?
C11 O6 Nd1 95.9(3) 4_456 4_456 ?
Nd1 O6 Nd1 113.41(13) . 4_456 ?
O2 C1 O1 121.0(5) . . ?
O2 C1 C2 118.3(5) . . ?
O1 C1 C2 120.6(5) . . ?
O2 C1 Nd1 59.5(3) . . ?
O1 C1 Nd1 61.5(3) . . ?
C2 C1 Nd1 177.6(4) . . ?
C3 C2 C4 119.5(5) . . ?
C3 C2 C1 120.1(5) . . ?
C4 C2 C1 120.4(5) . . ?
C2 C3 C6 119.1(5) . . ?
C5 C4 C2 120.7(5) . . ?
O6 C11 O5 121.3(4) 4_556 4_456 ?
O6 C11 C12 118.5(4) 4_556 . ?
O5 C11 C12 120.0(4) 4_456 . ?
O6 C11 Nd1 59.4(2) 4_556 . ?
O5 C11 Nd1 62.0(2) 4_456 . ?
C12 C11 Nd1 176.9(3) . . ?
C6 C12 C5 118.7(5) 7_566 7_566 ?
C6 C12 C11 125.5(4) 7_566 . ?
C5 C12 C11 115.9(4) 7_566 . ?
C4 C5 C12 119.6(5) . 7_565 ?
C12 C6 C3 122.3(5) 7_565 . ?
C12 C6 N2 119.2(5) 7_565 . ?
C3 C6 N2 118.4(5) . . ?
O11 N2 O10 123.5(7) . . ?
O11 N2 C6 117.3(6) . . ?
O10 N2 C6 119.2(6) . . ?
O8 N1 O9 125.6(15) . . ?
O3 C7 C8 118.1(5) . . ?
C9 C8 C10 119.7(5) . . ?
C9 C8 C7 121.8(5) . . ?
C10 C8 C7 118.5(5) . . ?

_refine_diff_density_max         2.410
_refine_diff_density_min         -1.933
_refine_diff_density_rms         0.177

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P b c a'
_symmetry_int_tables_number      61
_chemical_absolute_configuration ?


#===END
