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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b
_audit_block_doi                 10.5517/cc1450p0
_database_code_depnum_ccdc_archive 'CCDC 1047511'
_audit_update_record             
;
2015-02-05 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 Eu N O12'
_chemical_formula_weight         624.29

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

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

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

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

_cell_length_a                   9.0855(10)
_cell_length_b                   18.021(2)
_cell_length_c                   14.2701(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.531(2)
_cell_angle_gamma                90
_cell_volume                     2239.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    2.868
_shelx_estimated_absorpt_T_min   0.501
_shelx_estimated_absorpt_T_max   0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_T_max  0.532
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13450
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.869
_diffrn_reflns_theta_max         28.194
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5274
_reflns_number_gt                4482
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.6914P]
 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         5274
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_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
Eu1 Eu 0.69153(3) 1.07568(2) 0.51215(2) 0.01747(13) Uani 1 1 d . . . . .
C10 C 0.3501(7) 0.8502(3) 0.1911(5) 0.0306(13) Uani 1 1 d . . . . .
H10 H 0.3177 0.8029 0.2023 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6295(8) 0.7501(3) 0.2659(5) 0.0341(14) Uani 1 1 d . . . . .
H6 H 0.5730 0.7374 0.2028 0.041 Uiso 1 1 calc R U . . .
C11 C 0.2949(7) 0.9640(4) 0.1115(4) 0.0323(13) Uani 1 1 d . . . . .
H11 H 0.2244 0.9950 0.0693 0.039 Uiso 1 1 calc R U . . .
O6 O 0.5374(5) 1.0693(2) 0.3443(3) 0.0243(9) Uani 1 1 d . . . . .
O5 O 0.7759(5) 1.1016(3) 0.3610(3) 0.0305(9) Uani 1 1 d . . . . .
C4 C 0.8249(7) 0.7201(3) 0.4148(5) 0.0364(15) Uani 1 1 d . . . . .
C15 C 0.6016(6) 1.1064(3) 0.1993(4) 0.0213(10) Uani 1 1 d . . . . .
C9 C 0.4985(6) 0.8718(3) 0.2389(4) 0.0220(10) Uani 1 1 d . . . . .
C20 C 0.6400(6) 1.0906(3) 0.3065(4) 0.0207(10) Uani 1 1 d . . . . .
C7 C 0.6073(7) 0.8195(3) 0.3046(4) 0.0237(11) Uani 1 1 d . . . . .
C12 C 0.4426(6) 0.9898(3) 0.1550(4) 0.0212(10) Uani 1 1 d . . . . .
C14 C 0.4935(7) 1.0634(3) 0.1300(4) 0.0242(11) Uani 1 1 d . . . . .
C13 C 0.5460(6) 0.9416(3) 0.2183(4) 0.0188(10) Uani 1 1 d . . . . .
H13 H 0.6469 0.9565 0.2467 0.023 Uiso 1 1 calc R U . . .
N1 N 0.2516(6) 0.8952(3) 0.1291(4) 0.0290(11) Uani 1 1 d . . . . .
C2 C 0.6943(6) 0.8387(3) 0.3985(4) 0.0210(10) Uani 1 1 d . . . . .
C18 C 0.4907(8) 1.1581(3) 0.0084(5) 0.0302(12) Uani 1 1 d . . . . .
H18 H 0.4489 1.1764 -0.0546 0.036 Uiso 1 1 calc R U . . .
C19 C 0.4422(7) 1.0902(3) 0.0347(4) 0.0266(12) Uani 1 1 d . . . . .
H19 H 0.3736 1.0619 -0.0126 0.032 Uiso 1 1 calc R U . . .
C3 C 0.8034(7) 0.7888(3) 0.4526(5) 0.0294(12) Uani 1 1 d . . . . .
H3 H 0.8625 0.8018 0.5151 0.035 Uiso 1 1 calc R U . . .
C17 C 0.6021(7) 1.1989(3) 0.0763(4) 0.0255(11) Uani 1 1 d . . . . .
C16 C 0.6560(6) 1.1716(3) 0.1713(4) 0.0238(11) Uani 1 1 d . . . . .
H16 H 0.7308 1.1982 0.2171 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7346(8) 0.7010(3) 0.3212(5) 0.0362(14) Uani 1 1 d . . . . .
H5 H 0.7457 0.6544 0.2959 0.043 Uiso 1 1 calc R U . . .
C8 C 0.9399(9) 0.6649(4) 0.4662(6) 0.0507(19) Uani 1 1 d . . . . .
C1 C 0.6765(6) 0.9132(3) 0.4429(4) 0.0199(10) Uani 1 1 d . . . . .
O1 O 0.7880(4) 0.9566(2) 0.4641(3) 0.0273(9) Uani 1 1 d . . . . .
O3 O 1.0072(8) 0.6814(4) 0.5539(5) 0.079(2) Uani 1 1 d . . . . .
H3A H 1.0692 0.6487 0.5783 0.118 Uiso 1 1 calc R U . . .
O4 O 0.9747(11) 0.6109(4) 0.4295(6) 0.104(3) Uani 1 1 d . . . . .
C21 C 0.6482(7) 1.2742(3) 0.0513(4) 0.0256(11) Uani 1 1 d . . . . .
O2 O 0.5514(5) 0.9321(2) 0.4574(3) 0.0252(9) Uani 1 1 d . . . . .
O8 O 0.6033(7) 1.2973(3) -0.0345(3) 0.0417(12) Uani 1 1 d . . . . .
O7 O 0.7282(6) 1.3149(2) 0.1186(3) 0.0376(10) Uani 1 1 d . . . . .
O10 O 0.7329(4) 1.0039(3) 0.6604(3) 0.0279(9) Uani 1 1 d . . . . .
H10A H 0.8094 0.9667 0.6624 0.042 Uiso 1 1 d R U . . .
H10B H 0.6386 0.9804 0.6613 0.042 Uiso 1 1 d R U . . .
O9 O 0.9559(5) 1.0854(3) 0.5841(4) 0.0390(12) Uani 1 1 d . . . . .
H9B H 1.0056 1.0416 0.5697 0.059 Uiso 1 1 d R U . . .
H9A H 0.9761 1.0903 0.6536 0.059 Uiso 1 1 d R U . . .
O11 O 0.9836(15) 0.9198(9) 0.7281(12) 0.232(11) Uani 1 1 d . . . . .
O12 O 0.0986(12) 0.1071(13) 0.7789(10) 0.254(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O9 2.334(4) . ?
Eu1 O2 2.372(4) 3_676 ?
Eu1 O6 2.409(4) . ?
Eu1 O10 2.416(4) . ?
Eu1 O7 2.453(4) 4_586 ?
Eu1 O8 2.454(5) 4_586 ?
Eu1 O1 2.487(4) . ?
Eu1 O5 2.529(4) . ?
Eu1 C21 2.812(6) 4_586 ?
Eu1 C20 2.850(6) . ?
Eu1 O2 2.892(4) . ?
Eu1 C1 3.080(5) . ?
Eu1 H9B 2.8036 . ?
Eu1 H9A 2.8031 . ?
C10 N1 1.337(8) . ?
C10 C9 1.383(8) . ?
C10 H10 0.9300 . ?
C6 C5 1.374(9) . ?
C6 C7 1.405(8) . ?
C6 H6 0.9300 . ?
C11 N1 1.347(8) . ?
C11 C12 1.388(8) . ?
C11 H11 0.9300 . ?
O6 C20 1.263(7) . ?
O5 C20 1.274(7) . ?
C4 C3 1.385(9) . ?
C4 C5 1.398(10) . ?
C4 C8 1.477(9) . ?
C15 C16 1.378(7) . ?
C15 C14 1.410(8) . ?
C15 C20 1.496(8) . ?
C9 C13 1.388(7) . ?
C9 C7 1.488(8) . ?
C7 C2 1.391(8) . ?
C12 C13 1.405(7) . ?
C12 C14 1.482(7) . ?
C14 C19 1.393(9) . ?
C13 H13 0.9300 . ?
C2 C3 1.398(8) . ?
C2 C1 1.514(7) . ?
C18 C19 1.387(8) . ?
C18 C17 1.396(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C3 H3 0.9300 . ?
C17 C16 1.393(8) . ?
C17 C21 1.494(7) . ?
C16 H16 0.9300 . ?
C5 H5 0.9300 . ?
C8 O4 1.190(10) . ?
C8 O3 1.262(10) . ?
C1 O1 1.247(7) . ?
C1 O2 1.259(7) . ?
O3 H3A 0.8200 . ?
C21 O8 1.246(7) . ?
C21 O7 1.262(7) . ?
C21 Eu1 2.812(6) 4_585 ?
O2 Eu1 2.372(4) 3_676 ?
O8 Eu1 2.454(5) 4_585 ?
O7 Eu1 2.454(4) 4_585 ?
O10 H10A 0.9600 . ?
O10 H10B 0.9600 . ?
O9 H9B 0.9600 . ?
O9 H9A 0.9600 . ?

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
O9 Eu1 O2 144.93(17) . 3_676 ?
O9 Eu1 O6 132.47(17) . . ?
O2 Eu1 O6 82.60(15) 3_676 . ?
O9 Eu1 O10 76.75(17) . . ?
O2 Eu1 O10 74.29(14) 3_676 . ?
O6 Eu1 O10 138.31(14) . . ?
O9 Eu1 O7 74.08(16) . 4_586 ?
O2 Eu1 O7 84.46(15) 3_676 4_586 ?
O6 Eu1 O7 126.31(14) . 4_586 ?
O10 Eu1 O7 85.88(14) . 4_586 ?
O9 Eu1 O8 105.37(18) . 4_586 ?
O2 Eu1 O8 81.68(16) 3_676 4_586 ?
O6 Eu1 O8 73.85(14) . 4_586 ?
O10 Eu1 O8 133.98(14) . 4_586 ?
O7 Eu1 O8 52.75(15) 4_586 4_586 ?
O9 Eu1 O1 77.70(15) . . ?
O2 Eu1 O1 114.76(13) 3_676 . ?
O6 Eu1 O1 80.54(14) . . ?
O10 Eu1 O1 78.47(15) . . ?
O7 Eu1 O1 150.20(15) 4_586 . ?
O8 Eu1 O1 147.53(15) 4_586 . ?
O9 Eu1 O5 80.65(16) . . ?
O2 Eu1 O5 133.68(14) 3_676 . ?
O6 Eu1 O5 52.60(14) . . ?
O10 Eu1 O5 146.72(14) . . ?
O7 Eu1 O5 111.03(16) 4_586 . ?
O8 Eu1 O5 75.60(15) 4_586 . ?
O1 Eu1 O5 73.03(15) . . ?
O9 Eu1 C21 91.43(17) . 4_586 ?
O2 Eu1 C21 80.23(15) 3_676 4_586 ?
O6 Eu1 C21 99.70(15) . 4_586 ?
O10 Eu1 C21 109.69(16) . 4_586 ?
O7 Eu1 C21 26.63(16) 4_586 4_586 ?
O8 Eu1 C21 26.26(15) 4_586 4_586 ?
O1 Eu1 C21 164.77(15) . 4_586 ?
O5 Eu1 C21 94.88(16) . 4_586 ?
O9 Eu1 C20 107.01(18) . . ?
O2 Eu1 C20 107.79(15) 3_676 . ?
O6 Eu1 C20 26.10(15) . . ?
O10 Eu1 C20 153.00(15) . . ?
O7 Eu1 C20 121.05(15) 4_586 . ?
O8 Eu1 C20 71.81(14) 4_586 . ?
O1 Eu1 C20 76.39(15) . . ?
O5 Eu1 C20 26.54(14) . . ?
C21 Eu1 C20 97.05(15) 4_586 . ?
O9 Eu1 O2 120.32(14) . . ?
O2 Eu1 O2 68.63(14) 3_676 . ?
O6 Eu1 O2 66.56(12) . . ?
O10 Eu1 O2 72.80(14) . . ?
O7 Eu1 O2 149.12(14) 4_586 . ?
O8 Eu1 O2 132.59(16) 4_586 . ?
O1 Eu1 O2 46.84(11) . . ?
O5 Eu1 O2 98.74(14) . . ?
C21 Eu1 O2 147.00(14) 4_586 . ?
C20 Eu1 O2 82.84(14) . . ?
O9 Eu1 C1 99.13(16) . . ?
O2 Eu1 C1 92.53(14) 3_676 . ?
O6 Eu1 C1 71.08(13) . . ?
O10 Eu1 C1 75.74(15) . . ?
O7 Eu1 C1 161.49(14) 4_586 . ?
O8 Eu1 C1 144.91(15) 4_586 . ?
O1 Eu1 C1 22.85(14) . . ?
O5 Eu1 C1 84.18(15) . . ?
C21 Eu1 C1 169.08(16) 4_586 . ?
C20 Eu1 C1 77.28(15) . . ?
O2 Eu1 C1 24.07(13) . . ?
O9 Eu1 H9B 18.8 . . ?
O2 Eu1 H9B 148.9 3_676 . ?
O6 Eu1 H9B 122.4 . . ?
O10 Eu1 H9B 74.6 . . ?
O7 Eu1 H9B 92.7 4_586 . ?
O8 Eu1 H9B 120.7 4_586 . ?
O1 Eu1 H9B 58.9 . . ?
O5 Eu1 H9B 76.1 . . ?
C21 Eu1 H9B 109.9 4_586 . ?
C20 Eu1 H9B 100.2 . . ?
O2 Eu1 H9B 102.5 . . ?
C1 Eu1 H9B 80.5 . . ?
O9 Eu1 H9A 18.9 . . ?
O2 Eu1 H9A 126.1 3_676 . ?
O6 Eu1 H9A 151.2 . . ?
O10 Eu1 H9A 62.5 . . ?
O7 Eu1 H9A 62.8 4_586 . ?
O8 Eu1 H9A 105.7 4_586 . ?
O1 Eu1 H9A 87.4 . . ?
O5 Eu1 H9A 98.9 . . ?
C21 Eu1 H9A 85.4 4_586 . ?
C20 Eu1 H9A 125.5 . . ?
O2 Eu1 H9A 121.6 . . ?
C1 Eu1 H9A 105.6 . . ?
H9B Eu1 H9A 32.5 . . ?
N1 C10 C9 122.1(5) . . ?
N1 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C5 C6 C7 120.2(6) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
N1 C11 C12 121.5(5) . . ?
N1 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C20 O6 Eu1 96.9(4) . . ?
C20 O5 Eu1 90.9(3) . . ?
C3 C4 C5 118.9(6) . . ?
C3 C4 C8 124.5(7) . . ?
C5 C4 C8 116.7(6) . . ?
C16 C15 C14 120.0(5) . . ?
C16 C15 C20 117.4(5) . . ?
C14 C15 C20 121.7(5) . . ?
C10 C9 C13 117.9(5) . . ?
C10 C9 C7 120.9(5) . . ?
C13 C9 C7 121.0(5) . . ?
O6 C20 O5 119.4(5) . . ?
O6 C20 C15 120.6(5) . . ?
O5 C20 C15 119.9(5) . . ?
O6 C20 Eu1 57.0(3) . . ?
O5 C20 Eu1 62.5(3) . . ?
C15 C20 Eu1 173.1(4) . . ?
C2 C7 C6 119.6(5) . . ?
C2 C7 C9 122.9(5) . . ?
C6 C7 C9 117.3(5) . . ?
C11 C12 C13 117.7(5) . . ?
C11 C12 C14 121.4(5) . . ?
C13 C12 C14 120.8(5) . . ?
C19 C14 C15 117.9(5) . . ?
C19 C14 C12 120.3(5) . . ?
C15 C14 C12 121.7(5) . . ?
C9 C13 C12 120.4(5) . . ?
C9 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C10 N1 C11 120.4(5) . . ?
C7 C2 C3 119.5(5) . . ?
C7 C2 C1 121.6(5) . . ?
C3 C2 C1 118.9(5) . . ?
C19 C18 C17 120.0(6) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 121.7(6) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C4 C3 C2 121.1(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C16 C17 C18 118.3(5) . . ?
C16 C17 C21 120.6(5) . . ?
C18 C17 C21 120.7(5) . . ?
C15 C16 C17 121.8(5) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C6 C5 C4 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
O4 C8 O3 120.9(8) . . ?
O4 C8 C4 124.8(8) . . ?
O3 C8 C4 114.2(7) . . ?
O1 C1 O2 120.0(5) . . ?
O1 C1 C2 118.8(5) . . ?
O2 C1 C2 121.2(5) . . ?
O1 C1 Eu1 50.7(3) . . ?
O2 C1 Eu1 69.5(3) . . ?
C2 C1 Eu1 167.9(4) . . ?
C1 O1 Eu1 106.4(3) . . ?
C8 O3 H3A 109.5 . . ?
O8 C21 O7 120.8(5) . . ?
O8 C21 C17 120.1(5) . . ?
O7 C21 C17 119.0(5) . . ?
O8 C21 Eu1 60.6(3) . 4_585 ?
O7 C21 Eu1 60.6(3) . 4_585 ?
C17 C21 Eu1 170.5(4) . 4_585 ?
C1 O2 Eu1 160.9(4) . 3_676 ?
C1 O2 Eu1 86.4(3) . . ?
Eu1 O2 Eu1 111.37(14) 3_676 . ?
C21 O8 Eu1 93.1(4) . 4_585 ?
C21 O7 Eu1 92.7(3) . 4_585 ?
Eu1 O10 H10A 109.4 . . ?
Eu1 O10 H10B 109.4 . . ?
H10A O10 H10B 109.5 . . ?
Eu1 O9 H9B 109.4 . . ?
Eu1 O9 H9A 109.4 . . ?
H9B O9 H9A 109.5 . . ?

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
N1 C10 C9 C13 -2.3(9) . . . . ?
N1 C10 C9 C7 -177.7(6) . . . . ?
Eu1 O6 C20 O5 4.5(5) . . . . ?
Eu1 O6 C20 C15 -172.3(4) . . . . ?
Eu1 O5 C20 O6 -4.3(5) . . . . ?
Eu1 O5 C20 C15 172.6(4) . . . . ?
C16 C15 C20 O6 132.7(5) . . . . ?
C14 C15 C20 O6 -37.0(8) . . . . ?
C16 C15 C20 O5 -44.2(7) . . . . ?
C14 C15 C20 O5 146.2(6) . . . . ?
C5 C6 C7 C2 1.2(9) . . . . ?
C5 C6 C7 C9 176.5(6) . . . . ?
C10 C9 C7 C2 -131.1(6) . . . . ?
C13 C9 C7 C2 53.6(8) . . . . ?
C10 C9 C7 C6 53.8(8) . . . . ?
C13 C9 C7 C6 -121.6(6) . . . . ?
N1 C11 C12 C13 0.0(9) . . . . ?
N1 C11 C12 C14 175.4(6) . . . . ?
C16 C15 C14 C19 -1.7(8) . . . . ?
C20 C15 C14 C19 167.7(5) . . . . ?
C16 C15 C14 C12 174.5(5) . . . . ?
C20 C15 C14 C12 -16.2(8) . . . . ?
C11 C12 C14 C19 -36.1(8) . . . . ?
C13 C12 C14 C19 139.2(6) . . . . ?
C11 C12 C14 C15 147.9(6) . . . . ?
C13 C12 C14 C15 -36.8(8) . . . . ?
C10 C9 C13 C12 3.6(8) . . . . ?
C7 C9 C13 C12 179.0(5) . . . . ?
C11 C12 C13 C9 -2.5(8) . . . . ?
C14 C12 C13 C9 -178.0(5) . . . . ?
C9 C10 N1 C11 -0.2(10) . . . . ?
C12 C11 N1 C10 1.4(10) . . . . ?
C6 C7 C2 C3 0.5(8) . . . . ?
C9 C7 C2 C3 -174.6(5) . . . . ?
C6 C7 C2 C1 179.0(5) . . . . ?
C9 C7 C2 C1 4.0(8) . . . . ?
C17 C18 C19 C14 4.8(9) . . . . ?
C15 C14 C19 C18 -2.2(9) . . . . ?
C12 C14 C19 C18 -178.4(6) . . . . ?
C5 C4 C3 C2 -0.4(10) . . . . ?
C8 C4 C3 C2 178.6(7) . . . . ?
C7 C2 C3 C4 -0.9(9) . . . . ?
C1 C2 C3 C4 -179.4(6) . . . . ?
C19 C18 C17 C16 -3.4(9) . . . . ?
C19 C18 C17 C21 -176.0(6) . . . . ?
C14 C15 C16 C17 3.0(8) . . . . ?
C20 C15 C16 C17 -166.8(5) . . . . ?
C18 C17 C16 C15 -0.5(9) . . . . ?
C21 C17 C16 C15 172.2(5) . . . . ?
C7 C6 C5 C4 -2.5(10) . . . . ?
C3 C4 C5 C6 2.1(10) . . . . ?
C8 C4 C5 C6 -177.0(7) . . . . ?
C3 C4 C8 O4 -168.5(10) . . . . ?
C5 C4 C8 O4 10.6(14) . . . . ?
C3 C4 C8 O3 7.9(12) . . . . ?
C5 C4 C8 O3 -173.0(8) . . . . ?
C7 C2 C1 O1 -116.8(6) . . . . ?
C3 C2 C1 O1 61.8(7) . . . . ?
C7 C2 C1 O2 62.3(7) . . . . ?
C3 C2 C1 O2 -119.1(6) . . . . ?
C7 C2 C1 Eu1 -87.9(18) . . . . ?
C3 C2 C1 Eu1 90.7(18) . . . . ?
O2 C1 O1 Eu1 -6.7(6) . . . . ?
C2 C1 O1 Eu1 172.4(4) . . . . ?
C16 C17 C21 O8 177.8(6) . . . . ?
C18 C17 C21 O8 -9.7(9) . . . . ?
C16 C17 C21 O7 -4.8(9) . . . . ?
C18 C17 C21 O7 167.7(6) . . . . ?
O1 C1 O2 Eu1 -153.9(9) . . . 3_676 ?
C2 C1 O2 Eu1 27.0(15) . . . 3_676 ?
Eu1 C1 O2 Eu1 -159.5(12) . . . 3_676 ?
O1 C1 O2 Eu1 5.5(5) . . . . ?
C2 C1 O2 Eu1 -173.6(5) . . . . ?
O7 C21 O8 Eu1 -8.3(6) . . . 4_585 ?
C17 C21 O8 Eu1 169.1(5) . . . 4_585 ?
O8 C21 O7 Eu1 8.3(6) . . . 4_585 ?
C17 C21 O7 Eu1 -169.1(5) . . . 4_585 ?

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
O3 H3A N1 0.82 1.79 2.574(8) 158.7 4_676
O10 H10A O11 0.96 1.80 2.676(10) 149.8 .
O10 H10B O6 0.96 1.81 2.772(6) 175.3 3_676
O9 H9B O1 0.96 2.07 2.715(6) 123.5 3_776
O9 H9A O12 0.96 1.84 2.740(12) 154.5 1_665

_refine_diff_density_max         1.493
_refine_diff_density_min         -1.731
_refine_diff_density_rms         0.379

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/cc1450q1
_database_code_depnum_ccdc_archive 'CCDC 1047512'
_audit_update_record             
;
2015-02-05 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 N Nd O12'
_chemical_formula_weight         616.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.125(3)
_cell_length_b                   17.970(6)
_cell_length_c                   14.297(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.386(5)
_cell_angle_gamma                90
_cell_volume                     2249.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_F_000             1212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    2.376
_shelx_estimated_absorpt_T_min   0.536
_shelx_estimated_absorpt_T_max   0.599
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_T_max  0.565
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13683
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.868
_diffrn_reflns_theta_max         28.382
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5375
_reflns_number_gt                4845
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1378P)²+1.2100P]
 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         5375
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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
O6 O 0.4472(5) 0.9325(2) 0.0453(3) 0.0221(8) Uani 1 1 d . . . . .
O3 O 0.2752(5) 1.3119(2) 0.3848(3) 0.0307(9) Uani 1 1 d . . . . .
O4 O 0.4052(6) 1.2952(2) 0.5358(3) 0.0388(11) Uani 1 1 d . . . . .
C8 C 0.3565(6) 1.2718(3) 0.4526(4) 0.0235(10) Uani 1 1 d . . . . .
Nd01 Nd 0.30923(3) 1.07616(2) -0.01166(2) 0.01312(15) Uani 1 1 d . . . . .
O9 O 0.2670(4) 1.0031(2) -0.1619(3) 0.0276(8) Uani 1 1 d . . . . .
H9A H 0.1839 0.9691 -0.1670 0.041 Uiso 1 1 d R U . . .
H9B H 0.3579 0.9756 -0.1603 0.041 Uiso 1 1 d R U . . .
O5 O 0.2074(4) 0.9544(2) 0.0332(3) 0.0243(8) Uani 1 1 d . . . . .
O10 O 0.0395(5) 1.0870(3) -0.0855(4) 0.0364(11) Uani 1 1 d . . . . .
H10A H 0.0189 1.0863 -0.1552 0.055 Uiso 1 1 d R U . . .
H10B H -0.0118 1.0460 -0.0653 0.055 Uiso 1 1 d R U . . .
O2 O 0.4657(5) 1.06909(19) 0.1595(3) 0.0220(8) Uani 1 1 d . . . . .
C19 C 0.3720(7) 0.7493(3) 0.2326(4) 0.0250(11) Uani 1 1 d . . . . .
H19 H 0.4322 0.7353 0.2941 0.030 Uiso 1 1 calc R U . . .
O1 O 0.2281(5) 1.1012(3) 0.1424(3) 0.0281(8) Uani 1 1 d . . . . .
C13 C 0.4575(6) 0.9402(3) 0.2823(4) 0.0174(9) Uani 1 1 d . . . . .
H13 H 0.3580 0.9560 0.2535 0.021 Uiso 1 1 calc R U . . .
C21 C 0.0573(7) 0.6656(4) 0.0314(5) 0.0390(15) Uani 1 1 d . . . . .
C6 C 0.5627(7) 1.0880(3) 0.4665(4) 0.0254(11) Uani 1 1 d . . . . .
H6 H 0.6331 1.0600 0.5129 0.030 Uiso 1 1 calc R U . . .
C1 C 0.3613(6) 1.0898(3) 0.1954(4) 0.0175(9) Uani 1 1 d . . . . .
C14 C 0.3929(5) 0.8183(3) 0.1965(4) 0.0174(9) Uani 1 1 d . . . . .
O8 O 0.0246(8) 0.6107(3) 0.0719(5) 0.073(2) Uani 1 1 d . . . . .
O11 O 1.0086(12) 0.9249(9) 0.7693(10) 0.204(10) Uani 1 1 d . . . . .
C9 C 0.5596(6) 0.9877(2) 0.3467(4) 0.0175(9) Uani 1 1 d . . . . .
C17 C 0.1760(6) 0.7194(3) 0.0853(4) 0.0256(11) Uani 1 1 d . . . . .
C15 C 0.3071(5) 0.8383(2) 0.1013(4) 0.0157(9) Uani 1 1 d . . . . .
C3 C 0.3463(6) 1.1690(3) 0.3322(4) 0.0211(10) Uani 1 1 d . . . . .
H3 H 0.2683 1.1947 0.2879 0.025 Uiso 1 1 calc R U . . .
C12 C 0.5020(6) 0.8704(3) 0.2608(3) 0.0176(9) Uani 1 1 d . . . . .
N1 N 0.7473(5) 0.8930(3) 0.3695(4) 0.0272(10) Uani 1 1 d . . . . .
C7 C 0.5090(6) 1.0612(3) 0.3724(4) 0.0193(10) Uani 1 1 d . . . . .
C2 C 0.4025(6) 1.1052(3) 0.3034(4) 0.0192(9) Uani 1 1 d . . . . .
C5 C 0.5137(7) 1.1559(3) 0.4934(4) 0.0256(11) Uani 1 1 d . . . . .
H5 H 0.5552 1.1740 0.5562 0.031 Uiso 1 1 calc R U . . .
C16 C 0.1983(6) 0.7884(3) 0.0466(4) 0.0223(10) Uani 1 1 d . . . . .
H16 H 0.1406 0.8014 -0.0159 0.027 Uiso 1 1 calc R U . . .
C20 C 0.3219(6) 0.9121(3) 0.0572(4) 0.0159(9) Uani 1 1 d . . . . .
O7 O -0.0064(7) 0.6817(4) -0.0555(5) 0.072(2) Uani 1 1 d . . . . .
H7 H -0.0696 0.6497 -0.0799 0.108 Uiso 1 1 calc R U . . .
C4 C 0.4037(6) 1.1965(3) 0.4270(4) 0.0213(10) Uani 1 1 d . . . . .
C10 C 0.7055(6) 0.9617(3) 0.3882(4) 0.0240(11) Uani 1 1 d . . . . .
H10 H 0.7765 0.9924 0.4301 0.029 Uiso 1 1 calc R U . . .
C18 C 0.2632(7) 0.7001(3) 0.1792(4) 0.0292(12) Uani 1 1 d . . . . .
H18 H 0.2483 0.6544 0.2057 0.035 Uiso 1 1 calc R U . . .
C11 C 0.6500(6) 0.8483(3) 0.3087(4) 0.0249(11) Uani 1 1 d . . . . .
H11 H 0.6817 0.8007 0.2978 0.030 Uiso 1 1 calc R U . . .
O12 O 0.903(2) 0.1131(17) 0.7213(11) 0.273(13) 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
O6 C20 1.257(6) . ?
O6 Nd01 2.408(4) 3_675 ?
O6 Nd01 2.887(4) . ?
O3 C8 1.266(7) . ?
O3 Nd01 2.464(4) 4_586 ?
O4 C8 1.222(7) . ?
O4 Nd01 2.497(4) 4_586 ?
C8 C4 1.496(6) . ?
C8 Nd01 2.835(5) 4_586 ?
Nd01 O10 2.396(5) . ?
Nd01 O6 2.408(4) 3_675 ?
Nd01 O9 2.454(4) . ?
Nd01 O2 2.464(4) . ?
Nd01 O3 2.464(4) 4_585 ?
Nd01 O4 2.497(4) 4_585 ?
Nd01 O5 2.530(4) . ?
Nd01 O1 2.555(4) . ?
Nd01 C8 2.835(5) 4_585 ?
Nd01 C1 2.873(5) . ?
O9 H9A 0.9600 . ?
O9 H9B 0.9600 . ?
O5 C20 1.259(6) . ?
O10 H10A 0.9600 . ?
O10 H10B 0.9600 . ?
O2 C1 1.259(7) . ?
C19 C14 1.377(7) . ?
C19 C18 1.386(7) . ?
C19 H19 0.9300 . ?
O1 C1 1.254(6) . ?
C13 C12 1.381(6) . ?
C13 C9 1.400(7) . ?
C13 H13 0.9300 . ?
C21 O8 1.223(9) . ?
C21 O7 1.249(9) . ?
C21 C17 1.494(8) . ?
C6 C7 1.383(8) . ?
C6 C5 1.390(8) . ?
C6 H6 0.9300 . ?
C1 C2 1.508(7) . ?
C14 C15 1.412(7) . ?
C14 C12 1.481(6) . ?
C9 C10 1.377(7) . ?
C9 C7 1.479(6) . ?
C17 C16 1.396(7) . ?
C17 C18 1.397(8) . ?
C15 C16 1.401(7) . ?
C15 C20 1.491(6) . ?
C3 C2 1.366(7) . ?
C3 C4 1.397(7) . ?
C3 H3 0.9300 . ?
C12 C11 1.389(7) . ?
N1 C11 1.325(7) . ?
N1 C10 1.341(7) . ?
C7 C2 1.415(7) . ?
C5 C4 1.379(8) . ?
C5 H5 0.9300 . ?
C16 H16 0.9300 . ?
O7 H7 0.8200 . ?
C10 H10 0.9300 . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?

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
C20 O6 Nd01 159.1(3) . 3_675 ?
C20 O6 Nd01 87.6(3) . . ?
Nd01 O6 Nd01 110.79(13) 3_675 . ?
C8 O3 Nd01 93.3(3) . 4_586 ?
C8 O4 Nd01 92.9(3) . 4_586 ?
O4 C8 O3 121.5(5) . . ?
O4 C8 C4 120.0(5) . . ?
O3 C8 C4 118.3(5) . . ?
O4 C8 Nd01 61.6(3) . 4_586 ?
O3 C8 Nd01 60.2(2) . 4_586 ?
C4 C8 Nd01 169.9(4) . 4_586 ?
O10 Nd01 O6 143.90(17) . 3_675 ?
O10 Nd01 O9 76.67(16) . . ?
O6 Nd01 O9 73.51(14) 3_675 . ?
O10 Nd01 O2 132.62(16) . . ?
O6 Nd01 O2 83.48(15) 3_675 . ?
O9 Nd01 O2 138.23(13) . . ?
O10 Nd01 O3 74.30(15) . 4_585 ?
O6 Nd01 O3 84.24(14) 3_675 4_585 ?
O9 Nd01 O3 87.07(14) . 4_585 ?
O2 Nd01 O3 125.31(13) . 4_585 ?
O10 Nd01 O4 106.40(17) . 4_585 ?
O6 Nd01 O4 80.89(15) 3_675 4_585 ?
O9 Nd01 O4 133.63(14) . 4_585 ?
O2 Nd01 O4 73.57(13) . 4_585 ?
O3 Nd01 O4 51.90(13) 4_585 4_585 ?
O10 Nd01 O5 77.12(14) . . ?
O6 Nd01 O5 114.86(12) 3_675 . ?
O9 Nd01 O5 77.34(14) . . ?
O2 Nd01 O5 81.66(13) . . ?
O3 Nd01 O5 149.91(13) 4_585 . ?
O4 Nd01 O5 149.03(14) 4_585 . ?
O10 Nd01 O1 81.63(16) . . ?
O6 Nd01 O1 133.81(14) 3_675 . ?
O9 Nd01 O1 146.84(14) . . ?
O2 Nd01 O1 51.70(13) . . ?
O3 Nd01 O1 110.88(14) 4_585 . ?
O4 Nd01 O1 76.54(15) 4_585 . ?
O5 Nd01 O1 73.56(14) . . ?
O10 Nd01 C8 91.83(16) . 4_585 ?
O6 Nd01 C8 80.23(14) 3_675 4_585 ?
O9 Nd01 C8 110.63(15) . 4_585 ?
O2 Nd01 C8 98.84(14) . 4_585 ?
O3 Nd01 C8 26.48(15) 4_585 4_585 ?
O4 Nd01 C8 25.49(15) 4_585 4_585 ?
O5 Nd01 C8 164.77(14) . 4_585 ?
O1 Nd01 C8 94.69(15) . 4_585 ?
O10 Nd01 C1 107.34(17) . . ?
O6 Nd01 C1 108.53(15) 3_675 . ?
O9 Nd01 C1 152.51(14) . . ?
O2 Nd01 C1 25.85(15) . . ?
O3 Nd01 C1 120.36(14) 4_585 . ?
O4 Nd01 C1 72.39(14) 4_585 . ?
O5 Nd01 C1 77.20(14) . . ?
O1 Nd01 C1 25.88(14) . . ?
C8 Nd01 C1 96.56(15) 4_585 . ?
O10 Nd01 O6 120.59(14) . . ?
O6 Nd01 O6 69.21(13) 3_675 . ?
O9 Nd01 O6 73.55(13) . . ?
O2 Nd01 O6 65.74(12) . . ?
O3 Nd01 O6 150.50(14) 4_585 . ?
O4 Nd01 O6 131.26(16) 4_585 . ?
O5 Nd01 O6 46.93(11) . . ?
O1 Nd01 O6 97.08(13) . . ?
C8 Nd01 O6 146.74(14) 4_585 . ?
C1 Nd01 O6 81.56(13) . . ?
Nd01 O9 H9A 109.4 . . ?
Nd01 O9 H9B 109.4 . . ?
H9A O9 H9B 109.5 . . ?
C20 O5 Nd01 104.8(3) . . ?
Nd01 O10 H10A 109.4 . . ?
Nd01 O10 H10B 109.4 . . ?
H10A O10 H10B 109.5 . . ?
C1 O2 Nd01 95.6(3) . . ?
C14 C19 C18 121.4(5) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C1 O1 Nd01 91.4(3) . . ?
C12 C13 C9 121.2(5) . . ?
C12 C13 H13 119.4 . . ?
C9 C13 H13 119.4 . . ?
O8 C21 O7 123.5(6) . . ?
O8 C21 C17 121.1(6) . . ?
O7 C21 C17 115.4(6) . . ?
C7 C6 C5 121.4(5) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O1 C1 O2 121.2(5) . . ?
O1 C1 C2 120.5(5) . . ?
O2 C1 C2 118.2(5) . . ?
O1 C1 Nd01 62.7(3) . . ?
O2 C1 Nd01 58.6(3) . . ?
C2 C1 Nd01 172.5(4) . . ?
C19 C14 C15 119.6(4) . . ?
C19 C14 C12 118.5(4) . . ?
C15 C14 C12 121.9(4) . . ?
C10 C9 C13 117.3(4) . . ?
C10 C9 C7 121.9(4) . . ?
C13 C9 C7 120.7(4) . . ?
C16 C17 C18 119.6(5) . . ?
C16 C17 C21 122.5(5) . . ?
C18 C17 C21 117.9(5) . . ?
C16 C15 C14 119.2(4) . . ?
C16 C15 C20 117.9(4) . . ?
C14 C15 C20 122.9(4) . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C13 C12 C11 117.1(5) . . ?
C13 C12 C14 121.6(4) . . ?
C11 C12 C14 121.0(4) . . ?
C11 N1 C10 120.9(5) . . ?
C6 C7 C2 117.9(5) . . ?
C6 C7 C9 120.2(5) . . ?
C2 C7 C9 121.8(5) . . ?
C3 C2 C7 120.1(5) . . ?
C3 C2 C1 117.2(5) . . ?
C7 C2 C1 122.3(5) . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O6 C20 O5 120.3(5) . . ?
O6 C20 C15 120.7(4) . . ?
O5 C20 C15 118.9(4) . . ?
C21 O7 H7 109.5 . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 C8 120.9(5) . . ?
C3 C4 C8 120.1(5) . . ?
N1 C10 C9 121.4(5) . . ?
N1 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C19 C18 C17 119.7(5) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N1 C11 C12 121.9(5) . . ?
N1 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?

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
Nd01 O4 C8 O3 -6.1(6) 4_586 . . . ?
Nd01 O4 C8 C4 168.6(4) 4_586 . . . ?
Nd01 O3 C8 O4 6.2(6) 4_586 . . . ?
Nd01 O3 C8 C4 -168.6(4) 4_586 . . . ?
Nd01 O1 C1 O2 -4.0(5) . . . . ?
Nd01 O1 C1 C2 172.2(4) . . . . ?
Nd01 O2 C1 O1 4.1(5) . . . . ?
Nd01 O2 C1 C2 -172.1(4) . . . . ?
C18 C19 C14 C15 -3.1(8) . . . . ?
C18 C19 C14 C12 174.9(5) . . . . ?
C12 C13 C9 C10 -0.6(8) . . . . ?
C12 C13 C9 C7 -177.5(5) . . . . ?
O8 C21 C17 C16 -169.1(7) . . . . ?
O7 C21 C17 C16 9.4(10) . . . . ?
O8 C21 C17 C18 8.6(11) . . . . ?
O7 C21 C17 C18 -172.9(7) . . . . ?
C19 C14 C15 C16 2.2(7) . . . . ?
C12 C14 C15 C16 -175.7(5) . . . . ?
C19 C14 C15 C20 179.5(5) . . . . ?
C12 C14 C15 C20 1.6(7) . . . . ?
C9 C13 C12 C11 2.6(8) . . . . ?
C9 C13 C12 C14 177.0(5) . . . . ?
C19 C14 C12 C13 -122.8(6) . . . . ?
C15 C14 C12 C13 55.2(7) . . . . ?
C19 C14 C12 C11 51.4(7) . . . . ?
C15 C14 C12 C11 -130.6(5) . . . . ?
C5 C6 C7 C2 0.3(9) . . . . ?
C5 C6 C7 C9 -178.1(5) . . . . ?
C10 C9 C7 C6 -35.1(8) . . . . ?
C13 C9 C7 C6 141.7(6) . . . . ?
C10 C9 C7 C2 146.5(5) . . . . ?
C13 C9 C7 C2 -36.7(7) . . . . ?
C4 C3 C2 C7 6.9(8) . . . . ?
C4 C3 C2 C1 -165.9(5) . . . . ?
C6 C7 C2 C3 -5.3(8) . . . . ?
C9 C7 C2 C3 173.1(5) . . . . ?
C6 C7 C2 C1 167.1(5) . . . . ?
C9 C7 C2 C1 -14.5(8) . . . . ?
O1 C1 C2 C3 -42.1(7) . . . . ?
O2 C1 C2 C3 134.2(5) . . . . ?
O1 C1 C2 C7 145.3(5) . . . . ?
O2 C1 C2 C7 -38.4(7) . . . . ?
C7 C6 C5 C4 3.3(9) . . . . ?
C18 C17 C16 C15 -0.1(9) . . . . ?
C21 C17 C16 C15 177.5(6) . . . . ?
C14 C15 C16 C17 -0.6(8) . . . . ?
C20 C15 C16 C17 -178.1(5) . . . . ?
Nd01 O6 C20 O5 -146.0(8) 3_675 . . . ?
Nd01 O6 C20 O5 6.2(5) . . . . ?
Nd01 O6 C20 C15 35.1(13) 3_675 . . . ?
Nd01 O6 C20 C15 -172.7(4) . . . . ?
Nd01 O5 C20 O6 -7.4(6) . . . . ?
Nd01 O5 C20 C15 171.6(4) . . . . ?
C16 C15 C20 O6 -121.8(6) . . . . ?
C14 C15 C20 O6 60.9(7) . . . . ?
C16 C15 C20 O5 59.2(7) . . . . ?
C14 C15 C20 O5 -118.1(6) . . . . ?
C6 C5 C4 C3 -1.8(8) . . . . ?
C6 C5 C4 C8 -176.2(5) . . . . ?
C2 C3 C4 C5 -3.3(8) . . . . ?
C2 C3 C4 C8 171.1(5) . . . . ?
O4 C8 C4 C5 -6.7(8) . . . . ?
O3 C8 C4 C5 168.2(5) . . . . ?
Nd01 C8 C4 C5 89(2) 4_586 . . . ?
O4 C8 C4 C3 179.0(6) . . . . ?
O3 C8 C4 C3 -6.2(8) . . . . ?
Nd01 C8 C4 C3 -85(2) 4_586 . . . ?
C11 N1 C10 C9 1.3(9) . . . . ?
C13 C9 C10 N1 -1.4(8) . . . . ?
C7 C9 C10 N1 175.4(5) . . . . ?
C14 C19 C18 C17 2.3(9) . . . . ?
C16 C17 C18 C19 -0.7(9) . . . . ?
C21 C17 C18 C19 -178.4(6) . . . . ?
C10 N1 C11 C12 0.9(9) . . . . ?
C13 C12 C11 N1 -2.8(8) . . . . ?
C14 C12 C11 N1 -177.2(5) . . . . ?

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
O7 H7 N1 0.82 1.80 2.578(7) 159.2 4_475
O10 H10B O5 0.96 1.96 2.672(6) 128.8 3_575
O10 H10A O12 0.96 1.85 2.731(14) 151.6 1_464
O9 H9B O2 0.96 1.80 2.754(6) 175.5 3_675
O9 H9A O11 0.96 1.79 2.681(9) 153.4 1_454
O9 H9B O2 0.96 1.80 2.754(6) 175.5 3_675
O10 H10A O12 0.96 1.85 2.731(14) 151.6 1_464
O10 H10B O5 0.96 1.96 2.672(6) 128.8 3_575
O7 H7 N1 0.82 1.80 2.578(7) 159.2 4_475

_refine_diff_density_max         1.789
_refine_diff_density_min         -2.674
_refine_diff_density_rms         0.451

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/cc1450r2
_database_code_depnum_ccdc_archive 'CCDC 1047513'
_audit_update_record             
;
2015-02-05 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 N O12 Sm'
_chemical_formula_weight         622.68

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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.083(3)
_cell_length_b                   17.974(5)
_cell_length_c                   14.258(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.256(4)
_cell_angle_gamma                90
_cell_volume                     2234.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_F_000             1220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    2.696
_shelx_estimated_absorpt_T_min   0.519
_shelx_estimated_absorpt_T_max   0.589
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_T_max  0.553
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13588
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.870
_diffrn_reflns_theta_max         28.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5380
_reflns_number_gt                4806
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²]
 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         5380
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.2516
_refine_ls_wR_factor_gt          0.1675
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.084
_refine_ls_shift/su_mean         0.010

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
Sm1 Sm 0.69098(3) -0.07598(2) 0.51133(2) 0.0120(2) Uani 1 1 d . . . . .
O6 O 0.7745(6) -0.1017(3) 0.3584(3) 0.0246(10) Uani 1 1 d . . . . .
O5 O 0.5353(6) -0.0690(2) 0.3423(4) 0.0185(10) Uani 1 1 d . . . . .
O2 O 0.7901(5) 0.0438(3) 0.4648(4) 0.0247(10) Uani 1 1 d . . . . .
O4 O 0.9771(12) 0.3891(4) 0.4268(6) 0.075(3) Uani 1 1 d . . . . .
O3 O 1.0056(9) 0.3182(4) 0.5559(6) 0.065(2) Uani 1 1 d . . . . .
H3A H 1.0694 0.3500 0.5808 0.097 Uiso 1 1 calc R U . . .
O1 O 0.5480(6) 0.0685(3) 0.4521(5) 0.0247(12) Uani 1 1 d . . . . .
O7 O 0.7256(6) -0.3141(3) 0.1148(4) 0.0286(11) Uani 1 1 d . . . . .
O8 O 0.6024(8) -0.2962(3) -0.0350(4) 0.0361(14) Uani 1 1 d . . . . .
O10 O 0.9581(7) -0.0852(3) 0.5852(5) 0.0304(13) Uani 1 1 d . . . . .
H10A H 0.9764 -0.0970 0.6532 0.046 Uiso 1 1 d R U . . .
H10B H 1.0061 -0.0386 0.5789 0.046 Uiso 1 1 d R U . . .
O9 O 0.7322(5) -0.0046(3) 0.6603(4) 0.0250(10) Uani 1 1 d . . . . .
H9B H 0.6449 0.0268 0.6557 0.037 Uiso 1 1 d R U . . .
H9A H 0.8222 0.0256 0.6692 0.037 Uiso 1 1 d R U . . .
N1 N 0.2520(7) 0.1061(4) 0.1292(4) 0.0250(12) Uani 1 1 d . . . . .
C20 C 0.6420(8) -0.0900(4) 0.3075(5) 0.0164(12) Uani 1 1 d . . . . .
C18 C 0.4886(9) -0.1573(4) 0.0077(5) 0.0244(13) Uani 1 1 d . . . . .
H18 H 0.4475 -0.1755 -0.0552 0.029 Uiso 1 1 calc R U . . .
C16 C 0.6563(7) -0.1702(3) 0.1695(4) 0.0178(11) Uani 1 1 d . . . . .
H16 H 0.7345 -0.1959 0.2138 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2945(8) 0.0379(4) 0.1113(5) 0.0237(14) Uani 1 1 d . . . . .
H11 H 0.2240 0.0072 0.0688 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6285(9) 0.2511(4) 0.2667(6) 0.0256(14) Uani 1 1 d . . . . .
H6 H 0.5691 0.2643 0.2045 0.031 Uiso 1 1 calc R U . . .
C9 C 0.4988(7) 0.1286(3) 0.2390(4) 0.0160(11) Uani 1 1 d . . . . .
C15 C 0.5994(7) -0.1056(3) 0.1982(4) 0.0159(11) Uani 1 1 d . . . . .
C19 C 0.4399(9) -0.0891(4) 0.0352(5) 0.0210(13) Uani 1 1 d . . . . .
H19 H 0.3699 -0.0609 -0.0114 0.025 Uiso 1 1 calc R U . . .
C4 C 0.8242(8) 0.2803(4) 0.4137(5) 0.0230(13) Uani 1 1 d . . . . .
C14 C 0.4926(8) -0.0622(3) 0.1293(5) 0.0176(12) Uani 1 1 d . . . . .
C13 C 0.5440(7) 0.0596(4) 0.2185(5) 0.0156(11) Uani 1 1 d . . . . .
H13 H 0.6441 0.0442 0.2475 0.019 Uiso 1 1 calc R U . . .
C12 C 0.4422(7) 0.0115(3) 0.1546(4) 0.0171(11) Uani 1 1 d . . . . .
C7 C 0.6075(7) 0.1817(3) 0.3041(5) 0.0163(11) Uani 1 1 d . . . . .
C3 C 0.8029(7) 0.2109(4) 0.4517(6) 0.0239(14) Uani 1 1 d . . . . .
H3 H 0.8626 0.1975 0.5137 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7342(9) 0.3002(4) 0.3191(6) 0.0282(15) Uani 1 1 d . . . . .
H5 H 0.7471 0.3463 0.2929 0.034 Uiso 1 1 calc R U . . .
C17 C 0.5986(8) -0.1974(3) 0.0754(5) 0.0201(12) Uani 1 1 d . . . . .
C2 C 0.6948(7) 0.1622(3) 0.3987(5) 0.0153(11) Uani 1 1 d . . . . .
C1 C 0.6757(7) 0.0880(3) 0.4398(5) 0.0140(11) Uani 1 1 d . . . . .
C10 C 0.3506(8) 0.1516(4) 0.1923(5) 0.0229(14) Uani 1 1 d . . . . .
H10 H 0.3186 0.1989 0.2046 0.028 Uiso 1 1 calc R U . . .
C21 C 0.6467(8) -0.2733(3) 0.0501(6) 0.0244(14) Uani 1 1 d . . . . .
C8 C 0.9447(9) 0.3343(5) 0.4684(8) 0.041(2) Uani 1 1 d . . . . .
O12 O -0.0158(16) 0.4238(10) 0.2289(15) 0.199(13) Uani 1 1 d . . . . .
O11 O 0.907(2) 0.1151(15) 0.2284(9) 0.168(8) 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
Sm1 O10 2.365(6) . ?
Sm1 O1 2.374(5) 3_656 ?
Sm1 O9 2.419(5) . ?
Sm1 O7 2.433(5) 4_556 ?
Sm1 O5 2.433(5) . ?
Sm1 O8 2.462(5) 4_556 ?
Sm1 O2 2.495(5) . ?
Sm1 O6 2.544(5) . ?
Sm1 C21 2.816(6) 4_556 ?
Sm1 C20 2.825(7) . ?
Sm1 O1 2.920(5) . ?
O6 C20 1.237(8) . ?
O5 C20 1.263(9) . ?
O2 C1 1.277(8) . ?
O4 C8 1.228(11) . ?
O3 C8 1.249(12) . ?
O3 H3A 0.8200 . ?
O1 C1 1.270(8) . ?
O1 Sm1 2.374(5) 3_656 ?
O7 C21 1.238(9) . ?
O7 Sm1 2.433(5) 4 ?
O8 C21 1.238(9) . ?
O8 Sm1 2.462(5) 4 ?
O10 H10A 0.9600 . ?
O10 H10B 0.9600 . ?
O9 H9B 0.9600 . ?
O9 H9A 0.9600 . ?
N1 C10 1.354(9) . ?
N1 C11 1.330(10) . ?
C20 C15 1.523(9) . ?
C18 C17 1.382(10) . ?
C18 C19 1.396(9) . ?
C18 H18 0.9300 . ?
C16 C15 1.379(8) . ?
C16 C17 1.385(9) . ?
C16 H16 0.9300 . ?
C11 C12 1.394(9) . ?
C11 H11 0.9300 . ?
C6 C5 1.364(10) . ?
C6 C7 1.390(9) . ?
C6 H6 0.9300 . ?
C9 C13 1.363(8) . ?
C9 C10 1.388(9) . ?
C9 C7 1.495(8) . ?
C15 C14 1.408(9) . ?
C19 C14 1.380(10) . ?
C19 H19 0.9300 . ?
C4 C3 1.395(9) . ?
C4 C5 1.413(10) . ?
C4 C8 1.506(9) . ?
C14 C12 1.479(8) . ?
C13 C12 1.400(9) . ?
C13 H13 0.9300 . ?
C7 C2 1.405(9) . ?
C3 C2 1.374(9) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C17 C21 1.506(8) . ?
C2 C1 1.485(8) . ?
C10 H10 0.9300 . ?
C21 Sm1 2.816(6) 4 ?

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
O10 Sm1 O1 142.5(2) . 3_656 ?
O10 Sm1 O9 76.0(2) . . ?
O1 Sm1 O9 72.72(18) 3_656 . ?
O10 Sm1 O7 74.38(19) . 4_556 ?
O1 Sm1 O7 83.3(2) 3_656 4_556 ?
O9 Sm1 O7 86.35(17) . 4_556 ?
O10 Sm1 O5 133.2(2) . . ?
O1 Sm1 O5 84.3(2) 3_656 . ?
O9 Sm1 O5 138.31(16) . . ?
O7 Sm1 O5 125.69(17) 4_556 . ?
O10 Sm1 O8 105.8(2) . 4_556 ?
O1 Sm1 O8 82.1(2) 3_656 4_556 ?
O9 Sm1 O8 133.56(18) . 4_556 ?
O7 Sm1 O8 51.85(17) 4_556 4_556 ?
O5 Sm1 O8 74.13(16) . 4_556 ?
O10 Sm1 O2 77.13(17) . . ?
O1 Sm1 O2 115.45(16) 3_656 . ?
O9 Sm1 O2 78.31(19) . . ?
O7 Sm1 O2 150.16(17) 4_556 . ?
O5 Sm1 O2 81.06(18) . . ?
O8 Sm1 O2 148.09(19) 4_556 . ?
O10 Sm1 O6 81.6(2) . . ?
O1 Sm1 O6 135.17(19) 3_656 . ?
O9 Sm1 O6 147.05(17) . . ?
O7 Sm1 O6 110.70(18) 4_556 . ?
O5 Sm1 O6 52.40(17) . . ?
O8 Sm1 O6 75.74(18) 4_556 . ?
O2 Sm1 O6 73.27(18) . . ?
O10 Sm1 C21 91.7(2) . 4_556 ?
O1 Sm1 C21 79.76(18) 3_656 4_556 ?
O9 Sm1 C21 109.5(2) . 4_556 ?
O7 Sm1 C21 26.0(2) 4_556 4_556 ?
O5 Sm1 C21 99.72(19) . 4_556 ?
O8 Sm1 C21 26.0(2) 4_556 4_556 ?
O2 Sm1 C21 164.70(18) . 4_556 ?
O6 Sm1 C21 95.0(2) . 4_556 ?
O10 Sm1 C20 107.4(2) . . ?
O1 Sm1 C20 109.9(2) 3_656 . ?
O9 Sm1 C20 153.06(18) . . ?
O7 Sm1 C20 120.51(18) 4_556 . ?
O5 Sm1 C20 26.46(18) . . ?
O8 Sm1 C20 72.24(17) 4_556 . ?
O2 Sm1 C20 76.58(19) . . ?
O6 Sm1 C20 25.97(18) . . ?
C21 Sm1 C20 97.2(2) 4_556 . ?
O10 Sm1 O1 120.59(16) . . ?
O1 Sm1 O1 69.70(19) 3_656 . ?
O9 Sm1 O1 74.31(18) . . ?
O7 Sm1 O1 150.34(18) 4_556 . ?
O5 Sm1 O1 65.12(16) . . ?
O8 Sm1 O1 131.78(19) 4_556 . ?
O2 Sm1 O1 47.15(14) . . ?
O6 Sm1 O1 97.39(17) . . ?
C21 Sm1 O1 146.70(17) 4_556 . ?
C20 Sm1 O1 81.51(18) . . ?
C20 O6 Sm1 89.8(4) . . ?
C20 O5 Sm1 94.4(4) . . ?
C1 O2 Sm1 106.6(4) . . ?
C8 O3 H3A 109.5 . . ?
C1 O1 Sm1 160.2(5) . 3_656 ?
C1 O1 Sm1 86.4(4) . . ?
Sm1 O1 Sm1 110.29(19) 3_656 . ?
C21 O7 Sm1 94.6(4) . 4 ?
C21 O8 Sm1 93.2(4) . 4 ?
Sm1 O10 H10A 109.4 . . ?
Sm1 O10 H10B 109.5 . . ?
H10A O10 H10B 109.5 . . ?
Sm1 O9 H9B 109.3 . . ?
Sm1 O9 H9A 109.4 . . ?
H9B O9 H9A 109.5 . . ?
C10 N1 C11 120.8(6) . . ?
O6 C20 O5 123.3(6) . . ?
O6 C20 C15 119.7(6) . . ?
O5 C20 C15 116.9(6) . . ?
O6 C20 Sm1 64.2(4) . . ?
O5 C20 Sm1 59.2(4) . . ?
C15 C20 Sm1 172.2(4) . . ?
C17 C18 C19 119.1(6) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C15 C16 C17 120.9(6) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
N1 C11 C12 121.5(6) . . ?
N1 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C5 C6 C7 121.4(7) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C13 C9 C10 118.6(6) . . ?
C13 C9 C7 121.9(6) . . ?
C10 C9 C7 119.4(5) . . ?
C16 C15 C14 120.1(6) . . ?
C16 C15 C20 116.8(6) . . ?
C14 C15 C20 122.7(6) . . ?
C14 C19 C18 122.0(7) . . ?
C14 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C3 C4 C5 119.4(6) . . ?
C3 C4 C8 122.3(7) . . ?
C5 C4 C8 118.2(6) . . ?
C19 C14 C15 117.9(6) . . ?
C19 C14 C12 120.3(6) . . ?
C15 C14 C12 121.7(6) . . ?
C9 C13 C12 121.2(6) . . ?
C9 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C11 C12 C13 117.2(6) . . ?
C11 C12 C14 121.5(6) . . ?
C13 C12 C14 121.3(6) . . ?
C6 C7 C2 119.5(6) . . ?
C6 C7 C9 118.2(6) . . ?
C2 C7 C9 122.2(5) . . ?
C2 C3 C4 120.8(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C6 C5 C4 119.3(6) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C16 C17 C18 119.7(6) . . ?
C16 C17 C21 119.7(6) . . ?
C18 C17 C21 120.4(6) . . ?
C3 C2 C7 119.5(6) . . ?
C3 C2 C1 120.0(6) . . ?
C7 C2 C1 120.4(5) . . ?
O1 C1 O2 119.5(6) . . ?
O1 C1 C2 120.9(6) . . ?
O2 C1 C2 119.5(5) . . ?
N1 C10 C9 120.7(6) . . ?
N1 C10 H10 119.6 . . ?
C9 C10 H10 119.7 . . ?
O8 C21 O7 119.7(6) . . ?
O8 C21 C17 120.0(7) . . ?
O7 C21 C17 120.3(6) . . ?
O8 C21 Sm1 60.8(3) . 4 ?
O7 C21 Sm1 59.4(3) . 4 ?
C17 C21 Sm1 170.0(5) . 4 ?
O3 C8 O4 124.7(8) . . ?
O3 C8 C4 115.0(7) . . ?
O4 C8 C4 120.3(8) . . ?

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
Sm1 O6 C20 O5 3.9(7) . . . . ?
Sm1 O6 C20 C15 -172.3(5) . . . . ?
Sm1 O5 C20 O6 -4.1(7) . . . . ?
Sm1 O5 C20 C15 172.2(5) . . . . ?
C10 N1 C11 C12 -1.5(12) . . . . ?
C17 C16 C15 C14 -6.6(10) . . . . ?
C17 C16 C15 C20 166.0(6) . . . . ?
O6 C20 C15 C16 42.0(9) . . . . ?
O5 C20 C15 C16 -134.4(6) . . . . ?
O6 C20 C15 C14 -145.5(7) . . . . ?
O5 C20 C15 C14 38.0(9) . . . . ?
C17 C18 C19 C14 -3.4(11) . . . . ?
C18 C19 C14 C15 0.4(11) . . . . ?
C18 C19 C14 C12 178.0(7) . . . . ?
C16 C15 C14 C19 4.6(10) . . . . ?
C20 C15 C14 C19 -167.7(6) . . . . ?
C16 C15 C14 C12 -173.0(6) . . . . ?
C20 C15 C14 C12 14.8(10) . . . . ?
C10 C9 C13 C12 -2.3(10) . . . . ?
C7 C9 C13 C12 -177.7(6) . . . . ?
N1 C11 C12 C13 0.4(11) . . . . ?
N1 C11 C12 C14 -175.6(7) . . . . ?
C9 C13 C12 C11 1.6(10) . . . . ?
C9 C13 C12 C14 177.5(6) . . . . ?
C19 C14 C12 C11 34.8(10) . . . . ?
C15 C14 C12 C11 -147.7(7) . . . . ?
C19 C14 C12 C13 -141.0(7) . . . . ?
C15 C14 C12 C13 36.5(10) . . . . ?
C5 C6 C7 C2 1.3(11) . . . . ?
C5 C6 C7 C9 -175.0(7) . . . . ?
C13 C9 C7 C6 122.6(7) . . . . ?
C10 C9 C7 C6 -52.7(9) . . . . ?
C13 C9 C7 C2 -53.6(9) . . . . ?
C10 C9 C7 C2 131.1(7) . . . . ?
C5 C4 C3 C2 -0.6(11) . . . . ?
C8 C4 C3 C2 -178.1(7) . . . . ?
C7 C6 C5 C4 -0.3(12) . . . . ?
C3 C4 C5 C6 -0.1(12) . . . . ?
C8 C4 C5 C6 177.4(8) . . . . ?
C15 C16 C17 C18 3.6(10) . . . . ?
C15 C16 C17 C21 -171.4(6) . . . . ?
C19 C18 C17 C16 1.4(10) . . . . ?
C19 C18 C17 C21 176.3(7) . . . . ?
C4 C3 C2 C7 1.7(10) . . . . ?
C4 C3 C2 C1 178.9(6) . . . . ?
C6 C7 C2 C3 -2.1(10) . . . . ?
C9 C7 C2 C3 174.1(6) . . . . ?
C6 C7 C2 C1 -179.3(6) . . . . ?
C9 C7 C2 C1 -3.1(9) . . . . ?
Sm1 O1 C1 O2 142.3(13) 3_656 . . . ?
Sm1 O1 C1 O2 -5.9(6) . . . . ?
Sm1 O1 C1 C2 -36.4(19) 3_656 . . . ?
Sm1 O1 C1 C2 175.4(6) . . . . ?
Sm1 O2 C1 O1 7.2(8) . . . . ?
Sm1 O2 C1 C2 -174.1(5) . . . . ?
C3 C2 C1 O1 121.0(7) . . . . ?
C7 C2 C1 O1 -61.8(9) . . . . ?
C3 C2 C1 O2 -57.6(9) . . . . ?
C7 C2 C1 O2 119.6(7) . . . . ?
C11 N1 C10 C9 0.7(11) . . . . ?
C13 C9 C10 N1 1.2(10) . . . . ?
C7 C9 C10 N1 176.6(6) . . . . ?
Sm1 O8 C21 O7 8.6(8) 4 . . . ?
Sm1 O8 C21 C17 -168.5(6) 4 . . . ?
Sm1 O7 C21 O8 -8.7(8) 4 . . . ?
Sm1 O7 C21 C17 168.4(6) 4 . . . ?
C16 C17 C21 O8 -176.0(7) . . . . ?
C18 C17 C21 O8 9.1(10) . . . . ?
C16 C17 C21 O7 6.9(10) . . . . ?
C18 C17 C21 O7 -168.1(7) . . . . ?
C16 C17 C21 Sm1 92(3) . . . 4 ?
C18 C17 C21 Sm1 -83(3) . . . 4 ?
C3 C4 C8 O3 -11.8(13) . . . . ?
C5 C4 C8 O3 170.7(9) . . . . ?
C3 C4 C8 O4 168.1(10) . . . . ?
C5 C4 C8 O4 -9.4(14) . . . . ?

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
O9 H9A O12 0.96 1.74 2.656(11) 159.2 4_666
O9 H9B O5 0.96 1.81 2.758(7) 167.8 3_656
O10 H10B O2 0.96 2.11 2.684(7) 116.6 3_756
O10 H10A O11 0.96 1.76 2.652(13) 154.0 3_756
O3 H3A N1 0.82 1.79 2.577(9) 159.9 4_666

_refine_diff_density_max         3.152
_refine_diff_density_min         -7.250
_refine_diff_density_rms         0.757

_shelxl_version_number           2013-2

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_audit_block_doi                 10.5517/cc1450s3
_database_code_depnum_ccdc_archive 'CCDC 1047514'
_audit_update_record             
;
2015-02-05 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 N O12 Tb'
_chemical_formula_weight         631.25

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

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

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

_cell_length_a                   9.0138(12)
_cell_length_b                   17.945(2)
_cell_length_c                   14.1406(19)
_cell_angle_alpha                90
_cell_angle_beta                 105.705(2)
_cell_angle_gamma                90
_cell_volume                     2202.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.281
_shelx_estimated_absorpt_T_min   0.460
_shelx_estimated_absorpt_T_max   0.560
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.415
_exptl_absorpt_correction_T_max  0.519
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13323
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.270
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5292
_reflns_number_gt                4275
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0901P)²+0.1053P]
 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         5292
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
Tb1 Tb 0.19483(3) 1.07687(2) 0.51165(2) 0.01669(11) Uani 1 1 d . . . . .
O1 O 0.0401(5) 1.0687(2) 0.3467(3) 0.0239(9) Uani 1 1 d . . . . .
O2 O 0.2800(5) 1.1008(3) 0.3618(3) 0.0306(10) Uani 1 1 d . . . . .
C14 C 0.1068(7) 0.8181(3) 0.3052(4) 0.0224(12) Uani 1 1 d . . . . .
C1 C 0.1448(7) 1.0897(3) 0.3090(5) 0.0222(12) Uani 1 1 d . . . . .
C9 C -0.0567(7) 0.9895(3) 0.1574(4) 0.0230(12) Uani 1 1 d . . . . .
C2 C 0.1052(7) 1.1061(3) 0.2010(4) 0.0214(11) Uani 1 1 d . . . . .
C15 C 0.1939(6) 0.8382(3) 0.4002(4) 0.0218(12) Uani 1 1 d . . . . .
C13 C 0.0458(7) 0.9413(3) 0.2171(4) 0.0216(12) Uani 1 1 d . . . . .
H13 H 0.1475 0.9560 0.2438 0.026 Uiso 1 1 calc R U . . .
C6 C -0.0584(8) 1.0910(3) 0.0334(5) 0.0289(14) Uani 1 1 d . . . . .
H6 H -0.1299 1.0637 -0.0135 0.035 Uiso 1 1 calc R U . . .
C7 C -0.0037(8) 1.0638(3) 0.1293(5) 0.0251(13) Uani 1 1 d . . . . .
C12 C -0.0008(7) 0.8711(3) 0.2377(5) 0.0251(12) Uani 1 1 d . . . . .
C10 C -0.2045(8) 0.9641(4) 0.1151(5) 0.0363(16) Uani 1 1 d . . . . .
H10 H -0.2751 0.9957 0.0738 0.044 Uiso 1 1 calc R U . . .
C19 C 0.1298(9) 0.7488(3) 0.2657(6) 0.0372(16) Uani 1 1 d . . . . .
H19 H 0.0731 0.7353 0.2028 0.045 Uiso 1 1 calc R U . . .
C11 C -0.1499(8) 0.8495(4) 0.1883(5) 0.0316(14) Uani 1 1 d . . . . .
H11 H -0.1802 0.8008 0.1954 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3259(8) 0.7199(4) 0.4139(6) 0.0391(17) Uani 1 1 d . . . . .
C18 C 0.2391(8) 0.7006(4) 0.3225(5) 0.0339(15) Uani 1 1 d . . . . .
H18 H 0.2533 0.6540 0.2974 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3023(7) 0.7891(3) 0.4526(5) 0.0256(13) Uani 1 1 d . . . . .
H16 H 0.3611 0.8022 0.5152 0.031 Uiso 1 1 calc R U . . .
N1 N -0.2491(7) 0.8948(3) 0.1322(4) 0.0312(12) Uani 1 1 d . . . . .
O6 O 0.5023(8) 0.6799(4) 0.5597(5) 0.076(2) Uani 1 1 d . . . . .
H6A H 0.5651 0.6476 0.5847 0.115 Uiso 1 1 calc R U . . .
O5 O 0.4814(9) 0.6114(4) 0.4246(6) 0.085(3) Uani 1 1 d . . . . .
C21 C 0.4444(9) 0.6652(5) 0.4696(6) 0.0456(19) Uani 1 1 d . . . . .
C4 C 0.1060(8) 1.1996(3) 0.0769(5) 0.0273(13) Uani 1 1 d . . . . .
C3 C 0.1617(7) 1.1715(3) 0.1707(5) 0.0260(13) Uani 1 1 d . . . . .
H3 H 0.2398 1.1971 0.2152 0.031 Uiso 1 1 calc R U . . .
C5 C -0.0059(9) 1.1588(4) 0.0087(4) 0.0314(15) Uani 1 1 d . . . . .
H5 H -0.0457 1.1776 -0.0543 0.038 Uiso 1 1 calc R U . . .
O4 O 0.1096(7) 1.2974(3) -0.0369(3) 0.0409(12) Uani 1 1 d . . . . .
O3 O 0.2313(6) 1.3157(3) 0.1199(3) 0.0372(12) Uani 1 1 d . . . . .
C8 C 0.1528(8) 1.2745(3) 0.0501(4) 0.0255(13) Uani 1 1 d . . . . .
C20 C 0.1702(6) 0.9125(3) 0.4428(4) 0.0172(11) Uani 1 1 d . . . . .
O7 O 0.2826(5) 0.9575(2) 0.4641(3) 0.0257(9) Uani 1 1 d . . . . .
O8 O 0.0445(5) 0.9296(2) 0.4575(4) 0.0312(11) Uani 1 1 d . . . . .
O9 O 0.2301(5) 1.0071(3) 0.6569(3) 0.0254(9) Uani 1 1 d . . . . .
H9A H 0.3291 0.9833 0.6722 0.030 Uiso 1 1 d R U . . .
H9B H 0.1508 0.9700 0.6477 0.030 Uiso 1 1 d R U . . .
O10 O 0.4577(5) 1.0830(3) 0.5819(4) 0.0368(12) Uani 1 1 d . . . . .
H10A H 0.4843 1.1321 0.6082 0.044 Uiso 1 1 d R U . . .
H10B H 0.5106 1.0729 0.5329 0.044 Uiso 1 1 d R U . . .
O11 O 0.4829(11) 0.9256(7) 0.7282(10) 0.182(8) Uani 1 1 d . . . . .
O12 O 0.5888(13) 0.1129(11) 0.7676(10) 0.199(8) 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
Tb1 O10 2.311(5) . ?
Tb1 O8 2.317(4) 3_576 ?
Tb1 O9 2.352(4) . ?
Tb1 O1 2.377(4) . ?
Tb1 O4 2.422(5) 4_586 ?
Tb1 O3 2.428(4) 4_586 ?
Tb1 O7 2.441(4) . ?
Tb1 O2 2.479(4) . ?
Tb1 C8 2.769(6) 4_586 ?
Tb1 C1 2.788(6) . ?
O1 C1 1.260(8) . ?
O2 C1 1.261(8) . ?
C14 C19 1.403(9) . ?
C14 C15 1.407(8) . ?
C14 C12 1.501(8) . ?
C1 C2 1.501(8) . ?
C9 C13 1.376(8) . ?
C9 C10 1.381(9) . ?
C9 C7 1.504(8) . ?
C2 C3 1.392(8) . ?
C2 C7 1.424(9) . ?
C15 C16 1.374(8) . ?
C15 C20 1.501(8) . ?
C13 C12 1.384(8) . ?
C13 H13 0.9300 . ?
C6 C5 1.383(9) . ?
C6 C7 1.400(9) . ?
C6 H6 0.9300 . ?
C12 C11 1.392(9) . ?
C10 N1 1.349(9) . ?
C10 H10 0.9300 . ?
C19 C18 1.391(10) . ?
C19 H19 0.9300 . ?
C11 N1 1.306(9) . ?
C11 H11 0.9300 . ?
C17 C18 1.363(11) . ?
C17 C16 1.397(9) . ?
C17 C21 1.506(10) . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?
O6 C21 1.268(10) . ?
O6 H6A 0.8200 . ?
O5 C21 1.250(10) . ?
C4 C3 1.380(9) . ?
C4 C5 1.398(10) . ?
C4 C8 1.489(8) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
O4 C8 1.256(7) . ?
O4 Tb1 2.422(5) 4_585 ?
O3 C8 1.281(8) . ?
O3 Tb1 2.428(4) 4_585 ?
C8 Tb1 2.769(6) 4_585 ?
C20 O8 1.245(7) . ?
C20 O7 1.266(7) . ?
O8 Tb1 2.317(4) 3_576 ?
O9 H9A 0.9600 . ?
O9 H9B 0.9600 . ?
O10 H10A 0.9600 . ?
O10 H10B 0.9600 . ?

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
O10 Tb1 O8 145.08(19) . 3_576 ?
O10 Tb1 O9 76.68(17) . . ?
O8 Tb1 O9 73.81(16) 3_576 . ?
O10 Tb1 O1 133.32(17) . . ?
O8 Tb1 O1 81.56(17) 3_576 . ?
O9 Tb1 O1 136.82(15) . . ?
O10 Tb1 O4 106.68(18) . 4_586 ?
O8 Tb1 O4 81.95(17) 3_576 4_586 ?
O9 Tb1 O4 134.47(16) . 4_586 ?
O1 Tb1 O4 73.87(15) . 4_586 ?
O10 Tb1 O3 75.10(17) . 4_586 ?
O8 Tb1 O3 83.97(17) 3_576 4_586 ?
O9 Tb1 O3 84.76(16) . 4_586 ?
O1 Tb1 O3 127.66(15) . 4_586 ?
O4 Tb1 O3 54.37(16) 4_586 4_586 ?
O10 Tb1 O7 77.85(15) . . ?
O8 Tb1 O7 113.31(15) 3_576 . ?
O9 Tb1 O7 78.26(15) . . ?
O1 Tb1 O7 79.82(14) . . ?
O4 Tb1 O7 147.26(16) 4_586 . ?
O3 Tb1 O7 150.71(15) 4_586 . ?
O10 Tb1 O2 80.83(17) . . ?
O8 Tb1 O2 133.59(17) 3_576 . ?
O9 Tb1 O2 147.02(15) . . ?
O1 Tb1 O2 53.61(15) . . ?
O4 Tb1 O2 75.17(17) 4_586 . ?
O3 Tb1 O2 112.38(17) 4_586 . ?
O7 Tb1 O2 73.63(16) . . ?
O10 Tb1 C8 92.76(18) . 4_586 ?
O8 Tb1 C8 80.07(17) 3_576 4_586 ?
O9 Tb1 C8 109.52(16) . 4_586 ?
O1 Tb1 C8 100.20(16) . 4_586 ?
O4 Tb1 C8 26.95(16) 4_586 4_586 ?
O3 Tb1 C8 27.56(17) 4_586 4_586 ?
O7 Tb1 C8 166.32(16) . 4_586 ?
O2 Tb1 C8 95.25(17) . 4_586 ?
O10 Tb1 C1 107.45(19) . . ?
O8 Tb1 C1 107.35(18) 3_576 . ?
O9 Tb1 C1 152.59(15) . . ?
O1 Tb1 C1 26.76(17) . . ?
O4 Tb1 C1 71.40(16) 4_586 . ?
O3 Tb1 C1 122.63(16) 4_586 . ?
O7 Tb1 C1 76.31(16) . . ?
O2 Tb1 C1 26.90(17) . . ?
C8 Tb1 C1 97.47(16) 4_586 . ?
C1 O1 Tb1 95.1(4) . . ?
C1 O2 Tb1 90.3(4) . . ?
C19 C14 C15 120.2(6) . . ?
C19 C14 C12 116.6(5) . . ?
C15 C14 C12 122.9(5) . . ?
O1 C1 O2 120.7(6) . . ?
O1 C1 C2 119.3(6) . . ?
O2 C1 C2 119.8(5) . . ?
O1 C1 Tb1 58.1(3) . . ?
O2 C1 Tb1 62.8(3) . . ?
C2 C1 Tb1 172.1(4) . . ?
C13 C9 C10 117.8(6) . . ?
C13 C9 C7 120.7(5) . . ?
C10 C9 C7 121.1(6) . . ?
C3 C2 C7 118.0(5) . . ?
C3 C2 C1 118.2(5) . . ?
C7 C2 C1 123.2(5) . . ?
C16 C15 C14 118.8(5) . . ?
C16 C15 C20 120.7(5) . . ?
C14 C15 C20 120.4(5) . . ?
C9 C13 C12 120.7(6) . . ?
C9 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C5 C6 C7 119.8(6) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 119.8(6) . . ?
C6 C7 C9 120.7(6) . . ?
C2 C7 C9 119.4(5) . . ?
C13 C12 C11 117.0(6) . . ?
C13 C12 C14 122.0(5) . . ?
C11 C12 C14 120.9(5) . . ?
N1 C10 C9 121.8(6) . . ?
N1 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C18 C19 C14 118.7(7) . . ?
C18 C19 H19 120.7 . . ?
C14 C19 H19 120.7 . . ?
N1 C11 C12 122.7(6) . . ?
N1 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C18 C17 C16 119.2(6) . . ?
C18 C17 C21 118.3(7) . . ?
C16 C17 C21 122.4(7) . . ?
C17 C18 C19 121.6(6) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C15 C16 C17 121.4(6) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C11 N1 C10 119.7(6) . . ?
C21 O6 H6A 109.5 . . ?
O5 C21 O6 125.3(8) . . ?
O5 C21 C17 119.1(7) . . ?
O6 C21 C17 115.5(7) . . ?
C3 C4 C5 118.6(6) . . ?
C3 C4 C8 121.3(6) . . ?
C5 C4 C8 119.9(6) . . ?
C4 C3 C2 122.4(6) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C6 C5 C4 121.2(6) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C8 O4 Tb1 92.1(4) . 4_585 ?
C8 O3 Tb1 91.2(3) . 4_585 ?
O4 C8 O3 121.7(5) . . ?
O4 C8 C4 120.8(6) . . ?
O3 C8 C4 117.4(5) . . ?
O4 C8 Tb1 60.9(3) . 4_585 ?
O3 C8 Tb1 61.3(3) . 4_585 ?
C4 C8 Tb1 169.5(4) . 4_585 ?
O8 C20 O7 120.6(5) . . ?
O8 C20 C15 121.4(5) . . ?
O7 C20 C15 118.0(5) . . ?
C20 O7 Tb1 109.1(3) . . ?
C20 O8 Tb1 162.8(4) . 3_576 ?
Tb1 O9 H9A 109.3 . . ?
Tb1 O9 H9B 109.3 . . ?
H9A O9 H9B 109.5 . . ?
Tb1 O10 H10A 109.3 . . ?
Tb1 O10 H10B 109.4 . . ?
H10A O10 H10B 109.5 . . ?

_refine_diff_density_max         1.409
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.258

_shelxl_version_number           2013-2

