# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ce
_database_code_depnum_ccdc_archive 'CCDC 1412701'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Ce (H2 O)4 (C21 H10 N O8)'
_chemical_formula_sum            'C21 H18 Ce N O12'
_chemical_formula_weight         616.48

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'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   14.7932(12)
_cell_length_b                   14.7382(11)
_cell_length_c                   10.6919(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.2890(10)
_cell_angle_gamma                90.00
_cell_volume                     2156.9(3)
_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_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1220
_exptl_absorpt_coefficient_mu    2.181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_T_max  0.7646
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6258
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2456
_reflns_number_gt                2216
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0347P)²+7.8058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2456
_refine_ls_number_parameters     159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ce1 Ce 0.5000 0.525852(17) 0.2500 0.03109(10) Uani 1 2 d S . .
O1 O 0.4516(2) 0.64266(17) 0.3758(3) 0.0453(7) Uani 1 1 d . . .
O2 O 0.4550(2) 0.58530(18) 0.5702(3) 0.0504(7) Uani 1 1 d . . .
O3 O 0.3209(3) 0.7488(2) 0.8536(3) 0.0642(9) Uani 1 1 d . . .
O4 O 0.2912(2) 0.8982(2) 0.8281(3) 0.0542(8) Uani 1 1 d . . .
O1W O 0.6585(2) 0.4676(2) 0.2225(3) 0.0564(8) Uani 1 1 d . . .
H11 H 0.7032 0.4614 0.2991 0.085 Uiso 1 1 d R . .
H12 H 0.6472 0.4175 0.1822 0.085 Uiso 1 1 d R . .
O2W O 0.3456(2) 0.5996(2) 0.0624(3) 0.0534(8) Uani 1 1 d . . .
H21 H 0.3017 0.6074 0.0932 0.080 Uiso 1 1 d R . .
H22 H 0.3611 0.6499 0.0393 0.080 Uiso 1 1 d R . .
C1 C 0.4429(3) 0.6498(2) 0.4883(3) 0.0317(7) Uani 1 1 d . . .
C2 C 0.4148(2) 0.7417(2) 0.5271(3) 0.0279(7) Uani 1 1 d . . .
C3 C 0.3796(3) 0.7441(2) 0.6326(3) 0.0315(7) Uani 1 1 d . . .
H3 H 0.3755 0.6902 0.6754 0.038 Uiso 1 1 calc R . .
C4 C 0.3509(3) 0.8246(2) 0.6744(3) 0.0334(7) Uani 1 1 d . . .
C5 C 0.3562(4) 0.9052(3) 0.6084(4) 0.0495(11) Uani 1 1 d . . .
H5 H 0.3361 0.9595 0.6340 0.059 Uiso 1 1 calc R . .
C6 C 0.3914(4) 0.9046(3) 0.5041(4) 0.0482(11) Uani 1 1 d . . .
H6 H 0.3950 0.9588 0.4618 0.058 Uiso 1 1 calc R . .
C7 C 0.4214(3) 0.8241(2) 0.4623(3) 0.0307(7) Uani 1 1 d D . .
C8 C 0.3166(3) 0.8231(3) 0.7923(4) 0.0426(9) Uani 1 1 d . . .
C9 C 0.4610(3) 0.8290(2) 0.3514(3) 0.0305(7) Uani 1 1 d D . .
C10 C 0.4034(4) 0.8273(5) 0.2197(4) 0.099(3) Uani 1 1 d D . .
H10 H 0.3360 0.8236 0.1941 0.119 Uiso 1 1 calc R . .
N1 N 0.4431(3) 0.8309(4) 0.1215(4) 0.106(3) Uani 0.50 1 d P . -1
H1 H 0.4028 0.8348 0.0365 0.127 Uiso 0.50 1 calc PR . -1
C11 C 0.4431(3) 0.8309(4) 0.1215(4) 0.106(3) Uani 0.50 1 d PD . -2
H11A H 0.4005 0.8350 0.0316 0.127 Uiso 0.50 1 calc PR . -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
Ce1 O2 2.419(3) 2_564 ?
Ce1 O2 2.419(3) 5_666 ?
Ce1 O1 2.453(2) 6_656 ?
Ce1 O1 2.453(2) . ?
Ce1 O1W 2.616(3) 6_656 ?
Ce1 O1W 2.616(3) . ?
Ce1 O2W 2.636(3) 6_656 ?
Ce1 O2W 2.636(3) . ?
O1 C1 1.261(4) . ?
O2 C1 1.258(4) . ?
O2 Ce1 2.419(3) 5_666 ?
O3 C8 1.264(5) . ?
O4 C8 1.273(5) . ?
O1W H11 0.8400 . ?
O1W H12 0.8400 . ?
O2W H21 0.8400 . ?
O2W H22 0.8400 . ?
C1 C2 1.521(4) . ?
C2 C3 1.410(4) . ?
C2 C7 1.420(4) . ?
C3 C4 1.390(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(5) . ?
C4 C8 1.528(4) . ?
C5 C6 1.398(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(5) . ?
C6 H6 0.9300 . ?
C7 C9 1.511(4) . ?
C9 C11 1.337(6) 6_656 ?
C9 N1 1.337(6) 6_656 ?
C9 C10 1.341(5) . ?
C10 N1 1.384(6) . ?
C10 H10 0.9300 . ?
N1 C9 1.337(6) 6_656 ?
N1 H1 0.8800 . ?

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 Ce1 O2 94.76(14) 2_564 5_666 ?
O2 Ce1 O1 95.10(9) 2_564 6_656 ?
O2 Ce1 O1 149.50(11) 5_666 6_656 ?
O2 Ce1 O1 149.50(11) 2_564 . ?
O2 Ce1 O1 95.10(9) 5_666 . ?
O1 Ce1 O1 90.85(12) 6_656 . ?
O2 Ce1 O1W 83.06(10) 2_564 6_656 ?
O2 Ce1 O1W 71.13(11) 5_666 6_656 ?
O1 Ce1 O1W 138.80(10) 6_656 6_656 ?
O1 Ce1 O1W 73.02(10) . 6_656 ?
O2 Ce1 O1W 71.13(11) 2_564 . ?
O2 Ce1 O1W 83.06(10) 5_666 . ?
O1 Ce1 O1W 73.02(10) 6_656 . ?
O1 Ce1 O1W 138.80(10) . . ?
O1W Ce1 O1W 141.71(14) 6_656 . ?
O2 Ce1 O2W 141.43(11) 2_564 6_656 ?
O2 Ce1 O2W 77.11(10) 5_666 6_656 ?
O1 Ce1 O2W 77.22(9) 6_656 6_656 ?
O1 Ce1 O2W 69.02(10) . 6_656 ?
O1W Ce1 O2W 127.21(9) 6_656 6_656 ?
O1W Ce1 O2W 70.48(10) . 6_656 ?
O2 Ce1 O2W 77.11(10) 2_564 . ?
O2 Ce1 O2W 141.43(11) 5_666 . ?
O1 Ce1 O2W 69.02(10) 6_656 . ?
O1 Ce1 O2W 77.22(9) . . ?
O1W Ce1 O2W 70.48(10) 6_656 . ?
O1W Ce1 O2W 127.21(9) . . ?
O2W Ce1 O2W 131.26(14) 6_656 . ?
C1 O1 Ce1 137.5(2) . . ?
C1 O2 Ce1 171.2(3) . 5_666 ?
Ce1 O1W H11 109.5 . . ?
Ce1 O1W H12 109.5 . . ?
H11 O1W H12 109.5 . . ?
Ce1 O2W H21 109.5 . . ?
Ce1 O2W H22 109.5 . . ?
H21 O2W H22 109.5 . . ?
O2 C1 O1 124.1(3) . . ?
O2 C1 C2 117.7(3) . . ?
O1 C1 C2 118.1(3) . . ?
C3 C2 C7 118.9(3) . . ?
C3 C2 C1 117.5(3) . . ?
C7 C2 C1 123.6(3) . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C8 119.4(3) . . ?
C5 C4 C8 121.9(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 118.8(3) . . ?
C6 C7 C9 118.4(3) . . ?
C2 C7 C9 122.8(3) . . ?
O3 C8 O4 124.0(3) . . ?
O3 C8 C4 118.2(4) . . ?
O4 C8 C4 117.6(4) . . ?
C11 C9 N1 0.00(9) 6_656 6_656 ?
C11 C9 C10 115.3(3) 6_656 . ?
N1 C9 C10 115.3(3) 6_656 . ?
C11 C9 C7 121.8(3) 6_656 . ?
N1 C9 C7 121.8(3) 6_656 . ?
C10 C9 C7 122.9(4) . . ?
C9 C10 N1 120.9(4) . . ?
C9 C10 H10 119.6 . . ?
N1 C10 H10 119.6 . . ?
C9 N1 C10 123.7(4) 6_656 . ?
C9 N1 H1 118.1 6_656 . ?
C10 N1 H1 118.1 . . ?

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
O2 Ce1 O1 C1 103.7(4) 2_564 . . . ?
O2 Ce1 O1 C1 -4.6(4) 5_666 . . . ?
O1 Ce1 O1 C1 -154.7(4) 6_656 . . . ?
O1W Ce1 O1 C1 63.8(4) 6_656 . . . ?
O1W Ce1 O1 C1 -89.9(4) . . . . ?
O2W Ce1 O1 C1 -78.7(4) 6_656 . . . ?
O2W Ce1 O1 C1 137.0(4) . . . . ?
Ce1 O2 C1 O1 113.3(15) 5_666 . . . ?
Ce1 O2 C1 C2 -67.4(18) 5_666 . . . ?
Ce1 O1 C1 O2 -4.3(7) . . . . ?
Ce1 O1 C1 C2 176.4(2) . . . . ?
O2 C1 C2 C3 -16.2(5) . . . . ?
O1 C1 C2 C3 163.2(3) . . . . ?
O2 C1 C2 C7 164.4(4) . . . . ?
O1 C1 C2 C7 -16.2(5) . . . . ?
C7 C2 C3 C4 0.3(5) . . . . ?
C1 C2 C3 C4 -179.2(3) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C2 C3 C4 C8 -178.1(3) . . . . ?
C3 C4 C5 C6 -1.2(7) . . . . ?
C8 C4 C5 C6 177.6(4) . . . . ?
C4 C5 C6 C7 0.5(7) . . . . ?
C5 C6 C7 C2 0.5(7) . . . . ?
C5 C6 C7 C9 -178.5(4) . . . . ?
C3 C2 C7 C6 -0.9(5) . . . . ?
C1 C2 C7 C6 178.5(4) . . . . ?
C3 C2 C7 C9 178.0(3) . . . . ?
C1 C2 C7 C9 -2.5(5) . . . . ?
C3 C4 C8 O3 4.1(6) . . . . ?
C5 C4 C8 O3 -174.7(4) . . . . ?
C3 C4 C8 O4 179.7(4) . . . . ?
C5 C4 C8 O4 1.0(6) . . . . ?
C6 C7 C9 C11 97.8(5) . . . 6_656 ?
C2 C7 C9 C11 -81.2(5) . . . 6_656 ?
C6 C7 C9 N1 97.8(5) . . . 6_656 ?
C2 C7 C9 N1 -81.2(5) . . . 6_656 ?
C6 C7 C9 C10 -85.4(6) . . . . ?
C2 C7 C9 C10 95.6(6) . . . . ?
C11 C9 C10 N1 -2.3(8) 6_656 . . . ?
N1 C9 C10 N1 -2.3(8) 6_656 . . . ?
C7 C9 C10 N1 -179.3(3) . . . . ?
C9 C10 N1 C9 5.5(7) . . . 6_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
O1W H11 O4 0.84 2.40 2.712(5) 102.6 4_564
O2W H21 O4 0.84 1.87 2.696(4) 169.2 7_566
O2W H22 O3 0.84 2.35 3.055(4) 141.8 1_554
N1 H1 O3 0.88 2.26 3.002(6) 142.1 1_554
N1 H1 O4 0.88 2.40 3.245(5) 160.3 1_554

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.099
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nd-sr
_database_code_depnum_ccdc_archive 'CCDC 1412702'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Nd (H2 O) (C20 H10 N O8)'
_chemical_formula_sum            'C21 H12 N Nd O9'
_chemical_formula_weight         566.56

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   9.3219(6)
_cell_length_b                   10.5274(6)
_cell_length_c                   11.1369(7)
_cell_angle_alpha                64.340(1)
_cell_angle_beta                 80.881(1)
_cell_angle_gamma                82.009(1)
_cell_volume                     969.64(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             554
_exptl_absorpt_coefficient_mu    2.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5480
_exptl_absorpt_correction_T_max  0.6844
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5663
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4248
_reflns_number_gt                3868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0591P)²+0.7510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4248
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.17063(2) 0.59794(2) 0.506025(18) 0.01944(9) Uani 1 1 d . . .
O1 O 0.3891(3) 0.7507(3) 0.4082(3) 0.0275(6) Uani 1 1 d . . .
O2 O 0.1723(3) 0.8597(4) 0.3817(4) 0.0354(8) Uani 1 1 d . . .
O3 O 0.0647(3) 1.2847(4) 0.4565(4) 0.0317(7) Uani 1 1 d . . .
O4 O 0.2463(3) 1.3974(3) 0.4583(3) 0.0324(7) Uani 1 1 d . . .
O5 O 0.9904(3) 0.5878(3) 0.3411(3) 0.0289(7) Uani 1 1 d . . .
O6 O 1.2042(4) 0.6667(4) 0.2536(3) 0.0416(9) Uani 1 1 d . . .
O7 O 1.1884(4) 0.6338(4) -0.3048(3) 0.0394(8) Uani 1 1 d . . .
O8 O 1.3218(4) 0.5058(5) -0.1421(4) 0.0523(11) Uani 1 1 d . . .
O1W O 0.3815(4) 0.4511(4) 0.6270(3) 0.0364(8) Uani 1 1 d . . .
H11 H 0.4252 0.4032 0.5865 0.055 Uiso 1 1 calc R . .
H12 H 0.3510 0.3966 0.7054 0.055 Uiso 1 1 calc R . .
N1 N 0.5835(4) 0.8977(4) 0.1800(4) 0.0333(9) Uani 1 1 d . . .
H1 H 0.4954 0.9000 0.1706 0.040 Uiso 1 1 calc R . .
C1 C 0.3045(5) 0.8619(5) 0.3813(4) 0.0235(8) Uani 1 1 d . . .
C2 C 0.3607(4) 0.9984(4) 0.3579(4) 0.0221(8) Uani 1 1 d . . .
C3 C 0.2628(4) 1.0890(4) 0.3955(4) 0.0227(8) Uani 1 1 d . . .
H3 H 0.1659 1.0680 0.4212 0.027 Uiso 1 1 calc R . .
C4 C 0.3033(4) 1.2092(4) 0.3962(4) 0.0238(8) Uani 1 1 d . . .
C5 C 0.4462(5) 1.2411(5) 0.3590(6) 0.0357(11) Uani 1 1 d . . .
H5 H 0.4763 1.3200 0.3624 0.043 Uiso 1 1 calc R . .
C6 C 0.5438(5) 1.1546(6) 0.3166(6) 0.0384(12) Uani 1 1 d . . .
H6 H 0.6398 1.1779 0.2891 0.046 Uiso 1 1 calc R . .
C7 C 0.5047(5) 1.0341(5) 0.3134(5) 0.0269(9) Uani 1 1 d . . .
C8 C 0.1950(4) 1.3045(4) 0.4411(4) 0.0226(8) Uani 1 1 d . . .
C9 C 0.6179(5) 0.9581(5) 0.2564(4) 0.0278(9) Uani 1 1 d . . .
C10 C 0.6825(5) 0.8355(5) 0.1199(4) 0.0246(8) Uani 1 1 d . . .
H10 H 0.6520 0.7942 0.0705 0.030 Uiso 1 1 calc R . .
C11 C 0.8265(5) 0.8299(5) 0.1276(4) 0.0276(9) Uani 1 1 d . . .
C12 C 0.8680(5) 0.8904(5) 0.2031(4) 0.0285(9) Uani 1 1 d . . .
H12A H 0.9662 0.8885 0.2109 0.034 Uiso 1 1 calc R . .
C13 C 0.7645(5) 0.9538(5) 0.2670(5) 0.0295(9) Uani 1 1 d . . .
H13 H 0.7936 0.9941 0.3180 0.035 Uiso 1 1 calc R . .
C14 C 0.9276(5) 0.7632(5) 0.0528(4) 0.0288(9) Uani 1 1 d . . .
C15 C 0.9043(6) 0.7934(6) -0.0766(5) 0.0398(12) Uani 1 1 d . . .
H15 H 0.8244 0.8538 -0.1133 0.048 Uiso 1 1 calc R . .
C16 C 0.9973(5) 0.7358(6) -0.1522(4) 0.0353(11) Uani 1 1 d . . .
H16 H 0.9791 0.7564 -0.2387 0.042 Uiso 1 1 calc R . .
C17 C 1.1169(5) 0.6480(5) -0.1004(4) 0.0250(9) Uani 1 1 d . . .
C18 C 1.1424(5) 0.6175(5) 0.0283(4) 0.0244(8) Uani 1 1 d . . .
H18 H 1.2234 0.5582 0.0636 0.029 Uiso 1 1 calc R . .
C19 C 1.0505(5) 0.6732(5) 0.1045(4) 0.0234(8) Uani 1 1 d . . .
C20 C 1.0826(5) 0.6393(5) 0.2429(4) 0.0252(9) Uani 1 1 d . . .
C21 C 1.2159(5) 0.5883(5) -0.1863(4) 0.0285(9) Uani 1 1 d . . .


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 O1 2.571(3) . ?
Nd1 O2 2.493(3) . ?
Nd1 O3 2.432(3) 2_576 ?
Nd1 O4 2.383(3) 1_545 ?
Nd1 O5 2.721(3) 1_455 ?
Nd1 O5 2.470(3) 2_666 ?
Nd1 O6 2.558(3) 1_455 ?
Nd1 O7 2.330(3) 1_456 ?
Nd1 O1W 2.502(3) . ?
O1 C1 1.263(5) . ?
O2 C1 1.235(5) . ?
O3 C8 1.233(5) . ?
O3 Nd1 2.432(3) 2_576 ?
O4 C8 1.242(5) . ?
O4 Nd1 2.383(3) 1_565 ?
O5 C20 1.244(5) . ?
O5 Nd1 2.470(3) 2_666 ?
O5 Nd1 2.721(3) 1_655 ?
O6 C20 1.243(6) . ?
O6 Nd1 2.558(3) 1_655 ?
O7 C21 1.250(5) . ?
O7 Nd1 2.330(3) 1_654 ?
O8 C21 1.231(6) . ?
O1W H11 0.8400 . ?
O1W H12 0.8400 . ?
N1 C10 1.321(5) . ?
N1 C9 1.357(6) . ?
N1 H1 0.8400 . ?
C1 C2 1.500(6) . ?
C2 C3 1.379(6) . ?
C2 C7 1.399(6) . ?
C3 C4 1.374(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(6) . ?
C4 C8 1.506(5) . ?
C5 C6 1.373(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(7) . ?
C6 H6 0.9300 . ?
C7 C9 1.465(6) . ?
C9 C13 1.384(6) . ?
C10 C11 1.350(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(6) . ?
C11 C14 1.466(6) . ?
C12 C13 1.377(6) . ?
C12 H12A 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.382(6) . ?
C14 C19 1.406(6) . ?
C15 C16 1.376(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(5) . ?
C17 C21 1.497(6) . ?
C18 C19 1.364(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.494(5) . ?

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
O7 Nd1 O4 130.49(12) 1_456 1_545 ?
O7 Nd1 O3 76.03(12) 1_456 2_576 ?
O4 Nd1 O3 134.27(11) 1_545 2_576 ?
O7 Nd1 O5 84.90(12) 1_456 2_666 ?
O4 Nd1 O5 73.96(11) 1_545 2_666 ?
O3 Nd1 O5 72.64(11) 2_576 2_666 ?
O7 Nd1 O2 85.58(13) 1_456 . ?
O4 Nd1 O2 136.82(12) 1_545 . ?
O3 Nd1 O2 68.78(11) 2_576 . ?
O5 Nd1 O2 141.42(10) 2_666 . ?
O7 Nd1 O1W 68.35(12) 1_456 . ?
O4 Nd1 O1W 67.15(11) 1_545 . ?
O3 Nd1 O1W 141.29(11) 2_576 . ?
O5 Nd1 O1W 89.22(11) 2_666 . ?
O2 Nd1 O1W 121.30(12) . . ?
O7 Nd1 O6 153.48(14) 1_456 1_455 ?
O4 Nd1 O6 68.56(12) 1_545 1_455 ?
O3 Nd1 O6 104.01(12) 2_576 1_455 ?
O5 Nd1 O6 120.84(11) 2_666 1_455 ?
O2 Nd1 O6 70.30(12) . 1_455 ?
O1W Nd1 O6 114.61(12) . 1_455 ?
O7 Nd1 O1 82.95(12) 1_456 . ?
O4 Nd1 O1 104.07(10) 1_545 . ?
O3 Nd1 O1 117.16(10) 2_576 . ?
O5 Nd1 O1 161.73(11) 2_666 . ?
O2 Nd1 O1 50.89(10) . . ?
O1W Nd1 O1 73.63(11) . . ?
O6 Nd1 O1 73.41(11) 1_455 . ?
O7 Nd1 O5 146.50(11) 1_456 1_455 ?
O4 Nd1 O5 70.75(10) 1_545 1_455 ?
O3 Nd1 O5 71.87(10) 2_576 1_455 ?
O5 Nd1 O5 76.72(10) 2_666 1_455 ?
O2 Nd1 O5 91.54(11) . 1_455 ?
O1W Nd1 O5 137.81(10) . 1_455 ?
O6 Nd1 O5 48.67(10) 1_455 1_455 ?
O1 Nd1 O5 120.30(10) . 1_455 ?
C1 O1 Nd1 90.7(3) . . ?
C1 O2 Nd1 95.0(3) . . ?
C8 O3 Nd1 138.6(3) . 2_576 ?
C8 O4 Nd1 140.8(3) . 1_565 ?
C20 O5 Nd1 153.1(3) . 2_666 ?
C20 O5 Nd1 90.5(3) . 1_655 ?
Nd1 O5 Nd1 103.28(10) 2_666 1_655 ?
C20 O6 Nd1 98.3(3) . 1_655 ?
C21 O7 Nd1 150.8(3) . 1_654 ?
Nd1 O1W H11 109.5 . . ?
Nd1 O1W H12 109.5 . . ?
H11 O1W H12 109.5 . . ?
C10 N1 C9 122.9(4) . . ?
C10 N1 H1 118.6 . . ?
C9 N1 H1 118.6 . . ?
O2 C1 O1 121.2(4) . . ?
O2 C1 C2 118.0(4) . . ?
O1 C1 C2 120.6(4) . . ?
C3 C2 C7 118.5(4) . . ?
C3 C2 C1 115.7(4) . . ?
C7 C2 C1 125.6(4) . . ?
C4 C3 C2 122.3(4) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 C8 119.3(4) . . ?
C3 C4 C8 121.2(4) . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 122.6(4) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C6 C7 C2 118.2(4) . . ?
C6 C7 C9 116.3(4) . . ?
C2 C7 C9 125.3(4) . . ?
O3 C8 O4 125.9(4) . . ?
O3 C8 C4 117.9(4) . . ?
O4 C8 C4 116.2(4) . . ?
N1 C9 C13 116.4(4) . . ?
N1 C9 C7 120.6(4) . . ?
C13 C9 C7 122.8(4) . . ?
N1 C10 C11 122.3(4) . . ?
N1 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C12 117.4(4) . . ?
C10 C11 C14 117.9(4) . . ?
C12 C11 C14 124.7(4) . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C9 120.8(4) . . ?
C12 C13 H13 119.6 . . ?
C9 C13 H13 119.6 . . ?
C15 C14 C19 118.0(4) . . ?
C15 C14 C11 118.7(4) . . ?
C19 C14 C11 123.2(4) . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 119.3(4) . . ?
C16 C17 C21 118.6(4) . . ?
C18 C17 C21 122.0(4) . . ?
C19 C18 C17 120.9(4) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C14 120.3(4) . . ?
C18 C19 C20 119.4(4) . . ?
C14 C19 C20 120.3(4) . . ?
O5 C20 O6 122.5(4) . . ?
O5 C20 C19 120.9(4) . . ?
O6 C20 C19 116.6(4) . . ?
O5 C20 Nd1 65.0(2) . 1_655 ?
O6 C20 Nd1 57.5(2) . 1_655 ?
C19 C20 Nd1 173.4(3) . 1_655 ?
O8 C21 O7 123.5(4) . . ?
O8 C21 C17 120.6(4) . . ?
O7 C21 C17 115.8(4) . . ?

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
O7 Nd1 O1 C1 -82.0(3) 1_456 . . . ?
O4 Nd1 O1 C1 148.0(2) 1_545 . . . ?
O3 Nd1 O1 C1 -11.7(3) 2_576 . . . ?
O5 Nd1 O1 C1 -130.6(3) 2_666 . . . ?
O2 Nd1 O1 C1 8.1(2) . . . . ?
O1W Nd1 O1 C1 -151.4(3) . . . . ?
O6 Nd1 O1 C1 85.9(3) 1_455 . . . ?
O5 Nd1 O1 C1 72.3(3) 1_455 . . . ?
C20 Nd1 O1 C1 78.9(3) 1_455 . . . ?
O7 Nd1 O2 C1 76.2(3) 1_456 . . . ?
O4 Nd1 O2 C1 -74.2(3) 1_545 . . . ?
O3 Nd1 O2 C1 152.9(3) 2_576 . . . ?
O5 Nd1 O2 C1 152.3(2) 2_666 . . . ?
O1W Nd1 O2 C1 14.9(3) . . . . ?
O6 Nd1 O2 C1 -92.6(3) 1_455 . . . ?
O1 Nd1 O2 C1 -8.3(2) . . . . ?
O5 Nd1 O2 C1 -137.2(3) 1_455 . . . ?
C20 Nd1 O2 C1 -115.7(3) 1_455 . . . ?
Nd1 O2 C1 O1 15.4(4) . . . . ?
Nd1 O2 C1 C2 -160.1(3) . . . . ?
Nd1 O1 C1 O2 -14.9(4) . . . . ?
Nd1 O1 C1 C2 160.5(3) . . . . ?
O2 C1 C2 C3 27.0(6) . . . . ?
O1 C1 C2 C3 -148.6(4) . . . . ?
O2 C1 C2 C7 -159.0(4) . . . . ?
O1 C1 C2 C7 25.4(6) . . . . ?
C7 C2 C3 C4 -2.9(6) . . . . ?
C1 C2 C3 C4 171.5(4) . . . . ?
C2 C3 C4 C5 -0.2(7) . . . . ?
C2 C3 C4 C8 -178.4(4) . . . . ?
C3 C4 C5 C6 2.6(7) . . . . ?
C8 C4 C5 C6 -179.2(5) . . . . ?
C4 C5 C6 C7 -1.8(9) . . . . ?
C5 C6 C7 C2 -1.4(8) . . . . ?
C5 C6 C7 C9 175.5(5) . . . . ?
C3 C2 C7 C6 3.7(7) . . . . ?
C1 C2 C7 C6 -170.2(4) . . . . ?
C3 C2 C7 C9 -173.0(4) . . . . ?
C1 C2 C7 C9 13.2(7) . . . . ?
Nd1 O3 C8 O4 10.1(7) 2_576 . . . ?
Nd1 O3 C8 C4 -169.4(3) 2_576 . . . ?
Nd1 O4 C8 O3 -6.4(8) 1_565 . . . ?
Nd1 O4 C8 C4 173.1(3) 1_565 . . . ?
C5 C4 C8 O3 170.4(4) . . . . ?
C3 C4 C8 O3 -11.4(6) . . . . ?
C5 C4 C8 O4 -9.2(6) . . . . ?
C3 C4 C8 O4 169.0(4) . . . . ?
C10 N1 C9 C13 1.0(7) . . . . ?
C10 N1 C9 C7 175.8(4) . . . . ?
C6 C7 C9 N1 -142.3(5) . . . . ?
C2 C7 C9 N1 34.4(7) . . . . ?
C6 C7 C9 C13 32.1(7) . . . . ?
C2 C7 C9 C13 -151.2(5) . . . . ?
C9 N1 C10 C11 -1.4(7) . . . . ?
N1 C10 C11 C12 0.9(7) . . . . ?
N1 C10 C11 C14 -177.6(4) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C14 C11 C12 C13 178.3(4) . . . . ?
C11 C12 C13 C9 -0.2(7) . . . . ?
N1 C9 C13 C12 -0.2(7) . . . . ?
C7 C9 C13 C12 -174.9(4) . . . . ?
C10 C11 C14 C15 43.2(7) . . . . ?
C12 C11 C14 C15 -135.2(5) . . . . ?
C10 C11 C14 C19 -139.0(5) . . . . ?
C12 C11 C14 C19 42.6(7) . . . . ?
C19 C14 C15 C16 0.9(8) . . . . ?
C11 C14 C15 C16 178.8(5) . . . . ?
C14 C15 C16 C17 -0.8(9) . . . . ?
C15 C16 C17 C18 0.3(8) . . . . ?
C15 C16 C17 C21 -179.6(5) . . . . ?
C16 C17 C18 C19 0.1(7) . . . . ?
C21 C17 C18 C19 -180.0(4) . . . . ?
C17 C18 C19 C14 -0.1(7) . . . . ?
C17 C18 C19 C20 -179.3(4) . . . . ?
C15 C14 C19 C18 -0.4(7) . . . . ?
C11 C14 C19 C18 -178.3(4) . . . . ?
C15 C14 C19 C20 178.8(5) . . . . ?
C11 C14 C19 C20 0.9(7) . . . . ?
Nd1 O5 C20 O6 -119.1(6) 2_666 . . . ?
Nd1 O5 C20 O6 2.5(5) 1_655 . . . ?
Nd1 O5 C20 C19 61.7(8) 2_666 . . . ?
Nd1 O5 C20 C19 -176.6(4) 1_655 . . . ?
Nd1 O5 C20 Nd1 -121.7(6) 2_666 . . 1_655 ?
Nd1 O6 C20 O5 -2.7(5) 1_655 . . . ?
Nd1 O6 C20 C19 176.4(3) 1_655 . . . ?
C18 C19 C20 O5 -125.1(5) . . . . ?
C14 C19 C20 O5 55.7(6) . . . . ?
C18 C19 C20 O6 55.7(6) . . . . ?
C14 C19 C20 O6 -123.5(5) . . . . ?
C18 C19 C20 Nd1 83(3) . . . 1_655 ?
C14 C19 C20 Nd1 -96(3) . . . 1_655 ?
Nd1 O7 C21 O8 43.2(10) 1_654 . . . ?
Nd1 O7 C21 C17 -140.9(5) 1_654 . . . ?
C16 C17 C21 O8 -177.8(5) . . . . ?
C18 C17 C21 O8 2.3(7) . . . . ?
C16 C17 C21 O7 6.2(7) . . . . ?
C18 C17 C21 O7 -173.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H11 O1 0.84 2.19 2.904(4) 142.8 2_666
O1W H12 O8 0.84 2.40 2.827(5) 112.7 1_456

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         2.322
_refine_diff_density_min         -2.280
_refine_diff_density_rms         0.152
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_eu
_database_code_depnum_ccdc_archive 'CCDC 1412703'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H12 Eu N O9'
_chemical_formula_weight         574.28

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   18.3160(14)
_cell_length_b                   12.2002(9)
_cell_length_c                   9.5032(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.0860(10)
_cell_angle_gamma                90.00
_cell_volume                     1938.7(3)
_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_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    3.293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.334
_exptl_absorpt_correction_T_max  0.687
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5806
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2208
_reflns_number_gt                2070
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0479P)²+9.0227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2208
_refine_ls_number_parameters     150
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.205
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.5000 0.36567(2) 0.7500 0.01607(12) Uani 1 2 d S . .
O1 O 0.5437(2) 0.2034(3) 0.6331(5) 0.0346(9) Uani 1 1 d U . .
O2 O 0.6410(2) 0.3009(4) 0.7937(6) 0.0617(14) Uani 1 1 d U . .
O3 O 0.9129(2) 0.1225(3) 0.9780(4) 0.0275(8) Uani 1 1 d U . .
O4 O 0.9406(2) 0.0208(3) 0.8143(4) 0.0313(8) Uani 1 1 d U . .
O1W O 0.6180(6) -0.1216(6) 0.5477(11) 0.044(2) Uani 0.50 1 d PU . .
H1W1 H 0.5768 -0.1610 0.5153 0.066 Uiso 0.50 1 d PR . .
H1W2 H 0.6553 -0.1559 0.5374 0.066 Uiso 0.50 1 d PR . .
C1 C 0.6166(3) 0.2286(4) 0.6953(5) 0.0199(9) Uani 1 1 d U . .
C2 C 0.6762(2) 0.1690(4) 0.6502(5) 0.0169(8) Uani 1 1 d U . .
C3 C 0.7543(3) 0.1556(3) 0.7615(5) 0.0161(8) Uani 1 1 d U . .
H3 H 0.7686 0.1857 0.8591 0.019 Uiso 1 1 calc R . .
C4 C 0.8112(2) 0.0973(4) 0.7281(5) 0.0177(8) Uani 1 1 d U . .
C5 C 0.7897(3) 0.0560(5) 0.5803(6) 0.0315(11) Uani 1 1 d U . .
H5 H 0.8271 0.0179 0.5562 0.038 Uiso 1 1 calc R . .
C6 C 0.7129(3) 0.0710(5) 0.4685(6) 0.0323(12) Uani 1 1 d U . .
H6 H 0.6997 0.0445 0.3694 0.039 Uiso 1 1 calc R . .
C7 C 0.6550(3) 0.1255(4) 0.5029(5) 0.0215(9) Uani 1 1 d U . .
C8 C 0.8945(2) 0.0781(3) 0.8502(5) 0.0166(8) Uani 1 1 d U . .
C9 C 0.5363(2) 0.2320(4) 0.3137(5) 0.0194(9) Uani 1 1 d U . .
H9 H 0.5604 0.2981 0.3572 0.023 Uiso 1 1 calc R . .
C10 C 0.5733(3) 0.1335(4) 0.3764(6) 0.0215(9) Uani 1 1 d U . .
N1 N 0.5360(3) 0.0395(4) 0.3128(6) 0.0322(11) Uani 0.50 1 d P . 1
H1 H 0.5583 -0.0235 0.3528 0.039 Uiso 0.50 1 calc PR . 1
C11 C 0.5360(3) 0.0395(4) 0.3128(6) 0.0322(11) Uani 0.50 1 d PU . 2
H11 H 0.5596 -0.0271 0.3551 0.039 Uiso 0.50 1 calc PR . 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
Eu1 O4 2.383(3) 8_657 ?
Eu1 O4 2.383(3) 3_455 ?
Eu1 O3 2.425(3) 7_657 ?
Eu1 O3 2.425(3) 4_454 ?
Eu1 O1 2.554(4) . ?
Eu1 O1 2.554(4) 6_657 ?
Eu1 O2 2.567(4) 6_657 ?
Eu1 O2 2.567(4) . ?
Eu1 C1 2.922(4) 6_657 ?
Eu1 C1 2.922(4) . ?
O1 C1 1.258(6) . ?
O2 C1 1.229(6) . ?
O3 C8 1.245(5) . ?
O3 Eu1 2.425(3) 7_657 ?
O4 C8 1.246(5) . ?
O4 Eu1 2.383(3) 3_545 ?
O1W H1W1 0.8401 . ?
O1W H1W2 0.8400 . ?
C1 C2 1.512(6) . ?
C2 C7 1.396(6) . ?
C2 C3 1.399(6) . ?
C3 C4 1.401(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(6) . ?
C4 C8 1.512(5) . ?
C5 C6 1.386(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(7) . ?
C6 H6 0.9300 . ?
C7 C10 1.493(6) . ?
C9 C9 1.386(8) 6_656 ?
C9 C10 1.389(6) . ?
C9 H9 0.9300 . ?
C10 N1 1.346(6) . ?
N1 N1 1.370(9) 6_656 ?
N1 H1 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Eu1 O4 74.8(2) 8_657 3_455 ?
O4 Eu1 O3 93.19(12) 8_657 7_657 ?
O4 Eu1 O3 81.38(11) 3_455 7_657 ?
O4 Eu1 O3 81.38(11) 8_657 4_454 ?
O4 Eu1 O3 93.19(12) 3_455 4_454 ?
O3 Eu1 O3 173.19(16) 7_657 4_454 ?
O4 Eu1 O1 104.32(14) 8_657 . ?
O4 Eu1 O1 169.76(12) 3_455 . ?
O3 Eu1 O1 108.86(12) 7_657 . ?
O3 Eu1 O1 76.63(13) 4_454 . ?
O4 Eu1 O1 169.76(12) 8_657 6_657 ?
O4 Eu1 O1 104.32(14) 3_455 6_657 ?
O3 Eu1 O1 76.63(13) 7_657 6_657 ?
O3 Eu1 O1 108.86(12) 4_454 6_657 ?
O1 Eu1 O1 78.37(19) . 6_657 ?
O4 Eu1 O2 137.46(13) 8_657 6_657 ?
O4 Eu1 O2 75.63(17) 3_455 6_657 ?
O3 Eu1 O2 111.79(15) 7_657 6_657 ?
O3 Eu1 O2 70.44(14) 4_454 6_657 ?
O1 Eu1 O2 99.48(17) . 6_657 ?
O1 Eu1 O2 50.09(12) 6_657 6_657 ?
O4 Eu1 O2 75.63(17) 8_657 . ?
O4 Eu1 O2 137.46(13) 3_455 . ?
O3 Eu1 O2 70.44(14) 7_657 . ?
O3 Eu1 O2 111.79(15) 4_454 . ?
O1 Eu1 O2 50.09(12) . . ?
O1 Eu1 O2 99.48(16) 6_657 . ?
O2 Eu1 O2 144.2(2) 6_657 . ?
O4 Eu1 C1 160.60(13) 8_657 6_657 ?
O4 Eu1 C1 88.05(14) 3_455 6_657 ?
O3 Eu1 C1 93.15(13) 7_657 6_657 ?
O3 Eu1 C1 90.74(12) 4_454 6_657 ?
O1 Eu1 C1 90.90(13) . 6_657 ?
O1 Eu1 C1 25.45(12) 6_657 6_657 ?
O2 Eu1 C1 24.82(13) 6_657 6_657 ?
O2 Eu1 C1 123.75(17) . 6_657 ?
O4 Eu1 C1 88.05(13) 8_657 . ?
O4 Eu1 C1 160.60(13) 3_455 . ?
O3 Eu1 C1 90.74(12) 7_657 . ?
O3 Eu1 C1 93.15(13) 4_454 . ?
O1 Eu1 C1 25.45(12) . . ?
O1 Eu1 C1 90.90(13) 6_657 . ?
O2 Eu1 C1 123.75(17) 6_657 . ?
O2 Eu1 C1 24.82(13) . . ?
C1 Eu1 C1 110.17(19) 6_657 . ?
C1 O1 Eu1 93.8(3) . . ?
C1 O2 Eu1 93.9(3) . . ?
C8 O3 Eu1 149.8(3) . 7_657 ?
C8 O4 Eu1 161.1(3) . 3_545 ?
H1W1 O1W H1W2 108.9 . . ?
O2 C1 O1 121.3(4) . . ?
O2 C1 C2 118.7(4) . . ?
O1 C1 C2 120.0(4) . . ?
O2 C1 Eu1 61.2(3) . . ?
O1 C1 Eu1 60.7(2) . . ?
C2 C1 Eu1 172.1(3) . . ?
C7 C2 C3 119.6(4) . . ?
C7 C2 C1 122.0(4) . . ?
C3 C2 C1 118.4(4) . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 C8 120.0(4) . . ?
C3 C4 C8 121.0(4) . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 119.2(4) . . ?
C2 C7 C10 124.0(4) . . ?
C6 C7 C10 116.7(4) . . ?
O3 C8 O4 124.6(4) . . ?
O3 C8 C4 117.9(4) . . ?
O4 C8 C4 117.5(4) . . ?
C9 C9 C10 120.0(3) 6_656 . ?
C9 C9 H9 120.0 6_656 . ?
C10 C9 H9 120.0 . . ?
N1 C10 C9 118.4(4) . . ?
N1 C10 C7 117.7(4) . . ?
C9 C10 C7 123.7(4) . . ?
C10 N1 N1 121.5(3) . 6_656 ?
C10 N1 H1 119.2 . . ?
N1 N1 H1 119.2 6_656 . ?

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
O4 Eu1 O1 C1 51.8(3) 8_657 . . . ?
O4 Eu1 O1 C1 135.7(7) 3_455 . . . ?
O3 Eu1 O1 C1 -46.7(3) 7_657 . . . ?
O3 Eu1 O1 C1 129.1(3) 4_454 . . . ?
O1 Eu1 O1 C1 -118.0(4) 6_657 . . . ?
O2 Eu1 O1 C1 -163.7(3) 6_657 . . . ?
O2 Eu1 O1 C1 -5.0(3) . . . . ?
C1 Eu1 O1 C1 -140.3(3) 6_657 . . . ?
O4 Eu1 O2 C1 -118.0(4) 8_657 . . . ?
O4 Eu1 O2 C1 -165.3(3) 3_455 . . . ?
O3 Eu1 O2 C1 143.2(4) 7_657 . . . ?
O3 Eu1 O2 C1 -43.7(4) 4_454 . . . ?
O1 Eu1 O2 C1 5.1(3) . . . . ?
O1 Eu1 O2 C1 71.2(4) 6_657 . . . ?
O2 Eu1 O2 C1 42.8(4) 6_657 . . . ?
C1 Eu1 O2 C1 62.8(5) 6_657 . . . ?
Eu1 O2 C1 O1 -9.4(6) . . . . ?
Eu1 O2 C1 C2 171.0(4) . . . . ?
Eu1 O1 C1 O2 9.4(6) . . . . ?
Eu1 O1 C1 C2 -171.0(4) . . . . ?
O4 Eu1 C1 O2 58.8(4) 8_657 . . . ?
O4 Eu1 C1 O2 31.1(6) 3_455 . . . ?
O3 Eu1 C1 O2 -34.4(4) 7_657 . . . ?
O3 Eu1 C1 O2 140.1(4) 4_454 . . . ?
O1 Eu1 C1 O2 -170.8(6) . . . . ?
O1 Eu1 C1 O2 -111.0(4) 6_657 . . . ?
O2 Eu1 C1 O2 -151.4(3) 6_657 . . . ?
C1 Eu1 C1 O2 -128.0(4) 6_657 . . . ?
O4 Eu1 C1 O1 -130.4(3) 8_657 . . . ?
O4 Eu1 C1 O1 -158.0(3) 3_455 . . . ?
O3 Eu1 C1 O1 136.5(3) 7_657 . . . ?
O3 Eu1 C1 O1 -49.1(3) 4_454 . . . ?
O1 Eu1 C1 O1 59.8(4) 6_657 . . . ?
O2 Eu1 C1 O1 19.4(4) 6_657 . . . ?
O2 Eu1 C1 O1 170.8(6) . . . . ?
C1 Eu1 C1 O1 42.8(3) 6_657 . . . ?
O4 Eu1 C1 C2 -33(2) 8_657 . . . ?
O4 Eu1 C1 C2 -61(2) 3_455 . . . ?
O3 Eu1 C1 C2 -126(2) 7_657 . . . ?
O3 Eu1 C1 C2 48(2) 4_454 . . . ?
O1 Eu1 C1 C2 97(2) . . . . ?
O1 Eu1 C1 C2 157(2) 6_657 . . . ?
O2 Eu1 C1 C2 117(2) 6_657 . . . ?
O2 Eu1 C1 C2 -92(2) . . . . ?
C1 Eu1 C1 C2 140(2) 6_657 . . . ?
O2 C1 C2 C7 -150.5(6) . . . . ?
O1 C1 C2 C7 29.9(7) . . . . ?
Eu1 C1 C2 C7 -63(2) . . . . ?
O2 C1 C2 C3 31.0(7) . . . . ?
O1 C1 C2 C3 -148.6(5) . . . . ?
Eu1 C1 C2 C3 119(2) . . . . ?
C7 C2 C3 C4 -1.1(7) . . . . ?
C1 C2 C3 C4 177.4(4) . . . . ?
C2 C3 C4 C5 2.2(7) . . . . ?
C2 C3 C4 C8 -177.2(4) . . . . ?
C3 C4 C5 C6 -0.8(8) . . . . ?
C8 C4 C5 C6 178.5(5) . . . . ?
C4 C5 C6 C7 -1.6(9) . . . . ?
C3 C2 C7 C6 -1.3(7) . . . . ?
C1 C2 C7 C6 -179.8(5) . . . . ?
C3 C2 C7 C10 179.0(4) . . . . ?
C1 C2 C7 C10 0.5(7) . . . . ?
C5 C6 C7 C2 2.6(8) . . . . ?
C5 C6 C7 C10 -177.6(5) . . . . ?
Eu1 O3 C8 O4 -19.6(10) 7_657 . . . ?
Eu1 O3 C8 C4 162.3(5) 7_657 . . . ?
Eu1 O4 C8 O3 109.5(9) 3_545 . . . ?
Eu1 O4 C8 C4 -72.3(11) 3_545 . . . ?
C5 C4 C8 O3 175.4(5) . . . . ?
C3 C4 C8 O3 -5.3(7) . . . . ?
C5 C4 C8 O4 -2.9(7) . . . . ?
C3 C4 C8 O4 176.5(4) . . . . ?
C9 C9 C10 N1 -1.5(9) 6_656 . . . ?
C9 C9 C10 C7 173.6(5) 6_656 . . . ?
C2 C7 C10 N1 -122.7(5) . . . . ?
C6 C7 C10 N1 57.5(7) . . . . ?
C2 C7 C10 C9 62.1(7) . . . . ?
C6 C7 C10 C9 -117.7(6) . . . . ?
C9 C10 N1 N1 1.4(10) . . . 6_656 ?
C7 C10 N1 N1 -174.1(6) . . . 6_656 ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.096
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.159
####################################################################### 
# 
# 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_sm
_database_code_depnum_ccdc_archive 'CCDC 1412704'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Sm (H2 O) (C17 H10 N O8), 1.5H2 O'
_chemical_formula_sum            'C21 H15 N O10.5 Sm'
_chemical_formula_weight         599.69

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.4281(6)
_cell_length_b                   10.5623(7)
_cell_length_c                   11.1893(7)
_cell_angle_alpha                64.0602(9)
_cell_angle_beta                 80.8746(9)
_cell_angle_gamma                82.0709(8)
_cell_volume                     986.36(11)
_cell_formula_units_Z            2
_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_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    3.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5050
_exptl_absorpt_correction_T_max  0.6257
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6073
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4374
_reflns_number_gt                4070
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0328P)²+0.8158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4374
_refine_ls_number_parameters     318
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.668481(15) 0.098948(15) 0.506428(15) 0.02004(6) Uani 1 1 d . . .
O1 O 0.4868(3) 0.0869(3) 0.3431(2) 0.0344(5) Uani 1 1 d . . .
O2 O 0.6955(3) 0.1746(3) 0.2558(3) 0.0506(7) Uani 1 1 d . . .
O3 O 0.6846(3) 0.1334(3) -0.3048(3) 0.0459(7) Uani 1 1 d . . .
O4 O 0.8185(3) 0.0061(3) -0.1412(3) 0.0563(8) Uani 1 1 d . . .
O5 O -0.1115(2) 0.2501(2) 0.4094(3) 0.0326(5) Uani 1 1 d . . .
O6 O -0.3288(3) 0.3582(3) 0.3893(3) 0.0418(6) Uani 1 1 d . . .
O7 O -0.4355(2) 0.7859(2) 0.4593(3) 0.0337(5) Uani 1 1 d . . .
O8 O -0.2543(2) 0.9040(3) 0.4539(3) 0.0359(6) Uani 1 1 d . . .
O1w O 0.8770(3) -0.0483(3) 0.6255(3) 0.0408(6) Uani 1 1 d D . .
H11 H 0.895(5) -0.046(5) 0.696(3) 0.073(17) Uiso 1 1 d D . .
H12 H 0.935(4) -0.110(4) 0.612(5) 0.077(17) Uiso 1 1 d D . .
O2w O -0.0380(7) 0.2323(8) 0.0513(7) 0.0654(13) Uani 0.50 1 d PU A 1
H21 H -0.1096 0.2180 0.1096 0.098 Uiso 0.50 1 d PR A 1
H22 H -0.0057 0.1569 0.0453 0.098 Uiso 0.50 1 d PR A 1
O2w' O -0.1439(7) 0.3650(7) 0.0797(7) 0.0654(13) Uani 0.50 1 d P B 2
H23 H -0.1941 0.3029 0.1398 0.098 Uiso 0.50 1 d PR B 2
H24 H -0.1127 0.3412 0.0172 0.098 Uiso 0.50 1 d PR B 2
O3w' O 0.0107(9) 0.1818(9) -0.0293(7) 0.079(2) Uani 0.50 1 d PU C 2
H31 H 0.0655 0.1230 0.0252 0.118 Uiso 0.50 1 d PR C 2
H32 H -0.0480 0.1395 -0.0453 0.118 Uiso 0.50 1 d PR C 2
N1 N 0.1797(3) 0.3373(3) 0.1179(3) 0.0335(7) Uani 0.50 1 d P D 1
H1 H 0.1512 0.2980 0.0717 0.040 Uiso 0.50 1 calc PR D 1
C1' C 0.1797(3) 0.3373(3) 0.1179(3) 0.0335(7) Uani 0.50 1 d P D 2
H1' H 0.1496 0.2958 0.0691 0.040 Uiso 0.50 1 calc PR D 2
C1 C 0.5777(4) 0.1429(3) 0.2436(3) 0.0295(7) Uani 1 1 d . . .
C2 C 0.5457(3) 0.1769(3) 0.1043(3) 0.0247(6) Uani 1 1 d . . .
C3 C 0.6392(3) 0.1195(3) 0.0284(3) 0.0249(6) Uani 1 1 d . . .
H3 H 0.7193 0.0608 0.0643 0.030 Uiso 1 1 calc R . .
C4 C 0.6139(3) 0.1494(3) -0.1013(3) 0.0257(6) Uani 1 1 d . . .
C5 C 0.4946(4) 0.2377(4) -0.1546(4) 0.0371(8) Uani 1 1 d . . .
H5 H 0.4770 0.2578 -0.2408 0.045 Uiso 1 1 calc R . .
C6 C 0.4023(4) 0.2956(4) -0.0798(4) 0.0407(9) Uani 1 1 d . . .
H6 H 0.3233 0.3556 -0.1167 0.049 Uiso 1 1 calc R . .
C7 C 0.4254(4) 0.2654(4) 0.0503(3) 0.0299(7) Uani 1 1 d . D .
C8 C 0.7132(3) 0.0893(4) -0.1869(3) 0.0302(7) Uani 1 1 d . . .
C9 C 0.3239(4) 0.3332(4) 0.1251(3) 0.0303(7) Uani 1 1 d . . .
C10 C 0.3638(4) 0.3954(4) 0.1998(4) 0.0320(7) Uani 1 1 d . D .
H10 H 0.4608 0.3956 0.2065 0.038 Uiso 1 1 calc R . .
C11 C 0.2606(4) 0.4570(4) 0.2641(4) 0.0331(7) Uani 1 1 d . . .
H11A H 0.2891 0.4973 0.3148 0.040 Uiso 1 1 calc R D .
C12 C 0.1152(4) 0.4600(3) 0.2546(4) 0.0311(7) Uani 1 1 d . D .
C13 C 0.0808(3) 0.3995(3) 0.1790(3) 0.0324(7) Uani 0.50 1 d P D 1
H13 H -0.0158 0.4014 0.1694 0.039 Uiso 0.50 1 calc PR D 1
N13' N 0.0808(3) 0.3995(3) 0.1790(3) 0.0324(7) Uani 0.50 1 d P D 2
H13' H -0.0106 0.4013 0.1699 0.039 Uiso 0.50 1 calc PR D 2
C14 C 0.0024(3) 0.5367(3) 0.3122(4) 0.0305(7) Uani 1 1 d . . .
C15 C 0.0410(4) 0.6587(4) 0.3121(5) 0.0474(11) Uani 1 1 d . D .
H15 H 0.1356 0.6830 0.2832 0.057 Uiso 1 1 calc R . .
C16 C -0.0572(4) 0.7460(4) 0.3540(4) 0.0422(9) Uani 1 1 d . . .
H16 H -0.0280 0.8268 0.3536 0.051 Uiso 1 1 calc R D .
C17 C -0.1976(3) 0.7125(3) 0.3959(3) 0.0264(6) Uani 1 1 d . D .
C18 C -0.2379(3) 0.5892(3) 0.3987(3) 0.0249(6) Uani 1 1 d . . .
H18 H -0.3331 0.5666 0.4271 0.030 Uiso 1 1 calc R D .
C19 C -0.1401(3) 0.4988(3) 0.3603(3) 0.0235(6) Uani 1 1 d . D .
C20 C -0.1955(3) 0.3601(3) 0.3859(3) 0.0262(6) Uani 1 1 d . . .
C21 C -0.3052(3) 0.8085(3) 0.4398(3) 0.0255(6) Uani 1 1 d . . .


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 O1 2.748(3) . ?
Sm1 O1 2.439(2) 2_656 ?
Sm1 O2 2.537(3) . ?
Sm1 O5 2.591(2) 1_655 ?
Sm1 O6 2.467(2) 1_655 ?
Sm1 O7 2.420(2) 2_566 ?
Sm1 O3 2.326(2) 1_556 ?
Sm1 O8 2.372(2) 1_645 ?
Sm1 O1w 2.497(2) . ?
O1 C1 1.259(4) . ?
O1 Sm1 2.439(2) 2_656 ?
O2 C1 1.246(4) . ?
O3 C8 1.254(4) . ?
O3 Sm1 2.326(2) 1_554 ?
O4 C8 1.244(4) . ?
O5 C20 1.262(4) . ?
O5 Sm1 2.591(2) 1_455 ?
O6 C20 1.254(4) . ?
O6 Sm1 2.467(2) 1_455 ?
O7 C21 1.251(4) . ?
O7 Sm1 2.420(2) 2_566 ?
O8 C21 1.253(4) . ?
O8 Sm1 2.372(2) 1_465 ?
O1w H11 0.844(10) . ?
O1w H12 0.844(10) . ?
O2w H21 0.8400 . ?
O2w H22 0.8401 . ?
O2w H24 1.2003 . ?
O2w' H21 1.4379 . ?
O2w' H23 0.8400 . ?
O2w' H24 0.8400 . ?
O3w' H22 0.7542 . ?
O3w' H31 0.8401 . ?
O3w' H32 0.8399 . ?
N1 C13 1.338(4) . ?
N1 C9 1.368(4) . ?
N1 H1 0.8800 . ?
C1 C2 1.510(4) . ?
C2 C3 1.390(4) . ?
C2 C7 1.398(5) . ?
C3 C4 1.397(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(5) . ?
C4 C8 1.510(4) . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(5) . ?
C6 H6 0.9300 . ?
C7 C9 1.487(4) . ?
C9 C10 1.386(5) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.358(4) . ?
C12 C14 1.485(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(5) . ?
C14 C19 1.409(4) . ?
C15 C16 1.390(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(4) . ?
C17 C21 1.514(4) . ?
C18 C19 1.392(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.515(4) . ?
C20 Sm1 2.872(3) 1_455 ?

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 Sm1 O8 131.50(10) 1_556 1_645 ?
O3 Sm1 O7 76.70(9) 1_556 2_566 ?
O8 Sm1 O7 134.09(8) 1_645 2_566 ?
O3 Sm1 O1 84.83(10) 1_556 2_656 ?
O8 Sm1 O1 74.74(8) 1_645 2_656 ?
O7 Sm1 O1 73.12(8) 2_566 2_656 ?
O3 Sm1 O6 84.09(10) 1_556 1_655 ?
O8 Sm1 O6 136.70(9) 1_645 1_655 ?
O7 Sm1 O6 68.72(8) 2_566 1_655 ?
O1 Sm1 O6 141.75(8) 2_656 1_655 ?
O3 Sm1 O1w 69.03(9) 1_556 . ?
O8 Sm1 O1w 67.08(9) 1_645 . ?
O7 Sm1 O1w 142.52(9) 2_566 . ?
O1 Sm1 O1w 88.81(9) 2_656 . ?
O6 Sm1 O1w 120.57(9) 1_655 . ?
O3 Sm1 O2 152.97(10) 1_556 . ?
O8 Sm1 O2 68.86(10) 1_645 . ?
O7 Sm1 O2 101.54(10) 2_566 . ?
O1 Sm1 O2 120.90(8) 2_656 . ?
O6 Sm1 O2 70.52(10) 1_655 . ?
O1w Sm1 O2 115.86(10) . . ?
O3 Sm1 O5 83.22(9) 1_556 1_655 ?
O8 Sm1 O5 102.39(8) 1_645 1_655 ?
O7 Sm1 O5 118.29(7) 2_566 1_655 ?
O1 Sm1 O5 160.78(8) 2_656 1_655 ?
O6 Sm1 O5 51.42(7) 1_655 1_655 ?
O1w Sm1 O5 72.87(9) . 1_655 ?
O2 Sm1 O5 73.85(8) . 1_655 ?
O3 Sm1 O1 145.78(8) 1_556 . ?
O8 Sm1 O1 70.34(8) 1_645 . ?
O7 Sm1 O1 70.72(7) 2_566 . ?
O1 Sm1 O1 76.09(8) 2_656 . ?
O6 Sm1 O1 93.50(8) 1_655 . ?
O1w Sm1 O1 137.21(8) . . ?
O2 Sm1 O1 48.70(8) . . ?
O5 Sm1 O1 121.39(7) 1_655 . ?
C1 O1 Sm1 154.1(2) . 2_656 ?
C1 O1 Sm1 89.6(2) . . ?
Sm1 O1 Sm1 103.91(8) 2_656 . ?
C1 O2 Sm1 100.0(2) . . ?
C8 O3 Sm1 151.6(3) . 1_554 ?
C20 O5 Sm1 89.50(18) . 1_455 ?
C20 O6 Sm1 95.44(19) . 1_455 ?
C21 O7 Sm1 139.0(2) . 2_566 ?
C21 O8 Sm1 140.2(2) . 1_465 ?
Sm1 O1w H11 121(3) . . ?
Sm1 O1w H12 131(3) . . ?
H11 O1w H12 108.1(17) . . ?
H21 O2w H22 110.3 . . ?
H21 O2w H24 73.8 . . ?
H22 O2w H24 152.2 . . ?
H21 O2w' H23 59.2 . . ?
H21 O2w' H24 60.5 . . ?
H23 O2w' H24 110.3 . . ?
H22 O3w' H31 57.1 . . ?
H22 O3w' H32 101.7 . . ?
H31 O3w' H32 109.9 . . ?
C13 N1 C9 121.9(3) . . ?
C13 N1 H1 119.1 . . ?
C9 N1 H1 119.1 . . ?
O2 C1 O1 121.7(3) . . ?
O2 C1 C2 117.7(3) . . ?
O1 C1 C2 120.6(3) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 118.8(3) . . ?
C7 C2 C1 121.5(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 C8 118.4(3) . . ?
C3 C4 C8 122.0(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 119.2(3) . . ?
C6 C7 C9 118.6(3) . . ?
C2 C7 C9 122.2(3) . . ?
O4 C8 O3 124.1(3) . . ?
O4 C8 C4 120.4(3) . . ?
O3 C8 C4 115.5(3) . . ?
N1 C9 C10 117.1(3) . . ?
N1 C9 C7 117.8(3) . . ?
C10 C9 C7 125.1(3) . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C13 C12 C11 116.6(3) . . ?
C13 C12 C14 120.7(3) . . ?
C11 C12 C14 122.5(3) . . ?
N1 C13 C12 122.9(3) . . ?
N1 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C15 C14 C19 118.5(3) . . ?
C15 C14 C12 116.2(3) . . ?
C19 C14 C12 125.3(3) . . ?
C14 C15 C16 122.1(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 C21 119.7(3) . . ?
C18 C17 C21 121.2(3) . . ?
C17 C18 C19 122.0(3) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C14 118.6(3) . . ?
C18 C19 C20 115.5(3) . . ?
C14 C19 C20 125.6(3) . . ?
O6 C20 O5 121.7(3) . . ?
O6 C20 C19 117.1(3) . . ?
O5 C20 C19 121.1(3) . . ?
O6 C20 Sm1 58.79(17) . 1_455 ?
O5 C20 Sm1 64.45(17) . 1_455 ?
C19 C20 Sm1 163.6(2) . 1_455 ?
O7 C21 O8 125.8(3) . . ?
O7 C21 C17 118.0(3) . . ?
O8 C21 C17 116.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Sm1 O1 C1 144.2(2) 1_556 . . . ?
O8 Sm1 O1 C1 -79.24(19) 1_645 . . . ?
O7 Sm1 O1 C1 125.6(2) 2_566 . . . ?
O1 Sm1 O1 C1 -157.7(2) 2_656 . . . ?
O6 Sm1 O1 C1 59.56(19) 1_655 . . . ?
O1w Sm1 O1 C1 -85.1(2) . . . . ?
O2 Sm1 O1 C1 -0.54(19) . . . . ?
O5 Sm1 O1 C1 13.6(2) 1_655 . . . ?
O3 Sm1 O1 Sm1 -58.06(19) 1_556 . . 2_656 ?
O8 Sm1 O1 Sm1 78.50(9) 1_645 . . 2_656 ?
O7 Sm1 O1 Sm1 -76.69(9) 2_566 . . 2_656 ?
O1 Sm1 O1 Sm1 0.0 2_656 . . 2_656 ?
O6 Sm1 O1 Sm1 -142.70(9) 1_655 . . 2_656 ?
O1w Sm1 O1 Sm1 72.60(14) . . . 2_656 ?
O2 Sm1 O1 Sm1 157.20(15) . . . 2_656 ?
O5 Sm1 O1 Sm1 171.30(7) 1_655 . . 2_656 ?
O3 Sm1 O2 C1 -133.9(2) 1_556 . . . ?
O8 Sm1 O2 C1 82.5(2) 1_645 . . . ?
O7 Sm1 O2 C1 -50.5(2) 2_566 . . . ?
O1 Sm1 O2 C1 26.6(3) 2_656 . . . ?
O6 Sm1 O2 C1 -112.8(2) 1_655 . . . ?
O1w Sm1 O2 C1 131.8(2) . . . . ?
O5 Sm1 O2 C1 -166.9(2) 1_655 . . . ?
O1 Sm1 O2 C1 0.56(19) . . . . ?
Sm1 O2 C1 O1 -1.1(4) . . . . ?
Sm1 O2 C1 C2 177.6(2) . . . . ?
Sm1 O1 C1 O2 -121.5(5) 2_656 . . . ?
Sm1 O1 C1 O2 1.0(3) . . . . ?
Sm1 O1 C1 C2 59.8(6) 2_656 . . . ?
Sm1 O1 C1 C2 -177.6(3) . . . . ?
O2 C1 C2 C3 58.4(4) . . . . ?
O1 C1 C2 C3 -123.0(3) . . . . ?
O2 C1 C2 C7 -121.0(4) . . . . ?
O1 C1 C2 C7 57.7(4) . . . . ?
C7 C2 C3 C4 -0.1(5) . . . . ?
C1 C2 C3 C4 -179.5(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C2 C3 C4 C8 179.9(3) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C8 C4 C5 C6 -179.4(3) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C5 C6 C7 C2 1.0(6) . . . . ?
C5 C6 C7 C9 178.8(4) . . . . ?
C3 C2 C7 C6 -0.6(5) . . . . ?
C1 C2 C7 C6 178.8(3) . . . . ?
C3 C2 C7 C9 -178.2(3) . . . . ?
C1 C2 C7 C9 1.2(5) . . . . ?
Sm1 O3 C8 O4 40.3(7) 1_554 . . . ?
Sm1 O3 C8 C4 -142.5(4) 1_554 . . . ?
C5 C4 C8 O4 -177.6(4) . . . . ?
C3 C4 C8 O4 2.8(5) . . . . ?
C5 C4 C8 O3 5.1(5) . . . . ?
C3 C4 C8 O3 -174.5(3) . . . . ?
C13 N1 C9 C10 0.5(5) . . . . ?
C13 N1 C9 C7 -178.2(3) . . . . ?
C6 C7 C9 N1 43.8(5) . . . . ?
C2 C7 C9 N1 -138.6(3) . . . . ?
C6 C7 C9 C10 -134.8(4) . . . . ?
C2 C7 C9 C10 42.8(5) . . . . ?
N1 C9 C10 C11 0.6(5) . . . . ?
C7 C9 C10 C11 179.2(3) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C10 C11 C12 C14 -174.3(3) . . . . ?
C9 N1 C13 C12 -1.4(6) . . . . ?
C11 C12 C13 N1 1.2(5) . . . . ?
C14 C12 C13 N1 175.5(3) . . . . ?
C13 C12 C14 C15 -141.1(4) . . . . ?
C11 C12 C14 C15 32.9(6) . . . . ?
C13 C12 C14 C19 35.8(5) . . . . ?
C11 C12 C14 C19 -150.2(4) . . . . ?
C19 C14 C15 C16 -2.0(7) . . . . ?
C12 C14 C15 C16 175.2(4) . . . . ?
C14 C15 C16 C17 -0.6(7) . . . . ?
C15 C16 C17 C18 1.6(6) . . . . ?
C15 C16 C17 C21 -179.2(4) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C21 C17 C18 C19 -179.2(3) . . . . ?
C17 C18 C19 C14 -2.6(5) . . . . ?
C17 C18 C19 C20 172.4(3) . . . . ?
C15 C14 C19 C18 3.5(5) . . . . ?
C12 C14 C19 C18 -173.4(3) . . . . ?
C15 C14 C19 C20 -170.9(4) . . . . ?
C12 C14 C19 C20 12.2(6) . . . . ?
Sm1 O6 C20 O5 14.7(3) 1_455 . . . ?
Sm1 O6 C20 C19 -161.8(2) 1_455 . . . ?
Sm1 O5 C20 O6 -13.9(3) 1_455 . . . ?
Sm1 O5 C20 C19 162.5(3) 1_455 . . . ?
C18 C19 C20 O6 26.4(4) . . . . ?
C14 C19 C20 O6 -159.1(3) . . . . ?
C18 C19 C20 O5 -150.2(3) . . . . ?
C14 C19 C20 O5 24.3(5) . . . . ?
C18 C19 C20 Sm1 -44.7(9) . . . 1_455 ?
C14 C19 C20 Sm1 129.8(7) . . . 1_455 ?
Sm1 O7 C21 O8 12.6(6) 2_566 . . . ?
Sm1 O7 C21 C17 -167.8(2) 2_566 . . . ?
Sm1 O8 C21 O7 -3.7(6) 1_465 . . . ?
Sm1 O8 C21 C17 176.7(2) 1_465 . . . ?
C16 C17 C21 O7 170.2(4) . . . . ?
C18 C17 C21 O7 -10.6(5) . . . . ?
C16 C17 C21 O8 -10.2(5) . . . . ?
C18 C17 C21 O8 169.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1w H11 O4 0.844(10) 2.12(2) 2.867(4) 147(4) 1_556
O1w H12 O5 0.844(10) 2.124(15) 2.956(3) 168(4) 2_656
N1 H1 O2w 0.88 2.08 2.800(7) 138.3 .
N13' H13' O2w' 0.88 1.90 2.678(7) 146.0 .

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         1.135
_refine_diff_density_min         -1.094
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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_bbb
_database_code_depnum_ccdc_archive 'CCDC 1412705'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C21 H7 N O8 Tb'

_chemical_formula_weight         560.20



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'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   C2/c



loop_

_symmetry_equiv_pos_as_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                   17.72(4)

_cell_length_b                   12.11(2)

_cell_length_c                   9.324(19)

_cell_angle_alpha                90.00

_cell_angle_beta                 113.41(3)

_cell_angle_gamma                90.00

_cell_volume                     1836(6)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    231

_cell_measurement_theta_min      2.51

_cell_measurement_theta_max      18.43



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.23

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.11

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.027

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1076

_exptl_absorpt_coefficient_mu    3.905

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.4670

_exptl_absorpt_correction_T_max  0.6733

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  0

_diffrn_standards_decay_%        0

_diffrn_reflns_number            3737

_diffrn_reflns_av_R_equivalents  0.1187

_diffrn_reflns_av_sigmaI/netI    0.2015

_diffrn_reflns_limit_h_min       -21

_diffrn_reflns_limit_h_max       21

_diffrn_reflns_limit_k_min       -14

_diffrn_reflns_limit_k_max       10

_diffrn_reflns_limit_l_min       -11

_diffrn_reflns_limit_l_max       10

_diffrn_reflns_theta_min         2.51

_diffrn_reflns_theta_max         25.48

_reflns_number_total             1653

_reflns_number_gt                1064

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         1653

_refine_ls_number_parameters     141

_refine_ls_number_restraints     38

_refine_ls_R_factor_all          0.1249

_refine_ls_R_factor_gt           0.0812

_refine_ls_wR_factor_ref         0.1752

_refine_ls_wR_factor_gt          0.1582

_refine_ls_goodness_of_fit_ref   1.017

_refine_ls_restrained_S_all      1.009

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group





















C11 C 0.5376(8) 0.5421(13) 0.3181(18) 0.043(4) Uani 0.50 1 d P . 1
H11 H 0.5612 0.4756 0.3640 0.052 Uiso 0.50 1 calc PR . 1
N1 N 0.5376(8) 0.5421(13) 0.3181(18) 0.043(4) Uani 0.50 1 d P . 2
Tb1 Tb 0.5000 0.86785(10) 0.7500 0.0288(4) Uani 1 2 d S . .
O1 O 0.5421(6) 0.7093(10) 0.6345(14) 0.055(3) Uani 1 1 d . . .
O2 O 0.6385(9) 0.8031(15) 0.792(2) 0.116(7) Uani 1 1 d . . .
O3 O 0.9151(6) 0.6201(9) 0.9826(13) 0.043(3) Uani 1 1 d . . .
O4 O 0.9424(7) 0.5171(10) 0.8171(13) 0.052(3) Uani 1 1 d . . .
C1 C 0.6568(9) 0.6229(14) 0.5107(18) 0.041(4) Uani 1 1 d . . .
C2 C 0.6766(9) 0.6721(12) 0.6529(18) 0.030(4) Uani 1 1 d U . .
C3 C 0.7558(8) 0.6557(11) 0.7663(16) 0.028(3) Uani 1 1 d U . .
H3 H 0.7699 0.6846 0.8661 0.033 Uiso 1 1 calc R . .
C4 C 0.8135(8) 0.5969(12) 0.7319(16) 0.028(3) Uani 1 1 d U . .
C5 C 0.7915(9) 0.5560(13) 0.5865(18) 0.037(4) Uani 1 1 d U . .
H5 H 0.8296 0.5155 0.5627 0.044 Uiso 1 1 calc R . .
C6 C 0.7153(9) 0.5723(15) 0.4740(19) 0.046(5) Uani 1 1 d . . .
H6 H 0.7030 0.5490 0.3722 0.056 Uiso 1 1 calc R . .
C7 C 0.6164(8) 0.7350(14) 0.6964(19) 0.032(4) Uani 1 1 d . . .
C8 C 0.8952(9) 0.5761(13) 0.8536(18) 0.030(3) Uani 1 1 d U . .
C9 C 0.5736(8) 0.6362(15) 0.3787(17) 0.033(4) Uani 1 1 d . . .
C10 C 0.5350(9) 0.7349(14) 0.3135(18) 0.039(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

































C11 C9 1.32(2) . ?
C11 C11 1.43(3) 2_655 ?
C11 H11 0.9300 . ?
Tb1 O4 2.282(11) 4_656 ?
Tb1 O4 2.282(11) 3_455 ?
Tb1 O3 2.350(12) 7_667 ?
Tb1 O3 2.350(12) 8_465 ?
Tb1 O2 2.455(13) 2_656 ?
Tb1 O2 2.455(13) . ?
Tb1 O1 2.458(12) . ?
Tb1 O1 2.458(12) 2_656 ?
Tb1 C7 2.813(14) 2_656 ?
Tb1 C7 2.813(14) . ?
O1 C7 1.249(17) . ?
O2 C7 1.161(19) . ?
O3 C8 1.232(17) . ?
O3 Tb1 2.350(12) 7_667 ?
O4 C8 1.246(15) . ?
O4 Tb1 2.282(11) 3_545 ?
C1 C6 1.359(19) . ?
C1 C2 1.37(2) . ?
C1 C9 1.51(2) . ?
C2 C3 1.40(2) . ?
C2 C7 1.492(17) . ?
C3 C4 1.384(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.35(2) . ?
C4 C8 1.46(2) . ?
C5 C6 1.36(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C9 C10 1.39(2) . ?
C10 C10 1.33(3) 2_655 ?



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



















































































C9 C11 C11 120.1(9) . 2_655 ?
C9 C11 H11 119.9 . . ?
C11 C11 H11 119.9 2_655 . ?
O4 Tb1 O4 75.2(6) 4_656 3_455 ?
O4 Tb1 O3 94.3(4) 4_656 7_667 ?
O4 Tb1 O3 80.0(4) 3_455 7_667 ?
O4 Tb1 O3 80.0(4) 4_656 8_465 ?
O4 Tb1 O3 94.3(4) 3_455 8_465 ?
O3 Tb1 O3 172.9(6) 7_667 8_465 ?
O4 Tb1 O2 137.5(5) 4_656 2_656 ?
O4 Tb1 O2 76.6(6) 3_455 2_656 ?
O3 Tb1 O2 111.5(5) 7_667 2_656 ?
O3 Tb1 O2 70.9(5) 8_465 2_656 ?
O4 Tb1 O2 76.6(6) 4_656 . ?
O4 Tb1 O2 137.5(5) 3_455 . ?
O3 Tb1 O2 70.9(5) 7_667 . ?
O3 Tb1 O2 111.5(5) 8_465 . ?
O2 Tb1 O2 142.8(9) 2_656 . ?
O4 Tb1 O1 104.6(4) 4_656 . ?
O4 Tb1 O1 170.2(4) 3_455 . ?
O3 Tb1 O1 109.6(4) 7_667 . ?
O3 Tb1 O1 76.2(4) 8_465 . ?
O2 Tb1 O1 98.0(6) 2_656 . ?
O2 Tb1 O1 50.3(4) . . ?
O4 Tb1 O1 170.2(4) 4_656 2_656 ?
O4 Tb1 O1 104.6(4) 3_455 2_656 ?
O3 Tb1 O1 76.2(4) 7_667 2_656 ?
O3 Tb1 O1 109.6(4) 8_465 2_656 ?
O2 Tb1 O1 50.3(4) 2_656 2_656 ?
O2 Tb1 O1 98.0(6) . 2_656 ?
O1 Tb1 O1 77.3(6) . 2_656 ?
O4 Tb1 C7 160.2(5) 4_656 2_656 ?
O4 Tb1 C7 88.0(5) 3_455 2_656 ?
O3 Tb1 C7 93.0(4) 7_667 2_656 ?
O3 Tb1 C7 91.1(4) 8_465 2_656 ?
O2 Tb1 C7 24.3(4) 2_656 2_656 ?
O2 Tb1 C7 123.1(6) . 2_656 ?
O1 Tb1 C7 90.2(4) . 2_656 ?
O1 Tb1 C7 26.3(4) 2_656 2_656 ?
O4 Tb1 C7 88.0(5) 4_656 . ?
O4 Tb1 C7 160.2(5) 3_455 . ?
O3 Tb1 C7 91.1(4) 7_667 . ?
O3 Tb1 C7 93.0(4) 8_465 . ?
O2 Tb1 C7 123.1(6) 2_656 . ?
O2 Tb1 C7 24.3(4) . . ?
O1 Tb1 C7 26.3(4) . . ?
O1 Tb1 C7 90.2(4) 2_656 . ?
C7 Tb1 C7 110.2(7) 2_656 . ?
C7 O1 Tb1 92.9(10) . . ?
C7 O2 Tb1 95.4(11) . . ?
C8 O3 Tb1 151.3(10) . 7_667 ?
C8 O4 Tb1 161.9(11) . 3_545 ?
C6 C1 C2 120.9(15) . . ?
C6 C1 C9 116.0(14) . . ?
C2 C1 C9 122.5(13) . . ?
C1 C2 C3 117.8(12) . . ?
C1 C2 C7 123.4(14) . . ?
C3 C2 C7 118.6(13) . . ?
C4 C3 C2 120.7(13) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 118.5(14) . . ?
C5 C4 C8 121.2(12) . . ?
C3 C4 C8 120.2(13) . . ?
C4 C5 C6 121.8(13) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.7(15) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O2 C7 O1 120.2(14) . . ?
O2 C7 C2 120.8(14) . . ?
O1 C7 C2 118.9(15) . . ?
O2 C7 Tb1 60.3(8) . . ?
O1 C7 Tb1 60.8(8) . . ?
C2 C7 Tb1 173.8(11) . . ?
O3 C8 O4 123.4(14) . . ?
O3 C8 C4 119.6(12) . . ?
O4 C8 C4 116.9(13) . . ?
C11 C9 C10 119.0(14) . . ?
C11 C9 C1 114.0(16) . . ?
C10 C9 C1 126.9(16) . . ?
C10 C10 C9 120.7(9) 2_655 . ?



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
















































































O4 Tb1 O1 C7 52.6(10) 4_656 . . . ?
O4 Tb1 O1 C7 140(2) 3_455 . . . ?
O3 Tb1 O1 C7 -47.5(10) 7_667 . . . ?
O3 Tb1 O1 C7 128.2(10) 8_465 . . . ?
O2 Tb1 O1 C7 -163.7(10) 2_656 . . . ?
O2 Tb1 O1 C7 -5.7(10) . . . . ?
O1 Tb1 O1 C7 -117.6(11) 2_656 . . . ?
C7 Tb1 O1 C7 -140.7(9) 2_656 . . . ?
O4 Tb1 O2 C7 -116.1(15) 4_656 . . . ?
O4 Tb1 O2 C7 -165.8(11) 3_455 . . . ?
O3 Tb1 O2 C7 144.5(15) 7_667 . . . ?
O3 Tb1 O2 C7 -42.6(16) 8_465 . . . ?
O2 Tb1 O2 C7 43.8(13) 2_656 . . . ?
O1 Tb1 O2 C7 6.1(11) . . . . ?
O1 Tb1 O2 C7 72.2(15) 2_656 . . . ?
C7 Tb1 O2 C7 63.7(18) 2_656 . . . ?
C6 C1 C2 C3 -9(2) . . . . ?
C9 C1 C2 C3 -179.1(15) . . . . ?
C6 C1 C2 C7 176.0(16) . . . . ?
C9 C1 C2 C7 6(3) . . . . ?
C1 C2 C3 C4 4(2) . . . . ?
C7 C2 C3 C4 179.3(13) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C2 C3 C4 C8 -177.3(14) . . . . ?
C3 C4 C5 C6 1(3) . . . . ?
C8 C4 C5 C6 178.2(16) . . . . ?
C4 C5 C6 C1 -6(3) . . . . ?
C2 C1 C6 C5 10(3) . . . . ?
C9 C1 C6 C5 -179.2(16) . . . . ?
Tb1 O2 C7 O1 -11(2) . . . . ?
Tb1 O2 C7 C2 173.0(13) . . . . ?
Tb1 O1 C7 O2 11(2) . . . . ?
Tb1 O1 C7 C2 -172.9(12) . . . . ?
C1 C2 C7 O2 -155(2) . . . . ?
C3 C2 C7 O2 30(3) . . . . ?
C1 C2 C7 O1 29(2) . . . . ?
C3 C2 C7 O1 -146.6(15) . . . . ?
C1 C2 C7 Tb1 -56(11) . . . . ?
C3 C2 C7 Tb1 128(10) . . . . ?
O4 Tb1 C7 O2 61.0(15) 4_656 . . . ?
O4 Tb1 C7 O2 29(2) 3_455 . . . ?
O3 Tb1 C7 O2 -33.3(15) 7_667 . . . ?
O3 Tb1 C7 O2 140.9(15) 8_465 . . . ?
O2 Tb1 C7 O2 -150.0(12) 2_656 . . . ?
O1 Tb1 C7 O2 -169(2) . . . . ?
O1 Tb1 C7 O2 -109.4(15) 2_656 . . . ?
C7 Tb1 C7 O2 -126.8(15) 2_656 . . . ?
O4 Tb1 C7 O1 -129.7(10) 4_656 . . . ?
O4 Tb1 C7 O1 -161.3(11) 3_455 . . . ?
O3 Tb1 C7 O1 136.0(10) 7_667 . . . ?
O3 Tb1 C7 O1 -49.8(10) 8_465 . . . ?
O2 Tb1 C7 O1 19.3(12) 2_656 . . . ?
O2 Tb1 C7 O1 169(2) . . . . ?
O1 Tb1 C7 O1 59.9(11) 2_656 . . . ?
C7 Tb1 C7 O1 42.4(8) 2_656 . . . ?
O4 Tb1 C7 C2 -41(11) 4_656 . . . ?
O4 Tb1 C7 C2 -73(11) 3_455 . . . ?
O3 Tb1 C7 C2 -135(11) 7_667 . . . ?
O3 Tb1 C7 C2 39(11) 8_465 . . . ?
O2 Tb1 C7 C2 108(11) 2_656 . . . ?
O2 Tb1 C7 C2 -102(11) . . . . ?
O1 Tb1 C7 C2 89(11) . . . . ?
O1 Tb1 C7 C2 149(11) 2_656 . . . ?
C7 Tb1 C7 C2 131(11) 2_656 . . . ?
Tb1 O3 C8 O4 -21(3) 7_667 . . . ?
Tb1 O3 C8 C4 162.3(14) 7_667 . . . ?
Tb1 O4 C8 O3 113(3) 3_545 . . . ?
Tb1 O4 C8 C4 -70(4) 3_545 . . . ?
C5 C4 C8 O3 175.6(15) . . . . ?
C3 C4 C8 O3 -7(2) . . . . ?
C5 C4 C8 O4 -1(2) . . . . ?
C3 C4 C8 O4 175.9(14) . . . . ?
C11 C11 C9 C10 4(2) 2_655 . . . ?
C11 C11 C9 C1 -173.6(16) 2_655 . . . ?
C6 C1 C9 C11 62(2) . . . . ?
C2 C1 C9 C11 -127.5(17) . . . . ?
C6 C1 C9 C10 -115.2(18) . . . . ?
C2 C1 C9 C10 56(2) . . . . ?
C11 C9 C10 C10 -4(2) . . . 2_655 ?
C1 C9 C10 C10 173.0(16) . . . 2_655 ?



_diffrn_measured_fraction_theta_max 0.974

_diffrn_reflns_theta_full        25.48

_diffrn_measured_fraction_theta_full 0.974

_refine_diff_density_max         1.492

_refine_diff_density_min         -2.169

_refine_diff_density_rms         0.282

####################################################################### 
# 
# 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_er
_database_code_depnum_ccdc_archive 'CCDC 1412706'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Er (C21 H10 N O8), H2 O'
_chemical_formula_sum            'C21 H12 Er N O9'
_chemical_formula_weight         589.58

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_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                   18.3160(14)
_cell_length_b                   12.2002(9)
_cell_length_c                   9.5032(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.0860(10)
_cell_angle_gamma                90.00
_cell_volume                     1938.7(3)
_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            pink
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.020
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1140
_exptl_absorpt_coefficient_mu    4.387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3135
_exptl_absorpt_correction_T_max  0.3135
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5806
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2208
_reflns_number_gt                2070
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0685P)²+22.0500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2208
_refine_ls_number_parameters     150
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Er1 Er 0.5000 0.36567(3) 0.7500 0.01628(15) Uani 1 2 d S . .
O1 O 0.5437(3) 0.2033(4) 0.6328(6) 0.0284(11) Uani 1 1 d U . .
O2 O 0.6411(3) 0.3012(6) 0.7940(8) 0.0523(17) Uani 1 1 d U . .
O3 O 0.9130(3) 0.1224(4) 0.9781(5) 0.0219(10) Uani 1 1 d U . .
O4 O 0.9408(3) 0.0211(4) 0.8141(5) 0.0250(10) Uani 1 1 d U . .
O1W O 0.6181(8) -0.1214(8) 0.5470(14) 0.038(3) Uani 0.50 1 d PU . .
H1W1 H 0.5769 -0.1608 0.5146 0.057 Uiso 0.50 1 d PR . .
H1W2 H 0.6554 -0.1557 0.5367 0.057 Uiso 0.50 1 d PR . .
C1 C 0.6167(3) 0.2288(5) 0.6951(6) 0.0145(10) Uani 1 1 d U . .
C2 C 0.6762(3) 0.1692(4) 0.6502(6) 0.0116(10) Uani 1 1 d U . .
C3 C 0.7542(3) 0.1557(4) 0.7616(6) 0.0110(9) Uani 1 1 d U . .
H3 H 0.7685 0.1858 0.8591 0.013 Uiso 1 1 calc R . .
C4 C 0.8113(3) 0.0973(5) 0.7280(6) 0.0124(10) Uani 1 1 d U . .
C5 C 0.7897(4) 0.0560(6) 0.5800(7) 0.0252(13) Uani 1 1 d U . .
H5 H 0.8270 0.0179 0.5559 0.030 Uiso 1 1 calc R . .
C6 C 0.7130(4) 0.0711(6) 0.4684(7) 0.0259(14) Uani 1 1 d U . .
H6 H 0.6998 0.0447 0.3692 0.031 Uiso 1 1 calc R . .
C7 C 0.6549(4) 0.1256(5) 0.5030(7) 0.0163(11) Uani 1 1 d U . .
C8 C 0.8946(3) 0.0782(4) 0.8500(6) 0.0116(10) Uani 1 1 d U . .
C9 C 0.5364(3) 0.2323(5) 0.3140(6) 0.0142(10) Uani 1 1 d U . .
H9 H 0.5605 0.2983 0.3576 0.017 Uiso 1 1 calc R . .
C10 C 0.5733(4) 0.1333(4) 0.3767(7) 0.0163(11) Uani 1 1 d U . .
N1 N 0.5359(4) 0.0393(5) 0.3131(7) 0.0265(13) Uani 0.50 1 d P . 1
H1 H 0.5581 -0.0236 0.3533 0.032 Uiso 0.50 1 calc PR . 1
C11 C 0.5359(4) 0.0393(5) 0.3131(7) 0.0265(13) Uani 0.50 1 d PU . 2
H11 H 0.5594 -0.0272 0.3556 0.032 Uiso 0.50 1 calc PR . 2


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 O4 2.384(4) 8_657 ?
Er1 O4 2.384(4) 3_455 ?
Er1 O3 2.424(4) 4_454 ?
Er1 O3 2.424(4) 7_657 ?
Er1 O1 2.556(5) . ?
Er1 O1 2.556(5) 6_657 ?
Er1 O2 2.567(5) 6_657 ?
Er1 O2 2.567(5) . ?
O1 C1 1.261(7) . ?
O2 C1 1.233(8) . ?
O3 C8 1.245(7) . ?
O3 Er1 2.424(4) 7_657 ?
O4 C8 1.246(7) . ?
O4 Er1 2.384(4) 3_545 ?
O1W H1W1 0.8401 . ?
O1W H1W2 0.8400 . ?
C1 C2 1.509(7) . ?
C2 C3 1.398(7) . ?
C2 C7 1.396(8) . ?
C3 C4 1.406(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(8) . ?
C4 C8 1.511(7) . ?
C5 C6 1.385(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(8) . ?
C6 H6 0.9300 . ?
C7 C10 1.490(8) . ?
C9 C10 1.393(7) . ?
C9 C9 1.391(10) 6_656 ?
C9 H9 0.9300 . ?
C10 N1 1.346(8) . ?
N1 N1 1.371(12) 6_656 ?
N1 H1 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Er1 O4 74.6(3) 8_657 3_455 ?
O4 Er1 O3 81.35(14) 8_657 4_454 ?
O4 Er1 O3 93.13(16) 3_455 4_454 ?
O4 Er1 O3 93.13(16) 8_657 7_657 ?
O4 Er1 O3 81.35(14) 3_455 7_657 ?
O3 Er1 O3 173.1(2) 4_454 7_657 ?
O4 Er1 O1 104.43(18) 8_657 . ?
O4 Er1 O1 169.70(15) 3_455 . ?
O3 Er1 O1 76.63(17) 4_454 . ?
O3 Er1 O1 108.95(15) 7_657 . ?
O4 Er1 O1 169.70(15) 8_657 6_657 ?
O4 Er1 O1 104.43(18) 3_455 6_657 ?
O3 Er1 O1 108.95(15) 4_454 6_657 ?
O3 Er1 O1 76.63(17) 7_657 6_657 ?
O1 Er1 O1 78.4(2) . 6_657 ?
O4 Er1 O2 137.29(17) 8_657 6_657 ?
O4 Er1 O2 75.7(2) 3_455 6_657 ?
O3 Er1 O2 70.40(18) 4_454 6_657 ?
O3 Er1 O2 111.9(2) 7_657 6_657 ?
O1 Er1 O2 99.5(2) . 6_657 ?
O1 Er1 O2 50.22(16) 6_657 6_657 ?
O4 Er1 O2 75.7(2) 8_657 . ?
O4 Er1 O2 137.29(17) 3_455 . ?
O3 Er1 O2 111.9(2) 4_454 . ?
O3 Er1 O2 70.40(18) 7_657 . ?
O1 Er1 O2 50.22(16) . . ?
O1 Er1 O2 99.5(2) 6_657 . ?
O2 Er1 O2 144.3(3) 6_657 . ?
C1 O1 Er1 93.7(3) . . ?
C1 O2 Er1 93.9(4) . . ?
C8 O3 Er1 150.0(4) . 7_657 ?
C8 O4 Er1 160.9(4) . 3_545 ?
H1W1 O1W H1W2 108.9 . . ?
O2 C1 O1 121.3(5) . . ?
O2 C1 C2 118.8(5) . . ?
O1 C1 C2 119.9(5) . . ?
C3 C2 C7 119.7(5) . . ?
C3 C2 C1 118.4(5) . . ?
C7 C2 C1 121.9(5) . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.8(5) . . ?
C5 C4 C8 120.1(5) . . ?
C3 C4 C8 121.0(5) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.9(6) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 119.2(5) . . ?
C6 C7 C10 116.7(5) . . ?
C2 C7 C10 124.1(5) . . ?
O4 C8 O3 124.5(5) . . ?
O4 C8 C4 117.5(5) . . ?
O3 C8 C4 118.0(5) . . ?
C10 C9 C9 119.9(3) . 6_656 ?
C10 C9 H9 120.1 . . ?
C9 C9 H9 120.1 6_656 . ?
N1 C10 C9 118.6(5) . . ?
N1 C10 C7 117.8(5) . . ?
C9 C10 C7 123.5(5) . . ?
C10 N1 N1 121.5(3) . 6_656 ?
C10 N1 H1 119.2 . . ?
N1 N1 H1 119.2 6_656 . ?

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
O4 Er1 O1 C1 51.8(4) 8_657 . . . ?
O4 Er1 O1 C1 134.9(8) 3_455 . . . ?
O3 Er1 O1 C1 129.0(4) 4_454 . . . ?
O3 Er1 O1 C1 -46.7(4) 7_657 . . . ?
O1 Er1 O1 C1 -118.1(4) 6_657 . . . ?
O2 Er1 O1 C1 -163.9(4) 6_657 . . . ?
O2 Er1 O1 C1 -5.1(4) . . . . ?
O4 Er1 O2 C1 -117.9(5) 8_657 . . . ?
O4 Er1 O2 C1 -165.0(4) 3_455 . . . ?
O3 Er1 O2 C1 -43.6(5) 4_454 . . . ?
O3 Er1 O2 C1 143.4(5) 7_657 . . . ?
O1 Er1 O2 C1 5.2(4) . . . . ?
O1 Er1 O2 C1 71.4(5) 6_657 . . . ?
O2 Er1 O2 C1 42.9(5) 6_657 . . . ?
Er1 O2 C1 O1 -9.5(7) . . . . ?
Er1 O2 C1 C2 171.2(5) . . . . ?
Er1 O1 C1 O2 9.6(7) . . . . ?
Er1 O1 C1 C2 -171.1(5) . . . . ?
O2 C1 C2 C3 30.8(9) . . . . ?
O1 C1 C2 C3 -148.5(6) . . . . ?
O2 C1 C2 C7 -150.7(7) . . . . ?
O1 C1 C2 C7 30.0(9) . . . . ?
C7 C2 C3 C4 -1.0(9) . . . . ?
C1 C2 C3 C4 177.6(5) . . . . ?
C2 C3 C4 C5 2.1(9) . . . . ?
C2 C3 C4 C8 -177.2(5) . . . . ?
C3 C4 C5 C6 -0.8(10) . . . . ?
C8 C4 C5 C6 178.6(6) . . . . ?
C4 C5 C6 C7 -1.7(12) . . . . ?
C5 C6 C7 C2 2.9(11) . . . . ?
C5 C6 C7 C10 -177.4(6) . . . . ?
C3 C2 C7 C6 -1.5(9) . . . . ?
C1 C2 C7 C6 180.0(6) . . . . ?
C3 C2 C7 C10 178.8(5) . . . . ?
C1 C2 C7 C10 0.3(9) . . . . ?
Er1 O4 C8 O3 109.2(11) 3_545 . . . ?
Er1 O4 C8 C4 -72.5(13) 3_545 . . . ?
Er1 O3 C8 O4 -19.2(12) 7_657 . . . ?
Er1 O3 C8 C4 162.5(6) 7_657 . . . ?
C5 C4 C8 O4 -2.8(9) . . . . ?
C3 C4 C8 O4 176.6(6) . . . . ?
C5 C4 C8 O3 175.6(6) . . . . ?
C3 C4 C8 O3 -5.0(8) . . . . ?
C9 C9 C10 N1 -1.6(11) 6_656 . . . ?
C9 C9 C10 C7 173.5(7) 6_656 . . . ?
C6 C7 C10 N1 57.6(9) . . . . ?
C2 C7 C10 N1 -122.8(7) . . . . ?
C6 C7 C10 C9 -117.5(7) . . . . ?
C2 C7 C10 C9 62.2(9) . . . . ?
C9 C10 N1 N1 1.6(13) . . . 6_656 ?
C7 C10 N1 N1 -173.8(8) . . . 6_656 ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.552
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.236
