# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1472875'
_audit_update_record             
;
2016-04-07 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 N O11 Pr'
_chemical_formula_weight         463.12

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'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   15.489(6)
_cell_length_b                   6.174(2)
_cell_length_c                   16.745(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.294(7)
_cell_angle_gamma                90.00
_cell_volume                     1447.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3868
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    3.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5195
_exptl_absorpt_correction_T_max  0.5776
_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
_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            6539
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.13
_reflns_number_total             2558
_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)+(0.0409P)²+13.0162P] 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         2558
_refine_ls_number_parameters     220
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.008
_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
C1 C 0.1284(5) 0.5955(13) 0.1176(5) 0.0227(16) Uani 1 1 d . . .
C2 C 0.0320(5) 0.6434(15) 0.0897(6) 0.0307(19) Uani 1 1 d . . .
H2 H 0.0033 0.7508 0.0477 0.037 Uiso 1 1 calc R . .
C3 C -0.0203(6) 0.5314(16) 0.1246(7) 0.038(2) Uani 1 1 d . . .
H3 H -0.0846 0.5637 0.1060 0.046 Uiso 1 1 calc R . .
C4 C 0.0210(6) 0.3720(18) 0.1866(7) 0.042(2) Uani 1 1 d . . .
H4 H -0.0156 0.2944 0.2085 0.051 Uiso 1 1 calc R . .
C5 C 0.1181(6) 0.3270(16) 0.2165(6) 0.037(2) Uani 1 1 d . . .
H5 H 0.1471 0.2244 0.2606 0.045 Uiso 1 1 calc R . .
C6 C 0.1711(5) 0.4351(13) 0.1805(5) 0.0220(16) Uani 1 1 d . . .
C7 C 0.3224(6) 0.2738(16) 0.2789(6) 0.033(2) Uani 1 1 d . . .
H7A H 0.2930 0.1324 0.2733 0.039 Uiso 1 1 calc R . .
H7B H 0.3250 0.3423 0.3320 0.039 Uiso 1 1 calc R . .
C8 C 0.4219(6) 0.2497(13) 0.2847(6) 0.0271(18) Uani 1 1 d . . .
C9 C 0.1591(6) 0.9145(13) 0.0514(6) 0.031(2) Uani 1 1 d . . .
H9A H 0.1370 0.9932 0.0893 0.038 Uiso 1 1 calc R . .
H9B H 0.1069 0.9079 -0.0072 0.038 Uiso 1 1 calc R . .
C10 C 0.2430(6) 1.0337(13) 0.0474(5) 0.0250(17) Uani 1 1 d . . .
N1 N 0.3040(6) 0.6669(12) -0.0957(5) 0.0332(17) Uani 1 1 d . . .
O12 O 0.2671(4) 0.4041(10) 0.2031(4) 0.0295(13) Uani 1 1 d . . .
O13 O 0.1859(4) 0.6998(9) 0.0847(4) 0.0253(12) Uani 1 1 d . . .
O14 O 0.3132(4) 0.9249(9) 0.0537(5) 0.0354(15) Uani 1 1 d . . .
O15 O 0.3802(4) 0.7657(13) 0.2278(5) 0.0429(17) Uani 1 1 d D . .
H1W H 0.439(2) 0.78(2) 0.259(7) 0.064 Uiso 1 1 d D . .
H2W H 0.359(8) 0.78(2) 0.266(6) 0.064 Uiso 1 1 d D . .
O16 O 0.2346(4) 0.2353(9) 0.0389(4) 0.0296(13) Uani 1 1 d . . .
O17 O 0.4339(4) 0.3054(11) 0.2183(4) 0.0372(15) Uani 1 1 d . . .
O18 O 0.4296(5) 0.2554(11) 0.0434(5) 0.0455(17) Uani 1 1 d D . .
H3W H 0.420(9) 0.138(11) 0.064(8) 0.068 Uiso 1 1 d D . .
H4W H 0.471(6) 0.29(2) 0.025(8) 0.068 Uiso 1 1 d D . .
O19 O 0.5170(4) 0.6701(10) 0.1472(4) 0.0323(14) Uani 1 1 d . . .
O20 O 0.2456(4) 0.5737(12) -0.0734(4) 0.0430(17) Uani 1 1 d . . .
O21 O 0.3879(4) 0.6856(11) -0.0375(4) 0.0386(15) Uani 1 1 d . . .
O22 O 0.2791(5) 0.7344(13) -0.1711(5) 0.054(2) Uani 1 1 d . . .
Pr1 Pr 0.34828(3) 0.54229(7) 0.09380(3) 0.01961(17) 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
C1 C6 1.389(11) . ?
C1 O13 1.389(9) . ?
C1 C2 1.392(11) . ?
C2 C3 1.371(13) . ?
C3 C4 1.374(14) . ?
C4 C5 1.395(12) . ?
C5 C6 1.380(11) . ?
C6 O12 1.383(9) . ?
C7 O12 1.436(10) . ?
C7 C8 1.510(11) . ?
C8 O19 1.231(10) 2_645 ?
C8 O17 1.251(10) . ?
C9 O13 1.429(10) . ?
C9 C10 1.520(11) . ?
C10 O14 1.244(10) . ?
C10 O16 1.253(10) 1_565 ?
N1 O22 1.225(9) . ?
N1 O21 1.253(10) . ?
N1 O20 1.256(10) . ?
O12 Pr1 2.761(6) . ?
O13 Pr1 2.640(5) . ?
O14 Pr1 2.453(6) . ?
O15 Pr1 2.496(7) . ?
O16 C10 1.253(10) 1_545 ?
O16 Pr1 2.481(6) . ?
O17 Pr1 2.426(6) . ?
O18 Pr1 2.518(7) . ?
O19 C8 1.231(10) 2_655 ?
O19 Pr1 2.501(5) . ?
O20 Pr1 2.569(6) . ?
O21 Pr1 2.674(6) . ?

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
C6 C1 O13 116.9(7) . . ?
C6 C1 C2 120.1(7) . . ?
O13 C1 C2 123.0(7) . . ?
C3 C2 C1 119.6(8) . . ?
C2 C3 C4 120.9(8) . . ?
C3 C4 C5 119.8(8) . . ?
C6 C5 C4 119.9(8) . . ?
O12 C6 C1 114.5(7) . . ?
O12 C6 C5 125.8(7) . . ?
C1 C6 C5 119.7(7) . . ?
O12 C7 C8 108.6(7) . . ?
O19 C8 O17 125.8(7) 2_645 . ?
O19 C8 C7 117.3(7) 2_645 . ?
O17 C8 C7 116.8(7) . . ?
O13 C9 C10 110.8(6) . . ?
O14 C10 O16 126.2(8) . 1_565 ?
O14 C10 C9 117.9(7) . . ?
O16 C10 C9 115.9(7) 1_565 . ?
O22 N1 O21 122.3(8) . . ?
O22 N1 O20 120.9(8) . . ?
O21 N1 O20 116.8(7) . . ?
C6 O12 C7 119.0(6) . . ?
C6 O12 Pr1 121.1(4) . . ?
C7 O12 Pr1 119.4(4) . . ?
C1 O13 C9 117.2(6) . . ?
C1 O13 Pr1 124.2(4) . . ?
C9 O13 Pr1 118.3(4) . . ?
C10 O14 Pr1 128.8(5) . . ?
C10 O16 Pr1 133.9(5) 1_545 . ?
C8 O17 Pr1 134.0(5) . . ?
C8 O19 Pr1 136.8(5) 2_655 . ?
N1 O20 Pr1 99.8(5) . . ?
N1 O21 Pr1 94.7(4) . . ?
O17 Pr1 O14 142.4(2) . . ?
O17 Pr1 O16 84.2(2) . . ?
O14 Pr1 O16 126.54(19) . . ?
O17 Pr1 O15 74.6(3) . . ?
O14 Pr1 O15 69.5(2) . . ?
O16 Pr1 O15 126.3(2) . . ?
O17 Pr1 O19 77.2(2) . . ?
O14 Pr1 O19 82.5(2) . . ?
O16 Pr1 O19 147.27(19) . . ?
O15 Pr1 O19 74.27(19) . . ?
O17 Pr1 O18 72.3(2) . . ?
O14 Pr1 O18 132.0(2) . . ?
O16 Pr1 O18 73.5(2) . . ?
O15 Pr1 O18 139.0(3) . . ?
O19 Pr1 O18 75.3(2) . . ?
O17 Pr1 O20 147.0(2) . . ?
O14 Pr1 O20 70.6(2) . . ?
O16 Pr1 O20 69.1(2) . . ?
O15 Pr1 O20 136.9(3) . . ?
O19 Pr1 O20 115.57(19) . . ?
O18 Pr1 O20 81.6(3) . . ?
O17 Pr1 O13 115.42(18) . . ?
O14 Pr1 O13 62.32(17) . . ?
O16 Pr1 O13 75.66(18) . . ?
O15 Pr1 O13 70.50(19) . . ?
O19 Pr1 O13 136.78(19) . . ?
O18 Pr1 O13 147.2(2) . . ?
O20 Pr1 O13 77.2(2) . . ?
O17 Pr1 O21 132.32(19) . . ?
O14 Pr1 O21 63.7(2) . . ?
O16 Pr1 O21 108.9(2) . . ?
O15 Pr1 O21 122.0(2) . . ?
O19 Pr1 O21 67.52(19) . . ?
O18 Pr1 O21 68.5(2) . . ?
O20 Pr1 O21 48.05(19) . . ?
O13 Pr1 O21 112.25(18) . . ?
O17 Pr1 O12 58.70(17) . . ?
O14 Pr1 O12 111.66(19) . . ?
O16 Pr1 O12 63.74(19) . . ?
O15 Pr1 O12 63.0(2) . . ?
O19 Pr1 O12 124.23(18) . . ?
O18 Pr1 O12 116.0(2) . . ?
O20 Pr1 O12 120.03(18) . . ?
O13 Pr1 O12 57.29(16) . . ?
O21 Pr1 O12 167.67(17) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.13
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.902
_refine_diff_density_min         -1.613
_refine_diff_density_rms         0.194
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1472876'
_audit_update_record             
;
2016-04-07 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 La N O11'
_chemical_formula_weight         461.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   15.489(6)
_cell_length_b                   6.174(2)
_cell_length_c                   16.745(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.294(7)
_cell_angle_gamma                90.00
_cell_volume                     1447.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6756
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    3.011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5571
_exptl_absorpt_correction_T_max  0.6132
_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
_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            8831
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.40
_reflns_number_total             2607
_reflns_number_gt                2489
_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)+(0.0116P)²+1.3248P] 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         2607
_refine_ls_number_parameters     220
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0163
_refine_ls_R_factor_gt           0.0154
_refine_ls_wR_factor_ref         0.0371
_refine_ls_wR_factor_gt          0.0366
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.12570(15) 0.5934(4) 0.11751(15) 0.0204(5) Uani 1 1 d . . .
C2 C 0.03032(16) 0.6383(4) 0.09051(17) 0.0283(5) Uani 1 1 d . . .
H2 H 0.0012 0.7453 0.0484 0.034 Uiso 1 1 calc R . .
C3 C -0.02213(18) 0.5256(5) 0.12543(19) 0.0350(6) Uani 1 1 d . . .
H3 H -0.0866 0.5563 0.1072 0.042 Uiso 1 1 calc R . .
C4 C 0.02113(18) 0.3682(5) 0.18719(19) 0.0383(7) Uani 1 1 d . . .
H4 H -0.0143 0.2910 0.2105 0.046 Uiso 1 1 calc R . .
C5 C 0.11786(18) 0.3225(4) 0.21541(18) 0.0333(6) Uani 1 1 d . . .
H5 H 0.1470 0.2164 0.2579 0.040 Uiso 1 1 calc R . .
C6 C 0.16995(15) 0.4343(4) 0.18039(15) 0.0216(5) Uani 1 1 d . . .
C7 C 0.32019(17) 0.2726(4) 0.27761(16) 0.0277(5) Uani 1 1 d . . .
H7A H 0.2907 0.1314 0.2722 0.033 Uiso 1 1 calc R . .
H7B H 0.3227 0.3417 0.3306 0.033 Uiso 1 1 calc R . .
C8 C 0.41991(16) 0.2474(4) 0.28392(16) 0.0247(5) Uani 1 1 d . . .
C9 C 0.15498(17) 0.9125(4) 0.05192(18) 0.0294(6) Uani 1 1 d . . .
H9A H 0.1345 0.9908 0.0910 0.035 Uiso 1 1 calc R . .
H9B H 0.1017 0.9061 -0.0061 0.035 Uiso 1 1 calc R . .
C10 C 0.23758(17) 1.0299(4) 0.04594(15) 0.0217(5) Uani 1 1 d . . .
N1 N 0.30662(16) 0.6655(4) -0.09647(14) 0.0310(5) Uani 1 1 d . . .
O12 O 0.26532(11) 0.4015(3) 0.20222(11) 0.0254(4) Uani 1 1 d . . .
O13 O 0.18308(10) 0.6977(3) 0.08476(11) 0.0229(3) Uani 1 1 d . . .
O14 O 0.30657(13) 0.9222(3) 0.04907(13) 0.0343(4) Uani 1 1 d . . .
O15 O 0.37976(14) 0.7705(4) 0.22619(13) 0.0413(5) Uani 1 1 d D . .
H1W H 0.4392(14) 0.788(6) 0.252(2) 0.062 Uiso 1 1 d D . .
H2W H 0.358(2) 0.755(6) 0.2637(19) 0.062 Uiso 1 1 d D . .
O16 O 0.22863(12) 0.2298(3) 0.03591(11) 0.0280(4) Uani 1 1 d . . .
O17 O 0.43368(12) 0.3042(3) 0.21915(12) 0.0363(5) Uani 1 1 d . . .
O18 O 0.42951(15) 0.2462(3) 0.04345(16) 0.0444(5) Uani 1 1 d D . .
H3W H 0.413(3) 0.120(3) 0.039(2) 0.067 Uiso 1 1 d D . .
H4W H 0.4810(17) 0.242(6) 0.039(2) 0.067 Uiso 1 1 d D . .
O19 O 0.51862(11) 0.6672(3) 0.14752(11) 0.0300(4) Uani 1 1 d . . .
O20 O 0.24735(14) 0.5660(4) -0.07831(12) 0.0431(5) Uani 1 1 d . . .
O21 O 0.38988(13) 0.6868(3) -0.03672(12) 0.0360(4) Uani 1 1 d . . .
O22 O 0.28318(17) 0.7388(4) -0.17000(13) 0.0521(6) Uani 1 1 d . . .
La1 La 0.346896(8) 0.53750(2) 0.091983(8) 0.01655(5) 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
C1 C2 1.376(3) . ?
C1 C6 1.388(3) . ?
C1 O13 1.386(3) . ?
C2 C3 1.376(4) . ?
C3 C4 1.368(4) . ?
C4 C5 1.394(4) . ?
C5 C6 1.370(3) . ?
C6 O12 1.377(3) . ?
C7 O12 1.426(3) . ?
C7 C8 1.510(3) . ?
C8 O19 1.239(3) 2_645 ?
C8 O17 1.242(3) . ?
C9 O13 1.430(3) . ?
C9 C10 1.510(3) . ?
C10 O14 1.241(3) . ?
C10 O16 1.246(3) 1_565 ?
N1 O22 1.213(3) . ?
N1 O20 1.245(3) . ?
N1 O21 1.256(3) . ?
N1 La1 3.048(2) . ?
O12 La1 2.7753(18) . ?
O13 La1 2.6774(18) . ?
O14 La1 2.4829(19) . ?
O15 La1 2.530(2) . ?
O16 C10 1.246(3) 1_545 ?
O16 La1 2.5250(17) . ?
O17 La1 2.4435(18) . ?
O18 La1 2.534(2) . ?
O19 C8 1.239(3) 2_655 ?
O19 La1 2.5431(18) . ?
O20 La1 2.604(2) . ?
O21 La1 2.677(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.3(2) . . ?
C2 C1 O13 123.8(2) . . ?
C6 C1 O13 115.88(19) . . ?
C1 C2 C3 120.3(2) . . ?
C4 C3 C2 119.6(2) . . ?
C3 C4 C5 120.6(2) . . ?
C6 C5 C4 119.8(2) . . ?
C5 C6 O12 125.0(2) . . ?
C5 C6 C1 119.4(2) . . ?
O12 C6 C1 115.6(2) . . ?
O12 C7 C8 108.92(19) . . ?
O19 C8 O17 124.8(2) 2_645 . ?
O19 C8 C7 117.6(2) 2_645 . ?
O17 C8 C7 117.5(2) . . ?
O13 C9 C10 110.07(19) . . ?
O14 C10 O16 125.5(2) . 1_565 ?
O14 C10 C9 118.6(2) . . ?
O16 C10 C9 115.9(2) 1_565 . ?
O22 N1 O20 120.0(2) . . ?
O22 N1 O21 122.0(2) . . ?
O20 N1 O21 118.0(2) . . ?
O22 N1 La1 171.11(18) . . ?
O20 N1 La1 57.69(12) . . ?
O21 N1 La1 61.07(12) . . ?
C6 O12 C7 118.91(18) . . ?
C6 O12 La1 121.37(13) . . ?
C7 O12 La1 119.29(13) . . ?
C1 O13 C9 116.20(18) . . ?
C1 O13 La1 124.46(13) . . ?
C9 O13 La1 119.13(13) . . ?
C10 O14 La1 129.10(16) . . ?
C10 O16 La1 132.40(15) 1_545 . ?
C8 O17 La1 133.76(15) . . ?
C8 O19 La1 137.23(16) 2_655 . ?
N1 O20 La1 98.47(14) . . ?
N1 O21 La1 94.67(14) . . ?
O17 La1 O14 142.46(7) . . ?
O17 La1 O16 85.53(6) . . ?
O14 La1 O16 124.00(6) . . ?
O17 La1 O15 74.58(8) . . ?
O14 La1 O15 69.11(7) . . ?
O16 La1 O15 126.64(6) . . ?
O17 La1 O18 72.29(8) . . ?
O14 La1 O18 133.26(7) . . ?
O16 La1 O18 74.47(7) . . ?
O15 La1 O18 138.67(7) . . ?
O17 La1 O19 76.53(6) . . ?
O14 La1 O19 84.21(6) . . ?
O16 La1 O19 148.44(6) . . ?
O15 La1 O19 73.39(6) . . ?
O18 La1 O19 75.42(7) . . ?
O17 La1 O20 147.34(7) . . ?
O14 La1 O20 70.15(7) . . ?
O16 La1 O20 69.37(6) . . ?
O15 La1 O20 137.26(8) . . ?
O18 La1 O20 80.83(8) . . ?
O19 La1 O20 114.62(6) . . ?
O17 La1 O21 132.16(6) . . ?
O14 La1 O21 63.64(6) . . ?
O16 La1 O21 110.49(6) . . ?
O15 La1 O21 119.65(7) . . ?
O18 La1 O21 69.68(7) . . ?
O19 La1 O21 66.73(6) . . ?
O20 La1 O21 47.91(6) . . ?
O17 La1 O13 114.52(5) . . ?
O14 La1 O13 61.12(5) . . ?
O16 La1 O13 74.83(6) . . ?
O15 La1 O13 69.95(6) . . ?
O18 La1 O13 147.82(6) . . ?
O19 La1 O13 136.31(6) . . ?
O20 La1 O13 79.59(6) . . ?
O21 La1 O13 113.16(5) . . ?
O17 La1 O12 58.62(6) . . ?
O14 La1 O12 110.62(6) . . ?
O16 La1 O12 63.62(6) . . ?
O15 La1 O12 63.72(6) . . ?
O18 La1 O12 115.74(6) . . ?
O19 La1 O12 123.66(5) . . ?
O20 La1 O12 121.60(6) . . ?
O21 La1 O12 168.62(5) . . ?
O13 La1 O12 56.62(5) . . ?
O17 La1 N1 148.01(6) . . ?
O14 La1 N1 62.45(6) . . ?
O16 La1 N1 90.86(6) . . ?
O15 La1 N1 130.30(7) . . ?
O18 La1 N1 76.12(7) . . ?
O19 La1 N1 90.94(6) . . ?
O20 La1 N1 23.84(6) . . ?
O21 La1 N1 24.26(6) . . ?
O13 La1 N1 94.97(5) . . ?
O12 La1 N1 144.80(5) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_1s5
_database_code_depnum_ccdc_archive 'CCDC 1472877'
_audit_update_record             
;
2016-04-07 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 Ce N O11'
_chemical_formula_weight         462.33

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'

_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                   15.4860(7)
_cell_length_b                   6.1777(3)
_cell_length_c                   16.8851(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.4770(10)
_cell_angle_gamma                90
_cell_volume                     1458.28(12)
_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       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.106
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.182
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_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            8253
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.457
_diffrn_reflns_theta_max         27.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3250
_reflns_number_gt                3020
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3250
_refine_ls_number_parameters     222
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0165
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0469
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_restrained_S_all      1.302
_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
Ce1 Ce 0.34766(2) 0.54022(3) 0.09281(2) 0.01510(8) Uani 1 1 d . . . . .
C1 C 0.1265(2) 0.5949(5) 0.11738(19) 0.0190(6) Uani 1 1 d . . . . .
C2 C 0.0309(2) 0.6409(6) 0.0899(2) 0.0267(7) Uani 1 1 d . . . . .
H2 H 0.0019 0.7475 0.0479 0.032 Uiso 1 1 calc R U . . .
C3 C -0.0218(3) 0.5288(6) 0.1248(3) 0.0332(8) Uani 1 1 d . . . . .
H3 H -0.0863 0.5604 0.1062 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0207(2) 0.3708(7) 0.1868(2) 0.0359(8) Uani 1 1 d . . . . .
H4 H -0.0154 0.2950 0.2096 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1179(2) 0.3233(6) 0.2157(2) 0.0309(8) Uani 1 1 d . . . . .
H5 H 0.1468 0.2174 0.2581 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1705(2) 0.4360(5) 0.1806(2) 0.0203(6) Uani 1 1 d . . . . .
C7 C 0.3204(2) 0.2728(6) 0.2776(2) 0.0260(7) Uani 1 1 d . . . . .
H7A H 0.2907 0.1318 0.2716 0.031 Uiso 1 1 calc R U . . .
H7B H 0.3231 0.3407 0.3304 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4199(2) 0.2483(5) 0.28364(19) 0.0224(6) Uani 1 1 d . . . . .
C9 C 0.1563(2) 0.9148(5) 0.0520(2) 0.0268(7) Uani 1 1 d . . . . .
H9A H 0.1355 0.9929 0.0905 0.032 Uiso 1 1 calc R U . . .
H9B H 0.1032 0.9085 -0.0059 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2402(2) 1.0328(5) 0.0469(2) 0.0200(6) Uani 1 1 d . . . . .
N1 N 0.3058(2) 0.6657(5) -0.09611(17) 0.0278(6) Uani 1 1 d . . . . .
O1 O 0.18456(14) 0.6996(3) 0.08472(14) 0.0220(4) Uani 1 1 d . . . . .
O2 O 0.26589(14) 0.4040(4) 0.20276(14) 0.0243(5) Uani 1 1 d . . . . .
O3 O 0.43378(15) 0.3068(4) 0.21902(15) 0.0330(6) Uani 1 1 d . . . . .
O4 O 0.48201(14) 0.1684(4) 0.35259(14) 0.0281(5) Uani 1 1 d . . . . .
O5 O 0.23092(15) 1.2329(3) 0.03714(14) 0.0260(5) Uani 1 1 d . . . . .
O6 O 0.30948(18) 0.9239(4) 0.05105(18) 0.0312(6) Uani 1 1 d . . . . .
O7 O 0.37998(17) 0.7700(5) 0.22664(16) 0.0380(6) Uani 1 1 d D . . . .
O8 O 0.42904(19) 0.2510(4) 0.0431(2) 0.0409(6) Uani 1 1 d D . . . .
O9 O 0.24637(19) 0.5701(5) -0.07615(17) 0.0394(7) Uani 1 1 d . . . . .
O10 O 0.38961(16) 0.6866(4) -0.03657(16) 0.0339(6) Uani 1 1 d . . . . .
O11 O 0.2818(2) 0.7374(5) -0.17009(16) 0.0486(7) Uani 1 1 d . . . . .
H8B H 0.4802(17) 0.263(6) 0.039(3) 0.058 Uiso 1 1 d D U . . .
H8A H 0.409(3) 0.128(3) 0.043(3) 0.058 Uiso 1 1 d D U . . .
H7A' H 0.353(2) 0.756(9) 0.260(2) 0.081(18) Uiso 1 1 d D . . . .
H7B' H 0.4380(9) 0.795(7) 0.250(2) 0.050(13) Uiso 1 1 d 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
Ce1 O3 2.440(2) . ?
Ce1 O6 2.471(2) . ?
Ce1 O5 2.509(2) 1_545 ?
Ce1 O4 2.518(2) 2_655 ?
Ce1 O8 2.528(2) . ?
Ce1 O7 2.530(2) . ?
Ce1 O9 2.605(3) . ?
Ce1 O1 2.6592(19) . ?
Ce1 O10 2.689(2) . ?
Ce1 O2 2.790(2) . ?
C1 C2 1.377(4) . ?
C1 C6 1.393(4) . ?
C1 O1 1.399(3) . ?
C2 C3 1.380(5) . ?
C3 C4 1.375(5) . ?
C4 C5 1.399(5) . ?
C5 C6 1.385(4) . ?
C6 O2 1.373(4) . ?
C7 O2 1.431(3) . ?
C7 C8 1.508(4) . ?
C8 O4 1.249(3) . ?
C8 O3 1.252(4) . ?
C9 O1 1.434(4) . ?
C9 C10 1.523(4) . ?
C10 O6 1.243(4) . ?
C10 O5 1.247(3) . ?
N1 O11 1.223(3) . ?
N1 O9 1.255(4) . ?
N1 O10 1.261(3) . ?
O4 Ce1 2.518(2) 2_645 ?
O5 Ce1 2.509(2) 1_565 ?

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 Ce1 O6 142.17(9) . . ?
O3 Ce1 O5 85.13(8) . 1_545 ?
O6 Ce1 O5 125.00(8) . 1_545 ?
O3 Ce1 O4 76.89(8) . 2_655 ?
O6 Ce1 O4 83.52(8) . 2_655 ?
O5 Ce1 O4 147.95(8) 1_545 2_655 ?
O3 Ce1 O8 73.08(9) . . ?
O6 Ce1 O8 132.48(9) . . ?
O5 Ce1 O8 73.89(8) 1_545 . ?
O4 Ce1 O8 75.56(8) 2_655 . ?
O3 Ce1 O7 74.20(10) . . ?
O6 Ce1 O7 69.37(9) . . ?
O5 Ce1 O7 126.38(8) 1_545 . ?
O4 Ce1 O7 73.92(7) 2_655 . ?
O8 Ce1 O7 139.25(9) . . ?
O3 Ce1 O9 147.56(9) . . ?
O6 Ce1 O9 70.24(9) . . ?
O5 Ce1 O9 69.26(7) 1_545 . ?
O4 Ce1 O9 114.90(8) 2_655 . ?
O8 Ce1 O9 80.68(10) . . ?
O7 Ce1 O9 137.15(10) . . ?
O3 Ce1 O1 114.46(7) . . ?
O6 Ce1 O1 61.62(7) . . ?
O5 Ce1 O1 75.26(7) 1_545 . ?
O4 Ce1 O1 136.42(7) 2_655 . ?
O8 Ce1 O1 147.41(8) . . ?
O7 Ce1 O1 69.92(7) . . ?
O9 Ce1 O1 78.83(8) . . ?
O3 Ce1 O10 132.52(7) . . ?
O6 Ce1 O10 63.74(8) . . ?
O5 Ce1 O10 109.69(7) 1_545 . ?
O4 Ce1 O10 67.09(7) 2_655 . ?
O8 Ce1 O10 68.84(9) . . ?
O7 Ce1 O10 120.86(9) . . ?
O9 Ce1 O10 47.81(7) . . ?
O1 Ce1 O10 112.94(7) . . ?
O3 Ce1 O2 58.30(7) . . ?
O6 Ce1 O2 110.97(8) . . ?
O5 Ce1 O2 63.95(7) 1_545 . ?
O4 Ce1 O2 123.72(7) 2_655 . ?
O8 Ce1 O2 116.18(8) . . ?
O7 Ce1 O2 63.05(8) . . ?
O9 Ce1 O2 121.23(7) . . ?
O1 Ce1 O2 56.83(6) . . ?
O10 Ce1 O2 168.37(7) . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 O1 123.5(3) . . ?
C6 C1 O1 116.3(2) . . ?
C1 C2 C3 120.0(3) . . ?
C4 C3 C2 120.3(3) . . ?
C3 C4 C5 120.4(3) . . ?
C6 C5 C4 119.2(3) . . ?
O2 C6 C5 125.0(3) . . ?
O2 C6 C1 115.1(3) . . ?
C5 C6 C1 119.9(3) . . ?
O2 C7 C8 108.3(2) . . ?
O4 C8 O3 125.1(3) . . ?
O4 C8 C7 117.2(3) . . ?
O3 C8 C7 117.7(2) . . ?
O1 C9 C10 109.8(2) . . ?
O6 C10 O5 126.2(3) . . ?
O6 C10 C9 118.3(3) . . ?
O5 C10 C9 115.5(3) . . ?
O11 N1 O9 120.6(3) . . ?
O11 N1 O10 122.3(3) . . ?
O9 N1 O10 117.1(3) . . ?
C1 O1 C9 116.1(2) . . ?
C1 O1 Ce1 124.43(17) . . ?
C9 O1 Ce1 119.24(17) . . ?
C6 O2 C7 118.6(2) . . ?
C6 O2 Ce1 121.20(17) . . ?
C7 O2 Ce1 119.61(16) . . ?
C8 O3 Ce1 134.21(19) . . ?
C8 O4 Ce1 136.9(2) . 2_645 ?
C10 O5 Ce1 132.6(2) . 1_565 ?
C10 O6 Ce1 129.0(2) . . ?
N1 O9 Ce1 99.32(18) . . ?
N1 O10 Ce1 95.04(17) . . ?

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.268

