# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_018PGD
_audit_block_doi                 10.5517/cc12n10s
_database_code_depnum_ccdc_archive 'CCDC 1002354'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.ultsonch.2015.02.003 2015
_audit_update_record             
;
2014-05-12 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 Ce N4 O11'
_chemical_formula_sum            'C12 H11 Ce N4 O11'
_chemical_formula_weight         527.37

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   7.9321(2)
_cell_length_b                   14.7305(3)
_cell_length_c                   27.7895(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3247.03(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2539
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      28.50

_exptl_crystal_description       parallepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      2.15
_exptl_crystal_density_diffrn    2.158
_exptl_crystal_density_method    floatation
_exptl_crystal_F_000             2056
_exptl_absorpt_coefficient_mu    2.878
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5874
_exptl_absorpt_correction_T_max  0.7339
_exptl_absorpt_process_details   
;
Oxford Diffraction Poland (2009). CrysAlis Red,
Version 1.171.33.42
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'KUMA KM-4 with CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36926
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         29.73
_reflns_number_total             4369
_reflns_number_gt                3385
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
Oxford Diffraction Poland (2009). CrysAlis CCD,
Version 1.171.33.42
;
_computing_cell_refinement       
;
Oxford Diffraction Poland (2009). CrysAlis Red,
Version 1.171.33.42
;
_computing_data_reduction        
;
Oxford Diffraction Poland (2009). CrysAlis Red,
Version 1.171.33.42
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular
Structure Visualisation, University of Bonn, Germany
;

_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0186P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4369
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0425
_refine_ls_wR_factor_gt          0.0402
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
Ce Ce 0.014784(14) 0.888950(7) 0.128666(4) 0.01278(4) Uani 1 1 d . . .
O5 O 0.3294(2) 0.88389(15) 0.12912(6) 0.0350(4) Uani 1 1 d . . .
H51 H 0.378(4) 0.886(2) 0.1552(6) 0.052 Uiso 1 1 d . . .
H52 H 0.393(3) 0.885(2) 0.1058(7) 0.052 Uiso 1 1 d . . .
O6 O 0.0908(2) 0.72710(11) 0.11152(7) 0.0287(4) Uani 1 1 d . . .
H61 H 0.160(3) 0.7007(17) 0.0946(8) 0.043 Uiso 1 1 d . . .
H62 H 0.044(3) 0.6873(14) 0.1270(8) 0.043 Uiso 1 1 d . . .
O7 O -0.2190(2) 0.77774(11) 0.15688(6) 0.0252(4) Uani 1 1 d . . .
H71 H -0.298(2) 0.8066(16) 0.1679(9) 0.038 Uiso 1 1 d . . .
H72 H -0.203(4) 0.7404(14) 0.1782(7) 0.038 Uiso 1 1 d . . .
N1 N 0.1082(3) 1.02268(12) 0.19502(6) 0.0208(4) Uani 1 1 d . . .
C2 C 0.1101(3) 0.99515(14) 0.24107(7) 0.0156(5) Uani 1 1 d . . .
C3 C 0.1437(3) 1.05606(15) 0.27803(8) 0.0167(5) Uani 1 1 d . . .
N4 N 0.1682(3) 1.14500(13) 0.26916(7) 0.0261(5) Uani 1 1 d . . .
C5 C 0.1634(4) 1.17120(17) 0.22336(9) 0.0323(6) Uani 1 1 d . . .
H5 H 0.1798 1.2321 0.2160 0.039 Uiso 1 1 calc R . .
C6 C 0.1346(3) 1.11039(16) 0.18658(9) 0.0289(6) Uani 1 1 d . . .
H6 H 0.1337 1.1313 0.1550 0.035 Uiso 1 1 calc R . .
C7 C 0.0660(3) 0.89607(15) 0.24909(8) 0.0170(4) Uani 1 1 d . . .
O1 O 0.0258(2) 0.87221(10) 0.29027(5) 0.0252(4) Uani 1 1 d . . .
O2 O 0.0717(2) 0.84649(10) 0.21232(5) 0.0236(4) Uani 1 1 d . . .
C8 C 0.1649(3) 1.03143(14) 0.33031(8) 0.0172(5) Uani 1 1 d . . .
O3 O 0.2782(2) 0.97655(11) 0.34100(6) 0.0274(4) Uani 1 1 d . . .
O4 O 0.0736(2) 1.07272(11) 0.36016(6) 0.0275(4) Uani 1 1 d . . .
N11 N 0.1520(2) 0.89096(12) 0.03388(6) 0.0161(4) Uani 1 1 d . . .
C12 C 0.1979(3) 0.97406(14) 0.01930(8) 0.0134(4) Uani 1 1 d . . .
C13 C 0.2702(3) 0.98893(14) -0.02564(8) 0.0153(5) Uani 1 1 d . . .
N14 N 0.2942(3) 0.91678(13) -0.05397(7) 0.0211(4) Uani 1 1 d . . .
H14 H 0.338(3) 0.9227(16) -0.0825(4) 0.025 Uiso 1 1 d . . .
C15 C 0.2461(3) 0.83365(16) -0.04091(9) 0.0261(6) Uani 1 1 d . . .
H15 H 0.2607 0.7847 -0.0616 0.031 Uiso 1 1 calc R . .
C16 C 0.1747(3) 0.82146(15) 0.00355(8) 0.0234(5) Uani 1 1 d . . .
H16 H 0.1414 0.7635 0.0129 0.028 Uiso 1 1 calc R . .
C17 C 0.1687(3) 1.05085(14) 0.05454(8) 0.0167(5) Uani 1 1 d . . .
O11 O 0.2412(2) 1.12344(11) 0.04656(6) 0.0331(5) Uani 1 1 d . . .
O12 O 0.0709(2) 1.03326(10) 0.08880(5) 0.0221(4) Uani 1 1 d . . .
C18 C 0.3186(3) 1.08031(15) -0.04734(8) 0.0174(5) Uani 1 1 d . . .
O13 O 0.4692(2) 1.09962(12) -0.04781(7) 0.0345(4) Uani 1 1 d . . .
O14 O 0.1973(2) 1.12426(10) -0.06446(6) 0.0205(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
Ce O3 2.4283(16) 6_556 ?
Ce O12 2.4382(15) . ?
Ce O2 2.4493(15) . ?
Ce O14 2.4600(15) 5_575 ?
Ce O5 2.4970(17) . ?
Ce O6 2.5050(16) . ?
Ce O7 2.5954(17) . ?
Ce N1 2.7982(18) . ?
Ce N11 2.8502(18) . ?
O5 H51 0.82(2) . ?
O5 H52 0.82(2) . ?
O6 H61 0.82(2) . ?
O6 H62 0.82(2) . ?
O7 H71 0.82(2) . ?
O7 H72 0.82(2) . ?
N1 C6 1.330(3) . ?
N1 C2 1.343(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.517(3) . ?
C3 N4 1.347(3) . ?
C3 C8 1.507(3) . ?
N4 C5 1.331(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.239(3) . ?
C7 O2 1.257(3) . ?
C8 O3 1.245(3) . ?
C8 O4 1.258(3) . ?
O3 Ce 2.4283(16) 6_656 ?
N11 C16 1.338(3) . ?
N11 C12 1.340(3) . ?
C12 C13 1.392(3) . ?
C12 C17 1.514(3) . ?
C13 N14 1.336(3) . ?
C13 C18 1.524(3) . ?
N14 C15 1.333(3) . ?
N14 H14 0.87(2) . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O11 1.234(2) . ?
C17 O12 1.255(3) . ?
C18 O13 1.228(3) . ?
C18 O14 1.254(3) . ?
O14 Ce 2.4600(15) 5_575 ?

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 Ce O12 80.54(5) 6_556 . ?
O3 Ce O2 87.06(6) 6_556 . ?
O12 Ce O2 128.33(5) . . ?
O3 Ce O14 76.43(6) 6_556 5_575 ?
O12 Ce O14 82.20(5) . 5_575 ?
O2 Ce O14 142.59(6) . 5_575 ?
O3 Ce O5 141.86(6) 6_556 . ?
O12 Ce O5 81.13(6) . . ?
O2 Ce O5 78.66(6) . . ?
O14 Ce O5 133.22(6) 5_575 . ?
O3 Ce O6 139.28(6) 6_556 . ?
O12 Ce O6 134.38(5) . . ?
O2 Ce O6 83.86(6) . . ?
O14 Ce O6 87.22(6) 5_575 . ?
O5 Ce O6 74.45(7) . . ?
O3 Ce O7 71.25(5) 6_556 . ?
O12 Ce O7 144.89(6) . . ?
O2 Ce O7 71.56(6) . . ?
O14 Ce O7 71.38(5) 5_575 . ?
O5 Ce O7 133.92(6) . . ?
O6 Ce O7 68.21(6) . . ?
O3 Ce N1 66.53(6) 6_556 . ?
O12 Ce N1 68.73(5) . . ?
O2 Ce N1 60.37(5) . . ?
O14 Ce N1 135.62(5) 5_575 . ?
O5 Ce N1 75.70(6) . . ?
O6 Ce N1 137.02(6) . . ?
O7 Ce N1 115.75(6) . . ?
O3 Ce N11 127.61(5) 6_556 . ?
O12 Ce N11 60.08(5) . . ?
O2 Ce N11 144.04(5) . . ?
O14 Ce N11 65.89(5) 5_575 . ?
O5 Ce N11 67.87(5) . . ?
O6 Ce N11 75.06(5) . . ?
O7 Ce N11 123.95(5) . . ?
N1 Ce N11 120.04(5) . . ?
Ce O5 H51 118(2) . . ?
Ce O5 H52 128(2) . . ?
H51 O5 H52 114(3) . . ?
Ce O6 H61 136(2) . . ?
Ce O6 H62 118(2) . . ?
H61 O6 H62 106(3) . . ?
Ce O7 H71 110(2) . . ?
Ce O7 H72 122(2) . . ?
H71 O7 H72 101(3) . . ?
C6 N1 C2 117.38(19) . . ?
C6 N1 Ce 127.55(15) . . ?
C2 N1 Ce 114.74(13) . . ?
N1 C2 C3 120.77(19) . . ?
N1 C2 C7 115.34(18) . . ?
C3 C2 C7 123.84(19) . . ?
N4 C3 C2 121.4(2) . . ?
N4 C3 C8 113.23(19) . . ?
C2 C3 C8 125.34(19) . . ?
C5 N4 C3 116.9(2) . . ?
N4 C5 C6 121.7(2) . . ?
N4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
N1 C6 C5 121.8(2) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
O1 C7 O2 126.5(2) . . ?
O1 C7 C2 117.90(19) . . ?
O2 C7 C2 115.56(19) . . ?
C7 O2 Ce 128.07(14) . . ?
O3 C8 O4 124.9(2) . . ?
O3 C8 C3 117.8(2) . . ?
O4 C8 C3 117.1(2) . . ?
C8 O3 Ce 170.35(15) . 6_656 ?
C16 N11 C12 118.14(19) . . ?
C16 N11 Ce 128.73(14) . . ?
C12 N11 Ce 113.13(13) . . ?
N11 C12 C13 121.8(2) . . ?
N11 C12 C17 116.45(18) . . ?
C13 C12 C17 121.72(19) . . ?
N14 C13 C12 117.5(2) . . ?
N14 C13 C18 115.69(19) . . ?
C12 C13 C18 126.7(2) . . ?
C15 N14 C13 122.0(2) . . ?
C15 N14 H14 117.1(16) . . ?
C13 N14 H14 120.9(16) . . ?
N14 C15 C16 118.9(2) . . ?
N14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N11 C16 C15 121.5(2) . . ?
N11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
O11 C17 O12 127.1(2) . . ?
O11 C17 C12 117.4(2) . . ?
O12 C17 C12 115.52(18) . . ?
C17 O12 Ce 129.60(14) . . ?
O13 C18 O14 128.5(2) . . ?
O13 C18 C13 117.0(2) . . ?
O14 C18 C13 114.4(2) . . ?
C18 O14 Ce 139.41(14) . 5_575 ?

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
O5 H51 O1 0.82(2) 1.93(2) 2.734(2) 167(3) 6_656
O5 H52 O13 0.82(2) 1.96(2) 2.777(3) 173(3) 5_675
O6 H61 O11 0.82(2) 1.92(2) 2.714(2) 162(3) 8_655
O6 H62 O4 0.82(2) 1.96(2) 2.737(2) 158(3) 3_545
O7 H71 O1 0.82(2) 2.06(2) 2.862(2) 168(3) 6_556
O7 H72 N4 0.82(2) 2.05(2) 2.865(3) 179(3) 3_545
N14 H14 O4 0.87(2) 1.74(2) 2.611(2) 176(2) 2_574

_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        28.50
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.095
####################################################################### 
# 
# 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_ir1
_database_code_depnum_ccdc_archive 'CCDC 1040889'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 La N4 O11'
_chemical_formula_sum            'C12 H11 La N4 O11'
_chemical_formula_weight         526.16

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   7.9559(5)
_cell_length_b                   14.7492(8)
_cell_length_c                   27.8802(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3271.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3539
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      28.80

_exptl_crystal_description       parallepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      2.13
_exptl_crystal_density_diffrn    2.136
_exptl_crystal_density_method    floatation
_exptl_crystal_F_000             2048
_exptl_absorpt_coefficient_mu    2.685
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   
;
Oxford Diffraction Poland (2009). CrysAlis Red,
Version 1.171.33.42
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'KUMA KM-4 with CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42639
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         29.79
_reflns_number_total             4478
_reflns_number_gt                3371
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
Oxford Diffraction Poland (2009). CrysAlis CCD,
Version 1.171.33.42
;
_computing_cell_refinement       
;
Oxford Diffraction Poland (2009). CrysAlis Red,
Version 1.171.33.42
;
_computing_data_reduction        
;
Oxford Diffraction Poland (2009). CrysAlis Red,
Version 1.171.33.42
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular
Structure Visualisation, University of Bonn, Germany
;

_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0145P)²+4.3163P] 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         4478
_refine_ls_number_parameters     274
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0499
_refine_ls_wR_factor_gt          0.0446
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.009
_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
La La 0.016034(17) 0.888168(10) 0.128703(5) 0.01357(5) Uani 1 1 d . . .
O5 O 0.3323(3) 0.88236(19) 0.12875(8) 0.0364(6) Uani 1 1 d D . .
H51 H 0.380(4) 0.885(3) 0.1548(7) 0.055 Uiso 1 1 d D . .
H52 H 0.395(4) 0.884(3) 0.1055(9) 0.055 Uiso 1 1 d D . .
O6 O 0.0910(3) 0.72517(14) 0.11126(9) 0.0301(5) Uani 1 1 d D . .
H61 H 0.157(4) 0.701(2) 0.0929(11) 0.045 Uiso 1 1 d D . .
H62 H 0.037(4) 0.6840(17) 0.1235(12) 0.045 Uiso 1 1 d D . .
O7 O -0.2197(3) 0.77705(15) 0.15727(8) 0.0270(5) Uani 1 1 d D . .
H71 H -0.301(3) 0.805(2) 0.1680(12) 0.040 Uiso 1 1 d D . .
H72 H -0.204(5) 0.7379(18) 0.1776(9) 0.040 Uiso 1 1 d D . .
N1 N 0.1086(3) 1.02246(16) 0.19566(8) 0.0213(5) Uani 1 1 d . . .
C2 C 0.1108(4) 0.99511(18) 0.24147(9) 0.0166(6) Uani 1 1 d . . .
C3 C 0.1438(4) 1.0560(2) 0.27843(10) 0.0187(6) Uani 1 1 d . . .
N4 N 0.1675(4) 1.14468(16) 0.26924(9) 0.0265(6) Uani 1 1 d . . .
C5 C 0.1618(5) 1.1713(2) 0.22380(11) 0.0342(8) Uani 1 1 d . . .
H5 H 0.1764 1.2324 0.2166 0.041 Uiso 1 1 calc R . .
C6 C 0.1347(4) 1.1103(2) 0.18695(11) 0.0318(7) Uani 1 1 d . . .
H6 H 0.1347 1.1310 0.1554 0.038 Uiso 1 1 calc R . .
C7 C 0.0674(3) 0.89605(19) 0.24954(10) 0.0181(6) Uani 1 1 d . . .
O1 O 0.0272(3) 0.87229(13) 0.29070(7) 0.0256(5) Uani 1 1 d . . .
O2 O 0.0732(3) 0.84631(13) 0.21320(7) 0.0258(5) Uani 1 1 d . . .
C8 C 0.1661(4) 1.03122(18) 0.33025(10) 0.0176(6) Uani 1 1 d . . .
O3 O 0.2788(3) 0.97725(14) 0.34087(8) 0.0281(5) Uani 1 1 d . . .
O4 O 0.0742(3) 1.07209(14) 0.36020(7) 0.0289(5) Uani 1 1 d . . .
N11 N 0.1529(3) 0.89110(16) 0.03339(8) 0.0173(5) Uani 1 1 d . . .
C12 C 0.1986(3) 0.97408(18) 0.01892(9) 0.0144(6) Uani 1 1 d . . .
C13 C 0.2700(3) 0.98912(19) -0.02588(10) 0.0167(6) Uani 1 1 d . . .
N14 N 0.2931(3) 0.91705(17) -0.05429(9) 0.0212(6) Uani 1 1 d D . .
H14 H 0.334(4) 0.927(2) -0.0828(5) 0.025 Uiso 1 1 d D . .
C15 C 0.2452(4) 0.8338(2) -0.04128(11) 0.0264(7) Uani 1 1 d . . .
H15 H 0.2598 0.7848 -0.0619 0.032 Uiso 1 1 calc R . .
C16 C 0.1744(4) 0.8222(2) 0.00289(11) 0.0247(7) Uani 1 1 d . . .
H16 H 0.1400 0.7645 0.0120 0.030 Uiso 1 1 calc R . .
C17 C 0.1712(4) 1.05087(19) 0.05431(10) 0.0180(6) Uani 1 1 d . . .
O11 O 0.2435(3) 1.12319(14) 0.04600(8) 0.0338(6) Uani 1 1 d . . .
O12 O 0.0738(3) 1.03358(13) 0.08861(7) 0.0237(5) Uani 1 1 d . . .
C18 C 0.3197(4) 1.08090(19) -0.04740(10) 0.0177(6) Uani 1 1 d . . .
O13 O 0.4695(3) 1.09941(16) -0.04782(8) 0.0349(5) Uani 1 1 d . . .
O14 O 0.1992(2) 1.12446(13) -0.06424(7) 0.0216(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
La O3 2.451(2) 6_556 ?
La O12 2.4618(19) . ?
La O2 2.477(2) . ?
La O14 2.4891(19) 5_575 ?
La O5 2.518(2) . ?
La O6 2.524(2) . ?
La O7 2.615(2) . ?
La N1 2.820(2) . ?
La N11 2.872(2) . ?
O5 H51 0.820(5) . ?
O5 H52 0.820(5) . ?
O6 H61 0.820(5) . ?
O6 H62 0.819(5) . ?
O7 H71 0.819(5) . ?
O7 H72 0.819(5) . ?
N1 C6 1.335(4) . ?
N1 C2 1.339(3) . ?
C2 C3 1.392(4) . ?
C2 C7 1.518(4) . ?
C3 N4 1.346(4) . ?
C3 C8 1.501(4) . ?
N4 C5 1.327(4) . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.242(3) . ?
C7 O2 1.252(3) . ?
C8 O3 1.235(3) . ?
C8 O4 1.263(3) . ?
O3 La 2.451(2) 6_656 ?
N11 C16 1.336(4) . ?
N11 C12 1.339(3) . ?
C12 C13 1.390(4) . ?
C12 C17 1.518(4) . ?
C13 N14 1.338(4) . ?
C13 C18 1.533(4) . ?
N14 C15 1.335(4) . ?
N14 H14 0.870(5) . ?
C15 C16 1.365(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O11 1.234(3) . ?
C17 O12 1.257(3) . ?
C18 O13 1.223(3) . ?
C18 O14 1.246(3) . ?
O14 La 2.4891(19) 5_575 ?

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 La O12 80.44(7) 6_556 . ?
O3 La O2 86.89(7) 6_556 . ?
O12 La O2 127.92(7) . . ?
O3 La O14 76.14(7) 6_556 5_575 ?
O12 La O14 82.29(7) . 5_575 ?
O2 La O14 142.58(7) . 5_575 ?
O3 La O5 141.96(8) 6_556 . ?
O12 La O5 80.98(8) . . ?
O2 La O5 78.91(7) . . ?
O14 La O5 133.25(7) 5_575 . ?
O3 La O6 139.39(7) 6_556 . ?
O12 La O6 134.28(7) . . ?
O2 La O6 84.40(7) . . ?
O14 La O6 87.26(7) 5_575 . ?
O5 La O6 74.43(8) . . ?
O3 La O7 71.24(7) 6_556 . ?
O12 La O7 144.91(7) . . ?
O2 La O7 71.69(7) . . ?
O14 La O7 71.32(7) 5_575 . ?
O5 La O7 134.05(8) . . ?
O6 La O7 68.36(7) . . ?
O3 La N1 66.13(8) 6_556 . ?
O12 La N1 68.89(7) . . ?
O2 La N1 59.84(7) . . ?
O14 La N1 135.25(7) 5_575 . ?
O5 La N1 76.27(8) . . ?
O6 La N1 137.30(8) . . ?
O7 La N1 115.21(7) . . ?
O3 La N11 127.17(7) 6_556 . ?
O12 La N11 59.74(6) . . ?
O2 La N11 144.48(7) . . ?
O14 La N11 66.04(6) 5_575 . ?
O5 La N11 67.79(7) . . ?
O6 La N11 75.32(7) . . ?
O7 La N11 124.28(7) . . ?
N1 La N11 120.20(7) . . ?
La O5 H51 117(3) . . ?
La O5 H52 128(3) . . ?
H51 O5 H52 115(4) . . ?
La O6 H61 134(3) . . ?
La O6 H62 120(3) . . ?
H61 O6 H62 106(4) . . ?
La O7 H71 111(3) . . ?
La O7 H72 123(3) . . ?
H71 O7 H72 103(3) . . ?
C6 N1 C2 117.6(2) . . ?
C6 N1 La 127.03(19) . . ?
C2 N1 La 115.03(17) . . ?
N1 C2 C3 120.9(3) . . ?
N1 C2 C7 115.4(2) . . ?
C3 C2 C7 123.6(2) . . ?
N4 C3 C2 120.8(3) . . ?
N4 C3 C8 113.8(2) . . ?
C2 C3 C8 125.3(3) . . ?
C5 N4 C3 117.7(3) . . ?
N4 C5 C6 121.5(3) . . ?
N4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
N1 C6 C5 121.4(3) . . ?
N1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O1 C7 O2 126.3(3) . . ?
O1 C7 C2 117.8(2) . . ?
O2 C7 C2 115.8(2) . . ?
C7 O2 La 128.08(18) . . ?
O3 C8 O4 124.7(3) . . ?
O3 C8 C3 118.3(3) . . ?
O4 C8 C3 116.9(3) . . ?
C8 O3 La 170.9(2) . 6_656 ?
C16 N11 C12 118.0(2) . . ?
C16 N11 La 128.74(19) . . ?
C12 N11 La 113.30(17) . . ?
N11 C12 C13 121.8(3) . . ?
N11 C12 C17 116.6(2) . . ?
C13 C12 C17 121.6(2) . . ?
N14 C13 C12 117.5(3) . . ?
N14 C13 C18 115.8(2) . . ?
C12 C13 C18 126.7(3) . . ?
C15 N14 C13 122.0(2) . . ?
C15 N14 H14 120(2) . . ?
C13 N14 H14 118(2) . . ?
N14 C15 C16 118.6(3) . . ?
N14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N11 C16 C15 122.1(3) . . ?
N11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
O11 C17 O12 127.3(3) . . ?
O11 C17 C12 117.1(3) . . ?
O12 C17 C12 115.6(2) . . ?
C17 O12 La 129.58(18) . . ?
O13 C18 O14 129.2(3) . . ?
O13 C18 C13 116.9(3) . . ?
O14 C18 C13 113.9(2) . . ?
C18 O14 La 139.70(18) . 5_575 ?

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
O5 H51 O1 0.820(5) 1.928(11) 2.733(3) 167(4) 6_656
O5 H52 O13 0.820(5) 1.950(8) 2.766(3) 173(4) 5_675
O6 H61 O11 0.820(5) 1.907(12) 2.703(3) 163(4) 8_655
O6 H62 O4 0.819(5) 1.926(10) 2.731(3) 167(4) 3_545
O7 H71 O1 0.819(5) 2.049(10) 2.852(3) 167(4) 6_556
O7 H72 N4 0.819(5) 2.042(6) 2.860(3) 177(4) 3_545
N14 H14 O4 0.870(5) 1.749(8) 2.612(3) 171(3) 2_574

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        29.20
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.123
