# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_lal1
_database_code_depnum_ccdc_archive 'CCDC 1849130'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2019-01-02 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            'C26 H18 La N9 O9'
_chemical_formula_weight         739.40

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.1366(3)
_cell_length_b                   14.1095(3)
_cell_length_c                   20.9641(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.052(3)
_cell_angle_gamma                90
_cell_volume                     2702.53(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8376
_cell_measurement_theta_min      2.3940
_cell_measurement_theta_max      31.2330

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.655
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9854
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.740
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4657
_reflns_number_gt                4222
_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0351P)²+2.0194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4657
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
La01 La 0.33384(2) 0.24495(2) 0.39450(2) 0.01661(8) Uani 1 1 d . . . . .
O71 O 0.1270(3) 0.23036(15) 0.48097(12) 0.0322(6) Uani 1 1 d . . . . .
O72 O 0.2315(2) 0.09633(15) 0.46360(11) 0.0307(5) Uani 1 1 d . . . . .
O52 O 0.5935(2) 0.33249(14) 0.40123(10) 0.0244(5) Uani 1 1 d . . . . .
O62 O 0.5024(2) 0.23609(14) 0.28801(11) 0.0254(5) Uani 1 1 d . . . . .
O51 O 0.4341(2) 0.41274(15) 0.34724(10) 0.0236(5) Uani 1 1 d . . . . .
O61 O 0.2802(2) 0.28237(17) 0.27004(10) 0.0280(5) Uani 1 1 d . . . . .
O53 O 0.6630(2) 0.45492(15) 0.34648(10) 0.0285(5) Uani 1 1 d . . . . .
O73 O 0.0385(3) 0.10331(18) 0.52523(13) 0.0452(7) Uani 1 1 d . . . . .
N15 N 0.2894(3) 0.39932(16) 0.47276(11) 0.0202(5) Uani 1 1 d . . . . .
O63 O 0.4444(3) 0.30066(18) 0.19633(11) 0.0381(6) Uani 1 1 d . . . . .
N71 N 0.1301(3) 0.14204(18) 0.49065(13) 0.0286(6) Uani 1 1 d . . . . .
N11 N 0.0884(3) 0.17509(16) 0.34077(11) 0.0204(5) Uani 1 1 d . . . . .
N16 N 0.0957(3) 0.35955(16) 0.38034(11) 0.0189(5) Uani 1 1 d . . . . .
N12 N 0.3408(3) 0.07044(16) 0.33701(11) 0.0207(5) Uani 1 1 d . . . . .
N13 N 0.5396(3) 0.11128(16) 0.42860(12) 0.0205(5) Uani 1 1 d . . . . .
C30 C 0.1975(3) 0.4749(2) 0.45270(14) 0.0200(6) Uani 1 1 d . . . . .
N61 N 0.4104(3) 0.27333(18) 0.24976(12) 0.0249(6) Uani 1 1 d . . . . .
N14 N 0.4642(3) 0.25262(15) 0.51207(12) 0.0195(6) Uani 1 1 d . . . . .
N51 N 0.5657(3) 0.40105(17) 0.36457(11) 0.0208(5) Uani 1 1 d . . . . .
C32 C 0.1099(3) 0.6352(2) 0.45507(16) 0.0274(7) Uani 1 1 d . . . . .
H32 H 0.1115 0.6954 0.4732 0.033 Uiso 1 1 calc R U . . .
C35 C 0.0987(3) 0.45459(19) 0.40347(14) 0.0204(6) Uani 1 1 d . . . . .
C31 C 0.2019(3) 0.5658(2) 0.47813(15) 0.0247(7) Uani 1 1 d . . . . .
H31 H 0.2671 0.5799 0.5108 0.030 Uiso 1 1 calc R U . . .
C25 C 0.6377(3) 0.1916(2) 0.58789(15) 0.0255(7) Uani 1 1 d . . . . .
H25 H 0.7071 0.1460 0.5984 0.031 Uiso 1 1 calc R U . . .
C27 C 0.5046(3) 0.3318(2) 0.61197(14) 0.0255(7) Uani 1 1 d . . . . .
H27 H 0.4812 0.3816 0.6391 0.031 Uiso 1 1 calc R U . . .
C13 C -0.1617(3) 0.1079(2) 0.27914(15) 0.0275(7) Uani 1 1 d . . . . .
H13 H -0.2450 0.0860 0.2583 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2233(3) 0.0345(2) 0.31368(14) 0.0240(7) Uani 1 1 d . . . . .
H16 H 0.2247 -0.0270 0.2977 0.029 Uiso 1 1 calc R U . . .
C22 C 0.5726(3) 0.03530(19) 0.38647(14) 0.0219(6) Uani 1 1 d . . . . .
C17 C 0.4711(3) 0.0158(2) 0.33788(14) 0.0225(6) Uani 1 1 d . . . . .
C23 C 0.5947(3) 0.1110(2) 0.48474(14) 0.0233(7) Uani 1 1 d . . . . .
H23 H 0.6550 0.0611 0.4971 0.028 Uiso 1 1 calc R U . . .
C29 C 0.3361(3) 0.3978(2) 0.53051(14) 0.0231(6) Uani 1 1 d . . . . .
H29 H 0.3052 0.4442 0.5590 0.028 Uiso 1 1 calc R U . . .
C36 C -0.0267(3) 0.3236(2) 0.36429(14) 0.0229(7) Uani 1 1 d . . . . .
H36 H -0.1122 0.3587 0.3691 0.027 Uiso 1 1 calc R U . . .
C24 C 0.5646(3) 0.1876(2) 0.52984(14) 0.0205(6) Uani 1 1 d . . . . .
C15 C 0.0867(3) 0.0891(2) 0.31189(13) 0.0210(6) Uani 1 1 d . . . . .
C19 C 0.6279(4) -0.1085(2) 0.29923(17) 0.0333(8) Uani 1 1 d . . . . .
H19 H 0.6471 -0.1566 0.2701 0.040 Uiso 1 1 calc R U . . .
C21 C 0.7006(3) -0.0181(2) 0.39126(15) 0.0269(7) Uani 1 1 d . . . . .
H21 H 0.7680 -0.0051 0.4233 0.032 Uiso 1 1 calc R U . . .
C26 C 0.6056(4) 0.2650(2) 0.63012(17) 0.0312(8) Uani 1 1 d . . . . .
H26 H 0.6515 0.2686 0.6697 0.037 Uiso 1 1 calc R U . . .
C11 C -0.0339(3) 0.2271(2) 0.33824(15) 0.0223(6) Uani 1 1 d . . . . .
C34 C 0.0082(3) 0.5260(2) 0.37952(15) 0.0258(7) Uani 1 1 d . . . . .
H34 H -0.0564 0.5130 0.3464 0.031 Uiso 1 1 calc R U . . .
C28 C 0.4372(3) 0.3242(2) 0.55232(14) 0.0208(6) Uani 1 1 d . . . . .
C18 C 0.5017(4) -0.0560(2) 0.29336(15) 0.0284(7) Uani 1 1 d . . . . .
H18 H 0.4370 -0.0679 0.2601 0.034 Uiso 1 1 calc R U . . .
C20 C 0.7272(4) -0.0908(2) 0.34809(17) 0.0330(8) Uani 1 1 d . . . . .
H20 H 0.8113 -0.1276 0.3519 0.040 Uiso 1 1 calc R U . . .
C14 C -0.0357(3) 0.0544(2) 0.28022(14) 0.0267(7) Uani 1 1 d . . . . .
H14 H -0.0326 -0.0043 0.2600 0.032 Uiso 1 1 calc R U . . .
C33 C 0.0151(3) 0.6160(2) 0.40513(16) 0.0289(7) Uani 1 1 d . . . . .
H33 H -0.0442 0.6638 0.3888 0.035 Uiso 1 1 calc R U . . .
C12 C -0.1621(3) 0.1947(2) 0.30946(15) 0.0264(7) Uani 1 1 d . . . . .
H12 H -0.2469 0.2312 0.3107 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
La01 O71 2.628(2) . ?
La01 O52 2.679(2) . ?
La01 N11 2.695(2) . ?
La01 O61 2.706(2) . ?
La01 O72 2.715(2) . ?
La01 O62 2.716(2) . ?
La01 O51 2.725(2) . ?
La01 N16 2.727(2) . ?
La01 N14 2.738(3) . ?
La01 N12 2.742(2) . ?
La01 N13 2.757(2) . ?
La01 N15 2.757(2) . ?
O71 N71 1.263(3) . ?
O72 N71 1.264(3) . ?
O52 N51 1.261(3) . ?
O62 N61 1.274(4) . ?
O51 N51 1.266(3) . ?
O61 N61 1.270(3) . ?
O53 N51 1.230(3) . ?
O73 N71 1.235(3) . ?
N15 C29 1.283(4) . ?
N15 C30 1.420(4) . ?
O63 N61 1.225(3) . ?
N11 C11 1.338(4) . ?
N11 C15 1.355(4) . ?
N16 C36 1.273(4) . ?
N16 C35 1.426(3) . ?
N12 C16 1.284(4) . ?
N12 C17 1.418(4) . ?
N13 C23 1.280(4) . ?
N13 C22 1.421(4) . ?
C30 C31 1.390(4) . ?
C30 C35 1.400(4) . ?
N14 C28 1.339(4) . ?
N14 C24 1.350(4) . ?
C32 C31 1.377(4) . ?
C32 C33 1.385(5) . ?
C32 H32 0.9300 . ?
C35 C34 1.396(4) . ?
C31 H31 0.9300 . ?
C25 C24 1.389(4) . ?
C25 C26 1.393(5) . ?
C25 H25 0.9300 . ?
C27 C26 1.373(5) . ?
C27 C28 1.398(4) . ?
C27 H27 0.9300 . ?
C13 C14 1.377(4) . ?
C13 C12 1.380(4) . ?
C13 H13 0.9300 . ?
C16 C15 1.467(4) . ?
C16 H16 0.9300 . ?
C22 C21 1.395(4) . ?
C22 C17 1.404(4) . ?
C17 C18 1.406(4) . ?
C23 C24 1.463(4) . ?
C23 H23 0.9300 . ?
C29 C28 1.463(4) . ?
C29 H29 0.9300 . ?
C36 C11 1.469(4) . ?
C36 H36 0.9300 . ?
C15 C14 1.389(4) . ?
C19 C18 1.376(4) . ?
C19 C20 1.390(5) . ?
C19 H19 0.9300 . ?
C21 C20 1.390(4) . ?
C21 H21 0.9300 . ?
C26 H26 0.9300 . ?
C11 C12 1.394(4) . ?
C34 C33 1.380(4) . ?
C34 H34 0.9300 . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C14 H14 0.9300 . ?
C33 H33 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O71 La01 O52 129.59(7) . . ?
O71 La01 N11 70.19(8) . . ?
O52 La01 N11 158.02(7) . . ?
O71 La01 O61 123.41(7) . . ?
O52 La01 O61 96.93(6) . . ?
N11 La01 O61 61.22(7) . . ?
O71 La01 O72 47.41(6) . . ?
O52 La01 O72 129.31(7) . . ?
N11 La01 O72 69.73(7) . . ?
O61 La01 O72 127.07(7) . . ?
O71 La01 O62 166.41(8) . . ?
O52 La01 O62 64.00(7) . . ?
N11 La01 O62 96.42(7) . . ?
O61 La01 O62 47.07(7) . . ?
O72 La01 O62 126.78(6) . . ?
O71 La01 O51 124.12(6) . . ?
O52 La01 O51 47.20(6) . . ?
N11 La01 O51 116.46(7) . . ?
O61 La01 O51 62.66(6) . . ?
O72 La01 O51 168.78(6) . . ?
O62 La01 O51 63.27(6) . . ?
O71 La01 N16 63.08(7) . . ?
O52 La01 N16 116.04(7) . . ?
N11 La01 N16 60.52(7) . . ?
O61 La01 N16 68.63(7) . . ?
O72 La01 N16 103.93(7) . . ?
O62 La01 N16 113.00(7) . . ?
O51 La01 N16 73.37(6) . . ?
O71 La01 N14 72.21(8) . . ?
O52 La01 N14 63.25(7) . . ?
N11 La01 N14 138.72(7) . . ?
O61 La01 N14 159.76(7) . . ?
O72 La01 N14 72.54(7) . . ?
O62 La01 N14 119.69(7) . . ?
O51 La01 N14 98.45(6) . . ?
N16 La01 N14 114.88(7) . . ?
O71 La01 N12 104.47(7) . . ?
O52 La01 N12 114.60(7) . . ?
N11 La01 N12 60.50(7) . . ?
O61 La01 N12 75.86(7) . . ?
O72 La01 N12 63.20(6) . . ?
O62 La01 N12 65.42(6) . . ?
O51 La01 N12 127.75(6) . . ?
N16 La01 N12 120.23(7) . . ?
N14 La01 N12 114.88(7) . . ?
O71 La01 N13 104.96(7) . . ?
O52 La01 N13 72.42(6) . . ?
N11 La01 N13 115.16(7) . . ?
O61 La01 N13 120.42(7) . . ?
O72 La01 N13 64.44(7) . . ?
O62 La01 N13 78.15(7) . . ?
O51 La01 N13 117.34(6) . . ?
N16 La01 N13 167.90(7) . . ?
N14 La01 N13 59.85(7) . . ?
N12 La01 N13 58.90(7) . . ?
O71 La01 N15 62.94(7) . . ?
O52 La01 N15 74.65(6) . . ?
N11 La01 N15 114.50(7) . . ?
O61 La01 N15 113.14(7) . . ?
O72 La01 N15 103.98(7) . . ?
O62 La01 N15 127.54(6) . . ?
O51 La01 N15 65.15(6) . . ?
N16 La01 N15 58.56(7) . . ?
N14 La01 N15 59.82(7) . . ?
N12 La01 N15 167.00(7) . . ?
N13 La01 N15 119.13(7) . . ?
N71 O71 La01 99.93(17) . . ?
N71 O72 La01 95.64(16) . . ?
N51 O52 La01 98.24(15) . . ?
N61 O62 La01 97.12(16) . . ?
N51 O51 La01 95.85(15) . . ?
N61 O61 La01 97.70(17) . . ?
C29 N15 C30 119.2(2) . . ?
C29 N15 La01 119.93(19) . . ?
C30 N15 La01 120.27(18) . . ?
O73 N71 O71 121.1(3) . . ?
O73 N71 O72 122.3(3) . . ?
O71 N71 O72 116.6(2) . . ?
C11 N11 C15 117.6(3) . . ?
C11 N11 La01 120.72(19) . . ?
C15 N11 La01 121.55(18) . . ?
C36 N16 C35 118.8(2) . . ?
C36 N16 La01 119.54(19) . . ?
C35 N16 La01 120.34(18) . . ?
C16 N12 C17 119.5(2) . . ?
C16 N12 La01 120.13(19) . . ?
C17 N12 La01 120.14(18) . . ?
C23 N13 C22 119.1(2) . . ?
C23 N13 La01 120.55(19) . . ?
C22 N13 La01 119.97(18) . . ?
C31 C30 C35 119.3(3) . . ?
C31 C30 N15 124.2(3) . . ?
C35 C30 N15 116.4(2) . . ?
O63 N61 O61 120.8(3) . . ?
O63 N61 O62 122.5(3) . . ?
O61 N61 O62 116.6(2) . . ?
C28 N14 C24 117.6(3) . . ?
C28 N14 La01 121.13(19) . . ?
C24 N14 La01 121.11(18) . . ?
O53 N51 O52 121.1(2) . . ?
O53 N51 O51 121.2(2) . . ?
O52 N51 O51 117.7(2) . . ?
C31 C32 C33 120.5(3) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C34 C35 C30 119.9(3) . . ?
C34 C35 N16 123.0(3) . . ?
C30 C35 N16 117.1(3) . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C24 C25 C26 119.0(3) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C26 C27 C28 119.4(3) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N12 C16 C15 120.9(3) . . ?
N12 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C21 C22 C17 119.9(3) . . ?
C21 C22 N13 122.7(3) . . ?
C17 C22 N13 117.3(3) . . ?
C22 C17 C18 119.4(3) . . ?
C22 C17 N12 117.2(2) . . ?
C18 C17 N12 123.4(3) . . ?
N13 C23 C24 121.2(3) . . ?
N13 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
N15 C29 C28 121.1(3) . . ?
N15 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
N16 C36 C11 120.5(3) . . ?
N16 C36 H36 119.8 . . ?
C11 C36 H36 119.8 . . ?
N14 C24 C25 122.7(3) . . ?
N14 C24 C23 116.9(3) . . ?
C25 C24 C23 120.4(3) . . ?
N11 C15 C14 122.6(3) . . ?
N11 C15 C16 116.7(3) . . ?
C14 C15 C16 120.7(3) . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C27 C26 C25 118.4(3) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
N11 C11 C12 122.6(3) . . ?
N11 C11 C36 117.2(3) . . ?
C12 C11 C36 120.1(3) . . ?
C33 C34 C35 119.8(3) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
N14 C28 C27 122.7(3) . . ?
N14 C28 C29 117.1(3) . . ?
C27 C28 C29 120.2(3) . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C13 C14 C15 119.1(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C34 C33 C32 120.1(3) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?

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
La01 O71 N71 O73 -173.7(2) . . . . ?
La01 O71 N71 O72 6.8(3) . . . . ?
La01 O72 N71 O73 174.0(3) . . . . ?
La01 O72 N71 O71 -6.5(3) . . . . ?
C29 N15 C30 C31 29.2(4) . . . . ?
La01 N15 C30 C31 -159.7(2) . . . . ?
C29 N15 C30 C35 -151.7(3) . . . . ?
La01 N15 C30 C35 19.4(3) . . . . ?
La01 O61 N61 O63 -166.8(2) . . . . ?
La01 O61 N61 O62 12.2(3) . . . . ?
La01 O62 N61 O63 166.9(2) . . . . ?
La01 O62 N61 O61 -12.1(3) . . . . ?
La01 O52 N51 O53 -170.2(2) . . . . ?
La01 O52 N51 O51 10.0(2) . . . . ?
La01 O51 N51 O53 170.5(2) . . . . ?
La01 O51 N51 O52 -9.8(2) . . . . ?
C31 C30 C35 C34 1.4(4) . . . . ?
N15 C30 C35 C34 -177.7(2) . . . . ?
C31 C30 C35 N16 -178.2(2) . . . . ?
N15 C30 C35 N16 2.6(4) . . . . ?
C36 N16 C35 C34 -36.7(4) . . . . ?
La01 N16 C35 C34 156.5(2) . . . . ?
C36 N16 C35 C30 142.9(3) . . . . ?
La01 N16 C35 C30 -23.9(3) . . . . ?
C33 C32 C31 C30 -1.8(4) . . . . ?
C35 C30 C31 C32 0.0(4) . . . . ?
N15 C30 C31 C32 179.0(3) . . . . ?
C17 N12 C16 C15 -179.8(2) . . . . ?
La01 N12 C16 C15 5.7(4) . . . . ?
C23 N13 C22 C21 -26.2(4) . . . . ?
La01 N13 C22 C21 161.2(2) . . . . ?
C23 N13 C22 C17 154.8(3) . . . . ?
La01 N13 C22 C17 -17.8(3) . . . . ?
C21 C22 C17 C18 -1.7(4) . . . . ?
N13 C22 C17 C18 177.3(2) . . . . ?
C21 C22 C17 N12 177.8(3) . . . . ?
N13 C22 C17 N12 -3.2(4) . . . . ?
C16 N12 C17 C22 -151.5(3) . . . . ?
La01 N12 C17 C22 23.0(3) . . . . ?
C16 N12 C17 C18 28.0(4) . . . . ?
La01 N12 C17 C18 -157.6(2) . . . . ?
C22 N13 C23 C24 179.8(3) . . . . ?
La01 N13 C23 C24 -7.6(4) . . . . ?
C30 N15 C29 C28 -176.7(2) . . . . ?
La01 N15 C29 C28 12.2(4) . . . . ?
C35 N16 C36 C11 177.9(3) . . . . ?
La01 N16 C36 C11 -15.2(4) . . . . ?
C28 N14 C24 C25 1.1(4) . . . . ?
La01 N14 C24 C25 177.1(2) . . . . ?
C28 N14 C24 C23 -178.9(2) . . . . ?
La01 N14 C24 C23 -2.9(3) . . . . ?
C26 C25 C24 N14 0.7(4) . . . . ?
C26 C25 C24 C23 -179.3(3) . . . . ?
N13 C23 C24 N14 7.1(4) . . . . ?
N13 C23 C24 C25 -172.9(3) . . . . ?
C11 N11 C15 C14 0.2(4) . . . . ?
La01 N11 C15 C14 -175.6(2) . . . . ?
C11 N11 C15 C16 178.3(3) . . . . ?
La01 N11 C15 C16 2.4(3) . . . . ?
N12 C16 C15 N11 -5.5(4) . . . . ?
N12 C16 C15 C14 172.6(3) . . . . ?
C17 C22 C21 C20 -0.3(4) . . . . ?
N13 C22 C21 C20 -179.2(3) . . . . ?
C28 C27 C26 C25 0.2(5) . . . . ?
C24 C25 C26 C27 -1.3(5) . . . . ?
C15 N11 C11 C12 2.4(4) . . . . ?
La01 N11 C11 C12 178.3(2) . . . . ?
C15 N11 C11 C36 -174.3(3) . . . . ?
La01 N11 C11 C36 1.6(3) . . . . ?
N16 C36 C11 N11 9.2(4) . . . . ?
N16 C36 C11 C12 -167.6(3) . . . . ?
C30 C35 C34 C33 -1.0(4) . . . . ?
N16 C35 C34 C33 178.7(3) . . . . ?
C24 N14 C28 C27 -2.3(4) . . . . ?
La01 N14 C28 C27 -178.3(2) . . . . ?
C24 N14 C28 C29 175.6(2) . . . . ?
La01 N14 C28 C29 -0.3(3) . . . . ?
C26 C27 C28 N14 1.7(5) . . . . ?
C26 C27 C28 C29 -176.2(3) . . . . ?
N15 C29 C28 N14 -8.0(4) . . . . ?
N15 C29 C28 C27 170.0(3) . . . . ?
C20 C19 C18 C17 -0.9(5) . . . . ?
C22 C17 C18 C19 2.3(4) . . . . ?
N12 C17 C18 C19 -177.2(3) . . . . ?
C22 C21 C20 C19 1.7(5) . . . . ?
C18 C19 C20 C21 -1.0(5) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
N11 C15 C14 C13 -1.5(4) . . . . ?
C16 C15 C14 C13 -179.5(3) . . . . ?
C35 C34 C33 C32 -0.9(4) . . . . ?
C31 C32 C33 C34 2.3(5) . . . . ?
C14 C13 C12 C11 2.3(4) . . . . ?
N11 C11 C12 C13 -3.7(5) . . . . ?
C36 C11 C12 C13 172.9(3) . . . . ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.108



####################################################################### 
# 
# 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_cel1
_database_code_depnum_ccdc_archive 'CCDC 1849131'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2019-01-02 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            'C26 H18 Ce N9 O9'
_chemical_formula_weight         740.61

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'
Ce Ce -0.2486 2.6331 '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'

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

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

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

_cell_length_a                   15.0921(16)
_cell_length_b                   10.8118(8)
_cell_length_c                   19.5232(17)
_cell_angle_alpha                90
_cell_angle_beta                 118.320(13)
_cell_angle_gamma                90
_cell_volume                     2804.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    3916
_cell_measurement_theta_min      2.3560
_cell_measurement_theta_max      30.3400

_exptl_crystal_description       'block shaped'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             1468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.694
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6863
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.362
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2463
_reflns_number_gt                2078
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_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)+(0.0510P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2463
_refine_ls_number_parameters     207
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O53 O 0.6483(3) -0.0143(4) 0.8755(2) 0.0420(12) Uani 1 1 d . . . . .
O51 O 0.5219(3) -0.1433(3) 0.8308(2) 0.0285(10) Uani 1 1 d . . . . .
Ce01 Ce 0.5000 -0.34918(4) 0.7500 0.0272(2) Uani 1 2 d S T P . .
O52 O 0.6533(3) -0.1860(4) 0.8175(2) 0.0314(10) Uani 1 1 d . . . . .
N51 N 0.6094(4) -0.1132(4) 0.8417(2) 0.0294(12) Uani 1 1 d . . . . .
N11 N 0.3090(4) -0.4376(4) 0.6749(2) 0.0329(13) Uani 1 1 d . . . . .
C11 C 0.2564(5) -0.4583(6) 0.7124(3) 0.0362(16) Uani 1 1 d . . . . .
N12 N 0.4064(4) -0.3783(4) 0.5908(2) 0.0293(12) Uani 1 1 d . . . . .
C12 C 0.1584(5) -0.5035(6) 0.6763(3) 0.0432(18) Uani 1 1 d . . . . .
H12A H 0.1233 -0.5158 0.7041 0.052 Uiso 1 1 calc R U . . .
N13 N 0.6078(4) -0.3749(4) 0.6709(2) 0.0280(12) Uani 1 1 d . . . . .
C13 C 0.1146(5) -0.5297(6) 0.5972(3) 0.0401(17) Uani 1 1 d . . . . .
H13A H 0.0501 -0.5629 0.5714 0.048 Uiso 1 1 calc R U . . .
C14 C 0.1662(5) -0.5067(5) 0.5578(3) 0.0335(15) Uani 1 1 d . . . . .
H14A H 0.1365 -0.5213 0.5045 0.040 Uiso 1 1 calc R U . . .
C15 C 0.2651(5) -0.4606(5) 0.5979(3) 0.0321(15) Uani 1 1 d . . . . .
C16 C 0.3208(5) -0.4312(5) 0.5567(3) 0.0329(15) Uani 1 1 d . . . . .
H16A H 0.2935 -0.4513 0.5042 0.039 Uiso 1 1 calc R U . . .
C17 C 0.4588(5) -0.3498(5) 0.5486(3) 0.0281(14) Uani 1 1 d . . . . .
C18 C 0.4094(5) -0.3204(5) 0.4685(3) 0.0337(15) Uani 1 1 d . . . . .
H18A H 0.3395 -0.3178 0.4409 0.040 Uiso 1 1 calc R U . . .
C19 C 0.4651(6) -0.2961(6) 0.4320(3) 0.0402(18) Uani 1 1 d . . . . .
H19A H 0.4326 -0.2777 0.3791 0.048 Uiso 1 1 calc R U . . .
C20 C 0.5689(5) -0.2980(5) 0.4718(3) 0.0380(16) Uani 1 1 d . . . . .
H20A H 0.6059 -0.2827 0.4458 0.046 Uiso 1 1 calc R U . . .
C21 C 0.6181(5) -0.3232(5) 0.5515(3) 0.0340(15) Uani 1 1 d . . . . .
H21A H 0.6881 -0.3222 0.5790 0.041 Uiso 1 1 calc R U . . .
C22 C 0.5637(5) -0.3493(5) 0.5893(3) 0.0278(14) Uani 1 1 d . . . . .
C23 C 0.6926(5) -0.4314(6) 0.7033(3) 0.0377(16) Uani 1 1 d . . . . .
H23 H 0.7224 -0.4558 0.6733 0.045 Uiso 1 1 calc R U . . .
N61 N 0.5000 -0.6286(13) 0.7500 0.077(8) Uiso 0.5 2 d DS U P A 1
O61 O 0.4794(10) -0.5699(10) 0.7962(6) 0.061(4) Uiso 0.5 1 d D U P A 1
O63 O 0.5000 -0.7454(11) 0.7500 0.063(4) Uiso 0.5 2 d DS U P A 1
N61A N 0.4790(4) -0.6321(8) 0.7436(5) 0.021(4) Uiso 0.25 1 d D U P A 2
O61A O 0.5077(8) -0.5772(8) 0.8078(3) 0.030(3) Uiso 0.5 1 d D U P A 2
O63A O 0.4386(10) -0.7371(9) 0.7304(6) 0.042(4) Uiso 0.25 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O53 N51 1.248(6) . ?
O51 N51 1.277(7) . ?
O51 Ce01 2.657(4) . ?
Ce01 O61 2.621(10) 2_656 ?
Ce01 O61 2.621(10) . ?
Ce01 O51 2.657(4) 2_656 ?
Ce01 O61A 2.691(8) 2_656 ?
Ce01 O61A 2.691(8) . ?
Ce01 O52 2.704(4) . ?
Ce01 O52 2.704(4) 2_656 ?
Ce01 N11 2.713(5) . ?
Ce01 N11 2.713(5) 2_656 ?
Ce01 N13 2.736(5) 2_656 ?
Ce01 N13 2.736(5) . ?
O52 N51 1.256(6) . ?
N11 C11 1.329(8) . ?
N11 C15 1.348(6) . ?
C11 C12 1.391(9) . ?
C11 C23 1.479(7) 2_656 ?
N12 C16 1.275(8) . ?
N12 C17 1.419(8) . ?
C12 C13 1.391(8) . ?
C12 H12A 0.9300 . ?
N13 C23 1.282(8) . ?
N13 C22 1.432(6) . ?
C13 C14 1.351(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.408(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.447(9) . ?
C16 H16A 0.9300 . ?
C17 C22 1.394(9) . ?
C17 C18 1.413(7) . ?
C18 C19 1.361(9) . ?
C18 H18A 0.9300 . ?
C19 C20 1.380(9) . ?
C19 H19A 0.9300 . ?
C20 C21 1.396(7) . ?
C20 H20A 0.9300 . ?
C21 C22 1.370(9) . ?
C21 H21A 0.9300 . ?
C23 C11 1.479(7) 2_656 ?
C23 H23 0.9300 . ?
N61 O61 1.257(5) . ?
N61 O61 1.257(5) 2_656 ?
N61 O63 1.263(8) . ?
N61A N61A 0.561(11) 2_656 ?
N61A O63A 1.256(8) . ?
N61A O61A 1.261(8) 2_656 ?
N61A O61A 1.263(8) . ?
N61A O63A 1.580(11) 2_656 ?
O61A N61A 1.261(8) 2_656 ?
O63A N61A 1.580(11) 2_656 ?
O63A O63A 1.64(3) 2_656 ?

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
N51 O51 Ce01 98.0(3) . . ?
O61 Ce01 O61 48.9(3) 2_656 . ?
O61 Ce01 O51 164.9(3) 2_656 . ?
O61 Ce01 O51 124.04(17) . . ?
O61 Ce01 O51 124.04(17) 2_656 2_656 ?
O61 Ce01 O51 164.9(3) . 2_656 ?
O51 Ce01 O51 66.21(16) . 2_656 ?
O51 Ce01 O61A 170.08(14) . 2_656 ?
O51 Ce01 O61A 123.37(13) 2_656 2_656 ?
O51 Ce01 O61A 123.37(13) . . ?
O51 Ce01 O61A 170.08(14) 2_656 . ?
O61A Ce01 O61A 47.2(2) 2_656 . ?
O61 Ce01 O52 123.2(3) 2_656 . ?
O61 Ce01 O52 129.8(3) . . ?
O51 Ce01 O52 47.73(13) . . ?
O51 Ce01 O52 65.12(11) 2_656 . ?
O61A Ce01 O52 131.2(2) 2_656 . ?
O61A Ce01 O52 122.5(2) . . ?
O61 Ce01 O52 129.8(3) 2_656 2_656 ?
O61 Ce01 O52 123.2(3) . 2_656 ?
O51 Ce01 O52 65.13(11) . 2_656 ?
O51 Ce01 O52 47.73(13) 2_656 2_656 ?
O61A Ce01 O52 122.5(2) 2_656 2_656 ?
O61A Ce01 O52 131.2(2) . 2_656 ?
O52 Ce01 O52 98.53(17) . 2_656 ?
O61 Ce01 N11 76.3(3) 2_656 . ?
O61 Ce01 N11 66.2(3) . . ?
O51 Ce01 N11 114.63(14) . . ?
O51 Ce01 N11 99.97(13) 2_656 . ?
O61A Ce01 N11 68.1(3) 2_656 . ?
O61A Ce01 N11 74.2(2) . . ?
O52 Ce01 N11 159.61(14) . . ?
O52 Ce01 N11 61.46(13) 2_656 . ?
O61 Ce01 N11 66.2(3) 2_656 2_656 ?
O61 Ce01 N11 76.3(3) . 2_656 ?
O51 Ce01 N11 99.97(13) . 2_656 ?
O51 Ce01 N11 114.64(14) 2_656 2_656 ?
O61A Ce01 N11 74.2(2) 2_656 2_656 ?
O61A Ce01 N11 68.1(3) . 2_656 ?
O52 Ce01 N11 61.46(13) . 2_656 ?
O52 Ce01 N11 159.61(14) 2_656 2_656 ?
N11 Ce01 N11 138.8(2) . 2_656 ?
O61 Ce01 N13 107.51(19) 2_656 2_656 ?
O61 Ce01 N13 60.92(18) . 2_656 ?
O51 Ce01 N13 71.92(13) . 2_656 ?
O51 Ce01 N13 118.73(13) 2_656 2_656 ?
O61A Ce01 N13 102.95(19) 2_656 2_656 ?
O61A Ce01 N13 65.8(2) . 2_656 ?
O52 Ce01 N13 113.06(13) . 2_656 ?
O52 Ce01 N13 74.99(13) 2_656 2_656 ?
N11 Ce01 N13 60.38(13) . 2_656 ?
N11 Ce01 N13 115.00(14) 2_656 2_656 ?
O61 Ce01 N13 60.92(18) 2_656 . ?
O61 Ce01 N13 107.51(19) . . ?
O51 Ce01 N13 118.73(14) . . ?
O51 Ce01 N13 71.92(13) 2_656 . ?
O61A Ce01 N13 65.8(2) 2_656 . ?
O61A Ce01 N13 102.95(19) . . ?
O52 Ce01 N13 74.99(13) . . ?
O52 Ce01 N13 113.06(13) 2_656 . ?
N11 Ce01 N13 115.01(14) . . ?
N11 Ce01 N13 60.38(13) 2_656 . ?
N13 Ce01 N13 168.33(19) 2_656 . ?
N51 O52 Ce01 96.3(3) . . ?
O53 N51 O52 122.4(5) . . ?
O53 N51 O51 119.8(5) . . ?
O52 N51 O51 117.8(5) . . ?
C11 N11 C15 118.5(5) . . ?
C11 N11 Ce01 121.4(3) . . ?
C15 N11 Ce01 120.1(4) . . ?
N11 C11 C12 123.3(5) . . ?
N11 C11 C23 116.6(6) . 2_656 ?
C12 C11 C23 120.0(6) . 2_656 ?
C16 N12 C17 119.9(5) . . ?
C16 N12 Ce01 119.4(4) . . ?
C17 N12 Ce01 120.1(3) . . ?
C11 C12 C13 117.7(7) . . ?
C11 C12 H12A 121.1 . . ?
C13 C12 H12A 121.1 . . ?
C23 N13 C22 117.9(5) . . ?
C23 N13 Ce01 119.5(4) . . ?
C22 N13 Ce01 121.4(4) . . ?
C14 C13 C12 119.7(6) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 119.6(5) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
N11 C15 C14 121.0(6) . . ?
N11 C15 C16 118.2(5) . . ?
C14 C15 C16 120.7(5) . . ?
N12 C16 C15 121.3(5) . . ?
N12 C16 H16A 119.3 . . ?
C15 C16 H16A 119.3 . . ?
C22 C17 C18 119.3(6) . . ?
C22 C17 N12 117.6(5) . . ?
C18 C17 N12 123.1(6) . . ?
C19 C18 C17 119.4(6) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C18 C19 C20 121.4(5) . . ?
C18 C19 H19A 119.3 . . ?
C20 C19 H19A 119.3 . . ?
C19 C20 C21 119.5(6) . . ?
C19 C20 H20A 120.3 . . ?
C21 C20 H20A 120.3 . . ?
C22 C21 C20 120.2(6) . . ?
C22 C21 H21A 119.9 . . ?
C20 C21 H21A 119.9 . . ?
C21 C22 C17 120.2(5) . . ?
C21 C22 N13 123.9(6) . . ?
C17 C22 N13 115.9(6) . . ?
N13 C23 C11 120.9(6) . 2_656 ?
N13 C23 H23 119.6 . . ?
C11 C23 H23 119.6 2_656 . ?
O61 N61 O61 119.3(9) . 2_656 ?
O61 N61 O63 120.4(5) . . ?
O61 N61 O63 120.4(5) 2_656 . ?
O61 N61 Ce01 59.6(5) . . ?
O61 N61 Ce01 59.6(5) 2_656 . ?
O63 N61 Ce01 180.0 . . ?
N61 O61 Ce01 95.9(5) . . ?
N61A N61A O63A 115.3(4) 2_656 . ?
N61A N61A O61A 77.3(14) 2_656 2_656 ?
O63A N61A O61A 120.4(8) . 2_656 ?
N61A N61A O61A 77.0(14) 2_656 . ?
O63A N61A O61A 122.2(9) . . ?
O61A N61A O61A 117.3(7) 2_656 . ?
N61A N61A O63A 45.9(6) 2_656 2_656 ?
O63A N61A O63A 69.4(10) . 2_656 ?
O61A N61A O63A 101.3(7) 2_656 2_656 ?
O61A N61A O63A 99.8(7) . 2_656 ?
N61A O61A N61A 25.7(5) 2_656 . ?
N61A O61A Ce01 95.1(4) 2_656 . ?
N61A O61A Ce01 95.1(4) . . ?
N61A O63A N61A 18.7(3) . 2_656 ?
N61A O63A O63A 64.7(4) . 2_656 ?
N61A O63A O63A 45.9(6) 2_656 2_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
Ce01 O52 N51 O53 -176.5(4) . . . . ?
Ce01 O52 N51 O51 3.7(4) . . . . ?
Ce01 O51 N51 O53 176.4(4) . . . . ?
Ce01 O51 N51 O52 -3.7(4) . . . . ?
C15 N11 C11 C12 0.4(9) . . . . ?
Ce01 N11 C11 C12 180.0(5) . . . . ?
C15 N11 C11 C23 -179.8(5) . . . 2_656 ?
Ce01 N11 C11 C23 -0.3(7) . . . 2_656 ?
N11 C11 C12 C13 1.0(10) . . . . ?
C23 C11 C12 C13 -178.7(6) 2_656 . . . ?
C11 C12 C13 C14 -2.4(10) . . . . ?
C12 C13 C14 C15 2.3(10) . . . . ?
C11 N11 C15 C14 -0.6(9) . . . . ?
Ce01 N11 C15 C14 179.9(4) . . . . ?
C11 N11 C15 C16 176.6(6) . . . . ?
Ce01 N11 C15 C16 -3.0(7) . . . . ?
C13 C14 C15 N11 -0.8(9) . . . . ?
C13 C14 C15 C16 -177.8(6) . . . . ?
C17 N12 C16 C15 -179.5(5) . . . . ?
Ce01 N12 C16 C15 8.8(8) . . . . ?
N11 C15 C16 N12 -4.0(9) . . . . ?
C14 C15 C16 N12 173.1(6) . . . . ?
C16 N12 C17 C22 -149.9(5) . . . . ?
Ce01 N12 C17 C22 21.7(6) . . . . ?
C16 N12 C17 C18 31.2(8) . . . . ?
Ce01 N12 C17 C18 -157.2(4) . . . . ?
C22 C17 C18 C19 2.1(8) . . . . ?
N12 C17 C18 C19 -179.0(5) . . . . ?
C17 C18 C19 C20 -0.8(9) . . . . ?
C18 C19 C20 C21 -1.2(9) . . . . ?
C19 C20 C21 C22 1.9(9) . . . . ?
C20 C21 C22 C17 -0.6(8) . . . . ?
C20 C21 C22 N13 -179.3(5) . . . . ?
C18 C17 C22 C21 -1.4(8) . . . . ?
N12 C17 C22 C21 179.6(5) . . . . ?
C18 C17 C22 N13 177.4(5) . . . . ?
N12 C17 C22 N13 -1.5(7) . . . . ?
C23 N13 C22 C21 -33.4(8) . . . . ?
Ce01 N13 C22 C21 159.1(4) . . . . ?
C23 N13 C22 C17 147.8(6) . . . . ?
Ce01 N13 C22 C17 -19.7(6) . . . . ?
C22 N13 C23 C11 178.6(5) . . . 2_656 ?
Ce01 N13 C23 C11 -13.6(8) . . . 2_656 ?
O61 N61 O61 Ce01 0.000(3) 2_656 . . . ?
O63 N61 O61 Ce01 180.000(2) . . . . ?
O63A N61A O61A N61A 111.9(9) . . . 2_656 ?
O61A N61A O61A N61A -68.1(9) 2_656 . . 2_656 ?
O63A N61A O61A N61A 40.1(8) 2_656 . . 2_656 ?
N61A N61A O61A Ce01 91.3(8) 2_656 . . . ?
O63A N61A O61A Ce01 -156.8(4) . . . . ?
O61A N61A O61A Ce01 23.2(4) 2_656 . . . ?
O63A N61A O61A Ce01 131.4(6) 2_656 . . . ?
O61A N61A O63A N61A 90(2) 2_656 . . 2_656 ?
O61A N61A O63A N61A -90(2) . . . 2_656 ?
O63A N61A O63A N61A -1(2) 2_656 . . 2_656 ?
N61A N61A O63A O63A 1(2) 2_656 . . 2_656 ?
O61A N61A O63A O63A 91.2(7) 2_656 . . 2_656 ?
O61A N61A O63A O63A -88.8(7) . . . 2_656 ?

_refine_diff_density_max         0.980
_refine_diff_density_min         -1.404
_refine_diff_density_rms         0.247



