# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_4
_database_code_depnum_ccdc_archive 'CCDC 1539689'
_audit_update_record             
;
2017-03-22 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 N8 O13 Sm'
_chemical_formula_weight         749.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.9386(3)
_cell_length_b                   11.0774(3)
_cell_length_c                   14.0776(4)
_cell_angle_alpha                84.0560(10)
_cell_angle_beta                 67.7610(10)
_cell_angle_gamma                64.3570(10)
_cell_volume                     1419.69(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8786
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.34

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             750
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.147
_shelx_estimated_absorpt_T_min   0.547
_shelx_estimated_absorpt_T_max   0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21303
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5807
_reflns_number_gt                5080
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0290P)²+0.3366P] 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         5807
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0583
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
Sm1 Sm 0.27845(2) 0.38082(2) 0.36826(2) 0.02015(5) Uani 1 1 d . . . . .
O3 O -0.5294(2) 0.3997(2) 0.41314(19) 0.0417(6) Uani 1 1 d . . . . .
O4 O -0.4549(2) 0.2342(2) 0.30196(16) 0.0297(5) Uani 1 1 d . . . . .
C5 C -0.4285(3) 0.3053(3) 0.3505(2) 0.0250(6) Uani 1 1 d . . . . .
O2 O -0.1494(2) 0.4116(2) 0.53090(16) 0.0277(5) Uani 1 1 d . . . . .
O9 O 0.2448(3) 0.3210(3) 0.54266(19) 0.0452(6) Uani 1 1 d . . . . .
N1 N 0.0932(2) 0.0586(2) 0.14934(18) 0.0231(5) Uani 1 1 d . . . . .
H1N H 0.0704 0.0343 0.1048 0.028 Uiso 1 1 calc R U . . .
N2 N 0.2291(2) 0.0091(2) 0.14004(18) 0.0208(5) Uani 1 1 d . . . . .
O5 O 0.5150(2) -0.1014(2) 0.12319(17) 0.0370(6) Uani 1 1 d . . . . .
O7 O 0.1838(2) -0.0644(2) -0.03074(18) 0.0398(6) Uani 1 1 d . . . . .
O11 O 0.1871(3) 0.5646(3) 0.2529(2) 0.0505(7) Uani 1 1 d . . . . .
O6 O 0.6724(2) -0.2868(2) -0.19445(16) 0.0324(5) Uani 1 1 d . . . . .
O1 O 0.0476(2) 0.3994(2) 0.39680(17) 0.0333(5) Uani 1 1 d . . . . .
C9 C 0.3319(3) -0.0705(3) 0.0586(2) 0.0209(6) Uani 1 1 d . . . . .
N3 N 0.5896(2) -0.2028(2) -0.03198(18) 0.0246(5) Uani 1 1 d . . . . .
H3N H 0.6775 -0.2406 -0.0334 0.029 Uiso 1 1 calc R U . . .
O8 O 0.2929(3) 0.1524(2) 0.3879(2) 0.0428(6) Uani 1 1 d . . . . .
O13 O 1.1164(3) 0.3074(3) 0.0413(2) 0.0514(7) Uani 1 1 d . . . . .
C16 C 0.1644(4) 0.2918(3) 0.6181(3) 0.0401(8) Uani 1 1 d . . . . .
H16 H 0.0648 0.3344 0.6311 0.048 Uiso 1 1 calc R U . . .
N6 N 0.2070(4) 0.2051(3) 0.6825(3) 0.0536(9) Uani 1 1 d . . . . .
C18 C 0.1036(7) 0.1791(5) 0.7738(4) 0.106(2) Uani 1 1 d . . . . .
H18A H 0.0067 0.2473 0.7855 0.159 Uiso 1 1 calc R U . . .
H18B H 0.1283 0.1800 0.8322 0.159 Uiso 1 1 calc R U . . .
H18C H 0.1077 0.0928 0.7638 0.159 Uiso 1 1 calc R U . . .
C17 C 0.3602(6) 0.1298(6) 0.6650(5) 0.095(2) Uani 1 1 d . . . . .
H17A H 0.4165 0.1642 0.6088 0.143 Uiso 1 1 calc R U . . .
H17B H 0.3897 0.0369 0.6485 0.143 Uiso 1 1 calc R U . . .
H17C H 0.3764 0.1381 0.7259 0.143 Uiso 1 1 calc R U . . .
N7 N 0.3040(4) 0.5778(3) 0.2077(3) 0.0538(9) Uani 1 1 d . . . . .
O10 O 0.4090(3) 0.5023(3) 0.2330(3) 0.0648(8) Uani 1 1 d . . . . .
O12 O 0.3138(5) 0.6596(4) 0.1430(3) 0.1006(13) Uani 1 1 d . . . . .
C4 C -0.2732(3) 0.2740(3) 0.3305(2) 0.0204(6) Uani 1 1 d . . . . .
C1 C -0.0636(3) 0.3779(3) 0.4392(2) 0.0202(6) Uani 1 1 d . . . . .
C2 C -0.0974(3) 0.3078(3) 0.3736(2) 0.0182(6) Uani 1 1 d . . . . .
C3 C -0.2421(3) 0.3356(3) 0.3927(2) 0.0203(6) Uani 1 1 d . . . . .
H3 H -0.3174 0.3956 0.4474 0.024 Uiso 1 1 calc R U . . .
C6 C -0.1607(3) 0.1809(3) 0.2499(2) 0.0204(6) Uani 1 1 d . . . . .
H6 H -0.1820 0.1386 0.2086 0.024 Uiso 1 1 calc R U . . .
C7 C -0.0176(3) 0.1523(3) 0.2324(2) 0.0192(6) Uani 1 1 d . . . . .
C10 C 0.4818(3) -0.1236(3) 0.0562(2) 0.0228(6) Uani 1 1 d . . . . .
C11 C 0.5690(3) -0.2259(3) -0.1161(2) 0.0231(6) Uani 1 1 d . . . . .
N4 N 0.4284(3) -0.1783(3) -0.10982(19) 0.0292(6) Uani 1 1 d . . . . .
H4N H 0.4152 -0.1970 -0.1619 0.035 Uiso 1 1 calc R U . . .
C12 C 0.3051(3) -0.1027(3) -0.0272(2) 0.0250(6) Uani 1 1 d . . . . .
C8 C 0.0150(3) 0.2179(3) 0.2918(2) 0.0203(6) Uani 1 1 d . . . . .
H8 H 0.1113 0.2017 0.2771 0.024 Uiso 1 1 calc R U . . .
C13 C 0.3115(4) 0.0466(3) 0.3515(3) 0.0357(8) Uani 1 1 d . . . . .
H13 H 0.3651 0.0245 0.2814 0.043 Uiso 1 1 calc R U . . .
N5 N 0.2605(4) -0.0367(3) 0.4051(2) 0.0494(8) Uani 1 1 d . . . . .
C15 C 0.2904(7) -0.1628(5) 0.3594(4) 0.0864(18) Uani 1 1 d . . . . .
H15A H 0.3470 -0.1704 0.2871 0.130 Uiso 1 1 calc R U . . .
H15B H 0.1999 -0.1655 0.3692 0.130 Uiso 1 1 calc R U . . .
H15C H 0.3441 -0.2360 0.3916 0.130 Uiso 1 1 calc R U . . .
C20 C 0.7546(5) 0.5553(4) 0.1773(4) 0.0769(15) Uani 1 1 d . . . . .
H20A H 0.7900 0.5786 0.2221 0.115 Uiso 1 1 calc R U . . .
H20B H 0.6772 0.5302 0.2174 0.115 Uiso 1 1 calc R U . . .
H20C H 0.7184 0.6310 0.1396 0.115 Uiso 1 1 calc R U . . .
N8 N 0.8730(3) 0.4432(3) 0.1057(3) 0.0484(8) Uani 1 1 d . . . . .
C19 C 1.0085(4) 0.3988(4) 0.1006(3) 0.0483(10) Uani 1 1 d . . . . .
H19 H 1.0239 0.4406 0.1462 0.058 Uiso 1 1 calc R U . . .
C21 C 0.8375(5) 0.3863(5) 0.0389(4) 0.0729(14) Uani 1 1 d . . . . .
H21A H 0.8092 0.4503 -0.0090 0.109 Uiso 1 1 calc R U . . .
H21B H 0.7582 0.3636 0.0788 0.109 Uiso 1 1 calc R U . . .
H21C H 0.9213 0.3068 0.0018 0.109 Uiso 1 1 calc R U . . .
C14 C 0.1735(8) -0.0022(6) 0.5144(4) 0.104(2) Uani 1 1 d . . . . .
H14A H 0.1210 -0.0567 0.5392 0.156 Uiso 1 1 calc R U . . .
H14B H 0.1055 0.0908 0.5249 0.156 Uiso 1 1 calc R U . . .
H14C H 0.2366 -0.0181 0.5511 0.156 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
Sm1 O1 2.3188(19) . ?
Sm1 O2 2.3758(19) 2_566 ?
Sm1 O9 2.407(2) . ?
Sm1 O8 2.459(2) . ?
Sm1 O4 2.4842(19) 1_655 ?
Sm1 O3 2.505(2) 1_655 ?
Sm1 O6 2.531(2) 2_655 ?
Sm1 O10 2.560(3) . ?
Sm1 O11 2.562(3) . ?
Sm1 C5 2.855(3) 1_655 ?
Sm1 N7 2.996(3) . ?
O3 C5 1.243(3) . ?
O3 Sm1 2.505(2) 1_455 ?
O4 C5 1.276(3) . ?
O4 Sm1 2.4842(19) 1_455 ?
C5 C4 1.495(4) . ?
C5 Sm1 2.856(3) 1_455 ?
O2 C1 1.251(3) . ?
O2 Sm1 2.3758(19) 2_566 ?
O9 C16 1.214(4) . ?
N1 N2 1.300(3) . ?
N1 C7 1.415(3) . ?
N1 H1N 0.8600 . ?
N2 C9 1.316(3) . ?
O5 C10 1.211(3) . ?
O7 C12 1.225(3) . ?
O11 N7 1.260(4) . ?
O6 C11 1.225(3) . ?
O6 Sm1 2.531(2) 2_655 ?
O1 C1 1.251(3) . ?
C9 C12 1.457(4) . ?
C9 C10 1.471(4) . ?
N3 C11 1.354(4) . ?
N3 C10 1.387(3) . ?
N3 H3N 0.8600 . ?
O8 C13 1.231(4) . ?
O13 C19 1.229(5) . ?
C16 N6 1.310(5) . ?
C16 H16 0.9300 . ?
N6 C17 1.444(6) . ?
N6 C18 1.455(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N7 O12 1.226(4) . ?
N7 O10 1.249(4) . ?
C4 C3 1.378(4) . ?
C4 C6 1.398(4) . ?
C1 C2 1.500(4) . ?
C2 C8 1.391(4) . ?
C2 C3 1.394(4) . ?
C3 H3 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(4) . ?
C11 N4 1.363(4) . ?
N4 C12 1.382(3) . ?
N4 H4N 0.8600 . ?
C8 H8 0.9300 . ?
C13 N5 1.309(5) . ?
C13 H13 0.9300 . ?
N5 C15 1.451(5) . ?
N5 C14 1.455(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C20 N8 1.454(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N8 C19 1.320(5) . ?
N8 C21 1.430(6) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sm1 O2 84.52(7) . 2_566 ?
O1 Sm1 O9 89.05(9) . . ?
O2 Sm1 O9 74.82(8) 2_566 . ?
O1 Sm1 O8 73.40(8) . . ?
O2 Sm1 O8 137.61(8) 2_566 . ?
O9 Sm1 O8 69.20(9) . . ?
O1 Sm1 O4 146.29(7) . 1_655 ?
O2 Sm1 O4 128.56(7) 2_566 1_655 ?
O9 Sm1 O4 93.59(8) . 1_655 ?
O8 Sm1 O4 76.21(8) . 1_655 ?
O1 Sm1 O3 156.16(7) . 1_655 ?
O2 Sm1 O3 76.93(7) 2_566 1_655 ?
O9 Sm1 O3 71.85(9) . 1_655 ?
O8 Sm1 O3 111.04(8) . 1_655 ?
O4 Sm1 O3 52.16(6) 1_655 1_655 ?
O1 Sm1 O6 80.63(7) . 2_655 ?
O2 Sm1 O6 139.81(7) 2_566 2_655 ?
O9 Sm1 O6 141.39(8) . 2_655 ?
O8 Sm1 O6 72.19(8) . 2_655 ?
O4 Sm1 O6 76.46(6) 1_655 2_655 ?
O3 Sm1 O6 123.19(7) 1_655 2_655 ?
O1 Sm1 O10 124.75(9) . . ?
O2 Sm1 O10 85.27(9) 2_566 . ?
O9 Sm1 O10 139.05(10) . . ?
O8 Sm1 O10 137.02(10) . . ?
O4 Sm1 O10 71.33(9) 1_655 . ?
O3 Sm1 O10 68.92(10) 1_655 . ?
O6 Sm1 O10 73.39(9) 2_655 . ?
O1 Sm1 O11 76.11(9) . . ?
O2 Sm1 O11 72.87(8) 2_566 . ?
O9 Sm1 O11 145.46(8) . . ?
O8 Sm1 O11 132.36(9) . . ?
O4 Sm1 O11 116.07(8) 1_655 . ?
O3 Sm1 O11 111.68(9) 1_655 . ?
O6 Sm1 O11 67.38(8) 2_655 . ?
O10 Sm1 O11 49.05(9) . . ?
O1 Sm1 C5 168.15(9) . 1_655 ?
O2 Sm1 C5 102.18(7) 2_566 1_655 ?
O9 Sm1 C5 83.39(9) . 1_655 ?
O8 Sm1 C5 95.33(9) . 1_655 ?
O4 Sm1 C5 26.50(7) 1_655 1_655 ?
O3 Sm1 C5 25.76(7) 1_655 1_655 ?
O6 Sm1 C5 99.66(7) 2_655 1_655 ?
O10 Sm1 C5 66.08(9) . 1_655 ?
O11 Sm1 C5 115.07(9) . 1_655 ?
O1 Sm1 N7 100.60(10) . . ?
O2 Sm1 N7 77.84(8) 2_566 . ?
O9 Sm1 N7 149.95(9) . . ?
O8 Sm1 N7 140.81(9) . . ?
O4 Sm1 N7 93.74(9) 1_655 . ?
O3 Sm1 N7 90.08(10) 1_655 . ?
O6 Sm1 N7 68.63(8) 2_655 . ?
O10 Sm1 N7 24.40(9) . . ?
O11 Sm1 N7 24.65(9) . . ?
C5 Sm1 N7 90.43(10) 1_655 . ?
C5 O3 Sm1 93.07(17) . 1_455 ?
C5 O4 Sm1 93.21(16) . 1_455 ?
O3 C5 O4 121.1(3) . . ?
O3 C5 C4 120.0(2) . . ?
O4 C5 C4 118.9(2) . . ?
O3 C5 Sm1 61.16(15) . 1_455 ?
O4 C5 Sm1 60.30(14) . 1_455 ?
C4 C5 Sm1 173.7(2) . 1_455 ?
C1 O2 Sm1 132.88(19) . 2_566 ?
C16 O9 Sm1 142.8(2) . . ?
N2 N1 C7 120.4(2) . . ?
N2 N1 H1N 119.8 . . ?
C7 N1 H1N 119.8 . . ?
N1 N2 C9 119.7(2) . . ?
N7 O11 Sm1 97.3(2) . . ?
C11 O6 Sm1 139.61(19) . 2_655 ?
C1 O1 Sm1 156.5(2) . . ?
N2 C9 C12 124.1(2) . . ?
N2 C9 C10 115.6(2) . . ?
C12 C9 C10 120.2(2) . . ?
C11 N3 C10 125.9(2) . . ?
C11 N3 H3N 117.1 . . ?
C10 N3 H3N 117.1 . . ?
C13 O8 Sm1 150.8(2) . . ?
O9 C16 N6 125.1(4) . . ?
O9 C16 H16 117.5 . . ?
N6 C16 H16 117.5 . . ?
C16 N6 C17 120.9(4) . . ?
C16 N6 C18 122.0(4) . . ?
C17 N6 C18 117.0(4) . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N6 C17 H17A 109.5 . . ?
N6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O12 N7 O10 122.2(4) . . ?
O12 N7 O11 121.9(4) . . ?
O10 N7 O11 115.8(3) . . ?
O12 N7 Sm1 179.2(3) . . ?
O10 N7 Sm1 57.83(19) . . ?
O11 N7 Sm1 58.01(18) . . ?
N7 O10 Sm1 97.8(2) . . ?
C3 C4 C6 120.6(2) . . ?
C3 C4 C5 119.8(2) . . ?
C6 C4 C5 119.6(2) . . ?
O1 C1 O2 125.5(3) . . ?
O1 C1 C2 116.8(2) . . ?
O2 C1 C2 117.7(2) . . ?
C8 C2 C3 119.9(2) . . ?
C8 C2 C1 120.1(2) . . ?
C3 C2 C1 120.0(2) . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C7 C6 C4 119.2(2) . . ?
C7 C6 H6 120.4 . . ?
C4 C6 H6 120.4 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 N1 117.5(2) . . ?
C8 C7 N1 121.7(2) . . ?
O5 C10 N3 119.9(3) . . ?
O5 C10 C9 125.1(2) . . ?
N3 C10 C9 115.1(2) . . ?
O6 C11 N3 121.4(3) . . ?
O6 C11 N4 121.5(3) . . ?
N3 C11 N4 117.1(2) . . ?
C11 N4 C12 125.8(2) . . ?
C11 N4 H4N 117.1 . . ?
C12 N4 H4N 117.1 . . ?
O7 C12 N4 120.0(3) . . ?
O7 C12 C9 124.4(3) . . ?
N4 C12 C9 115.5(2) . . ?
C7 C8 C2 119.6(2) . . ?
C7 C8 H8 120.2 . . ?
C2 C8 H8 120.2 . . ?
O8 C13 N5 124.2(3) . . ?
O8 C13 H13 117.9 . . ?
N5 C13 H13 117.9 . . ?
C13 N5 C15 122.1(3) . . ?
C13 N5 C14 118.7(3) . . ?
C15 N5 C14 119.2(4) . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 N8 C21 121.4(4) . . ?
C19 N8 C20 121.1(4) . . ?
C21 N8 C20 117.4(4) . . ?
O13 C19 N8 126.1(4) . . ?
O13 C19 H19 116.9 . . ?
N8 C19 H19 116.9 . . ?
N8 C21 H21A 109.5 . . ?
N8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sm1 O3 C5 O4 -6.9(3) 1_455 . . . ?
Sm1 O3 C5 C4 172.8(3) 1_455 . . . ?
Sm1 O4 C5 O3 7.0(3) 1_455 . . . ?
Sm1 O4 C5 C4 -172.8(2) 1_455 . . . ?
C7 N1 N2 C9 -175.2(3) . . . . ?
N1 N2 C9 C12 3.5(4) . . . . ?
N1 N2 C9 C10 -178.8(3) . . . . ?
Sm1 O9 C16 N6 144.5(3) . . . . ?
O9 C16 N6 C17 -3.1(6) . . . . ?
O9 C16 N6 C18 177.5(5) . . . . ?
Sm1 O11 N7 O12 -179.1(4) . . . . ?
Sm1 O11 N7 O10 1.0(4) . . . . ?
O12 N7 O10 Sm1 179.1(4) . . . . ?
O11 N7 O10 Sm1 -1.0(4) . . . . ?
O3 C5 C4 C3 10.0(5) . . . . ?
O4 C5 C4 C3 -170.2(3) . . . . ?
O3 C5 C4 C6 -170.9(3) . . . . ?
O4 C5 C4 C6 8.8(4) . . . . ?
Sm1 O1 C1 O2 64.6(6) . . . . ?
Sm1 O1 C1 C2 -116.6(4) . . . . ?
Sm1 O2 C1 O1 52.2(4) 2_566 . . . ?
Sm1 O2 C1 C2 -126.7(2) 2_566 . . . ?
O1 C1 C2 C8 29.6(4) . . . . ?
O2 C1 C2 C8 -151.4(3) . . . . ?
O1 C1 C2 C3 -148.6(3) . . . . ?
O2 C1 C2 C3 30.4(4) . . . . ?
C6 C4 C3 C2 1.8(4) . . . . ?
C5 C4 C3 C2 -179.2(3) . . . . ?
C8 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 178.2(3) . . . . ?
C3 C4 C6 C7 -0.8(4) . . . . ?
C5 C4 C6 C7 -179.8(3) . . . . ?
C4 C6 C7 C8 -1.9(4) . . . . ?
C4 C6 C7 N1 -179.3(3) . . . . ?
N2 N1 C7 C6 -167.4(3) . . . . ?
N2 N1 C7 C8 15.2(4) . . . . ?
C11 N3 C10 O5 -173.9(3) . . . . ?
C11 N3 C10 C9 5.0(4) . . . . ?
N2 C9 C10 O5 1.4(5) . . . . ?
C12 C9 C10 O5 179.3(3) . . . . ?
N2 C9 C10 N3 -177.4(3) . . . . ?
C12 C9 C10 N3 0.4(4) . . . . ?
Sm1 O6 C11 N3 174.0(2) 2_655 . . . ?
Sm1 O6 C11 N4 -6.1(5) 2_655 . . . ?
C10 N3 C11 O6 173.0(3) . . . . ?
C10 N3 C11 N4 -7.0(5) . . . . ?
O6 C11 N4 C12 -176.5(3) . . . . ?
N3 C11 N4 C12 3.5(5) . . . . ?
C11 N4 C12 O7 179.4(3) . . . . ?
C11 N4 C12 C9 1.4(5) . . . . ?
N2 C9 C12 O7 -3.5(5) . . . . ?
C10 C9 C12 O7 178.8(3) . . . . ?
N2 C9 C12 N4 174.4(3) . . . . ?
C10 C9 C12 N4 -3.2(4) . . . . ?
C6 C7 C8 C2 3.6(4) . . . . ?
N1 C7 C8 C2 -179.1(3) . . . . ?
C3 C2 C8 C7 -2.6(4) . . . . ?
C1 C2 C8 C7 179.2(3) . . . . ?
Sm1 O8 C13 N5 -156.0(3) . . . . ?
O8 C13 N5 C15 -177.4(4) . . . . ?
O8 C13 N5 C14 1.4(6) . . . . ?
C21 N8 C19 O13 -0.3(6) . . . . ?
C20 N8 C19 O13 -178.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O7 0.86 1.96 2.629(3) 133.8 .
N3 H3N O13 0.86 2.01 2.862(3) 173.0 2_755
C16 H16 O11 0.93 2.41 3.261(5) 151.8 2_566
C18 H18A O11 0.96 2.44 3.344(6) 157.4 2_566
N4 H4N O4 0.86 1.90 2.717(3) 158.2 2
C13 H13 O5 0.93 2.34 3.239(4) 161.3 .
C15 H15A O5 0.96 2.63 3.514(6) 153.0 .

_refine_diff_density_max         0.788
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.107

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1539688'
_audit_update_record             
;
2017-03-22 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 N8 Nd O13'
_chemical_formula_weight         743.74

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.9927(3)
_cell_length_b                   11.1065(3)
_cell_length_c                   14.1247(4)
_cell_angle_alpha                84.0120(10)
_cell_angle_beta                 67.888(2)
_cell_angle_gamma                64.1610(10)
_cell_volume                     1434.23(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.02

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_F_000             746
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.888
_shelx_estimated_absorpt_T_min   0.558
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20942
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.658
_diffrn_reflns_theta_max         26.054
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5653
_reflns_number_gt                5223
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0365P)²+1.4986P] 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         5653
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0631
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
Nd1 Nd 0.27884(2) 0.38066(2) 0.36819(2) 0.02264(6) Uani 1 1 d . . . . .
O3 O 0.8515(2) 0.4098(2) 0.52949(15) 0.0318(4) Uani 1 1 d . . . . .
O4 O 1.0469(2) 0.3987(2) 0.39634(17) 0.0373(5) Uani 1 1 d . . . . .
C5 C 0.9365(3) 0.3771(3) 0.4382(2) 0.0235(5) Uani 1 1 d . . . . .
O8 O 0.2948(3) 0.1502(2) 0.3871(2) 0.0487(6) Uani 1 1 d . . . . .
O1 O 0.5484(2) 0.2335(2) 0.29990(15) 0.0318(4) Uani 1 1 d . . . . .
C8 C 0.8405(3) 0.1803(3) 0.2489(2) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.8196 0.1382 0.2076 0.028 Uiso 1 1 calc R U . . .
N1 N 1.0936(2) 0.0588(2) 0.14883(17) 0.0261(5) Uani 1 1 d . . . . .
H1N H 1.0711 0.0346 0.1043 0.031 Uiso 1 1 calc R U . . .
N2 N 1.2290(2) 0.0095(2) 0.13995(16) 0.0240(5) Uani 1 1 d . . . . .
O7 O 1.5138(2) -0.1005(2) 0.12368(16) 0.0405(5) Uani 1 1 d . . . . .
O5 O 1.1846(2) -0.0641(2) -0.03051(17) 0.0431(6) Uani 1 1 d . . . . .
C6 C 1.0155(3) 0.2174(3) 0.29113(19) 0.0224(5) Uani 1 1 d . . . . .
H6 H 1.1113 0.2013 0.2768 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9031(3) 0.3070(2) 0.37237(19) 0.0206(5) Uani 1 1 d . . . . .
O2 O 0.4735(2) 0.3964(3) 0.41335(18) 0.0461(6) Uani 1 1 d . . . . .
C7 C 0.9834(3) 0.1521(3) 0.23152(19) 0.0222(5) Uani 1 1 d . . . . .
C9 C 1.3315(3) -0.0699(3) 0.05866(19) 0.0233(5) Uani 1 1 d . . . . .
N3 N 1.4276(2) -0.1778(3) -0.10879(18) 0.0328(6) Uani 1 1 d . . . . .
H3N H 1.4145 -0.1968 -0.1606 0.039 Uiso 1 1 calc R U . . .
O6 O 1.6708(2) -0.2861(2) -0.19283(15) 0.0364(5) Uani 1 1 d . . . . .
N8 N 0.8754(3) 0.4414(3) 0.1043(3) 0.0542(8) Uani 1 1 d . . . . .
C13 C 0.3110(4) 0.0461(3) 0.3515(2) 0.0383(7) Uani 1 1 d . . . . .
H13 H 0.3628 0.0245 0.2815 0.046 Uiso 1 1 calc R U . . .
N5 N 0.2607(4) -0.0368(3) 0.4049(2) 0.0570(9) Uani 1 1 d . . . . .
C14 C 0.2897(8) -0.1623(5) 0.3598(4) 0.096(2) Uani 1 1 d . . . . .
H14A H 0.3402 -0.1675 0.2871 0.144 Uiso 1 1 calc R U . . .
H14B H 0.1995 -0.1670 0.3736 0.144 Uiso 1 1 calc R U . . .
H14C H 0.3487 -0.2357 0.3888 0.144 Uiso 1 1 calc R U . . .
C15 C 0.1739(9) -0.0019(6) 0.5139(4) 0.118(3) Uani 1 1 d . . . . .
H15A H 0.2370 -0.0202 0.5508 0.177 Uiso 1 1 calc R U . . .
H15B H 0.1194 -0.0542 0.5383 0.177 Uiso 1 1 calc R U . . .
H15C H 0.1082 0.0917 0.5243 0.177 Uiso 1 1 calc R U . . .
O11 O 0.1875(3) 0.5663(3) 0.2522(2) 0.0560(7) Uani 1 1 d . . . . .
N7 N 0.3035(4) 0.5797(3) 0.2076(3) 0.0602(9) Uani 1 1 d . . . . .
O12 O 0.3119(5) 0.6615(4) 0.1428(3) 0.1112(15) Uani 1 1 d . . . . .
O10 O 0.4080(3) 0.5051(3) 0.2328(3) 0.0694(8) Uani 1 1 d . . . . .
C1 C 0.5735(3) 0.3039(3) 0.3492(2) 0.0273(6) Uani 1 1 d . . . . .
C2 C 0.7284(3) 0.2728(3) 0.3293(2) 0.0236(5) Uani 1 1 d . . . . .
C10 C 1.4811(3) -0.1230(3) 0.0568(2) 0.0259(5) Uani 1 1 d . . . . .
N4 N 1.5884(2) -0.2019(2) -0.03085(17) 0.0265(5) Uani 1 1 d . . . . .
H4N H 1.6760 -0.2395 -0.0323 0.032 Uiso 1 1 calc R U . . .
C11 C 1.5676(3) -0.2251(3) -0.1148(2) 0.0272(6) Uani 1 1 d . . . . .
C12 C 1.3053(3) -0.1024(3) -0.0270(2) 0.0286(6) Uani 1 1 d . . . . .
C3 C 0.7591(3) 0.3348(3) 0.39164(19) 0.0226(5) Uani 1 1 d . . . . .
H3 H 0.6841 0.3947 0.4461 0.027 Uiso 1 1 calc R U . . .
O9 O 0.2440(3) 0.3204(3) 0.54451(18) 0.0497(6) Uani 1 1 d . . . . .
C16 C 0.1646(4) 0.2908(3) 0.6200(3) 0.0439(8) Uani 1 1 d . . . . .
H16 H 0.0653 0.3336 0.6333 0.053 Uiso 1 1 calc R U . . .
N6 N 0.2070(4) 0.2042(3) 0.6839(3) 0.0603(9) Uani 1 1 d . . . . .
C17 C 0.3591(6) 0.1303(6) 0.6669(5) 0.104(2) Uani 1 1 d . . . . .
H17A H 0.4127 0.1742 0.6193 0.156 Uiso 1 1 calc R U . . .
H17B H 0.3934 0.0410 0.6395 0.156 Uiso 1 1 calc R U . . .
H17C H 0.3726 0.1265 0.7307 0.156 Uiso 1 1 calc R U . . .
O13 O 1.1181(3) 0.3062(3) 0.0404(2) 0.0557(7) Uani 1 1 d . . . . .
C19 C 1.0110(4) 0.3973(4) 0.0993(3) 0.0532(9) Uani 1 1 d . . . . .
H19 H 1.0262 0.4393 0.1446 0.064 Uiso 1 1 calc R U . . .
C20 C 0.7573(5) 0.5532(5) 0.1762(4) 0.0829(16) Uani 1 1 d . . . . .
H20A H 0.7936 0.5781 0.2193 0.124 Uiso 1 1 calc R U . . .
H20B H 0.6821 0.5270 0.2176 0.124 Uiso 1 1 calc R U . . .
H20C H 0.7184 0.6283 0.1389 0.124 Uiso 1 1 calc R U . . .
C21 C 0.8404(6) 0.3854(5) 0.0386(4) 0.0777(14) Uani 1 1 d . . . . .
H21A H 0.9242 0.3065 0.0012 0.117 Uiso 1 1 calc R U . . .
H21B H 0.8108 0.4497 -0.0086 0.117 Uiso 1 1 calc R U . . .
H21C H 0.7624 0.3619 0.0785 0.117 Uiso 1 1 calc R U . . .
C18 C 0.1047(8) 0.1773(6) 0.7745(5) 0.123(3) Uani 1 1 d . . . . .
H18A H 0.0073 0.2413 0.7834 0.184 Uiso 1 1 calc R U . . .
H18B H 0.1249 0.1846 0.8336 0.184 Uiso 1 1 calc R U . . .
H18C H 0.1146 0.0884 0.7662 0.184 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
Nd1 O4 2.3470(19) 1_455 ?
Nd1 O3 2.4069(18) 2_666 ?
Nd1 O9 2.440(2) . ?
Nd1 O8 2.481(2) . ?
Nd1 O1 2.5172(19) . ?
Nd1 O2 2.528(2) . ?
Nd1 O6 2.5589(19) 2_755 ?
Nd1 O11 2.584(3) . ?
Nd1 O10 2.588(3) . ?
Nd1 C1 2.877(3) . ?
O3 C5 1.250(3) . ?
O3 Nd1 2.4069(18) 2_666 ?
O4 C5 1.250(3) . ?
O4 Nd1 2.3471(19) 1_655 ?
C5 C4 1.504(3) . ?
O8 C13 1.223(4) . ?
O1 C1 1.272(3) . ?
C8 C7 1.386(3) . ?
C8 C2 1.396(4) . ?
C8 H8 0.9300 . ?
N1 N2 1.301(3) . ?
N1 C7 1.414(3) . ?
N1 H1N 0.8600 . ?
N2 C9 1.317(3) . ?
O7 C10 1.211(3) . ?
O5 C12 1.224(3) . ?
C6 C4 1.390(3) . ?
C6 C7 1.390(4) . ?
C6 H6 0.9300 . ?
C4 C3 1.393(3) . ?
O2 C1 1.244(3) . ?
C9 C12 1.456(4) . ?
C9 C10 1.477(4) . ?
N3 C11 1.364(4) . ?
N3 C12 1.376(3) . ?
N3 H3N 0.8600 . ?
O6 C11 1.227(3) . ?
O6 Nd1 2.5590(19) 2_755 ?
N8 C19 1.327(5) . ?
N8 C21 1.412(6) . ?
N8 C20 1.457(5) . ?
C13 N5 1.308(4) . ?
C13 H13 0.9300 . ?
N5 C14 1.447(5) . ?
N5 C15 1.458(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O11 N7 1.260(4) . ?
N7 O12 1.228(4) . ?
N7 O10 1.245(5) . ?
C1 C2 1.498(3) . ?
C2 C3 1.385(4) . ?
C10 N4 1.385(3) . ?
N4 C11 1.358(4) . ?
N4 H4N 0.8600 . ?
C3 H3 0.9300 . ?
O9 C16 1.218(4) . ?
C16 N6 1.304(5) . ?
C16 H16 0.9300 . ?
N6 C17 1.438(6) . ?
N6 C18 1.457(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O13 C19 1.225(5) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Nd1 O3 84.82(7) 1_455 2_666 ?
O4 Nd1 O9 88.80(8) 1_455 . ?
O3 Nd1 O9 74.47(8) 2_666 . ?
O4 Nd1 O8 73.28(8) 1_455 . ?
O3 Nd1 O8 137.66(8) 2_666 . ?
O9 Nd1 O8 69.40(9) . . ?
O4 Nd1 O1 146.22(7) 1_455 . ?
O3 Nd1 O1 128.43(6) 2_666 . ?
O9 Nd1 O1 94.44(8) . . ?
O8 Nd1 O1 76.48(8) . . ?
O4 Nd1 O2 156.60(7) 1_455 . ?
O3 Nd1 O2 77.43(7) 2_666 . ?
O9 Nd1 O2 71.93(9) . . ?
O8 Nd1 O2 110.38(8) . . ?
O1 Nd1 O2 51.66(6) . . ?
O4 Nd1 O6 80.68(7) 1_455 2_755 ?
O3 Nd1 O6 140.06(7) 2_666 2_755 ?
O9 Nd1 O6 141.51(8) . 2_755 ?
O8 Nd1 O6 72.11(8) . 2_755 ?
O1 Nd1 O6 75.98(6) . 2_755 ?
O2 Nd1 O6 122.68(6) . 2_755 ?
O4 Nd1 O11 76.48(9) 1_455 . ?
O3 Nd1 O11 73.05(8) 2_666 . ?
O9 Nd1 O11 145.30(8) . . ?
O8 Nd1 O11 132.47(9) . . ?
O1 Nd1 O11 115.28(8) . . ?
O2 Nd1 O11 111.95(9) . . ?
O6 Nd1 O11 67.44(8) 2_755 . ?
O4 Nd1 O10 124.63(9) 1_455 . ?
O3 Nd1 O10 85.00(9) 2_666 . ?
O9 Nd1 O10 139.13(10) . . ?
O8 Nd1 O10 137.22(10) . . ?
O1 Nd1 O10 71.14(9) . . ?
O2 Nd1 O10 69.27(9) . . ?
O6 Nd1 O10 73.48(9) 2_755 . ?
O11 Nd1 O10 48.54(9) . . ?
O4 Nd1 C1 168.03(8) 1_455 . ?
O3 Nd1 C1 102.37(7) 2_666 . ?
O9 Nd1 C1 84.02(8) . . ?
O8 Nd1 C1 95.18(8) . . ?
O1 Nd1 C1 26.20(7) . . ?
O2 Nd1 C1 25.57(7) . . ?
O6 Nd1 C1 99.07(7) 2_755 . ?
O11 Nd1 C1 114.61(9) . . ?
O10 Nd1 C1 66.11(9) . . ?
C5 O3 Nd1 132.62(18) . 2_666 ?
C5 O4 Nd1 156.7(2) . 1_655 ?
O3 C5 O4 125.5(2) . . ?
O3 C5 C4 117.6(2) . . ?
O4 C5 C4 116.9(2) . . ?
C13 O8 Nd1 151.0(2) . . ?
C1 O1 Nd1 92.90(15) . . ?
C7 C8 C2 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
C2 C8 H8 120.4 . . ?
N2 N1 C7 120.2(2) . . ?
N2 N1 H1N 119.9 . . ?
C7 N1 H1N 119.9 . . ?
N1 N2 C9 119.5(2) . . ?
C4 C6 C7 119.4(2) . . ?
C4 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C4 C3 120.3(2) . . ?
C6 C4 C5 119.9(2) . . ?
C3 C4 C5 119.7(2) . . ?
C1 O2 Nd1 93.11(16) . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 N1 117.4(2) . . ?
C6 C7 N1 121.7(2) . . ?
N2 C9 C12 124.3(2) . . ?
N2 C9 C10 115.4(2) . . ?
C12 C9 C10 120.3(2) . . ?
C11 N3 C12 125.7(2) . . ?
C11 N3 H3N 117.2 . . ?
C12 N3 H3N 117.2 . . ?
C11 O6 Nd1 139.75(19) . 2_755 ?
C19 N8 C21 121.7(4) . . ?
C19 N8 C20 120.7(4) . . ?
C21 N8 C20 117.5(4) . . ?
O8 C13 N5 124.5(3) . . ?
O8 C13 H13 117.8 . . ?
N5 C13 H13 117.8 . . ?
C13 N5 C14 122.2(3) . . ?
C13 N5 C15 118.6(3) . . ?
C14 N5 C15 119.2(4) . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N7 O11 Nd1 97.5(2) . . ?
O12 N7 O10 122.5(4) . . ?
O12 N7 O11 121.3(4) . . ?
O10 N7 O11 116.2(3) . . ?
N7 O10 Nd1 97.8(2) . . ?
O2 C1 O1 121.8(2) . . ?
O2 C1 C2 119.6(2) . . ?
O1 C1 C2 118.6(2) . . ?
O2 C1 Nd1 61.33(14) . . ?
O1 C1 Nd1 60.90(13) . . ?
C2 C1 Nd1 173.8(2) . . ?
C3 C2 C8 120.6(2) . . ?
C3 C2 C1 119.7(2) . . ?
C8 C2 C1 119.8(2) . . ?
O7 C10 N4 120.1(2) . . ?
O7 C10 C9 125.1(2) . . ?
N4 C10 C9 114.8(2) . . ?
C11 N4 C10 125.9(2) . . ?
C11 N4 H4N 117.1 . . ?
C10 N4 H4N 117.1 . . ?
O6 C11 N4 121.3(3) . . ?
O6 C11 N3 121.4(3) . . ?
N4 C11 N3 117.3(2) . . ?
O5 C12 N3 120.1(3) . . ?
O5 C12 C9 124.2(2) . . ?
N3 C12 C9 115.7(2) . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C16 O9 Nd1 143.5(2) . . ?
O9 C16 N6 125.6(4) . . ?
O9 C16 H16 117.2 . . ?
N6 C16 H16 117.2 . . ?
C16 N6 C17 120.7(4) . . ?
C16 N6 C18 122.3(4) . . ?
C17 N6 C18 117.0(4) . . ?
N6 C17 H17A 109.5 . . ?
N6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O13 C19 N8 125.9(4) . . ?
O13 C19 H19 117.1 . . ?
N8 C19 H19 117.1 . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C21 H21A 109.5 . . ?
N8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Nd1 O3 C5 O4 52.4(4) 2_666 . . . ?
Nd1 O3 C5 C4 -127.0(2) 2_666 . . . ?
Nd1 O4 C5 O3 63.8(6) 1_655 . . . ?
Nd1 O4 C5 C4 -116.8(4) 1_655 . . . ?
C7 N1 N2 C9 -175.1(2) . . . . ?
C7 C6 C4 C3 -2.3(4) . . . . ?
C7 C6 C4 C5 179.3(2) . . . . ?
O3 C5 C4 C6 -151.0(3) . . . . ?
O4 C5 C4 C6 29.6(4) . . . . ?
O3 C5 C4 C3 30.6(4) . . . . ?
O4 C5 C4 C3 -148.8(3) . . . . ?
C2 C8 C7 C6 -1.8(4) . . . . ?
C2 C8 C7 N1 -179.5(2) . . . . ?
C4 C6 C7 C8 3.2(4) . . . . ?
C4 C6 C7 N1 -179.2(2) . . . . ?
N2 N1 C7 C8 -167.2(2) . . . . ?
N2 N1 C7 C6 15.1(4) . . . . ?
N1 N2 C9 C12 3.3(4) . . . . ?
N1 N2 C9 C10 -178.7(2) . . . . ?
Nd1 O8 C13 N5 -154.6(4) . . . . ?
O8 C13 N5 C14 -176.6(5) . . . . ?
O8 C13 N5 C15 2.6(7) . . . . ?
Nd1 O11 N7 O12 -179.6(4) . . . . ?
Nd1 O11 N7 O10 0.7(4) . . . . ?
O12 N7 O10 Nd1 179.6(4) . . . . ?
O11 N7 O10 Nd1 -0.7(4) . . . . ?
Nd1 O2 C1 O1 -7.6(3) . . . . ?
Nd1 O2 C1 C2 172.9(2) . . . . ?
Nd1 O1 C1 O2 7.6(3) . . . . ?
Nd1 O1 C1 C2 -172.9(2) . . . . ?
C7 C8 C2 C3 -0.6(4) . . . . ?
C7 C8 C2 C1 -179.8(2) . . . . ?
O2 C1 C2 C3 8.5(4) . . . . ?
O1 C1 C2 C3 -171.0(3) . . . . ?
O2 C1 C2 C8 -172.3(3) . . . . ?
O1 C1 C2 C8 8.2(4) . . . . ?
N2 C9 C10 O7 1.1(4) . . . . ?
C12 C9 C10 O7 179.2(3) . . . . ?
N2 C9 C10 N4 -177.5(2) . . . . ?
C12 C9 C10 N4 0.6(4) . . . . ?
O7 C10 N4 C11 -174.0(3) . . . . ?
C9 C10 N4 C11 4.7(4) . . . . ?
Nd1 O6 C11 N4 174.3(2) 2_755 . . . ?
Nd1 O6 C11 N3 -5.8(5) 2_755 . . . ?
C10 N4 C11 O6 173.0(3) . . . . ?
C10 N4 C11 N3 -6.9(4) . . . . ?
C12 N3 C11 O6 -176.3(3) . . . . ?
C12 N3 C11 N4 3.6(4) . . . . ?
C11 N3 C12 O5 179.2(3) . . . . ?
C11 N3 C12 C9 1.2(4) . . . . ?
N2 C9 C12 O5 -3.3(5) . . . . ?
C10 C9 C12 O5 178.8(3) . . . . ?
N2 C9 C12 N3 174.7(3) . . . . ?
C10 C9 C12 N3 -3.2(4) . . . . ?
C8 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C4 -179.3(2) . . . . ?
C6 C4 C3 C2 -0.1(4) . . . . ?
C5 C4 C3 C2 178.3(2) . . . . ?
Nd1 O9 C16 N6 143.8(3) . . . . ?
O9 C16 N6 C17 -2.1(7) . . . . ?
O9 C16 N6 C18 178.0(5) . . . . ?
C21 N8 C19 O13 -0.4(6) . . . . ?
C20 N8 C19 O13 -178.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O5 0.86 1.96 2.628(3) 133.7 .
N3 H3N O1 0.86 1.90 2.722(3) 158.7 2_755
C13 H13 O7 0.93 2.35 3.241(4) 161.3 1_455
N4 H4N O13 0.86 2.01 2.866(3) 173.1 2_855
C16 H16 O11 0.93 2.42 3.277(4) 152.6 2_566
C18 H18A O11 0.96 2.45 3.359(7) 157.9 2_566

_refine_diff_density_max         1.334
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.115

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1539690'
_audit_update_record             
;
2017-03-22 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 Dy N8 O13'
_chemical_formula_weight         762.00

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'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.8661(4)
_cell_length_b                   11.0292(5)
_cell_length_c                   14.0228(6)
_cell_angle_alpha                84.312(2)
_cell_angle_beta                 67.6040(10)
_cell_angle_gamma                64.7230(10)
_cell_volume                     1400.96(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.42

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_F_000             758
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    2.746
_shelx_estimated_absorpt_T_min   0.474
_shelx_estimated_absorpt_T_max   0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.54
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23464
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_max         26.425
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5752
_reflns_number_gt                5212
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0345P)²+0.3282P] 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         5752
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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
Dy1 Dy 0.27832(2) 0.37966(2) 0.36890(2) 0.02133(6) Uani 1 1 d . . . . .
O4 O -0.4597(2) 0.2347(2) 0.30509(17) 0.0285(5) Uani 1 1 d . . . . .
O3 O -0.5339(2) 0.4044(3) 0.4135(2) 0.0413(6) Uani 1 1 d . . . . .
C5 C -0.4327(3) 0.3079(3) 0.3524(2) 0.0242(6) Uani 1 1 d . . . . .
O2 O -0.1511(2) 0.4159(2) 0.53237(17) 0.0283(5) Uani 1 1 d . . . . .
O6 O 0.6739(2) -0.2866(2) -0.19813(17) 0.0321(5) Uani 1 1 d . . . . .
O1 O 0.0511(2) 0.3978(2) 0.39856(19) 0.0323(5) Uani 1 1 d . . . . .
N1 N 0.0921(3) 0.0591(2) 0.14968(19) 0.0238(5) Uani 1 1 d . . . . .
H1N H 0.0690 0.0351 0.1048 0.029 Uiso 1 1 calc R U . . .
N2 N 0.2284(3) 0.0089(2) 0.14008(19) 0.0224(5) Uani 1 1 d . . . . .
O5 O 0.1827(2) -0.0632(3) -0.03217(19) 0.0415(6) Uani 1 1 d . . . . .
O7 O 0.5161(2) -0.1022(3) 0.12244(18) 0.0378(6) Uani 1 1 d . . . . .
O8 O 0.2902(3) 0.1547(2) 0.3896(2) 0.0424(6) Uani 1 1 d . . . . .
C4 C -0.2765(3) 0.2753(3) 0.3325(2) 0.0204(6) Uani 1 1 d . . . . .
O9 O 0.2470(3) 0.3211(3) 0.5398(2) 0.0450(6) Uani 1 1 d . . . . .
C1 C -0.0633(3) 0.3798(3) 0.4407(2) 0.0211(6) Uani 1 1 d . . . . .
C2 C -0.0984(3) 0.3093(3) 0.3749(2) 0.0184(6) Uani 1 1 d . . . . .
C9 C 0.3317(3) -0.0714(3) 0.0578(2) 0.0213(6) Uani 1 1 d . . . . .
N3 N 0.4276(3) -0.1776(3) -0.1116(2) 0.0310(6) Uani 1 1 d . . . . .
H3N H 0.4141 -0.1963 -0.1639 0.037 Uiso 1 1 calc R U . . .
C3 C -0.2443(3) 0.3382(3) 0.3950(2) 0.0200(6) Uani 1 1 d . . . . .
H3 H -0.3196 0.3991 0.4498 0.024 Uiso 1 1 calc R U . . .
C20 C 0.7513(6) 0.5570(5) 0.1794(4) 0.0747(15) Uani 1 1 d . . . . .
H20A H 0.6728 0.5321 0.2193 0.112 Uiso 1 1 calc R U . . .
H20B H 0.7159 0.6328 0.1415 0.112 Uiso 1 1 calc R U . . .
H20C H 0.7865 0.5804 0.2248 0.112 Uiso 1 1 calc R U . . .
N8 N 0.8704(4) 0.4445(3) 0.1074(3) 0.0491(8) Uani 1 1 d . . . . .
C19 C 1.0074(5) 0.4005(4) 0.1021(3) 0.0490(10) Uani 1 1 d . . . . .
H19 H 1.0231 0.4429 0.1477 0.059 Uiso 1 1 calc R U . . .
O13 O 1.1152(3) 0.3086(3) 0.0423(2) 0.0525(7) Uani 1 1 d . . . . .
C21 C 0.8362(6) 0.3867(6) 0.0397(5) 0.0713(14) Uani 1 1 d . . . . .
H21A H 0.9205 0.3069 0.0030 0.107 Uiso 1 1 calc R U . . .
H21B H 0.8092 0.4502 -0.0088 0.107 Uiso 1 1 calc R U . . .
H21C H 0.7558 0.3642 0.0794 0.107 Uiso 1 1 calc R U . . .
C16 C 0.1642(4) 0.2917(4) 0.6157(3) 0.0402(8) Uani 1 1 d . . . . .
H16 H 0.0643 0.3337 0.6280 0.048 Uiso 1 1 calc R U . . .
N6 N 0.2055(4) 0.2058(3) 0.6804(3) 0.0544(9) Uani 1 1 d . . . . .
C18 C 0.3588(6) 0.1305(6) 0.6638(5) 0.092(2) Uani 1 1 d . . . . .
H18A H 0.4152 0.1720 0.6141 0.138 Uiso 1 1 calc R U . . .
H18B H 0.3915 0.0400 0.6383 0.138 Uiso 1 1 calc R U . . .
H18C H 0.3718 0.1294 0.7279 0.138 Uiso 1 1 calc R U . . .
C17 C 0.1006(7) 0.1795(6) 0.7721(5) 0.104(2) Uani 1 1 d . . . . .
H17A H 0.0033 0.2475 0.7838 0.155 Uiso 1 1 calc R U . . .
H17B H 0.1247 0.1807 0.8310 0.155 Uiso 1 1 calc R U . . .
H17C H 0.1047 0.0928 0.7617 0.155 Uiso 1 1 calc R U . . .
C8 C 0.0147(3) 0.2188(3) 0.2926(2) 0.0200(6) Uani 1 1 d . . . . .
H8 H 0.1117 0.2027 0.2775 0.024 Uiso 1 1 calc R U . . .
C7 C -0.0186(3) 0.1527(3) 0.2329(2) 0.0203(6) Uani 1 1 d . . . . .
C10 C 0.3046(3) -0.1021(3) -0.0290(2) 0.0266(7) Uani 1 1 d . . . . .
C11 C 0.5693(3) -0.2258(3) -0.1186(2) 0.0233(6) Uani 1 1 d . . . . .
N4 N 0.5910(3) -0.2038(2) -0.0339(2) 0.0248(5) Uani 1 1 d . . . . .
H4N H 0.6794 -0.2421 -0.0357 0.030 Uiso 1 1 calc R U . . .
C12 C 0.4824(3) -0.1247(3) 0.0554(2) 0.0237(6) Uani 1 1 d . . . . .
C6 C -0.1638(3) 0.1820(3) 0.2517(2) 0.0218(6) Uani 1 1 d . . . . .
H6 H -0.1857 0.1395 0.2105 0.026 Uiso 1 1 calc R U . . .
O11 O 0.4086(4) 0.4986(3) 0.2348(3) 0.0642(9) Uani 1 1 d . . . . .
N7 N 0.3048(5) 0.5730(4) 0.2089(3) 0.0537(9) Uani 1 1 d . . . . .
O12 O 0.3137(5) 0.6553(4) 0.1439(3) 0.0953(13) Uani 1 1 d . . . . .
O10 O 0.1866(3) 0.5598(3) 0.2551(2) 0.0512(7) Uani 1 1 d . . . . .
C13 C 0.3112(4) 0.0491(3) 0.3515(3) 0.0353(8) Uani 1 1 d . . . . .
H13 H 0.3663 0.0277 0.2811 0.042 Uiso 1 1 calc R U . . .
C14 C 0.2931(7) -0.1628(5) 0.3574(4) 0.0809(18) Uani 1 1 d . . . . .
H14A H 0.2035 -0.1644 0.3618 0.121 Uiso 1 1 calc R U . . .
H14B H 0.3405 -0.2354 0.3931 0.121 Uiso 1 1 calc R U . . .
H14C H 0.3570 -0.1726 0.2861 0.121 Uiso 1 1 calc R U . . .
C15 C 0.1722(8) -0.0030(6) 0.5139(4) 0.098(2) Uani 1 1 d . . . . .
H15A H 0.1136 -0.0530 0.5366 0.147 Uiso 1 1 calc R U . . .
H15B H 0.1092 0.0915 0.5259 0.147 Uiso 1 1 calc R U . . .
H15C H 0.2354 -0.0257 0.5519 0.147 Uiso 1 1 calc R U . . .
N5 N 0.2604(4) -0.0360(3) 0.4047(3) 0.0493(9) 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
Dy1 O1 2.263(2) . ?
Dy1 O2 2.326(2) 2_566 ?
Dy1 O9 2.353(3) . ?
Dy1 O8 2.422(2) . ?
Dy1 O4 2.432(2) 1_655 ?
Dy1 O3 2.472(2) 1_655 ?
Dy1 O6 2.478(2) 2_655 ?
Dy1 O11 2.516(3) . ?
Dy1 O10 2.526(3) . ?
Dy1 C5 2.810(3) 1_655 ?
O4 C5 1.278(4) . ?
O4 Dy1 2.432(2) 1_455 ?
O3 C5 1.241(4) . ?
O3 Dy1 2.472(2) 1_455 ?
C5 C4 1.493(4) . ?
C5 Dy1 2.810(3) 1_455 ?
O2 C1 1.250(4) . ?
O2 Dy1 2.326(2) 2_566 ?
O6 C11 1.231(4) . ?
O6 Dy1 2.478(2) 2_655 ?
O1 C1 1.250(3) . ?
N1 N2 1.297(3) . ?
N1 C7 1.408(4) . ?
N1 H1N 0.8600 . ?
N2 C9 1.320(4) . ?
O5 C10 1.224(4) . ?
O7 C12 1.210(4) . ?
O8 C13 1.224(4) . ?
C4 C3 1.391(4) . ?
C4 C6 1.392(4) . ?
O9 C16 1.224(5) . ?
C1 C2 1.505(4) . ?
C2 C3 1.392(4) . ?
C2 C8 1.393(4) . ?
C9 C10 1.456(4) . ?
C9 C12 1.473(4) . ?
N3 C11 1.363(4) . ?
N3 C10 1.373(4) . ?
N3 H3N 0.8600 . ?
C3 H3 0.9300 . ?
C20 N8 1.454(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N8 C19 1.328(5) . ?
N8 C21 1.426(6) . ?
C19 O13 1.229(5) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C16 N6 1.304(5) . ?
C16 H16 0.9300 . ?
N6 C18 1.442(6) . ?
N6 C17 1.459(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8 C7 1.393(4) . ?
C8 H8 0.9300 . ?
C7 C6 1.388(4) . ?
C11 N4 1.358(4) . ?
N4 C12 1.391(4) . ?
N4 H4N 0.8600 . ?
C6 H6 0.9300 . ?
O11 N7 1.241(5) . ?
N7 O12 1.228(5) . ?
N7 O10 1.264(5) . ?
C13 N5 1.316(5) . ?
C13 H13 0.9300 . ?
C14 N5 1.450(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N5 1.446(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Dy1 O2 84.07(7) . 2_566 ?
O1 Dy1 O9 89.22(9) . . ?
O2 Dy1 O9 75.28(9) 2_566 . ?
O1 Dy1 O8 73.20(9) . . ?
O2 Dy1 O8 137.31(9) 2_566 . ?
O9 Dy1 O8 68.90(9) . . ?
O1 Dy1 O4 146.35(7) . 1_655 ?
O2 Dy1 O4 128.75(7) 2_566 1_655 ?
O9 Dy1 O4 92.41(9) . 1_655 ?
O8 Dy1 O4 76.10(8) . 1_655 ?
O1 Dy1 O3 155.20(8) . 1_655 ?
O2 Dy1 O3 76.04(7) 2_566 1_655 ?
O9 Dy1 O3 71.64(9) . 1_655 ?
O8 Dy1 O3 112.25(9) . 1_655 ?
O4 Dy1 O3 53.09(7) 1_655 1_655 ?
O1 Dy1 O6 80.89(7) . 2_655 ?
O2 Dy1 O6 139.49(8) 2_566 2_655 ?
O9 Dy1 O6 141.33(9) . 2_655 ?
O8 Dy1 O6 72.45(9) . 2_655 ?
O4 Dy1 O6 76.99(7) 1_655 2_655 ?
O3 Dy1 O6 123.90(7) 1_655 2_655 ?
O1 Dy1 O11 125.02(10) . . ?
O2 Dy1 O11 85.28(10) 2_566 . ?
O9 Dy1 O11 138.73(10) . . ?
O8 Dy1 O11 137.32(11) . . ?
O4 Dy1 O11 71.88(10) 1_655 . ?
O3 Dy1 O11 68.46(10) 1_655 . ?
O6 Dy1 O11 73.41(10) 2_655 . ?
O1 Dy1 O10 75.75(10) . . ?
O2 Dy1 O10 72.70(9) 2_566 . ?
O9 Dy1 O10 145.73(9) . . ?
O8 Dy1 O10 132.02(9) . . ?
O4 Dy1 O10 117.16(9) 1_655 . ?
O3 Dy1 O10 111.34(10) 1_655 . ?
O6 Dy1 O10 67.20(9) 2_655 . ?
O11 Dy1 O10 49.64(10) . . ?
O1 Dy1 C5 168.20(9) . 1_655 ?
O2 Dy1 C5 101.82(8) 2_566 1_655 ?
O9 Dy1 C5 82.52(9) . 1_655 ?
O8 Dy1 C5 95.88(9) . 1_655 ?
O4 Dy1 C5 27.00(8) 1_655 1_655 ?
O3 Dy1 C5 26.18(8) 1_655 1_655 ?
O6 Dy1 C5 100.35(8) 2_655 1_655 ?
O11 Dy1 C5 66.10(10) . 1_655 ?
O10 Dy1 C5 115.66(9) . 1_655 ?
C5 O4 Dy1 93.24(17) . 1_455 ?
C5 O3 Dy1 92.31(18) . 1_455 ?
O3 C5 O4 121.0(3) . . ?
O3 C5 C4 120.3(3) . . ?
O4 C5 C4 118.7(3) . . ?
O3 C5 Dy1 61.52(15) . 1_455 ?
O4 C5 Dy1 59.76(14) . 1_455 ?
C4 C5 Dy1 173.9(2) . 1_455 ?
C1 O2 Dy1 133.6(2) . 2_566 ?
C11 O6 Dy1 139.4(2) . 2_655 ?
C1 O1 Dy1 158.4(2) . . ?
N2 N1 C7 120.6(2) . . ?
N2 N1 H1N 119.7 . . ?
C7 N1 H1N 119.7 . . ?
N1 N2 C9 119.7(2) . . ?
C13 O8 Dy1 149.5(3) . . ?
C3 C4 C6 120.4(2) . . ?
C3 C4 C5 119.7(2) . . ?
C6 C4 C5 119.9(2) . . ?
C16 O9 Dy1 141.5(3) . . ?
O1 C1 O2 125.6(3) . . ?
O1 C1 C2 116.9(3) . . ?
O2 C1 C2 117.4(2) . . ?
C3 C2 C8 120.5(2) . . ?
C3 C2 C1 119.6(2) . . ?
C8 C2 C1 119.8(2) . . ?
N2 C9 C10 124.1(3) . . ?
N2 C9 C12 115.3(3) . . ?
C10 C9 C12 120.5(2) . . ?
C11 N3 C10 126.1(3) . . ?
C11 N3 H3N 117.0 . . ?
C10 N3 H3N 117.0 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 N8 C21 121.1(4) . . ?
C19 N8 C20 121.0(4) . . ?
C21 N8 C20 117.8(4) . . ?
O13 C19 N8 125.6(4) . . ?
O13 C19 H19 117.2 . . ?
N8 C19 H19 117.2 . . ?
N8 C21 H21A 109.5 . . ?
N8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O9 C16 N6 124.8(4) . . ?
O9 C16 H16 117.6 . . ?
N6 C16 H16 117.6 . . ?
C16 N6 C18 121.2(4) . . ?
C16 N6 C17 122.2(4) . . ?
C18 N6 C17 116.6(5) . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N6 C17 H17A 109.5 . . ?
N6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C8 C2 119.5(2) . . ?
C7 C8 H8 120.3 . . ?
C2 C8 H8 120.3 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 N1 118.1(2) . . ?
C8 C7 N1 121.6(2) . . ?
O5 C10 N3 120.1(3) . . ?
O5 C10 C9 124.4(3) . . ?
N3 C10 C9 115.5(3) . . ?
O6 C11 N4 121.0(3) . . ?
O6 C11 N3 121.8(3) . . ?
N4 C11 N3 117.2(3) . . ?
C11 N4 C12 125.6(3) . . ?
C11 N4 H4N 117.2 . . ?
C12 N4 H4N 117.2 . . ?
O7 C12 N4 119.8(3) . . ?
O7 C12 C9 125.3(3) . . ?
N4 C12 C9 114.8(3) . . ?
C7 C6 C4 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C4 C6 H6 120.1 . . ?
N7 O11 Dy1 98.1(2) . . ?
O12 N7 O11 123.2(4) . . ?
O12 N7 O10 121.4(4) . . ?
O11 N7 O10 115.4(3) . . ?
N7 O10 Dy1 96.9(2) . . ?
O8 C13 N5 123.7(4) . . ?
O8 C13 H13 118.2 . . ?
N5 C13 H13 118.2 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 N5 C15 118.9(4) . . ?
C13 N5 C14 121.9(4) . . ?
C15 N5 C14 119.2(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
Dy1 O3 C5 O4 -6.4(3) 1_455 . . . ?
Dy1 O3 C5 C4 173.3(3) 1_455 . . . ?
Dy1 O4 C5 O3 6.6(3) 1_455 . . . ?
Dy1 O4 C5 C4 -173.2(3) 1_455 . . . ?
C7 N1 N2 C9 -175.3(3) . . . . ?
O3 C5 C4 C3 10.9(5) . . . . ?
O4 C5 C4 C3 -169.3(3) . . . . ?
O3 C5 C4 C6 -169.3(3) . . . . ?
O4 C5 C4 C6 10.5(5) . . . . ?
Dy1 O1 C1 O2 63.1(7) . . . . ?
Dy1 O1 C1 C2 -117.3(5) . . . . ?
Dy1 O2 C1 O1 53.5(4) 2_566 . . . ?
Dy1 O2 C1 C2 -126.1(2) 2_566 . . . ?
O1 C1 C2 C3 -150.3(3) . . . . ?
O2 C1 C2 C3 29.3(4) . . . . ?
O1 C1 C2 C8 27.8(4) . . . . ?
O2 C1 C2 C8 -152.6(3) . . . . ?
N1 N2 C9 C10 4.2(5) . . . . ?
N1 N2 C9 C12 -179.0(3) . . . . ?
C6 C4 C3 C2 1.4(5) . . . . ?
C5 C4 C3 C2 -178.8(3) . . . . ?
C8 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C21 N8 C19 O13 -0.8(6) . . . . ?
C20 N8 C19 O13 -178.2(4) . . . . ?
Dy1 O9 C16 N6 145.2(4) . . . . ?
O9 C16 N6 C18 -3.6(7) . . . . ?
O9 C16 N6 C17 177.2(5) . . . . ?
C3 C2 C8 C7 -2.8(4) . . . . ?
C1 C2 C8 C7 179.1(3) . . . . ?
C2 C8 C7 C6 3.5(4) . . . . ?
C2 C8 C7 N1 -179.2(3) . . . . ?
N2 N1 C7 C6 -166.9(3) . . . . ?
N2 N1 C7 C8 15.7(4) . . . . ?
C11 N3 C10 O5 179.2(3) . . . . ?
C11 N3 C10 C9 0.5(5) . . . . ?
N2 C9 C10 O5 -4.4(5) . . . . ?
C12 C9 C10 O5 179.0(3) . . . . ?
N2 C9 C10 N3 174.2(3) . . . . ?
C12 C9 C10 N3 -2.4(4) . . . . ?
Dy1 O6 C11 N4 172.9(2) 2_655 . . . ?
Dy1 O6 C11 N3 -7.3(5) 2_655 . . . ?
C10 N3 C11 O6 -175.9(3) . . . . ?
C10 N3 C11 N4 4.0(5) . . . . ?
O6 C11 N4 C12 172.8(3) . . . . ?
N3 C11 N4 C12 -7.0(5) . . . . ?
C11 N4 C12 O7 -173.3(3) . . . . ?
C11 N4 C12 C9 5.1(4) . . . . ?
N2 C9 C12 O7 1.3(5) . . . . ?
C10 C9 C12 O7 178.2(3) . . . . ?
N2 C9 C12 N4 -177.0(3) . . . . ?
C10 C9 C12 N4 -0.1(4) . . . . ?
C8 C7 C6 C4 -1.8(5) . . . . ?
N1 C7 C6 C4 -179.2(3) . . . . ?
C3 C4 C6 C7 -0.7(5) . . . . ?
C5 C4 C6 C7 179.5(3) . . . . ?
Dy1 O11 N7 O12 178.7(4) . . . . ?
Dy1 O11 N7 O10 -0.6(4) . . . . ?
O12 N7 O10 Dy1 -178.7(4) . . . . ?
O11 N7 O10 Dy1 0.6(4) . . . . ?
Dy1 O8 C13 N5 -158.1(4) . . . . ?
O8 C13 N5 C15 1.2(7) . . . . ?
O8 C13 N5 C14 -177.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O5 0.86 1.96 2.632(3) 133.8 .
N3 H3N O4 0.86 1.89 2.703(3) 156.4 2
C16 H16 O10 0.93 2.40 3.238(5) 150.6 2_566
C17 H17A O10 0.96 2.44 3.343(7) 156.5 2_566
N4 H4N O13 0.86 2.00 2.852(4) 173.0 2_755
C13 H13 O7 0.93 2.35 3.241(4) 159.7 .
C14 H14C O7 0.96 2.57 3.470(6) 155.2 .


_refine_diff_density_max         2.381
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.123

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1539687'
_audit_update_record             
;
2017-03-22 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 Ce N8 O13'
_chemical_formula_weight         739.62

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   11.0424(3)
_cell_length_b                   11.1343(3)
_cell_length_c                   14.1570(4)
_cell_angle_alpha                83.8450(10)
_cell_angle_beta                 68.087(2)
_cell_angle_gamma                63.8570(10)
_cell_volume                     1446.21(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9110
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.33

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_F_000             742
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.651
_shelx_estimated_absorpt_T_min   0.629
_shelx_estimated_absorpt_T_max   0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20269
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.340
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5897
_reflns_number_gt                5190
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0398P)²+0.2092P] 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         5897
_refine_ls_number_parameters     394
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0645
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.27888(2) 0.38114(2) 0.36820(2) 0.02250(6) Uani 1 1 d . . . . .
O2 O -0.1469(2) 0.4078(2) 0.52757(15) 0.0329(5) Uani 1 1 d . . . . .
O4 O -0.44826(19) 0.2331(2) 0.29745(15) 0.0342(5) Uani 1 1 d . . . . .
O3 O -0.5230(2) 0.3926(2) 0.41314(18) 0.0471(6) Uani 1 1 d . . . . .
C5 C -0.4230(3) 0.3015(3) 0.3477(2) 0.0281(6) Uani 1 1 d . . . . .
O13 O 1.1189(3) 0.3055(3) 0.0395(2) 0.0563(7) Uani 1 1 d . . . . .
O6 O 0.6702(2) -0.2867(2) -0.19057(15) 0.0376(5) Uani 1 1 d . . . . .
O10 O 0.1883(3) 0.5705(3) 0.2512(2) 0.0606(7) Uani 1 1 d . . . . .
O12 O 0.3129(5) 0.6642(4) 0.1417(3) 0.1167(14) Uani 1 1 d . . . . .
O11 O 0.4091(3) 0.5070(3) 0.2318(3) 0.0765(9) Uani 1 1 d . . . . .
O1 O 0.0456(2) 0.3995(2) 0.39487(17) 0.0390(5) Uani 1 1 d . . . . .
N1 N 0.0950(2) 0.0582(2) 0.14839(17) 0.0254(5) Uani 1 1 d . . . . .
H1N H 0.0727 0.0337 0.1041 0.030 Uiso 1 1 calc R U . . .
N2 N 0.2298(2) 0.0093(2) 0.13948(16) 0.0236(5) Uani 1 1 d . . . . .
O7 O 0.1854(2) -0.0648(2) -0.02979(16) 0.0418(5) Uani 1 1 d . . . . .
O5 O 0.5137(2) -0.0996(2) 0.12385(15) 0.0401(5) Uani 1 1 d . . . . .
N7 N 0.3049(4) 0.5825(3) 0.2069(3) 0.0628(9) Uani 1 1 d . . . . .
C1 C -0.0633(3) 0.3762(2) 0.4367(2) 0.0234(5) Uani 1 1 d . . . . .
C2 C -0.0958(3) 0.3057(2) 0.37098(19) 0.0210(5) Uani 1 1 d . . . . .
C7 C -0.0154(3) 0.1515(3) 0.23057(19) 0.0222(5) Uani 1 1 d . . . . .
C9 C 0.3321(3) -0.0701(3) 0.05902(19) 0.0227(5) Uani 1 1 d . . . . .
N3 N 0.4279(2) -0.1785(2) -0.10732(18) 0.0325(6) Uani 1 1 d . . . . .
H3N H 0.4149 -0.1981 -0.1588 0.039 Uiso 1 1 calc R U . . .
C21 C 0.8421(5) 0.3846(5) 0.0372(4) 0.0807(14) Uani 1 1 d . . . . .
H21A H 0.8151 0.4483 -0.0112 0.121 Uiso 1 1 calc R U . . .
H21B H 0.7627 0.3636 0.0765 0.121 Uiso 1 1 calc R U . . .
H21C H 0.9248 0.3043 0.0015 0.121 Uiso 1 1 calc R U . . .
N8 N 0.8771(3) 0.4405(3) 0.1035(3) 0.0545(8) Uani 1 1 d . . . . .
C20 C 0.7584(5) 0.5521(5) 0.1747(4) 0.0868(16) Uani 1 1 d . . . . .
H20A H 0.7943 0.5790 0.2168 0.130 Uiso 1 1 calc R U . . .
H20B H 0.6852 0.5246 0.2169 0.130 Uiso 1 1 calc R U . . .
H20C H 0.7174 0.6261 0.1372 0.130 Uiso 1 1 calc R U . . .
C19 C 1.0118(4) 0.3964(4) 0.0987(3) 0.0536(9) Uani 1 1 d . . . . .
H19 H 1.0269 0.4378 0.1441 0.064 Uiso 1 1 calc R U . . .
C4 C -0.2694(3) 0.2713(3) 0.3278(2) 0.0230(5) Uani 1 1 d . . . . .
O9 O 0.2422(3) 0.3194(3) 0.54643(18) 0.0517(6) Uani 1 1 d . . . . .
C16 C 0.1645(4) 0.2903(3) 0.6221(3) 0.0448(8) Uani 1 1 d . . . . .
H16 H 0.0653 0.3338 0.6359 0.054 Uiso 1 1 calc R U . . .
N6 N 0.2076(4) 0.2035(3) 0.6855(3) 0.0624(9) Uani 1 1 d . . . . .
C17 C 0.3590(6) 0.1304(6) 0.6684(5) 0.114(2) Uani 1 1 d . . . . .
H17A H 0.3968 0.0456 0.6325 0.171 Uiso 1 1 calc R U . . .
H17B H 0.3718 0.1157 0.7328 0.171 Uiso 1 1 calc R U . . .
H17C H 0.4096 0.1809 0.6285 0.171 Uiso 1 1 calc R U . . .
C8 C 0.0160(3) 0.2168(2) 0.29009(19) 0.0221(5) Uani 1 1 d . . . . .
H8 H 0.1113 0.2010 0.2758 0.027 Uiso 1 1 calc R U . . .
C10 C 0.3063(3) -0.1028(3) -0.0264(2) 0.0286(6) Uani 1 1 d . . . . .
C11 C 0.5673(3) -0.2252(3) -0.1131(2) 0.0265(6) Uani 1 1 d . . . . .
N4 N 0.5879(2) -0.2015(2) -0.02956(16) 0.0261(5) Uani 1 1 d . . . . .
H4N H 0.6753 -0.2390 -0.0307 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4808(3) -0.1224(3) 0.0573(2) 0.0253(5) Uani 1 1 d . . . . .
C6 C -0.1574(3) 0.1794(3) 0.24775(19) 0.0237(5) Uani 1 1 d . . . . .
H6 H -0.1780 0.1373 0.2064 0.028 Uiso 1 1 calc R U . . .
C3 C -0.2388(3) 0.3330(3) 0.3901(2) 0.0227(5) Uani 1 1 d . . . . .
H3 H -0.3136 0.3924 0.4444 0.027 Uiso 1 1 calc R U . . .
O8 O 0.2972(3) 0.1480(2) 0.38553(19) 0.0506(6) Uani 1 1 d . . . . .
C13 C 0.3122(3) 0.0438(3) 0.3510(3) 0.0405(7) Uani 1 1 d . . . . .
H13 H 0.3635 0.0211 0.2815 0.049 Uiso 1 1 calc R U . . .
N5 N 0.2610(4) -0.0373(3) 0.4052(2) 0.0608(9) Uani 1 1 d . U . . .
C14 C 0.2882(7) -0.1625(5) 0.3611(4) 0.107(2) Uani 1 1 d . U . . .
H14A H 0.1976 -0.1647 0.3734 0.161 Uiso 1 1 calc R U . . .
H14B H 0.3444 -0.2361 0.3917 0.161 Uiso 1 1 calc R U . . .
H14C H 0.3406 -0.1695 0.2889 0.161 Uiso 1 1 calc R U . . .
C15 C 0.1759(8) -0.0020(6) 0.5136(4) 0.127(3) Uani 1 1 d . U . . .
H15A H 0.2391 -0.0150 0.5494 0.190 Uiso 1 1 calc R U . . .
H15B H 0.1265 -0.0579 0.5396 0.190 Uiso 1 1 calc R U . . .
H15C H 0.1062 0.0903 0.5234 0.190 Uiso 1 1 calc R U . . .
C18 C 0.1068(7) 0.1777(6) 0.7772(5) 0.129(3) Uani 1 1 d . . . . .
H18A H 0.1280 0.1858 0.8354 0.193 Uiso 1 1 calc R U . . .
H18B H 0.1166 0.0887 0.7702 0.193 Uiso 1 1 calc R U . . .
H18C H 0.0094 0.2416 0.7862 0.193 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
Ce1 O1 2.3767(18) . ?
Ce1 O2 2.4384(18) 2_566 ?
Ce1 O9 2.473(2) . ?
Ce1 O8 2.505(2) . ?
Ce1 O3 2.551(2) 1_655 ?
Ce1 O4 2.5542(18) 1_655 ?
Ce1 O6 2.595(2) 2_655 ?
Ce1 O10 2.612(3) . ?
Ce1 O11 2.624(3) . ?
Ce1 C5 2.911(3) 1_655 ?
O2 C1 1.247(3) . ?
O2 Ce1 2.4383(18) 2_566 ?
O4 C5 1.271(3) . ?
O4 Ce1 2.5542(18) 1_455 ?
O3 C5 1.248(3) . ?
O3 Ce1 2.551(2) 1_455 ?
C5 C4 1.494(3) . ?
C5 Ce1 2.911(3) 1_455 ?
O13 C19 1.230(4) . ?
O6 C11 1.227(3) . ?
O6 Ce1 2.595(2) 2_655 ?
O10 N7 1.264(4) . ?
O12 N7 1.231(4) . ?
O11 N7 1.242(5) . ?
O1 C1 1.255(3) . ?
N1 N2 1.300(3) . ?
N1 C7 1.415(3) . ?
N1 H1N 0.8600 . ?
N2 C9 1.316(3) . ?
O7 C10 1.229(3) . ?
O5 C12 1.213(3) . ?
C1 C2 1.504(3) . ?
C2 C8 1.388(3) . ?
C2 C3 1.391(3) . ?
C7 C6 1.385(3) . ?
C7 C8 1.390(3) . ?
C9 C10 1.456(4) . ?
C9 C12 1.471(4) . ?
N3 C11 1.362(3) . ?
N3 C10 1.374(3) . ?
N3 H3N 0.8600 . ?
C21 N8 1.423(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N8 C19 1.322(5) . ?
N8 C20 1.458(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19 0.9300 . ?
C4 C3 1.385(4) . ?
C4 C6 1.396(3) . ?
O9 C16 1.214(4) . ?
C16 N6 1.301(4) . ?
C16 H16 0.9300 . ?
N6 C17 1.435(6) . ?
N6 C18 1.460(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8 H8 0.9300 . ?
C11 N4 1.358(3) . ?
N4 C12 1.385(3) . ?
N4 H4N 0.8600 . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
O8 C13 1.227(4) . ?
C13 N5 1.304(4) . ?
C13 H13 0.9300 . ?
N5 C14 1.449(5) . ?
N5 C15 1.457(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ce1 O2 85.09(6) . 2_566 ?
O1 Ce1 O9 88.61(8) . . ?
O2 Ce1 O9 74.10(8) 2_566 . ?
O1 Ce1 O8 73.44(8) . . ?
O2 Ce1 O8 137.84(7) 2_566 . ?
O9 Ce1 O8 69.63(8) . . ?
O1 Ce1 O3 157.50(7) . 1_655 ?
O2 Ce1 O3 78.18(6) 2_566 1_655 ?
O9 Ce1 O3 72.48(8) . 1_655 ?
O8 Ce1 O3 109.64(8) . 1_655 ?
O1 Ce1 O4 146.05(6) . 1_655 ?
O2 Ce1 O4 128.47(6) 2_566 1_655 ?
O9 Ce1 O4 95.59(8) . 1_655 ?
O8 Ce1 O4 76.56(7) . 1_655 ?
O3 Ce1 O4 51.07(6) 1_655 1_655 ?
O1 Ce1 O6 80.39(7) . 2_655 ?
O2 Ce1 O6 140.27(7) 2_566 2_655 ?
O9 Ce1 O6 141.51(8) . 2_655 ?
O8 Ce1 O6 71.88(8) . 2_655 ?
O3 Ce1 O6 122.03(6) 1_655 2_655 ?
O4 Ce1 O6 75.48(6) 1_655 2_655 ?
O1 Ce1 O10 76.98(9) . . ?
O2 Ce1 O10 73.15(8) 2_566 . ?
O9 Ce1 O10 145.12(8) . . ?
O8 Ce1 O10 132.87(9) . . ?
O3 Ce1 O10 111.70(9) 1_655 . ?
O4 Ce1 O10 114.13(8) 1_655 . ?
O6 Ce1 O10 67.62(8) 2_655 . ?
O1 Ce1 O11 124.54(9) . . ?
O2 Ce1 O11 85.38(9) 2_566 . ?
O9 Ce1 O11 139.53(10) . . ?
O8 Ce1 O11 136.65(10) . . ?
O3 Ce1 O11 69.33(9) 1_655 . ?
O4 Ce1 O11 70.34(9) 1_655 . ?
O6 Ce1 O11 73.30(9) 2_655 . ?
O10 Ce1 O11 48.04(9) . . ?
O1 Ce1 C5 167.99(8) . 1_655 ?
O2 Ce1 C5 102.81(7) 2_566 1_655 ?
O9 Ce1 C5 84.96(8) . 1_655 ?
O8 Ce1 C5 94.78(8) . 1_655 ?
O3 Ce1 C5 25.33(7) 1_655 1_655 ?
O4 Ce1 C5 25.85(7) 1_655 1_655 ?
O6 Ce1 C5 98.45(7) 2_655 1_655 ?
O10 Ce1 C5 113.79(9) . 1_655 ?
O11 Ce1 C5 65.78(9) . 1_655 ?
C1 O2 Ce1 132.66(18) . 2_566 ?
C5 O4 Ce1 92.97(15) . 1_455 ?
C5 O3 Ce1 93.69(16) . 1_455 ?
O3 C5 O4 121.7(2) . . ?
O3 C5 C4 119.4(2) . . ?
O4 C5 C4 118.9(2) . . ?
O3 C5 Ce1 60.98(14) . 1_455 ?
O4 C5 Ce1 61.18(13) . 1_455 ?
C4 C5 Ce1 173.5(2) . 1_455 ?
C11 O6 Ce1 139.72(18) . 2_655 ?
N7 O10 Ce1 97.7(2) . . ?
N7 O11 Ce1 97.8(2) . . ?
C1 O1 Ce1 155.7(2) . . ?
N2 N1 C7 120.4(2) . . ?
N2 N1 H1N 119.8 . . ?
C7 N1 H1N 119.8 . . ?
N1 N2 C9 119.7(2) . . ?
O12 N7 O11 122.7(4) . . ?
O12 N7 O10 120.8(4) . . ?
O11 N7 O10 116.5(3) . . ?
O2 C1 O1 125.3(2) . . ?
O2 C1 C2 117.8(2) . . ?
O1 C1 C2 116.9(2) . . ?
C8 C2 C3 120.2(2) . . ?
C8 C2 C1 120.2(2) . . ?
C3 C2 C1 119.6(2) . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 N1 117.6(2) . . ?
C8 C7 N1 121.7(2) . . ?
N2 C9 C10 124.2(2) . . ?
N2 C9 C12 115.5(2) . . ?
C10 C9 C12 120.3(2) . . ?
C11 N3 C10 125.7(2) . . ?
C11 N3 H3N 117.1 . . ?
C10 N3 H3N 117.1 . . ?
N8 C21 H21A 109.5 . . ?
N8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 N8 C21 121.7(4) . . ?
C19 N8 C20 121.2(4) . . ?
C21 N8 C20 117.0(4) . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O13 C19 N8 125.8(4) . . ?
O13 C19 H19 117.1 . . ?
N8 C19 H19 117.1 . . ?
C3 C4 C6 120.5(2) . . ?
C3 C4 C5 119.7(2) . . ?
C6 C4 C5 119.8(2) . . ?
C16 O9 Ce1 144.8(2) . . ?
O9 C16 N6 125.8(4) . . ?
O9 C16 H16 117.1 . . ?
N6 C16 H16 117.1 . . ?
C16 N6 C17 120.5(4) . . ?
C16 N6 C18 122.6(4) . . ?
C17 N6 C18 116.9(4) . . ?
N6 C17 H17A 109.5 . . ?
N6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C8 C7 119.6(2) . . ?
C2 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
O7 C10 N3 120.2(3) . . ?
O7 C10 C9 124.0(2) . . ?
N3 C10 C9 115.8(2) . . ?
O6 C11 N4 121.2(2) . . ?
O6 C11 N3 121.5(3) . . ?
N4 C11 N3 117.3(2) . . ?
C11 N4 C12 125.7(2) . . ?
C11 N4 H4N 117.1 . . ?
C12 N4 H4N 117.1 . . ?
O5 C12 N4 119.8(2) . . ?
O5 C12 C9 125.3(2) . . ?
N4 C12 C9 114.9(2) . . ?
C7 C6 C4 119.3(2) . . ?
C7 C6 H6 120.4 . . ?
C4 C6 H6 120.4 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C13 O8 Ce1 152.1(2) . . ?
O8 C13 N5 124.4(3) . . ?
O8 C13 H13 117.8 . . ?
N5 C13 H13 117.8 . . ?
C13 N5 C14 122.0(3) . . ?
C13 N5 C15 119.0(3) . . ?
C14 N5 C15 119.1(4) . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ce1 O3 C5 O4 -7.6(3) 1_455 . . . ?
Ce1 O3 C5 C4 172.5(2) 1_455 . . . ?
Ce1 O4 C5 O3 7.6(3) 1_455 . . . ?
Ce1 O4 C5 C4 -172.6(2) 1_455 . . . ?
C7 N1 N2 C9 -175.4(2) . . . . ?
Ce1 O11 N7 O12 -179.7(4) . . . . ?
Ce1 O11 N7 O10 -0.6(4) . . . . ?
Ce1 O10 N7 O12 179.7(4) . . . . ?
Ce1 O10 N7 O11 0.6(4) . . . . ?
Ce1 O2 C1 O1 51.7(4) 2_566 . . . ?
Ce1 O2 C1 C2 -127.5(2) 2_566 . . . ?
Ce1 O1 C1 O2 64.2(5) . . . . ?
Ce1 O1 C1 C2 -116.6(4) . . . . ?
O2 C1 C2 C8 -150.6(3) . . . . ?
O1 C1 C2 C8 30.1(4) . . . . ?
O2 C1 C2 C3 31.0(4) . . . . ?
O1 C1 C2 C3 -148.2(3) . . . . ?
N2 N1 C7 C6 -167.4(2) . . . . ?
N2 N1 C7 C8 14.8(4) . . . . ?
N1 N2 C9 C10 3.7(4) . . . . ?
N1 N2 C9 C12 -178.7(2) . . . . ?
C21 N8 C19 O13 -0.3(6) . . . . ?
C20 N8 C19 O13 -178.1(4) . . . . ?
O3 C5 C4 C3 7.8(4) . . . . ?
O4 C5 C4 C3 -172.1(3) . . . . ?
O3 C5 C4 C6 -173.4(3) . . . . ?
O4 C5 C4 C6 6.7(4) . . . . ?
Ce1 O9 C16 N6 143.7(3) . . . . ?
O9 C16 N6 C17 -1.2(7) . . . . ?
O9 C16 N6 C18 177.5(5) . . . . ?
C3 C2 C8 C7 -2.3(4) . . . . ?
C1 C2 C8 C7 179.4(2) . . . . ?
C6 C7 C8 C2 3.4(4) . . . . ?
N1 C7 C8 C2 -178.9(2) . . . . ?
C11 N3 C10 O7 179.2(3) . . . . ?
C11 N3 C10 C9 0.7(4) . . . . ?
N2 C9 C10 O7 -3.7(5) . . . . ?
C12 C9 C10 O7 178.8(3) . . . . ?
N2 C9 C10 N3 174.8(3) . . . . ?
C12 C9 C10 N3 -2.7(4) . . . . ?
Ce1 O6 C11 N4 175.27(19) 2_655 . . . ?
Ce1 O6 C11 N3 -4.5(5) 2_655 . . . ?
C10 N3 C11 O6 -176.3(3) . . . . ?
C10 N3 C11 N4 3.9(4) . . . . ?
O6 C11 N4 C12 173.2(3) . . . . ?
N3 C11 N4 C12 -7.0(4) . . . . ?
C11 N4 C12 O5 -174.0(3) . . . . ?
C11 N4 C12 C9 5.0(4) . . . . ?
N2 C9 C12 O5 1.3(4) . . . . ?
C10 C9 C12 O5 179.0(3) . . . . ?
N2 C9 C12 N4 -177.6(2) . . . . ?
C10 C9 C12 N4 0.1(4) . . . . ?
C8 C7 C6 C4 -1.9(4) . . . . ?
N1 C7 C6 C4 -179.7(2) . . . . ?
C3 C4 C6 C7 -0.7(4) . . . . ?
C5 C4 C6 C7 -179.5(2) . . . . ?
C6 C4 C3 C2 1.7(4) . . . . ?
C5 C4 C3 C2 -179.5(2) . . . . ?
C8 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 178.1(2) . . . . ?
Ce1 O8 C13 N5 -152.6(4) . . . . ?
O8 C13 N5 C14 -176.9(5) . . . . ?
O8 C13 N5 C15 2.1(7) . . . . ?

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
N1 H1N O7 0.86 1.96 2.625(3) 133.8 .
N3 H3N O4 0.86 1.91 2.728(3) 159.2 2
C16 H16 O10 0.93 2.44 3.295(4) 153.8 2_566
N4 H4N O13 0.86 2.01 2.869(3) 173.0 2_755
C13 H13 O5 0.93 2.33 3.236(4) 163.0 .
C18 H18C O10 0.96 2.45 3.365(7) 158.3 2_566

_refine_diff_density_max         0.829
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.108

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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 1539686'
_audit_update_record             
;
2017-03-22 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 La N8 O13'
_chemical_formula_weight         738.41

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   11.0950(3)
_cell_length_b                   11.1629(3)
_cell_length_c                   14.1758(4)
_cell_angle_alpha                83.7360(10)
_cell_angle_beta                 68.205(2)
_cell_angle_gamma                63.6940(10)
_cell_volume                     1458.14(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8920
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      26.37

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.541
_shelx_estimated_absorpt_T_min   0.630
_shelx_estimated_absorpt_T_max   0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14640
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.253
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5871
_reflns_number_gt                5296
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0413P)²+0.1433P] 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         5871
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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
La1 La 0.27896(2) 0.38147(2) 0.36805(2) 0.02290(6) Uani 1 1 d . . . . .
O4 O -0.4460(2) 0.2330(2) 0.29561(15) 0.0351(4) Uani 1 1 d . . . . .
O3 O -0.5204(2) 0.3897(2) 0.41293(17) 0.0495(6) Uani 1 1 d . . . . .
C5 C -0.4210(3) 0.3003(3) 0.3468(2) 0.0292(6) Uani 1 1 d . . . . .
O2 O -0.1463(2) 0.40600(19) 0.52658(14) 0.0335(4) Uani 1 1 d . . . . .
O6 O 0.6694(2) -0.2877(2) -0.18895(14) 0.0382(5) Uani 1 1 d . . . . .
O1 O 0.0446(2) 0.3992(2) 0.39429(17) 0.0410(5) Uani 1 1 d . . . . .
N1 N 0.0955(2) 0.0582(2) 0.14814(16) 0.0266(5) Uani 1 1 d . . . . .
H1N H 0.0734 0.0340 0.1038 0.032 Uiso 1 1 calc R U . . .
N2 N 0.2304(2) 0.0092(2) 0.13922(16) 0.0239(4) Uani 1 1 d . . . . .
O5 O 0.1860(2) -0.0648(2) -0.02953(16) 0.0429(5) Uani 1 1 d . . . . .
O7 O 0.5134(2) -0.0995(2) 0.12374(15) 0.0416(5) Uani 1 1 d . . . . .
O8 O 0.2988(3) 0.1461(2) 0.38475(19) 0.0522(6) Uani 1 1 d . . . . .
C4 C -0.2678(3) 0.2702(3) 0.32687(19) 0.0240(5) Uani 1 1 d . . . . .
O9 O 0.2416(3) 0.3189(3) 0.54766(17) 0.0528(6) Uani 1 1 d . . . . .
C1 C -0.0630(3) 0.3748(2) 0.4359(2) 0.0254(5) Uani 1 1 d . . . . .
C2 C -0.0952(3) 0.3050(2) 0.37032(18) 0.0217(5) Uani 1 1 d . . . . .
C9 C 0.3318(3) -0.0699(2) 0.05911(18) 0.0242(5) Uani 1 1 d . . . . .
N3 N 0.4278(2) -0.1785(2) -0.10643(17) 0.0327(5) Uani 1 1 d . . . . .
H3N H 0.4149 -0.1980 -0.1579 0.039 Uiso 1 1 calc R U . . .
C3 C -0.2378(3) 0.3317(2) 0.38931(19) 0.0235(5) Uani 1 1 d . . . . .
H3 H -0.3123 0.3905 0.4437 0.028 Uiso 1 1 calc R U . . .
C20 C 0.7604(5) 0.5507(4) 0.1740(4) 0.0896(16) Uani 1 1 d . . . . .
H20A H 0.7970 0.5790 0.2145 0.134 Uiso 1 1 calc R U . . .
H20B H 0.6893 0.5223 0.2175 0.134 Uiso 1 1 calc R U . . .
H20C H 0.7171 0.6240 0.1368 0.134 Uiso 1 1 calc R U . . .
N8 N 0.8785(3) 0.4395(3) 0.1025(2) 0.0557(8) Uani 1 1 d . . . . .
C19 C 1.0125(4) 0.3958(4) 0.0978(3) 0.0535(9) Uani 1 1 d . . . . .
H19 H 1.0273 0.4374 0.1431 0.064 Uiso 1 1 calc R U . . .
O13 O 1.1192(3) 0.3055(3) 0.0393(2) 0.0561(6) Uani 1 1 d . . . . .
C21 C 0.8436(6) 0.3836(5) 0.0371(4) 0.0818(13) Uani 1 1 d . . . . .
H21A H 0.9279 0.3071 -0.0020 0.123 Uiso 1 1 calc R U . . .
H21B H 0.8097 0.4492 -0.0081 0.123 Uiso 1 1 calc R U . . .
H21C H 0.7696 0.3566 0.0770 0.123 Uiso 1 1 calc R U . . .
C16 C 0.1642(4) 0.2898(3) 0.6233(3) 0.0467(8) Uani 1 1 d . . . . .
H16 H 0.0655 0.3325 0.6370 0.056 Uiso 1 1 calc R U . . .
N6 N 0.2087(4) 0.2036(3) 0.6867(2) 0.0647(9) Uani 1 1 d . . . . .
C18 C 0.3593(6) 0.1296(6) 0.6693(5) 0.116(2) Uani 1 1 d . . . . .
H18A H 0.4097 0.1803 0.6303 0.174 Uiso 1 1 calc R U . . .
H18B H 0.3965 0.0458 0.6326 0.174 Uiso 1 1 calc R U . . .
H18C H 0.3727 0.1132 0.7335 0.174 Uiso 1 1 calc R U . . .
C17 C 0.1087(7) 0.1774(6) 0.7780(4) 0.128(3) Uani 1 1 d . . . . .
H17A H 0.0114 0.2352 0.7831 0.193 Uiso 1 1 calc R U . . .
H17B H 0.1234 0.1940 0.8369 0.193 Uiso 1 1 calc R U . . .
H17C H 0.1255 0.0857 0.7738 0.193 Uiso 1 1 calc R U . . .
C8 C 0.0169(3) 0.2163(2) 0.28927(18) 0.0233(5) Uani 1 1 d . . . . .
H8 H 0.1116 0.2012 0.2750 0.028 Uiso 1 1 calc R U . . .
C7 C -0.0142(3) 0.1507(2) 0.22997(18) 0.0232(5) Uani 1 1 d . . . . .
C10 C 0.3062(3) -0.1028(3) -0.0260(2) 0.0282(5) Uani 1 1 d . . . . .
C11 C 0.5667(3) -0.2254(3) -0.11235(19) 0.0269(5) Uani 1 1 d . . . . .
N4 N 0.5875(2) -0.2015(2) -0.02908(16) 0.0271(5) Uani 1 1 d . . . . .
H4N H 0.6744 -0.2387 -0.0300 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4803(3) -0.1221(2) 0.05729(19) 0.0259(5) Uani 1 1 d . . . . .
C6 C -0.1560(3) 0.1787(2) 0.24698(19) 0.0244(5) Uani 1 1 d . . . . .
H6 H -0.1763 0.1370 0.2055 0.029 Uiso 1 1 calc R U . . .
O11 O 0.4077(4) 0.5103(3) 0.2315(3) 0.0787(9) Uani 1 1 d . . . . .
N7 N 0.3037(5) 0.5855(3) 0.2063(3) 0.0658(9) Uani 1 1 d . . . . .
O12 O 0.3120(5) 0.6666(4) 0.1414(3) 0.1235(15) Uani 1 1 d . . . . .
O10 O 0.1881(3) 0.5729(3) 0.2505(2) 0.0620(7) Uani 1 1 d . . . . .
C13 C 0.3118(4) 0.0431(3) 0.3507(2) 0.0412(7) Uani 1 1 d . . . . .
H13 H 0.3617 0.0207 0.2812 0.049 Uiso 1 1 calc R U . . .
C14 C 0.2868(8) -0.1620(5) 0.3617(4) 0.111(2) Uani 1 1 d . . . . .
H14A H 0.1965 -0.1647 0.3758 0.166 Uiso 1 1 calc R U . . .
H14B H 0.3449 -0.2358 0.3910 0.166 Uiso 1 1 calc R U . . .
H14C H 0.3364 -0.1682 0.2893 0.166 Uiso 1 1 calc R U . . .
C15 C 0.1766(9) -0.0009(6) 0.5140(4) 0.134(3) Uani 1 1 d . . . . .
H15A H 0.1249 -0.0544 0.5404 0.201 Uiso 1 1 calc R U . . .
H15B H 0.1094 0.0921 0.5235 0.201 Uiso 1 1 calc R U . . .
H15C H 0.2406 -0.0165 0.5494 0.201 Uiso 1 1 calc R U . . .
N5 N 0.2606(4) -0.0374(3) 0.4051(2) 0.0639(9) 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
La1 O1 2.4042(18) . ?
La1 O2 2.4641(17) 2_566 ?
La1 O9 2.495(2) . ?
La1 O8 2.530(2) . ?
La1 O3 2.5720(19) 1_655 ?
La1 O4 2.5835(18) 1_655 ?
La1 O6 2.6152(18) 2_655 ?
La1 O10 2.631(3) . ?
La1 O11 2.649(3) . ?
La1 C5 2.939(3) 1_655 ?
O4 C5 1.273(3) . ?
O4 La1 2.5835(18) 1_455 ?
O3 C5 1.246(3) . ?
O3 La1 2.5719(19) 1_455 ?
C5 C4 1.496(3) . ?
C5 La1 2.939(3) 1_455 ?
O2 C1 1.248(3) . ?
O2 La1 2.4641(17) 2_566 ?
O6 C11 1.227(3) . ?
O6 La1 2.6152(18) 2_655 ?
O1 C1 1.256(3) . ?
N1 N2 1.305(3) . ?
N1 C7 1.411(3) . ?
N1 H1N 0.8600 . ?
N2 C9 1.313(3) . ?
O5 C10 1.227(3) . ?
O7 C12 1.215(3) . ?
O8 C13 1.224(4) . ?
C4 C3 1.386(3) . ?
C4 C6 1.397(3) . ?
O9 C16 1.216(4) . ?
C1 C2 1.500(3) . ?
C2 C8 1.394(3) . ?
C2 C3 1.395(3) . ?
C9 C10 1.455(3) . ?
C9 C12 1.474(4) . ?
N3 C11 1.361(3) . ?
N3 C10 1.375(3) . ?
N3 H3N 0.8600 . ?
C3 H3 0.9300 . ?
C20 N8 1.460(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N8 C19 1.321(5) . ?
N8 C21 1.416(6) . ?
C19 O13 1.225(4) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C16 N6 1.303(4) . ?
C16 H16 0.9300 . ?
N6 C18 1.432(6) . ?
N6 C17 1.459(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8 C7 1.392(3) . ?
C8 H8 0.9300 . ?
C7 C6 1.389(3) . ?
C11 N4 1.358(3) . ?
N4 C12 1.386(3) . ?
N4 H4N 0.8600 . ?
C6 H6 0.9300 . ?
O11 N7 1.243(5) . ?
N7 O12 1.226(4) . ?
N7 O10 1.266(4) . ?
C13 N5 1.304(4) . ?
C13 H13 0.9300 . ?
C14 N5 1.447(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N5 1.467(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 La1 O2 85.43(6) . 2_566 ?
O1 La1 O9 88.41(8) . . ?
O2 La1 O9 73.96(7) 2_566 . ?
O1 La1 O8 73.34(8) . . ?
O2 La1 O8 138.01(7) 2_566 . ?
O9 La1 O8 69.75(8) . . ?
O1 La1 O3 158.01(7) . 1_655 ?
O2 La1 O3 78.72(6) 2_566 1_655 ?
O9 La1 O3 72.68(8) . 1_655 ?
O8 La1 O3 108.99(8) . 1_655 ?
O1 La1 O4 145.91(6) . 1_655 ?
O2 La1 O4 128.34(6) 2_566 1_655 ?
O9 La1 O4 96.25(7) . 1_655 ?
O8 La1 O4 76.71(7) . 1_655 ?
O3 La1 O4 50.52(6) 1_655 1_655 ?
O1 La1 O6 80.40(6) . 2_655 ?
O2 La1 O6 140.28(7) 2_566 2_655 ?
O9 La1 O6 141.69(8) . 2_655 ?
O8 La1 O6 71.94(7) . 2_655 ?
O3 La1 O6 121.43(6) 1_655 2_655 ?
O4 La1 O6 75.13(6) 1_655 2_655 ?
O1 La1 O10 77.27(9) . . ?
O2 La1 O10 73.14(8) 2_566 . ?
O9 La1 O10 144.94(8) . . ?
O8 La1 O10 133.03(8) . . ?
O3 La1 O10 111.91(9) 1_655 . ?
O4 La1 O10 113.57(8) 1_655 . ?
O6 La1 O10 67.61(8) 2_655 . ?
O1 La1 O11 124.39(9) . . ?
O2 La1 O11 85.04(9) 2_566 . ?
O9 La1 O11 139.66(9) . . ?
O8 La1 O11 136.82(10) . . ?
O3 La1 O11 69.62(9) 1_655 . ?
O4 La1 O11 70.27(9) 1_655 . ?
O6 La1 O11 73.25(9) 2_655 . ?
O10 La1 O11 47.60(9) . . ?
O1 La1 C5 167.74(8) . 1_655 ?
O2 La1 C5 102.95(7) 2_566 1_655 ?
O9 La1 C5 85.41(8) . 1_655 ?
O8 La1 C5 94.57(8) . 1_655 ?
O3 La1 C5 25.01(7) 1_655 1_655 ?
O4 La1 C5 25.63(6) 1_655 1_655 ?
O6 La1 C5 98.02(6) 2_655 1_655 ?
O10 La1 C5 113.52(9) . 1_655 ?
O11 La1 C5 65.95(9) . 1_655 ?
C5 O4 La1 92.98(15) . 1_455 ?
C5 O3 La1 94.21(15) . 1_455 ?
O3 C5 O4 121.7(2) . . ?
O3 C5 C4 119.5(2) . . ?
O4 C5 C4 118.8(2) . . ?
O3 C5 La1 60.78(14) . 1_455 ?
O4 C5 La1 61.39(13) . 1_455 ?
C4 C5 La1 173.4(2) . 1_455 ?
C1 O2 La1 132.59(17) . 2_566 ?
C11 O6 La1 139.59(18) . 2_655 ?
C1 O1 La1 155.4(2) . . ?
N2 N1 C7 120.5(2) . . ?
N2 N1 H1N 119.7 . . ?
C7 N1 H1N 119.7 . . ?
N1 N2 C9 119.7(2) . . ?
C13 O8 La1 152.2(2) . . ?
C3 C4 C6 120.4(2) . . ?
C3 C4 C5 119.6(2) . . ?
C6 C4 C5 120.0(2) . . ?
C16 O9 La1 145.1(2) . . ?
O2 C1 O1 125.4(2) . . ?
O2 C1 C2 117.6(2) . . ?
O1 C1 C2 117.0(2) . . ?
C8 C2 C3 120.3(2) . . ?
C8 C2 C1 119.9(2) . . ?
C3 C2 C1 119.8(2) . . ?
N2 C9 C10 124.4(2) . . ?
N2 C9 C12 115.4(2) . . ?
C10 C9 C12 120.1(2) . . ?
C11 N3 C10 126.2(2) . . ?
C11 N3 H3N 116.9 . . ?
C10 N3 H3N 116.9 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 N8 C21 121.8(4) . . ?
C19 N8 C20 121.0(4) . . ?
C21 N8 C20 117.2(4) . . ?
O13 C19 N8 126.0(4) . . ?
O13 C19 H19 117.0 . . ?
N8 C19 H19 117.0 . . ?
N8 C21 H21A 109.5 . . ?
N8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O9 C16 N6 125.2(4) . . ?
O9 C16 H16 117.4 . . ?
N6 C16 H16 117.4 . . ?
C16 N6 C18 121.0(4) . . ?
C16 N6 C17 122.0(4) . . ?
C18 N6 C17 117.0(4) . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N6 C17 H17A 109.5 . . ?
N6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C8 C2 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C2 C8 H8 120.3 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 N1 117.7(2) . . ?
C8 C7 N1 121.6(2) . . ?
O5 C10 N3 120.5(2) . . ?
O5 C10 C9 123.9(2) . . ?
N3 C10 C9 115.6(2) . . ?
O6 C11 N4 120.9(2) . . ?
O6 C11 N3 122.0(2) . . ?
N4 C11 N3 117.2(2) . . ?
C11 N4 C12 125.4(2) . . ?
C11 N4 H4N 117.3 . . ?
C12 N4 H4N 117.3 . . ?
O7 C12 N4 119.4(2) . . ?
O7 C12 C9 125.3(2) . . ?
N4 C12 C9 115.3(2) . . ?
C7 C6 C4 119.5(2) . . ?
C7 C6 H6 120.3 . . ?
C4 C6 H6 120.3 . . ?
N7 O11 La1 98.0(2) . . ?
O12 N7 O11 122.4(4) . . ?
O12 N7 O10 121.3(4) . . ?
O11 N7 O10 116.3(3) . . ?
N7 O10 La1 98.2(2) . . ?
O8 C13 N5 124.5(3) . . ?
O8 C13 H13 117.8 . . ?
N5 C13 H13 117.8 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 N5 C14 122.0(3) . . ?
C13 N5 C15 118.5(3) . . ?
C14 N5 C15 119.4(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
La1 O3 C5 O4 -7.7(3) 1_455 . . . ?
La1 O3 C5 C4 172.5(2) 1_455 . . . ?
La1 O4 C5 O3 7.7(3) 1_455 . . . ?
La1 O4 C5 C4 -172.5(2) 1_455 . . . ?
C7 N1 N2 C9 -175.6(2) . . . . ?
O3 C5 C4 C3 7.0(4) . . . . ?
O4 C5 C4 C3 -172.9(2) . . . . ?
O3 C5 C4 C6 -174.3(3) . . . . ?
O4 C5 C4 C6 5.8(4) . . . . ?
La1 O2 C1 O1 50.9(4) 2_566 . . . ?
La1 O2 C1 C2 -127.8(2) 2_566 . . . ?
La1 O1 C1 O2 64.6(5) . . . . ?
La1 O1 C1 C2 -116.7(4) . . . . ?
O2 C1 C2 C8 -150.8(2) . . . . ?
O1 C1 C2 C8 30.5(4) . . . . ?
O2 C1 C2 C3 30.7(4) . . . . ?
O1 C1 C2 C3 -148.0(3) . . . . ?
N1 N2 C9 C10 3.6(4) . . . . ?
N1 N2 C9 C12 -178.8(2) . . . . ?
C6 C4 C3 C2 1.9(4) . . . . ?
C5 C4 C3 C2 -179.3(2) . . . . ?
C8 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 178.1(2) . . . . ?
C21 N8 C19 O13 -0.1(6) . . . . ?
C20 N8 C19 O13 -178.3(3) . . . . ?
La1 O9 C16 N6 144.4(3) . . . . ?
O9 C16 N6 C18 -2.4(6) . . . . ?
O9 C16 N6 C17 177.8(5) . . . . ?
C3 C2 C8 C7 -2.5(4) . . . . ?
C1 C2 C8 C7 179.0(2) . . . . ?
C2 C8 C7 C6 3.9(4) . . . . ?
C2 C8 C7 N1 -178.9(2) . . . . ?
N2 N1 C7 C6 -167.5(2) . . . . ?
N2 N1 C7 C8 15.2(4) . . . . ?
C11 N3 C10 O5 179.3(3) . . . . ?
C11 N3 C10 C9 0.8(4) . . . . ?
N2 C9 C10 O5 -3.6(4) . . . . ?
C12 C9 C10 O5 178.9(3) . . . . ?
N2 C9 C10 N3 174.9(2) . . . . ?
C12 C9 C10 N3 -2.7(4) . . . . ?
La1 O6 C11 N4 176.33(19) 2_655 . . . ?
La1 O6 C11 N3 -3.1(5) 2_655 . . . ?
C10 N3 C11 O6 -176.8(3) . . . . ?
C10 N3 C11 N4 3.7(4) . . . . ?
O6 C11 N4 C12 173.7(3) . . . . ?
N3 C11 N4 C12 -6.9(4) . . . . ?
C11 N4 C12 O7 -174.2(3) . . . . ?
C11 N4 C12 C9 5.0(4) . . . . ?
N2 C9 C12 O7 1.4(4) . . . . ?
C10 C9 C12 O7 179.2(3) . . . . ?
N2 C9 C12 N4 -177.7(2) . . . . ?
C10 C9 C12 N4 0.0(4) . . . . ?
C8 C7 C6 C4 -2.3(4) . . . . ?
N1 C7 C6 C4 -179.6(2) . . . . ?
C3 C4 C6 C7 -0.6(4) . . . . ?
C5 C4 C6 C7 -179.3(2) . . . . ?
La1 O11 N7 O12 -179.4(4) . . . . ?
La1 O11 N7 O10 -0.3(4) . . . . ?
O12 N7 O10 La1 179.4(4) . . . . ?
O11 N7 O10 La1 0.3(4) . . . . ?
La1 O8 C13 N5 -151.0(4) . . . . ?
O8 C13 N5 C14 -176.2(5) . . . . ?
O8 C13 N5 C15 2.4(7) . . . . ?

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
N1 H1N O5 0.86 1.96 2.626(3) 133.7 .
N3 H3N O4 0.86 1.91 2.729(3) 159.9 2
C16 H16 O10 0.93 2.44 3.305(5) 153.9 2_566
C17 H17A O10 0.96 2.46 3.374(7) 158.0 2_566
N4 H4N O13 0.86 2.02 2.880(3) 173.0 2_755
C13 H13 O7 0.93 2.34 3.241(4) 162.9 .
N1 H1N O5 0.86 1.96 2.626(3) 133.7 .
N3 H3N O4 0.86 1.91 2.729(3) 159.9 2
C16 H16 O10 0.93 2.44 3.305(5) 153.9 2_566
C17 H17A O10 0.96 2.46 3.374(7) 158.0 2_566
N4 H4N O13 0.86 2.02 2.880(3) 173.0 2_755
C13 H13 O7 0.93 2.34 3.241(4) 162.9 .

_refine_diff_density_max         1.192
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.113

_shelxl_version_number           2014/6

