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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1448209'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 La N8 O10'
_chemical_formula_weight         610.29

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'
La La -0.2871 2.4523 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.8400(6)
_cell_length_b                   10.5881(6)
_cell_length_c                   11.9083(7)
_cell_angle_alpha                101.3140(10)
_cell_angle_beta                 111.1760(10)
_cell_angle_gamma                93.0810(10)
_cell_volume                     1123.84(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3573
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.90

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    1.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3946
_exptl_absorpt_correction_T_max  0.7182
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8491
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.40
_reflns_number_total             5601
_reflns_number_gt                4880
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0316P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5601
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
La1 La 0.590694(16) 0.183348(15) 0.265978(14) 0.03199(6) Uani 1 1 d . . .
C1 C 0.9738(7) 0.3034(5) -0.0220(5) 0.104(2) Uani 1 1 d . . .
H1A H 0.8982 0.3439 -0.0896 0.18(3) Uiso 1 1 d R . .
H1B H 1.0420 0.3665 -0.0162 0.094(16) Uiso 1 1 d R . .
H1C H 0.9729 0.2238 -0.0506 0.14(2) Uiso 1 1 d R . .
C2 C 0.9120(4) 0.3316(3) 0.0772(3) 0.0565(9) Uani 1 1 d . . .
C3 C 0.9379(4) 0.4367(3) 0.1734(3) 0.0533(9) Uani 1 1 d . . .
H3 H 1.0010 0.5129 0.1930 0.056(10) Uiso 1 1 d R . .
C4 C 0.8516(3) 0.4053(3) 0.2368(3) 0.0367(6) Uani 1 1 d . . .
C5 C 0.8351(3) 0.4811(3) 0.3471(3) 0.0342(6) Uani 1 1 d . . .
C6 C 0.9032(3) 0.6088(3) 0.4015(3) 0.0404(7) Uani 1 1 d . . .
H6 H 0.9624 0.6484 0.3693 0.051(10) Uiso 1 1 d R . .
C7 C 0.8817(3) 0.6757(3) 0.5041(3) 0.0455(7) Uani 1 1 d . . .
H7 H 0.9240 0.7615 0.5403 0.061(10) Uiso 1 1 d R . .
C8 C 0.7966(3) 0.6132(3) 0.5517(3) 0.0410(7) Uani 1 1 d . . .
H8 H 0.7811 0.6568 0.6209 0.045(9) Uiso 1 1 d R . .
C9 C 0.7347(3) 0.4841(3) 0.4958(2) 0.0334(6) Uani 1 1 d . . .
C10 C 0.6497(3) 0.4101(3) 0.5453(3) 0.0342(6) Uani 1 1 d . . .
C11 C 0.6392(3) 0.4368(3) 0.6612(3) 0.0403(7) Uani 1 1 d . . .
H11 H 0.6829 0.5103 0.7251 0.046(9) Uiso 1 1 d R . .
C12 C 0.5519(3) 0.3315(3) 0.6620(3) 0.0407(7) Uani 1 1 d . . .
C13 C 0.5004(5) 0.3016(4) 0.7595(3) 0.0595(10) Uani 1 1 d . . .
H13A H 0.5497 0.2265 0.7856 0.15(2) Uiso 1 1 d R . .
H13B H 0.5332 0.3732 0.8251 0.123(19) Uiso 1 1 d R . .
H13C H 0.3984 0.2758 0.7262 0.20(3) Uiso 1 1 d R . .
C14 C 0.8512(3) -0.0172(3) 0.1996(3) 0.0501(8) Uani 1 1 d . . .
H14A H 0.9124 0.0631 0.2520 0.052(9) Uiso 1 1 d R . .
H14B H 0.8689 -0.0343 0.1233 0.051(9) Uiso 1 1 d R . .
C15 C 0.8938(4) -0.1260(4) 0.2624(4) 0.0638(10) Uani 1 1 d . . .
H15A H 0.8358 -0.2057 0.2108 0.095(16) Uiso 1 1 d R . .
H15B H 0.9948 -0.1330 0.2789 0.096(15) Uiso 1 1 d R . .
H15C H 0.8788 -0.1090 0.3382 0.089(15) Uiso 1 1 d R . .
N1 N 0.8145(3) 0.2447(3) 0.0857(2) 0.0514(7) Uani 1 1 d . . .
H1 H 0.7799 0.1703 0.0346 0.062 Uiso 1 1 calc R . .
N2 N 0.7764(3) 0.2869(2) 0.1839(2) 0.0420(6) Uani 1 1 d . . .
N3 N 0.7517(2) 0.4198(2) 0.3931(2) 0.0330(5) Uani 1 1 d . . .
N4 N 0.5713(3) 0.2961(2) 0.4768(2) 0.0398(6) Uani 1 1 d . . .
N5 N 0.5141(3) 0.2502(2) 0.5505(2) 0.0442(6) Uani 1 1 d . . .
H5 H 0.4592 0.1766 0.5285 0.053 Uiso 1 1 calc R . .
N6 N 0.4252(3) 0.3141(3) 0.0581(2) 0.0455(6) Uani 1 1 d . . .
N7 N 0.2744(3) 0.0510(3) 0.1616(3) 0.0526(7) Uani 1 1 d . . .
N8 N 0.7186(3) 0.0353(3) 0.4656(2) 0.0466(6) Uani 1 1 d . . .
O1 O 0.4757(3) 0.3718(2) 0.17039(19) 0.0519(6) Uani 1 1 d . . .
O2 O 0.4510(2) 0.1962(2) 0.03456(19) 0.0503(6) Uani 1 1 d . . .
O3 O 0.3554(3) 0.3648(3) -0.0235(3) 0.0779(8) Uani 1 1 d . . .
O4 O 0.3198(2) 0.1595(3) 0.2384(2) 0.0604(7) Uani 1 1 d . . .
O5 O 0.3690(2) -0.0101(2) 0.1342(2) 0.0518(6) Uani 1 1 d . . .
O6 O 0.1453(3) 0.0076(3) 0.1137(3) 0.0949(11) Uani 1 1 d . . .
O7 O 0.7992(2) 0.1230(2) 0.4511(2) 0.0485(5) Uani 1 1 d . . .
O8 O 0.5844(2) 0.0127(2) 0.3938(2) 0.0459(5) Uani 1 1 d . . .
O9 O 0.7664(3) -0.0277(3) 0.5431(3) 0.0817(9) Uani 1 1 d . . .
O10 O 0.6991(2) -0.0002(2) 0.17179(18) 0.0412(5) Uani 1 1 d . . .
H10 H 0.6311 -0.0662 0.1105 0.049 Uiso 1 1 calc R . .


_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 O10 2.5312(18) . ?
La1 O4 2.558(2) . ?
La1 O8 2.592(2) . ?
La1 O1 2.600(2) . ?
La1 O7 2.628(2) . ?
La1 O2 2.633(2) . ?
La1 N4 2.638(2) . ?
La1 N2 2.645(2) . ?
La1 O5 2.684(2) . ?
La1 N3 2.725(2) . ?
C1 C2 1.501(5) . ?
C2 N1 1.338(4) . ?
C2 C3 1.369(5) . ?
C3 C4 1.390(4) . ?
C4 N2 1.331(4) . ?
C4 C5 1.466(4) . ?
C5 N3 1.341(3) . ?
C5 C6 1.394(4) . ?
C6 C7 1.379(4) . ?
C7 C8 1.375(4) . ?
C8 C9 1.395(4) . ?
C9 N3 1.349(3) . ?
C9 C10 1.459(4) . ?
C10 N4 1.333(3) . ?
C10 C11 1.395(4) . ?
C11 C12 1.373(4) . ?
C12 N5 1.342(3) . ?
C12 C13 1.503(4) . ?
C14 O10 1.441(3) . ?
C14 C15 1.492(5) . ?
N1 N2 1.356(3) . ?
N4 N5 1.349(3) . ?
N6 O3 1.211(4) . ?
N6 O1 1.255(3) . ?
N6 O2 1.284(3) . ?
N7 O6 1.209(3) . ?
N7 O5 1.262(3) . ?
N7 O4 1.262(3) . ?
N8 O9 1.217(4) . ?
N8 O8 1.266(3) . ?
N8 O7 1.267(3) . ?

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
O10 La1 O4 121.52(7) . . ?
O10 La1 O8 77.62(7) . . ?
O4 La1 O8 78.89(8) . . ?
O10 La1 O1 128.05(7) . . ?
O4 La1 O1 72.48(8) . . ?
O8 La1 O1 148.92(7) . . ?
O10 La1 O7 73.48(7) . . ?
O4 La1 O7 123.04(8) . . ?
O8 La1 O7 48.95(7) . . ?
O1 La1 O7 145.44(7) . . ?
O10 La1 O2 84.03(7) . . ?
O4 La1 O2 76.32(8) . . ?
O8 La1 O2 134.82(7) . . ?
O1 La1 O2 48.50(7) . . ?
O7 La1 O2 155.82(7) . . ?
O10 La1 N4 141.89(8) . . ?
O4 La1 N4 71.45(7) . . ?
O8 La1 N4 69.85(7) . . ?
O1 La1 N4 89.45(7) . . ?
O7 La1 N4 70.35(8) . . ?
O2 La1 N4 133.37(8) . . ?
O10 La1 N2 72.35(7) . . ?
O4 La1 N2 142.24(9) . . ?
O8 La1 N2 138.08(8) . . ?
O1 La1 N2 72.38(8) . . ?
O7 La1 N2 94.05(8) . . ?
O2 La1 N2 70.27(8) . . ?
N4 La1 N2 121.40(7) . . ?
O10 La1 O5 73.09(7) . . ?
O4 La1 O5 48.54(7) . . ?
O8 La1 O5 69.39(7) . . ?
O1 La1 O5 99.11(7) . . ?
O7 La1 O5 114.16(7) . . ?
O2 La1 O5 65.84(7) . . ?
N4 La1 O5 111.58(7) . . ?
N2 La1 O5 125.87(7) . . ?
O10 La1 N3 122.10(6) . . ?
O4 La1 N3 116.33(7) . . ?
O8 La1 N3 116.97(7) . . ?
O1 La1 N3 67.61(7) . . ?
O7 La1 N3 77.99(7) . . ?
O2 La1 N3 107.80(7) . . ?
N4 La1 N3 60.94(7) . . ?
N2 La1 N3 60.61(7) . . ?
O5 La1 N3 163.81(7) . . ?
N1 C2 C3 106.1(3) . . ?
N1 C2 C1 121.6(3) . . ?
C3 C2 C1 132.3(4) . . ?
C2 C3 C4 106.1(3) . . ?
N2 C4 C3 110.6(3) . . ?
N2 C4 C5 119.3(2) . . ?
C3 C4 C5 130.0(3) . . ?
N3 C5 C6 122.1(3) . . ?
N3 C5 C4 116.1(2) . . ?
C6 C5 C4 121.9(3) . . ?
C7 C6 C5 119.1(3) . . ?
C8 C7 C6 119.0(3) . . ?
C7 C8 C9 119.4(3) . . ?
N3 C9 C8 121.7(3) . . ?
N3 C9 C10 116.2(2) . . ?
C8 C9 C10 122.2(2) . . ?
N4 C10 C11 110.7(3) . . ?
N4 C10 C9 119.3(2) . . ?
C11 C10 C9 129.9(2) . . ?
C12 C11 C10 105.9(3) . . ?
N5 C12 C11 105.9(3) . . ?
N5 C12 C13 122.5(3) . . ?
C11 C12 C13 131.6(3) . . ?
O10 C14 C15 112.5(3) . . ?
C2 N1 N2 112.4(3) . . ?
C4 N2 N1 104.7(2) . . ?
C4 N2 La1 122.56(18) . . ?
N1 N2 La1 132.69(18) . . ?
C5 N3 C9 118.7(2) . . ?
C5 N3 La1 120.78(16) . . ?
C9 N3 La1 120.08(17) . . ?
C10 N4 N5 104.7(2) . . ?
C10 N4 La1 122.30(18) . . ?
N5 N4 La1 131.70(17) . . ?
C12 N5 N4 112.9(2) . . ?
O3 N6 O1 122.8(3) . . ?
O3 N6 O2 121.6(3) . . ?
O1 N6 O2 115.7(3) . . ?
O6 N7 O5 120.8(3) . . ?
O6 N7 O4 121.8(3) . . ?
O5 N7 O4 117.4(2) . . ?
O9 N8 O8 120.2(3) . . ?
O9 N8 O7 122.4(3) . . ?
O8 N8 O7 117.3(3) . . ?
N6 O1 La1 99.12(18) . . ?
N6 O2 La1 96.67(16) . . ?
N7 O4 La1 99.93(17) . . ?
N7 O5 La1 93.82(17) . . ?
N8 O7 La1 96.01(17) . . ?
N8 O8 La1 97.75(17) . . ?
C14 O10 La1 129.23(17) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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 1448210'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 Ce N8 O10'
_chemical_formula_weight         611.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.8357(11)
_cell_length_b                   10.5776(12)
_cell_length_c                   11.8760(13)
_cell_angle_alpha                101.212(2)
_cell_angle_beta                 111.261(2)
_cell_angle_gamma                93.071(2)
_cell_volume                     1119.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5034
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      28.33

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             606
_exptl_absorpt_coefficient_mu    2.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4020
_exptl_absorpt_correction_T_max  0.6006
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         O
_diffrn_standards_interval_count O
_diffrn_standards_interval_time  O
_diffrn_standards_decay_%        O
_diffrn_reflns_number            8380
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.39
_reflns_number_total             5551
_reflns_number_gt                5044
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0283P)²+0.5306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5551
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ce1 Ce 0.090938(15) 0.185119(13) 0.265922(12) 0.02981(5) Uani 1 1 d . . .
C1 C -0.0014(4) 0.3001(3) 0.7579(3) 0.0559(8) Uani 1 1 d . . .
H1A H 0.0748 0.3489 0.8397 0.124(19) Uiso 1 1 d R . .
H1B H -0.0899 0.3295 0.7475 0.16(3) Uiso 1 1 d R . .
H1C H -0.0009 0.2108 0.7561 0.14(2) Uiso 1 1 d R . .
C2 C 0.0505(3) 0.3307(3) 0.6611(3) 0.0391(6) Uani 1 1 d . . .
C3 C 0.1385(3) 0.4361(3) 0.6613(2) 0.0388(6) Uani 1 1 d . . .
H3 H 0.1824 0.5092 0.7256 0.053(9) Uiso 1 1 d R . .
C4 C 0.1490(3) 0.4099(2) 0.5450(2) 0.0328(5) Uani 1 1 d . . .
C5 C 0.2345(3) 0.4845(2) 0.4954(2) 0.0317(5) Uani 1 1 d . . .
C6 C 0.2972(3) 0.6134(3) 0.5525(3) 0.0393(6) Uani 1 1 d . . .
H6A H 0.2824 0.6572 0.6221 0.042(8) Uiso 1 1 d R . .
C7 C 0.3825(3) 0.6750(3) 0.5034(3) 0.0433(7) Uani 1 1 d . . .
H7 H 0.4251 0.7609 0.5392 0.053(9) Uiso 1 1 d R . .
C8 C 0.4036(3) 0.6087(3) 0.4006(3) 0.0400(6) Uani 1 1 d . . .
H8 H 0.4628 0.6483 0.3681 0.057(10) Uiso 1 1 d R . .
C9 C 0.3347(3) 0.4808(2) 0.3460(2) 0.0332(5) Uani 1 1 d . . .
C10 C 0.3507(3) 0.4050(3) 0.2353(2) 0.0353(5) Uani 1 1 d . . .
C11 C 0.4381(4) 0.4346(3) 0.1714(3) 0.0507(8) Uani 1 1 d . . .
H11 H 0.5022 0.5104 0.1905 0.068(11) Uiso 1 1 d R . .
C12 C 0.4094(4) 0.3294(3) 0.0742(3) 0.0560(9) Uani 1 1 d . . .
C13 C 0.4710(7) 0.3008(5) -0.0254(5) 0.0971(18) Uani 1 1 d . . .
H13A H 0.3955 0.2992 -0.1053 0.18(3) Uiso 1 1 d R . .
H13B H 0.5480 0.3681 -0.0044 0.103(17) Uiso 1 1 d R . .
H13C H 0.5039 0.2183 -0.0249 0.17(3) Uiso 1 1 d R . .
C14 C 0.3501(3) -0.0153(3) 0.1991(3) 0.0475(7) Uani 1 1 d . . .
H14A H 0.3669 -0.0332 0.1224 0.062(11) Uiso 1 1 d R . .
H14B H 0.4118 0.0650 0.2512 0.060(10) Uiso 1 1 d R . .
C15 C 0.3928(4) -0.1244(4) 0.2627(3) 0.0589(9) Uani 1 1 d . . .
H15A H 0.3342 -0.2032 0.2128 0.084(14) Uiso 1 1 d R . .
H15B H 0.4923 -0.1326 0.2778 0.071(12) Uiso 1 1 d R . .
H15C H 0.3801 -0.1068 0.3389 0.103(17) Uiso 1 1 d R . .
N1 N 0.0123(3) 0.2495(2) 0.5483(2) 0.0418(6) Uani 1 1 d . . .
H1 H -0.0436 0.1763 0.5255 0.050 Uiso 1 1 calc R . .
N2 N 0.0710(3) 0.2955(2) 0.4751(2) 0.0374(5) Uani 1 1 d . . .
N3 N 0.2514(2) 0.4195(2) 0.39276(19) 0.0312(4) Uani 1 1 d . . .
N4 N 0.2742(3) 0.2865(2) 0.1825(2) 0.0408(5) Uani 1 1 d . . .
N5 N 0.3109(3) 0.2433(2) 0.0838(2) 0.0481(6) Uani 1 1 d . . .
H5 H 0.2752 0.1689 0.0328 0.058 Uiso 1 1 calc R . .
N6 N 0.2177(3) 0.0373(2) 0.4643(2) 0.0442(6) Uani 1 1 d . . .
N7 N -0.2239(3) 0.0522(3) 0.1621(2) 0.0499(6) Uani 1 1 d . . .
N8 N -0.0752(3) 0.3138(2) 0.0575(2) 0.0429(5) Uani 1 1 d . . .
O1 O 0.2986(2) 0.1255(2) 0.45021(19) 0.0460(5) Uani 1 1 d . . .
O2 O 0.0837(2) 0.01515(19) 0.39201(19) 0.0440(5) Uani 1 1 d . . .
O3 O 0.2647(3) -0.0265(3) 0.5418(3) 0.0786(8) Uani 1 1 d . . .
O4 O -0.1781(2) 0.1612(2) 0.2393(2) 0.0569(6) Uani 1 1 d . . .
O5 O -0.1285(2) -0.0086(2) 0.1348(2) 0.0497(5) Uani 1 1 d . . .
O6 O -0.3535(3) 0.0099(3) 0.1156(3) 0.0910(10) Uani 1 1 d . . .
O7 O -0.0236(3) 0.3725(2) 0.17060(19) 0.0500(5) Uani 1 1 d . . .
O8 O -0.0492(2) 0.1965(2) 0.03467(18) 0.0475(5) Uani 1 1 d . . .
O9 O -0.1440(3) 0.3653(3) -0.0237(2) 0.0755(8) Uani 1 1 d . . .
O10 O 0.1974(2) 0.00229(18) 0.17163(17) 0.0390(4) Uani 1 1 d . . .
H10 H 0.1289 -0.0635 0.1103 0.047 Uiso 1 1 calc R . .


_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 O10 2.5133(18) . ?
Ce1 O4 2.541(2) . ?
Ce1 O2 2.567(2) . ?
Ce1 O7 2.582(2) . ?
Ce1 O1 2.606(2) . ?
Ce1 N2 2.612(2) . ?
Ce1 O8 2.619(2) . ?
Ce1 N4 2.623(2) . ?
Ce1 O5 2.670(2) . ?
Ce1 N3 2.704(2) . ?
C1 C2 1.496(4) . ?
C2 N1 1.352(3) . ?
C2 C3 1.373(4) . ?
C3 C4 1.398(4) . ?
C4 N2 1.338(3) . ?
C4 C5 1.465(4) . ?
C5 N3 1.349(3) . ?
C5 C6 1.395(4) . ?
C6 C7 1.384(4) . ?
C7 C8 1.375(4) . ?
C8 C9 1.397(4) . ?
C9 N3 1.347(3) . ?
C9 C10 1.466(4) . ?
C10 N4 1.335(3) . ?
C10 C11 1.396(4) . ?
C11 C12 1.371(5) . ?
C12 N5 1.344(4) . ?
C12 C13 1.502(5) . ?
C14 O10 1.447(3) . ?
C14 C15 1.496(5) . ?
N1 N2 1.351(3) . ?
N4 N5 1.353(3) . ?
N6 O3 1.218(3) . ?
N6 O2 1.264(3) . ?
N6 O1 1.268(3) . ?
N7 O6 1.209(3) . ?
N7 O5 1.266(3) . ?
N7 O4 1.268(3) . ?
N8 O9 1.206(3) . ?
N8 O7 1.262(3) . ?
N8 O8 1.278(3) . ?

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
O10 Ce1 O4 121.29(7) . . ?
O10 Ce1 O2 77.54(7) . . ?
O4 Ce1 O2 78.44(8) . . ?
O10 Ce1 O7 128.00(6) . . ?
O4 Ce1 O7 72.67(8) . . ?
O2 Ce1 O7 148.79(7) . . ?
O10 Ce1 O1 73.70(7) . . ?
O4 Ce1 O1 122.87(8) . . ?
O2 Ce1 O1 49.37(6) . . ?
O7 Ce1 O1 145.33(7) . . ?
O10 Ce1 N2 141.90(7) . . ?
O4 Ce1 N2 71.04(7) . . ?
O2 Ce1 N2 69.77(7) . . ?
O7 Ce1 N2 89.59(7) . . ?
O1 Ce1 N2 70.35(7) . . ?
O10 Ce1 O8 83.66(6) . . ?
O4 Ce1 O8 76.43(8) . . ?
O2 Ce1 O8 134.12(6) . . ?
O7 Ce1 O8 48.83(6) . . ?
O1 Ce1 O8 155.73(7) . . ?
N2 Ce1 O8 133.55(7) . . ?
O10 Ce1 N4 72.16(7) . . ?
O4 Ce1 N4 142.37(8) . . ?
O2 Ce1 N4 138.26(7) . . ?
O7 Ce1 N4 72.46(8) . . ?
O1 Ce1 N4 94.15(7) . . ?
N2 Ce1 N4 122.19(7) . . ?
O8 Ce1 N4 70.19(7) . . ?
O10 Ce1 O5 72.49(7) . . ?
O4 Ce1 O5 48.92(7) . . ?
O2 Ce1 O5 68.84(7) . . ?
O7 Ce1 O5 99.46(7) . . ?
O1 Ce1 O5 113.95(7) . . ?
N2 Ce1 O5 111.41(7) . . ?
O8 Ce1 O5 65.66(7) . . ?
N4 Ce1 O5 125.34(7) . . ?
O10 Ce1 N3 122.28(6) . . ?
O4 Ce1 N3 116.39(7) . . ?
O2 Ce1 N3 117.14(6) . . ?
O7 Ce1 N3 67.77(7) . . ?
O1 Ce1 N3 77.72(6) . . ?
N2 Ce1 N3 61.21(7) . . ?
O8 Ce1 N3 108.34(6) . . ?
N4 Ce1 N3 61.11(7) . . ?
O5 Ce1 N3 164.32(7) . . ?
N1 C2 C3 106.0(2) . . ?
N1 C2 C1 122.4(3) . . ?
C3 C2 C1 131.6(3) . . ?
C2 C3 C4 105.7(2) . . ?
N2 C4 C3 111.2(2) . . ?
N2 C4 C5 118.9(2) . . ?
C3 C4 C5 129.9(2) . . ?
N3 C5 C6 122.3(2) . . ?
N3 C5 C4 115.6(2) . . ?
C6 C5 C4 122.0(2) . . ?
C7 C6 C5 118.4(3) . . ?
C8 C7 C6 119.7(2) . . ?
C7 C8 C9 118.9(3) . . ?
N3 C9 C8 122.0(2) . . ?
N3 C9 C10 116.1(2) . . ?
C8 C9 C10 121.8(2) . . ?
N4 C10 C11 110.4(2) . . ?
N4 C10 C9 119.0(2) . . ?
C11 C10 C9 130.6(3) . . ?
C12 C11 C10 106.1(3) . . ?
N5 C12 C11 106.0(3) . . ?
N5 C12 C13 122.2(3) . . ?
C11 C12 C13 131.8(3) . . ?
O10 C14 C15 112.5(3) . . ?
N2 N1 C2 112.9(2) . . ?
C4 N2 N1 104.3(2) . . ?
C4 N2 Ce1 122.63(17) . . ?
N1 N2 Ce1 131.88(16) . . ?
C9 N3 C5 118.5(2) . . ?
C9 N3 Ce1 120.52(16) . . ?
C5 N3 Ce1 120.42(16) . . ?
C10 N4 N5 104.8(2) . . ?
C10 N4 Ce1 122.59(17) . . ?
N5 N4 Ce1 132.52(18) . . ?
C12 N5 N4 112.6(2) . . ?
O3 N6 O2 120.0(3) . . ?
O3 N6 O1 122.9(3) . . ?
O2 N6 O1 117.1(2) . . ?
O6 N7 O5 122.0(3) . . ?
O6 N7 O4 121.0(3) . . ?
O5 N7 O4 117.0(2) . . ?
O9 N8 O7 122.2(3) . . ?
O9 N8 O8 122.2(3) . . ?
O7 N8 O8 115.6(2) . . ?
N6 O1 Ce1 95.76(16) . . ?
N6 O2 Ce1 97.73(15) . . ?
N7 O4 Ce1 99.97(17) . . ?
N7 O5 Ce1 93.79(16) . . ?
N8 O7 Ce1 98.87(16) . . ?
N8 O8 Ce1 96.63(15) . . ?
C14 O10 Ce1 129.25(17) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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 1448211'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N8 O10 Pr'
_chemical_formula_weight         612.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.8334(6)
_cell_length_b                   10.5636(7)
_cell_length_c                   11.8353(8)
_cell_angle_alpha                101.1470(10)
_cell_angle_beta                 111.3090(10)
_cell_angle_gamma                93.0680(10)
_cell_volume                     1113.40(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4371
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.33

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3923
_exptl_absorpt_correction_T_max  0.6134
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8277
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         28.37
_reflns_number_total             5516
_reflns_number_gt                4967
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.3066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5516
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pr1 Pr 0.408885(15) 0.813746(13) 0.234102(13) 0.03030(6) Uani 1 1 d . . .
C1 C 0.0320(8) 0.7002(5) 0.5277(6) 0.0944(18) Uani 1 1 d . . .
H1A H -0.0345 0.6225 0.5238 0.109(18) Uiso 1 1 d R . .
H1B H -0.0485 0.7637 0.5018 0.22(4) Uiso 1 1 d R . .
H1C H 0.0956 0.7353 0.6014 0.16(3) Uiso 1 1 d R . .
C2 C 0.0924(5) 0.6719(4) 0.4273(3) 0.0536(9) Uani 1 1 d . . .
C3 C 0.0637(4) 0.5665(3) 0.3301(3) 0.0517(8) Uani 1 1 d . . .
H3A H -0.0003 0.4906 0.3114 0.082(14) Uiso 1 1 d R . .
C4 C 0.1500(3) 0.5959(3) 0.2654(3) 0.0359(6) Uani 1 1 d . . .
C5 C 0.1655(3) 0.5200(3) 0.1544(3) 0.0326(6) Uani 1 1 d . . .
C6 C 0.0963(3) 0.3924(3) 0.0999(3) 0.0409(7) Uani 1 1 d . . .
H6 H 0.0367 0.3534 0.1327 0.052(10) Uiso 1 1 d R . .
C7 C 0.1179(3) 0.3256(3) -0.0030(3) 0.0438(7) Uani 1 1 d . . .
H7 H 0.0756 0.2393 -0.0388 0.052(10) Uiso 1 1 d R . .
C8 C 0.2021(3) 0.3871(3) -0.0523(3) 0.0403(7) Uani 1 1 d . . .
H8 H 0.2160 0.3435 -0.1226 0.051(10) Uiso 1 1 d R . .
C9 C 0.2658(3) 0.5162(3) 0.0046(3) 0.0327(6) Uani 1 1 d . . .
C10 C 0.3510(3) 0.5906(3) -0.0446(3) 0.0331(6) Uani 1 1 d . . .
C11 C 0.3621(3) 0.5652(3) -0.1604(3) 0.0406(7) Uani 1 1 d . . .
H11 H 0.3185 0.4921 -0.2252 0.047(9) Uiso 1 1 d R . .
C12 C 0.4510(3) 0.6704(3) -0.1604(3) 0.0405(7) Uani 1 1 d . . .
C13 C 0.5026(5) 0.7011(4) -0.2573(3) 0.0557(9) Uani 1 1 d . . .
H13A H 0.4624 0.7717 -0.2905 0.115(19) Uiso 1 1 d R . .
H13B H 0.4881 0.6263 -0.3236 0.114(18) Uiso 1 1 d R . .
H13C H 0.6135 0.7280 -0.2180 0.19(3) Uiso 1 1 d R . .
C14 C 0.1506(4) 1.0135(3) 0.3007(3) 0.0468(7) Uani 1 1 d . . .
H14A H 0.0890 0.9336 0.2474 0.051(10) Uiso 1 1 d R . .
H14B H 0.1329 1.0302 0.3772 0.060(11) Uiso 1 1 d R . .
C15 C 0.1083(4) 1.1228(4) 0.2369(4) 0.0596(10) Uani 1 1 d . . .
H15A H 0.1671 1.2016 0.2895 0.096(17) Uiso 1 1 d R . .
H15B H 0.0072 1.1306 0.2200 0.071(13) Uiso 1 1 d R . .
H15C H 0.1232 1.1064 0.1605 0.090(16) Uiso 1 1 d R . .
N1 N 0.4881(3) 0.7512(2) -0.0471(2) 0.0420(6) Uani 1 1 d . . .
H1 H 0.5436 0.8248 -0.0237 0.050 Uiso 1 1 calc R . .
N2 N 0.4290(3) 0.7041(2) 0.0254(2) 0.0382(5) Uani 1 1 d . . .
N3 N 0.2492(2) 0.5813(2) 0.1077(2) 0.0315(5) Uani 1 1 d . . .
N4 N 0.2267(3) 0.7138(2) 0.3184(2) 0.0397(6) Uani 1 1 d . . .
N5 N 0.1911(3) 0.7574(3) 0.4175(2) 0.0466(6) Uani 1 1 d . . .
H5 H 0.2275 0.8318 0.4686 0.056 Uiso 1 1 calc R . .
N6 N 0.2823(3) 0.9613(3) 0.0367(3) 0.0438(6) Uani 1 1 d . . .
N7 N 0.7222(3) 0.9466(3) 0.3371(3) 0.0489(7) Uani 1 1 d . . .
N8 N 0.5744(3) 0.6854(3) 0.4414(2) 0.0436(6) Uani 1 1 d . . .
O1 O 0.2017(2) 0.8731(2) 0.0510(2) 0.0452(5) Uani 1 1 d . . .
O2 O 0.4167(2) 0.98319(19) 0.1089(2) 0.0425(5) Uani 1 1 d . . .
O3 O 0.2344(4) 1.0248(3) -0.0415(3) 0.0767(9) Uani 1 1 d . . .
O4 O 0.6748(2) 0.8377(2) 0.2599(2) 0.0551(6) Uani 1 1 d . . .
O5 O 0.6276(3) 1.0073(2) 0.3651(2) 0.0502(6) Uani 1 1 d . . .
O6 O 0.8522(3) 0.9895(3) 0.3842(3) 0.0884(10) Uani 1 1 d . . .
O7 O 0.5224(3) 0.6273(2) 0.3281(2) 0.0482(5) Uani 1 1 d . . .
O8 O 0.5487(2) 0.8036(2) 0.46453(19) 0.0462(5) Uani 1 1 d . . .
O9 O 0.6448(4) 0.6344(3) 0.5233(3) 0.0748(9) Uani 1 1 d . . .
O10 O 0.3034(2) 0.99603(19) 0.32823(18) 0.0386(5) Uani 1 1 d . . .
H10 H 0.3720 1.0619 0.3896 0.046 Uiso 1 1 calc R . .


_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
Pr1 O10 2.4996(19) . ?
Pr1 O4 2.513(2) . ?
Pr1 O2 2.550(2) . ?
Pr1 O7 2.558(2) . ?
Pr1 O1 2.587(2) . ?
Pr1 O8 2.597(2) . ?
Pr1 N2 2.599(2) . ?
Pr1 N4 2.612(2) . ?
Pr1 O5 2.663(2) . ?
Pr1 N3 2.682(2) . ?
C1 C2 1.500(5) . ?
C2 N5 1.342(4) . ?
C2 C3 1.370(5) . ?
C3 C4 1.393(4) . ?
C4 N4 1.330(4) . ?
C4 C5 1.465(4) . ?
C5 N3 1.346(4) . ?
C5 C6 1.394(4) . ?
C6 C7 1.378(4) . ?
C7 C8 1.375(5) . ?
C8 C9 1.397(4) . ?
C9 N3 1.350(3) . ?
C9 C10 1.456(4) . ?
C10 N2 1.329(3) . ?
C10 C11 1.390(4) . ?
C11 C12 1.376(4) . ?
C12 N1 1.352(4) . ?
C12 C13 1.493(4) . ?
C14 O10 1.448(4) . ?
C14 C15 1.495(5) . ?
N1 N2 1.348(3) . ?
N4 N5 1.348(3) . ?
N6 O3 1.219(4) . ?
N6 O2 1.265(3) . ?
N6 O1 1.266(3) . ?
N7 O6 1.214(4) . ?
N7 O5 1.262(4) . ?
N7 O4 1.266(3) . ?
N8 O9 1.210(4) . ?
N8 O7 1.260(3) . ?
N8 O8 1.284(3) . ?

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
O10 Pr1 O4 121.18(7) . . ?
O10 Pr1 O2 77.46(7) . . ?
O4 Pr1 O2 78.15(8) . . ?
O10 Pr1 O7 128.25(7) . . ?
O4 Pr1 O7 72.78(9) . . ?
O2 Pr1 O7 148.60(8) . . ?
O10 Pr1 O1 73.57(7) . . ?
O4 Pr1 O1 122.96(8) . . ?
O2 Pr1 O1 49.74(7) . . ?
O7 Pr1 O1 145.11(7) . . ?
O10 Pr1 O8 83.47(7) . . ?
O4 Pr1 O8 76.47(8) . . ?
O2 Pr1 O8 133.64(7) . . ?
O7 Pr1 O8 49.32(7) . . ?
O1 Pr1 O8 155.44(7) . . ?
O10 Pr1 N2 141.91(8) . . ?
O4 Pr1 N2 70.84(8) . . ?
O2 Pr1 N2 69.80(7) . . ?
O7 Pr1 N2 89.36(7) . . ?
O1 Pr1 N2 70.59(8) . . ?
O8 Pr1 N2 133.64(7) . . ?
O10 Pr1 N4 71.98(7) . . ?
O4 Pr1 N4 142.54(9) . . ?
O2 Pr1 N4 138.28(8) . . ?
O7 Pr1 N4 72.67(8) . . ?
O1 Pr1 N4 93.95(8) . . ?
O8 Pr1 N4 70.24(8) . . ?
N2 Pr1 N4 122.59(7) . . ?
O10 Pr1 O5 72.30(7) . . ?
O4 Pr1 O5 49.01(7) . . ?
O2 Pr1 O5 68.60(7) . . ?
O7 Pr1 O5 99.69(8) . . ?
O1 Pr1 O5 113.97(7) . . ?
O8 Pr1 O5 65.42(7) . . ?
N2 Pr1 O5 111.35(8) . . ?
N4 Pr1 O5 125.04(8) . . ?
O10 Pr1 N3 122.30(7) . . ?
O4 Pr1 N3 116.49(7) . . ?
O2 Pr1 N3 117.23(7) . . ?
O7 Pr1 N3 67.71(7) . . ?
O1 Pr1 N3 77.55(7) . . ?
O8 Pr1 N3 108.73(7) . . ?
N2 Pr1 N3 61.31(7) . . ?
N4 Pr1 N3 61.40(7) . . ?
O5 Pr1 N3 164.52(7) . . ?
N5 C2 C3 106.0(3) . . ?
N5 C2 C1 122.3(4) . . ?
C3 C2 C1 131.7(4) . . ?
C2 C3 C4 106.1(3) . . ?
N4 C4 C3 110.3(3) . . ?
N4 C4 C5 119.1(3) . . ?
C3 C4 C5 130.7(3) . . ?
N3 C5 C6 122.2(3) . . ?
N3 C5 C4 116.0(2) . . ?
C6 C5 C4 121.7(3) . . ?
C7 C6 C5 118.8(3) . . ?
C8 C7 C6 119.7(3) . . ?
C7 C8 C9 118.9(3) . . ?
N3 C9 C8 121.9(3) . . ?
N3 C9 C10 115.5(2) . . ?
C8 C9 C10 122.6(3) . . ?
N2 C10 C11 111.0(3) . . ?
N2 C10 C9 118.9(2) . . ?
C11 C10 C9 130.1(3) . . ?
C12 C11 C10 106.1(3) . . ?
N1 C12 C11 105.4(3) . . ?
N1 C12 C13 122.8(3) . . ?
C11 C12 C13 131.8(3) . . ?
O10 C14 C15 112.3(3) . . ?
N2 N1 C12 112.8(2) . . ?
C10 N2 N1 104.8(2) . . ?
C10 N2 Pr1 122.61(19) . . ?
N1 N2 Pr1 131.39(17) . . ?
C5 N3 C9 118.4(2) . . ?
C5 N3 Pr1 120.58(17) . . ?
C9 N3 Pr1 120.44(17) . . ?
C4 N4 N5 105.2(2) . . ?
C4 N4 Pr1 122.32(19) . . ?
N5 N4 Pr1 132.46(19) . . ?
C2 N5 N4 112.4(3) . . ?
O3 N6 O2 120.3(3) . . ?
O3 N6 O1 122.5(3) . . ?
O2 N6 O1 117.2(3) . . ?
O6 N7 O5 121.4(3) . . ?
O6 N7 O4 122.0(3) . . ?
O5 N7 O4 116.6(3) . . ?
O9 N8 O7 122.6(3) . . ?
O9 N8 O8 121.9(3) . . ?
O7 N8 O8 115.4(3) . . ?
N6 O1 Pr1 95.61(18) . . ?
N6 O2 Pr1 97.46(16) . . ?
N7 O4 Pr1 100.64(18) . . ?
N7 O5 Pr1 93.47(17) . . ?
N8 O7 Pr1 98.88(17) . . ?
N8 O8 Pr1 96.34(16) . . ?
C14 O10 Pr1 129.12(17) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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 1448212'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N8 Nd O10'
_chemical_formula_weight         615.62

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'
Nd Nd -0.1943 3.0179 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.847(3)
_cell_length_b                   10.559(3)
_cell_length_c                   11.810(4)
_cell_angle_alpha                100.957(5)
_cell_angle_beta                 111.374(4)
_cell_angle_gamma                93.104(5)
_cell_volume                     1112.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3061
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.46

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             610
_exptl_absorpt_coefficient_mu    2.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3412
_exptl_absorpt_correction_T_max  0.6323
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5625
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3885
_reflns_number_gt                3493
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0272P)²+0.6507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3885
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0558
_refine_ls_wR_factor_gt          0.0544
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.40868(2) 0.312820(17) 0.234017(17) 0.03230(7) Uani 1 1 d . . .
C1 C 0.5050(5) 0.2027(4) -0.2560(4) 0.0587(11) Uani 1 1 d . . .
H1A H 0.5951 0.1562 -0.2456 0.19(4) Uiso 1 1 d R . .
H1B H 0.4344 0.1697 -0.3311 0.11(2) Uiso 1 1 d R . .
H1C H 0.5397 0.2928 -0.2376 0.13(2) Uiso 1 1 d R . .
C2 C 0.4516(4) 0.1722(4) -0.1597(3) 0.0430(9) Uani 1 1 d . . .
C3 C 0.3632(4) 0.0660(3) -0.1603(3) 0.0404(8) Uani 1 1 d . . .
H3 H 0.3197 -0.0070 -0.2251 0.032(9) Uiso 1 1 d R . .
C4 C 0.3511(4) 0.0914(3) -0.0447(3) 0.0350(8) Uani 1 1 d . . .
C5 C 0.2659(3) 0.0167(3) 0.0048(3) 0.0343(7) Uani 1 1 d . . .
C6 C 0.2026(4) -0.1123(3) -0.0519(3) 0.0403(8) Uani 1 1 d . . .
H6 H 0.2174 -0.1559 -0.1217 0.042(10) Uiso 1 1 d R . .
C7 C 0.1177(4) -0.1733(3) -0.0024(4) 0.0455(9) Uani 1 1 d . . .
H7 H 0.0746 -0.2591 -0.0384 0.059(12) Uiso 1 1 d R . .
C8 C 0.0972(4) -0.1064(3) 0.1008(3) 0.0431(9) Uani 1 1 d . . .
H8 H 0.0391 -0.1452 0.1349 0.035(9) Uiso 1 1 d R . .
C9 C 0.1659(4) 0.0206(3) 0.1550(3) 0.0359(8) Uani 1 1 d . . .
C10 C 0.1515(4) 0.0967(3) 0.2666(3) 0.0372(8) Uani 1 1 d . . .
C11 C 0.0660(5) 0.0681(4) 0.3318(4) 0.0533(10) Uani 1 1 d . . .
H11 H 0.0016 -0.0076 0.3126 0.073(14) Uiso 1 1 d R . .
C12 C 0.0944(5) 0.1731(4) 0.4289(4) 0.0569(11) Uani 1 1 d . . .
C13 C 0.0336(9) 0.2023(5) 0.5301(6) 0.095(2) Uani 1 1 d . . .
H13A H -0.0283 0.1321 0.5354 0.101(18) Uiso 1 1 d R . .
H13B H 0.1287 0.2137 0.5963 0.17(4) Uiso 1 1 d R . .
H13C H -0.0100 0.2810 0.5374 0.19(4) Uiso 1 1 d R . .
C14 C 0.1516(4) 0.5133(4) 0.3007(4) 0.0487(9) Uani 1 1 d . . .
H14A H 0.1341 0.5294 0.3775 0.063(13) Uiso 1 1 d R . .
H14B H 0.0895 0.4340 0.2470 0.055(11) Uiso 1 1 d R . .
C15 C 0.1097(5) 0.6226(4) 0.2371(4) 0.0620(12) Uani 1 1 d . . .
H15A H 0.1253 0.6066 0.1605 0.102(19) Uiso 1 1 d R . .
H15B H 0.0083 0.6306 0.2200 0.098(18) Uiso 1 1 d R . .
H15C H 0.1692 0.7015 0.2906 0.090(17) Uiso 1 1 d R . .
N1 N 0.4893(3) 0.2519(3) -0.0464(3) 0.0441(7) Uani 1 1 d . . .
H1 H 0.5451 0.3252 -0.0230 0.053 Uiso 1 1 calc R . .
N2 N 0.4305(3) 0.2047(3) 0.0266(3) 0.0387(7) Uani 1 1 d . . .
N3 N 0.2497(3) 0.0819(2) 0.1086(3) 0.0343(6) Uani 1 1 d . . .
N4 N 0.2285(3) 0.2143(3) 0.3189(3) 0.0415(7) Uani 1 1 d . . .
N5 N 0.1931(4) 0.2586(3) 0.4186(3) 0.0506(8) Uani 1 1 d . . .
H5 H 0.2295 0.3330 0.4694 0.061 Uiso 1 1 calc R . .
N6 N 0.2815(4) 0.4598(3) 0.0374(3) 0.0462(8) Uani 1 1 d . . .
N7 N 0.7197(3) 0.4456(3) 0.3365(3) 0.0497(8) Uani 1 1 d . . .
N8 N 0.5745(3) 0.1856(3) 0.4412(3) 0.0458(7) Uani 1 1 d . . .
O1 O 0.2018(3) 0.3711(2) 0.0519(2) 0.0474(6) Uani 1 1 d . . .
O2 O 0.4164(3) 0.4822(2) 0.1097(2) 0.0444(6) Uani 1 1 d . . .
O3 O 0.2336(4) 0.5230(3) -0.0415(3) 0.0786(10) Uani 1 1 d . . .
O4 O 0.6731(3) 0.3365(3) 0.2599(3) 0.0574(7) Uani 1 1 d . . .
O5 O 0.6258(3) 0.5064(2) 0.3648(2) 0.0507(7) Uani 1 1 d . . .
O6 O 0.8506(3) 0.4874(4) 0.3830(4) 0.0912(12) Uani 1 1 d . . .
O7 O 0.5222(3) 0.1277(2) 0.3272(2) 0.0505(7) Uani 1 1 d . . .
O8 O 0.5489(3) 0.3038(2) 0.4643(2) 0.0493(6) Uani 1 1 d . . .
O9 O 0.6446(4) 0.1340(3) 0.5229(3) 0.0790(10) Uani 1 1 d . . .
O10 O 0.3047(2) 0.4947(2) 0.3279(2) 0.0410(6) Uani 1 1 d . . .
H10 H 0.3736 0.5602 0.3892 0.049 Uiso 1 1 calc R . .


_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 O10 2.489(2) . ?
Nd1 O4 2.501(3) . ?
Nd1 O2 2.534(3) . ?
Nd1 O7 2.537(3) . ?
Nd1 O1 2.569(3) . ?
Nd1 O8 2.586(3) . ?
Nd1 N2 2.587(3) . ?
Nd1 N4 2.594(3) . ?
Nd1 O5 2.656(2) . ?
Nd1 N3 2.667(3) . ?
C1 C2 1.494(5) . ?
C2 N1 1.346(4) . ?
C2 C3 1.379(5) . ?
C3 C4 1.390(5) . ?
C4 N2 1.337(4) . ?
C4 C5 1.460(5) . ?
C5 N3 1.354(4) . ?
C5 C6 1.396(4) . ?
C6 C7 1.377(5) . ?
C7 C8 1.377(5) . ?
C8 C9 1.388(5) . ?
C9 N3 1.344(4) . ?
C9 C10 1.466(5) . ?
C10 N4 1.327(4) . ?
C10 C11 1.388(5) . ?
C11 C12 1.368(6) . ?
C12 N5 1.344(5) . ?
C12 C13 1.511(6) . ?
C14 O10 1.455(4) . ?
C14 C15 1.490(6) . ?
N1 N2 1.351(4) . ?
N4 N5 1.354(4) . ?
N6 O3 1.219(4) . ?
N6 O1 1.265(4) . ?
N6 O2 1.270(4) . ?
N7 O6 1.220(4) . ?
N7 O5 1.260(4) . ?
N7 O4 1.265(4) . ?
N8 O9 1.209(4) . ?
N8 O7 1.264(4) . ?
N8 O8 1.285(4) . ?

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
O10 Nd1 O4 121.01(8) . . ?
O10 Nd1 O2 77.18(8) . . ?
O4 Nd1 O2 78.22(9) . . ?
O10 Nd1 O7 128.52(8) . . ?
O4 Nd1 O7 72.46(10) . . ?
O2 Nd1 O7 148.40(9) . . ?
O10 Nd1 O1 73.61(8) . . ?
O4 Nd1 O1 123.34(9) . . ?
O2 Nd1 O1 50.17(8) . . ?
O7 Nd1 O1 144.92(8) . . ?
O10 Nd1 O8 83.27(8) . . ?
O4 Nd1 O8 76.23(9) . . ?
O2 Nd1 O8 133.10(8) . . ?
O7 Nd1 O8 49.72(8) . . ?
O1 Nd1 O8 155.24(8) . . ?
O10 Nd1 N2 142.06(9) . . ?
O4 Nd1 N2 70.45(9) . . ?
O2 Nd1 N2 69.93(9) . . ?
O7 Nd1 N2 89.05(9) . . ?
O1 Nd1 N2 70.99(9) . . ?
O8 Nd1 N2 133.48(9) . . ?
O10 Nd1 N4 71.94(9) . . ?
O4 Nd1 N4 142.44(10) . . ?
O2 Nd1 N4 138.19(9) . . ?
O7 Nd1 N4 73.02(9) . . ?
O1 Nd1 N4 93.69(9) . . ?
O8 Nd1 N4 70.36(9) . . ?
N2 Nd1 N4 123.20(9) . . ?
O10 Nd1 O5 71.88(8) . . ?
O4 Nd1 O5 49.25(8) . . ?
O2 Nd1 O5 68.35(8) . . ?
O7 Nd1 O5 99.78(9) . . ?
O1 Nd1 O5 114.09(8) . . ?
O8 Nd1 O5 65.12(8) . . ?
N2 Nd1 O5 111.10(9) . . ?
N4 Nd1 O5 124.70(9) . . ?
O10 Nd1 N3 122.41(8) . . ?
O4 Nd1 N3 116.55(8) . . ?
O2 Nd1 N3 117.45(8) . . ?
O7 Nd1 N3 67.79(9) . . ?
O1 Nd1 N3 77.29(8) . . ?
O8 Nd1 N3 109.08(8) . . ?
N2 Nd1 N3 61.72(8) . . ?
N4 Nd1 N3 61.58(9) . . ?
O5 Nd1 N3 164.83(8) . . ?
N1 C2 C3 105.7(3) . . ?
N1 C2 C1 122.7(3) . . ?
C3 C2 C1 131.5(3) . . ?
C2 C3 C4 105.8(3) . . ?
N2 C4 C3 111.1(3) . . ?
N2 C4 C5 118.6(3) . . ?
C3 C4 C5 130.3(3) . . ?
N3 C5 C6 122.0(3) . . ?
N3 C5 C4 115.4(3) . . ?
C6 C5 C4 122.5(3) . . ?
C7 C6 C5 118.6(3) . . ?
C8 C7 C6 119.6(3) . . ?
C7 C8 C9 119.1(3) . . ?
N3 C9 C8 122.2(3) . . ?
N3 C9 C10 115.7(3) . . ?
C8 C9 C10 122.1(3) . . ?
N4 C10 C11 110.3(3) . . ?
N4 C10 C9 119.0(3) . . ?
C11 C10 C9 130.7(3) . . ?
C12 C11 C10 106.6(3) . . ?
N5 C12 C11 105.7(3) . . ?
N5 C12 C13 122.2(4) . . ?
C11 C12 C13 132.1(4) . . ?
O10 C14 C15 112.4(3) . . ?
C2 N1 N2 113.0(3) . . ?
C4 N2 N1 104.3(3) . . ?
C4 N2 Nd1 122.5(2) . . ?
N1 N2 Nd1 131.8(2) . . ?
C9 N3 C5 118.3(3) . . ?
C9 N3 Nd1 120.7(2) . . ?
C5 N3 Nd1 120.5(2) . . ?
C10 N4 N5 105.1(3) . . ?
C10 N4 Nd1 122.4(2) . . ?
N5 N4 Nd1 132.4(2) . . ?
C12 N5 N4 112.3(3) . . ?
O3 N6 O1 122.8(3) . . ?
O3 N6 O2 120.1(3) . . ?
O1 N6 O2 117.1(3) . . ?
O6 N7 O5 122.0(3) . . ?
O6 N7 O4 120.9(4) . . ?
O5 N7 O4 117.1(3) . . ?
O9 N8 O7 122.5(3) . . ?
O9 N8 O8 122.1(3) . . ?
O7 N8 O8 115.3(3) . . ?
N6 O1 Nd1 95.6(2) . . ?
N6 O2 Nd1 97.1(2) . . ?
N7 O4 Nd1 100.4(2) . . ?
N7 O5 Nd1 93.04(19) . . ?
N8 O7 Nd1 98.9(2) . . ?
N8 O8 Nd1 95.98(19) . . ?
C14 O10 Nd1 129.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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 1448213'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N8 O10 Sm'
_chemical_formula_weight         621.74

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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.8205(15)
_cell_length_b                   10.5371(16)
_cell_length_c                   11.7288(18)
_cell_angle_alpha                100.895(2)
_cell_angle_beta                 111.404(2)
_cell_angle_gamma                92.993(2)
_cell_volume                     1099.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4287
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.29

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             614
_exptl_absorpt_coefficient_mu    2.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3091
_exptl_absorpt_correction_T_max  0.5714
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8268
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         28.40
_reflns_number_total             5459
_reflns_number_gt                4939
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0321P)²+0.2053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5459
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0610
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.908131(15) 0.310898(13) 0.233981(12) 0.02953(5) Uani 1 1 d . . .
C1 C 1.0067(5) 0.2050(4) -0.2557(3) 0.0547(9) Uani 1 1 d . . .
H1A H 1.1119 0.2286 -0.2172 0.15(3) Uiso 1 1 d R . .
H1B H 0.9787 0.1318 -0.3206 0.117(19) Uiso 1 1 d R . .
H1C H 0.9619 0.2793 -0.2830 0.114(19) Uiso 1 1 d R . .
C2 C 0.9536(4) 0.1729(3) -0.1586(3) 0.0387(7) Uani 1 1 d . . .
C3 C 0.8636(3) 0.0673(3) -0.1605(3) 0.0389(7) Uani 1 1 d . . .
H3 H 0.8200 -0.0052 -0.2264 0.039(9) Uiso 1 1 d R . .
C4 C 0.8518(3) 0.0915(3) -0.0438(3) 0.0328(6) Uani 1 1 d . . .
C5 C 0.7659(3) 0.0169(3) 0.0053(3) 0.0320(6) Uani 1 1 d . . .
C6 C 0.7020(3) -0.1120(3) -0.0522(3) 0.0390(7) Uani 1 1 d . . .
H6 H 0.7174 -0.1557 -0.1222 0.057(11) Uiso 1 1 d R . .
C7 C 0.6169(4) -0.1733(3) -0.0026(3) 0.0433(7) Uani 1 1 d . . .
H7 H 0.5734 -0.2591 -0.0394 0.055(10) Uiso 1 1 d R . .
C8 C 0.5970(3) -0.1062(3) 0.1017(3) 0.0399(7) Uani 1 1 d . . .
H8 H 0.5379 -0.1454 0.1352 0.052(10) Uiso 1 1 d R . .
C9 C 0.6660(3) 0.0211(3) 0.1562(3) 0.0337(6) Uani 1 1 d . . .
C10 C 0.6523(3) 0.0982(3) 0.2681(3) 0.0352(6) Uani 1 1 d . . .
C11 C 0.5663(4) 0.0694(3) 0.3341(3) 0.0508(8) Uani 1 1 d . . .
H11 H 0.5017 -0.0059 0.3159 0.073(13) Uiso 1 1 d R . .
C12 C 0.5968(5) 0.1758(4) 0.4318(4) 0.0530(9) Uani 1 1 d . . .
C13 C 0.5373(8) 0.2058(5) 0.5338(5) 0.0900(17) Uani 1 1 d . . .
H13A H 0.5811 0.1419 0.5897 0.16(3) Uiso 1 1 d R . .
H13B H 0.5885 0.2911 0.5907 0.20(4) Uiso 1 1 d R . .
H13C H 0.4420 0.1973 0.5084 0.17(3) Uiso 1 1 d R . .
C14 C 0.6536(3) 0.5123(3) 0.3005(3) 0.0457(7) Uani 1 1 d . . .
H14A H 0.6370 0.5289 0.3783 0.069(12) Uiso 1 1 d R . .
H14B H 0.5910 0.4327 0.2472 0.060(11) Uiso 1 1 d R . .
C15 C 0.6107(4) 0.6216(4) 0.2365(4) 0.0590(10) Uani 1 1 d . . .
H15A H 0.6259 0.6057 0.1590 0.080(14) Uiso 1 1 d R . .
H15B H 0.5083 0.6283 0.2196 0.093(16) Uiso 1 1 d R . .
H15C H 0.6693 0.7016 0.2901 0.098(17) Uiso 1 1 d R . .
N1 N 0.9903(3) 0.2528(2) -0.0446(2) 0.0406(6) Uani 1 1 d . . .
H1 H 1.0462 0.3263 -0.0206 0.049 Uiso 1 1 calc R . .
N2 N 0.9301(3) 0.2054(2) 0.0278(2) 0.0374(5) Uani 1 1 d . . .
N3 N 0.7491(3) 0.0825(2) 0.1088(2) 0.0308(5) Uani 1 1 d . . .
N4 N 0.7308(3) 0.2153(2) 0.3203(2) 0.0391(6) Uani 1 1 d . . .
N5 N 0.6963(3) 0.2598(3) 0.4208(2) 0.0458(6) Uani 1 1 d . . .
H5 H 0.7340 0.3340 0.4721 0.055 Uiso 1 1 calc R . .
N6 N 0.7824(3) 0.4575(3) 0.0387(2) 0.0428(6) Uani 1 1 d . . .
N7 N 1.2172(3) 0.4432(3) 0.3356(3) 0.0473(7) Uani 1 1 d . . .
N8 N 1.0738(3) 0.1854(3) 0.4405(2) 0.0420(6) Uani 1 1 d . . .
O1 O 0.7020(2) 0.3689(2) 0.0533(2) 0.0433(5) Uani 1 1 d . . .
O2 O 0.9167(2) 0.4795(2) 0.1113(2) 0.0408(5) Uani 1 1 d . . .
O3 O 0.7340(4) 0.5211(3) -0.0408(3) 0.0725(8) Uani 1 1 d . . .
O4 O 1.1700(3) 0.3343(2) 0.2591(2) 0.0528(6) Uani 1 1 d . . .
O5 O 1.1241(3) 0.5044(2) 0.3645(2) 0.0484(5) Uani 1 1 d . . .
O6 O 1.3487(3) 0.4846(3) 0.3819(3) 0.0837(10) Uani 1 1 d . . .
O7 O 1.0205(3) 0.1273(2) 0.3262(2) 0.0463(5) Uani 1 1 d . . .
O8 O 1.0482(3) 0.3036(2) 0.46376(19) 0.0450(5) Uani 1 1 d . . .
O9 O 1.1457(4) 0.1341(3) 0.5227(3) 0.0744(9) Uani 1 1 d . . .
O10 O 0.8067(2) 0.4922(2) 0.32735(18) 0.0378(5) Uani 1 1 d . . .
H10 H 0.8764 0.5576 0.3888 0.045 Uiso 1 1 calc R . .


_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 O10 2.4590(19) . ?
Sm1 O4 2.473(2) . ?
Sm1 O7 2.504(2) . ?
Sm1 O2 2.505(2) . ?
Sm1 O1 2.539(2) . ?
Sm1 N2 2.554(2) . ?
Sm1 O8 2.558(2) . ?
Sm1 N4 2.562(2) . ?
Sm1 N3 2.643(2) . ?
Sm1 O5 2.645(2) . ?
C1 C2 1.498(4) . ?
C2 N1 1.348(4) . ?
C2 C3 1.376(4) . ?
C3 C4 1.392(4) . ?
C4 N2 1.337(4) . ?
C4 C5 1.455(4) . ?
C5 N3 1.348(3) . ?
C5 C6 1.396(4) . ?
C6 C7 1.376(5) . ?
C7 C8 1.377(5) . ?
C8 C9 1.390(4) . ?
C9 N3 1.345(4) . ?
C9 C10 1.462(4) . ?
C10 N4 1.327(4) . ?
C10 C11 1.394(4) . ?
C11 C12 1.374(5) . ?
C12 N5 1.342(4) . ?
C12 C13 1.503(5) . ?
C14 O10 1.455(4) . ?
C14 C15 1.489(5) . ?
N1 N2 1.347(3) . ?
N4 N5 1.350(3) . ?
N6 O3 1.221(4) . ?
N6 O2 1.262(3) . ?
N6 O1 1.268(3) . ?
N7 O6 1.222(4) . ?
N7 O5 1.253(4) . ?
N7 O4 1.260(3) . ?
N8 O9 1.209(4) . ?
N8 O7 1.261(3) . ?
N8 O8 1.281(3) . ?

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
O10 Sm1 O4 120.53(7) . . ?
O10 Sm1 O7 128.82(7) . . ?
O4 Sm1 O7 72.64(9) . . ?
O10 Sm1 O2 76.71(7) . . ?
O4 Sm1 O2 77.88(8) . . ?
O7 Sm1 O2 148.31(8) . . ?
O10 Sm1 O1 73.49(7) . . ?
O4 Sm1 O1 123.48(8) . . ?
O7 Sm1 O1 144.76(7) . . ?
O2 Sm1 O1 50.69(7) . . ?
O10 Sm1 N2 141.72(8) . . ?
O4 Sm1 N2 70.22(8) . . ?
O7 Sm1 N2 89.17(8) . . ?
O2 Sm1 N2 69.84(7) . . ?
O1 Sm1 N2 71.13(8) . . ?
O10 Sm1 O8 83.02(7) . . ?
O4 Sm1 O8 76.22(8) . . ?
O7 Sm1 O8 50.24(7) . . ?
O2 Sm1 O8 132.31(7) . . ?
O1 Sm1 O8 154.87(7) . . ?
N2 Sm1 O8 133.78(8) . . ?
O10 Sm1 N4 72.00(8) . . ?
O4 Sm1 N4 142.50(9) . . ?
O7 Sm1 N4 73.15(8) . . ?
O2 Sm1 N4 138.24(8) . . ?
O1 Sm1 N4 93.58(8) . . ?
N2 Sm1 N4 124.01(8) . . ?
O8 Sm1 N4 70.30(8) . . ?
O10 Sm1 N3 122.61(7) . . ?
O4 Sm1 N3 116.84(7) . . ?
O7 Sm1 N3 67.92(7) . . ?
O2 Sm1 N3 117.68(7) . . ?
O1 Sm1 N3 76.98(7) . . ?
N2 Sm1 N3 62.12(7) . . ?
O8 Sm1 N3 109.67(7) . . ?
N4 Sm1 N3 61.98(7) . . ?
O10 Sm1 O5 71.28(7) . . ?
O4 Sm1 O5 49.38(7) . . ?
O7 Sm1 O5 100.10(8) . . ?
O2 Sm1 O5 67.84(7) . . ?
O1 Sm1 O5 114.01(7) . . ?
N2 Sm1 O5 110.86(8) . . ?
O8 Sm1 O5 64.84(8) . . ?
N4 Sm1 O5 124.21(8) . . ?
N3 Sm1 O5 165.31(8) . . ?
N1 C2 C3 105.9(3) . . ?
N1 C2 C1 122.6(3) . . ?
C3 C2 C1 131.5(3) . . ?
C2 C3 C4 105.8(3) . . ?
N2 C4 C3 110.9(3) . . ?
N2 C4 C5 118.7(2) . . ?
C3 C4 C5 130.4(3) . . ?
N3 C5 C6 122.3(3) . . ?
N3 C5 C4 115.1(2) . . ?
C6 C5 C4 122.6(3) . . ?
C7 C6 C5 118.7(3) . . ?
C6 C7 C8 119.3(3) . . ?
C7 C8 C9 119.2(3) . . ?
N3 C9 C8 122.1(3) . . ?
N3 C9 C10 115.2(2) . . ?
C8 C9 C10 122.6(3) . . ?
N4 C10 C11 110.8(3) . . ?
N4 C10 C9 119.0(3) . . ?
C11 C10 C9 130.2(3) . . ?
C12 C11 C10 105.7(3) . . ?
N5 C12 C11 105.9(3) . . ?
N5 C12 C13 122.4(4) . . ?
C11 C12 C13 131.6(4) . . ?
O10 C14 C15 113.0(3) . . ?
N2 N1 C2 112.8(2) . . ?
C4 N2 N1 104.7(2) . . ?
C4 N2 Sm1 122.39(19) . . ?
N1 N2 Sm1 131.75(18) . . ?
C9 N3 C5 118.2(2) . . ?
C9 N3 Sm1 120.66(18) . . ?
C5 N3 Sm1 120.43(18) . . ?
C10 N4 N5 104.8(2) . . ?
C10 N4 Sm1 122.49(19) . . ?
N5 N4 Sm1 132.64(19) . . ?
C12 N5 N4 112.6(3) . . ?
O3 N6 O2 120.3(3) . . ?
O3 N6 O1 122.5(3) . . ?
O2 N6 O1 117.2(2) . . ?
O6 N7 O5 121.9(3) . . ?
O6 N7 O4 120.9(3) . . ?
O5 N7 O4 117.1(3) . . ?
O9 N8 O7 122.5(3) . . ?
O9 N8 O8 122.0(3) . . ?
O7 N8 O8 115.5(3) . . ?
N6 O1 Sm1 95.14(17) . . ?
N6 O2 Sm1 96.96(16) . . ?
N7 O4 Sm1 100.74(18) . . ?
N7 O5 Sm1 92.55(18) . . ?
N8 O7 Sm1 98.71(17) . . ?
N8 O8 Sm1 95.53(16) . . ?
C14 O10 Sm1 129.47(18) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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 1448214'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 Eu N8 O10'
_chemical_formula_weight         623.34

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'
Eu Eu -0.1578 3.6682 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.8278(17)
_cell_length_b                   10.5328(17)
_cell_length_c                   11.7056(19)
_cell_angle_alpha                100.796(2)
_cell_angle_beta                 111.442(2)
_cell_angle_gamma                93.031(2)
_cell_volume                     1098.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3746
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      28.58

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    2.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3114
_exptl_absorpt_correction_T_max  0.7203
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5573
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3838
_reflns_number_gt                3557
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0225P)²+0.4583P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3838
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0550
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.092183(17) 0.190001(14) 0.266034(14) 0.03092(7) Uani 1 1 d . . .
C1 C -0.0072(5) 0.2951(4) 0.7552(4) 0.0542(10) Uani 1 1 d . . .
H1A H 0.0220 0.2138 0.7716 0.092(17) Uiso 1 1 d R . .
H1B H 0.0429 0.3639 0.8288 0.091(16) Uiso 1 1 d R . .
H1C H -0.1098 0.2944 0.7270 0.15(3) Uiso 1 1 d R . .
C2 C 0.0466(4) 0.3262(3) 0.6584(3) 0.0412(8) Uani 1 1 d . . .
C3 C 0.1361(4) 0.4322(3) 0.6606(3) 0.0398(8) Uani 1 1 d . . .
H3 H 0.1794 0.5048 0.7263 0.042(10) Uiso 1 1 d R . .
C4 C 0.1483(3) 0.4085(3) 0.5440(3) 0.0342(7) Uani 1 1 d . . .
C5 C 0.2344(3) 0.4827(3) 0.4945(3) 0.0338(7) Uani 1 1 d . . .
C6 C 0.2986(4) 0.6112(3) 0.5519(3) 0.0408(8) Uani 1 1 d . . .
H6 H 0.2840 0.6549 0.6224 0.063(12) Uiso 1 1 d R . .
C7 C 0.3832(4) 0.6718(3) 0.5018(3) 0.0440(9) Uani 1 1 d . . .
H7 H 0.4260 0.7579 0.5382 0.042(10) Uiso 1 1 d R . .
C8 C 0.4040(4) 0.6058(3) 0.3981(3) 0.0426(8) Uani 1 1 d . . .
H8 H 0.4642 0.6448 0.3653 0.058(12) Uiso 1 1 d R . .
C9 C 0.3340(3) 0.4782(3) 0.3431(3) 0.0343(7) Uani 1 1 d . . .
C10 C 0.3477(4) 0.4016(3) 0.2314(3) 0.0349(7) Uani 1 1 d . . .
C11 C 0.4324(5) 0.4291(4) 0.1642(4) 0.0515(10) Uani 1 1 d . . .
H11 H 0.4973 0.5036 0.1822 0.069(13) Uiso 1 1 d R . .
C12 C 0.4016(5) 0.3231(4) 0.0668(4) 0.0529(10) Uani 1 1 d . . .
C13 C 0.4603(8) 0.2927(5) -0.0360(6) 0.0882(18) Uani 1 1 d . . .
H13C H 0.5665 0.3292 -0.0045 0.14(3) Uiso 1 1 d R . .
H13D H 0.4588 0.1981 -0.0624 0.13(2) Uiso 1 1 d R . .
H13E H 0.4083 0.3258 -0.1060 0.15(3) Uiso 1 1 d R . .
C14 C 0.3459(4) -0.0119(4) 0.1989(4) 0.0484(9) Uani 1 1 d . . .
H14A H 0.4087 0.0677 0.2519 0.051(11) Uiso 1 1 d R . .
H14B H 0.3618 -0.0290 0.1208 0.067(13) Uiso 1 1 d R . .
C15 C 0.3881(5) -0.1207(4) 0.2632(4) 0.0616(11) Uani 1 1 d . . .
H15A H 0.3280 -0.1997 0.2103 0.12(2) Uiso 1 1 d R . .
H15B H 0.4895 -0.1293 0.2794 0.085(16) Uiso 1 1 d R . .
H15C H 0.3743 -0.1038 0.3410 0.089(17) Uiso 1 1 d R . .
N1 N 0.0092(3) 0.2466(3) 0.5444(3) 0.0404(7) Uani 1 1 d . . .
H1 H -0.0470 0.1733 0.5204 0.049 Uiso 1 1 calc R . .
N2 N 0.0695(3) 0.2943(3) 0.4716(3) 0.0380(6) Uani 1 1 d . . .
N3 N 0.2507(3) 0.4176(2) 0.3908(2) 0.0322(6) Uani 1 1 d . . .
N4 N 0.2689(3) 0.2842(3) 0.1791(3) 0.0398(7) Uani 1 1 d . . .
N5 N 0.3029(4) 0.2390(3) 0.0786(3) 0.0455(7) Uani 1 1 d . . .
H5 H 0.2654 0.1645 0.0276 0.055 Uiso 1 1 calc R . .
N6 N 0.2180(4) 0.0425(3) 0.4614(3) 0.0442(7) Uani 1 1 d . . .
N7 N -0.2167(3) 0.0575(3) 0.1645(3) 0.0485(8) Uani 1 1 d . . .
N8 N -0.0738(3) 0.3151(3) 0.0598(3) 0.0432(7) Uani 1 1 d . . .
O1 O 0.2979(3) 0.1322(2) 0.4455(2) 0.0448(6) Uani 1 1 d . . .
O2 O 0.0837(3) 0.0217(2) 0.3881(2) 0.0414(6) Uani 1 1 d . . .
O3 O 0.2669(4) -0.0200(3) 0.5410(3) 0.0738(9) Uani 1 1 d . . .
O4 O -0.1681(3) 0.1669(3) 0.2407(2) 0.0541(7) Uani 1 1 d . . .
O5 O -0.1232(3) -0.0043(2) 0.1347(2) 0.0493(6) Uani 1 1 d . . .
O6 O -0.3475(3) 0.0162(4) 0.1186(3) 0.0847(11) Uani 1 1 d . . .
O7 O -0.0196(3) 0.3727(2) 0.1749(2) 0.0479(6) Uani 1 1 d . . .
O8 O -0.0478(3) 0.1965(2) 0.0368(2) 0.0469(6) Uani 1 1 d . . .
O9 O -0.1460(4) 0.3658(3) -0.0228(3) 0.0737(9) Uani 1 1 d . . .
O10 O 0.1922(2) 0.0087(2) 0.1726(2) 0.0381(5) Uani 1 1 d . . .
H10 H 0.1222 -0.0566 0.1114 0.046 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O10 2.452(2) . ?
Eu1 O4 2.458(3) . ?
Eu1 O7 2.487(3) . ?
Eu1 O2 2.492(2) . ?
Eu1 O1 2.525(2) . ?
Eu1 O8 2.545(2) . ?
Eu1 N2 2.544(3) . ?
Eu1 N4 2.555(3) . ?
Eu1 N3 2.634(3) . ?
Eu1 O5 2.649(2) . ?
C1 C2 1.493(5) . ?
C2 N1 1.345(4) . ?
C2 C3 1.375(5) . ?
C3 C4 1.392(5) . ?
C4 N2 1.343(4) . ?
C4 C5 1.456(4) . ?
C5 N3 1.346(4) . ?
C5 C6 1.393(4) . ?
C6 C7 1.372(5) . ?
C7 C8 1.371(5) . ?
C8 C9 1.396(5) . ?
C9 N3 1.343(4) . ?
C9 C10 1.457(5) . ?
C10 N4 1.332(4) . ?
C10 C11 1.390(5) . ?
C11 C12 1.369(5) . ?
C12 N5 1.341(5) . ?
C12 C13 1.506(6) . ?
C14 O10 1.464(4) . ?
C14 C15 1.483(6) . ?
N1 N2 1.352(4) . ?
N4 N5 1.348(4) . ?
N6 O3 1.211(4) . ?
N6 O2 1.264(4) . ?
N6 O1 1.280(4) . ?
N7 O6 1.216(4) . ?
N7 O4 1.264(4) . ?
N7 O5 1.265(4) . ?
N8 O9 1.207(4) . ?
N8 O7 1.266(4) . ?
N8 O8 1.287(4) . ?

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
O10 Eu1 O4 120.34(8) . . ?
O10 Eu1 O7 129.05(8) . . ?
O4 Eu1 O7 72.43(9) . . ?
O10 Eu1 O2 76.52(8) . . ?
O4 Eu1 O2 78.01(9) . . ?
O7 Eu1 O2 148.20(8) . . ?
O10 Eu1 O1 73.40(8) . . ?
O4 Eu1 O1 123.85(9) . . ?
O7 Eu1 O1 144.66(8) . . ?
O2 Eu1 O1 50.90(8) . . ?
O10 Eu1 O8 82.82(8) . . ?
O4 Eu1 O8 76.02(9) . . ?
O7 Eu1 O8 50.62(8) . . ?
O2 Eu1 O8 131.98(8) . . ?
O1 Eu1 O8 154.58(8) . . ?
O10 Eu1 N2 141.72(9) . . ?
O4 Eu1 N2 70.06(9) . . ?
O7 Eu1 N2 89.00(9) . . ?
O2 Eu1 N2 69.81(8) . . ?
O1 Eu1 N2 71.45(9) . . ?
O8 Eu1 N2 133.79(9) . . ?
O10 Eu1 N4 71.85(8) . . ?
O4 Eu1 N4 142.48(10) . . ?
O7 Eu1 N4 73.52(9) . . ?
O2 Eu1 N4 138.01(9) . . ?
O1 Eu1 N4 93.28(9) . . ?
O8 Eu1 N4 70.41(9) . . ?
N2 Eu1 N4 124.54(9) . . ?
O10 Eu1 N3 122.83(8) . . ?
O4 Eu1 N3 116.81(8) . . ?
O7 Eu1 N3 67.82(8) . . ?
O2 Eu1 N3 117.79(8) . . ?
O1 Eu1 N3 76.98(8) . . ?
O8 Eu1 N3 109.89(8) . . ?
N2 Eu1 N3 62.38(8) . . ?
N4 Eu1 N3 62.26(8) . . ?
O10 Eu1 O5 70.79(8) . . ?
O4 Eu1 O5 49.68(8) . . ?
O7 Eu1 O5 100.28(8) . . ?
O2 Eu1 O5 67.78(8) . . ?
O1 Eu1 O5 113.99(8) . . ?
O8 Eu1 O5 64.55(8) . . ?
N2 Eu1 O5 110.85(8) . . ?
N4 Eu1 O5 123.76(9) . . ?
N3 Eu1 O5 165.55(8) . . ?
N1 C2 C3 106.3(3) . . ?
N1 C2 C1 122.6(3) . . ?
C3 C2 C1 131.1(3) . . ?
C2 C3 C4 105.7(3) . . ?
N2 C4 C3 110.9(3) . . ?
N2 C4 C5 118.3(3) . . ?
C3 C4 C5 130.7(3) . . ?
N3 C5 C6 122.1(3) . . ?
N3 C5 C4 115.3(3) . . ?
C6 C5 C4 122.6(3) . . ?
C7 C6 C5 118.5(3) . . ?
C8 C7 C6 120.1(3) . . ?
C7 C8 C9 118.6(3) . . ?
N3 C9 C8 121.9(3) . . ?
N3 C9 C10 115.7(3) . . ?
C8 C9 C10 122.4(3) . . ?
N4 C10 C11 110.2(3) . . ?
N4 C10 C9 118.8(3) . . ?
C11 C10 C9 131.0(3) . . ?
C12 C11 C10 106.3(3) . . ?
N5 C12 C11 106.0(3) . . ?
N5 C12 C13 122.3(4) . . ?
C11 C12 C13 131.7(4) . . ?
O10 C14 C15 112.7(3) . . ?
C2 N1 N2 112.7(3) . . ?
C4 N2 N1 104.5(3) . . ?
C4 N2 Eu1 122.3(2) . . ?
N1 N2 Eu1 132.0(2) . . ?
C9 N3 C5 118.6(3) . . ?
C9 N3 Eu1 120.4(2) . . ?
C5 N3 Eu1 120.4(2) . . ?
C10 N4 N5 105.1(3) . . ?
C10 N4 Eu1 122.3(2) . . ?
N5 N4 Eu1 132.6(2) . . ?
C12 N5 N4 112.4(3) . . ?
O3 N6 O2 121.4(3) . . ?
O3 N6 O1 122.7(3) . . ?
O2 N6 O1 115.9(3) . . ?
O6 N7 O4 121.5(4) . . ?
O6 N7 O5 121.8(3) . . ?
O4 N7 O5 116.6(3) . . ?
O9 N8 O7 123.2(3) . . ?
O9 N8 O8 121.9(3) . . ?
O7 N8 O8 114.9(3) . . ?
N6 O1 Eu1 95.58(19) . . ?
N6 O2 Eu1 97.60(18) . . ?
N7 O4 Eu1 101.4(2) . . ?
N7 O5 Eu1 92.14(19) . . ?
N8 O7 Eu1 98.9(2) . . ?
N8 O8 Eu1 95.49(18) . . ?
C14 O10 Eu1 129.53(19) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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 1448215'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 Gd N8 O10'
_chemical_formula_weight         628.63

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'
Gd Gd -0.1653 3.9035 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.8238(6)
_cell_length_b                   10.5226(6)
_cell_length_c                   11.6761(7)
_cell_angle_alpha                100.6990(10)
_cell_angle_beta                 111.4740(10)
_cell_angle_gamma                92.9820(10)
_cell_volume                     1094.13(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3644
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      29.22

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             618
_exptl_absorpt_coefficient_mu    3.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2852
_exptl_absorpt_correction_T_max  0.6707
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5524
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3818
_reflns_number_gt                3495
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0282P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3818
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0491
_refine_ls_wR_factor_gt          0.0481
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.407488(16) 0.309302(13) 0.733895(13) 0.03136(6) Uani 1 1 d . . .
C1 C 0.5082(5) 0.2056(4) 0.2448(4) 0.0553(10) Uani 1 1 d . . .
H1C H 0.4629 0.2856 0.2188 0.13(2) Uiso 1 1 d R . .
H1D H 0.4842 0.1413 0.1718 0.102(16) Uiso 1 1 d R . .
H1E H 0.6134 0.2347 0.2833 0.13(2) Uiso 1 1 d R . .
C2 C 0.4548(4) 0.1744(3) 0.3418(3) 0.0397(7) Uani 1 1 d . . .
C3 C 0.3645(4) 0.0685(3) 0.3399(3) 0.0402(7) Uani 1 1 d . . .
H3 H 0.3211 -0.0041 0.2740 0.042(9) Uiso 1 1 d R . .
C4 C 0.3521(3) 0.0921(3) 0.4565(3) 0.0332(7) Uani 1 1 d . . .
C5 C 0.2654(3) 0.0173(3) 0.5055(3) 0.0344(7) Uani 1 1 d . . .
C6 C 0.2018(3) -0.1111(3) 0.4485(3) 0.0404(7) Uani 1 1 d . . .
H6 H 0.2169 -0.1549 0.3782 0.047(9) Uiso 1 1 d R . .
C7 C 0.1170(4) -0.1721(3) 0.4983(3) 0.0469(8) Uani 1 1 d . . .
H7 H 0.0741 -0.2582 0.4622 0.050(10) Uiso 1 1 d R . .
C8 C 0.0965(4) -0.1058(3) 0.6024(3) 0.0421(8) Uani 1 1 d . . .
H8 H 0.0372 -0.1452 0.6357 0.048(10) Uiso 1 1 d R . .
C9 C 0.1657(3) 0.0214(3) 0.6568(3) 0.0346(7) Uani 1 1 d . . .
C10 C 0.1526(3) 0.0989(3) 0.7692(3) 0.0363(7) Uani 1 1 d . . .
C11 C 0.0681(4) 0.0719(3) 0.8364(3) 0.0526(9) Uani 1 1 d . . .
H11 H 0.0031 -0.0020 0.8183 0.065(12) Uiso 1 1 d R . .
C12 C 0.0988(4) 0.1774(4) 0.9342(4) 0.0524(9) Uani 1 1 d . . .
C13 C 0.0405(7) 0.2093(5) 1.0372(5) 0.0887(17) Uani 1 1 d . . .
H13A H 0.1159 0.1750 1.1095 0.12(2) Uiso 1 1 d R . .
H13B H -0.0386 0.1489 1.0243 0.089(15) Uiso 1 1 d R . .
H13C H 0.0459 0.2967 1.0652 0.18(3) Uiso 1 1 d R . .
C14 C 0.1552(4) 0.5100(3) 0.8014(4) 0.0500(9) Uani 1 1 d . . .
H14A H 0.0917 0.4303 0.7494 0.062(11) Uiso 1 1 d R . .
H14B H 0.1407 0.5283 0.8804 0.066(12) Uiso 1 1 d R . .
C15 C 0.1116(4) 0.6201(4) 0.7362(4) 0.0598(10) Uani 1 1 d . . .
H15A H 0.1744 0.6985 0.7854 0.104(18) Uiso 1 1 d R . .
H15B H 0.0126 0.6318 0.7247 0.082(14) Uiso 1 1 d R . .
H15C H 0.1195 0.6002 0.6565 0.080(14) Uiso 1 1 d R . .
N1 N 0.4909(3) 0.2533(3) 0.4562(2) 0.0414(6) Uani 1 1 d . . .
H1 H 0.5468 0.3268 0.4806 0.050 Uiso 1 1 calc R . .
N2 N 0.4303(3) 0.2050(2) 0.5286(2) 0.0385(6) Uani 1 1 d . . .
N3 N 0.2497(3) 0.0827(2) 0.6096(2) 0.0334(6) Uani 1 1 d . . .
N4 N 0.2321(3) 0.2163(2) 0.8212(2) 0.0402(6) Uani 1 1 d . . .
N5 N 0.1986(3) 0.2619(3) 0.9222(3) 0.0454(7) Uani 1 1 d . . .
H5 H 0.2365 0.3363 0.9732 0.054 Uiso 1 1 calc R . .
N6 N 0.2821(3) 0.4559(3) 0.5393(3) 0.0443(7) Uani 1 1 d . . .
N7 N 0.7153(3) 0.4418(3) 0.8358(3) 0.0495(7) Uani 1 1 d . . .
N8 N 0.5729(3) 0.1854(3) 0.9392(3) 0.0435(7) Uani 1 1 d . . .
O1 O 0.2026(2) 0.3665(2) 0.5550(2) 0.0449(5) Uani 1 1 d . . .
O2 O 0.4166(2) 0.4780(2) 0.6127(2) 0.0425(5) Uani 1 1 d . . .
O3 O 0.2322(3) 0.5189(3) 0.4589(3) 0.0740(8) Uani 1 1 d . . .
O4 O 0.6665(3) 0.3321(2) 0.7591(2) 0.0548(6) Uani 1 1 d . . .
O5 O 0.6228(3) 0.5043(2) 0.8653(2) 0.0498(6) Uani 1 1 d . . .
O6 O 0.8464(3) 0.4822(3) 0.8803(3) 0.0868(10) Uani 1 1 d . . .
O7 O 0.5186(3) 0.1273(2) 0.8250(2) 0.0474(6) Uani 1 1 d . . .
O8 O 0.5472(3) 0.3033(2) 0.9629(2) 0.0453(5) Uani 1 1 d . . .
O9 O 0.6462(3) 0.1341(3) 1.0221(3) 0.0746(9) Uani 1 1 d . . .
O10 O 0.3086(2) 0.4899(2) 0.82722(19) 0.0385(5) Uani 1 1 d . . .
H10 H 0.3787 0.5554 0.8880 0.046 Uiso 1 1 calc R . .


_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
Gd1 O10 2.437(2) . ?
Gd1 O4 2.446(2) . ?
Gd1 O7 2.473(2) . ?
Gd1 O2 2.484(2) . ?
Gd1 O1 2.508(2) . ?
Gd1 O8 2.534(2) . ?
Gd1 N2 2.538(2) . ?
Gd1 N4 2.540(3) . ?
Gd1 N3 2.623(2) . ?
Gd1 O5 2.654(2) . ?
C1 C2 1.491(5) . ?
C2 N1 1.345(4) . ?
C2 C3 1.379(5) . ?
C3 C4 1.390(4) . ?
C4 N2 1.331(4) . ?
C4 C5 1.457(4) . ?
C5 N3 1.347(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.372(5) . ?
C7 C8 1.373(5) . ?
C8 C9 1.389(4) . ?
C9 N3 1.345(4) . ?
C9 C10 1.463(4) . ?
C10 N4 1.334(4) . ?
C10 C11 1.386(5) . ?
C11 C12 1.367(5) . ?
C12 N5 1.352(4) . ?
C12 C13 1.504(5) . ?
C14 O10 1.459(4) . ?
C14 C15 1.499(5) . ?
N1 N2 1.351(4) . ?
N4 N5 1.349(4) . ?
N6 O3 1.221(4) . ?
N6 O2 1.264(3) . ?
N6 O1 1.273(3) . ?
N7 O6 1.217(4) . ?
N7 O5 1.258(4) . ?
N7 O4 1.268(3) . ?
N8 O9 1.212(4) . ?
N8 O7 1.256(3) . ?
N8 O8 1.279(3) . ?

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
O10 Gd1 O4 120.18(7) . . ?
O10 Gd1 O7 128.96(7) . . ?
O4 Gd1 O7 72.49(9) . . ?
O10 Gd1 O2 76.36(7) . . ?
O4 Gd1 O2 77.88(8) . . ?
O7 Gd1 O2 148.24(8) . . ?
O10 Gd1 O1 73.57(7) . . ?
O4 Gd1 O1 123.93(8) . . ?
O7 Gd1 O1 144.52(7) . . ?
O2 Gd1 O1 51.25(7) . . ?
O10 Gd1 O8 82.61(7) . . ?
O4 Gd1 O8 76.00(8) . . ?
O7 Gd1 O8 50.75(7) . . ?
O2 Gd1 O8 131.54(7) . . ?
O1 Gd1 O8 154.52(8) . . ?
O10 Gd1 N2 141.88(8) . . ?
O4 Gd1 N2 70.04(8) . . ?
O7 Gd1 N2 88.95(8) . . ?
O2 Gd1 N2 70.12(8) . . ?
O1 Gd1 N2 71.50(8) . . ?
O8 Gd1 N2 133.80(8) . . ?
O10 Gd1 N4 71.79(8) . . ?
O4 Gd1 N4 142.47(9) . . ?
O7 Gd1 N4 73.51(8) . . ?
O2 Gd1 N4 138.03(8) . . ?
O1 Gd1 N4 93.23(8) . . ?
O8 Gd1 N4 70.38(8) . . ?
N2 Gd1 N4 124.68(8) . . ?
O10 Gd1 N3 122.95(7) . . ?
O4 Gd1 N3 116.84(8) . . ?
O7 Gd1 N3 67.81(8) . . ?
O2 Gd1 N3 118.09(7) . . ?
O1 Gd1 N3 76.85(7) . . ?
O8 Gd1 N3 110.04(7) . . ?
N2 Gd1 N3 62.36(8) . . ?
N4 Gd1 N3 62.42(8) . . ?
O10 Gd1 O5 70.53(7) . . ?
O4 Gd1 O5 49.77(8) . . ?
O7 Gd1 O5 100.45(8) . . ?
O2 Gd1 O5 67.38(7) . . ?
O1 Gd1 O5 113.98(7) . . ?
O8 Gd1 O5 64.53(7) . . ?
N2 Gd1 O5 110.88(8) . . ?
N4 Gd1 O5 123.60(8) . . ?
N3 Gd1 O5 165.69(7) . . ?
N1 C2 C3 105.5(3) . . ?
N1 C2 C1 123.2(3) . . ?
C3 C2 C1 131.3(3) . . ?
C2 C3 C4 106.0(3) . . ?
N2 C4 C3 110.9(3) . . ?
N2 C4 C5 118.5(3) . . ?
C3 C4 C5 130.5(3) . . ?
N3 C5 C6 122.2(3) . . ?
N3 C5 C4 114.9(3) . . ?
C6 C5 C4 122.9(3) . . ?
C7 C6 C5 118.8(3) . . ?
C6 C7 C8 119.7(3) . . ?
C7 C8 C9 118.8(3) . . ?
N3 C9 C8 122.4(3) . . ?
N3 C9 C10 114.9(3) . . ?
C8 C9 C10 122.7(3) . . ?
N4 C10 C11 110.4(3) . . ?
N4 C10 C9 118.8(3) . . ?
C11 C10 C9 130.8(3) . . ?
C12 C11 C10 106.6(3) . . ?
N5 C12 C11 105.6(3) . . ?
N5 C12 C13 121.8(4) . . ?
C11 C12 C13 132.5(4) . . ?
O10 C14 C15 112.7(3) . . ?
C2 N1 N2 112.9(3) . . ?
C4 N2 N1 104.6(2) . . ?
C4 N2 Gd1 122.5(2) . . ?
N1 N2 Gd1 131.62(18) . . ?
C9 N3 C5 118.1(3) . . ?
C9 N3 Gd1 120.82(19) . . ?
C5 N3 Gd1 120.57(19) . . ?
C10 N4 N5 105.0(3) . . ?
C10 N4 Gd1 122.4(2) . . ?
N5 N4 Gd1 132.52(19) . . ?
N4 N5 C12 112.3(3) . . ?
O3 N6 O2 121.0(3) . . ?
O3 N6 O1 122.4(3) . . ?
O2 N6 O1 116.6(3) . . ?
O6 N7 O5 122.2(3) . . ?
O6 N7 O4 120.8(3) . . ?
O5 N7 O4 117.0(3) . . ?
O9 N8 O7 122.6(3) . . ?
O9 N8 O8 121.7(3) . . ?
O7 N8 O8 115.7(3) . . ?
N6 O1 Gd1 95.35(18) . . ?
N6 O2 Gd1 96.78(17) . . ?
N7 O4 Gd1 101.41(19) . . ?
N7 O5 Gd1 91.62(18) . . ?
N8 O7 Gd1 98.57(17) . . ?
N8 O8 Gd1 94.95(17) . . ?
C14 O10 Gd1 129.33(18) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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 1448216'
_audit_update_record             
;
2016-03-15 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N8 O10 Tb'
_chemical_formula_weight         630.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.8370(10)
_cell_length_b                   10.5202(11)
_cell_length_c                   11.6498(12)
_cell_angle_alpha                100.558(2)
_cell_angle_beta                 111.491(2)
_cell_angle_gamma                92.907(2)
_cell_volume                     1093.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3982
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.26

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    3.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3179
_exptl_absorpt_correction_T_max  0.5725
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5634
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3828
_reflns_number_gt                3556
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0218P)²+0.6248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3828
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0469
_refine_ls_wR_factor_gt          0.0460
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.907161(16) 0.307734(14) 0.234048(13) 0.02680(6) Uani 1 1 d . . .
O1 O 1.0181(3) 0.1260(2) 0.3250(2) 0.0412(6) Uani 1 1 d . . .
O2 O 1.0469(3) 0.3031(2) 0.4631(2) 0.0400(6) Uani 1 1 d . . .
O3 O 1.1468(3) 0.1334(3) 0.5228(3) 0.0679(9) Uani 1 1 d . . .
O4 O 1.1229(3) 0.5038(2) 0.3651(2) 0.0463(6) Uani 1 1 d . . .
O5 O 1.1647(3) 0.3309(3) 0.2589(2) 0.0474(6) Uani 1 1 d . . .
O6 O 1.3456(3) 0.4801(3) 0.3793(3) 0.0799(10) Uani 1 1 d . . .
O7 O 0.7027(2) 0.3653(2) 0.0553(2) 0.0397(5) Uani 1 1 d . . .
O8 O 0.9169(2) 0.4760(2) 0.1136(2) 0.0378(5) Uani 1 1 d . . .
O9 O 0.7337(3) 0.5183(3) -0.0403(3) 0.0678(8) Uani 1 1 d . . .
O10 O 0.8095(2) 0.4880(2) 0.3268(2) 0.0344(5) Uani 1 1 d . . .
H10 H 0.8798 0.5532 0.3875 0.041 Uiso 1 1 calc R . .
N1 N 0.6999(3) 0.2624(3) 0.4240(3) 0.0421(7) Uani 1 1 d . . .
H1 H 0.7377 0.3364 0.4748 0.058(12) Uiso 1 1 d R . .
N2 N 0.7331(3) 0.2159(3) 0.3220(2) 0.0347(6) Uani 1 1 d . . .
N3 N 0.7491(3) 0.0830(2) 0.1104(2) 0.0280(6) Uani 1 1 d . . .
N4 N 0.9305(3) 0.2047(3) 0.0298(2) 0.0337(6) Uani 1 1 d . . .
N5 N 0.9913(3) 0.2534(3) -0.0430(3) 0.0372(6) Uani 1 1 d . . .
H5 H 1.0471 0.3264 -0.0186 0.053(12) Uiso 1 1 d R . .
N6 N 1.0738(3) 0.1853(3) 0.4402(3) 0.0397(7) Uani 1 1 d . . .
N7 N 1.2150(3) 0.4403(3) 0.3352(3) 0.0449(7) Uani 1 1 d . . .
N8 N 0.7828(3) 0.4540(3) 0.0399(3) 0.0398(7) Uani 1 1 d . . .
C1 C 0.5421(7) 0.2116(5) 0.5396(5) 0.0828(17) Uani 1 1 d . . .
H1A H 0.6246 0.2418 0.6208 0.15(3) Uiso 1 1 d R . .
H1B H 0.4873 0.1381 0.5374 0.12(2) Uiso 1 1 d R . .
H1C H 0.4869 0.2827 0.5211 0.17(3) Uiso 1 1 d R . .
C2 C 0.5993(4) 0.1791(4) 0.4361(4) 0.0471(9) Uani 1 1 d . . .
C3 C 0.5671(4) 0.0728(4) 0.3377(3) 0.0467(9) Uani 1 1 d . . .
H3 H 0.5022 -0.0022 0.3197 0.061(12) Uiso 1 1 d R . .
C4 C 0.6525(3) 0.0994(3) 0.2705(3) 0.0324(7) Uani 1 1 d . . .
C5 C 0.6652(3) 0.0211(3) 0.1583(3) 0.0302(7) Uani 1 1 d . . .
C6 C 0.5960(4) -0.1050(3) 0.1039(3) 0.0379(8) Uani 1 1 d . . .
H6 H 0.5363 -0.1439 0.1372 0.052(11) Uiso 1 1 d R . .
C7 C 0.6158(4) -0.1726(3) -0.0008(3) 0.0398(8) Uani 1 1 d . . .
H7 H 0.5725 -0.2584 -0.0370 0.059(12) Uiso 1 1 d R . .
C8 C 0.7011(3) -0.1115(3) -0.0511(3) 0.0360(8) Uani 1 1 d . . .
H8 H 0.7153 -0.1551 -0.1219 0.035(9) Uiso 1 1 d R . .
C9 C 0.7650(3) 0.0167(3) 0.0060(3) 0.0293(7) Uani 1 1 d . . .
C10 C 0.8522(3) 0.0922(3) -0.0433(3) 0.0294(7) Uani 1 1 d . . .
C11 C 0.8644(3) 0.0688(3) -0.1606(3) 0.0344(7) Uani 1 1 d . . .
H11 H 0.8204 -0.0036 -0.2263 0.027(8) Uiso 1 1 d R . .
C12 C 0.9546(4) 0.1741(3) -0.1580(3) 0.0350(7) Uani 1 1 d . . .
C13 C 1.0086(5) 0.2062(4) -0.2547(4) 0.0499(10) Uani 1 1 d . . .
H13A H 0.9437 0.2726 -0.2985 0.13(2) Uiso 1 1 d R . .
H13B H 1.0099 0.1416 -0.3169 0.108(19) Uiso 1 1 d R . .
H13C H 1.1043 0.2607 -0.2094 0.16(3) Uiso 1 1 d R . .
C14 C 0.6130(5) 0.6192(5) 0.2361(4) 0.0580(11) Uani 1 1 d . . .
H14A H 0.6725 0.6988 0.2889 0.087(16) Uiso 1 1 d R . .
H14B H 0.5114 0.6267 0.2209 0.079(14) Uiso 1 1 d R . .
H14C H 0.6257 0.6028 0.1572 0.088(16) Uiso 1 1 d R . .
C15 C 0.6558(4) 0.5094(4) 0.3011(4) 0.0439(9) Uani 1 1 d . . .
H15A H 0.6407 0.5262 0.3799 0.048(10) Uiso 1 1 d R . .
H15B H 0.5931 0.4297 0.2485 0.062(12) Uiso 1 1 d R . .


_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
Tb1 O10 2.425(2) . ?
Tb1 O5 2.437(2) . ?
Tb1 O1 2.465(2) . ?
Tb1 O8 2.471(2) . ?
Tb1 O7 2.503(2) . ?
Tb1 N4 2.524(3) . ?
Tb1 O2 2.526(2) . ?
Tb1 N2 2.529(3) . ?
Tb1 N3 2.611(3) . ?
Tb1 O4 2.668(2) . ?
O1 N6 1.268(3) . ?
O2 N6 1.281(4) . ?
O3 N6 1.211(4) . ?
O4 N7 1.262(4) . ?
O5 N7 1.267(4) . ?
O6 N7 1.214(4) . ?
O7 N8 1.270(3) . ?
O8 N8 1.264(4) . ?
O9 N8 1.223(4) . ?
O10 C15 1.467(4) . ?
O10 H10 0.9300 . ?
N1 C2 1.352(4) . ?
N1 N2 1.359(4) . ?
N1 H1 0.8579 . ?
N2 C4 1.332(4) . ?
N3 C9 1.353(4) . ?
N3 C5 1.354(4) . ?
N4 C10 1.333(4) . ?
N4 N5 1.355(4) . ?
N5 C12 1.352(4) . ?
N5 H5 0.8572 . ?
C1 C2 1.501(5) . ?
C1 H1A 0.9774 . ?
C1 H1B 0.9108 . ?
C1 H1C 0.9568 . ?
C2 C3 1.375(5) . ?
C3 C4 1.391(5) . ?
C3 H3 0.9299 . ?
C4 C5 1.462(4) . ?
C5 C6 1.382(4) . ?
C6 C7 1.379(5) . ?
C6 H6 0.9298 . ?
C7 C8 1.380(5) . ?
C7 H7 0.9295 . ?
C8 C9 1.391(4) . ?
C8 H8 0.9297 . ?
C9 C10 1.468(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.372(5) . ?
C11 H11 0.9291 . ?
C12 C13 1.491(5) . ?
C13 H13A 1.0456 . ?
C13 H13B 0.9036 . ?
C13 H13C 0.9819 . ?
C14 C15 1.491(5) . ?
C14 H14A 0.9591 . ?
C14 H14B 0.9586 . ?
C14 H14C 0.9590 . ?
C15 H15A 0.9696 . ?
C15 H15B 0.9699 . ?

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
O10 Tb1 O5 119.85(8) . . ?
O10 Tb1 O1 129.18(7) . . ?
O5 Tb1 O1 72.64(9) . . ?
O10 Tb1 O8 76.17(7) . . ?
O5 Tb1 O8 77.52(8) . . ?
O1 Tb1 O8 148.06(8) . . ?
O10 Tb1 O7 73.52(7) . . ?
O5 Tb1 O7 123.85(8) . . ?
O1 Tb1 O7 144.48(8) . . ?
O8 Tb1 O7 51.50(7) . . ?
O10 Tb1 N4 141.76(8) . . ?
O5 Tb1 N4 69.91(8) . . ?
O1 Tb1 N4 88.89(8) . . ?
O8 Tb1 N4 70.09(8) . . ?
O7 Tb1 N4 71.62(8) . . ?
O10 Tb1 O2 82.39(7) . . ?
O5 Tb1 O2 75.95(8) . . ?
O1 Tb1 O2 51.20(7) . . ?
O8 Tb1 O2 130.92(7) . . ?
O7 Tb1 O2 154.32(8) . . ?
N4 Tb1 O2 133.94(8) . . ?
O10 Tb1 N2 71.85(8) . . ?
O5 Tb1 N2 142.62(9) . . ?
O1 Tb1 N2 73.66(8) . . ?
O8 Tb1 N2 138.10(8) . . ?
O7 Tb1 N2 93.20(8) . . ?
N4 Tb1 N2 125.03(8) . . ?
O2 Tb1 N2 70.54(8) . . ?
O10 Tb1 N3 122.84(7) . . ?
O5 Tb1 N3 117.29(8) . . ?
O1 Tb1 N3 68.01(8) . . ?
O8 Tb1 N3 118.22(7) . . ?
O7 Tb1 N3 76.63(8) . . ?
N4 Tb1 N3 62.69(8) . . ?
O2 Tb1 N3 110.57(7) . . ?
N2 Tb1 N3 62.42(8) . . ?
O10 Tb1 O4 70.34(7) . . ?
O5 Tb1 O4 49.62(8) . . ?
O1 Tb1 O4 100.68(8) . . ?
O8 Tb1 O4 66.91(7) . . ?
O7 Tb1 O4 113.76(8) . . ?
N4 Tb1 O4 110.55(8) . . ?
O2 Tb1 O4 64.38(8) . . ?
N2 Tb1 O4 123.63(8) . . ?
N3 Tb1 O4 166.10(8) . . ?
N6 O1 Tb1 98.18(18) . . ?
N6 O2 Tb1 94.90(17) . . ?
N7 O4 Tb1 91.26(19) . . ?
N7 O5 Tb1 102.29(19) . . ?
N8 O7 Tb1 94.91(18) . . ?
N8 O8 Tb1 96.58(17) . . ?
C15 O10 Tb1 129.52(19) . . ?
C15 O10 H10 115.2 . . ?
Tb1 O10 H10 115.2 . . ?
C2 N1 N2 112.3(3) . . ?
C2 N1 H1 123.6 . . ?
N2 N1 H1 124.1 . . ?
C4 N2 N1 104.7(3) . . ?
C4 N2 Tb1 122.8(2) . . ?
N1 N2 Tb1 132.4(2) . . ?
C9 N3 C5 117.7(3) . . ?
C9 N3 Tb1 120.64(19) . . ?
C5 N3 Tb1 121.0(2) . . ?
C10 N4 N5 104.3(2) . . ?
C10 N4 Tb1 122.7(2) . . ?
N5 N4 Tb1 131.7(2) . . ?
C12 N5 N4 112.6(3) . . ?
C12 N5 H5 123.7 . . ?
N4 N5 H5 123.7 . . ?
O3 N6 O1 122.0(3) . . ?
O3 N6 O2 122.4(3) . . ?
O1 N6 O2 115.6(3) . . ?
O6 N7 O4 122.0(3) . . ?
O6 N7 O5 121.3(3) . . ?
O4 N7 O5 116.6(3) . . ?
O9 N8 O8 120.5(3) . . ?
O9 N8 O7 122.5(3) . . ?
O8 N8 O7 117.0(3) . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 107.0 . . ?
H1A C1 H1B 112.2 . . ?
C2 C1 H1C 105.2 . . ?
H1A C1 H1C 108.3 . . ?
H1B C1 H1C 114.1 . . ?
N1 C2 C3 105.8(3) . . ?
N1 C2 C1 121.8(4) . . ?
C3 C2 C1 132.3(4) . . ?
C2 C3 C4 106.1(3) . . ?
C2 C3 H3 127.3 . . ?
C4 C3 H3 126.6 . . ?
N2 C4 C3 111.0(3) . . ?
N2 C4 C5 118.6(3) . . ?
C3 C4 C5 130.4(3) . . ?
N3 C5 C6 122.4(3) . . ?
N3 C5 C4 114.4(3) . . ?
C6 C5 C4 123.2(3) . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 118.8(3) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
N3 C9 C8 122.5(3) . . ?
N3 C9 C10 114.5(3) . . ?
C8 C9 C10 123.0(3) . . ?
N4 C10 C11 111.4(3) . . ?
N4 C10 C9 118.2(3) . . ?
C11 C10 C9 130.4(3) . . ?
C12 C11 C10 105.7(3) . . ?
C12 C11 H11 127.7 . . ?
C10 C11 H11 126.6 . . ?
N5 C12 C11 106.0(3) . . ?
N5 C12 C13 122.6(3) . . ?
C11 C12 C13 131.4(3) . . ?
C12 C13 H13A 107.8 . . ?
C12 C13 H13B 119.5 . . ?
H13A C13 H13B 106.8 . . ?
C12 C13 H13C 107.5 . . ?
H13A C13 H13C 101.2 . . ?
H13B C13 H13C 112.4 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 108.4 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 110.3 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.4 . . ?
O10 C15 C14 112.7(3) . . ?
O10 C15 H15A 109.3 . . ?
C14 C15 H15A 109.6 . . ?
O10 C15 H15B 108.1 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.7 . . ?

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
O10 H10 O2 0.93 1.96 2.827(3) 154.6 2_766
N1 H1 O4 0.86 2.22 3.056(4) 164.8 2_766

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.072
