# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 1443936'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O9 Sm'
_chemical_formula_weight         553.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -5.3236 12.2178 '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                   6.0501(9)
_cell_length_b                   13.625(2)
_cell_length_c                   13.700(3)
_cell_angle_alpha                112.682(16)
_cell_angle_beta                 97.805(15)
_cell_angle_gamma                92.550(12)
_cell_volume                     1026.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    796
_cell_measurement_theta_min      7.7600
_cell_measurement_theta_max      58.5620

_exptl_crystal_description       strip
_exptl_crystal_colour            'pale yellow '
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    21.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2427
_exptl_absorpt_correction_T_max  0.2727
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6032
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_sigmaI/netI    0.1877
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         67.25
_reflns_number_total             3684
_reflns_number_gt                2310
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0612P)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         3684
_refine_ls_number_parameters     346
_refine_ls_number_restraints     1197
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0790
_refine_ls_wR_factor_ref         0.2071
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      0.898
_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 0.44904(13) 0.16566(6) 1.06863(6) 0.0353(2) Uani 1 1 d U . .
N1 N 0.254(4) -0.3085(18) 0.3601(17) 0.068(3) Uani 0.699(9) 1 d PU A 1
N1' N 0.350(8) -0.259(3) 0.392(3) 0.062(4) Uani 0.301(9) 1 d PDU A 2
O1 O 0.3517(15) -0.0235(7) 0.9114(7) 0.0393(19) Uani 1 1 d U . .
O2 O 0.1800(15) 0.1107(7) 0.8993(7) 0.0427(19) Uani 1 1 d U . .
O3 O -0.1536(14) -0.0747(7) 0.8792(7) 0.0385(19) Uani 1 1 d U . .
O4 O -0.3841(15) -0.1985(8) 0.7454(7) 0.044(2) Uani 1 1 d U . .
O5 O -0.078(3) -0.2179(13) 0.4111(12) 0.063(3) Uani 0.699(9) 1 d PU A 1
O6 O 0.4244(15) 0.3210(7) 1.0183(8) 0.044(2) Uani 1 1 d U . .
O7 O 0.1714(16) 0.3020(7) 1.1135(8) 0.046(2) Uani 1 1 d U . .
O8 O 0.7864(16) 0.2798(8) 1.1894(8) 0.046(2) Uani 1 1 d DU B .
H8A H 0.8358 0.3126 1.1539 0.056 Uiso 1 1 d R . .
O9 O 0.7272(15) 0.1446(8) 0.9537(8) 0.048(2) Uani 1 1 d U . .
H9A H 0.8478 0.1830 0.9903 0.072 Uiso 1 1 d R . .
H9B H 0.7520 0.0794 0.9275 0.072 Uiso 1 1 d R . .
O5' O 0.275(6) -0.078(3) 0.485(3) 0.058(3) Uani 0.301(9) 1 d PU A 2
C1 C 0.217(2) 0.0157(11) 0.8611(11) 0.037(2) Uani 1 1 d U . .
C2 C 0.131(2) -0.0469(12) 0.7435(11) 0.040(2) Uani 1 1 d U . .
C3 C 0.254(3) -0.0366(13) 0.6700(12) 0.051(3) Uani 1 1 d U A .
H3 H 0.3874 0.0087 0.6941 0.061 Uiso 1 1 calc R . .
C4 C 0.183(3) -0.0931(13) 0.5589(13) 0.055(3) Uani 1 1 d U . .
H4 H 0.2707 -0.0866 0.5107 0.067 Uiso 0.699(9) 1 d PR A 1
C5 C -0.017(3) -0.1575(14) 0.5220(13) 0.059(3) Uani 1 1 d U A .
H5 H -0.0664 -0.1928 0.4486 0.070 Uiso 0.301(9) 1 d PR A 2
C6 C -0.147(3) -0.1702(13) 0.5943(12) 0.053(3) Uani 1 1 d U . .
H6 H -0.2812 -0.2149 0.5696 0.064 Uiso 1 1 calc R A .
C7 C -0.074(2) -0.1163(12) 0.7008(11) 0.041(2) Uani 1 1 d U A .
C8 C -0.212(2) -0.1297(12) 0.7813(12) 0.040(2) Uani 1 1 d U . .
C9 C 0.091(4) -0.239(2) 0.3471(19) 0.058(3) Uani 0.699(9) 1 d PU A 1
C10 C 0.419(4) -0.330(2) 0.282(2) 0.064(4) Uani 0.699(9) 1 d PU A 1
H10 H 0.5316 -0.3739 0.2827 0.076 Uiso 0.699(9) 1 calc PR A 1
C11 C 0.398(4) -0.284(2) 0.2116(19) 0.059(4) Uani 0.699(9) 1 d PU A 1
H11 H 0.5061 -0.2923 0.1677 0.071 Uiso 0.699(9) 1 calc PR A 1
C12 C 0.238(7) -0.229(2) 0.2009(19) 0.054(3) Uani 0.699(9) 1 d PU A 1
H12 H 0.2279 -0.2037 0.1464 0.065 Uiso 0.699(9) 1 calc PR A 1
C13 C 0.086(4) -0.206(2) 0.2654(18) 0.059(3) Uani 0.699(9) 1 d PU A 1
H13 H -0.0285 -0.1661 0.2542 0.071 Uiso 0.699(9) 1 calc PR A 1
C14 C 0.242(2) 0.3446(11) 1.0555(11) 0.037(3) Uani 1 1 d U . .
C15 C 0.115(2) 0.4246(11) 1.0279(11) 0.035(3) Uani 1 1 d U . .
C16 C 0.189(2) 0.4657(11) 0.9567(12) 0.043(3) Uani 1 1 d U . .
H16 H 0.3170 0.4429 0.9275 0.052 Uiso 1 1 calc R . .
C17 C 0.074(2) 0.5395(11) 0.9297(12) 0.046(3) Uani 1 1 d U . .
H17 H 0.1249 0.5653 0.8822 0.056 Uiso 1 1 calc R . .
C18 C 0.817(4) 0.3628(18) 1.3028(15) 0.122(6) Uani 1 1 d DU . .
H18A H 0.9773 0.3846 1.3186 0.146 Uiso 1 1 d R B .
H18B H 0.7946 0.3199 1.3437 0.146 Uiso 1 1 d R . .
C19 C 0.728(7) 0.469(2) 1.363(3) 0.143(13) Uani 0.60(3) 1 d PDU B 1
H19A H 0.6755 0.5004 1.3127 0.215 Uiso 0.60(3) 1 calc PR B 1
H19B H 0.8466 0.5173 1.4160 0.215 Uiso 0.60(3) 1 calc PR B 1
H19C H 0.6071 0.4575 1.3966 0.215 Uiso 0.60(3) 1 calc PR B 1
C9' C 0.293(9) -0.161(3) 0.396(2) 0.057(4) Uani 0.301(9) 1 d PDU A 2
C10' C 0.348(9) -0.342(3) 0.293(3) 0.058(4) Uani 0.301(9) 1 d PDU A 2
H10' H 0.3577 -0.4114 0.2884 0.070 Uiso 0.301(9) 1 calc PR A 2
C11' C 0.332(9) -0.320(3) 0.202(2) 0.059(4) Uani 0.301(9) 1 d PDU A 2
H11' H 0.3625 -0.3710 0.1384 0.070 Uiso 0.301(9) 1 calc PR A 2
C12' C 0.271(15) -0.222(4) 0.206(3) 0.058(4) Uani 0.301(9) 1 d PDU A 2
H12' H 0.2331 -0.2115 0.1433 0.070 Uiso 0.301(9) 1 calc PR A 2
C13' C 0.265(9) -0.141(3) 0.304(3) 0.058(4) Uani 0.301(9) 1 d PDU A 2
H13' H 0.2433 -0.0721 0.3083 0.070 Uiso 0.301(9) 1 calc PR A 2
C19' C 0.704(7) 0.365(4) 1.399(3) 0.082(11) Uani 0.40(3) 1 d PDU B 2
H19D H 0.6254 0.2962 1.3804 0.123 Uiso 0.40(3) 1 d PR B 2
H19E H 0.6005 0.4185 1.4146 0.123 Uiso 0.40(3) 1 d PR B 2
H19F H 0.8180 0.3814 1.4603 0.123 Uiso 0.40(3) 1 d PR B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O1 2.409(9) 2_657 ?
Sm1 O9 2.409(8) . ?
Sm1 O3 2.465(8) 2_557 ?
Sm1 O6 2.471(8) . ?
Sm1 O2 2.474(10) . ?
Sm1 O8 2.477(10) . ?
Sm1 O4 2.500(9) 2_557 ?
Sm1 O7 2.516(9) . ?
Sm1 O1 2.621(9) . ?
Sm1 C8 2.837(13) 2_557 ?
Sm1 C14 2.846(13) . ?
Sm1 C1 2.901(15) . ?
N1 C9 1.44(3) . ?
N1 C10 1.52(3) . ?
N1' C9' 1.381(8) . ?
N1' C10' 1.382(8) . ?
O1 C1 1.264(14) . ?
O1 Sm1 2.409(9) 2_657 ?
O2 C1 1.239(15) . ?
O3 C8 1.249(16) . ?
O3 Sm1 2.465(8) 2_557 ?
O4 C8 1.276(16) . ?
O4 Sm1 2.500(9) 2_557 ?
O5 C9 1.40(2) . ?
O5 C5 1.41(2) . ?
O6 C14 1.283(14) . ?
O7 C14 1.255(14) . ?
O8 C18 1.508(14) . ?
O5' C4 1.29(3) . ?
O5' C9' 1.33(4) . ?
C1 C2 1.506(19) . ?
C2 C3 1.374(17) . ?
C2 C7 1.432(19) . ?
C3 C4 1.41(2) . ?
C4 C5 1.37(2) . ?
C5 C6 1.399(19) . ?
C6 C7 1.35(2) . ?
C7 C8 1.528(17) . ?
C8 Sm1 2.837(13) 2_557 ?
C9 C13 1.36(3) . ?
C10 C11 1.33(3) . ?
C11 C12 1.28(4) . ?
C12 C13 1.33(4) . ?
C14 C15 1.494(16) . ?
C15 C17 1.375(17) 2_567 ?
C15 C16 1.408(17) . ?
C16 C17 1.383(17) . ?
C17 C15 1.375(17) 2_567 ?
C18 C19 1.530(17) . ?
C18 C19' 1.551(17) . ?
C9' C13' 1.382(8) . ?
C10' C11' 1.383(8) . ?
C11' C12' 1.382(8) . ?
C12' C13' 1.380(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sm1 O9 76.4(3) 2_657 . ?
O1 Sm1 O3 80.6(3) 2_657 2_557 ?
O9 Sm1 O3 146.0(3) . 2_557 ?
O1 Sm1 O6 151.1(3) 2_657 . ?
O9 Sm1 O6 76.4(3) . . ?
O3 Sm1 O6 128.1(3) 2_557 . ?
O1 Sm1 O2 114.4(3) 2_657 . ?
O9 Sm1 O2 83.9(3) . . ?
O3 Sm1 O2 83.2(3) 2_557 . ?
O6 Sm1 O2 71.9(3) . . ?
O1 Sm1 O8 83.1(3) 2_657 . ?
O9 Sm1 O8 75.7(3) . . ?
O3 Sm1 O8 126.0(3) 2_557 . ?
O6 Sm1 O8 81.1(3) . . ?
O2 Sm1 O8 149.3(3) . . ?
O1 Sm1 O4 82.8(3) 2_657 2_557 ?
O9 Sm1 O4 145.3(3) . 2_557 ?
O3 Sm1 O4 52.7(3) 2_557 2_557 ?
O6 Sm1 O4 115.5(3) . 2_557 ?
O2 Sm1 O4 130.4(3) . 2_557 ?
O8 Sm1 O4 74.4(3) . 2_557 ?
O1 Sm1 O7 154.6(3) 2_657 . ?
O9 Sm1 O7 128.7(3) . . ?
O3 Sm1 O7 78.0(3) 2_557 . ?
O6 Sm1 O7 52.6(3) . . ?
O2 Sm1 O7 76.6(3) . . ?
O8 Sm1 O7 98.5(3) . . ?
O4 Sm1 O7 73.3(3) 2_557 . ?
O1 Sm1 O1 63.5(3) 2_657 . ?
O9 Sm1 O1 72.6(3) . . ?
O3 Sm1 O1 74.9(3) 2_557 . ?
O6 Sm1 O1 116.3(3) . . ?
O2 Sm1 O1 50.9(3) . . ?
O8 Sm1 O1 138.1(3) . . ?
O4 Sm1 O1 121.8(3) 2_557 . ?
O7 Sm1 O1 122.7(3) . . ?
O1 Sm1 C8 81.7(3) 2_657 2_557 ?
O9 Sm1 C8 158.1(4) . 2_557 ?
O3 Sm1 C8 26.0(4) 2_557 2_557 ?
O6 Sm1 C8 124.9(3) . 2_557 ?
O2 Sm1 C8 106.5(4) . 2_557 ?
O8 Sm1 C8 100.8(4) . 2_557 ?
O4 Sm1 C8 26.7(4) 2_557 2_557 ?
O7 Sm1 C8 73.1(3) . 2_557 ?
O1 Sm1 C8 98.6(4) . 2_557 ?
O1 Sm1 C14 175.7(4) 2_657 . ?
O9 Sm1 C14 102.6(3) . . ?
O3 Sm1 C14 102.0(3) 2_557 . ?
O6 Sm1 C14 26.7(3) . . ?
O2 Sm1 C14 69.5(4) . . ?
O8 Sm1 C14 92.6(4) . . ?
O4 Sm1 C14 96.0(3) 2_557 . ?
O7 Sm1 C14 26.1(3) . . ?
O1 Sm1 C14 120.4(3) . . ?
C8 Sm1 C14 99.2(4) 2_557 . ?
O1 Sm1 C1 89.3(4) 2_657 . ?
O9 Sm1 C1 76.6(3) . . ?
O3 Sm1 C1 78.5(3) 2_557 . ?
O6 Sm1 C1 93.6(4) . . ?
O2 Sm1 C1 25.1(3) . . ?
O8 Sm1 C1 152.2(3) . . ?
O4 Sm1 C1 131.2(4) 2_557 . ?
O7 Sm1 C1 99.7(3) . . ?
O1 Sm1 C1 25.8(3) . . ?
C8 Sm1 C1 104.5(4) 2_557 . ?
C14 Sm1 C1 94.5(4) . . ?
C9 N1 C10 113.6(19) . . ?
C9' N1' C10' 119.7(8) . . ?
C1 O1 Sm1 153.9(9) . 2_657 ?
C1 O1 Sm1 89.5(8) . . ?
Sm1 O1 Sm1 116.5(3) 2_657 . ?
C1 O2 Sm1 97.1(8) . . ?
C8 O3 Sm1 93.9(8) . 2_557 ?
C8 O4 Sm1 91.5(8) . 2_557 ?
C9 O5 C5 118.5(18) . . ?
C14 O6 Sm1 93.2(7) . . ?
C14 O7 Sm1 91.8(8) . . ?
C18 O8 Sm1 131.4(11) . . ?
C4 O5' C9' 119(4) . . ?
O2 C1 O1 122.4(14) . . ?
O2 C1 C2 117.0(12) . . ?
O1 C1 C2 119.4(12) . . ?
O2 C1 Sm1 57.8(8) . . ?
O1 C1 Sm1 64.6(8) . . ?
C2 C1 Sm1 166.1(9) . . ?
C3 C2 C7 116.4(14) . . ?
C3 C2 C1 118.9(14) . . ?
C7 C2 C1 124.7(12) . . ?
C2 C3 C4 121.4(15) . . ?
O5' C4 C5 115(2) . . ?
O5' C4 C3 124(2) . . ?
C5 C4 C3 119.9(15) . . ?
C4 C5 C6 120.4(16) . . ?
C4 C5 O5 118.7(15) . . ?
C6 C5 O5 120.6(16) . . ?
C7 C6 C5 118.7(16) . . ?
C6 C7 C2 123.1(13) . . ?
C6 C7 C8 119.7(14) . . ?
C2 C7 C8 117.2(13) . . ?
O3 C8 O4 121.7(12) . . ?
O3 C8 C7 120.1(13) . . ?
O4 C8 C7 118.2(13) . . ?
O3 C8 Sm1 60.1(7) . 2_557 ?
O4 C8 Sm1 61.8(7) . 2_557 ?
C7 C8 Sm1 176.0(9) . 2_557 ?
C13 C9 O5 121(2) . . ?
C13 C9 N1 120(2) . . ?
O5 C9 N1 119(2) . . ?
C11 C10 N1 118(2) . . ?
C12 C11 C10 124(3) . . ?
C11 C12 C13 122(2) . . ?
C12 C13 C9 122(2) . . ?
O7 C14 O6 121.1(12) . . ?
O7 C14 C15 121.0(12) . . ?
O6 C14 C15 118.0(11) . . ?
O7 C14 Sm1 62.1(7) . . ?
O6 C14 Sm1 60.1(6) . . ?
C15 C14 Sm1 169.4(10) . . ?
C17 C15 C16 118.2(12) 2_567 . ?
C17 C15 C14 122.0(12) 2_567 . ?
C16 C15 C14 119.8(11) . . ?
C17 C16 C15 120.7(12) . . ?
C15 C17 C16 121.1(13) 2_567 . ?
O8 C18 C19 137(3) . . ?
O8 C18 C19' 130(3) . . ?
C19 C18 C19' 66(2) . . ?
O5' C9' N1' 125(3) . . ?
O5' C9' C13' 115(3) . . ?
N1' C9' C13' 119.8(8) . . ?
N1' C10' C11' 119.6(8) . . ?
C12' C11' C10' 119.6(9) . . ?
C13' C12' C11' 119.7(9) . . ?
C12' C13' C9' 120.0(8) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.100
_refine_diff_density_min         -1.299
_refine_diff_density_rms         0.194
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1443938'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Gd N O9'
_chemical_formula_weight         560.59

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'
O O 0.0106 0.0060 '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'
Gd Gd -0.1653 3.9035 '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                   6.0069(10)
_cell_length_b                   13.694(2)
_cell_length_c                   13.732(2)
_cell_angle_alpha                112.299(2)
_cell_angle_beta                 91.789(2)
_cell_angle_gamma                98.976(2)
_cell_volume                     1027.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1038
_cell_measurement_theta_min      7.7940
_cell_measurement_theta_max      70.7010

_exptl_crystal_description       strip
_exptl_crystal_colour            'pale yellow '
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    3.279
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6390
_exptl_absorpt_correction_T_max  0.6568
_exptl_absorpt_process_details   asASas

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11033
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3622
_reflns_number_gt                3369
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0482P)²+1.5718P] 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         3622
_refine_ls_number_parameters     331
_refine_ls_number_restraints     1116
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.197(3) 0.7870(7) 0.7076(8) 0.063(3) Uani 0.449(6) 1 d PDU A 1
N1' N 0.2768(17) 0.7976(7) 0.7290(8) 0.058(3) Uani 0.551(6) 1 d PDU A 2
O1 O -0.3284(6) 0.1076(3) 0.7977(3) 0.0386(8) Uani 1 1 d U B .
O2 O -0.0761(6) 0.0136(3) 0.8159(3) 0.0424(9) Uani 1 1 d U B .
O3 O 0.2170(6) -0.0494(3) 0.6416(3) 0.0412(8) Uani 1 1 d U B .
H3B H 0.1488 -0.1124 0.6309 0.062 Uiso 1 1 d R . .
H3C H 0.3086 -0.0258 0.6972 0.062 Uiso 1 1 d R . .
O4 O 0.2791(7) 0.1806(3) 0.7756(3) 0.0433(9) Uani 1 1 d U B .
O5 O 0.1548(5) 0.0906(3) 0.5273(3) 0.0336(7) Uani 1 1 d U . .
O6 O 0.3296(6) 0.1028(3) 0.3941(3) 0.0377(8) Uani 1 1 d U . .
O7 O 0.6598(6) 0.1189(3) 0.5766(3) 0.0346(7) Uani 1 1 d U . .
O8 O 0.8945(6) 0.2511(3) 0.6981(3) 0.0443(9) Uani 1 1 d U . .
O9 O 0.2510(18) 0.5160(7) 0.5825(8) 0.062(2) Uani 0.449(6) 1 d PU A 1
O9' O 0.5896(15) 0.5874(6) 0.7167(7) 0.065(2) Uani 0.551(6) 1 d PU A 2
C1 C -0.2559(8) 0.0498(4) 0.8412(4) 0.0333(10) Uani 1 1 d U . .
C2 C -0.3830(8) 0.0245(4) 0.9233(4) 0.0321(10) Uani 1 1 d U . .
C3 C -0.3102(9) -0.0440(5) 0.9657(4) 0.0420(12) Uani 1 1 d U . .
H3 H -0.1828 -0.0738 0.9429 0.050 Uiso 1 1 calc R . .
C4 C -0.4271(9) -0.0681(5) 1.0418(4) 0.0426(12) Uani 1 1 d U . .
H4 H -0.3773 -0.1140 1.0696 0.051 Uiso 1 1 calc R . .
C5 C 0.2915(8) 0.1433(4) 0.4888(4) 0.0297(9) Uani 1 1 d U . .
C6 C 0.3867(9) 0.2590(4) 0.5517(4) 0.0353(10) Uani 1 1 d U A .
C7 C 0.5882(9) 0.2959(4) 0.6175(4) 0.0382(11) Uani 1 1 d U . .
C8 C 0.6617(12) 0.4054(5) 0.6718(5) 0.0567(14) Uani 1 1 d U A .
H8 H 0.7963 0.4304 0.7160 0.068 Uiso 1 1 calc R . .
C9 C 0.5348(13) 0.4785(5) 0.6605(6) 0.0649(15) Uani 1 1 d U . .
H9 H 0.5835 0.5518 0.6978 0.078 Uiso 0.449(6) 1 calc PR A 1
C10 C 0.3399(12) 0.4418(5) 0.5947(5) 0.0598(14) Uani 1 1 d U A .
H10 H 0.2567 0.4904 0.5863 0.072 Uiso 0.551(6) 1 calc PR A 2
C11 C 0.2634(10) 0.3324(4) 0.5399(5) 0.0465(12) Uani 1 1 d U . .
H11 H 0.1295 0.3082 0.4953 0.056 Uiso 1 1 calc R A .
C12 C 0.7231(8) 0.2173(4) 0.6310(4) 0.0346(10) Uani 1 1 d U . .
C13 C 0.232(2) 0.6062(7) 0.6649(7) 0.055(2) Uani 0.449(6) 1 d PDU A 1
C14 C 0.234(3) 0.6913(8) 0.6353(7) 0.057(2) Uani 0.449(6) 1 d PDU A 1
H14 H 0.2610 0.6841 0.5668 0.069 Uiso 0.449(6) 1 calc PR A 1
C16 C 0.1310(12) 0.7899(5) 0.8004(5) 0.0712(18) Uani 1 1 d DU . .
H16 H 0.0902 0.8530 0.8460 0.085 Uiso 1 1 d R A .
C17 C 0.1205(13) 0.7070(5) 0.8336(5) 0.0820(19) Uani 1 1 d DU A .
H17 H 0.0701 0.7122 0.8984 0.098 Uiso 1 1 d R . .
C18 C 0.187(3) 0.6140(8) 0.7644(9) 0.062(3) Uani 0.449(6) 1 d PDU A 1
H18 H 0.2012 0.5582 0.7857 0.074 Uiso 0.449(6) 1 calc PR A 1
C19 C 0.333(2) 0.2984(10) 0.8480(10) 0.136(4) Uani 1 1 d U . .
H19A H 0.3345 0.2990 0.9189 0.163 Uiso 1 1 d R B .
H19B H 0.4904 0.3203 0.8390 0.163 Uiso 1 1 d R . .
C20 C 0.218(4) 0.3984(14) 0.8527(15) 0.077(5) Uani 0.424(16) 1 d PU B 1
H20A H 0.1509 0.3851 0.7835 0.115 Uiso 0.424(16) 1 calc PR B 1
H20B H 0.3318 0.4624 0.8764 0.115 Uiso 0.424(16) 1 calc PR B 1
H20C H 0.1038 0.4074 0.9010 0.115 Uiso 0.424(16) 1 calc PR B 1
C13' C 0.4274(17) 0.6512(8) 0.7415(9) 0.057(2) Uani 0.551(6) 1 d PDU A 2
C14' C 0.4350(17) 0.7320(8) 0.7059(9) 0.057(2) Uani 0.551(6) 1 d PDU A 2
H14' H 0.5498 0.7428 0.6652 0.068 Uiso 0.551(6) 1 calc PR A 2
C18' C 0.264(2) 0.6370(8) 0.8054(11) 0.066(3) Uani 0.551(6) 1 d PDU A 2
H18' H 0.2544 0.5814 0.8292 0.080 Uiso 0.551(6) 1 d PR A 2
C20' C 0.195(5) 0.360(2) 0.9523(19) 0.197(11) Uani 0.576(16) 1 d PU B 2
H20D H 0.1230 0.3059 0.9751 0.295 Uiso 0.576(16) 1 d PR B 2
H20E H 0.3034 0.4116 1.0080 0.295 Uiso 0.576(16) 1 d PR B 2
H20F H 0.0828 0.3957 0.9355 0.295 Uiso 0.576(16) 1 d PR B 2
Gd1 Gd -0.05242(3) 0.064799(17) 0.663113(16) 0.02663(10) Uani 1 1 d U . .
H21 H 0.374(10) 0.155(5) 0.786(5) 0.040 Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.334(7) . ?
N1 C14 1.368(8) . ?
N1' C16 1.358(7) . ?
N1' C14' 1.371(7) . ?
O1 C1 1.275(6) . ?
O1 Gd1 2.486(3) . ?
O2 C1 1.262(6) . ?
O2 Gd1 2.453(3) . ?
O3 Gd1 2.371(3) . ?
O4 C19 1.515(12) . ?
O4 Gd1 2.414(4) . ?
O5 C5 1.266(5) . ?
O5 Gd1 2.380(3) . ?
O5 Gd1 2.648(3) 2_556 ?
O6 C5 1.250(6) . ?
O6 Gd1 2.452(3) 2_556 ?
O7 C12 1.257(6) . ?
O7 Gd1 2.426(3) 1_655 ?
O8 C12 1.262(6) . ?
O8 Gd1 2.485(4) 1_655 ?
O9 C10 1.279(10) . ?
O9 C13 1.346(13) . ?
O9' C9 1.373(10) . ?
O9' C13' 1.374(11) . ?
C1 C2 1.497(6) . ?
C2 C4 1.384(7) 2_457 ?
C2 C3 1.392(7) . ?
C3 C4 1.389(7) . ?
C4 C2 1.384(7) 2_457 ?
C5 C6 1.494(7) . ?
C5 Gd1 2.926(5) 2_556 ?
C6 C7 1.389(8) . ?
C6 C11 1.391(7) . ?
C7 C8 1.387(8) . ?
C7 C12 1.505(7) . ?
C8 C9 1.398(9) . ?
C9 C10 1.358(10) . ?
C10 C11 1.389(8) . ?
C12 Gd1 2.813(5) 1_655 ?
C13 C18 1.367(8) . ?
C13 C14 1.371(8) . ?
C16 C17 1.368(5) . ?
C17 C18' 1.345(7) . ?
C17 C18 1.397(7) . ?
C19 C20 1.61(2) . ?
C19 C20' 1.68(2) . ?
C13' C14' 1.365(7) . ?
C13' C18' 1.376(8) . ?
Gd1 O7 2.426(3) 1_455 ?
Gd1 O6 2.452(4) 2_556 ?
Gd1 O8 2.485(4) 1_455 ?
Gd1 O5 2.648(3) 2_556 ?
Gd1 C12 2.813(5) 1_455 ?
Gd1 C5 2.926(5) 2_556 ?

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
C16 N1 C14 118.2(6) . . ?
C16 N1' C14' 117.9(6) . . ?
C1 O1 Gd1 91.8(3) . . ?
C1 O2 Gd1 93.7(3) . . ?
C19 O4 Gd1 134.0(5) . . ?
C5 O5 Gd1 154.8(3) . . ?
C5 O5 Gd1 89.5(3) . 2_556 ?
Gd1 O5 Gd1 115.53(12) . 2_556 ?
C5 O6 Gd1 99.2(3) . 2_556 ?
C12 O7 Gd1 94.2(3) . 1_655 ?
C12 O8 Gd1 91.3(3) . 1_655 ?
C10 O9 C13 121.8(9) . . ?
C9 O9' C13' 121.9(9) . . ?
O2 C1 O1 120.4(4) . . ?
O2 C1 C2 119.4(4) . . ?
O1 C1 C2 120.2(4) . . ?
C4 C2 C3 119.0(4) 2_457 . ?
C4 C2 C1 121.2(4) 2_457 . ?
C3 C2 C1 119.8(4) . . ?
C4 C3 C2 120.2(5) . . ?
C2 C4 C3 120.8(5) 2_457 . ?
O6 C5 O5 120.4(4) . . ?
O6 C5 C6 118.7(4) . . ?
O5 C5 C6 120.4(4) . . ?
O6 C5 Gd1 55.8(2) . 2_556 ?
O5 C5 Gd1 64.8(3) . 2_556 ?
C6 C5 Gd1 167.3(3) . 2_556 ?
C7 C6 C11 119.5(5) . . ?
C7 C6 C5 124.4(4) . . ?
C11 C6 C5 116.1(5) . . ?
C8 C7 C6 119.6(5) . . ?
C8 C7 C12 120.4(5) . . ?
C6 C7 C12 120.0(5) . . ?
C7 C8 C9 120.4(6) . . ?
C10 C9 O9' 116.7(6) . . ?
C10 C9 C8 119.7(6) . . ?
O9' C9 C8 123.6(7) . . ?
O9 C10 C9 113.9(7) . . ?
O9 C10 C11 125.1(8) . . ?
C9 C10 C11 120.7(6) . . ?
C10 C11 C6 120.1(6) . . ?
O7 C12 O8 121.3(4) . . ?
O7 C12 C7 119.2(5) . . ?
O8 C12 C7 119.5(5) . . ?
O7 C12 Gd1 59.3(2) . 1_655 ?
O8 C12 Gd1 62.0(3) . 1_655 ?
C7 C12 Gd1 175.7(3) . 1_655 ?
O9 C13 C18 126.4(8) . . ?
O9 C13 C14 111.7(8) . . ?
C18 C13 C14 121.5(6) . . ?
N1 C14 C13 119.3(6) . . ?
N1 C16 N1' 22.4(8) . . ?
N1 C16 C17 124.8(5) . . ?
N1' C16 C17 119.7(5) . . ?
C18' C17 C16 122.4(5) . . ?
C18' C17 C18 27.7(8) . . ?
C16 C17 C18 116.4(5) . . ?
C13 C18 C17 119.1(6) . . ?
O4 C19 C20 131.5(11) . . ?
O4 C19 C20' 126.0(14) . . ?
C20 C19 C20' 59.8(13) . . ?
C14' C13' O9' 119.4(7) . . ?
C14' C13' C18' 120.0(6) . . ?
O9' C13' C18' 120.6(7) . . ?
C13' C14' N1' 121.3(6) . . ?
C17 C18' C13' 117.9(6) . . ?
O3 Gd1 O5 77.03(11) . . ?
O3 Gd1 O4 75.79(13) . . ?
O5 Gd1 O4 82.89(13) . . ?
O3 Gd1 O7 146.38(12) . 1_455 ?
O5 Gd1 O7 80.96(11) . 1_455 ?
O4 Gd1 O7 126.30(12) . 1_455 ?
O3 Gd1 O6 84.06(13) . 2_556 ?
O5 Gd1 O6 115.00(11) . 2_556 ?
O4 Gd1 O6 149.39(13) . 2_556 ?
O7 Gd1 O6 82.59(12) 1_455 2_556 ?
O3 Gd1 O2 75.59(12) . . ?
O5 Gd1 O2 150.14(11) . . ?
O4 Gd1 O2 79.07(13) . . ?
O7 Gd1 O2 128.88(11) 1_455 . ?
O6 Gd1 O2 73.70(12) 2_556 . ?
O3 Gd1 O8 145.01(13) . 1_455 ?
O5 Gd1 O8 81.88(12) . 1_455 ?
O4 Gd1 O8 74.13(13) . 1_455 ?
O7 Gd1 O8 53.06(11) 1_455 1_455 ?
O6 Gd1 O8 130.49(12) 2_556 1_455 ?
O2 Gd1 O8 115.19(13) . 1_455 ?
O3 Gd1 O1 128.21(11) . . ?
O5 Gd1 O1 154.23(11) . . ?
O4 Gd1 O1 97.45(13) . . ?
O7 Gd1 O1 78.17(11) 1_455 . ?
O6 Gd1 O1 77.11(12) 2_556 . ?
O2 Gd1 O1 52.94(11) . . ?
O8 Gd1 O1 73.55(12) 1_455 . ?
O3 Gd1 O5 73.04(12) . 2_556 ?
O5 Gd1 O5 64.47(13) . 2_556 ?
O4 Gd1 O5 138.82(11) . 2_556 ?
O7 Gd1 O5 74.64(11) 1_455 2_556 ?
O6 Gd1 O5 50.53(10) 2_556 2_556 ?
O2 Gd1 O5 117.42(12) . 2_556 ?
O8 Gd1 O5 121.62(11) 1_455 2_556 ?
O1 Gd1 O5 122.95(11) . 2_556 ?
O3 Gd1 C12 158.17(13) . 1_455 ?
O5 Gd1 C12 81.17(12) . 1_455 ?
O4 Gd1 C12 100.48(14) . 1_455 ?
O7 Gd1 C12 26.45(13) 1_455 1_455 ?
O6 Gd1 C12 106.50(14) 2_556 1_455 ?
O2 Gd1 C12 125.35(12) . 1_455 ?
O8 Gd1 C12 26.63(13) 1_455 1_455 ?
O1 Gd1 C12 73.41(12) . 1_455 ?
O5 Gd1 C12 98.60(13) 2_556 1_455 ?
O3 Gd1 C5 76.22(13) . 2_556 ?
O5 Gd1 C5 90.08(12) . 2_556 ?
O4 Gd1 C5 151.99(13) . 2_556 ?
O7 Gd1 C5 78.74(12) 1_455 2_556 ?
O6 Gd1 C5 24.94(11) 2_556 2_556 ?
O2 Gd1 C5 94.77(13) . 2_556 ?
O8 Gd1 C5 131.78(12) 1_455 2_556 ?
O1 Gd1 C5 100.41(12) . 2_556 ?
O5 Gd1 C5 25.64(11) 2_556 2_556 ?
C12 Gd1 C5 105.19(14) 1_455 2_556 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.299
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.126
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1443937'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Eu N O9'
_chemical_formula_weight         555.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -8.9294 11.1857 '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                   6.0198(7)
_cell_length_b                   13.6689(17)
_cell_length_c                   13.6699(17)
_cell_angle_alpha                112.195(12)
_cell_angle_beta                 92.182(10)
_cell_angle_gamma                98.036(11)
_cell_volume                     1026.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1038
_cell_measurement_theta_min      7.7940
_cell_measurement_theta_max      70.7010

_exptl_crystal_description       strip
_exptl_crystal_colour            'pale yellow '
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             546
_exptl_absorpt_coefficient_mu    22.341
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.2680
_exptl_absorpt_correction_T_max  0.3038
_exptl_absorpt_process_details   sdasd

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6044
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_sigmaI/netI    0.1274
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         67.22
_reflns_number_total             3688
_reflns_number_gt                2803
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0789P)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         3688
_refine_ls_number_parameters     309
_refine_ls_number_restraints     968
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1851
_refine_ls_wR_factor_gt          0.1642
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      0.941
_refine_ls_shift/su_max          0.014
_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 0.55255(10) 0.93342(5) 0.83593(5) 0.0318(2) Uani 1 1 d U . .
O1 O 0.6101(13) 0.7481(6) 0.8034(7) 0.0514(18) Uani 1 1 d U . .
O2 O 0.8461(12) 0.8815(5) 0.9245(6) 0.0393(15) Uani 1 1 d U . .
O3 O 1.3475(11) 0.9097(5) 0.9754(6) 0.0370(15) Uani 1 1 d U . .
O4 O 1.1749(12) 0.8980(6) 1.1086(6) 0.0436(16) Uani 1 1 d U . .
O5 O 0.5760(12) 0.9837(6) 0.6813(6) 0.0457(17) Uani 1 1 d U . .
O6 O 0.8295(12) 0.8899(6) 0.7014(6) 0.0428(16) Uani 1 1 d U . .
O7 O 0.2217(13) 0.8159(6) 0.7225(6) 0.0496(18) Uani 1 1 d DU . .
H7A H 0.1053 0.8411 0.7244 0.074 Uiso 1 1 d R . .
O8 O 0.2789(13) 1.0478(6) 0.8544(6) 0.0490(19) Uani 1 1 d U . .
H8C H 0.2060 1.0495 0.9069 0.073 Uiso 1 1 d R . .
H8D H 0.1886 1.0236 0.7981 0.073 Uiso 1 1 d R . .
C1 C 0.7848(18) 0.7832(8) 0.8715(9) 0.0392(19) Uani 1 1 d U . .
C2 C 0.9223(19) 0.7044(8) 0.8853(9) 0.042(2) Uani 1 1 d U A .
C3 C 1.1292(18) 0.7420(9) 0.9511(9) 0.042(2) Uani 1 1 d U . .
C4 C 1.250(2) 0.6689(9) 0.9632(10) 0.047(2) Uani 1 1 d U A .
H4 H 1.3819 0.6937 1.0089 0.056 Uiso 1 1 calc R . .
C5 C 1.184(2) 0.5599(10) 0.9102(11) 0.057(2) Uani 1 1 d U . .
C7 C 0.853(2) 0.5954(9) 0.8338(10) 0.053(2) Uani 1 1 d U . .
H7 H 0.7167 0.5703 0.7910 0.063 Uiso 1 1 calc R A .
C15 C 0.7546(16) 0.9484(8) 0.6569(8) 0.0342(19) Uani 1 1 d U . .
C16 C 0.8823(17) 0.9741(9) 0.5743(8) 0.037(2) Uani 1 1 d U . .
C17 C 1.0751(18) 0.9323(9) 0.5422(9) 0.044(2) Uani 1 1 d U . .
H17 H 1.1263 0.8869 0.5711 0.053 Uiso 1 1 calc R . .
C18 C 1.1930(18) 0.9570(9) 0.4676(9) 0.044(2) Uani 1 1 d U . .
H18 H 1.3217 0.9277 0.4456 0.053 Uiso 1 1 calc R . .
C19 C 1.2154(16) 0.8572(8) 1.0154(8) 0.0337(18) Uani 1 1 d U . .
C6 C 0.981(2) 0.5223(10) 0.8440(11) 0.059(2) Uani 1 1 d U A .
H5 H 1.2699 0.5125 0.9182 0.071 Uiso 0.332(4) 1 d PR A 1
O9 O 0.922(2) 0.4122(10) 0.7849(12) 0.065(3) Uani 0.665(8) 1 d PU A 1
C9 C 1.087(3) 0.3503(14) 0.7592(16) 0.054(3) Uani 0.665(8) 1 d PU A 1
C10 C 1.076(4) 0.2658(15) 0.7948(16) 0.059(3) Uani 0.665(8) 1 d PU A 1
H10 H 0.9546 0.2516 0.8304 0.071 Uiso 0.665(8) 1 calc PR A 1
C14 C 1.242(4) 0.3563(16) 0.6903(18) 0.061(3) Uani 0.665(8) 1 d PU A 1
H14 H 1.2420 0.4071 0.6604 0.074 Uiso 0.665(8) 1 d PR A 1
H6 H 0.9328 0.4490 0.8079 0.074 Uiso 0.665(8) 1 d PR A 2
O9' O 1.274(4) 0.483(2) 0.917(2) 0.061(3) Uani 0.335(8) 1 d PU A 2
C9' C 1.289(7) 0.394(3) 0.833(3) 0.061(4) Uani 0.335(8) 1 d PU A 2
C10' C 1.261(7) 0.298(3) 0.858(3) 0.059(4) Uani 0.335(8) 1 d PU A 2
H10' H 1.2519 0.3026 0.9271 0.071 Uiso 0.335(8) 1 calc PR A 2
C14' C 1.335(8) 0.387(3) 0.732(4) 0.064(4) Uani 0.335(8) 1 d PU A 2
H14' H 1.3271 0.4428 0.7095 0.076 Uiso 0.335(8) 1 calc PR A 2
N1 N 1.247(2) 0.2027(9) 0.7764(10) 0.067(2) Uani 1 1 d U . .
C12 C 1.374(3) 0.2107(11) 0.7058(12) 0.073(3) Uani 1 1 d U A .
H12 H 1.4625 0.1578 0.6782 0.088 Uiso 1 1 calc R . .
C13 C 1.392(3) 0.2920(11) 0.6662(12) 0.073(3) Uani 1 1 d U . .
H13 H 1.4406 0.2819 0.5998 0.087 Uiso 1 1 d R A .
C20 C 0.180(3) 0.7047(10) 0.6511(16) 0.121(5) Uani 1 1 d DU . .
H20A H 0.1088 0.7078 0.5877 0.146 Uiso 1 1 calc R . .
H20B H 0.0581 0.6750 0.6814 0.146 Uiso 1 1 calc R . .
C21 C 0.307(4) 0.6102(17) 0.605(2) 0.224(12) Uani 1 1 d DU . .
H21A H 0.2422 0.5524 0.6239 0.336 Uiso 1 1 calc R . .
H21B H 0.4628 0.6324 0.6325 0.336 Uiso 1 1 calc R . .
H21C H 0.2957 0.5865 0.5288 0.336 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 O8 2.382(7) . ?
Eu1 O3 2.407(7) 1_455 ?
Eu1 O2 2.436(7) . ?
Eu1 O7 2.437(8) . ?
Eu1 O5 2.460(7) . ?
Eu1 O4 2.471(7) 2_777 ?
Eu1 O1 2.478(7) . ?
Eu1 O6 2.490(7) . ?
Eu1 O3 2.638(7) 2_777 ?
Eu1 C19 2.923(11) 2_777 ?
Eu1 Eu1 4.2666(13) 2_677 ?
O1 C1 1.285(13) . ?
O2 C1 1.253(12) . ?
O3 C19 1.272(11) . ?
O3 Eu1 2.407(7) 1_655 ?
O3 Eu1 2.638(7) 2_777 ?
O4 C19 1.232(12) . ?
O4 Eu1 2.471(7) 2_777 ?
O5 C15 1.245(11) . ?
O6 C15 1.289(11) . ?
O7 C20 1.441(9) . ?
C1 C2 1.507(13) . ?
C2 C7 1.379(15) . ?
C2 C3 1.418(15) . ?
C3 C4 1.368(14) . ?
C3 C19 1.487(15) . ?
C4 C5 1.378(16) . ?
C5 O9' 1.28(2) . ?
C5 C6 1.400(18) . ?
C7 C6 1.388(16) . ?
C15 C16 1.509(13) . ?
C16 C17 1.379(13) . ?
C16 C18 1.390(14) 2_776 ?
C17 C18 1.380(15) . ?
C18 C16 1.390(14) 2_776 ?
C19 Eu1 2.923(11) 2_777 ?
C6 O9 1.398(17) . ?
O9 C9 1.37(2) . ?
C9 C14 1.37(3) . ?
C9 C10 1.41(2) . ?
C10 N1 1.41(2) . ?
C14 C13 1.31(2) . ?
O9' C9' 1.34(4) . ?
C9' C14' 1.40(6) . ?
C9' C10' 1.47(5) . ?
C10' N1 1.35(4) . ?
C14' C13 1.37(4) . ?
N1 C12 1.280(18) . ?
C12 C13 1.402(19) . ?
C20 C21 1.534(9) . ?

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
O8 Eu1 O3 77.5(2) . 1_455 ?
O8 Eu1 O2 146.8(3) . . ?
O3 Eu1 O2 81.1(2) 1_455 . ?
O8 Eu1 O7 75.7(3) . . ?
O3 Eu1 O7 83.2(3) 1_455 . ?
O2 Eu1 O7 126.6(2) . . ?
O8 Eu1 O5 75.3(2) . . ?
O3 Eu1 O5 150.7(2) 1_455 . ?
O2 Eu1 O5 128.1(2) . . ?
O7 Eu1 O5 79.6(3) . . ?
O8 Eu1 O4 83.9(3) . 2_777 ?
O3 Eu1 O4 114.9(2) 1_455 2_777 ?
O2 Eu1 O4 82.4(2) . 2_777 ?
O7 Eu1 O4 149.2(3) . 2_777 ?
O5 Eu1 O4 73.0(3) . 2_777 ?
O8 Eu1 O1 144.9(3) . . ?
O3 Eu1 O1 81.8(3) 1_455 . ?
O2 Eu1 O1 53.5(2) . . ?
O7 Eu1 O1 73.9(3) . . ?
O5 Eu1 O1 115.4(3) . . ?
O4 Eu1 O1 130.9(3) 2_777 . ?
O8 Eu1 O6 127.7(2) . . ?
O3 Eu1 O6 154.3(2) 1_455 . ?
O2 Eu1 O6 77.8(2) . . ?
O7 Eu1 O6 97.7(3) . . ?
O5 Eu1 O6 52.7(2) . . ?
O4 Eu1 O6 76.8(2) 2_777 . ?
O1 Eu1 O6 73.9(3) . . ?
O8 Eu1 O3 73.3(2) . 2_777 ?
O3 Eu1 O3 64.6(3) 1_455 2_777 ?
O2 Eu1 O3 74.6(2) . 2_777 ?
O7 Eu1 O3 139.1(2) . 2_777 ?
O5 Eu1 O3 116.7(2) . 2_777 ?
O4 Eu1 O3 50.3(2) 2_777 2_777 ?
O1 Eu1 O3 121.9(2) . 2_777 ?
O6 Eu1 O3 122.4(2) . 2_777 ?
O8 Eu1 C19 76.0(3) . 2_777 ?
O3 Eu1 C19 90.3(3) 1_455 2_777 ?
O2 Eu1 C19 79.0(2) . 2_777 ?
O7 Eu1 C19 151.7(3) . 2_777 ?
O5 Eu1 C19 93.7(3) . 2_777 ?
O4 Eu1 C19 24.6(2) 2_777 2_777 ?
O1 Eu1 C19 132.5(3) . 2_777 ?
O6 Eu1 C19 99.9(3) . 2_777 ?
O3 Eu1 C19 25.8(2) 2_777 2_777 ?
O8 Eu1 Eu1 72.59(18) . 2_677 ?
O3 Eu1 Eu1 33.94(17) 1_455 2_677 ?
O2 Eu1 Eu1 75.46(16) . 2_677 ?
O7 Eu1 Eu1 113.61(19) . 2_677 ?
O5 Eu1 Eu1 140.34(18) . 2_677 ?
O4 Eu1 Eu1 80.96(16) 2_777 2_677 ?
O1 Eu1 Eu1 104.3(2) . 2_677 ?
O6 Eu1 Eu1 147.11(18) . 2_677 ?
O3 Eu1 Eu1 30.63(14) 2_777 2_677 ?
C19 Eu1 Eu1 56.40(19) 2_777 2_677 ?
C1 O1 Eu1 91.1(6) . . ?
C1 O2 Eu1 93.9(6) . . ?
C19 O3 Eu1 154.6(7) . 1_655 ?
C19 O3 Eu1 89.7(6) . 2_777 ?
Eu1 O3 Eu1 115.4(3) 1_655 2_777 ?
C19 O4 Eu1 98.7(6) . 2_777 ?
C15 O5 Eu1 94.1(6) . . ?
C15 O6 Eu1 91.7(5) . . ?
C20 O7 Eu1 133.2(9) . . ?
O2 C1 O1 121.4(9) . . ?
O2 C1 C2 119.5(10) . . ?
O1 C1 C2 119.0(10) . . ?
C7 C2 C3 118.7(10) . . ?
C7 C2 C1 121.3(11) . . ?
C3 C2 C1 120.0(10) . . ?
C4 C3 C2 118.8(10) . . ?
C4 C3 C19 117.3(10) . . ?
C2 C3 C19 123.7(9) . . ?
C3 C4 C5 122.6(12) . . ?
O9' C5 C4 129.1(17) . . ?
O9' C5 C6 111.9(17) . . ?
C4 C5 C6 118.8(11) . . ?
C2 C7 C6 121.8(12) . . ?
O5 C15 O6 120.3(9) . . ?
O5 C15 C16 119.6(9) . . ?
O6 C15 C16 120.1(8) . . ?
C17 C16 C18 119.8(10) . 2_776 ?
C17 C16 C15 120.9(9) . . ?
C18 C16 C15 119.3(9) 2_776 . ?
C16 C17 C18 120.8(10) . . ?
C17 C18 C16 119.5(10) . 2_776 ?
O4 C19 O3 120.8(10) . . ?
O4 C19 C3 120.3(9) . . ?
O3 C19 C3 118.6(10) . . ?
O4 C19 Eu1 56.7(5) . 2_777 ?
O3 C19 Eu1 64.5(6) . 2_777 ?
C3 C19 Eu1 168.2(7) . 2_777 ?
O9 C6 C7 122.1(13) . . ?
O9 C6 C5 118.6(12) . . ?
C7 C6 C5 119.2(12) . . ?
C9 O9 C6 119.3(14) . . ?
C14 C9 O9 124.1(17) . . ?
C14 C9 C10 118.4(18) . . ?
O9 C9 C10 116.9(18) . . ?
N1 C10 C9 119.9(18) . . ?
C13 C14 C9 121.1(18) . . ?
C5 O9' C9' 123(3) . . ?
O9' C9' C14' 127(4) . . ?
O9' C9' C10' 113(4) . . ?
C14' C9' C10' 120(4) . . ?
N1 C10' C9' 118(3) . . ?
C13 C14' C9' 116(4) . . ?
C12 N1 C10' 111(2) . . ?
C12 N1 C10 114.7(13) . . ?
C10' N1 C10 56.1(18) . . ?
N1 C12 C13 126.0(14) . . ?
C14 C13 C14' 31.7(19) . . ?
C14 C13 C12 117.5(16) . . ?
C14' C13 C12 116(2) . . ?
O7 C20 C21 139.8(17) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.22
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.066
_refine_diff_density_min         -1.347
_refine_diff_density_rms         0.174
####################################################################### 
# 
# 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_exp_7481
_database_code_depnum_ccdc_archive 'CCDC 1509530'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Dy N O9'
_chemical_formula_weight         565.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -9.8046 9.8477 '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                   5.9650(4)
_cell_length_b                   13.6324(11)
_cell_length_c                   13.7320(9)
_cell_angle_alpha                111.858(7)
_cell_angle_beta                 91.543(5)
_cell_angle_gamma                98.856(6)
_cell_volume                     1019.69(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2346
_cell_measurement_theta_min      6.8940
_cell_measurement_theta_max      71.5810

_exptl_crystal_description       bar
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    20.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2966
_exptl_absorpt_correction_T_max  0.3340
_exptl_absorpt_process_details   wswsw

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6067
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         67.24
_reflns_number_total             3650
_reflns_number_gt                2990
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1015P)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         3650
_refine_ls_number_parameters     336
_refine_ls_number_restraints     1181
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1701
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      0.935
_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
C18 C 0.304(5) 0.1177(19) 0.111(3) 0.242(14) Uani 1 1 d DU . .
H18A H 0.4013 0.1145 0.1662 0.364 Uiso 1 1 calc R . .
H18B H 0.3945 0.1261 0.0568 0.364 Uiso 1 1 calc R . .
H18C H 0.1942 0.0526 0.0817 0.364 Uiso 1 1 calc R . .
Dy1 Dy 0.55387(8) 0.43686(4) 0.33765(4) 0.0290(2) Uani 1 1 d U . .
O1 O 0.8270(12) 0.6006(5) 0.3942(5) 0.0382(13) Uani 1 1 d U . .
O2 O 0.6534(11) 0.5901(5) 0.5291(5) 0.0350(13) Uani 1 1 d U . .
O3 O 1.1619(10) 0.6156(5) 0.5771(5) 0.0329(13) Uani 1 1 d U . .
O4 O 1.3951(12) 0.7491(5) 0.6973(5) 0.0432(15) Uani 1 1 d U . .
O5 O 0.5792(11) 0.4908(6) 0.1878(5) 0.0399(14) Uani 1 1 d U . .
O6 O 0.8289(11) 0.3951(6) 0.2053(5) 0.0398(14) Uani 1 1 d U . .
O7 O 0.2188(12) 0.3219(5) 0.2247(5) 0.0424(15) Uani 1 1 d DU . .
H7A H 0.3347 0.3540 0.2117 0.064 Uiso 1 1 d R . .
O8 O 0.2845(11) 0.5491(5) 0.3586(5) 0.0390(15) Uani 1 1 d U . .
H8B H 0.2559 0.5734 0.4227 0.058 Uiso 1 1 d R . .
H8C H 0.3376 0.6011 0.3411 0.058 Uiso 1 1 d R . .
C1 C 0.7931(16) 0.6437(7) 0.4911(7) 0.0312(16) Uani 1 1 d U . .
C2 C 0.8840(16) 0.7568(7) 0.5516(7) 0.0335(16) Uani 1 1 d U A .
C3 C 1.0909(18) 0.7932(8) 0.6158(7) 0.0396(18) Uani 1 1 d U . .
C4 C 1.165(2) 0.9035(8) 0.6690(9) 0.050(2) Uani 1 1 d U A .
H4 H 1.2996 0.9280 0.7132 0.060 Uiso 1 1 calc R . .
C5 C 1.043(2) 0.9768(9) 0.6572(10) 0.056(2) Uani 1 1 d U . .
H5 H 1.0952 1.0501 0.6920 0.068 Uiso 0.471(8) 1 calc PR A 2
C6 C 0.840(2) 0.9395(9) 0.5926(9) 0.051(2) Uani 1 1 d U A .
H6 H 0.7550 0.9882 0.5850 0.061 Uiso 0.529(8) 1 calc PR A 1
C7 C 0.7649(19) 0.8316(8) 0.5400(8) 0.0440(19) Uani 1 1 d U . .
H7 H 0.6307 0.8083 0.4956 0.053 Uiso 1 1 calc R A .
O9 O 1.093(3) 1.0884(11) 0.7156(12) 0.055(3) Uani 0.529(8) 1 d PU A 1
C8 C 0.928(2) 1.1531(11) 0.7446(12) 0.051(3) Uani 0.529(8) 1 d PDU A 1
C9 C 0.936(2) 1.2328(11) 0.7062(11) 0.048(3) Uani 0.529(8) 1 d PDU A 1
H9 H 1.0517 1.2431 0.6649 0.058 Uiso 0.529(8) 1 calc PR A 1
N1 N 0.774(2) 1.2975(10) 0.7286(11) 0.049(3) Uani 0.529(8) 1 d PDU A 1
C10 C 0.605(2) 1.2818(12) 0.7894(13) 0.053(3) Uani 0.529(8) 1 d PDU A 1
H10 H 0.4952 1.3257 0.8047 0.064 Uiso 0.529(8) 1 calc PR A 1
C11 C 0.597(2) 1.2020(13) 0.8278(13) 0.055(3) Uani 0.529(8) 1 d PDU A 1
H11 H 0.4809 1.1915 0.8688 0.066 Uiso 0.529(8) 1 calc PR A 1
C12 C 0.759(3) 1.1376(11) 0.8057(12) 0.053(3) Uani 0.529(8) 1 d PDU A 1
H12 H 0.7547 1.0836 0.8321 0.063 Uiso 0.529(8) 1 calc PR A 1
N1' N 0.697(4) 1.2859(18) 0.7053(18) 0.052(3) Uani 0.471(8) 1 d PU A 2
C8' C 0.738(4) 1.1099(18) 0.6646(19) 0.049(3) Uani 0.471(8) 1 d PU A 2
C9' C 0.739(4) 1.2001(17) 0.6421(19) 0.047(3) Uani 0.471(8) 1 d PU A 2
H9' H 0.7742 1.1965 0.5754 0.056 Uiso 0.471(8) 1 calc PR A 2
C12' C 0.697(4) 1.113(2) 0.765(2) 0.053(3) Uani 0.471(8) 1 d PU A 2
H12' H 0.6794 1.0513 0.7797 0.063 Uiso 0.471(8) 1 calc PR A 2
O9' O 0.749(3) 1.0153(13) 0.5820(13) 0.053(3) Uani 0.471(8) 1 d PU A 2
C11' C 0.683(5) 1.217(2) 0.845(2) 0.053(3) Uani 0.471(8) 1 d PU A 2
H11' H 0.6718 1.2289 0.9155 0.064 Uiso 0.471(8) 1 calc PR A 2
C10' C 0.686(5) 1.297(2) 0.806(2) 0.051(3) Uani 0.471(8) 1 d PU A 2
H10' H 0.6807 1.3651 0.8550 0.061 Uiso 0.471(8) 1 calc PR A 2
C13 C 0.7611(17) 0.4539(8) 0.1605(7) 0.0369(19) Uani 1 1 d U . .
C14 C 0.8848(17) 0.4777(8) 0.0777(7) 0.0366(19) Uani 1 1 d U . .
C15 C 0.8091(18) 0.5436(9) 0.0352(7) 0.042(2) Uani 1 1 d U . .
H15 H 0.6808 0.5733 0.0587 0.051 Uiso 1 1 calc R . .
C16 C 0.9221(18) 0.5671(9) -0.0434(8) 0.042(2) Uani 1 1 d U . .
H16 H 0.8695 0.6119 -0.0725 0.050 Uiso 1 1 calc R . .
C17 C 1.2247(17) 0.7162(8) 0.6309(7) 0.0365(17) Uani 1 1 d U . .
C19 C 0.181(3) 0.2133(10) 0.1558(16) 0.123(6) Uani 1 1 d DU . .
H19A H 0.1153 0.2169 0.0920 0.147 Uiso 1 1 calc R . .
H19B H 0.0532 0.1832 0.1843 0.147 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
C18 C19 1.529(9) . ?
Dy1 O8 2.337(6) . ?
Dy1 O2 2.344(6) 2_666 ?
Dy1 O3 2.376(6) 2_766 ?
Dy1 O1 2.400(7) . ?
Dy1 O5 2.430(6) . ?
Dy1 O7 2.432(7) . ?
Dy1 O6 2.449(6) . ?
Dy1 O4 2.467(7) 2_766 ?
Dy1 O2 2.660(6) . ?
Dy1 C17 2.788(9) 2_766 ?
Dy1 C13 2.827(8) . ?
Dy1 C1 2.933(9) . ?
O1 C1 1.275(10) . ?
O2 C1 1.273(10) . ?
O2 Dy1 2.344(6) 2_666 ?
O3 C17 1.280(11) . ?
O3 Dy1 2.376(6) 2_766 ?
O4 C17 1.254(12) . ?
O4 Dy1 2.467(7) 2_766 ?
O5 C13 1.273(11) . ?
O6 C13 1.279(11) . ?
O7 C19 1.408(8) . ?
C1 C2 1.458(13) . ?
C2 C7 1.381(13) . ?
C2 C3 1.406(14) . ?
C3 C4 1.397(14) . ?
C3 C17 1.481(13) . ?
C4 C5 1.376(16) . ?
C5 C6 1.386(16) . ?
C5 O9 1.408(17) . ?
C6 O9' 1.292(18) . ?
C6 C7 1.369(15) . ?
O9 C8 1.387(18) . ?
C8 C9 1.369(8) . ?
C8 C12 1.370(8) . ?
C9 N1 1.372(8) . ?
N1 C10 1.369(8) . ?
C10 C11 1.370(8) . ?
C11 C12 1.373(8) . ?
N1' C9' 1.24(3) . ?
N1' C10' 1.34(3) . ?
C8' C9' 1.37(3) . ?
C8' O9' 1.38(3) . ?
C8' C12' 1.39(3) . ?
C12' C11' 1.46(3) . ?
C11' C10' 1.37(4) . ?
C13 C14 1.481(11) . ?
C14 C15 1.360(13) . ?
C14 C16 1.398(14) 2_765 ?
C15 C16 1.397(13) . ?
C16 C14 1.398(14) 2_765 ?
C17 Dy1 2.788(9) 2_766 ?

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
O8 Dy1 O2 77.0(2) . 2_666 ?
O8 Dy1 O3 146.1(2) . 2_766 ?
O2 Dy1 O3 81.0(2) 2_666 2_766 ?
O8 Dy1 O1 84.6(2) . . ?
O2 Dy1 O1 114.8(2) 2_666 . ?
O3 Dy1 O1 81.7(2) 2_766 . ?
O8 Dy1 O5 75.3(2) . . ?
O2 Dy1 O5 150.0(2) 2_666 . ?
O3 Dy1 O5 129.0(2) 2_766 . ?
O1 Dy1 O5 73.7(2) . . ?
O8 Dy1 O7 75.2(2) . . ?
O2 Dy1 O7 83.0(2) 2_666 . ?
O3 Dy1 O7 127.2(2) 2_766 . ?
O1 Dy1 O7 149.4(2) . . ?
O5 Dy1 O7 79.1(2) . . ?
O8 Dy1 O6 128.4(2) . . ?
O2 Dy1 O6 154.1(2) 2_666 . ?
O3 Dy1 O6 78.2(2) 2_766 . ?
O1 Dy1 O6 77.3(2) . . ?
O5 Dy1 O6 53.3(2) . . ?
O7 Dy1 O6 97.4(2) . . ?
O8 Dy1 O4 144.3(2) . 2_766 ?
O2 Dy1 O4 81.6(2) 2_666 2_766 ?
O3 Dy1 O4 53.9(2) 2_766 2_766 ?
O1 Dy1 O4 130.6(2) . 2_766 ?
O5 Dy1 O4 115.7(2) . 2_766 ?
O7 Dy1 O4 74.1(2) . 2_766 ?
O6 Dy1 O4 73.6(2) . 2_766 ?
O8 Dy1 O2 73.5(2) . . ?
O2 Dy1 O2 64.0(2) 2_666 . ?
O3 Dy1 O2 73.8(2) 2_766 . ?
O1 Dy1 O2 50.87(19) . . ?
O5 Dy1 O2 117.6(2) . . ?
O7 Dy1 O2 138.5(2) . . ?
O6 Dy1 O2 123.4(2) . . ?
O4 Dy1 O2 121.2(2) 2_766 . ?
O8 Dy1 C17 157.8(2) . 2_766 ?
O2 Dy1 C17 80.9(2) 2_666 2_766 ?
O3 Dy1 C17 27.2(2) 2_766 2_766 ?
O1 Dy1 C17 106.5(3) . 2_766 ?
O5 Dy1 C17 125.9(2) . 2_766 ?
O7 Dy1 C17 100.5(3) . 2_766 ?
O6 Dy1 C17 73.5(2) . 2_766 ?
O4 Dy1 C17 26.7(3) 2_766 2_766 ?
O2 Dy1 C17 98.3(2) . 2_766 ?
O8 Dy1 C13 101.5(3) . . ?
O2 Dy1 C13 173.4(3) 2_666 . ?
O3 Dy1 C13 103.0(3) 2_766 . ?
O1 Dy1 C13 71.1(2) . . ?
O5 Dy1 C13 26.7(3) . . ?
O7 Dy1 C13 90.5(3) . . ?
O6 Dy1 C13 26.9(2) . . ?
O4 Dy1 C13 96.5(2) 2_766 . ?
O2 Dy1 C13 122.0(2) . . ?
C17 Dy1 C13 100.3(3) 2_766 . ?
O8 Dy1 C1 76.8(2) . . ?
O2 Dy1 C1 89.7(2) 2_666 . ?
O3 Dy1 C1 77.7(2) 2_766 . ?
O1 Dy1 C1 25.2(2) . . ?
O5 Dy1 C1 95.0(2) . . ?
O7 Dy1 C1 152.0(2) . . ?
O6 Dy1 C1 100.8(2) . . ?
O4 Dy1 C1 131.6(2) 2_766 . ?
O2 Dy1 C1 25.7(2) . . ?
C17 Dy1 C1 105.0(3) 2_766 . ?
C13 Dy1 C1 96.2(2) . . ?
C1 O1 Dy1 101.5(5) . . ?
C1 O2 Dy1 154.6(6) . 2_666 ?
C1 O2 Dy1 89.2(5) . . ?
Dy1 O2 Dy1 116.0(2) 2_666 . ?
C17 O3 Dy1 94.6(5) . 2_766 ?
C17 O4 Dy1 91.1(6) . 2_766 ?
C13 O5 Dy1 94.3(5) . . ?
C13 O6 Dy1 93.3(5) . . ?
C19 O7 Dy1 131.4(10) . . ?
O2 C1 O1 118.2(8) . . ?
O2 C1 C2 120.8(8) . . ?
O1 C1 C2 120.3(8) . . ?
O2 C1 Dy1 65.1(5) . . ?
O1 C1 Dy1 53.3(5) . . ?
C2 C1 Dy1 166.2(6) . . ?
C7 C2 C3 118.8(9) . . ?
C7 C2 C1 117.6(9) . . ?
C3 C2 C1 123.5(8) . . ?
C4 C3 C2 119.0(9) . . ?
C4 C3 C17 120.1(10) . . ?
C2 C3 C17 120.8(9) . . ?
C5 C4 C3 121.3(11) . . ?
C4 C5 C6 118.8(11) . . ?
C4 C5 O9 124.9(13) . . ?
C6 C5 O9 115.8(12) . . ?
O9' C6 C7 125.8(13) . . ?
O9' C6 C5 113.3(12) . . ?
C7 C6 C5 120.7(10) . . ?
C6 C7 C2 121.3(11) . . ?
C8 O9 C5 123.8(14) . . ?
C9 C8 C12 120.3(7) . . ?
C9 C8 O9 116.8(12) . . ?
C12 C8 O9 122.9(12) . . ?
C8 C9 N1 120.0(7) . . ?
C10 N1 C9 119.7(7) . . ?
N1 C10 C11 120.4(7) . . ?
C10 C11 C12 119.9(7) . . ?
C8 C12 C11 119.7(7) . . ?
C9' N1' C10' 118(2) . . ?
C9' C8' O9' 118(2) . . ?
C9' C8' C12' 120(2) . . ?
O9' C8' C12' 122(2) . . ?
N1' C9' C8' 124(2) . . ?
C8' C12' C11' 117(2) . . ?
C6 O9' C8' 123.1(17) . . ?
C10' C11' C12' 114(2) . . ?
N1' C10' C11' 127(2) . . ?
O5 C13 O6 118.1(8) . . ?
O5 C13 C14 119.9(9) . . ?
O6 C13 C14 122.0(8) . . ?
O5 C13 Dy1 59.0(4) . . ?
O6 C13 Dy1 59.9(4) . . ?
C14 C13 Dy1 172.1(7) . . ?
C15 C14 C16 120.3(8) . 2_765 ?
C15 C14 C13 119.5(9) . . ?
C16 C14 C13 120.2(9) 2_765 . ?
C14 C15 C16 120.7(9) . . ?
C15 C16 C14 119.0(9) . 2_765 ?
O4 C17 O3 120.3(9) . . ?
O4 C17 C3 120.2(9) . . ?
O3 C17 C3 119.4(9) . . ?
O4 C17 Dy1 62.2(5) . 2_766 ?
O3 C17 Dy1 58.2(5) . 2_766 ?
C3 C17 Dy1 175.7(7) . 2_766 ?
O7 C19 C18 141.5(19) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.24
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.547
_refine_diff_density_min         -1.262
_refine_diff_density_rms         0.191
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1443939'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O9 Tb'
_chemical_formula_weight         562.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -9.1472 9.1891 '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                   5.9813(5)
_cell_length_b                   13.6544(16)
_cell_length_c                   13.7610(13)
_cell_angle_alpha                111.815(10)
_cell_angle_beta                 91.528(7)
_cell_angle_gamma                98.989(8)
_cell_volume                     1026.18(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1449
_cell_measurement_theta_min      6.4500
_cell_measurement_theta_max      70.6050

_exptl_crystal_description       strip
_exptl_crystal_colour            'pale yellow '
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             550
_exptl_absorpt_coefficient_mu    17.410
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.3754
_exptl_absorpt_correction_T_max  0.4214
_exptl_absorpt_process_details   sasdas

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6093
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_sigmaI/netI    0.1208
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         67.19
_reflns_number_total             3666
_reflns_number_gt                2715
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1338P)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         3666
_refine_ls_number_parameters     318
_refine_ls_number_restraints     1069
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.2376
_refine_ls_wR_factor_gt          0.1956
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      0.936
_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
Tb1 Tb 0.55415(10) 0.43710(5) 0.33814(5) 0.0422(3) Uani 1 1 d U . .
O1 O 0.8321(14) 0.3948(7) 0.2046(6) 0.0522(17) Uani 1 1 d U . .
O2 O 0.5784(13) 0.4903(7) 0.1869(7) 0.0542(18) Uani 1 1 d U . .
O3 O 0.8394(14) 0.3839(6) 0.4220(6) 0.0515(17) Uani 1 1 d U . .
O4 O 0.6048(15) 0.2517(7) 0.3018(7) 0.0567(18) Uani 1 1 d U . .
O5 O 1.3461(13) 0.4097(6) 0.4714(6) 0.0480(17) Uani 1 1 d U . .
O6 O 1.1738(13) 0.3972(6) 0.6052(6) 0.0478(17) Uani 1 1 d U . .
O7 O 0.2823(14) 0.5512(7) 0.3569(7) 0.056(2) Uani 1 1 d U . .
H7A H 0.2083 0.5529 0.4092 0.085 Uiso 1 1 d R . .
H7B H 0.3506 0.6141 0.3670 0.085 Uiso 1 1 d R . .
O8 O 0.2205(14) 0.3231(7) 0.2248(7) 0.0544(18) Uani 1 1 d DU . .
H8A H 0.1183 0.3524 0.2139 0.082 Uiso 1 1 d R . .
O9 O 0.906(3) -0.0876(14) 0.2855(16) 0.073(3) Uani 0.548(11) 1 d PU A 1
H9 H 1.2412 0.0073 0.4120 0.087 Uiso 0.548(11) 1 d PR A 1
O9' O 1.247(4) -0.0175(17) 0.4148(18) 0.070(3) Uani 0.452(11) 1 d PU A 2
H10 H 0.9105 -0.0498 0.3103 0.084 Uiso 0.452(11) 1 d PR A 2
C1 C 0.7579(19) 0.4529(10) 0.1615(9) 0.046(2) Uani 1 1 d U . .
C2 C 0.8853(19) 0.4774(10) 0.0786(8) 0.045(2) Uani 1 1 d U . .
C3 C 0.810(2) 0.5440(11) 0.0343(10) 0.055(3) Uani 1 1 d U . .
H3 H 0.6823 0.5742 0.0574 0.066 Uiso 1 1 calc R . .
C4 C 1.078(2) 0.4341(10) 0.0442(10) 0.052(2) Uani 1 1 d U . .
H4 H 1.1316 0.3902 0.0740 0.062 Uiso 1 1 calc R . .
C5 C 0.773(2) 0.2828(10) 0.3669(9) 0.046(2) Uani 1 1 d U . .
C6 C 0.912(2) 0.2060(10) 0.3846(10) 0.052(2) Uani 1 1 d U A .
C7 C 1.116(2) 0.2426(9) 0.4494(9) 0.046(2) Uani 1 1 d U . .
C8 C 1.235(2) 0.1679(10) 0.4610(11) 0.057(2) Uani 1 1 d U A .
H8 H 1.3675 0.1910 0.5061 0.069 Uiso 1 1 calc R . .
C9 C 1.157(3) 0.0572(11) 0.4056(12) 0.066(2) Uani 1 1 d U . .
C10 C 0.963(3) 0.0233(11) 0.3445(13) 0.069(3) Uani 1 1 d U A .
C11 C 0.843(3) 0.0967(11) 0.3315(12) 0.063(2) Uani 1 1 d U . .
H11 H 0.7117 0.0718 0.2855 0.076 Uiso 1 1 calc R A .
C12 C 1.205(2) 0.3551(9) 0.5086(9) 0.045(2) Uani 1 1 d U . .
C13 C 1.071(2) -0.1511(11) 0.2689(14) 0.076(3) Uani 0.548(11) 1 d PDU A 1
C14 C 1.085(2) -0.2298(10) 0.3082(12) 0.077(4) Uani 0.548(11) 1 d PDU A 1
H14 H 0.9816 -0.2415 0.3536 0.092 Uiso 0.548(11) 1 calc PR A 1
N1 N 1.2541(18) -0.2908(6) 0.2797(8) 0.079(3) Uani 1 1 d DU . .
C16 C 1.375(2) -0.2892(7) 0.1957(9) 0.083(3) Uani 1 1 d DU A .
H16 H 1.4666 -0.3400 0.1668 0.100 Uiso 1 1 d R . .
C17 C 1.359(3) -0.2118(12) 0.1552(12) 0.077(4) Uani 0.548(11) 1 d PDU A 1
H17 H 1.4406 -0.2097 0.0993 0.092 Uiso 0.548(11) 1 d PR A 1
C18 C 1.219(3) -0.1377(11) 0.1976(14) 0.074(3) Uani 0.548(11) 1 d PDU A 1
H18 H 1.2257 -0.0789 0.1784 0.089 Uiso 0.548(11) 1 d PR A 1
C19 C 0.175(4) 0.2068(10) 0.1525(18) 0.121(5) Uani 1 1 d DU . .
H19A H 0.1445 0.2113 0.0849 0.145 Uiso 1 1 calc R . .
H19B H 0.0277 0.1818 0.1708 0.145 Uiso 1 1 calc R . .
C20 C 0.281(5) 0.1077(17) 0.122(3) 0.178(10) Uani 1 1 d DU . .
H20A H 0.4066 0.1147 0.0814 0.267 Uiso 1 1 calc R . .
H20B H 0.1698 0.0462 0.0804 0.267 Uiso 1 1 calc R . .
H20C H 0.3341 0.0988 0.1840 0.267 Uiso 1 1 calc R . .
C13' C 1.263(4) -0.1024(7) 0.3349(13) 0.070(3) Uani 0.452(11) 1 d PDU A 2
C14' C 1.220(4) -0.1952(9) 0.3550(10) 0.075(4) Uani 0.452(11) 1 d PDU A 2
H14' H 1.1679 -0.1933 0.4186 0.089 Uiso 0.452(11) 1 calc PR A 2
C17' C 1.408(5) -0.1978(11) 0.1731(15) 0.081(4) Uani 0.452(11) 1 d PDU A 2
H17' H 1.4777 -0.1978 0.1135 0.097 Uiso 0.452(11) 1 d PR A 2
C18' C 1.337(4) -0.1064(9) 0.2396(15) 0.075(4) Uani 0.452(11) 1 d PDU A 2
H18' H 1.3409 -0.0477 0.2203 0.091 Uiso 0.452(11) 1 d PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O5 2.353(7) 1_455 ?
Tb1 O7 2.378(8) . ?
Tb1 O3 2.383(8) . ?
Tb1 O6 2.418(8) 2_766 ?
Tb1 O8 2.428(9) . ?
Tb1 O2 2.447(8) . ?
Tb1 O4 2.461(9) . ?
Tb1 O1 2.480(7) . ?
Tb1 O5 2.656(8) 2_766 ?
Tb1 C12 2.948(12) 2_766 ?
O1 C1 1.274(14) . ?
O2 C1 1.263(13) . ?
O3 C5 1.294(14) . ?
O4 C5 1.235(15) . ?
O5 C12 1.282(12) . ?
O5 Tb1 2.353(7) 1_655 ?
O5 Tb1 2.656(8) 2_766 ?
O6 C12 1.270(13) . ?
O6 Tb1 2.418(8) 2_766 ?
O8 C19 1.504(9) . ?
O9 C13 1.387(19) . ?
O9 C10 1.41(2) . ?
O9' C9 1.27(2) . ?
O9' C13' 1.29(2) . ?
C1 C2 1.498(14) . ?
C2 C3 1.390(17) . ?
C2 C4 1.391(15) . ?
C3 C4 1.388(16) 2_765 ?
C4 C3 1.388(16) 2_765 ?
C5 C6 1.519(15) . ?
C6 C11 1.383(18) . ?
C6 C7 1.401(18) . ?
C7 C8 1.382(17) . ?
C7 C12 1.447(16) . ?
C8 C9 1.409(19) . ?
C9 C10 1.33(2) . ?
C10 C11 1.379(19) . ?
C12 Tb1 2.948(12) 2_766 ?
C13 C18 1.3813(9) . ?
C13 C14 1.3816(9) . ?
C14 N1 1.3821(9) . ?
N1 C14' 1.3825(9) . ?
N1 C16 1.3841(8) . ?
C16 C17 1.3809(9) . ?
C16 C17' 1.3822(9) . ?
C17 C18 1.3810(9) . ?
C19 C20 1.506(9) . ?
C13' C18' 1.3814(9) . ?
C13' C14' 1.3820(9) . ?
C17' C18' 1.3814(9) . ?

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
O5 Tb1 O7 77.8(3) 1_455 . ?
O5 Tb1 O3 81.4(3) 1_455 . ?
O7 Tb1 O3 147.3(3) . . ?
O5 Tb1 O6 114.9(3) 1_455 2_766 ?
O7 Tb1 O6 83.9(3) . 2_766 ?
O3 Tb1 O6 82.3(3) . 2_766 ?
O5 Tb1 O8 83.2(3) 1_455 . ?
O7 Tb1 O8 74.9(3) . . ?
O3 Tb1 O8 127.3(3) . . ?
O6 Tb1 O8 148.6(3) 2_766 . ?
O5 Tb1 O2 149.9(3) 1_455 . ?
O7 Tb1 O2 74.5(3) . . ?
O3 Tb1 O2 128.7(3) . . ?
O6 Tb1 O2 73.8(3) 2_766 . ?
O8 Tb1 O2 78.4(3) . . ?
O5 Tb1 O4 82.0(3) 1_455 . ?
O7 Tb1 O4 144.7(3) . . ?
O3 Tb1 O4 53.9(3) . . ?
O6 Tb1 O4 131.2(3) 2_766 . ?
O8 Tb1 O4 74.2(3) . . ?
O2 Tb1 O4 114.9(3) . . ?
O5 Tb1 O1 154.0(3) 1_455 . ?
O7 Tb1 O1 127.6(3) . . ?
O3 Tb1 O1 77.7(3) . . ?
O6 Tb1 O1 77.6(3) 2_766 . ?
O8 Tb1 O1 97.2(3) . . ?
O2 Tb1 O1 53.4(3) . . ?
O4 Tb1 O1 73.2(3) . . ?
O5 Tb1 O5 64.2(3) 1_455 2_766 ?
O7 Tb1 O5 74.0(3) . 2_766 ?
O3 Tb1 O5 74.3(3) . 2_766 ?
O6 Tb1 O5 50.7(2) 2_766 2_766 ?
O8 Tb1 O5 138.7(3) . 2_766 ?
O2 Tb1 O5 117.8(3) . 2_766 ?
O4 Tb1 O5 121.8(3) . 2_766 ?
O1 Tb1 O5 123.3(3) . 2_766 ?
O5 Tb1 C12 89.9(3) 1_455 2_766 ?
O7 Tb1 C12 77.0(3) . 2_766 ?
O3 Tb1 C12 78.0(3) . 2_766 ?
O6 Tb1 C12 24.9(3) 2_766 2_766 ?
O8 Tb1 C12 151.9(3) . 2_766 ?
O2 Tb1 C12 95.2(3) . 2_766 ?
O4 Tb1 C12 131.9(3) . 2_766 ?
O1 Tb1 C12 100.7(3) . 2_766 ?
O5 Tb1 C12 25.8(2) 2_766 2_766 ?
C1 O1 Tb1 91.2(6) . . ?
C1 O2 Tb1 93.0(7) . . ?
C5 O3 Tb1 93.8(7) . . ?
C5 O4 Tb1 91.6(7) . . ?
C12 O5 Tb1 154.1(8) . 1_655 ?
C12 O5 Tb1 90.0(7) . 2_766 ?
Tb1 O5 Tb1 115.8(3) 1_655 2_766 ?
C12 O6 Tb1 101.6(7) . 2_766 ?
C19 O8 Tb1 132.0(10) . . ?
C13 O9 C10 119.9(18) . . ?
C9 O9' C13' 122(2) . . ?
O2 C1 O1 121.5(10) . . ?
O2 C1 C2 119.0(10) . . ?
O1 C1 C2 119.5(10) . . ?
C3 C2 C4 119.0(10) . . ?
C3 C2 C1 119.6(10) . . ?
C4 C2 C1 121.3(10) . . ?
C4 C3 C2 120.7(11) 2_765 . ?
C3 C4 C2 120.3(11) 2_765 . ?
O4 C5 O3 120.7(10) . . ?
O4 C5 C6 122.3(11) . . ?
O3 C5 C6 117.0(11) . . ?
C11 C6 C7 118.4(12) . . ?
C11 C6 C5 119.7(13) . . ?
C7 C6 C5 121.8(11) . . ?
C8 C7 C6 118.5(12) . . ?
C8 C7 C12 118.4(12) . . ?
C6 C7 C12 123.1(11) . . ?
C7 C8 C9 121.0(14) . . ?
O9' C9 C10 114.0(17) . . ?
O9' C9 C8 125.9(17) . . ?
C10 C9 C8 119.9(13) . . ?
C9 C10 C11 119.9(14) . . ?
C9 C10 O9 116.7(15) . . ?
C11 C10 O9 122.9(16) . . ?
C10 C11 C6 122.1(15) . . ?
O6 C12 O5 117.6(11) . . ?
O6 C12 C7 120.0(9) . . ?
O5 C12 C7 121.4(10) . . ?
O6 C12 Tb1 53.4(6) . 2_766 ?
O5 C12 Tb1 64.3(6) . 2_766 ?
C7 C12 Tb1 165.6(8) . 2_766 ?
C18 C13 C14 119.72(10) . . ?
C18 C13 O9 113.5(12) . . ?
C14 C13 O9 126.4(12) . . ?
C13 C14 N1 119.64(10) . . ?
C14 N1 C14' 40.4(11) . . ?
C14 N1 C16 119.42(11) . . ?
C14' N1 C16 119.35(11) . . ?
C17 C16 C17' 14.9(17) . . ?
C17 C16 N1 119.58(9) . . ?
C17' C16 N1 119.39(10) . . ?
C16 C17 C18 119.80(10) . . ?
C17 C18 C13 119.76(12) . . ?
O8 C19 C20 141.1(19) . . ?
O9' C13' C18' 126.6(14) . . ?
O9' C13' C14' 113.4(14) . . ?
C18' C13' C14' 119.67(11) . . ?
C13' C14' N1 119.53(10) . . ?
C18' C17' C16 119.65(10) . . ?
C17' C18' C13' 119.74(12) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        67.19
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.288
_refine_diff_density_min         -1.463
_refine_diff_density_rms         0.267
