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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1445808'
_audit_update_record             
;
2016-01-07 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 Eu N4 O6'
_chemical_formula_weight         609.38

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                   9.868(3)
_cell_length_b                   9.903(4)
_cell_length_c                   12.895(4)
_cell_angle_alpha                87.003(6)
_cell_angle_beta                 72.541(6)
_cell_angle_gamma                73.377(6)
_cell_volume                     1151.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      22.95

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    2.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_T_max  0.758
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6099
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4239
_reflns_number_gt                3453
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0422P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4239
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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
Eu1 Eu 0.11595(4) -0.06920(3) 0.60266(2) 0.03086(12) Uani 1 1 d . . .
O1 O -0.0578(5) 0.1319(4) 0.5707(3) 0.0402(11) Uani 1 1 d . . .
O2 O -0.1856(6) 0.3087(5) 0.4986(4) 0.0693(17) Uani 1 1 d . . .
O3 O 0.2075(5) -0.2518(5) 0.7213(3) 0.0431(11) Uani 1 1 d . . .
O4 O 0.3774(5) -0.2013(5) 0.5843(4) 0.0473(12) Uani 1 1 d . . .
O5 O 0.2470(5) 0.0316(5) 0.4490(4) 0.0435(11) Uani 1 1 d . . .
O6 O 0.1052(5) 0.1349(4) 0.3441(3) 0.0380(10) Uani 1 1 d . . .
N1 N 0.0316(6) 0.9576(5) 1.1940(4) 0.0339(12) Uani 1 1 d . . .
N2 N -0.2250(6) 0.9047(5) 1.3151(4) 0.0350(12) Uani 1 1 d . . .
N4 N 0.0053(6) 0.6710(5) 0.8993(4) 0.0352(12) Uani 1 1 d . . .
H4 H 0.0819 0.6677 0.8444 0.042 Uiso 1 1 calc R . .
N3 N -0.2082(6) 0.6366(5) 0.9984(4) 0.0409(13) Uani 1 1 d . . .
C1 C 0.1594(7) 0.9777(7) 1.1364(5) 0.0417(16) Uani 1 1 d . . .
H1 H 0.1990 1.0335 1.1679 0.050 Uiso 1 1 calc R . .
C2 C 0.2388(8) 0.9213(7) 1.0319(5) 0.0473(18) Uani 1 1 d . . .
H2 H 0.3296 0.9368 0.9957 0.057 Uiso 1 1 calc R . .
C3 C 0.1788(7) 0.8418(7) 0.9836(5) 0.0403(16) Uani 1 1 d . . .
H3 H 0.2283 0.8037 0.9134 0.048 Uiso 1 1 calc R . .
C4 C 0.0446(7) 0.8188(6) 1.0400(5) 0.0309(14) Uani 1 1 d . . .
C5 C -0.0266(7) 0.8759(6) 1.1469(5) 0.0321(14) Uani 1 1 d . . .
C6 C -0.1641(7) 0.8507(6) 1.2115(5) 0.0315(14) Uani 1 1 d . . .
C7 C -0.3490(8) 0.8783(7) 1.3753(5) 0.0427(17) Uani 1 1 d . . .
H7 H -0.3883 0.9130 1.4470 0.051 Uiso 1 1 calc R . .
C8 C -0.4237(8) 0.8016(7) 1.3371(5) 0.0483(18) Uani 1 1 d . . .
H8 H -0.5114 0.7870 1.3816 0.058 Uiso 1 1 calc R . .
C9 C -0.3648(8) 0.7487(7) 1.2324(5) 0.0449(17) Uani 1 1 d . . .
H9 H -0.4128 0.6976 1.2048 0.054 Uiso 1 1 calc R . .
C10 C -0.2328(7) 0.7708(6) 1.1668(5) 0.0343(15) Uani 1 1 d . . .
C11 C -0.1609(7) 0.7155(6) 1.0587(5) 0.0351(15) Uani 1 1 d . . .
C12 C -0.0289(7) 0.7382(6) 0.9982(4) 0.0322(14) Uani 1 1 d . . .
C13 C -0.1029(7) 0.6113(6) 0.9037(5) 0.0340(14) Uani 1 1 d . . .
C14 C -0.1062(8) 0.5265(6) 0.8143(5) 0.0378(16) Uani 1 1 d . . .
C15 C 0.0008(8) 0.5065(7) 0.7131(5) 0.0442(17) Uani 1 1 d . . .
H15 H 0.0760 0.5500 0.6993 0.053 Uiso 1 1 calc R . .
C16 C -0.0040(8) 0.4226(7) 0.6332(5) 0.0436(17) Uani 1 1 d . . .
H16 H 0.0687 0.4089 0.5662 0.052 Uiso 1 1 calc R . .
C17 C -0.1161(7) 0.3588(6) 0.6519(5) 0.0359(15) Uani 1 1 d . . .
C18 C -0.2257(8) 0.3811(7) 0.7513(5) 0.0478(18) Uani 1 1 d . . .
H18 H -0.3023 0.3396 0.7637 0.057 Uiso 1 1 calc R . .
C19 C -0.2215(8) 0.4646(7) 0.8320(5) 0.0453(17) Uani 1 1 d . . .
H19 H -0.2956 0.4798 0.8983 0.054 Uiso 1 1 calc R . .
C20 C -0.1226(7) 0.2628(7) 0.5676(5) 0.0370(15) Uani 1 1 d . . .
C21 C 0.3405(8) -0.2819(7) 0.6567(6) 0.0408(16) Uani 1 1 d . . .
C22 C 0.4497(9) -0.4174(8) 0.6697(8) 0.083(3) Uani 1 1 d . . .
H22A H 0.5474 -0.4175 0.6258 0.124 Uiso 1 1 calc R . .
H22B H 0.4242 -0.4952 0.6470 0.124 Uiso 1 1 calc R . .
H22C H 0.4474 -0.4262 0.7447 0.124 Uiso 1 1 calc R . .
C23 C 0.2232(8) 0.1059(7) 0.3705(5) 0.0411(16) Uani 1 1 d . . .
C24 C 0.3424(10) 0.1670(11) 0.3048(8) 0.091(3) Uani 1 1 d . . .
H24A H 0.4217 0.1459 0.3371 0.136 Uiso 1 1 calc R . .
H24B H 0.3031 0.2674 0.3030 0.136 Uiso 1 1 calc R . .
H24C H 0.3793 0.1270 0.2320 0.136 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 O1 2.337(4) . ?
Eu1 O6 2.350(4) 2_556 ?
Eu1 O5 2.364(4) . ?
Eu1 O3 2.457(4) . ?
Eu1 O4 2.482(5) . ?
Eu1 O2 2.580(5) 2_556 ?
Eu1 N2 2.608(5) 2_567 ?
Eu1 O1 2.613(4) 2_556 ?
Eu1 N1 2.703(5) 2_567 ?
Eu1 Eu1 3.9481(10) 2_556 ?
O1 C20 1.275(7) . ?
O1 Eu1 2.613(4) 2_556 ?
O2 C20 1.230(7) . ?
O2 Eu1 2.580(5) 2_556 ?
O3 C21 1.285(8) . ?
O4 C21 1.235(7) . ?
O5 C23 1.259(7) . ?
O6 C23 1.262(7) . ?
O6 Eu1 2.350(4) 2_556 ?
N1 C1 1.323(8) . ?
N1 C5 1.371(7) . ?
N1 Eu1 2.703(5) 2_567 ?
N2 C7 1.326(8) . ?
N2 C6 1.357(7) . ?
N2 Eu1 2.608(5) 2_567 ?
N4 C13 1.347(8) . ?
N4 C12 1.373(7) . ?
N4 H4 0.8600 . ?
N3 C13 1.325(8) . ?
N3 C11 1.386(7) . ?
C1 C2 1.391(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(8) . ?
C4 C12 1.437(8) . ?
C5 C6 1.446(8) . ?
C6 C10 1.416(8) . ?
C7 C8 1.393(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.365(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.418(8) . ?
C11 C12 1.377(8) . ?
C13 C14 1.475(8) . ?
C14 C15 1.392(9) . ?
C14 C19 1.397(9) . ?
C15 C16 1.376(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(9) . ?
C17 C20 1.508(8) . ?
C18 C19 1.379(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C21 C22 1.499(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.491(9) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Eu1 O6 76.94(15) . 2_556 ?
O1 Eu1 O5 74.61(15) . . ?
O6 Eu1 O5 136.47(14) 2_556 . ?
O1 Eu1 O3 152.26(15) . . ?
O6 Eu1 O3 87.18(14) 2_556 . ?
O5 Eu1 O3 130.31(15) . . ?
O1 Eu1 O4 149.84(15) . . ?
O6 Eu1 O4 132.72(15) 2_556 . ?
O5 Eu1 O4 77.71(15) . . ?
O3 Eu1 O4 52.62(14) . . ?
O1 Eu1 O2 123.26(14) . 2_556 ?
O6 Eu1 O2 76.10(17) 2_556 2_556 ?
O5 Eu1 O2 92.91(18) . 2_556 ?
O3 Eu1 O2 73.13(15) . 2_556 ?
O4 Eu1 O2 69.56(16) . 2_556 ?
O1 Eu1 N2 88.37(15) . 2_567 ?
O6 Eu1 N2 135.16(15) 2_556 2_567 ?
O5 Eu1 N2 76.08(15) . 2_567 ?
O3 Eu1 N2 87.11(15) . 2_567 ?
O4 Eu1 N2 73.45(16) . 2_567 ?
O2 Eu1 N2 142.87(17) 2_556 2_567 ?
O1 Eu1 O1 74.34(14) . 2_556 ?
O6 Eu1 O1 70.86(14) 2_556 2_556 ?
O5 Eu1 O1 70.15(14) . 2_556 ?
O3 Eu1 O1 121.85(14) . 2_556 ?
O4 Eu1 O1 107.14(14) . 2_556 ?
O2 Eu1 O1 49.85(13) 2_556 2_556 ?
N2 Eu1 O1 145.02(14) 2_567 2_556 ?
O1 Eu1 N1 77.89(14) . 2_567 ?
O6 Eu1 N1 73.79(14) 2_556 2_567 ?
O5 Eu1 N1 129.65(15) . 2_567 ?
O3 Eu1 N1 75.88(15) . 2_567 ?
O4 Eu1 N1 112.08(15) . 2_567 ?
O2 Eu1 N1 137.35(17) 2_556 2_567 ?
N2 Eu1 N1 61.69(15) 2_567 2_567 ?
O1 Eu1 N1 138.90(15) 2_556 2_567 ?
C20 O1 Eu1 157.9(4) . . ?
C20 O1 Eu1 92.8(3) . 2_556 ?
Eu1 O1 Eu1 105.66(14) . 2_556 ?
C20 O2 Eu1 95.5(4) . 2_556 ?
C21 O3 Eu1 92.2(4) . . ?
C21 O4 Eu1 92.4(4) . . ?
C23 O5 Eu1 139.4(4) . . ?
C23 O6 Eu1 136.8(4) . 2_556 ?
C1 N1 C5 117.4(5) . . ?
C1 N1 Eu1 123.0(4) . 2_567 ?
C5 N1 Eu1 119.6(4) . 2_567 ?
C7 N2 C6 118.6(5) . . ?
C7 N2 Eu1 118.6(4) . 2_567 ?
C6 N2 Eu1 122.6(4) . 2_567 ?
C13 N4 C12 107.6(5) . . ?
C13 N4 H4 126.2 . . ?
C12 N4 H4 126.2 . . ?
C13 N3 C11 104.2(5) . . ?
N1 C1 C2 124.6(6) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C3 C2 C1 118.0(6) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 C12 124.7(5) . . ?
C5 C4 C12 116.4(5) . . ?
N1 C5 C4 121.4(6) . . ?
N1 C5 C6 117.2(5) . . ?
C4 C5 C6 121.4(5) . . ?
N2 C6 C10 121.1(6) . . ?
N2 C6 C5 118.7(5) . . ?
C10 C6 C5 120.2(5) . . ?
N2 C7 C8 123.7(6) . . ?
N2 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C9 C8 C7 118.2(6) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C10 120.2(6) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C6 118.1(5) . . ?
C9 C10 C11 124.1(6) . . ?
C6 C10 C11 117.8(6) . . ?
C12 C11 N3 110.6(5) . . ?
C12 C11 C10 121.7(5) . . ?
N3 C11 C10 127.8(6) . . ?
N4 C12 C11 105.1(5) . . ?
N4 C12 C4 132.4(6) . . ?
C11 C12 C4 122.5(5) . . ?
N3 C13 N4 112.5(5) . . ?
N3 C13 C14 122.8(6) . . ?
N4 C13 C14 124.6(6) . . ?
C15 C14 C19 118.9(6) . . ?
C15 C14 C13 122.5(6) . . ?
C19 C14 C13 118.6(6) . . ?
C16 C15 C14 120.5(6) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.4(6) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 119.7(6) . . ?
C16 C17 C20 122.0(6) . . ?
C18 C17 C20 118.4(6) . . ?
C19 C18 C17 120.3(6) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.2(6) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
O2 C20 O1 121.7(6) . . ?
O2 C20 C17 121.7(6) . . ?
O1 C20 C17 116.6(5) . . ?
O4 C21 O3 120.6(6) . . ?
O4 C21 C22 120.5(7) . . ?
O3 C21 C22 118.9(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 O6 125.1(6) . . ?
O5 C23 C24 117.6(6) . . ?
O6 C23 C24 117.2(6) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Eu1 O1 C20 140.8(11) 2_556 . . . ?
O5 Eu1 O1 C20 -72.5(11) . . . . ?
O3 Eu1 O1 C20 84.2(12) . . . . ?
O4 Eu1 O1 C20 -48.4(12) . . . . ?
O2 Eu1 O1 C20 -155.7(11) 2_556 . . . ?
N2 Eu1 O1 C20 3.5(11) 2_567 . . . ?
O1 Eu1 O1 C20 -145.7(12) 2_556 . . . ?
N1 Eu1 O1 C20 64.9(11) 2_567 . . . ?
O6 Eu1 O1 Eu1 -73.47(16) 2_556 . . 2_556 ?
O5 Eu1 O1 Eu1 73.23(16) . . . 2_556 ?
O3 Eu1 O1 Eu1 -130.1(3) . . . 2_556 ?
O4 Eu1 O1 Eu1 97.3(3) . . . 2_556 ?
O2 Eu1 O1 Eu1 -10.0(3) 2_556 . . 2_556 ?
N2 Eu1 O1 Eu1 149.24(17) 2_567 . . 2_556 ?
O1 Eu1 O1 Eu1 0.0 2_556 . . 2_556 ?
N1 Eu1 O1 Eu1 -149.39(18) 2_567 . . 2_556 ?
O1 Eu1 O3 C21 -160.3(4) . . . . ?
O6 Eu1 O3 C21 145.1(4) 2_556 . . . ?
O5 Eu1 O3 C21 -10.4(4) . . . . ?
O4 Eu1 O3 C21 -8.1(3) . . . . ?
O2 Eu1 O3 C21 68.8(4) 2_556 . . . ?
N2 Eu1 O3 C21 -79.4(4) 2_567 . . . ?
O1 Eu1 O3 C21 79.8(4) 2_556 . . . ?
N1 Eu1 O3 C21 -140.9(4) 2_567 . . . ?
Eu1 Eu1 O3 C21 109.1(4) 2_556 . . . ?
O1 Eu1 O4 C21 162.9(4) . . . . ?
O6 Eu1 O4 C21 -29.5(4) 2_556 . . . ?
O5 Eu1 O4 C21 -173.4(4) . . . . ?
O3 Eu1 O4 C21 8.4(3) . . . . ?
O2 Eu1 O4 C21 -75.6(4) 2_556 . . . ?
N2 Eu1 O4 C21 107.6(4) 2_567 . . . ?
O1 Eu1 O4 C21 -109.0(4) 2_556 . . . ?
N1 Eu1 O4 C21 58.5(4) 2_567 . . . ?
Eu1 Eu1 O4 C21 -133.8(3) 2_556 . . . ?
O1 Eu1 O5 C23 -28.4(6) . . . . ?
O6 Eu1 O5 C23 22.6(7) 2_556 . . . ?
O3 Eu1 O5 C23 165.6(6) . . . . ?
O4 Eu1 O5 C23 163.7(6) . . . . ?
O2 Eu1 O5 C23 95.4(6) 2_556 . . . ?
N2 Eu1 O5 C23 -120.5(6) 2_567 . . . ?
O1 Eu1 O5 C23 50.2(6) 2_556 . . . ?
N1 Eu1 O5 C23 -87.7(6) 2_567 . . . ?
Eu1 Eu1 O5 C23 13.0(6) 2_556 . . . ?
C5 N1 C1 C2 -0.3(10) . . . . ?
Eu1 N1 C1 C2 179.6(5) 2_567 . . . ?
N1 C1 C2 C3 1.7(10) . . . . ?
C1 C2 C3 C4 -1.0(10) . . . . ?
C2 C3 C4 C5 -1.1(9) . . . . ?
C2 C3 C4 C12 179.9(6) . . . . ?
C1 N1 C5 C4 -1.8(8) . . . . ?
Eu1 N1 C5 C4 178.2(4) 2_567 . . . ?
C1 N1 C5 C6 178.2(6) . . . . ?
Eu1 N1 C5 C6 -1.7(7) 2_567 . . . ?
C3 C4 C5 N1 2.5(9) . . . . ?
C12 C4 C5 N1 -178.3(5) . . . . ?
C3 C4 C5 C6 -177.5(6) . . . . ?
C12 C4 C5 C6 1.7(8) . . . . ?
C7 N2 C6 C10 1.6(9) . . . . ?
Eu1 N2 C6 C10 -175.0(4) 2_567 . . . ?
C7 N2 C6 C5 -178.2(6) . . . . ?
Eu1 N2 C6 C5 5.2(7) 2_567 . . . ?
N1 C5 C6 N2 -2.1(8) . . . . ?
C4 C5 C6 N2 177.9(5) . . . . ?
N1 C5 C6 C10 178.0(5) . . . . ?
C4 C5 C6 C10 -1.9(9) . . . . ?
C6 N2 C7 C8 -2.1(10) . . . . ?
Eu1 N2 C7 C8 174.6(5) 2_567 . . . ?
N2 C7 C8 C9 1.1(11) . . . . ?
C7 C8 C9 C10 0.4(10) . . . . ?
C8 C9 C10 C6 -0.8(10) . . . . ?
C8 C9 C10 C11 177.6(6) . . . . ?
N2 C6 C10 C9 -0.2(9) . . . . ?
C5 C6 C10 C9 179.6(6) . . . . ?
N2 C6 C10 C11 -178.7(6) . . . . ?
C5 C6 C10 C11 1.1(9) . . . . ?
C13 N3 C11 C12 1.1(7) . . . . ?
C13 N3 C11 C10 -180.0(6) . . . . ?
C9 C10 C11 C12 -178.6(6) . . . . ?
C6 C10 C11 C12 -0.2(9) . . . . ?
C9 C10 C11 N3 2.5(11) . . . . ?
C6 C10 C11 N3 -179.1(6) . . . . ?
C13 N4 C12 C11 -0.5(6) . . . . ?
C13 N4 C12 C4 -179.8(6) . . . . ?
N3 C11 C12 N4 -0.4(7) . . . . ?
C10 C11 C12 N4 -179.4(5) . . . . ?
N3 C11 C12 C4 179.1(5) . . . . ?
C10 C11 C12 C4 0.0(9) . . . . ?
C3 C4 C12 N4 -2.4(10) . . . . ?
C5 C4 C12 N4 178.5(6) . . . . ?
C3 C4 C12 C11 178.4(6) . . . . ?
C5 C4 C12 C11 -0.7(9) . . . . ?
C11 N3 C13 N4 -1.4(7) . . . . ?
C11 N3 C13 C14 178.5(6) . . . . ?
C12 N4 C13 N3 1.2(7) . . . . ?
C12 N4 C13 C14 -178.7(6) . . . . ?
N3 C13 C14 C15 176.5(6) . . . . ?
N4 C13 C14 C15 -3.5(10) . . . . ?
N3 C13 C14 C19 -3.2(9) . . . . ?
N4 C13 C14 C19 176.8(6) . . . . ?
C19 C14 C15 C16 -2.5(10) . . . . ?
C13 C14 C15 C16 177.8(6) . . . . ?
C14 C15 C16 C17 0.9(10) . . . . ?
C15 C16 C17 C18 1.0(10) . . . . ?
C15 C16 C17 C20 -178.2(6) . . . . ?
C16 C17 C18 C19 -1.2(10) . . . . ?
C20 C17 C18 C19 178.0(6) . . . . ?
C17 C18 C19 C14 -0.4(10) . . . . ?
C15 C14 C19 C18 2.3(10) . . . . ?
C13 C14 C19 C18 -178.0(6) . . . . ?
Eu1 O2 C20 O1 -2.4(7) 2_556 . . . ?
Eu1 O2 C20 C17 176.6(6) 2_556 . . . ?
Eu1 O1 C20 O2 149.5(8) . . . . ?
Eu1 O1 C20 O2 2.4(7) 2_556 . . . ?
Eu1 O1 C20 C17 -29.6(15) . . . . ?
Eu1 O1 C20 C17 -176.7(5) 2_556 . . . ?
C16 C17 C20 O2 -88.4(9) . . . . ?
C18 C17 C20 O2 92.4(8) . . . . ?
C16 C17 C20 O1 90.6(8) . . . . ?
C18 C17 C20 O1 -88.5(8) . . . . ?
Eu1 O4 C21 O3 -14.9(6) . . . . ?
Eu1 O4 C21 C22 164.3(6) . . . . ?
Eu1 O3 C21 O4 15.1(6) . . . . ?
Eu1 O3 C21 C22 -164.2(6) . . . . ?
Eu1 O5 C23 O6 -11.0(11) . . . . ?
Eu1 O5 C23 C24 167.7(6) . . . . ?
Eu1 O6 C23 O5 -6.5(10) 2_556 . . . ?
Eu1 O6 C23 C24 174.8(6) 2_556 . . . ?

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
N4 H4 O3 0.86 1.99 2.788(7) 154.7 1_565
C8 H8 O4 0.93 2.51 3.207(8) 132.2 1_466
C1 H1 O6 0.93 2.34 2.997(7) 127.4 1_566
C7 H7 O5 0.93 2.38 3.007(7) 124.2 2_567

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.134
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1569809'
_audit_update_record             
;
2017-08-19 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H42 Eu2 N8 O12'
_chemical_formula_weight         1250.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Eu Eu -0.1578 3.6682 '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                   9.8401(15)
_cell_length_b                   10.4399(16)
_cell_length_c                   13.681(2)
_cell_angle_alpha                92.681(2)
_cell_angle_beta                 110.976(2)
_cell_angle_gamma                109.933(2)
_cell_volume                     1210.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3263
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.92

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9018
_exptl_absorpt_correction_T_max  0.9491
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6370
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4458
_reflns_number_gt                3936
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0471P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4458
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.6989(6) 0.9373(5) 0.3717(4) 0.0472(11) Uani 1 1 d . . .
H1 H 0.6250 0.9779 0.3503 0.057 Uiso 1 1 calc R . .
C2 C 0.7392(6) 0.9041(5) 0.4731(4) 0.0484(11) Uani 1 1 d . . .
H2 H 0.6936 0.9235 0.5180 0.058 Uiso 1 1 calc R . .
C3 C 0.8462(6) 0.8429(5) 0.5058(3) 0.0459(11) Uani 1 1 d . . .
H3 H 0.8743 0.8199 0.5731 0.055 Uiso 1 1 calc R . .
C4 C 0.9127(5) 0.8156(4) 0.4371(3) 0.0376(10) Uani 1 1 d . . .
C5 C 0.8657(5) 0.8522(4) 0.3339(3) 0.0365(9) Uani 1 1 d . . .
C6 C 0.9311(5) 0.8254(4) 0.2590(3) 0.0391(10) Uani 1 1 d . . .
C7 C 0.9432(6) 0.8445(5) 0.0944(4) 0.0486(12) Uani 1 1 d . . .
H7 H 0.9105 0.8722 0.0292 0.058 Uiso 1 1 calc R . .
C8 C 1.0532(6) 0.7807(5) 0.1144(4) 0.0540(13) Uani 1 1 d . . .
H8 H 1.0926 0.7674 0.0640 0.065 Uiso 1 1 calc R . .
C9 C 1.1007(6) 0.7388(5) 0.2103(4) 0.0492(12) Uani 1 1 d . . .
H9 H 1.1730 0.6962 0.2253 0.059 Uiso 1 1 calc R . .
C10 C 1.0410(5) 0.7600(5) 0.2852(3) 0.0399(10) Uani 1 1 d . . .
C11 C 1.0840(5) 0.7216(5) 0.3885(3) 0.0415(10) Uani 1 1 d . . .
C12 C 1.0245(5) 0.7499(4) 0.4588(3) 0.0383(10) Uani 1 1 d . . .
C13 C 1.1893(5) 0.6475(4) 0.5275(3) 0.0404(10) Uani 1 1 d . . .
C14 C 1.2822(5) 0.5820(5) 0.6023(3) 0.0419(10) Uani 1 1 d . . .
C15 C 1.2874(6) 0.5781(6) 0.7046(4) 0.0566(13) Uani 1 1 d . . .
H15 H 1.2312 0.6186 0.7284 0.068 Uiso 1 1 calc R . .
C16 C 1.3755(7) 0.5146(7) 0.7720(4) 0.0676(16) Uani 1 1 d . . .
H16 H 1.3771 0.5118 0.8402 0.081 Uiso 1 1 calc R . .
C17 C 1.4617(6) 0.4548(6) 0.7382(4) 0.0583(14) Uani 1 1 d . . .
H17 H 1.5226 0.4137 0.7837 0.070 Uiso 1 1 calc R . .
C18 C 1.4553(6) 0.4577(5) 0.6373(4) 0.0541(12) Uani 1 1 d . . .
H18 H 1.5109 0.4168 0.6133 0.065 Uiso 1 1 calc R . .
C19 C 1.3670(6) 0.5208(5) 0.5702(4) 0.0487(11) Uani 1 1 d . . .
H19 H 1.3647 0.5220 0.5017 0.058 Uiso 1 1 calc R . .
C20 C 0.9770(5) 1.2304(5) 0.1979(3) 0.0408(10) Uani 1 1 d . . .
C21 C 1.1235(6) 1.3618(6) 0.2381(5) 0.0635(15) Uani 1 1 d . . .
H21A H 1.2069 1.3469 0.2932 0.095 Uiso 1 1 calc R . .
H21B H 1.1023 1.4354 0.2662 0.095 Uiso 1 1 calc R . .
H21C H 1.1546 1.3866 0.1804 0.095 Uiso 1 1 calc R . .
C22 C 0.3959(6) 0.7381(5) 0.0190(3) 0.0435(11) Uani 1 1 d . . .
C23 C 0.2519(6) 0.6049(5) -0.0182(5) 0.0581(13) Uani 1 1 d . . .
H23A H 0.2829 0.5273 -0.0197 0.087 Uiso 1 1 calc R . .
H23B H 0.1813 0.6034 -0.0886 0.087 Uiso 1 1 calc R . .
H23C H 0.1999 0.5992 0.0298 0.087 Uiso 1 1 calc R . .
C24 C 0.5948(5) 0.9210(5) -0.1532(3) 0.0413(10) Uani 1 1 d . . .
C25 C 0.6493(6) 0.8807(6) -0.2347(4) 0.0590(14) Uani 1 1 d . . .
H25A H 0.7624 0.9188 -0.2062 0.089 Uiso 1 1 calc R . .
H25B H 0.6091 0.9161 -0.2977 0.089 Uiso 1 1 calc R . .
H25C H 0.6113 0.7814 -0.2524 0.089 Uiso 1 1 calc R . .
N1 N 0.7599(4) 0.9142(4) 0.3043(3) 0.0411(9) Uani 1 1 d . . .
N2 N 0.8841(4) 0.8670(4) 0.1634(3) 0.0419(9) Uani 1 1 d . . .
N3 N 1.1872(5) 0.6569(4) 0.4307(3) 0.0452(9) Uani 1 1 d . . .
N4 N 1.0943(4) 0.7028(4) 0.5489(3) 0.0411(9) Uani 1 1 d . . .
H4 H 1.0801 0.7076 0.6073 0.049 Uiso 1 1 calc R . .
O1 O 0.8932(4) 1.2004(3) 0.2513(2) 0.0474(8) Uani 1 1 d . . .
O2 O 0.9421(4) 1.1517(3) 0.1131(2) 0.0483(8) Uani 1 1 d . . .
O3 O 0.5249(4) 0.7432(3) 0.0872(3) 0.0589(10) Uani 1 1 d . . .
O4 O 0.3849(4) 0.8454(3) -0.0180(2) 0.0490(8) Uani 1 1 d . . .
O6 O 0.6716(4) 0.9189(3) -0.0574(2) 0.0482(8) Uani 1 1 d . . .
O5 O 0.5223(4) 1.0442(4) 0.1852(2) 0.0485(8) Uani 1 1 d . . .
Eu1 Eu 0.68752(2) 0.98986(2) 0.114474(15) 0.03767(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.319(6) . ?
C1 C2 1.396(6) . ?
C2 C3 1.366(6) . ?
C3 C4 1.391(6) . ?
C4 C5 1.434(5) . ?
C4 C12 1.438(6) . ?
C5 N1 1.360(5) . ?
C5 C6 1.452(6) . ?
C6 N2 1.368(5) . ?
C6 C10 1.419(6) . ?
C7 N2 1.323(6) . ?
C7 C8 1.409(7) . ?
C8 C9 1.373(6) . ?
C9 C10 1.394(6) . ?
C10 C11 1.441(6) . ?
C11 C12 1.361(6) . ?
C11 N3 1.380(5) . ?
C12 N4 1.384(5) . ?
C13 N3 1.325(6) . ?
C13 N4 1.357(6) . ?
C13 C14 1.474(6) . ?
C14 C19 1.377(7) . ?
C14 C15 1.386(7) . ?
C15 C16 1.385(7) . ?
C16 C17 1.392(8) . ?
C17 C18 1.362(7) . ?
C18 C19 1.381(6) . ?
C20 O2 1.254(5) . ?
C20 O1 1.260(6) . ?
C20 C21 1.509(7) . ?
C20 Eu1 2.872(5) . ?
C22 O3 1.259(5) . ?
C22 O4 1.273(5) . ?
C22 C23 1.508(7) . ?
C22 Eu1 2.950(5) . ?
C24 O5 1.261(5) 2_675 ?
C24 O6 1.262(5) . ?
C24 C25 1.499(7) . ?
N1 Eu1 2.670(3) . ?
N2 Eu1 2.584(4) . ?
O1 Eu1 2.510(3) . ?
O2 Eu1 2.506(3) . ?
O3 Eu1 2.450(3) . ?
O4 Eu1 2.363(3) 2_675 ?
O4 Eu1 2.692(3) . ?
O6 Eu1 2.366(3) . ?
O5 C24 1.261(5) 2_675 ?
O5 Eu1 2.368(3) . ?
Eu1 O4 2.363(3) 2_675 ?
Eu1 Eu1 3.9742(6) 2_675 ?

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
N1 C1 C2 123.7(4) . . ?
C3 C2 C1 119.2(5) . . ?
C2 C3 C4 119.0(4) . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 C12 125.8(4) . . ?
C5 C4 C12 115.5(4) . . ?
N1 C5 C4 120.7(4) . . ?
N1 C5 C6 118.4(4) . . ?
C4 C5 C6 120.9(4) . . ?
N2 C6 C10 121.6(4) . . ?
N2 C6 C5 117.5(4) . . ?
C10 C6 C5 120.9(4) . . ?
N2 C7 C8 123.5(4) . . ?
C9 C8 C7 118.3(5) . . ?
C8 C9 C10 120.2(4) . . ?
C9 C10 C6 118.1(4) . . ?
C9 C10 C11 124.8(4) . . ?
C6 C10 C11 117.1(4) . . ?
C12 C11 N3 111.3(4) . . ?
C12 C11 C10 121.4(4) . . ?
N3 C11 C10 127.3(4) . . ?
C11 C12 N4 105.3(4) . . ?
C11 C12 C4 124.2(4) . . ?
N4 C12 C4 130.5(4) . . ?
N3 C13 N4 112.3(4) . . ?
N3 C13 C14 123.7(4) . . ?
N4 C13 C14 124.0(4) . . ?
C19 C14 C15 117.9(4) . . ?
C19 C14 C13 119.4(4) . . ?
C15 C14 C13 122.7(4) . . ?
C16 C15 C14 120.7(5) . . ?
C15 C16 C17 120.4(5) . . ?
C18 C17 C16 118.8(5) . . ?
C17 C18 C19 120.7(5) . . ?
C14 C19 C18 121.6(5) . . ?
O2 C20 O1 121.1(4) . . ?
O2 C20 C21 119.6(5) . . ?
O1 C20 C21 119.3(4) . . ?
O2 C20 Eu1 60.6(2) . . ?
O1 C20 Eu1 60.7(2) . . ?
C21 C20 Eu1 176.5(3) . . ?
O3 C22 O4 120.6(4) . . ?
O3 C22 C23 120.1(4) . . ?
O4 C22 C23 119.3(4) . . ?
O3 C22 Eu1 54.8(2) . . ?
O4 C22 Eu1 65.8(2) . . ?
C23 C22 Eu1 173.8(3) . . ?
O5 C24 O6 125.2(4) 2_675 . ?
O5 C24 C25 117.7(4) 2_675 . ?
O6 C24 C25 117.0(4) . . ?
C1 N1 C5 118.6(4) . . ?
C1 N1 Eu1 122.3(3) . . ?
C5 N1 Eu1 119.1(3) . . ?
C7 N2 C6 118.4(4) . . ?
C7 N2 Eu1 119.3(3) . . ?
C6 N2 Eu1 122.4(3) . . ?
C13 N3 C11 104.3(4) . . ?
C13 N4 C12 106.8(4) . . ?
C20 O1 Eu1 93.3(3) . . ?
C20 O2 Eu1 93.6(3) . . ?
C22 O3 Eu1 100.4(3) . . ?
C22 O4 Eu1 167.7(3) . 2_675 ?
C22 O4 Eu1 88.6(3) . . ?
Eu1 O4 Eu1 103.49(12) 2_675 . ?
C24 O6 Eu1 138.6(3) . . ?
C24 O5 Eu1 138.0(3) 2_675 . ?
O4 Eu1 O6 76.32(11) 2_675 . ?
O4 Eu1 O5 75.64(11) 2_675 . ?
O6 Eu1 O5 136.14(10) . . ?
O4 Eu1 O3 126.75(11) 2_675 . ?
O6 Eu1 O3 81.78(12) . . ?
O5 Eu1 O3 88.76(13) . . ?
O4 Eu1 O2 76.61(11) 2_675 . ?
O6 Eu1 O2 76.17(11) . . ?
O5 Eu1 O2 127.78(11) . . ?
O3 Eu1 O2 142.63(12) . . ?
O4 Eu1 O1 83.86(11) 2_675 . ?
O6 Eu1 O1 127.35(11) . . ?
O5 Eu1 O1 81.93(11) . . ?
O3 Eu1 O1 144.62(10) . . ?
O2 Eu1 O1 51.76(10) . . ?
O4 Eu1 N2 144.36(12) 2_675 . ?
O6 Eu1 N2 80.20(10) . . ?
O5 Eu1 N2 138.06(11) . . ?
O3 Eu1 N2 74.84(12) . . ?
O2 Eu1 N2 71.96(11) . . ?
O1 Eu1 N2 89.59(11) . . ?
O4 Eu1 N1 144.90(11) 2_675 . ?
O6 Eu1 N1 138.74(11) . . ?
O5 Eu1 N1 75.69(11) . . ?
O3 Eu1 N1 72.18(11) . . ?
O2 Eu1 N1 106.20(11) . . ?
O1 Eu1 N1 72.45(11) . . ?
N2 Eu1 N1 62.63(11) . . ?
O4 Eu1 O4 76.51(12) 2_675 . ?
O6 Eu1 O4 70.00(11) . . ?
O5 Eu1 O4 71.10(10) . . ?
O3 Eu1 O4 50.36(9) . . ?
O2 Eu1 O4 140.72(10) . . ?
O1 Eu1 O4 149.74(10) . . ?
N2 Eu1 O4 119.62(11) . . ?
N1 Eu1 O4 112.29(11) . . ?
O4 Eu1 C20 77.88(11) 2_675 . ?
O6 Eu1 C20 101.54(12) . . ?
O5 Eu1 C20 104.71(12) . . ?
O3 Eu1 C20 154.75(11) . . ?
O2 Eu1 C20 25.84(11) . . ?
O1 Eu1 C20 25.98(11) . . ?
N2 Eu1 C20 81.03(12) . . ?
N1 Eu1 C20 90.28(12) . . ?
O4 Eu1 C20 154.28(11) . . ?
O4 Eu1 C22 102.05(12) 2_675 . ?
O6 Eu1 C22 75.23(12) . . ?
O5 Eu1 C22 78.47(13) . . ?
O3 Eu1 C22 24.83(11) . . ?
O2 Eu1 C22 150.80(12) . . ?
O1 Eu1 C22 157.33(12) . . ?
N2 Eu1 C22 97.38(12) . . ?
N1 Eu1 C22 91.61(12) . . ?
O4 Eu1 C22 25.55(10) . . ?
C20 Eu1 C22 176.63(12) . . ?
O4 Eu1 Eu1 41.19(8) 2_675 2_675 ?
O6 Eu1 Eu1 68.15(7) . 2_675 ?
O5 Eu1 Eu1 68.48(7) . 2_675 ?
O3 Eu1 Eu1 85.62(7) . 2_675 ?
O2 Eu1 Eu1 112.74(7) . 2_675 ?
O1 Eu1 Eu1 121.42(7) . 2_675 ?
N2 Eu1 Eu1 144.88(8) . 2_675 ?
N1 Eu1 Eu1 138.02(8) . 2_675 ?
O4 Eu1 Eu1 35.32(6) . 2_675 ?
C20 Eu1 Eu1 119.04(8) . 2_675 ?
C22 Eu1 Eu1 60.86(8) . 2_675 ?

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
N4 H4 O1 0.86 2.01 2.815(5) 156.1 2_776

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.130
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.106
####################################################################### 
# 
# 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 1569810'
_audit_update_record             
;
2017-08-19 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H42 N8 O12 Tb2'
_chemical_formula_sum            'C50 H42 N8 O12 Tb2'
_chemical_formula_weight         1264.78

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                   9.780(2)
_cell_length_b                   10.418(2)
_cell_length_c                   13.614(4)
_cell_angle_alpha                73.167(6)
_cell_angle_beta                 68.983(4)
_cell_angle_gamma                69.942(4)
_cell_volume                     1194.1(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1011
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      19.49

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    3.010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_T_max  0.516
_exptl_absorpt_process_details   multi-scan2008

_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_reflns_number            6242
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.1041
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4444
_reflns_number_gt                2925
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0490P)²+0.9273P] 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         4392
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_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 0.92728(5) 0.49048(5) 0.38511(3) 0.04367(17) Uani 1 1 d . . .
O1 O 0.6719(7) 0.6509(6) 0.3864(5) 0.0556(17) Uani 1 1 d . . .
O2 O 0.8599(7) 0.6976(6) 0.2494(4) 0.0527(16) Uani 1 1 d . . .
O3 O 1.0649(8) 0.2469(6) 0.4120(5) 0.066(2) Uani 1 1 d . . .
O4 O 1.0988(7) 0.3467(6) 0.5183(4) 0.0525(16) Uani 1 1 d . . .
O5 O 1.1602(7) 0.5433(6) 0.3165(5) 0.0539(17) Uani 1 1 d . . .
O6 O 0.7744(7) 0.4194(6) 0.5561(5) 0.0529(16) Uani 1 1 d . . .
N1 N 1.0455(8) 0.4160(7) 0.1971(5) 0.0410(17) Uani 1 1 d . . .
N2 N 0.7793(8) 0.3669(7) 0.3375(5) 0.0419(17) Uani 1 1 d . . .
N3 N 0.9556(8) 0.2033(7) -0.0489(5) 0.0457(19) Uani 1 1 d . . .
H3N H 1.0288 0.2070 -0.1074 0.055 Uiso 1 1 calc R . .
N4 N 0.7417(8) 0.1591(8) 0.0699(5) 0.0486(19) Uani 1 1 d . . .
C1 C 1.1739(11) 0.4394(10) 0.1285(7) 0.053(2) Uani 1 1 d . . .
H1 H 1.2258 0.4826 0.1487 0.064 Uiso 1 1 calc R . .
C2 C 1.2362(11) 0.4032(10) 0.0279(7) 0.054(2) Uani 1 1 d . . .
H2 H 1.3285 0.4197 -0.0165 0.065 Uiso 1 1 calc R . .
C3 C 1.1618(10) 0.3441(9) -0.0046(7) 0.048(2) Uani 1 1 d . . .
H3 H 1.2017 0.3213 -0.0724 0.058 Uiso 1 1 calc R . .
C4 C 1.0240(10) 0.3166(8) 0.0632(6) 0.042(2) Uani 1 1 d . . .
C5 C 0.9352(10) 0.2512(9) 0.0413(7) 0.045(2) Uani 1 1 d . . .
C6 C 0.8060(10) 0.2223(9) 0.1114(7) 0.047(2) Uani 1 1 d . . .
C7 C 0.7456(10) 0.2597(9) 0.2153(6) 0.046(2) Uani 1 1 d . . .
C8 C 0.6103(10) 0.2403(10) 0.2895(7) 0.053(3) Uani 1 1 d . . .
H8 H 0.5514 0.1994 0.2741 0.064 Uiso 1 1 calc R . .
C9 C 0.5641(11) 0.2815(10) 0.3850(7) 0.058(3) Uani 1 1 d . . .
H9 H 0.4745 0.2672 0.4358 0.070 Uiso 1 1 calc R . .
C10 C 0.6500(12) 0.3442(10) 0.4058(7) 0.060(3) Uani 1 1 d . . .
H10 H 0.6159 0.3724 0.4714 0.072 Uiso 1 1 calc R . .
C11 C 0.8291(10) 0.3266(9) 0.2409(6) 0.044(2) Uani 1 1 d . . .
C12 C 0.9671(10) 0.3542(9) 0.1672(6) 0.042(2) Uani 1 1 d . . .
C13 C 0.8388(11) 0.1498(9) -0.0273(7) 0.046(2) Uani 1 1 d . . .
C14 C 0.8206(11) 0.0823(9) -0.1025(7) 0.051(2) Uani 1 1 d . . .
C15 C 0.9180(12) 0.0794(10) -0.2046(7) 0.062(3) Uani 1 1 d . . .
H15 H 0.9971 0.1214 -0.2286 0.074 Uiso 1 1 calc R . .
C16 C 0.8976(12) 0.0132(12) -0.2716(8) 0.070(3) Uani 1 1 d . . .
H16 H 0.9661 0.0076 -0.3394 0.084 Uiso 1 1 calc R . .
C17 C 0.7788(12) -0.0431(10) -0.2388(8) 0.060(3) Uani 1 1 d . . .
H17 H 0.7629 -0.0832 -0.2852 0.072 Uiso 1 1 calc R . .
C18 C 0.6838(11) -0.0406(9) -0.1388(8) 0.054(2) Uani 1 1 d . . .
H18 H 0.6047 -0.0825 -0.1156 0.065 Uiso 1 1 calc R . .
C19 C 0.7017(11) 0.0227(10) -0.0704(8) 0.057(3) Uani 1 1 d . . .
H19 H 0.6336 0.0254 -0.0023 0.069 Uiso 1 1 calc R . .
C24 C 0.7215(12) 0.7300(10) 0.3004(7) 0.051(2) Uani 1 1 d . . .
C25 C 0.6157(12) 0.8624(10) 0.2606(8) 0.066(3) Uani 1 1 d . . .
H25A H 0.5924 0.8508 0.2015 0.099 Uiso 1 1 calc R . .
H25B H 0.6634 0.9369 0.2376 0.099 Uiso 1 1 calc R . .
H25C H 0.5236 0.8841 0.3174 0.099 Uiso 1 1 calc R . .
C20 C 1.1250(10) 0.2404(9) 0.4793(7) 0.045(2) Uani 1 1 d . . .
C21 C 1.2315(12) 0.1056(10) 0.5163(8) 0.066(3) Uani 1 1 d . . .
H21A H 1.2178 0.0304 0.4967 0.099 Uiso 1 1 calc R . .
H21B H 1.2098 0.0897 0.5927 0.099 Uiso 1 1 calc R . .
H21C H 1.3346 0.1110 0.4830 0.099 Uiso 1 1 calc R . .
C22 C 1.2438(11) 0.5790(9) 0.3492(6) 0.045(2) Uani 1 1 d . . .
C23 C 1.3805(11) 0.6193(11) 0.2678(7) 0.067(3) Uani 1 1 d . . .
H23A H 1.3656 0.7177 0.2583 0.100 Uiso 1 1 calc R . .
H23B H 1.3948 0.5963 0.2009 0.100 Uiso 1 1 calc R . .
H23C H 1.4687 0.5699 0.2923 0.100 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
Tb1 O5 2.324(6) . ?
Tb1 O4 2.329(5) 2_766 ?
Tb1 O6 2.339(6) . ?
Tb1 O3 2.420(6) . ?
Tb1 O2 2.468(6) . ?
Tb1 O1 2.481(6) . ?
Tb1 N2 2.570(7) . ?
Tb1 N1 2.627(6) . ?
Tb1 O4 2.689(6) . ?
Tb1 C24 2.857(10) . ?
Tb1 C20 2.925(9) . ?
Tb1 Tb1 3.9490(13) 2_766 ?
O1 C24 1.263(10) . ?
O2 C24 1.255(10) . ?
O3 C20 1.230(10) . ?
O4 C20 1.274(9) . ?
O4 Tb1 2.329(5) 2_766 ?
O5 C22 1.254(10) . ?
O6 C22 1.240(9) 2_766 ?
N1 C1 1.321(10) . ?
N1 C12 1.372(10) . ?
N2 C10 1.324(11) . ?
N2 C11 1.365(9) . ?
N3 C13 1.343(11) . ?
N3 C5 1.380(9) . ?
N3 H3N 0.8600 . ?
N4 C13 1.331(10) . ?
N4 C6 1.379(10) . ?
C1 C2 1.391(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.341(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.421(12) . ?
C4 C12 1.440(10) . ?
C5 C6 1.352(11) . ?
C6 C7 1.436(11) . ?
C7 C8 1.385(11) . ?
C7 C11 1.418(12) . ?
C8 C9 1.358(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(13) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.428(11) . ?
C13 C14 1.487(11) . ?
C14 C15 1.376(12) . ?
C14 C19 1.379(13) . ?
C15 C16 1.391(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.356(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.347(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(12) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C24 C25 1.502(12) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C20 C21 1.508(12) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O6 1.240(9) 2_766 ?
C22 C23 1.498(12) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Tb1 O4 76.0(2) . 2_766 ?
O5 Tb1 O6 135.5(2) . . ?
O4 Tb1 O6 75.9(2) 2_766 . ?
O5 Tb1 O3 88.0(2) . . ?
O4 Tb1 O3 126.4(2) 2_766 . ?
O6 Tb1 O3 81.7(2) . . ?
O5 Tb1 O2 81.9(2) . . ?
O4 Tb1 O2 84.0(2) 2_766 . ?
O6 Tb1 O2 128.1(2) . . ?
O3 Tb1 O2 144.5(2) . . ?
O5 Tb1 O1 128.0(2) . . ?
O4 Tb1 O1 76.4(2) 2_766 . ?
O6 Tb1 O1 76.6(2) . . ?
O3 Tb1 O1 143.2(2) . . ?
O2 Tb1 O1 52.10(19) . . ?
O5 Tb1 N2 138.6(2) . . ?
O4 Tb1 N2 143.8(2) 2_766 . ?
O6 Tb1 N2 80.0(2) . . ?
O3 Tb1 N2 75.2(2) . . ?
O2 Tb1 N2 90.1(2) . . ?
O1 Tb1 N2 71.9(2) . . ?
O5 Tb1 N1 75.4(2) . . ?
O4 Tb1 N1 144.9(2) 2_766 . ?
O6 Tb1 N1 139.2(2) . . ?
O3 Tb1 N1 72.2(2) . . ?
O2 Tb1 N1 72.2(2) . . ?
O1 Tb1 N1 106.5(2) . . ?
N2 Tb1 N1 63.5(2) . . ?
O5 Tb1 O4 70.7(2) . . ?
O4 Tb1 O4 76.4(2) 2_766 . ?
O6 Tb1 O4 69.6(2) . . ?
O3 Tb1 O4 50.09(19) . . ?
O2 Tb1 O4 149.4(2) . . ?
O1 Tb1 O4 140.67(19) . . ?
N2 Tb1 O4 119.4(2) . . ?
N1 Tb1 O4 112.16(19) . . ?
O5 Tb1 C24 104.8(3) . . ?
O4 Tb1 C24 78.0(2) 2_766 . ?
O6 Tb1 C24 102.3(3) . . ?
O3 Tb1 C24 155.0(2) . . ?
O2 Tb1 C24 26.0(2) . . ?
O1 Tb1 C24 26.2(2) . . ?
N2 Tb1 C24 81.2(2) . . ?
N1 Tb1 C24 90.1(2) . . ?
O4 Tb1 C24 154.4(2) . . ?
O5 Tb1 C20 78.0(2) . . ?
O4 Tb1 C20 102.2(2) 2_766 . ?
O6 Tb1 C20 75.1(2) . . ?
O3 Tb1 C20 24.3(2) . . ?
O2 Tb1 C20 156.7(2) . . ?
O1 Tb1 C20 151.1(2) . . ?
N2 Tb1 C20 97.2(2) . . ?
N1 Tb1 C20 91.3(2) . . ?
O4 Tb1 C20 25.78(19) . . ?
C24 Tb1 C20 177.2(3) . . ?
O5 Tb1 Tb1 68.42(14) . 2_766 ?
O4 Tb1 Tb1 41.46(15) 2_766 2_766 ?
O6 Tb1 Tb1 67.58(14) . 2_766 ?
O3 Tb1 Tb1 85.03(15) . 2_766 ?
O2 Tb1 Tb1 121.64(14) . 2_766 ?
O1 Tb1 Tb1 112.82(14) . 2_766 ?
N2 Tb1 Tb1 144.14(15) . 2_766 ?
N1 Tb1 Tb1 137.70(15) . 2_766 ?
O4 Tb1 Tb1 34.99(12) . 2_766 ?
C24 Tb1 Tb1 119.46(17) . 2_766 ?
C20 Tb1 Tb1 60.76(17) . 2_766 ?
C24 O1 Tb1 93.8(6) . . ?
C24 O2 Tb1 94.6(5) . . ?
C20 O3 Tb1 101.5(5) . . ?
C20 O4 Tb1 168.7(6) . 2_766 ?
C20 O4 Tb1 87.5(5) . . ?
Tb1 O4 Tb1 103.6(2) 2_766 . ?
C22 O5 Tb1 137.8(5) . . ?
C22 O6 Tb1 138.9(6) 2_766 . ?
C1 N1 C12 118.4(7) . . ?
C1 N1 Tb1 123.4(6) . . ?
C12 N1 Tb1 118.3(5) . . ?
C10 N2 C11 118.5(8) . . ?
C10 N2 Tb1 120.3(6) . . ?
C11 N2 Tb1 121.2(6) . . ?
C13 N3 C5 106.5(7) . . ?
C13 N3 H3N 126.8 . . ?
C5 N3 H3N 126.8 . . ?
C13 N4 C6 102.4(7) . . ?
N1 C1 C2 124.0(9) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C1 119.3(9) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.3(8) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 126.6(8) . . ?
C3 C4 C12 117.6(8) . . ?
C5 C4 C12 115.7(8) . . ?
C6 C5 N3 105.1(8) . . ?
C6 C5 C4 124.1(8) . . ?
N3 C5 C4 130.8(8) . . ?
C5 C6 N4 112.4(7) . . ?
C5 C6 C7 121.5(8) . . ?
N4 C6 C7 126.1(8) . . ?
C8 C7 C11 118.2(7) . . ?
C8 C7 C6 125.1(8) . . ?
C11 C7 C6 116.7(8) . . ?
C9 C8 C7 119.7(8) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.6(9) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
N2 C10 C9 123.4(9) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
N2 C11 C7 120.7(8) . . ?
N2 C11 C12 117.8(8) . . ?
C7 C11 C12 121.5(7) . . ?
N1 C12 C11 119.2(7) . . ?
N1 C12 C4 120.4(8) . . ?
C11 C12 C4 120.4(8) . . ?
N4 C13 N3 113.6(8) . . ?
N4 C13 C14 122.5(8) . . ?
N3 C13 C14 123.8(7) . . ?
C15 C14 C19 118.7(9) . . ?
C15 C14 C13 121.8(9) . . ?
C19 C14 C13 119.5(8) . . ?
C14 C15 C16 119.7(9) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.5(9) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.7(9) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 121.1(9) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C14 120.2(8) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
O2 C24 O1 119.3(9) . . ?
O2 C24 C25 120.6(9) . . ?
O1 C24 C25 120.0(9) . . ?
O2 C24 Tb1 59.4(5) . . ?
O1 C24 Tb1 60.0(5) . . ?
C25 C24 Tb1 175.5(6) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C20 O4 120.8(9) . . ?
O3 C20 C21 120.0(8) . . ?
O4 C20 C21 119.2(8) . . ?
O3 C20 Tb1 54.1(5) . . ?
O4 C20 Tb1 66.7(5) . . ?
C21 C20 Tb1 173.5(6) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 C22 O5 125.7(9) 2_766 . ?
O6 C22 C23 116.8(9) 2_766 . ?
O5 C22 C23 117.5(7) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 Tb1 O1 C24 30.9(6) . . . . ?
O4 Tb1 O1 C24 90.5(5) 2_766 . . . ?
O6 Tb1 O1 C24 169.0(5) . . . . ?
O3 Tb1 O1 C24 -135.4(5) . . . . ?
O2 Tb1 O1 C24 -2.5(5) . . . . ?
N2 Tb1 O1 C24 -107.3(5) . . . . ?
N1 Tb1 O1 C24 -53.2(5) . . . . ?
O4 Tb1 O1 C24 138.0(5) . . . . ?
C20 Tb1 O1 C24 -178.8(5) . . . . ?
Tb1 Tb1 O1 C24 110.7(5) 2_766 . . . ?
O5 Tb1 O2 C24 -151.5(5) . . . . ?
O4 Tb1 O2 C24 -74.9(5) 2_766 . . . ?
O6 Tb1 O2 C24 -8.1(6) . . . . ?
O3 Tb1 O2 C24 133.4(5) . . . . ?
O1 Tb1 O2 C24 2.5(5) . . . . ?
N2 Tb1 O2 C24 69.3(5) . . . . ?
N1 Tb1 O2 C24 131.3(5) . . . . ?
O4 Tb1 O2 C24 -125.1(5) . . . . ?
C20 Tb1 O2 C24 178.0(6) . . . . ?
Tb1 Tb1 O2 C24 -93.1(5) 2_766 . . . ?
O5 Tb1 O3 C20 64.6(6) . . . . ?
O4 Tb1 O3 C20 -6.4(7) 2_766 . . . ?
O6 Tb1 O3 C20 -72.0(6) . . . . ?
O2 Tb1 O3 C20 137.7(5) . . . . ?
O1 Tb1 O3 C20 -126.2(6) . . . . ?
N2 Tb1 O3 C20 -153.7(6) . . . . ?
N1 Tb1 O3 C20 139.9(6) . . . . ?
O4 Tb1 O3 C20 -1.7(5) . . . . ?
C24 Tb1 O3 C20 -173.4(7) . . . . ?
Tb1 Tb1 O3 C20 -3.9(5) 2_766 . . . ?
O5 Tb1 O4 C20 -102.6(5) . . . . ?
O4 Tb1 O4 C20 177.8(6) 2_766 . . . ?
O6 Tb1 O4 C20 98.0(5) . . . . ?
O3 Tb1 O4 C20 1.6(5) . . . . ?
O2 Tb1 O4 C20 -130.4(5) . . . . ?
O1 Tb1 O4 C20 130.4(5) . . . . ?
N2 Tb1 O4 C20 33.0(5) . . . . ?
N1 Tb1 O4 C20 -38.0(5) . . . . ?
C24 Tb1 O4 C20 173.5(6) . . . . ?
Tb1 Tb1 O4 C20 177.8(6) 2_766 . . . ?
O5 Tb1 O4 Tb1 79.7(2) . . . 2_766 ?
O4 Tb1 O4 Tb1 0.0 2_766 . . 2_766 ?
O6 Tb1 O4 Tb1 -79.8(2) . . . 2_766 ?
O3 Tb1 O4 Tb1 -176.1(4) . . . 2_766 ?
O2 Tb1 O4 Tb1 51.8(4) . . . 2_766 ?
O1 Tb1 O4 Tb1 -47.4(4) . . . 2_766 ?
N2 Tb1 O4 Tb1 -144.7(2) . . . 2_766 ?
N1 Tb1 O4 Tb1 144.2(2) . . . 2_766 ?
C24 Tb1 O4 Tb1 -4.3(7) . . . 2_766 ?
C20 Tb1 O4 Tb1 -177.8(6) . . . 2_766 ?
O4 Tb1 O5 C22 30.9(9) 2_766 . . . ?
O6 Tb1 O5 C22 -21.4(10) . . . . ?
O3 Tb1 O5 C22 -97.5(9) . . . . ?
O2 Tb1 O5 C22 116.7(9) . . . . ?
O1 Tb1 O5 C22 90.7(9) . . . . ?
N2 Tb1 O5 C22 -162.4(8) . . . . ?
N1 Tb1 O5 C22 -169.6(9) . . . . ?
O4 Tb1 O5 C22 -49.4(9) . . . . ?
C24 Tb1 O5 C22 104.2(9) . . . . ?
C20 Tb1 O5 C22 -75.1(9) . . . . ?
Tb1 Tb1 O5 C22 -12.0(8) 2_766 . . . ?
O5 Tb1 O6 C22 20.8(10) . . . 2_766 ?
O4 Tb1 O6 C22 -31.5(8) 2_766 . . 2_766 ?
O3 Tb1 O6 C22 99.4(9) . . . 2_766 ?
O2 Tb1 O6 C22 -102.0(9) . . . 2_766 ?
O1 Tb1 O6 C22 -110.6(9) . . . 2_766 ?
N2 Tb1 O6 C22 175.8(9) . . . 2_766 ?
N1 Tb1 O6 C22 149.7(8) . . . 2_766 ?
O4 Tb1 O6 C22 49.0(8) . . . 2_766 ?
C24 Tb1 O6 C22 -105.6(9) . . . 2_766 ?
C20 Tb1 O6 C22 75.5(9) . . . 2_766 ?
Tb1 Tb1 O6 C22 11.4(8) 2_766 . . 2_766 ?
O5 Tb1 N1 C1 -5.5(7) . . . . ?
O4 Tb1 N1 C1 30.9(9) 2_766 . . . ?
O6 Tb1 N1 C1 -151.1(6) . . . . ?
O3 Tb1 N1 C1 -98.1(7) . . . . ?
O2 Tb1 N1 C1 80.6(7) . . . . ?
O1 Tb1 N1 C1 120.5(7) . . . . ?
N2 Tb1 N1 C1 179.9(8) . . . . ?
O4 Tb1 N1 C1 -67.2(7) . . . . ?
C24 Tb1 N1 C1 99.8(7) . . . . ?
C20 Tb1 N1 C1 -82.7(7) . . . . ?
Tb1 Tb1 N1 C1 -37.3(8) 2_766 . . . ?
O5 Tb1 N1 C12 176.9(6) . . . . ?
O4 Tb1 N1 C12 -146.7(5) 2_766 . . . ?
O6 Tb1 N1 C12 31.3(7) . . . . ?
O3 Tb1 N1 C12 84.3(6) . . . . ?
O2 Tb1 N1 C12 -97.0(6) . . . . ?
O1 Tb1 N1 C12 -57.1(6) . . . . ?
N2 Tb1 N1 C12 2.3(6) . . . . ?
O4 Tb1 N1 C12 115.2(6) . . . . ?
C24 Tb1 N1 C12 -77.8(6) . . . . ?
C20 Tb1 N1 C12 99.7(6) . . . . ?
Tb1 Tb1 N1 C12 145.1(5) 2_766 . . . ?
O5 Tb1 N2 C10 172.5(6) . . . . ?
O4 Tb1 N2 C10 -29.6(8) 2_766 . . . ?
O6 Tb1 N2 C10 19.2(7) . . . . ?
O3 Tb1 N2 C10 103.1(7) . . . . ?
O2 Tb1 N2 C10 -109.6(7) . . . . ?
O1 Tb1 N2 C10 -59.9(7) . . . . ?
N1 Tb1 N2 C10 -179.6(7) . . . . ?
O4 Tb1 N2 C10 78.7(7) . . . . ?
C24 Tb1 N2 C10 -85.1(7) . . . . ?
C20 Tb1 N2 C10 92.5(7) . . . . ?
Tb1 Tb1 N2 C10 44.3(8) 2_766 . . . ?
O5 Tb1 N2 C11 -9.3(8) . . . . ?
O4 Tb1 N2 C11 148.6(6) 2_766 . . . ?
O6 Tb1 N2 C11 -162.7(6) . . . . ?
O3 Tb1 N2 C11 -78.7(6) . . . . ?
O2 Tb1 N2 C11 68.6(6) . . . . ?
O1 Tb1 N2 C11 118.3(6) . . . . ?
N1 Tb1 N2 C11 -1.4(6) . . . . ?
O4 Tb1 N2 C11 -103.1(6) . . . . ?
C24 Tb1 N2 C11 93.1(6) . . . . ?
C20 Tb1 N2 C11 -89.3(6) . . . . ?
Tb1 Tb1 N2 C11 -137.5(5) 2_766 . . . ?
C12 N1 C1 C2 -1.0(14) . . . . ?
Tb1 N1 C1 C2 -178.6(7) . . . . ?
N1 C1 C2 C3 1.8(15) . . . . ?
C1 C2 C3 C4 -1.3(14) . . . . ?
C2 C3 C4 C5 -178.0(9) . . . . ?
C2 C3 C4 C12 0.1(13) . . . . ?
C13 N3 C5 C6 0.1(9) . . . . ?
C13 N3 C5 C4 179.7(9) . . . . ?
C3 C4 C5 C6 177.3(9) . . . . ?
C12 C4 C5 C6 -0.9(13) . . . . ?
C3 C4 C5 N3 -2.3(16) . . . . ?
C12 C4 C5 N3 179.6(8) . . . . ?
N3 C5 C6 N4 -0.6(10) . . . . ?
C4 C5 C6 N4 179.7(8) . . . . ?
N3 C5 C6 C7 -178.8(8) . . . . ?
C4 C5 C6 C7 1.5(14) . . . . ?
C13 N4 C6 C5 0.8(10) . . . . ?
C13 N4 C6 C7 178.9(9) . . . . ?
C5 C6 C7 C8 176.5(9) . . . . ?
N4 C6 C7 C8 -1.4(15) . . . . ?
C5 C6 C7 C11 -0.8(13) . . . . ?
N4 C6 C7 C11 -178.7(8) . . . . ?
C11 C7 C8 C9 -2.0(14) . . . . ?
C6 C7 C8 C9 -179.2(9) . . . . ?
C7 C8 C9 C10 1.3(15) . . . . ?
C11 N2 C10 C9 0.5(14) . . . . ?
Tb1 N2 C10 C9 178.7(7) . . . . ?
C8 C9 C10 N2 -0.6(16) . . . . ?
C10 N2 C11 C7 -1.2(12) . . . . ?
Tb1 N2 C11 C7 -179.4(6) . . . . ?
C10 N2 C11 C12 178.8(8) . . . . ?
Tb1 N2 C11 C12 0.5(10) . . . . ?
C8 C7 C11 N2 1.9(13) . . . . ?
C6 C7 C11 N2 179.4(8) . . . . ?
C8 C7 C11 C12 -178.0(8) . . . . ?
C6 C7 C11 C12 -0.5(13) . . . . ?
C1 N1 C12 C11 179.2(8) . . . . ?
Tb1 N1 C12 C11 -3.1(10) . . . . ?
C1 N1 C12 C4 -0.2(12) . . . . ?
Tb1 N1 C12 C4 177.5(6) . . . . ?
N2 C11 C12 N1 1.7(12) . . . . ?
C7 C11 C12 N1 -178.3(8) . . . . ?
N2 C11 C12 C4 -178.8(7) . . . . ?
C7 C11 C12 C4 1.1(13) . . . . ?
C3 C4 C12 N1 0.7(12) . . . . ?
C5 C4 C12 N1 179.0(8) . . . . ?
C3 C4 C12 C11 -178.8(8) . . . . ?
C5 C4 C12 C11 -0.4(12) . . . . ?
C6 N4 C13 N3 -0.8(10) . . . . ?
C6 N4 C13 C14 177.5(8) . . . . ?
C5 N3 C13 N4 0.4(10) . . . . ?
C5 N3 C13 C14 -177.8(8) . . . . ?
N4 C13 C14 C15 176.9(9) . . . . ?
N3 C13 C14 C15 -5.1(14) . . . . ?
N4 C13 C14 C19 -2.1(14) . . . . ?
N3 C13 C14 C19 176.0(9) . . . . ?
C19 C14 C15 C16 -1.9(15) . . . . ?
C13 C14 C15 C16 179.1(9) . . . . ?
C14 C15 C16 C17 2.9(17) . . . . ?
C15 C16 C17 C18 -3.1(17) . . . . ?
C16 C17 C18 C19 2.5(15) . . . . ?
C17 C18 C19 C14 -1.6(15) . . . . ?
C15 C14 C19 C18 1.3(15) . . . . ?
C13 C14 C19 C18 -179.7(8) . . . . ?
Tb1 O2 C24 O1 -4.4(9) . . . . ?
Tb1 O2 C24 C25 174.7(7) . . . . ?
Tb1 O1 C24 O2 4.4(8) . . . . ?
Tb1 O1 C24 C25 -174.8(7) . . . . ?
O5 Tb1 C24 O2 29.2(5) . . . . ?
O4 Tb1 C24 O2 101.0(5) 2_766 . . . ?
O6 Tb1 C24 O2 173.5(5) . . . . ?
O3 Tb1 C24 O2 -89.6(8) . . . . ?
O1 Tb1 C24 O2 -175.5(9) . . . . ?
N2 Tb1 C24 O2 -108.8(5) . . . . ?
N1 Tb1 C24 O2 -45.7(5) . . . . ?
O4 Tb1 C24 O2 105.3(6) . . . . ?
C20 Tb1 C24 O2 -164(5) . . . . ?
Tb1 Tb1 C24 O2 102.5(5) 2_766 . . . ?
O5 Tb1 C24 O1 -155.2(5) . . . . ?
O4 Tb1 C24 O1 -83.4(5) 2_766 . . . ?
O6 Tb1 C24 O1 -10.9(5) . . . . ?
O3 Tb1 C24 O1 85.9(7) . . . . ?
O2 Tb1 C24 O1 175.5(9) . . . . ?
N2 Tb1 C24 O1 66.7(5) . . . . ?
N1 Tb1 C24 O1 129.8(5) . . . . ?
O4 Tb1 C24 O1 -79.1(8) . . . . ?
C20 Tb1 C24 O1 12(5) . . . . ?
Tb1 Tb1 C24 O1 -82.0(5) 2_766 . . . ?
O5 Tb1 C24 C25 -63(9) . . . . ?
O4 Tb1 C24 C25 9(9) 2_766 . . . ?
O6 Tb1 C24 C25 81(9) . . . . ?
O3 Tb1 C24 C25 178(9) . . . . ?
O2 Tb1 C24 C25 -92(9) . . . . ?
O1 Tb1 C24 C25 92(9) . . . . ?
N2 Tb1 C24 C25 159(9) . . . . ?
N1 Tb1 C24 C25 -138(9) . . . . ?
O4 Tb1 C24 C25 13(10) . . . . ?
C20 Tb1 C24 C25 104(10) . . . . ?
Tb1 Tb1 C24 C25 10(9) 2_766 . . . ?
Tb1 O3 C20 O4 3.2(9) . . . . ?
Tb1 O3 C20 C21 -176.7(7) . . . . ?
Tb1 O4 C20 O3 166(2) 2_766 . . . ?
Tb1 O4 C20 O3 -2.9(8) . . . . ?
Tb1 O4 C20 C21 -14(3) 2_766 . . . ?
Tb1 O4 C20 C21 177.0(8) . . . . ?
Tb1 O4 C20 Tb1 169(3) 2_766 . . . ?
O5 Tb1 C20 O3 -112.7(6) . . . . ?
O4 Tb1 C20 O3 174.8(6) 2_766 . . . ?
O6 Tb1 C20 O3 103.2(6) . . . . ?
O2 Tb1 C20 O3 -81.8(8) . . . . ?
O1 Tb1 C20 O3 90.9(7) . . . . ?
N2 Tb1 C20 O3 25.6(6) . . . . ?
N1 Tb1 C20 O3 -37.8(6) . . . . ?
O4 Tb1 C20 O3 177.0(9) . . . . ?
C24 Tb1 C20 O3 80(5) . . . . ?
Tb1 Tb1 C20 O3 175.5(6) 2_766 . . . ?
O5 Tb1 C20 O4 70.4(5) . . . . ?
O4 Tb1 C20 O4 -2.2(6) 2_766 . . . ?
O6 Tb1 C20 O4 -73.8(5) . . . . ?
O3 Tb1 C20 O4 -177.0(9) . . . . ?
O2 Tb1 C20 O4 101.2(7) . . . . ?
O1 Tb1 C20 O4 -86.1(7) . . . . ?
N2 Tb1 C20 O4 -151.4(5) . . . . ?
N1 Tb1 C20 O4 145.2(5) . . . . ?
C24 Tb1 C20 O4 -97(5) . . . . ?
Tb1 Tb1 C20 O4 -1.5(4) 2_766 . . . ?
O5 Tb1 C20 C21 -86(6) . . . . ?
O4 Tb1 C20 C21 -159(6) 2_766 . . . ?
O6 Tb1 C20 C21 130(6) . . . . ?
O3 Tb1 C20 C21 26(6) . . . . ?
O2 Tb1 C20 C21 -55(6) . . . . ?
O1 Tb1 C20 C21 117(6) . . . . ?
N2 Tb1 C20 C21 52(6) . . . . ?
N1 Tb1 C20 C21 -11(6) . . . . ?
O4 Tb1 C20 C21 -157(6) . . . . ?
C24 Tb1 C20 C21 107(7) . . . . ?
Tb1 Tb1 C20 C21 -158(6) 2_766 . . . ?
Tb1 O5 C22 O6 9.6(15) . . . 2_766 ?
Tb1 O5 C22 C23 -172.5(6) . . . . ?

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
N3 H3N O2 0.86 2.01 2.808(9) 154.4 2_765

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.146
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1569811'
_audit_update_record             
;
2017-08-19 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H42 Dy2 N8 O12'
_chemical_formula_sum            'C50 H42 Dy2 N8 O12'
_chemical_formula_weight         1271.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.8152(19)
_cell_length_b                   10.379(2)
_cell_length_c                   13.594(3)
_cell_angle_alpha                73.302(3)
_cell_angle_beta                 69.411(3)
_cell_angle_gamma                70.576(3)
_cell_volume                     1199.6(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1916
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.57

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             626
_exptl_absorpt_coefficient_mu    3.163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5703
_exptl_absorpt_correction_T_max  0.6315
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6339
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4417
_reflns_number_gt                3560
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0473P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4417
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.007
_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
C1 C 0.1502(8) 0.3451(7) 0.4058(5) 0.0561(18) Uani 1 1 d . . .
H1 H 0.1166 0.3736 0.4711 0.067 Uiso 1 1 calc R . .
C2 C 0.0637(8) 0.2810(7) 0.3848(5) 0.0572(18) Uani 1 1 d . . .
H2 H -0.0259 0.2676 0.4352 0.069 Uiso 1 1 calc R . .
C3 C 0.1094(7) 0.2373(7) 0.2901(5) 0.0521(17) Uani 1 1 d . . .
H3 H 0.0519 0.1936 0.2755 0.063 Uiso 1 1 calc R . .
C4 C 0.2442(7) 0.2592(6) 0.2151(4) 0.0422(14) Uani 1 1 d . . .
C5 C 0.3015(7) 0.2209(6) 0.1128(5) 0.0445(15) Uani 1 1 d . . .
C6 C 0.4322(7) 0.2506(6) 0.0422(4) 0.0427(14) Uani 1 1 d . . .
C7 C 0.5217(7) 0.3160(6) 0.0650(4) 0.0408(14) Uani 1 1 d . . .
C8 C 0.6570(7) 0.3433(6) -0.0041(5) 0.0494(16) Uani 1 1 d . . .
H8 H 0.6947 0.3209 -0.0718 0.059 Uiso 1 1 calc R . .
C9 C 0.7330(8) 0.4034(7) 0.0290(5) 0.0525(16) Uani 1 1 d . . .
H9 H 0.8245 0.4206 -0.0154 0.063 Uiso 1 1 calc R . .
C10 C 0.6728(8) 0.4389(6) 0.1297(4) 0.0493(16) Uani 1 1 d . . .
H10 H 0.7261 0.4800 0.1509 0.059 Uiso 1 1 calc R . .
C11 C 0.4687(7) 0.3529(6) 0.1674(4) 0.0420(14) Uani 1 1 d . . .
C12 C 0.3288(7) 0.3252(6) 0.2423(4) 0.0422(14) Uani 1 1 d . . .
C13 C 0.3360(7) 0.1464(6) -0.0273(4) 0.0447(15) Uani 1 1 d . . .
C14 C 0.3176(7) 0.0807(6) -0.1030(5) 0.0452(15) Uani 1 1 d . . .
C15 C 0.2001(8) 0.0191(7) -0.0707(5) 0.0532(17) Uani 1 1 d . . .
H15 H 0.1345 0.0199 -0.0020 0.064 Uiso 1 1 calc R . .
C16 C 0.1783(8) -0.0438(7) -0.1386(5) 0.0591(18) Uani 1 1 d . . .
H16 H 0.0977 -0.0836 -0.1162 0.071 Uiso 1 1 calc R . .
C17 C 0.2764(9) -0.0473(8) -0.2400(6) 0.064(2) Uani 1 1 d . . .
H17 H 0.2623 -0.0894 -0.2862 0.077 Uiso 1 1 calc R . .
C18 C 0.3949(9) 0.0116(9) -0.2722(6) 0.073(2) Uani 1 1 d . . .
H18 H 0.4618 0.0079 -0.3402 0.088 Uiso 1 1 calc R . .
C19 C 0.4166(8) 0.0763(7) -0.2052(5) 0.0588(19) Uani 1 1 d . . .
H19 H 0.4969 0.1166 -0.2284 0.071 Uiso 1 1 calc R . .
C20 C 0.2233(8) 0.7285(7) 0.3019(5) 0.0460(15) Uani 1 1 d . . .
C21 C 0.1208(8) 0.8598(7) 0.2596(6) 0.0642(19) Uani 1 1 d . . .
H21A H 0.0516 0.9037 0.3179 0.096 Uiso 1 1 calc R . .
H21B H 0.0656 0.8380 0.2233 0.096 Uiso 1 1 calc R . .
H21C H 0.1795 0.9217 0.2104 0.096 Uiso 1 1 calc R . .
C22 C 0.2571(7) 0.4218(7) 0.6496(5) 0.0475(15) Uani 1 1 d . . .
C23 C 0.1204(8) 0.3811(8) 0.7306(5) 0.0598(18) Uani 1 1 d . . .
H23A H 0.0376 0.4155 0.6998 0.090 Uiso 1 1 calc R . .
H23B H 0.0945 0.4204 0.7927 0.090 Uiso 1 1 calc R . .
H23C H 0.1417 0.2815 0.7508 0.090 Uiso 1 1 calc R . .
C24 C 0.6215(7) 0.2412(6) 0.4817(5) 0.0463(15) Uani 1 1 d . . .
C25 C 0.7262(8) 0.1072(7) 0.5182(5) 0.0603(18) Uani 1 1 d . . .
H25A H 0.7152 0.0326 0.4957 0.090 Uiso 1 1 calc R . .
H25B H 0.7024 0.0886 0.5949 0.090 Uiso 1 1 calc R . .
H25C H 0.8282 0.1147 0.4875 0.090 Uiso 1 1 calc R . .
N1 N 0.2801(6) 0.3684(5) 0.3372(4) 0.0436(12) Uani 1 1 d . . .
N2 N 0.5426(6) 0.4170(5) 0.1973(4) 0.0446(12) Uani 1 1 d . . .
N3 N 0.2416(6) 0.1561(5) 0.0696(4) 0.0502(13) Uani 1 1 d . . .
N4 N 0.4520(6) 0.2022(5) -0.0483(4) 0.0453(12) Uani 1 1 d . . .
H4N H 0.5242 0.2068 -0.1067 0.054 Uiso 1 1 calc R . .
O1 O 0.5949(5) 0.3472(4) 0.5203(3) 0.0530(11) Uani 1 1 d . . .
O2 O 0.5596(5) 0.2488(4) 0.4120(3) 0.0585(12) Uani 1 1 d . . .
O3 O 0.1740(5) 0.6487(5) 0.3862(3) 0.0529(11) Uani 1 1 d . . .
O4 O 0.3619(5) 0.6987(4) 0.2493(3) 0.0505(11) Uani 1 1 d . . .
O5 O 0.2764(5) 0.4182(5) 0.5534(3) 0.0528(11) Uani 1 1 d . . .
O6 O 0.6588(5) 0.5435(5) 0.3170(3) 0.0521(11) Uani 1 1 d . . .
Dy1 Dy 0.42713(3) 0.49051(3) 0.38482(2) 0.04237(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.338(8) . ?
C1 C2 1.379(9) . ?
C2 C3 1.363(8) . ?
C3 C4 1.399(8) . ?
C4 C5 1.425(8) . ?
C4 C12 1.427(8) . ?
C5 N3 1.369(7) . ?
C5 C6 1.374(8) . ?
C6 N4 1.389(7) . ?
C6 C7 1.427(8) . ?
C7 C8 1.395(8) . ?
C7 C11 1.421(7) . ?
C8 C9 1.362(8) . ?
C9 C10 1.391(8) . ?
C10 N2 1.332(7) . ?
C11 N2 1.348(7) . ?
C11 C12 1.455(8) . ?
C12 N1 1.360(7) . ?
C13 N3 1.327(7) . ?
C13 N4 1.351(7) . ?
C13 C14 1.474(8) . ?
C14 C15 1.380(8) . ?
C14 C19 1.391(8) . ?
C15 C16 1.380(8) . ?
C16 C17 1.378(9) . ?
C17 C18 1.371(10) . ?
C18 C19 1.381(9) . ?
C20 O3 1.251(7) . ?
C20 O4 1.273(7) . ?
C20 C21 1.498(9) . ?
C20 Dy1 2.841(7) . ?
C22 O6 1.253(7) 2_666 ?
C22 O5 1.264(7) . ?
C22 C23 1.504(8) . ?
C24 O1 1.264(7) . ?
C24 O2 1.267(7) . ?
C24 C25 1.499(9) . ?
C24 Dy1 2.932(7) . ?
N1 Dy1 2.541(5) . ?
N2 Dy1 2.623(4) . ?
O1 Dy1 2.315(4) 2_666 ?
O1 Dy1 2.691(5) . ?
O2 Dy1 2.399(4) . ?
O3 Dy1 2.478(4) . ?
O4 Dy1 2.469(4) . ?
O5 Dy1 2.317(4) . ?
O6 C22 1.253(7) 2_666 ?
O6 Dy1 2.322(4) . ?
Dy1 O1 2.315(4) 2_666 ?
Dy1 Dy1 3.9476(8) 2_666 ?

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
N1 C1 C2 123.5(6) . . ?
C3 C2 C1 120.0(6) . . ?
C2 C3 C4 119.0(6) . . ?
C3 C4 C5 124.0(5) . . ?
C3 C4 C12 118.1(5) . . ?
C5 C4 C12 117.9(5) . . ?
N3 C5 C6 111.2(5) . . ?
N3 C5 C4 128.4(6) . . ?
C6 C5 C4 120.4(5) . . ?
C5 C6 N4 104.8(5) . . ?
C5 C6 C7 124.2(5) . . ?
N4 C6 C7 131.0(5) . . ?
C8 C7 C11 118.2(5) . . ?
C8 C7 C6 125.2(5) . . ?
C11 C7 C6 116.6(5) . . ?
C9 C8 C7 119.1(6) . . ?
C8 C9 C10 119.4(6) . . ?
N2 C10 C9 123.3(6) . . ?
N2 C11 C7 121.9(5) . . ?
N2 C11 C12 118.1(5) . . ?
C7 C11 C12 120.0(5) . . ?
N1 C12 C4 121.6(5) . . ?
N1 C12 C11 117.5(5) . . ?
C4 C12 C11 120.9(5) . . ?
N3 C13 N4 112.4(5) . . ?
N3 C13 C14 123.8(5) . . ?
N4 C13 C14 123.8(5) . . ?
C15 C14 C19 118.9(5) . . ?
C15 C14 C13 119.0(5) . . ?
C19 C14 C13 122.1(6) . . ?
C16 C15 C14 121.1(6) . . ?
C17 C16 C15 119.7(6) . . ?
C18 C17 C16 119.6(6) . . ?
C17 C18 C19 121.1(6) . . ?
C18 C19 C14 119.6(6) . . ?
O3 C20 O4 120.5(6) . . ?
O3 C20 C21 121.0(6) . . ?
O4 C20 C21 118.5(6) . . ?
O3 C20 Dy1 60.5(3) . . ?
O4 C20 Dy1 60.2(3) . . ?
C21 C20 Dy1 176.3(4) . . ?
O6 C22 O5 125.9(6) 2_666 . ?
O6 C22 C23 117.6(5) 2_666 . ?
O5 C22 C23 116.5(6) . . ?
O1 C24 O2 119.7(6) . . ?
O1 C24 C25 120.1(6) . . ?
O2 C24 C25 120.2(5) . . ?
O1 C24 Dy1 66.5(3) . . ?
O2 C24 Dy1 53.3(3) . . ?
C25 C24 Dy1 172.7(4) . . ?
C1 N1 C12 117.8(5) . . ?
C1 N1 Dy1 120.4(4) . . ?
C12 N1 Dy1 121.9(4) . . ?
C10 N2 C11 118.0(5) . . ?
C10 N2 Dy1 123.0(4) . . ?
C11 N2 Dy1 119.1(4) . . ?
C13 N3 C5 104.7(5) . . ?
C13 N4 C6 107.0(5) . . ?
C24 O1 Dy1 168.2(4) . 2_666 ?
C24 O1 Dy1 87.9(4) . . ?
Dy1 O1 Dy1 103.83(16) 2_666 . ?
C24 O2 Dy1 101.7(4) . . ?
C20 O3 Dy1 93.4(4) . . ?
C20 O4 Dy1 93.3(4) . . ?
C22 O5 Dy1 138.3(4) . . ?
C22 O6 Dy1 137.7(4) 2_666 . ?
O1 Dy1 O5 76.82(14) 2_666 . ?
O1 Dy1 O6 75.56(15) 2_666 . ?
O5 Dy1 O6 135.77(14) . . ?
O1 Dy1 O2 126.60(15) 2_666 . ?
O5 Dy1 O2 81.33(16) . . ?
O6 Dy1 O2 88.21(16) . . ?
O1 Dy1 O4 83.52(14) 2_666 . ?
O5 Dy1 O4 128.19(15) . . ?
O6 Dy1 O4 81.79(15) . . ?
O2 Dy1 O4 144.67(14) . . ?
O1 Dy1 O3 76.85(15) 2_666 . ?
O5 Dy1 O3 76.25(15) . . ?
O6 Dy1 O3 128.59(15) . . ?
O2 Dy1 O3 142.43(16) . . ?
O4 Dy1 O3 52.58(14) . . ?
O1 Dy1 N1 144.11(16) 2_666 . ?
O5 Dy1 N1 79.57(14) . . ?
O6 Dy1 N1 138.57(14) . . ?
O2 Dy1 N1 75.08(16) . . ?
O4 Dy1 N1 90.35(15) . . ?
O3 Dy1 N1 71.51(15) . . ?
O1 Dy1 N2 144.42(15) 2_666 . ?
O5 Dy1 N2 138.75(14) . . ?
O6 Dy1 N2 75.43(14) . . ?
O2 Dy1 N2 72.33(14) . . ?
O4 Dy1 N2 72.36(14) . . ?
O3 Dy1 N2 106.43(15) . . ?
N1 Dy1 N2 63.48(15) . . ?
O1 Dy1 O1 76.17(16) 2_666 . ?
O5 Dy1 O1 69.22(14) . . ?
O6 Dy1 O1 71.05(13) . . ?
O2 Dy1 O1 50.52(13) . . ?
O4 Dy1 O1 149.28(14) . . ?
O3 Dy1 O1 139.99(13) . . ?
N1 Dy1 O1 119.49(14) . . ?
N2 Dy1 O1 112.74(14) . . ?
O1 Dy1 C20 77.81(16) 2_666 . ?
O5 Dy1 C20 101.82(17) . . ?
O6 Dy1 C20 105.25(17) . . ?
O2 Dy1 C20 154.98(16) . . ?
O4 Dy1 C20 26.57(15) . . ?
O3 Dy1 C20 26.07(15) . . ?
N1 Dy1 C20 81.06(16) . . ?
N2 Dy1 C20 90.44(16) . . ?
O1 Dy1 C20 153.80(15) . . ?
O1 Dy1 C24 101.68(17) 2_666 . ?
O5 Dy1 C24 74.65(16) . . ?
O6 Dy1 C24 77.95(16) . . ?
O2 Dy1 C24 25.02(15) . . ?
O4 Dy1 C24 157.00(16) . . ?
O3 Dy1 C24 150.36(15) . . ?
N1 Dy1 C24 97.62(17) . . ?
N2 Dy1 C24 91.93(16) . . ?
O1 Dy1 C24 25.52(14) . . ?
C20 Dy1 C24 176.42(17) . . ?
O1 Dy1 Dy1 41.45(11) 2_666 2_666 ?
O5 Dy1 Dy1 67.93(10) . 2_666 ?
O6 Dy1 Dy1 68.43(9) . 2_666 ?
O2 Dy1 Dy1 85.19(10) . 2_666 ?
O4 Dy1 Dy1 121.33(10) . 2_666 ?
O3 Dy1 Dy1 112.88(10) . 2_666 ?
N1 Dy1 Dy1 144.17(10) . 2_666 ?
N2 Dy1 Dy1 137.78(12) . 2_666 ?
O1 Dy1 Dy1 34.71(8) . 2_666 ?
C20 Dy1 Dy1 119.20(11) . 2_666 ?
C24 Dy1 Dy1 60.23(11) . 2_666 ?

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
N4 H4N O4 0.86 2.02 2.825(6) 155.5 2_665

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.270
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.117
####################################################################### 
# 
# 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_h
_database_code_depnum_ccdc_archive 'CCDC 1569808'
_audit_update_record             
;
2017-08-19 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H42 N8 O12 Sm2'
_chemical_formula_sum            'C50 H42 N8 O12 Sm2'
_chemical_formula_weight         1247.64

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                   9.8132(17)
_cell_length_b                   10.4297(19)
_cell_length_c                   13.608(2)
_cell_angle_alpha                92.386(3)
_cell_angle_beta                 110.825(2)
_cell_angle_gamma                110.486(3)
_cell_volume                     1197.3(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4359
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.8

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             618
_exptl_absorpt_coefficient_mu    2.501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.123
_exptl_absorpt_correction_T_max  0.184
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6273
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4459
_reflns_number_gt                4064
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0524P)²+1.0913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4394
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.1992(5) 0.4367(5) 0.3729(3) 0.0462(10) Uani 1 1 d . . .
H1 H 0.1261 0.4781 0.3518 0.055 Uiso 1 1 calc R . .
C2 C 0.2383(6) 0.4027(5) 0.4739(3) 0.0482(10) Uani 1 1 d . . .
H2 H 0.1918 0.4203 0.5188 0.058 Uiso 1 1 calc R . .
C3 C 0.3467(5) 0.3429(5) 0.5061(3) 0.0446(10) Uani 1 1 d . . .
H3 H 0.3762 0.3209 0.5740 0.054 Uiso 1 1 calc R . .
C4 C 0.4127(5) 0.3150(4) 0.4367(3) 0.0386(9) Uani 1 1 d . . .
C5 C 0.5243(5) 0.2516(4) 0.4594(3) 0.0393(9) Uani 1 1 d . . .
C6 C 0.5838(5) 0.2230(4) 0.3880(3) 0.0406(9) Uani 1 1 d . . .
C7 C 0.5399(5) 0.2613(4) 0.2851(3) 0.0411(9) Uani 1 1 d . . .
C8 C 0.6008(6) 0.2404(5) 0.2102(3) 0.0497(11) Uani 1 1 d . . .
H8 H 0.6739 0.1988 0.2253 0.060 Uiso 1 1 calc R . .
C9 C 0.5515(6) 0.2820(5) 0.1144(4) 0.0546(12) Uani 1 1 d . . .
H9 H 0.5904 0.2690 0.0633 0.065 Uiso 1 1 calc R . .
C10 C 0.4427(6) 0.3440(5) 0.0943(3) 0.0493(11) Uani 1 1 d . . .
H10 H 0.4093 0.3707 0.0284 0.059 Uiso 1 1 calc R . .
C11 C 0.4312(5) 0.3260(4) 0.2591(3) 0.0384(9) Uani 1 1 d . . .
C12 C 0.3653(5) 0.3524(4) 0.3349(3) 0.0357(8) Uani 1 1 d . . .
C13 C 0.6885(5) 0.1491(4) 0.5275(3) 0.0413(9) Uani 1 1 d . . .
C14 C 0.7808(5) 0.0844(4) 0.6025(3) 0.0421(9) Uani 1 1 d . . .
C15 C 0.7854(6) 0.0796(6) 0.7050(4) 0.0589(13) Uani 1 1 d . . .
H15 H 0.7288 0.1193 0.7290 0.071 Uiso 1 1 calc R . .
C16 C 0.8729(7) 0.0165(7) 0.7714(4) 0.0680(15) Uani 1 1 d . . .
H16 H 0.8748 0.0135 0.8400 0.082 Uiso 1 1 calc R . .
C17 C 0.9578(6) -0.0424(6) 0.7376(4) 0.0576(12) Uani 1 1 d . . .
H17 H 1.0180 -0.0840 0.7834 0.069 Uiso 1 1 calc R . .
C18 C 0.9529(6) -0.0391(5) 0.6369(4) 0.0545(11) Uani 1 1 d . . .
H18 H 1.0090 -0.0798 0.6132 0.065 Uiso 1 1 calc R . .
C19 C 0.8655(6) 0.0238(5) 0.5695(4) 0.0512(11) Uani 1 1 d . . .
H19 H 0.8636 0.0256 0.5008 0.061 Uiso 1 1 calc R . .
C20 C -0.1051(6) 0.2378(4) 0.0199(3) 0.0447(10) Uani 1 1 d . . .
C21 C -0.2502(6) 0.1053(5) -0.0171(4) 0.0611(13) Uani 1 1 d . . .
H21A H -0.2206 0.0272 -0.0204 0.092 Uiso 1 1 calc R . .
H21B H -0.3219 0.1052 -0.0869 0.092 Uiso 1 1 calc R . .
H21C H -0.3010 0.0987 0.0322 0.092 Uiso 1 1 calc R . .
C22 C 0.0957(5) 0.4220(5) -0.1537(3) 0.0433(9) Uani 1 1 d . . .
C23 C 0.1493(6) 0.3819(6) -0.2359(4) 0.0581(12) Uani 1 1 d . . .
H23A H 0.2619 0.4082 -0.2044 0.087 Uiso 1 1 calc R . .
H23B H 0.1226 0.4289 -0.2947 0.087 Uiso 1 1 calc R . .
H23C H 0.0978 0.2830 -0.2614 0.087 Uiso 1 1 calc R . .
C24 C 0.4799(5) 0.7320(5) 0.1981(3) 0.0421(9) Uani 1 1 d . . .
C25 C 0.6247(6) 0.8631(6) 0.2383(5) 0.0650(14) Uani 1 1 d . . .
H25A H 0.7096 0.8477 0.2918 0.098 Uiso 1 1 calc R . .
H25B H 0.6039 0.9350 0.2692 0.098 Uiso 1 1 calc R . .
H25C H 0.6541 0.8914 0.1801 0.098 Uiso 1 1 calc R . .
N1 N 0.2605(4) 0.4134(4) 0.3048(3) 0.0413(8) Uani 1 1 d . . .
N2 N 0.3834(4) 0.3672(4) 0.1638(3) 0.0422(8) Uani 1 1 d . . .
N3 N 0.5928(4) 0.2037(4) 0.5491(2) 0.0406(8) Uani 1 1 d . . .
H3N H 0.5779 0.2076 0.6075 0.049 Uiso 1 1 calc R . .
N4 N 0.6860(5) 0.1592(4) 0.4305(3) 0.0468(8) Uani 1 1 d . . .
O1 O 0.4441(4) 0.6536(3) 0.1136(2) 0.0507(7) Uani 1 1 d . . .
O2 O 0.3945(4) 0.7014(3) 0.2514(2) 0.0482(7) Uani 1 1 d . . .
O5 O 0.1721(4) 0.4200(3) -0.0580(2) 0.0488(7) Uani 1 1 d . . .
O6 O 0.0215(4) 0.5438(4) 0.1855(2) 0.0507(8) Uani 1 1 d . . .
O7 O 0.0219(4) 0.2423(3) 0.0876(3) 0.0598(9) Uani 1 1 d . . .
O8 O -0.1151(4) 0.3446(3) -0.0170(2) 0.0483(7) Uani 1 1 d . . .
Sm1 Sm 0.18713(2) 0.49004(2) 0.114553(14) 0.03764(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.326(5) . ?
C1 C2 1.386(6) . ?
C2 C3 1.367(6) . ?
C3 C4 1.393(6) . ?
C4 C12 1.414(5) . ?
C4 C5 1.419(6) . ?
C5 C6 1.369(6) . ?
C5 N3 1.375(5) . ?
C6 N4 1.368(5) . ?
C6 C7 1.430(5) . ?
C7 C8 1.395(6) . ?
C7 C11 1.405(6) . ?
C8 C9 1.367(6) . ?
C9 C10 1.386(7) . ?
C10 N2 1.327(6) . ?
C11 N2 1.357(5) . ?
C11 C12 1.460(6) . ?
C12 N1 1.347(5) . ?
C13 N4 1.320(5) . ?
C13 N3 1.360(5) . ?
C13 C14 1.464(6) . ?
C14 C19 1.379(6) . ?
C14 C15 1.384(6) . ?
C15 C16 1.371(7) . ?
C16 C17 1.375(7) . ?
C17 C18 1.357(7) . ?
C18 C19 1.376(6) . ?
C20 O7 1.242(6) . ?
C20 O8 1.261(5) . ?
C20 C21 1.499(7) . ?
C22 O5 1.255(5) . ?
C22 O6 1.259(5) 2_565 ?
C22 C23 1.495(6) . ?
C24 O1 1.244(5) . ?
C24 O2 1.263(5) . ?
C24 C25 1.488(7) . ?
N1 Sm1 2.667(3) . ?
N2 Sm1 2.585(3) . ?
O1 Sm1 2.507(3) . ?
O2 Sm1 2.508(3) . ?
O5 Sm1 2.367(3) . ?
O6 C22 1.259(5) 2_565 ?
O6 Sm1 2.366(3) . ?
O7 Sm1 2.450(3) . ?
O8 Sm1 2.369(3) 2_565 ?
O8 Sm1 2.674(3) . ?
Sm1 O8 2.369(3) 2_565 ?
Sm1 Sm1 3.9621(6) 2_565 ?

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
N1 C1 C2 123.5(4) . . ?
C3 C2 C1 118.7(4) . . ?
C2 C3 C4 119.7(4) . . ?
C3 C4 C12 117.8(4) . . ?
C3 C4 C5 125.4(4) . . ?
C12 C4 C5 116.8(4) . . ?
C6 C5 N3 105.3(4) . . ?
C6 C5 C4 123.7(4) . . ?
N3 C5 C4 131.0(4) . . ?
N4 C6 C5 110.9(4) . . ?
N4 C6 C7 128.2(4) . . ?
C5 C6 C7 120.9(4) . . ?
C8 C7 C11 118.5(4) . . ?
C8 C7 C6 123.9(4) . . ?
C11 C7 C6 117.7(4) . . ?
C9 C8 C7 119.0(4) . . ?
C8 C9 C10 119.2(4) . . ?
N2 C10 C9 123.7(4) . . ?
N2 C11 C7 122.0(4) . . ?
N2 C11 C12 117.2(3) . . ?
C7 C11 C12 120.8(3) . . ?
N1 C12 C4 121.9(4) . . ?
N1 C12 C11 117.9(3) . . ?
C4 C12 C11 120.1(3) . . ?
N4 C13 N3 112.0(3) . . ?
N4 C13 C14 124.2(4) . . ?
N3 C13 C14 123.8(4) . . ?
C19 C14 C15 118.2(4) . . ?
C19 C14 C13 118.9(4) . . ?
C15 C14 C13 122.9(4) . . ?
C16 C15 C14 120.3(5) . . ?
C15 C16 C17 120.8(5) . . ?
C18 C17 C16 119.3(4) . . ?
C17 C18 C19 120.5(5) . . ?
C18 C19 C14 120.9(4) . . ?
O7 C20 O8 120.9(4) . . ?
O7 C20 C21 120.1(4) . . ?
O8 C20 C21 119.0(4) . . ?
O5 C22 O6 125.0(4) . 2_565 ?
O5 C22 C23 117.4(4) . . ?
O6 C22 C23 117.6(4) 2_565 . ?
O1 C24 O2 120.6(4) . . ?
O1 C24 C25 120.5(4) . . ?
O2 C24 C25 118.9(4) . . ?
C1 N1 C12 118.3(3) . . ?
C1 N1 Sm1 121.8(3) . . ?
C12 N1 Sm1 119.9(3) . . ?
C10 N2 C11 117.7(4) . . ?
C10 N2 Sm1 119.5(3) . . ?
C11 N2 Sm1 122.9(3) . . ?
C13 N3 C5 106.8(3) . . ?
C13 N4 C6 104.9(4) . . ?
C24 O1 Sm1 94.1(3) . . ?
C24 O2 Sm1 93.6(2) . . ?
C22 O5 Sm1 138.7(3) . . ?
C22 O6 Sm1 138.2(3) 2_565 . ?
C20 O7 Sm1 100.1(3) . . ?
C20 O8 Sm1 167.5(3) . 2_565 ?
C20 O8 Sm1 88.9(3) . . ?
Sm1 O8 Sm1 103.38(11) 2_565 . ?
O6 Sm1 O5 136.24(10) . . ?
O6 Sm1 O8 75.63(11) . 2_565 ?
O5 Sm1 O8 76.19(10) . 2_565 ?
O6 Sm1 O7 88.62(12) . . ?
O5 Sm1 O7 82.06(12) . . ?
O8 Sm1 O7 126.56(10) 2_565 . ?
O6 Sm1 O1 127.63(11) . . ?
O5 Sm1 O1 76.19(10) . . ?
O8 Sm1 O1 76.76(11) 2_565 . ?
O7 Sm1 O1 142.88(12) . . ?
O6 Sm1 O2 81.99(11) . . ?
O5 Sm1 O2 127.07(11) . . ?
O8 Sm1 O2 83.94(10) 2_565 . ?
O7 Sm1 O2 144.67(10) . . ?
O1 Sm1 O2 51.47(10) . . ?
O6 Sm1 N2 138.03(10) . . ?
O5 Sm1 N2 80.19(10) . . ?
O8 Sm1 N2 144.44(11) 2_565 . ?
O7 Sm1 N2 74.93(11) . . ?
O1 Sm1 N2 72.01(11) . . ?
O2 Sm1 N2 89.61(11) . . ?
O6 Sm1 N1 76.17(10) . . ?
O5 Sm1 N1 138.44(10) . . ?
O8 Sm1 N1 145.32(10) 2_565 . ?
O7 Sm1 N1 72.19(10) . . ?
O1 Sm1 N1 105.71(10) . . ?
O2 Sm1 N1 72.50(10) . . ?
N2 Sm1 N1 62.14(10) . . ?
O6 Sm1 O8 71.12(10) . . ?
O5 Sm1 O8 70.23(10) . . ?
O8 Sm1 O8 76.62(11) 2_565 . ?
O7 Sm1 O8 50.05(9) . . ?
O1 Sm1 O8 141.08(9) . . ?
O2 Sm1 O8 149.90(10) . . ?
N2 Sm1 O8 119.42(10) . . ?
N1 Sm1 O8 112.36(10) . . ?
O6 Sm1 Sm1 68.48(7) . 2_565 ?
O5 Sm1 Sm1 68.22(7) . 2_565 ?
O8 Sm1 Sm1 41.05(8) 2_565 2_565 ?
O7 Sm1 Sm1 85.57(7) . 2_565 ?
O1 Sm1 Sm1 112.85(7) . 2_565 ?
O2 Sm1 Sm1 121.39(7) . 2_565 ?
N2 Sm1 Sm1 144.88(8) . 2_565 ?
N1 Sm1 Sm1 138.46(8) . 2_565 ?
O8 Sm1 Sm1 35.57(6) . 2_565 ?

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
N3 H3N O2 0.86 1.99 2.796(4) 155.7 2_666

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         1.746
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.104
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1569807'
_audit_update_record             
;
2017-08-19 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 N4 O6 Sm'
_chemical_formula_weight         607.77

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                   9.892(4)
_cell_length_b                   9.957(4)
_cell_length_c                   12.798(5)
_cell_angle_alpha                73.081(7)
_cell_angle_beta                 86.820(7)
_cell_angle_gamma                73.951(7)
_cell_volume                     1158.5(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1944
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      23.12

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             598
_exptl_absorpt_coefficient_mu    2.583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5951
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4190
_reflns_number_gt                3382
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0390P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4150
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.004
_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 0.57045(3) 0.38429(3) 0.89738(2) 0.03648(13) Uani 1 1 d . . .
O1 O -0.1978(5) 0.3117(6) 0.0020(4) 0.0835(17) Uani 1 1 d . . .
O2 O -0.3684(4) 0.4486(5) 0.0700(3) 0.0466(10) Uani 1 1 d . . .
O3 O 0.7517(4) 0.2987(5) 0.7771(3) 0.0537(11) Uani 1 1 d . . .
O4 O 0.7006(5) 0.1277(5) 0.9107(4) 0.0603(12) Uani 1 1 d . . .
O5 O 0.6365(4) 0.6020(5) 0.8446(3) 0.0498(11) Uani 1 1 d . . .
O6 O 0.5280(4) 0.7450(5) 0.9476(3) 0.0512(11) Uani 1 1 d . . .
N1 N 0.4590(5) 0.5275(6) 0.6957(4) 0.0439(12) Uani 1 1 d . . .
N2 N 0.4076(5) 0.2729(6) 0.8176(4) 0.0479(13) Uani 1 1 d . . .
N3 N 0.1357(5) 0.2901(6) 0.5012(4) 0.0513(14) Uani 1 1 d . . .
N4 N 0.1709(5) 0.5020(6) 0.4017(4) 0.0461(13) Uani 1 1 d . . .
H4 H 0.1675 0.5778 0.3472 0.055 Uiso 1 1 calc R . .
C1 C 0.4792(6) 0.6538(7) 0.6388(5) 0.0505(17) Uani 1 1 d . . .
H1 H 0.5355 0.6929 0.6706 0.061 Uiso 1 1 calc R . .
C2 C 0.4224(7) 0.7331(7) 0.5346(5) 0.0542(17) Uani 1 1 d . . .
H2 H 0.4379 0.8231 0.4989 0.065 Uiso 1 1 calc R . .
C3 C 0.3425(6) 0.6724(7) 0.4866(5) 0.0497(16) Uani 1 1 d . . .
H3 H 0.3051 0.7202 0.4162 0.060 Uiso 1 1 calc R . .
C4 C 0.3180(6) 0.5407(7) 0.5430(4) 0.0411(14) Uani 1 1 d . . .
C5 C 0.3773(6) 0.4699(7) 0.6490(4) 0.0404(14) Uani 1 1 d . . .
C6 C 0.3523(6) 0.3332(7) 0.7137(5) 0.0412(14) Uani 1 1 d . . .
C7 C 0.3818(7) 0.1507(7) 0.8757(5) 0.0553(18) Uani 1 1 d . . .
H7 H 0.4177 0.1114 0.9471 0.066 Uiso 1 1 calc R . .
C8 C 0.3052(7) 0.0763(7) 0.8386(5) 0.0575(18) Uani 1 1 d . . .
H8 H 0.2911 -0.0105 0.8833 0.069 Uiso 1 1 calc R . .
C9 C 0.2508(7) 0.1340(7) 0.7343(5) 0.0582(18) Uani 1 1 d . . .
H9 H 0.1991 0.0860 0.7069 0.070 Uiso 1 1 calc R . .
C10 C 0.2725(6) 0.2643(7) 0.6689(5) 0.0433(15) Uani 1 1 d . . .
C11 C 0.2150(6) 0.3367(7) 0.5605(5) 0.0448(15) Uani 1 1 d . . .
C12 C 0.2383(6) 0.4672(7) 0.5018(5) 0.0445(15) Uani 1 1 d . . .
C13 C 0.1111(6) 0.3931(7) 0.4065(5) 0.0447(15) Uani 1 1 d . . .
C14 C 0.0260(6) 0.3905(7) 0.3170(5) 0.0471(16) Uani 1 1 d . . .
C15 C -0.0363(7) 0.2782(8) 0.3330(5) 0.0556(18) Uani 1 1 d . . .
H15 H -0.0212 0.2049 0.3990 0.067 Uiso 1 1 calc R . .
C16 C -0.1205(7) 0.2727(8) 0.2527(5) 0.0602(19) Uani 1 1 d . . .
H16 H -0.1620 0.1965 0.2647 0.072 Uiso 1 1 calc R . .
C17 C -0.1430(6) 0.3823(7) 0.1537(5) 0.0468(16) Uani 1 1 d . . .
C18 C -0.0817(7) 0.4945(7) 0.1365(5) 0.0584(18) Uani 1 1 d . . .
H18 H -0.0980 0.5681 0.0706 0.070 Uiso 1 1 calc R . .
C19 C 0.0050(7) 0.4994(7) 0.2171(5) 0.0552(18) Uani 1 1 d . . .
H19 H 0.0483 0.5743 0.2044 0.066 Uiso 1 1 calc R . .
C20 C -0.2415(7) 0.3809(7) 0.0687(5) 0.0500(16) Uani 1 1 d . . .
C21 C 0.7794(7) 0.1667(8) 0.8366(6) 0.0533(17) Uani 1 1 d . . .
C22 C 0.9129(9) 0.0580(10) 0.8213(9) 0.114(4) Uani 1 1 d . . .
H22A H 0.9916 0.0785 0.8479 0.171 Uiso 1 1 calc R . .
H22B H 0.9235 0.0649 0.7450 0.171 Uiso 1 1 calc R . .
H22C H 0.9088 -0.0386 0.8611 0.171 Uiso 1 1 calc R . .
C23 C 0.6095(7) 0.7174(8) 0.8720(5) 0.0499(16) Uani 1 1 d . . .
C24 C 0.6725(10) 0.8354(9) 0.8083(8) 0.114(4) Uani 1 1 d . . .
H24A H 0.6011 0.9268 0.7895 0.172 Uiso 1 1 calc R . .
H24B H 0.7116 0.8137 0.7428 0.172 Uiso 1 1 calc R . .
H24C H 0.7455 0.8416 0.8516 0.172 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 O2 2.326(4) 2_566 ?
Sm1 O5 2.337(4) . ?
Sm1 O6 2.352(4) 2_667 ?
Sm1 O3 2.433(4) . ?
Sm1 O4 2.483(5) . ?
Sm1 O1 2.536(4) 1_656 ?
Sm1 N2 2.588(5) . ?
Sm1 O2 2.615(4) 1_656 ?
Sm1 N1 2.686(5) . ?
Sm1 C21 2.810(7) . ?
Sm1 C20 2.940(6) 1_656 ?
Sm1 Sm1 3.9362(12) 2_667 ?
O1 C20 1.236(7) . ?
O1 Sm1 2.536(4) 1_454 ?
O2 C20 1.252(7) . ?
O2 Sm1 2.326(4) 2_566 ?
O2 Sm1 2.615(4) 1_454 ?
O3 C21 1.275(7) . ?
O4 C21 1.236(7) . ?
O5 C23 1.253(7) . ?
O6 C23 1.268(7) . ?
O6 Sm1 2.352(4) 2_667 ?
N1 C1 1.320(7) . ?
N1 C5 1.360(7) . ?
N2 C7 1.313(7) . ?
N2 C6 1.364(7) . ?
N3 C13 1.323(7) . ?
N3 C11 1.371(7) . ?
N4 C13 1.357(7) . ?
N4 C12 1.384(7) . ?
N4 H4 0.8600 . ?
C1 C2 1.394(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(7) . ?
C4 C12 1.423(8) . ?
C5 C6 1.451(8) . ?
C6 C10 1.414(8) . ?
C7 C8 1.379(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.366(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.431(7) . ?
C11 C12 1.372(8) . ?
C13 C14 1.469(8) . ?
C14 C15 1.380(9) . ?
C14 C19 1.397(8) . ?
C15 C16 1.380(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.392(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(9) . ?
C17 C20 1.506(7) . ?
C18 C19 1.397(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 Sm1 2.940(6) 1_454 ?
C21 C22 1.503(10) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.492(9) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Sm1 O5 77.80(15) 2_566 . ?
O2 Sm1 O6 74.55(15) 2_566 2_667 ?
O5 Sm1 O6 136.22(14) . 2_667 ?
O2 Sm1 O3 151.73(15) 2_566 . ?
O5 Sm1 O3 86.38(15) . . ?
O6 Sm1 O3 130.88(15) 2_667 . ?
O2 Sm1 O4 149.29(15) 2_566 . ?
O5 Sm1 O4 132.68(15) . . ?
O6 Sm1 O4 78.17(15) 2_667 . ?
O3 Sm1 O4 52.71(14) . . ?
O2 Sm1 O1 124.08(14) 2_566 1_656 ?
O5 Sm1 O1 78.13(17) . 1_656 ?
O6 Sm1 O1 90.06(17) 2_667 1_656 ?
O3 Sm1 O1 74.03(15) . 1_656 ?
O4 Sm1 O1 69.20(16) . 1_656 ?
O2 Sm1 N2 87.48(15) 2_566 . ?
O5 Sm1 N2 135.77(15) . . ?
O6 Sm1 N2 76.12(15) 2_667 . ?
O3 Sm1 N2 87.79(15) . . ?
O4 Sm1 N2 72.39(16) . . ?
O1 Sm1 N2 141.08(17) 1_656 . ?
O2 Sm1 O2 74.54(13) 2_566 1_656 ?
O5 Sm1 O2 69.97(13) . 1_656 ?
O6 Sm1 O2 70.32(13) 2_667 1_656 ?
O3 Sm1 O2 121.77(13) . 1_656 ?
O4 Sm1 O2 109.11(14) . 1_656 ?
O1 Sm1 O2 49.86(13) 1_656 1_656 ?
N2 Sm1 O2 145.02(14) . 1_656 ?
O2 Sm1 N1 77.17(14) 2_566 . ?
O5 Sm1 N1 73.80(14) . . ?
O6 Sm1 N1 130.05(14) 2_667 . ?
O3 Sm1 N1 75.98(15) . . ?
O4 Sm1 N1 111.31(15) . . ?
O1 Sm1 N1 139.78(17) 1_656 . ?
N2 Sm1 N1 62.26(15) . . ?
O2 Sm1 N1 137.71(14) 1_656 . ?
O2 Sm1 C21 169.10(16) 2_566 . ?
O5 Sm1 C21 109.05(18) . . ?
O6 Sm1 C21 104.08(18) 2_667 . ?
O3 Sm1 C21 26.93(16) . . ?
O4 Sm1 C21 26.08(16) . . ?
O1 Sm1 C21 66.42(16) 1_656 . ?
N2 Sm1 C21 81.73(18) . . ?
O2 Sm1 C21 115.48(16) 1_656 . ?
N1 Sm1 C21 96.32(18) . . ?
O2 Sm1 C20 99.47(16) 2_566 1_656 ?
O5 Sm1 C20 71.61(16) . 1_656 ?
O6 Sm1 C20 80.21(16) 2_667 1_656 ?
O3 Sm1 C20 97.50(17) . 1_656 ?
O4 Sm1 C20 89.43(17) . 1_656 ?
O1 Sm1 C20 24.70(16) 1_656 1_656 ?
N2 Sm1 C20 152.56(18) . 1_656 ?
O2 Sm1 C20 25.18(14) 1_656 1_656 ?
N1 Sm1 C20 145.14(17) . 1_656 ?
C21 Sm1 C20 90.86(18) . 1_656 ?
O2 Sm1 Sm1 39.82(9) 2_566 2_667 ?
O5 Sm1 Sm1 69.37(10) . 2_667 ?
O6 Sm1 Sm1 67.59(10) 2_667 2_667 ?
O3 Sm1 Sm1 150.50(10) . 2_667 ?
O4 Sm1 Sm1 136.52(10) . 2_667 ?
O1 Sm1 Sm1 84.42(10) 1_656 2_667 ?
N2 Sm1 Sm1 121.23(12) . 2_667 ?
O2 Sm1 Sm1 34.72(9) 1_656 2_667 ?
N1 Sm1 Sm1 111.12(11) . 2_667 ?
C21 Sm1 Sm1 150.01(13) . 2_667 ?
C20 Sm1 Sm1 59.73(13) 1_656 2_667 ?
C20 O1 Sm1 96.3(4) . 1_454 ?
C20 O2 Sm1 160.6(4) . 2_566 ?
C20 O2 Sm1 92.1(3) . 1_454 ?
Sm1 O2 Sm1 105.46(13) 2_566 1_454 ?
C21 O3 Sm1 93.2(4) . . ?
C21 O4 Sm1 91.9(4) . . ?
C23 O5 Sm1 137.1(4) . . ?
C23 O6 Sm1 138.1(4) . 2_667 ?
C1 N1 C5 117.6(5) . . ?
C1 N1 Sm1 122.8(4) . . ?
C5 N1 Sm1 119.7(4) . . ?
C7 N2 C6 118.0(5) . . ?
C7 N2 Sm1 119.9(4) . . ?
C6 N2 Sm1 122.1(4) . . ?
C13 N3 C11 104.2(5) . . ?
C13 N4 C12 106.5(5) . . ?
C13 N4 H4 126.7 . . ?
C12 N4 H4 126.7 . . ?
N1 C1 C2 124.9(5) . . ?
N1 C1 H1 117.5 . . ?
C2 C1 H1 117.5 . . ?
C3 C2 C1 117.2(6) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 118.8(5) . . ?
C3 C4 C12 125.0(5) . . ?
C5 C4 C12 116.1(5) . . ?
N1 C5 C4 121.5(5) . . ?
N1 C5 C6 117.1(5) . . ?
C4 C5 C6 121.5(5) . . ?
N2 C6 C10 121.1(5) . . ?
N2 C6 C5 118.8(5) . . ?
C10 C6 C5 120.2(5) . . ?
N2 C7 C8 124.7(6) . . ?
N2 C7 H7 117.6 . . ?
C8 C7 H7 117.6 . . ?
C9 C8 C7 118.1(6) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C10 120.1(6) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C6 118.1(5) . . ?
C9 C10 C11 124.3(5) . . ?
C6 C10 C11 117.6(5) . . ?
N3 C11 C12 111.4(5) . . ?
N3 C11 C10 127.5(6) . . ?
C12 C11 C10 121.0(5) . . ?
C11 C12 N4 105.0(5) . . ?
C11 C12 C4 123.6(5) . . ?
N4 C12 C4 131.4(6) . . ?
N3 C13 N4 112.8(5) . . ?
N3 C13 C14 123.4(6) . . ?
N4 C13 C14 123.8(6) . . ?
C15 C14 C19 119.3(5) . . ?
C15 C14 C13 118.9(6) . . ?
C19 C14 C13 121.8(6) . . ?
C14 C15 C16 121.3(6) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 119.4(6) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.0(5) . . ?
C18 C17 C20 120.5(6) . . ?
C16 C17 C20 119.4(6) . . ?
C17 C18 C19 120.6(6) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 119.3(6) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
O1 C20 O2 121.7(5) . . ?
O1 C20 C17 120.4(6) . . ?
O2 C20 C17 117.9(5) . . ?
O1 C20 Sm1 59.0(3) . 1_454 ?
O2 C20 Sm1 62.8(3) . 1_454 ?
C17 C20 Sm1 178.1(5) . 1_454 ?
O4 C21 O3 120.7(6) . . ?
O4 C21 C22 119.1(7) . . ?
O3 C21 C22 120.1(7) . . ?
O4 C21 Sm1 62.0(4) . . ?
O3 C21 Sm1 59.8(3) . . ?
C22 C21 Sm1 166.5(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 O6 125.2(6) . . ?
O5 C23 C24 118.1(6) . . ?
O6 C23 C24 116.6(6) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Sm1 O3 C21 -156.5(4) 2_566 . . . ?
O5 Sm1 O3 C21 147.9(4) . . . . ?
O6 Sm1 O3 C21 -6.6(4) 2_667 . . . ?
O4 Sm1 O3 C21 -6.6(3) . . . . ?
O1 Sm1 O3 C21 69.2(4) 1_656 . . . ?
N2 Sm1 O3 C21 -76.0(4) . . . . ?
O2 Sm1 O3 C21 84.2(4) 1_656 . . . ?
N1 Sm1 O3 C21 -137.9(4) . . . . ?
C20 Sm1 O3 C21 77.0(4) 1_656 . . . ?
Sm1 Sm1 O3 C21 113.9(4) 2_667 . . . ?
O2 Sm1 O4 C21 159.1(3) 2_566 . . . ?
O5 Sm1 O4 C21 -29.1(4) . . . . ?
O6 Sm1 O4 C21 -173.2(4) 2_667 . . . ?
O3 Sm1 O4 C21 6.8(4) . . . . ?
O1 Sm1 O4 C21 -78.6(4) 1_656 . . . ?
N2 Sm1 O4 C21 107.8(4) . . . . ?
O2 Sm1 O4 C21 -109.1(4) 1_656 . . . ?
N1 Sm1 O4 C21 58.1(4) . . . . ?
C20 Sm1 O4 C21 -93.1(4) 1_656 . . . ?
Sm1 Sm1 O4 C21 -135.1(3) 2_667 . . . ?
O2 Sm1 O5 C23 31.8(6) 2_566 . . . ?
O6 Sm1 O5 C23 -20.0(6) 2_667 . . . ?
O3 Sm1 O5 C23 -171.8(6) . . . . ?
O4 Sm1 O5 C23 -143.9(5) . . . . ?
O1 Sm1 O5 C23 -97.4(6) 1_656 . . . ?
N2 Sm1 O5 C23 105.1(6) . . . . ?
O2 Sm1 O5 C23 -46.0(6) 1_656 . . . ?
N1 Sm1 O5 C23 111.8(6) . . . . ?
C21 Sm1 O5 C23 -157.0(6) . . . . ?
C20 Sm1 O5 C23 -72.7(6) 1_656 . . . ?
Sm1 Sm1 O5 C23 -8.9(5) 2_667 . . . ?
O2 Sm1 N1 C1 83.1(5) 2_566 . . . ?
O5 Sm1 N1 C1 2.3(5) . . . . ?
O6 Sm1 N1 C1 139.8(4) 2_667 . . . ?
O3 Sm1 N1 C1 -88.0(5) . . . . ?
O4 Sm1 N1 C1 -127.8(5) . . . . ?
O1 Sm1 N1 C1 -45.3(6) 1_656 . . . ?
N2 Sm1 N1 C1 177.1(5) . . . . ?
O2 Sm1 N1 C1 34.1(6) 1_656 . . . ?
C21 Sm1 N1 C1 -105.8(5) . . . . ?
C20 Sm1 N1 C1 -5.1(6) 1_656 . . . ?
Sm1 Sm1 N1 C1 61.9(5) 2_667 . . . ?
O2 Sm1 N1 C5 -96.5(4) 2_566 . . . ?
O5 Sm1 N1 C5 -177.3(4) . . . . ?
O6 Sm1 N1 C5 -39.8(5) 2_667 . . . ?
O3 Sm1 N1 C5 92.4(4) . . . . ?
O4 Sm1 N1 C5 52.5(4) . . . . ?
O1 Sm1 N1 C5 135.1(4) 1_656 . . . ?
N2 Sm1 N1 C5 -2.6(4) . . . . ?
O2 Sm1 N1 C5 -145.5(4) 1_656 . . . ?
C21 Sm1 N1 C5 74.6(4) . . . . ?
C20 Sm1 N1 C5 175.3(4) 1_656 . . . ?
Sm1 Sm1 N1 C5 -117.7(4) 2_667 . . . ?
O2 Sm1 N2 C7 -102.9(5) 2_566 . . . ?
O5 Sm1 N2 C7 -172.5(4) . . . . ?
O6 Sm1 N2 C7 -28.2(5) 2_667 . . . ?
O3 Sm1 N2 C7 105.0(5) . . . . ?
O4 Sm1 N2 C7 53.6(5) . . . . ?
O1 Sm1 N2 C7 44.1(6) 1_656 . . . ?
O2 Sm1 N2 C7 -44.8(6) 1_656 . . . ?
N1 Sm1 N2 C7 -179.7(5) . . . . ?
C21 Sm1 N2 C7 78.6(5) . . . . ?
C20 Sm1 N2 C7 2.9(7) 1_656 . . . ?
Sm1 Sm1 N2 C7 -80.7(5) 2_667 . . . ?
O2 Sm1 N2 C6 80.5(4) 2_566 . . . ?
O5 Sm1 N2 C6 10.9(5) . . . . ?
O6 Sm1 N2 C6 155.2(5) 2_667 . . . ?
O3 Sm1 N2 C6 -71.7(4) . . . . ?
O4 Sm1 N2 C6 -123.1(4) . . . . ?
O1 Sm1 N2 C6 -132.6(4) 1_656 . . . ?
O2 Sm1 N2 C6 138.6(4) 1_656 . . . ?
N1 Sm1 N2 C6 3.7(4) . . . . ?
C21 Sm1 N2 C6 -98.0(4) . . . . ?
C20 Sm1 N2 C6 -173.7(4) 1_656 . . . ?
Sm1 Sm1 N2 C6 102.7(4) 2_667 . . . ?
C5 N1 C1 C2 0.4(9) . . . . ?
Sm1 N1 C1 C2 -179.2(5) . . . . ?
N1 C1 C2 C3 -1.9(10) . . . . ?
C1 C2 C3 C4 2.0(9) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
C2 C3 C4 C12 -179.5(6) . . . . ?
C1 N1 C5 C4 1.0(8) . . . . ?
Sm1 N1 C5 C4 -179.4(4) . . . . ?
C1 N1 C5 C6 -178.1(5) . . . . ?
Sm1 N1 C5 C6 1.5(7) . . . . ?
C3 C4 C5 N1 -0.8(9) . . . . ?
C12 C4 C5 N1 178.0(5) . . . . ?
C3 C4 C5 C6 178.3(6) . . . . ?
C12 C4 C5 C6 -2.9(8) . . . . ?
C7 N2 C6 C10 -1.6(9) . . . . ?
Sm1 N2 C6 C10 175.0(4) . . . . ?
C7 N2 C6 C5 178.8(6) . . . . ?
Sm1 N2 C6 C5 -4.6(7) . . . . ?
N1 C5 C6 N2 1.9(8) . . . . ?
C4 C5 C6 N2 -177.2(5) . . . . ?
N1 C5 C6 C10 -177.7(5) . . . . ?
C4 C5 C6 C10 3.1(8) . . . . ?
C6 N2 C7 C8 1.7(10) . . . . ?
Sm1 N2 C7 C8 -175.1(5) . . . . ?
N2 C7 C8 C9 -0.7(11) . . . . ?
C7 C8 C9 C10 -0.3(10) . . . . ?
C8 C9 C10 C6 0.3(10) . . . . ?
C8 C9 C10 C11 -177.2(6) . . . . ?
N2 C6 C10 C9 0.7(9) . . . . ?
C5 C6 C10 C9 -179.7(6) . . . . ?
N2 C6 C10 C11 178.4(5) . . . . ?
C5 C6 C10 C11 -2.0(8) . . . . ?
C13 N3 C11 C12 0.0(7) . . . . ?
C13 N3 C11 C10 -178.9(6) . . . . ?
C9 C10 C11 N3 -2.9(10) . . . . ?
C6 C10 C11 N3 179.7(6) . . . . ?
C9 C10 C11 C12 178.4(6) . . . . ?
C6 C10 C11 C12 0.9(9) . . . . ?
N3 C11 C12 N4 -0.3(7) . . . . ?
C10 C11 C12 N4 178.6(5) . . . . ?
N3 C11 C12 C4 -179.7(5) . . . . ?
C10 C11 C12 C4 -0.8(9) . . . . ?
C13 N4 C12 C11 0.5(6) . . . . ?
C13 N4 C12 C4 179.9(6) . . . . ?
C3 C4 C12 C11 -179.5(6) . . . . ?
C5 C4 C12 C11 1.8(9) . . . . ?
C3 C4 C12 N4 1.2(11) . . . . ?
C5 C4 C12 N4 -177.5(6) . . . . ?
C11 N3 C13 N4 0.4(7) . . . . ?
C11 N3 C13 C14 -178.6(6) . . . . ?
C12 N4 C13 N3 -0.6(7) . . . . ?
C12 N4 C13 C14 178.4(5) . . . . ?
N3 C13 C14 C15 2.5(9) . . . . ?
N4 C13 C14 C15 -176.4(6) . . . . ?
N3 C13 C14 C19 -178.5(6) . . . . ?
N4 C13 C14 C19 2.6(9) . . . . ?
C19 C14 C15 C16 -1.0(10) . . . . ?
C13 C14 C15 C16 178.1(6) . . . . ?
C14 C15 C16 C17 0.1(10) . . . . ?
C15 C16 C17 C18 -0.1(10) . . . . ?
C15 C16 C17 C20 -176.5(6) . . . . ?
C16 C17 C18 C19 0.9(10) . . . . ?
C20 C17 C18 C19 177.2(6) . . . . ?
C15 C14 C19 C18 1.7(10) . . . . ?
C13 C14 C19 C18 -177.4(6) . . . . ?
C17 C18 C19 C14 -1.7(10) . . . . ?
Sm1 O1 C20 O2 3.8(8) 1_454 . . . ?
Sm1 O1 C20 C17 -177.9(6) 1_454 . . . ?
Sm1 O2 C20 O1 -158.6(9) 2_566 . . . ?
Sm1 O2 C20 O1 -3.7(7) 1_454 . . . ?
Sm1 O2 C20 C17 23.1(16) 2_566 . . . ?
Sm1 O2 C20 C17 178.0(5) 1_454 . . . ?
Sm1 O2 C20 Sm1 -154.9(13) 2_566 . . 1_454 ?
C18 C17 C20 O1 96.1(9) . . . . ?
C16 C17 C20 O1 -87.5(9) . . . . ?
C18 C17 C20 O2 -85.6(8) . . . . ?
C16 C17 C20 O2 90.8(8) . . . . ?
Sm1 O4 C21 O3 -12.0(6) . . . . ?
Sm1 O4 C21 C22 164.7(6) . . . . ?
Sm1 O3 C21 O4 12.2(6) . . . . ?
Sm1 O3 C21 C22 -164.4(6) . . . . ?
O2 Sm1 C21 O4 -74.5(10) 2_566 . . . ?
O5 Sm1 C21 O4 157.8(3) . . . . ?
O6 Sm1 C21 O4 6.8(4) 2_667 . . . ?
O3 Sm1 C21 O4 -168.1(6) . . . . ?
O1 Sm1 C21 O4 90.6(4) 1_656 . . . ?
N2 Sm1 C21 O4 -66.5(4) . . . . ?
O2 Sm1 C21 O4 81.4(4) 1_656 . . . ?
N1 Sm1 C21 O4 -127.2(4) . . . . ?
C20 Sm1 C21 O4 86.9(4) 1_656 . . . ?
Sm1 Sm1 C21 O4 76.2(5) 2_667 . . . ?
O2 Sm1 C21 O3 93.5(10) 2_566 . . . ?
O5 Sm1 C21 O3 -34.2(4) . . . . ?
O6 Sm1 C21 O3 174.9(3) 2_667 . . . ?
O4 Sm1 C21 O3 168.1(6) . . . . ?
O1 Sm1 C21 O3 -101.3(4) 1_656 . . . ?
N2 Sm1 C21 O3 101.5(4) . . . . ?
O2 Sm1 C21 O3 -110.5(4) 1_656 . . . ?
N1 Sm1 C21 O3 40.8(4) . . . . ?
C20 Sm1 C21 O3 -105.0(4) 1_656 . . . ?
Sm1 Sm1 C21 O3 -115.7(4) 2_667 . . . ?
O2 Sm1 C21 C22 -173(2) 2_566 . . . ?
O5 Sm1 C21 C22 59(2) . . . . ?
O6 Sm1 C21 C22 -91(2) 2_667 . . . ?
O3 Sm1 C21 C22 94(2) . . . . ?
O4 Sm1 C21 C22 -98(2) . . . . ?
O1 Sm1 C21 C22 -8(2) 1_656 . . . ?
N2 Sm1 C21 C22 -165(2) . . . . ?
O2 Sm1 C21 C22 -17(2) 1_656 . . . ?
N1 Sm1 C21 C22 134(2) . . . . ?
C20 Sm1 C21 C22 -11(2) 1_656 . . . ?
Sm1 Sm1 C21 C22 -22(3) 2_667 . . . ?
Sm1 O5 C23 O6 0.9(10) . . . . ?
Sm1 O5 C23 C24 -176.3(5) . . . . ?
Sm1 O6 C23 O5 19.4(10) 2_667 . . . ?
Sm1 O6 C23 C24 -163.4(6) 2_667 . . . ?

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
N4 H4 O3 0.86 1.99 2.787(7) 154.3 2_666

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.114
