# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 La N O12'
_chemical_formula_weight         539.18

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   16.616(3)
_cell_length_b                   6.6445(13)
_cell_length_c                   18.857(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.80(2)
_cell_angle_gamma                90.00
_cell_volume                     1806.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4157
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    2.433
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5289
_exptl_absorpt_correction_T_max  0.6418
_exptl_absorpt_process_details   SADABS

_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17746
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4157
_reflns_number_gt                3823
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0283P)²+1.9504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4157
_refine_ls_number_parameters     302
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.016
_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
C11 C 0.4113(2) 1.1131(5) 1.1962(2) 0.0315(8) Uani 1 1 d . . .
O9 O 0.0500(2) 0.9900(4) 0.90421(16) 0.0422(7) Uani 1 1 d . . .
O10 O -0.08695(16) 0.3288(4) 0.84174(14) 0.0272(5) Uani 1 1 d . . .
O4 O -0.10442(15) 0.8628(3) 0.64917(12) 0.0231(4) Uani 1 1 d . . .
La1 La 0.041554(10) 0.60151(2) 0.911767(9) 0.01371(6) Uani 1 1 d . . .
C2 C -0.14519(19) 0.8613(4) 0.75312(16) 0.0165(5) Uani 1 1 d . . .
O3 O -0.01207(14) 0.7008(3) 0.76570(12) 0.0240(4) Uani 1 1 d . . .
O2 O -0.06035(13) 0.6556(3) 0.97554(12) 0.0201(4) Uani 1 1 d . . .
O5 O 0.16465(14) 0.7496(3) 1.05734(13) 0.0252(4) Uani 1 1 d . . .
C9 C 0.31366(19) 0.8838(4) 1.08864(17) 0.0189(6) Uani 1 1 d . . .
O6 O 0.20792(15) 0.7248(4) 0.96416(13) 0.0322(5) Uani 1 1 d . . .
N1 N -0.12316(16) 0.7889(4) 0.82663(13) 0.0173(5) Uani 1 1 d . . .
O1 O -0.19183(16) 0.7207(5) 0.97362(14) 0.0395(6) Uani 1 1 d . . .
C7 C -0.14231(19) 0.7306(4) 0.94228(16) 0.0186(5) Uani 1 1 d . . .
C1 C -0.08206(19) 0.8031(4) 0.72060(16) 0.0173(5) Uani 1 1 d . . .
C5 C -0.25773(19) 0.9447(4) 0.81940(17) 0.0177(5) Uani 1 1 d . . .
C8 C 0.22321(19) 0.7786(4) 1.03445(17) 0.0201(6) Uani 1 1 d . . .
C12 C 0.4833(2) 1.0787(6) 1.1805(2) 0.0347(8) Uani 1 1 d . . .
C6 C -0.17690(18) 0.8280(4) 0.85988(15) 0.0160(5) Uani 1 1 d . . .
C14 C 0.3865(2) 0.8498(5) 1.07343(19) 0.0246(6) Uani 1 1 d . . .
C10 C 0.32599(18) 1.0160(5) 1.15143(17) 0.0203(6) Uani 1 1 d . . .
C4 C -0.2807(2) 1.0182(5) 0.74218(18) 0.0253(6) Uani 1 1 d . . .
C3 C -0.2251(2) 0.9768(5) 0.70819(17) 0.0228(6) Uani 1 1 d . . .
C15 C 0.5526(2) 0.9062(6) 1.1063(2) 0.0380(9) Uani 1 1 d . . .
O7 O 0.53573(19) 0.7741(5) 1.0492(2) 0.0537(8) Uani 1 1 d . . .
H7 H 0.5830 0.7552 1.0465 0.081 Uiso 1 1 calc R . .
O8 O 0.62569(19) 0.9892(7) 1.1466(2) 0.0722(11) Uani 1 1 d . . .
C13 C 0.4716(2) 0.9446(5) 1.1195(2) 0.0273(6) Uani 1 1 d . . .
O11 O 0.19658(18) 0.9344(4) 0.82242(17) 0.0384(6) Uani 1 1 d . . .
O12 O 0.6740(3) 0.6958(7) 0.0217(3) 0.0773(13) Uani 1 1 d D . .
H6 H -0.236(4) 1.027(9) 0.658(4) 0.093 Uiso 1 1 d . . .
H10A H -0.120(4) 0.303(10) 0.860(4) 0.093 Uiso 1 1 d . . .
H5 H -0.334(4) 1.109(8) 0.714(4) 0.093 Uiso 1 1 d . . .
H10B H -0.112(5) 0.354(10) 0.799(4) 0.093 Uiso 1 1 d . . .
H11A H 0.199(4) 0.880(10) 0.863(4) 0.093 Uiso 1 1 d . . .
H2 H 0.422(4) 1.203(9) 1.236(4) 0.093 Uiso 1 1 d . . .
H4 H 0.380(4) 0.766(9) 1.033(3) 0.093 Uiso 1 1 d . . .
H11B H 0.252(4) 0.961(9) 0.837(4) 0.093 Uiso 1 1 d . . .
H9A H 0.101(4) 1.046(10) 0.924(4) 0.093 Uiso 1 1 d . . .
H9B H 0.008(5) 1.074(10) 0.885(4) 0.093 Uiso 1 1 d . . .
H1 H 0.541(4) 1.149(9) 1.213(4) 0.093 Uiso 1 1 d . . .
H12B H 0.662(3) 0.665(10) -0.0261(13) 0.093 Uiso 1 1 d D . .
H12A H 0.7319(10) 0.681(10) 0.052(2) 0.093 Uiso 1 1 d 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
C11 C12 1.386(5) . ?
C11 C10 1.396(4) . ?
C11 H2 0.91(6) . ?
O9 La1 2.593(3) . ?
O9 H9A 0.83(6) . ?
O9 H9B 0.82(6) . ?
O10 La1 2.604(2) . ?
O10 H10A 0.80(7) . ?
O10 H10B 0.72(7) . ?
O4 C1 1.270(3) . ?
O4 La1 2.474(2) 2_556 ?
La1 O4 2.474(2) 2_546 ?
La1 O3 2.525(2) . ?
La1 O2 2.543(2) . ?
La1 O6 2.564(2) . ?
La1 O2 2.621(2) 3_567 ?
La1 O5 2.666(2) . ?
La1 N1 2.693(2) . ?
C2 N1 1.335(3) . ?
C2 C3 1.397(4) . ?
C2 C1 1.505(4) . ?
O3 C1 1.247(3) . ?
O2 C7 1.284(3) . ?
O2 La1 2.621(2) 3_567 ?
O5 C8 1.260(3) . ?
C9 C14 1.394(4) . ?
C9 C10 1.405(4) . ?
C9 C8 1.505(4) . ?
O6 C8 1.271(3) . ?
N1 C6 1.347(3) . ?
O1 C7 1.231(3) . ?
C7 C6 1.509(4) . ?
C5 C4 1.397(4) . ?
C5 C6 1.403(4) . ?
C5 C10 1.509(4) 3_577 ?
C12 C13 1.391(5) . ?
C12 H1 0.96(6) . ?
C14 C13 1.390(4) . ?
C14 H4 0.91(6) . ?
C10 C5 1.509(4) 3_577 ?
C4 C3 1.389(4) . ?
C4 H5 0.98(6) . ?
C3 H6 0.94(6) . ?
C15 O8 1.200(5) . ?
C15 O7 1.308(5) . ?
C15 C13 1.505(4) . ?
O7 H7 0.8200 . ?
O11 H11A 0.82(7) . ?
O11 H11B 0.83(6) . ?
O12 H12B 0.844(10) . ?
O12 H12A 0.846(10) . ?

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
C12 C11 C10 121.3(3) . . ?
C12 C11 H2 117(4) . . ?
C10 C11 H2 122(4) . . ?
La1 O9 H9A 120(4) . . ?
La1 O9 H9B 130(5) . . ?
H9A O9 H9B 110(6) . . ?
La1 O10 H10A 120(5) . . ?
La1 O10 H10B 106(5) . . ?
H10A O10 H10B 114(6) . . ?
C1 O4 La1 136.43(18) . 2_556 ?
O4 La1 O3 70.27(7) 2_546 . ?
O4 La1 O2 147.60(7) 2_546 . ?
O3 La1 O2 121.47(7) . . ?
O4 La1 O6 76.15(7) 2_546 . ?
O3 La1 O6 93.74(7) . . ?
O2 La1 O6 128.06(7) . . ?
O4 La1 O9 124.46(9) 2_546 . ?
O3 La1 O9 71.30(8) . . ?
O2 La1 O9 87.27(9) . . ?
O6 La1 O9 68.01(9) . . ?
O4 La1 O10 75.37(8) 2_546 . ?
O3 La1 O10 82.69(8) . . ?
O2 La1 O10 76.54(7) . . ?
O6 La1 O10 150.79(8) . . ?
O9 La1 O10 135.88(8) . . ?
O4 La1 O2 92.92(7) 2_546 3_567 ?
O3 La1 O2 152.85(7) . 3_567 ?
O2 La1 O2 63.11(8) . 3_567 ?
O6 La1 O2 102.98(7) . 3_567 ?
O9 La1 O2 134.86(8) . 3_567 ?
O10 La1 O2 72.25(7) . 3_567 ?
O4 La1 O5 115.46(7) 2_546 . ?
O3 La1 O5 134.51(7) . . ?
O2 La1 O5 79.12(7) . . ?
O6 La1 O5 49.97(7) . . ?
O9 La1 O5 69.78(8) . . ?
O10 La1 O5 142.66(7) . . ?
O2 La1 O5 71.61(7) 3_567 . ?
O4 La1 N1 123.93(7) 2_546 . ?
O3 La1 N1 61.69(7) . . ?
O2 La1 N1 59.88(7) . . ?
O6 La1 N1 131.59(8) . . ?
O9 La1 N1 64.77(8) . . ?
O10 La1 N1 71.64(7) . . ?
O2 La1 N1 117.45(7) 3_567 . ?
O5 La1 N1 118.40(7) . . ?
N1 C2 C3 121.0(2) . . ?
N1 C2 C1 116.3(2) . . ?
C3 C2 C1 122.6(2) . . ?
C1 O3 La1 126.18(17) . . ?
C7 O2 La1 128.16(17) . . ?
C7 O2 La1 108.62(16) . 3_567 ?
La1 O2 La1 116.89(8) . 3_567 ?
C8 O5 La1 91.81(17) . . ?
C14 C9 C10 119.8(3) . . ?
C14 C9 C8 117.5(3) . . ?
C10 C9 C8 122.7(3) . . ?
C8 O6 La1 96.33(17) . . ?
C2 N1 C6 120.7(2) . . ?
C2 N1 La1 117.30(17) . . ?
C6 N1 La1 121.61(17) . . ?
O1 C7 O2 123.0(3) . . ?
O1 C7 C6 120.9(3) . . ?
O2 C7 C6 116.0(2) . . ?
O3 C1 O4 125.2(3) . . ?
O3 C1 C2 117.7(2) . . ?
O4 C1 C2 117.1(2) . . ?
C4 C5 C6 116.9(3) . . ?
C4 C5 C10 117.0(3) . 3_577 ?
C6 C5 C10 126.0(3) . 3_577 ?
O5 C8 O6 121.7(3) . . ?
O5 C8 C9 121.3(3) . . ?
O6 C8 C9 117.0(2) . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H1 119(4) . . ?
C13 C12 H1 121(4) . . ?
N1 C6 C5 122.0(2) . . ?
N1 C6 C7 113.3(2) . . ?
C5 C6 C7 124.7(2) . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H4 118(4) . . ?
C9 C14 H4 121(4) . . ?
C11 C10 C9 118.5(3) . . ?
C11 C10 C5 114.9(3) . 3_577 ?
C9 C10 C5 126.5(3) . 3_577 ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H5 120(4) . . ?
C5 C4 H5 119(4) . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H6 124(4) . . ?
C2 C3 H6 117(4) . . ?
O8 C15 O7 124.4(3) . . ?
O8 C15 C13 121.6(4) . . ?
O7 C15 C13 114.0(3) . . ?
C15 O7 H7 109.5 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 C15 122.4(3) . . ?
C12 C13 C15 118.5(3) . . ?
H11A O11 H11B 104(6) . . ?
H12B O12 H12A 106.0(17) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.744
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.106

_database_code_depnum_ccdc_archive 'CCDC 979204'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 N2 O23 Sm2'
_chemical_formula_weight         1083.23

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                   6.9630(14)
_cell_length_b                   10.796(2)
_cell_length_c                   12.320(3)
_cell_angle_alpha                69.70(3)
_cell_angle_beta                 87.50(3)
_cell_angle_gamma                79.76(3)
_cell_volume                     854.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3925
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.105
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    3.504
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4995
_exptl_absorpt_correction_T_max  0.5408
_exptl_absorpt_process_details   SADABS

_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6997
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2992
_reflns_number_gt                2828
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0132P)²+6.1156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     271
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 1.17820(4) 0.15176(3) 0.43094(2) 0.01536(10) Uani 1 1 d . . .
O1 O 0.7658(8) 1.1888(4) -0.0561(4) 0.0347(12) Uani 1 1 d . . .
H1 H 0.7862 1.2699 -0.1098 0.052 Uiso 1 1 d R . .
O2 O 0.7190(8) 1.0995(5) -0.1897(4) 0.0355(12) Uani 1 1 d . . .
O3 O 0.7814(6) 0.9454(4) 0.3534(3) 0.0203(9) Uani 1 1 d . . .
O4 O 0.8421(7) 0.7243(4) 0.4232(4) 0.0267(10) Uani 1 1 d . . .
O6 O 1.2333(6) 0.3577(4) 0.2899(4) 0.0261(10) Uani 1 1 d . A .
O7 O 0.5229(6) 0.1485(4) 0.4813(4) 0.0228(9) Uani 1 1 d . . .
O8 O 0.8470(6) 0.0936(4) 0.5081(3) 0.0174(9) Uani 1 1 d . . .
N1 N 0.8870(7) 0.3456(4) 0.3789(4) 0.0164(10) Uani 1 1 d . . .
C1 C 0.9138(8) 0.4692(5) 0.3111(5) 0.0161(12) Uani 1 1 d . A .
C2 C 0.7607(9) 0.5805(5) 0.2849(5) 0.0175(12) Uani 1 1 d . . .
C3 C 0.5812(9) 0.5584(6) 0.3356(5) 0.0241(14) Uani 1 1 d . . .
H3 H 0.4796 0.6305 0.3250 0.029 Uiso 1 1 calc R . .
C4 C 0.5522(9) 0.4294(6) 0.4020(5) 0.0199(13) Uani 1 1 d . . .
H4 H 0.4314 0.4138 0.4338 0.024 Uiso 1 1 calc R . .
C5 C 0.7085(8) 0.3255(5) 0.4190(5) 0.0137(11) Uani 1 1 d . . .
C6 C 0.7727(9) 0.7138(6) 0.1951(5) 0.0186(12) Uani 1 1 d . . .
C7 C 0.7826(8) 0.8307(5) 0.2177(5) 0.0166(12) Uani 1 1 d . . .
C8 C 0.7729(9) 0.9521(6) 0.1254(5) 0.0190(12) Uani 1 1 d . . .
H8 H 0.7798 1.0301 0.1401 0.023 Uiso 1 1 calc R . .
C9 C 0.7529(9) 0.9577(6) 0.0113(5) 0.0201(13) Uani 1 1 d . . .
C10 C 0.7440(11) 0.8408(6) -0.0114(5) 0.0284(15) Uani 1 1 d . . .
H10 H 0.7328 0.8435 -0.0872 0.034 Uiso 1 1 calc R . .
C11 C 0.7520(11) 0.7212(6) 0.0795(5) 0.0292(15) Uani 1 1 d . . .
H11 H 0.7435 0.6437 0.0643 0.035 Uiso 1 1 calc R . .
C12 C 0.7437(9) 1.0885(6) -0.0893(5) 0.0244(14) Uani 1 1 d . . .
C13 C 0.8044(8) 0.8311(6) 0.3388(5) 0.0178(12) Uani 1 1 d . . .
C14 C 1.1182(10) 0.4722(6) 0.2641(6) 0.0272(15) Uani 1 1 d . . .
C15 C 0.6877(8) 0.1792(5) 0.4757(5) 0.0149(12) Uani 1 1 d . . .
O11 O 0.8765(19) 0.3724(11) 0.0835(9) 0.052(3) Uani 0.50 1 d P . .
H11A H 0.8280 0.3044 0.0865 0.078 Uiso 0.50 1 d PR . .
H11B H 0.7852 0.4357 0.0847 0.078 Uiso 0.50 1 d PR . .
O9 O 0.9940(7) 0.1452(4) 0.2661(4) 0.0285(10) Uani 1 1 d . . .
H9A H 0.9105 0.2290 0.2240 0.043 Uiso 1 1 d R . .
H9B H 0.9065 0.0801 0.2871 0.043 Uiso 1 1 d R . .
O10 O 1.3964(7) 0.0765(4) 0.2936(4) 0.0284(10) Uani 1 1 d . . .
H10A H 1.3427 0.0249 0.2669 0.043 Uiso 1 1 d R . .
H10B H 1.5079 0.0307 0.3277 0.043 Uiso 1 1 d R . .
O5B O 1.165(2) 0.5752(13) 0.1904(13) 0.031(3) Uani 0.60(3) 1 d PU A 2
O5A O 1.166(4) 0.586(2) 0.224(2) 0.031(3) Uani 0.40(3) 1 d PU A 1
O13 O 0.476(3) 0.411(2) 0.0963(15) 0.118(5) Uani 0.510(13) 1 d P B 2
H13B H 0.4181 0.4593 0.1333 0.177 Uiso 0.510(13) 1 d PR B 2
H13A H 0.5853 0.4346 0.0731 0.177 Uiso 0.510(13) 1 d PR B 2
O12 O 0.612(3) 0.326(2) 0.1614(16) 0.118(5) Uani 0.490(13) 1 d P B 1
H12A H 0.5185 0.3277 0.1183 0.177 Uiso 0.490(13) 1 d PR B 1
H12B H 0.5717 0.3731 0.2035 0.177 Uiso 0.490(13) 1 d PR B 1


_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 O6 2.382(4) . ?
Sm1 O10 2.475(5) . ?
Sm1 O9 2.477(4) . ?
Sm1 O7 2.496(4) 1_655 ?
Sm1 O3 2.503(4) 2_766 ?
Sm1 O8 2.527(4) 2_756 ?
Sm1 O8 2.554(4) . ?
Sm1 N1 2.564(5) . ?
Sm1 O4 2.572(4) 2_766 ?
Sm1 C13 2.916(6) 2_766 ?
O1 C12 1.317(8) . ?
O1 H1 0.9269 . ?
O2 C12 1.218(8) . ?
O3 C13 1.290(7) . ?
O3 Sm1 2.503(4) 2_766 ?
O4 C13 1.251(7) . ?
O4 Sm1 2.572(4) 2_766 ?
O6 C14 1.292(8) . ?
O7 C15 1.243(7) . ?
O7 Sm1 2.496(4) 1_455 ?
O8 C15 1.290(7) . ?
O8 Sm1 2.527(4) 2_756 ?
N1 C5 1.344(7) . ?
N1 C1 1.347(7) . ?
C1 C2 1.410(8) . ?
C1 C14 1.515(9) . ?
C2 C3 1.395(9) . ?
C2 C6 1.494(8) . ?
C3 C4 1.394(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(8) . ?
C4 H4 0.9300 . ?
C5 C15 1.520(7) . ?
C6 C7 1.398(8) . ?
C6 C11 1.411(8) . ?
C7 C8 1.399(8) . ?
C7 C13 1.507(8) . ?
C8 C9 1.398(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.397(9) . ?
C9 C12 1.515(8) . ?
C10 C11 1.379(8) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 Sm1 2.916(6) 2_766 ?
C14 O5B 1.253(14) . ?
C14 O5A 1.26(2) . ?
O11 H11A 0.8499 . ?
O11 H11B 0.8501 . ?
O9 H9A 0.9690 . ?
O9 H9B 0.9716 . ?
O10 H10A 0.8781 . ?
O10 H10B 0.8786 . ?
O13 H13B 0.8502 . ?
O13 H13A 0.8500 . ?
O13 H12A 0.8403 . ?
O13 H12B 1.3994 . ?
O12 H13A 1.2834 . ?
O12 H12A 0.8496 . ?
O12 H12B 0.8504 . ?

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
O6 Sm1 O10 77.23(15) . . ?
O6 Sm1 O9 81.16(15) . . ?
O10 Sm1 O9 68.10(15) . . ?
O6 Sm1 O7 79.94(14) . 1_655 ?
O10 Sm1 O7 71.32(15) . 1_655 ?
O9 Sm1 O7 138.02(15) . 1_655 ?
O6 Sm1 O3 133.40(14) . 2_766 ?
O10 Sm1 O3 124.62(14) . 2_766 ?
O9 Sm1 O3 142.93(14) . 2_766 ?
O7 Sm1 O3 71.92(14) 1_655 2_766 ?
O6 Sm1 O8 151.91(15) . 2_756 ?
O10 Sm1 O8 77.72(14) . 2_756 ?
O9 Sm1 O8 77.87(14) . 2_756 ?
O7 Sm1 O8 103.72(13) 1_655 2_756 ?
O3 Sm1 O8 72.53(13) 2_766 2_756 ?
O6 Sm1 O8 126.10(13) . . ?
O10 Sm1 O8 130.49(14) . . ?
O9 Sm1 O8 73.33(14) . . ?
O7 Sm1 O8 145.99(13) 1_655 . ?
O3 Sm1 O8 74.07(13) 2_766 . ?
O8 Sm1 O8 64.60(15) 2_756 . ?
O6 Sm1 N1 63.58(15) . . ?
O10 Sm1 N1 126.54(15) . . ?
O9 Sm1 N1 71.07(15) . . ?
O7 Sm1 N1 129.79(14) 1_655 . ?
O3 Sm1 N1 108.79(15) 2_766 . ?
O8 Sm1 N1 124.89(14) 2_756 . ?
O8 Sm1 N1 63.43(13) . . ?
O6 Sm1 O4 85.74(15) . 2_766 ?
O10 Sm1 O4 143.60(15) . 2_766 ?
O9 Sm1 O4 140.85(15) . 2_766 ?
O7 Sm1 O4 74.18(15) 1_655 2_766 ?
O3 Sm1 O4 51.50(13) 2_766 2_766 ?
O8 Sm1 O4 122.22(13) 2_756 2_766 ?
O8 Sm1 O4 85.43(14) . 2_766 ?
N1 Sm1 O4 70.05(15) . 2_766 ?
O6 Sm1 C13 109.30(16) . 2_766 ?
O10 Sm1 C13 139.24(15) . 2_766 ?
O9 Sm1 C13 151.46(16) . 2_766 ?
O7 Sm1 C13 70.51(15) 1_655 2_766 ?
O3 Sm1 C13 26.14(14) 2_766 2_766 ?
O8 Sm1 C13 97.96(14) 2_756 2_766 ?
O8 Sm1 C13 79.36(15) . 2_766 ?
N1 Sm1 C13 89.50(16) . 2_766 ?
O4 Sm1 C13 25.37(14) 2_766 2_766 ?
C12 O1 H1 120.8 . . ?
C13 O3 Sm1 95.1(3) . 2_766 ?
C13 O4 Sm1 92.8(4) . 2_766 ?
C14 O6 Sm1 126.4(4) . . ?
C15 O7 Sm1 160.8(4) . 1_455 ?
C15 O8 Sm1 117.1(3) . 2_756 ?
C15 O8 Sm1 121.7(3) . . ?
Sm1 O8 Sm1 115.40(15) 2_756 . ?
C5 N1 C1 119.6(5) . . ?
C5 N1 Sm1 120.8(3) . . ?
C1 N1 Sm1 119.6(4) . . ?
N1 C1 C2 121.8(5) . . ?
N1 C1 C14 113.0(5) . . ?
C2 C1 C14 125.2(5) . . ?
C3 C2 C1 117.2(5) . . ?
C3 C2 C6 118.5(5) . . ?
C1 C2 C6 123.8(5) . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 117.9(6) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 122.5(5) . . ?
N1 C5 C15 114.8(5) . . ?
C4 C5 C15 122.5(5) . . ?
C7 C6 C11 119.1(5) . . ?
C7 C6 C2 125.2(5) . . ?
C11 C6 C2 115.4(5) . . ?
C6 C7 C8 119.4(5) . . ?
C6 C7 C13 122.3(5) . . ?
C8 C7 C13 118.4(5) . . ?
C9 C8 C7 120.8(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 119.8(5) . . ?
C10 C9 C12 118.9(5) . . ?
C8 C9 C12 121.2(5) . . ?
C11 C10 C9 119.4(6) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C6 121.4(6) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
O2 C12 O1 123.8(6) . . ?
O2 C12 C9 123.7(6) . . ?
O1 C12 C9 112.5(5) . . ?
O4 C13 O3 120.5(5) . . ?
O4 C13 C7 121.5(5) . . ?
O3 C13 C7 118.0(5) . . ?
O4 C13 Sm1 61.8(3) . 2_766 ?
O3 C13 Sm1 58.8(3) . 2_766 ?
C7 C13 Sm1 175.7(4) . 2_766 ?
O5B C14 O5A 21.5(12) . . ?
O5B C14 O6 120.8(9) . . ?
O5A C14 O6 126.9(12) . . ?
O5B C14 C1 122.3(8) . . ?
O5A C14 C1 115.6(12) . . ?
O6 C14 C1 116.0(5) . . ?
O7 C15 O8 124.2(5) . . ?
O7 C15 C5 119.0(5) . . ?
O8 C15 C5 116.7(5) . . ?
H11A O11 H11B 109.5 . . ?
Sm1 O9 H9A 114.3 . . ?
Sm1 O9 H9B 114.6 . . ?
H9A O9 H9B 103.9 . . ?
Sm1 O10 H10A 110.8 . . ?
Sm1 O10 H10B 110.7 . . ?
H10A O10 H10B 108.1 . . ?
H13B O13 H13A 109.5 . . ?
H13B O13 H12A 130.6 . . ?
H13A O13 H12A 96.1 . . ?
H13B O13 H12B 71.5 . . ?
H13A O13 H12B 80.8 . . ?
H12A O13 H12B 71.9 . . ?
H13A O12 H12A 68.8 . . ?
H13A O12 H12B 88.1 . . ?
H12A O12 H12B 109.7 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.636
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.154


_database_code_depnum_ccdc_archive 'CCDC 979207'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 Eu2 N2 O23'
_chemical_formula_weight         1086.45

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                   6.9200(14)
_cell_length_b                   10.760(2)
_cell_length_c                   12.246(2)
_cell_angle_alpha                69.62(3)
_cell_angle_beta                 87.57(3)
_cell_angle_gamma                79.86(3)
_cell_volume                     841.2(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2952
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             530
_exptl_absorpt_coefficient_mu    3.798
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3960
_exptl_absorpt_correction_T_max  0.5178
_exptl_absorpt_process_details   SADABS

_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6982
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_sigmaI/netI    0.0850
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2952
_reflns_number_gt                2563
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0595P)²+5.0692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2952
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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 0.67708(6) -0.34819(4) 0.93076(4) 0.01868(18) Uani 1 1 d . . .
O1 O 0.3456(8) -0.4064(6) 1.0093(5) 0.0189(12) Uani 1 1 d . . .
O2 O 0.0205(9) -0.3522(6) 0.9809(6) 0.0245(14) Uani 1 1 d . . .
O3 O 0.7324(9) -0.1435(6) 0.7907(6) 0.0285(15) Uani 1 1 d . . .
O4 O 0.6682(12) 0.0782(7) 0.7032(8) 0.051(2) Uani 1 1 d . . .
O5 O 0.2199(11) 0.6000(7) 0.3090(6) 0.0351(17) Uani 1 1 d . . .
O6 O 0.2667(11) 0.6891(6) 0.4432(6) 0.0349(17) Uani 1 1 d . . .
H6 H 0.2549 0.7589 0.3865 0.052 Uiso 1 1 d R . .
O7 O 0.2821(9) 0.4446(6) 0.8541(5) 0.0212(13) Uani 1 1 d . . .
O8 O 0.3440(11) 0.2237(6) 0.9241(5) 0.0304(15) Uani 1 1 d . . .
O9 O 0.4942(10) -0.3549(7) 0.7667(6) 0.0325(16) Uani 1 1 d . . .
H9A H 0.4527 -0.4238 0.7657 0.049 Uiso 1 1 d R . .
H9B H 0.4840 -0.2930 0.6996 0.049 Uiso 1 1 d R . .
O10 O 0.8957(10) -0.4240(7) 0.7950(6) 0.0297(15) Uani 1 1 d . . .
H10A H 0.8636 -0.4789 0.7661 0.045 Uiso 1 1 d R . .
H10B H 1.0035 -0.3951 0.7767 0.045 Uiso 1 1 d R . .
N1 N 0.3882(11) -0.1560(7) 0.8781(6) 0.0198(15) Uani 1 1 d . . .
C1 C 0.2089(13) -0.1754(8) 0.9194(7) 0.0195(18) Uani 1 1 d . . .
C2 C 0.0533(13) -0.0704(8) 0.9020(8) 0.0231(19) Uani 1 1 d . . .
H2 H -0.0682 -0.0863 0.9339 0.028 Uiso 1 1 calc R . .
C3 C 0.0805(13) 0.0595(9) 0.8361(8) 0.0224(19) Uani 1 1 d . . .
H3 H -0.0203 0.1324 0.8262 0.027 Uiso 1 1 calc R . .
C4 C 0.2625(12) 0.0782(8) 0.7852(7) 0.0171(17) Uani 1 1 d . . .
C5 C 0.4130(13) -0.0327(8) 0.8116(7) 0.0177(18) Uani 1 1 d . . .
C6 C 0.6182(14) -0.0280(9) 0.7644(8) 0.027(2) Uani 1 1 d . . .
C7 C 0.1879(13) -0.3210(8) 0.9759(7) 0.0184(18) Uani 1 1 d . . .
C8 C 0.2730(12) 0.2132(9) 0.6954(7) 0.0200(18) Uani 1 1 d . . .
C9 C 0.2839(13) 0.3299(8) 0.7189(7) 0.0190(18) Uani 1 1 d . . .
C10 C 0.3043(13) 0.3303(8) 0.8391(7) 0.0188(18) Uani 1 1 d . . .
C11 C 0.2738(13) 0.4514(8) 0.6231(8) 0.0233(19) Uani 1 1 d . . .
H11 H 0.2828 0.5298 0.6371 0.028 Uiso 1 1 calc R . .
C12 C 0.2511(12) 0.4585(8) 0.5105(8) 0.0203(18) Uani 1 1 d . . .
C13 C 0.2439(13) 0.5887(9) 0.4097(8) 0.0228(19) Uani 1 1 d . . .
C14 C 0.2437(16) 0.3410(10) 0.4883(8) 0.032(2) Uani 1 1 d . . .
H14 H 0.2335 0.3437 0.4121 0.038 Uiso 1 1 calc R . .
C15 C 0.2515(15) 0.2204(9) 0.5800(8) 0.029(2) Uani 1 1 d . . .
H15 H 0.2423 0.1428 0.5647 0.035 Uiso 1 1 calc R . .
O13 O 0.969(4) 0.932(3) 0.585(2) 0.110(7) Uani 0.506(19) 1 d PG A 1
H13A H 0.9947 0.8644 0.6477 0.165 Uiso 0.506(19) 1 d PR A 1
H13B H 0.8781 0.9897 0.5977 0.165 Uiso 0.506(19) 1 d PR A 1
O12 O 1.106(4) 0.830(3) 0.655(2) 0.110(7) Uani 0.494(19) 1 d P A 2
H12B H 1.1759 0.8269 0.5973 0.165 Uiso 0.494(19) 1 d PR A 2
H12A H 0.9855 0.8409 0.6373 0.165 Uiso 0.494(19) 1 d PR A 2
O11 O 0.372(3) 0.8743(17) 0.5822(14) 0.053(4) Uani 0.50 1 d P . .
H11B H 0.3195 0.8476 0.5179 0.080 Uiso 0.50 1 d PR . .
H11A H 0.2668 0.9185 0.6068 0.080 Uiso 0.50 1 d PR . .


_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 O3 2.355(6) . ?
Eu1 O9 2.447(7) . ?
Eu1 O10 2.453(6) . ?
Eu1 O2 2.469(6) 1_655 ?
Eu1 O7 2.481(6) 2_657 ?
Eu1 O1 2.514(6) 2_647 ?
Eu1 N1 2.533(7) . ?
Eu1 O1 2.545(6) . ?
Eu1 O8 2.558(6) 2_657 ?
Eu1 C10 2.900(8) 2_657 ?
Eu1 Eu1 4.2619(16) 2_647 ?
O1 C7 1.275(10) . ?
O1 Eu1 2.514(6) 2_647 ?
O2 C7 1.255(10) . ?
O2 Eu1 2.469(6) 1_455 ?
O3 C6 1.292(11) . ?
O4 C6 1.228(12) . ?
O5 C13 1.212(11) . ?
O6 C13 1.317(11) . ?
O6 H6 0.8200 . ?
O7 C10 1.288(10) . ?
O7 Eu1 2.481(6) 2_657 ?
O8 C10 1.247(11) . ?
O8 Eu1 2.558(6) 2_657 ?
O9 H9A 0.8449 . ?
O9 H9B 0.8551 . ?
O10 H10A 0.8497 . ?
O10 H10B 0.8500 . ?
N1 C5 1.330(10) . ?
N1 C1 1.343(11) . ?
C1 C2 1.380(12) . ?
C1 C7 1.507(11) . ?
C2 C3 1.391(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(12) . ?
C4 C8 1.497(12) . ?
C5 C6 1.512(13) . ?
C8 C9 1.397(12) . ?
C8 C15 1.402(13) . ?
C9 C11 1.413(12) . ?
C9 C10 1.487(12) . ?
C10 Eu1 2.900(8) 2_657 ?
C11 C12 1.368(13) . ?
C11 H11 0.9300 . ?
C12 C14 1.392(13) . ?
C12 C13 1.505(12) . ?
C14 C15 1.383(13) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
O13 H13A 0.8500 . ?
O13 H13B 0.8501 . ?
O13 H12A 0.9550 . ?
O12 H13A 0.7870 . ?
O12 H12B 0.8499 . ?
O12 H12A 0.8500 . ?
O11 H11B 1.0269 . ?
O11 H11A 0.8991 . ?

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
O3 Eu1 O9 81.3(2) . . ?
O3 Eu1 O10 77.6(2) . . ?
O9 Eu1 O10 68.3(2) . . ?
O3 Eu1 O2 80.0(2) . 1_655 ?
O9 Eu1 O2 137.8(2) . 1_655 ?
O10 Eu1 O2 70.9(2) . 1_655 ?
O3 Eu1 O7 133.1(2) . 2_657 ?
O9 Eu1 O7 143.1(2) . 2_657 ?
O10 Eu1 O7 124.2(2) . 2_657 ?
O2 Eu1 O7 71.8(2) 1_655 2_657 ?
O3 Eu1 O1 151.6(2) . 2_647 ?
O9 Eu1 O1 77.7(2) . 2_647 ?
O10 Eu1 O1 76.9(2) . 2_647 ?
O2 Eu1 O1 103.20(19) 1_655 2_647 ?
O7 Eu1 O1 72.93(19) 2_657 2_647 ?
O3 Eu1 N1 63.5(2) . . ?
O9 Eu1 N1 71.0(2) . . ?
O10 Eu1 N1 126.7(2) . . ?
O2 Eu1 N1 130.0(2) 1_655 . ?
O7 Eu1 N1 109.0(2) 2_657 . ?
O1 Eu1 N1 125.3(2) 2_647 . ?
O3 Eu1 O1 126.2(2) . . ?
O9 Eu1 O1 73.7(2) . . ?
O10 Eu1 O1 130.8(2) . . ?
O2 Eu1 O1 145.7(2) 1_655 . ?
O7 Eu1 O1 73.86(19) 2_657 . ?
O1 Eu1 O1 65.2(2) 2_647 . ?
N1 Eu1 O1 63.6(2) . . ?
O3 Eu1 O8 85.4(2) . 2_657 ?
O9 Eu1 O8 140.7(2) . 2_657 ?
O10 Eu1 O8 143.6(2) . 2_657 ?
O2 Eu1 O8 74.6(2) 1_655 2_657 ?
O7 Eu1 O8 51.65(19) 2_657 2_657 ?
O1 Eu1 O8 122.82(19) 2_647 2_657 ?
N1 Eu1 O8 69.9(2) . 2_657 ?
O1 Eu1 O8 85.1(2) . 2_657 ?
O3 Eu1 C10 108.9(2) . 2_657 ?
O9 Eu1 C10 151.7(2) . 2_657 ?
O10 Eu1 C10 138.8(2) . 2_657 ?
O2 Eu1 C10 70.5(2) 1_655 2_657 ?
O7 Eu1 C10 26.2(2) 2_657 2_657 ?
O1 Eu1 C10 98.5(2) 2_647 2_657 ?
N1 Eu1 C10 89.6(2) . 2_657 ?
O1 Eu1 C10 79.2(2) . 2_657 ?
O8 Eu1 C10 25.4(2) 2_657 2_657 ?
O3 Eu1 Eu1 150.70(16) . 2_647 ?
O9 Eu1 Eu1 73.00(16) . 2_647 ?
O10 Eu1 Eu1 104.91(16) . 2_647 ?
O2 Eu1 Eu1 128.90(14) 1_655 2_647 ?
O7 Eu1 Eu1 70.17(14) 2_657 2_647 ?
O1 Eu1 Eu1 32.83(13) 2_647 2_647 ?
N1 Eu1 Eu1 94.32(16) . 2_647 ?
O1 Eu1 Eu1 32.38(13) . 2_647 ?
O8 Eu1 Eu1 105.56(15) 2_657 2_647 ?
C10 Eu1 Eu1 88.61(16) 2_657 2_647 ?
C7 O1 Eu1 117.8(5) . 2_647 ?
C7 O1 Eu1 121.1(5) . . ?
Eu1 O1 Eu1 114.8(2) 2_647 . ?
C7 O2 Eu1 161.0(6) . 1_455 ?
C6 O3 Eu1 126.9(6) . . ?
C13 O6 H6 109.4 . . ?
C10 O7 Eu1 95.4(5) . 2_657 ?
C10 O8 Eu1 92.8(5) . 2_657 ?
Eu1 O9 H9A 124.0 . . ?
Eu1 O9 H9B 123.3 . . ?
H9A O9 H9B 111.8 . . ?
Eu1 O10 H10A 120.1 . . ?
Eu1 O10 H10B 119.9 . . ?
H10A O10 H10B 120.0 . . ?
C5 N1 C1 118.7(8) . . ?
C5 N1 Eu1 120.3(6) . . ?
C1 N1 Eu1 120.9(5) . . ?
N1 C1 C2 122.2(8) . . ?
N1 C1 C7 114.5(7) . . ?
C2 C1 C7 123.1(8) . . ?
C1 C2 C3 119.1(9) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 118.6(8) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 118.1(8) . . ?
C5 C4 C8 124.8(8) . . ?
C3 C4 C8 116.7(8) . . ?
N1 C5 C4 122.9(8) . . ?
N1 C5 C6 112.8(7) . . ?
C4 C5 C6 124.2(7) . . ?
O4 C6 O3 123.4(9) . . ?
O4 C6 C5 121.7(8) . . ?
O3 C6 C5 115.0(8) . . ?
O2 C7 O1 123.9(7) . . ?
O2 C7 C1 119.0(7) . . ?
O1 C7 C1 117.0(7) . . ?
C9 C8 C15 119.6(8) . . ?
C9 C8 C4 125.4(8) . . ?
C15 C8 C4 114.7(7) . . ?
C8 C9 C11 117.6(8) . . ?
C8 C9 C10 122.6(8) . . ?
C11 C9 C10 119.8(8) . . ?
O8 C10 O7 120.1(8) . . ?
O8 C10 C9 121.7(7) . . ?
O7 C10 C9 118.2(8) . . ?
O8 C10 Eu1 61.8(4) . 2_657 ?
O7 C10 Eu1 58.4(4) . 2_657 ?
C9 C10 Eu1 175.9(6) . 2_657 ?
C12 C11 C9 122.7(8) . . ?
C12 C11 H11 118.7 . . ?
C9 C11 H11 118.7 . . ?
C11 C12 C14 119.1(8) . . ?
C11 C12 C13 121.7(8) . . ?
C14 C12 C13 119.2(8) . . ?
O5 C13 O6 123.7(8) . . ?
O5 C13 C12 123.8(8) . . ?
O6 C13 C12 112.4(8) . . ?
C15 C14 C12 119.9(9) . . ?
C15 C14 H14 120.1 . . ?
C12 C14 H14 120.1 . . ?
C14 C15 C8 121.1(9) . . ?
C14 C15 H15 119.4 . . ?
C8 C15 H15 119.4 . . ?
H13A O13 H13B 109.5 . . ?
H13A O13 H12A 20.4 . . ?
H13B O13 H12A 118.9 . . ?
H13A O12 H12B 121.7 . . ?
H13A O12 H12A 23.3 . . ?
H12B O12 H12A 109.5 . . ?
H11B O11 H11A 105.2 . . ?

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
O3 Eu1 O1 C7 -1.7(7) . . . . ?
O9 Eu1 O1 C7 -67.6(6) . . . . ?
O10 Eu1 O1 C7 -108.1(6) . . . . ?
O2 Eu1 O1 C7 131.9(6) 1_655 . . . ?
O7 Eu1 O1 C7 130.3(6) 2_657 . . . ?
O1 Eu1 O1 C7 -151.4(7) 2_647 . . . ?
N1 Eu1 O1 C7 8.9(6) . . . . ?
O8 Eu1 O1 C7 78.9(6) 2_657 . . . ?
C10 Eu1 O1 C7 103.9(6) 2_657 . . . ?
Eu1 Eu1 O1 C7 -151.4(7) 2_647 . . . ?
O3 Eu1 O1 Eu1 149.7(2) . . . 2_647 ?
O9 Eu1 O1 Eu1 83.7(3) . . . 2_647 ?
O10 Eu1 O1 Eu1 43.3(4) . . . 2_647 ?
O2 Eu1 O1 Eu1 -76.7(4) 1_655 . . 2_647 ?
O7 Eu1 O1 Eu1 -78.3(2) 2_657 . . 2_647 ?
O1 Eu1 O1 Eu1 0.0 2_647 . . 2_647 ?
N1 Eu1 O1 Eu1 160.3(3) . . . 2_647 ?
O8 Eu1 O1 Eu1 -129.7(3) 2_657 . . 2_647 ?
C10 Eu1 O1 Eu1 -104.7(3) 2_657 . . 2_647 ?
O9 Eu1 O3 C6 84.7(8) . . . . ?
O10 Eu1 O3 C6 154.3(8) . . . . ?
O2 Eu1 O3 C6 -133.2(8) 1_655 . . . ?
O7 Eu1 O3 C6 -80.0(8) 2_657 . . . ?
O1 Eu1 O3 C6 127.5(7) 2_647 . . . ?
N1 Eu1 O3 C6 11.7(7) . . . . ?
O1 Eu1 O3 C6 22.3(8) . . . . ?
O8 Eu1 O3 C6 -58.1(7) 2_657 . . . ?
C10 Eu1 O3 C6 -68.0(8) 2_657 . . . ?
Eu1 Eu1 O3 C6 55.8(9) 2_647 . . . ?
O3 Eu1 N1 C5 -8.7(6) . . . . ?
O9 Eu1 N1 C5 -98.4(6) . . . . ?
O10 Eu1 N1 C5 -56.5(7) . . . . ?
O2 Eu1 N1 C5 38.9(7) 1_655 . . . ?
O7 Eu1 N1 C5 120.7(6) 2_657 . . . ?
O1 Eu1 N1 C5 -157.1(6) 2_647 . . . ?
O1 Eu1 N1 C5 -179.2(7) . . . . ?
O8 Eu1 N1 C5 86.3(6) 2_657 . . . ?
C10 Eu1 N1 C5 102.7(6) 2_657 . . . ?
Eu1 Eu1 N1 C5 -168.7(6) 2_647 . . . ?
O3 Eu1 N1 C1 173.3(7) . . . . ?
O9 Eu1 N1 C1 83.6(6) . . . . ?
O10 Eu1 N1 C1 125.5(6) . . . . ?
O2 Eu1 N1 C1 -139.1(6) 1_655 . . . ?
O7 Eu1 N1 C1 -57.2(6) 2_657 . . . ?
O1 Eu1 N1 C1 24.9(7) 2_647 . . . ?
O1 Eu1 N1 C1 2.8(6) . . . . ?
O8 Eu1 N1 C1 -91.7(6) 2_657 . . . ?
C10 Eu1 N1 C1 -75.3(6) 2_657 . . . ?
Eu1 Eu1 N1 C1 13.3(6) 2_647 . . . ?
C5 N1 C1 C2 -4.7(12) . . . . ?
Eu1 N1 C1 C2 173.3(6) . . . . ?
C5 N1 C1 C7 170.0(7) . . . . ?
Eu1 N1 C1 C7 -12.0(9) . . . . ?
N1 C1 C2 C3 2.3(13) . . . . ?
C7 C1 C2 C3 -171.9(8) . . . . ?
C1 C2 C3 C4 3.0(13) . . . . ?
C2 C3 C4 C5 -5.7(13) . . . . ?
C2 C3 C4 C8 167.5(8) . . . . ?
C1 N1 C5 C4 1.7(12) . . . . ?
Eu1 N1 C5 C4 -176.3(6) . . . . ?
C1 N1 C5 C6 -175.8(7) . . . . ?
Eu1 N1 C5 C6 6.2(9) . . . . ?
C3 C4 C5 N1 3.5(13) . . . . ?
C8 C4 C5 N1 -169.1(8) . . . . ?
C3 C4 C5 C6 -179.3(8) . . . . ?
C8 C4 C5 C6 8.1(13) . . . . ?
Eu1 O3 C6 O4 168.9(8) . . . . ?
Eu1 O3 C6 C5 -12.9(11) . . . . ?
N1 C5 C6 O4 -178.5(9) . . . . ?
C4 C5 C6 O4 4.0(14) . . . . ?
N1 C5 C6 O3 3.3(11) . . . . ?
C4 C5 C6 O3 -174.2(8) . . . . ?
Eu1 O2 C7 O1 -145.1(14) 1_455 . . . ?
Eu1 O2 C7 C1 30(2) 1_455 . . . ?
Eu1 O1 C7 O2 6.5(11) 2_647 . . . ?
Eu1 O1 C7 O2 157.1(6) . . . . ?
Eu1 O1 C7 C1 -168.9(5) 2_647 . . . ?
Eu1 O1 C7 C1 -18.3(10) . . . . ?
N1 C1 C7 O2 -155.9(8) . . . . ?
C2 C1 C7 O2 18.7(13) . . . . ?
N1 C1 C7 O1 19.8(11) . . . . ?
C2 C1 C7 O1 -165.6(8) . . . . ?
C5 C4 C8 C9 -109.5(10) . . . . ?
C3 C4 C8 C9 77.9(11) . . . . ?
C5 C4 C8 C15 76.6(11) . . . . ?
C3 C4 C8 C15 -96.0(10) . . . . ?
C15 C8 C9 C11 -0.4(13) . . . . ?
C4 C8 C9 C11 -174.0(8) . . . . ?
C15 C8 C9 C10 179.2(8) . . . . ?
C4 C8 C9 C10 5.6(13) . . . . ?
Eu1 O8 C10 O7 3.4(8) 2_657 . . . ?
Eu1 O8 C10 C9 -177.5(7) 2_657 . . . ?
Eu1 O7 C10 O8 -3.5(9) 2_657 . . . ?
Eu1 O7 C10 C9 177.4(6) 2_657 . . . ?
C8 C9 C10 O8 11.7(13) . . . . ?
C11 C9 C10 O8 -168.7(8) . . . . ?
C8 C9 C10 O7 -169.2(8) . . . . ?
C11 C9 C10 O7 10.4(12) . . . . ?
C8 C9 C10 Eu1 -136(8) . . . 2_657 ?
C11 C9 C10 Eu1 44(8) . . . 2_657 ?
C8 C9 C11 C12 1.0(13) . . . . ?
C10 C9 C11 C12 -178.7(8) . . . . ?
C9 C11 C12 C14 -2.0(14) . . . . ?
C9 C11 C12 C13 -179.0(8) . . . . ?
C11 C12 C13 O5 -178.4(9) . . . . ?
C14 C12 C13 O5 4.6(14) . . . . ?
C11 C12 C13 O6 1.7(12) . . . . ?
C14 C12 C13 O6 -175.3(8) . . . . ?
C11 C12 C14 C15 2.5(15) . . . . ?
C13 C12 C14 C15 179.6(9) . . . . ?
C12 C14 C15 C8 -2.0(16) . . . . ?
C9 C8 C15 C14 0.9(14) . . . . ?
C4 C8 C15 C14 175.2(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         3.131
_refine_diff_density_min         -1.924
_refine_diff_density_rms         0.227




_database_code_depnum_ccdc_archive 'CCDC 979201'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Gd N O12'
_chemical_formula_weight         557.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   14.467(3)
_cell_length_b                   7.2520(15)
_cell_length_c                   20.749(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.16(2)
_cell_angle_gamma                90.00
_cell_volume                     1757.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4007
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.49

_exptl_crystal_description       0
_exptl_crystal_colour            0
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1084
_exptl_absorpt_coefficient_mu    3.844
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3918
_exptl_absorpt_correction_T_max  0.5136
_exptl_absorpt_process_details   SADABS

_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17078
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4007
_reflns_number_gt                3610
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0367P)²+0.4437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4007
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.003
_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
O6 O 0.8223(2) 0.7913(4) 1.00204(15) 0.0298(6) Uani 1 1 d . . .
C10 C 0.7678(3) 0.7683(5) 0.9272(2) 0.0228(7) Uani 1 1 d . . .
C9 C 0.6495(3) 0.6829(5) 0.8841(2) 0.0191(7) Uani 1 1 d . . .
Gd1 Gd 1.007402(12) 0.20714(2) 0.872574(8) 0.01584(7) Uani 1 1 d . . .
C11 C 0.5883(3) 0.7050(5) 0.9160(2) 0.0210(7) Uani 1 1 d . . .
O10 O 0.8722(2) -0.0013(4) 0.76661(16) 0.0265(6) Uani 1 1 d . . .
O9 O 1.0071(2) -0.0975(4) 0.92374(16) 0.0263(6) Uani 1 1 d . . .
O1 O 0.9034(2) 0.2415(4) 0.92569(16) 0.0313(6) Uani 1 1 d . . .
N1 N 0.8263(2) 0.4046(4) 0.79163(16) 0.0194(6) Uani 1 1 d . . .
O5 O 0.8017(3) 0.8114(5) 0.88680(19) 0.0464(9) Uani 1 1 d . . .
O3 O 0.9660(2) 0.3513(4) 0.75091(15) 0.0256(5) Uani 1 1 d . . .
C8 C 0.5989(3) 0.5902(5) 0.81106(19) 0.0183(6) Uani 1 1 d . . .
O2 O 0.7640(3) 0.3445(5) 0.93088(18) 0.0422(8) Uani 1 1 d . . .
C12 C 0.4748(3) 0.6420(5) 0.8745(2) 0.0226(7) Uani 1 1 d . . .
C3 C 0.6647(3) 0.5438(5) 0.77823(19) 0.0182(6) Uani 1 1 d . . .
C6 C 0.7966(3) 0.4846(5) 0.72408(19) 0.0197(7) Uani 1 1 d . . .
O4 O 0.86805(19) 0.5495(4) 0.64865(14) 0.0254(5) Uani 1 1 d . . .
C2 C 0.7639(3) 0.4323(5) 0.81940(19) 0.0203(7) Uani 1 1 d . . .
O11 O 1.0742(3) 0.5258(5) 0.9077(2) 0.0519(10) Uani 1 1 d . . .
C4 C 0.6288(3) 0.6095(5) 0.7039(2) 0.0232(7) Uani 1 1 d . . .
C7 C 0.8827(3) 0.4589(5) 0.70571(19) 0.0201(6) Uani 1 1 d . . .
C14 C 0.4223(3) 0.5637(5) 0.7990(2) 0.0240(7) Uani 1 1 d . . .
C1 C 0.8113(3) 0.3324(5) 0.8974(2) 0.0247(7) Uani 1 1 d . . .
C5 C 0.6960(3) 0.5857(5) 0.6765(2) 0.0235(7) Uani 1 1 d . . .
C15 C 0.4836(3) 0.5358(5) 0.7680(2) 0.0232(7) Uani 1 1 d . . .
O7 O 0.4665(2) 0.7521(5) 0.97812(19) 0.0430(8) Uani 1 1 d . . .
O8 O 0.3117(2) 0.6141(5) 0.87627(17) 0.0426(8) Uani 1 1 d . . .
C13 C 0.4096(3) 0.6662(6) 0.9091(2) 0.0265(8) Uani 1 1 d . . .
O12 O 0.6660(4) 0.3683(6) 0.4838(3) 0.0511(9) Uani 1 1 d . . .
H1 H 0.628(3) 0.750(6) 0.964(2) 0.021(10) Uiso 1 1 d . . .
H3 H 0.445(3) 0.483(6) 0.716(2) 0.021(10) Uiso 1 1 d . . .
H4 H 0.567(4) 0.686(6) 0.676(3) 0.038(13) Uiso 1 1 d . . .
H2 H 0.348(3) 0.522(6) 0.772(2) 0.029(11) Uiso 1 1 d . . .
H5 H 0.667(4) 0.630(8) 0.626(3) 0.049(14) Uiso 1 1 d . . .
H10A H 0.911(4) -0.054(7) 0.753(3) 0.030(11) Uiso 1 1 d . . .
H7 H 0.427(5) 0.780(8) 0.997(4) 0.062(18) Uiso 1 1 d . . .
H11A H 1.137(5) 0.540(9) 0.960(4) 0.08(2) Uiso 1 1 d . . .
H11B H 1.047(5) 0.607(11) 0.885(4) 0.06(2) Uiso 1 1 d . . .
H10B H 0.824(5) 0.027(9) 0.725(3) 0.066(19) Uiso 1 1 d . . .
H9A H 0.957(4) -0.134(8) 0.913(3) 0.048(17) Uiso 1 1 d . . .
H9B H 1.063(5) -0.137(9) 0.985(4) 0.070(17) Uiso 1 1 d . . .
H12B H 0.735(7) 0.371(13) 0.522(5) 0.13(4) Uiso 1 1 d . . .
H12A H 0.690(6) 0.303(9) 0.466(4) 0.07(2) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 C10 1.271(4) . ?
O6 Gd1 2.297(3) 3_767 ?
C10 O5 1.234(5) . ?
C10 C9 1.519(5) . ?
C9 C11 1.392(5) . ?
C9 C8 1.406(5) . ?
Gd1 O6 2.297(3) 3_767 ?
Gd1 O1 2.344(3) . ?
Gd1 O4 2.384(2) 2_746 ?
Gd1 O10 2.423(3) . ?
Gd1 O11 2.444(4) . ?
Gd1 O9 2.452(3) . ?
Gd1 O3 2.458(3) . ?
Gd1 N1 2.558(3) . ?
C11 C12 1.406(5) . ?
C11 H1 0.88(4) . ?
O10 H10A 0.85(5) . ?
O10 H10B 0.75(6) . ?
O9 H9A 0.68(5) . ?
O9 H9B 1.07(6) . ?
O1 C1 1.277(4) . ?
N1 C6 1.333(4) . ?
N1 C2 1.342(4) . ?
O3 C7 1.268(4) . ?
C8 C15 1.405(4) . ?
C8 C3 1.500(4) . ?
O2 C1 1.232(4) . ?
C12 C14 1.395(5) . ?
C12 C13 1.495(5) . ?
C3 C4 1.389(5) . ?
C3 C2 1.413(4) . ?
C6 C5 1.391(5) . ?
C6 C7 1.513(4) . ?
O4 C7 1.258(4) . ?
O4 Gd1 2.384(2) 2_756 ?
C2 C1 1.519(5) . ?
O11 H11A 0.92(6) . ?
O11 H11B 0.71(7) . ?
C4 C5 1.397(5) . ?
C4 H4 0.91(5) . ?
C14 C15 1.386(5) . ?
C14 H2 0.92(4) . ?
C5 H5 0.93(5) . ?
C15 H3 0.95(4) . ?
O7 C13 1.314(5) . ?
O7 H7 0.90(6) . ?
O8 C13 1.215(4) . ?
O12 H12B 0.84(8) . ?
O12 H12A 0.79(7) . ?

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
C10 O6 Gd1 149.5(2) . 3_767 ?
O5 C10 O6 126.0(3) . . ?
O5 C10 C9 117.7(3) . . ?
O6 C10 C9 116.3(3) . . ?
C11 C9 C8 119.6(3) . . ?
C11 C9 C10 119.1(3) . . ?
C8 C9 C10 121.3(3) . . ?
O6 Gd1 O1 91.37(10) 3_767 . ?
O6 Gd1 O4 77.82(9) 3_767 2_746 ?
O1 Gd1 O4 154.47(10) . 2_746 ?
O6 Gd1 O10 141.55(10) 3_767 . ?
O1 Gd1 O10 95.41(11) . . ?
O4 Gd1 O10 80.04(9) 2_746 . ?
O6 Gd1 O11 71.73(12) 3_767 . ?
O1 Gd1 O11 90.56(14) . . ?
O4 Gd1 O11 107.43(12) 2_746 . ?
O10 Gd1 O11 145.68(12) . . ?
O6 Gd1 O9 77.80(10) 3_767 . ?
O1 Gd1 O9 74.14(10) . . ?
O4 Gd1 O9 80.94(9) 2_746 . ?
O10 Gd1 O9 67.92(10) . . ?
O11 Gd1 O9 145.49(12) . . ?
O6 Gd1 O3 127.58(10) 3_767 . ?
O1 Gd1 O3 127.06(8) . . ?
O4 Gd1 O3 76.52(9) 2_746 . ?
O10 Gd1 O3 75.90(10) . . ?
O11 Gd1 O3 73.62(12) . . ?
O9 Gd1 O3 140.02(9) . . ?
O6 Gd1 N1 137.70(10) 3_767 . ?
O1 Gd1 N1 63.65(9) . . ?
O4 Gd1 N1 137.75(9) 2_746 . ?
O10 Gd1 N1 77.73(10) . . ?
O11 Gd1 N1 74.82(12) . . ?
O9 Gd1 N1 121.71(9) . . ?
O3 Gd1 N1 63.46(8) . . ?
C9 C11 C12 120.8(3) . . ?
C9 C11 H1 115(3) . . ?
C12 C11 H1 124(3) . . ?
Gd1 O10 H10A 104(3) . . ?
Gd1 O10 H10B 126(5) . . ?
H10A O10 H10B 96(5) . . ?
Gd1 O9 H9A 119(5) . . ?
Gd1 O9 H9B 124(3) . . ?
H9A O9 H9B 102(5) . . ?
C1 O1 Gd1 128.6(2) . . ?
C6 N1 C2 120.4(3) . . ?
C6 N1 Gd1 120.2(2) . . ?
C2 N1 Gd1 119.3(2) . . ?
C7 O3 Gd1 124.8(2) . . ?
C15 C8 C9 119.2(3) . . ?
C15 C8 C3 118.7(3) . . ?
C9 C8 C3 122.0(3) . . ?
C14 C12 C11 119.1(3) . . ?
C14 C12 C13 120.4(3) . . ?
C11 C12 C13 120.5(3) . . ?
C4 C3 C2 116.7(3) . . ?
C4 C3 C8 120.4(3) . . ?
C2 C3 C8 123.0(3) . . ?
N1 C6 C5 121.9(3) . . ?
N1 C6 C7 114.2(3) . . ?
C5 C6 C7 123.9(3) . . ?
C7 O4 Gd1 134.3(2) . 2_756 ?
N1 C2 C3 121.8(3) . . ?
N1 C2 C1 113.0(3) . . ?
C3 C2 C1 125.2(3) . . ?
Gd1 O11 H11A 114(4) . . ?
Gd1 O11 H11B 128(5) . . ?
H11A O11 H11B 117(7) . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 120(3) . . ?
C5 C4 H4 118(3) . . ?
O4 C7 O3 125.2(3) . . ?
O4 C7 C6 117.8(3) . . ?
O3 C7 C6 117.0(3) . . ?
C15 C14 C12 120.4(3) . . ?
C15 C14 H2 121(3) . . ?
C12 C14 H2 119(3) . . ?
O2 C1 O1 123.6(3) . . ?
O2 C1 C2 120.9(3) . . ?
O1 C1 C2 115.4(3) . . ?
C6 C5 C4 117.6(3) . . ?
C6 C5 H5 125(3) . . ?
C4 C5 H5 117(3) . . ?
C14 C15 C8 120.5(3) . . ?
C14 C15 H3 118(2) . . ?
C8 C15 H3 122(2) . . ?
C13 O7 H7 116(4) . . ?
O8 C13 O7 122.1(3) . . ?
O8 C13 C12 123.6(3) . . ?
O7 C13 C12 114.4(3) . . ?
H12B O12 H12A 81(7) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         3.764
_refine_diff_density_min         -1.516
_refine_diff_density_rms         0.152
_database_code_depnum_ccdc_archive 'CCDC 979202'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N O12 Tb'
_chemical_formula_weight         559.19

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           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   14.448(3)
_cell_length_b                   7.1938(14)
_cell_length_c                   20.630(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.15(2)
_cell_angle_gamma                90.00
_cell_volume                     1731.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3976
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    4.156
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3686
_exptl_absorpt_correction_T_max  0.4903
_exptl_absorpt_process_details   SADABS

_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14156
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_sigmaI/netI    0.0864
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.64
_reflns_number_total             3976
_reflns_number_gt                3233
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0637P)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    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3976
_refine_ls_number_parameters     280
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.50733(2) 0.70782(5) 0.872325(17) 0.01938(14) Uani 1 1 d . . .
O6 O 0.3238(4) 1.2916(7) 1.0026(3) 0.0328(12) Uani 1 1 d . . .
C13 C 0.0894(6) 1.2052(10) 0.9166(4) 0.0229(14) Uani 1 1 d . . .
N1 N 0.3280(4) 0.9040(8) 0.7921(3) 0.0216(11) Uani 1 1 d . . .
O11 O 0.5080(4) 0.4032(7) 0.9232(3) 0.0298(11) Uani 1 1 d D . .
H11A H 0.4467 0.3601 0.9143 0.036 Uiso 1 1 d RD . .
O4 O 0.2659(5) 0.8441(9) 0.9316(3) 0.0422(15) Uani 1 1 d . . .
C15 C 0.2696(6) 1.2687(10) 0.9281(4) 0.0261(15) Uani 1 1 d . . .
O3 O 0.4054(4) 0.7445(8) 0.9260(3) 0.0323(12) Uani 1 1 d . . .
C8 C 0.1001(5) 1.0900(10) 0.8117(4) 0.0223(13) Uani 1 1 d . . .
O7 O -0.0325(5) 1.2544(10) 0.9789(4) 0.0447(16) Uani 1 1 d . . .
O5 O 0.3019(5) 1.3150(9) 0.8871(4) 0.0492(17) Uani 1 1 d . . .
O8 O -0.1871(4) 1.1133(10) 0.8758(3) 0.0435(15) Uani 1 1 d . . .
H8A H -0.2131 1.1558 0.8988 0.065 Uiso 1 1 calc R . .
C5 C 0.1660(5) 1.0433(10) 0.7786(4) 0.0214(13) Uani 1 1 d . . .
O2 O 0.4663(4) 0.8511(8) 0.7509(3) 0.0285(11) Uani 1 1 d . . .
C9 C -0.0161(6) 1.0363(11) 0.7673(4) 0.0265(14) Uani 1 1 d . . .
C2 C 0.2973(5) 0.9858(10) 0.7241(4) 0.0203(13) Uani 1 1 d . . .
C7 C 0.3122(6) 0.8328(11) 0.8980(4) 0.0287(16) Uani 1 1 d . . .
C11 C -0.0242(5) 1.1430(10) 0.8747(4) 0.0217(13) Uani 1 1 d . . .
C1 C 0.3840(6) 0.9584(11) 0.7057(4) 0.0250(14) Uani 1 1 d . . .
C14 C 0.1506(6) 1.1852(9) 0.8850(4) 0.0216(14) Uani 1 1 d . . .
O10 O 0.5737(6) 1.0233(9) 0.9065(4) 0.0561(17) Uani 1 1 d . . .
H10A H 0.5259 1.1124 0.8855 0.067 Uiso 1 1 d R . .
H10B H 0.6449 1.0457 0.9395 0.067 Uiso 1 1 d R . .
C4 C 0.1295(6) 1.1103(11) 0.7037(4) 0.0261(15) Uani 1 1 d . . .
C10 C -0.0764(6) 1.0647(11) 0.7989(4) 0.0275(15) Uani 1 1 d . . .
C6 C 0.2653(6) 0.9320(10) 0.8199(4) 0.0225(13) Uani 1 1 d . . .
C3 C 0.1970(6) 1.0862(11) 0.6766(4) 0.0277(15) Uani 1 1 d . . .
C12 C -0.0899(6) 1.1684(12) 0.9084(5) 0.0324(17) Uani 1 1 d . . .
O9 O 0.3736(4) 0.5033(7) 0.7665(3) 0.0319(11) Uani 1 1 d . . .
H9A H 0.3054 0.5392 0.7309 0.038 Uiso 1 1 d R . .
H9B H 0.3943 0.3942 0.7644 0.038 Uiso 1 1 d R . .
O1 O 0.3681(4) 1.0500(8) 0.6482(3) 0.0293(11) Uani 1 1 d . . .
O12 O 0.1680(5) 0.6340(10) 0.9835(4) 0.0521(16) Uani 1 1 d . . .
H12A H 0.1059 0.6957 0.9594 0.063 Uiso 1 1 d R . .
H12B H 0.1860 0.5625 1.0222 0.063 Uiso 1 1 d R . .
H2 H -0.155(8) 1.029(15) 0.774(5) 0.063 Uiso 1 1 d . . .
H4 H 0.076(9) 1.213(14) 0.681(6) 0.063 Uiso 1 1 d . . .
H1 H 0.137(9) 1.267(13) 0.973(6) 0.063 Uiso 1 1 d . . .
H5 H 0.176(8) 1.114(15) 0.620(5) 0.063 Uiso 1 1 d . . .
H3 H -0.062(8) 1.002(14) 0.710(6) 0.063 Uiso 1 1 d . . .
H11B H 0.5620(11) 0.342(10) 0.963(4) 0.063 Uiso 1 1 d 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
Tb1 O6 2.277(5) 3_677 ?
Tb1 O3 2.321(5) . ?
Tb1 O1 2.368(5) 2_646 ?
Tb1 O9 2.385(5) . ?
Tb1 O10 2.402(6) . ?
Tb1 O11 2.427(5) . ?
Tb1 O2 2.436(5) . ?
Tb1 N1 2.527(5) . ?
O6 C15 1.257(9) . ?
O6 Tb1 2.277(5) 3_677 ?
C13 C14 1.381(9) . ?
C13 C11 1.402(9) . ?
C13 H1 1.04(10) . ?
N1 C2 1.333(8) . ?
N1 C6 1.344(8) . ?
O11 H11A 0.8501 . ?
O11 H11B 0.849(10) . ?
O4 C7 1.217(8) . ?
C15 O5 1.229(9) . ?
C15 C14 1.518(9) . ?
O3 C7 1.278(9) . ?
C8 C14 1.409(9) . ?
C8 C9 1.412(9) . ?
C8 C5 1.500(9) . ?
O7 C12 1.327(9) . ?
O8 C12 1.211(9) . ?
O8 H8A 0.8200 . ?
C5 C4 1.393(9) . ?
C5 C6 1.409(9) . ?
O2 C1 1.254(8) . ?
C9 C10 1.377(9) . ?
C9 H3 0.99(9) . ?
C2 C3 1.380(9) . ?
C2 C1 1.521(8) . ?
C7 C6 1.508(9) . ?
C11 C10 1.392(9) . ?
C11 C12 1.483(9) . ?
C1 O1 1.254(8) . ?
O10 H10A 0.8500 . ?
O10 H10B 0.8500 . ?
C4 C3 1.391(9) . ?
C4 H4 0.96(10) . ?
C10 H2 0.96(9) . ?
C3 H5 1.04(9) . ?
O9 H9A 0.8500 . ?
O9 H9B 0.8501 . ?
O1 Tb1 2.368(5) 2_656 ?
O12 H12A 0.8500 . ?
O12 H12B 0.8500 . ?

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
O6 Tb1 O3 90.9(2) 3_677 . ?
O6 Tb1 O1 77.55(19) 3_677 2_646 ?
O3 Tb1 O1 154.53(18) . 2_646 ?
O6 Tb1 O9 141.87(18) 3_677 . ?
O3 Tb1 O9 96.18(19) . . ?
O1 Tb1 O9 80.28(17) 2_646 . ?
O6 Tb1 O10 71.9(2) 3_677 . ?
O3 Tb1 O10 90.5(2) . . ?
O1 Tb1 O10 107.0(2) 2_646 . ?
O9 Tb1 O10 145.0(2) . . ?
O6 Tb1 O11 77.49(18) 3_677 . ?
O3 Tb1 O11 74.86(18) . . ?
O1 Tb1 O11 80.46(18) 2_646 . ?
O9 Tb1 O11 68.48(17) . . ?
O10 Tb1 O11 145.8(2) . . ?
O6 Tb1 O2 127.78(19) 3_677 . ?
O3 Tb1 O2 127.16(16) . . ?
O1 Tb1 O2 76.64(17) 2_646 . ?
O9 Tb1 O2 75.26(18) . . ?
O10 Tb1 O2 73.4(2) . . ?
O11 Tb1 O2 139.72(18) . . ?
O6 Tb1 N1 137.76(19) 3_677 . ?
O3 Tb1 N1 63.58(17) . . ?
O1 Tb1 N1 138.12(17) 2_646 . ?
O9 Tb1 N1 77.36(18) . . ?
O10 Tb1 N1 75.0(2) . . ?
O11 Tb1 N1 121.93(17) . . ?
O2 Tb1 N1 63.67(16) . . ?
C15 O6 Tb1 149.8(5) . 3_677 ?
C14 C13 C11 121.2(6) . . ?
C14 C13 H1 113(6) . . ?
C11 C13 H1 126(6) . . ?
C2 N1 C6 119.6(5) . . ?
C2 N1 Tb1 120.8(4) . . ?
C6 N1 Tb1 119.5(4) . . ?
Tb1 O11 H11A 119.9 . . ?
Tb1 O11 H11B 131(3) . . ?
H11A O11 H11B 105.3 . . ?
O5 C15 O6 126.2(7) . . ?
O5 C15 C14 117.5(7) . . ?
O6 C15 C14 116.2(6) . . ?
C7 O3 Tb1 129.6(4) . . ?
C14 C8 C9 119.7(6) . . ?
C14 C8 C5 122.1(6) . . ?
C9 C8 C5 118.3(6) . . ?
C12 O8 H8A 109.5 . . ?
C4 C5 C6 116.8(6) . . ?
C4 C5 C8 120.1(6) . . ?
C6 C5 C8 123.1(6) . . ?
C1 O2 Tb1 125.1(4) . . ?
C10 C9 C8 119.6(6) . . ?
C10 C9 H3 116(5) . . ?
C8 C9 H3 123(5) . . ?
N1 C2 C3 122.4(6) . . ?
N1 C2 C1 113.2(6) . . ?
C3 C2 C1 124.4(6) . . ?
O4 C7 O3 124.2(6) . . ?
O4 C7 C6 121.6(6) . . ?
O3 C7 C6 114.1(6) . . ?
C10 C11 C13 118.9(6) . . ?
C10 C11 C12 120.3(6) . . ?
C13 C11 C12 120.8(6) . . ?
O2 C1 O1 126.2(6) . . ?
O2 C1 C2 116.9(5) . . ?
O1 C1 C2 116.8(6) . . ?
C13 C14 C8 119.1(6) . . ?
C13 C14 C15 120.1(6) . . ?
C8 C14 C15 120.8(6) . . ?
Tb1 O10 H10A 120.0 . . ?
Tb1 O10 H10B 120.0 . . ?
H10A O10 H10B 120.0 . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4 117(7) . . ?
C5 C4 H4 118(6) . . ?
C9 C10 C11 121.1(6) . . ?
C9 C10 H2 125(6) . . ?
C11 C10 H2 113(6) . . ?
N1 C6 C5 122.0(6) . . ?
N1 C6 C7 113.2(6) . . ?
C5 C6 C7 124.8(6) . . ?
C2 C3 C4 118.1(6) . . ?
C2 C3 H5 113(5) . . ?
C4 C3 H5 128(5) . . ?
O8 C12 O7 122.2(7) . . ?
O8 C12 C11 123.5(7) . . ?
O7 C12 C11 114.3(6) . . ?
Tb1 O9 H9A 120.2 . . ?
Tb1 O9 H9B 119.8 . . ?
H9A O9 H9B 120.0 . . ?
C1 O1 Tb1 133.4(4) . 2_656 ?
H12A O12 H12B 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         4.404
_refine_diff_density_min         -1.807
_refine_diff_density_rms         0.237
_database_code_depnum_ccdc_archive 'CCDC 979208'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Dy N O12'
_chemical_formula_weight         562.77

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'
Dy Dy -0.1892 4.4098 '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           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   14.496(3)
_cell_length_b                   7.1990(14)
_cell_length_c                   20.714(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.33(2)
_cell_angle_gamma                90.00
_cell_volume                     1741.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3966
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.48

_exptl_crystal_description       0
_exptl_crystal_colour            0
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1092
_exptl_absorpt_coefficient_mu    4.362
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3545
_exptl_absorpt_correction_T_max  0.4758
_exptl_absorpt_process_details   SADABS

_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16730
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3966
_reflns_number_gt                3650
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0265P)²+2.4450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3966
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0593
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
H11 H 0.233(9) 0.887(15) 1.019(6) 0.16(4) Uiso 1 1 d . . .
Dy1 Dy 0.492890(11) 0.291264(19) 0.627825(7) 0.01478(6) Uani 1 1 d . . .
O3 O 0.6752(2) -0.2897(3) 0.49620(14) 0.0281(5) Uani 1 1 d . . .
C8 C 0.9102(3) -0.2046(4) 0.58339(19) 0.0186(6) Uani 1 1 d . . .
O9 O 0.6278(2) 0.4975(4) 0.73293(15) 0.0249(5) Uani 1 1 d . . .
O10 O 0.4928(2) 0.5947(4) 0.57719(15) 0.0247(5) Uani 1 1 d . . .
N1 N 0.6711(2) 0.0955(4) 0.70746(14) 0.0175(5) Uani 1 1 d . . .
C7 C 0.7304(3) -0.2683(5) 0.57147(19) 0.0199(6) Uani 1 1 d . . .
O6 O 0.5929(2) 0.2566(4) 0.57318(14) 0.0291(6) Uani 1 1 d . . .
O2 O 1.0326(2) -0.2526(5) 0.52151(17) 0.0393(7) Uani 1 1 d . . .
O4 O 0.6968(2) -0.3157(4) 0.61178(17) 0.0428(8) Uani 1 1 d . . .
O5 O 0.7332(2) 0.1566(4) 0.56799(17) 0.0387(7) Uani 1 1 d . . .
C5 C 0.8992(2) -0.0907(4) 0.68878(17) 0.0167(6) Uani 1 1 d . . .
C4 C 1.0142(3) -0.0377(5) 0.73221(19) 0.0210(6) Uani 1 1 d . . .
O7 O 0.53231(19) 0.1486(3) 0.74863(13) 0.0245(5) Uani 1 1 d . . .
C12 C 0.7018(3) 0.0144(4) 0.77611(17) 0.0183(6) Uani 1 1 d . . .
O1 O 1.1872(2) -0.1131(5) 0.62405(15) 0.0392(7) Uani 1 1 d . . .
O11 O 0.4268(3) -0.0249(5) 0.5935(2) 0.0480(9) Uani 1 1 d . . .
C2 C 1.0237(3) -0.1426(5) 0.62544(18) 0.0202(6) Uani 1 1 d . . .
C14 C 0.7339(3) 0.0675(4) 0.67998(17) 0.0171(6) Uani 1 1 d . . .
C15 C 0.6855(3) 0.1669(5) 0.60140(19) 0.0229(7) Uani 1 1 d . . .
C10 C 0.8690(3) -0.1117(5) 0.79628(19) 0.0222(6) Uani 1 1 d . . .
C9 C 0.8332(2) -0.0444(4) 0.72140(17) 0.0170(6) Uani 1 1 d . . .
C3 C 1.0763(3) -0.0654(5) 0.70134(19) 0.0227(6) Uani 1 1 d . . .
C13 C 0.6153(3) 0.0406(4) 0.79421(17) 0.0188(6) Uani 1 1 d . . .
O8 O 0.63017(19) -0.0511(3) 0.85154(13) 0.0238(5) Uani 1 1 d . . .
C6 C 0.8489(3) -0.1839(4) 0.61498(18) 0.0176(6) Uani 1 1 d . . .
C1 C 1.0890(3) -0.1666(5) 0.5910(2) 0.0253(7) Uani 1 1 d . . .
C11 C 0.8023(3) -0.0872(5) 0.82356(19) 0.0228(7) Uani 1 1 d . . .
O12 O 0.1666(3) 0.8680(5) 0.9843(3) 0.0485(8) Uani 1 1 d . . .
H2 H 1.149(3) -0.031(6) 0.729(2) 0.026(10) Uiso 1 1 d . . .
H4 H 0.928(4) -0.180(6) 0.825(3) 0.031(11) Uiso 1 1 d . . .
H5 H 0.826(3) -0.134(5) 0.873(2) 0.022(9) Uiso 1 1 d . . .
H1 H 0.868(3) -0.258(5) 0.529(2) 0.017(9) Uiso 1 1 d . . .
H3 H 1.052(3) 0.012(5) 0.785(2) 0.025(10) Uiso 1 1 d . . .
H6 H 0.592(3) 0.551(6) 0.744(2) 0.022(10) Uiso 1 1 d . . .
H7 H 0.682(4) 0.456(7) 0.776(3) 0.050(14) Uiso 1 1 d . . .
H13 H 0.548(4) 0.621(7) 0.587(3) 0.048(15) Uiso 1 1 d . . .
H12 H 0.447(4) 0.623(7) 0.531(3) 0.039(13) Uiso 1 1 d . . .
H8 H 0.374(7) -0.058(11) 0.553(5) 0.11(3) Uiso 1 1 d . . .
H10 H 0.190(6) 0.799(8) 0.969(4) 0.07(2) Uiso 1 1 d . . .
H9 H 0.456(5) -0.104(9) 0.611(3) 0.050(18) Uiso 1 1 d . . .
H14 H 1.073(4) -0.285(6) 0.509(3) 0.045(14) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O3 2.263(2) 3_656 ?
Dy1 O6 2.322(2) . ?
Dy1 O8 2.357(2) 2_656 ?
Dy1 O9 2.393(2) . ?
Dy1 O11 2.408(3) . ?
Dy1 O10 2.423(2) . ?
Dy1 O7 2.439(2) . ?
Dy1 N1 2.516(3) . ?
O3 C7 1.272(4) . ?
O3 Dy1 2.263(2) 3_656 ?
C8 C6 1.388(4) . ?
C8 C2 1.402(4) . ?
C8 H1 0.98(4) . ?
O9 H6 0.79(4) . ?
O9 H7 0.82(5) . ?
O10 H13 0.73(5) . ?
O10 H12 0.81(5) . ?
N1 C14 1.345(4) . ?
N1 C12 1.346(4) . ?
C7 O4 1.237(4) . ?
C7 C6 1.516(4) . ?
O6 C15 1.277(4) . ?
O2 C1 1.315(4) . ?
O2 H14 0.81(5) . ?
O5 C15 1.236(4) . ?
C5 C4 1.399(4) . ?
C5 C6 1.414(4) . ?
C5 C9 1.500(4) . ?
C4 C3 1.394(4) . ?
C4 H3 0.96(4) . ?
O7 C13 1.264(4) . ?
C12 C11 1.389(4) . ?
C12 C13 1.518(4) . ?
O1 C1 1.220(4) . ?
O11 H8 0.77(8) . ?
O11 H9 0.67(6) . ?
C2 C3 1.393(4) . ?
C2 C1 1.495(4) . ?
C14 C9 1.412(4) . ?
C14 C15 1.517(4) . ?
C10 C11 1.390(4) . ?
C10 C9 1.399(4) . ?
C10 H4 0.86(4) . ?
C3 H2 0.89(4) . ?
C13 O8 1.261(4) . ?
O8 Dy1 2.357(2) 2_646 ?
C11 H5 0.93(4) . ?
O12 H11 0.80(10) . ?
O12 H10 0.76(7) . ?

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
O3 Dy1 O6 90.56(10) 3_656 . ?
O3 Dy1 O8 77.67(9) 3_656 2_656 ?
O6 Dy1 O8 153.96(8) . 2_656 ?
O3 Dy1 O9 141.82(9) 3_656 . ?
O6 Dy1 O9 95.76(10) . . ?
O8 Dy1 O9 80.49(9) 2_656 . ?
O3 Dy1 O11 71.80(12) 3_656 . ?
O6 Dy1 O11 90.49(12) . . ?
O8 Dy1 O11 107.29(12) 2_656 . ?
O9 Dy1 O11 145.39(11) . . ?
O3 Dy1 O10 77.82(9) 3_656 . ?
O6 Dy1 O10 74.10(9) . . ?
O8 Dy1 O10 80.70(9) 2_656 . ?
O9 Dy1 O10 67.97(9) . . ?
O11 Dy1 O10 145.74(11) . . ?
O3 Dy1 O7 127.07(9) 3_656 . ?
O6 Dy1 O7 128.34(8) . . ?
O8 Dy1 O7 76.07(8) 2_656 . ?
O9 Dy1 O7 76.08(9) . . ?
O11 Dy1 O7 73.45(11) . . ?
O10 Dy1 O7 139.79(9) . . ?
O3 Dy1 N1 137.60(9) 3_656 . ?
O6 Dy1 N1 64.16(8) . . ?
O8 Dy1 N1 138.08(8) 2_656 . ?
O9 Dy1 N1 77.45(9) . . ?
O11 Dy1 N1 74.83(12) . . ?
O10 Dy1 N1 121.71(9) . . ?
O7 Dy1 N1 64.28(8) . . ?
C7 O3 Dy1 149.8(2) . 3_656 ?
C6 C8 C2 121.1(3) . . ?
C6 C8 H1 116(2) . . ?
C2 C8 H1 123(2) . . ?
Dy1 O9 H6 104(3) . . ?
Dy1 O9 H7 120(4) . . ?
H6 O9 H7 104(4) . . ?
Dy1 O10 H13 113(4) . . ?
Dy1 O10 H12 122(3) . . ?
H13 O10 H12 105(5) . . ?
C14 N1 C12 120.0(3) . . ?
C14 N1 Dy1 119.74(19) . . ?
C12 N1 Dy1 120.26(19) . . ?
O4 C7 O3 125.5(3) . . ?
O4 C7 C6 118.0(3) . . ?
O3 C7 C6 116.4(3) . . ?
C15 O6 Dy1 128.5(2) . . ?
C1 O2 H14 114(4) . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 C9 119.0(3) . . ?
C6 C5 C9 122.3(3) . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H3 120(2) . . ?
C5 C4 H3 119(2) . . ?
C13 O7 Dy1 124.48(19) . . ?
N1 C12 C11 121.8(3) . . ?
N1 C12 C13 113.7(3) . . ?
C11 C12 C13 124.4(3) . . ?
Dy1 O11 H8 125(6) . . ?
Dy1 O11 H9 129(5) . . ?
H8 O11 H9 103(7) . . ?
C3 C2 C8 119.0(3) . . ?
C3 C2 C1 120.4(3) . . ?
C8 C2 C1 120.5(3) . . ?
N1 C14 C9 122.0(3) . . ?
N1 C14 C15 112.6(3) . . ?
C9 C14 C15 125.3(3) . . ?
O5 C15 O6 124.0(3) . . ?
O5 C15 C14 121.1(3) . . ?
O6 C15 C14 115.0(3) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H4 116(3) . . ?
C9 C10 H4 122(3) . . ?
C10 C9 C14 116.5(3) . . ?
C10 C9 C5 120.4(3) . . ?
C14 C9 C5 123.1(3) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H2 120(2) . . ?
C4 C3 H2 120(2) . . ?
O8 C13 O7 125.6(3) . . ?
O8 C13 C12 117.5(3) . . ?
O7 C13 C12 116.9(3) . . ?
C13 O8 Dy1 134.2(2) . 2_646 ?
C8 C6 C5 119.8(3) . . ?
C8 C6 C7 119.5(3) . . ?
C5 C6 C7 120.7(3) . . ?
O1 C1 O2 121.6(3) . . ?
O1 C1 C2 123.6(3) . . ?
O2 C1 C2 114.7(3) . . ?
C12 C11 C10 118.1(3) . . ?
C12 C11 H5 121(2) . . ?
C10 C11 H5 121(2) . . ?
H11 O12 H10 83(8) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         3.801
_refine_diff_density_min         -0.988
_refine_diff_density_rms         0.124
_database_code_depnum_ccdc_archive 'CCDC 979198'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Ho N O12'
_chemical_formula_weight         565.20

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'
Ho Ho -0.2175 4.6783 '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           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   14.476(3)
_cell_length_b                   7.1810(14)
_cell_length_c                   20.617(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.13(2)
_cell_angle_gamma                90.00
_cell_volume                     1731.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3955
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    4.643
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3364
_exptl_absorpt_correction_T_max  0.4570
_exptl_absorpt_process_details   SADABS

_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17108
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3955
_reflns_number_gt                3474
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0241P)²+3.2144P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3955
_refine_ls_number_parameters     286
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
O12 O 0.1660(4) 0.8661(6) 0.9841(3) 0.0548(12) Uani 1 1 d . . .
H12A H 0.2271 0.9132 1.0200 0.082 Uiso 1 1 d R . .
Ho1 Ho 0.493057(15) 0.20920(3) 0.128013(11) 0.01747(7) Uani 1 1 d . . .
O1 O 0.3711(3) 0.0519(5) 0.14860(18) 0.0256(7) Uani 1 1 d . . .
O3 O 0.4084(3) -0.2552(5) 0.4273(2) 0.0316(8) Uani 1 1 d . . .
O4 O 0.2679(3) -0.1576(5) 0.4322(2) 0.0403(9) Uani 1 1 d . . .
O6 O 0.3044(3) 0.3160(6) 0.3890(2) 0.0454(10) Uani 1 1 d . . .
O5 O 0.3254(3) 0.2893(5) 0.50430(19) 0.0321(8) Uani 1 1 d . . .
O7 O -0.0321(3) 0.2519(6) 0.4783(2) 0.0430(10) Uani 1 1 d . . .
O8 O -0.1867(3) 0.1127(6) 0.3752(2) 0.0424(9) Uani 1 1 d . . .
O11 O 0.4926(3) -0.0925(5) 0.0772(2) 0.0269(7) Uani 1 1 d . . .
O2 O 0.4686(3) -0.1488(5) 0.25167(18) 0.0262(7) Uani 1 1 d . . .
O10 O 0.6274(3) 0.0039(5) 0.23230(19) 0.0272(7) Uani 1 1 d D . .
O9 O 0.4271(4) 0.5239(5) 0.0941(2) 0.0500(11) Uani 1 1 d D . .
N1 N 0.3301(3) -0.0951(5) 0.2929(2) 0.0184(7) Uani 1 1 d . . .
C1 C 0.3860(4) -0.0408(6) 0.2063(3) 0.0218(9) Uani 1 1 d . . .
C2 C 0.2993(4) -0.0144(6) 0.2239(2) 0.0210(9) Uani 1 1 d . . .
C3 C 0.1991(4) 0.0878(6) 0.1768(3) 0.0249(10) Uani 1 1 d . . .
H3 H 0.1771 0.1384 0.1281 0.030 Uiso 1 1 calc R . .
C4 C 0.1329(4) 0.1123(6) 0.2042(3) 0.0241(9) Uani 1 1 d . . .
H4 H 0.0634 0.1746 0.1720 0.029 Uiso 1 1 calc R . .
C5 C 0.1680(3) 0.0459(6) 0.2786(2) 0.0197(8) Uani 1 1 d . . .
C6 C 0.2675(4) -0.0663(6) 0.3202(2) 0.0202(8) Uani 1 1 d . . .
C7 C 0.3160(4) -0.1669(6) 0.3990(3) 0.0241(9) Uani 1 1 d . . .
C8 C 0.1024(3) 0.0912(6) 0.3117(2) 0.0197(8) Uani 1 1 d . . .
C9 C 0.1523(3) 0.1842(6) 0.3850(2) 0.0185(8) Uani 1 1 d . . .
C10 C 0.2705(4) 0.2690(6) 0.4290(3) 0.0236(9) Uani 1 1 d . . .
C11 C 0.0908(4) 0.2040(6) 0.4169(3) 0.0209(9) Uani 1 1 d . . .
H11 H 0.1256 0.2581 0.4672 0.025 Uiso 1 1 calc R . .
C12 C -0.0229(4) 0.1435(6) 0.3742(3) 0.0227(9) Uani 1 1 d . . .
C13 C -0.0883(4) 0.1664(7) 0.4085(3) 0.0285(10) Uani 1 1 d . . .
C14 C -0.0744(4) 0.0653(6) 0.2988(3) 0.0235(9) Uani 1 1 d . . .
H14 H -0.1509 0.0302 0.2688 0.028 Uiso 1 1 calc R . .
C15 C -0.0125(3) 0.0390(6) 0.2679(3) 0.0234(9) Uani 1 1 d . . .
H15 H -0.0479 -0.0139 0.2173 0.028 Uiso 1 1 calc R . .
H11B H 0.445(4) -0.116(7) 0.029(3) 0.028 Uiso 1 1 d . . .
H10B H 0.681(3) 0.055(6) 0.2756(17) 0.028 Uiso 1 1 d D . .
H11A H 0.545(5) -0.121(8) 0.087(3) 0.028 Uiso 1 1 d . . .
H10A H 0.591(4) -0.062(7) 0.246(3) 0.028 Uiso 1 1 d . . .
H12B H 0.192(5) 0.803(7) 0.965(3) 0.028 Uiso 1 1 d . . .
H7A H -0.073(5) 0.277(7) 0.489(3) 0.028 Uiso 1 1 d . . .
H9A H 0.366(2) 0.549(5) 0.0485(14) 0.028 Uiso 1 1 d D . .
H9B H 0.459(3) 0.628(3) 0.114(2) 0.028 Uiso 1 1 d 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
O12 H12A 0.8200 . ?
O12 H12B 0.81(5) . ?
Ho1 O5 2.258(3) 4_565 ?
Ho1 O3 2.306(3) 2_655 ?
Ho1 O1 2.336(3) . ?
Ho1 O10 2.377(3) . ?
Ho1 O9 2.392(4) . ?
Ho1 O11 2.405(3) . ?
Ho1 O2 2.425(3) 2_655 ?
Ho1 N1 2.503(3) 2_655 ?
O1 C1 1.265(5) . ?
O3 C7 1.269(5) . ?
O3 Ho1 2.306(3) 2_645 ?
O4 C7 1.232(5) . ?
O6 C10 1.228(5) . ?
O5 C10 1.268(5) . ?
O5 Ho1 2.258(3) 4_566 ?
O7 C13 1.315(6) . ?
O7 H7A 0.77(5) . ?
O8 C13 1.223(5) . ?
O11 H11B 0.83(5) . ?
O11 H11A 0.69(5) . ?
O2 C1 1.260(5) . ?
O2 Ho1 2.425(3) 2_645 ?
O10 H10B 0.846(10) . ?
O10 H10A 0.88(5) . ?
O9 H9A 0.848(10) . ?
O9 H9B 0.848(10) . ?
N1 C6 1.337(5) . ?
N1 C2 1.345(5) . ?
N1 Ho1 2.503(3) 2_645 ?
C1 C2 1.510(6) . ?
C2 C3 1.387(6) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(6) . ?
C5 C8 1.496(5) . ?
C6 C7 1.519(6) . ?
C8 C15 1.397(6) . ?
C8 C9 1.401(6) . ?
C9 C11 1.391(5) . ?
C9 C10 1.514(6) . ?
C11 C12 1.402(6) . ?
C11 H11 0.9300 . ?
C12 C14 1.386(6) . ?
C12 C13 1.487(6) . ?
C14 C15 1.385(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H12A O12 H12B 96.2 . . ?
O5 Ho1 O3 90.43(12) 4_565 2_655 ?
O5 Ho1 O1 77.47(11) 4_565 . ?
O3 Ho1 O1 153.83(11) 2_655 . ?
O5 Ho1 O10 141.84(12) 4_565 . ?
O3 Ho1 O10 95.80(12) 2_655 . ?
O1 Ho1 O10 80.73(11) . . ?
O5 Ho1 O9 71.78(13) 4_565 . ?
O3 Ho1 O9 90.41(15) 2_655 . ?
O1 Ho1 O9 107.23(14) . . ?
O10 Ho1 O9 145.42(13) . . ?
O5 Ho1 O11 77.71(12) 4_565 . ?
O3 Ho1 O11 74.20(12) 2_655 . ?
O1 Ho1 O11 80.53(11) . . ?
O10 Ho1 O11 68.03(12) . . ?
O9 Ho1 O11 145.65(13) . . ?
O5 Ho1 O2 126.79(12) 4_565 2_655 ?
O3 Ho1 O2 128.62(11) 2_655 2_655 ?
O1 Ho1 O2 76.06(10) . 2_655 ?
O10 Ho1 O2 76.34(11) . 2_655 ?
O9 Ho1 O2 73.32(13) . 2_655 ?
O11 Ho1 O2 139.91(12) . 2_655 ?
O5 Ho1 N1 137.64(12) 4_565 2_655 ?
O3 Ho1 N1 64.35(11) 2_655 2_655 ?
O1 Ho1 N1 138.17(11) . 2_655 ?
O10 Ho1 N1 77.39(11) . 2_655 ?
O9 Ho1 N1 74.83(13) . 2_655 ?
O11 Ho1 N1 121.93(11) . 2_655 ?
O2 Ho1 N1 64.39(10) 2_655 2_655 ?
C1 O1 Ho1 134.1(3) . . ?
C7 O3 Ho1 128.3(3) . 2_645 ?
C10 O5 Ho1 149.7(3) . 4_566 ?
C13 O7 H7A 110(4) . . ?
Ho1 O11 H11B 119(4) . . ?
Ho1 O11 H11A 115(5) . . ?
H11B O11 H11A 107(5) . . ?
C1 O2 Ho1 124.3(3) . 2_645 ?
Ho1 O10 H10B 116(4) . . ?
Ho1 O10 H10A 108(3) . . ?
H10B O10 H10A 104(5) . . ?
Ho1 O9 H9A 120(3) . . ?
Ho1 O9 H9B 133(3) . . ?
H9A O9 H9B 105.4(16) . . ?
C6 N1 C2 119.7(4) . . ?
C6 N1 Ho1 119.9(3) . 2_645 ?
C2 N1 Ho1 120.4(3) . 2_645 ?
O2 C1 O1 125.7(4) . . ?
O2 C1 C2 117.3(4) . . ?
O1 C1 C2 117.0(4) . . ?
N1 C2 C3 121.7(4) . . ?
N1 C2 C1 113.3(4) . . ?
C3 C2 C1 124.9(4) . . ?
C4 C3 C2 118.2(4) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 116.4(4) . . ?
C4 C5 C8 120.9(4) . . ?
C6 C5 C8 122.7(4) . . ?
N1 C6 C5 122.2(4) . . ?
N1 C6 C7 112.1(4) . . ?
C5 C6 C7 125.7(4) . . ?
O4 C7 O3 124.0(4) . . ?
O4 C7 C6 120.8(4) . . ?
O3 C7 C6 115.3(4) . . ?
C15 C8 C9 119.1(4) . . ?
C15 C8 C5 118.7(4) . . ?
C9 C8 C5 122.2(4) . . ?
C11 C9 C8 119.4(4) . . ?
C11 C9 C10 119.2(4) . . ?
C8 C9 C10 121.3(4) . . ?
O6 C10 O5 125.5(4) . . ?
O6 C10 C9 117.8(4) . . ?
O5 C10 C9 116.7(4) . . ?
C9 C11 C12 120.9(4) . . ?
C9 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C14 C12 C11 119.1(4) . . ?
C14 C12 C13 120.4(4) . . ?
C11 C12 C13 120.5(4) . . ?
O8 C13 O7 121.8(4) . . ?
O8 C13 C12 123.7(4) . . ?
O7 C13 C12 114.6(4) . . ?
C15 C14 C12 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C12 C14 H14 119.8 . . ?
C14 C15 C8 120.8(4) . . ?
C14 C15 H15 119.6 . . ?
C8 C15 H15 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.971
_refine_diff_density_min         -1.474
_refine_diff_density_rms         0.136
_database_code_depnum_ccdc_archive 'CCDC 979203'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Er N O12'
_chemical_formula_weight         567.53

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'
Er Er -0.2586 4.9576 '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           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   14.580(3)
_cell_length_b                   7.1880(14)
_cell_length_c                   20.756(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.16(2)
_cell_angle_gamma                90.00
_cell_volume                     1756.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3993
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1100
_exptl_absorpt_coefficient_mu    4.849
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3240
_exptl_absorpt_correction_T_max  0.4438
_exptl_absorpt_process_details   SADABS

_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16620
_diffrn_reflns_av_R_equivalents  0.1121
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.58
_reflns_number_total             3993
_reflns_number_gt                3359
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0653P)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    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3993
_refine_ls_number_parameters     267
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.1739(4) 1.2887(6) 0.4951(3) 0.0303(11) Uani 1 1 d . . .
Er1 Er -0.00687(2) 0.71001(3) 0.628057(13) 0.01754(13) Uani 1 1 d . . .
C2 C 0.2997(5) 1.0885(9) 0.8237(3) 0.0277(13) Uani 1 1 d . . .
H2 H 0.3214 1.1368 0.8725 0.033 Uiso 1 1 calc R . .
C10 C 0.5740(5) 1.0672(9) 0.7014(3) 0.0247(12) Uani 1 1 d . . .
H10 H 0.6505 1.0346 0.7315 0.030 Uiso 1 1 calc R . .
C4 C 0.3672(5) 1.1158(9) 0.7960(3) 0.0250(13) Uani 1 1 d . . .
H4 H 0.4354 1.1805 0.8273 0.030 Uiso 1 1 calc R . .
C6 C 0.2322(5) 0.9345(8) 0.6798(3) 0.0212(11) Uani 1 1 d . . .
C12 C 0.5885(6) 1.1673(10) 0.5921(4) 0.0299(14) Uani 1 1 d . . .
O2 O 0.6869(4) 1.1138(9) 0.6258(3) 0.0423(13) Uani 1 1 d . . .
C7 C 0.1819(6) 0.8327(9) 0.6006(4) 0.0262(13) Uani 1 1 d . . .
C14 C 0.3471(5) 1.1834(9) 0.6145(3) 0.0215(12) Uani 1 1 d . . .
C3 C 0.1133(5) 0.9602(8) 0.7941(3) 0.0214(11) Uani 1 1 d . . .
C11 C 0.5225(5) 1.1432(9) 0.6262(3) 0.0238(12) Uani 1 1 d . . .
C5 C 0.3312(5) 1.0452(8) 0.7209(3) 0.0196(11) Uani 1 1 d . . .
O9 O -0.0709(5) 1.0252(7) 0.5945(3) 0.0477(14) Uani 1 1 d . . .
H9A H -0.0233 1.1140 0.6155 0.057 Uiso 1 1 d R . .
H9B H -0.1415 1.0482 0.5617 0.057 Uiso 1 1 d R . .
C8 C 0.3970(5) 1.0925(9) 0.6887(3) 0.0216(12) Uani 1 1 d . . .
O7 O 0.0303(4) 0.8531(6) 0.7479(2) 0.0266(9) Uani 1 1 d . . .
O8 O 0.1281(4) 1.0517(6) 0.8512(2) 0.0254(9) Uani 1 1 d . . .
C1 C 0.1992(5) 0.9863(8) 0.7752(3) 0.0217(12) Uani 1 1 d . . .
O4 O 0.1942(5) 1.3164(9) 0.6102(3) 0.0479(15) Uani 1 1 d . . .
O1 O 0.5319(4) 1.2530(9) 0.5216(3) 0.0432(13) Uani 1 1 d . . .
H1 H 0.5765 1.2848 0.5118 0.065 Uiso 1 1 calc R . .
O5 O 0.2305(4) 0.8430(8) 0.5671(3) 0.0381(12) Uani 1 1 d . . .
C9 C 0.5122(5) 1.0389(9) 0.7325(3) 0.0258(12) Uani 1 1 d . . .
H9 H 0.5473 0.9844 0.7825 0.031 Uiso 1 1 calc R . .
O6 O 0.0902(4) 0.7448(7) 0.5727(3) 0.0320(10) Uani 1 1 d . . .
O11 O -0.0081(4) 0.4069(6) 0.5774(2) 0.0261(9) Uani 1 1 d D . .
H11A H 0.0526 0.3640 0.5860 0.031 Uiso 1 1 d RD . .
O10 O 0.1265(4) 0.5072(6) 0.7322(2) 0.0283(10) Uani 1 1 d . . .
H10A H 0.1939 0.5441 0.7673 0.034 Uiso 1 1 d R . .
H10B H 0.1068 0.3975 0.7344 0.034 Uiso 1 1 d R . .
N1 N 0.1688(4) 0.9064(7) 0.7069(3) 0.0219(10) Uani 1 1 d . . .
C15 C 0.2288(5) 1.2697(9) 0.5700(4) 0.0212(12) Uani 1 1 d . . .
C13 C 0.4088(6) 1.2045(8) 0.5830(4) 0.0232(13) Uani 1 1 d . . .
H13 H 0.3747 1.2592 0.5331 0.028 Uiso 1 1 calc R . .
O12 O 0.6670(5) 0.3639(9) 0.4842(4) 0.0537(15) Uani 1 1 d . . .
H12A H 0.7293 0.4233 0.5080 0.064 Uiso 1 1 d R . .
H12B H 0.6520 0.2802 0.4504 0.064 Uiso 1 1 d R . .
H11B H -0.0596(18) 0.386(12) 0.5283(15) 0.06(3) Uiso 1 1 d 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
O3 C15 1.269(7) . ?
O3 Er1 2.262(5) 3_576 ?
Er1 O3 2.262(5) 3_576 ?
Er1 O6 2.303(5) . ?
Er1 O8 2.346(4) 2_546 ?
Er1 O10 2.370(4) . ?
Er1 O9 2.392(5) . ?
Er1 O11 2.415(4) . ?
Er1 O7 2.439(4) . ?
Er1 N1 2.507(5) . ?
C2 C1 1.400(8) . ?
C2 C4 1.417(8) . ?
C2 H2 0.9300 . ?
C10 C11 1.384(8) . ?
C10 C9 1.400(8) . ?
C10 H10 0.9300 . ?
C4 C5 1.413(8) . ?
C4 H4 0.9300 . ?
C6 N1 1.350(7) . ?
C6 C5 1.411(8) . ?
C6 C7 1.535(8) . ?
C12 O2 1.230(8) . ?
C12 O1 1.334(8) . ?
C12 C11 1.502(9) . ?
C7 O5 1.253(7) . ?
C7 O6 1.268(8) . ?
C14 C13 1.400(8) . ?
C14 C8 1.415(8) . ?
C14 C15 1.527(8) . ?
C3 O8 1.258(7) . ?
C3 O7 1.268(7) . ?
C3 C1 1.529(8) . ?
C11 C13 1.411(9) . ?
C5 C8 1.497(8) . ?
O9 H9A 0.8500 . ?
O9 H9B 0.8500 . ?
C8 C9 1.412(8) . ?
O8 Er1 2.346(4) 2_556 ?
C1 N1 1.340(7) . ?
O4 C15 1.249(8) . ?
O1 H1 0.8200 . ?
C9 H9 0.9300 . ?
O11 H11A 0.8501 . ?
O11 H11B 0.850(10) . ?
O10 H10A 0.8499 . ?
O10 H10B 0.8500 . ?
C13 H13 0.9300 . ?
O12 H12A 0.8500 . ?
O12 H12B 0.8500 . ?

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
C15 O3 Er1 149.9(5) . 3_576 ?
O3 Er1 O6 90.28(18) 3_576 . ?
O3 Er1 O8 77.52(16) 3_576 2_546 ?
O6 Er1 O8 153.60(16) . 2_546 ?
O3 Er1 O10 142.16(16) 3_576 . ?
O6 Er1 O10 96.11(17) . . ?
O8 Er1 O10 80.56(15) 2_546 . ?
O3 Er1 O9 72.07(17) 3_576 . ?
O6 Er1 O9 90.1(2) . . ?
O8 Er1 O9 107.79(18) 2_546 . ?
O10 Er1 O9 144.81(18) . . ?
O3 Er1 O11 77.60(15) 3_576 . ?
O6 Er1 O11 74.29(17) . . ?
O8 Er1 O11 80.21(15) 2_546 . ?
O10 Er1 O11 68.50(15) . . ?
O9 Er1 O11 145.73(16) . . ?
O3 Er1 O7 126.40(17) 3_576 . ?
O6 Er1 O7 129.12(16) . . ?
O8 Er1 O7 75.82(14) 2_546 . ?
O10 Er1 O7 76.16(16) . . ?
O9 Er1 O7 73.19(17) . . ?
O11 Er1 O7 139.91(15) . . ?
O3 Er1 N1 137.67(17) 3_576 . ?
O6 Er1 N1 64.70(16) . . ?
O8 Er1 N1 138.03(14) 2_546 . ?
O10 Er1 N1 77.21(16) . . ?
O9 Er1 N1 74.31(18) . . ?
O11 Er1 N1 122.31(15) . . ?
O7 Er1 N1 64.55(15) . . ?
C1 C2 C4 117.6(5) . . ?
C1 C2 H2 121.2 . . ?
C4 C2 H2 121.2 . . ?
C11 C10 C9 120.6(6) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C5 C4 C2 120.2(6) . . ?
C5 C4 H4 119.9 . . ?
C2 C4 H4 119.9 . . ?
N1 C6 C5 122.8(5) . . ?
N1 C6 C7 111.3(5) . . ?
C5 C6 C7 126.0(5) . . ?
O2 C12 O1 121.8(6) . . ?
O2 C12 C11 123.6(6) . . ?
O1 C12 C11 114.7(6) . . ?
O5 C7 O6 124.4(6) . . ?
O5 C7 C6 119.8(6) . . ?
O6 C7 C6 115.8(5) . . ?
C13 C14 C8 119.9(6) . . ?
C13 C14 C15 118.8(5) . . ?
C8 C14 C15 121.2(5) . . ?
O8 C3 O7 125.9(5) . . ?
O8 C3 C1 117.8(5) . . ?
O7 C3 C1 116.3(5) . . ?
C10 C11 C13 119.5(6) . . ?
C10 C11 C12 120.3(6) . . ?
C13 C11 C12 120.1(5) . . ?
C6 C5 C4 116.7(5) . . ?
C6 C5 C8 123.8(5) . . ?
C4 C5 C8 119.5(5) . . ?
Er1 O9 H9A 120.1 . . ?
Er1 O9 H9B 119.9 . . ?
H9A O9 H9B 120.0 . . ?
C9 C8 C14 118.7(5) . . ?
C9 C8 C5 118.8(5) . . ?
C14 C8 C5 122.4(5) . . ?
C3 O7 Er1 124.4(4) . . ?
C3 O8 Er1 134.3(4) . 2_556 ?
N1 C1 C2 122.6(5) . . ?
N1 C1 C3 114.1(5) . . ?
C2 C1 C3 123.3(5) . . ?
C12 O1 H1 109.5 . . ?
C10 C9 C8 120.5(5) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C7 O6 Er1 128.2(4) . . ?
Er1 O11 H11A 119.8 . . ?
Er1 O11 H11B 117(5) . . ?
H11A O11 H11B 105.1 . . ?
Er1 O10 H10A 120.1 . . ?
Er1 O10 H10B 119.9 . . ?
H10A O10 H10B 120.0 . . ?
C1 N1 C6 119.7(5) . . ?
C1 N1 Er1 120.3(4) . . ?
C6 N1 Er1 120.0(4) . . ?
O4 C15 O3 125.4(6) . . ?
O4 C15 C14 117.5(5) . . ?
O3 C15 C14 117.1(5) . . ?
C14 C13 C11 120.5(5) . . ?
C14 C13 H13 119.8 . . ?
C11 C13 H13 119.8 . . ?
H12A O12 H12B 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         3.619
_refine_diff_density_min         -3.281
_refine_diff_density_rms         0.250
_database_code_depnum_ccdc_archive 'CCDC 979199'
