# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

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#                                CCDC 
# 
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# 
#  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.
#
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#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_Gd

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 F18 Gd N2 O9'
_chemical_formula_sum            'C25 H22 F18 Gd N2 O9'
_chemical_formula_weight         993.70

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'
F F 0.0171 0.0103 '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   P2(1)/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                   15.996(3)
_cell_length_b                   14.115(3)
_cell_length_c                   16.603(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.26(3)
_cell_angle_gamma                90.00
_cell_volume                     3443.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    113
_cell_measurement_reflns_used    12475
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      27.9

_exptl_crystal_description       prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    2.074
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28260
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         25.01
_reflns_number_total             6070
_reflns_number_gt                5599
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_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)+(0.0357P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6070
_refine_ls_number_parameters     505
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.316303(9) 0.076630(9) 0.399807(9) 0.01654(6) Uani 1 1 d . . .
O8 O 0.26735(14) -0.07947(12) 0.37990(14) 0.0215(5) Uani 1 1 d . . .
O3 O 0.19477(14) 0.07252(13) 0.25628(14) 0.0245(5) Uani 1 1 d . . .
O2 O 0.37769(13) 0.01743(12) 0.55365(13) 0.0199(4) Uani 1 1 d . . .
O6 O 0.27154(14) 0.23683(13) 0.38475(14) 0.0233(5) Uani 1 1 d . . .
F15 F 0.33722(13) 0.26883(13) 0.09308(13) 0.0376(5) Uani 1 1 d . . .
O7 O 0.43755(14) -0.02135(14) 0.40253(14) 0.0220(5) Uani 1 1 d D . .
H7A H 0.4399 -0.0708 0.4331 0.033 Uiso 1 1 d R . .
O1 O 0.20788(14) 0.09086(13) 0.46085(14) 0.0222(5) Uani 1 1 d . . .
F7 F 0.59002(13) 0.25377(15) 0.60969(13) 0.0450(5) Uani 1 1 d . . .
F3 F 0.09969(15) 0.05328(19) 0.60616(16) 0.0635(7) Uani 1 1 d . . .
F14 F 0.43234(13) 0.15776(13) 0.14621(13) 0.0401(5) Uani 1 1 d . . .
O4 O 0.36278(13) 0.13910(13) 0.28747(13) 0.0226(5) Uani 1 1 d . . .
F9 F 0.60573(14) 0.24197(17) 0.48558(15) 0.0580(6) Uani 1 1 d . . .
C14 C 0.2001(2) 0.06485(19) 0.5323(2) 0.0217(7) Uani 1 1 d . . .
O5 O 0.44570(13) 0.17138(13) 0.48001(13) 0.0199(4) Uani 1 1 d . . .
F17 F 0.07411(16) 0.11400(17) 0.02516(15) 0.0663(7) Uani 1 1 d . . .
F5 F 0.44682(15) -0.12168(15) 0.67577(15) 0.0514(6) Uani 1 1 d . . .
N2 N 0.21099(16) -0.13315(16) 0.31642(16) 0.0212(5) Uani 1 1 d . . .
F6 F 0.47434(17) 0.00997(15) 0.74413(16) 0.0671(7) Uani 1 1 d . . .
F4 F 0.37360(18) -0.08112(19) 0.75175(18) 0.0796(9) Uani 1 1 d . . .
C20 C 0.0660(2) -0.0870(2) 0.3064(3) 0.0340(8) Uani 1 1 d . . .
H20A H 0.0948 -0.0359 0.3457 0.051 Uiso 1 1 calc R . .
H20B H 0.0117 -0.1055 0.3136 0.051 Uiso 1 1 calc R . .
H20C H 0.0508 -0.0668 0.2470 0.051 Uiso 1 1 calc R . .
N1 N 0.14630(19) -0.21285(17) 0.19151(18) 0.0307(6) Uani 1 1 d . . .
F1 F 0.10343(15) 0.18417(15) 0.5399(2) 0.0728(9) Uani 1 1 d . . .
C7 C 0.3109(2) 0.3149(2) 0.3964(2) 0.0250(7) Uani 1 1 d . . .
C12 C 0.3460(2) -0.0016(2) 0.6116(2) 0.0230(7) Uani 1 1 d . . .
C19 C 0.2146(2) -0.1541(2) 0.2378(2) 0.0241(7) Uani 1 1 d . . .
C15 C 0.1120(2) 0.0900(2) 0.5364(2) 0.0295(8) Uani 1 1 d . . .
C4 C 0.3244(2) 0.1677(2) 0.2077(2) 0.0222(7) Uani 1 1 d . . .
C13 C 0.2618(2) 0.0182(2) 0.6065(2) 0.0279(7) Uani 1 1 d . . .
H13 H 0.2447 0.0010 0.6518 0.034 Uiso 1 1 calc R . .
C11 C 0.4101(2) -0.0489(2) 0.6970(2) 0.0312(8) Uani 1 1 d . . .
C23 C 0.1004(2) -0.2473(2) 0.2504(2) 0.0304(8) Uani 1 1 d . . .
C9 C 0.4606(2) 0.2583(2) 0.4748(2) 0.0235(7) Uani 1 1 d . . .
O9 O 0.13021(18) -0.24662(18) 0.11228(17) 0.0489(7) Uani 1 1 d . . .
C1 C 0.0880(2) 0.0829(2) 0.1076(2) 0.0332(8) Uani 1 1 d . . .
C10 C 0.5579(2) 0.2847(2) 0.5242(2) 0.0297(8) Uani 1 1 d . . .
C2 C 0.1802(2) 0.1041(2) 0.1786(2) 0.0254(7) Uani 1 1 d . . .
C5 C 0.3833(2) 0.2197(2) 0.1691(2) 0.0274(7) Uani 1 1 d . . .
F8 F 0.57438(15) 0.37571(14) 0.5267(2) 0.0855(10) Uani 1 1 d . . .
C18 C 0.2828(2) -0.1218(2) 0.2085(2) 0.0290(7) Uani 1 1 d . . .
H18 H 0.3294 -0.0812 0.2506 0.035 Uiso 1 1 calc R . .
C22 C 0.1303(2) -0.1701(2) 0.3264(2) 0.0268(7) Uani 1 1 d . . .
C3 C 0.2370(2) 0.1540(2) 0.1497(2) 0.0272(7) Uani 1 1 d . . .
H3 H 0.2166 0.1774 0.0928 0.033 Uiso 1 1 calc R . .
C21 C 0.1539(2) -0.2055(3) 0.4222(2) 0.0429(10) Uani 1 1 d . . .
H21A H 0.2028 -0.2506 0.4380 0.064 Uiso 1 1 calc R . .
H21B H 0.1014 -0.2351 0.4257 0.064 Uiso 1 1 calc R . .
H21C H 0.1722 -0.1527 0.4617 0.064 Uiso 1 1 calc R . .
C8 C 0.4015(2) 0.3309(2) 0.4353(2) 0.0266(7) Uani 1 1 d . . .
H8 H 0.4239 0.3916 0.4354 0.032 Uiso 1 1 calc R . .
C24 C 0.0023(2) -0.2532(3) 0.1957(3) 0.0459(10) Uani 1 1 d . . .
H24A H -0.0182 -0.1941 0.1658 0.069 Uiso 1 1 calc R . .
H24B H -0.0303 -0.2664 0.2321 0.069 Uiso 1 1 calc R . .
H24C H -0.0085 -0.3031 0.1534 0.069 Uiso 1 1 calc R . .
C16 C 0.3186(3) -0.1868(3) 0.1544(2) 0.0412(9) Uani 1 1 d . . .
H16A H 0.3835 -0.1863 0.1686 0.049 Uiso 1 1 calc R . .
H16B H 0.2899 -0.2483 0.1372 0.049 Uiso 1 1 calc R . .
F12 F 0.2110(2) 0.41347(17) 0.4236(2) 0.0824(10) Uani 1 1 d . . .
F11 F 0.18613(17) 0.38833(17) 0.28729(18) 0.0739(8) Uani 1 1 d . . .
F2 F 0.04495(13) 0.06281(13) 0.46132(14) 0.0397(5) Uani 1 1 d . . .
F13 F 0.43693(14) 0.28040(14) 0.22843(14) 0.0460(5) Uani 1 1 d . . .
F16 F 0.07376(14) -0.00981(13) 0.09964(15) 0.0515(6) Uani 1 1 d . . .
F18 F 0.02712(14) 0.1204(2) 0.13048(18) 0.0786(9) Uani 1 1 d . . .
F10 F 0.28879(16) 0.47926(15) 0.3607(2) 0.0923(11) Uani 1 1 d . . .
C6 C 0.2496(3) 0.4001(2) 0.3670(3) 0.0355(8) Uani 1 1 d . . .
C17 C 0.2655(3) -0.1021(2) 0.1094(3) 0.0402(9) Uani 1 1 d . . .
H17A H 0.2044 -0.1122 0.0656 0.048 Uiso 1 1 calc R . .
H17B H 0.2983 -0.0501 0.0970 0.048 Uiso 1 1 calc R . .
C25 C 0.1395(3) -0.3454(2) 0.2839(3) 0.0501(11) Uani 1 1 d . . .
H25A H 0.1242 -0.3883 0.2353 0.075 Uiso 1 1 calc R . .
H25B H 0.1143 -0.3683 0.3240 0.075 Uiso 1 1 calc R . .
H25C H 0.2045 -0.3411 0.3135 0.075 Uiso 1 1 calc R . .
H7B H 0.4886(17) -0.011(3) 0.402(3) 0.063(14) 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
Gd1 O8 2.3178(18) . ?
Gd1 O1 2.338(2) . ?
Gd1 O6 2.3552(19) . ?
Gd1 O7 2.3679(19) . ?
Gd1 O5 2.381(2) . ?
Gd1 O3 2.409(2) . ?
Gd1 O4 2.4298(19) . ?
Gd1 O2 2.491(2) . ?
O8 N2 1.322(3) . ?
O3 C2 1.296(4) . ?
O2 C12 1.281(3) . ?
O6 C7 1.245(4) . ?
F15 C5 1.372(4) . ?
O1 C14 1.294(4) . ?
F7 C10 1.376(4) . ?
F3 C15 1.353(4) . ?
F14 C5 1.327(3) . ?
O4 C4 1.285(4) . ?
F9 C10 1.321(4) . ?
C14 C13 1.402(4) . ?
C14 C15 1.480(4) . ?
O5 C9 1.259(3) . ?
F17 C1 1.370(4) . ?
F5 C11 1.299(4) . ?
N2 C19 1.363(4) . ?
N2 C22 1.462(4) . ?
F6 C11 1.314(4) . ?
F4 C11 1.339(4) . ?
C20 C22 1.507(4) . ?
N1 O9 1.325(3) . ?
N1 C19 1.345(4) . ?
N1 C23 1.516(4) . ?
F1 C15 1.340(4) . ?
C7 C8 1.352(4) . ?
C7 C6 1.506(5) . ?
C12 C13 1.345(4) . ?
C12 C11 1.536(4) . ?
C19 C18 1.432(4) . ?
C15 F2 1.340(4) . ?
C4 C3 1.362(4) . ?
C4 C5 1.520(4) . ?
C23 C24 1.473(5) . ?
C23 C25 1.531(5) . ?
C23 C22 1.591(4) . ?
C9 C8 1.373(4) . ?
C9 C10 1.493(4) . ?
C1 F18 1.290(4) . ?
C1 F16 1.326(3) . ?
C1 C2 1.510(5) . ?
C10 F8 1.309(4) . ?
C2 C3 1.377(4) . ?
C5 F13 1.332(4) . ?
C18 C16 1.543(4) . ?
C18 C17 1.582(5) . ?
C22 C21 1.564(4) . ?
C16 C17 1.486(5) . ?
F12 C6 1.326(4) . ?
F11 C6 1.323(4) . ?
F10 C6 1.306(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Gd1 O1 82.92(7) . . ?
O8 Gd1 O6 145.70(7) . . ?
O1 Gd1 O6 73.56(7) . . ?
O8 Gd1 O7 71.07(7) . . ?
O1 Gd1 O7 141.66(7) . . ?
O6 Gd1 O7 140.82(7) . . ?
O8 Gd1 O5 141.61(7) . . ?
O1 Gd1 O5 109.83(7) . . ?
O6 Gd1 O5 71.38(7) . . ?
O7 Gd1 O5 78.04(7) . . ?
O8 Gd1 O3 74.98(7) . . ?
O1 Gd1 O3 89.07(7) . . ?
O6 Gd1 O3 79.94(7) . . ?
O7 Gd1 O3 109.86(7) . . ?
O5 Gd1 O3 138.64(7) . . ?
O8 Gd1 O4 115.09(7) . . ?
O1 Gd1 O4 143.70(7) . . ?
O6 Gd1 O4 75.08(7) . . ?
O7 Gd1 O4 74.34(7) . . ?
O5 Gd1 O4 76.32(7) . . ?
O3 Gd1 O4 67.76(7) . . ?
O8 Gd1 O2 78.55(7) . . ?
O1 Gd1 O2 69.13(7) . . ?
O6 Gd1 O2 114.27(7) . . ?
O7 Gd1 O2 78.25(7) . . ?
O5 Gd1 O2 73.22(7) . . ?
O3 Gd1 O2 147.52(6) . . ?
O4 Gd1 O2 142.43(6) . . ?
N2 O8 Gd1 138.09(17) . . ?
C2 O3 Gd1 137.21(19) . . ?
C12 O2 Gd1 136.73(19) . . ?
C7 O6 Gd1 136.0(2) . . ?
C14 O1 Gd1 136.87(19) . . ?
C4 O4 Gd1 137.62(18) . . ?
O1 C14 C13 130.5(3) . . ?
O1 C14 C15 114.3(3) . . ?
C13 C14 C15 115.2(3) . . ?
C9 O5 Gd1 130.90(19) . . ?
O8 N2 C19 127.9(2) . . ?
O8 N2 C22 118.0(2) . . ?
C19 N2 C22 113.9(2) . . ?
O9 N1 C19 125.7(3) . . ?
O9 N1 C23 124.8(3) . . ?
C19 N1 C23 108.7(3) . . ?
O6 C7 C8 127.0(3) . . ?
O6 C7 C6 115.6(3) . . ?
C8 C7 C6 117.3(3) . . ?
O2 C12 C13 126.3(3) . . ?
O2 C12 C11 117.8(3) . . ?
C13 C12 C11 115.8(3) . . ?
N1 C19 N2 110.4(3) . . ?
N1 C19 C18 123.9(3) . . ?
N2 C19 C18 125.7(3) . . ?
F2 C15 F1 105.5(3) . . ?
F2 C15 F3 110.6(3) . . ?
F1 C15 F3 106.9(3) . . ?
F2 C15 C14 108.4(3) . . ?
F1 C15 C14 110.9(2) . . ?
F3 C15 C14 114.2(3) . . ?
O4 C4 C3 128.5(3) . . ?
O4 C4 C5 117.5(3) . . ?
C3 C4 C5 113.8(3) . . ?
C12 C13 C14 119.6(3) . . ?
F5 C11 F6 109.3(3) . . ?
F5 C11 F4 106.3(3) . . ?
F6 C11 F4 105.0(3) . . ?
F5 C11 C12 107.6(3) . . ?
F6 C11 C12 110.8(3) . . ?
F4 C11 C12 117.6(3) . . ?
C24 C23 N1 106.8(3) . . ?
C24 C23 C25 110.8(3) . . ?
N1 C23 C25 107.0(3) . . ?
C24 C23 C22 116.2(3) . . ?
N1 C23 C22 102.8(2) . . ?
C25 C23 C22 112.3(3) . . ?
O5 C9 C8 130.3(3) . . ?
O5 C9 C10 112.9(3) . . ?
C8 C9 C10 116.6(3) . . ?
F18 C1 F16 108.3(3) . . ?
F18 C1 F17 108.6(3) . . ?
F16 C1 F17 105.2(3) . . ?
F18 C1 C2 107.9(3) . . ?
F16 C1 C2 110.5(3) . . ?
F17 C1 C2 116.1(3) . . ?
F8 C10 F9 108.4(3) . . ?
F8 C10 F7 106.8(3) . . ?
F9 C10 F7 107.7(3) . . ?
F8 C10 C9 114.6(3) . . ?
F9 C10 C9 107.3(3) . . ?
F7 C10 C9 111.8(2) . . ?
O3 C2 C3 129.7(3) . . ?
O3 C2 C1 116.4(3) . . ?
C3 C2 C1 113.9(3) . . ?
F14 C5 F13 110.8(3) . . ?
F14 C5 F15 103.4(2) . . ?
F13 C5 F15 108.1(2) . . ?
F14 C5 C4 109.7(2) . . ?
F13 C5 C4 109.0(3) . . ?
F15 C5 C4 115.8(3) . . ?
C19 C18 C16 121.1(3) . . ?
C19 C18 C17 124.4(3) . . ?
C16 C18 C17 56.8(2) . . ?
N2 C22 C20 104.6(2) . . ?
N2 C22 C21 111.1(3) . . ?
C20 C22 C21 110.1(3) . . ?
N2 C22 C23 99.0(2) . . ?
C20 C22 C23 113.1(3) . . ?
C21 C22 C23 117.7(3) . . ?
C4 C3 C2 117.4(3) . . ?
C7 C8 C9 120.6(3) . . ?
C17 C16 C18 62.9(2) . . ?
F10 C6 F11 103.3(3) . . ?
F10 C6 F12 108.0(3) . . ?
F11 C6 F12 109.8(3) . . ?
F10 C6 C7 116.0(3) . . ?
F11 C6 C7 111.6(3) . . ?
F12 C6 C7 108.1(3) . . ?
C16 C17 C18 60.3(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
O1 Gd1 O8 N2 98.5(3) . . . . ?
O6 Gd1 O8 N2 51.9(3) . . . . ?
O7 Gd1 O8 N2 -110.1(3) . . . . ?
O5 Gd1 O8 N2 -148.4(2) . . . . ?
O3 Gd1 O8 N2 7.5(2) . . . . ?
O4 Gd1 O8 N2 -48.5(3) . . . . ?
O2 Gd1 O8 N2 168.5(3) . . . . ?
O8 Gd1 O3 C2 -134.2(3) . . . . ?
O1 Gd1 O3 C2 142.9(3) . . . . ?
O6 Gd1 O3 C2 69.4(3) . . . . ?
O7 Gd1 O3 C2 -71.2(3) . . . . ?
O5 Gd1 O3 C2 23.2(3) . . . . ?
O4 Gd1 O3 C2 -8.5(3) . . . . ?
O2 Gd1 O3 C2 -170.7(2) . . . . ?
O8 Gd1 O2 C12 -76.3(3) . . . . ?
O1 Gd1 O2 C12 10.5(2) . . . . ?
O6 Gd1 O2 C12 70.2(3) . . . . ?
O7 Gd1 O2 C12 -149.0(3) . . . . ?
O5 Gd1 O2 C12 130.1(3) . . . . ?
O3 Gd1 O2 C12 -40.4(3) . . . . ?
O4 Gd1 O2 C12 167.2(2) . . . . ?
O8 Gd1 O6 C7 -175.8(2) . . . . ?
O1 Gd1 O6 C7 135.5(3) . . . . ?
O7 Gd1 O6 C7 -23.3(3) . . . . ?
O5 Gd1 O6 C7 17.3(3) . . . . ?
O3 Gd1 O6 C7 -132.5(3) . . . . ?
O4 Gd1 O6 C7 -63.0(3) . . . . ?
O2 Gd1 O6 C7 78.2(3) . . . . ?
O8 Gd1 O1 C14 73.0(3) . . . . ?
O6 Gd1 O1 C14 -132.3(3) . . . . ?
O7 Gd1 O1 C14 26.1(3) . . . . ?
O5 Gd1 O1 C14 -69.7(3) . . . . ?
O3 Gd1 O1 C14 147.9(3) . . . . ?
O4 Gd1 O1 C14 -163.5(2) . . . . ?
O2 Gd1 O1 C14 -7.4(2) . . . . ?
O8 Gd1 O4 C4 74.9(3) . . . . ?
O1 Gd1 O4 C4 -39.2(3) . . . . ?
O6 Gd1 O4 C4 -70.1(3) . . . . ?
O7 Gd1 O4 C4 134.7(3) . . . . ?
O5 Gd1 O4 C4 -144.1(3) . . . . ?
O3 Gd1 O4 C4 15.0(3) . . . . ?
O2 Gd1 O4 C4 179.3(2) . . . . ?
Gd1 O1 C14 C13 3.5(5) . . . . ?
Gd1 O1 C14 C15 -177.58(18) . . . . ?
O8 Gd1 O5 C9 172.6(2) . . . . ?
O1 Gd1 O5 C9 -83.3(2) . . . . ?
O6 Gd1 O5 C9 -19.3(2) . . . . ?
O7 Gd1 O5 C9 135.8(2) . . . . ?
O3 Gd1 O5 C9 29.3(3) . . . . ?
O4 Gd1 O5 C9 59.3(2) . . . . ?
O2 Gd1 O5 C9 -143.0(2) . . . . ?
Gd1 O8 N2 C19 61.1(4) . . . . ?
Gd1 O8 N2 C22 -113.8(3) . . . . ?
Gd1 O6 C7 C8 -9.5(5) . . . . ?
Gd1 O6 C7 C6 173.2(2) . . . . ?
Gd1 O2 C12 C13 -9.1(5) . . . . ?
Gd1 O2 C12 C11 172.87(19) . . . . ?
O9 N1 C19 N2 179.8(3) . . . . ?
C23 N1 C19 N2 -9.7(3) . . . . ?
O9 N1 C19 C18 -2.4(5) . . . . ?
C23 N1 C19 C18 168.2(3) . . . . ?
O8 N2 C19 N1 178.6(2) . . . . ?
C22 N2 C19 N1 -6.3(3) . . . . ?
O8 N2 C19 C18 0.8(5) . . . . ?
C22 N2 C19 C18 175.9(3) . . . . ?
O1 C14 C15 F2 48.8(3) . . . . ?
C13 C14 C15 F2 -132.1(3) . . . . ?
O1 C14 C15 F1 -66.5(4) . . . . ?
C13 C14 C15 F1 112.6(3) . . . . ?
O1 C14 C15 F3 172.7(2) . . . . ?
C13 C14 C15 F3 -8.3(4) . . . . ?
Gd1 O4 C4 C3 -15.2(5) . . . . ?
Gd1 O4 C4 C5 168.16(18) . . . . ?
O2 C12 C13 C14 -0.6(5) . . . . ?
C11 C12 C13 C14 177.4(3) . . . . ?
O1 C14 C13 C12 3.6(5) . . . . ?
C15 C14 C13 C12 -175.3(3) . . . . ?
O2 C12 C11 F5 -50.7(4) . . . . ?
C13 C12 C11 F5 131.1(3) . . . . ?
O2 C12 C11 F6 68.8(4) . . . . ?
C13 C12 C11 F6 -109.4(3) . . . . ?
O2 C12 C11 F4 -170.6(3) . . . . ?
C13 C12 C11 F4 11.2(4) . . . . ?
O9 N1 C23 C24 -46.5(4) . . . . ?
C19 N1 C23 C24 142.8(3) . . . . ?
O9 N1 C23 C25 72.2(4) . . . . ?
C19 N1 C23 C25 -98.5(3) . . . . ?
O9 N1 C23 C22 -169.4(3) . . . . ?
C19 N1 C23 C22 20.0(3) . . . . ?
Gd1 O5 C9 C8 16.0(5) . . . . ?
Gd1 O5 C9 C10 -167.78(19) . . . . ?
O5 C9 C10 F8 -174.1(3) . . . . ?
C8 C9 C10 F8 2.6(4) . . . . ?
O5 C9 C10 F9 65.5(3) . . . . ?
C8 C9 C10 F9 -117.8(3) . . . . ?
O5 C9 C10 F7 -52.4(3) . . . . ?
C8 C9 C10 F7 124.3(3) . . . . ?
Gd1 O3 C2 C3 1.9(5) . . . . ?
Gd1 O3 C2 C1 -178.96(19) . . . . ?
F18 C1 C2 O3 59.8(4) . . . . ?
F16 C1 C2 O3 -58.4(4) . . . . ?
F17 C1 C2 O3 -178.1(3) . . . . ?
F18 C1 C2 C3 -121.0(3) . . . . ?
F16 C1 C2 C3 120.8(3) . . . . ?
F17 C1 C2 C3 1.2(4) . . . . ?
O4 C4 C5 F14 78.8(3) . . . . ?
C3 C4 C5 F14 -98.4(3) . . . . ?
O4 C4 C5 F13 -42.7(3) . . . . ?
C3 C4 C5 F13 140.2(3) . . . . ?
O4 C4 C5 F15 -164.7(2) . . . . ?
C3 C4 C5 F15 18.2(4) . . . . ?
N1 C19 C18 C16 -35.0(5) . . . . ?
N2 C19 C18 C16 142.5(3) . . . . ?
N1 C19 C18 C17 33.7(5) . . . . ?
N2 C19 C18 C17 -148.8(3) . . . . ?
O8 N2 C22 C20 76.6(3) . . . . ?
C19 N2 C22 C20 -99.0(3) . . . . ?
O8 N2 C22 C21 -42.1(3) . . . . ?
C19 N2 C22 C21 142.3(3) . . . . ?
O8 N2 C22 C23 -166.5(2) . . . . ?
C19 N2 C22 C23 17.9(3) . . . . ?
C24 C23 C22 N2 -137.6(3) . . . . ?
N1 C23 C22 N2 -21.3(3) . . . . ?
C25 C23 C22 N2 93.3(3) . . . . ?
C24 C23 C22 C20 -27.4(4) . . . . ?
N1 C23 C22 C20 88.8(3) . . . . ?
C25 C23 C22 C20 -156.5(3) . . . . ?
C24 C23 C22 C21 102.8(4) . . . . ?
N1 C23 C22 C21 -140.9(3) . . . . ?
C25 C23 C22 C21 -26.3(4) . . . . ?
O4 C4 C3 C2 0.8(5) . . . . ?
C5 C4 C3 C2 177.6(3) . . . . ?
O3 C2 C3 C4 5.5(5) . . . . ?
C1 C2 C3 C4 -173.6(3) . . . . ?
O6 C7 C8 C9 -6.4(5) . . . . ?
C6 C7 C8 C9 170.8(3) . . . . ?
O5 C9 C8 C7 2.5(5) . . . . ?
C10 C9 C8 C7 -173.6(3) . . . . ?
C19 C18 C16 C17 113.2(4) . . . . ?
O6 C7 C6 F10 -165.3(3) . . . . ?
C8 C7 C6 F10 17.1(5) . . . . ?
O6 C7 C6 F11 -47.5(4) . . . . ?
C8 C7 C6 F11 135.0(3) . . . . ?
O6 C7 C6 F12 73.4(4) . . . . ?
C8 C7 C6 F12 -104.2(4) . . . . ?
C19 C18 C17 C16 -107.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7B O2 0.833(18) 1.97(2) 2.751(3) 156(4) 3_656
O7 H7A O5 0.86 2.32 2.983(3) 135.1 3_656

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.084


_database_code_depnum_ccdc_archive 'CCDC 998207'
#######################################################################
#
#                 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_Tb

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 F18 N2 O9 Tb'
_chemical_formula_sum            'C25 H22 F18 N2 O9 Tb'
_chemical_formula_weight         995.37

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'
F F 0.0171 0.0103 '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                   15.978(3)
_cell_length_b                   14.130(3)
_cell_length_c                   16.588(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.08(3)
_cell_angle_gamma                90.00
_cell_volume                     3445.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    113
_cell_measurement_reflns_used    12475
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      27.9

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1940
_exptl_absorpt_coefficient_mu    2.201
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26485
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.01
_reflns_number_total             6057
_reflns_number_gt                5604
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_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)+(0.0400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6057
_refine_ls_number_parameters     505
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0596
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.316541(7) 0.075941(8) 0.400437(7) 0.01535(6) Uani 1 1 d . . .
O8 O 0.26995(12) -0.07884(12) 0.38180(12) 0.0217(4) Uani 1 1 d . . .
O4 O 0.19528(12) 0.07057(12) 0.25985(12) 0.0240(4) Uani 1 1 d . . .
O6 O 0.37711(10) 0.01755(13) 0.55269(11) 0.0202(4) Uani 1 1 d . . .
F6 F 0.04536(11) 0.06212(12) 0.46106(12) 0.0342(4) Uani 1 1 d . . .
O1 O 0.27090(11) 0.23368(13) 0.38479(12) 0.0246(4) Uani 1 1 d . . .
O5 O 0.20822(11) 0.08993(13) 0.46014(12) 0.0214(4) Uani 1 1 d . . .
F13 F 0.33555(11) 0.26774(13) 0.09440(11) 0.0379(4) Uani 1 1 d . . .
O7 O 0.43714(11) -0.02001(13) 0.40306(12) 0.0223(4) Uani 1 1 d D . .
H7A H 0.4391 -0.0679 0.4317 0.033 Uiso 1 1 calc R . .
F5 F 0.10037(12) 0.05487(17) 0.60658(13) 0.0552(6) Uani 1 1 d . . .
F14 F 0.43049(11) 0.15747(13) 0.14706(11) 0.0410(4) Uani 1 1 d . . .
O3 O 0.36183(10) 0.13697(13) 0.28891(11) 0.0232(4) Uani 1 1 d . . .
F1 F 0.47462(13) 0.01005(14) 0.74351(12) 0.0579(6) Uani 1 1 d . . .
O2 O 0.44404(11) 0.16958(12) 0.48024(11) 0.0210(4) Uani 1 1 d . . .
F15 F 0.43473(12) 0.27959(14) 0.22958(12) 0.0455(5) Uani 1 1 d . . .
F3 F 0.37361(15) -0.08086(17) 0.75189(15) 0.0714(8) Uani 1 1 d . . .
N1 N 0.21443(13) -0.13225(15) 0.31751(14) 0.0212(5) Uani 1 1 d . . .
C12 C 0.20032(17) 0.06469(18) 0.53157(18) 0.0217(6) Uani 1 1 d . . .
F2 F 0.44735(12) -0.12167(14) 0.67498(13) 0.0465(5) Uani 1 1 d . . .
N2 N 0.15073(15) -0.21168(17) 0.19213(15) 0.0305(5) Uani 1 1 d . . .
F4 F 0.10358(11) 0.18463(14) 0.53797(16) 0.0635(7) Uani 1 1 d . . .
C19 C 0.21891(17) -0.15222(19) 0.23929(18) 0.0248(6) Uani 1 1 d . . .
C14 C 0.34580(16) -0.00138(19) 0.61099(17) 0.0225(6) Uani 1 1 d . . .
C7 C 0.30945(17) 0.3117(2) 0.39666(16) 0.0247(6) Uani 1 1 d . . .
C13 C 0.26159(17) 0.0182(2) 0.60625(18) 0.0266(6) Uani 1 1 d . . .
H13 H 0.2442 0.0012 0.6516 0.032 Uiso 1 1 calc R . .
O9 O 0.13596(15) -0.24521(17) 0.11309(15) 0.0476(6) Uani 1 1 d . . .
C18 C 0.28659(18) -0.1186(2) 0.20960(19) 0.0288(6) Uani 1 1 d . . .
H18 H 0.3326 -0.0775 0.2515 0.035 Uiso 1 1 calc R . .
C11 C 0.11151(18) 0.0909(2) 0.5355(2) 0.0288(7) Uani 1 1 d . . .
C9 C 0.45908(17) 0.2563(2) 0.47602(17) 0.0239(6) Uani 1 1 d . . .
C15 C 0.4101(2) -0.0487(2) 0.6971(2) 0.0307(7) Uani 1 1 d . . .
C10 C 0.55590(18) 0.2828(2) 0.52559(19) 0.0298(6) Uani 1 1 d . . .
C1 C 0.38163(18) 0.2188(2) 0.17004(18) 0.0271(6) Uani 1 1 d . . .
C2 C 0.32287(17) 0.16637(19) 0.20883(17) 0.0229(6) Uani 1 1 d . . .
C21 C 0.10531(18) -0.2475(2) 0.2510(2) 0.0304(7) Uani 1 1 d . . .
F16 F 0.57183(13) 0.37421(14) 0.52923(18) 0.0762(8) Uani 1 1 d . . .
F11 F 0.20930(19) 0.40954(18) 0.42440(18) 0.0831(9) Uani 1 1 d . . .
C8 C 0.39972(17) 0.3289(2) 0.43566(18) 0.0279(6) Uani 1 1 d . . .
H8 H 0.4218 0.3898 0.4353 0.033 Uiso 1 1 calc R . .
C4 C 0.17941(18) 0.1033(2) 0.18127(19) 0.0263(6) Uani 1 1 d . . .
C24 C 0.13418(17) -0.1712(2) 0.32795(19) 0.0279(6) Uani 1 1 d . . .
C3 C 0.23554(17) 0.1537(2) 0.15184(18) 0.0268(6) Uani 1 1 d . . .
H3 H 0.2145 0.1781 0.0953 0.032 Uiso 1 1 calc R . .
C16 C 0.2689(2) -0.0983(2) 0.1104(2) 0.0368(7) Uani 1 1 d . . .
H16A H 0.2080 -0.1092 0.0668 0.044 Uiso 1 1 calc R . .
H16B H 0.3009 -0.0457 0.0980 0.044 Uiso 1 1 calc R . .
C17 C 0.3230(2) -0.1819(2) 0.1554(2) 0.0399(8) Uani 1 1 d . . .
H17A H 0.3879 -0.1803 0.1694 0.048 Uiso 1 1 calc R . .
H17B H 0.2953 -0.2437 0.1383 0.048 Uiso 1 1 calc R . .
C25 C 0.1584(2) -0.2084(3) 0.4236(2) 0.0461(9) Uani 1 1 d . . .
H25A H 0.2076 -0.2529 0.4385 0.069 Uiso 1 1 calc R . .
H25B H 0.1062 -0.2388 0.4270 0.069 Uiso 1 1 calc R . .
H25C H 0.1764 -0.1562 0.4638 0.069 Uiso 1 1 calc R . .
C6 C 0.2474(2) 0.3961(2) 0.3674(2) 0.0347(7) Uani 1 1 d . . .
C22 C 0.1440(2) -0.3449(2) 0.2831(3) 0.0542(10) Uani 1 1 d . . .
H22A H 0.1322 -0.3861 0.2338 0.081 Uiso 1 1 calc R . .
H22B H 0.1158 -0.3702 0.3200 0.081 Uiso 1 1 calc R . .
H22C H 0.2084 -0.3401 0.3159 0.081 Uiso 1 1 calc R . .
C20 C 0.0070(2) -0.2535(3) 0.1960(2) 0.0479(9) Uani 1 1 d . . .
H20A H -0.0133 -0.1946 0.1657 0.072 Uiso 1 1 calc R . .
H20B H -0.0258 -0.2660 0.2325 0.072 Uiso 1 1 calc R . .
H20C H -0.0037 -0.3036 0.1542 0.072 Uiso 1 1 calc R . .
F17 F 0.58738(11) 0.25072(14) 0.61067(11) 0.0422(5) Uani 1 1 d . . .
F8 F 0.07445(11) -0.01106(13) 0.10087(13) 0.0521(5) Uani 1 1 d . . .
F18 F 0.60388(12) 0.24159(16) 0.48578(13) 0.0562(6) Uani 1 1 d . . .
F9 F 0.07165(14) 0.11532(17) 0.02903(13) 0.0682(7) Uani 1 1 d . . .
F7 F 0.02640(12) 0.1155(2) 0.13641(17) 0.0853(9) Uani 1 1 d . . .
C5 C 0.0869(2) 0.0817(2) 0.1111(2) 0.0344(7) Uani 1 1 d . . .
F10 F 0.18396(15) 0.38360(18) 0.28763(16) 0.0774(7) Uani 1 1 d . . .
C23 C 0.0692(2) -0.0892(2) 0.3091(2) 0.0360(8) Uani 1 1 d . . .
H23A H 0.0983 -0.0375 0.3474 0.054 Uiso 1 1 calc R . .
H23B H 0.0161 -0.1082 0.3186 0.054 Uiso 1 1 calc R . .
H23C H 0.0518 -0.0696 0.2493 0.054 Uiso 1 1 calc R . .
F12 F 0.28618(15) 0.47543(16) 0.3602(2) 0.0969(10) Uani 1 1 d . . .
H7B H 0.4879(16) -0.002(3) 0.408(2) 0.075(13) 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 O8 2.2919(17) . ?
Tb1 O5 2.3150(17) . ?
Tb1 O1 2.3278(19) . ?
Tb1 O7 2.3425(17) . ?
Tb1 O2 2.3535(18) . ?
Tb1 O4 2.378(2) . ?
Tb1 O3 2.3957(17) . ?
Tb1 O6 2.4658(18) . ?
O8 N1 1.324(3) . ?
O4 C4 1.311(3) . ?
O6 C14 1.279(3) . ?
F6 C11 1.336(3) . ?
O1 C7 1.240(3) . ?
O5 C12 1.290(3) . ?
F13 C1 1.368(3) . ?
O7 H7A 0.8200 . ?
O7 H7B 0.820(18) . ?
F5 C11 1.358(4) . ?
F14 C1 1.319(3) . ?
O3 C2 1.295(3) . ?
F1 C15 1.312(4) . ?
O2 C9 1.256(3) . ?
F15 C1 1.333(3) . ?
F3 C15 1.337(3) . ?
N1 C19 1.357(3) . ?
N1 C24 1.467(3) . ?
C12 C13 1.405(4) . ?
C12 C11 1.493(4) . ?
F2 C15 1.313(4) . ?
N2 O9 1.325(3) . ?
N2 C19 1.355(3) . ?
N2 C21 1.514(4) . ?
F4 C11 1.333(3) . ?
C19 C18 1.434(4) . ?
C14 C13 1.345(3) . ?
C14 C15 1.547(4) . ?
C7 C8 1.351(4) . ?
C7 C6 1.505(4) . ?
C13 H13 0.9300 . ?
C18 C17 1.536(4) . ?
C18 C16 1.582(4) . ?
C18 H18 0.9800 . ?
C9 C8 1.380(4) . ?
C9 C10 1.487(4) . ?
C10 F16 1.313(3) . ?
C10 F18 1.327(3) . ?
C10 F17 1.376(3) . ?
C1 C2 1.522(4) . ?
C2 C3 1.356(4) . ?
C21 C20 1.477(4) . ?
C21 C22 1.518(4) . ?
C21 C24 1.594(4) . ?
F11 C6 1.323(4) . ?
C8 H8 0.9300 . ?
C4 C3 1.376(4) . ?
C4 C5 1.511(4) . ?
C24 C23 1.504(4) . ?
C24 C25 1.569(4) . ?
C3 H3 0.9300 . ?
C16 C17 1.481(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C6 F12 1.309(4) . ?
C6 F10 1.326(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
F8 C5 1.326(3) . ?
F9 C5 1.371(4) . ?
F7 C5 1.287(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Tb1 O5 83.19(6) . . ?
O8 Tb1 O1 145.86(6) . . ?
O5 Tb1 O1 73.25(6) . . ?
O8 Tb1 O7 70.82(6) . . ?
O5 Tb1 O7 142.09(6) . . ?
O1 Tb1 O7 140.87(6) . . ?
O8 Tb1 O2 140.91(6) . . ?
O5 Tb1 O2 109.81(6) . . ?
O1 Tb1 O2 71.86(6) . . ?
O7 Tb1 O2 77.91(6) . . ?
O8 Tb1 O4 74.96(6) . . ?
O5 Tb1 O4 87.93(7) . . ?
O1 Tb1 O4 79.75(6) . . ?
O7 Tb1 O4 110.35(7) . . ?
O2 Tb1 O4 139.67(6) . . ?
O8 Tb1 O3 114.82(6) . . ?
O5 Tb1 O3 143.36(6) . . ?
O1 Tb1 O3 75.25(6) . . ?
O7 Tb1 O3 74.18(6) . . ?
O2 Tb1 O3 77.00(6) . . ?
O4 Tb1 O3 68.33(6) . . ?
O8 Tb1 O6 78.18(6) . . ?
O5 Tb1 O6 69.48(6) . . ?
O1 Tb1 O6 114.50(6) . . ?
O7 Tb1 O6 78.32(6) . . ?
O2 Tb1 O6 72.92(6) . . ?
O4 Tb1 O6 146.67(6) . . ?
O3 Tb1 O6 142.69(5) . . ?
N1 O8 Tb1 137.09(15) . . ?
C4 O4 Tb1 136.85(17) . . ?
C14 O6 Tb1 137.01(15) . . ?
C7 O1 Tb1 135.96(17) . . ?
C12 O5 Tb1 136.72(16) . . ?
Tb1 O7 H7A 109.5 . . ?
Tb1 O7 H7B 126(3) . . ?
H7A O7 H7B 112.3 . . ?
C2 O3 Tb1 137.60(15) . . ?
C9 O2 Tb1 131.27(16) . . ?
O8 N1 C19 128.2(2) . . ?
O8 N1 C24 117.4(2) . . ?
C19 N1 C24 114.3(2) . . ?
O5 C12 C13 130.8(2) . . ?
O5 C12 C11 114.1(2) . . ?
C13 C12 C11 115.0(2) . . ?
O9 N2 C19 125.7(2) . . ?
O9 N2 C21 125.0(2) . . ?
C19 N2 C21 108.4(2) . . ?
N2 C19 N1 110.4(2) . . ?
N2 C19 C18 123.5(2) . . ?
N1 C19 C18 126.1(2) . . ?
O6 C14 C13 126.3(2) . . ?
O6 C14 C15 118.3(2) . . ?
C13 C14 C15 115.4(2) . . ?
O1 C7 C8 127.4(3) . . ?
O1 C7 C6 115.4(2) . . ?
C8 C7 C6 117.1(3) . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 C16 124.4(2) . . ?
C17 C18 C16 56.70(19) . . ?
C19 C18 H18 114.2 . . ?
C17 C18 H18 114.2 . . ?
C16 C18 H18 114.2 . . ?
F4 C11 F6 106.3(2) . . ?
F4 C11 F5 107.5(2) . . ?
F6 C11 F5 111.3(2) . . ?
F4 C11 C12 110.6(2) . . ?
F6 C11 C12 107.7(2) . . ?
F5 C11 C12 113.3(3) . . ?
O2 C9 C8 130.0(2) . . ?
O2 C9 C10 113.3(2) . . ?
C8 C9 C10 116.7(2) . . ?
F1 C15 F2 108.8(2) . . ?
F1 C15 F3 105.5(3) . . ?
F2 C15 F3 106.8(3) . . ?
F1 C15 C14 110.6(2) . . ?
F2 C15 C14 106.9(2) . . ?
F3 C15 C14 117.8(2) . . ?
F16 C10 F18 108.4(2) . . ?
F16 C10 F17 106.9(2) . . ?
F18 C10 F17 108.4(2) . . ?
F16 C10 C9 114.5(2) . . ?
F18 C10 C9 107.0(2) . . ?
F17 C10 C9 111.5(2) . . ?
F14 C1 F15 111.1(2) . . ?
F14 C1 F13 103.5(2) . . ?
F15 C1 F13 108.1(2) . . ?
F14 C1 C2 109.6(2) . . ?
F15 C1 C2 108.6(2) . . ?
F13 C1 C2 115.8(2) . . ?
O3 C2 C3 128.5(2) . . ?
O3 C2 C1 117.5(2) . . ?
C3 C2 C1 114.0(2) . . ?
C20 C21 N2 106.5(3) . . ?
C20 C21 C22 110.7(3) . . ?
N2 C21 C22 107.3(2) . . ?
C20 C21 C24 115.9(2) . . ?
N2 C21 C24 103.3(2) . . ?
C22 C21 C24 112.4(3) . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
O4 C4 C3 129.5(3) . . ?
O4 C4 C5 116.4(2) . . ?
C3 C4 C5 114.1(3) . . ?
N1 C24 C23 104.5(2) . . ?
N1 C24 C25 111.4(2) . . ?
C23 C24 C25 110.2(3) . . ?
N1 C24 C21 98.7(2) . . ?
C23 C24 C21 113.2(2) . . ?
C25 C24 C21 117.6(3) . . ?
C2 C3 C4 117.2(3) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C17 C16 C18 60.09(19) . . ?
C17 C16 H16A 117.8 . . ?
C18 C16 H16A 117.8 . . ?
C17 C16 H16B 117.8 . . ?
C18 C16 H16B 117.8 . . ?
H16A C16 H16B 114.9 . . ?
C16 C17 C18 63.2(2) . . ?
C16 C17 H17A 117.4 . . ?
C18 C17 H17A 117.4 . . ?
C16 C17 H17B 117.4 . . ?
C18 C17 H17B 117.4 . . ?
H17A C17 H17B 114.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F12 C6 F11 108.0(3) . . ?
F12 C6 F10 103.1(3) . . ?
F11 C6 F10 110.3(3) . . ?
F12 C6 C7 115.6(3) . . ?
F11 C6 C7 108.3(3) . . ?
F10 C6 C7 111.4(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F7 C5 F8 108.3(3) . . ?
F7 C5 F9 109.4(3) . . ?
F8 C5 F9 104.8(3) . . ?
F7 C5 C4 107.9(3) . . ?
F8 C5 C4 110.5(2) . . ?
F9 C5 C4 115.7(3) . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 Tb1 O8 N1 98.7(2) . . . . ?
O1 Tb1 O8 N1 52.6(3) . . . . ?
O7 Tb1 O8 N1 -109.3(2) . . . . ?
O2 Tb1 O8 N1 -148.04(19) . . . . ?
O4 Tb1 O8 N1 9.1(2) . . . . ?
O3 Tb1 O8 N1 -47.9(2) . . . . ?
O6 Tb1 O8 N1 169.1(2) . . . . ?
O8 Tb1 O4 C4 -134.9(3) . . . . ?
O5 Tb1 O4 C4 141.6(2) . . . . ?
O1 Tb1 O4 C4 68.3(2) . . . . ?
O7 Tb1 O4 C4 -72.4(2) . . . . ?
O2 Tb1 O4 C4 22.9(3) . . . . ?
O3 Tb1 O4 C4 -9.8(2) . . . . ?
O6 Tb1 O4 C4 -172.3(2) . . . . ?
O8 Tb1 O6 C14 -77.0(2) . . . . ?
O5 Tb1 O6 C14 10.1(2) . . . . ?
O1 Tb1 O6 C14 69.5(2) . . . . ?
O7 Tb1 O6 C14 -149.6(2) . . . . ?
O2 Tb1 O6 C14 129.7(2) . . . . ?
O4 Tb1 O6 C14 -40.2(3) . . . . ?
O3 Tb1 O6 C14 167.4(2) . . . . ?
O8 Tb1 O1 C7 -176.5(2) . . . . ?
O5 Tb1 O1 C7 135.1(2) . . . . ?
O7 Tb1 O1 C7 -24.2(3) . . . . ?
O2 Tb1 O1 C7 17.0(2) . . . . ?
O4 Tb1 O1 C7 -134.0(2) . . . . ?
O3 Tb1 O1 C7 -63.9(2) . . . . ?
O6 Tb1 O1 C7 77.7(2) . . . . ?
O8 Tb1 O5 C12 73.2(2) . . . . ?
O1 Tb1 O5 C12 -131.8(2) . . . . ?
O7 Tb1 O5 C12 26.9(3) . . . . ?
O2 Tb1 O5 C12 -68.8(2) . . . . ?
O4 Tb1 O5 C12 148.3(2) . . . . ?
O3 Tb1 O5 C12 -163.6(2) . . . . ?
O6 Tb1 O5 C12 -6.7(2) . . . . ?
O8 Tb1 O3 C2 76.6(3) . . . . ?
O5 Tb1 O3 C2 -37.2(3) . . . . ?
O1 Tb1 O3 C2 -68.7(2) . . . . ?
O7 Tb1 O3 C2 136.1(3) . . . . ?
O2 Tb1 O3 C2 -143.0(3) . . . . ?
O4 Tb1 O3 C2 16.0(2) . . . . ?
O6 Tb1 O3 C2 -179.9(2) . . . . ?
O8 Tb1 O2 C9 173.34(19) . . . . ?
O5 Tb1 O2 C9 -82.6(2) . . . . ?
O1 Tb1 O2 C9 -18.7(2) . . . . ?
O7 Tb1 O2 C9 136.1(2) . . . . ?
O4 Tb1 O2 C9 28.8(2) . . . . ?
O3 Tb1 O2 C9 59.8(2) . . . . ?
O6 Tb1 O2 C9 -142.5(2) . . . . ?
Tb1 O8 N1 C19 60.7(3) . . . . ?
Tb1 O8 N1 C24 -115.3(2) . . . . ?
Tb1 O5 C12 C13 2.5(4) . . . . ?
Tb1 O5 C12 C11 -178.53(17) . . . . ?
O9 N2 C19 N1 -179.7(3) . . . . ?
C21 N2 C19 N1 -10.1(3) . . . . ?
O9 N2 C19 C18 -1.3(4) . . . . ?
C21 N2 C19 C18 168.4(3) . . . . ?
O8 N1 C19 N2 178.4(2) . . . . ?
C24 N1 C19 N2 -5.5(3) . . . . ?
O8 N1 C19 C18 0.0(4) . . . . ?
C24 N1 C19 C18 176.0(3) . . . . ?
Tb1 O6 C14 C13 -8.9(4) . . . . ?
Tb1 O6 C14 C15 173.04(18) . . . . ?
Tb1 O1 C7 C8 -9.0(4) . . . . ?
Tb1 O1 C7 C6 173.87(18) . . . . ?
O6 C14 C13 C12 -0.7(4) . . . . ?
C15 C14 C13 C12 177.4(3) . . . . ?
O5 C12 C13 C14 4.1(5) . . . . ?
C11 C12 C13 C14 -174.9(2) . . . . ?
N2 C19 C18 C17 -35.5(4) . . . . ?
N1 C19 C18 C17 142.8(3) . . . . ?
N2 C19 C18 C16 33.2(4) . . . . ?
N1 C19 C18 C16 -148.5(3) . . . . ?
O5 C12 C11 F4 -66.1(3) . . . . ?
C13 C12 C11 F4 113.0(3) . . . . ?
O5 C12 C11 F6 49.6(3) . . . . ?
C13 C12 C11 F6 -131.3(3) . . . . ?
O5 C12 C11 F5 173.2(2) . . . . ?
C13 C12 C11 F5 -7.7(3) . . . . ?
Tb1 O2 C9 C8 14.5(4) . . . . ?
Tb1 O2 C9 C10 -167.95(17) . . . . ?
O6 C14 C15 F1 68.2(3) . . . . ?
C13 C14 C15 F1 -110.1(3) . . . . ?
O6 C14 C15 F2 -50.2(3) . . . . ?
C13 C14 C15 F2 131.5(3) . . . . ?
O6 C14 C15 F3 -170.3(3) . . . . ?
C13 C14 C15 F3 11.4(4) . . . . ?
O2 C9 C10 F16 -173.8(3) . . . . ?
C8 C9 C10 F16 4.1(4) . . . . ?
O2 C9 C10 F18 66.1(3) . . . . ?
C8 C9 C10 F18 -116.0(3) . . . . ?
O2 C9 C10 F17 -52.3(3) . . . . ?
C8 C9 C10 F17 125.6(3) . . . . ?
Tb1 O3 C2 C3 -15.5(4) . . . . ?
Tb1 O3 C2 C1 167.37(18) . . . . ?
F14 C1 C2 O3 78.2(3) . . . . ?
F15 C1 C2 O3 -43.4(3) . . . . ?
F13 C1 C2 O3 -165.2(2) . . . . ?
F14 C1 C2 C3 -99.3(3) . . . . ?
F15 C1 C2 C3 139.1(2) . . . . ?
F13 C1 C2 C3 17.3(4) . . . . ?
O9 N2 C21 C20 -47.8(4) . . . . ?
C19 N2 C21 C20 142.5(3) . . . . ?
O9 N2 C21 C22 70.8(4) . . . . ?
C19 N2 C21 C22 -99.0(3) . . . . ?
O9 N2 C21 C24 -170.3(2) . . . . ?
C19 N2 C21 C24 20.0(3) . . . . ?
O1 C7 C8 C9 -7.2(4) . . . . ?
C6 C7 C8 C9 169.9(3) . . . . ?
O2 C9 C8 C7 3.8(5) . . . . ?
C10 C9 C8 C7 -173.6(2) . . . . ?
Tb1 O4 C4 C3 3.0(5) . . . . ?
Tb1 O4 C4 C5 -178.46(18) . . . . ?
O8 N1 C24 C23 76.8(3) . . . . ?
C19 N1 C24 C23 -99.7(3) . . . . ?
O8 N1 C24 C25 -42.2(3) . . . . ?
C19 N1 C24 C25 141.3(3) . . . . ?
O8 N1 C24 C21 -166.4(2) . . . . ?
C19 N1 C24 C21 17.1(3) . . . . ?
C20 C21 C24 N1 -136.9(3) . . . . ?
N2 C21 C24 N1 -21.0(3) . . . . ?
C22 C21 C24 N1 94.4(3) . . . . ?
C20 C21 C24 C23 -27.0(4) . . . . ?
N2 C21 C24 C23 89.0(3) . . . . ?
C22 C21 C24 C23 -155.7(2) . . . . ?
C20 C21 C24 C25 103.4(3) . . . . ?
N2 C21 C24 C25 -140.6(2) . . . . ?
C22 C21 C24 C25 -25.3(3) . . . . ?
O3 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 C4 177.3(2) . . . . ?
O4 C4 C3 C2 5.8(5) . . . . ?
C5 C4 C3 C2 -172.8(3) . . . . ?
C19 C18 C16 C17 -107.5(3) . . . . ?
C19 C18 C17 C16 113.2(3) . . . . ?
O1 C7 C6 F12 -164.4(3) . . . . ?
C8 C7 C6 F12 18.1(4) . . . . ?
O1 C7 C6 F11 74.3(3) . . . . ?
C8 C7 C6 F11 -103.2(3) . . . . ?
O1 C7 C6 F10 -47.2(4) . . . . ?
C8 C7 C6 F10 135.4(3) . . . . ?
O4 C4 C5 F7 58.0(4) . . . . ?
C3 C4 C5 F7 -123.2(3) . . . . ?
O4 C4 C5 F8 -60.2(4) . . . . ?
C3 C4 C5 F8 118.6(3) . . . . ?
O4 C4 C5 F9 -179.2(2) . . . . ?
C3 C4 C5 F9 -0.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O2 0.82 2.36 2.990(3) 134.7 3_656
O7 H7B O6 0.820(18) 2.01(2) 2.764(2) 153(4) 3_656

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.082

_database_code_depnum_ccdc_archive 'CCDC 998208'
