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

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 F6 O7 Yb, C2 H4 O2'
_chemical_formula_sum            'C8 H9 F6 O9 Yb'
_chemical_formula_weight         536.19

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'
O O 0.0106 0.0060 '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'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.940(2)
_cell_length_b                   9.659(2)
_cell_length_c                   10.774(2)
_cell_angle_alpha                86.50(3)
_cell_angle_beta                 79.25(3)
_cell_angle_gamma                76.36(3)
_cell_volume                     788.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      25.44

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.258
_exptl_crystal_F_000             506
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    6.035
_shelx_estimated_absorpt_T_min   0.325
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3054
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'Bruker APEX2'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13147
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         25.524
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2804
_reflns_number_gt                2744
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0062P)²+12.6584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2804
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb 0.21381(4) 0.07374(3) -0.00815(2) 0.01048(11) Uani 1 1 d . . . . .
F1 F 0.3311(7) 0.3345(5) 0.3427(4) 0.0350(12) Uani 1 1 d . . . . .
F2 F 0.3237(7) 0.1292(5) 0.4313(4) 0.0356(12) Uani 1 1 d . . . . .
F3 F 0.5759(7) 0.1756(7) 0.3614(5) 0.0531(16) Uani 1 1 d . . . . .
F4 F 0.2649(7) -0.3875(6) 0.1971(7) 0.066(2) Uani 1 1 d . . . . .
F5 F 0.5445(9) -0.4865(6) 0.1412(8) 0.072(2) Uani 1 1 d . . . . .
F6 F 0.4524(12) -0.3640(8) 0.3057(6) 0.081(3) Uani 1 1 d . . . . .
O1 O 0.0602(7) -0.5043(5) -0.1877(5) 0.0199(11) Uani 1 1 d . . . . .
O2 O 0.1563(9) -0.6274(6) -0.3688(5) 0.0297(13) Uani 1 1 d . . . . .
H2 H 0.152(14) -0.694(12) -0.314(11) 0.05(3) Uiso 1 1 d . . . . .
O3 O 0.2603(6) 0.1521(5) 0.1792(4) 0.0158(10) Uani 1 1 d . . . . .
O4 O 0.3082(6) -0.1388(5) 0.1002(5) 0.0180(10) Uani 1 1 d . . . . .
O5 O 0.4400(7) -0.0676(5) -0.1457(5) 0.0203(11) Uani 1 1 d . . . . .
O6 O 0.3929(6) 0.2258(5) -0.0801(5) 0.0188(10) Uani 1 1 d . . . . .
O7 O 0.0396(6) -0.0291(5) -0.1269(4) 0.0120(9) Uani 1 1 d . . . . .
O8 O 0.1464(6) 0.1472(5) -0.2147(4) 0.0154(10) Uani 1 1 d . . . . .
O9 O 0.0105(7) 0.2938(6) 0.0092(5) 0.0166(10) Uani 1 1 d . . . . .
H9A H 0.019(17) 0.339(14) -0.050(14) 0.07(4) Uiso 1 1 d . . . . .
H9B H -0.012(15) 0.337(12) 0.073(12) 0.05(3) Uiso 1 1 d . . . . .
C1 C 0.1130(10) -0.5085(8) -0.3024(7) 0.0193(15) Uani 1 1 d . . . . .
C2 C 0.1311(13) -0.3772(9) -0.3841(8) 0.033(2) Uani 1 1 d . . . . .
H2A H 0.1018 -0.2935 -0.3305 0.050 Uiso 1 1 calc R U . . .
H2B H 0.0507 -0.3635 -0.4449 0.050 Uiso 1 1 calc R U . . .
H2C H 0.2525 -0.3899 -0.4297 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4120(9) 0.1322(7) 0.2065(6) 0.0118(13) Uani 1 1 d . . . . .
C4 C 0.4126(10) 0.1942(8) 0.3370(7) 0.0200(15) Uani 1 1 d . . . . .
C5 C 0.4247(10) -0.3705(8) 0.1873(8) 0.0254(17) Uani 1 1 d . . . . .
C6 C 0.4492(9) -0.2302(7) 0.1138(6) 0.0149(14) Uani 1 1 d . . . . .
C7 C 0.0621(8) 0.0547(7) -0.2229(6) 0.0127(13) Uani 1 1 d . . . . .
C8 C -0.0027(10) 0.0427(9) -0.3424(7) 0.0183(15) Uani 1 1 d . . . . .
H8A H -0.076(11) -0.011(9) -0.332(8) 0.02(2) Uiso 1 1 d . . . . .
H8B H -0.049(13) 0.133(11) -0.374(9) 0.04(3) Uiso 1 1 d . . . . .
H8C H 0.104(13) -0.003(10) -0.406(9) 0.04(3) 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
Yb1 O6 2.284(5) . ?
Yb1 O3 2.319(4) . ?
Yb1 O5 2.320(5) . ?
Yb1 O4 2.333(5) . ?
Yb1 O9 2.340(5) . ?
Yb1 O7 2.365(4) 2 ?
Yb1 O8 2.411(5) . ?
Yb1 O7 2.450(4) . ?
Yb1 C7 2.835(7) . ?
Yb1 C3 3.175(6) . ?
Yb1 Yb1 3.9519(12) 2 ?
Yb1 H9A 2.72(13) . ?
F1 C4 1.357(9) . ?
F2 C4 1.338(8) . ?
F3 C4 1.339(9) . ?
F4 C5 1.302(9) . ?
F5 C5 1.340(10) . ?
F6 C5 1.342(10) . ?
O1 C1 1.228(9) . ?
O2 C1 1.331(9) . ?
O2 H2 0.85(11) . ?
O3 C3 1.261(8) . ?
O4 C6 1.278(9) . ?
O5 C3 1.271(8) 2_655 ?
O6 C6 1.248(8) 2_655 ?
O7 C7 1.286(8) . ?
O7 Yb1 2.365(4) 2 ?
O8 C7 1.252(8) . ?
O9 H9A 0.76(14) . ?
O9 H9B 0.80(12) . ?
C1 C2 1.519(10) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 O5 1.271(8) 2_655 ?
C3 C4 1.563(9) . ?
C5 C6 1.561(10) . ?
C6 O6 1.248(8) 2_655 ?
C7 C8 1.493(9) . ?
C8 H8A 0.86(9) . ?
C8 H8B 0.93(10) . ?
C8 H8C 1.01(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
O6 Yb1 O3 78.21(17) . . ?
O6 Yb1 O5 77.55(18) . . ?
O3 Yb1 O5 121.62(18) . . ?
O6 Yb1 O4 122.70(17) . . ?
O3 Yb1 O4 77.22(17) . . ?
O5 Yb1 O4 73.03(18) . . ?
O6 Yb1 O9 78.85(18) . . ?
O3 Yb1 O9 79.78(19) . . ?
O5 Yb1 O9 143.36(19) . . ?
O4 Yb1 O9 143.59(18) . . ?
O6 Yb1 O7 149.15(17) . 2 ?
O3 Yb1 O7 81.32(15) . 2 ?
O5 Yb1 O7 133.19(16) . 2 ?
O4 Yb1 O7 73.95(16) . 2 ?
O9 Yb1 O7 74.98(17) . 2 ?
O6 Yb1 O8 76.22(17) . . ?
O3 Yb1 O8 144.55(16) . . ?
O5 Yb1 O8 75.88(17) . . ?
O4 Yb1 O8 137.80(17) . . ?
O9 Yb1 O8 71.52(18) . . ?
O7 Yb1 O8 109.88(16) 2 . ?
O6 Yb1 O7 128.12(16) . . ?
O3 Yb1 O7 151.01(15) . . ?
O5 Yb1 O7 80.46(17) . . ?
O4 Yb1 O7 93.89(16) . . ?
O9 Yb1 O7 92.73(17) . . ?
O7 Yb1 O7 69.69(17) 2 . ?
O8 Yb1 O7 52.95(15) . . ?
O6 Yb1 C7 101.66(18) . . ?
O3 Yb1 C7 161.31(18) . . ?
O5 Yb1 C7 75.98(18) . . ?
O4 Yb1 C7 116.82(18) . . ?
O9 Yb1 C7 81.86(19) . . ?
O7 Yb1 C7 90.58(16) 2 . ?
O8 Yb1 C7 26.05(17) . . ?
O7 Yb1 C7 26.92(16) . . ?
O6 Yb1 C3 69.18(17) . . ?
O3 Yb1 C3 19.65(17) . . ?
O5 Yb1 C3 102.09(18) . . ?
O4 Yb1 C3 70.49(17) . . ?
O9 Yb1 C3 95.16(18) . . ?
O7 Yb1 C3 97.07(15) 2 . ?
O8 Yb1 C3 144.81(15) . . ?
O7 Yb1 C3 162.23(15) . . ?
C7 Yb1 C3 170.80(17) . . ?
O6 Yb1 Yb1 153.71(13) . 2 ?
O3 Yb1 Yb1 116.86(12) . 2 ?
O5 Yb1 Yb1 107.87(13) . 2 ?
O4 Yb1 Yb1 82.91(12) . 2 ?
O9 Yb1 Yb1 82.79(12) . 2 ?
O7 Yb1 Yb1 35.54(10) 2 2 ?
O8 Yb1 Yb1 80.22(11) . 2 ?
O7 Yb1 Yb1 34.14(10) . 2 ?
C7 Yb1 Yb1 56.87(13) . 2 ?
C3 Yb1 Yb1 131.60(11) . 2 ?
O6 Yb1 H9A 69(3) . . ?
O3 Yb1 H9A 89(3) . . ?
O5 Yb1 H9A 129(3) . . ?
O4 Yb1 H9A 158(3) . . ?
O9 Yb1 H9A 15(3) . . ?
O7 Yb1 H9A 88(3) 2 . ?
O8 Yb1 H9A 59(3) . . ?
O7 Yb1 H9A 90(3) . . ?
C7 Yb1 H9A 73(3) . . ?
C3 Yb1 H9A 102(3) . . ?
Yb1 Yb1 H9A 88(3) 2 . ?
C1 O2 H2 105(7) . . ?
C3 O3 Yb1 122.1(4) . . ?
C6 O4 Yb1 140.7(4) . . ?
C3 O5 Yb1 165.6(5) 2_655 . ?
C6 O6 Yb1 142.5(5) 2_655 . ?
C7 O7 Yb1 133.1(4) . 2 ?
C7 O7 Yb1 93.5(4) . . ?
Yb1 O7 Yb1 110.31(17) 2 . ?
C7 O8 Yb1 96.2(4) . . ?
Yb1 O9 H9A 113(10) . . ?
Yb1 O9 H9B 120(8) . . ?
H9A O9 H9B 114(10) . . ?
O1 C1 O2 123.9(7) . . ?
O1 C1 C2 123.3(7) . . ?
O2 C1 C2 112.8(6) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C3 O5 129.8(6) . 2_655 ?
O3 C3 C4 113.5(6) . . ?
O5 C3 C4 116.7(6) 2_655 . ?
O3 C3 Yb1 38.2(3) . . ?
O5 C3 Yb1 91.6(4) 2_655 . ?
C4 C3 Yb1 151.7(4) . . ?
F2 C4 F3 106.5(6) . . ?
F2 C4 F1 106.3(6) . . ?
F3 C4 F1 110.0(6) . . ?
F2 C4 C3 110.9(5) . . ?
F3 C4 C3 112.0(6) . . ?
F1 C4 C3 110.8(6) . . ?
F4 C5 F5 111.6(7) . . ?
F4 C5 F6 106.4(7) . . ?
F5 C5 F6 103.6(8) . . ?
F4 C5 C6 111.9(6) . . ?
F5 C5 C6 113.5(6) . . ?
F6 C5 C6 109.3(6) . . ?
O6 C6 O4 130.7(6) 2_655 . ?
O6 C6 C5 113.0(6) 2_655 . ?
O4 C6 C5 116.3(6) . . ?
O8 C7 O7 117.3(6) . . ?
O8 C7 C8 119.8(6) . . ?
O7 C7 C8 122.9(6) . . ?
O8 C7 Yb1 57.7(3) . . ?
O7 C7 Yb1 59.6(3) . . ?
C8 C7 Yb1 175.2(5) . . ?
C7 C8 H8A 112(6) . . ?
C7 C8 H8B 110(6) . . ?
H8A C8 H8B 112(8) . . ?
C7 C8 H8C 107(5) . . ?
H8A C8 H8C 108(8) . . ?
H8B C8 H8C 108(8) . . ?

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
Yb1 O3 C3 O5 -2.0(9) . . . 2_655 ?
Yb1 O3 C3 C4 179.8(4) . . . . ?
O3 C3 C4 F2 63.2(8) . . . . ?
O5 C3 C4 F2 -115.2(7) 2_655 . . . ?
Yb1 C3 C4 F2 63.5(11) . . . . ?
O3 C3 C4 F3 -177.9(6) . . . . ?
O5 C3 C4 F3 3.6(9) 2_655 . . . ?
Yb1 C3 C4 F3 -177.6(7) . . . . ?
O3 C3 C4 F1 -54.6(8) . . . . ?
O5 C3 C4 F1 126.9(6) 2_655 . . . ?
Yb1 C3 C4 F1 -54.4(11) . . . . ?
Yb1 O4 C6 O6 11.4(12) . . . 2_655 ?
Yb1 O4 C6 C5 -170.3(5) . . . . ?
F4 C5 C6 O6 -165.8(7) . . . 2_655 ?
F5 C5 C6 O6 -38.4(10) . . . 2_655 ?
F6 C5 C6 O6 76.6(9) . . . 2_655 ?
F4 C5 C6 O4 15.6(10) . . . . ?
F5 C5 C6 O4 142.9(7) . . . . ?
F6 C5 C6 O4 -102.0(8) . . . . ?
Yb1 O8 C7 O7 2.9(6) . . . . ?
Yb1 O8 C7 C8 -175.2(6) . . . . ?
Yb1 O7 C7 O8 119.4(6) 2 . . . ?
Yb1 O7 C7 O8 -2.9(6) . . . . ?
Yb1 O7 C7 C8 -62.5(9) 2 . . . ?
Yb1 O7 C7 C8 175.2(6) . . . . ?
Yb1 O7 C7 Yb1 122.3(5) 2 . . . ?

_refine_diff_density_max         2.423
_refine_diff_density_min         -1.181
_refine_diff_density_rms         0.198

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 996572'
