# 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 2016

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

data_LKM5195_0m
_database_code_depnum_ccdc_archive 'CCDC 1421004'
_audit_update_record             
;
2015-08-27 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'N,N-dimethylethanol ammonium tetrakis(trifluoroacetato)cerate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Ce F12 N O9'
_chemical_formula_weight         682.35

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'
Ce Ce -0.2486 2.6331 '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'

_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                   8.7485(9)
_cell_length_b                   11.5996(13)
_cell_length_c                   12.3113(13)
_cell_angle_alpha                109.6251(17)
_cell_angle_beta                 101.8129(15)
_cell_angle_gamma                104.2412(17)
_cell_volume                     1082.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3327
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      28.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.093
_exptl_crystal_F_000             658
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.249
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5938
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.850
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4329
_reflns_number_gt                3954
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0409P)²+2.7173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4329
_refine_ls_number_parameters     315
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.063
_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_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
Ce1 Ce 0.71994(3) 0.96008(2) -0.04703(2) 0.01203(8) Uani 1 1 d . . . . .
F1 F 0.0945(3) 0.8725(3) -0.3254(3) 0.0380(7) Uani 1 1 d . . . . .
F2 F 0.2758(4) 0.9465(4) -0.4015(3) 0.0483(9) Uani 1 1 d . . . . .
F3 F 0.1993(4) 0.7457(3) -0.4318(3) 0.0456(9) Uani 1 1 d . . . . .
F4 F 0.2106(5) 0.6091(3) 0.0464(4) 0.0634(12) Uani 1 1 d . . . . .
F5 F 0.4655(5) 0.6253(4) 0.0902(3) 0.0606(11) Uani 1 1 d . . . . .
F6 F 0.3092(4) 0.5309(3) -0.0940(3) 0.0425(8) Uani 1 1 d . . . . .
F7 F 0.8414(4) 0.5725(3) -0.3414(3) 0.0410(8) Uani 1 1 d . . . . .
F8 F 1.0928(3) 0.6586(3) -0.2238(3) 0.0374(7) Uani 1 1 d . . . . .
F9 F 0.9024(5) 0.5548(3) -0.1728(3) 0.0456(8) Uani 1 1 d . . . . .
O1 O 0.5032(4) 0.8770(3) -0.2559(3) 0.0198(6) Uani 1 1 d . . . . .
O2 O 0.3587(4) 0.9485(3) -0.1349(3) 0.0196(6) Uani 1 1 d . . . . .
O3 O 0.4969(3) 0.7739(3) -0.0560(3) 0.0182(6) Uani 1 1 d . . . . .
O4 O 0.3303(4) 0.8406(3) 0.0506(3) 0.0197(6) Uani 1 1 d . . . . .
O5 O 0.7515(3) 0.7518(3) -0.1869(3) 0.0180(6) Uani 1 1 d . . . . .
O6 O 1.0203(4) 0.8583(3) -0.0881(3) 0.0201(6) Uani 1 1 d . . . . .
O7 O 0.8548(4) 0.8798(3) 0.0967(3) 0.0196(6) Uani 1 1 d . . . . .
O8 O 1.1325(3) 0.9773(3) 0.1806(3) 0.0179(6) Uani 1 1 d . . . . .
C1 C 0.3781(5) 0.8994(4) -0.2357(4) 0.0151(8) Uani 1 1 d . . . . .
C2 C 0.2344(6) 0.8653(5) -0.3496(4) 0.0256(10) Uani 1 1 d . . . . .
C3 C 0.3942(5) 0.7623(4) 0.0006(4) 0.0144(8) Uani 1 1 d . . . . .
C4 C 0.3431(6) 0.6298(5) 0.0103(4) 0.0259(10) Uani 1 1 d . . . . .
C5 C 0.9009(5) 0.7619(4) -0.1610(4) 0.0151(8) Uani 1 1 d . . . . .
C6 C 0.9366(5) 0.6364(4) -0.2255(4) 0.0211(9) Uani 1 1 d . . . . .
C7 C 0.9929(5) 0.9059(4) 0.1682(4) 0.0154(8) Uani 1 1 d . . . . .
C8 C 0.9927(6) 0.8381(5) 0.2556(4) 0.0264(10) Uani 1 1 d . . . . .
F10 F 1.0479(12) 0.7422(8) 0.2275(8) 0.0664(11) Uani 0.5 1 d D . P A 1
F11 F 0.8672(11) 0.8397(8) 0.3004(8) 0.0664(11) Uani 0.5 1 d D U P A 1
F12 F 1.0658(10) 0.9237(8) 0.3720(8) 0.0664(11) Uani 0.5 1 d D U P A 1
F10' F 0.9605(11) 0.7091(9) 0.1962(8) 0.0664(11) Uani 0.5 1 d D U P A 2
F11' F 0.8388(12) 0.7795(8) 0.2568(8) 0.0664(11) Uani 0.5 1 d D U P A 2
F12' F 1.1384(11) 0.8778(8) 0.3392(7) 0.0664(11) Uani 0.5 1 d D . P A 2
O9 O 0.4790(4) 0.5943(3) 0.6075(3) 0.0242(7) Uani 1 1 d . . . . .
H9 H 0.5659 0.6332 0.6643 0.036 Uiso 1 1 calc R U . . .
N1 N 0.4493(5) 0.3251(4) 0.5712(3) 0.0215(8) Uani 1 1 d . . . . .
H1 H 0.5054 0.3737 0.5307 0.026 Uiso 1 1 calc R U . . .
C9 C 0.3599(6) 0.5198(5) 0.6419(4) 0.0244(10) Uani 1 1 d . . . . .
H9A H 0.2565 0.4749 0.5752 0.029 Uiso 1 1 calc R U . . .
H9B H 0.3385 0.5772 0.7106 0.029 Uiso 1 1 calc R U . . .
C10 C 0.4205(6) 0.4212(4) 0.6759(4) 0.0226(9) Uani 1 1 d . . . . .
H10A H 0.5234 0.4666 0.7431 0.027 Uiso 1 1 calc R U . . .
H10B H 0.3390 0.3744 0.7029 0.027 Uiso 1 1 calc R U . . .
C11 C 0.2911(6) 0.2262(5) 0.4800(4) 0.0331(12) Uani 1 1 d . . . . .
H11A H 0.2340 0.1764 0.5171 0.050 Uiso 1 1 calc R U . . .
H11B H 0.3147 0.1692 0.4135 0.050 Uiso 1 1 calc R U . . .
H11C H 0.2225 0.2691 0.4503 0.050 Uiso 1 1 calc R U . . .
C12 C 0.5608(7) 0.2610(5) 0.6155(5) 0.0357(12) Uani 1 1 d . . . . .
H12A H 0.6653 0.3258 0.6697 0.054 Uiso 1 1 calc R U . . .
H12B H 0.5787 0.2011 0.5477 0.054 Uiso 1 1 calc R U . . .
H12C H 0.5103 0.2146 0.6579 0.054 Uiso 1 1 calc R U . . .


_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
Ce1 O2 2.452(3) 2_675 ?
Ce1 O4 2.470(3) 2_675 ?
Ce1 O8 2.471(3) 2_775 ?
Ce1 O6 2.473(3) 2_775 ?
Ce1 O3 2.482(3) . ?
Ce1 O7 2.486(3) . ?
Ce1 O1 2.564(3) . ?
Ce1 O5 2.571(3) . ?
F1 C2 1.332(5) . ?
F2 C2 1.325(6) . ?
F3 C2 1.329(6) . ?
F4 C4 1.320(6) . ?
F5 C4 1.322(6) . ?
F6 C4 1.319(5) . ?
F7 C6 1.334(5) . ?
F8 C6 1.321(5) . ?
F9 C6 1.326(5) . ?
O1 C1 1.239(5) . ?
O2 C1 1.245(5) . ?
O2 Ce1 2.452(3) 2_675 ?
O3 C3 1.254(5) . ?
O4 C3 1.238(5) . ?
O4 Ce1 2.470(3) 2_675 ?
O5 C5 1.246(5) . ?
O6 C5 1.230(5) . ?
O6 Ce1 2.473(3) 2_775 ?
O7 C7 1.238(5) . ?
O8 C7 1.242(5) . ?
O8 Ce1 2.471(3) 2_775 ?
C1 C2 1.538(6) . ?
C3 C4 1.543(6) . ?
C5 C6 1.548(6) . ?
C7 C8 1.530(6) . ?
C8 F10 1.290(11) . ?
C8 F12' 1.324(10) . ?
C8 F11 1.328(11) . ?
C8 F12 1.344(10) . ?
C8 F10' 1.351(11) . ?
C8 F11' 1.357(10) . ?
F11 F12 1.646(10) . ?
F10' F11' 1.643(11) . ?
O9 C9 1.413(5) . ?
O9 H9 0.8200 . ?
N1 C11 1.487(6) . ?
N1 C12 1.488(6) . ?
N1 C10 1.508(6) . ?
N1 H1 0.9800 . ?
C9 C10 1.515(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Ce1 O4 74.36(10) 2_675 2_675 ?
O2 Ce1 O8 142.38(10) 2_675 2_775 ?
O4 Ce1 O8 74.01(10) 2_675 2_775 ?
O2 Ce1 O6 78.81(10) 2_675 2_775 ?
O4 Ce1 O6 74.39(10) 2_675 2_775 ?
O8 Ce1 O6 73.50(9) 2_775 2_775 ?
O2 Ce1 O3 75.83(10) 2_675 . ?
O4 Ce1 O3 121.79(10) 2_675 . ?
O8 Ce1 O3 139.49(9) 2_775 . ?
O6 Ce1 O3 143.74(10) 2_775 . ?
O2 Ce1 O7 75.99(10) 2_675 . ?
O4 Ce1 O7 140.52(10) 2_675 . ?
O8 Ce1 O7 119.15(10) 2_775 . ?
O6 Ce1 O7 74.76(10) 2_775 . ?
O3 Ce1 O7 74.25(10) . . ?
O2 Ce1 O1 118.48(10) 2_675 . ?
O4 Ce1 O1 76.97(10) 2_675 . ?
O8 Ce1 O1 72.91(9) 2_775 . ?
O6 Ce1 O1 140.55(10) 2_775 . ?
O3 Ce1 O1 75.22(10) . . ?
O7 Ce1 O1 141.18(10) . . ?
O2 Ce1 O5 142.95(10) 2_675 . ?
O4 Ce1 O5 140.51(9) 2_675 . ?
O8 Ce1 O5 73.68(10) 2_775 . ?
O6 Ce1 O5 116.58(10) 2_775 . ?
O3 Ce1 O5 73.27(9) . . ?
O7 Ce1 O5 76.36(10) . . ?
O1 Ce1 O5 72.30(9) . . ?
C1 O1 Ce1 105.9(2) . . ?
C1 O2 Ce1 171.8(3) . 2_675 ?
C3 O3 Ce1 134.5(3) . . ?
C3 O4 Ce1 139.3(3) . 2_675 ?
C5 O5 Ce1 109.4(3) . . ?
C5 O6 Ce1 173.5(3) . 2_775 ?
C7 O7 Ce1 139.4(3) . . ?
C7 O8 Ce1 136.8(3) . 2_775 ?
O1 C1 O2 127.4(4) . . ?
O1 C1 C2 114.9(4) . . ?
O2 C1 C2 117.6(4) . . ?
F2 C2 F3 107.1(4) . . ?
F2 C2 F1 107.7(4) . . ?
F3 C2 F1 107.1(4) . . ?
F2 C2 C1 109.9(4) . . ?
F3 C2 C1 111.8(4) . . ?
F1 C2 C1 113.0(4) . . ?
O4 C3 O3 130.1(4) . . ?
O4 C3 C4 115.8(4) . . ?
O3 C3 C4 114.0(4) . . ?
F6 C4 F4 106.9(4) . . ?
F6 C4 F5 107.5(4) . . ?
F4 C4 F5 107.3(4) . . ?
F6 C4 C3 112.4(4) . . ?
F4 C4 C3 112.7(4) . . ?
F5 C4 C3 109.8(4) . . ?
O6 C5 O5 127.3(4) . . ?
O6 C5 C6 117.4(4) . . ?
O5 C5 C6 115.2(4) . . ?
F8 C6 F9 107.7(4) . . ?
F8 C6 F7 107.3(4) . . ?
F9 C6 F7 106.2(4) . . ?
F8 C6 C5 113.1(4) . . ?
F9 C6 C5 110.2(4) . . ?
F7 C6 C5 112.0(4) . . ?
O7 C7 O8 130.8(4) . . ?
O7 C7 C8 115.0(4) . . ?
O8 C7 C8 114.3(4) . . ?
F10 C8 F11 124.4(7) . . ?
F10 C8 F12 113.1(6) . . ?
F11 C8 F12 76.1(6) . . ?
F12' C8 F10' 103.5(6) . . ?
F12' C8 F11' 129.2(6) . . ?
F10' C8 F11' 74.7(5) . . ?
F10 C8 C7 113.9(5) . . ?
F12' C8 C7 113.8(5) . . ?
F11 C8 C7 111.6(5) . . ?
F12 C8 C7 111.8(5) . . ?
F10' C8 C7 111.1(5) . . ?
F11' C8 C7 113.8(5) . . ?
C8 F11 F12 52.4(5) . . ?
C8 F12 F11 51.5(5) . . ?
C8 F10' F11' 52.8(5) . . ?
C8 F11' F10' 52.5(5) . . ?
C9 O9 H9 109.5 . . ?
C11 N1 C12 110.6(4) . . ?
C11 N1 C10 112.1(4) . . ?
C12 N1 C10 110.8(4) . . ?
C11 N1 H1 107.7 . . ?
C12 N1 H1 107.7 . . ?
C10 N1 H1 107.7 . . ?
O9 C9 C10 110.8(4) . . ?
O9 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
O9 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C9 112.3(4) . . ?
N1 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
O9 H9 O5 0.82 1.97 2.776(4) 168.3 1_556
N1 H1 O9 0.98 1.88 2.786(5) 152.1 2_666
C10 H10A F5 0.97 2.61 3.116(5) 112.9 2_666
C10 H10B F11' 0.97 2.32 3.274(9) 166.4 2_666
C11 H11A F11 0.96 2.62 3.495(10) 151.2 2_666

_refine_diff_density_max         2.055
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.126

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
