# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


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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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data_x12093
_database_code_depnum_ccdc_archive 'CCDC 881135'
#TrackingRef '11165_web_deposit_cif_file_0_WesleyHenderson_1336500813.(AN)6-LiPF6.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 F6 Li N6 P'
_chemical_formula_weight         398.23

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'A m a 2'

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

_cell_length_a                   14.830(3)
_cell_length_b                   9.2250(16)
_cell_length_c                   14.606(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1998.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    8800
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.89
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9142
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110
_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-Nonius Kappa Axis X8 Apex2'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26318
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         34.02
_reflns_number_total             3787
_reflns_number_gt                3070
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SIR92
_computing_structure_refinement  XL
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0609P)^2^+0.3423P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), 1691 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
#C1S C 0.5000 0.5000 0.4422(3) 0.0610(8) Uani 0.50 1 d P A 3
#C3S C 0.2500 0.9967(2) 0.62729(16) 0.0376(5) Uani 0.50 1 d P B 4
Li1 Li 0.2500 0.9906(3) 0.1284(3) 0.0276(7) Uani 1 2 d S . .
N1 N 0.2500 0.87102(19) 0.01242(13) 0.0338(4) Uani 1 2 d S . .
C1 C 0.2500 0.79630(18) -0.05018(16) 0.0270(3) Uani 1 2 d S . .
C2 C 0.2500 0.7007(2) -0.12912(15) 0.0299(4) Uani 1 2 d S . .
H2A H 0.2205 0.6092 -0.1131 0.045 Uiso 0.50 1 calc PR . .
H2B H 0.3123 0.6816 -0.1481 0.045 Uiso 0.50 1 calc PR . .
H2C H 0.2172 0.7469 -0.1796 0.045 Uiso 0.50 1 calc PR . .
N2 N 0.2500 0.85751(18) 0.24011(13) 0.0290(3) Uani 1 2 d S . .
C3 C 0.2500 0.80561(19) 0.31137(15) 0.0263(4) Uani 1 2 d S . .
C4 C 0.2500 0.7418(2) 0.40183(16) 0.0345(4) Uani 1 2 d S . .
H4A H 0.2634 0.6380 0.3971 0.052 Uiso 0.50 1 calc PR . .
H4B H 0.1906 0.7551 0.4301 0.052 Uiso 0.50 1 calc PR . .
H4C H 0.2960 0.7891 0.4396 0.052 Uiso 0.50 1 calc PR . .
N3 N 0.36352(8) 1.11259(13) 0.13965(9) 0.0327(3) Uani 1 1 d . . .
C5 C 0.42950(9) 1.16925(14) 0.15689(10) 0.0281(3) Uani 1 1 d . . .
C6 C 0.51489(10) 1.23927(19) 0.17823(14) 0.0367(4) Uani 1 1 d . . .
H6A H 0.5053 1.3437 0.1855 0.055 Uiso 1 1 calc R . .
H6B H 0.5577 1.2222 0.1283 0.055 Uiso 1 1 calc R . .
H6C H 0.5391 1.1990 0.2352 0.055 Uiso 1 1 calc R . .
P1 P 0.5000 1.0000 0.44125(4) 0.02621(11) Uani 0.566(12) 2 d SP . 1
F1 F 0.5671(3) 1.0190(5) 0.5200(3) 0.0662(11) Uani 0.566(12) 1 d P . 1
F2 F 0.5736(3) 1.0211(4) 0.3586(3) 0.0449(8) Uani 0.566(12) 1 d P . 1
F3 F 0.4524(5) 1.1557(5) 0.4571(6) 0.107(2) Uani 0.566(12) 1 d P . 1
P1' P 0.5000 1.0000 0.44125(4) 0.02621(11) Uani 0.434(12) 2 d SP . 2
F1' F 0.5701(4) 1.0806(12) 0.5090(5) 0.076(2) Uani 0.434(12) 1 d P . 2
F2' F 0.5634(6) 1.0780(17) 0.3782(7) 0.120(4) Uani 0.434(12) 1 d P . 2
F3' F 0.5278(4) 0.8457(6) 0.4252(4) 0.099(2) Uani 0.434(12) 1 d P . 2
C1S C 0.5000 0.5000 0.4422(3) 0.0610(8) Uani 1 0.5 d P A 3
H1S1 H 0.5589 0.4562 0.4294 0.092 Uiso 0.50 1 calc PR A 3
H1S2 H 0.4736 0.4543 0.4966 0.092 Uiso 0.50 1 calc PR A 3
H1S3 H 0.5076 0.6041 0.4533 0.092 Uiso 0.50 1 calc PR A 3
C2S C 0.4421(2) 0.4789(3) 0.3662(2) 0.0320(6) Uani 0.50 1 d P A 3
N1S N 0.3927(2) 0.4794(4) 0.3059(3) 0.0435(7) Uani 0.50 1 d P A 3
C3S C 0.2500 0.9967(2) 0.62729(16) 0.0376(5) Uani 1 0.50 d P B 4
H3S1 H 0.2851 0.9069 0.6234 0.056 Uiso 0.50 1 calc PR B 4
H3S2 H 0.2911 1.0794 0.6334 0.056 Uiso 0.50 1 calc PR B 4
H3S3 H 0.2137 1.0081 0.5717 0.056 Uiso 0.50 1 calc PR B 4
C4S C 0.19192(19) 0.9906(3) 0.7052(2) 0.0283(5) Uani 0.50 1 d P B 4
N2S N 0.1437(2) 0.9865(3) 0.7655(2) 0.0352(6) Uani 0.50 1 d P B 4

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Li1 0.0249(15) 0.0279(15) 0.0300(17) -0.0017(13) 0.000 0.000
N1 0.0428(10) 0.0291(8) 0.0295(9) -0.0015(7) 0.000 0.000
C1 0.0270(8) 0.0236(7) 0.0304(10) 0.0004(8) 0.000 0.000
C2 0.0326(9) 0.0283(8) 0.0287(10) -0.0052(8) 0.000 0.000
N2 0.0279(8) 0.0276(7) 0.0314(9) -0.0007(7) 0.000 0.000
C3 0.0233(8) 0.0227(7) 0.0330(10) -0.0044(7) 0.000 0.000
C4 0.0422(11) 0.0328(9) 0.0284(10) 0.0003(8) 0.000 0.000
N3 0.0316(6) 0.0310(6) 0.0354(7) -0.0020(5) 0.0025(5) -0.0037(4)
C5 0.0292(6) 0.0236(5) 0.0315(7) -0.0013(5) 0.0013(5) 0.0008(5)
C6 0.0302(7) 0.0317(7) 0.0482(11) -0.0036(7) -0.0056(7) -0.0030(6)
P1 0.02375(18) 0.02530(19) 0.0296(2) 0.000 0.000 -0.00185(16)
F1 0.068(2) 0.060(2) 0.0703(19) 0.0128(17) -0.0503(17) -0.0128(15)
F2 0.0383(12) 0.0564(15) 0.0401(14) 0.0147(10) 0.0187(10) 0.0082(11)
F3 0.124(4) 0.071(2) 0.128(4) -0.064(2) -0.076(3) 0.069(2)
P1' 0.02375(18) 0.02530(19) 0.0296(2) 0.000 0.000 -0.00185(16)
F1' 0.0459(19) 0.115(6) 0.067(3) -0.032(3) -0.0073(18) -0.027(3)
F2' 0.093(4) 0.174(9) 0.092(5) 0.062(6) 0.016(3) -0.058(5)
F3' 0.154(5) 0.051(2) 0.093(4) -0.036(2) -0.081(4) 0.064(2)
C1S 0.0441(12) 0.111(2) 0.0279(10) 0.000 0.000 -0.0190(14)
C2S 0.0287(13) 0.0349(13) 0.0324(15) 0.0053(11) 0.0066(11) 0.0003(10)
N1S 0.0309(14) 0.0526(17) 0.0470(18) 0.0085(14) -0.0004(14) -0.0019(12)
C3S 0.0384(11) 0.0462(12) 0.0284(11) -0.0012(9) 0.000 0.000
C4S 0.0248(11) 0.0250(11) 0.0351(14) -0.0023(10) -0.0043(11) -0.0003(9)
N2S 0.0312(13) 0.0362(14) 0.0381(15) -0.0005(11) 0.0046(12) -0.0011(10)

_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
Li1 N1 2.021(4) . ?
Li1 N3 2.032(2) . ?
Li1 N3 2.032(2) 4 ?
Li1 N2 2.042(4) . ?
N1 C1 1.145(3) . ?
C1 C2 1.451(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 C3 1.146(3) . ?
C3 C4 1.446(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N3 C5 1.1377(18) . ?
C5 C6 1.455(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
P1 F1 1.532(4) . ?
P1 F1 1.532(4) 2_675 ?
P1 F3 1.617(4) . ?
P1 F3 1.617(4) 2_675 ?
P1 F2 1.639(4) 2_675 ?
P1 F2 1.639(4) . ?
F2' F3' 1.672(17) 2_675 ?
F3' F2' 1.672(17) 2_675 ?
C1S C2S 1.417(4) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
C2S N1S 1.146(5) . ?
C3S C4S 1.429(4) . ?
C3S H3S1 0.9800 . ?
C3S H3S2 0.9800 . ?
C3S H3S3 0.9800 . ?
C4S N2S 1.134(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
N1 Li1 N3 111.73(13) . . ?
N1 Li1 N3 111.73(13) . 4 ?
N3 Li1 N3 111.90(15) . 4 ?
N1 Li1 N2 109.98(16) . . ?
N3 Li1 N2 105.56(14) . . ?
N3 Li1 N2 105.56(14) 4 . ?
C1 N1 Li1 176.1(2) . . ?
N1 C1 C2 179.6(2) . . ?
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 . . ?
C3 N2 Li1 167.75(18) . . ?
N2 C3 C4 179.31(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 N3 Li1 170.12(16) . . ?
N3 C5 C6 178.86(16) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
F1 P1 F1 82.6(4) . 2_675 ?
F1 P1 F3 94.3(2) . . ?
F1 P1 F3 73.2(5) 2_675 . ?
F1 P1 F3 73.2(5) . 2_675 ?
F1 P1 F3 94.3(2) 2_675 2_675 ?
F3 P1 F3 163.5(6) . 2_675 ?
F1 P1 F2 178.7(3) . 2_675 ?
F1 P1 F2 96.2(3) 2_675 2_675 ?
F3 P1 F2 85.43(16) . 2_675 ?
F3 P1 F2 106.9(4) 2_675 2_675 ?
F1 P1 F2 96.2(3) . . ?
F1 P1 F2 178.7(3) 2_675 . ?
F3 P1 F2 106.9(4) . . ?
F3 P1 F2 85.43(16) 2_675 . ?
F2 P1 F2 85.1(3) 2_675 . ?
N1S C2S C1S 171.6(3) . . ?
N2S C4S C3S 178.0(3) . . ?

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
N3 Li1 N1 C1 116.88(13) . . . . ?
N3 Li1 N1 C1 -116.88(13) 4 . . . ?
N2 Li1 N1 C1 0.000(6) . . . . ?
Li1 N1 C1 C2 0.00(11) . . . . ?
N1 Li1 N2 C3 180.000(3) . . . . ?
N3 Li1 N2 C3 59.33(11) . . . . ?
N3 Li1 N2 C3 -59.33(11) 4 . . . ?
Li1 N2 C3 C4 0.00(7) . . . . ?
N1 Li1 N3 C5 -116.7(8) . . . . ?
N3 Li1 N3 C5 117.2(8) 4 . . . ?
N2 Li1 N3 C5 2.9(9) . . . . ?
Li1 N3 C5 C6 77(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        32.63
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.044