Synthesis and X-ray crystal structure of fluorous imidazolium salts

Article abstract of DOI:10.1007/BF03246551

Synthesis of two salts involving CH₂O spacer between the imidazole nitrogen and hexafluoroisopropyl group in the fluorous imidazolium cations is reported. Such an insertion would result in the formation of a-ammonium ether. The two fluorous imidazolium salts involve one or two-CH ₂OCH(CF₃)₂ groups attached to the imidazole nitrogen atoms. These products were synthesized from the reaction between methyimidazole and imidazole as nucleophiles and sevochlorane, ClCH ₂OCH(CF₃)₂, as electrophile, in different molar ratios. The resulting products have been characterized by ¹H, ¹³C, and ¹⁹F NMR and FTIR spectroscopy. Also, the single crystal X-ray diffraction analysis for the symmetrically substituted imidazolium product is presented. The preliminary animal tests indicated no anesthetic property but the two tested salts were found to behave as calmative.

Full text of DOI:10.1007/BF03246551

J. Iran. Chem. Soc., Vol. 8, No. 4, December 2011, pp. 958-964.
JOURIrNaAnLiaOnF THE
Chemical Society
ꢀꢀꢀꢀꢀꢀ
ꢀ
Synthesis and X-Ray Crystal Structure of Fluorous Imidazolium Salts
A. Moghimia,*, H.R. Khavassib, A.H. Benvidic, M. Vojdanic and N. Faghihimoghaddamc
aDepartment of Chemistry, Imam Hossein University, Tehran, Iran, P.O. Box 16575-347
bDepartment of Chemistry, Shahid Beheshti University, Tehran, Iran
cDepartment of Chemistry, Islamic Azad University, North Branch, Tehran, Iran
(Received 21 December 2010, Accepted 24 February 2011)
Synthesis of two salts involving CH2O spacer between the imidazole nitrogen and hexafluoroisopropyl group in the fluorous
imidazolium cations is reported. Such an insertion would result in the formation of α-ammonium ether. The two fluorous
imidazolium salts involve one or two -CH2OCH(CF3)2 groups attached to the imidazole nitrogen atoms. These products were
synthesized from the reaction between methyimidazole and imidazole as nucleophiles and sevochlorane, ClCH2OCH(CF3)2, as
1
electrophile, in different molar ratios. The resulting products have been characterized by H, 13C, and 19F NMR and FTIR
spectroscopy. Also, the single crystal X-ray diffraction analysis for the symmetrically substituted imidazolium product is
presented. The preliminary animal tests indicated no anesthetic property but the two tested salts were found to behave as
calmative.
Keywords: Imidazole, Imidazolium, Fluorous, α-Ammonium ether, X-Ray crystal structure
INTRODUCTION
have been comprehensively reviewed. The synthesis of each
member of fluoroalkylated imidazolium salts, on the other
hand, needs its own specific strategy [3-10].
From the synthetic point of view, there are two general
approaches to prepare novel 1,3-dialkylimidazolium salts. In
the first approach, the alkyl group attached to the nitrogen
atom of imidazole ring is modified. In the second, the anion of
dialkylimidazolium salt is exchanged [1-4]. One way to apply
structural modifications on dialkylimidazolium salts is to
induce fluorine atom either on the cationic or anionic parts to
reach fluorous imidazolium salts. An exploration of the
literature indicates that the number of imidazolium-based salts
containing fluoroanions is much larger since the former can be
easily obtained by the anion exchange process [1,2].
Imidazolium salts containing fluoroanions such as (FH)nF-,
Some of the reported fluorous imidazolium cations are
shown in Fig. 1. As is clear, fluoroalkyl groups are directly or
indirectly, by (CH2)n spacers, attached to one or two imidazole
nitrogen atoms. A review of the fluorinated imidazolium
cations revealed no report on the insertion of CH2O spacer
between the imidazole nitrogen and hexafluoroisopropyl
groups. Such an insertion would result in the formation of α-
ammonium ether, as shown in Fig. 2. Here, we report the first
synthesis of fluorous imidazolium salts (2) and (4) involving
one or two CH2OCH(CF3)2 groups attached to the imidazole
nitrogen atoms as well as the X-ray single crystal data
obtained for salt (4). Considering the fact that CH2OCH(CF3)2
group in the prepared salts forms the major part of the
chemical structure of sevofluorane FCH2OCH(CF3)2, a well-
-
-
-
-
-
-
-
BF4 , PF6 , N(SO2CF3)2 , OSO2CF3 , AsF6 , SbF6 and NbF6
*Corresponding author. E-mail: samoghimi@yahoo.com

Moghimi et al.
N
N
N
N
N
N
R2
R1
R2
R1
R
Mes
R = CH2C8F17
R1,R2 = CH2C6F13 , CH2C8F17
R1 = Mes ; R2 = C2H4C6F13
R1 = Mes ; R2 = CH2C8F17
R1,R2 = CH2C6F13 , CH2C8F17
( b )
R =
CH2CH2C6F13
( c )
( a )
N
N
CF2CF2H
R
C8F17
N
N
N
N
SO3
C8F17
R = CH3 , C2H5
( d )
( e )
( f )
ꢀ
Fig. 1. Some of the selected fluorous imidazolium cations reported in the literature.
N
N
N
N
CH2OCH(CF3)2
(F3C)2HCOH2C
CH2OCH(CF3)2
H3C
( 4 )
( 2 )
ꢀ
Fig. 2. Imidazolium salts reported in the current research.
and the mixture was stirred while cooling at 0 °C in an ice
bath for 2 h and then stirred for 3 h at RT. Afterward, water
(10 g) was gradually added while vigorously stirring for 15
min. The organic phase was separated and distilled to get SVC
known general inhalation anesthetic, the current water soluble
molecules are expected to be biologically active.
EXPERIMENTAL
1
(4.25 g) in 85% yield. H NMR (CDCl3): δ 4.66 (septet,
3JFCCH = 5.73 Hz, 1H), 5.56 (s, 2H). 13C NMR (CDCl3): δ 72.8
1,1,1,3,3,3-Hexa fluoro isopropanol (HFIP), imidazole and
methyl imidazole were prepared from Merck. NMR spectra
were recorded with a Brucker spectrometer (1H NMR spectra
at 250.13 MHz, 13C NMR spectra at 62.90 MHz and 19F NMR
spectra at 235.13 MHz). Chemical shifts are reported on the δ
scale relative to TMS. FTIR spectra were recorded on a Perkin
Elmer spectrophotometer using KBr disc. Melting points were
determined using Mettler.
2
2
(septet, JFCC = 33.4 Hz), 80 (s), 121.0 (dq, JFC = 28.31 Hz,
3JFCCC = 3.02 Hz). 19F NMR (CDCl3): δ -73.34 (d, J = 6.34 Hz,
6F).
Synthesis of 1-(1,1,1,3,3,3-Hexafluoroproisopoxy-
methyl)-3-methylimidazolium Salt 2
To a sample tube (20 ml) containing methyl imidazole
(0.82 g, 0.01 mol) was added SVC (2.17 g, 0.01 mol) at room
temperature and the mixture was stirred for 3 days. The
resulting viscose liquid was recrystallized from acetonitrile.
The white crystals were obtained and washed by 2 × 2 ml
diethyl ether and vacuum dried to get 2.49 g pure product 2
in 91% yield. 1H NMR (DMSO+D2O): δ 3.84 (s, 3H), 6.07 (s,
2H), 6.46 (septet, 3JFCCH = 6.25 Hz, 1H), 7.81 (s, 1H), 8.09 (s,
Synthesis of 1,1,1,3,3,3-Hexafluoro(2-chloromethoxy)
propane (Sevochlorane, 1)
To a 100 ml flask containing aluminum trichloride (4 g,
0.03 mol) was added cold (0 °C) HFIP (5 g, 0.03 mol) and the
mixture was stirred for 1 h at 0 °C. Then, trioxane (0.89 g,
0.01 mol) was added to the reaction mixture in a single portion
ꢀ
959

Synthesis and X-Ray Crystal Structure of Fluorous Imidazolium Salts
1H), 9.70 (s, 1H). 13C NMR (DMSO+D2O): δ 36.59 (s), 72.8
isopropanol (HFIP) using AlCl3 and trioxane. The reaction
2
2
(septet, JFCC = 31.45 Hz), 78.4 (s), 123.8 (q, JFC = 283 Hz),
122.8 (s), 124.7 (s), 138.7 (s). 19F NMR (DMSO+D2O): δ
-74.10 (d, J = 6.35 Hz, 6F). IR (neat) ν: 3178.32(s),
2728.11(s), 1585.17(s), 1560.54(s)1, 1382.76(s), 1293.29(s),
1121.24(s), 1000.56(s), 897.02(s), 870.13(s), 688.22(s).
temperature was kept constant at 0 °C for 2 h and then raised
to room temperature. The reaction kinetics was followed by 1H
and 19F NMR spectroscopy to optimize the reaction time.
After 3 h at RT, 90% conversion was achieved and the product
SVC was extracted. Since the organic phase consisted of SVC
1 and some percent of the corresponding bisacetal, the crude
SVC was distilled to obtain pure SVC in 85% yield.
Synthesis
of
Bis-1,3-(1,1,1,3,3,3-hexafluoroiso-
propoxymethyl)imidazolium Salt 4
Imidazolium salt 4 was prepared by two methods as
follows: Method A: To a sample tube, containing imidazole
(0.34 g, 0.005 mol) was added SVC (3.25 g, 0.015 mol) at
room temperature and the mixture was stirred for 2 days. The
resulting precipitate was filtered off and dissolved in
acetonitrile (3 ml). After 1 day, the colorless crystals were
obtained. The crystalline product was washed by 2 × 2 ml
diethyl ether and vacuum dried to get 0.79 g pure product in
Synthesis of 1-(1,1,1,3,3,3-Hexafluoroisopropoxy-
methyl)-3-methylimidazolium Salt (2)
The solvent free reaction of equimolar amounts of methyl
imidazole and SVC was followed at room temperature
(Scheme 1). After two days, the single-phase reaction mixture
gradually became viscose. The mixture was washed with ether
to dissolve unreacted starting materials. The remaining sample
was then recrystallized from acetonitrile and crystalline
product, m.p.: 130-131 °C, was obtained in 91% yield. To
characterize the obtained product, the corresponding 1H NMR
spectrum was analyzed. The presence of both imidazole ring
and CH2OCH(CF3)2 group was verified based on the known
three 1H peaks in the 7.8 to 10 ppm, a singlet at 3.84 ppm for
methyl imidazole and more importantly a singlet at 6.07 ppm
for the deshielded methylene hydrogens of -OCH2N+ and a
septet at 6.46 ppm for CH(CF3)2 hydrogen. This was further
confirmed by 13C and 19F NMR data. The expected septet peak
at 72.8 ppm for CH carbon of CH(CF3)2 and a singlet at 78.4
ppm for N+CH2O carbon in 13C NMR spectrum and a single
doublet at -74.1 ppm in 19F NMR spectrum further confirmed
the chemical structure of imidazolium salt 2. The observation
of no more peaks in the three NMR spectra confirmed the
purity of salt 2. Contrary to 1-methyl-3-propyl imidazolium
salt, the imidazolium salt 2 was not an ionic liquid.
1
3
34% yield. H NMR (DMSO+D2O): δ 5.77 (septet, JFCCH
=
5.75 Hz, 2H), 6.05 (s, 4H), 8.01 (s, 2H), 9.65 (s, 1H). 13C
2
NMR (DMSO+D2O): δ 74.1 (septet, JFCC = 31.45 Hz), 79.4
2
(s), 123.4 (q, JFC = 283 Hz), 123.4 (s), 138.9 (s). 19F NMR
(DMSO+D2O): δ -74.75 (d, J = 5.17 Hz, 6F). IR (neat) ν:
3079.71(s), 2905.79(s), 2739.13(s), 1559.20(s) 1407.45(s),
1110.84(s), 999.18(s), 898.01(s), 872.72(s), 688.46(s),
533.10(s).
Method B:A 50 ml round bottom flask equipped with a
condenser and magnetic stirrer containing 5 ml THF was
charged with imidazole (0.5 g, 7.3 mmol) and NaH ( 0.18 g,
7.3 mmol) and the mixture was refluxed at 70 °C for 6 h. The
solvent was evaporated to get a white solid. To this was added
sevochlorane (3.0 g, 13.5 mmol) and the reaction mixture was
stirred at RT for 24 h. The resulting NaCl precipitate was
filtered out and the filtrate was kept in a closed vial sample for
3 days to obtain 1.7 g crystalline product 4 in 67% yield. m.p.:
158-159 °C.
Synthesis
of
Bis-1,3-(1,1,1,3,3,3-hexafluoroiso-
propoxymethyl)imidazolium Salt 4
RESULTS AND DISCUSSION
Imidazolium salt 4 was prepared by two methods. In the
first method, imidazole and SVC reacted at room temperature
in the absence of a base. In the second, imidazole was first
deprotonated by NaH and then reacted with SVC. In the first
method, the 1:1 molar ratio was tried first and the reaction
mixture, after being stirred for 2 days at RT, was dissolved in
acetonitrile. The white crystalline precipitate filtered, dried
Synthesis of 1,1,1,3,3,3-Hexafluoro(2-chloromethoxy)
propane (Sevochlorane, 1)
The reported procedure for the synthesis of sevochlorane
(SVC) was followed with some modifications [11]. It involved
one-step
chloromethylation
of 1,1,1,3,3,3-hexafluoro
ꢀ
960

Moghimi et al.
OH
Cl
CF3
AlCl3
O
F3C
CF3
trioxane
F3C
SVC
(1)
CF3
CF3
O
H3C
H3C
N
N
N
N
+
Cl
(2)
H
Cl
O
F3C
F3C
CF3
CF3
N
N
F3C
F3C
O
O
O
F3C
CF3
+
N
N
N
N
+
(3)
Cl
(4)
N
Na N
(4)
ꢀ
Scheme 1. Synthesis of imidazolium salts
ꢀ
and identified by NMR spectroscopy and found to be
imidazolium salt 4 (4% yield). Then, the same reaction was
repeated using imidazole and SVC in 1:3 molar ratio. After 24
h, a solid-liquid double-phase mixture was achieved. In order
to identify the composition of the precipitate, a sample was
relative integration of imidazolium and CH2 peaks in 1H NMR
spectrum and the existence of one septet at 5.77 ppm (3JFCCH
=
5.75 Hz, 2H) for CH(CF3)2 and a single singlet at 6.05 ppm
(4H), clearly were in support of the formation of a double
alkylated product 4. Also, a doublet at 74.75 ppm (J = 5.17
Hz, 12F) in 19F, a septet at 74.1 ppm (2JFCC = 31.45 Hz) and a
singlet at 79.4 ppm in 13C NMR spectra clearly confirm the
characterization. Single crystal structure analysis was
performed on salt 4 to clarify the solid phase chemical
structure.
Sevofluorane with the chemical structure FH2COCH(CF3)2
is a known general inhalation anesthetic. This and other
inhalation anesthetics have been deemed unsuitable for
parenteral administration due to their low aqueous solubility,
thereby making them difficult to formulate for intravenous
administration. As noted earlier, structural modification of
sevofluorane by replacing F with imidazolium cation was one
of the goals in the current research to prepare water soluble
salts containing (CF3)2CHO-CH2 moity and to evaluate the
structure and biological activities relationship. In order to
evaluate the anesthetic properties of salts 2 and 4, they were
injected as intravenous aq. solutions to mice and the general
behavior of the animals was followed. The preliminary tests
indicated no anesthetic property. However, calmative property
was noticed for both salts. The biological studies are underway
in more details.
1
dissolved in DMSO-d6 and analyzed by H and 19F NMR.
Three species were recognized two of which showed the
presence of both imidazole ring and CH2CH(CF3) group.
Accordingly, imidazolium chloride, imidazolium salts 3 and 4
were distinguished as the products. Imidazolium chloride and
imidazolium salt 3 are produced as a result of HCl absorption
and monoalkylation reaction while Imidazolium salt 4 is
produced from the second alkylation reaction on 3. The
resulting precipitate, however, was recrystallized from
acetonitrile to get imidazolium salt 4 in 34% yield. Salt 4
melts at 157-158 °C without decomposition, absorbs water
rapidly, dissolves in water and DMSO, and is not soluble in
chloroform and ether.
In the second method, imidazole was first deprotonated by
NaH in THF followed by THF evaporation. The resulting
sodium salt reacted with SVC, and NaCl precipitate was
filtered out. The filtrate was kept in a closed vial sample for 3
days to obtain 1.7 g crystalline pure product 4 in higher yield,
67%. m.p.: 158-159 °C.
The characterization of imidazolium salt
4
was
straightforward because of the symmetry of the molecule. The
ꢀ
961

Synthesis and X-Ray Crystal Structure of Fluorous Imidazolium Salts
X-Ray Crystal Structure of Imidazolium Salt 4
A summary of the X-ray crystallography data for salt 4 is
presented in Table 1 and the molecular structure is shown in
Fig. 3. Table 2 lists bond lengths, bond angles and torsion
angles. As is clear, the molecular structure consists of
imidazolium cation and anionic fragment Cl-.
CONCLUSIONS
(CF3)2CH-O-CH2Cl reacted with methylimidazole and
imidazole in 1:1 and 2:1 mole ratio, respectively, to achieve
the corresponding fluorous imidazolium chloride salts. The
1
characterization was performed by H, 13C and 19F NMR
spectroscopy. The chemical structure of the symmetrically
substituted imidazolium cation was verified by X-ray
crystallography.
ACKNOWLEDGMENTS
We are grateful to Imam Hossein University for financial
support.
Fig. 3. ORTEP plot of imidazolium salt 4.
Table 1. The X-Ray Crystallography Data for Imidazolium Salt 4
Empirical formula
Formula weight
Crystal system
Space group, Z
Unit cell dimension
C11H9N2O2F12Cl
464.65
Monoclinic
P21/n
Z = 4
α = 90.00˚
a = 10.613(10)
b = 12.1493(8)
c = 14.1964(14)
β = 109.852(8)˚
γ = 90.00˚
Unit cell volume
1726.3 A3
̊
Temperature (K)
298(2)
0.355
1.788
920
Adsorption coefficient (mm-1)
Calculation density (mg m-3)
F (0 0 0)
Crystal size (mm)
R value
0.40 × 0.32 × 0.24
0.0402
Rw value
θ range for data collection (deg)
Limiting indices
Reflection collected/unique
Completeness to θmax
Goodness of fit on F2
Final R indices[1.2sigma (1)]
0.1425
2.09 to 29.28
-14 < h < 14, -16 < k < 15, -19 < l < 19
12361/4629 [R(int) = 0.0343]
98.2%
1.067
R1 = 0.0611, wR2 = 0.1249
ꢀ
962

Moghimi et al.
Table 2. Selected Bond Lengths (A
̊
), Bond Angles (˚) and Torsion Angles (˚) for Imidazolium Sal4t
C(1)-F(2)
C(1)-F(3)
C(1)-F(1)
C(1)-C(2)
C(2)-O(1)
C(2)-C(3)
C(3)-F(6)
C(3)-F(5)
C(3)-F(4)
C(4)-O(1)
C(4)-N(1)
C(5)-N(2)
C(5)-N(1)
1.315(4)
C(6)-C(7)
C(6)-N(1)
C(7)-N(2)
C(8)-O(2)
C(8)-N(2)
C(9)-O(2)
C(9)-C(11)
C(9)-C(10)
C(10)-F(8)
C(10)-F(9)
C(10)-F(7)
C(11)-F(10)
C(11)-F(11)
C(11)-F(12)
1.332(4)
1.378(3)
1.379(3)
1.325(4)
1.328(4)
1.514(4)
1.407(3)
1.469(4)
1.313(4)
1.319(4)
1.328(4)
1.409(3)
1.456(3)
1322(3)
1.327(3)
405(3)
1.
1.461(3)
1.406(3)
1.518(4)
1.519(4)
1.314(4)
1.317(4)
1.336(4)
1.310(4)
1.321(4)
1.326(4)
F(2)-C(1)-F(3)
F(2)-C(1)-F(1)
F(3)-C(1)-F(1)
F(2)-C(1)-C(2)
F(3)-C(1)-C(2)
F(1)-C(1)-C(2)
O(1)-C(2)-C(3)
O(1)-C(2)-C(1)
C(3)-C(2)-C(1)
F(6)-C(3)-F(5)
F(6)-C(3)-F(4)
F(5)-C(3)-F(4)
F(6)-C(3)-C(2)
F(5)-C(3)-C(2)
F(4)-C(3)-C(2)
O(1)-C(4)-N(1)
N(2)-C(5)-N(1)
C(7)-C(6)-N(1)
C(6)-C(7)-N(2)
O(2)-C(8)-N(2)
O(2)-C(9)-C(11)
108.6(3)
107.2(3)
107.3(3)
111.9(3)
109.7(2)
111.9(3)
106.9(2)
108.6(2)
113.8(2)
108.6(3)
105.7(3)
106.7(3)
110.4(3)
111.6(3)
113.3(3)
111.0(2)
108.4(2)
107.2(2)
107.2(2)
111.1(2)
108.2(2)
107.2(2)
113.3(3)
107.2(3)
107.8(3)
107.6(3)
112.6(3)
111.6(3)
109.8(3)
108.4(3)
107.1(3)
107.0(3)
113.3(3)
110.7(3)
110.1(1)
116.01(18)
116.56(19)
108.5(2)
125.5(2)
125.9(2)
108.7(2)
125.1(2)
126.1(2)
O(2)-C(9)-C(10)
C(11)-C(9)-C(10)
F(8)-C(10)-F(9)
F(8)-C(10)-F(7)
F(9)-C(10)-F(7)
F(8)-C(10)-C(9)
F(9)-C(10)-C(9)
F(7)-C(10)-C(9)
F(10)-C(11)-F(11)
F(10)-C(11)-F(12)
F(11)-C(11)-F(12)
F(10)-C(11)-C(9)
F(11)-C(11)-C(9)
F(12)-C(11)-C(9)
C(2)-O(1)-C(4)
C(8)-O(2)-C(9)
C(5)-N(1)-C(6)
C(5)-N(1)-C(4)
C(6)-N(1)-C(4)
C(5)-N(2)-C(7)
C(5)-N(2)-C(8)
C(7)-N(2)-C(8)
F(2)-C(1)-C(2)-O(1)
F(3)-C(1)-C(2)-O(1)
F(1)-C(1)-C(2)-O(1)
F(2)-C(1)-C(2)-C(3)
F(3)-C(1)-C(2)-C(3)
F(1)-C(1)-C(2)-C(3)
O(1)-C(2)-C(3)-F(6)
C(1)-C(2)-C(3)-F(6)
O(1)-C(2)-C(3)-F(5)
C(1)-C(2)-C(3)-F(5)
O(1)-C(2)-C(3)-F(4)
C(2)-C(2)-C(3)-F(4)
N(1)-C(6)-C(7)-N(2)
O(2)-C(9)-C(10)-F(8)
C(11)-C(9)-C(10)-F(8)
O(2)-C(9)-C(10)-F(9)
C(11)-C(9)-C(10)-F(9)
O(2)-C(9)-C(10)-F(7)
C(11)-C(9)-C(10)-F(7)
O(2)-C(9)-C(11)-F(10)
C(10)-C(9)-C(11)-F(10)
-178.3(2)
61.1(3)
-57.9(3)
-59.3(3)
-179.9(3)
61.1(3)
-171.7(3)
69.7(4)
O(2)-C(9)-C(11)-F(11)
C(10)-C(9)-C(11)-F(11)
O(2)-C(9)-C(11)-F(12)
C(10)-C(9)-C(11)-F(12)
C (3)-C(2)-O(1)-C(4)
C(1)-C(2)-O(1)-C(4)
N(1)-C(4)-O(1)-C(2)
N(2)-C(8)-O(2)-C(9)
C(11)-C(9)-O(2)-C(8)
C(10)-C(9)-O(2)-C(8)
N(2)-C(5)-N(1)-C(6)
N(2)-C(5)-N(1)-C(4)
C(7)-C(6)-N(1)-C(5)
C(7)-C(6)-N(1)-C(4)
O(1)-C(4)-N(1)-C(5)
O(1)-C(4)-N(1)-C(6)
N(1)-C(5)-N(2)-C(7)
N(1)-C(5)-N(2)-C(8)
C(6)-C(7)-N(2)-C(5)
C(6)-C(7)-N(2)-C(8)
O(2)-C(8)-N(2)-C(5)
O(2)-C(8)-N(2)-C(7)
-5305(3)
-172.2(3)
138.6(2)
-98.2(2)
-77.1(3)
78.3(3)
-62.1(3)
178.0(3)
177.1(3)
57.2(4)
113.7(2)
-123.9(3)
-0.5(3)
178.3(2)
0.8(3)
56.3(3)
-63.6(4)
-.08(4)
-51.4(4)
67.8(4)
-177.9(3)
118.5(3)
-63.0(3)
0.0(3)
-172.1(4)
-52.9(4)
68.6(3)
-172.1(3)
66.4(4)
-175.9(2)
0.5(3)
-52.3(4)
176.3(3)
69.8(3)
-105.3(3)
ꢀ
963

Synthesis and X-Ray Crystal Structure of Fluorous Imidazolium Salts
SUPPLEMENTARY DATA
J. Cvačka, J. Kvíčala, J. Fluorine Chem. 130 (2009)
929.
Crystallographic data (excluding structure factors) for the
structure in this paper have been deposited with the
Cambridge Crystallographic Data Centre as the supplementary
publication no.
CCDC 781832 for compound 4. These data can be obtained
free of charge on application to CCDC, 12 Union Road,
Cambridge, CB12 1EZ, UK, fax: +44 1223 366 033, e-mail:
deposit@ccdc.cam.ac.uk or on the web www: http://www.
ccdc.cam.ac.uk.
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