electronic reprint

Acta Crystallographica Section E

Structure Reports
Online
ISSN 1600-5368
Editors: W.T. A. Harrison, J. Simpson and
M. Weil

3,5-Bis(3-methylimidazolium-1-ylmethyl)toluene
bis(hexafluorophosphate)

Abbas Washeel, Rosenani A. Haque, Siang Guan Teoh, Chin Sing Yeap and
Hoong-Kun Fun

Acta Cryst. (2010). E66, o556

This open-access article is distributed under the terms of the Creative Commons Attribution Licence
http://creativecommons.org/licenses/by/2.0/uk/legalcode, which permits unrestricted use, distribution, and
reproduction in any medium, provided the original authors and source are cited.

ISSN 1600-5368 Acta Crystallographica Section E

Volume 61 Structure Reports
Part 11
Online
November 2005 Editors: W. Clegg and D. G. Watson
Acta Crystallographica Section E: Structure Reports Online is the IUCr’s highly popu-
lar open-access structural journal. It provides a simple and easily accessible publication
mechanism for the growing number of inorganic, metal-organic and organic crystal struc-
Inorganic compounds

Metal-organic compounds
ture determinations. The electronic submission, validation, refereeing and publication
Organic compounds

facilities of the journal ensure very rapid and high-quality publication, whilst key indica-
tors and validation reports provide measures of structural reliability. In 2007, the journal
published over 5000 structures. The average publication time is less than one month.

journals.iucr.org
International Union of Crystallography * Chester

Crystallography Journals Online is available from journals.iucr.org

Acta Cryst. (2010). E66, o556 Washeel et al. · C17 H22 N4 2+ ·2PF6 −
organic compounds
Acta Crystallographica Section E
Data collection
Structure Reports
Online Bruker SMART APEXII CCD 42881 measured reflections
area-detector diffractometer 11275 independent reflections
ISSN 1600-5368 Absorption correction: multi-scan 7988 reflections with I > 2(I)
(SADABS; Bruker, 2009) Rint = 0.034
Tmin = 0.858, Tmax = 0.942
3,5-Bis(3-methylimidazolium-1-yl- Refinement
methyl)toluene bis(hexafluorophosphate) R[F 2 > 2(F 2)] = 0.052 319 parameters
wR(F 2) = 0.149 H-atom parameters constrained
S = 1.03
max = 0.62 e Å3
Abbas Washeel,a Rosenani A. Haque,a Siang Guan Teoh,a 11275 reflections
min = 0.44 e Å3
Chin Sing Yeapb‡ and Hoong-Kun Funb*§
a
Table 1
School of Chemical Science, Universiti Sains Malaysia, 11800 USM, Penang, Hydrogen-bond geometry (Å,  ).
Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains
Malaysia, 11800 USM, Penang, Malaysia D—H  A D—H H  A D  A D—H  A
Correspondence e-mail: hkfun@usm.my
C1—H1A  F2 i
0.93 2.47 3.3431 (16) 157
C5—H5A  F8ii 0.93 2.39 3.2686 (16) 157
Received 21 January 2010; accepted 30 January 2010
C8—H8A  F12ii 0.93 2.40 3.2808 (16) 158
C9—H9A  F4i 0.93 2.41 3.2513 (19) 151
Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 Å; C10—H10A  F4iii 0.93 2.38 3.2967 (17) 169
R factor = 0.052; wR factor = 0.149; data-to-parameter ratio = 35.3. C12—H12B  F5iv 0.97 2.42 3.3040 (18) 150
C14—H14A  F8iii 0.93 2.55 3.283 (2) 136
C14—H14A  F10iii 0.93 2.53 3.3050 (19) 141
C15—H15A  F7v 0.93 2.50 3.2568 (19) 139
The asymmetric unit of the title N-heterocyclic carbene C16—H16B  F9vi 0.96 2.48 3.135 (2) 125
compound, C17H22N42+2PF6, consists of one N-heterocyclic C16—H16C  F2 0.96 2.48 3.314 (2) 146
C17—H17C  F11 0.96 2.42 3.3563 (18) 166
carbene dication and two hexafluorophosphate anions. The
Symmetry codes: (i) x þ 1; y  12; z þ 12; (ii) x þ 1; y þ 12; z þ 12; (iii) x; y þ 12; z þ 12;
two imidazole rings are twisted away from but to the same side (iv) x þ 1; y; z; (v) x þ 1; y þ 12; z þ 12; (vi) x þ 2; y þ 12; z þ 12.
of the central toluene ring, making dihedral angles of 76.69 (7)
and 78.03 (7) with the central ring. In the crystal, the Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT
components are linked by C—H  F interactions, generating a (Bruker, 2009); data reduction: SAINT; program(s) used to solve
three-dimensional network. structure: SHELXTL (Sheldrick, 2008); program(s) used to refine
structure: SHELXTL; molecular graphics: SHELXTL; software used
to prepare material for publication: SHELXTL and PLATON (Spek,
Related literature 2009).
For background to N-heterocyclic carbenes, see: Wanzlick &
Schönherr (1968); Öfele (1968); Arduengo et al. (1991). For AW, RAH and SGT thank Universiti Sains Malaysia (USM)
applications of N-heterocyclic carbene derivatives, see: Meyer for the FRGS fund (203/PKIMIA/671115). HKF and CSY
et al. (2009); Ray et al. (2007); Medvetz et al. (2008). For a thank USM for the Research University Golden Goose grant
related structure, see: Jiang (2009). For the synthesis, see; Dias (1001/PFIZIK/811012). CSY thanks USM for the award of a
& Jin (1994). For the stability of the temperature controller USM Fellowship.
used for the data collection, see: Cosier & Glazer (1986).
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: TK2620).

References
Arduengo, A. J. III, Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113,
361–363.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,
Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
Experimental Dias, H. V. R. & Jin, W. (1994). Tetrahedron Lett. 35, 1365–1366.
Jiang, P. (2009). Acta Cryst. E65, o2177.
Crystal data Medvetz, D. A., Hindi, K. M., Panzner, M. J., Ditto, A. J., Yun, Y. H. & Young,
C17H22N42+2PF6 V = 2331.78 (8) Å3 W. J. (2008). Met. Based Drugs, Article ID 384010.
Mr = 572.33 Z=4 Meyer, D., Taige, M. A., Zeller, A., Hohlfeld, K., Ahrens, S. & Strassner, T.
Monoclinic, P21 =c Mo K radiation (2009). Organometallics, 28, 2142–2149.
a = 6.1289 (1) Å  = 0.30 mm1 Öfele, K. (1968). J. Organomet. Chem. 12, P42–P43.
b = 19.0139 (4) Å T = 100 K Ray, S., Mohan, R., Singh, J. K., Samantaray, M. K., Shaikh, M. M., Panda, D. &
c = 20.1770 (4) Å 0.53  0.28  0.20 mm Ghosh, P. (2007). J. Am. Chem. Soc. 129, 15042–15053.
 = 97.390 (1) Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
‡ Thomson Reuters ResearcherID: A-5523-2009. Wanzlick, H.-W. & Schönherr, H.-J. (1968). Angew. Chem. Int. Ed. Engl. 7,
§ Thomson Reuters ResearcherID: A-3561-2009. 141–142.

o556 Washeel et al. doi:10.1107/S1600536810003739 Acta Cryst. (2010). E66, o556

electronic reprint

 
  

electronic reprint
 
 
  


 
 


 

 

 
! "#$% &''!

()*(+, -./0'"+12 "



   !" #$%&#'!()$%&*+,-,().'!

()
/!,   !,!/#01 ((,, !, 
0# 1 /#01  ((
2"  !1##,2 2"32" 
, 2 1 0!  #1 ! 0#14 0"1  !2,,# ! 2 
#" 2%  5 (
6,  17 !2 !, 2"3  !2#
8 9 #,7 2"3#7#! 2:#,  2#%  ! 0# 71,02
5#7% )

6,220 !, 2" 0#  ! , # # ,3!0  ", ",
 ;1

6,1 2"2 2" ,  !#00<1(
, !,2#% 
14)444(#=4=4:44: " ,23202#7  !
= >!  #

 >! :* "7
6, 2#% 1 # ! 2, 010
# ,2# !,12&1#,#1 !9
(9 #9)
=9 ? ,,1"7

6, ,3!0  ", ", &,  ,#2  &2 0@AAA;,# 1
 #;1
6

 
 

6,   2" 0#  ""# !  1 , " #0 ! B * < ((:
 6   #  0  ! =
 2 2,  0
1=
22  :# 32 2,2#% 
(19
22   ###
6,
230 !03#=9=C! :,
6,&" #0  ## , ,# ,#,,3=
2
CD;
=19
22  2, 2  ### ,1! ,
6,,230!#1 71,

6,1""  ## ,# ,## ##! 2, 2, 

6,# 

19
))E 2
"
F:9:(C
  # 7"   !, 0  
2"0

 


/ 2 "  #1 2#!#01#12 # ,4G

(=
(9>#  G
 

H
6, 11 0"2 # ""#! ,2,1 0"

!

electronic reprint

 
  

 

;1

6,2 000 !, 2" 0# ,E" " #!  
 2

;1

6,"&1 !, 2" 0#7 ## ,3, 1,2 
0&#=B &
I2 0,# 1 #, #,#



 
!
"  #    "


9:JAD;K  G

G9
== 3G
=512K=
5  L 5 M# NG
99=>
2 FD "2! 2(()! 
G
)( > OG
=4==
?
G(
=(: > PG
=22K
G
99: > GC
QG(9
=( ? R &  0
G==
9)) >= 
=S
)S
22
G:


R0&+5/86/DTIIB# 
9#"#! 
#!! 2
8#  0F!! 0#0 9())!  ,!UV!
1", "G
=:
W#X O23G=
:?O2G
?
/ "   F20
%GK(Y
#$#.R0&(
2G
))23G
(: &GK=Y=
:))20#!  GK==Y==

%

electronic reprint
 
 
  

"' ( 
D2 2  F007#
8!2  2, #
ZH023F!0 + # 2  F#!!; 02"
# 1  F!#! 21, 01
"UV G
 
)" G
:(  2"2 #
)GLV  J
9= J
99
#G
=
,G J L=
9!  [LV 23G

=("2 [\23G
>K=
 [\2GK
::>K=

#*
3$'&"
6, "#, #2 !]3! # 2  "!  1  *
^%()  "1
 C

-&
/#3",#,#,#1  

" 2#01,!0 723
6,
#&  0#7#0,2  !##1#  1.   #
"2 0# ,,#!#22
/"" 32  " 2 !#0#
! 21#7 71

"

*%""
8!2 !1/ZZ! 
6, 1,#"!  8#1 # !!##  7 
"! "#  , % ! 17
6,,, #3"  !UV 0# ! 01"
! 1 
# 7 ,,  !! ! !2
"! #  0 1
, # #"! # /ZZ# 71


 (
  
*
+, 
**( *
(
-./0
1  2  _LH
 
(9( 
== 
:9( 
:9(
 
9::) 
:9: 
9=: 
)(
= 
9=( 
:) 
= 
:
: 
)((:( 
:9 
=::) 
:
 
)( 
(:9 
===9 
::
/ 
)) 
9: 
=(( 
(_
 
9(9 
()9 
== 
(
= 
(= 
=:9 
= 

=/ 
)=)) 
=: 
(: 
_
: 
 
==99 
==) 
:
 
( 
9:9 
=)=:= 
=
/ 
==9 
9:9 
: 
)_
 
( 
=)9 
=99 
(
9 
(= 
:=:)9 
::9 
):=
9/ 
9= 
9 
=): 
=:_
9R 
==( 
 
::( 
=:_



electronic reprint

 
  
) 
 
9:: 
===: 

)/ 
( 
((( 
:) 
_
( 
(= 
(:9 
:))9 
)9=
(/ 
):) 
 
:= 
=:_
 
)9 
((=) 
:99 
(==
/ 
9( 
99 
:9 
=_
 
= 
9):( 
::((9 
==
/ 
:( 
= 
) 
:(_
R 
:= 
== 
9:( 
:(_
 
)(9 
: 
:)= 
:(_
 
) 
=(()9 
=) 
)=
/ 
=== 
=(9( 
: 
=:_
R 
=: 
:9 
= 
=:_
= 
:( 
:9 
= 

=/ 
9 
: 
)( 
_
: 
(== 
::(=) 
:(9 
==
:/ 
(:) 
:=== 
::9 
=9_
 
):= 
:) 
=(()=) 
==
/ 
9= 
:=) 
:= 
=)_
 
))= 
) 
==) 
==
/ 
(( 
=9 
): 
:_
R 
) 
= 
=:( 
:_
 
99) 
:= 
)9 
:_
9 
99 
=))) 
9 
=9=
9/ 
) 
((: 
= 
:_
9R 
:)= 
 
) 
:_
9 
() 
= 
) 
:_
D 
:):: 
:))() 
9: 
9
; 
9:9= 
:(( 
): 
==))
; 
:)9 
9= 
9)() 
=)
;= 
(: 
:)( 
(9 
:=:
;: 
:(9 
:(: 
(=: 
:9
; 
) 
:)9 
:9 
::=
; 
:)(9( 
:== 
()= 
:))=
D 
 
)=) 
:=(9 
)
;9 
=(99: 
( 
=( 
=
;) 
(9 
(: K
=: 
:
;( 
(: 
99( 
=( 
:
; 
() 
):= 
:= 
:
; 
: 
:9) 
= 
9:
; 
9)) 
 
:=9 
=

(*( *

(
-./0
  ==  = =
 
9: 
: 
:: 
: 
: 
9:
 
: 
) 
: 
): 
(: 
(:
= 
 
( 
=: K
9: 
::: 
=:

&

electronic reprint
 
 
  
: 
:) 
: 
: K
9: 
: K
::
 
==9 
): 
= K
:9 
 K
==:
 
) 
 
( K
: 
9: K
):
= 
) 
 
( K
: 
: 
:
: 
 
( 
= K
: 
: 
9:
 
 
 
 
: 
: 
9:
 
=9 
) 
 
=: 
: 
:
9 
:9 
9 
9 
): 
) 

) 
( 
)9 
= K
): 
=:: K
9:
( 
=:9 
= 
) K
 
= 

 
( 
=9 
( K
( 
= 

 
:)) 
=9 
 
= 
:) K
9
 
=) 
 
:9 K
=: 
= 
:
= 
= 
 
 K
=: 
=9: 
=:
: 
:=9) 
9 
:9 K
) 
: K

 
=9 
=:9 
= K
9) 
: K
9
 
=)) 
9 
=() 
: K
)( K

9 
=(9 
===9 
9 K
9: 
 K
=(
D 
99=: 
) 
9:: 
9 
=9 

; 
9(= 
=9( 
=: 
9= 
:= 
:
; 
=( 
:: 
9 
9: 
(: K
=:
;= 
9: 
(9 
=) K
=: 
: K

;: 
=(( 
(= 
=: 
) 
): K
9:
; 
:9 
)9) 
:9: K
( 
: 
):
; 
::( 
(: 
9) K
:=: K
 
(
D 
99): 
: 
=9 
 
=9 K
)
;9 
(: 
:) 
::= K
:: 
= 
)(:
;) 
= 
()9 
((: 
(=: 
):: 
:
;( 
9): 
:9) 
(= 
: K
: 
(
; 
::9 
(: 
=) 
:9: 
=( 
::
; 
:) 
( 
: 
 
:: K
)
; 
= 
:( 
 
:: K
 K


3(
*
(
-.450
@) 
== @/ 
(=
@( 
=9() @/ 
(
@9 
:99 @R 
(
@) 
=):9 @ 
(
@ 
=() @/ 
(9
@ 
::99 @R 
(9
=@= 
=(: =@=/ 
(=
=@: 
=)) :@ 
=:9
=@ 
:) :@:/ 
(=
:@= 
=:9 @/ 
(=
:@ 
=9(( @/ 
(
:@ 
:)( @R 
(
@ 
=)( @ 
(
@ 
=(( 9@9/ 
(



electronic reprint

 
  
@/ 
(= 9@9R 
(
@= 
=(:9 9@9 
(
@9 
(( D@; 
(=
=@: 
=(() D@; 
())
=@=/ 
(= D@; 
(
:@ 
=(9) D@;: 
9(
:@ 
:=) D@;= 
(
@ 
=)(9) D@; 
=
@/ 
(= D@;( 
(
@9 
=) D@; 
(
9@9/ 
(9 D@; 
(9
9@9R 
(9 D@;) 
()(
)@)/ 
(= D@; 
:
(@ 
= D@;9 
=(
(@(/ 
(=
)@@( )
( =@@R (
=
)@@9 
) :@@R (
=
(@@9 
: /@@R )

)@@ )
9 :@=@= )
(
)@@ 
 :@=@=/ 

@@ 
= =@=@=/ 

=@=@: )
= @:@= 9

=@=@ 
( @:@:/ 
:
:@=@ 
): =@:@:/ 
:
=@:@ )
9 :@@: 9
:=
=@:@ 
9= :@@/ 

@:@ 
)= :@@/ 

@@ 
( :@@/ (

@@/ (
 :@@R (

@@/ (
 /@@R (

=@@ )
= :@@ (

=@@9 
( /@@ (

@@9 
9) R@@ (

@=@: 
9 @9@9/ (

@=@=/ (
 @9@9R (

:@=@=/ (
 9/@9@9R (

@:@= (
9 @9@9 (

@:@ )
) 9/@9@9 (

=@:@ 
: 9R@9@9 (

@@: 
: ;@D@; (
9
@@/ 
 ;@D@; )(

:@@/ 
 ;@D@; )(
:
@@ (
) ;@D@;: )(

@@9 
)9 ;@D@;: 9)
)(9
@@9 (
= ;@D@;: )(
)=
@9@ 
 ;@D@;= (
:9
@9@9/ (
 ;@D@;= (

@9@9/ (
 ;@D@;= 9)
(
@9@9R (
 ;:@D@;= )(
((

'

electronic reprint
 
 
  
@9@9R (
 ;@D@; 9)
9=9
9/@9@9R )
 ;@D@; )(
9
@)@ )
: ;@D@; )(
(
@)@)/ 
) ;:@D@; )(
=
@)@)/ 
) ;=@D@; )(
=
@(@ 
)( ;(@D@; )(
)
@(@(/ 
 ;(@D@; (
=(
@(@(/ 
 ;@D@; (
)
(@@ 9
= ;(@D@;) )(
)
(@@/ 
: ;@D@;) 9)
=9
@@/ 
: ;@D@;) (
9
@@/ (
 ;(@D@; (

@@R (
 ;@D@; ))
)99
/@@R (
 ;@D@; 9(
=9
@@ (
 ;)@D@; )(
:9
/@@ (
 ;(@D@;9 9(
:
R@@ (
 ;@D@;9 (
=
=@@: 
 ;@D@;9 )(
(
=@@/ (
= ;)@D@;9 (

:@@/ (
= ;@D@;9 (
=9
@@@= 
:( 9@@)@ 9
()
@@@9 K9(
9 )@@(@ K
:
@@=@: 
(( 9@@(@ K9
((
9@@=@: 9(
( @(@@ 
99
@=@:@ K
:( )@@@( 

@=@:@ 9)
9( @@@( 9(
)=
=@:@@ 
)( =@=@@: K
(9:
@:@@ K9(
( :@=@@: 9
)
@@@ K
)=( @:@@= K:

@@@9 9
 =@:@@= =(
)
:@@@ 
( @:@=@= K
:
:@@@9 K9
9 @:@=@= K9(

)@@9@ K)
)9 :@=@=@: 
9:
(@@9@ (
( @=@=@: 9(

@@9@ K)
( =@=@:@ K
:
@@9@ (
: @=@:@ K9(

@@)@ K
= =@:@@: 
=9
@@)@ K9(
 =@:@@: K

(@@)@ 
:9 @:@@: 9(
==


6  6(
-.450
@AAA @ AAA AAA @AAA
 
(= 
:9 =
=:= 9
@/AAA;
 
(= 
=( =
) 9
@/AAA;)
 
(= 
: =
)) )
)@)/AAA;
 
(= 
: =
=( 
(@(/AAA;:
 
(= 
=) =
(99 (
@/AAA;:

(

electronic reprint

 
  

@RAAA;7 
(9 
: =
=:) 
:@:/AAA;) 
(= 
 =
)= =
 
(= 
= =
=( :
:@:/AAA;
7 
(= 
 =
)( =(
@/AAA;9
7 
( 
:) =
= 
@RAAA;(
@AAA; 
( 
:) =
=: :
9@9AAA; 
( 
: =
==) 
+22 #F K1JKLK2JL. 1JKJL2JL. 1KJL2JL.7 1J2.7 K1JJLK2JL.7
K1JJLK2JL

)

electronic reprint
 
 
  

$!

*

electronic reprint

 
  

$%

!+

electronic reprint