1,4-Bis(2-benzimidazolyl)benzene

Article abstract of DOI:10.1107/S0108270100003978

The title compound, C₂₀H₁₄N₄, lies about an inversion centre and the benzimidazole moiety and the phenyl ring are twisted by 30.9(1)°. The benzimidazole moiety is completely planar, with a maximum deviation of 0.009 (2) angstroms. Intermolecular N-H···N hydrogen bonds give rise to a layered structure, with the layers stacked by van der Waals interactions.

Full text of DOI:10.1107/S0108270100003978

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
the context of modelling biological systems (Bouwman et al.,
990; Pujar & Bharamgoudar, 1988). The present work reports
the crystal and molecular structure of the title compound, (I).
1
ISSN 0108-2701
1
,4-Bis(2-benzimidazolyl)benzene
a
a
a
a
The asymmetric unit contains half the molecule and the other
half is inversion related (Fig. 1) (1 � x, � y, 1 � z). The average
bond distances and angles for the benzimidazole ring is in
good agreement with those of other substituted bis(benz-
Fengli Bei, Fangfang Jian, Xujie Yang, Lude Lu, Xin
a
b
b
Wang, S. Shanmuga Sundara Raj and Hoong-Kun Fun *
a
Materials Chemistry Laboratory, Nanjing University of Science and Technology,
b
Nanjing, 210094, People's Republic of China, and X-ray Crystallography Unit,
imidazole) compounds (Matthews et al., 1996; Ozbey et al.,
ꢁ
School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my
1
and at C8 [119.2 (2) ], are similar to those found in related
998). The two internal-ring bond angles, at C7 [113.3 (2) ]
ꢁ
compounds (Rajnikant et al., 1995). The C7ÐC8 bond length,
1
Received 3 February 2000
Accepted 10 March 2000
Ê
.468 (3) A, is close to the standard value for a single-bond
length between trigonally linked C atoms (Cruickshank &
Sparks, 1960). The bond lengths of CÐN in the imidazole ring
Ê
are in the range 1.320±1.400 A, which are shorter than the
The title compound, C H N , lies about an inversion
4
2
0
14
Ê
single-bond length of 1.48 A and longer than the typical C
centre and the benzimidazole moiety and the phenyl ring
ꢁ
N
Ê
are twisted by 30.9 (1) . The benzimidazole moiety is
maximum deviation of
distance of 1.28 A, indicating partial double-bond character.
This can be interpreted in terms of conjugation in the
completely planar, with
Ê
a
ꢁ
0
.009 (2) A. Intermolecular NÐHÁ Á ÁN hydrogen bonds give
heterocycle. The phenyl ring is twisted through 30.9 (1) with
the benzimidazole moiety along the C7ÐC8 bond. The
benzimidazole moiety is completely planar, with a maximum
rise to a layered structure, with the layers stacked by van
der Waals interactions.
ꢁ
deviation of 0.009 (2) for C2; the dihedral angle between the
ꢁ
aromatic ring and the ®ve-membered ring is only 0.1 (1) .
The molecule forms a two-dimensional network bonded
through intermolecular NÐHÁ Á ÁN hydrogen bonds. The
hydrogen-bonded layers, parallel to (001), are stacked upon
one another by translation and held together by van der Waals
attractions.
Comment
Benzimidazole is an interesting heterocyclic ring because it
is present in various naturally occurring drugs such as
omeprazole, astemizole and emedastine difumarate (Sakai et
al., 1989). The ef®cacy of substituted benzimidazoles in the
treatment of parasitic infections is well known (Brown et al.,
1
961; Preston, 1974; Sarkar et al., 1984). Substituted benz-
imidazole moieties are established pharmacophores in para-
sitic chemotherapy. Bis(2-benzimidazoles) and some
substituted bis(2-benzimidazolyl)alkanes have attracted much
interest because of their wide-ranging antiviral activity
Experimental
The title compound was prepared from benzene-1,4-dicarboxylic acid
and 1,2-diaminobenzene in 66% yield using a modi®ed Phillips
reaction (Addison & Burke, 1981; Addison et al., 1983) and was
recrystallized from methanol. The single crystals suitable for X-ray
analysis were then obtained by slow evaporation at room tempera-
ture from the EtOH solvent.
(
Tidwell et al., 1993) and also because of the coordination
chemistry of azoles acting as ligands in transition metal
compounds. Such compounds are increasingly being studied in
Figure 1
The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme [symmetry code: (i) 1 � x, � y, 1 � z].
7
18 # 2000 International Union of Crystallography ꢀ Printed in Great Britain ± all rights reserved
Acta Cryst. (2000). C56, 718±719

organic compounds
Crystal data
Table 2
Hydrogen-bonding geometry (A, ).
Ê
ꢁ
C
20
H
14
N
4
Mo Kꢀ radiation
Cell parameters from 3853
re¯ections
r
M = 310.35
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
Orthorhombic, Pbca
Ê
a = 10.2400 (3) A
Ê
b = 9.7505 (2) A
c = 15.0310 (4) A
Ê
V = 1500.77 (7) A
ꢁ
ꢁ = 2.71±28.32
i
� 1
N2ÐH2AÁ Á ÁN1
0.86
2.17
3.033 (2)
175
ꢂ = 0.085 mm
T = 293 (2) K
Ê
1
1
Symmetry code: (i) � x; y � ; z.
3
2
2
Needle, dark red
0.50 Â 0.12 Â 0.10 mm
Z = 4
�
3
D
x
= 1.374 Mg m
The authors would like to thank the Malaysian Government
and Universiti Sains Malaysia for research grant R & D No.
305/p®zik/622004. SSSR thanks the Universiti Sains Malaysia
for a Visiting Postdoctoral Fellowship.
Data collection
Siemens SMART CCD area-
detector diffractometer
Rint = 0.076
ꢁ
ꢁ
max = 28.28
!
scans
h = � 9 ! 13
k = � 12 ! 12
l = � 19 ! 19
9
1
1
577 measured re¯ections
846 independent re¯ections
223 re¯ections with I > 2ꢃ(I)
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SK1369). A packing diagram of (I) has also been
deposited. Services for accessing these data are described at the back of
the journal.
Re®nement
2
2
2
2
Re®nement on F
2
o
w = 1/[ꢃ (F ) + (0.0584P)
2
R[F > 2ꢃ(F )] = 0.067
wR(F ) = 0.155
S = 1.117
+ 0.4289P]
where P = (F
2
2
2
c
o
+ 2F
)/3
References
(Á/ꢃ)max < 0.001
Ê
Áꢄmax = 0.185 e A
� 3
� 3
1
1
846 re¯ections
09 parameters
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Áꢄmin = � 0.298 e AÊ
H-atom parameters constrained
1
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1
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Table 1
Selected geometric parameters (A, ).
Ê
ꢁ
Cruickshank, D. W. J. & Sparks, R. A. (1960). Proc. R. Soc. A258, 270±285.
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N1ÐC6
N2ÐC7
N2ÐC1
1.320 (3)
1.400 (3)
1.359 (2)
1.379 (3)
C8ÐC10
C8ÐC9
C9ÐC10
1.386 (3)
1.398 (3)
1.377 (3)
1.377 (3)
i
1538.
i
C10ÐC9
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104.4 (2)
C7ÐN2ÐC1
107.0 (2)
425.
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1
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6
Data collection: SMART (Siemens, 1996); cell re®nement: SAINT
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(
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to prepare material for publication: SHELXTL and PLATON (Spek,
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C. C. & Hall, J. E. (1993). Antimicrob. Agents Chemother. 37, 1713±1716.
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Acta Cryst. (2000). C56, 718±719
Fengli Bei et al. ꢀ
C H
20 14
N
4
719