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Volume 70 
Part 5 
Pages o610-o611  
May 2014  

Received 4 April 2014
Accepted 22 April 2014
Online 26 April 2014

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.041
wR = 0.128
Data-to-parameter ratio = 18.7
Details
Open access

1-(4-Bromo­benz­yl)-2-(4-bromo­phen­yl)-1H-benzimidazole

aKey Laboratory of Organosilicon Chemistry and Material Technology of the Ministry of Education, Hangzhou Normal University, No. 58, Haishu Road, Hangzhou, 311121, People's Republic of China
Correspondence e-mail: quzr@hznu.edu.cn

There are two mol­ecules in the asymmetric unit of the title compound, C20H14Br2N2. In the first, the dihedral angles between the mean plane of the benzimidazole group and those of the 4-bromo­benzyl and 4-chloro­phenyl groups are 50.72 (17) and 71.29 (16)°, respectively, while the corresponding angles in the second mol­ecule are 42.09 (16) and 89.05 (17)°. The 4-bromo­benzyl and 4-bromo­phenyl groups make an angle of 68.1 (2) and 85.1 (21)° with each other in the two mol­ecules. In the crystal, weak C-H...N and C-H...Br hydrogen bonds link the mol­ecules along the c-axis direction. Br...Br inter­actions [3.5733 (9)Å] are also observed.

Related literature

For the chemistry of benzimidazoles, see: Steel (1990[Steel, P. J. (1990). Coord. Chem. Rev. 106, 227-265.]); Bhattacharya & Chaudhuri (2008[Bhattacharya, S. & Chaudhuri, P. (2008). Curr. Med. Chem. 15, 1762-1777.]); Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]); Boiani & González (2005[Boiani, M. & González, M. (2005). Mini Rev. Med. Chem. 5, 409-424.]); Bai et al. (2001[Bai, Y., Lu, J., Shi, Z. & Yang, B. (2001). Synlett, 12, 544-546.]); Hasegawa et al. (1999[Hasegawa, E., Yoneoka, A., Suzuki, K., Kato, T., Kitazume, T. & Yangi, K. (1999). Tetrahedron, 55, 12957-12968.]); Bouwman et al. (1990[Bouwman, E., Driessen, W. L. & Reedjik, J. (1990). Coord. Chem. Rev. 104, 143-172.]); Pujar & Bharamgoudar (1988[Pujar, M. A. & Bharamgoudar, T. D. (1988). Transition Met. Chem. 13, 423-425.]). For their use in sunthesis, see: Sasaki et al. (1991[Sasaki, C., Nakajima, K. & Kojima, M. (1991). Bull. Chem. Soc. Jpn, 64, 1318-1324.]); Wan et al. (2009[Wan, J.-P., Gan, S.-F., Wu J.-M. & Pan, Y.-J. (2009). Green Chem. 11, 1633-1637.]).

[Scheme 1]

Experimental

Crystal data
  • C20H14Br2N2

  • Mr = 442.15

  • Triclinic, [P \overline 1]

  • a = 9.7537 (9) Å

  • b = 10.5758 (10) Å

  • c = 17.8255 (17) Å

  • [alpha] = 83.435 (2)°

  • [beta] = 81.702 (2)°

  • [gamma] = 75.621 (2)°

  • V = 1756.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.62 mm-1

  • T = 293 K

  • 0.30 × 0.26 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.258, Tmax = 0.398

  • 22195 measured reflections

  • 8094 independent reflections

  • 5171 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.128

  • S = 1.03

  • 8094 reflections

  • 433 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.78 e Å-3

  • [Delta][rho]min = -0.51 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13...Br3i 0.93 2.85 3.433 (4) 122
C26-H26...N4ii 0.93 2.62 3.513 (4) 161
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x, -y+2, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supporting information for this paper is available from the IUCr electronic archives (Reference: BX2457 ).


Acknowledgements

This work was supported by a start-up grant from Hangzhou Normal University to Z-RQ.

References

Bai, Y., Lu, J., Shi, Z. & Yang, B. (2001). Synlett, 12, 544-546.
Bhattacharya, S. & Chaudhuri, P. (2008). Curr. Med. Chem. 15, 1762-1777.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Boiani, M. & González, M. (2005). Mini Rev. Med. Chem. 5, 409-424.  [CrossRef] [PubMed] [ChemPort]
Bouwman, E., Driessen, W. L. & Reedjik, J. (1990). Coord. Chem. Rev. 104, 143-172.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hasegawa, E., Yoneoka, A., Suzuki, K., Kato, T., Kitazume, T. & Yangi, K. (1999). Tetrahedron, 55, 12957-12968.  [Web of Science] [CrossRef] [ChemPort]
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Pujar, M. A. & Bharamgoudar, T. D. (1988). Transition Met. Chem. 13, 423-425.  [CrossRef] [ChemPort] [Web of Science]
Sasaki, C., Nakajima, K. & Kojima, M. (1991). Bull. Chem. Soc. Jpn, 64, 1318-1324.  [CrossRef] [ChemPort] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Steel, P. J. (1990). Coord. Chem. Rev. 106, 227-265.  [CrossRef] [ChemPort] [Web of Science]
Wan, J.-P., Gan, S.-F., Wu J.-M. & Pan, Y.-J. (2009). Green Chem. 11, 1633-1637.


Acta Cryst (2014). E70, o610-o611   [ doi:10.1107/S1600536814009076 ]

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