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Volume 70 
Part 1 
Pages o55-o56  
January 2014  

Received 4 December 2013
Accepted 9 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.001 Å
R = 0.057
wR = 0.160
Data-to-parameter ratio = 47.6
Details
Open access

2-(Naphthalen-1-yl)-1-phenyl-1H-benzimid­azole benzene hemisolvate

aResearch and Development Center, Bharathiar University, Coimbatore 641 046, Tamilnadu, India,bDepartment of Chemistry, S.K.P. Engineering College, Thiruvannamalai 606 611, Tamilnadu, India,cPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,dDepartment of Chemistry, Annamaliar College of Engineering, Mudaiyur 606 902, Tamilnadu, India, and eDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: thiruvalluvar.a@gmail.com

In the title compound, C23H16N2·0.5C6H6, the benzimidazole unit [maximum deviation = 0.0258 (6) Å] and the naphthalene ring system [maximum deviation = 0.0254 (6) Å] are both essentially planar and make a dihedral angle of 61.955 (17)°. The imidazole ring makes dihedral angle of 61.73 (4)° with the phenyl ring. An intra­molecular C-H...N hydrogen bond generates an S(6) ring motif. In the crystal, seven weak C-H...[pi] inter­actions involving the fused ring system, the benzene solvent mol­ecule, the imidazole phenyl rings are observed, leading to a three-dimensional architecture.

Related literature

For linear and non-linear optical properties and the thermal stability of benzimidazole-based chromophores, see: Cross et al. (1995[Cross, E. M., White, K. M., Moshrefzadeh, R. S. & Francis, C. V. (1995). Macromolecules, 28, 2526-2532.]). For imidazole as a component of vitamin B12, purine and caffeine, see: Brown (2005[Brown, K. L. (2005). Chem. Rev. 105, 2075-2150.]). For commercial and therapeutic applications of substituted benzimidazole derivatives, see: Spasov et al. (1999[Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.]). For related crystal structures, see: Jayamoorthy et al. (2012[Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.], 2013[Jayamoorthy, K., Mohandas, T., Sakthivel, P. & Jayabharathi, J. (2013). Acta Cryst. E69, o244.]); Rosepriya et al. (2011[Rosepriya, S., Thiruvalluvar, A., Jayamoorthy, K., Jayabharathi, J. & Linden, A. (2011). Acta Cryst. E67, o3519.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C23H16N2·0.5C6H6

  • Mr = 359.43

  • Triclinic, [P \overline 1]

  • a = 8.5529 (3) Å

  • b = 9.4517 (3) Å

  • c = 11.8936 (3) Å

  • [alpha] = 86.334 (2)°

  • [beta] = 89.838 (2)°

  • [gamma] = 75.051 (3)°

  • V = 926.94 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 123 K

  • 0.72 × 0.59 × 0.42 mm

Data collection
  • Agilent Xcalibur Ruby Gemini diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), using a multifaceted crystal model (Clark & Reid, 1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.963, Tmax = 0.977

  • 57784 measured reflections

  • 12045 independent reflections

  • 9086 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.160

  • S = 1.05

  • 12045 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg4 and Cg8 are the centroids of the N1/C2/N3/C9/C8 imidazole ring, the C4-C9 fused benzene ring, the C11-C16 phenyl ring, the C21-C24,C30/C29 fused benzene ring and the C1A,C2A,C3A',C1A',C2A',C3A benzene ring, respectively.

D-H...A D-H H...A D...A D-H...A
C28-H28...N3 0.95 2.61 3.2113 (10) 121
C7-H7...Cg4i 0.95 2.75 3.6019 (8) 150
C15-H15...Cg8ii 0.95 2.99 3.6981 (9) 132
C15-H15...Cg8iii 0.95 2.99 3.6981 (9) 132
C22-H22...Cg1iv 0.95 2.91 3.6478 (8) 136
C24-H24...Cg3v 0.95 2.76 3.4888 (9) 134
C26-H26...Cg2iii 0.95 2.87 3.5801 (9) 133
C27-H27...Cg1iii 0.95 2.97 3.7258 (8) 137
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z; (v) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2179 ).


Acknowledgements

SMP thanks Annamaliar College of Engineering, Mudaiyur, for providing constant support for this research. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Brown, K. L. (2005). Chem. Rev. 105, 2075-2150.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [IUCr Journals]
Cross, E. M., White, K. M., Moshrefzadeh, R. S. & Francis, C. V. (1995). Macromolecules, 28, 2526-2532.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jayamoorthy, K., Mohandas, T., Sakthivel, P. & Jayabharathi, J. (2013). Acta Cryst. E69, o244.  [CSD] [CrossRef] [IUCr Journals]
Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.  [CSD] [CrossRef] [IUCr Journals]
Rosepriya, S., Thiruvalluvar, A., Jayamoorthy, K., Jayabharathi, J. & Linden, A. (2011). Acta Cryst. E67, o3519.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o55-o56   [ doi:10.1107/S160053681303331X ]

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