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Volume 69 
Part 2 
Page o174  
February 2013  

Received 17 December 2012
Accepted 21 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.004 Å
R = 0.070
wR = 0.227
Data-to-parameter ratio = 15.1
Details
Open access

4-[Amino(3-methylphenyl)methylidene]-2-(3-methylphenyl)-1H-imidazol-5(4H)-one ethanol hemisolvate

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore, India 570 006, and bDepartment of Chemistry, Calicut University, Kerala, India 673635
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title compound, C18H17N3O·0.5C2H5OH, the dihedral angles between the central imidazole rings and the pendant benzene rings are 42.06 (15) and 2.01 (16)° in one asymmetric molecule and 47.91 (15) and 7.31 (14)° in the other. An intramolecular N-H...O hydrogen bond occurs in each imidazole molecule. In the crystal, the components are connected by O-H...N, N-H...O, C-H...O and N-H...N hydrogen bonds. Weak aromatic [pi]-[pi] interactions also occur [shortest centroid-centroid distance = 3.684 (3) Å].

Related literature

For background to imidazoles, see: Shi et al. (2011[Shi, F., Zeng, X.-N., Wu, F.-Y., Yan, S., Zheng, W.-F. & Tu, S.-J. (2011). J. Heterocycl. Chem. 49, 59-63.]). For a related structure, see: Chang et al. (2012[Chang, M.-J., Tsai, H.-Y., Fang, T.-C., Luo, M.-H. & Chen, K.-Y. (2012). Acta Cryst. E68, o902-o903.]). For further synthetic details, see: Shafi et al. (2005[Shafi, P. M., Sobha, T. D. & Basheer, P. A. M. (2005). Indian J. Chem. Sect. B, 44, 1298-1300.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17N3O·0.5C2H6O

  • Mr = 314.38

  • Triclinic, [P \overline 1]

  • a = 8.227 (4) Å

  • b = 13.505 (7) Å

  • c = 16.044 (8) Å

  • [alpha] = 87.451 (8)°

  • [beta] = 78.869 (9)°

  • [gamma] = 80.241 (9)°

  • V = 1723.6 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 300 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Oxford Diffraction Xcalibur CCD diffractometer

  • 16691 measured reflections

  • 6512 independent reflections

  • 4294 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.227

  • S = 1.02

  • 6512 reflections

  • 430 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3B-H3B1...O1B 0.86 2.07 2.748 (3) 135
O2-H2...N1B 1.09 1.84 2.917 (3) 170
N3B-H3B2...N1A 0.86 2.37 3.033 (3) 134
N2A-H2A...O1Ai 0.86 1.95 2.803 (3) 170
N2B-H2B...O1Bii 0.86 1.97 2.805 (3) 164
N3A-H3A1...O1A 0.86 2.12 2.783 (3) 134
N3A-H3A2...O2iii 0.86 2.02 2.857 (3) 163
C12A-H12A...O1Ai 0.93 2.59 3.492 (4) 164
C12B-H12B...O1Bii 0.93 2.54 3.455 (3) 168
C16B-H16B...O2 0.93 2.37 3.284 (4) 168
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7015 ).


Acknowledgements

SMK thanks UGC-BRS and the University of Mysore for the award of a fellowship.

References

Chang, M.-J., Tsai, H.-Y., Fang, T.-C., Luo, M.-H. & Chen, K.-Y. (2012). Acta Cryst. E68, o902-o903.  [CSD] [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Shafi, P. M., Sobha, T. D. & Basheer, P. A. M. (2005). Indian J. Chem. Sect. B, 44, 1298-1300.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shi, F., Zeng, X.-N., Wu, F.-Y., Yan, S., Zheng, W.-F. & Tu, S.-J. (2011). J. Heterocycl. Chem. 49, 59-63.  [CrossRef]


Acta Cryst (2013). E69, o174  [ doi:10.1107/S160053681205163X ]

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