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Volume 69 
Part 10 
Page o1576  
October 2013  

Received 16 September 2013
Accepted 17 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.046
wR = 0.103
Data-to-parameter ratio = 15.4
Details
Open access

(E)-N-(1,3-Benzodioxol-5-yl)-1-(4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]methoxy}phenyl)methanimine

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C20H18N4O3, the dihedral angles between the central benzene ring and the 1H-1,2,3-triazole ring and the fused benzene ring are 65.34 (19) and 3.64 (18)°, respectively. The dioxole ring adopts a shallow envelope conformation, with the methylene C atom displaced by 0.156 (5) Å from the other four atoms (r.m.s. deviation = 0.007Å). In the crystal, the molecules are linked by C-H...O and C-H...N hydrogen bonds, generating a three-dimensional network.

Related literature

For background to Schiff base compounds, see: Arora et al. (2002[Arora, K., Gupta, A. & Agarwal, D. D. (2002). Asian J. Chem. 14, 1611-1615.]); Calligaris & Randaccio (1987[Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, p 715. Oxford: Pergamon.]); Macho et al. (2004[Macho, V., Kralik, M., Hudec, J. & Cingelova, J. (2004). J. Mol. Catal. A Chem. 209, 69-73.]); Singh et al. (2012[Singh, P., Raj, R., Kumar, V., Mahajan, M. P., Bedi, P. M. S., Kaur, T. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 594-600.]); Tanaka & Shiraishi (2000[Tanaka, K. & Shiraishi, R. (2000). Green Chem. 2, 272-273.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N4O3

  • Mr = 362.38

  • Orthorhombic, P 21 21 21

  • a = 5.1506 (6) Å

  • b = 15.334 (2) Å

  • c = 22.965 (5) Å

  • V = 1813.8 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.69 × 0.39 × 0.20 mm

Data collection
  • STOE IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.956, Tmax = 0.985

  • 13771 measured reflections

  • 3770 independent reflections

  • 2125 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.103

  • S = 0.90

  • 3770 reflections

  • 245 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O3i 0.93 2.59 3.471 (4) 157
C7-H7B...N2ii 0.97 2.59 3.380 (5) 138
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (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.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7140 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

Arora, K., Gupta, A. & Agarwal, D. D. (2002). Asian J. Chem. 14, 1611-1615.  [ChemPort]
Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, p 715. Oxford: Pergamon.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Macho, V., Kralik, M., Hudec, J. & Cingelova, J. (2004). J. Mol. Catal. A Chem. 209, 69-73.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Singh, P., Raj, R., Kumar, V., Mahajan, M. P., Bedi, P. M. S., Kaur, T. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 594-600.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Tanaka, K. & Shiraishi, R. (2000). Green Chem. 2, 272-273.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1576  [ doi:10.1107/S1600536813025749 ]

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