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Volume 68 
Part 11 
Page o3221  
November 2012  

Received 14 October 2012
Accepted 22 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.109
Data-to-parameter ratio = 14.9
Details
Open access

1-(1H-1,2,3-Benzotriazol-1-yl)-2-(4-methoxyphenyl)ethanone

aChemistry Department, Faculty of Science, King Abdulaziz University PO Box 80203 , Jeddah 21589, Saudi Arabia,bCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University PO Box 80203, Jeddah 21589, Saudi Arabia,cDepartment of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, 44519, Egypt, and dDepartment of Chemistry, Government College University, Faisalabad 38040, Pakistan
Correspondence e-mail: aasiri2@kau.edu.sa, hafizshafique@hotmail.com

In the title compound, C15H13N3O2, the dihedral angle between the benzotriazole ring system (r.m.s. deviation = 0.0124 Å) and the benzene ring is 76.21 (3)°. The methoxy C atom deviates from its benzene ring plane by 0.063 (2)Å. In the crystal, inversion dimers linked by pairs of C-H...O hydrogen bonds generate R22(12) loops.

Related literature

For chemical background, see: Katritzky et al. (1996a[Katritzky, A. R., Soleiman, M. & Yang, B. (1996a). Heteroat. Chem. 7, 365-367.],b[Katritzky, A. R., Yang, B. & Qian, Y. (1996b). Synlett, pp. 701-702.], 2005[Katritzky, A. R., Suzuki, K. & Wang, Z. (2005). Synlett, pp. 1656-1665.], 2010[Katritzky, A. R., Abo-Dya, N. E., Tala, S. R., Ghazvini-Zadeh, E. H., Bajaj, K. & El-Feky, S. A. (2010). Synlett, pp. 1337-1340.]). For a related structure, see: Selvarathy Grace et al. (2012[Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.]). For related literature, see: Zou et al. (2006[Zou, X., Wang, X., Cheng, C., Kong, L. & Mao, H. (2006). Tetrahedron Lett. 47, 3767-3771.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13N3O2

  • Mr = 267.28

  • Monoclinic, P 21 /c

  • a = 5.4209 (1) Å

  • b = 24.4894 (5) Å

  • c = 10.0555 (2) Å

  • [beta] = 98.552 (2)°

  • V = 1320.07 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.75 mm-1

  • T = 296 K

  • 0.34 × 0.17 × 0.16 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas CCD) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.784, Tmax = 0.889

  • 6122 measured reflections

  • 2707 independent reflections

  • 2340 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.109

  • S = 1.08

  • 2707 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O1i 0.93 2.40 3.1912 (16) 143
Symmetry code: (i) -x, -y+1, -z+1.

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: 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6975 ).


Acknowledgements

The authors thank the Deanship of Scientific Research at King Abdulaziz University for support of this research via Research Group Track of grant No. (3-102/428).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Katritzky, A. R., Abo-Dya, N. E., Tala, S. R., Ghazvini-Zadeh, E. H., Bajaj, K. & El-Feky, S. A. (2010). Synlett, pp. 1337-1340.  [ISI] [CrossRef]
Katritzky, A. R., Soleiman, M. & Yang, B. (1996a). Heteroat. Chem. 7, 365-367.  [CrossRef] [ChemPort] [ISI]
Katritzky, A. R., Suzuki, K. & Wang, Z. (2005). Synlett, pp. 1656-1665.  [ISI] [CrossRef]
Katritzky, A. R., Yang, B. & Qian, Y. (1996b). Synlett, pp. 701-702.  [CrossRef]
Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zou, X., Wang, X., Cheng, C., Kong, L. & Mao, H. (2006). Tetrahedron Lett. 47, 3767-3771.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3221  [ doi:10.1107/S1600536812043759 ]

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