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

Asiri, A.M.; Abo-Dya, N.E.; Arshad, M.N.; Alamry, K.A.; Shafiq, M.

doi:10.1107/S1600536812043759

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 (C-C) = 0.002 Å
R = 0.039
wR = 0.109
Data-to-parameter ratio = 14.9
Details

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

Abdullah M. Asiri,^a,^b ^* Nader E. Abo-Dya,^c Muhammad Nadeem Arshad,^b Khalid A. Alamry ^a,^b and Muhammad Shafiq ^d ^*

^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-HO hydrogen bonds generate R₂²(12) loops.

Related literature

For chemical background, see: Katritzky et al. (1996a,b, 2005, 2010). For a related structure, see: Selvarathy Grace et al. (2012). For related literature, see: Zou et al. (2006).

Experimental

Crystal data

C₁₅H₁₃N₃O₂
M_r = 267.28
Monoclinic, P 2₁ /c
a = 5.4209 (1) Å
b = 24.4894 (5) Å
c = 10.0555 (2) Å
= 98.552 (2)°
V = 1320.07 (4) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.784, T_max = 0.889
6122 measured reflections
2707 independent reflections
2340 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.109
S = 1.08
2707 reflections
182 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O1ⁱ	0.93	2.40	3.1912 (16)	143
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and X-SEED (Barbour, 2001).

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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
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.
Katritzky, A. R., Soleiman, M. & Yang, B. (1996a). Heteroat. Chem. 7, 365-367.
Katritzky, A. R., Suzuki, K. & Wang, Z. (2005). Synlett, pp. 1656-1665.
Katritzky, A. R., Yang, B. & Qian, Y. (1996b). Synlett, pp. 701-702.
Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zou, X., Wang, X., Cheng, C., Kong, L. & Mao, H. (2006). Tetrahedron Lett. 47, 3767-3771.

organic compounds