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Volume 68 
Part 11 
Page o3179  
November 2012  

Received 9 October 2012
Accepted 14 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.141
Data-to-parameter ratio = 15.5
Details
Open access

1-(Benzotriazol-1-yl)-2-bromoethanone

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: mnachemist@hotmail.com, hafizshafique@hotmail.com

In the title compound C8H6BrN3O, the benzotriazole ring is essentially planar (r.m.s. deviation = 0.0034 Å) and the bromoacetyl unit is twisted at a dihedral angle of 15.24 (16)° with respect to it. In the crystal, pairs of C-H...O hydrogen bondings result in the formation of inversion dimers, forming R22(12) rings, which are connected by further C-H...O interactions into chains extending along the b-axis direction.

Related literature

For the biological activity of the title compound, see: Nakagawa et al. (1973[Nakagawa, Y., Ichihara, S., Niki, T., Suzuki, A., Shimosato, K. & Ogata, K. (1973). Jpn Patent JP48054066A.]). For the crystal structure of a closely related compound, see: Selvarathy Grace et al. (2012[Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.]). For graph-set notation, 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
  • C8H6BrN3O

  • Mr = 240.07

  • Monoclinic, P 21 /n

  • a = 12.4815 (4) Å

  • b = 4.7207 (1) Å

  • c = 15.4780 (5) Å

  • [beta] = 103.468 (3)°

  • V = 886.91 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 6.02 mm-1

  • T = 296 K

  • 0.28 × 0.11 × 0.05 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 = 0.284, Tmax = 0.753

  • 4362 measured reflections

  • 1833 independent reflections

  • 1507 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.141

  • S = 1.07

  • 1833 reflections

  • 118 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.51 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 2.50 3.266 (3) 139
C8-H8B...O1ii 0.97 2.47 3.413 (4) 163
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y+1, 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: 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: PV2595 ).


Acknowledgements

The authors would like to thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via the 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]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.  [CSD] [CrossRef] [details]
Nakagawa, Y., Ichihara, S., Niki, T., Suzuki, A., Shimosato, K. & Ogata, K. (1973). Jpn Patent JP48054066A.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3179  [ doi:10.1107/S1600536812042900 ]

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