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

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

doi:10.1107/S1600536812042900

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 (C-C) = 0.004 Å
R = 0.044
wR = 0.141
Data-to-parameter ratio = 15.5
Details

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

Abdullah M. Asiri,^a,^b Nader E. Abo-Dya,^c Muhammad Nadeem Arshad ^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: 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-HO hydrogen bondings result in the formation of inversion dimers, forming R₂²(12) rings, which are connected by further C-HO interactions into chains extending along the b-axis direction.

Related literature

For the biological activity of the title compound, see: Nakagawa et al. (1973). For the crystal structure of a closely related compound, see: Selvarathy Grace et al. (2012). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₈H₆BrN₃O
M_r = 240.07
Monoclinic, P 2₁ /n
a = 12.4815 (4) Å
b = 4.7207 (1) Å
c = 15.4780 (5) Å
= 103.468 (3)°
V = 886.91 (4) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.284, T_max = 0.753
4362 measured reflections
1833 independent reflections
1507 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.141
S = 1.07
1833 reflections
118 parameters
H-atom parameters constrained
_max = 0.43 e Å^-3
_min = -0.51 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O1ⁱ	0.93	2.50	3.266 (3)	139
C8-H8BO1ⁱⁱ	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); 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: 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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References