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Volume 68 
Part 12 
Page o3432  
December 2012  

Received 14 October 2012
Accepted 30 October 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.032
wR = 0.068
Data-to-parameter ratio = 9.9
Details
Open access

1-Chloro-1H-1,2,3-benzotriazole

aDepartment of Pharmacy, The First Affiliated Hospital, Chengdu Medical College, Chengdu 610500, People's Republic of China
Correspondence e-mail: zhenglinli326@163.com

The title compound, C6H4ClN3, is essentially planar, with a maximum deviation of 0.007 (3) Å. In the crystal, a short contact of 2.818 (3) Å is observed between N and Cl atoms of adjacent molecules.

Related literature

For related structures of benzotriazole derivatives, see: Jebas et al. (2012[Jebas, S. R., Selvarathy Grace, P., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o2239.]); Guo et al. (2012[Guo, T., Cao, G. & Xu, S. (2012). Acta Cryst. E68, o1409.]); Selvarathy et al. (2012[Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.]); Xu & Shen (2012[Xu, S. & Shen, Y. (2012). Acta Cryst. E68, o1066.]). For applications of the title compound, see: Hunter et al. (2006[Hunter, R., Caira, M. & Stellenboom, N. (2006). J. Org. Chem. 71, 8268-8271.]) and references cited therein. For the biological activity of benzotriazole derivatives, see: Gaikwad et al. (2012[Gaikwad, N. D., Patil, S. V. & Bodade, V. D. (2012). Bioorg. Med. Chem. Lett. 22, 3449-3454.]); Dubey et al. (2011[Dubey, A., Srivastava, S. K. & Srivastava, S. D. (2011). Bioorg. Med. Chem. Lett. 21, 569-573.]).

[Scheme 1]

Experimental

Crystal data
  • C6H4ClN3

  • Mr = 153.57

  • Orthorhombic, F d d 2

  • a = 22.8022 (11) Å

  • b = 14.2637 (8) Å

  • c = 8.2259 (4) Å

  • V = 2675.4 (2) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 293 K

  • 0.42 × 0.34 × 0.32 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.979, Tmax = 1.000

  • 1503 measured reflections

  • 918 independent reflections

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

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.060

  • S = 1.06

  • 918 reflections

  • 91 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 275 Friedel pairs

  • Flack parameter: 0.00 (8)

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5634 ).


Acknowledgements

This project was supported by Applied Basic Research Programs of Science & Technology Department of Sichuan Province (No. 2012JY0035) and the research fund of Chengdu Medical College, China (No. CYZ11-021).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Dubey, A., Srivastava, S. K. & Srivastava, S. D. (2011). Bioorg. Med. Chem. Lett. 21, 569-573.  [CrossRef] [ChemPort] [PubMed]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gaikwad, N. D., Patil, S. V. & Bodade, V. D. (2012). Bioorg. Med. Chem. Lett. 22, 3449-3454.  [CrossRef] [ChemPort] [PubMed]
Guo, T., Cao, G. & Xu, S. (2012). Acta Cryst. E68, o1409.  [CSD] [CrossRef] [details]
Hunter, R., Caira, M. & Stellenboom, N. (2006). J. Org. Chem. 71, 8268-8271.  [CrossRef] [PubMed] [ChemPort]
Jebas, S. R., Selvarathy Grace, P., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o2239.  [CSD] [CrossRef] [details]
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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Xu, S. & Shen, Y. (2012). Acta Cryst. E68, o1066.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3432  [ doi:10.1107/S1600536812044820 ]

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