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Volume 68 
Part 12 
Page o3402  
December 2012  

Received 6 November 2012
Accepted 12 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.109
Data-to-parameter ratio = 12.2
Details
Open access

(E)-3-Chloro-N'-hydroxybenzene-1-carboximidamide

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Chemistry, U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India, and cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

The title compound, C7H7ClN2O, crystallizes with two independent molecules in the asymmetric unit. The compound adopts an E configuration across the C=N double bond, as the -OH group and the benzene ring are on opposite sides of the double bond while the H atom of the hydroxy group is directed away from the -NH2 group. In the crystal, molecules are linked to one another through O-H...N and N-H...O hydrogen bonds, forming chains along [010].

Related literature

For related syntheses and the biological activity of oxadiazoles, see: Kundu et al. (2012[Kundu, M., Singh, J., Singh, B., Ghosh, T., Maiti, B. C. & Maity, T. K. (2012). Indian J. Chem. Sect. B, 51, 493-497.]); Sakamoto et al. (2007[Sakamoto, T., Cullen, M. D., Hartman, T. L., Watson, K. M., Buckheit, R. W., Pannecouque, C., DeClercq, E. & Cushman, M. (2007). J. Med. Chem. 50, 3314-3319.]); Tyrkov & Sukhenko (2004[Tyrkov, A. G. & Sukhenko, L. T. (2004). Pharm. Chem. J. 38, 30-38.]). For hydrogen-bond motifs, 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
  • C7H7ClN2O

  • Mr = 170.60

  • Triclinic, [P \overline 1]

  • a = 5.0018 (17) Å

  • b = 10.984 (4) Å

  • c = 14.407 (6) Å

  • [alpha] = 74.000 (12)°

  • [beta] = 89.952 (12)°

  • [gamma] = 89.877 (11)°

  • V = 760.9 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.44 mm-1

  • T = 298 K

  • 0.24 × 0.22 × 0.20 mm

Data collection
  • Bruker SMART X2S diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.902, Tmax = 0.917

  • 14972 measured reflections

  • 2655 independent reflections

  • 2192 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.109

  • S = 1.05

  • 2655 reflections

  • 218 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...N4i 0.82 2.09 2.811 (2) 147
N3-H3B...O1ii 0.92 (3) 2.32 (3) 3.006 (2) 131 (2)
O1-H1...N2iii 0.82 2.08 2.805 (2) 147
N1-H1B...O2iv 0.87 (3) 2.36 (3) 3.006 (3) 132 (3)
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x, -y+1, -z; (iii) -x-1, -y+2, -z; (iv) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004[Bruker (2004). APEX, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). APEX, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2159 ).


Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, Tumkur, for his constant encouragement, and Professor T. N. Guru Row and Vijithkumar, S. S. C. U, Indian Institute of Science, Bangalore, for their help with the data collection. They also thank Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kundu, M., Singh, J., Singh, B., Ghosh, T., Maiti, B. C. & Maity, T. K. (2012). Indian J. Chem. Sect. B, 51, 493-497.
Sakamoto, T., Cullen, M. D., Hartman, T. L., Watson, K. M., Buckheit, R. W., Pannecouque, C., DeClercq, E. & Cushman, M. (2007). J. Med. Chem. 50, 3314-3319.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tyrkov, A. G. & Sukhenko, L. T. (2004). Pharm. Chem. J. 38, 30-38.  [CrossRef]


Acta Cryst (2012). E68, o3402  [ doi:10.1107/S1600536812046612 ]

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