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Volume 69 
Part 7 
Page o1180  
July 2013  

Received 13 June 2013
Accepted 24 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 10.5
Details
Open access

N'-Hydroxypyridine-2-carboximidamide

aDepartment of Studies and Research in Chemistry, U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,cDepartment of Studies and Research in Physics, U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India,dTadimety Aromatics Pvt Ltd, Hirehally Industrial Area, Tumkur, Karnataka 572 168, India, and eSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, Karnataka 560 012, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

The title molecule, C6H7N3O, is almost planar (r.m.s. deviation = 0.0068 Å) and adopts an E conformation about the C=N double bond. In the crystal, molecules are linked by pairs of strong N-H...N hydrogen bonds, forming inversion dimers with R22(10) motifs. The dimers are further linked into C(3) chains through O-H...N hydrogen bonds.

Related literature

For the pharmaceutical and biological activity of substituted N'-hydroxybenzamidines and 1,2,4-oxadiazole derivatives, 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(7), 30-38.]). For a related structure, see: Sreenivasa et al. (2012[Sreenivasa, S., ManojKumar, K. E., Suchetan, P. A., Mohan, N. R. & Palakshamurthy, B. S. (2012). Acta Cryst. E68, o3402.])

[Scheme 1]

Experimental

Crystal data
  • C6H7N3O

  • Mr = 137.15

  • Monoclinic, C 2/c

  • a = 21.367 (5) Å

  • b = 4.6382 (11) Å

  • c = 13.003 (3) Å

  • [beta] = 105.468 (12)°

  • V = 1242.0 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.33 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.979

  • 8242 measured reflections

  • 1086 independent reflections

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

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.081

  • S = 1.08

  • 1086 reflections

  • 103 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N3i 0.903 (18) 1.859 (19) 2.7537 (14) 170.5 (17)
N2-H2N2...N1ii 0.86 (1) 2.44 (1) 3.1753 (16) 144 (1)
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6916 ).


Acknowledgements

The authors thank Dr S. C. Sharma, Ex-Vice Chancellor, Tumkur University, Tumkur, for his constant encouragement, and Professor T. N. Guru Row, S. S. C. U, Indian Institute of Science, Bangalore, for his guidance and support.

References

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Kundu, M., Singh, J., Singh, B., Ghosh, T., Maiti, B. C. & Maity, T. K. (2012). Indian J. Chem. Sect. B, 51, 493-497.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sreenivasa, S., ManojKumar, K. E., Suchetan, P. A., Mohan, N. R. & Palakshamurthy, B. S. (2012). Acta Cryst. E68, o3402.  [CrossRef] [IUCr Journals]
Tyrkov, A. G. & Sukhenko, L. T. (2004). Pharm. Chem. J.. 38(7), 30-38.


Acta Cryst (2013). E69, o1180  [ doi:10.1107/S1600536813017418 ]

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