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Volume 69 
Part 3 
Pages o370-o371  
March 2013  

Received 2 February 2013
Accepted 2 February 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.116
Data-to-parameter ratio = 16.3
Details
Open access

(Z)-N-[2-(N'-Hydroxycarbamimidoyl)phenyl]acetamide

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and cDepartment of Chemistry, Mangalore University, Karnataka, India
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title compound, C9H11N3O2, contains two molecules (A and B), which exist in Z conformations with respect to their C=N double bond. The dihedral angles between the benzene ring and the pendant hydroxycarbamimidoyl and acetamide groups are 28.58 (7) and 1.30 (5)°, respectively, in molecule A and 25.04 (7) and 27.85 (9)°, respectively, in molecule B. An intramolecular N-H...N hydrogen bond generates an S(6) ring in both molecules. Molecule A also features an intramolecular C-H...O interaction, which closes an S(6) ring. In the crystal, the molecules are linked by N-H...O, N-H...N, O-H...O, O-H...N, C-H...O and C-H...N hydrogen bonds and C-H...[pi] interactions, generating a three-dimensional network.

Related literature

For background and applications of amidoximes, see: Clapp (1976[Clapp, L. B. (1976). In Advances in Heterocyclic Chemistry, Vol. 20, edited by A. R. Katritzky & A. J. Boulton, pp. 65-116. New York: Academic Press.], 1984[Clapp, L. B. (1984). In Comprehensive Heterocyclic Chemistry, Vol. 6, edited by K. T. Potts, pp. 365-392. Oxford: Pergamon Press.]); Jochims (1996[Jochims, J. C. (1996). In Comprehensive Heterocyclic Chemistry II, Vol. 52, edited by A. R. Katritzky, C. W. Rees & E. F. V. Scriven, pp. 179-228. Oxford: Pergamon Press.]); Fylaktakidou et al. (2008[Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E., Varella, E. & Nicolaides, D. N. (2008). Curr. Pharm. Des. 14, 1001-1047.]); Mansuy & Boucher (2004[Mansuy, D. & Boucher, J. L. (2004). Free Radic. Biol. Med. 37, 1105-1121.]); Kontogiorgis & Hadjipavlou-Litina (2002[Kontogiorgis, C. A. & Hadjipavlou-Litina, D. J. (2002). Arzneim. Forsch. Drug. Res. 52, 205-210.]); Wang et al. (2002[Wang, P. G., Xian, M., Tang, X., Wu, X., Wen, Z., Cai, T. & Janczuk, A. J. (2002). Chem. Rev. 102, 1091-1134.]). 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.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C9H11N3O2

  • Mr = 193.21

  • Triclinic, [P \overline 1]

  • a = 8.7813 (12) Å

  • b = 9.5432 (13) Å

  • c = 11.9770 (15) Å

  • [alpha] = 80.722 (2)°

  • [beta] = 78.531 (2)°

  • [gamma] = 70.181 (2)°

  • V = 920.6 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.35 × 0.20 × 0.05 mm

Data collection
  • Bruker APEX DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.995

  • 12849 measured reflections

  • 4680 independent reflections

  • 3815 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.07

  • 4680 reflections

  • 287 parameters

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

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A-C6A and C1B-C6B benzene rings, respectively.

D-H...A D-H H...A D...A D-H...A
N3A-H3NA...N1A 0.883 (19) 2.048 (19) 2.7463 (18) 135.2 (15)
N3B-H3NB...N1B 0.86 (2) 1.963 (19) 2.6798 (17) 139.7 (17)
N2B-H1NB...O2Bi 0.88 (2) 2.10 (2) 2.9725 (17) 173.0 (17)
N2A-H2NA...O2Aii 0.87 (3) 2.53 (2) 3.3004 (17) 149.0 (17)
N2A-H2NA...N2Biii 0.87 (3) 2.54 (2) 3.2522 (18) 139.6 (17)
N2B-H2NB...O2Aiv 0.903 (19) 2.12 (2) 2.8900 (17) 142.1 (16)
O1A-H1OA...O1B 0.933 (19) 1.844 (19) 2.7733 (15) 173.9 (18)
O1B-H1OB...N1Av 0.951 (18) 1.809 (18) 2.7597 (15) 177.0 (17)
C2A-H2AA...O2A 0.95 2.22 2.8556 (17) 123
C5A-H5AA...O2Bvi 0.95 2.55 3.2773 (17) 133
C9A-H9AC...N1B 0.98 2.56 3.499 (2) 160
C4A-H4AA...Cg2ii 0.95 2.95 3.7524 (16) 143
C3B-H3BA...Cg1vii 0.95 2.88 3.6645 (17) 141
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+1; (iv) x+1, y, z; (v) -x+2, -y, -z+1; (vi) x, y+1, z-1; (vii) x, y, z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7034 ).


Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/CIPPM813040). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Clapp, L. B. (1976). In Advances in Heterocyclic Chemistry, Vol. 20, edited by A. R. Katritzky & A. J. Boulton, pp. 65-116. New York: Academic Press.
Clapp, L. B. (1984). In Comprehensive Heterocyclic Chemistry, Vol. 6, edited by K. T. Potts, pp. 365-392. Oxford: Pergamon Press.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E., Varella, E. & Nicolaides, D. N. (2008). Curr. Pharm. Des. 14, 1001-1047.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jochims, J. C. (1996). In Comprehensive Heterocyclic Chemistry II, Vol. 52, edited by A. R. Katritzky, C. W. Rees & E. F. V. Scriven, pp. 179-228. Oxford: Pergamon Press.
Kontogiorgis, C. A. & Hadjipavlou-Litina, D. J. (2002). Arzneim. Forsch. Drug. Res. 52, 205-210.  [ChemPort]
Mansuy, D. & Boucher, J. L. (2004). Free Radic. Biol. Med. 37, 1105-1121.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wang, P. G., Xian, M., Tang, X., Wu, X., Wen, Z., Cai, T. & Janczuk, A. J. (2002). Chem. Rev. 102, 1091-1134.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o370-o371   [ doi:10.1107/S1600536813003371 ]

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