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

Fun, H.-K.; Ooi, C.W.; Dinesha; Viveka, S.; Nagaraja, G.K.

doi:10.1107/S1600536813003371

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 (C-C) = 0.002 Å
R = 0.042
wR = 0.116
Data-to-parameter ratio = 16.3
Details

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

Hoong-Kun Fun,^a,^b ^*⁺ Chin Wei Ooi,^a ⁺⁺ Dinesha,^c S. Viveka ^c and G.K. Nagaraja ^c

^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-HN hydrogen bond generates an S(6) ring in both molecules. Molecule A also features an intramolecular C-HO interaction, which closes an S(6) ring. In the crystal, the molecules are linked by N-HO, N-HN, O-HO, O-HN, C-HO and C-HN hydrogen bonds and C-H [pi] interactions, generating a three-dimensional network.

Related literature

For background and applications of amidoximes, see: Clapp (1976, 1984); Jochims (1996); Fylaktakidou et al. (2008); Mansuy & Boucher (2004); Kontogiorgis & Hadjipavlou-Litina (2002); Wang et al. (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₉H₁₁N₃O₂
M_r = 193.21
Triclinic, $[P \overline 1]$
a = 8.7813 (12) Å
b = 9.5432 (13) Å
c = 11.9770 (15) Å
= 80.722 (2)°
= 78.531 (2)°
= 70.181 (2)°
V = 920.6 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.965, T_max = 0.995
12849 measured reflections
4680 independent reflections
3815 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(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
_max = 0.34 e Å^-3
_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-HA	D-H	HA	DA	D-HA
N3A-H3NAN1A	0.883 (19)	2.048 (19)	2.7463 (18)	135.2 (15)
N3B-H3NBN1B	0.86 (2)	1.963 (19)	2.6798 (17)	139.7 (17)
N2B-H1NBO2Bⁱ	0.88 (2)	2.10 (2)	2.9725 (17)	173.0 (17)
N2A-H2NAO2Aⁱⁱ	0.87 (3)	2.53 (2)	3.3004 (17)	149.0 (17)
N2A-H2NAN2Bⁱⁱⁱ	0.87 (3)	2.54 (2)	3.2522 (18)	139.6 (17)
N2B-H2NBO2A^iv	0.903 (19)	2.12 (2)	2.8900 (17)	142.1 (16)
O1A-H1OAO1B	0.933 (19)	1.844 (19)	2.7733 (15)	173.9 (18)
O1B-H1OBN1A^v	0.951 (18)	1.809 (18)	2.7597 (15)	177.0 (17)
C2A-H2AAO2A	0.95	2.22	2.8556 (17)	123
C5A-H5AAO2B^vi	0.95	2.55	3.2773 (17)	133
C9A-H9ACN1B	0.98	2.56	3.499 (2)	160
C4A-H4AACg2ⁱⁱ	0.95	2.95	3.7524 (16)	143
C3B-H3BACg1^vii	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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.
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.
Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E., Varella, E. & Nicolaides, D. N. (2008). Curr. Pharm. Des. 14, 1001-1047.
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.
Mansuy, D. & Boucher, J. L. (2004). Free Radic. Biol. Med. 37, 1105-1121.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, P. G., Xian, M., Tang, X., Wu, X., Wen, Z., Cai, T. & Janczuk, A. J. (2002). Chem. Rev. 102, 1091-1134.

organic compounds