(E)-2-(2-Hy­droxy-5-iodo­benzyl­idene)hydrazinecarboxamide

Bikas, R.; Nikbakht Sardari, S.; Hosseini, S.S.; Shahverdizadeh, G.H.; Notash, B.

doi:10.1107/S1600536812010197

Volume 68
Part 4
Page o1090
April 2012

Received 10 February 2012
Accepted 7 March 2012
Online 17 March 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
R = 0.029
wR = 0.056
Data-to-parameter ratio = 18.8
Details

(E)-2-(2-Hydroxy-5-iodobenzylidene)hydrazinecarboxamide

Rahman Bikas,^a ^* Samra Nikbakht Sardari,^b Seyed Sajjad Hosseini,^b Gholam Hossein Shahverdizadeh ^c and Behrouz Notash ^d

^aYoung Researchers Club, Tabriz Branch, Islamic Azad University, Tabriz, Iran,^bDepartment of Chemistry, Ardabil Branch, Islamic Azad University, Ardabil, Iran,^cDepartment of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, PO Box 1655, Tabriz, Iran, and ^dDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran, 1983963113, Iran
Correspondence e-mail: bikas_r@yahoo.com

In the title molecule, C₈H₈IN₃O₂, there is an intramolecular O-HN hydrogen bond between the hydroxy group and the imine N atom, which generates an S(6) ring. In the crystal, the carbonyl O atom accepts two different N-HO hydrogen bonds, which connect molecules with two R₂²(8) motifs.

Related literature

For historical background to semicarbazones, see: Arapov et al. (1987); Pickart et al. (1983). For related structures see: Bikas et al. (2010, 2012a,b); Monfared et al. (2010a). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008). For catalytic applications of aroylhydrazones, see: Monfared et al. (2010b). For a similiar structure, see: Abboud et al. (1995).

Experimental

Crystal data

C₈H₈IN₃O₂
M_r = 305.07
Monoclinic, P 2/c
a = 9.1066 (18) Å
b = 7.6277 (15) Å
c = 14.375 (3) Å
= 95.31 (3)°
V = 994.3 (3) Å³
Z = 4
Mo K radiation
= 3.20 mm^-1
T = 120 K
0.25 × 0.13 × 0.12 mm

Data collection

Stoe IPDS 2T diffractometer
Absorption correction: numerical (shape of crystal determined optically; X-RED32 and X-SHAPE, Stoe & Cie, 2005) T_min = 0.502, T_max = 0.700
10438 measured reflections
2686 independent reflections
2362 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.056
S = 1.13
2686 reflections
143 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.75 e Å^-3
_min = -0.71 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3BO2ⁱ	0.81 (4)	2.13 (4)	2.920 (3)	163 (3)
N2-H2O2ⁱⁱ	0.80 (4)	2.00 (4)	2.800 (3)	176 (3)
O1-H1N1	0.84 (2)	1.88 (3)	2.628 (3)	147 (4)
Symmetry codes: (i) $[-x+3, y, -z+{\script{3\over 2}}]$ ; (ii) -x+3, -y+2, -z+2.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2154 ).

Acknowledgements

The authors are grateful to the Islamic Azad University (Tabriz Branch) and the Islamic Azad University (Ardabil Branch) for financial support.

References

Abboud, K. A., Summers, S. P. & Palenik, G. J. (1995). Acta Cryst. C51, 1707-1709.
Arapov, O. V., Alferva, O. F., Levocheskaya, E. I. & Krasilnikov, I. (1987). Radiobiologiya, 27, 843-846.
Bikas, R., Anarjan, P. M., Ng, S. W. & Tiekink, E. R. T. (2012a). Acta Cryst. E68, o193.
Bikas, R., Anarjan, P. M., Ng, S. W. & Tiekink, E. R. T. (2012b). Acta Cryst. E68, o413-o414.
Bikas, R., Hosseini Monfared, H., Kazak, C., Arslan, N. B. & Bijanzad, K. (2010). Acta Cryst. E66, o2015.
Carvalho, S. R., da Silva, E. F., de Souza, M. V. N., Lourenco, M. C. S. & Vicente, F. R. (2008). Bioorg. Med. Chem. Lett. 18, 538-541.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Monfared, H. H., Bikas, R. & Mayer, P. (2010a). Acta Cryst. E66, o236-o237.
Monfared, H. H., Bikas, R. & Mayer, P. (2010b). Inorg. Chim. Acta, 363, 574-2583.
Pickart, L., Goodwin, W. H., Burgua, W., Murphy, T. B. & Johnson, D. K. (1983). Biochem. Pharmacol. 32, 3868-3871.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.

organic compounds