2-[((E)-2-{2-[(E)-2-Hy­droxy­benzyl­idene]hydrazinecarbon­yl}hydrazinyl­idene)meth­yl]phenol

Bikas, R.; Anarjan, P.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811053268

Volume 68
Part 1
Page o193
January 2012

Received 9 December 2011
Accepted 10 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.075
Data-to-parameter ratio = 6.9
Details

2-[((E)-2-{2-[(E)-2-Hydroxybenzylidene]hydrazinecarbonyl}hydrazinylidene)methyl]phenol

Rahman Bikas,^a ⁺ Parisa Mahboubi Anarjan,^b Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c ^*

^aYoung Researchers Club, Tabriz Branch, Islamic Azad University, Tabriz, Iran,^bDepartment of Chemistry, University of Zanjan 45195-313, Zanjan, Iran,^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

The molecule of the title compound, C₁₅H₁₄N₄O₃, is completed by the application of crystallographic twofold symmetry, with the carbonyl group lying on the rotation axis. The molecule is close to planar: the greatest deviation of a torsion angle from 0° is 7.3 (2)° about the bond linking the phenol ring to the rest of the molecule. An intramolecular O-HN(imine) hydrogen bond is formed in each half of the molecule. The carbonyl O atom is anti with respect to the amine H atoms and this allows for the formation of N-HO(hydroxyl) hydrogen bonds in the crystal, which results in supramolecular layers lying parallel to (100).

Related literature

For the structures of related carbohydrazides, see: Bikas et al. (2010a,b).

Experimental

Crystal data

C₁₅H₁₄N₄O₃
M_r = 298.30
Orthorhombic, A b a 2
a = 14.3101 (4) Å
b = 9.3620 (2) Å
c = 10.2697 (2) Å
V = 1375.84 (6) Å³
Z = 4
Cu K radiation
= 0.86 mm^-1
T = 100 K
0.25 × 0.25 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.342, T_max = 1.000
2323 measured reflections
757 independent reflections
750 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.075
S = 1.10
757 reflections
110 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2N2	0.86 (3)	1.79 (4)	2.5710 (17)	150 (3)
N1-H1O2ⁱ	0.89 (3)	2.12 (3)	2.983 (2)	161 (2)
Symmetry code: (i) $[-x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6561 ).

Acknowledgements

The authors are grateful to the Islamic Azad University (Tabriz Branch), the University of Zanjan and the University of Malaya for support of this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bikas, R., Hosseini Monfared, H., Bijanzad, K., Koroglu, A. & Kazak, C. (2010a). Acta Cryst. E66, o2073.
Bikas, R., Hosseini Monfared, H., Kazak, C., Arslan, N. B. & Bijanzad, K. (2010b). Acta Cryst. E66, o2015.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds