1,2-Bis[(1,3-benzodioxol-5-yl)methyl­idene]hydrazine

Jasinski, J.P.; Golen, J.A.; Praveen, A.S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811050793

Volume 68
Part 1
Page o7
January 2012

Received 23 November 2011
Accepted 25 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 170 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.118
Data-to-parameter ratio = 17.5
Details

1,2-Bis[(1,3-benzodioxol-5-yl)methylidene]hydrazine

Jerry P. Jasinski,^a ^* James A. Golen,^a A. S. Praveen,^b B. Narayana ^c and H. S. Yathirajan ^b

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
Correspondence e-mail: jjasinski@keene.edu

The complete molecule of the title compound, C₁₆H₁₂N₂O₄, is generated by the application of a centre of inversion. The (1,3-benzodioxol-5-yl)methylidene fused-ring system is approximately planar (r.m.s. deviation = 0.020 Å) and is essentially coplanar with the central hydrazine group [dihedral angle = 5.08 (9)°]. Weak [pi] - [pi] intermolecular interactions are observed [centroid-centroid distance = 3.8553 (8) Å], providing some packing stability.

Related literature

For the biological activity of Schiff bases, see: Aydogan et al. (2001); Desai et al. (2001); El-Masry et al. (2000); Hodnett & Dunn (1970); Pandey et al. (1999); Singh & Dash (1988); Taggi et al. (2002); Xu et al. (1997). For the crystallography and coordination chemistry of compounds containing the azine functionality or a diimine linkage, see: Xu et al. (1997); Kundu et al. (2005). For related structures, see: Liu et al. (2007); Odabasoglu et al. (2007); Zhang & Zheng (2008); Zheng et al. (2005a,b).

Experimental

Crystal data

C₁₆H₁₂N₂O₄
M_r = 296.28
Monoclinic, P 2₁ /c
a = 6.1835 (2) Å
b = 4.5970 (2) Å
c = 23.8487 (10) Å
= 96.080 (4)°
V = 674.10 (5) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 170 K
0.28 × 0.25 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.971, T_max = 0.992
4759 measured reflections
1746 independent reflections
1402 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.118
S = 1.04
1746 reflections
100 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.18 e Å^-3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5026 ).

Acknowledgements

ASP thanks the University of Mysore for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Aydogan, F., Ocal, N., Turgut, Z. & Yolacan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.
Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83-90.
El-Masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429-1438.
Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem. 13, 768-770.
Kundu, N., Chatterjee, P. B., Chaudhury, M. & Tiekink, E. R. T. (2005). Acta Cryst. E61, m1583-m1585.
Liu, G., Xie, L., Wang, Y. & Wang, J.-D. (2007). Acta Cryst. E63, o2611.
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Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
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Zhang, C.-N. & Zheng, Y.-F. (2008). Acta Cryst. E64, o36.
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organic compounds