N-Cyclo­heptyl­idene-N′-(2,4-dinitro­phenyl)hydrazine

Kia, R.; Fun, H.-K.; Kargar, H.

doi:10.1107/S1600536809002657

Volume 65
Part 2
Page o382
February 2009

Received 10 January 2009
Accepted 21 January 2009
Online 23 January 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.039
wR = 0.113
Data-to-parameter ratio = 30.0
Details

N-Cycloheptylidene-N'-(2,4-dinitrophenyl)hydrazine

Reza Kia,^a Hoong-Kun Fun ^a ^* and Hadi Kargar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
Correspondence e-mail: hkfun@usm.my

The title compound, C₁₃H₁₆N₄O₄, is a new hydrazone. An intramolecular N-HO hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The nitro groups in the ortho and para positions are almost coplanar with the benzene ring to which they are bound, making dihedral angles of 0.60 (11) and 3.18 (11)°, respectively. Pairs of intermolecular C-HO hydrogen bonds link neighbouring molecules into inversion dimers with R₂²(10) motifs. The crystal structure is further stabilized by intermolecular [pi] - [pi] interactions, with a benzene centroid-to-centroid distance of 3.6601 (4) Å.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For related literature on the applications of hydrazone, see, for example: Niknam et al., (2005); Guillaumont & Nakamura (2000); Raj & Kurup (2006); Okabe et al. (1993).

Experimental

Crystal data

C₁₃H₁₆N₄O₄
M_r = 292.30
Monoclinic, P 2₁ /n
a = 6.9721 (1) Å
b = 23.7359 (5) Å
c = 8.2274 (2) Å
= 102.351 (1)°
V = 1330.03 (5) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 100.0 (1) K
0.51 × 0.45 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.946, T_max = 0.991
26146 measured reflections
5824 independent reflections
4916 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.113
S = 1.04
5824 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.43 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O2	0.888 (14)	1.947 (14)	2.6225 (9)	131.7 (12)
C2-H2AO3ⁱ	0.95	2.52	3.3165 (10)	142
Symmetry code: (i) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2114 ).

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a postdoctoral research fellowship. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Guillaumont, D. & Nakamura, S. (2000). Dyes Pigm. 46, 85-92.
Niknam, K., Kiasat, A. R. & Karimi, S. (2005). Synth. Commun. 35, 2231-2236.
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.
Raj, B. N. B. & Kurup, M. R. P. (2006). Spectrochim. Acta Part A, 66, 898-903.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds