1-[1-(4-Chloro­phen­yl)ethyl­idene]carbono­hydrazide

Du, L.; Du, L.; Wang, S.

doi:10.1107/S1600536809030384

Volume 65
Part 9
Page o2130
September 2009

Received 7 July 2009
Accepted 31 July 2009
Online 12 August 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.045
wR = 0.126
Data-to-parameter ratio = 13.4
Details

1-[1-(4-Chlorophenyl)ethylidene]carbonohydrazide

Lingyun Du,^a ^* Lei Du ^a and Shuhao Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
Correspondence e-mail: dulingyun@lcu.edu.cn

The molecular skeleton of the title molecule, C₉H₁₁ClN₄O, is essentially planar, the dihedral angle between the ring and the and N/N/C plane being 6.7 (3)°. In the crystal, intermolecular N-HO and N-HN hydrogen bonds link the molecules into ribbons propagated along [010].

Related literature

For the biological activity of carbonohydrazide derivatives, see: Loncle et al. (2004). For related structures, see Meyers et al. (1995).

Experimental

Crystal data

C₉H₁₁ClN₄O
M_r = 226.67
Monoclinic, P 2₁ /c
a = 14.6429 (14) Å
b = 9.6041 (12) Å
c = 7.4327 (9) Å
= 90.102 (1)°
V = 1045.3 (2) Å³
Z = 4
Mo K radiation
= 0.34 mm^-1
T = 298 K
0.40 × 0.30 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.875, T_max = 0.960
4419 measured reflections
1837 independent reflections
1085 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.126
S = 1.01
1837 reflections
137 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N4ⁱ	0.86	2.24	3.024 (3)	152
N3-H3O1ⁱⁱ	0.86	2.09	2.850 (3)	147
N4-H4AO1ⁱⁱⁱ	0.89	2.34	3.206 (3)	164
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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: CV2587 ).

Acknowledgements

The authors acknowledge financial support by the Science Foundation of China (grant No. 20877037).

References

Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem. 39, 1067-1071.
Meyers, C. Y., Kolb, V. M. & Robinson, P. D. (1995). Acta Cryst. C51, 775-777.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

organic compounds