(E)-2-[2-(4-Fluoro­benzyl­idene)hydrazinocarbon­yl]-N-isopropyl­benzamide

Liu, M.; Duan, Y.; Wang, Y.; Zhang, W.-X.; Liu, S.

doi:10.1107/S1600536809022181

Volume 65
Part 7
Page o1599
July 2009

Received 28 March 2009
Accepted 10 June 2009
Online 17 June 2009

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.069
Data-to-parameter ratio = 16.8
Details

(E)-2-[2-(4-Fluorobenzylidene)hydrazinocarbonyl]-N-isopropylbenzamide

Ming Liu,^a ^* Yousheng Duan,^a Yi Wang,^a Wen-Xiong Zhang ^b and Shangzhong Liu ^a

^aDepartment of Applied Chemistry, China Agriculture University, 100193 Beijing, People's Republic of China, and ^bCollege of Chemistry and Molecular Engineering, Peking University, 100871 Beijing, People's Republic of China
Correspondence e-mail: shangzho@cau.edu.cn

The title compound, C₁₈H₁₈FN₃O₂, adopts a trans conformation with respect to the C=N double bond. The dihedral angle between the two benzene rings is: 59.73 (6)°. Two independent N-HO hydrogen bonds link the molecules into layers parallel to (101).

Related literature

For biologically active phthalic diamides, see: Coronado et al. (1994); Tohnishi et al. (2000). For the preparation of the title compound, see: Zaky (2002); Shigeru et al. (2003).

Experimental

Crystal data

C₁₈H₁₈FN₃O₂
M_r = 327.35
Monoclinic, P 2₁ /n
a = 13.316 (3) Å
b = 8.8904 (18) Å
c = 14.102 (3) Å
= 91.10 (3)°
V = 1669.2 (6) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 123 K
0.30 × 0.30 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi,1995) T_min = 0.944, T_max = 0.972
15335 measured reflections
3833 independent reflections
2302 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.069
S = 1.02
3833 reflections
228 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.24 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H1O2ⁱ	0.875 (15)	2.127 (15)	2.9887 (16)	168.4 (14)
N1-H2O1ⁱⁱ	0.850 (15)	1.976 (15)	2.8256 (16)	177.8 (15)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z+1.

Data collection: RAPID-AUTO (Rigaku, 2000); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Molecular Structure Corporation and Rigaku, 2000); 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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2090 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSFC) (grant No. 20572129), National Basic Research Program of China (2003CB114405) and National Key Project of Scientific and Technical Supporting Programs Funded by Ministry of Science & Technology of China (No. 2006BAE01AE01-11).

References

Coronado, R., Morrissette, J., Sukhareva, M. & Vaughan, D. M. (1994). Am. J. Physiol. 266, 1485-1504.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Molecular Structure Corporation and Rigaku (2000). CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Rigaku (2000). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shigeru, N., Takeshi, S., Etsuko, M. & Yasuo, K. (2003). Synth. Commun. 33, 87-98.
Tohnishi, M., Nakao, H., Kohno, E., Nishida, T., Furuya, T., Shimizu, T., Seo, A., Sakata, K., Fujioka, S. & Kanno, H. (2000). Eur. Patent No. EP1006107.
Zaky, H. T. (2002). Heterocycl. Commun. 8, 355-360.

organic compounds