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

Ming Liu; Yousheng Duan; Yi Wang; Wen-Xiong Zhang; Shangzhong Liu

doi:10.1107/S1600536809022181

. 2009 Jun 17;65(Pt 7):o1599. doi: 10.1107/S1600536809022181

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

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

PMCID: PMC2969323 PMID: 21582873

Abstract

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—H⋯O 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,
a = 13.316 (3) Å
b = 8.8904 (18) Å
c = 14.102 (3) Å
β = 91.10 (3)°
V = 1669.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.069
S = 1.02
3833 reflections
228 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022181/ya2090sup1.cif

e-65-o1599-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022181/ya2090Isup2.hkl

e-65-o1599-Isup2.hkl^{(187.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O2ⁱ	0.875 (15)	2.127 (15)	2.9887 (16)	168.4 (14)
N1—H2⋯O1ⁱⁱ	0.850 (15)	1.976 (15)	2.8256 (16)	177.8 (15)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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).

supplementary crystallographic information

Comment

Phthalic diamides possess insecticidal properties due to their ability to activate ryanodine receptor (Coronado et al., 1994; Tohnishi et al., 2000). The title compound (I), a new phthalic diamide derivative, was synthesized by the condensation of N-aminophthalimide with 4-fluorobenzaldehyde followed by a ring-opening reaction using isopropyl amine (Zaky, 2002; Shigeru et al., 2003).

The molecular structure of the title compound is shown in Fig. 1. Molecule was proved to be a trans -isomer with respect to the C9=N2 double bond.

There are two independent N—H···O bonds (Table 1), which link molecules into the layers parallel to (101) plane (Fig. 2).

Experimental

To a solution of N-aminophthalimide (1.62 g, 10 mmol) and 4-fluorobenzaldehyde (1.24 g, 10 mmol) in 1,4-dioxane (100 ml), 12 N HCl (0.1 ml) was added at room temperature. After stirring for 5–10 min, a solution of isopropyl amine (1.16 g, 20 mmol) in 1,4-dioxane (10 ml) was added; the reaction mixture was stirred overnight at room temperature. After the solvent was evaporated under reduced pressure, the resulting mixture was dissolved in ethyl acetate (80 ml), washed with H₂O (3×30 ml) and dried with anhydrous sodium sulfate to give the title compound (2.01 g, 61.5%). Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of ethanol solution at room temperature over one week.