(E)-2-Furyl methyl ketone 2,4-dinitro­phenyl­hydrazone

Shang Shan; Yu-Liang Tian; Shan-Heng Wang; Wen-Long Wang; Ying-Li Xu

doi:10.1107/S1600536808015122

. 2008 May 24;64(Pt 6):o1153. doi: 10.1107/S1600536808015122

(E)-2-Furyl methyl ketone 2,4-dinitrophenylhydrazone

Shang Shan ^a,^*, Yu-Liang Tian ^a, Shan-Heng Wang ^a, Wen-Long Wang ^a, Ying-Li Xu ^a

PMCID: PMC2961490 PMID: 21202661

Abstract

Crystals of the title compound, C₁₂H₁₀N₄O₅, were obtained from a condensation reaction of 2,4-dinitrophenylhydrazine and 2-furyl methyl ketone. The molecule displays a nearly planar structure, and the furan ring is slightly twisted by a dihedral angle of 12.62 (6)° with respect to the phenylhydrazone plane. The face-to-face separation of 3.287 (7) Å between parallel benzene rings of adjacent molecules indicates the existence of π–π stacking between dinitrophenyl rings in the crystal structure.

Related literature

For general background, see: Okabe et al. (1993 ▶); Shan et al. (2003a ▶, 2006 ▶). For related structures, see: Vickery et al. (1985 ▶); Fan et al. (2004 ▶); Shan et al. (2003b ▶).

Experimental

Crystal data

C₁₂H₁₀N₄O₅
M _r = 290.24
Monoclinic,
a = 9.8917 (8) Å
b = 12.8477 (15) Å
c = 10.6549 (12) Å
β = 111.63 (2)°
V = 1258.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 (2) K
0.36 × 0.23 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: none
12121 measured reflections
2858 independent reflections
1784 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.111
S = 1.03
2858 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015122/om2233sup1.cif

e-64-o1153-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015122/om2233Isup2.hkl

e-64-o1153-Isup2.hkl^{(137.4KB, 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—H3⋯O1	0.86	1.97	2.6063 (15)	130
C9—H9⋯O4ⁱ	0.93	2.41	3.334 (2)	172
C11—H11⋯O2ⁱⁱ	0.93	2.41	3.1530 (19)	137

Open in a new tab

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

Acknowledgments

The work was supported by the Natural Science Foundation of Zhejiang Province, China (No. M203027).

supplementary crystallographic information

Comment

As some phenylhydrazone derivatives have shown to be potentially DNA damaging and mutagenic agents (Okabe et al., 1993), a series of new phenylhydrazone derivatives have been synthesized in our laboratory (Shan et al., 2003a; Shan et al., 2006). As part of the ongoing investigation, the title compound has recently been prepared and its crystal structure is reported here.

The molecular structure of the title compound is shown in Fig. 1. The molecule displays an approximately planar structure, the furan ring is slightly twisted with respect to the phenylhydrazone plane with a dihedral angle of 12.62 (6)°. The N4—C7 bond distance (Table 1) indicates a typical C=N double dond. The molecule assumes an E configuration with the phenylhydrazine and furan located on the opposite sides of the C=N bond. An intramolecular hydrogen bond is observed between the N3-imino and the adjacent N1-nitro groups; such a hydrogen bonding is a common feature in o-nitrophenylhydrazine compounds (Vickery et al., 1985; Fan et al., 2004).

A partially overlapped arrangement of parallel benzene rings of adjacent molecules is illustrated in Fig. 2. The face-to-face separation of 3.287 (7) Å strongly indicates the existence of π-π stacking between parallel dinitrophenyl rings of adjacent molecules in the crystal. It agrees with that found in a related dinitrophenylhydrazine compound, isobutylaldehyde 2,4-dinitrophenylhydrazone (Shan et al., 2003b).

The crystal structure also contains intermolecular weak C—H···O hydrogen bonding (Table 2).

Experimental

2,4-Dinitrophenylhydrazine (0.4 g, 2 mmol) was dissolved in ethanol (10 ml), and H₂SO₄ solution (98%, 0.5 ml) was slowly added to the ethanol solution with stirring. The solution was heated at 333 K for several min until the solution cleared. 2-Furyl methylketone (0.22 g, 2 mmol) was added to the above solution with continuous stirring, and the mixture was refluxed for 30 min. When the solution had cooled to room temperature brown powder crystals appeared. The powder crystals were separated and washed with water three times. Recrystallization from an absolute ethanol solution yielded well shaped single crystals.