N′-tert-Butyl-5-(4-chloro­phen­yl)furan-2-carbohydrazide

Xi-Chen Li; Ying Li; Zi-Ning Cui; Xin-Ling Yang; Yun Ling

doi:10.1107/S1600536808003486

. 2008 Feb 6;64(Pt 3):o561. doi: 10.1107/S1600536808003486

N′-tert-Butyl-5-(4-chlorophenyl)furan-2-carbohydrazide

Xi-Chen Li ^a, Ying Li ^a, Zi-Ning Cui ^a, Xin-Ling Yang ^a, Yun Ling ^a,^*

PMCID: PMC2960804 PMID: 21201904

Abstract

In the title molecule, C₁₅H₁₇ClN₂O₂, the furan and benzene rings form a dihedral angle of 15.35 (8)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains extended in the [010] direction.

Related literature

For general background, see: Wing (1988 ▶); Wing et al. (1988 ▶); Dhadialla et al. (1998 ▶); Heller et al. (1992 ▶); Mao et al. (2004 ▶). For details of some monoacylhydrazines and diacylhydrazines containing furan, see: Yang et al. (2002 ▶); Li et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₇ClN₂O₂
M _r = 292.76
Orthorhombic,
a = 9.3770 (7) Å
b = 9.7861 (7) Å
c = 16.0119 (12) Å
V = 1469.32 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 113 (2) K
0.32 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.921, T _max = 0.949
13814 measured reflections
3496 independent reflections
2754 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.056
S = 0.96
3496 reflections
192 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1490 Friedel pairs
Flack parameter: 0.00 (4)

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003486/cv2380sup1.cif

e-64-0o561-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003486/cv2380Isup2.hkl

e-64-0o561-Isup2.hkl^{(171.5KB, 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
N1—H1A⋯O2ⁱ	0.882 (15)	2.026 (16)	2.8744 (15)	160.9 (14)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Basic Research Programme of China (grant No. 2003CB114405), the National Natural Science Foundation of China (grant No. 20672138) and the National High Technology Research and Development Programme of China (grant No. 2006AA10A201). The authors also thank the State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, People’s Republic of China.

supplementary crystallographic information

Comment

As one of molting hormone analogs, symmetrical N'-tert-butyl-N,N'-dibenzoylhydrazine (RH-5849) was first found to be a nonsteroidal ecdysone agonist in 1988 (Wing, 1988; Wing et al., 1988). Afterward, several diacylhydrazine compounds were commercially developed as insect growth regulators (IGRs) which were widely used in agriculture (Dhadialla et al., 1998; Heller et al., 1992; Mao et al., 2004). Recently, we synthesized a series of di- or mono- acylhydrazines containing furan for further study on the structure-activity relationship between monoacylhydrazines and diacylhydrazines. It was found that they both had good insecticidal activities (Yang et al., 2002; Li et al., 2006). In order to study the structural character and conformation of the monoacylhydrazine containing furan, the crystal structure of the title compound, (I), has been determined.

In (I) (Fig. 1), the benzene (C1—C6) and furan (O1/C7—C10) rings form a dihedral angle of 15.35 (8)°. The carbonyl group attached to the furan ring is almost coplanar with it. In the crystal, the intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains extended in direction [010].

Experimental

The title compound, (I), was synthesized by the reaction of 5-(4-chlorophenyl)furan-2-carbonyl chloride (0.96 g, 4 mmol) with tert-butylhydrazine hydrochloride (1.99 g, 16 mmol) using sodium hydroxide (10%, 8.0 g, 20 mmol) as the acid-binding agent. The mixture was stirred at room temperature for 5 h and filtered to obtain a yellow solution. Then the organic phase was separated and dried with anhydrous magnesium sulfate overnight. After removal of the solvent, the residue was purified by vacuum column chromatography on silica gel with petroleum ether and ethyl acetate as the eluent (V _{petroleum ether}: V _{ethyl acetate} = 3:1) and then recrystallized from hexane–ethyl acetate (V_hexane: V_{ethyl acetate}= 1:1) to give colourless crystals suitable for X-ray diffraction (Li et al., 2006).