N-(4-Chloro­phen­yl)-4-(2-oxocyclo­pent­yl)butyramide

Lin-Tao Yu; Jiang-Tao Wei; Xiang-Ge Zhou

doi:10.1107/S1600536808042505

. 2008 Dec 20;65(Pt 1):o162. doi: 10.1107/S1600536808042505

N-(4-Chlorophenyl)-4-(2-oxocyclopentyl)butyramide

Lin-Tao Yu ^a, Jiang-Tao Wei ^a, Xiang-Ge Zhou ^a,^*

PMCID: PMC2968074 PMID: 21581619

Abstract

In the title compound, C₁₅H₁₈ClNO₂, the amide group is coplanar with the chlorophenyl group, making a dihedral angle of 1.71 (12)°. The cyclopentanone ring adopts a twist conformation. A weak intramolecular C—H⋯O hydrogen bond is observed. Molecules are linked into cyclic centrosymmetric dimers by paired N—H⋯O hydrogen bonds.

Related literature

For the synthesis of cyathin terpenoids, see: Drège et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₈ClNO₂
M _r = 279.75
Triclinic,
a = 5.5897 (2) Å
b = 8.8847 (3) Å
c = 14.6480 (4) Å
α = 80.906 (2)°
β = 86.436 (2)°
γ = 85.351 (2)°
V = 715.05 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 (2) K
0.42 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.895, T _max = 0.948
8899 measured reflections
3273 independent reflections
1648 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.147
S = 1.01
3273 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042505/ci2743sup1.cif

e-65-0o162-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042505/ci2743Isup2.hkl

e-65-0o162-Isup2.hkl^{(160.5KB, 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—H1N⋯O1ⁱ	0.86	2.17	2.980 (2)	158
C15—H15⋯O2	0.93	2.29	2.889 (2)	121

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the NSFC (grant Nos. 20672075 and 20771076) and Sichuan University for financial support.

supplementary crystallographic information

Comment

2-Oxocyclopentyl carboxylic acid derivatives are a class of starting materials important for the preparation of cyathin terpenoids (Drège et al., 2006). We report here the crystal structure of the title compound, a oxocyclopentyl derivative.

Bond lengths and angles are normal. The amide group is almost coplanar with the benzene ring system (Fig. 1). The C8/C9/N1/O2 and C10—C15 planes form dihedral angle of 1.71 (12)°. The cyclopentanone ring adopts a twist conformation. An intramolecular C15—H15···O2 hydrogen bond is observed.

The crystal packing is stabilized by N—H···O hydrogen bonds (Table 1). The molecules are linked into cyclic centrosymmetric dimers by paired N—H···O hydrogen bonds.

Experimental

A mixture of spiro[4,4]nonane-1,6-dione (1 mmol), p-chloroaniline (2.2 mmol) and iodine (0.1 mmol) was stirred in refluxing dichloromethane (20 ml) for 24 h to afford the title compound. Single crystals suitable for X-ray diffraction were obtained by slow evaporation an ethyl acetate solution.