N-Cyclo­hexyl-2-(5-fluoro-1H-indol-3-yl)-2-oxoacetamide

Dan-Li Tian; Gang Luo; Hong Chen; Xiao-Wei Tang; Yong-Feng Liu

doi:10.1107/S1600536811024299

. 2011 Jun 30;67(Pt 7):o1851. doi: 10.1107/S1600536811024299

N-Cyclohexyl-2-(5-fluoro-1H-indol-3-yl)-2-oxoacetamide

Dan-Li Tian ^a, Gang Luo ^a, Hong Chen ^b,^c,^*, Xiao-Wei Tang ^b, Yong-Feng Liu ^b

PMCID: PMC3151783 PMID: 21837216

Abstract

In title compound, C₁₆H₁₇FN₂O₂, the cyclohexane ring adopts a chair conformation.. The crystal packing is stabilized by weak π–π stacking interactions [centroid–centroid distance = 3.503 (5) Å] and intermolecular C—H⋯O, N—H⋯O and N—H⋯F hydrogen-bond interactions.

Related literature

For the biological activity of the title compound and its derivatives, see: Souli et al. (2008 ▶); Chai et al. (2006 ▶); Radwan et al. (2007 ▶); Karthikeyan et al. (2009 ▶). For the preparation, see: Bacher et al. (2001 ▶). For bond-length and angle data for similar structures, see: Liu et al. (2011 ▶); Sonar et al. (2006 ▶).

Experimental

Crystal data

C₁₆H₁₇FN₂O₂
M _r = 288.32
Monoclinic,
a = 11.5065 (15) Å
b = 9.7666 (12) Å
c = 12.3139 (16) Å
β = 96.639 (5)°
V = 1374.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.980, T _max = 0.988
18432 measured reflections
3717 independent reflections
3007 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.098
S = 1.04
3717 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: CrystalClear (Rigaku, 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024299/hg5056sup1.cif

e-67-o1851-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024299/hg5056Isup2.hkl

e-67-o1851-Isup2.hkl^{(182.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024299/hg5056Isup3.cml

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
N2—H2⋯F1ⁱ	0.905 (13)	2.275 (13)	3.1234 (11)	156.1 (11)
N1—H1⋯O2ⁱⁱ	0.939 (14)	1.863 (14)	2.7786 (11)	164.5 (13)
C8—H8⋯O1ⁱⁱⁱ	0.95	2.31	3.0586 (12)	136

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 30873363), the Program of the Science Foundation of Tianjin (08JCYBJC070000) and the Major Program of the Science Foundation of Tianjin (09ZCKFSH01700).

supplementary crystallographic information

Comment

Indole and their derivatives are well known as substances with biologically activity such as anti-cancer (Souli et al., 2008), anti-virus(Chai et al., 2006), anti-tubercular (Karthikeyan et al., 2009), and anti-inflammatory (Radwan et al., 2007). In recent years, our recent study is paying attention to synthesize different kinds of indole derivatives with improved bioactivities. In this paper, we reported the crystal structure of title compound.

In title compound, C₁₆H₁₇FN₂O₂, bond lengths and angles are normal and in good agreement with those reported previously (Liu et al., 2011; Sonar, et al., 2006). The cyclohexane ring (C11—C16) adopts a chair conformation. π—π interactions are indicated by the short distance (Cg1···Cg2 distance of 3.503 (5) Å, symmetry code: -x,1 - y,-z) between the centroids of the pyrrole ring (N1/C1/C6—C8) (Cg1) and benzene ring C1—C6 (Cg2) (Table 1). There are weaker C—H···O N—H···F and N—H···O intermolecular interactions, which stabilized the structure (Table 1)

Experimental

The target compound was synthesized by two steps. Oxalyl chloride was added dropwise to 5-fluorine indole in dry ether. 5-fluorine indole-3-yl-glyoxyl chloride which was the crude product, cyclohexane, two drops of triethylamine were in dry dichloromethane. The reaction mixture was washed with water and dried over Na₂SO₄ and concentrated in vacuo (Bacher et al., 2001). The residue was resolved in a methanol solution. Slow evaporation over two week at room temperature gave light-white crystals suitable for X-ray analysis.