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

Jing Liu; Yong-Feng Liu; Shi Zhang; Ying Gao; Hong Chen

doi:10.1107/S1600536810054656

. 2011 Jan 8;67(Pt 2):o288. doi: 10.1107/S1600536810054656

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

Jing Liu ^a, Yong-Feng Liu ^b, Shi Zhang ^b, Ying Gao ^b, Hong Chen ^c,^*

PMCID: PMC3051520 PMID: 21522980

Abstract

In the title compound, C₁₇H₂₀N₂O₃, the cyclohexane ring adopts a chair conformation. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into layers parallel to the ac plane.

Related literature

For the biological activity of indole derivatives, see: Souli et al. (2008 ▶); Chai et al. (2006 ▶); Radwan et al. (2007 ▶); Karthikeyan et al., (2009 ▶). For details of the synthesis, see: Bacher et al. (2001 ▶). For similar structures, see: Feng et al. (2008 ▶); Sonar et al. (2006 ▶).

Experimental

Crystal data

C₁₇H₂₀N₂O₃
M _r = 300.35
Monoclinic,
a = 5.083 (3) Å
b = 27.336 (13) Å
c = 5.220 (3) Å
β = 91.977 (12)°
V = 724.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.981, T _max = 0.991
7342 measured reflections
1764 independent reflections
1569 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.076
S = 1.02
1764 reflections
208 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054656/cv5025sup1.cif

e-67-0o288-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054656/cv5025Isup2.hkl

e-67-0o288-Isup2.hkl^{(86.9KB, 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
N1—H1⋯O2ⁱ	0.96 (3)	1.90 (3)	2.840 (2)	164 (3)
N2—H2⋯O3ⁱⁱ	0.88 (3)	2.09 (3)	2.926 (3)	160 (3)

Open in a new tab

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

Acknowledgments

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

supplementary crystallographic information

Comment

Indole and their derivatives are well known as substances exhibiting various biological activiies, such as anti-cancer (Souli et al., 2008), anti-viral (Chai et al., 2006), anti-tubercular (Karthikeyan et al., 2009) and anti-inflammatory (Radwan et al., 2007). In our search for new indole derivatives with improved activities, we have synthesized the title compound, (I). Here we report its crystal structure.

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Feng et al., 2008; Sonar et al., 2006). The cyclohexane ring (C12—C17) adopts a chair conformation. In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to the ac plane.

Experimental

The target compound was synthesized by two steps. Oxalyl chloride was added dropwise to a solution of 5-methoxy-indole in dry ether, the crude product 5-methoxyindol-3-yl-glyoxyl chloride, cyclohexylamine, two drops of triethylamine in dry dichloromethane. The reaction mixture was washed with water and dried over MgSO4 and concentrated in vacuo (Bacher et al., 2001). The residue was resolved in a methanol solution. Slow evaporation over two weeks at room temperature gave light-yellow crystals suitable for X-ray analysis.