Methyl 3-[(1-butyl-1H-indol-3-yl)carbonyl­amino]propionate

Gang Huang; Xing Yan Xu; Xiang Chao Zeng; Gui Hong Tang; Dong Dong Li

doi:10.1107/S1600536809029973

. 2009 Aug 8;65(Pt 9):o2063. doi: 10.1107/S1600536809029973

Methyl 3-[(1-butyl-1H-indol-3-yl)carbonylamino]propionate

Gang Huang ^a, Xing Yan Xu ^a, Xiang Chao Zeng ^a,^*, Gui Hong Tang ^a, Dong Dong Li ^a

PMCID: PMC2969888 PMID: 21577487

Abstract

In the title molecule, C₁₇H₂₂N₂O₃, the mean plane of the terminal (C=O)OMe fragment and the indole plane form a dihedral angle of 78.94 (3)°. Intermolecular N—H⋯O hydrogen bonds link the molecules into chains extended along the c axis. The crystal packing exhibits π–π interactions, indicated by the short distance of 3.472 (2) Å between the centroids of the five-membered heterocycles of neighbouring molecules.

Related literature

For the bioactivity of indole derivatives, see: Fabio et al. (2007 ▶); Sharma et al. (2004 ▶). For related structures, see: Zeng et al. (2005 ▶); Siddiquee et al. (2009 ▶).

Experimental

Crystal data

C₁₇H₂₂N₂O₃
M _r = 302.37
Monoclinic,
a = 14.144 (3) Å
b = 12.685 (3) Å
c = 9.198 (2) Å
β = 107.151 (4)°
V = 1576.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.46 × 0.42 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.961, T _max = 0.985
7760 measured reflections
3093 independent reflections
2169 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.135
S = 1.05
3093 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: SMART (Bruker,1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; 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 datablocks I, global. DOI: 10.1107/S1600536809029973/cv2594sup1.cif

e-65-o2063-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029973/cv2594Isup2.hkl

e-65-o2063-Isup2.hkl^{(151.8KB, 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
N2—H2⋯O1ⁱ	0.88	2.07	2.860 (2)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Natural Science Foundation of Guangdong Province, China (grant No. 06300581) for generous support of this study.

supplementary crystallographic information

Comment

Many indole derivatives show important bioactivities, such as metabotropic receptor antagonists (Fabio et al., 2007) and protein kinase inhibiting activity (Sharma et al., 2004). In continuation of our previous structural investigations of 3-trichloroacetylindole (Zeng et al., 2005), we report here the crystal structure of the title compound, (I).

In (I) (Fig.1), all bond lengths and angles are unexceptional and correspond to those observed in the related compounds (Zeng et al., 2005; Siddiquee et al., 2009). In the crystal structure, adjacent molecules are linked through N2—H2A···O1 hydrogen bonds, forming chains extending along the c axis. The crystal packing exhibits π–π interactions proved by short distance of 3.472 (2) Å between the centroids of five-membered heterocycles of the neighbouring molecules.

Experimental

A suspension of potassium carbonate (1.80 g, 13.0 mmol), 1-bromobutane (0.35 ml, 3.25 mmol) and methyl 3-(1H-Indole-3-carbonyl)aminopropionate (0.80 g, 3.25 mmol) in acetonitrile (30 ml) magnetically stirred at 328 K for 72 h. After filtration, the filtrate was evaporated in vacuo, and the residue was recrystallized with ethanol/water solution (1:1 v/v). Then the recrystallized solid was further purified by column chromatography on silica gel (petroleum ether/EtOAc, 1:1 v/v) to yield I (m.p. 367 K, 91.6%). Colourless crystals suitable for X-ray analysis were obtained over a period of five days by slow evaporation at room temperature of a petroleum ether/EtOAc solution (1:1 v/v).