3-(7-Meth­oxy-β-carbolin-1-yl)propionic acid monohydrate

Dong-Mei Dai; Jia-Liang Zhong; Hui-Mei An; Jian-Wei Zou

doi:10.1107/S160053681101350X

. 2011 Apr 16;67(Pt 5):o1167. doi: 10.1107/S160053681101350X

3-(7-Methoxy-β-carbolin-1-yl)propionic acid monohydrate

Dong-Mei Dai ^a,^*, Jia-Liang Zhong ^b, Hui-Mei An ^c, Jian-Wei Zou ^a

PMCID: PMC3089168 PMID: 21754473

Abstract

In the title compound, C₁₅H₁₄N₂O₃·H₂O [systematic name: 3-(7-methoxy-9H-pyrido[3,4-b]indol-1-yl)propanoic acid monohydrate], the fused rings make dhedral angles of 0.4 (1), 1.1 (2) and 1.4 (2)°. In the crystal, the water molecule is involved in the formation of three independent hydrogen-bonded chains via O—H⋯O and N—H⋯O hydrogen bonds, while the carboxy group forms an intermolecular O—H⋯N hydrogen bond.

Related literature

For the isolation of the title compound, see: Kardono et al. (1991 ▶). For the preparation, see: Kardono et al. (1991 ▶). For its pharmacological activity, see: Kuo et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₃·H₂O
M _r = 288.30
Monoclinic,
a = 4.5114 (1) Å
b = 10.8637 (2) Å
c = 28.0865 (3) Å
β = 92.414 (1)°
V = 1375.31 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 296 K
0.12 × 0.10 × 0.05 mm

Data collection

Bruker APEXII diffractometer
9119 measured reflections
2366 independent reflections
2048 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.116
S = 1.05
2366 reflections
201 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101350X/mw2003sup1.cif

e-67-o1167-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101350X/mw2003Isup2.hkl

e-67-o1167-Isup2.hkl^{(116.3KB, 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
N13—H13A⋯OWⁱ	0.86	1.86	2.7224 (18)	180
O5′—H5′A⋯N2ⁱⁱ	0.82	1.79	2.5965 (18)	169
OW—HWA⋯O5′ⁱⁱⁱ	0.85 (3)	1.92 (3)	2.7514 (19)	169 (2)
OW—HWB⋯O4′^iv	0.87 (3)	1.89 (3)	2.764 (2)	175 (2)

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

supplementary crystallographic information

Comment

The title compound, (I), was isolated from the roots of Eurycoma longifolia. It is prepared according to the procedure of Kardono et al. (Kardono et al., 1991) and recrystallized from methanol.

Bond lengths and angles are in agreement with reported literature values (Allen et al., 1987). The rings (A, B and C) are each essentially planar with r.m.s deviations of 0.0018 (5) Å, 0.0027 (8)Å and 0.0052 (16) Å, respectively. The dihedral angles between the rings are A/B =1.1 (2)°, A/C = 0.4 (1)° and B/C=1.4 (2)°. The lattice water molecule is involved in formation of three independent hydrogen-bonded chains via O—H···O and N—H···O hydrogen bonds while the carboxy group forms an intermolecular O—H···N hydrogen bond (Fig.2 and Table 1). The lattice water molecules could be considered to be a hydrogen-bond bridge which provide further stability to the crystal lattice.

Experimental

The title compound was prepared according to the procedure of Kardono et al., 1991.Crystals suitable for data collection were obtained by slow evaporation from methanol solution at 283 K over a period of two weeks.