2-(3-Hy­droxy­benzyl­amino)­acetic acid

Li-Hua Zhi; Wei-Na Wu

doi:10.1107/S1600536811024226

. 2011 Jun 25;67(Pt 7):o1791. doi: 10.1107/S1600536811024226

2-(3-Hydroxybenzylamino)acetic acid

Li-Hua Zhi ^a, Wei-Na Wu ^a,^*

PMCID: PMC3152044 PMID: 21837164

Abstract

There are two independent 2-(3-hydroxybenzylamino)acetic acid molecules, C₉H₁₁NO₃, in the asymmetric unit of the title compound. The dihedral angle between the benzene rings of the two independent molecules is 58.12 (4)°. The crystal packing is stablized by intermolecular O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the anti-tumor and artificial nuclease activity of copper complexes with substituted amino acid ligands, see: Jia et al. (2010 ▶). graphic file with name e-67-o1791-scheme1.jpg

Experimental

Crystal data

C₉H₁₁NO₃
M _r = 181.19
Monoclinic,
a = 11.9779 (3) Å
b = 8.0267 (2) Å
c = 9.3835 (2) Å
β = 101.391 (2)°
V = 884.39 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.23 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.980, T _max = 0.988
7436 measured reflections
1999 independent reflections
1815 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.134
S = 1.07
1999 reflections
235 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024226/vm2101sup1.cif

e-67-o1791-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024226/vm2101Isup2.hkl

e-67-o1791-Isup2.hkl^{(98.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024226/vm2101Isup3.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
N1—H1A⋯O4	0.86	2.25	2.891 (3)	132
O3—H3C⋯O2ⁱ	0.82	1.84	2.639 (4)	166
N2—H2C⋯O2ⁱⁱ	0.86	2.28	2.910 (3)	130
O6—H6A⋯O4ⁱⁱⁱ	0.82	1.85	2.646 (4)	165

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

Acknowledgments

The authors are grateful for financial support from the Doctoral Foundation of Henan Polytechnic University (B2009–65 648359 and B2009–70 648364).

supplementary crystallographic information

Comment

In recent years, substituted amino acid complexes have received extensive attention because of primarily their biological and pharmaceutical activities (Lei Jia et al., 2010). As part of our studies of substituted amino acids, the title compound was synthesized and characterized by X-ray diffraction.

The asymmetric of the title compound, 2C₉H₁₁NO₃, contains two independent 2-(3-hydroxybenzylamino)acetic acid molecules (Fig. 1). Each benzene ring is essentially planar [mean deviations of 0.0066 Å for ring C4—C9 and 0.0030 Å for ring C13—C18]. The torsion angles C12—N2 –C11—C10 and C2—N1—C3—C4 are -163.2 (2)° and -55.5 (3)°, respectively. The dihedral angle between the benzene rings in two independent amino acid molecules is 58.12 (4)°. In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds are helpful to stabilize the packing (Table 1, Fig. 2).

Experimental

To a clear solution of glycine (0.75 g, 10 mmol) and NaOH (0.40 g, 10 mmol) in a solvent mixture of water (10 mL) and methanol (20 mL), was added 3-hydroxy benzaldehyde (1.22 g, 10 mmol) and the resulting yellow solution was stirred for 3 h. After cooling to 273 K, a slight excess of NaBH₄ (0.46 g, 12 mmol) was added. The yellow color slowly discharged after 20–30 min and the pH value was maintained 5–6 by addition of acetic acid. Colorless blocks of the title compound were obtained by slow evaporation of the reaction mixture.