4-[(2-Carb­oxy­eth­yl)amino]­benzoic acid monohydrate

Chunman Jia; Shangwen Chen; Wenbing Yuan

doi:10.1107/S1600536812009518

. 2012 Mar 17;68(Pt 4):o1098. doi: 10.1107/S1600536812009518

4-[(2-Carboxyethyl)amino]benzoic acid monohydrate

Chunman Jia ^a, Shangwen Chen ^a, Wenbing Yuan ^a,^*

PMCID: PMC3344050 PMID: 22589959

Abstract

In the title compound, C₁₀H₁₁NO₄·H₂O, the carboxyl group is twisted at a dihedral angle of 6.1 (3)° with respect to the benzene ring. In the crystal, the organic molecules are linked by pairs of O—H⋯O hydrogen bonds involving both carboxyl groups, forming zigzag chains propagating along the b-axis direction. The water molecules form [100] chains linked by O—H⋯O hydrogen bonds. The organic molecule and water chains are cross-linked by N—H⋯O_water and O_water—H⋯O hydrogen bonds, generating (001) sheets.

Related literature

For synthetic background, see: Kurd & Hayao (1952 ▶); Yong et al. (2004 ▶).

Experimental

Crystal data

C₁₀H₁₁NO₄·H₂O
M _r = 227.21
Orthorhombic,
a = 4.9387 (19) Å
b = 19.700 (7) Å
c = 21.616 (8) Å
V = 2103.1 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.50 × 0.20 × 0.10 mm

Data collection

Rigaku AFC-7S Mercury diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.944, T _max = 0.989
15116 measured reflections
2401 independent reflections
2059 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.167
S = 1.09
2401 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 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/S1600536812009518/hb6663sup1.cif

e-68-o1098-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009518/hb6663Isup2.hkl

e-68-o1098-Isup2.hkl^{(118.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009518/hb6663Isup3.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
N7—H7⋯O5	0.97	2.04	3.009 (2)	175
O2—H2⋯O4ⁱ	0.95	1.74	2.662 (2)	165
O3—H1⋯O1ⁱⁱ	1.04	1.63	2.622 (2)	159
O5—H5A⋯O2ⁱⁱⁱ	0.88	2.44	3.103 (2)	133
O5—H5A⋯O4^iv	0.88	2.52	3.129 (2)	127
O5—H5B⋯O5^iv	0.91	2.01	2.890 (2)	163

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

Acknowledgments

The authors would like to acknowledge the NSFC grants (grant Nos. 20761003, 21061005), the Hainan Natural Science Foundation (grant No. 210011), the Education Department of Hainan Province (grant No. Hjkj2008–23) and Hainan University (grant No. qnjj1169) for financial support.

supplementary crystallographic information

Comment

The N-substitute β-alanine derivatives, as chelating or bridging muti-caboxylate ligands, have been applied to synthesis various novel metal-organic coordination polymers(Yong et al. 2004). It was firstly reported the reaction of propiolactone with aniline derivatives to synthesis the title compound I (Kurd & Hayao 1952). The molecular structure of the title compound I is shown in Fig. 1.

In the compound I, the carboxyl group attached to the benzene ring is twisted from its plane at 6.05 (29)°. For this compound, there are four main hydrongen bonds, and their distances are 2.622(O3—H1···O1ⁱ), 2.662(O2—H2···O4^iv), 2.889(O5—H5B···O5ⁱⁱⁱ) and 3.009(N7—H7···O5)Å, respectively. Throngh the intermolecular hydrogen bonds(O3—H1···O1ⁱ, O2—H2···O4^iv) in carboxyl groups, generating R₂²(8) loops, two title compound I moleculars connect together and form a Z-type one-dimensional polymer. The crystal waters form the water chains in the structure via hydrogen bonds(O5—H5B···O5ⁱⁱⁱ). Morever, there are hydrogen bonds N7—H7···O5 between the crystal waters and compounds. As a result, all these hydrogen bonds connect the title compond I molculars into a layer (Fig. 2).

Symmetry codes: (i) -x + 3/2, y - 1/2, z; (ii) -x + 1, -y + 1, -z + 1; (iii) x + 1/2, -y + 1/2, -z + 1; (iv) -x + 3/2, y + 1/2, z.

Experimental

The title compound (I) was prepared using a slightly modified published procedure (Yong et al. 2004). A solution of KOH (11.2 g, 0.2 mol) in water (60 ml) was added dropwise to a solution of 3-chloropropanonic acid (10.9 g, 0.1 mol) in water (50 ml). To the resulting alkline solution, p-aminobenzonic(13.7 g, 0.1 mol) was slowly added, and the mixture was refluxed for 36 h. The solution was filtered and cooled to room temperature, then acidified with HCl solution until the desired white precipitated, which were collected by filtration. Pure compound (I) was obstained by crystallizing from methanol. Colourless blocks of (I) were obstained by slow evaporation of methanol solution.