2-Amino-4-chloro­benzoic acid

Abeer Mohamed Farag; Siang Guan Teoh; Hasnah Osman; Chin Sing Yeap; Hoong-Kun Fun

doi:10.1107/S1600536810050166

. 2010 Dec 4;67(Pt 1):o37. doi: 10.1107/S1600536810050166

2-Amino-4-chlorobenzoic acid

Abeer Mohamed Farag ^a, Siang Guan Teoh ^a, Hasnah Osman ^a, Chin Sing Yeap ^b,^‡, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC3050223 PMID: 21522747

Abstract

The title compound, C₇H₆ClNO₂, is almost planar, with an r.m.s. deviation of 0.040 Å. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked into centrosymmetric dimers by pairs of O—H⋯O hydrogen bonds. These dimers are stacked along [010].

Related literature

For the pharmacological properties of quinazolinone derivatives, see: Prakash Naik et al. (2009 ▶); Bembenek et al. (2010 ▶); Miller et al. (2010 ▶); Sikorska et al. (1998 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₇H₆ClNO₂
M _r = 171.58
Monoclinic,
a = 15.4667 (10) Å
b = 3.7648 (2) Å
c = 23.7598 (15) Å
β = 93.015 (3)°
V = 1381.59 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 100 K
0.53 × 0.17 × 0.05 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.780, T _max = 0.975
34764 measured reflections
3645 independent reflections
3175 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.089
S = 1.07
3645 reflections
112 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050166/hb5757sup1.cif

e-67-00o37-sup1.cif^{(15KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050166/hb5757Isup2.hkl

e-67-00o37-Isup2.hkl^{(178.8KB, 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
O2—H1O2⋯O1ⁱ	0.853 (16)	1.787 (16)	2.6354 (8)	173.0 (16)
N1—H1N1⋯O1	0.851 (15)	2.102 (14)	2.6918 (9)	126.0 (13)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the RU research grant (815002). AMF thanks the Libyan Government for providing a scholarship. HKF and CSY thank USM for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Anthranilic acid is required as a starting compound to prepare quinoline derivatives. Quinazolinones are well known as biologically active compounds. Quinazolinones have been studied for their interesting pharmacological properties such as analgesic, antiinflammatory, antibacterial, anticonvulsant, antihypertensive, antimalarial, anticancer activities and as treatment of diabetic complications such as cataracts, nephropathy and neuropathy (Prakash Naik et al., 2009), as well as used as prolyl hydroxylase inhibitors (Bembenek et al., 2010) and antibacterial drugs (Miller et al., 2010). New complexes have been prepared from 2-amino-4-chlorobenzoic acid by Sikorska et al., (1998).

The title compound (Fig. 1) is almost planar with maximum deviation of 0.097 (1) Å at atom O1. An intramolecular N1—H1N1···O1 hydrogen bond generates S(6) ring motif (Bernstein et al., 1995). In the crystal, the molecules are linked into centrosymmetric dimers by O2—H1O2···O1 hydrogen bonds and these dimers are stacked down b axis (Fig. 2, Table 1).

Experimental

The attempt to prepare the Schiff base ligand by stirring 2-amino-4-chlorobenzoic acid (1 mol) and salicyldehyde (1 mol) together at 70 °C for 3 h in 10 ml of ethanol was unsuccessful. The resulting orange solution was filtered and orange needles were formed after a few days of slow evaporation of the solvent at room temperature. Unfortunately, the crystals were that of the starting material (2-amino-4-chlorobenzoic acid) with melting point 119 °C.