(E)-(2-Chloro­benzyl­idene)amino 2-amino-4-chloro­benzoate

Weiyan Yin; Zhi Wang; Ying Liang; Zi-Wen Yang

doi:10.1107/S1600536812003844

. 2012 Feb 17;68(Pt 3):o770. doi: 10.1107/S1600536812003844

(E)-(2-Chlorobenzylidene)amino 2-amino-4-chlorobenzoate

Weiyan Yin ^a,^*, Zhi Wang ^a, Ying Liang ^a, Zi-Wen Yang ^a

PMCID: PMC3297841 PMID: 22412644

Abstract

In the title compound, C₁₄H₁₀Cl₂N₂O₂, the configuration about the C=N double bond is E and the dihedral angle between the benzene rings is 1.75 (5)°. An intramolecular N—H⋯O interaction generates an S(6) ring. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, resulting in [101] chains.

Related literature

For background to 2-amino-4-chlorobenzoic acid derivatives, see: Jahnke et al. (2010 ▶); Lee et al. (2005 ▶). For a related structure, see: Seong et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₁₀Cl₂N₂O₂
M _r = 309.14
Monoclinic,
a = 7.4034 (5) Å
b = 23.8190 (15) Å
c = 7.6362 (5) Å
β = 96.382 (1)°
V = 1338.23 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 100 K
0.16 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.926, T _max = 0.953
12076 measured reflections
3879 independent reflections
3637 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.084
S = 1.05
3879 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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) global, I. DOI: 10.1107/S1600536812003844/hb6586sup1.cif

e-68-0o770-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003844/hb6586Isup2.hkl

e-68-0o770-Isup2.hkl^{(190.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812003844/hb6586Isup3.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
N2—H2B⋯O2	0.88	2.02	2.6653 (12)	130
N2—H2A⋯O2ⁱ	0.88	2.19	2.9332 (12)	142

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge financial support of this work by the Foundation of Hubei Agricultural Scientific and Technological Innovation.

supplementary crystallographic information

Comment

2-Amino-4-chlorobenzoic acid derivatives show diverse biological properties such as inhibitor of the prostaglandin H2 synthase peroxidase activity (Lee et al., 2005) and allosteric inhibitors of Bcr-Abl (Jahnke et al., 2010). As a part of our studies of 2-aminobenzoic acid-containing compounds with potential biological activities, we report here the crystal structure of the title compound, (I) (Fig. 1).

The conformation of the N—H and the C=O bonds in the 2-aminobenzoic acid segment is similar to that observed in other 2-aminobenzoic acid compound (Seong et al., 2008). The dihedral angles between the two phenyl rings is 1.75 (5)°. The molecular structure is linked by N—H···O hydrogen-bonds (Table 1).

Experimental

Dicyclohexylcarbodiimide (1.1 g, 5.0 mmol) and 4-dimethylamiopryidine(0.25 g, 1.0 mmol) was added to a mixture of 2-chlorobenzaldehyde oxime (0.78 g, 5.0 mmol) and 2-amino-4-chlorobenzoic acid (0.86 g, 5.0 mmol) in dichloromethane (30 ml). The reaction mixture was stirred for 14 h at 353 k. The product was collected by filtration give a gray solid and recrystallization from its ether solution yielded colourless prisms of (I) after a few days.