3-[(E)-(2,4-Dichloro­pbenzyl­idene)amino]­benzoic acid

Muhammad Akmal; Waseeq Ahmad Siddiqui; M Nawaz Tahir; Adnan Ashraf; Farhat Nosheen

doi:10.1107/S1600536810051470

. 2010 Dec 18;67(Pt 1):o157. doi: 10.1107/S1600536810051470

3-[(E)-(2,4-Dichloropbenzylidene)amino]benzoic acid

Muhammad Akmal ^a, Waseeq Ahmad Siddiqui ^a, M Nawaz Tahir ^b,^*, Adnan Ashraf ^a, Farhat Nosheen ^a

PMCID: PMC3050322 PMID: 21522664

Abstract

In the crystal of the title compound, C₁₄H₉Cl₂NO₂, inversion-related dimers with R ₂ ²(8) ring motifs are formed by intermolecular O—H⋯O hydrogen bonding. The 3-aminobenzoic acid group and the 2,4-dichlobenzaldehyde moiety subtend a dihedral angle of 55.10 (2)°. The H atom of the carboxyl group is disordered over two sites with equal occupancies.

Related literature

For our project on the synthesis of various Schiff bases of 2,4-dichlorobenzaldehyde, see: Hayat et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₉Cl₂NO₂
M _r = 294.12
Triclinic,
a = 7.4065 (2) Å
b = 7.6176 (3) Å
c = 11.5330 (4) Å
α = 86.946 (2)°
β = 80.433 (1)°
γ = 85.833 (2)°
V = 639.38 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 296 K
0.32 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.903, T _max = 0.932
9596 measured reflections
2293 independent reflections
2048 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.084
S = 1.05
2293 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051470/bg2380sup1.cif

e-67-0o157-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051470/bg2380Isup2.hkl

e-67-0o157-Isup2.hkl^{(110.4KB, 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
O1—H1⋯O2ⁱ	0.82	1.83	2.6364 (17)	170
O2—H2⋯O1ⁱ	0.82	1.84	2.6364 (17)	162

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) is being reported as a part of our project related to the synthesis of various Schiff bases of 2,4-dichlorobenzaldehyde (Hayat et al., 2010) and then their metal complexation.

In the title compound, C₁₄H₉Cl₂NO₂, the 3-aminobenzoic group A (C1—C7/N1/O1/O2, ring centroid Cg1) and 2,4-dichlobenzaldehyde moiety B (C7—C14/CL1/CL2, ring centroid Cg2) are planar with r. m. s. deviation of 0.0200 and 0.0352 Å, respectively. The A/B dihedral angle is 55.10 (2)°. An S(5) ring motif is formed due to an intramolecular H-bond of the C—H···Cl type (Fig. 1 and Table 1). The title compound consists of H-bonded dimers due to intermolecular H-bondings of the O—H···O type (Table 1, Fig. 1) with R₂²(8) ring motifs (Bernstein et al., 1995). There exist π–π interactions between phenyl rings, connecting dimers into a 3D arrangement. The ring in the aminobenzoic group (Cg1) interacts with its symmetrry related ones Cg1ⁱ and Cg1ⁱⁱ, (i: -x, -y, - z, ii: -x, 1 - y, -z, intercentroid distances 4.1122 (9), 4.4517 (9)Å; interplanar separations: 3.3935 (6), 3.4518 (6)Å, respectively); the one in the dichlobenzaldehyde group (Cg2), in turn, interacts with Cg2ⁱⁱⁱ and Cg2^iv, (iii: -x, -y, 1 - z, iv: 1- x, -y, 1 - z; intercentroid distances 4.2926 (9), 4.0256 (9) Å; interplanar separations: 3.5346 (6), 3.5224 (6) Å, respectively). The H-atom of the carboxylate group is disordered over two sites with equal occupancy ratio.

Experimental

A mixture of m-aminobenzoic acid (0.25 g, 1.82 mmol) and 2,4-dichlorobenzaldehyde (0.32 g, 1.82 mmol) in absolute ethanol (20 ml) with few drops of acetic acid was heated to reflux (2 h), cooled to room temperature and filtered. The yellow precipitates were washed with the same solvent and dried at room temperature to get 0.47 g of the title compound (1.62 mmol, 89%). The crude material was dissolved in methanol and subjected to slow evaporation. Light yellow prisms of (I) were obtained after 48 h.