5-[(E)-(2-Fluoro­benzyl­idene)amino]-2-hy­droxy­benzoic acid

M Nawaz Tahir; Muhammad Ilyas Tariq; Riaz H Tariq

doi:10.1107/S160053681103162X

. 2011 Aug 17;67(Pt 9):o2372. doi: 10.1107/S160053681103162X

5-[(E)-(2-Fluorobenzylidene)amino]-2-hydroxybenzoic acid

M Nawaz Tahir ^a,^*, Muhammad Ilyas Tariq ^b, Riaz H Tariq ^c

PMCID: PMC3200747 PMID: 22058978

Abstract

In the title compound, C₁₄H₁₀FNO₃, the dihedral angle between the two benzene rings is 32.66 (14)°. An S(6) ring motif is formed due to an intramolecular O—H⋯O hydrogen bond between the hydroxy and carbonyl groups. In the crystal, molecules are consolidated into dimers with R ₂ ²(8) ring motifs by pairs of O—H⋯O hydrogen bonds.

Related literature

For background and related crystal structures, see: Tahir & Shad (2010 ▶); Tahir et al. (2010a ▶,b ▶,c ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₀FNO₃
M _r = 259.23
Monoclinic,
a = 15.5688 (16) Å
b = 4.7139 (4) Å
c = 16.2248 (16) Å
β = 92.412 (4)°
V = 1189.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.30 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.972, T _max = 0.983
15880 measured reflections
2161 independent reflections
1156 reflections with I > 2σ(I)
R _int = 0.079

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.127
S = 1.01
2161 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103162X/tk2774sup1.cif

e-67-o2372-sup1.cif^{(21.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103162X/tk2774Isup2.hkl

e-67-o2372-Isup2.hkl^{(104.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681103162X/tk2774Isup3.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
O1—H1⋯O2ⁱ	0.88 (3)	1.77 (3)	2.642 (3)	176 (3)
O3—H3⋯O2	0.92 (3)	1.78 (3)	2.617 (3)	152 (3)

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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, former Vice Chancellor, University of Sargodha. Pakistan.

supplementary crystallographic information

Comment

Recently, we reported crystal structures containing the 5-amino-2-hydroxybenzoic acid moiety i.e. (II) 2-hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate (Tahir & Shad, 2010), (III) i.e. 2-{[(E)-1,3-benzodioxol-5-yl]methylideneamino}benzoic acid (Tahir et al., 2010b), (IV) i.e. 5-[(E)-(2,6-dichlorobenzylidene)amino]-2-hydroxybenzoic acid (Tahir et al., 2010a) and (V) i.e. 2-hydroxy-5-{[(E)-4-methoxybenzylidene]azaniumyl}benzoate (Tahir et al., 2010c). The title compound (I), (Fig. 1) was prepared in continuation of the synthesis of various molecules having 5-amino-2-hydroxybenzoic acid.

In (I), group A (C1—C7/N1/O1—O3), derived from 5-amino-2-hydroxybenzoic acid, and group B (C8—C14/F1), derived from 2-fluorobenzaldehyde, are each planar with r.m.s. deviations of 0.0164 and 0.0182 Å, respectively. The A/B dihedral angle between is 32.78 (7)°. There exists an intramolecular O—H···O hydrogen bond which completes a S(6) ring motif (Table 1, Fig. 1). In the crystal packing the molecules are stabilized in the form of dimers due to intermolecular O—H···O hydrogen bonds (Table 1, Fig. 2) which form a R₂²(8) ring motif (Bernstein et al., 1995).

Experimental

Equimolar quantities of 5-amino-2-hydroxybenzoic acid and 2-fluorobenzaldehyde were refluxed in methanol for 45 min resulting in yellow-brown solution. The solution was kept at room temperature which afforded violet prisms after 48 h.