4-Bromo-2-[(E)-(2-fluoro-5-nitro­phenyl)iminometh­yl]phenol

Shaaban K Mohamed; Mehmet Akkurt; Peter N Horton; Antar A Abdelhamid; Adel A Marzouk

doi:10.1107/S1600536812050696

. 2012 Dec 19;69(Pt 1):o107. doi: 10.1107/S1600536812050696

4-Bromo-2-[(E)-(2-fluoro-5-nitrophenyl)iminomethyl]phenol

Shaaban K Mohamed ^a,^b, Mehmet Akkurt ^c,^*, Peter N Horton ^d, Antar A Abdelhamid ^a,^b, Adel A Marzouk ^e

PMCID: PMC3588360 PMID: 23476369

Abstract

The molecular conformation of the title compound, C₁₃H₈BrFN₂O₃, is essentially planar, with maximum deviations of 0.076 (1) and −0.080 (2) Å for the O atoms of the NO₂ group. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, pairs of molecules are linked via two pairs of C—H⋯O hydrogen bonds, forming inversion dimers that enclose R ² ₂(7)R ² ₂(10)R ² ₂(7) ring motifs.

Related literature

For the synthesis and biological activity of azomethines, see: Przybylski et al. (2009 ▶); Kalaivani et al. (2012 ▶); Blair et al. (2000 ▶). For the synthesis of fluorinated azomethines, see: Mohamed et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₃H₈BrFN₂O₃
M _r = 339.11
Monoclinic,
a = 4.5082 (9) Å
b = 19.815 (4) Å
c = 13.853 (3) Å
β = 95.484 (5)°
V = 1231.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.36 mm⁻¹
T = 100 K
0.24 × 0.04 × 0.03 mm

Data collection

Rigaku AFC12 (Right) diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ▶) T _min = 0.500, T _max = 0.906
8107 measured reflections
2811 independent reflections
2633 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.025
wR(F ²) = 0.059
S = 1.05
2811 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: CrystalClear-SM Expert (Rigaku, 2012 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(18.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050696/xu5665sup1.cif

e-69-0o107-sup1.cif^{(18.1KB, cif)}

Click here for additional data file.^{(138KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050696/xu5665Isup2.hkl

e-69-0o107-Isup2.hkl^{(138KB, hkl)}

Click here for additional data file.^{(4.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812050696/xu5665Isup3.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⋯N1	0.84	1.86	2.601 (2)	146
C7—H7⋯O3ⁱ	0.95	2.45	3.399 (3)	173
C13—H13⋯O3ⁱ	0.95	2.48	3.430 (3)	173

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Symmetry code: (i) Inline graphic .

Acknowledgments

The EPSRC National Crystallography Service is gratefully acknowledged for the X-ray diffraction data. AAA and SKM thank the Ministry of Higher Education of Egypt for financial support of this collaporative project. The authors are also thankful to Manchester Metropolitan University and Erciyes University for supporting this study.

supplementary crystallographic information

Comment

Schiff bases have been shown to exhibit a broad range of biological activities, including antifungal, antibacterial, antimalarial, antiproliferative, anti-inflammatory, antiviral, and antipyretic properties (Przybylski et al., 2009; Kalaivani et al., 2012). Among such compounds, the fluorinated Schiff's bases were considered to possess a distingushed biological activity due to the dramatic affect of fluorine atom on the metabolism and distribution of drug molecules in the body (Blair et al., 2000). Further to our on going study on synthesis of bioactive fluorinated compounds (Mohamed et al., 2012) we herein report the synthesis and crystal structure of a new fluorinated azomethine derivative.

In the title compound (I), (Fig. 1), the molecular conformation is essentially planar, with maxium deviations of 0.076 (1) and -0.080 (2) Å, respectively, for O2 and O3. The C1–C7–N1–C8 torsion angle is 179.92 (16)°. The bond lengths and angles in (I) are within the normal range (Allen et al., 1987).

Molecular conformation is stabilized by O—H···N hydrogen bond (Table 1), forming an S(6) ring motif. In the crystal, the pairs of molecules are linked by C—H···O interactions (Table 1, Fig. 2), generating R²₂(7)R²₂(10)R²₂(7) ring motifs (Bernstein et al., 1995) along the [001] direction.

Experimental

A mixture of 1 mmol (156 mg) 2-fluoro-5-nitroaniline and 1 mmol (201 mg) 5-bromo-2-hydroxybenzaldehyde in 50 ml e thanol was heated at 350 K and monitored by TLC till completion after 12 h. A mass solid product was deposited once the reaction mixture was allowed to cool at room temperature. The crude product was filtered dried under vacuum and washed by ethanol. Pure yellow rods (m.p. 465 K) suitable for X-ray diffraction were obtained in an excellent yield (92%) by crystallization of crude product from ethanol.