2-Bromo-4-chloro-6-[(1-phenyl­ethyl)­imino­meth­yl]phenol

Xinli Zhang

doi:10.1107/S1600536808031383

. 2008 Oct 9;64(Pt 11):o2084. doi: 10.1107/S1600536808031383

2-Bromo-4-chloro-6-[(1-phenylethyl)iminomethyl]phenol

Xinli Zhang ^a,^*

PMCID: PMC2959591 PMID: 21580949

Abstract

The title compound, C₁₅H₁₃BrClNO, is a Schiff base derived from the condensation of equimolar quantities of 3-bromo-5-chlorosalicylaldehyde and 1-phenylethanamine. The structure displays a trans configuration with respect to the imine C=N double bond. The N atom is also involved in an intramolecular O—H—N hydrogen bond, which stabilizes the configuration of the compound.

Related literature

Schiff base ligands have demonstrated significant biological activities and new examples are being tested for their antimicrobial activity (Ali et al., 2002 ▶; Cukurovali et al., 2002 ▶) and antiviral activity (Tarafder et al., 2002 ▶).

Experimental

Crystal data

C₁₅H₁₃BrClNO
M _r = 338.62
Monoclinic,
a = 21.764 (2) Å
b = 9.5088 (13) Å
c = 15.3591 (16) Å
β = 113.426 (2)°
V = 2916.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 2.99 mm⁻¹
T = 298 (2) K
0.36 × 0.22 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.412, T _max = 0.600 (expected range = 0.389–0.566)
7192 measured reflections
2574 independent reflections
1377 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.108
S = 1.00
2574 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.37 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 datablocks I, global. DOI: 10.1107/S1600536808031383/gw2049sup1.cif

e-64-o2084-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031383/gw2049Isup2.hkl

e-64-o2084-Isup2.hkl^{(126.5KB, 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⋯N1	0.82	1.87	2.591 (4)	147

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Acknowledgments

The author is grateful for a research grant (No. 08JZ09) supported by the Phytochemistry Key Laboratory of Shaanxi province.

supplementary crystallographic information

Comment

In recent years, the role of Schiff base and its derivatives in biological processes have become a topic of study. Schiff base ligands have demonstrated significant biological activities and new examples are being tested for their antitumor, antimicrobial and antiviral activities (Tarafder et al., 2002; Cukurovali et al., 2002; Ali et al., 2002). These properties stimulated our interest in this field. Crystals of the title compound, (I), were obtained as a new Schiff base compound. The title compound (I) is an 3-bromine-5-chloro-salicylaldehyde derivative. All bond lengths and bond angles are in the normal ranges and comparable to those observed in a similar salicylaldehyde Schiff base. its molecular Structure and a Crystal packing are illusrated in Figs. 1 and 2, respectively. The C1═N1 bond length of 1.257 (5) Å conforms to the value for a double bond. The torsional angles of C8—N1–2 and N1—C1—C2—C7 are 176.5 (4)° and -175.6 (4)°, respectively. Atom O1 deviates from the benzene mean plane by 0.026 (3)°, whereas atoms Br and Cl by 0.072 (4)° and 0.047 (4)°, respectively. The molecular structure adopts a trans configuration about the C1═N1 bond. In the molecule, there exists a intramolecular O—H—N hydrogen bond involving hydroxy atom O1 and imine atom N1 (Table 1). Furthermore, a more interesting phenomenon observed is shown in Fig. 2. Pairs of phen ligands from neighbouring complexes are interleaved to form a pi–pi stacking along the c axis. The distance between two phen ring Centroids are 3.744 (3) Å indicating significant pi–pi stacking packing interactions. The structure of (I) is thus stabilized by the hydrogen-bond system and aromatic-ring stacking interactions.

Experimental

3-bromine-5-Chlorosalicylaldehyde (0.1 mmol, 23.55 mg) and 1-phenylethanamine (0.1 mmol, 12.1 mg) were dissolved in methanol (10 ml). The mixture was stirred for 30 min at room temperature to give a clear brown solution. After allowing the resulting solution to stand in air for 7 d, yellow block-shaped crystals of (I) were formed on slow evaporation of the solvent. The crystals were collected, washed with methanol and dried in a vacuum desiccator using anhydrous CaCl₂ (yield 54%). Analysis found: C 46.32%, H 3.35%, calculated for C₁₅H₁₃Br_ClN_O: C 46.33%, H 3.35%.