(E)-4-[(4-Bromo­phen­yl)imino­meth­yl]-2-meth­oxy­phenol

Karla Fejfarová; Michal Dušek; Sepideh Maghsodlou Rad; Aliakbar Dehno Khalaji

doi:10.1107/S1600536812031704

. 2012 Jul 18;68(Pt 8):o2466. doi: 10.1107/S1600536812031704

(E)-4-[(4-Bromophenyl)iminomethyl]-2-methoxyphenol

Karla Fejfarová ^a,^*, Michal Dušek ^a, Sepideh Maghsodlou Rad ^b, Aliakbar Dehno Khalaji ^b

PMCID: PMC3414922 PMID: 22904909

Abstract

In the crystal structure of the title compound, C₁₄H₁₂BrNO₂, the dihedral angle between the rings is 37.87 (10)° and the molecule has an E conformation about the central C=N bond. In the crystal, molecules are connected by intermolecular O—H⋯N hydrogen bonds into zigzag chains running parallel to the b axis. The packing also features C—H⋯O interactions.

Related literature

For Schiff base derivatives and related structures, see: Fejfarová et al. (2010a ▶,b ▶); Özek et al. (2009 ▶, 2010 ▶); Akkurt et al. (2008 ▶); Khalaji et al. (2007 ▶, 2009 ▶). For applications and properties of Schiff base compounds, see: da Silva et al. (2011 ▶); Dalapati et al. (2011 ▶); Sun et al. (2012 ▶).

Experimental

Crystal data

C₁₄H₁₂BrNO₂
M _r = 306.2
Monoclinic,
a = 6.5692 (3) Å
b = 11.4323 (4) Å
c = 17.5552 (9) Å
β = 97.798 (4)°
V = 1306.22 (10) Å³
Z = 4
Cu Kα radiation
μ = 4.24 mm⁻¹
T = 120 K
0.33 × 0.13 × 0.04 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.432, T _max = 1
12474 measured reflections
2320 independent reflections
1991 reflections with I > 3σ(I)
R _int = 0.044

Refinement

R[F ² > 3σ(F ²)] = 0.028
wR(F ²) = 0.067
S = 1.65
2320 reflections
166 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031704/pk2433sup1.cif

e-68-o2466-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031704/pk2433Isup2.hkl

e-68-o2466-Isup2.hkl^{(91.5KB, 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
C2—H2⋯O2ⁱ	0.96	2.31	3.247 (3)	165
C14—H14⋯O2ⁱⁱ	0.96	2.40	3.325 (3)	163
O2—H2o⋯N1ⁱⁱⁱ	0.85 (2)	1.98 (2)	2.787 (2)	158 (3)

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

We acknowledge Golestan University for partial support of this work, the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics, Prague, and the Praemium Academiae Project of the Academy of Sciences of the Czech Republic.

supplementary crystallographic information

Comment

Schiff base compounds exhibit a broad range of biological activities, including antifungal and antibacterial properties (da Silva et al., 2011). They are used as anion sensors (Dalapati et al., 2011) and as non-linear optics compounds (Sun et al., 2012).

The present work is part of a ongoing structural study of Schiff bases (Khalaji et al., 2009; Fejfarová et al., 2010a,b) and we report here the structure of (E)-(4-hydroxy-3-methoxybenzylidene)-4-bromoaniline, (1). In the crystal, the dihedral angle between the two phenyl rings is 37.87 (10)° and the molecule has an E conformation about the central C=N bond. The methoxy group is slightly twisted from the attached benzene ring [C2—C3—O1—C7 = 13.8 (3)°]. The C=N and C—N bond lengths of 1.283 (3) Å and 1.419 (3) Å agree well with the corresponding distances in other Schiff bases (Akkurt et al., 2008; Özek et al., 2009, 2010; Khalaji et al., 2007, 2009; Fejfarová et al., 2010a,b).

The molecules are connected by intermolecular O—H···N hydrogen bonds, forming zigzag chains parallel to the b axis (Fig. 2). The crystal structure is further stabilized by intermolecular C—H···O hydrogen bonds.

Experimental

To a stirring solution of the 4-hydroxy-3-methoxybenzaldehyde (0.2 mmol, in 5 ml of methanol) was added 4-bromoaniline (0.2 mmol) in 10 ml of methanol, and the mixture was stirred for 1 h in air at 323 K and was then left at room temperature for several days without disturbance yielding suitable crystals of (1) that subsequently were filtered off and washed with Et₂O. Yield: 91%.