2-[(3,4-Di­chloro­benzyl­idene)amino]-4-methyl­phenol

Muhammet Kose; Ilyas Gonul; Vickie McKee

doi:10.1107/S1600536813013585

. 2013 May 25;69(Pt 6):o961. doi: 10.1107/S1600536813013585

2-[(3,4-Dichlorobenzylidene)amino]-4-methylphenol

Muhammet Kose ^a,^*, Ilyas Gonul ^b, Vickie McKee ^c

PMCID: PMC3685100 PMID: 23795119

Abstract

In the title compound, C₁₄H₁₁Cl₂NO, the dihedral angle between the benzene rings is 15.36 (8)°. A phenol–imine-type intramolecular O—H⋯N hydrogen bond generates an S(5) ring motif. In the crystal, a pair of weak C—H⋯O hydrogen bonds form an R ₂ ¹(7) ring motif involving glide-plane-related molecules. The molecules linked via these interactions form chains along [101].

Related literature

For Schiff bases, see: Akine & Nabeshima (2009 ▶); Vigato & Tamburini (2004 ▶). For related structures, see: Efil et al. (2012 ▶); Fridman & Kaftory (2007 ▶); Jiao et al. (2006 ▶); Wang & Wang (2007 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₁Cl₂NO
M _r = 280.14
Monoclinic,
a = 4.6074 (7) Å
b = 21.680 (3) Å
c = 12.7907 (18) Å
β = 93.342 (2)°
V = 1275.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 150 K
0.64 × 0.14 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2009 ▶) T _min = 0.743, T _max = 0.966
12828 measured reflections
3159 independent reflections
2556 reflections with I2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.094
S = 1.02
3159 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Click here for additional data file.^{(16.6KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013585/fy2096sup1.cif

e-69-0o961-sup1.cif^{(16.6KB, cif)}

Click here for additional data file.^{(155KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013585/fy2096Isup2.hkl

e-69-0o961-Isup2.hkl^{(155KB, hkl)}

Click here for additional data file.^{(4.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813013585/fy2096Isup3.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
C5—H5⋯O1ⁱ	0.95	2.67	3.618 (2)	174
C8—H8⋯O1ⁱ	0.95	2.65	3.562 (2)	162
O1—H1⋯N1	0.81	2.16	2.6612 (17)	121

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to Loughborough University for the data collection and Cukurova University for financial support (to IG).

supplementary crystallographic information

Comment

Schiff base condensations yield compounds with wide uses as ligands (Akine et al., 2009; Vigato et al., 2004). The title compound was prepared as a part of an investigation of the coordination and biological properties of Schiff base ligands.

The title compound adopts E configuration with respect to the imine C=N double bond with a C9—C8—N1—C6 torsion angle = -179.98 (13)°. The azomethine (C8═N1) bond distance is 1.2765 (19) Å and within the normal C═N values. The dihedral angle between the two benzene rings is 15.36 (8)°. There is a phenol-imine type intramolecular hydrogen bond (O1H···N1) in the structure forming a S(5) hydrogen bonding motif. There are two intermolecular weak hydrogen bond type (C5H···O1 and C8H···O1) interactions, resulting in a R¹₂(7) hydrogen-bonding motif. Molecules are linked via weak hydrogen bonding form hydrogen-bond chains along the ac diagonal (Fig. 2, Table 1).

There is evidence of π-π stacking in the structure. The C3—C9 section of the molecule is stacked with the C6*—C12* section of an adjacent molecule (* = x + 1, y, z). N1 and C10* are seperated by a distance of 3.302 (2) Å. There is also π-Cl interaction in the structure: Cl2 is stacked with C3** of an adjacent molecule (** = 1/2 - x, 1/2 + y, 3/2 - z) with a distance of 3.407 (2) Å (Fig. 3).

Experimental

A solution of 3,4-dichlorobenzaldehyde (0.0.525 g, 3 mmol) in methanol (25 ml) was added to a methanolic solution (20 ml) of 2-amino-4-methylphenol (0.740 g, 6 mmol). The mixture was stirred for two hours at room temperature and left for air evaporation. After two days, yellow crystals suitable for X-ray diffraction study were collected by filtration.