2-Eth­oxy-6-{(E)-[(4-methyl­phen­yl)imino]­meth­yl}phenol

Muhammad Ashraf Shaheen; M Nawaz Tahir; Rana Muhammad Irfan; Shahid Iqbal; Saeed Ahmad

doi:10.1107/S1600536812024798

. 2012 Jun 13;68(Pt 7):o2011. doi: 10.1107/S1600536812024798

2-Ethoxy-6-{(E)-[(4-methylphenyl)imino]methyl}phenol

Muhammad Ashraf Shaheen ^a, M Nawaz Tahir ^b,^*, Rana Muhammad Irfan ^a, Shahid Iqbal ^a, Saeed Ahmad ^c

PMCID: PMC3393282 PMID: 22807839

Abstract

The asymmetric unit of the title compound, C₁₆H₁₇NO₂, contains two molecules in which the dihedral angles between the 3-ethoxy-2-hydroxybenzaldehyde and toluidine moieties are 16.87 (8) and 19.93 (6)°. S(6) rings are present in both molecules due to intramolecular O—H⋯N hydrogen bonds. In the crystal, one of the molecules is dimerized with an inversion-generated partner, due to two C—H⋯O interactions. This generates an R ₂ ²(8) loop.

Related literature

For related crystal structures, see: Albayrak et al. (2010 ▶); Özek et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₇NO₂
M _r = 255.31
Monoclinic,
a = 29.5126 (11) Å
b = 6.8703 (3) Å
c = 28.2167 (13) Å
β = 102.986 (3)°
V = 5574.9 (4) Å³
Z = 16
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.975, T _max = 0.985
20559 measured reflections
5040 independent reflections
2075 reflections with I > 2σ(I)
R _int = 0.083

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.181
S = 0.98
5040 reflections
346 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 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 for Windows (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/S1600536812024798/hb6825sup1.cif

e-68-o2011-sup1.cif^{(34.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024798/hb6825Isup2.hkl

e-68-o2011-Isup2.hkl^{(241.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812024798/hb6825Isup3.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	0.82	1.86	2.584 (4)	147
O3—H3⋯N2	0.82	1.86	2.585 (3)	147
C24—H24A⋯O4ⁱ	0.96	2.59	3.470 (4)	153

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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, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1) has been synthesized as a derivative for the complexation and other studies.

The crystal structures of 2-ethoxy-6-((phenylimino)methyl)phenol (Albayrak et al., 2010) and (E)-2-ethoxy-6-[(4-ethoxyphenyl)iminomethyl]phenol (Özek et al., 2010) have been published which are related to the title compound (I).

In (I), two molecules in the asymmetric unit are present, which differ slightly from each other geometrically. In one molecule, the group A (C1—C9/O1/O2) of 3-ethoxy-2-hydroxybenzaldehyde and group B (N1/C10—C16) of toluidine moieties are planar with r. m. s. deviation of 0.0270 Å and 0.0105 Å, respectively. The dihedral angle between A/B is 19.93 (6)°. In second molecule, the similar groups C (C18—C25/O3/O4) and D (N2/C26—C32) are also planar with r. m. s. deviation of 0.0184 Å and 0.0193 Å, respectively and the dihedral angle between C/D is 16.87 (8)°. In both molecules S(6) ring motif is present due to classical H–bonding of O—H···N type (Table 1, Fig. 2). The second molecule which is more planar is dimerized with itself from ethoxy groups with R₂²(8) ring motif due to C—H···O type of H–bonding (Table 1, Fig. 2).

Experimental

Equal molar ratio of 4-toluidine and 3-ethoxy-2-hydroxybenzaldehyde was refluxed in methanol for 2 h and orange prisms of (I) were obtained after 72 h by the slow evaporation at room temperature.