2-{[4-(Diethyl­amino)­phen­yl]imino­methyl}-4,6-diiodo­phenol

A Thirugnan Sundar; G Rajagopal; S Murugavel; A Subbiah Pandi

doi:10.1107/S160053681004417X

. 2010 Nov 6;66(Pt 12):o3089. doi: 10.1107/S160053681004417X

2-{[4-(Diethylamino)phenyl]iminomethyl}-4,6-diiodophenol

A Thirugnan Sundar ^a, G Rajagopal ^b, S Murugavel ^c, A Subbiah Pandi ^d,^*

PMCID: PMC3011799 PMID: 21589396

Abstract

In the title compound, C₁₇H₁₈I₂N₂O, the dihedral angle between the aromatic rings is 5.4 (1)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by C—H⋯π and π–π interactions [centroid–centroid distance = 3.697 (1) Å].

Related literature

For Schiff base compounds in coordination chemistry, see: Weber et al. (2007 ▶); Chen et al. (2008 ▶). For their role in biological processes, see: May et al. (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Manvizhi et al. (2010 ▶).

Experimental

Crystal data

C₁₇H₁₈I₂N₂O
M _r = 520.13
Monoclinic,
a = 11.5562 (5) Å
b = 11.1325 (5) Å
c = 15.1207 (6) Å
β = 111.958 (2)°
V = 1804.15 (13) Å³
Z = 4
Mo Kα radiation
μ = 3.49 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.450, T _max = 0.572
26163 measured reflections
7041 independent reflections
4445 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.105
S = 1.01
7041 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 1.14 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004417X/bt5392sup1.cif

e-66-o3089-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004417X/bt5392Isup2.hkl

e-66-o3089-Isup2.hkl^{(337.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.592 (3)	148
C16—H16B⋯Cg1ⁱⁱ	0.97	2.94	3.845 (4)	155

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Symmetry code: (i) Inline graphic .

Acknowledgments

ASP thanks Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Schiff base compounds have received considerable attention for many years, primarily due to their importance in the development of coordination chemistry related to magnetism (Weber et al., 2007), catalysis (Chen et al., 2008) and biological processes (May et al., 2004). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound has been carried out.

The molecular structure is illustrated in Fig. 1. The geometric parameters of the title molecule agrees well with those reported for a similar structure (Manvizhi et al., 2010). The dihedral angle between the aromatic rings is 5.4 (1)°, showing that both the rings are almost coplanar.

In addition to the van der Waals interactions, the crystal packing is stabilized by C-H···π hydrogen bonds as well as by π-π interactions. The intramolecular O-H···N hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The crystal packing (Fig. 2) is stabilized by C-H···π interactions between a H16B atom and a neighbouring ring, with a C16-H16B···Cg1ⁱ separation of 2.94 Å (Fig. 2 and Table 1; Cg1 is the centroid of the C8-C13 ring ring, symmetry code as in Fig. 2). The molecular packing (Fig. 2) is further stabilized by π-π interactions with a Cg1···Cg2ⁱⁱ and a Cg2···Cg1ⁱⁱ separation of 3.697 (1)Å and 3.697 (1)Å, respectively (Fig. 2; Cg1 and Cg2 are the centroids of the C8-C13 benzene ring and C1-C6 benzene ring, respectively, symmetry code as in Table 1).

Experimental

An ethanoic solution (30 ml) and N,N-diethyl aniline (10 mmol) was magnetically stirred in a round bottom flask followed by dropwise addition of 3,5-diiodosalicylaldehyde (10 mmol). The reaction mixture was then refluxed for two hours and upon cooling to 273K a yellow crystalline solid precipitated from the mixture. Single yellow crystals were obtained, filtered off, washed with ice cold ethanol and air dried.