2-[(2,6-Diisopropyl­phen­yl)imino­meth­yl]-4-iodo­phenol

P Balamurugan; K Kanmani Raja; I Mohammed Bilal; G Chakkaravarthi; G Rajagopal

doi:10.1107/S1600536812023653

. 2012 May 31;68(Pt 6):o1915. doi: 10.1107/S1600536812023653

2-[(2,6-Diisopropylphenyl)iminomethyl]-4-iodophenol

P Balamurugan ^a, K Kanmani Raja ^b, I Mohammed Bilal ^c, G Chakkaravarthi ^d,^*, G Rajagopal ^e,^*

PMCID: PMC3379471 PMID: 22719669

Abstract

The asymmetric unit of title compound, C₁₉H₂₂INO, contains two independent molecules. Classical intramolecular O—H⋯N hydrogen bonds stabilize the molecular structures. The crystal structure is stabilized by weak intermolecular C—H⋯π and π–π [centroid–centroid = 3.8622 (18) Å] interactions. In both molecules, the aromatic rings are nearly perpendicular to each other [dihedral angles = 84.26 (17) and 86.69 (15)°].

Related literature

For the biological activity of Schiff base ligands, see: Santos et al. (2001 ▶). For related strucutures, see: Raja et al. (2008 ▶); Lin et al. (2005 ▶).

Experimental

Crystal data

C₁₉H₂₂INO
M _r = 407.28
Triclinic,
a = 5.9891 (2) Å
b = 12.4270 (5) Å
c = 25.8832 (10) Å
α = 83.065 (2)°
β = 84.860 (3)°
γ = 76.408 (2)°
V = 1855.00 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.73 mm⁻¹
T = 295 K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.662, T _max = 0.724
45699 measured reflections
10505 independent reflections
7252 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.111
S = 1.01
10505 reflections
407 parameters
H-atom parameters constrained
Δρ_max = 0.91 e Å⁻³
Δρ_min = −0.65 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023653/rk2360sup1.cif

e-68-o1915-sup1.cif^{(38.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023653/rk2360Isup2.hkl

e-68-o1915-Isup2.hkl^{(503.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812023653/rk2360Isup3.cml

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

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

Cg2 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	1.88	2.606 (3)	147
O2—H2A⋯N2	0.82	1.91	2.617 (3)	143
C16—H16A⋯Cg2ⁱ	0.96	2.91	3.785 (5)	153

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors wish to acknowledge the SAIF, IIT Madras, for the data collection.

supplementary crystallographic information

Comment

Schiff base derivatives exhibit antibacterial, antitumor and antitoxic activities (Santos et al., 2001). The asymmetric unit of the title compound I, (Fig. 1), contains two independent molecules. The geometric parameters in I are comparable with the similar reported structures (Lin et al., 2005; Raja et al., 2008). The dihedral angles between the benzene rings (C1-C6) and (C8-C13) & (C20-C25) and (C27-C32) are 84.26 (17)° and 86.69 (15)°. Further, both molecules adopts anti-periplanar (C1-C7-N1-C8 = 177.2 (2)° and C20-C26-N2-C27 = 175.8 (2)°) conformation about C═N bond.

The molecular structure is stabilized by weak intramolecular O–H···N hydrogen bonds and the crystal structure exhibit weak intermolecular C–H···π (Cg2ⁱ) (Table 1, Fig. 2) and π–π interactions (Cg1···Cg1ⁱⁱ) with distance 3.8622 (18)Å. Cg1 is the centroid of (C1-C6) ring; Cg2 is the centroid of (C8-C13) ring. Symmetry codes: (i) x-1, y, z; (ii) 1-x, 1-y, -z.

Experimental

An ethanolic solution (10 ml) of 2,6-diisopropylaniline (2 mmol) was stirred in a round bottom flask followed by drop wise addition of ethanolic solution (10 ml) of 5-iodosalicylaldehyde (2 mmol). The reaction mixture was then refluxed for 3 h and upon cooling to 273 K. A yellow solid precipitate from the reaction mixture was filtered out, washed with ice cold ethanol and dried over anhydrous CaCl₂. Single crystals of good diffraction quality were obtained by the recrystallization of compound from ethanol solution by slow evaporation. Yield: 70 %.