4,4′,6,6′-Tetra-tert-butyl-2,2′-[1,2-phenyl­enebis(nitrilo­methyl­idyne)]diphenol acetone solvate

Naser Eltaher Eltayeb; Siang Guan Teoh; Suchada Chantrapromma; Hoong-Kun Fun; Rohana Adnan

doi:10.1107/S1600536808003905

. 2008 Feb 13;64(Pt 3):o576–o577. doi: 10.1107/S1600536808003905

4,4′,6,6′-Tetra-tert-butyl-2,2′-[1,2-phenylenebis(nitrilomethylidyne)]diphenol acetone solvate

Naser Eltaher Eltayeb ^a,^‡, Siang Guan Teoh ^a, Suchada Chantrapromma ^b,^§, Hoong-Kun Fun ^c,^*, Rohana Adnan ^a

PMCID: PMC2960780 PMID: 21201917

Abstract

In the Schiff base molecule of the title compound, C₃₆H₄₈N₂O₂·C₃H₆O, the central benzene ring makes dihedral angles of 46.64 (10) and 49.34 (10)° with the two outer benzene rings, and the two outer benzene rings form an angle of 39.13 (8)°. There are two intramolecular O—H⋯N hydrogen bonds involving the two hydroxy groups, which generate S(6) ring motifs. In the crystal structure, the Schiff base molecules are linked into a chain along the a axis by C—H⋯π interactions. The acetone solvent molecules are attached to the chain via C—H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶). For biological activities of Schiff base compounds, see: Dao et al. (2000 ▶); Eltayeb & Ahmed (2005a ▶,b ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶). For related structures, see: Eltayeb, Teoh, Chantrapromma et al. (2007 ▶); Eltayeb, Teoh, Teh et al. (2007a ▶,b ▶).

Experimental

Crystal data

C₃₆H₄₈N₂O₂·C₃H₆O
M _r = 598.84
Triclinic,
a = 10.0008 (2) Å
b = 12.0020 (3) Å
c = 17.0366 (4) Å
α = 82.068 (1)°
β = 86.320 (1)°
γ = 65.764 (1)°
V = 1846.76 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 (2) K
0.59 × 0.55 × 0.43 mm

Data collection

Bruker SMART APEX2 CCD area-detecto diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.962, T _max = 0.972
26090 measured reflections
8384 independent reflections
5874 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.183
S = 1.04
8384 reflections
419 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003905/ci2559sup1.cif

e-64-0o576-sup1.cif^{(30.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003905/ci2559Isup2.hkl

e-64-0o576-Isup2.hkl^{(410.1KB, hkl)}

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

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

Cg1 and Cg2 are the C1–C6 and C15–C20 ring centroids, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.89 (2)	1.76 (3)	2.5809 (19)	153 (3)
O2—H1O2⋯N2	0.87 (3)	1.78 (3)	2.5956 (19)	155 (3)
C7—H7A⋯O3	0.93	2.58	3.460 (6)	158
C30—H30B⋯O2	0.96	2.36	2.994 (3)	123
C31—H31A⋯O2	0.96	2.34	2.989 (3)	124
C34—H34C⋯O1	0.96	2.32	2.968 (3)	124
C35—H35A⋯O1	0.96	2.35	2.996 (3)	124
C24—H24B⋯Cg2ⁱ	0.96	2.97	3.877 (3)	158
C26—H26A⋯Cg1ⁱⁱ	0.96	2.89	3.798 (2)	157

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

Acknowledgments

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation, Malaysia (MOSTI), and Universiti Sains Malaysia for the E-Science Fund research grant (PKIMIA/613308) and facilities. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. The authors also thank Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) grant No. 203/PFIZIK/671064.

supplementary crystallographic information

Comment

Schiff base compounds have received much attention because of their potential applications. Some of these compounds exhibit various pharmacological activities, such as anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). Recently, we have reported the crystal structures of 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(5-methylphenol) (Eltayeb et al., 2007a) and 6,6'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007b). In this paper, we report the crystal structure of the title compound, obtained by the reaction of o-phenylenediamine and 3,5-di-tert-butylsalicylaldehyde.

In the molecular structure of the title compound, the central benzene ring (C8–13) makes dihedral angles of 46.64 (10)° and 49.34 (10)°, respectively, with the two outer benzene rings, C1—C6 and C15—C20. The dihedral angle between the two outer benzene rings is 39.13 (8)°. The C8–N1–C7–C6 and C13–N2–C14–C15 torsion angles are 178.16 (15)° and -178.34 (16)°, respectively. Bond lengths and angles in the title compound are in normal ranges (Allen et al., 1987) and are comparable to those in related structures (Eltayeb et al., 2007; Eltayeb et al., 2007a,b).

The two intramolecular O—H···O hydrogen bonds, O1—H1O1···N1 and O2—H1O2···N2, generate S(6) ring motifs (Bernstein et al., 1995). In addition, intramolecular C—H···O interactions (Table 1) are observed.

In the crystal structure, the acetone molecule is linked to the Schiff base molecule via a C—H···O hydrogen bond. The crystal structure is further stabilized by C—H···π interactions involving the C1–C6 (centroid Cg1) and C15–C20 (centroid Cg2) rings, which link the molecules into a chain along the a axis.

Experimental

The title compound was synthesized by adding 3,5-di-tert-butylsalicylaldehyde (0.936 g, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (20 ml). The mixture was refluxed with stirring for 30 min. The resultant yellow solution was filtered. The yellow precipitate obtained after a few days, was dissolved in acetone (20 ml). Orange single crystals suitable for X-ray diffraction were formed after 6 d of slow evaporation of the acetone at room temperature.