2-[(E)-(4-Methyl­phen­yl)imino­meth­yl]-6-(morpholin-4-ylmeth­yl)phenol

Mehmet Akkurt; Sevim Türktekin; Aliasghar Jarrahpour; Hashem Sharghi; Seid Ali Torabi Badrabady; Mahdi Aberi; Orhan Büyükgüngör

doi:10.1107/S1600536810052311

. 2010 Dec 18;67(Pt 1):o147–o148. doi: 10.1107/S1600536810052311

2-[(E)-(4-Methylphenyl)iminomethyl]-6-(morpholin-4-ylmethyl)phenol

Mehmet Akkurt ^a,^*, Sevim Türktekin ^a, Aliasghar Jarrahpour ^b, Hashem Sharghi ^b, Seid Ali Torabi Badrabady ^b, Mahdi Aberi ^b, Orhan Büyükgüngör ^c

PMCID: PMC3050317 PMID: 21522655

Abstract

In the title compound, C₁₉H₂₂N₂O₂, the morpholine ring adopts an almost perfect normal chair conformation with puckering parameters Q _T, θ and ϕ of 0.5642 (18) Å, 177.32 (17) and ϕ = 10 (4)°, respectively. The two benzene rings make a dihedral angle of 42.67 (8)° with each other. An intramolecular O—H⋯N hydrogen bond helps to stabilize the molecular conformation. Aromatic C—H⋯π interactions and π–π stacking interactions [centroid–centroid distance = 3.6155 (15) Å] between the benzene rings contribute to the stabilization of the crystal structure.

Related literature

For general background to Schiff bases with an azomethine or imine group (—C=N—), see: Akkurt et al. (2008 ▶); Dhar & Taploo (1982 ▶); Emregül et al. (2006 ▶); Jarrahpour & Khalili (2006 ▶); Jarrahpour et al. (2007 ▶); Mladenova et al. (2002 ▶); Przybylski et al. (2009 ▶); Sessler et al. (2006 ▶); Singh et al. (2006 ▶). For a similar structure, see: Akkurt et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₉H₂₂N₂O₂
M _r = 310.39
Triclinic,
a = 9.807 (3) Å
b = 10.091 (3) Å
c = 10.528 (3) Å
α = 99.78 (2)°
β = 109.34 (2)°
γ = 115.18 (2)°
V = 828.7 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.53 × 0.40 × 0.23 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.958, T _max = 0.982
15421 measured reflections
3443 independent reflections
2894 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.121
S = 1.08
3443 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052311/si2317sup1.cif

e-67-0o147-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052311/si2317Isup2.hkl

e-67-0o147-Isup2.hkl^{(168.8KB, hkl)}

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

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

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.6261 (18)	147
C19—H19A⋯Cg2ⁱ	0.97	2.96	3.732 (3)	137

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). AJ, HS, SATB and MA thank the Shiraz University Research Council for financial support (grant No. 89-GR—SC-23).

supplementary crystallographic information

Comment

Schiff bases, named for Hugo Schiff with the azomethine or imine group (—C═ N—) usually synthesized by condensation of a primary amine and an active carbonyl group under specific conditions. These compounds show a broad range of applications such as corrosion inhibitors (Emregül et al., 2006), catalysts (Sessler et al., 2006), pigments and polymer stabilizers. Schiff bases possess high biological activities including antibacterial (Jarrahpour et al., 2006), antifungal (Singh et al., 2006), antitumor (Mladenova et al., 2002), antimalarial (Przybylski et al., 2009), antiviral (Jarrahpour et al., 2007) and antipyretic properties (Dhar et al., 1982). Schiff bases are also good intermediates for the synthesis of other chemical substances such as 2-azetidinones.

As shown in Fig. 1, the morpholine ring (N2/O2/C16–C19) of the title compound (I) adopts a chair conformation with puckering parameters Q_T, θ and φ of 0.5642 (18) Å, 177.32 (17) ° and φ = 10 (4) ° (Cremer & Pople (1975). The dihedral angle between the (C1–C6) and (C9–C14) benzene rings in (I) is 42.67 (8)°. The bond lengths exhibit normal values (Allen et al. 1987) and are comparable with those in our similar structure previously published (Akkurt et al., 2008).

The molecular conformation of (I) is stabilized by intramolecular weak C12—H12···N2 and strong O1—H1···N1 hydrogen bonds (Table 1). In the crystal structure, a C—H···π interaction (Table 1) and a π-π stacking interaction between the C9–C14 benzene rings contribute to the stabilization of the crystal packing [Cg3···Cg3ⁱⁱ(symmetry code ii = 1 - x, 1 - y, -z) = 3.6155 (15) Å, where Cg3 is a centroid of the C9–C14 benzene ring]. Fig. 2 shows the crystal packing of (I) down the a axis.

Experimental

Reaction of 2-hydroxy-3-(morpholinomethyl)benzaldehyde with 4-methylaniline in refluxing ethanol gave Schiff base (I) that recrystallized from ethanol to give orange crystals in 85% yield. [mp: 377–379 K]. IR (KBr, cm^-1): 1615.2 (C═N), 3170.6–3310.5 (OH). ¹H-NMR (250 MHz, CDCl₃) δ (p.p.m): 2.30 (Me, s, 3H), 2.51 (CH₂, t, 4H, J = 4.5), 3.60 (CH₂, s, 2H), 3.69 (CH₂, t, 4H, J = 4.5), 6.81–7.38 (m, ArH, 7H), 8.56 (HC═N, s, 1H), 13.68 (OH, s, 1H). ¹³C-NMR (CDCl₃) δ (p.p.m): 21.0 (Me), 53.5 (N—CH₂), 56.4 (CH₂), 66.8 (O—CH₂), 118.5–159.7 (C=C aromatic carbons), 161.3 (C=N).