Diethyl 5-[(2-hydr­oxy-1-naphth­yl)methyl­ideneamino]-3-methyl­thio­phene-2,4-dicarboxyl­ate

Mehmet Akkurt; Şerife Pınar Yalçın; Abdullah Mohamed Asiri; Orhan Büyükgüngör

doi:10.1107/S1600536808011628

. 2008 Apr 26;64(Pt 5):o923. doi: 10.1107/S1600536808011628

Diethyl 5-[(2-hydroxy-1-naphthyl)methylideneamino]-3-methylthiophene-2,4-dicarboxylate

Mehmet Akkurt ^a,^*, Şerife Pınar Yalçın ^a, Abdullah Mohamed Asiri ^b, Orhan Büyükgüngör ^c

PMCID: PMC2961336 PMID: 21202404

Abstract

In the title compound, C₂₂H₂₁NO₅S, the 2-naphthol group and the thiophene ring are almost coplanar, with a dihedral angle of 5.75 (7)°. The structure is stabilized by intramolecular O—H⋯O, O—H⋯N and C—H⋯S, and intermolecular C—H⋯O hydrogen-bonding interactions.

Related literature

For related structures, see: Akkurt, Karaca et al. (2008 ▶); Akkurt, Yıldırım et al. (2008 ▶); Asiri & Badahdah (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₂H₂₁NO₅S
M _r = 411.47
Triclinic,
a = 8.7111 (4) Å
b = 11.5319 (5) Å
c = 11.9778 (5) Å
α = 61.594 (3)°
β = 79.489 (3)°
γ = 89.334 (3)°
V = 1036.67 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 (2) K
0.63 × 0.38 × 0.10 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie) T _min = 0.890, T _max = 0.981
18909 measured reflections
4047 independent reflections
3397 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.111
S = 1.06
4047 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011628/sj2483sup1.cif

e-64-0o923-sup1.cif^{(26KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011628/sj2483Isup2.hkl

e-64-0o923-Isup2.hkl^{(194.3KB, hkl)}

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—H1A⋯O3	0.82	2.58	3.209 (2)	135
O1—H1A⋯N1	0.82	1.83	2.561 (2)	147
C1—H1⋯S1	0.93	2.59	3.0263 (18)	109
C7—H7⋯O4ⁱ	0.93	2.37	3.269 (3)	163
C16—H16C⋯O4	0.96	2.25	2.978 (3)	132
C21—H21B⋯O2ⁱⁱ	0.97	2.60	3.565 (3)	175

Open in a new tab

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

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).

supplementary crystallographic information

Comment

We recently reported the structures of 4-[(2-hydroxy-1-naphthyl)methylideneamino]benzoic acid (Akkurt, Yıldırım et al., 2008) and 2-[(2-Hydroxybenzylidene) amino]-3-methoxycarbonyl-3,4,5,6-tetrahydrobenzo[d] thiophene (Akkurt, Karaca et al., 2008). In this communication, we report the structure of the title compound, 4-[(2-hydroxynaphth-1-yl methylidene) amino]-3,5-diethoxycarbonyl- 4-methylthiophene (I), as a part of an ongoing investigation into the development of anil derivatives.

In the title compound (Fig. 1), all values of the geometric parameters are normal (Allen et al., 1987). The naphthalen-2-ol group and thiophene ring are each almost planar, with maximum deviations of -0.020 (1) Å for O1 and 0.008 (2) Å for C15, respectively, and the respective ring planes are oriented with a dihedral angle of 5.75 (7)° between them. Intramolecular O1—H1A···O3, O1—H1A···N1 and C1—H1···S hydrogen bonds effect this conformation and the structure is further stabilised by intermolecular C—H···O hydrogen bonding interactions (Table 1 and Fig. 2).

Experimental

The title compound, I, was prepared by the method of Asiri & Badahdah (2007) and recrystallised from ethanol. [Yield 99%, mp: 448 K].