(IUCr) Methyl 2-(2-hydroxybenzylideneamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

Volume 64
Part 5
Page o869
May 2008

Received 15 April 2008
Accepted 16 April 2008
Online 18 April 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.122
Data-to-parameter ratio = 15.4
Details

Methyl 2-(2-hydroxybenzylideneamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

Mehmet Akkurt,^a ^* Selvi Karaca,^a Abdullah Mohamed Asiri ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey,^bChemistry Department, Faculty of Science, King Abdul-Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C₁₇H₁₇NO₃S, the cyclohexene ring is essentially planar, with a maximum deviation of 0.006 (1) Å. The cyclohexene ring adopts a half-chair conformation. The dihedral angle between the thiophene and benzene rings is 29.7 (1)°. The molecular structure exhibits intramolecular O-HO, O-HN and C-HS hydrogen bonds, which generate one S(5) and two S(6) motifs. There is also a C-H [pi] interaction between the cyclohexene ring system and the [pi] -system of the benzene ring.

Related literature

For related literature, see: Akkurt et al. (2008); Allen et al. (1987); Asiri & Badahdah (2007); Bernstein et al. (1995); Cremer & Pople (1975); Etter (1990).

Experimental

Crystal data

C₁₇H₁₇NO₃S
M_r = 315.39
Monoclinic, P 2₁ /c
a = 7.6107 (4) Å
b = 21.2154 (9) Å
c = 11.1827 (7) Å
= 123.342 (4)°
V = 1508.41 (16) Å³
Z = 4
Mo K radiation
= 0.23 mm^-1
T = 293 (2) K
0.60 × 0.47 × 0.23 mm

Data collection

Stoe IPDS2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.876, T_max = 0.950
8036 measured reflections
3086 independent reflections
2361 reflections with I > 2(I)
R_int = 0.078

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.121
S = 0.99
3086 reflections
200 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2	0.82	2.50	3.102 (2)	132
O1-H1N1	0.82	1.88	2.607 (2)	146
C7-H7S1	0.93	2.69	3.0725 (19)	105
C15-H15ACgⁱ	0.97	2.92	3.782 (3)	150
Symmetry code: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg is the centroid of the benzene ring.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: IS2289 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

Akkurt, M., Yildirim, S. Ö., Asiri, A. M. & McKee, V. (2008). Acta Cryst. E64, o682.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Asiri, A. M. & Badahdah, K. O. (2007). Molecules, 12, 1796-1804.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

organic compounds