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Volume 69 
Part 7 
Pages o1116-o1117  
July 2013  

Received 5 June 2013
Accepted 13 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.043
wR = 0.104
Data-to-parameter ratio = 11.8
Details
Open access

Ethyl 2-[(2-hydroxybenzylidene)amino]-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate

aDepartment of Chemistry, Hitit University, 19030 Çorum, Turkey,bDepartment of Physics, Dicle University, 21280 Sur, Diyarbakir, Turkey, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The title compound, C18H20N2O3S, exists as the phenol-imine form in the crystal and there are bifurcated intramolecular O-H...(N/O) hydrogen bonds present. The conformation about the C=N bond is anti (1E); the C=N imine bond length is 1.287 (4) Å and the C=N-C angle is 122.5 (3)°. In the tetrahydrothienopyridine moiety, the six-membered ring has a flattened-boat conformation. In the crystal, molecules are stacked nearly parallel to (110) and a weak C-H...[pi] interaction is observed. The carbonyl O atom is disordered over two positions and was refined with a fixed occupancy ratio of 0.7:0.3.

Related literature

For investigations of tautomerism and intramolecular hydrogen bonds in 2-hydroxy Schiff bases in both solution and the solid state, see: Hayvali et al. (2003[Hayvali, Z., Hayvali, M., Kiliç, Z., Hökelek, T. & Weber, E. (2003). J. Incl. Phenom. Macrocycl. Chem. 45, 285-294.]); Pizzala et al. (2000[Pizzala, H., Carles, M., Stone, W. E. E. & Thevand, A. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 935-939.]); Kaitner & Pavlovic (1996[Kaitner, B. & Pavlovic, G. (1996). Acta Cryst. C52, 2573-2575.]). For the role of tautomerism in Schiff bases in distinguishing their photochromic and thermochromic characteristics, see: Hadjoudis (1981[Hadjoudis, E. (1981). J. Photochem. 17, 355-367.]); Dürr (1989[Dürr, H. (1989). Angew. Chem. Int. Ed. Engl. 28, 413-431.]); Moustakali-Mavridis et al. (1980[Moustakali-Mavridis, I., Hadjoudis, B. & Mavridis, A. (1980). Acta Cryst. B36, 1126-1130.]). For keto-amine and phenol-imine forms observed in naphthaldimine and salicylaldimine Schiff bases, see: Gavranic et al. (1996[Gavranic, M., Kaitner, B. & Mestrovic, E. (1996). J. Chem. Crystallogr. 26, 23-28.]); Kaitner & Pavlovic (1996[Kaitner, B. & Pavlovic, G. (1996). Acta Cryst. C52, 2573-2575.]); Pizzala et al. (2000[Pizzala, H., Carles, M., Stone, W. E. E. & Thevand, A. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 935-939.]); Hökelek et al. (2004[Hökelek, T., Bilge, S., Demiriz, S., Özgüç, B. & Kiliç, Z. (2004). Acta Cryst. C60, o803-o805.]). For related structures, see: Hökelek et al. (2000[Hökelek, T., Akduran, N., Yildiz, M. & Kiliç, Z. (2000). Anal. Sci. 16, 553-554.], 2004[Hökelek, T., Bilge, S., Demiriz, S., Özgüç, B. & Kiliç, Z. (2004). Acta Cryst. C60, o803-o805.]);Yildiz et al. (1998[Yildiz, M., Kiliç, Z. & Hökelek, T. (1998). J. Mol. Struct. 441, 1-10.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C18H20N2O3S

  • Mr = 344.42

  • Orthorhombic, P n a 21

  • a = 22.0243 (5) Å

  • b = 16.1559 (4) Å

  • c = 4.8055 (1) Å

  • V = 1709.90 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 296 K

  • 0.35 × 0.15 × 0.10 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.912, Tmax = 0.980

  • 11744 measured reflections

  • 2778 independent reflections

  • 2120 reflections with I > 2[sigma](I)

  • Rint = 0.062

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.104

  • S = 1.02

  • 2778 reflections

  • 236 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 691 Friedel pairs

  • Flack parameter: 0.08 (11)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of ring B (S1/C8-C10/C14).

D-H...A D-H H...A D...A D-H...A
O1-H1...O3 0.90 (5) 2.40 (5) 3.053 (4) 129 (4)
O1-H1...N1 0.90 (5) 1.79 (5) 2.605 (4) 148 (4)
C12-H12A...Cg1i 0.97 2.77 3.701 (3) 161
Symmetry code: (i) x, y, z-1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2610 ).


Acknowledgements

The authors are indebted to Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for the use of X-ray diffractometer.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dürr, H. (1989). Angew. Chem. Int. Ed. Engl. 28, 413-431.  [CrossRef] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Gavranic, M., Kaitner, B. & Mestrovic, E. (1996). J. Chem. Crystallogr. 26, 23-28.  [CrossRef] [ChemPort] [Web of Science]
Hadjoudis, E. (1981). J. Photochem. 17, 355-367.  [CrossRef] [ChemPort] [Web of Science]
Hayvali, Z., Hayvali, M., Kiliç, Z., Hökelek, T. & Weber, E. (2003). J. Incl. Phenom. Macrocycl. Chem. 45, 285-294.  [CSD] [CrossRef] [ChemPort]
Hökelek, T., Akduran, N., Yildiz, M. & Kiliç, Z. (2000). Anal. Sci. 16, 553-554.  [ChemPort]
Hökelek, T., Bilge, S., Demiriz, S., Özgüç, B. & Kiliç, Z. (2004). Acta Cryst. C60, o803-o805.  [CSD] [CrossRef] [IUCr Journals]
Kaitner, B. & Pavlovic, G. (1996). Acta Cryst. C52, 2573-2575.  [CSD] [CrossRef] [IUCr Journals]
Moustakali-Mavridis, I., Hadjoudis, B. & Mavridis, A. (1980). Acta Cryst. B36, 1126-1130.  [CrossRef] [IUCr Journals]
Pizzala, H., Carles, M., Stone, W. E. E. & Thevand, A. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 935-939.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yildiz, M., Kiliç, Z. & Hökelek, T. (1998). J. Mol. Struct. 441, 1-10.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1116-o1117   [ doi:10.1107/S1600536813016474 ]

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