Ethyl 2-[2-(4-hy­droxy-3-meth­oxy­benzyl­idene)hydrazin-1-yl­idene]-3,4-dimethyl-2,3-dihydro-1,3-thia­zole-5-carboxyl­ate

Öztürk Yildirim, S.; Butcher, R.J.; Köysal, Y.; Kantar, E.N.; Belder, A.

doi:10.1107/S1600536812043772

Volume 68
Part 11
Pages o3213-o3214
November 2012

Received 19 October 2012
Accepted 22 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.099
Data-to-parameter ratio = 14.9
Details

Ethyl 2-[2-(4-hydroxy-3-methoxybenzylidene)hydrazin-1-ylidene]-3,4-dimethyl-2,3-dihydro-1,3-thiazole-5-carboxylate

Sema Öztürk Yildirim,^a,^b Ray J. Butcher,^a ^* Yavuz Köysal,^c Esen Nur Kantar ^d and Ayse Belder ^e

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^cYesilyurt Demir Celik Vocational School, Ondokuz Mayis University, Samsun, Turkey,^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, TR-55139 Samsun, Turkey, and ^eDepartment of Chemistry, Karabük University, 78200 Karabük, Turkey
Correspondence e-mail: rbutcher99@yahoo.com

The title compound, C₁₆H₁₉N₃O₄S, is almost planar, with a dihedral angle of 2.88 (9)° between the mean planes of the benzene and thiazole rings. The molecule adopts an E conformation about the two C=N bonds, with a C-N-N-C torsion angle of -177.01 (11)°. An intramolecular C-HO hydrogen bond exists between a thiazole methyl group and the formic acid ethyl ester carbonyl O atom. In the crystal, molecules are linked by O--HO hydrogen bonds, forming chains propagating along [2-10]. The chains are linked via C-HO hydrogen bonds with R₂²(12) ring motifs, forming sheets lying parallel to (12-2). The sheets are further linked through out-of-plane C-HN hydrogen bonds with R₂²(12) ring motifs and C-H [pi] interactions, forming an interesting three-dimensional supramolecular architecture.

Related literature

For the various biological activities of 1,3-thiazoles, 1,3,4-thiadiazoles and their derivatives, see: Shucla et al. (1984); Desai & Baxi (1992); Mullican et al. (1993); Chapleo et al. (1986); Turner et al. (1988); Mazzone et al. (1993); Miyamoto et al. (1985); Hanna et al. (1995); Oh et al. (2002). For the antimicrobial activity of thiadiazoles and related compounds, see: Sancak et al. (2007). For bond lengths of structurally related molecules, see: Imhof & Wunderle (2012); Randell et al. (2012). For details of the Cambridge Structural Database, see: Allen (2002). For synthetic details, see: Er et al. (2009). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₆H₁₉N₃O₄S
M_r = 349.40
Triclinic, $[P \overline 1]$
a = 6.8957 (3) Å
b = 10.2716 (5) Å
c = 12.7297 (6) Å
= 74.843 (4)°
= 87.579 (4)°
= 73.304 (4)°
V = 833.06 (7) Å³
Z = 2
Cu K radiation
= 1.96 mm^-1
T = 123 K
0.40 × 0.35 × 0.30 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011) T_min = 0.508, T_max = 0.591
5272 measured reflections
3316 independent reflections
3254 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.099
S = 1.02
3316 reflections
222 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 ring.

D-HA	D-H	HA	DA	D-HA
C7-H7AO2	0.98	2.28	3.0111 (19)	130
O4-H4OO2ⁱ	0.84	1.85	2.6878 (14)	176
C16-H16AO4ⁱⁱ	0.98	2.41	3.3824 (18)	171
C8-H8CN3ⁱⁱⁱ	0.98	2.62	3.3986 (19)	137
C6-H6BCg1^iv	0.98	2.96	3.6414 (16)	128
C7-H7CCg1^v	0.98	2.62	3.4762 (16)	146
Symmetry codes: (i) x-2, y+1, z; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1; (v) x+1, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2516 ).

Acknowledgements

RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Chapleo, C. B., Myers, M., Myers, P. L., Saville, J. F., Smith, A. C. B., Stilling, M. R., Tulloch, I. F., Walter, D. S. & Welbourne, A. P. (1986). J. Med. Chem. 29, 2273-2280.
Desai, K. & Baxi, A. J. (1992). Indian J. Pharm. Sci. 54, 183-188.
Er, M., Ünver, Y., Sancak, K., Degirmencioglu, I. & Karaoglu, S. A. (2009). Arkivoc, II, 149-167.
Hanna, M. A., Girges, M. M., Rasala, D. & Gawinecki, R. (1995). Arzneim. Forsch. Drug. Res. 45, 1074-1078.
Imhof, W. & Wunderle, J. (2012). Acta Cryst. E68, o2741.
Mazzone, G., Pignatello, R., Mazzone, S., Panico, A., Penisi, G., Castana, R. & Mazzone, P. (1993). Il Farmaco, 48, 1207-1224.
Miyamoto, K., Koshiura, R., Mori, M., Yokoi, H., Mori, C., Hasegawa, T. & Takatori, K. (1985). Chem. Pharm. Bull. 33, 5126-5129.
Mullican, M. D., Wilson, M. W., Connor, D. T., Kostlan, C. R., Schrier, D. J. & Dyer, R. D. (1993). J. Med. Chem. 36, 1090-1099.
Oh, C.-H., Cho, H.-W., Baek, D. & Cho, J.-H. (2002). Eur. J. Med. Chem. 37, 743-754.
Randell, N. M., Thompson, L. K. & Dawe, L. N. (2012). Acta Cryst. E68, o2711.
Sancak, K., Ünver, Y. & Er, M. (2007). Turk. J. Chem. 31, 125-134.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shucla, H. K., Desai, N. C., Astik, R. R. & Thaker, K. A. (1984). J. Indian Chem. Soc. 61, 168-171.
Turner, S., Myers, M., Gadie, B., Hale, S. A., Horsley, A., Nelson, A. J., Pape, R., Saville, J. F., Doxey, J. C. & Berridge, T. L. (1988). J. Med. Chem. 31, 906-913.

organic compounds