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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 [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.099
Data-to-parameter ratio = 14.9
Details
Open access

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

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-H...O 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--H...O hydrogen bonds, forming chains propagating along [2-10]. The chains are linked via C-H...O hydrogen bonds with R22(12) ring motifs, forming sheets lying parallel to (12-2). The sheets are further linked through out-of-plane C-H...N 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[Shucla, H. K., Desai, N. C., Astik, R. R. & Thaker, K. A. (1984). J. Indian Chem. Soc. 61, 168-171.]); Desai & Baxi (1992[Desai, K. & Baxi, A. J. (1992). Indian J. Pharm. Sci. 54, 183-188.]); Mullican et al. (1993[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.]); Chapleo et al. (1986[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.]); Turner et al. (1988[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.]); Mazzone et al. (1993[Mazzone, G., Pignatello, R., Mazzone, S., Panico, A., Penisi, G., Castana, R. & Mazzone, P. (1993). Il Farmaco, 48, 1207-1224.]); Miyamoto et al. (1985[Miyamoto, K., Koshiura, R., Mori, M., Yokoi, H., Mori, C., Hasegawa, T. & Takatori, K. (1985). Chem. Pharm. Bull. 33, 5126-5129.]); Hanna et al. (1995[Hanna, M. A., Girges, M. M., Rasala, D. & Gawinecki, R. (1995). Arzneim. Forsch. Drug. Res. 45, 1074-1078.]); Oh et al. (2002[Oh, C.-H., Cho, H.-W., Baek, D. & Cho, J.-H. (2002). Eur. J. Med. Chem. 37, 743-754.]). For the antimicrobial activity of thiadiazoles and related compounds, see: Sancak et al. (2007[Sancak, K., Ünver, Y. & Er, M. (2007). Turk. J. Chem. 31, 125-134.]). For bond lengths of structurally related molecules, see: Imhof & Wunderle (2012[Imhof, W. & Wunderle, J. (2012). Acta Cryst. E68, o2741.]); Randell et al. (2012[Randell, N. M., Thompson, L. K. & Dawe, L. N. (2012). Acta Cryst. E68, o2711.]). For details of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For synthetic details, see: Er et al. (2009[Er, M., Ünver, Y., Sancak, K., Degirmencioglu, I. & Karaoglu, S. A. (2009). Arkivoc, II, 149-167.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C16H19N3O4S

  • Mr = 349.40

  • Triclinic, [P \overline 1]

  • a = 6.8957 (3) Å

  • b = 10.2716 (5) Å

  • c = 12.7297 (6) Å

  • [alpha] = 74.843 (4)°

  • [beta] = 87.579 (4)°

  • [gamma] = 73.304 (4)°

  • V = 833.06 (7) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.508, Tmax = 0.591

  • 5272 measured reflections

  • 3316 independent reflections

  • 3254 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.099

  • S = 1.02

  • 3316 reflections

  • 222 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 ring.

D-H...A D-H H...A D...A D-H...A
C7-H7A...O2 0.98 2.28 3.0111 (19) 130
O4-H4O...O2i 0.84 1.85 2.6878 (14) 176
C16-H16A...O4ii 0.98 2.41 3.3824 (18) 171
C8-H8C...N3iii 0.98 2.62 3.3986 (19) 137
C6-H6B...Cg1iv 0.98 2.96 3.6414 (16) 128
C7-H7C...Cg1v 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[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ISI] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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.  [CrossRef] [ChemPort] [PubMed] [ISI]
Desai, K. & Baxi, A. J. (1992). Indian J. Pharm. Sci. 54, 183-188.  [ChemPort]
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.  [ChemPort]
Imhof, W. & Wunderle, J. (2012). Acta Cryst. E68, o2741.  [CSD] [CrossRef] [details]
Mazzone, G., Pignatello, R., Mazzone, S., Panico, A., Penisi, G., Castana, R. & Mazzone, P. (1993). Il Farmaco, 48, 1207-1224.  [ChemPort] [PubMed]
Miyamoto, K., Koshiura, R., Mori, M., Yokoi, H., Mori, C., Hasegawa, T. & Takatori, K. (1985). Chem. Pharm. Bull. 33, 5126-5129.  [CrossRef] [ChemPort] [PubMed]
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.  [CrossRef] [ChemPort] [PubMed] [ISI]
Oh, C.-H., Cho, H.-W., Baek, D. & Cho, J.-H. (2002). Eur. J. Med. Chem. 37, 743-754.  [ISI] [CrossRef] [PubMed] [ChemPort]
Randell, N. M., Thompson, L. K. & Dawe, L. N. (2012). Acta Cryst. E68, o2711.  [CSD] [CrossRef] [details]
Sancak, K., Ünver, Y. & Er, M. (2007). Turk. J. Chem. 31, 125-134.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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.  [CrossRef] [ChemPort] [PubMed] [ISI]


Acta Cryst (2012). E68, o3213-o3214   [ doi:10.1107/S1600536812043772 ]

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