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Volume 69 
Part 9 
Pages o1411-o1412  
September 2013  

Received 20 July 2013
Accepted 3 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.048
wR = 0.145
Data-to-parameter ratio = 12.5
Details
Open access

Ethyl 2-amino-4-(4-methyl-1,3-thiazol-5-yl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate

aDepartment of Chemistry, Madras Christian College, Tambaram, Chennai 600 059, Tamil Nadu, India, and bDepartment of Chemistry, IIT Madras, Chennai 600 036, Tamil Nadu, India
Correspondence e-mail: rjkmcc@yahoo.com

There are two independent molecules in the asymmetric unit of the title compound, C19H16N2O5S, in which the thiazole rings make dihedral angles of 80.89 (11) and 84.81 (11)° with the pyrano[3,2-c]chromene ring systems. An intramolecular N-H...O hydrogen bond involving the amino group occurs in each independent molecule. In the crystal, the amino groups are involved in N-H...O and N-H...N hydrogen bonds.

Related literature

Similar conformations were observed in the structures of ethyl 2-amino-5-oxo-4-(p-tolyl)-4H,5H-pyrano[3,2-c]chromene-8-carboxylate (Wang et al., 2004[Wang, J., Shi, D. & Wang, X. (2004). Acta Cryst. E60, o1725-o1727.]) and ethyl 2-amino-4-(2,4-dichlorophenyl)-4H-benzo[f]chromene-3-carboxylate (Shi et al., 2003[Shi, D.-Q., Wang, J., Wang, X., Zhuang, Q. & Yu, K. (2003). Acta Cryst. E59, o1733-o1734.]). For applications of 4H-chromene and its derivatives, see: Jeso & Nicolaou (2009[Jeso, V. & Nicolaou, K. C. (2009). Tetrahedron Lett. 50, 1161-1163.]); Alvey et al. (2008[Alvey, L., Prado, S., Huteau, V., Saint-Joanis, B., Michel, S., Koch, M., Cole, S. T., Tillequin, F. & Janin, Y. L. (2008). Bioorg. Med. Chem. 16, 8264-8272.], 2009[Alvey, L., Prado, S., Saint-Joanis, B., Michel, S., Koch, M., Cole, S. T., Tillequin, F. & Janin, Y. L. (2009). Eur. J. Med. Chem. 44, 2497-2505.]); Bedair et al. (2001[Bedair, A. H., Emam, H. A., El-Hady, N. A., Ahmed, K. A. R. & El-Agrody, A. M. (2001). Il Farmaco, 56, 965-973.]); El-Agrody et al. (2002[El-Agrody, A. M., Eid, F. A., Emam, H. A., Mohamed, H. M. & Bedair, A. H. (2002). Z. Naturforsch. Teil B, 57, 579-585.], 2011[El-Agrody, A. M., Sabry, N. M. & Motlaq, S. S. (2011). J. Chem. Res. 35, 77-83.]); Abd-El-Aziz et al. (2004[Abd-El-Aziz, A. S., El-Agrody, A. M., Bedair, A. H., Corkery, T. C. & Ata, A. (2004). Heterocycles, 63, 1793-1812.]); Sabry et al. (2011[Sabry, N. M., Mohamed, H. M., Khattab, E. S. A. E. H., Motlaq, S. S. & El-Agrody, A. M. (2011). Eur. J. Med. Chem. 46, 765-772.]).

[Scheme 1]

Experimental

Crystal data
  • C19H16N2O5S

  • Mr = 384.41

  • Monoclinic, P 21 /n

  • a = 15.6232 (10) Å

  • b = 15.0696 (9) Å

  • c = 15.9063 (11) Å

  • [beta] = 98.873 (2)°

  • V = 3700.1 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 298 K

  • 0.35 × 0.25 × 0.15 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.970

  • 18921 measured reflections

  • 6130 independent reflections

  • 3527 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.145

  • S = 1.03

  • 6130 reflections

  • 491 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1B...O4 0.86 2.11 2.698 (3) 125
N1-H1B...N2Ai 0.86 2.49 3.152 (3) 135
N1-H1C...N2ii 0.86 2.27 3.116 (4) 167
N1A-H1A2...N2Aiii 0.86 2.13 2.988 (4) 174
N1A-H1A1...O4A 0.86 2.09 2.690 (3) 126
N1A-H1A1...O4ii 0.86 2.52 2.936 (3) 111
Symmetry codes: (i) x, y, z+1; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2447 ).


Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the data collection and Orchid Chemicals and Pharmaceuticals, Chennai, India for providing necessary laboratory facilities.

References

Abd-El-Aziz, A. S., El-Agrody, A. M., Bedair, A. H., Corkery, T. C. & Ata, A. (2004). Heterocycles, 63, 1793-1812.  [ChemPort]
Alvey, L., Prado, S., Huteau, V., Saint-Joanis, B., Michel, S., Koch, M., Cole, S. T., Tillequin, F. & Janin, Y. L. (2008). Bioorg. Med. Chem. 16, 8264-8272.  [CrossRef] [PubMed] [ChemPort]
Alvey, L., Prado, S., Saint-Joanis, B., Michel, S., Koch, M., Cole, S. T., Tillequin, F. & Janin, Y. L. (2009). Eur. J. Med. Chem. 44, 2497-2505.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bedair, A. H., Emam, H. A., El-Hady, N. A., Ahmed, K. A. R. & El-Agrody, A. M. (2001). Il Farmaco, 56, 965-973.  [CrossRef] [PubMed] [ChemPort]
Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Agrody, A. M., Eid, F. A., Emam, H. A., Mohamed, H. M. & Bedair, A. H. (2002). Z. Naturforsch. Teil B, 57, 579-585.  [ChemPort]
El-Agrody, A. M., Sabry, N. M. & Motlaq, S. S. (2011). J. Chem. Res. 35, 77-83.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jeso, V. & Nicolaou, K. C. (2009). Tetrahedron Lett. 50, 1161-1163.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sabry, N. M., Mohamed, H. M., Khattab, E. S. A. E. H., Motlaq, S. S. & El-Agrody, A. M. (2011). Eur. J. Med. Chem. 46, 765-772.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shi, D.-Q., Wang, J., Wang, X., Zhuang, Q. & Yu, K. (2003). Acta Cryst. E59, o1733-o1734.  [CSD] [CrossRef] [ChemPort] [details]
Wang, J., Shi, D. & Wang, X. (2004). Acta Cryst. E60, o1725-o1727.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1411-o1412   [ doi:10.1107/S1600536813021703 ]

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