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Volume 68 
Part 11 
Pages o3199-o3200  
November 2012  

Received 15 October 2012
Accepted 17 October 2012
Online 24 October 2012

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.127
Data-to-parameter ratio = 15.9
Details
Open access

3-Ethyl-3-hydroxy-8-methoxyquinoline-2,4(1H,3H)-dione monohydrate

Stanislav Kafka,a Andrej Pevec,b* Karel Proisl,a Roman Kimmela and Janez Kosmrljb

aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Zlin 76272, Czech Republic, and bFaculty of Chemistry and Chemical Technology, University of Ljubljana, SI-1000 Ljubljana, Slovenia
Correspondence e-mail: andrej.pevec@fkkt.uni-lj.si

In the title hydrate, C12H13NO4·H2O, the piperidine ring that is fused to the benzene ring is in a sofa conformation with the chiral C atom lying 0.4084 (18) Å out of the plane of the nine fused-ring atoms. In the crystal, O-H...O and N-H...O hydrogen bonds link the organic molecules and water molecules into chains running along the b-axis direction. The chains are further connected into layers parallel to the bc plane by [pi]-[pi] interactions between inversion-related benzene rings [centroid-centroid distance = 3.8846 (9) Å].

Related literature

For methods of preparation of 3-alkyl- or 3-aryl-3-hydroxyquinoline-2,4-diones by oxidation of the corresponding 3-alkyl- or 3-arylquinolin-2-ones, see: Stadlbauer & Kappe (1982[Stadlbauer, W. & Kappe, T. (1982). Z. Naturforsch. Teil B, 37, 1196-1200.]); Stadlbauer et al. (1992[Stadlbauer, W., Lutschounig, H., Schindler, G., Witoszynskyj, T. & Kappe, T. (1992). J. Heterocycl. Chem. 29, 1535-1540.]). For naturally occurring 3-hydroxyquinoline-2,4-diones, see: Neuenhaus & Budzikiewicz (1979[Neuenhaus, W. & Budzikiewicz, H. (1979). Z. Naturforsch. Teil B, 34, 313-315.]); Luo et al. (2009[Luo, X. M., Qi, S. H., Yin, H., Gao, C. H. & Zhang, S. (2009). Chem. Pharm. Bull. 57, 600-602.]). For the biological activity of 3-hydroxyquinoline-2,4-diones, see: Prisyazhnyuk et al. (1984[Prisyazhnyuk, P. V., Patratii, V. K., Prodanchuk, N. G., Tashchuk, K. G. & Fedoryak, S. D. (1984). Khim. Farm. Zh. 18, 440-444.]); Luo et al. (2009[Luo, X. M., Qi, S. H., Yin, H., Gao, C. H. & Zhang, S. (2009). Chem. Pharm. Bull. 57, 600-602.]). For a related structure, see: Kafka et al. (2012[Kafka, S., Pevec, A., Proisl, K., Kimmel, R. & Kosmrlj, J. (2012). Acta Cryst. E68, o3198.]).

[Scheme 1]

Experimental

Crystal data

  • C12H13NO4·H2O

  • Mr = 253.25

  • Orthorhombic, P b c a

  • a = 16.5055 (4) Å

  • b = 8.8068 (2) Å

  • c = 16.6690 (4) Å

  • V = 2423.02 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.50 × 0.25 × 0.20 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.948, Tmax = 0.979

  • 5200 measured reflections

  • 2779 independent reflections

  • 1963 reflections with I > 2[sigma](I)

  • Rint = 0.019
Refinement

  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.127

  • S = 1.03

  • 2779 reflections

  • 175 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O1i 0.82 2.35 2.9430 (17) 130
N1-H1N...O1W 0.86 (1) 2.01 (2) 2.8438 (19) 163 (2)
O1W-H1W...O2ii 0.92 (2) 2.07 (2) 2.9425 (19) 158 (2)
O1W-H2W...O3iii 0.92 (2) 2.15 (2) 2.9401 (19) 144 (2)
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x, y+1, z; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.] and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5162 ).

Acknowledgements

This study was supported by the internal grant of TBU in Zlin (No. IGA/FT/2012/043), funded from the resources of specific university research, and the Slovenian Research Agency (Project P1-0230-0103 and Joint Project BI-CZ/07-08-018). This work was also partly supported through the infrastructure of the EN-FIST Centre of Excellence, Ljubljana.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Kafka, S., Pevec, A., Proisl, K., Kimmel, R. & Kosmrlj, J. (2012). Acta Cryst. E68, o3198.  [CrossRef] [details]
Luo, X. M., Qi, S. H., Yin, H., Gao, C. H. & Zhang, S. (2009). Chem. Pharm. Bull. 57, 600-602.  [CrossRef] [PubMed] [ChemPort]
Neuenhaus, W. & Budzikiewicz, H. (1979). Z. Naturforsch. Teil B, 34, 313-315.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.
Prisyazhnyuk, P. V., Patratii, V. K., Prodanchuk, N. G., Tashchuk, K. G. & Fedoryak, S. D. (1984). Khim. Farm. Zh. 18, 440-444.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stadlbauer, W. & Kappe, T. (1982). Z. Naturforsch. Teil B, 37, 1196-1200.
Stadlbauer, W., Lutschounig, H., Schindler, G., Witoszynskyj, T. & Kappe, T. (1992). J. Heterocycl. Chem. 29, 1535-1540.  [CrossRef] [ChemPort]

Acta Cryst (2012). E68, o3199-o3200   [ doi:10.1107/S1600536812043280 ]

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