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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

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

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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