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Volume 69 
Part 11 
Pages o1690-o1691  
November 2013  

Received 15 October 2013
Accepted 17 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.111
Data-to-parameter ratio = 12.9
Details
Open access

6-Hy­droxy-5-[(2-hy­droxy-4,4-dimethyl-6-oxo­cyclo­hex-1-en­yl)(4-nitro­phen­yl)meth­yl]-1,3-di­methyl­pyrimidine-2,4(1H,3H)-dione

aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India
Correspondence e-mail: saisukanyashri@gmail.com

In the title compound, C21H23N3O7, the pyrimidine­dione ring adopts a screw-boat conformation, whereas the cyclo­hexenone ring adopts an envelope conformation, with the C atom bearing the methyl groups as the flap atom. The dihedral angle between the mean planes of the pyrimidine­dione and cyclo­hexenone rings is 58.78 (2)°. The pyrimidine­dione and cyclo­hexenone rings form dihedral angles of 59.94 (3) and 54.73 (2)°, respectively, with the 4-nitro­phenyl ring. Relatively strong intra­molecular O-H...O hydrogen bonds are observed. In the crystal, mol­ecules are linked by C-H...O hydrogen bonds, forming a chain along the c-axis direction.

Related literature

For related syntheses, see: Horning & Horning (1946[Horning, E. C. & Horning, M. G. (1946). J. Org. Chem. 11, 95-99.]); Kaupp et al. (2003[Kaupp, G., Naimi-Jamal, M. R. & Schmeyers, J. (2003). Tetrahedron, 59, 3753-3760.]). For biological and pharmaceutical properties of pyrimidine derivatives, see: Ibrahim & El-Metwally (2010[Ibrahim, D. A. & El-Metwally, A. M. (2010). Eur. J. Med. Chem. 45, 1158-1166.]); Kappe (1993[Kappe, C. O. (1993). Tetrahedron, 49, 6937-6963.]); Campbell et al. (1988[Campbell, K. P., Leung, A. T. & Sharp, A. H. (1988). Trends Neurosci. 11, 425-430.]); Elinson et al. (2006[Elinson, M. N., Dorofeev, A. S., Feducovich, S. K., Gorbunov, S. V., Nasybullin, R. F., Stepanov, N. O. & Nikishin, G. I. (2006). Tetrahedron Lett. 47, 7629-7633.]); Sun et al. (2006[Sun, W., Cama, L. D., Birzin, E. T., Warrier, S., Locco, L., Mosley, R., Hammond, M. L. & Rohrer, S. P. (2006). Bioorg. Med. Chem. Lett. 16, 1468-1472.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the crystal structure of a related bis­dimedone derivative, see: Sughanya & Sureshbabu (2012[Sughanya, V. & Sureshbabu, N. (2012). Acta Cryst. E68, o2875-o2876.]). For the assignment of ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C21H23N3O7

  • Mr = 429.42

  • Monoclinic, P 21 /c

  • a = 12.7470 (2) Å

  • b = 14.0577 (3) Å

  • c = 11.7639 (2) Å

  • [beta] = 99.752 (1)°

  • V = 2077.55 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.996

  • 19038 measured reflections

  • 3655 independent reflections

  • 2930 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.111

  • S = 1.03

  • 3655 reflections

  • 284 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C14-H14B...O3i 0.97 2.57 3.328 (2) 135
C20-H20...O7i 0.93 2.53 3.153 (2) 125
O2-H2...O4 0.82 1.78 2.5932 (18) 172
O5-H5...O3 0.82 1.78 2.5863 (18) 167
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5316 ).


Acknowledgements

The authors thank Dr Babu Varghese and the SAIF, IIT Madras, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Bruker (2004). APEX2, SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Campbell, K. P., Leung, A. T. & Sharp, A. H. (1988). Trends Neurosci. 11, 425-430.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Elinson, M. N., Dorofeev, A. S., Feducovich, S. K., Gorbunov, S. V., Nasybullin, R. F., Stepanov, N. O. & Nikishin, G. I. (2006). Tetrahedron Lett. 47, 7629-7633.  [Web of Science] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Horning, E. C. & Horning, M. G. (1946). J. Org. Chem. 11, 95-99.  [CrossRef] [ChemPort] [PubMed]
Ibrahim, D. A. & El-Metwally, A. M. (2010). Eur. J. Med. Chem. 45, 1158-1166.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Kappe, C. O. (1993). Tetrahedron, 49, 6937-6963.  [CrossRef] [ChemPort]
Kaupp, G., Naimi-Jamal, M. R. & Schmeyers, J. (2003). Tetrahedron, 59, 3753-3760.  [Web of Science] [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sughanya, V. & Sureshbabu, N. (2012). Acta Cryst. E68, o2875-o2876.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sun, W., Cama, L. D., Birzin, E. T., Warrier, S., Locco, L., Mosley, R., Hammond, M. L. & Rohrer, S. P. (2006). Bioorg. Med. Chem. Lett. 16, 1468-1472.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1690-o1691   [ doi:10.1107/S1600536813028584 ]

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