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Volume 69 
Part 2 
Page o281  
February 2013  

Received 6 January 2013
Accepted 14 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.052
wR = 0.159
Data-to-parameter ratio = 25.4
Details
Open access

9-(2,4-Dinitrophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

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

In the title compound, C23H24N2O7, the central 4H-pyran ring adopts a flattened boat conformation, whereas both cyclohexenone rings adopt envelope conformations, the C atom bearing the dimethyl substituent being the flap atom in each case. The mean and maximum deviation of the pyran ring are 0.0379 (4) and 0.0605 (3) Å. The mean plane of the pyran ring and the dinitrobenzene ring make a dihedral angle of 85.88 (2)°.

Related literature

For the synthesis of xanthenes, see: Vanag & Stankevich (1960[Vanag, G. Y. & Stankevich, E. L. (1960). Zh. Obshch. Khim. 30, 3287-3290.]); Hilderbrand & Weissleder (2007[Hilderbrand, S. A. & Weissleder, R. (2007). Tetrahedron Lett. 48, 4383-4385.]). For their pharmaceutical properties, see: Dimmock et al. (1988[Dimmock, J. R., Raghavan, S. K. & Bigam, G. E. (1988). Eur. J. Med. Chem. 23, 111-117.]); Lambert et al. (1997[Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9706178.]); Poupelin et al. (1978[Poupelin, J. P., Saint-Ruf, G., Foussard-Blanpin, O., Narcisse, G., Uchida-Ernouf, G. & Lacroix, R. (1978). Eur. J. Med. Chem. 13, 67-71.]); Hideo (1981[Hideo, T. (1981). Jpn Kokai Tokkyo Koho JP 56 005480.]); Selvanayagam et al. (1996[Selvanayagam, Z. E., Gnanavendhan, S. G., Balakrishnan, K., Rao, R. B., Sivaraman, J., Subramanian, K., Puri, R. & Puri, R. K. (1996). J. Nat. Prod. 59, 664-667.]). 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 related structures, see: Odabasoglu et al. (2008[Odabasoglu, M., Kaya, M., Yildirir, Y. & Büyükgüngör, O. (2008). Acta Cryst. E64, o681.]); Reddy et al. (2009[Reddy, B. P., Vijayakumar, V., Narasimhamurthy, T., Suresh, J. & Lakshman, P. L. N. (2009). Acta Cryst. E65, o916.]); Mehdi et al. (2011[Mehdi, S. H., Sulaiman, O., Ghalib, R. M., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1719-o1720.]); Sughanya & Sureshbabu (2012[Sughanya, V. & Sureshbabu, N. (2012). Acta Cryst. E68, o1060.]). For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H24N2O7

  • Mr = 440.44

  • Monoclinic, P 21 /c

  • a = 9.7733 (3) Å

  • b = 19.6193 (5) Å

  • c = 11.7922 (3) Å

  • [beta] = 109.603 (1)°

  • V = 2130.04 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.35 × 0.30 × 0.25 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 = 0.905, Tmax = 0.975

  • 29785 measured reflections

  • 7327 independent reflections

  • 4793 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.159

  • S = 1.03

  • 7327 reflections

  • 289 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

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: IM2418 ).


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] [ISI] [details]
Bruker (2004). APEX2 , SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dimmock, J. R., Raghavan, S. K. & Bigam, G. E. (1988). Eur. J. Med. Chem. 23, 111-117.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hideo, T. (1981). Jpn Kokai Tokkyo Koho JP 56 005480.
Hilderbrand, S. A. & Weissleder, R. (2007). Tetrahedron Lett. 48, 4383-4385.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9706178.
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.  [ISI] [CrossRef] [ChemPort] [details]
Mehdi, S. H., Sulaiman, O., Ghalib, R. M., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1719-o1720.  [CSD] [CrossRef] [details]
Odabasoglu, M., Kaya, M., Yildirir, Y. & Büyükgüngör, O. (2008). Acta Cryst. E64, o681.  [CrossRef] [details]
Poupelin, J. P., Saint-Ruf, G., Foussard-Blanpin, O., Narcisse, G., Uchida-Ernouf, G. & Lacroix, R. (1978). Eur. J. Med. Chem. 13, 67-71.  [ChemPort]
Reddy, B. P., Vijayakumar, V., Narasimhamurthy, T., Suresh, J. & Lakshman, P. L. N. (2009). Acta Cryst. E65, o916.  [CSD] [CrossRef] [details]
Selvanayagam, Z. E., Gnanavendhan, S. G., Balakrishnan, K., Rao, R. B., Sivaraman, J., Subramanian, K., Puri, R. & Puri, R. K. (1996). J. Nat. Prod. 59, 664-667.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sughanya, V. & Sureshbabu, N. (2012). Acta Cryst. E68, o1060.  [CSD] [CrossRef] [details]
Vanag, G. Y. & Stankevich, E. L. (1960). Zh. Obshch. Khim. 30, 3287-3290.


Acta Cryst (2013). E69, o281  [ doi:10.1107/S1600536813001384 ]

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