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

Sureshbabu, N.; Sughanya, V.

doi:10.1107/S1600536813001384

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 (C-C) = 0.002 Å
R = 0.052
wR = 0.159
Data-to-parameter ratio = 25.4
Details

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

N. Sureshbabu ^a and V. Sughanya ^a ^*

^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); Hilderbrand & Weissleder (2007). For their pharmaceutical properties, see: Dimmock et al. (1988); Lambert et al. (1997); Poupelin et al. (1978); Hideo (1981); Selvanayagam et al. (1996). For bond-length data, see: Allen et al. (1987). For related structures, see: Odabasoglu et al. (2008); Reddy et al. (2009); Mehdi et al. (2011); Sughanya & Sureshbabu (2012). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₃H₂₄N₂O₇
M_r = 440.44
Monoclinic, P 2₁ /c
a = 9.7733 (3) Å
b = 19.6193 (5) Å
c = 11.7922 (3) Å
= 109.603 (1)°
V = 2130.04 (10) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.905, T_max = 0.975
29785 measured reflections
7327 independent reflections
4793 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.159
S = 1.03
7327 reflections
289 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.30 e Å^-3

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); 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

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organic compounds