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Volume 69 
Part 1 
Page o100  
January 2013  

Received 5 December 2012
Accepted 12 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.054
wR = 0.116
Data-to-parameter ratio = 16.0
Details
Open access

9-(4-Hydroxy-3-methoxyphenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India,bDepartment of Chemistry, Shivaji University, Kolhapur 416 004, India, and cDepartment of Agrochemicals and Pest Management, Shivaji University, Kolhapur 416 004 (MS), India.
Correspondence e-mail: rkvk.paper11@gmail.com

In the title molecule, C24H29NO4, the central ring of the acridinedione system adopts a flat boat conformation and the four essentially planar atoms of this ring [maximum deviation = 0.001 (2) Å] form a dihedral angle of 85.99 (12)° with the benzene ring. The two outer rings of the acridinedione system adopt sofa conformations. In the crystal, O-H...O and N-H...O hydrogen bonds link the molecules, forming a two-dimensional network parallel to (100).

Related literature

For applications of acridines, see: Murugan et al. (1998[Murugan, P., Shanmugasundaram, P., Ramakrishnan, V. T., Venkatachalapathy, B., Srividya, N., Ramamurthy, P., Gunasekaran, K. & Velmurugan, D. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 999-1003.]); Josephrajan et al. (2005[Josephrajan, T., Ramakrishnan, V. T., Kathiravan, G. & Muthumary, J. (2005). ARKIVOC, pp. 124-136.]); Srividya et al. (1998[Srividya, N., Ramamurthy, P. & Ramakrishnan, V. T. (1998). Spectrochim. Acta Part A, 54, 245-253.],1996[Srividya, N., Ramamurthy, P., Shanmugasundaram, P. & Ramakrishnan, V. T. (1996). J. Org. Chem. 61, 5083-5089.]). For related structures, see: Balamurugan et al. (2009[Balamurugan, P., Jagan, R., Thiagarajan, V. M., Yamin, B. & Sivakumar, K. (2009). Acta Cryst. E65, o271.]); Zhao & Teng (2008[Zhao, L.-L. & Teng, D. (2008). Acta Cryst. E64, o1772-o1773.]). For ring conformations, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]).

[Scheme 1]

Experimental

Crystal data
  • C24H29NO4

  • Mr = 395.48

  • Monoclinic, P 21 /c

  • a = 10.4828 (3) Å

  • b = 14.8973 (4) Å

  • c = 14.2059 (3) Å

  • [beta] = 101.609 (2)°

  • V = 2173.09 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.970, Tmax = 1.000

  • 63634 measured reflections

  • 4264 independent reflections

  • 2958 reflections with I > 2[sigma](I)

  • Rint = 0.078

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.116

  • S = 1.02

  • 4264 reflections

  • 267 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 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
O1-H1...O4i 0.82 2.12 2.800 (2) 141
N10-H10...O3ii 0.86 1.95 2.802 (2) 174
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5567 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

Balamurugan, P., Jagan, R., Thiagarajan, V. M., Yamin, B. & Sivakumar, K. (2009). Acta Cryst. E65, o271.  [CSD] [CrossRef] [details]
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
Josephrajan, T., Ramakrishnan, V. T., Kathiravan, G. & Muthumary, J. (2005). ARKIVOC, pp. 124-136.
Murugan, P., Shanmugasundaram, P., Ramakrishnan, V. T., Venkatachalapathy, B., Srividya, N., Ramamurthy, P., Gunasekaran, K. & Velmurugan, D. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 999-1003.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Srividya, N., Ramamurthy, P. & Ramakrishnan, V. T. (1998). Spectrochim. Acta Part A, 54, 245-253.
Srividya, N., Ramamurthy, P., Shanmugasundaram, P. & Ramakrishnan, V. T. (1996). J. Org. Chem. 61, 5083-5089.  [CrossRef] [ChemPort]
Zhao, L.-L. & Teng, D. (2008). Acta Cryst. E64, o1772-o1773.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o100  [ doi:10.1107/S1600536812050568 ]

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