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Volume 69 
Part 2 
Pages o297-o298  
February 2013  

Received 8 January 2013
Accepted 23 January 2013
Online 26 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.059
wR = 0.127
Data-to-parameter ratio = 10.6
Details
Open access

9-(3,4-Dimethoxyphenyl)-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, and bDepartment of Chemistry, Shivaji University, Kolhapur, 416 004 (MS), India
Correspondence e-mail: rkvk.paper11@gmail.com

The asymmetric unit of the title compound, C25H31NO4, contains two independent molecules. In one molecule, the benzene ring and an attached methoxy group were refined as disordered over two sets of sites in a 0.65 (4): 0.35 (4) ratio. In both molecules, the central ring of the acridinedione system adopts a flattened boat conformation. The four essentially planar atoms of this ring [maximum deviations = 0.006 (5) Å in both molecules] forms dihedral angles of 86.8 (2) and 87.6 (2)°, respectively, with the major and minor components in the disordered benzene ring and 87.3 (2)° with the benzene ring in the fully ordered molecule. The two outer rings of the acridinedione system adopt sofa conformations in both molecules. In the crystal, N-H...O hydrogen bonds form two independent chains along [100]. C-H...O hydrogen bonds link the chains, forming a three-dimensional network.

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.]); Leon et al. (2008[Leon, R., Rios, C., Contelles, J. M., Lopez, G. M., Garcia, A. G. & Villarroya, M. (2008). Eur. J. Med. Chem. 43, 668-674.]); 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.]); Kant et al. (2013a[Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Patil, P. P. & Deshmukh, M. B. (2013a). Acta Cryst. E69, o100.],b[Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Jagadale, S. D. & Deshmukh, M. B. (2013b). Acta Cryst. E69, o101.]). 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
  • C25H31NO4

  • Mr = 409.51

  • Orthorhombic, P c a 21

  • a = 14.1607 (6) Å

  • b = 15.3126 (10) Å

  • c = 21.1196 (14) Å

  • V = 4579.5 (5) Å3

  • Z = 8

  • 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 = 0.672, Tmax = 1.000

  • 14639 measured reflections

  • 6386 independent reflections

  • 4075 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.127

  • S = 1.01

  • 6386 reflections

  • 604 parameters

  • 53 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 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
N12A-H12A...O1Ai 0.86 2.07 2.846 (4) 150
N12B-H12B...O8Bii 0.86 2.05 2.885 (4) 165
C2A-H2AA...O1Bii 0.97 2.45 3.400 (6) 166
C16A-H16D...O25Aiii 0.96 2.61 3.477 (12) 150
C7A-H7AB...O27Biv 0.97 2.47 3.432 (6) 169
C7B-H7BB...O8Ai 0.97 2.57 3.507 (5) 162
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+1, z]; (ii) [x+{\script{1\over 2}}, -y, z]; (iii) [-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]; (iv) [-x, -y+1, 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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: LH5574 ).


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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Josephrajan, T., Ramakrishnan, V. T., Kathiravan, G. & Muthumary, J. (2005). ARKIVOC, pp. 124-136.
Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Patil, P. P. & Deshmukh, M. B. (2013a). Acta Cryst. E69, o100.  [CrossRef] [details]
Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Jagadale, S. D. & Deshmukh, M. B. (2013b). Acta Cryst. E69, o101.  [CrossRef] [details]
Leon, R., Rios, C., Contelles, J. M., Lopez, G. M., Garcia, A. G. & Villarroya, M. (2008). Eur. J. Med. Chem. 43, 668-674.  [ISI] [PubMed] [ChemPort]
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, o297-o298   [ doi:10.1107/S1600536813002250 ]

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