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

Kant, R.; Gupta, V.K.; Kapoor, K.; Patil, D.R.; Chandam, D.R.; Deshmukh, M.B.

doi:10.1107/S1600536813002250

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 (C-C) = 0.006 Å
Disorder in main residue
R = 0.059
wR = 0.127
Data-to-parameter ratio = 10.6
Details

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

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a D. R. Patil,^b D. R. Chandam ^b and Madhukar B. Deshmukh ^b

^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-HO hydrogen bonds form two independent chains along [100]. C-HO hydrogen bonds link the chains, forming a three-dimensional network.

Related literature

For applications of acridines, see: Murugan et al. (1998); Leon et al. (2008); Josephrajan et al. (2005); Srividya et al. (1998, 1996). For related structures, see: Balamurugan et al. (2009); Zhao & Teng (2008); Kant et al. (2013a,b). For ring conformations, see: Duax & Norton (1975).

Experimental

Crystal data

C₂₅H₃₁NO₄
M_r = 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 radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.672, T_max = 1.000
14639 measured reflections
6386 independent reflections
4075 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.127
S = 1.01
6386 reflections
604 parameters
53 restraints
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N12A-H12AO1Aⁱ	0.86	2.07	2.846 (4)	150
N12B-H12BO8Bⁱⁱ	0.86	2.05	2.885 (4)	165
C2A-H2AAO1Bⁱⁱ	0.97	2.45	3.400 (6)	166
C16A-H16DO25Aⁱⁱⁱ	0.96	2.61	3.477 (12)	150
C7A-H7ABO27B^iv	0.97	2.47	3.432 (6)	169
C7B-H7BBO8Aⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); 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.
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.
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.
Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Jagadale, S. D. & Deshmukh, M. B. (2013b). Acta Cryst. E69, o101.
Leon, R., Rios, C., Contelles, J. M., Lopez, G. M., Garcia, A. G. & Villarroya, M. (2008). Eur. J. Med. Chem. 43, 668-674.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
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.
Zhao, L.-L. & Teng, D. (2008). Acta Cryst. E64, o1772-o1773.