9-(3-Fluoro­phen­yl)-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.; Jagadale, S.D.; Deshmukh, M.B.

doi:10.1107/S1600536812050556

Volume 69
Part 1
Page o101
January 2013

Received 7 December 2012
Accepted 12 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.118
Data-to-parameter ratio = 15.3
Details

9-(3-Fluorophenyl)-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 S. D. Jagadale ^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

In the title molecule, C₂₃H₂₆FNO₂, the central ring of the acridinedione system adopts a slight boat conformation and the four essentially planar atoms of this ring [maximum deviation = 0.019 (1) Å] form a dihedral angle of 89.98 (6)° with the benzene ring. The two outer rings of the acridinedione system adopt sofa conformations. In the crystal, N-HO hydrogen bonds link the molecules, forming chains along [001].

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. (2013). For ring conformations, see: Duax & Norton (1975).

Experimental

Crystal data

C₂₃H₂₆FNO₂
M_r = 367.45
Monoclinic, P 2₁ /c
a = 11.0505 (3) Å
b = 12.8264 (3) Å
c = 13.8548 (3) Å
= 100.215 (2)°
V = 1932.63 (8) Å³
Z = 4
Mo K radiation
= 0.09 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 = 0.897, T_max = 1.000
30330 measured reflections
3789 independent reflections
2922 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.118
S = 1.03
3789 reflections
248 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N10-H10O1ⁱ	0.86	2.14	2.990 (2)	168
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5569 ).

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., Jagadale, S. D. & Deshmukh, M. B. (2013). 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.

organic compounds