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Volume 68 
Part 11 
Page o3177  
November 2012  

Received 25 September 2012
Accepted 11 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.108
Data-to-parameter ratio = 13.9
Details
Open access

4'-(4-Chlorophenyl)-3'-(4-methoxyphenyl)-3,4-dihydro-1H,4'H-spiro[acridine-2,5'-isoxazol]-1-one

aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Chemistry, School of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C28H21ClN2O3, the quinoline ring system is essentially planar with a maximum deviation of 0.0436 (17) Å. The isoxazole and cyclohexane rings adopt envelope conformations. The isoxazole ring is almost orthogonal to both the quinoline ring system and the cyclohexane ring, making dihedral angles of 85.75 (8) and 81.46 (9) °, respectively. The O atom deviates signifigantly from the six-membered carbocyclic ring by 0.3947 (16) Å. In the crystal, molecules are linked into inversion dimers via pairs of C-H...O interactions, resulting in R22(24) ring motifs.

Related literature

For the uses and biological importance of acridines, see: Asthana et al. (1991[Asthana, P., Rastogi, S., Ghose, S. & Das, S. R. (1991). Indian J. Chem. Sect. B. 30, 893-900.]); Di Giorgio et al. (2005[Di Giorgio, C., De Meo, M., Chiron, J., Delmas, F., Nikoyan, A., Severine, J., Dumeneil, G., Timon-David, P. & Galy, J.-P. (2005). Bioorg. Med. Chem. 13, 5560-5568.]); Talacki et al. (1974[Talacki, R., Carrell, H. L. & Glusker, J. P. (1974). Acta Cryst. B30, 1044-1047.]). For related structures, see: Sridharan et al. (2009[Sridharan, M., Rajendra Prasad, K. J. & Zeller, M. (2009). Acta Cryst. E65, o1064.]); Trzybinski et al. (2010[Trzybinski, D., Zadykowicz, B., Krzyminski, K., Sikorski, A. & Blazejowski, J. (2010). Acta Cryst. E66, o828-o829.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C28H21ClN2O3

  • Mr = 468.92

  • Monoclinic, P 21 /n

  • a = 12.1626 (4) Å

  • b = 16.2747 (6) Å

  • c = 12.1960 (4) Å

  • [beta] = 107.704 (2)°

  • V = 2299.78 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.932, Tmax = 0.951

  • 21438 measured reflections

  • 4288 independent reflections

  • 3335 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.108

  • S = 1.04

  • 4288 reflections

  • 308 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C22-H22B...O1i 0.96 2.54 3.351 (2) 142
Symmetry code: (i) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2592 ).


Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection.

References

Asthana, P., Rastogi, S., Ghose, S. & Das, S. R. (1991). Indian J. Chem. Sect. B. 30, 893-900.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Di Giorgio, C., De Meo, M., Chiron, J., Delmas, F., Nikoyan, A., Severine, J., Dumeneil, G., Timon-David, P. & Galy, J.-P. (2005). Bioorg. Med. Chem. 13, 5560-5568.  [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sridharan, M., Rajendra Prasad, K. J. & Zeller, M. (2009). Acta Cryst. E65, o1064.  [CSD] [CrossRef] [details]
Talacki, R., Carrell, H. L. & Glusker, J. P. (1974). Acta Cryst. B30, 1044-1047.  [CrossRef] [details] [ISI]
Trzybinski, D., Zadykowicz, B., Krzyminski, K., Sikorski, A. & Blazejowski, J. (2010). Acta Cryst. E66, o828-o829.  [CrossRef] [details]


Acta Cryst (2012). E68, o3177  [ doi:10.1107/S1600536812042523 ]

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