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Volume 68 
Part 12 
Page o3289  
December 2012  

Received 25 September 2012
Accepted 31 October 2012
Online 7 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.143
Data-to-parameter ratio = 20.0
Details
Open access

(2RS,5'RS)-3',4'-Bis(4-chlorophenyl)-3,4-dihydrospiro[acridine-2,5'(4'H)-[1,2]oxazol]-1(2H)-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

The title compound, C27H18Cl2N2O2, represents a racemic mixture of the corresponding R,R and S,S diastereomers. The isoxazoline ring adopts an envelope conformation with the spiro C atom deviating by 0.093 (2) Å from the rest of the ring. The six-membered keto-substituted carbocycle has a sofa conformation with the methylene C atom adjacent to the spiro center deviating by 0.289 (2) Å from the mean plane of the remaining atoms. In the crystal, molecules are linked via C-H...Cl interactions and C-Cl...O halogen bonds [2.958 (2) Å, 171.39 (7)°], which generate bifurcated R21(6) ring motifs resulting in C21[R21(6)] chains running parallel to [010].

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., Dumenil, 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
  • C27H18Cl2N2O2

  • Mr = 473.33

  • Monoclinic, P 21 /n

  • a = 7.6493 (4) Å

  • b = 15.1553 (7) Å

  • c = 19.4802 (8) Å

  • [beta] = 90.392 (1)°

  • V = 2258.24 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 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 = 0.895, Tmax = 0.924

  • 26147 measured reflections

  • 5960 independent reflections

  • 4189 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.143

  • S = 1.02

  • 5960 reflections

  • 298 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.66 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10A...Cl2i 0.97 2.78 3.681 (2) 154
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: LD2076 ).


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., Dumenil, 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, o3289  [ doi:10.1107/S1600536812045084 ]

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