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

Narayanan, P.; Maheswari, S.U.; Sethusankar, K.

doi:10.1107/S1600536812045084

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 (C-C) = 0.003 Å
R = 0.051
wR = 0.143
Data-to-parameter ratio = 20.0
Details

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

Ponmudisettu Narayanan,^a Shanmugavel Uma Maheswari ^b and Krishnan Sethusankar ^a ^*

^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-HCl interactions and C-ClO 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); Di Giorgio et al. (2005); Talacki et al. (1974). For related structures, see: Sridharan et al. (2009); Trzybinski et al. (2010). For graph-set notation, see: Bernstein et al.(1995)

Experimental

Crystal data

C₂₇H₁₈Cl₂N₂O₂
M_r = 473.33
Monoclinic, P 2₁ /n
a = 7.6493 (4) Å
b = 15.1553 (7) Å
c = 19.4802 (8) Å
= 90.392 (1)°
V = 2258.24 (18) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.895, T_max = 0.924
26147 measured reflections
5960 independent reflections
4189 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.143
S = 1.02
5960 reflections
298 parameters
H-atom parameters constrained
_max = 0.51 e Å^-3
_min = -0.66 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10ACl2ⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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

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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.
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Spek, A. L. (2009). Acta Cryst. D65, 148-155.
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Talacki, R., Carrell, H. L. & Glusker, J. P. (1974). Acta Cryst. B30, 1044-1047.
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