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

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

doi:10.1107/S1600536812042523

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 (C-C) = 0.003 Å
R = 0.037
wR = 0.108
Data-to-parameter ratio = 13.9
Details

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

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-HO interactions, resulting in R²₂(24) ring motifs.

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

C₂₈H₂₁ClN₂O₃
M_r = 468.92
Monoclinic, P 2₁ /n
a = 12.1626 (4) Å
b = 16.2747 (6) Å
c = 12.1960 (4) Å
= 107.704 (2)°
V = 2299.78 (14) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.932, T_max = 0.951
21438 measured reflections
4288 independent reflections
3335 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.108
S = 1.04
4288 reflections
308 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C22-H22BO1ⁱ	0.96	2.54	3.351 (2)	142
Symmetry code: (i) -x+1, -y, -z.

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: PV2592 ).

Acknowledgements

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

References

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