N-{3-[2-(4-Fluoro­phen­oxy)eth­yl]-2,4-dioxo-1,3-diaza­spiro­[4.5]decan-7-yl}-4-meth­oxy­benzene­sulfonamide

Vinduvahini, M.; Jeyaseelan, S.; Shylajakumari, J.; Revanasiddappa, H.D.; Devaru, V.B.

doi:10.1107/S1600536811053980

Volume 68
Part 1
Pages o194-o195
January 2012

Received 14 November 2011
Accepted 15 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.121
Data-to-parameter ratio = 13.8
Details

N-{3-[2-(4-Fluorophenoxy)ethyl]-2,4-dioxo-1,3-diazaspiro[4.5]decan-7-yl}-4-methoxybenzenesulfonamide

M. Vinduvahini,^a ^* S. Jeyaseelan,^b J. Shylajakumari,^c H. D. Revanasiddappa ^d and Venkatesh B. Devaru ^e

^aDepartment of Physics, Sri D Devaraja Urs Govt. First Grade College, Hunsur 571 105, Mysore District, Karnataka, India,^bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India,^cDepartment of Physics, AVK College for Women, Hassan 573 201, Karnataka, India,^dDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, Karnataka, India, and ^eDepartment of P.G. Studies in Physics, L V D College, Raichur 584 103, Karnataka, India
Correspondence e-mail: vinduvahinim@yahoo.in

In the title compound, C₂₃H₂₆FN₃O₆S, the two terminal aromatic rings form a dihedral angle of 49.26 (12)°. The cyclohexane ring adopts a chair conformation and the five-membered ring is essentially planar, with a maximum deviation from planarity of 0.0456 (19) Å. The dihedral angles between the five-membered ring and the methoxybenzene and fluorobenzene rings are 33.56 (11) and 81.94 (12)°, respectively. The crystal structure displays N-HO hydrogen bonds as well as weak intermolecular C-HO interactions.

Related literature

For the biological activity of related compounds, see: Cartwright et al. (2007); Collins (2000); Warshakoon et al. (2006) and for their pharmaceutical activity, see: Kiselyov et al. (2006); Sakthivel & Cook (2005); Eldrup et al. (2004); Bamford et al. (2005); Puerstinger et al. (2006).

Experimental

Crystal data

C₂₃H₂₆FN₃O₆S
M_r = 491.53
Monoclinic, P 2₁ /c
a = 11.926 (5) Å
b = 11.025 (5) Å
c = 18.508 (5) Å
= 97.271 (5)°
V = 2413.9 (16) Å³
Z = 4
Mo K radiation
= 0.19 mm^-1
T = 293 K
0.20 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED . Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.771, T_max = 1.000
21931 measured reflections
4240 independent reflections
3435 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.121
S = 1.04
4240 reflections
307 parameters
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.50 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N10-H10O5ⁱ	0.86	2.08	2.924 (2)	168
N11-H11O6ⁱⁱ	0.86	2.39	2.991 (3)	127
C20-H20AO4ⁱⁱⁱ	0.97	2.51	3.377 (3)	148
C31-H31O4^iv	0.93	2.48	3.327 (3)	152
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED . Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED . Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2365 ).

Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help with the data collection.

References

Bamford, M. J., et al. (2005). Bioorg. Med. Chem. Lett. 15, 3402-3406.
Cartwright, M. W., Sandford, G., Bousbaa, J., Yufit, D. S., Howard, J. A. K., Christopher, J. A. & Miller, D. D. (2007). Tetrahedron, 63, 7027-7035.
Collins, I. (2000). J. Chem. Soc. Perkin Trans. 1 pp. 2845-2861.
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Kiselyov, A. S., Semenova, M., Semenov, V. V. & Piatnitski, E. (2006). Bioorg. Med. Chem. Lett. 16, 1726-1730.
Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED . Oxford Diffraction Ltd, Yarnton, England.
Puerstinger, G., Paeshuyse, J., Herdewijn, P., Rozenski, J., Clercq, D. & Neyts, J. (2006). Bioorg. Med. Chem. Lett. 16, 5345-5349.
Sakthivel, K. & Cook, P. D. (2005). Tetrahedron Lett. 46, 3883-3887.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Warshakoon, N. C., Wu, S., Boyer, A., Kawamoto, R., Sheville, J., Renock, S., Xu, K., Pokross, M., Evdokimov, A. G., Walter, R. & Mekel, M. (2006). Bioorg. Med. Chem. Lett. 16, 5598-5601.

organic compounds