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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 [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.121
Data-to-parameter ratio = 13.8
Details
Open access

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

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-H...O hydrogen bonds as well as weak intermolecular C-H...O interactions.

Related literature

For the biological activity of related compounds, see: Cartwright et al. (2007[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 (2000[Collins, I. (2000). J. Chem. Soc. Perkin Trans. 1 pp. 2845-2861.]); Warshakoon et al. (2006[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.]) and for their pharmaceutical activity, see: Kiselyov et al. (2006[Kiselyov, A. S., Semenova, M., Semenov, V. V. & Piatnitski, E. (2006). Bioorg. Med. Chem. Lett. 16, 1726-1730.]); Sakthivel & Cook (2005[Sakthivel, K. & Cook, P. D. (2005). Tetrahedron Lett. 46, 3883-3887.]); Eldrup et al. (2004[Eldrup, A. B., et al. (2004). J. Med. Chem. 47, 5284-5297.]); Bamford et al. (2005[Bamford, M. J., et al. (2005). Bioorg. Med. Chem. Lett. 15, 3402-3406.]); Puerstinger et al. (2006[Puerstinger, G., Paeshuyse, J., Herdewijn, P., Rozenski, J., Clercq, D. & Neyts, J. (2006). Bioorg. Med. Chem. Lett. 16, 5345-5349.]).

[Scheme 1]

Experimental

Crystal data
  • C23H26FN3O6S

  • Mr = 491.53

  • Monoclinic, P 21 /c

  • a = 11.926 (5) Å

  • b = 11.025 (5) Å

  • c = 18.508 (5) Å

  • [beta] = 97.271 (5)°

  • V = 2413.9 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.771, Tmax = 1.000

  • 21931 measured reflections

  • 4240 independent reflections

  • 3435 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.121

  • S = 1.04

  • 4240 reflections

  • 307 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N10-H10...O5i 0.86 2.08 2.924 (2) 168
N11-H11...O6ii 0.86 2.39 2.991 (3) 127
C20-H20A...O4iii 0.97 2.51 3.377 (3) 148
C31-H31...O4iv 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[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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


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.  [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CSD] [CrossRef] [ChemPort]
Collins, I. (2000). J. Chem. Soc. Perkin Trans. 1 pp. 2845-2861.
Eldrup, A. B., et al. (2004). J. Med. Chem. 47, 5284-5297.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Kiselyov, A. S., Semenova, M., Semenov, V. V. & Piatnitski, E. (2006). Bioorg. Med. Chem. Lett. 16, 1726-1730.  [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort]
Sakthivel, K. & Cook, P. D. (2005). Tetrahedron Lett. 46, 3883-3887.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o194-o195   [ doi:10.1107/S1600536811053980 ]

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