N-[3-(4-Fluoro­benz­yl)-2,4-dioxo-1,3-diaza­spiro­[4.5]dec-8-yl]-2-methyl­benzene­sulfonamide

Jeyaseelan, S.; Vinduvahini, M.; Madaiah, M.; Bhattacharya, S.; Revanasiddappa, H.D.

doi:10.1107/S160053681105269X

Volume 68
Part 1
Pages o105-o106
January 2012

Received 16 November 2011
Accepted 7 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.114
Data-to-parameter ratio = 13.2
Details

N-[3-(4-Fluorobenzyl)-2,4-dioxo-1,3-diazaspiro[4.5]dec-8-yl]-2-methylbenzenesulfonamide

S. Jeyaseelan,^a M. Vinduvahini,^b ^* M. Madaiah,^c Suman Bhattacharya ^d and H. D. Revanasiddappa ^c

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India,^bDepartment of Physics, Sri D. Devaraja Urs Govt. First Grade College, Hunsur 571 105, Mysore District, Karnataka, India,^cDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, Karnataka, India, and ^dDepartment of Chemistry, Pondicherry, University, Pondicherry 605 014, India
Correspondence e-mail: vinduvahinim@yahoo.in

In the title compound, C₂₂H₂₄FN₃O₄S, the cyclohexane ring adopts a chair conformation and the five-membered ring is essentially planar, with a maximum deviation of 0.040 (2) Å. The dihedral angles between the five-membered ring and the tolyl and fluorobenzene rings are 56.74 (12) and 89.88 (12)°, respectively. The two terminal benzene rings make a dihedral angle of 63.53 (12)°. The crystal structure displays intermolecular C-HO and N-HO hydrogen bonds. An intramolecular C-HO hydrogen bond also occurs.

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

C₂₂H₂₄FN₃O₄S
M_r = 445.50
Monoclinic, P 2₁ /c
a = 5.8314 (3) Å
b = 26.3603 (11) Å
c = 13.8558 (7) Å
= 98.623 (5)°
V = 2105.80 (18) Å³
Z = 4
Mo K radiation
= 0.20 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
23208 measured reflections
3693 independent reflections
3034 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.114
S = 1.06
3693 reflections
280 parameters
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N7-H7O4ⁱ	0.86	2.04	2.885 (2)	166
N9-H9O6ⁱⁱ	0.86	2.24	3.013 (2)	149
C12-H12O3ⁱⁱⁱ	0.93	2.59	3.290 (3)	132
C31-H31AO6	0.96	2.20	2.973 (3)	137
C31-H31CO5^iv	0.96	2.47	3.238 (3)	137
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z; (iii) x+1, y, z; (iv) x-1, y, z.

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: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); 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: WN2460 ).

Acknowledgements

The authors thank Dr Binoy Krishna Saha, Department of Chemistry, Pondicherry University, for the data collection and Dr H. C. Devarajegowda, Department of Physics, Yuvaraja's Collage, University of Mysore, for his help and encouragement.

References

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Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.

organic compounds