Diethyl [(3-cyano-1-phenyl­sulfonyl-1H-indol-2-yl)meth­yl]phospho­nate

Karthikeyan, S.; Sethusankar, K.; Rajeshwaran, G.G.; Mohanakrishnan, A.K.; Velmurugan, D.

doi:10.1107/S1600536811008038

Volume 67
Part 4
Pages o818-o819
April 2011

Received 23 February 2011
Accepted 3 March 2011
Online 9 March 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.042
wR = 0.126
Data-to-parameter ratio = 18.2
Details

Diethyl [(3-cyano-1-phenylsulfonyl-1H-indol-2-yl)methyl]phosphonate

S. Karthikeyan,^a K. Sethusankar,^a ^* Ganesan Gobi Rajeshwaran,^b Arasambattu K. Mohanakrishnan ^b and D. Velmurugan ^c

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India,^bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C₂₀H₂₁N₂O₅PS, the indole ring is essentially planar, with a maximum deviation of -0.0083 (18) Å. The methyl C atom of the methylphosphonate group and the S atom lie 0.104 (2) and -0.2158 (6) Å, respectively, from the indole mean plane. The sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system, with a dihedral angle of 82.30 (8)°. The ethyl side chains are disordered over two sets of sites, with occupancy factors of 0.737 (5)/0.263 (5) and 0.529 (11)/0.471 (11). In the crystal, molecules are linked into centrosymmetric dimers via C-HO hydrogen bonds, resulting in an R₂²(18) graph-set motif. The crystal structure is further stabilized by C-H [pi] interactions.

Related literature

For applications of indole derivatives, see: Stevenson et al. (2000); Ho et al. (1986); Rajeswaran et al. (1999). For comparison of molecular dimensions, see: Bassindale (1984); Sethu Sankar et al. (2002); Allen (1981). For graph-set motif notations, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₀H₂₁N₂O₅PS
M_r = 432.42
Triclinic, $[P \overline 1]$
a = 9.198 (5) Å
b = 11.229 (5) Å
c = 11.992 (5) Å
= 65.569 (5)°
= 72.950 (5)°
= 72.204 (5)°
V = 1053.7 (9) Å³
Z = 2
Mo K radiation
= 0.26 mm^-1
T = 293 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
19331 measured reflections
5172 independent reflections
4201 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.126
S = 1.02
5172 reflections
284 parameters
10 restraints
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9/C10/C11/C12/C13/C14 ring and Cg2 is the centroid of the C1/C2/C3/C4/C5/C6 ring.

D-HA	D-H	HA	DA	D-HA
C10-H10O5ⁱ	0.93	2.35	3.229 (3)	157
C5-H5Cg1ⁱⁱ	0.93	2.63	3.501 (3)	157
C18-H18ACg2ⁱⁱⁱ	0.96	2.99	3.874 (8)	154
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+2; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: PV2393 ).

Acknowledgements

SK and KS thank the Technology Business Incubator (TBI), CAS in Crystallography and Biophysics, University of Madras, Maraimalai Campus, Chennai, and the Department of Science and Technology (DST) for data collection.

References

Allen, F. H. (1981). Acta Cryst. B37, 900-906.
Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Ho, C. Y., Haegman, W. E. & Perisco, F. (1986). J. Med. Chem. 29, 118-121.
Rajeswaran, W. G., Labroo, R. B., Cohen, L. A. & King, M. M. (1999). J. Org. Chem. 64, 1369-1371.
Sethu Sankar, K., Kannadasan, S., Velmurugan, D., Srinivasan, P. C. & Moon, J.-K. (2002). Acta Cryst. C58, o450-o454.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stevenson, G. I., Smith, A. L., Lewis, S. G., Nedevelil, J. G., Patel, S., Marwood, R. & Castro, J. L. (2000). Bioorg. Med. Chem. Lett. 10, 2697-2704.

organic compounds