(IUCr) Diethyl 2-[(5-methoxy-2-methyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate

Volume 65
Part 6
Pages o1418-o1419
June 2009

Received 31 March 2009
Accepted 21 May 2009
Online 29 May 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.053
wR = 0.176
Data-to-parameter ratio = 20.1
Details

Diethyl 2-[(5-methoxy-2-methyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate

T. Kavitha,^a M. Thenmozhi,^a V. Dhayalan,^b A. K. Mohanakrishnan ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C₂₄H₂₅NO₇S, the sulfonyl-bound phenyl ring is approximately perpendicular to the indole ring system [dihedral angle = 87.72 (5)°]. The methyl group of one of the ester units is disordered over two positions with occupancies of 0.527 (13) and 0.473 (13). An intramolecular C-HO hydrogen bond is observed. In the crystal structure, molecules are linked into a ribbon structure running along the c axis by intermolecular C-HO hydrogen bonds and C-H [pi] interactions involving the pyrrole ring.

Related literature

For general background on indoles, see: El-Sayed et al. (1986); Farhanullah et al. (2004); Okabe & Adachi (1998); Schollmeyer et al. (1995). For the Thorpe-Ingold effect, see: Bassindale (1984). For hybridization, see: Beddoes et al. (1986). For a related structure, see: Chakkaravarthi et al. (2008).

Experimental

Crystal data

C₂₄H₂₅NO₇S
M_r = 471.51
Triclinic, $[P \overline 1]$
a = 8.7597 (2) Å
b = 10.9029 (2) Å
c = 12.5186 (3) Å
= 88.402 (1)°
= 79.723 (1)°
= 83.635 (2)°
V = 1169.13 (4) Å³
Z = 2
Mo K radiation
= 0.18 mm^-1
T = 293 K
0.22 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.964, T_max = 0.971
27454 measured reflections
6218 independent reflections
4628 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.176
S = 1.07
6218 reflections
309 parameters
16 restraints
H-atom parameters constrained
_max = 0.66 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C2-C5 ring.

D-HA	D-H	HA	DA	D-HA
C6-H6O1	0.93	2.32	2.901 (3)	120
C14-H14O5ⁱ	0.93	2.42	3.349 (3)	173
C25-H25CCg1ⁱⁱ	0.96	2.92	3.515 (3)	140
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y+1, -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: CI2774 ).

Acknowledgements

TK thanks Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection.

References

Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.
Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o1139.
El-Sayed, K., Barnhart, D. M., Ammon, H. L. & Wassel, G. M. (1986). Acta Cryst. C42, 1383-1385.
Farhanullah, S. A., Maulik, P. R. & Ji Ram, V. (2004). Tetrahedron Lett. 45, 5099-5102.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.
Schollmeyer, D., Fischer, G. & Pindur, U. (1995). Acta Cryst. C51, 2572-2575.
Sheldrick, G. M. (2001). SADABS. University of Gottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds