rac-(Z)-Methyl 1-benzyl-3-[(3-hy­droxy­quinuclidin-2-yl­idene)meth­yl]-1H-indole-6-carboxyl­ate

Penthala, N.R.; Ponugoti, P.R.; Parkin, S.; Crooks, P.A.

doi:10.1107/S1600536812040731

Volume 68
Part 11
Page o3111
November 2012

Received 13 August 2012
Accepted 26 September 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.039
wR = 0.102
Data-to-parameter ratio = 14.7
Details

rac-(Z)-Methyl 1-benzyl-3-[(3-hydroxyquinuclidin-2-ylidene)methyl]-1H-indole-6-carboxylate

Narsimha Reddy Penthala,^a Purushotham Rao Ponugoti,^a Sean Parkin ^b and Peter A. Crooks ^a ^*

^aDept. of Pharm. Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA, and ^bDept. of Chemistry, University of Kentucky, Lexington KY 40506, USA
Correspondence e-mail: pacrooks@uams.edu

In the title compound, C₂₅H₂₆N₂O₃, the double bond connecting the aza-bicyclic and indole units has Z geometry. The compound was obtained as a racemate, and since the crystal is centrosymmetric it contains equal amounts of the S and R enantiomers. However, the structure is disordered such that the asymmetric unit contains both enantiomers in unequal amounts [refined occupancies 0.904 (2) and 0.096 (2)]. The dihedral angle between the benzene ring of the benzyl group and the mean plane of the indole ring is 76.07 (3) °. In the crystal, molecules are linked by O-HO_carbonyl hydrogen bonds into chains propagating in [110].

Related literature

For background literature, see: Sekhar et al., (2003), Amudhan et al., (2010). For the biological activity of N-benzyl indole quinuclidinone, see: Sonar et al. (2007). For a similar crystal structure, see: Sonar et al., (2004).

Experimental

Crystal data

C₂₅H₂₆N₂O₃
M_r = 402.48
Triclinic, $[P \overline 1]$
a = 6.1619 (1) Å
b = 10.3119 (2) Å
c = 16.5959 (3) Å
= 75.6705 (7)°
= 80.0939 (7)°
= 85.9410 (7)°
V = 1006.04 (3) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 90 K
0.28 × 0.22 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
9126 measured reflections
4597 independent reflections
3831 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.102
S = 1.04
4597 reflections
312 parameters
64 restraints
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO2ⁱ	0.84	1.97	2.7989 (13)	169
Symmetry code: (i) x-1, y-1, z.

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); 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: SHELXL97 and local procedures.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5242 ).

Acknowledgements

This investigation was supported by NIH/National Cancer Institute grant PO1 CA140409.

References

Amudhan, V., Reddy, Y. T., Sonar, V. N., Venkatraj, M., Crooks, P. A., Michael, L., Freeman, M. L. & Sekhar, K. R. (2010). Bioorg. Med. Chem. Lett. 20, 7323-7326.
Nonius (1998). COLLECT. Nonius, BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307-326. New York: Academic Press.
Sekhar, K. R., Crooks, P. A., Sonar, V. N., Friedman, D. B., Chan, J. Y., Meredith, M. J., Stames, J. H., Kelton, K. R., Summar, S. R., Sasi, S. & Freeman, M. L. (2003). Cancer Res. 63, 5636-5645.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sonar, V. N., Parkin, S. & Crooks, P. A. (2004). Acta Cryst. C60, o659-o661.
Sonar, V. N., Reddy, Y. T., Sekhar, K. R., Sowmya, S., Freeman, M. L. & Crooks, P. A. (2007). Bioorg. Med. Chem. Lett. 17(24), 6821-6824.

organic compounds