Dimethyl [1-(1-allyl-5-iodo-1H-indol-3-yl)-3-hydroxy­prop­yl]phospho­nate

Guo, Y.-C.; Wang, X.-F.; Ding, Y.

doi:10.1107/S1600536807068171

Volume 64
Part 2
Page o384
February 2008

Received 29 November 2007
Accepted 21 December 2007
Online 9 January 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.007 Å
R = 0.043
wR = 0.102
Data-to-parameter ratio = 16.9
Details

Dimethyl [1-(1-allyl-5-iodo-1H-indol-3-yl)-3-hydroxypropyl]phosphonate

Ying-Cen Guo,^a Xu-Fan Wang ^a and Yu Ding ^a ^*

^aKey Laboratory of Pesticides and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
Correspondence e-mail: dingyu508@gmail.com

In the title compound, C₁₆H₂₁INO₄P, the molecular structure is stabilized by a weak intramolecular C-HO hydrogen-bond interaction. The crystal packing is stabilized by strong intermolecular O-H O hydogen-bonding interactions to form a zigzag packing arrangement.

Related literature

For asymmetric synthesis of phosphorus compounds, see: Carlone et al. (2007); Yang, et al. (2007); Ibrahem et al. (2007). For related structures, see: Sonar et al. (2006); Chen et al. (2007); Butcher et al. (2007). For related literature, see: Allen et al. (1989); Horiguchi & Kandatsu (1959).

Experimental

Crystal data

C₁₆H₂₁INO₄P
M_r = 449.21
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.9983 (4) Å
b = 10.1295 (6) Å
c = 22.3722 (12) Å
V = 1812.57 (17) Å³
Z = 4
Mo K radiation
= 1.87 mm^-1
T = 294 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) T_min = 0.706, T_max = 0.835
10836 measured reflections
3564 independent reflections
3314 reflections with I > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.102
S = 1.04
3564 reflections
211 parameters
H-atom parameters constrained
_max = 0.69 e Å^-3
_min = -0.30 e Å^-3
Absolute structure: Flack (1983), 1503 Freidel pairs
Flack parameter: 0.00 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O1	0.98	2.47	2.873 (7)	104
O1-H1O4ⁱ	0.82	1.92	2.733 (6)	174
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2520 ).

Acknowledgements

The authors acknowledge financial support from the Natural Science Foundation of Hubei Province of China (No. 2006ABA175) and the Natural Science Foundation of Central China Normal University, and are indebted to Dr Guangmin Yao of Shijiazhuang Pharmaceutical Group, Zhongqi (sjz) Pharmaceutical Technology Co. Ltd, and Professor Wenjing Xiao and Dr Xianggao Meng of Central China Normal University, for their advice and support.

References

Allen, M. C., Fuhrer, W. & Tuck, B. (1989). J. Med. Chem. 32, 1652-1661.
Bruker (2001). SMART (Version 5.628), SAINT (Version 6.45) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Ashalatha, B. V. & Narayana, B. (2007). Acta Cryst. E63, o3505.
Carlone, A., Bartoli, G. & Bosco, M. (2007). Angew. Chem. Int. Ed. 46, 4504-4506.
Chen, A., Zou, J.-W. & Zhao, W.-N. (2007). Acta Cryst. E63, o3229.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Horiguchi, M. & Kandatsu, M. (1959). Nature (London), 184, 901.
Ibrahem, I., Rios, R. & Vesely, J. (2007). Angew. Chem. Int. Ed. 46, 4507-4510.
Sheldrick, G. M. (1997). SADABS and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sonar, V. N., Parkin, S. & Crooks, P. A. (2006). Acta Cryst. E62, o3328-o3330.
Yang, H., Hong, Y.-T. & Kim, S. (2007). Org. Lett. 9, 2281-2284.

organic compounds