N-[3-(tert-Butyl­dimethyl­siloxymeth­yl)-5-nitro­phen­yl]acetamide

Khan, G.S.; Clark, G.R.; Barker, D.

doi:10.1107/S1600536808030717

Volume 64
Part 10
Page o2031
October 2008

Received 12 September 2008
Accepted 24 September 2008
Online 27 September 2008

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.117
Data-to-parameter ratio = 16.1
Details

N-[3-(tert-Butyldimethylsiloxymethyl)-5-nitrophenyl]acetamide

Gul S. Khan,^a George R. Clark ^a ^* and David Barker ^a

^aChemistry Department, University of Auckland, Private Bag 92019, Auckland, New Zealand
Correspondence e-mail: g.clark@auckland.ac.nz

The title compound, C₁₅H₂₄N₂O₄Si, was prepared by the reaction of (3-acetamido-5-nitrobenzyl)methanol with tert-butyldimethylsilyl chloride and is a key intermediate in the synthesis of novel nonsymmetrical DNA minor groove-binding agents. There are two independent molecules in the structure, which differ primarily in the rotation about the C-O bond next to the Si atom. Two strong N-HO hydrogen bonds align the molecules into a wide ribbon extending approximately parallel to the b axis.

Related literature

For literature related to protecting groups, see: Jarowicki & Kocienski (1998); Kocienski (2004); Schelhaas & Waldmann (1996); Wetter & Oertle (1985); Wuts & Green (2006). For literature related to benzamides as minor groove binders, see: Barker et al. (2008); Gong & Yan (1997). For related literature, see: Crouch (2004); Desiraju & Steiner (1999); Nelson & Crouch (1996).

Experimental

Crystal data

C₁₅H₂₄N₂O₄Si
M_r = 324.45
Triclinic, $[P \overline 1]$
a = 9.5037 (3) Å
b = 10.0713 (3) Å
c = 18.1985 (5) Å
= 89.885 (1)°
= 86.009 (1)°
= 88.888 (1)°
V = 1737.31 (9) Å³
Z = 4
Mo K radiation
= 0.15 mm^-1
T = 90 (2) K
0.34 × 0.22 × 0.20 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) T_min = 0.878, T_max = 0.977
15951 measured reflections
6570 independent reflections
4732 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.117
S = 1.05
6570 reflections
409 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1AO1B	0.86	2.13	2.982 (2)	172
N1B-H1BO1Aⁱ	0.86	2.14	2.991 (2)	173
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 1995); cell refinement: SAINT (Bruker, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2117 ).

Acknowledgements

The authors acknowledge financial support from the Higher Education Commission of Pakistan and The University of Auckland, New Zealand.

References

Barker, D., Lehmann, A. L., Mai, A., Khan, G. S. & Ng, E. (2008). Tetrahedron Lett. 49, 1660-1664.
Bruker (1995). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Crouch, R. D. (2004). Tetrahedron, 60, 5833-5871.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond. IUCr Monographs on Crystallography 9. New York: Oxford University Press.
Gong, B. & Yan, Y. (1997). Biochem. Biophys. Res. Commun. 240, 557-560.
Jarowicki, K. & Kocienski, P. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 4005-4037.
Kocienski, P. J. (2004). Protein Groups, 3rd ed. New York, Stuttgart: Georg Thieme.
Nelson, T. D. & Crouch, R. D. (1996). Synthesis, 9, 1031-1069.
Schelhaas, M. & Waldmann, H. (1996). Angew. Chem. Int. Ed. 35, 2056-2083.
Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wetter, H. & Oertle, K. (1985). Tetrahedron Lett. 26, 5515-5518.
Wuts, P. G. & Green, T. W. (2006). Protective Groups in Organic Synthesis, 4th ed. Hoboken: Wiley.

organic compounds