1,3,3-Trimethyl-5-nitro-1-phenyl­indane

Ma, X.-Y.; Wu, D.-F.; Wang, Y.; Gao, G.-W.; Men, J.

doi:10.1107/S1600536810005647

Volume 66
Part 3
Page o645
March 2010

Received 30 January 2010
Accepted 10 February 2010
Online 17 February 2010

Key indicators
Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.004 Å
R = 0.057
wR = 0.195
Data-to-parameter ratio = 12.8
Details

1,3,3-Trimethyl-5-nitro-1-phenylindane

Xiao-Yan Ma,^a Di-Feng Wu,^b Yang Wang,^b Guo-Wei Gao ^b and Jian Men ^b ^*

^aCollege of Material and Chemical Engineering, Chengdu University of Technology, Chengdu 610059, People's Republic of China, and ^bDepartment of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
Correspondence e-mail: menjian@scu.edu.cn

In the title compound, C₁₈H₁₉NO₂, the five-membered ring of the indane fragment adopts an envelope conformation with the unsubstituted carbon atom at the flap displaced by 0.412 (3) Å from the plane formed by the other four atoms. The nitro group forms a dihedral angle of 5.3 (2)° with the indane benzene ring while the dihedral angle between the phenyl ring and the indane benzene ring is 76.74 (9)°.

Related literature

For general background to the synthesis, properties and applications of indane and its derivatives, see: Clark et al. (1998); Numata et al. (1976); Aliakbar et al. (2007). For a related structure, see: Men et al. (2008).

Experimental

Crystal data

C₁₈H₁₉NO₂
M_r = 281.34
Monoclinic, P 2₁ /c
a = 8.306 (3) Å
b = 17.600 (3) Å
c = 12.090 (4) Å
= 120.50 (3)°
V = 1522.8 (9) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 292 K
0.58 × 0.48 × 0.42 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
3123 measured reflections
2750 independent reflections
1600 reflections with I > 2(I)
R_int = 0.009
3 standard reflections every 200 reflections intensity decay: 2.1%

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.195
S = 1.12
3524 reflections
275 parameters
H-atom parameters constrained
_max = 0.52 e Å^-3
_min = -0.40 e Å^-3

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2417 ).

Acknowledgements

The authors gratefully thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

Aliakbar, T., Abdelkhalek, R. & Jacques, M. (2007). Catal. Commun. 8, 1153-1155.
Clark, W. M., Tickner-Eldridge, A. M., Huang, G. K.,Pridgen, L. N., Olsen, M. A., Mills, R. J., Lantos, I. & Baine, N. H. (1998). J. Am. Chem. Soc. 120, 4550-4551.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association Meeting, Pittsburgh, Abstract PA 104.
Men, J., Yang, M.-J., Jiang, Y., Chen, H. & Gao, G.-W. (2008). Acta Cryst. E64, o847.
Numata, S., Tsutomu, T. & Toshio, T. (1976). US Patent 3985818.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds