1,1,3-Trimethyl-3-(4-nitro­phen­yl)indane

Men, J.; Yi, S.-X.; Bo, F.; Chen, H.; Gao, G.-W.

doi:10.1107/S1600536808027633

Volume 64
Part 11
Page o2192
November 2008

Received 21 July 2008
Accepted 28 August 2008
Online 25 October 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.051
wR = 0.148
Data-to-parameter ratio = 14.3
Details

1,1,3-Trimethyl-3-(4-nitrophenyl)indane

Jian Men,^a Shi-Xu Yi,^a Fang Bo,^a Hua Chen ^a and Guo-Wei Gao ^a ^*

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
Correspondence e-mail: gaosunday@yahoo.com.cn

In the title compound, C₁₈H₁₉NO₂, the five-membered ring of the indane fragment adopts an envelope conformation, with the unsubstituted C atom, acting as the flap atom, deviating by 0.412 (3) Å from the plane through the remaining four atoms. The dihedral angle between the nitrophenyl ring and the indane benzene ring is 72.5 (1)°. The distances from the two O atoms to the plane of the adjacent benzene ring are 0.113 (4) and 0.064 (4) Å.

Related literature

For related literature, see: Bateman & Gordon (1976); Bezdek & Hrabak et al. (1979); Kumar et al. (1983); Men et al. (2008); Hanaineh-Abdelnour et al. (1999).

Experimental

Crystal data

C₁₈H₁₉NO₂
M_r = 281.34
Monoclinic, P 2₁ /c
a = 11.305 (4) Å
b = 11.422 (2) Å
c = 11.963 (2) Å
= 102.32 (4)°
V = 1509.1 (7) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 294 (2) K
0.48 × 0.42 × 0.40 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
3836 measured reflections
2808 independent reflections
1569 reflections with I > 2(I)
R_int = 0.005
3 standard reflections every 200 reflections intensity decay: 0.3%

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.148
S = 1.02
2808 reflections
197 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.18 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: KJ2096 ).

Acknowledgements

The authors are grateful to the National Undergraduates' Innovative Experiment Project of China for financial support and thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

Bateman, J. & Gordon, D. A. (1976). US Patent 3 983 092.
Bezdek, M. & Hrabak, F. J. (1979). Polym. Sci. Polym. Chem. Ed. 17, 2857.
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). American Crystallographic Association Pittsburgh Meeting, Abstract PA104.
Hanaineh-Abdelnour, L., Bayyuk, S. & Theodorie, R. (1999). Tetrahedron, 50, 11859-11870.
Kumar, D., Fohlen, G. M. & Parker, J. A. (1983). Macromol. Chem. 16, 1250-1257.
Men, J., Yang, M.-J., Jiang, Y., Chen, H. & Gao, G.-W. (2008). Acta Cryst. E64, o847.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds