2-(4,5,6,7,8,9-Hexahydro-6a-aza­phenyl­en-2-ylmethyl­ene)indan-1,3-dione

Belyakov, S.; Kampars, V.; Pastors, P.J.; Tokmakov, A.

doi:10.1107/S1600536808016346

Volume 64
Part 7
Page o1200
July 2008

Received 19 May 2008
Accepted 29 May 2008
Online 7 June 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.055
wR = 0.155
Data-to-parameter ratio = 14.5
Details

2-(4,5,6,7,8,9-Hexahydro-6a-azaphenylen-2-ylmethylene)indan-1,3-dione

Sergey Belyakov,^a ^* Valdis Kampars,^b Pauls J. Pastors ^b and Andrey Tokmakov ^a

^aLatvian Institute of Organic Synthesis, Riga LV 1006, Latvia, and ^bDepartment of Materials Science and Applied Chemistry, Riga Technical University, LV 1046, Latvia
Correspondence e-mail: serg@osi.lv

The title compound, C₂₂H₁₉NO₂, has potential for use as a new nonlinear optical material. Molecules are almost planar. One C atom of the heterocyclic ring system is disordered over two positions; the site occupancy factors are 0.6 and 0.4.

Related literature

For related literature, see: Honda et al. (1996); Allen (2002).

Experimental

Crystal data

C₂₂H₁₉NO₂
M_r = 329.38
Monoclinic, P 2₁ /n
a = 8.5125 (2) Å
b = 19.2973 (5) Å
c = 10.4969 (3) Å
= 109.5301 (10)°
V = 1625.10 (7) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 (2) K
0.26 × 0.19 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
6190 measured reflections
3685 independent reflections
2852 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.155
S = 1.01
3685 reflections
255 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.39 e Å^-3

Data collection: KappaCCD Server Software (Nonius, 1999); cell refinement: KappaCCD Server Software; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: maXus (Mackay et al., 1999) and SIR92 (Altomare et al., 1994); program(s) used to refine structure: maXus and SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (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: RK2090 ).

Acknowledgements

The authors acknowledge financial support from the Latvian Council of Science.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Honda, T., Fujii, I., Hirayama, N., Aoyama, N. & Miike, A. (1996). Acta Cryst. C52, 364-365.
Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (1999). maXus. Bruker-Nonius, Delft, The Netherlands, MacScience, Yokohama, Japan, and The University of Glasgow, Scotland.
Nonius (1999). KappaCCD Server Software. 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 & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds