5-p-Tolyl-1,2,3,3a-tetra­hydro­benzo[e]pyrrolo­[2,1-b][1,3]oxazepin-10(5H)-one

Jin, Y.-Z.; Liu, C.-E.; Zhang, R.-H.; Fu, D.-X.; Lv, Y.-K.

doi:10.1107/S1600536811020964

Volume 67
Part 7
Page o1593
July 2011

Received 11 May 2011
Accepted 31 May 2011
Online 11 June 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.053
wR = 0.188
Data-to-parameter ratio = 17.6
Details

5-p-Tolyl-1,2,3,3a-tetrahydrobenzo[e]pyrrolo[2,1-b][1,3]oxazepin-10(5H)-one

Yun-Zhou Jin,^a Cai-E Liu,^a Rong-Hua Zhang,^a ^* Da-Xu Fu ^a and Yao-Kang Lv ^a

^aChemistry Department, Tongji University, Shanghai 200092, People's Republic of China
Correspondence e-mail: tj_zrh@163.com

The structure of the title compound, C₁₉H₁₉NO₂, contains a seven-membered ring, which is fused to one five- and one six-membered ring, and carries a tolyl substituent. The two benzene rings are oriented relative to each other at a dihedral angle of 86.90 (7)°. In the crystal, molecules are linked by weak intermolecular C-HO hydrogen bonds.

Related literature

For general background to asymmetric photochemical reactions, see: Gould et al. (2001); Grätzel (2001); Korzeniewski & Zoladz (2001); Aubert et al. (2000). For related structures, see: Basaric et al. (2008); Griesbeck et al. (1997, 1999, 2002).

Experimental

Crystal data

C₁₉H₁₉NO₂
M_r = 293.35
Monoclinic, P 2₁ /c
a = 8.237 (3) Å
b = 16.868 (6) Å
c = 11.267 (4) Å
= 100.851 (6)°
V = 1537.6 (10) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 296 K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) T_min = 0.736, T_max = 1.000
13060 measured reflections
3501 independent reflections
2338 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.188
S = 1.01
3501 reflections
199 parameters
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5BO2ⁱ	0.96	2.42	3.354 (3)	163
C17-H17AO2ⁱⁱ	0.98	2.38	3.357 (3)	174
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2004); 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: EZ2247 ).

Acknowledgements

Financial support from the National Natural Science Foundation of China is gratefully acknowledged.

References

Aubert, C., Vos, M. H., Mathis, P., Eker, A. P. M. & Brettel, K. (2000). Nature (London), 405, 586-590.
Basaric, N., Horvat, M., Mlinaric-Majerski, K., Zimmermann, E., Neudörfl, J. & Griesbeck, A. G. (2008). Org. Lett. 10, 3965-3968.
Brandenburg, K. & Putz, H. (2004). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gould, I. R., Lenhard, J. R., Muenter, A. A., Godleski, S. A. & Farid, S. Y. (2001). Pure Appl. Chem. 73, 455-458.
Grätzel, M. (2001). Pure Appl. Chem. 73, 459-467.
Griesbeck, A. G., Heinrich, T., Oelgemöller, M., Heidtmann, A. & Molis, A. (2002). Helv. Chim. Acta, 85, 4561-4578.
Griesbeck, A. G., Henz, A., Kramer, W., Lex, J., Nerowski, F., Oelgemöller, M., Peters, K. & Peters, E.-M. (1997). Helv. Chim. Acta, 80, 912-933.
Griesbeck, A. G., Nerowski, F. & Lex, J. (1999). J. Org. Chem. 64, 5213-5217.
Korzeniewski, B. & Zoladz, J. A. (2001). Biophys. Chem. 92, 17-34.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds