5,11-Dimethyl­dibenzo[b,f][1,5]diazocine-6,12(5H,11H)-dione

Mahon, A.B.; Jensen, P.; Try, A.C.

doi:10.1107/S1600536808001281

Volume 64
Part 2
Page o469
February 2008

Received 7 January 2008
Accepted 13 January 2008
Online 18 January 2008

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.038
wR = 0.105
Data-to-parameter ratio = 17.2
Details

5,11-Dimethyldibenzo[b,f][1,5]diazocine-6,12(5H,11H)-dione

Andrew B. Mahon,^a Paul Jensen ^b and Andrew C. Try ^a ^*

^aDepartment of Chemistry and Biomolecular Sciences, Building F7B, Macquarie University, NSW 2109, Australia, and ^bCrystal Structure Analysis Facility, School of Chemistry, F11, University of Sydney, NSW 2006, Australia
Correspondence e-mail: andrew.try@mq.edu.au

In the molecule of the title compound, C₁₆H₁₄N₂O₂, an N,N'-dimethyldianthranilide, the two methyl groups are disordered over two positions; site occupation factors were kept fixed as 0.75:0.25 and 0.65:0.35. The dihedral angle between the two benzene rings is 75.57 (3)°.

Related literature

For related literature, see: Nadkarni & Hosangadi (1988). For related structures, see: Ebert et al. (1998); Nonnenmacher et al. (2000); Gordon-Wylie et al. (2004); Olszewska et al. (2004).

Experimental

Crystal data

C₁₆H₁₄N₂O₂
M_r = 266.29
Monoclinic, P 2₁ /c
a = 11.2715 (10) Å
b = 7.9113 (7) Å
c = 15.4100 (14) Å
= 101.611 (1)°
V = 1346.0 (2) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 150 (2) K
0.55 × 0.42 × 0.24 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.901, T_max = 0.979
12897 measured reflections
3175 independent reflections
2686 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.104
S = 1.04
3175 reflections
185 parameters
1 restraint
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.23 e Å^-3

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: modiCIFer (Guzei, 2005).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2415 ).

Acknowledgements

The authors thank the Australian Research Council for a Discovery Project grant to ACT (grant No. DP0345180), and Macquarie University for the award of a Macquarie University Research Development grant to ACT and the award of a PhD scholarship to ABM.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (1998). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.
Ebert, B. M., Ugi, I. K., Grosche, M., Herdtweck, E. & Herrmann, W. A. (1998). Tetrahedron, 54, 11887-11898.
Gordon-Wylie, S. W., Teplin, E., Morris, J. C., Trombley, M. I., McCarthy, S. M., Cleaver, W. M. & Clark, G. R. (2004). Cryst. Growth Des. 4, 789-797.
Guzei, I. A. (2005). modiCIFer. Version Dec-16-2005. University of Wisconsin-Madison, Madison, Wisconsin, USA.
Nadkarni, S. S. & Hosangadi, B. D. (1988). Indian J. Chem. Sect. B, 27, 225-228.
Nonnenmacher, E., Brouant, P., Mrozek, A., Karolak-Wojciechowska, J. & Barbe, J. (2000). J. Mol. Struct. 522, 263-269.
Olszewska, T., Gdaniec, M. & Polonski, T. (2004). J. Org. Chem. 69, 1248-1255.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds