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

Andrew B Mahon; Paul Jensen; Andrew C Try

doi:10.1107/S1600536808001281

. 2008 Jan 18;64(Pt 2):o469. doi: 10.1107/S1600536808001281

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

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

PMCID: PMC2960302 PMID: 21201495

Abstract

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,
a = 11.2715 (10) Å
b = 7.9113 (7) Å
c = 15.4100 (14) Å
β = 101.611 (1)°
V = 1346.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.104
S = 1.04
3175 reflections
185 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001281/hk2415sup1.cif

e-64-0o469-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001281/hk2415Isup2.hkl

e-64-0o469-Isup2.hkl^{(155.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

Several structures of the unsubstituted dianthranilide (i.e., lacking methyl groups on the nitrogen atoms) are present in the literature, including ethanol, DMF and pyridine solvates of racemic material (Gordon-Wylie et al., 2004) as well as a DMSO solvate of racemic material, unsolvated racemate and a DMSO solvate of enantiomerically pure crystals (Olszewska et al., 2004).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges. When the crystal structure was solved, the two methyl groups were found to be disordered. The dihedral angle between the two benzene rings is 75.57 (3)°.

The X-ray crystal structures of three N,N'-disubstituted dianthranilides have also been reported and in all cases they have a smaller dihedral angle between the two aryl rings of the dianthranilide in comparison with the structures of the unsubstituted compounds. The N,N'-di[1-(N-t-butylcarbamoyl)-1-(cyclohexyl)- methyl] (Ebert et al., 1998), N,N'-dibenzyl (Nonnenmacher et al., 2000) and N,N'-dicamphanoyl derivatives (Olszewska et al., 2004) have dihedral angles of 78.2, 83.9 and 77.5°, respectively.

Experimental

The title compound was prepared according to the literature procedure (Nadkarni & Hosangadi, 1988) in 89% yield. Single crystals of (I) were produced from slow evaporation of a dichloromethane solution.