2,2-Dimethyl-5-{[(4-nitro­phen­yl)amino]­methyl­idene}-1,3-dioxane-4,6-dione

Yang, Y.-H.; Li, Z.-C.; Luo, Y.-F.

doi:10.1107/S1600536811001103

Volume 67
Part 2
Page o412
February 2011

Received 10 December 2010
Accepted 8 January 2011
Online 15 January 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.052
wR = 0.126
Data-to-parameter ratio = 14.3
Details

2,2-Dimethyl-5-{[(4-nitrophenyl)amino]methylidene}-1,3-dioxane-4,6-dione

Ying-Hong Yang,^a Zi-Cheng Li ^a and You-Fu Luo ^a,^b ^*

^aDepartment of Pharmaceutical and Bioengineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China, and ^bState Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, People's Republic of China
Correspondence e-mail: luo_youfu@foxmail.com

In the title compound, C₁₃H₁₂N₂O₆, the dihedral angle between the benzene ring and the aminomethylene unit is 5.42 (16)°, while the angle between the aminomethylene unit and the dioxane ring is 3.06 (43)°. The dioxane ring shows a half-boat conformation, in which the C atom between the dioxane ring O atoms is 0.464 (10) Å out of the plane. An intramolecular N-HO hydrogen bond stabilizes the molecular conformation. In the crystal, a three-dimensional framework is built up via intermolecular N-HO hydrogen bonds.

Related literature

For the synthesis and biological activity of related compounds, see: Cassis et al. (1985); Griera et al. (1997); Darque et al. (2009).

Experimental

Crystal data

C₁₃H₁₂N₂O₆
M_r = 292.25
Monoclinic, P 2₁ /c
a = 12.2822 (8) Å
b = 12.2762 (7) Å
c = 9.2760 (6) Å
= 106.636 (7)°
V = 1340.08 (15) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 293 K
0.22 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.933, T_max = 1.0
6063 measured reflections
2741 independent reflections
1432 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.126
S = 1.00
2741 reflections
192 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O3ⁱ	0.86	2.65	3.411 (3)	148
N2-H2O4	0.86	2.15	2.771 (2)	129
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov, 2009); software used to prepare material for publication: OLEX2.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PB2051 ).

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

Cassis, R., Tapia, R. & Valderrama, J. A. (1985). Synth. Commun. 15, 125-133.
Darque, A., Dumetre, A., Hutter, S., Casano, G., Robin, M., Pannecouque, C. & Azas, N. (2009). Bioorg. Med. Chem. Lett. 19, 5962-5964.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Griera, R., Armengol, M., Reyes, A., Alvarez, M., Palomer, A., Cabre, F., Pascual, J., Garcia, M. L. & Mauleon, D. (1997). Eur. J. Med. Chem. 32, 547-570.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds