3,3′-Ethyl­enebis(3,4-dihydro-6-chloro-2H-1,3-benzoxazine)

Rivera, A.; Rojas, J.J.; Ríos-Motta, J.; Dušek, M.; Fejfarová, K.

doi:10.1107/S1600536810014248

Volume 66
Part 5
Page o1134
May 2010

Received 29 March 2010
Accepted 18 April 2010
Online 21 April 2010

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.030
wR = 0.103
Data-to-parameter ratio = 13.2
Details

3,3'-Ethylenebis(3,4-dihydro-6-chloro-2H-1,3-benzoxazine)

Augusto Rivera,^a ^* Jicli José Rojas,^a Jaime Ríos-Motta,^a Michal Dusek ^b and Karla Fejfarová ^b

^aDepartamento de Química, Universidad Nacional de Colombia, Bogotá, AA 14490, Colombia, and ^bInstitute of Physics, Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

The asymmetric unit of the title compound, C₁₈H₁₈Cl₂N₂O₂, contains one half of an independent molecule, the other half being generated via a centre of inversion at the molecular centroid. In the crystal structure, molecular chains are formed through non-classical C-H O hydrogen bonds between an axial H atom of the oxazine ring and the O atom of a neighbouring molecule.

Related literature

For the synthesis, see: Rivera et al. (1989). For related structures, see: Rivera et al. (1986); Huerta et al. (2006); Chen & Wu (2007); Ranjith et al. (2009). For uses of benzoxazines in polymer science, see Yaggi et al. (2009). For the biological activity of bis-benzoxazine compounds, see: Billmann & Dorman (1963); Heinisch et al. (2002).

Experimental

Crystal data

C₁₈H₁₈Cl₂N₂O₂
M_r = 365.3
Monoclinic, C 2/c
a = 18.9920 (5) Å
b = 5.8884 (2) Å
c = 17.8813 (5) Å
= 125.449 (4)°
V = 1629.03 (12) Å³
Z = 4
Cu K radiation
= 3.70 mm^-1
T = 120 K
0.30 × 0.19 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnto, England.]$ ), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)] T_min = 0.593, T_max = 0.787
12716 measured reflections
1442 independent reflections
1344 reflections with I > 3(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.103
S = 2.26
1442 reflections
109 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2BO1ⁱ	0.96	2.56	3.369 (2)	142
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnto, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnto, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2292 ).

Acknowledgements

We acknowledge the Dirección de Investigaciones Sede Bogotá (DIB) of the Universidad Nacional de Colombia, the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences (ASCR) for financial support of this work.

References

Billmann, J. H. & Dorman, L. C. (1963). J. Med. Chem. 6, 701-708.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Chen, X.-L. & Wu, M.-H. (2007). Acta Cryst. E63, o3684.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Heinisch, L., Wittmann, S., Stoiber, T., Berg, A., Ankel-Fuchs, D. & Mollmann, U. (2002). J. Med. Chem. 45, 3032-3039.
Huerta, R., Toscano, R. A. & Castillo, I. (2006). Acta Cryst. E62, o2938-o2940.
Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnto, England.
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Ranjith, S., Thenmozhi, S., Manikannan, R., Muthusubramanian, S. & Subbiahpandi, A. (2009). Acta Cryst. E65, o581.
Rivera, A., Aguilar, Z., Clavijo, D. & Joseph-Nathan, P. (1989). Anal. Quim. 85, 9-10.
Rivera, A., Ospina, E., Sanchez, A. & Joseph-Nathan, P. (1986). Heterocycles, 24, 2507-2510.
Yaggi, Y., Kiskan, B. & Ghosh, N. N. (2009). J. Polym. Sci. Part A Polym. Chem. 47, 5565-5576.

organic compounds