3,3′-(Ethane-1,2-di­yl)bis­(3,4-dihydro-2H-1,3-benzoxazine)

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

doi:10.1107/S1600536811053530

Volume 68
Part 1
Page o148
January 2012

Received 9 December 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.011 Å
R = 0.067
wR = 0.171
Data-to-parameter ratio = 6.7
Details

3,3'-(Ethane-1,2-diyl)bis(3,4-dihydro-2H-1,3-benzoxazine)

Augusto Rivera,^a ^* Jairo Camacho,^a Jaime Ríos-Motta,^a Karla Fejfarová ^b and Michal Dusek ^b

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

The title compound, C₁₈H₂₀N₂O₂, was prepared by Mannich-type reaction of phenol, ethane-1,2-diamine and formaldehyde. The heterocyclic rings adopt half-chair conformations. The acyclic methylene groups attached to the N atoms are in an axial position. In the crystal, weak C-HO hydrogen bonds link the molecules into dimers. These dimers are further connected via C-H [pi] contacts.

Related literature

For related structures see: Rivera et al. (2011, 2010). For the preparation of the title compound, see: Rivera et al. (1989). For ring conformations, see Cremer & Pople (1975). For weak hydrogen bonds, see: Desiraju & Steiner (1999).

Experimental

Crystal data

C₁₈H₂₀N₂O₂
M_r = 296.4
Monoclinic, P 2₁
a = 10.868 (2) Å
b = 5.1693 (13) Å
c = 13.327 (3) Å
= 102.623 (18)°
V = 730.6 (3) Å³
Z = 2
Cu K radiation
= 0.71 mm^-1
T = 120 K
0.97 × 0.10 × 0.04 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.77, T_max = 1
2799 measured reflections
1341 independent reflections
785 reflections with I > 3(I)
R_int = 0.079

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.171
S = 1.38
1341 reflections
199 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C12-C17 ring.

D-HA	D-H	HA	DA	D-HA
C11-H11aO2ⁱ	0.96	2.47	3.415 (10)	168
C11-H11bCg4ⁱⁱ	0.96	2.58	3.523 (10)	169
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+2]$ ; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: BT5748 ).

Acknowledgements

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

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond. Oxford University Press.
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Rivera, A., Aguilar, Z., Clavijo, D. & Joseph-Nathan, P. (1989). Anal. Quim. 85, 9-10.
Rivera, A., Camacho, J., Ríos-Motta, J., Pojarová, M. & Dusek, M. (2011). Acta Cryst. E67, o2028.
Rivera, A., Rojas, J. J., Ríos-Motta, J., Dusek, M. & Fejfarová, K. (2010). Acta Cryst. E66, o1134.

organic compounds