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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 [sigma](C-C) = 0.011 Å
R = 0.067
wR = 0.171
Data-to-parameter ratio = 6.7
Details
Open access

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

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-H...O 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[Rivera, A., Camacho, J., Ríos-Motta, J., Pojarová, M. & Dusek, M. (2011). Acta Cryst. E67, o2028.], 2010[Rivera, A., Rojas, J. J., Ríos-Motta, J., Dusek, M. & Fejfarová, K. (2010). Acta Cryst. E66, o1134.]). For the preparation of the title compound, see: Rivera et al. (1989[Rivera, A., Aguilar, Z., Clavijo, D. & Joseph-Nathan, P. (1989). Anal. Quim. 85, 9-10.]). For ring conformations, see Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For weak hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond. Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data
  • C18H20N2O2

  • Mr = 296.4

  • Monoclinic, P 21

  • a = 10.868 (2) Å

  • b = 5.1693 (13) Å

  • c = 13.327 (3) Å

  • [beta] = 102.623 (18)°

  • V = 730.6 (3) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.77, Tmax = 1

  • 2799 measured reflections

  • 1341 independent reflections

  • 785 reflections with I > 3[sigma](I)

  • Rint = 0.079

Refinement
  • R[F2 > 2[sigma](F2)] = 0.067

  • wR(F2) = 0.171

  • S = 1.38

  • 1341 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C12-C17 ring.

D-H...A D-H H...A D...A D-H...A
C11-H11a...O2i 0.96 2.47 3.415 (10) 168
C11-H11b...Cg4ii 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.]); 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.  [CrossRef] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
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.  [ChemPort]
Rivera, A., Camacho, J., Ríos-Motta, J., Pojarová, M. & Dusek, M. (2011). Acta Cryst. E67, o2028.  [CrossRef] [details]
Rivera, A., Rojas, J. J., Ríos-Motta, J., Dusek, M. & Fejfarová, K. (2010). Acta Cryst. E66, o1134.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o148  [ doi:10.1107/S1600536811053530 ]

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