[Journal logo]

Volume 69 
Part 9 
Page o1490  
September 2013  

Received 19 August 2013
Accepted 22 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.162
Data-to-parameter ratio = 20.1
Details
Open access

N-(4-Methoxyphenyl)-2,6-dimethyl-1,3-dioxan-4-amine

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India,bChemistry Department, GEBH, Sree Vidyanikethan Engineering College, A. Rangampet, Tirupati 517102, India, and cCentre for Organic and Medicinal Chemistry, VIT University, Vellore 632 014, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C13H19NO3, the dioxane ring adopts a chair conformation. Its mean plane is inclined to the 4-methoxyphenyl ring by 70.34 (9)°. In the crystal, molecules are linked by pairs of C-H...O hydrogen bonds, forming inversion dimers with an R22(16) ring motif. The dimers are linked via C-H...[pi] interactions, forming two-dimensional networks lying parallel to the ac plane.

Related literature

For biological properties of oxygen heterocycles, such as dioxane derivatives, see: Aubele et al. (2005[Aubele, D. L., Wan, S. & Floreancig, P. E. (2005). Angew. Chem. Int. Ed. 44, 3485-3488.]); Marucci et al. (2005[Marucci, G., Piero, A., Brasili, L., Buccioni, M., Giardiná, D., Gulini, U., Piergentili, A. & Sagratini, G. (2005). Med. Chem. Res. 14, 274-296.]). For some applications, see: Wang et al. (1994[Wang, G., Yuan, X.-Y., Liu, Y.-C. & Lei, X.-G. (1994). J. Am. Oil Chem. Soc. 74, 727-730.], 1996a[Wang, G. W., Yuan, X. Y., Lei, X. G. & Liu, Y. C. (1996a). Chin. J. Appl. Chem. 11, 114-115.],b[Wang, G. W., Yuan, X. Y., Liu, Y. C., Guo, Q. X. & Lei, X. G. (1996b). Indian J. Chem. Sect. B, 35, 583-585.]); Yuan et al. (2005[Yuan, X. Y., Yang, N. F., Luo, H. A. & Liu, Y. J. (2005). Chin. J. Org. Chem. 25, 1049-1052.]). For related crystal structures, see: Chuprunov et al. (1981[Chuprunov, E. V., Tarkhova, T. N., Korallova, T. Y., Simonov, M. A. & Belov, W. V. (1981). Zh. Strukt. Khim. 22, 191-192.]); Yuan et al. (2008[Yuan, X.-Y., Zhang, M. & Ng, S. W. (2008). Acta Cryst. E64, o1314.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C13H19NO3

  • Mr = 237.29

  • Monoclinic, P 21 /c

  • a = 9.6472 (6) Å

  • b = 13.8194 (8) Å

  • c = 10.5384 (6) Å

  • [beta] = 114.355 (3)°

  • V = 1279.93 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]) Tmin = 0.667, Tmax = 0.746

  • 12259 measured reflections

  • 3169 independent reflections

  • 2133 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.162

  • S = 1.03

  • 3169 reflections

  • 158 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of ring C2-C7 ring.

D-H...A D-H H...A D...A D-H...A
C6-H6...O3i 0.93 2.51 3.407 (2) 162
C1-H1B...Cg1ii 0.96 2.77 3.700 (3) 163
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2641 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. ZF and DV acknowledge the UGC (SAP-CAS) for departmental facilities. ZF also thanks the UGC for a meritorious fellowship.

References

Aubele, D. L., Wan, S. & Floreancig, P. E. (2005). Angew. Chem. Int. Ed. 44, 3485-3488.  [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
Chuprunov, E. V., Tarkhova, T. N., Korallova, T. Y., Simonov, M. A. & Belov, W. V. (1981). Zh. Strukt. Khim. 22, 191-192.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Marucci, G., Piero, A., Brasili, L., Buccioni, M., Giardiná, D., Gulini, U., Piergentili, A. & Sagratini, G. (2005). Med. Chem. Res. 14, 274-296.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wang, G. W., Yuan, X. Y., Lei, X. G. & Liu, Y. C. (1996a). Chin. J. Appl. Chem. 11, 114-115.
Wang, G. W., Yuan, X. Y., Liu, Y. C., Guo, Q. X. & Lei, X. G. (1996b). Indian J. Chem. Sect. B, 35, 583-585.
Wang, G., Yuan, X.-Y., Liu, Y.-C. & Lei, X.-G. (1994). J. Am. Oil Chem. Soc. 74, 727-730.  [CrossRef]
Yuan, X. Y., Yang, N. F., Luo, H. A. & Liu, Y. J. (2005). Chin. J. Org. Chem. 25, 1049-1052.  [ChemPort]
Yuan, X.-Y., Zhang, M. & Ng, S. W. (2008). Acta Cryst. E64, o1314.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1490  [ doi:10.1107/S1600536813023763 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.