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Volume 69 
Part 10 
Page o1561  
October 2013  

Received 6 September 2013
Accepted 11 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.119
Data-to-parameter ratio = 20.9
Details
Open access

2,6-Dimethyl-N-(2-methylphenyl)-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, C13H19NO2, the dioxane ring adopts a chair conformation and its mean plane makes a dihedral angle of 45.36 (8)° with the phenyl ring. In the crystal, molecules are linked by pairs of N-H...O hydrogen bonds, forming inversion dimers with R22(12) ring motifs. These dimers are consolidated by pairs of C-H...O hydrogen bonds with R22(8) ring motifs.

Related literature

For applications of 1,3-dioxane derivatives, see: Wang et al. (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.]). Dioxane rings are frequently encountered in many bioactive molecules, some of which are cytotoxic agents (Aubele et al., 2005[Aubele, D. L., Wan, S. & Floreancig, P. E. (2005). Angew. Chem. Int. Ed. 44, 3485-3488.]) and antimuscarinic agents (Marucci et al., 2005[Marucci, G., Piero, A., Brasili, L., Buccioni, M., Giardinà, D., Gulini, U., Piergentili, A. & Sagratini, G. (2005). Med. Chem. Res. 14, 274-296.]). 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.]); Thevenet et al. (2010[Thevenet, D., Neier, R. & Stoeckli-Evans, H. (2010). Acta Cryst. E66, o473-o474.]); Fatima et al. (2013[Fatima, Z., Rambabu, G., Reddy, B. P., Vijayakumar, V. & Velmurugan, D. (2013). Acta Cryst. E69, o1524.]). For hydrogen-bond 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
  • C13H19NO2

  • Mr = 221.29

  • Monoclinic, P 21 /c

  • a = 8.0209 (2) Å

  • b = 7.8762 (2) Å

  • c = 20.4293 (5) Å

  • [beta] = 99.066 (2)°

  • V = 1274.48 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 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 = 0.692, Tmax = 0.746

  • 12359 measured reflections

  • 3177 independent reflections

  • 2481 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.119

  • S = 1.03

  • 3177 reflections

  • 152 parameters

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.843 (15) 2.559 (15) 3.3688 (13) 161.3 (13)
C3-H3A...O1i 0.97 2.54 3.4950 (13) 167
Symmetry code: (i) -x+1, -y+1, -z+1.

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.]) and Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); 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: SU2643 ).


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 the 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.  [Web of Science] [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fatima, Z., Rambabu, G., Reddy, B. P., Vijayakumar, V. & Velmurugan, D. (2013). Acta Cryst. E69, o1524.  [CrossRef] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Marucci, G., Piero, A., Brasili, L., Buccioni, M., Giardinà, D., Gulini, U., Piergentili, A. & Sagratini, G. (2005). Med. Chem. Res. 14, 274-296.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Thevenet, D., Neier, R. & Stoeckli-Evans, H. (2010). Acta Cryst. E66, o473-o474.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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.
Yuan, X. Y., Yang, N. F., Luo, H. A. & Liu, Y. J. (2005). Chin. J. Org. Chem. 25, 1049-1052.  [ChemPort]


Acta Cryst (2013). E69, o1561  [ doi:10.1107/S1600536813025294 ]

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