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Volume 69 
Part 10 
Page o1579  
October 2013  

Received 10 September 2013
Accepted 17 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.092
Data-to-parameter ratio = 20.8
Details
Open access

N-(4-Bromophenyl)-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, C12H16BrNO2, the dioxane ring adopts a chair conformation and its mean plane makes a dihedral angle of 60.63 (12)° with the 4-bromophenyl ring. In the crystal, molecules are linked by pairs of N-H...O hydrogen bonds, forming inversion dimers with an R22(8) ring motif. These dimers are consolidated by pairs of C-H...O hydrogen bonds with an R22(16) ring motif. Adjacent dimers are connected via C-H...O hydrogen bonds, forming infinite chains propagating along the c-axis direction.

Related literature

For biological properties of dioxanes and applications of 1,3-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., Giardinà, D., Gulini, U., Piergentili, A. & Sagratini, G. (2005). Med. Chem. Res. 14, 274-296.]); Wang et al. (1996a[Wang, G. W., Yuan, X. Y., Liu, Y. C., Guo, Q. X. & Lei, X. G. (1996a). Indian J. Chem. Sect. B, 35, 583-585.],b[Wang, G. W., Yuan, X. Y., Lei, X. G. & Liu, Y. C. (1996b). Chin. J. Appl. Chem. 11, 114-115.]); 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.]); Thevenet et al. (2010[Thevenet, D., Neier, R. & Stoeckli-Evans, H. (2010). Acta Cryst. E66, o473-o474.]). 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
  • C12H16BrNO2

  • Mr = 286.17

  • Monoclinic, P 21 /c

  • a = 9.9367 (5) Å

  • b = 13.5660 (6) Å

  • c = 10.3206 (5) Å

  • [beta] = 115.543 (3)°

  • V = 1255.25 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.26 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, USA.]) Tmin = 0.310, Tmax = 0.746

  • 11981 measured reflections

  • 3119 independent reflections

  • 1819 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.092

  • S = 1.01

  • 3119 reflections

  • 150 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.82 (2) 2.66 (2) 3.465 (2) 168 (2)
C8-H8...O2i 0.93 2.51 3.352 (3) 150
C9-H9...O2ii 0.93 2.65 3.557 (3) 165
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: SU2646 ).


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, USA.
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]
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. (1996b). Chin. J. Appl. Chem. 11, 114-115.
Wang, G. W., Yuan, X. Y., Liu, Y. C., Guo, Q. X. & Lei, X. G. (1996a). 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, o1579  [ doi:10.1107/S1600536813025750 ]

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