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Volume 69 
Part 10 
Page o1524  
October 2013  

Received 1 September 2013
Accepted 5 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.137
Data-to-parameter ratio = 19.7
Details
Open access

N-(2-Fluorophenyl)-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, C12H16FNO3, the dioxane ring adopts a chair conformation with the methyl groups and amine N atom in equatorial positions. The best plane through the dioxane ring makes a dihedral angle of 43.16 (8)° with the phenyl ring. In the crystal, pairs of C-H...O hydrogen bonds link the molecules into centrosymmetric R22(8) dimers, which are linked into [100] chains by further C-H...O hydrogen bonds. The N-H group does not participate in hydrogen bonding.

Related literature

Dioxane rings are frequently encountered in structural motifs in many bioactive molecules such as 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 applications of this class of compounds, see: Wang, Yuan, Liu et al. (1996[Wang, G. W., Yuan, X. Y., Liu, Y. C., Guo, Q. X. & Lei, X. G. (1996). Indian J. Chem. Sect. B, 35, 583-585.]); Wang, Yuan, Lei & Liu (1996[Wang, G. W., Yuan, X. Y., Lei, X. G. & Liu, Y. C. (1996). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C12H16FNO2

  • Mr = 225.26

  • Monoclinic, C 2/c

  • a = 19.6219 (13) Å

  • b = 8.1603 (6) Å

  • c = 15.2396 (10) Å

  • [beta] = 95.950 (3)°

  • V = 2427.0 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.617, Tmax = 0.746

  • 11540 measured reflections

  • 3020 independent reflections

  • 1973 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.137

  • S = 1.03

  • 3020 reflections

  • 153 parameters

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5A...O2i 0.97 2.60 3.5563 (17) 169
C11-H11...O1ii 0.93 2.54 3.473 (2) 177
Symmetry codes: (i) -x, -y, -z+2; (ii) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z].

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: HB7132 ).


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 facilties. 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]
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]
Wang, G. W., Yuan, X. Y., Lei, X. G. & Liu, Y. C. (1996). Chin. J. Appl. Chem. 11, 114-115.
Wang, G. W., Yuan, X. Y., Liu, Y. C., Guo, Q. X. & Lei, X. G. (1996). 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, o1524  [ doi:10.1107/S1600536813024732 ]

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