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Volume 69 
Part 11 
Page o1602  
November 2013  

Received 10 September 2013
Accepted 26 September 2013
Online 2 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.129
Data-to-parameter ratio = 19.8
Details
Open access

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

aChemistry Department, GEBH, Sree Vidyanikethan Engineering College, A. Rangampet, Tirupati 517 102, India,bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and cCentre for Organic and Medicinal Chemistry, VIT University, Vellore 632 014, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C12H16FNO2, the dioxane ring adopts a chair conformation with the methyl substituents and the C-N bond in equatorial orientations. Its mean plane subtends a dihedral angle of 40.17 (6)° with the benzene ring. In the crystal, weak N-H...F hydrogen bonds link the mol­ecules into C(7) chains propagating in [100].

Related literature

For a related structure and background to dioxanes, see: Fatima et al. (2013[Fatima, Z., Rambabu, G., Reddy, B. P., Vijayakumar, V. & Velmurugan, D. (2013). Acta Cryst. E69, o1524.]).

[Scheme 1]

Experimental

Crystal data
  • C12H16FNO2

  • Mr = 225.26

  • Monoclinic, P 21 /n

  • a = 10.4924 (10) Å

  • b = 10.0614 (10) Å

  • c = 11.0379 (11) Å

  • [beta] = 90.136 (2)°

  • V = 1165.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 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 = 0.649, Tmax = 0.746

  • 10977 measured reflections

  • 2910 independent reflections

  • 2179 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.129

  • S = 1.01

  • 2910 reflections

  • 147 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...F1i 0.86 2.48 3.1556 (14) 136
Symmetry code: (i) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

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: HB7138 ).


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

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
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]


Acta Cryst (2013). E69, o1602  [ doi:10.1107/S1600536813026561 ]

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