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Volume 70 
Part 1 
Page o16  
January 2014  

Received 29 November 2013
Accepted 2 December 2013
Online 7 December 2013

Key indicators
Single-crystal Synchrotron study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 25.8
Details
Open access

N,N-Dimethyl-4-(pyren-1-yl)aniline

aFS-SCS, Deutsches Elecktronen-Synchrotron (DESY), Notkestrasse 85, 22607 Hamburg, Germany,bMax Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany, and cFS-PS, Deutsches Elecktronen-Synchrotron (DESY), Notkestrasse 85, 22607 Hamburg, Germany
Correspondence e-mail: sreevidya.thekku.veedu@desy.de, simone.techert@desy.de

In the title compound, C24H19N, the di­methyl­amino group is inclined to the benzene ring by 2.81 (9)°. Their mean plane makes a dihedral angle of 64.12 (2)° with the mean plane of the pyrene ring system [r.m.s. deviation = 0.031 (1) Å]. In the crystal, mol­ecules are linked via C-H...[pi] inter­actions, which connect neighbouring mol­ecules into columns along the c axis.

Related literature

For charge transfer involving donor and acceptor mol­ecules, see: Wasielewski (1992[Wasielewski, M. R. (1992). Chem. Rev. 92, 435-461.]); Willemse et al. (2000[Willemse, R. J., Piet, J. J., Warman, J. M., Hartl, F., Verhoeven, J. W. & Brouwer, A. M. (2000). J. Am. Chem. Soc. 122, 3721-3730.]). For a related structure, N,N-Diphenyl-4-(pyren-1-yl)aniline, see: Wang et al. (2010[Wang, Z.-Q., Zhang, R., Sun, X.-J., Zhang, Y.-P., Xu, Y. & Xu, C. (2010). Z. Kristallogr. New Cryst. Struct. 225, 573-575.]). For the synthesis of the title compound, see: Dewar & Mole (1956[Dewar, M. J. S. & Mole, T. (1956). J. Chem. Soc. 7, 1441-1443.]); Norman et al. (1958[Norman, R. O. C., Thompson, G. A. & Waters, W. A. (1958). J. Chem. Soc. 12, 175-179.]). For standard bond lengths, see. Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C24H19N

  • Mr = 321.40

  • Monoclinic, P 21 /c

  • a = 6.1270 (12) Å

  • b = 30.686 (6) Å

  • c = 9.478 (3) Å

  • [beta] = 113.35 (2)°

  • V = 1636.0 (8) Å3

  • Z = 4

  • Synchrotron radiation

  • [lambda] = 0.600 Å

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.30 × 0.15 × 0.10 mm

Data collection
  • Huber diffractometer with a Mar CCD detector

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.993

  • 47866 measured reflections

  • 5872 independent reflections

  • 4806 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.135

  • S = 1.08

  • 5872 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the C1-C6, C7-C10/C19/C20, C10-C13/C18/C19, C13-C18 and C17-C22 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C2-H2...Cg2i 0.95 2.93 3.6043 (15) 129
C6-H6...Cg5ii 0.95 2.90 3.6495 (15) 137
C22-H22...Cg1iii 0.95 2.68 3.5499 (15) 152
C23-H52A...Cg3i 0.98 2.74 3.5994 (15) 147
C24-H52E...Cg4ii 0.98 2.77 3.5284 (15) 135
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: XDS (Kabsch, 1993[Kabsch, W. (1993). J. Appl. Cryst. 26, 795-800.]); cell refinement: XDS; data reduction: XDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: 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: SU2671 ).


Acknowledgements

ST thanks the DFG, SFB 755 and SFB 1073 for financial support. STV thanks G. Busse and L. Busse for technical help.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.  [CrossRef]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dewar, M. J. S. & Mole, T. (1956). J. Chem. Soc. 7, 1441-1443.  [CrossRef]
Kabsch, W. (1993). J. Appl. Cryst. 26, 795-800.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Norman, R. O. C., Thompson, G. A. & Waters, W. A. (1958). J. Chem. Soc. 12, 175-179.  [CrossRef]
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, Z.-Q., Zhang, R., Sun, X.-J., Zhang, Y.-P., Xu, Y. & Xu, C. (2010). Z. Kristallogr. New Cryst. Struct. 225, 573-575.  [ChemPort]
Wasielewski, M. R. (1992). Chem. Rev. 92, 435-461.  [CrossRef] [ChemPort] [Web of Science]
Willemse, R. J., Piet, J. J., Warman, J. M., Hartl, F., Verhoeven, J. W. & Brouwer, A. M. (2000). J. Am. Chem. Soc. 122, 3721-3730.  [Web of Science] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o16  [ doi:10.1107/S1600536813032698 ]

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