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Volume 69 
Part 11 
Page o1722  
November 2013  

Received 16 October 2013
Accepted 22 October 2013
Online 31 October 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.121
Data-to-parameter ratio = 22.4
Details
Open access

4-Ethynyl-N,N-di­phenyl­aniline

aCollege of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053, People's Republic of China
Correspondence e-mail: wqwang2008@163.com

The asymmetric unit of the title compound, C20H15N, comprises two crystallographically independent mol­ecules (A and B). In each mol­ecule, the N atom adopts an approximately trigonal planar geometry, lying 0.009 (1) or 0.003 (1) Å from the plane defined by the C atoms of the aromatic substituents to which it is attached. In the crystal, mol­ecules are linked via C-H...[pi] inter­actions, forming a three-dimensional structure.

Related literature

For the synthesis and applications of the title compound, see: Onitsuka et al. (2006[Onitsuka, K., Ohara, N., Takei, F. & Takahashi, S. (2006). Dalton Trans. pp. 3693-3698.]); Li et al. (2012[Li, Q. T., Guo, H. M., Ma, L. H., Wu, W. H., Liu, Y. F. & Zhao, J. Z. (2012). J. Mater. Chem. 22, 5319-5329.]). For the crystal structures of related compounds, see: Zhang et al. (2012[Zhang, Z.-W., Liu, Y.-Q., Zhu, Y.-C. & Wu, J.-Y. (2012). Acta Cryst. E68, o1933.]); Narayanan et al. (2012[Narayanan, P., Sethusankar, K., Nandakumar, M. & Mohanakrishnan, A. K. (2012). Acta Cryst. E68, o2035.]).

[Scheme 1]

Experimental

Crystal data
  • C20H15N

  • Mr = 269.33

  • Orthorhombic, P c a 21

  • a = 9.0532 (8) Å

  • b = 16.8067 (15) Å

  • c = 19.2508 (18) Å

  • V = 2929.1 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.10 × 0.10 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.993, Tmax = 0.999

  • 29115 measured reflections

  • 8489 independent reflections

  • 8095 reflections with I > 2[sigma](I)

  • Rint = 0.103

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

  • wR(F2) = 0.121

  • S = 1.02

  • 8489 reflections

  • 379 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg4, Cg5 and Cg6 are the centroids of the C1-C6, C15-C21, C21-C26, C29-C34 and C35-C40 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C2-H2...Cg6 0.95 2.80 3.5375 (12) 136
C8-H8...Cg3i 0.95 2.66 3.5938 (15) 166
C12-H12...Cg5ii 0.95 2.77 3.6064 (15) 148
C20-H20...Cg4iii 0.95 2.72 3.5647 (12) 148
C28-H28...Cg5iv 0.95 2.92 3.5494 (17) 124
C34-H34...Cg1 0.95 2.88 3.6659 (13) 141
Symmetry codes: (i) [-x+2, -y, z+{\script{1\over 2}}]; (ii) [-x+{\script{5\over 2}}, y, z-{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]; (iv) [-x+{\script{3\over 2}}, y, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2001[Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). APEX2 and SAINT. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2660 ).


Acknowledgements

The authors are grateful to Hubei University of Arts and Science for financial support.

References

Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Li, Q. T., Guo, H. M., Ma, L. H., Wu, W. H., Liu, Y. F. & Zhao, J. Z. (2012). J. Mater. Chem. 22, 5319-5329.  [CrossRef] [ChemPort]
Narayanan, P., Sethusankar, K., Nandakumar, M. & Mohanakrishnan, A. K. (2012). Acta Cryst. E68, o2035.  [CrossRef] [IUCr Journals]
Onitsuka, K., Ohara, N., Takei, F. & Takahashi, S. (2006). Dalton Trans. pp. 3693-3698.  [CrossRef]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Zhang, Z.-W., Liu, Y.-Q., Zhu, Y.-C. & Wu, J.-Y. (2012). Acta Cryst. E68, o1933.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1722  [ doi:10.1107/S1600536813029036 ]

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