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Volume 66 
Part 5 
Page o1060  
May 2010  

Received 14 January 2010
Accepted 3 April 2010
Online 14 April 2010

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.156
Data-to-parameter ratio = 13.4
Details
Open access

Biphenyl-3,3',4,4'-tetraamine

aCollege of Sciences, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and bState Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
Correspondence e-mail: whuang@nju.edu.cn, whuang@nju.edu.cn

The title compound, C12H14N4, has a crystallographically imposed centre of symmetry. Intermolecular N-H...N hydrogen bonds between amino groups link adjacent molecules into a three-dimensional network where ten-membered hydrogen-bonded rings are observed.

Related literature

For a related compound, see: Dobrzycki & Wozniak (2007[Dobrzycki, L. & Wozniak, K. (2007). CrystEngComm, 9, 1029-1040.]).

[Scheme 1]

Experimental

Crystal data
  • C12H14N4

  • Mr = 214.27

  • Monoclinic, P 21 /c

  • a = 9.646 (4) Å

  • b = 7.476 (3) Å

  • c = 7.751 (3) Å

  • [beta] = 95.773 (5)°

  • V = 556.1 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 291 K

  • 0.14 × 0.12 × 0.10 mm

Data collection
  • Bruker SMART 1K CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.989, Tmax = 0.992

  • 2698 measured reflections

  • 979 independent reflections

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

  • Rint = 0.075

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.156

  • S = 1.09

  • 979 reflections

  • 73 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 0.90 2.39 3.224 (2) 154
N2-H2A...N1ii 0.90 2.35 3.124 (2) 145
Symmetry codes: (i) -x, -y+2, -z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2140 ).


Acknowledgements

WH acknowledges the National Natural Science Foundation of China (grant No. 20871065) and the Jiangsu Province Department of Science and Technology (grant No. BK2009226) for financial aid.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dobrzycki, L. & Wozniak, K. (2007). CrystEngComm, 9, 1029-1040.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2010). E66, o1060  [ doi:10.1107/S1600536810012511 ]

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