Biphenyl-3,3′,4,4′-tetra­amine

Qian, H.-F.; Huang, W.

doi:10.1107/S1600536810012511

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 (C-C) = 0.002 Å
R = 0.051
wR = 0.156
Data-to-parameter ratio = 13.4
Details

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

Hui-Fen Qian ^a ^* and Wei Huang ^b ^*

^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-HN 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).

Experimental

Crystal data

C₁₂H₁₄N₄
M_r = 214.27
Monoclinic, P 2₁ /c
a = 9.646 (4) Å
b = 7.476 (3) Å
c = 7.751 (3) Å
= 95.773 (5)°
V = 556.1 (4) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.989, T_max = 0.992
2698 measured reflections
979 independent reflections
724 reflections with I > 2(I)
R_int = 0.075

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.156
S = 1.09
979 reflections
73 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN2ⁱ	0.90	2.39	3.224 (2)	154
N2-H2AN1ⁱⁱ	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); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds