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Volume 69 
Part 3 
Page o452  
March 2013  

Received 18 February 2013
Accepted 22 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.004 Å
R = 0.052
wR = 0.128
Data-to-parameter ratio = 11.1
Details
Open access

3,4-Diaminobenzonitrile

aDepartment of Chemistry, State University of New York-College at Geneseo, 1 College Circle, Geneseo, NY 14454, USA
Correspondence e-mail: geiger@geneseo.edu

The non-H atoms in the structure of the title molecule, C7H7N3, are almost coplanar (r.m.s. deviation = 0.018 Å). The two amine groups each donate two and accept one weak N-H...N hydrogen bonds. N-H...N hydrogen bonding between the amine and nitrile groups results in chains parallel to [101] in the crystal structure. The chains are cross-linked by N-H...N hydrogen bonds between amine groups, giving rise to an infinite three-dimensional network.

Related literature

For the crystal structures of related compounds, see: Czapik & Gdaniec (2010[Czapik, A. & Gdaniec, M. (2010). Acta Cryst. C66, o198-o201.]); Stålhandske (1981[Stålhandske, C. (1981). Cryst. Struct. Commun. 10, 1081-1086.]).

[Scheme 1]

Experimental

Crystal data
  • C7H7N3

  • Mr = 133.16

  • Monoclinic, P 21 /c

  • a = 8.858 (3) Å

  • b = 10.536 (4) Å

  • c = 8.160 (3) Å

  • [beta] = 116.213 (12)°

  • V = 683.2 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 200 K

  • 0.50 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART X2S CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT, SADABS and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.85, Tmax = 0.99

  • 2149 measured reflections

  • 1188 independent reflections

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

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.128

  • S = 0.96

  • 1188 reflections

  • 107 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 0.89 (3) 2.37 (3) 3.251 (4) 168 (3)
N1-H1B...N3ii 0.91 (3) 2.31 (3) 3.147 (4) 154 (3)
N2-H2A...N1iii 0.90 (3) 2.36 (3) 3.246 (4) 173 (2)
N2-H2B...N3ii 0.93 (3) 2.42 (3) 3.303 (4) 159 (3)
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x+1, y, z+1; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT, SADABS and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT, SADABS and XSHELL. 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: XSHELL (Bruker, 2010[Bruker (2010). APEX2, SAINT, SADABS and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2053 ).


Acknowledgements

This work was supported by a Congressionally directed grant from the US Department of Education (grant No. P116Z100020) for the X-ray diffractometer

References

Bruker (2010). APEX2, SAINT, SADABS and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.
Czapik, A. & Gdaniec, M. (2010). Acta Cryst. C66, o198-o201.  [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stålhandske, C. (1981). Cryst. Struct. Commun. 10, 1081-1086.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o452  [ doi:10.1107/S1600536813005151 ]

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