[Journal logo]

Volume 69 
Part 5 
Page o658  
May 2013  

Received 11 March 2013
Accepted 27 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.081
Data-to-parameter ratio = 6.3
Details
Open access

An orthorhombic polymorph of 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 title compound, C7H7N3, is an orthorhombic polymorph that crystallizes in the space group Pca21. The previously reported monoclinic form [Geiger & Parsons (2013[Geiger, D. K. & Parsons, D. E. (2013). Acta Cryst. E69, o452.]) Acta Cryst. E69, o452] crystallizes in the space group P21/c (Z = 4). In the crystal, two independent HN-H...N[triple bond]C hydrogen bonds link the molecules into chains along the a-glide plane. Two further independent HN-H...NH2 hydrogen bonds join the chains, forming a three-dimensional network.

Related literature

For the structure of the monoclinic polymorph of the title compound, see: Geiger & Parsons (2013[Geiger, D. K. & Parsons, D. E. (2013). Acta Cryst. E69, o452.]). For the structures of the two crystalline forms of 1,2-diaminobenzene, 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

  • Orthorhombic, P c a 21

  • a = 17.425 (3) Å

  • b = 4.5225 (8) Å

  • c = 8.6167 (16) Å

  • V = 679.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 200 K

  • 0.60 × 0.30 × 0.30 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 = 0.84, Tmax = 0.98

  • 3295 measured reflections

  • 652 independent reflections

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

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.081

  • S = 1.08

  • 652 reflections

  • 103 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.09 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N3i 0.91 (3) 2.49 (3) 3.218 (3) 138 (2)
N1-H1B...N2ii 0.92 (3) 2.20 (3) 3.107 (3) 170 (3)
N2-H2A...N3i 0.95 (3) 2.22 (3) 3.152 (3) 168 (3)
N2-H2B...N1iii 0.89 (3) 2.41 (3) 3.210 (3) 149 (2)
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+1, z]; (ii) [-x+1, -y, z-{\script{1\over 2}}]; (iii) [-x+1, -y+1, 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: QK2056 ).


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] [ChemPort] [details]
Geiger, D. K. & Parsons, D. E. (2013). Acta Cryst. E69, o452.  [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] [ChemPort] [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, o658  [ doi:10.1107/S1600536813008489 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.