[Journal logo]

Volume 64 
Part 6 
Page o1140  
June 2008  

Received 14 May 2008
Accepted 16 May 2008
Online 21 May 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.005 Å
R = 0.055
wR = 0.136
Data-to-parameter ratio = 15.3
Details
Open access

Bis(3-aminophenyl) sulfone acetonitrile solvate

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: fangshi.li@njut.edu.cn

In the sulfone molecule of the title compound, C12H12N2O2S·C2H3N, the two benzene rings are oriented at a dihedral angle of 80.69 (3)°. Weak intramolecular C-H...O hydrogen bonds result in the formation of two five-membered rings, which both have envelope conformations. In the crystal structure, intermolecular N-H...O hydrogen bonds link the molecules.

Related literature

For related literature, see: Yang et al. (2003[Yang, C. P., Woo, E. M. & Jou, G. L. (2003). J. Therm. Anal. Calorim. 74, 843-852.]); Rudyk et al. (2003[Rudyk, H., Knaggs, M. H., Vasiljevic, S., Hope, J., Birkett, C. & Gilbert, I. H. (2003). Eur. J. Med. Chem. 38, 567-579.]); Ayyangar et al. (1981[Ayyangar, N. R., Lugade, A. G., Nikrad, P. V. & Sharma, V. K. (1981). Synthesis, pp. 640-643.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12N2O2S·C2H3N

  • Mr = 289.35

  • Orthorhombic, P b c a

  • a = 9.1690 (18) Å

  • b = 15.559 (3) Å

  • c = 20.960 (4) Å

  • V = 2990.2 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 294 (2) K

  • 0.40 × 0.30 × 0.30 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.917, Tmax = 0.937

  • 2674 measured reflections

  • 2674 independent reflections

  • 1644 reflections with I > 2[sigma](I)

  • 3 standard reflections frequency: 120 min intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.135

  • S = 1.03

  • 2674 reflections

  • 175 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6A...O1 0.93 2.53 2.913 (4) 105
C8-H8A...O2 0.93 2.53 2.906 (4) 104
N1-H1B...O1i 0.86 2.32 3.147 (5) 161
N2-H2B...O2ii 0.86 2.28 3.079 (4) 155
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2464 ).


References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Ayyangar, N. R., Lugade, A. G., Nikrad, P. V. & Sharma, V. K. (1981). Synthesis, pp. 640-643.  [CrossRef]
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Rudyk, H., Knaggs, M. H., Vasiljevic, S., Hope, J., Birkett, C. & Gilbert, I. H. (2003). Eur. J. Med. Chem. 38, 567-579.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]
Yang, C. P., Woo, E. M. & Jou, G. L. (2003). J. Therm. Anal. Calorim. 74, 843-852.  [CrossRef] [ChemPort]


Acta Cryst (2008). E64, o1140  [ doi:10.1107/S1600536808014840 ]

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.