Bis(3-amino­phen­yl) sulfone acetonitrile solvate

Yao, W.; Li, F.-S.; Yu, D.-S.; Lu, C.; Zhu, J.-N.

doi:10.1107/S1600536808014840

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 (C-C) = 0.005 Å
R = 0.055
wR = 0.136
Data-to-parameter ratio = 15.3
Details

Bis(3-aminophenyl) sulfone acetonitrile solvate

Wei Yao,^a Fang-Shi Li,^a ^* Da-Sheng Yu,^a Chui Lu ^a and Jin-Na Zhu ^a

^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-HO hydrogen bonds result in the formation of two five-membered rings, which both have envelope conformations. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules.

Related literature

For related literature, see: Yang et al. (2003); Rudyk et al. (2003); Ayyangar et al. (1981). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₂H₁₂N₂O₂S·C₂H₃N
M_r = 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 radiation
= 0.22 mm^-1
T = 294 (2) K
0.40 × 0.30 × 0.30 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.917, T_max = 0.937
2674 measured reflections
2674 independent reflections
1644 reflections with I > 2(I)
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.135
S = 1.03
2674 reflections
175 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6AO1	0.93	2.53	2.913 (4)	105
C8-H8AO2	0.93	2.53	2.906 (4)	104
N1-H1BO1ⁱ	0.86	2.32	3.147 (5)	161
N2-H2BO2ⁱⁱ	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); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003); 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.
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.
Rudyk, H., Knaggs, M. H., Vasiljevic, S., Hope, J., Birkett, C. & Gilbert, I. H. (2003). Eur. J. Med. Chem. 38, 567-579.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Yang, C. P., Woo, E. M. & Jou, G. L. (2003). J. Therm. Anal. Calorim. 74, 843-852.

organic compounds