N-(2-Nitro­phenyl­sulfon­yl)-N-(4-nitro­phenyl­sulfon­yl)methyl­amine

Lu, H.

doi:10.1107/S1600536808027499

Volume 64
Part 10
Page o1885
October 2008

Received 22 July 2008
Accepted 27 August 2008
Online 6 September 2008

Key indicators
Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.002 Å
R = 0.030
wR = 0.094
Data-to-parameter ratio = 15.6
Details

N-(2-Nitrophenylsulfonyl)-N-(4-nitrophenylsulfonyl)methylamine

Haiyan Lu ^a ^*

^aThe Graduate School of the Chinese Academy of Sciences, Beijing 100049, People's Republic of China
Correspondence e-mail: haiyan_lu2008@yahoo.cn

In the crystal structure of the title compound, C₁₃H₁₁N₃O₈S₂, molecules are linked by intermolecular C-HO hydrogen bonds into zigzag chains running parallel to the c axis. Centrosymmetrically related chains are further stabilized by aromatic [pi] - [pi] stacking interactions [centroid-centroid distance = 3.749 (3) Å] involving adjacent 4-nitrobenzene rings. Intramolecular C-HO hydrogen bonds are also present.

Related literature

For the crystal structures of related compounds, see: Henschel et al. (1996); Curtis & Pavkovic (1983). For details of the biological activities of sulfonamide compounds, see: Kamoshita et al. (1987). For details of the application of sulfonimade catalysts, see: Zhang et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₃H₁₁N₃O₈S₂
M_r = 401.37
Monoclinic, P 2₁ /c
a = 13.517 (3) Å
b = 9.994 (2) Å
c = 11.990 (2) Å
= 95.26 (3)°
V = 1613.0 (6) Å³
Z = 4
Mo K radiation
= 0.38 mm^-1
T = 153 (2) K
0.58 × 0.47 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi 1995) T_min = 0.750, T_max = 0.897
15376 measured reflections
3683 independent reflections
3540 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.094
S = 1.13
3683 reflections
236 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8BO7	0.95	2.53	2.902 (2)	104
C4-H4AO5	0.95	2.38	2.803 (2)	106
C13-H13AO7	0.98	2.54	2.978 (2)	107
C13-H13CO1	0.98	2.34	2.972 (2)	122
C1-H1AO6ⁱ	0.95	2.51	3.369 (2)	150
Symmetry code: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: RZ2239 ).

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.
Curtis, V. A. & Pavkovic, S. F. (1983). Acta Cryst. C39, 1077-1078.
Henschel, D., Hiemisch, O., Blaschette, A. & Jones, P. G. (1996). Z. Naturforsch. Teil B, 51, 1313-1315.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Kamoshita, K., Matsumoto, H. & Nagano, E. (1987). US Patent. US 4 670 046.
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Takyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, Z. B., Zhou, S. Y. & Nie, J. (2007). J. Mol. Catal. A Chem. 265, 9-14.

organic compounds