Triethyl­ammonium 4-(3,5-dinitro­benzamido)-N-(3,5-dinitro­benzo­yl)benzene­sulfonamidate

Waris, G.; Siddiqi, H.M.; Flörke, U.; Hussain, R.; Butt, M.S.

doi:10.1107/S1600536812050180

Volume 69
Part 1
Page o97
January 2013

Received 12 November 2012
Accepted 8 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.084
Data-to-parameter ratio = 16.6
Details

Triethylammonium 4-(3,5-dinitrobenzamido)-N-(3,5-dinitrobenzoyl)benzenesulfonamidate

Ghulam Waris,^a Humaira Masood Siddiqi,^a ^* Ulrich Flörke,^b Rizwan Hussain ^c and M. Saeed Butt ^a

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan,^bUniversität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany, and ^cNESCOM, PO Box 2216, Islamabad, Pakistan
Correspondence e-mail: humaira_siddiqi@yahoo.com

The molecular structure of the title salt, C₆H₁₆N⁺·C₂₀H₁₁N₆O₁₂S^-, shows a planar geometry of the benzamido-phenyl-sulfonyl moiety, with a dihedral angle of 1.59 (9)° between the aromatic ring planes. The central ring and the aromatic ring of the other dinitrobenzamide group are nearly perpendicular, making a dihedral angle of 89.55 (9)°. All nitro groups lie almost in plane with the associated aromatic rings, the O-N-C-C torsion angles ranging from 9.2 (2) to 24.3 (2)°. In the crystal, strong anion-anion N-HO and anion-cation hydrogen bonds form inversion dimers stacked along the a axis. Less prominent anion-anion C-HO interactions lead to the formation of a three-dimensional network including anion-anion dimers as well as anion-anion chains along [100?].

Related literature

For background to polyamide-imide and other high-temperature resistant polymeric materials, see: Kawakami et al. (2003). For the structure of phthalylsulfacetamide, see: Shin et al. (1984).

Experimental

Crystal data

C₆H₁₆N⁺·C₂₀H₁₁N₆O₁₂S^-
M_r = 661.61
Triclinic, $[P \overline 1]$
a = 9.1046 (12) Å
b = 13.2050 (18) Å
c = 13.3427 (18) Å
= 98.854 (3)°
= 105.147 (3)°
= 105.494 (3)°
V = 1448.3 (3) Å³
Z = 2
Mo K radiation
= 0.19 mm^-1
T = 130 K
0.38 × 0.37 × 0.19 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.931, T_max = 0.965
13859 measured reflections
6875 independent reflections
4652 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.084
S = 0.89
6875 reflections
415 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO8ⁱ	0.88	2.00	2.8611 (17)	165
N100-H10PO2ⁱⁱ	0.93	1.86	2.747 (2)	158
C13-H13AO8ⁱ	0.95	2.22	3.136 (2)	162
C3-H3AO8ⁱ	0.95	2.45	3.221 (2)	139
C6-H6AO11ⁱⁱⁱ	0.95	2.38	3.215 (2)	147
C9-H9AO10^iv	0.95	2.48	3.384 (2)	159
C20-H20AO3^v	0.95	2.31	3.225 (2)	163
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) -x+2, -y, -z+1; (iv) -x+1, -y, -z+1; (v) x+1, y, z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and local programs.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2607 ).

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing financial assistance for this project through the International Research Support Initiative Programe (IRSIP) and the Department of Chemistry, Quaid-i-Azam University Islamabad for providing research facilities.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kawakami, H., Nakajima, K., Shimizu, H. & Nagaoka, S. (2003). J. Membr. Sci. 212, 195-203.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shin, W., Kim, Y. C. & Koo, C. H. (1984). Bull. Korean Chem. Soc. 5, 23-26.

organic compounds