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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 [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.084
Data-to-parameter ratio = 16.6
Details
Open access

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

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-H...O and anion-cation hydrogen bonds form inversion dimers stacked along the a axis. Less prominent anion-anion C-H...O 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[Kawakami, H., Nakajima, K., Shimizu, H. & Nagaoka, S. (2003). J. Membr. Sci. 212, 195-203.]). For the structure of phthalylsulfacetamide, see: Shin et al. (1984[Shin, W., Kim, Y. C. & Koo, C. H. (1984). Bull. Korean Chem. Soc. 5, 23-26.]).

[Scheme 1]

Experimental

Crystal data
  • C6H16N+·C20H11N6O12S-

  • Mr = 661.61

  • Triclinic, [P \overline 1]

  • a = 9.1046 (12) Å

  • b = 13.2050 (18) Å

  • c = 13.3427 (18) Å

  • [alpha] = 98.854 (3)°

  • [beta] = 105.147 (3)°

  • [gamma] = 105.494 (3)°

  • V = 1448.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.931, Tmax = 0.965

  • 13859 measured reflections

  • 6875 independent reflections

  • 4652 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.084

  • S = 0.89

  • 6875 reflections

  • 415 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O8i 0.88 2.00 2.8611 (17) 165
N100-H10P...O2ii 0.93 1.86 2.747 (2) 158
C13-H13A...O8i 0.95 2.22 3.136 (2) 162
C3-H3A...O8i 0.95 2.45 3.221 (2) 139
C6-H6A...O11iii 0.95 2.38 3.215 (2) 147
C9-H9A...O10iv 0.95 2.48 3.384 (2) 159
C20-H20A...O3v 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[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shin, W., Kim, Y. C. & Koo, C. H. (1984). Bull. Korean Chem. Soc. 5, 23-26.  [ChemPort]


Acta Cryst (2013). E69, o97  [ doi:10.1107/S1600536812050180 ]

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