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

Ghulam Waris; Humaira Masood Siddiqi; Ulrich Flörke; Rizwan Hussain; M Saeed Butt

doi:10.1107/S1600536812050180

. 2012 Dec 15;69(Pt 1):o97. doi: 10.1107/S1600536812050180

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

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

PMCID: PMC3588331 PMID: 23476476

Abstract

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 ▶). For the structure of phthalylsulfacetamide, see: Shin et al. (1984 ▶). graphic file with name e-69-00o97-scheme1.jpg

Experimental

Crystal data

C₆H₁₆N⁺·C₂₀H₁₁N₆O₁₂S⁻
M _r = 661.61
Triclinic,
a = 9.1046 (12) Å
b = 13.2050 (18) Å
c = 13.3427 (18) Å
α = 98.854 (3)°
β = 105.147 (3)°
γ = 105.494 (3)°
V = 1448.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.084
S = 0.89
6875 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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 Material

Click here for additional data file.^{(27KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050180/pv2607sup1.cif

e-69-00o97-sup1.cif^{(27KB, cif)}

Click here for additional data file.^{(336.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050180/pv2607Isup2.hkl

e-69-00o97-Isup2.hkl^{(336.4KB, hkl)}

Click here for additional data file.^{(11.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812050180/pv2607Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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⋯O10^iv	0.95	2.48	3.384 (2)	159
C20—H20A⋯O3^v	0.95	2.31	3.225 (2)	163

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

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.

supplementary crystallographic information

Comment

In the past decade, the demand for polyamide-imide (PAI) and other high-temperature resistant polymeric materials has grown progressively because of their outstanding mechanical properties, excellent thermal stability (Kawakami et al., 2003), etc. The title compound is a starting material for such types of materials.

Experimental

In this preparation reagent grade quality chemicals were used without their further purification. In a 100 ml, three necked, round bottomed flask, equipped with a condenser, a nitrogen gas inlet tube, a thermometer and a magnetic stirrer, of sulfanilamide (1.39 g, 0.0086 mole) in dry dichloromethane (20 ml) and a few drops of N,N-dimethylformamide(DMF) stirred at 273–278 K for 30 minutes and 3,5- dinitrobenzoylchloride (3.72 g, 0.0161 mol) in dichloromethane (30 ml) was added dropwise by dropping funnel and stirring was continued for further 1 h under the same conditions. The reaction mixture was then refluxed for 45 min. The flask content was cooled to room temperature, poured into water and let it stand for 24 h. The resulting dark brown precipitates were filtered, washed with hot water and 5% NaOH solution. Finally, the product was washed with hot water and dried under vacuum at 350 K. The crude product was recrystallized from N,N-dimethylformamide(DMF). Yield: 87%; m.p 460–462 K.