1-(4-Nitrobenzoyl)-3-(4-nitrophenyl)thiourea acetone hemisolvate

In the title compound, C14H10N4O5S·0.5C3H6O, the nitrobenzoyl and nitrophenyl groups have trans and cis configurations, respectively, with respect to the thiourea S atom. The molecular conformation is stabilized by intramolecular N—H⋯O and C—H⋯S hydrogen bonds. The acetone solvent molecule possesses a crystallographically imposed twofold axis. In the crystal packing, thiourea molecules are linked by intermolecular C—H⋯O hydrogen-bond interactions to form chains running parallel to the c axis. The chains are further bridged via N—H⋯O and C—H⋯O hydrogen bonds involving the acetone molecules.

In the title compound, C 14 H 10 N 4 O 5 SÁ0.5C 3 H 6 O, the nitrobenzoyl and nitrophenyl groups have trans and cis configurations, respectively, with respect to the thiourea S atom. The molecular conformation is stabilized by intramolecular N-HÁ Á ÁO and C-HÁ Á ÁS hydrogen bonds. The acetone solvent molecule possesses a crystallographically imposed twofold axis. In the crystal packing, thiourea molecules are linked by intermolecular C-HÁ Á ÁO hydrogen-bond interactions to form chains running parallel to the c axis. The chains are further bridged via N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds involving the acetone molecules.
Financial support of this work by the Foundation of Northwest University for Nationalities is acknowledged.
As part of our research on thiourea coordination chemistry, we are interested in the study of the influence of noncovalent interactions, especially hydrogen bonds and π-π stacking interactions, on the coordination modes of benzoylthiourea with transition metal ions. In the present paper, the crystal structure of the title compound is reported.
In the molecule of the title compound ( Fig. 1), the nitrobenzoyl and nitrophenyl groups have trans and cis configurations, respectively, with respect of the thiourea S atom. The dihedral angle formed by the two aromatic rings is 7.68 (6)°.

Experimental
All reagents and organic solvents were of analytical reagent grade and commercially available. p-Nitrobenzoyl chloride (1.86 g) was treated with ammonium thiocyanate (1.20 g) in CH 2 Cl 2 under solid-liquid phase transfer catalysis conditions, using 3% polyethylene glycol-400 as catalyst, to give the corresponding benzoyl isothiocyanate, which was reacted with p-nitroaniline (1.38 g) to give the title compound. The solid was separated from the liquid phase by filtration, washed with CH 2 Cl 2 and then dried in air. Yellow single crystals suitable for X-ray analysis were obtained after one week by slow evaporation of an acetone solution. The infrared spectrum was recorded in the range of 4000-400 cm -1 on a Nicolet NEXUS 670 F T-IR spectrometer, using KBr pellets. 1 H NMR spectrum was obtained on an INOVA-400 MHz superconduction spectrometer, DMSO-d6 was used as solvent and TMS as internal standard, and the chemical shifts are expressed as delta.
Elemental analyses were carried out on a PE-2400 elemental analysis instrument. Melting point determination was performed in YRT-3 melting point instrument (Tianjin) and was uncorrected. All H atoms bound to C atoms were placed in calculated positions and refined using the riding model approximation, with C-H = 0.93-0.96 Å and with U iso (H) = 1.2U eq (C) or 1.5 U eq (C) for methyl H atoms. The H atoms bound to N atoms were located in a difference Fourier map and refined freely.   as those based on F, and R-factors based on ALL data will be even larger.