Diethyl 5,5′-thiobis[2-amino-4-(4-fluorophenyl)-1-phenyl-1H-pyrrole-3-carboxylate]

In the title compound, C38H32F2N4O4S, the ethyl chain of the ethoxycarbonyl group displays rotational disorder with site occupancy factors ca 0.6 and 0.4. The S atom lies on a twofold rotation axis. There are both inter- and intramolecular hydrogen bonds in the crystal structure. An intramolecular N—H⋯O hydrogen bond forms a six-membered ring, while an intermolecular N—H⋯F hydrogen bond results in a chain.

In the title compound, C 38 H 32 F 2 N 4 O 4 S, the ethyl chain of the ethoxycarbonyl group displays rotational disorder with site occupancy factors ca 0.6 and 0.4. The S atom lies on a twofold rotation axis. There are both inter-and intramolecular hydrogen bonds in the crystal structure. An intramolecular N-HÁ Á ÁO hydrogen bond forms a six-membered ring, while an intermolecular N-HÁ Á ÁF hydrogen bond results in a chain.
The title compound adopts a V conformation, which contains two parts which are same to each other, and each part comprises three rings, two phenyl rings and one pyrrole ring. In each part, the two phenyl rings are not conjugated with the pyrrole ring, with the dihedral angle of 49.07° and 73.04°, respectively.
All the bond lengths and angles (Table 1) in the title compound are within the normal range. The bond lengths of C7-C8 (1.356 Å) and C9-C10 (1.380 Å) in the pyrrole ring is obviously shorter than C-C (1.52 Å) but are close to normal C═C (1.32 Å), it is indicated that they are both C═C. The bond length of C7-C10 (1.454 Å) is between C-C and C═C.
X-ray analysis reveals that there exists both intermolecular hydrogen and intromolecular hydrogen bonds in the crystal structure (Fig. 2). The intromolecular N2-H2B···O1 hydrogen bond forms a six-membered ring, while the intermolecular N2-H2A···F1 hydrogen bond makes the molecule extended in line.

Experimental
A mixture of 2-(4-fluorophenyl)-2-oxo-N-phenylethanethioamide (3 mmol, 0.819 g), ethyl 2-cyanoacetate (3 mmol, 0.339 g), 10% NaOH solution (0.5 ml), and 15 ml e thanol in a 25 ml flask was stirred for 3 h at room temperature (monitored by TLC). The yellow solid was got by filtering. And then the solid was added to a stirred solution of acetic acid (1 ml) in ethanol (15 ml) at 313 K under MW for 30 min. After cooling to room temperature, the solid product was then got by filtering. The pure product was purified by recrystallization from ethanol (m.p. 498 K).

Special details
Geometry. All e.s. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.