( Z )-2-(1-(5-Methyl-1-(4-nitrophenyl)-1 H -1,2,3-triazol-4-yl)ethylidene)- N -phenylhydrazine-1-carbothioamide

: Reaction of equimolar equivalents of 1-(5-methyl-1-(4-nitrophenyl)-1 H -1,2,3-triazol-4-yl)ethan-1-one ( 1 ) and N -phenylhydrazinecarbothioamide ( 2 ) in boiling ethanol containing a catalytic amount of concentrated hydrochloric acid for 4 h gave ( Z )-2-(1-(5-methyl-1-(4-nitrophenyl)-1 H -1,2,3-triazol-4-yl)ethylidene)- N -phenylhydrazine-1-carbothioamide ( 3 ) with 88% yield. The structure of 3 was established using single-crystal X-ray diffraction and magnetic resonance spectroscopy.


NMR Spectroscopic Analysis
The 1 H NMR spectrum of 3 showed two exchangeable singlets, appearing at 9.71 and 10.92 ppm, due to the two NH protons. In addition, the two singlets that appeared at 2.54 and 2.64 ppm were attributed to the protons of the two methyl groups. The 13 C NMR spectrum of 3 showed the presence of a singlet at 177.0 ppm due to the thiocarbonyl carbon. Also observed are two singlets at 11.6 and 15.5 ppm due to the carbon atoms of the two methyl groups (see the Supplementary Material for details). It should be noted that the 1 H NMR spectrum of crude 3 contains a few signals with very low intensities that are possibly due to the presence of 2. Following crystallization, the purity of 3 was confirmed by microanalytical analysis (Section 3.2).

X-Ray Crystal Structure Description
The asymmetric unit of the crystal structure comprises three molecules (M1, M2, and M3) and is shown in Figure 1

NMR Spectroscopic Analysis
The 1 H NMR spectrum of 3 showed two exchangeable singlets, appearing at 9.71 and 10.92 ppm, due to the two NH protons. In addition, the two singlets that appeared at 2.54 and 2.64 ppm were attributed to the protons of the two methyl groups. The 13 C NMR spectrum of 3 showed the presence of a singlet at 177.0 ppm due to the thiocarbonyl carbon. Also observed are two singlets at 11.6 and 15.5 ppm due to the carbon atoms of the two methyl groups (see the Supplementary Material for details). It should be noted that the 1 H NMR spectrum of crude 3 contains a few signals with very low intensities that are possibly due to the presence of 2. Following crystallization, the purity of 3 was confirmed by microanalytical analysis (Section 3.2).

X-ray Crystal Structure Description
The asymmetric unit of the crystal structure comprises three molecules (M 1 , M 2 , and M 3 ) and is shown in Figure 1 In each of the three unique molecules, group B is planar with a maximum deviation from the least squares plane of no more than 0.031(2) Å. Intramolecular N-H . . . N hydrogen bonding contributes to the stabilization of these groups in the planar orientation (Table 1). Groups B and C are coplanar in each of the three molecules with twist angles  In each of the three unique molecules, group B is planar with a maximum deviation from the least squares plane of no more than 0.031(2) Å . Intramolecular N-H…N hydrogen bonding contributes to the stabilization of these groups in the planar orientation (Table 1). Groups B and C are coplanar in each of the three molecules with twist angles of 4.07 (8)

General
A Shimadzu IR Affinity-1 Spectrometer was used to record the IR spectrum of 3. A JEOLNMR spectrometer was used to record the 1 H (500 MHz) and 13 C NMR (125 MHz) spectra in deuterated dimethyl sulfoxide (DMSO-d6). The chemical shift (δ) was recorded in ppm and the coupling constant (J) was measured in Hz. Compound 2 was prepared based on a literature procedure [36].

General
A Shimadzu IR Affinity-1 Spectrometer was used to record the IR spectrum of 3. A JEOLNMR spectrometer was used to record the 1 H (500 MHz) and 13 C NMR (125 MHz) spectra in deuterated dimethyl sulfoxide (DMSO-d 6 ). The chemical shift (δ) was recorded in ppm and the coupling constant (J) was measured in Hz. Compound 2 was prepared based on a literature procedure [36].

Data Collection and Structure Refinement Details
An Agilent SuperNova Dual Atlas diffractometer using mirror monochromated MoKα radiation was used to collect single-crystal diffraction data. The structure of 3 was solved by direct methods using SHELXT [37] and refined by full-matrix least-squares methods on F 2 with SHELXL-2014 [38]. C 18