Crystal structure of N'-(acetylthiophene)propionylhydrazine, C9H12N2OS

C9H12N2OS, monoclinic, P121/c1 (no. 14), a = 4.1595(6) Å, b = 19.139(3) Å, c = 12.655(2) Å, 0 = 97.072(2)°, V = 999.7 Å, Z = 4, Rgt(F) = 0.038, wRref(F) = 0.111, T = 294 K. Source of material All commercially available reagents were used as supplied. The title compound was prepared by a method similar to that of reference [1] . A solution of acetylthiophene (0.1 mol, 12.6 g) in ethanol (10 ml) was added slowly to a solution of propionylhydrazine (0.1 mol, 8.8 g) in ethanol. The reaction mixture was refluxed for 4 hours with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield, 80 %). A ethanol solution of the title compound was slowly evaporated and colorless block crystals were obtained after one week. Chemical analysis — found: C, 54.28 %; H, 6.52 %; N, 14.02 %; S, 15.88 %; calculated for C9H12N2OS: C, 55.08 %; H, 6.16 %; N, 14.27 %; S, 16.33 %. Experimental details The hydrogen atom H2A was located from difference density map and was refined with d(N2—H2A) = 0.89(1) Å. All other H atoms were placed in calculated positions with d(C—H) = 0.93 0.97 Å and Uiso(H) = 1.2 1.5 Ueq of the respective carrier atom. Discussion Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application [2]. This may be attributed to unusual structural features in the resultant metal complexes and their biological activities [3,4]. By reaction with metal which could be utilized for preparation of one-, two-, and threedimensional networks and microporous solids [5]. In the title crystal structure, C5=N1 bond length of 1.276(2) Å is in accord to the value for a double bond and similar to the distance reported earlier [6]. The bond length of 1.346(4) Å is greater than the value for a double bond, and less than the value for a single bond, because of conjugation effects in the molecule. The neighbouring molecules display strong intramolecular hydrogen bond with d(N2−H2A···O1) = 2.953(2) Å. Through the intermolecular hydrogen bonds the molecules are assembled into layers . Z. Kristallogr. NCS 223 (2008) 509-510 / DOI 10.1524/ncrs.2008. 0224 509 © by Oldenbourg Wissenschaftsverlag, München Crystal: colorless block, size 0.16 × 0.18 × 0.60 mm Wavelength: Mo K2 radiation (0.71073 Å) ': 2.86 cm−1 Diffractometer, scan mode: Bruker SMART CCD, +/3 2#max: 52.68° N(hkl)measured, N(hkl)unique: 5620, 2032 Criterion for Iobs, N(hkl)gt: Iobs > 2 ! (Iobs), 1743 N(param)refined: 124 Programs: SHELXS-97 [7], SHELXL-97 [8], SHELXTL [9], WinGX [10] Table 1. Data collection and handling. H(1) 4e −0.1074 0.6343 0.3555 0.079 H(2) 4e 0.0108 0.6171 0.5421 0.082 H(3) 4e 0.3160 0.7138 0.6306 0.070 H(6A) 4e 0.8588 0.8566 0.6248 0.085 H(6B) 4e 0.6130 0.8042 0.6663 0.085 H(6C) 4e 0.5172 0.8829 0.6477 0.085 H(8A) 4e 0.3740 0.9287 0.2524 0.067 H(8B) 4e 0.7041 0.8949 0.2322 0.067 H(9A) 4e 0.5220 1.0325 0.1755 0.103 H(9B) 4e 0.5304 0.9707 0.0945 0.103 H(9C) 4e 0.8540 0.9992 0.1561 0.103 H(2A) 4e 0.807(5) 0.941(1) 0.503(1) 0.075(7) Table 2. Atomic coordinates and displacement parameters (in Å). Atom Site x y z Uiso