Crystal structure of [3,4]dioxole-N′-(2-chloro-5- nitrobenzylidene)benzohydrazide, C15H10ClN3O5

Abstract

C15H10ClN3O5, triclinic, P1 (no. 2), a = 4.890(2) A, b = 10.271(2) A, c = 14.804(3) A, 0 = 96.08(3)°, . = 90.56(3)°, = 90.05(3)°, V = 739.3 A, Z = 2, Rgt(F) = 0.060, wRref(F ) = 0.131, T = 298 K. Source of material [3,4]Dioxolebenzohydrazide (18.2 mg, 0.1 mmol) was dissolved in methanol (10 ml), then 2-chloro-5-nitrobenzaldehyde (18.6 mg, 0.1 mmol) was added slowly into the solution, and the mixture was stirred at room temperature for 3 h. The resulting solutionwas left in air for a few days, yielding colorless block-shaped crystals. Experimental details H2 was located in a difference map and refined with N—H distance restrained to 0.90(1) A. The other H atoms were placed in calculated positions with d(C—H) = 0.93 0.97 A, and with Uiso(H) = 1.2 Ueq(C). Discussion Recently, the crystal structures and biological properties of a large number of hydrazone derivatives and their metal complexes have been reported [1-5]. As part of the ongoing investigation of this class of compounds, the crystal structure of a new hydrazone derivative is reported in this paper. The molecular structure of the title compound consists of a [3,4]dioxolebenzohydrazide and a 2-chloro-5-nitrobenzylidene groups that are located on opposite sides of the C=N bond showing an E configuration. The dihedral angle between the two substituted benzene ringsC1-C6 andC9-C14 is 4.3(3)°. The dihedral angle between the nitro group O1−N3−O2 and the C1-C6 benzene ring is 5.6(3)°. The bond lengths and angles in the compound are in good agreement with the corresponding values observed in the similar structures [6-8]. The torsion angles ofC7−N1−N2−C8 and N1−N2−C8−C9 are 6.0(3)° and 6.3(3)°, respectively. The crystal structure is stabilized by intermolecular N−H···O hydrogen bonds. Z. Kristallogr. NCS 224 (2009) 229-230 / DOI 10.1524/ncrs.2009.0102 229 © by Oldenbourg Wissenschaftsverlag, Munchen Crystal: colorless block, size 0.27 × 0.30 × 0.30 mm Wavelength: Mo K0 radiation (0.71073 A) &: 2.92 cm−1 Diffractometer, scan mode: Bruker SMART 1000 CCD, 1 2max: 53.98° N(hkl)measured, N(hkl)unique: 5929, 3071 Criterion for Iobs, N(hkl)gt: Iobs > 2 !(Iobs), 1483 N(param)refined: 220 Programs: SHELXS-97 [9], SHELXL-97 [10], SHELXTL [11] Table 1. Data collection and handling. H(3) 2i 0.1507 −0.0987 0.8036 0.061 H(4) 2i 0.4592 −0.0124 0.9122 0.067 H(6) 2i 0.6854 0.2547 0.7494 0.049 H(7) 2i 0.1959 0.1916 0.5773 0.047 H(10) 2i 0.3563 0.2534 0.3233 0.047 H(13) 2i 0.8829 0.5860 0.2206 0.060 H(14) 2i 0.9600 0.5210 0.3649 0.048 H(15A) 2i 0.1287 0.4308 0.0668 0.091 H(15B) 2i 0.3398 0.3274 0.0235 0.091 H(2) 2i 0.349(3) 0.308(3) 0.476(2) 0.080 Table 2. Atomic coordinates and displacement parameters (in A). Atom Site x y z Uiso