H. Qian, He-ping Li, Zhigang Yin
2010
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Zeitschrift für Kristallographie - New Crystal Structures
Abstract
C13H10Cl2N2O2, monoclinic, P121/c1 (no. 14), a = 10.486(1) Å, b = 15.742(3) Å, c = 8.003(2) Å, * = 91.69(1)°, V = 1320.6 Å, Z = 4, Rgt(F) = 0.039, wRref(F ) = 0.089, T = 293 K. Source of material 2,4-Dichlorobenzaldehyde (2 mmol, 0.35 g) was dissolved in anhydrous methanol (10 ml), the mixture was stirred for several minitutes at room temperature. 4-Nitroaniline (2 mmol, 0.276 g) in methanol (5 ml) was added dropwise, and the mixture was stirred at room temperature for 2 h. The Schiff base was obtained and reduced with sodium borohydride (5 mmol, 0.185 g). The mixture was stirred for 4 h at RT, then evaporated to dryness, the product was recrystallised from dichloromethane. Colorless single crystals of the title compound were obtained after 3 d. Discussion The properties and molecular structure of complexes containing the nitroamine group are of interest as their complexes with transition metal exhibit superior activity as catalysts in polymerizations [1,2]. N-(2,4-dichlorobenzyl)-4-nitroaniline is a non-planar molecule. The 2,4-dichlorobenzene ring is nearly perpendicular to the nitrobenzene ring with a dihedral angle of 89.1(1)°. The nitro group is nearly co-planar with its benzene ring making a dihedral angle of 3.7(1)°. In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds which help to stablize the molecule packing. Z. Kristallogr. NCS 225 (2010) 253-254 / DOI 10.1524/ncrs.2010.0110 253 © by Oldenbourg Wissenschaftsverlag, München Crystal: colorless block, size 0.24 × 0.26 × 0.28 mm Wavelength: Mo Kα radiation (0.71073 Å) .: 4.89 cm−1 Diffractometer, scan mode: Bruker SMART CCD, ' 2,max: 52.94° N(hkl)measured, N(hkl)unique: 9106, 2698 Criterion for Iobs, N(hkl)gt: Iobs > 2 )(Iobs), 1125 N(param)refined: 172 Programs: SHELXS-97 [3], SHELXL-97 [4], SHELXTL [5] Table 1. Data collection and handling. H(1A) 4e −0.3913 0.5709 0.4368 0.066 H(12A) 4e −0.3311 0.8938 0.4274 0.071 H(10A) 4e −0.6345 0.7767 0.2191 0.067 H(2A) 4e 0.1947 0.6475 0.4023 0.074 H(7A) 4e −0.2177 0.5430 0.5829 0.074 H(7B) 4e −0.2055 0.6399 0.6243 0.074 H(9A) 4e −0.5536 0.6481 0.3016 0.064 H(4A) 4e −0.0438 0.5818 0.0255 0.082 H(5A) 4e −0.2080 0.5746 0.2073 0.074 H(13A) 4e −0.2444 0.7647 0.5067 0.066 Table 2. Atomic coordinates and displacement parameters (in Å). Atom Site x y z Uiso