X. Qiu
Mar 1, 2009
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Zeitschrift für Kristallographie - New Crystal Structures
Abstract
C16H17ClN2O5, monoclinic, P121/n1 (no. 14), a = 7.429(3) Å, b = 17.524(3) Å, c = 12.596(2) Å, = 91.196(3)°, V = 1639.5 Å, Z = 4, Rgt(F) = 0.062, wRref(F) = 0.162, T = 298 K. Source of material The title compound was prepared by the Schiff base condensation of equimolar (0.5 mmol each) solutions of 5-chlorosalicylaldehyde and 4-hydroxy-3-methoxybenzohydrazide in methanol (20 ml). Excess methanol was removed from the reaction mixture by distillation. The colourless solid was filtered and dried in air. Colourless block-shaped crystals suitable for X-ray diffraction were obtained from a methanol solution. Experimental details The imino H atom was located in a difference map and refined with N—H distance restrained to 0.90(1) Å. The remaining H atoms were positioned geometrically [d(C—H) = 0.93 0.96 Å, d(O—H) = 0.82 Å] and refined using a riding model, with Uiso(H) = 1.2 Ueq(C) and 1.5 Ueq(Cmethyl and O). Rotating group models were used for the methyl groups. Discussion Hyrazone compounds, obtained from the reaction of aldehydes with hydrazides, have been widely studied due to their excellent biological properties [1-3]. Recently, we have reported a few hydrazone compounds [4-6]. The title crystal structure consists of a Schiff base molecule and a methanol molecule. The Schiff base molecule has a trans configuration with respect to the methylidene group. The dihedral angle between the two phenyl rings is 2.5(2)°, indicating a nearly coplanar configuration of the molecule. The bond lengths and angles in the compound are found to have normal values and comparable to the values in the similar compounds [7-9]. The methanol molecules are linked to the Schiff base molecules through intraand intermolecular N−H···O and O−H···O hydrogen bonds. The molecules are linked into two-dimensional layers parallel to the bc plane by intermolecular O−H···O hydrogen bonds. Z. Kristallogr. NCS 224 (2009) 109-110 / DOI 10.1524/ncrs.2009.0051 109 © by Oldenbourg Wissenschaftsverlag, München Crystal: colorless block, size 0.23 × 0.25 × 0.27 mm Wavelength: Mo K0 radiation (0.71073 Å) %: 2.62 cm−1 Diffractometer, scan mode: Bruker SMART CCD, 2 2"max: 54° N(hkl)measured, N(hkl)unique: 13406, 3545 Criterion for Iobs, N(hkl)gt: Iobs > 2 !(Iobs), 1806 N(param)refined: 225 Programs: SHELXS-97 [10], SHELXL-97 [11], SHELXTL [12] Table 1. Data collection and handling. H(1) 4e 0.3679 0.4812 1.1716 0.091 H(4) 4e −0.0840 0.8761 0.6963 0.087 H(5) 4e 0.2790 0.4986 0.7179 0.097 H(3) 4e 0.4748 0.3117 1.2718 0.066 H(4A) 4e 0.4333 0.1973 1.1852 0.068 H(6) 4e 0.2476 0.3064 0.9268 0.057 H(7) 4e 0.2261 0.4426 0.9180 0.052 H(10) 4e 0.2188 0.7921 1.0324 0.044 H(13) 4e −0.0193 0.7446 0.6978 0.048 H(14) 4e 0.0751 0.6440 0.8027 0.045 H(15A) 4e 0.0962 0.9160 1.0837 0.098 H(15B) 4e 0.1898 0.9906 1.0441 0.098 H(15C) 4e 0.2984 0.9140 1.0508 0.098 H(16A) 4e 0.0318 0.4280 0.7514 0.140 H(16B) 4e 0.0465 0.4645 0.6382 0.140 H(16C) 4e −0.0676 0.5049 0.7252 0.140 H(2) 4e 0.210(5) 0.565(2) 0.8955(9) 0.080 Table 2. Atomic coordinates and displacement parameters (in Å). Atom Site x y z Uiso