(2RS)-2-(2,4-Difluorophenyl)-1-[(4-iodobenzyl)(methyl)amino]-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

In the title compound (common name: iodiconazole), C19H19F2IN4O, there is an intramolecular O—H⋯N hydrogen bond and molecules are linked by weak interactions only, namely C—H⋯N, C—H⋯O and C—H⋯F hydrogen bonds, and π-electron ring–π-electron ring interactions between the triazole rings with centroid–centroid distances of 3.725 (3) Å.


Related literature
For the pharmacological activity of azole compounds, see Fromtling (1988); Gallagher et al. (2003). For a liquid chromatography-tandem mass spectrometry (LC-MS/MS) assay for determination of trace amounts of iodiconazole in human plasma, see Gao et al. (2009). For an ultra-fast LC method for the determination of iodiconazole in microdialysis samples and its application in the calibration of laboratory-made linear probes, see Sun et al. (2010). For the high-performance liquid chromatographic (HPLC) determination of iodiconazole in rat plasma, see Wen et al. (2007). For the synthesis of iodiconazole, see Sheng et al. (2002); Zhang et al. (2001). For classification of the hydrogen bonds, see Gilli & Gilli (2009 Table 1 Hydrogen-bond geometry (Å , ). Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.  (Gallagher et al., 2003), too. In order to obtain new compounds with more potent activity, less toxicity and a broader antifungal spectrum, several azole compounds have been synthesized (Sheng et al., 2002;Zhang et al., 2001). Herein we report the crystal structure determination of the title compound which belongs to the same chemical class.
There is an intramolecular O1-H1···N1 hydrogen bond of moderate strength in the structure. (Table 1; For classification of the hydrogen bonds, see Gilli & Gilli, 2009). The molecules are linked by weak C-H···N, C-H···O and C-H···F hydrogen bonds (Table 1). Moreover, there are π-electron ring-π-electron ring interactions between the triazole rings with the centroid distances of 3.725 (3) Å with the symmetry code of the second ring is -x, y, 3/2-z.

Refinement
All the hydrogens were discernible in the difference electron density map. Despite of it the hydrogens attached to the C atoms were treated in the riding atom formalism: C aryl -H=0.93 , C methyl -H=0.96, C methylene -H=0.97 Å.

Figure 1
The title molecule with the atom-labelling scheme. The displacement ellipsoids are drawn at the 30% probability level.
The H atoms are shown as small spheres of arbitrary radius. H atoms treated by a mixture of independent and constrained refinement w = 1/[σ 2 (F o 2 ) + (0.0625P) 2 + 1.2617P] where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.66 e Å −3 Δρ min = −0.89 e Å −3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.0042 (2) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ (F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.