In the solid state, the title compound, C18H13N5O, adopts a conformation

In the solid state, the title compound, C18H13N5O, adopts a conformation whereby the phenyl ring and meth-oxyCbenzene-1,2-dicarbo-nitrile residue (r. (Table?1 ?). Encompassed within the chains are carbo-nitrile-N5?(benzene) inter-actions, Table?1 ?. The chains are connected into supra-molecular layers in the plane by benzene-C12H?N4(carbo-nitrile) inter-actions across a centre of inversion so that ten-membered ?HC3N2 synthons are formed, Fig.?2 ? and Table?1 YK 4-279 IC50 ?. Layers inter-digitate along the axis but do not form contacts within the standard distance criteria (Spek, 2009 ?), Fig.?3 ?. Figure 2 A view of the supra-molecular layer in the plane in (I). The layer is sustained by CH?N and CH?N inter-actions shown as orange and purple dashed lines, respectively. Figure 3 Unit cell contents for (I) shown in projection down the axis, showing the stacking of layers. The CH?N inter-actions are shown as orange dashed lines. Table 1 Hydrogen-bond geometry (?, ) Hirshfeld surface analysis YK 4-279 IC50 ? The program (Wolff (Spackman and H12 hydrogen atoms as donors dominate the mol-ecular packing. These inter-actions are easily recognized as bright-red spots, and YK 4-279 IC50 are designated as 1, 2 and 3 in a square box, respectively, on the Hirshfeld surface mapped with atoms, reflect the presence of short inter-molecular C?H contacts [C9?H3atoms (H10with respect to the relative orientation of the N- and C-bound residues to the central ring, a disposition is observed in each of (II) (Rostovtsev relationship is observed in (V) (Lpez-Ruiz program (Frisch conformation of (I) is in fact a high-energy conformation, being nearly 7 kcal mol?1 higher in energy than the low-energy conformation which, as shown in Fig.?10 ?, has a conformation of the aromatic rings. In the energy-minimized structure, the dihedral angles between the five-membered ring and the di-nitrile- and benzyl-benzene rings are 73.6 and 85.2, respectively, 9 and 6, respectively, from the comparable angles in the experimental structure. The dihedral angles between the aromatic YK 4-279 IC50 rings is 23.4. While the dihedral angles do not differ significantly between the experimental and gas-phase, energy-minimized structures, the relative conformations are quite distinct. The orientation of the terminal rings is most likely stabilized by intra-molecular C inter-actions, the shortest intra-molecular C?C contact between rings being 3.62??. The adoption of a different conformation in the experimental structure no doubt relates to the dictates of global crystal packing considerations. Figure 9 Energy profile (kcal mol?1) for conformations of (I) differing by a rotation (30 steps) about the OC bond. Figure 10 Overlay diagram of the experimental (red image) and energy-minimized (blue) structures of (I). The mol-ecules have been overlapped so that the five-membered rings are coincident. Synthesis and crystallization ? 3-(Prop-2-yn-1-yl-oxy)phthalo-nitrile (Jan (ArH), 3050 (ArH), 2226 (CN), 1600 (C=C, Ar). [315. Refinement details ? Crystal data, data collection and structure refinement details are summarized in Table?4 ?. Carbon-bound H atoms were placed in calculated positions (CH = 0.95C0.99??) and were included in the refinement in the riding model approximation, with = 315.33= 5.2454 (5) ?Cell parameters from 1806 reflections= 15.3860 (14) ? = 2.5C27.5= 19.042 (3) ? = 0.09 mm?1 = 90.927 (10)= 100 K= 1536.6 (3) ?3Prism, light-brown= 40.35 0.10 0.10 mm View it in a separate window Data collection Agilent Technologies SuperNova Dual diffractometer with an Atlas detector3527 independent reflectionsRadiation source: SuperNova (Mo) X-ray Source2099 reflections with > 2(= ?66Absorption correction: multi-scan (= ?1919= ?242115856 measured reflections View it in a separate window Refinement Refinement on = 1/[2(= (= 1.07(/)max < 0.0013527 reflectionsmax = 0.26 e ??3217 parametersmin = ?0.25 e ??3 View it in a separate window Special details Geometry. All esds (except the Rabbit Polyclonal to CDKA2 esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in.