3-(Prop-2-yn-1-yloxy)phthalonitrile

In the title compound, C11H6N2O {systematic name: 3-(prop-2-yn-1-yloxy)benzene-1,2-dicarbonitrile}, the 14 non-H atoms are approximately coplanar (r.m.s. deviation = 0.051 Å) with the terminal ethyne group being syn with the adjacent cyano residue. In the crystal, centrosymmetric dimers are connected by pairs of C—H⋯N interactions and these are linked into a supramolecular tape parallel to (1-30) via C—H⋯N interactions involving the same N atom as acceptor.

In the title compound, C 11 H 6 N 2 O {systematic name: 3-(prop-2-yn-1-yloxy)benzene-1,2-dicarbonitrile}, the 14 non-H atoms are approximately coplanar (r.m.s. deviation = 0.051 Å ) with the terminal ethyne group being syn with the adjacent cyano residue. In the crystal, centrosymmetric dimers are connected by pairs of C-HÁ Á ÁN interactions and these are linked into a supramolecular tape parallel to (130) via C-HÁ Á ÁN interactions involving the same N atom as acceptor.

Tiekink Comment
As part of our on-going study of functional phthalocyanines, we have previously reported the synthesis and structure (Chin et al., 2012) of precursor 4-(prop-2-ylnyloxy)phthalonitrile obtained by the S N Ar reaction of propagyl alcohol and 4-nitrophthalonitrile, facilitated by potassium carbonate in DMF following literature precedents (Wu et al., 1998;Seven et al., 2009). Despite increased steric hindrance, this method is also suitable for preparing the title compound, (I).
In ( atoms. The ethyne group is syn to the adjacent cyano group. In the crystal structure, centrosymmetrically pairs are connected into dimeric aggregates via C-H···N interactions and these are in turn linked into a supramolecular tape, parallel to (1 -3 0), via C-H···N interactions with translationally related dimeric aggregates, Fig. 2 and Table 1. As the N1 atom participates in both C-H···N interactions, it is bifurcated. Chains stack along the a axis with separations of 4.014 (4) Å between the benzene rings, corresponding to the length of the a axis, and with no significant intermolecular interactions between them.

Experimental
The title compound was prepared by modification of literature procedures (Wu et al., 1998;Seven et al., 2009). Under a nitrogen atmosphere, anhydrous potassium carbonate (1.60 g, 11.6 mmol) was added in three portions at 1 h intervals to a solution of propargyl alcohol (2.16 ml, 37.4 mmol) and 3-nitrophthalonitrile (1.01 g, 5.83 mmol) in dry N,N-dimethylformamide (10 ml). After 96 h, the crude reaction mixture was poured into water (200 ml) and stirred rapidly. The brown precipitate was collected by vacuum filtration, washed with water and dried to provide 0.91 g of material that was purified by silica gel column chromatography using CH 2 Cl 2 and recrystallized from CH 2 Cl 2 /hexane to yield 0.68 g program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).  The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Figure 2
A view of the unit-cell contents of (I) in projection down the a axis. The C-H···N hydrogen bonds are shown as blue dashed lines. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.28 e Å −3 Δρ min = −0.31 e Å −3 Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.