(E)-4-[7-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2,1,3-benzothiadiazol-4-yl]-2-[(neopentylimino)methyl]phenol

In the title molecule, C24H23N3O3S2, the benzothiadiazole ring system is essentially planar, with an r.m.s. deviation of 0.020 (8) Å. The thiophene and hydroxy-substitiuted rings form dihedral angles of 23.43 (9) and 35.45 (9)°, respectively, with the benzothiadiazole ring system. An intramolecular O—H⋯N hydrogen bond is observed. In the crystal, weak C—H⋯O hydrogen bonds and π–π stacking interactions [centroid–centroid distance = 3.880 (3) Å] link molecules into chains along [100]. In addition, there are short S⋯S contacts [3.532 (3) Å] which link these chains, forming a two-dimensional network parallel to (010).


Comment
The multiple functionalities of the title molecule make it a promising material for a range of applications. Both benzothiadiazole and 3,4-ethylenedioxythiophene containing compounds have been utilized in a wide range of applications including photovoltaics (Sendur et al., 2010), sensors (Tanriverdi et al., 2012;Holliday et al., 2006), non-linear optics and luminescent materials (Ellinger et al., 2011).
The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the benzothiadiazole moeity and the thiophene ring is 23.43 (9)° and the dihedral angle between the benzothiadiazole moeity and the phenol ring is 35.45 (9)°. The geometry of the ethylenedioxythiophene moiety is similar to other ethylenedioxythiophene containing compounds reported in the literature (Mejía et al., 2010;Wong et al., 2008). In the crystal, weak C-H···O hydrogen bonds and π-π stacking interactions (centroid-centroid distance = 3.880 (3) Å) link the molecules into chains along [100] (Fig. 2). The π-π interactions involve inversion related rings containing atoms C7-C12. In addition, there are short S···S contacts (3.532 (3) Å) which link these chains forming a two-dimensional network parallel to (010) (Fig. 3).

Experimental
The title compound was prepared by a condensation reaction between 5-(7-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5yl)benzo[c][1,2,5] thiadiazol-4-yl)-2-hydroxybenzaldehyde, prepared following Dinser (2013), and neopentylamine. The aryl aldehyde (1.41 g, 3.58 mmol) was dissolved in 120 ml of dichloromethane with the aid of sonication. To this solution was added 100 ml of ethanol followed by a concentrated solution of neopenylamine (0.24 ml, 2.05 mmol) dissolved in approximately 2 ml of ethanol. The reaction mixture was then further diluted with 98 ml of ethanol. The reaction mixture was stirred at room temperature for 5 h before the total solvent volume was reduced to approximately 100 ml by rotary evaporation at reduced pressure. Upon standing the product precipitated and was isolated by vacuum filtration. Single crystals suitable for X-ray diffraction were isolated from this sample

Refinement
The hydroxy H atom and the H atom bonded to C19 were refined independently with isotropic displacement parameters.
All other H atoms were positioned geometrically and refined using a riding-model approximation, with C-H = 0.93-0.97 Å and with U iso (H) = 1.2 times U eq (C) or U iso (H) = 1.5 times U eq (C methyl ).  The molecular structure of the title compound. Ellipsoids are drawn at the 50% probability level.  Crystal structure viewed along the b axis. Interactions are shown between O3 and H4a of neighboring molecules. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.26 e Å −3 Δρ min = −0.30 e Å −3 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 > σ(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.