(E)-6-Bromo-3-{2-[2-(4-chlorobenzylidene)hydrazinyl]thiazol-5-yl}-2H-chromen-2-one

In the title compound, C19H11N3O2SClBr, the chromene ring system and the thiazole ring are each approximately planar, with maximum deviations of 0.033 (3) Å and 0.006 (3) Å, respectively. The molecule adopts an E configuration about the central C=N double bond. The central thiazole ring makes dihedral angles of 9.06 (14)° and 12.07 (11)° with the chloro-substituted phenyl ring and the chromene ring, respectively. The molecular structure features a short C—H⋯O contact, which generates an S(6) ring motif. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, which link the molecules into chains along the b axis. π–π stacking interactions [centroid-centroid distance = 3.4813 (15) Å] are also present.

In the title compound, C 19 H 11 N 3 O 2 SClBr, the chromene ring system and the thiazole ring are each approximately planar, with maximum deviations of 0.033 (3) Å and 0.006 (3) Å , respectively. The molecule adopts an E configuration about the central C N double bond. The central thiazole ring makes dihedral angles of 9.06 (14) and 12.07 (11) with the chloro-substituted phenyl ring and the chromene ring, respectively. The molecular structure features a short C-HÁ Á ÁO contact, which generates an S(6) ring motif. The crystal structure is stabilized by intermolecular N-HÁ Á ÁO hydrogen bonds, which link the molecules into chains along the b axis.

Comment
Thiazolyl coumarin derivatives are reported to be associated with diverse applications. They have industrial applications as fluorescent probes, laser dyes (Samsonova et al., 2007) and luminescents (Bullock et al., 2009). They also exhibit a variety of biological activities as anticonvulsants (Siddiqui et al., 2009), analgesics, anti-inflammatory (Kalkhambkar et al., 2007) and antimicrobial agents (Kamal et al., 2009;Desai et al., 2008). The title compound is a new derivative of thiazolylcoumarin. We present here its crystal structure.
The molecular structure of the compound, (I), displays a trans configuration with respect to the C13═N3 double bond.

Refinement
Atom H1N2 was located from a difference Fourier map and refined freely [N-H = 0.81 (4) Å]. The remaining H atoms were positioned geometrically [C-H = 0.93 Å] and were refined using a riding model, with U iso (H) = 1.2 U eq (C). The highest residual electron density peak is located at 1.20 Å from Br1 and the deepest hole 0.91 located at from Br1.
supplementary materials sup-2 Figures   Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular hydrogen bond is shown as a dashed line.

Special details
Geometry. All esds (except the 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 the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq