3-(2-Amino-1,3-thiazol-4-yl)-6-bromo-2H-chromen-2-one

The molecule of the title compound, C12H7BrN2O2S, is essentially planar with a maximum deviation of 0.234 (3) Å from the mean plane through all non-H atoms. The dihedral angle between the coumarin ring plane and that of the five-membered thiazole ring is 12.9 (1)°. In the crystal, strong N—H⋯O, N—H⋯N and weak but highly directional C—H⋯O hydrogen bonds provide the links between the molecules. In addition, C—H⋯π and π–π interactions [centroid–centroid distances = 3.950 (3)–4.024 (3) Å] provide additional stability to the interlayer regions in the lattice.

The molecule of the title compound, C 12 H 7 BrN 2 O 2 S, is essentially planar with a maximum deviation of 0.234 (3) Å from the mean plane through all non-H atoms. The dihedral angle between the coumarin ring plane and that of the fivemembered thiazole ring is 12.9 (1) . In the crystal, strong N-HÁ Á ÁO, N-HÁ Á ÁN and weak but highly directional C-HÁ Á ÁO hydrogen bonds provide the links between the molecules. In addition, C-HÁ Á Á andinteractions [centroid-centroid distances = 3.950 (3)-4.024 (3) Å ] provide additional stability to the interlayer regions in the lattice.
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009  in the dye industry (Hooper et al., 1982 )and in the area of laser dyes (Nemkovich et al., 1997) based on the fact that such compounds show state dependent variations in their static dipole moments. The geometry and molecular packing patterns of several coumarins derivatives have been studied to evaluate the features of non-covalent interactions (Vishnumurthy et al., 2001). Against this background, and to obtain more information on such compounds the solid-state structure of the title compound is reported here.
The molecular structure consists of a bromo substituted coumarin ring attached to an amino thiazoyl moiety ( Figure 1).
This compound crystallizes in a monoclinic centrosymmetric space group with Z'=1. The molecule is approximately planar, with a dihedral angle between the two rings being 12.9 (1) °. An analysis of the weighted least-squares plane through the coumarin ring C1/O2 and the thiazoyl ring shows that it is planar with the largest displacement of -0.019 (2)Å for C9. A characteristic Br···S short contact with distance 3.411 (2)Å is observed in the crystal lattice. Strong N-H···N and N-H···O hydrogen bonds (involving both H2A and H2B of the amino group with the ring nitrogen N1 and keto oxygen O1) form R 2 2(8) [Bernstein et al., 1995] molecular dimers. These are linked by C(8) molecular chains along the crystallographic b axis forming a characteristic "chain of dimers". Furthermore, C-H···π interactions (involving H7 and the aromatic thiazoyl ring) provide additional stability forming chains along 'b' axis. Two such one-dimensional chains are linked by intermolecular C-H···O hydrogen bonds (involving H4 and O1) forming C(7) molecular chains along 'n' glide leading to the formation of a two dimensional sheet-like structure ( Figure 2). π-π Stacking interactions involving the C4/C9 aromatic ring, Cg···Cg

Experimental
The compounds were synthesized in accordance with the procedure reported in the literature (Venugopala et al., 2004).
Single crystals of the compound were grown both chloroform:methanol (1:1) by slow evaporation at 275-277 K.

Refinement
All H-atoms were positioned geometrically and refined using a riding model with d(C-H) = 0.93Å, U iso =1.2U eq (C) for aromatic and 0.86Å, U iso = 1.2U eq (N) for the NH atoms.
supplementary materials sup-2 Figures   Fig. 1. The structure of the title compound drawn with 50% probability displacement ellipsoids.