Bulgaria, 1371-1395 AD., Ivan Sisman, ½ Grosh, Youroukova 127.

Bulgaria, second empire, Ivan Shishman, Veliko Tarnovo mint, 1371–1395 AD.,
1/2 Grosso / half Grosh (ø 13-14 mm / 0,50 g), silver, axis about coin alignment ↑↓ (ca. 160°),
Obv.: half-length figure of virgin Mary orans facing; on her breast, nimbate head of the infant christ facing.
Rev.: Ivan Šišman standing facing with cross-tipped sceptre, monograms flanking.
Dochev 4440 ; Raduchev & Zhekov 1.15.9. ; Youroukova & Penchev 127 .

Ivan Shishman (Bulgarian: Иван Шишман) ruled as emperor (tsar) of Bulgaria in Tarnovo from 1371 to 3 June 1395. The authority of Ivan Shishman was limited to the central parts of the Bulgarian Empire.

Veliko Tarnovo (Bulgarian: Велико Търново, "Great Tarnovo") is a city in north central Bulgaria and the administrative centre of Veliko Tarnovo Province.
Often referred to as the "City of the Tsars", Veliko Tarnovo is located on the Yantra River and is famously known as the historical capital of the Second Bulgarian Empire.

More on https://en.wikipedia.org/wiki/Ivan_Shishman_of_Bulgaria ; https://en.wikipedia.org/wiki/Veliko_Tarnovo