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Five people were killed and 37 injured when a Russian missile struck the heart of the northern Ukrainian city of Chernihiv, the interior ministry said.
Eleven children were among those wounded. A main square, university building and a theatre have reportedly been damaged.
President Volodymyr Zelensky posted a short video showing heavily damaged parked cars.
Chernihiv is close to the border with Belarus.
It was occupied by Russia at the beginning of the invasion, but then recaptured by Ukrainian troops.
"A Russian missile hit right in the centre of the city, in our Chernihiv. A square, the polytechnic university, a theatre," President Zelensky posted on Telegram.
"An ordinary Saturday, which Russia turned into a day of pain and loss. There are dead, there are wounded," he added.
The city centre has been partially closed to allow emergency services access.
Elsewhere, Russia has claimed that a Ukrainian drone hit a military airfield in the northwest Novgorod region.
"As a result of the terrorist attack on the territory of the airfield, a fire broke out in the aircraft parking lot, which was promptly eliminated by fire brigades," the Russian defence ministry posted on Telegram.
One plane was damaged but no casualties have been reported, it added.
Ukraine has not commented on the alleged drone attack.