Russia’s move comes after Turkey’s president voiced “sadness” over the incident, saying he wished it hadn’t happened.

President Vladimir Putin ordered a series of economic sanctions against Turkey after a Russian fighter jet was shot down by Turkish forces and its pilot killed last week, as tensions over the war in Syria continue to escalate.

A decree published on the Kremlin’s website on Saturday came hours after Turkey’s President Recep Tayyip Erdogan voiced “sadness” over the incident, saying he wished it hadn’t happened.

“The circumstances are unprecedented. The gauntlet thrown down to Russia is unprecedented. So naturally the reaction is in line with this threat,” said Dmitry Peskov, Putin’s spokesman, discussing the new sanctions.

A senior Turkish official told Reuters the move would only worsen the standoff between Moscow and Ankara.

Russia is Turkey’s biggest supplier of natural gas and its second-largest trading partner.

Putin’s decree – which entered into force immediately – included a ban on some unspecified goods and forbids extensions of labour contracts for Turks working in Russia as of January 1.

It also ordered the end of chartered flights from Russia to Turkey, and for Russian tourism companies to stop selling vacation packages that would include a stay in Turkey.

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Russian analyst Lincoln Mitchell told Al Jazeera the sanctions would hurt both sides.

“Sanctions are a tool that the West has used against a number of countries, not least of which is Russia. We now see Russia taking a Western tool and using it,” said Mitchell. “These sanctions are not going to bring great happiness to ordinary Russians. These are pretty hard-hitting sanctions, ones that hit Turkey hard – but also could hit Russia hard.”

Putin’s decree also ended visa-free travel between Russia and Turkey and ordered the tightening of control over Turkish air carriers in Russia “for security reasons”.

The decree was issued “to protect Russian citizens from crimes”, a Kremlin statement said.

Ankara says the Russian fighter jet entered its airspace on Tuesday even though it was warned repeatedly not to. Moscow says its pilots got no warning at all.

Earlier on Saturday, Erdogan had again defended Turkey’s actions and criticised Russia for its moves in Syria before expressing his regrets over the shoot down. The jet’s pilot was shot dead by rebels after he ejected and parachuted into Syria.

“We wish it hadn’t happened, but it happened. I hope something like this doesn’t happen again,” Erdogan told a crowd of supporters.

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The Turkish president added that both sides should approach the issue in a more positive way, and renewed a call for a meeting with Putin on the sidelines of the UN’s climate change conference in Paris that starts on Monday.

Putin has so far refused to talk to Erdogan because Ankara has not yet apologised, a Putin aide said. Erdogan has said Turkey deserves the apology because its airspace was violated.