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In 2268, Loskene intercepted the USS Enterprise, ordering it to leave Tholian space. Loskene allowed the Enterprise an hour and fifty-three minutes, which the starship required to potentially rescue James T. Kirk, who was lost in spatial interphase.
When the allotted time expired and Loskene opened fire on the Enterprise, the Enterprise returned fire, temporarily disabling Loskene's ship. Loskene called for reinforcements and proceeded to form a Tholian web around the Enterprise. Before the web was completed, the Enterprise was able to escape and Loskene was defeated. (TOS: "The Tholian Web")