Create a List of FieldLookupValue's
List<FieldLookupValue> oLookupValues = new List<FieldLookupValue>();
Add a new FieldLookupValue for each file id
oLookupValues.Add(new FieldLookupValue() { LookupId = Convert.ToInt32(lookupID) });
When finished set the listitem to the List
listItem["FieldName"] = oLookupValues ;
listItem.Update();
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