diff --git a/compiler/backend/src/org/jetbrains/jet/codegen/ExpressionCodegen.java b/compiler/backend/src/org/jetbrains/jet/codegen/ExpressionCodegen.java
index bbe52384d2e..e2a3198802d 100644
--- a/compiler/backend/src/org/jetbrains/jet/codegen/ExpressionCodegen.java
+++ b/compiler/backend/src/org/jetbrains/jet/codegen/ExpressionCodegen.java
@@ -1881,9 +1881,18 @@ public class ExpressionCodegen extends JetVisitor<StackValue, StackValue> {
             StackValue leftValue = gen(expr);
             FunctionDescriptor op = (FunctionDescriptor) bindingContext.get(BindingContext.REFERENCE_TARGET, expression.getOperationReference());
             assert op != null;
-            leftValue.put(asmType(op.getValueParameters().get(0).getType()), v);
-            genToJVMStack(expression.getRight());
-            v.swap();
+            Type type = asmType(op.getValueParameters().get(0).getType());
+            if(type.getSize() == 1) {
+                leftValue.put(type, v);
+                genToJVMStack(expression.getRight());
+                v.swap();
+            }
+            else {
+                leftValue.put(type, v);
+                genToJVMStack(expression.getRight());
+                v.dupX2();
+                v.pop();
+            }
             invokeFunctionNoParams(op, Type.BOOLEAN_TYPE, v);
         }
         return StackValue.onStack(Type.BOOLEAN_TYPE);
diff --git a/compiler/backend/src/org/jetbrains/jet/codegen/JetTypeMapper.java b/compiler/backend/src/org/jetbrains/jet/codegen/JetTypeMapper.java
index 3deff66d90c..6261c2c9828 100644
--- a/compiler/backend/src/org/jetbrains/jet/codegen/JetTypeMapper.java
+++ b/compiler/backend/src/org/jetbrains/jet/codegen/JetTypeMapper.java
@@ -71,6 +71,20 @@ public class JetTypeMapper {
     public static final Type ARRAY_GENERIC_TYPE = Type.getType(Object[].class);
     public static final Type TUPLE0_TYPE = Type.getObjectType("jet/Tuple0");
 
+    public static final Type TYPE_ITERATOR = Type.getObjectType("jet/Iterator");
+    public static final Type TYPE_INT_RANGE = Type.getObjectType("jet/IntRange");
+    public static final Type TYPE_SHARED_VAR = Type.getObjectType("jet/runtime/SharedVar$Object");
+    public static final Type TYPE_SHARED_INT = Type.getObjectType("jet/runtime/SharedVar$Int");
+    public static final Type TYPE_SHARED_DOUBLE = Type.getObjectType("jet/runtime/SharedVar$Double");
+    public static final Type TYPE_SHARED_FLOAT = Type.getObjectType("jet/runtime/SharedVar$Float");
+    public static final Type TYPE_SHARED_BYTE = Type.getObjectType("jet/runtime/SharedVar$Byte");
+    public static final Type TYPE_SHARED_SHORT = Type.getObjectType("jet/runtime/SharedVar$Short");
+    public static final Type TYPE_SHARED_CHAR = Type.getObjectType("jet/runtime/SharedVar$Char");
+    public static final Type TYPE_SHARED_LONG = Type.getObjectType("jet/runtime/SharedVar$Long");
+    public static final Type TYPE_SHARED_BOOLEAN = Type.getObjectType("jet/runtime/SharedVar$Boolean");
+    public static final Type TYPE_FUNCTION0 = Type.getObjectType("jet/Function0");
+    public static final Type TYPE_FUNCTION1 = Type.getObjectType("jet/Function1");
+
     private JetStandardLibrary standardLibrary1;
     public BindingContext bindingContext;
     private ClosureAnnotator closureAnnotator;
@@ -148,20 +162,6 @@ public class JetTypeMapper {
     private final HashMap<KnownTypeKey, Type> knowTypes = Maps.newHashMap();
 
 
-    public static final Type TYPE_ITERATOR = Type.getObjectType("jet/Iterator");
-    public static final Type TYPE_INT_RANGE = Type.getObjectType("jet/IntRange");
-    public static final Type TYPE_SHARED_VAR = Type.getObjectType("jet/runtime/SharedVar$Object");
-    public static final Type TYPE_SHARED_INT = Type.getObjectType("jet/runtime/SharedVar$Int");
-    public static final Type TYPE_SHARED_DOUBLE = Type.getObjectType("jet/runtime/SharedVar$Double");
-    public static final Type TYPE_SHARED_FLOAT = Type.getObjectType("jet/runtime/SharedVar$Float");
-    public static final Type TYPE_SHARED_BYTE = Type.getObjectType("jet/runtime/SharedVar$Byte");
-    public static final Type TYPE_SHARED_SHORT = Type.getObjectType("jet/runtime/SharedVar$Short");
-    public static final Type TYPE_SHARED_CHAR = Type.getObjectType("jet/runtime/SharedVar$Char");
-    public static final Type TYPE_SHARED_LONG = Type.getObjectType("jet/runtime/SharedVar$Long");
-    public static final Type TYPE_SHARED_BOOLEAN = Type.getObjectType("jet/runtime/SharedVar$Boolean");
-    public static final Type TYPE_FUNCTION0 = Type.getObjectType("jet/Function0");
-    public static final Type TYPE_FUNCTION1 = Type.getObjectType("jet/Function1");
-
     public static boolean isIntPrimitive(Type type) {
         return type == Type.INT_TYPE || type == Type.SHORT_TYPE || type == Type.BYTE_TYPE || type == Type.CHAR_TYPE;
     }
diff --git a/compiler/testData/codegen/regressions/kt2416.kt b/compiler/testData/codegen/regressions/kt2416.kt
new file mode 100644
index 00000000000..81c2fb4c6ac
--- /dev/null
+++ b/compiler/testData/codegen/regressions/kt2416.kt
@@ -0,0 +1,13 @@
+fun main(args: Array<String>) {
+    9 in 0..9
+    val intRange = 0..9
+    9 in intRange
+    val charRange = '0'..'9'
+    '9' in charRange
+    val byteRange = 0.toByte()..9.toByte()
+    9.toByte() in byteRange
+    val longRange = 0.toLong()..9.toLong()
+    9.toLong() in longRange
+    val shortRange = 0.toShort()..9.toShort()
+    9.toShort() in shortRange
+}
\ No newline at end of file
diff --git a/compiler/tests/org/jetbrains/jet/codegen/ControlStructuresTest.java b/compiler/tests/org/jetbrains/jet/codegen/ControlStructuresTest.java
index 83c2aca2a40..a0a13a468b8 100644
--- a/compiler/tests/org/jetbrains/jet/codegen/ControlStructuresTest.java
+++ b/compiler/tests/org/jetbrains/jet/codegen/ControlStructuresTest.java
@@ -366,4 +366,9 @@ public class ControlStructuresTest extends CodegenTestCase {
         createEnvironmentWithFullJdk();
         blackBoxFile("regressions/kt2423.kt");
     }
+
+    public void testKt2416() {
+        createEnvironmentWithMockJdkAndIdeaAnnotations(ConfigurationKind.JDK_ONLY);
+        blackBoxFile("regressions/kt2416.kt");
+    }
 }
diff --git a/runtime/src/jet/ByteRange.java b/runtime/src/jet/ByteRange.java
index 716cb17890a..881e62758f9 100644
--- a/runtime/src/jet/ByteRange.java
+++ b/runtime/src/jet/ByteRange.java
@@ -39,6 +39,13 @@ public final class ByteRange implements Range<Byte>, ByteIterable {
         return item <= start && item > start + count;
     }
 
+    public boolean contains(byte item) {
+        if (count >= 0) {
+            return item >= start && item < start + count;
+        }
+        return item <= start && item > start + count;
+    }
+
     @Override
     public boolean equals(Object o) {
         if (this == o) {
diff --git a/runtime/src/jet/CharRange.java b/runtime/src/jet/CharRange.java
index c6bc191e179..1f41d6fe26b 100644
--- a/runtime/src/jet/CharRange.java
+++ b/runtime/src/jet/CharRange.java
@@ -39,6 +39,13 @@ public final class CharRange implements Range<Character>, CharIterable {
         return item <= start && item > start + count;
     }
 
+    public boolean contains(char item) {
+        if (count >= 0) {
+            return item >= start && item < start + count;
+        }
+        return item <= start && item > start + count;
+    }
+
     @Override
     public boolean equals(Object o) {
         if (this == o) {
diff --git a/runtime/src/jet/IntRange.java b/runtime/src/jet/IntRange.java
index 16ed6d57e2c..913bc287717 100644
--- a/runtime/src/jet/IntRange.java
+++ b/runtime/src/jet/IntRange.java
@@ -48,6 +48,13 @@ public final class IntRange implements Range<Integer>, IntIterable {
         return item <= start && item > start + count;
     }
 
+    public boolean contains(int item) {
+        if (count >= 0) {
+            return item >= start && item < start + count;
+        }
+        return item <= start && item > start + count;
+    }
+
     @Override
     public boolean equals(Object o) {
         if (this == o) {
diff --git a/runtime/src/jet/LongRange.java b/runtime/src/jet/LongRange.java
index 4b544faa7f3..f091be8de81 100644
--- a/runtime/src/jet/LongRange.java
+++ b/runtime/src/jet/LongRange.java
@@ -46,6 +46,13 @@ public final class LongRange implements Range<Long>, LongIterable {
         return item <= start && item > start + count;
     }
 
+    public boolean contains(long item) {
+        if (count >= 0) {
+            return item >= start && item < start + count;
+        }
+        return item <= start && item > start + count;
+    }
+
     @Override
     public boolean equals(Object o) {
         if (this == o) {
diff --git a/runtime/src/jet/ShortRange.java b/runtime/src/jet/ShortRange.java
index ff5423d0b91..6cddf3bba53 100644
--- a/runtime/src/jet/ShortRange.java
+++ b/runtime/src/jet/ShortRange.java
@@ -46,6 +46,13 @@ public final class ShortRange implements Range<Short>, ShortIterable {
         return item <= start && item > start + count;
     }
 
+    public boolean contains(short item) {
+        if (count >= 0) {
+            return item >= start && item < start + count;
+        }
+        return item <= start && item > start + count;
+    }
+
     @Override
     public boolean equals(Object o) {
         if (this == o) {