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copied!<p>I have a solution that works with your example data. It is not a universal solution and may fail with other examples, but it shows how to use recursions. I did not include any error handling. A real-world solution would have to.</p> <p>I use this helper method which gets the item type of the generic lists:</p> <pre><code>private static Type GetListItemType(Type listType) { Type itemType = null; foreach (Type interfaceType in listType.GetInterfaces()) { if (interfaceType.IsGenericType && interfaceType.GetGenericTypeDefinition() == typeof(IList<>)) { itemType = interfaceType.GetGenericArguments()[0]; break; } } return itemType; } </code></pre> <p>Now, the recursion:</p> <pre><code>public void SplitKeyValues(IList source, List<object> keys, List<object> values) { Type itemType = GetListItemType(source.GetType()); PropertyInfo[] properties = itemType.GetProperties(); for (int i = 0; i < source.Count; i++) { object item = source[i]; var itemValues = new List<object>(); values.Add(itemValues); foreach (PropertyInfo prop in properties) { if (typeof(IList).IsAssignableFrom(prop.PropertyType) && prop.PropertyType.IsGenericType) { // We have a List<T> or array Type genericArgType = GetListItemType(prop.PropertyType); if (genericArgType.IsValueType || genericArgType == typeof(string)) { // We have a list or array of a simple type if (i == 0) keys.Add(prop.Name); List<object> subValues = new List<object>(); itemValues.Add(subValues); subValues.AddRange( Enumerable.Cast<object>( (IEnumerable)prop.GetValue(item, null))); } else { // We have a list or array of a complex type List<object> subKeys = new List<object>(); if (i == 0) keys.Add(subKeys); List<object> subValues = new List<object>(); itemValues.Add(subValues); SplitKeyValues( (IList)prop.GetValue(item, null), subKeys, subValues); } } else if (prop.PropertyType.IsValueType || prop.PropertyType == typeof(string)) { // We have a simple type if (i == 0) keys.Add(prop.Name); itemValues.Add(prop.GetValue(item, null)); } else { // We have a complex type. // Does not occur in your example } } } } </code></pre> <p>I call it like this:</p> <pre><code>List<User> userList = InitializeObjects(); List<object> keys = new List<object>(); List<object> values = new List<object>(); SplitKeyValues(userList, keys, values); </code></pre> <p><code>InitializeObjects</code> initializes the user list as you did above.</p> <hr> <p><strong>UPDATE</strong></p> <p>The problem is that you are using an anonymous type <code>new { Friends = ... }</code>. You would have to create an anonymous type dynamically by using reflection. And that's pretty nasty. The article <a href="http://www.developmentalmadness.com/archive/2008/02/12/extend-anonymous-types-using.aspx" rel="nofollow noreferrer">"Extend Anonymous Types using Reflection.Emit"</a> seems to do it. (I didn't test it).</p> <p>Maybe an easier approach would do the job. I suggest creating a helper class for the description of class types.</p> <pre><code>public class Class { public string Name { get; set; } public List<object> Structure { get; set; } } </code></pre> <p>Now let's replace an else case in the code above:</p> <pre><code>... } else { // We have a list or array of a complex type List<object> subKeys = new List<object>(); var classDescr = new Class { Name = genericArgType.Name, Structure = subKeys }; if (i == 0) keys.Add(classDescr); List<object> subValues = new List<object>(); itemValues.Add(subValues); SplitKeyValues( (IList)prop.GetValue(item, null), subKeys, subValues); } ... </code></pre> <p>The result is: <img src="https://i.stack.imgur.com/JHNZj.png" alt="enter image description here"></p>

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