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In Paint.net, is it possible to select a quadrilateral area with diagonal faces? How?

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You can't split pixels if that's what your asking, a diagonal line will cut through pixels, so it will give you a saw-tooth pattern – Ivo Flipse♦ Feb 9 '10 at 9:56
I'm not a Paint.NET user, but as food for thought I'll tell you what I'd do in Photoshop. I'd select a normal (parallel to axis) rectangle, switch to quickmask mode, rotate the quickmask layer 45deg, and switch back. – monov Feb 9 '10 at 11:24
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You can do a rectagular selection and then choose the move selection tool. Press right mousebutton and rotat the rectangle.

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You can create a new layer. Use Line tool to draw a closed area. Then use the Magic Wand tool to create the selection. Switch to your previous layer and you have your selection

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It's not something that's built in, but there might be a plugin that will do what you want (or a good approximation - see Ivo's comment).

The plugins can be found on the Paint.NET forum plugins board

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