organic chemistry - Identifying an unknown compound(w/ NMR/IR)?

I need some help identifying the following unknown compound. Any suggestions or hints regarding the possible compound would be highly appreciated.

So far I am thinking the broad peak on the IR is an alcohol that somehow mixed with possible sp3 CH bonds.And the peak around 1600 around is I think a sp Carbon-Carbon bond. The compound should have four distinct groups of protons. Beyond this basic analysis, I couldn't really come up with a compound. Please help.

EDIT(07/09/14): I have updated the question with newer NMR(below the first NMR) and IR.

Some other additional info I worked out in the Lab:

look: white powder like solid.

mp: 116.3-119.0

Solubility Water - insoluble NaOH - insoluble Sulfuric Acid - soluble

Classification Tests: Water Insoluble Phenol Test - positive; a dark red precipitate formed. Chromic Acid Test - positive; green precipitate formed. Bromine Test for Unsaturation - positive; Bromine discoloration happened until about 2 ml of Bromine was added. White precipitate formed.

This is my first time doing these tests so please don't consider their results too strictly. My Instructor said IR is much safer way to determine functional groups.