We present deep CCD photometry of the very rich, intermediate aged (similar to the Hyades) open star cluster NGC 2099 (M37). The V, B-V color-magnitude diagram (CMD) for the cluster shows an extremely well populated and very tightly constrained main-sequence extending over 12 magnitudes from the turn-off. The CFH12K photometry for this cluster is faint enough (V ~ 24.5) to detect the remnants of the most massive progenitor cluster stars under the Type I SNe limit. Therefore, the CMD of the cluster also exhibits a well defined white dwarf `clump caused by the decreased rate of cooling of these stars as they age, and a subsequent gap with very few objects. The termination point (Mv = 11.95 +/- 0.30) of the white dwarf luminosity function gives a white dwarf cooling age of 566 +/- 154/176 Myrs which is in excellent agreement with the main-sequence turn-off isochrone age (520 Myrs). By carefully accounting for errors, we show that the cooling age confirms that models including convective core overshooting are preferred for young-intermediate aged clusters. We also derive the reddening (E(B-V) = 0.21 +/- 0.03) and distance ((m-M)v = 11.55 +/- 0.13) to NGC 2099 by matching main-sequence features in the cluster to a new fiducial main-sequence for the Hyades. As a continuing part of the goals of the CFHT Open Star Cluster Survey to better understand dynamical processes of open clusters, we also fit a King model to the cluster density distribution and investigate the cluster main-sequence luminosity and mass functions in increasing concentric annuli. We find some evidence for mass segregation within the boundary of NGC 2099 as expected given the clusters age relative to the dynamical age. The present global mass function for the cluster is found to be shallower than a Salpeter IMF.
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