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The Callistophytales nov. order is proposed for a small family of Pennsylvanian and possibly Permian pteridosperms. Plants conform to two species of Callistophyton and their reproductive organs. The small, eustelic sporophytes have a scrambling, shrub-like habit, profuse branching, adventitious roots and pinnately compound fern-like leaves with sphenopterid pinnules. Reproductive organs are borne on the abaxial surface of the pinnules, and consist of cardiocarpalean ovules and synangiate pollen organs with saccate pollen. Gametophyte development and reproductive biology conform closely to those of extant gymnosperms in the Coniferales. Anatomically preserved reproductive organs of the major groups of Paleozoic gymnosperms are compared, and a closer than currently recognized relationship of Paleozoic seed plants is proposed.