Pre 1920's CCM

I picked up some CCM parts and a bike from a friend. The bike is not a straight top tube, has an early type crank, 4 pinstyle. I was wondering what year the straight top tube went away and when the curved top tube started. When did the 4 pin style crank stop being produced. The bike also has the Hercules hub with no brake arm.

The other parts are early 4 pin type cranks and chainrings. 1 chainring was nickel plated a few years back and has not been used. The cranks are different. Anyone know what years they would have been used. I also got a real nice Triplex crank from same guy and some Gibson pedals, 1 set with PAT APP on the side, earlier than the 1923 pedals.

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