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The -num denotes the number of images you have. That is why you have an error on positives.dat(109) since the program is looking for 109th image but it doesn't exist. Set your -num to 108 and it will work.

If you want OpenCV to produce more samples then as Prasana said you will have to produce each sample individualy. You can write a bash script to do this. If I knew which operating system you are using I would provice that for you considering your image names can be calculated by an incrementing integer.