You should be able to modify https://crmcustomemails.codeplex.com/ to accomplish this. I don't think it has the capability to reference child entity attributes OOB, but it is a open source project and you should be able to make these modifications to the code. The new document generation feature in CRM2016 has the capability to iterate through the child records and fill a table in a word or excel template. But AFAIK, there is no SDK message to instantiate the template and send an email with the generated word document.
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