When did the realistic typesetting of chemical structures start? In many old chemistry books there were limitations on how chemical structures could be represented driven, presumably, by the desire to use available typesetting methods to save costs.

For example, this is a page from a book on industrial chemicals published in the 1930s:



The distorted hexagons are 6-membered aromatic rings but are typeset from vertical and 45° lines with none of the double bonds explicitly shown.

When and how did chemical typesetting become more "realistic" with, for example, proper hexagons for aromatic rings and the correct description of double bonds where appropriate?
this isn't a definite answer but it might show the direction:

I have an old copy of Namensreaktionen in der Organischen Chemie, 2nd ed. by Helmut Krauch and Werner Kunz, published in 1962 at Alfred Hüthig. First edition must have been published in 1960 or 1961.



Most of the arenes in the sketches have the proper shape. Once in a while they seem to be deliberately stretched to align centres that react.

All through the book there's a consistent notation for saturated centres, hydrogen atoms are mostly not omitted.