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For my AP Chemistry class we were told to make a molecular diagram that was "better than excellent" and the rest is up to us (we could choose the molecule and how we wanted to represent it).

My group chose benzoylmethylecgonine, or $\ce{C17H21NO4}$, also known as cocaine.

This is proving to be a difficult task as I now realize that cocaine is a pretty complicated molecule and I couldn't find much on the 3D molecular structure. If anyone could explain its chemical structure, it would be very appreciated.

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While I do not think that cocaine is a particularly interesting molecule, the crystal structure has been reported in Ronald J. Hrynchuk, Richard J. Barton, and Beverley E. Robertson, Can. J. Chem., 1983, 61, 481. There is also an open access paper of the XII IUCr Congress available, R. D. Hrynchuk, R. J. Barton and B. E. Robertson, Acta Cryst A, 1981, A37, C72. The crystal structure file has been deposited to ccdc.cam.ac.uk and can be downloaded free of charge. However, as far as I can see, it does only contain the information about the space group, etc, but no atomic co-ordinates.

However, the hydrochloride structure has also been reported in E. J. Gabe and W. H. Barnes, Acta Cryst., 1963, 16, 796-801. And the cif file can be also obtained at ccdc.cam.ac.uk.

I did a quick calculation on this geometry on the DF-BP86/def2-SVP level of theory, the plain xyz coordinates are attached at the end of this post. You can open them with molecular viewers such as Avogadro to create your own model.

The following, however, has been produced with the commercial ChemCraft program.
rotation of cocaine hydrochloride

I do not know how far you want to go with your presentation, there are some pictures on wikipedia. I can also recommend checking the record of it on ChemSpider.


Geometry of cocaine hydrochloride:

symmetry c1
Cl      -2.051693000     -0.493009000      4.153090000
C       -2.451519000     -3.565091000      6.602382000
C       -6.214292000      1.164927000      8.772468000
C       -7.187531000      2.140573000      9.037661000
C       -8.160694000      1.917991000     10.029303000
C       -8.167271000      0.711328000     10.754343000
C       -7.200746000     -0.269358000     10.489848000
C       -4.535361000     -2.199809000      5.904903000
C       -4.965503000     -2.410764000      3.577976000
C       -0.472992000     -3.311748000      5.082266000
C       -3.681531000     -2.746076000      7.063993000
C       -3.208615000     -1.681350000      8.100725000
C       -1.959949000     -0.929634000      7.627840000
C       -0.886578000     -1.913758000      7.125382000
C       -0.580604000     -3.058883000      8.128726000
C       -1.633721000     -4.157723000      7.786625000
C       -5.209882000     -1.120147000      9.257751000
C       -6.215633000     -0.043947000      9.503197000
H       -2.776079000     -4.325870000      5.870251000
H       -1.141638000     -5.101415000      7.477122000
H       -5.458897000      1.318599000      7.989093000
H       -7.190344000      3.080452000      8.463274000
H       -8.921920000      2.687588000     10.235464000
H       -8.932096000      0.535630000     11.527409000
H       -7.186414000     -1.224606000     11.036739000
H       -4.915209000     -3.233215000      2.840991000
H       -4.408859000     -1.522439000      3.213266000
H       -6.015572000     -2.140911000      3.803492000
H        0.202195000     -3.979332000      5.655364000
H       -4.361351000     -3.437105000      7.610613000
H       -1.009855000     -3.900141000      4.313786000
H        0.111577000     -2.526413000      4.564425000
H       -2.986886000     -2.247300000      9.031392000
H       -2.216795000     -0.241161000      6.793930000
H       -1.551394000     -0.325210000      8.463897000
H        0.011514000     -1.355303000      6.795935000
H        0.453167000     -3.437387000      7.998115000
H       -0.655253000     -2.701279000      9.175171000
H       -2.290875000     -4.410651000      8.642544000
N       -1.471722000     -2.634200000      5.937688000
O       -4.202728000     -0.704253000      8.439562000
O       -5.256578000     -2.245544000      9.737495000
O       -5.375360000     -1.329144000      6.012186000
O       -4.299429000     -2.894414000      4.763398000
H       -1.903686000     -1.736871000      5.153339000
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  • $\begingroup$ This was beyond amazing thank you. You mention that you don't find it an interesting molecule, what would you consider interesting? Either way, thanks so much. I really do appreciate it. $\endgroup$ – joshy.poo Feb 21 '15 at 5:18
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    $\begingroup$ @JohnSmith You are welcome. I consider small molecules like carbon monoxide way more interesting. Also small rings like cyclopropane, beta-lactames/lactones and boron compounds... cocaine's biological role is interesting, the molecule itself is just another organic compound. $\endgroup$ – Martin - マーチン Feb 21 '15 at 11:53
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You can also use this interactive image from chemapps.

For cocaine, go to https://chemapps.stolaf.edu/jmol/jmol.php?model=CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC

If you want any other molecule, replace "model=(SMILES of the molecule you want)"

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