Crystal and molecular structure and DFT calculations of the steroidal oxime 6E-hydroximino-androst-4-ene-3,17-dione ( C19H25NO3) a Molecule with Antiproliferative Activity
Palmer, R., Lisgarten, D., Cockcroft, J., Lisgarten, J., Talbert, R., Dines, T., Bansal, R., Chandra Archarya, P. and Amruta, S. 2018. Crystal and molecular structure and DFT calculations of the steroidal oxime 6E-hydroximino-androst-4-ene-3,17-dione ( C19H25NO3) a Molecule with Antiproliferative Activity. Journal of Chemical Crystallography. 49, pp. 1-8. https://doi.org/10.1007/s10870-018-0747-x
|Authors||Palmer, R., Lisgarten, D., Cockcroft, J., Lisgarten, J., Talbert, R., Dines, T., Bansal, R., Chandra Archarya, P. and Amruta, S.|
The single crystal X-ray structure of the novel steroid derivative, 6E-hydroximino-androst-4-ene-3,17-dione ( C19H25NO3) (code name RB-499), possessing antiproliferative activity against various cell lines is presented.
The analysis produced the following results: chemical formula C19H25NO3; Mr = 315.40; crystals are orthorhombic space group P212121 with Z = 4 molecules per unit cell with a = 6.2609(2), b = 12.5711(4), c = 20.0517(4) Å,Vc = 1578.18(7) Å3, crystal density Dc = 1.327 g/cm³. Structure determination was performed by direct methods, Fourier and full-matrix least-squares refinement. Hydrogens were located in the electron density and refined in position with isotropic thermal parameters.
The final R-index was 0.0324for 3140 reflections with I > 2σ and 308 parameters. The Absolute Structure Parameter − 0.07(5) confirms the correct allocation of the absolute configuration. The presence of the double bond C=O at position 3 in Ring A has caused a distortion from the usual chair conformation and created an unusual distorted sofa conformation folded across an approximate m-plane through C(1)–C(4). Ring B is a distorted chair, its conformation being influenced by the presence of the C(6)=N(6)–O(6)H group in position 6. Ring C is a symmetrical chair. Ring D exhibits both a distorted mirror symmetry conformation [influenced by the C(17)=O(17) group] and a distorted twofold conformation. DFT calculations indicated some degree of flexibility in rings A, C and D with ring A showing the greatest variation in torsion angles. The crystal packing is governed by H-bonds involving O(3), O(6) and O(17). DFT calculations of bond distances and angles, optimized at the B3LYP/6–31++G(d,p) level, were in good agreement with the X-ray structure.
|Journal||Journal of Chemical Crystallography|
|Journal citation||49, pp. 1-8|
|Digital Object Identifier (DOI)||https://doi.org/10.1007/s10870-018-0747-x|
|Funder||ESPRC (Grant Reference EP/K0390X/1)..|
|Online||09 Nov 2018|
|Publication process dates|
|Deposited||14 Dec 2018|
|Accepted||26 Oct 2018|
|Accepted author manuscript|
Open Access http://creativecommons.org/licenses/by/4.0/
|Contributors||Palmer, R., Lisgarten, D., Cockcroft, J., Lisgarten, J., Talbert, R., Dines, T., Bansal, R., Chandra, P. and Suryan, A.|
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