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Crystal structure of minocycline hydrochloride dihydrate form A, C23H28N3O7Cl (H2O)2

Published online by Cambridge University Press:  21 November 2018

Austin M. Wheatley ,
James A. Kaduk Open the ORCID record for James A. Kaduk [Opens in a new window] ,
Amy M. Gindhart  and
Thomas N. Blanton
Austin M. Wheatley
Affiliation:
North Central College, 131 S. Loomis St., Naperville, Illinois 60540
James A. Kaduk*
Affiliation:
North Central College, 131 S. Loomis St., Naperville, Illinois 60540 Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois 60616
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
*
a)Author to whom correspondence should be addressed. Electronic mail: kaduk@polycrystallography.com
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Abstract

The crystal structure of minocycline hydrochloride dihydrate has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Minocycline hydrochloride dihydrate crystallizes in space group P212121 (#19) with a = 7.40772(1), b = 14.44924(3), c = 22.33329(4) Å, V = 2390.465(12) Å3, and Z = 4. The minocycline cation is a zwitterion: both dimethylamino groups are protonated and one hydroxyl group is ionized. A potential ambiguity in the orientation of the amide group was resolved by considering Rietveld refinement residuals and displacement coefficients, as well as DFT energies. The crystal structure is dominated by hydrogen bonds. Both water molecules and a hydroxyl group act as donors to the chloride anion. Both protonated dimethyl amine groups act as donors to the ionized hydroxyl group. Several intramolecular O–H···O hydrogen groups help determine the conformation of the cation. The powder pattern is included in the Powder Diffraction File™ as entry 00-066-1606.

Keywords

minocycline hydrochloride dihydrateMinocin®powder diffractionRietveld refinementdensity functional theory
Type
New Diffraction Data
Information
Powder Diffraction , Volume 34 , Issue 1 , March 2019 , pp. 59 - 65
Copyright
Copyright © International Centre for Diffraction Data 2018 

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