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Crystal structure of levocetirizine dihydrochloride Form I, C21H27ClN2O3Cl2

Published online by Cambridge University Press:  20 April 2021

James A. Kaduk Open the ORCID record for James A. Kaduk [Opens in a new window] ,
Amy M. Gindhart  and
Thomas N. Blanton Open the ORCID record for Thomas N. Blanton [Opens in a new window]
James A. Kaduk*
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois60616, USA North Central College, 30 N. Brainard St., Naperville, Illinois60540, USA
Amy M. Gindhart
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois60616, USA North Central College, 30 N. Brainard St., Naperville, Illinois60540, USA
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania19073-3273, USA
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

The crystal structure of levocetirizine dihydrochloride Form I has been solved and refined using synchrotron X-ray powder diffraction data and optimized using density functional techniques. Levocetirizine dihydrochloride Form I apparently crystallizes in space group P21/n (#14) with a = 24.1318(21), b = 7.07606(9), c = 13.5205(7) Å, β = 97.9803(4)°, V = 2286.38(12) Å3, and Z = 4. The crystal structure consists of interleaved double columns of cations and anions along the short b-axis. The hydrogen bonds link the cations and anions along this axis. Each protonated nitrogen atom forms a strong N–H⋯Cl hydrogen bond to one of the chloride anions. The carboxylic acid group also forms an H-bond to Cl56, resulting in a ring with a graph set R1,2(10). The centrosymmetric P21/n model for the crystal structure of levocetirizine dihydrochloride is better than the non-centrosymmetric P21 model, even though levocetirizine is a chiral molecule; the sample exhibits weak second-harmonic generation, and three weak peaks which violate the glide plane are observed. The centrosymmetric model is better by statistical, graphical, and energetic measures, as well as by chemical reasonableness. To accommodate the chiral molecule in a centrosymmetric space group, the chiral central carbon atom was disordered over two half-occupied positions, so that each cation site could be occupied by a cation of the correct chirality. A powder pattern from a Le Bail extraction of this synchrotron data set is included in the Powder Diffraction File™ as entry 00-066-1627.

Keywords

levocetirizine dihydrochlorideXyzalpowder diffractionRietveld refinementdensity functional theory
Type
New Diffraction Data
Information
Powder Diffraction , Volume 36 , Issue 3 , September 2021 , pp. 181 - 189
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Copyright
Copyright © The Author(s), 2021. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

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