Dual chlorine-bifurcated acceptor cl center dot center dot center dot h-(n,o) hydrogen bonds in 4-(4-methylpiperazin-1-yl) methyl]benzoic acid dihydrochloride hemihydrate

Jasinski, Jerry P. and Butcher, Ray J. and Mallesha, L. and Mohana, K. N. and Yathirajan, H. S. and Narayana, B. (2009) Dual chlorine-bifurcated acceptor cl center dot center dot center dot h-(n,o) hydrogen bonds in 4-(4-methylpiperazin-1-yl) methyl]benzoic acid dihydrochloride hemihydrate. JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 39 (11). pp. 773-776. ISSN 1572-8854

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Official URL: http://doi.org/10.1007/s10870-009-9565-5

Abstract

The title compound, a salt of C13H20O2 (2+) 2Cl(-) 0.5 H2O, (I), crystallizes in the monoclinic space group C 2/c with unit cell parameters a = 34.091(4) angstrom, b = 7.2312(4) angstrom, c = 12.5827(5) angstrom, beta = 96.870(6)degrees, Z = 8. The dihedral angle between the mean plane of the benzyl ring and the piperazin-1-yl group is 80.4(2)degrees, while the angle between the mean planes of the carbonyl group with that of the benzyl and piperazin-1-yl rings measure 6.6(3)degrees and 76.8(3)degrees, respectively. A short C=O and slightly extended C-O carboxyl bond in concert with weak intermolecular C-O center dot center dot center dot Cg pi-ring interactions influences this twist angle with the benzyl ring and provides a slight interaction with the pi conjugation of the benzene ring. Hydrogen bonding has no effect on the carboxylic group. Two separate two-center (acceptor bifurcated) Cl-center dot center dot center dot H-(N,O) hydrogen bonds are observed between one chloride anion and a water molecule and the piperazin-1-yl ring and a second chloride anion with a carboxyl oxygen atom and the piperazin-1-yl ring. These direct intermolecular couplings link the molecule into chains along the 010] plane of the unit cell which influence the twist angles of the benzyl and piperazin-1-yl rings and help stabilize crystal packing in the unit cell.

Item Type: Article
Uncontrolled Keywords: Crystal structure; Hydrogen bonds; Hemihydrate; Benzoic acid; Piperazine; Salt; Chlorine-bifurcated acceptor Cl center dot center dot center dot H-(NO); Hydrogen bonds; MOPAC; AM1
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Shrirekha N
Date Deposited: 14 Aug 2019 07:53
Last Modified: 14 Aug 2019 07:54
URI: http://eprints.uni-mysore.ac.in/id/eprint/6370

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