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Dual Chlorine-Bifurcated Acceptor Cl···H–(N,O) Hydrogen Bonds in 4-[(4-Methylpiperazin-1-yl) Methyl]benzoic Acid Dihydrochloride Hemihydrate

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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) Å, b = 7.2312(4) Å, c = 12.5827(5) Å, β = 96.870(6)°, Z = 8. The dihedral angle between the mean plane of the benzyl ring and the piperazin-1-yl group is 80.4(2)°, 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)° and 76.8(3)°, respectively. A short C=O and slightly extended C–O carboxyl bond in concert with weak intermolecular C–O···Cg π-ring interactions influences this twist angle with the benzyl ring and provides a slight interaction with the π conjugation of the benzene ring. Hydrogen bonding has no effect on the carboxylic group. Two separate two-center (acceptor bifurcated) Cl−···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.

Graphical Abstract

Crystal Structure of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride hemihydrate is reported and its geometric and packing parameters described and compared to a MOPAC computational calculation.

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Acknowledgments

LM thanks the University of Mysore for use of their research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

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Authors and Affiliations

  1. Department of Chemistry, Keene State College, 229 Main Street, Keene, NH, 03435-2001, USA

    Jerry P. Jasinski

  2. Department of Chemistry, Howard University, 525 College Street NW, Washington, DC, 20059, USA

    Ray J. Butcher

  3. Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, India

    L. Mallesha, K. N. Mohana & H. S. Yathirajan

  4. Department of Studies in Chemistry, Mangalore University, Mangalagangotri, 574199, India

    B. Narayana

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  1. Jerry P. Jasinski
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  2. Ray J. Butcher
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  3. L. Mallesha
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  4. K. N. Mohana
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  5. H. S. Yathirajan
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Correspondence to Jerry P. Jasinski.

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Jasinski, J.P., Butcher, R.J., Mallesha, L. et al. Dual Chlorine-Bifurcated Acceptor Cl···H–(N,O) Hydrogen Bonds in 4-[(4-Methylpiperazin-1-yl) Methyl]benzoic Acid Dihydrochloride Hemihydrate. J Chem Crystallogr 39, 773–776 (2009). https://doi.org/10.1007/s10870-009-9565-5

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  • DOI: https://doi.org/10.1007/s10870-009-9565-5

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