Synthesis and crystal structure investigation of pyridine-2-(3'-mercaptopropanoic acid)-N-oxide by R. Ramasubramanian, S. Kumaresan, R. Thomas, A. David Stephen, and P. Kumaradhas

Crystal Research and Technology

Cryst. Res. Technol. 42, 1024 (2007) - Abstract -

Synthesis and crystal structure investigation of pyridine-2-(3'-mercaptopropanoic acid)-N-oxide

R. Ramasubramanian, S. Kumaresan, R. Thomas*, A. David Stephen**, and P. Kumaradhas**

Department of Chemistry, Manonmaniam Sundaranar University, Tirunelveli-627 012, India
*Chemistry and Physics of Materials Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore-560 064, India
**Department of Physics, Periyar University, Salem – 636 011, India

Keywords	mercaptopropanoic acid, hydrogen bonding, N-oxide, molecular packing
PACS	61.66.Hq
DOI	10.1002/crat.200710916

Pyridine-2-(3'-mercaptopropanoic acid)-N-oxide (I), is a higher homologue of 1-oxopyridinium-2-thioacetic acid (II) [1]. It crystallizes in monoclinic space group P2₁ with a = 9.2168(2) Å, b = 4.1423(2) Å, c = 11.3904(4) Å, β = 98.65(2)°, V = 429.93(3) Å³ and Z = 2. The least-squares refinement gave residual index R = 0.024 for 1070 observed reflections. The introduction of an additional methylene group in (II) causes a flip in the carboxylic acid group of (I) that facilitates the molecules to align infinite antiparallel chains through strong C-H...O interactions. The molecules are interlinked by O-H...O hydrogen bonding across the chains and forming an infinite screw chain along y-direction. The molecular packing is stabilized by O-H...O and C-H...O hydrogen bonding and π-π electron interactions. This is an important facet of the crystal packing.

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