Hydrogen bonding and conformational analysis of (R)-norcarnitine monohydrate.
(R)-4-(N,N-Dimethylammonio)-3-hydroxybutanoate [(R)-norcarnitine] monohydrate, C6H13NO3.H2O, Mr = 165.2, triclinic, P1, a = 5.9081 (5), b = 6.0438 (4), c = 6.9084 (7) A, alpha = 65.584 (6), beta = 81.957 (8), gamma = 77.771 (6) degrees, V = 219.1 (1) A3, Z = 1, Dx = 1.252 g cm-3, lambda(Cu K alpha) = 1.54184 A, mu = 8.46 cm-1, F(000) = 90, T = 296 K, R = 0.035 for 1763 observations (of 1772 unique data). Intermolecular hydrogen bonding dominates the structure. The molecule of water contacts three different zwitterions, with O...O distances 2.7767 (13), 2.720 (2) and 2.722 (2) A. A hydrogen bond between carboxylate and dimethylammonio links the zwitterions in head-to-tail motif, N...O 2.672 (2) A. Comparison with two other 4-ammonio-3-hydroxybutanoates reveals that the title compound adopts a different conformation along the backbone, N(+)--C--C(OH)--C--CO2-, with N(+)--C--C(OH)--C anti and C--C(OH)--C--CO2- gauche-.
Turnbull
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Department of Chemistry, Louisiana State University, Baton Rouge 70803-1804.
Fronczek
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FR
Gandour
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RD
D002331:Carnitine / Q000031:analogs & derivatives* / Q000737:chemistry; D003460:Crystallization; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D014961:X-Ray Diffraction
C053141:norcarnitine; D002331:Carnitine