J. Li, Zunjun Liang, X. Tai
2009
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Zeitschrift für Kristallographie - New Crystal Structures
Abstract
C13H18N2O5, monoclinic, C121 (no. 5), a = 11.277(1) Å, b = 6.8760(8) Å, c = 18.527(2) Å, = 102.680(2)°, V = 1401.6 Å, Z = 4, Rgt(F) = 0.053, wRref(F) = 0.130, T = 298 K. Source of material The solution of (S)-2-amino-3-(1H-indol-3-yl)propanoic acid (0.1 mol) in acetic acid (95 %, 30 ml) was stirred under reflux for 10 min. After cooling and filtration, filtrate was kept at room temperature for 10 days. Natural evaporation gave colourless single crystals of the title compound, suitable for X-ray analysis. Discussion Amino acids play an important role in methylation, detoxication and antioxidation. They are very useful in the pharmaceutical and food industries [1]. Tryptohan is the only one complicated amino acid with general-purpose physiological and biochemical functionals [2]. The asymmetric unit of the title crystal structure contains one (S)2-amino-3-(1H-indol-3-yl)propanoic acidate, one acetic acid and one water molecule. The geometry of molecule is close to the related compounds [Fe(L-trp)2(HL-trp)2]n [2] and (S)-2-[(S)-2acetamido-3-phenylpropanamido]-3-phenylpropanoic acid [3]. The indole ring is essentially plane. The crystal structure is stabilized by hydrogen bonds. The protonated N atoms interact with the (S)-2-amino-3-(1H-indol-3-yl)propanoic acidate anions, acetic acid and water through N−H···O hydrogen bonds. The water interacts with the (S)-2-amino-3-(1H-indol-3-yl)propanoic acidate, acetic acid and another water through C−H···O, O−H···O and N−H···O hydrogen bonds. Z. Kristallogr. NCS 224 (2009) 153-154 / DOI 10.1524/ncrs.2009.0068 153 © by Oldenbourg Wissenschaftsverlag, München Crystal: colorless block, size 0.05 × 0.08 × 0.35 mm Wavelength: Mo K0 radiation (0.71073 Å) %: 1.03 cm−1 Diffractometer, scan mode: Bruker SMART CCD, )/2 2"max: 50.06° N(hkl)measured, N(hkl)unique: 3543, 2357 Criterion for Iobs, N(hkl)gt: Iobs > 2 !(Iobs), 1505 N(param)refined: 183 Programs: SHELXS-97 [4], SHELXL-97 [5], SHELXTL [6] Table 1. Data collection and handling. H(1A) 4c 0.0839 0.3793 0.0625 0.054 H(1B) 4c 0.0038 0.2291 0.0798 0.054 H(1C) 4c 0.1175 0.2721 0.1316 0.054 H(2) 4c 0.4637 0.5666 0.2652 0.061 H(4A) 4c 0.3129 0.1065 0.2095 0.094 H(5A) 4c 0.8247 0.0048 0.0127 0.074 H(5B) 4c 0.9455 0.0099 0.0085 0.074 H(2A) 4c −0.0252 0.4127 0.1805 0.040 H(3A) 4c 0.0920 0.7013 0.1142 0.048 H(3B) 4c 0.0266 0.7422 0.1789 0.048 H(4) 4c 0.3158 0.6027 0.1510 0.058 H(8) 4c 0.4608 0.5503 0.4144 0.078 H(9) 4c 0.3296 0.5502 0.4927 0.091 H(10) 4c 0.1237 0.5769 0.4473 0.086 H(11) 4c 0.0435 0.6054 0.3228 0.063 H(13A) 4c 0.1766 0.1331 0.3742 0.099 H(13B) 4c 0.3178 0.1424 0.3823 0.099 H(13C) 4c 0.2509 −0.0589 0.3726 0.099 Table 2. Atomic coordinates and displacement parameters (in Å). Atom Site x y z Uiso