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From acid aqueous solutions of guanidinium carbonate and monochloroacetic acid, (ClH 2 C)COOH :H 2  NC( = NH)NH 2  ≧ 2.5, the compound [C(NH 2 ) 3 ] ⊕  [(ClH 2 C)COOH • • • OOC(CH 2 Cl)] ⊖  crystallizes with the space group C i  1 P1̄,  Z = 4, a = 1147.4 (5) pm, b= 1113.2 (5) pm, c = 876.5 (4) pm, α = 88.66 (2)°, β = 80.31 (2)°, γ = 84.41 (2)° (metastable phase I). Cooled to 77 K once, phase I transforms at room temperature slowly into the stable phase II, orthorhombic, D 2h  15  - Pbca, Z = 8, a= 1299.2 (4) pm, b= 1533.7 (4) pm, c= 1073.9 (3) pm. The crystal structure determinations show for both phases an ionic lattice with guanidinium cations [C(NH 2 ) 3 ] ⊕  and acid bis-(monochloroacetate) anions [(ClH 2 C)COOH • • • OOC(CH 2 Cl)] ⊖  in which a monochloroacetic acid molecule and a monochloroacetate ion are bound to the dimer anion by an asymmetric hydrogen bond O-H • • • O.

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Crystal Structures and  35 Cl NQR Spectra of the Metastable and the Stable Phase of Guanidinium bis-Monochloroacetate, [C(NH 2 ) 3  ] ⊕ [(ClH 2 C)COOH ••• OOC(CH 2 Cl)l ⊖