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. 2018 Nov 30;74(Pt 12):1903-1907.
doi: 10.1107/S2056989018016791. eCollection 2018 Dec 1.

Structures of the hydrate and dihydrate forms of the DNA-binding radioprotector methyl-pro-amine

Jonathan Michael White  1 , Samuel Charles Brydon  1 , Thomas Fellowes  1
Affiliations

Structures of the hydrate and dihydrate forms of the DNA-binding radioprotector methyl-pro-amine

Jonathan Michael White et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

Methyl pro-amine {N,N,3-trimethyl-4-[6-(4-methyl-piperazin-1-yl)-1H,3'H-[2,5'-bibenzo[d]imidazol]-2'-yl]aniline}, C28H35N7O2, crystallized as both a dihydrate, C28H31N7·2H2O, and monohydrate, C28H31N7·H2O, form from water in the presence of β-cyclo-dextrin, in the P21/c and P21/n space groups, respectively. The two structures adopt different conformations and tautomeric forms as a result of the differing crystal packing as dictated by hydrogen-bonding inter-actions. The dihydrate crystallizes as a three-dimensional hydrogen-bonded network, while the monohydrate crystallizes as a two-dimensional hydrogen-bonded network.

Keywords: crystal structure; hydrates; hydrogen bonding; tautomerism.

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Figures

Figure 1
Figure 1
Displacement ellipsoid plot of the asymmetric unit for dihydrate (1)·2H2O.
Figure 2
Figure 2
Displacement ellipsoid plot of the asymmetric unit for hydrate (1)·H2O.
Figure 3
Figure 3
Overlay for the structures of A; (1)·2H2O and B; (1)·H2O with DNA-bound (1). In the LH-structure the DNA-bond ligand is indicated by capped sticks, while in the RH structure it is ball and stick.
Figure 4
Figure 4
The water tetra­mer with diagonally hydrogen-bonded mol­ecules of (1).
Figure 5
Figure 5
The water tetra­mer with additional hydrogen-bonded inter­actions with (1).
Figure 6
Figure 6
The cross-linking N—H⋯N hydrogen bonds between benzimidazole moieties mol­ecules of (1).
Figure 7
Figure 7
Three-dimensional hydrogen-bonded network in (1)·2H2O.
Figure 8
Figure 8
Hydrogen bonding between (1) and the water mol­ecule in (1)·H2O.
Figure 9
Figure 9
Direct N—H⋯N hydrogen bonds between benzimidazole moieties of (1)·H2O.
Figure 10
Figure 10
Two-dimensional hydrogen-bonded network in (1)·H2O.
See this image and copyright information in PMC

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