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Dorzolamide hydro­chloride [systematic name: (4S)-trans-4-ethyl­ammonio-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thio­pyran-2-sulfonamide 7,7-dioxide chloride], C10H17N2O4S2+·Cl-, belongs to a class of drugs called carbonic anhydrase inhibitors. The ethyl­ammonio side chain is in an extended conformation and is protonated at the N atom, which is hydrogen bonded to the Cl- anion. The dihedral angle between the planes of the thio­phene ring and the sulfonamide group is 80.7 (1)°. A comparison is made with the dorzolamide bound in human carbonic anhydrase in the solid state. Hydrogen bonding is mediated by Cl- anions, resulting in indirect connectivity between the mol­ecules.

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In the title compound, 2C5H6N5+·C8H4O42−·C8H6O4·1.45H2O, the asymmetric unit comprises two adeninium cations, two half phthalate anions with crystallographic C2 symmetry, one neutral phthalic acid mol­ecule, and one fully occupied and one partially occupied site (0.45) for water mol­ecules. The adeninium cations form N—H...O hydrogen bonds with the phthalate anions. The cations also form infinite one-dimensional polymeric ribbons via N—H...N inter­actions. In the crystal packing, hydrogen-bonded columns of cations, anions and phthalate anions extend parallel to the c axis. The water mol­ecules crosslink adjacent columns into hydrogen-bonded layers.

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In the title compounds, C5H6N5+·C8H7O2·C8H8O2·H2O, (I), and C5H6N5+·C4H3O4·H2O, (II), the adeninium cations form N—H...O hydrogen bonds with their anion counterparts and adeninium–adeninium self-association base pairs with the R22(10) motif (Bernstein et al., 1995). A complete hydrogen-bonding motif analysis is presented. Conventional hydrogen bonds lead to layer structures in (I) and to two-dimensional infinite polymeric ribbons in (II). C—H...O inter­actions are found in both structures, while weak π–π stacking inter­actions are only observed in (I).

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In the benzene and phenol solvates of (S)-4-{3-[2-(dimethyl­amino)eth­yl]-1H-indol-5-ylmeth­yl}­oxazolidin-2-one, viz. C16H21N3O2·C6H6, (I), and C16H21N3O2·C6H5OH, (II), the host mol­ecule has three linked residues, namely a planar indole ring system, an ethyl­amine side chain and an oxazolidinone system. It has comparable features to that of sumatriptan, although the side-chain orientations of (I) and (II) differ from those of sumatriptan. Both (I) and (II) have host-guest-type structures. The host mol­ecule in (I) and (II) has an L-shaped form, with the oxazolidinone ring occupying the base and the remainder of the mol­ecule forming the upright section. In (I), each benzene guest mol­ecule is surrounded by four host mol­ecules, and these mol­ecules are linked by a combination of N-H...N, N-H...O and C-H...O hydrogen bonds into chains of edge-fused R44(33) rings. In (II), two independent mol­ecules are present in the asymmetric unit, with similar conformations. The heterocyclic components are connected through N-H...N, N-H...O and C-H...O inter­actions to form chains of edge-fused R64(38) rings, from which the phenol guest mol­ecules are pendent, linked by O-H...O hydrogen bonds. The structures are further stabilized by extensive C-­H...[pi] inter­actions.
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