Molecular Association of Almotriptan with Oxalate and Terephthalate Anions |
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Authors: | B Sridhar K Ravikumar H Krishnan A N Singh |
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Institution: | (1) Laboratory of X-Ray Crystallography, Indian Institute of Chemical Technology (IICT), Room No. 150, Hyderabad, 500 607, India;(2) S M S Pharma Research Centre, Hyderabad, 500 038, India |
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Abstract: | Abstract Crystal structures of anti-migraine drug almotriptan were crystallized with oxalic acid (I) and with terephthalic acid (II) and their crystal structures and molecular associations were determined using X-ray diffraction methods. Crystals of both
(I) and (II) are monoclinic, space group P21/c, with a = 5.6270(4) ?, b = 27.6419(19) ?, c = 13.6228(9) ?, β = 93.057(1)°, V = 2115.9(3) ?3, Z = 4 (I) and a = 13.3756(15) ?, b = 15.6065(17) ?, c = 10.7238(12) ?, β = 98.017(2)°, V = 2216.7(4) ?3, Z = 4 (II). In almotriptan oxalate {systematic name: N,N-dimethyl-2-5-(pyrrolidin-1-ylsulfonyl-methyl)-1H-indol-3-yl]-ethanaminium semioxalate}, C17H26N3O2S+, C2HO4
−, (I) and in almotriptan hemi terephthalate hydrate {systematic name: N,N-dimethyl-2-5-(pyrrolidin-1-ylsulfonyl-methyl)-1H-indol-3-yl]-ethanaminium hemi terephthalate monohydrate}, C17H26N3O2S+, 0.5(C8H4O4
2−), H2O, (II), both the almotriptan cations form a trimer with the corresponding anions via N–H···O hydrogen bonds. In (I), the oxalate salt is monoprotonated and in (II), the terephthalic acid is located across the inversion centre and exists as doubly protonated anion. In (I), the cation
and anion are interlinked by the N–H···O and O–H···O hydrogen bonds into continuous two-dimensional layers generate an R66(34) hydrogen-bonded motif tetramers running parallel to the (0 0 1) plane. In (II), the cation and water form a centrosymmetric
tetramer of R44(22) hydrogen-bonded motif via N–H···O and O–H···O hydrogen bonds and further cross-linked by centrosymmetric anions to form
an infinite three-dimensional supramolecular hydrogen-bonded networks. |
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