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4-(3-Methyl-anilino)-N-[N-(1-methyl-ethyl)carbamo-yl]pyridinium-3-sulfon-amidate (torasemide) methanol 0.25-solvate 0.25-hydrate.

ABSTRACT: The title compound, C(16)H(20)N(4)O(3)S·0.25CH(4)O·0.25H(2)O, is a hydrate/methanol solvate of torasemide, a diuretic drug used in the treatment of hypertension. The asymmetric unit contains two torasemide mol-ecules and half-occupied methanol and water mol-ecules. It is isomorphous with the previously reported nonsolvated T-II form of torasemide. The water mol-ecules contribute to the stability of the structure by participating in an extensive system of O-H?O hydrogen bonds; N-H?N and N-H?O hydrogen bonds are also present. Both asymmetric mol-ecules of torasemide form inversion dimers in the crystal.

SUBMITTER: Bartolucci G

PROVIDER: S-EPMC2977669 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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4-(3-Methyl-anilino)-N-[N-(1-methyl-ethyl)carbamo-yl]pyridinium-3-sulfon-amidate (torasemide) methanol 0.25-solvate 0.25-hydrate.

Bartolucci Gianluca G Bruni Bruno B Coran Silvia A SA Di Vaira Massimo M

Acta crystallographica. Section E, Structure reports online 20090408 Pt 5

The title compound, C(16)H(20)N(4)O(3)S·0.25CH(4)O·0.25H(2)O, is a hydrate/methanol solvate of torasemide, a diuretic drug used in the treatment of hypertension. The asymmetric unit contains two torasemide mol-ecules and half-occupied methanol and water mol-ecules. It is isomorphous with the previously reported nonsolvated T-II form of torasemide. The water mol-ecules contribute to the stability of the structure by participating in an extensive system of O-H⋯O hydrogen bonds; N-H⋯N and N-H⋯O hyd ...[more]

PMID: 21584012

Similar Datasets

4-(3-Methyl-anilino)-N-[N-(1-methyl-ethyl)carbamo-yl]pyridinium-3-sulfon-amidate (torasemide T-N): a low temperature redetermination.

Project description:The structure [Danilovski et al. (2001 ▶). Croat. Chim. Acta74, 103-120] of the T-N (non-solvated) polymorph of torasemide, C(16)H(20)N(4)O(3)S, a diuretic drug used in the treatment of hypertension, has been redetermined at low temperature. The zwitterionic form of the mol-ecule is confirmed, although GAUSSIAN03 calculations suggest that this form is less stable in the gas phase. The unit-cell contraction between 298 and 100 K is approximately isotropic and the largest structual change is in a C-N-C-C torsion angle, which differs by 11.4 (3)° between the room-temperature and low-temperature structures. There are two mol-ecules in the asymmetric unit, both of which contain an intra-molecular N-H⋯N hydrogen bond. In the crystal structure, both mol-ecules form inversion dimers linked by pairs of N-H⋯N hydrogen bonds. Further N-H⋯N and N-H⋯O hydrogen bonds lead to a three-dimensional network. The different hydrogen-bond arrangements and packing motifs in the polymorphs of torasemide are discussed in detail.

| S-EPMC2977670 | biostudies-literature

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Project description:The title compound, C(14)H(12)ClNO(3)·0.25H(2)O, exists in the keto-amine form, and the aromatic rings are oriented at a dihedral angle of 7.24 (7)°. Bifurcated intra-molecular N-H⋯(O,O) hydrogen bonds result in the formation of planar six- and five-membered rings. In the crystal structure, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains. π-π contacts between benzene rings [centroid-centroid distance = 3.5065 (9) Å] may further stabilize the structure. There also exists a weak C-H⋯π inter-action.

| S-EPMC2977782 | biostudies-literature

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| S-EPMC2980248 | biostudies-literature

Bis{4-[(E)-2-(1H-indol-3-yl)ethen-yl]-1-methyl-pyridinium} 4-fluoro-benzene-sulfonate nitrate 0.25-hydrate.

Project description:In the title compound, 2C(16)H(15)N(2) (+)·C(6)H(4)FO(3)S(-)·NO(3) (-)·0.25H(2)O, the two cations are nearly planar, with dihedral angles of 1.34?(14) and 4.6?(2)°, respectively, between the pyridinium and indole rings. The cations each adopt E configurations with respect to the C=C bonds and are inclined to each other with a dihedral angle of 77.66?(5)°. The ethenyl group of one cation is disordered over two sites with occupancies of 0.685?(12) and 0.315?(12), and the sulfonate group of the 4-fluoro-benzene-sulfonate anion is also disordered with occupancies of 0.535?(10) and 0.465?(10) for the two sets of O atoms. The anion is also inclined to the two cations, with dihedral angles between the mean planes of the benzene ring and the ?-conjugated systems of the cations of 24.72?(11) and 79.83?(11)°. In the crystal structure, the cations are stacked in an anti-parallel fashion into columns approximately along the a axis and are further linked through the anions into a three-dimensional network via N-H?O and C-H?O inter-actions. The water mol-ecule forms O-H?O hydrogen bonds to the nitrate anion and C-H?? inter-actions are also observed.

| S-EPMC2968363 | biostudies-literature

(E)-Methyl N'-[(1H-indol-3-yl)methyl-idene]hydrazinecarboxyl-ate 0.25-hydrate.

Project description:The asymmetric unit of the title compound, C(11)H(11)N(3)O(2)·0.25H(2)O, contains two independent organic mol-ecules and a water mol-ecule, which lies on a twofold rotation axis. The side chains of the two mol-ecules have slightly different orientations, the C=N-N-C torsion angle being -163.03 (15)° in one and -177.52 (14)° in the other, with each adopting a trans configuration with respect to the C=N bond. In the crystal, mol-ecules are linked into chains extending along b by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds and in addition, four inter-molecular C-H⋯π inter-actions are present.

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2-Amino-5-chloro-pyridinium (Z)-3-carb-oxy-prop-2-enoate 0.25-hydrate.

Project description:In the title hydrated salt, C(5)H(6)ClN(2) (+)·C(4)H(3)O(4) (-)·0.25H(2)O, the water O atom lies on a twofold axis with 0.25 occupancy. The 2-amino-5-chloro-pyridinium cation is almost planar, with a maximum deviation of 0.015 (3) Å. In the hydrogen malate anion, an intra-molecular O-H⋯O hydrogen bond generates an S(7) ring and results in a folded conformation. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl-ate O atoms of the anion via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The ion pairs are further connected via O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, forming layers parallel to the ab plane which stack down the c axis.

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Project description:The asymmetric unit of the title compound, C(6)H(9)N(2) (+)·C(6)H(4)NO(2) (-)·0.63H(2)O, contains two crystallographically independent 2-amino-5-methyl-pyridinium cations, a pair of picolinate anions and two water mol-ecules, one with an occupancy of 0.25. Both the 2-amino-5-methyl-pyridine mol-ecules are protonated at the pyridine N atoms. In the crystal structure, the cations, anions and water mol-ecules are linked via N-H?O, N-H?N and O-H?O hydrogen bonds, as well as by C-H?O contacts, forming a chain along the b axis. In addition, weak ?-? inter-actions are observed between pyridinium rings, with centroid-centroid distances of 3.5306?(13)?Å.

| S-EPMC2979649 | biostudies-literature

3-(2-Amino-5-nitro-anilino)-5,5-dimethyl-cyclo-hex-2-en-1-one 0.25-hydrate.

Project description:The asymmetric unit of the title compound, C(14)H(17)N(3)O(3)·0.25H(2)O, comprises two independent organic mol-ecules and a water mol-ecule lying on a crystallographic twofold rotation axis with 50% site occupancy. In both independent mol-ecules, the cyclo-hexene rings adopt envelope conformations but superposition of the two molecules shows that the flap atoms point in opposite directions. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds inter-connect adjacent mol-ecules into a three-dimensional network. Weak inter-molecular π-π aromatic stacking inter-actions [centroid-centroid distances = 3.4985 (9) and 3.6630 (9) Å] are also observed.

| S-EPMC3008006 | biostudies-literature

Ethyl (Z)-3-(4-methyl-anilino)-2-[(4-methyl-phen-yl)carbamo-yl]prop-2-enoate.

Project description:The title compound, C(20)H(22)N(2)O(3), is a secondary amine featuring an amide and an ester functionality in connection with a Michael system. The conformation about the C=C bond is E. Intra-molecular N-H?O hydrogen bonds occur. In the crystal, C-H?O contacts connect the mol-ecules into chains along the b-axis direction.

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Project description:In the crystal structure of the title salt, 2C(6)H(9)N(2) (+)·C(8)H(4)O(4) (2-)·4H(2)O, the terephthalate carboxyl-ate groups inter-acts with the 2-amino-4-methyl-pyridinium cations via a pair of N-H?O hydrogen bonds, forming an R(2) (2)(8) ring motif. The water mol-ecules form an R(6) (6)(12) ring motif through O-H?O hydrogen bonds and these motifs are fused, forming a supra-molecular chain along the c axis. The R(2) (2)(8) and R(6) (6)(12) ring motifs are connected via O-H?O hydrogen bonds. In addition, ?-? stacking inter-actions are observed between the pyridinium rings [centroid-centroid distance = 3.522?(12)?Å].

| S-EPMC3007316 | biostudies-literature

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