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In 2,4-diamino-5-( p-chlorophenyl)-6-ethylpyrimidinium hydrogen adipate, C12H14ClN4+·C6H9O4−, the protonated pyrimethamine cation interacts with the carboxylate group of the adipate ion through N—H...O hydrogen bonds, forming a cyclic hydrogen-bonded R22(8) motif. The carboxyl and carboxylate groups of the adipate ions are linked through O—H...O hydrogen bonds in a head-to-tail fashion, forming a chain. Anions and cations are further connected by an extensive network of N—H...O hydrogen bonds. [ABSTRACT FROM AUTHOR]

In the crystal structure of the title compound [systematic name: 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 3,5-dinitrobenzoate], C12H14ClN4+·C7H3N2O6−, the pyrimethamine molecule is protonated at one of the pyrimidine N atoms. The carboxylate group of the 3,5-dinitrobenzoate anion forms double hydrogen bonds of type N—H...O, resulting in a fork-like interaction with the protonated diaminopyrimidine rings [graph-set notation R22(8)]. This motif self-assembles through a DDAA array of quadruple hydrogen bonds. The crystal structure is also stabilized by C—H...O hydrogen bonds. [ABSTRACT FROM AUTHOR]

The title compound [systematic name: 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimdinium tetrafluoroborate], C12H14ClN4+·BF4−, is isomorphous with pyrimethamine perchlorate. The pyrimethamine (PMN) molecule is protonated at one of the pyrimidine N atoms. The protonated N atom and 2-amino group of the PMN cation interact with the tetrafluoroborate anion through a pair of N—H...F hydrogen bonds [graph set R22(8)]. The inversion-related PMN cations are linked through a pair of N—H...N hydrogen bonds. In addition to the base pairing, the F atoms bridge the 2-amino and 4-amino groups on either side of the paired bases, resulting in a complementary DADA array. [ABSTRACT FROM AUTHOR]

In the crystal structures of the title compounds, C6H10N3O2+·C7H5O3−·H2O, (I), C6H10N3O2+·C7H4NO4−·H2O, (II), and C6H10N3O2+·C4H5O6−·C6H9N3O2, (III), the 2-amino-4,6-di­meth­oxy­pyrimidinium cation [abbreviated as (MeO)2-Hampy+] inter­acts with the carboxyl­ate group of the corresponding anion through a pair of nearly parallel N—H⋯O hydrogen bonds to form R22(8) ring motifs. In (I), the (MeO)2-Hampy+ cation is centrosymmetrically paired through a pair of N—H⋯N hydrogen bonds involving the 2-amino group and a ring N atom forming an R22(8) motif. In (II), inversion-related R22(8) motifs (amino–pyrimidine–carboxyl­ate motifs) are further bridged by N—H⋯O hydrogen bonds on either side forming a DDAA array of quadruple hydrogen bonds. This array is extended further on either side by Owater—H⋯Ometh­oxy hydrogen bonds, resulting in an array of six hydrogen bonds ( ADDAAD). The water mol­ecule plays a pivotal role, and five hydrogen-bonded fused rings are formed around the water mol­ecule. In (III), the carb­oxy group of the tartrate anion inter­acts with the ring N atom and 2-amino group of the neutral (MeO)2-ampy mol­ecule through N—H⋯O and O—H⋯N hydrogen bonds. There is also an intra­molecular O—H⋯O hydrogen bond in the tartrate anion. In all three crystal structures, C—H⋯O hydrogen bonds are observed. [ABSTRACT FROM AUTHOR]

In the crystal structure of the title compound, C6H10N3+·C7H5O3-, the asymmetric unit contains four crystallographically independent 2-amino-4,6-dimethylpyrimidinium and salicylate ions (Z = 8). In each of these, one of the pyrimidine N atoms is protonated, and the carboxylate group of the salicylate ion interacts with the pyrimidine group through a pair of N—H…O hydrogen bonds, forming an R2²(8) motif. The pyrimidine cations also form base pairs via a pair of N—H…N hydrogen bonds (involving the amino group and the unprotonated ring N atom), forming another R2²(8) motif. Three such R2²(8) motifs, fused together, constitute a closed cyclic aggregate, and the linking of these aggregates, arranged in consecutive layers, can be analysed in terms of off-face stacking interactions. [ABSTRACT FROM AUTHOR]

In the title compounds, namely 2,4-diamino-5-[(3,4,5-trimethoxy­phenyl)methyl]­pyrimidin-1-ium pyridine-2-carboxyl­ate, C14H19N4O3+·C6H4NO2−, (I), and 2-amino-4,6-dimethyl­pyrimidin-1-ium pyridine-2-carboxyl­ate hemihydrate, C6H10N3+·C6H4NO2−·0.5H2O, (II), the trimethoprim and 2-amino-4,6-dimethyl­pyrimidin-1-ium cations are protonated at one of the pyrimidine N atoms. In (I), bifurcated hydrogen bonds are observed between a picolinate O atom, the protonated N atom and the 2-amino group; the graph-set designator is R21(6). The pyrimidine moieties of the trimethoprim cations are centrosymmetrically paired through a pair of N—H⋯N hydrogen bonds. In addition to the base pairing, one of the picolinate O atoms bridges the 2- and 4-amino groups on either side of the paired bases, resulting in a complementary DADA array. In (II), the carboxyl­ate group of the picolinate anion binds with the protonated pyrimidine N atom and the 2-amino group of the pyrimidine moiety through a pair of N—H⋯O hydrogen bonds, leading to the common ring motif R22(8). The water mol­ecule, which resides on a twofold rotation axis, bridges the carboxyl­ate group of the picolinate anion via O—H⋯O hydrogen bonds. [ABSTRACT FROM AUTHOR]

In the title compound [systematic name: 2,4-diamino-5-(3,4,5-trimethoxy­benz­yl)pyrimidinium tetrafluoroborate], C14H19N4O3+·BF4−, the trimethoprim (TMP) mol­ecule is protonated at one of the pyrimidine N atoms. The protonated N atom and 2-amine group of the TMP cation inter­act with the tetrafluoroborate anion through a pair of N—H⋯F hydrogen bonds [graph set R22(8)]. The inversion-related TMP cations are linked through a pair of N—H⋯N hydrogen bonds. The 2-amine group of one TMP cation and the 4-amine group of another cation are bridged by a meth­oxy O atom, via N—H⋯O hydrogen bonds. [ABSTRACT FROM AUTHOR]

In the title compound, C6H9N3·2C9H8O2, an amino­pyrimidine–cinnamic acid 1:2 cocrystal, the 2-amino-4,6-dimethyl­pyrimidine mol­ecule forms two eight-membered hydrogen-bonded rings [ R22(8) motif] with the carboxylic acid groups from two independent cinnamic acid mol­ecules via N—H⋯O and O—H⋯N hydrogen bonds. The cinnamic acid mol­ecules are linked by C—H⋯O hydrogen bonds to form chains along two axes. [ABSTRACT FROM AUTHOR]

The title compound, 2,4-diamino-5-(4-chloro­phen­yl)-6-ethyl­pyrimidine-1,3-diium dinitrate, C12H15ClN42+·2NO3−, contains two crystallographically independent pyrimethamine (PMN) mol­ecules, which differ in the relative orientations of the pyrimidine and benzene rings and of the eth­yl substitutents. In both pyrimethamine mol­ecules, all the pyrimidine N atoms are protonated, unlike most related compounds, in which only one pyrimidine N atom is protonated. The two pyrimethamine moieties are bridged by a variety of N—H⋯O(nitrate) inter­actions, including some three-centre hydrogen bonds. [ABSTRACT FROM AUTHOR]

Abstract: Interesting hydrogen-bonded supramolecular patterns have been achieved by hexafluorosilicate anion in the crystal structures of bis(thiabendazole) hexafluorosilicate dihydrate 1 and bis(pyrimethamine) hexafluorosilicate 2. In compound 1, the nitrogen atom of the benzimidazole ring rather than that of the thiazole ring is protonated. Water molecule is hydrogen-bonded with SiF6 2− anion through O–H⋯F hydrogen bonds to form a twelve membered cyclic hydrogen-bonded cluster. This cluster is self-organized to form a supramolecular chain. In the crystal structure of compound 2, the asymmetric unit contains two crystallographically independent protonated pyrimethamine (PMN) cations and a hexafluorosilicate SiF6 2− anion. The combination N–H⋯F and N–H⋯N hydrogen bonds results in the formation of complementary DADA (D and A represent donor and acceptor, respectively) array motif. It confirms that DADA array motif is a robust synthon in the crystal structures of diaminopyrimidine salts. [Copyright &y& Elsevier]

The title compound, [Sr(C9H5INO4S2)2(H2O)2]·H2O, is isomorphous with the corresponding calcium complex of ferron (8-hydroxy-7-iodo­quinoline-5-sulfonic acid). The asymmetric unit consists of one SrII ion, two organic ligands, two coordinated water mol­ecules and one uncoordinated water mol­ecule. The SrII ion has a pentagonal–bipyramidal coordination geometry made up of O atoms of three different sulfonate groups, deprotonated quinolinol O atoms of two different oxine rings and two water mol­ecules. In the ligands of type I, two O atoms of the sulfonate group are involved in coordination, whereas in type II ligands, only one O atom is involved. Ligands of type I are stacked on top of one another, each pair of adjacent members of the stack being related by an inversion centre. Ligands of type II are also stacked in a similar manner. These molecular stacks are cross-linked by Sr—O(sulfonate) and Sr—O(quinolinol) bonds, leading to an extended framework. This architecture is further stabilized by a number of O—H⋯O and N—H⋯O hydrogen bonds. [ABSTRACT FROM AUTHOR]

In the title compound [systematic name: 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidinium 2-hydroxy-3,5-dinitrobenzoate], C14H19N4O3+·C7H3N2O7−, the trimethoprimium (TMP) cation is protonated at one of the pyrimidine N atoms. The protonated N atom and the 2-amino group of the TMP cation interact with the carboxylate group of the 3,5-dinitrosalicylate anion through a pair of N—H...O hydrogen bonds. A typical intramolecular O—H...O hydrogen bond is observed in the anion. [ABSTRACT FROM AUTHOR]

In the title compound, C6H9N3·C7H6O3, the 2-amino-4,6-dimethyl­pyrimidine and 4-hydroxy­benzoic acid mol­ecules link together via N—H⋯O and O—H⋯N hydrogen bonds to form an eight-membered R22(8) ring. Further hydrogen bonds and C—H⋯O inter­actions result in the formation of a three-dimensional network. [ABSTRACT FROM AUTHOR]

In the title cocrystal, C6H9N3O2·C7H7NO2, the 2-amino-4,6-dimethoxy­pyrimidine mol­ecule inter­acts with the carboxyl group of the 4-amino­benzoic acid mol­ecule through N—H⋯O and O—H⋯N hydrogen bonds, forming a cyclic hydrogen-bonded motif [ R22(8)]. This motif further self-organizes through N—H⋯O hydrogen bonds to generate an array of six hydrogen bonds with the rings having the graph-set notation R23(6), R22(8), R42(8), R22(8) and R23(6). The 4-amino­benzoic acid mol­ecules self-assemble via N—H⋯O hydrogen bonds to form a supra­molecular chain along the c axis. [ABSTRACT FROM AUTHOR]

The title compound, C13H11NO3, was synthesized from 4-nitrophenol and benzyl bromide. The crystal structure is stabilized by C—H...π interactions involving two H atoms of the benzyloxy group [3.432 (2) Å and 148°, and 3.555 (2) Å and 148°]. [ABSTRACT FROM AUTHOR]

In the title mol-ecule, C10H10O4, the carb-oxy-lic acid group is twisted by 11.37 (15)° from the plane of the benzene ring and the acet-oxy group is twisted from this plane by 86.60 (17)°. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers with the expected R 2 (2)(8) graph-set motif.

The title mol-ecular salt, C10H12N3O3S(+)·C7H3N2O7 (-), protonation occurs at the amino N atom attached to the benzene ring of sulfamethoxazole. In the anion, there is an intra-molecular O-H⋯O hydrogen bond and the cation is linked to the anion by an N-H⋯O hydrogen bond. In the extended structure, the cations and anions are linked via N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonds, forming a three-dimensional framework.

In the title compound, C13H10ClNO, the dihedral angle between the planes of the aromatic rings is 51.42 (9)° and an intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. The Cl atom and the N atom are syn. No directional inter-actions beyond van der Waals contacts are observed in the crystal.

The title compound, C5H6N4O, is approximately planar, with an angle of 11.04 (15)° between the planes of the pyrimidine ring and the non-H atoms of the carboximidamide unit. The mol-ecule adopts an E configuration about the C=N double bond. In the crystal, adjacent mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(10) ring motif. The dimers are further linked via N-H⋯N and O-H⋯N hydrogen bonds into a sheet structure parallel to the ac plane. The crystal structure also features N-H⋯O and weak C-H⋯O hydrogen bonds and offset π-π stacking inter-actions between adjacent pyrimidine rings [centroid-centroid distance = 3.622 (1) Å].

In the crystal of the title compound, C6H9N3·C6H8O2, the 2-amino-4,6-di-methyl-pyrimidine and sorbic acid mol-ecules are linked through N-H⋯O and O-H⋯N hydrogen bonds, which generate a cyclic bimolecular heterosynthon with an R 2 (2)(8) graph-set motif. Further, two inversion-related pyrimidine mol-ecules are base-paired via a pair of N-H⋯N hydrogen bonds, forming a cyclic bimolecular homosynthon with a graph-set of R 2 (2)(8). A discrete hetero tetra-meric supra-molecular unit along the b axis is formed by the fusion of two heterosynthons and one homosynthon. An aromatic π-π inter-action [centroid-centroid distance = 3.7945 (16) Å] is observed between these tetra-meric units.

In the title complex, [Co(CO3)(NH3)4]ClO4, both the cation and anion lie on a mirror plane. The Co(III) ion is coordinated by two NH3 ligands and a chelating carbonato ligand in the equatorial sites and by two NH3 groups in the axial sites, forming a distorted octa-hedral geometry. In the crystal, N-H⋯O hydrogen bonds connect the anions and cations, forming a three-dimensional network.

In the crystal structure of the title compound, C(6)H(10)N(3) (+)·C(7)H(2)I(3)O(2) (-)·C(7)H(3)I(3)O(2), two R(2) (2)(8) motifs are observed. One is generated by the inter-action of the 2-amino-4,6-dimethyl-pyrimidin-1-ium cation with the carboxyl-ate group of the 2,3,5-triiodo-benzoate anion via N-H⋯O hydrogen bonds. The other R(2) (2)(8) motif is formed by the inter-action of two centrosymmentrically related pyrimidine moieties through N-H⋯N hydrogen bonds. The two motifs combine to form a linear heterotetra-meric unit. Heterotetra-meric units are linked by a carbox-yl-carboxyl-ate O-H⋯O hydrogen bond (involving the O-H group of neutral 2,3,5-triiodo-benzoic acid and an O atom of the anion), forming a supra-molecular chain along the a axis. In addition, components are held by weak I⋯O interactions in the range 3.023 (5) to 3.382 (5) Å and I⋯I inter-actions in the range 3.6327 (7) to 4.0025 (8) Å.

In the title salt, C(6)H(10)N(3)O(2) (+)·C(7)H(7)O(3)S(-), the 2-amino-4,6-dimeth-oxy-pyrimidinium cation inter-acts with the sulfonate group of the p-toluene-sulfonate anion via a pair of N-H⋯O hydrogen bonds, forming a cyclic hydrogen-bonded R(2) (2)(8) motif, which in the crystal is linked by further intemolecular N-H⋯O hydrogen bonds, forming supra-molecular chains along the c axis. Furthermore, neighboring chains are inter-linked via weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming layers.

In the crystal of the title compound C(10)H(17)NO, synthesized by the reaction of β-cyclo-citral with hydroxyl-amine hydro-chloride, inversion-related mol-ecules are linked by a pair of O-H⋯N hydrogen-bonding inter-actions between the oxime functionalities, forming R(2) (2)(6) loops. The molecular conformation is stabilized by intra-molecular methyl C-H⋯N inter-actions. The cyclohexene ring has the typical half-chair conformation.

In the crystal structure of the title salt, C(4)H(8)N(5) (+)·BF(4) (-), centrosymmetrically related cations undergo base pairing via a pair of N-H⋯N hydrogen bonds, forming an R(2) (2)(8) ring motif. The cations and anions inter-act via N-H⋯F hydrogen bonds, generating supra-molecular layers parallel to ([Formula: see text]20), which are in turn linked into a three-dimensional network, forming rings of R(6) (6)(24) graph-set motif. The crystal structure is further stabilized by π-π stacking inter-actions [centroid-centroid distance = 3.3361 (12) Å].

The cation and anion of the title mol-ecular salt, C(7)H(10)NO(+)·C(6)H(2)N(3)O(8) (-), are linked via an N-H⋯O hydrogen bond. An intra-molecular O-H⋯O hydrogen bond is also found in the anion. In the crystal, the anions self-assemble via O-H⋯O hydrogen bonds, forming a C(9) supra-molecular chain the b axis. Further inter-molecular N-H⋯O inter-actions also occur.

In the title complex, [ZnBr(2)(C(4)H(5)N(3)O)(2)], the central metal ion is coordinated to two bromide ions and endocyclic N atoms of the two cytosine mol-ecules leading to a distorted tetra-hedral geometry. The structure is isotypic with [CdBr(2)(C(4)H(5)N(3)O)(2)] [Muthiah et al. (2001). Acta Cryst. E57, m558-m560]. There are two inter-ligand N-H⋯Br hydrogen bonds, generating two hydrogen-bonded rings stabilizing the coordination sphere. The complex aggregates, forming supra-molecular chains, sheets and staircases through N-H⋯O and N-H⋯Br hydrogen bonding and π-π stacking inter-actions [centroid-centroid distance = 3.616 (2) Å].

In the title co-crystal C(6)H(9)N(3)O(2)·C(10)H(9)NO(2), the 4,6-dimeth-oxy-pyrimidin-2-amine mol-ecule inter-acts with the carboxyl group of the 2-(1H-indol-3-yl)acetic acid mol-ecule through N-H⋯O and O-H⋯N hydrogen bonds, forming a cyclic hydrogen-bonded R(2) (2)(8) motif, which is further linked by an N-H⋯N hydrogen bond, forming a supra-molecular chain along the c axis. Neighboring chains are inter-linked via C-H⋯O hydrogen bonds, forming a supra-molecular ladder.

The title compound, C(17)H(15)N(3)O(4)S, is a monoclinic polymorph with space group P2(1)/c of the previously reported triclinic form in P [Subashini et al. (2009 ▶). J. Chem. Crystallogr.39, 112-116]. In both polymorphs, intra-molecular O-H⋯N hydrogen bonds and dimer formation via a pair of inter-molecular N-H⋯N hydrogen bonds with an R(2) (2)(8) motif are observed. The two polymorphs differ in the next level of supra-molecular organization involving C-H⋯O hydrogen bonds with varied packing and different conformations.

In 2,4-diamino-6-methyl-1,3,5-triazin-1-ium (acetoguanaminium) hydrogen phthalate, C(4)H(8)N(5)(+) x C(8)H(5)O(4)(-), (I), acetoguanaminium hydrogen maleate, C(4)H(8)N(5)(+) x C(4)H(3)O(4)(-), (II), and acetoguanaminium 3-hydroxypicolinate monohydrate, C(4)H(8)N(5)(+) x C(6)H(4)NO(3)(-) x H(2)O, (III), the acetoguanaminium cations interact with the carboxylate groups of the corresponding anions via a pair of nearly parallel N-H...O hydrogen bonds, forming R(2)(2)(8) ring motifs. In (II) and (III), N-H...N base-pairing is observed, while there is none in (I). In (II), a series of fused R(3)(2)(8), R(2)(2)(8) and R(3)(2)(8) hydrogen-bonded rings plus fused R(2)(2)(8), R(6)(2)(12) and R(2)(2)(8) ring motifs occur alternately, aggregating into a supramolecular ladder-like arrangement. In (III), R(2)(2)(8) motifs occur on either side of a further ring formed by pairs of N-H...O hydrogen bonds, forming an array of three fused hydrogen-bonded rings. In (I) and (II), the anions form a typical intramolecular O-H...O hydrogen bond with graph set S(7), whereas in (III) an intramolecular hydrogen bond with graph set S(6) is formed.

In 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium (pyrimethaminium, PMNH) 4-methylbenzoate, C(12)H(14)ClN(4)(+) x C(8)H(7)O(2)(-), (I), pyrimethaminium 3-hydroxypicolinate, C(12)H(14)ClN(4)(+) x C(6)H(4)NO(3)(-), (II), and pyrimethaminium 2,4-dichlorobenzoate, C(12)H(14)ClN(4)(+) x C(7)H(3)Cl(2)O(2)(-), (III), the PMNH cations interact with the carboxylate groups of the corresponding anion via nearly parallel N-H...O hydrogen bonds, forming R(2)(2)(8) ring motifs. A description of the observed arrays of quadruple hydrogen bonds in (I) and (II) in terms of hydrogen donors and acceptors (the DA model), their graph-set motifs and the resulting supramolecular ladder is given. In (III), supramolecular chains along the b axis and helical chains along the a axis are formed via N-H...O hydrogen bonds involving the 2-amino and 4-amino groups of the PMNH cation, respectively. Weak Cl...Cl interactions are also found in (III).

In the title 1:1 adduct, C(6)H(9)N(3)·C(7)H(7)NO(2), the crystal structure is stabilized by hydrogen bonds involving two different R(2) (2)(8) motifs. One of them is formed by the inter-action of 2-amino-4,6-dimethyl-pyrimidine (AMPY) with the carboxyl group of anthranilic acid (AA) through N-H⋯O and O-H⋯N hydrogen bonds, whereas the other is formed through the inter-action of two centrosymmetrically related pyrimidines involving N-H⋯N hydrogen bonds. These two combined motifs form a heterotetra-mer. The heterotetra-mer sheets are stacked into three-dimensional network.

In the title compound, [U(C(9)H(4)INO(4)S)O(2)(H(2)O)(3)].2H(2)O, the asymmetric unit contains a UO(2)(2+) ion coordinated by the N and O atoms of a 7-iodo-8-oxidoquinoline-5-sulfonate dianion (ferron anion) and three coordinated water molecules, and two uncoordinated water molecules. The UO(2)(2+) ion exhibits a seven-coordinate pentagonal bipyramidal geometry. The usual sulfonate oxygen coordination is absent but the sulfonate O atoms, along with the coordinated and lattice water molecules, play a vital role in assembling the three-dimensional structure via an extensive network of intermolecular O-H...O hydrogen bonds and pi-pi stacking interactions.

In the crystal structures of 2-amino-4,6-dimethoxypyrimidinium 2,4,6-trinitrophenolate (picrate), C(6)H(10)N(3)O(2)(+).C(6)H(2)N(3)O(7)(-), (I), and 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium (pyrimethaminium or PMN) picrate dimethyl sulfoxide solvate, C(12)H(14)ClN(4)(+).C(6)H(2)N(3)O(7)(-).C(2)H(6)OS, (II), the 2-amino-4,6-dimethoxypyrimidine and PMN cations are protonated at one of the pyrimidine N atoms. The picrate anion interacts with the protonated cations through bifurcated N-H...O hydrogen bonds, forming R(2)(1)(6) and R(1)(2)(6) ring motifs. In (I), Z' = 2. In (II), two inversion-related PMN cations are connected through a pair of N-H...N hydrogen bonds involving the 4-amino group and the uncharged N atom of the pyrimidine ring, forming a cyclic hydrogen-bonded R(2)(2)(8) motif. In addition to the pairing, the O atom of the dimethyl sulfoxide solvent molecule bridges the 2-amino and 4-amino groups on both sides of the paired bases, resulting in a self-complementary ...DADA... array of quadruple hydrogen-bonding patterns.

In the title compound, C(6)H(10)N(3) (+)·C(7)H(3)N(2)O(6) (-)·2H(2)O, the amino-pyrimidine mol-ecule is protonated at one of the pyrimidine N atoms. The carboxyl-ate group of the 3,5-dinitro-benzoate anion inter-acts with the protonated pyrimidine N atom and the 2-amino group through a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) motif. Two inversion-related pyrimidine rings are linked via a pair of N-H⋯N hydrogen bonds, also forming an R(2) (2)(8) ring motif.

In the title compound, {(C(10)H(12)N(3)O(3)S)(2)[CdCl(4)]·H(2)O}(n), the Cd(II) atom is five-coordinate with a distorted trigonal-bipyramidal geometry formed by chloride ions. The Cd atom and two of the Cl atoms lie on a mirror plane. The cation is protonated on the amino group N atom; it is not coordinated to cadmium, but is hydrogen bonded to the chlorido ligands. Each water mol-ecule bridges two chlorido ligands, generating ring motifs along the -Cd-Cl-Cd- chains. The isoxazole unit and the amide groups are linked through a pair of N-H⋯N hydrogen bonds. The crystal structure is stabilized by N-H⋯O, O-H⋯Cl, C-H⋯N, N-H⋯Cl and C-H⋯O hydrogen bonds.

In the title cocrystal, C(6)H(9)N(3)O(2)·C(7)H(7)NO(2), the asymmetric unit contains two crystallographically independent 2-amino-4,6-dimeth-oxy pyrimidine-anthranilic acid adducts. The 2-amino-4,6-dimeth-oxy pyrimidine mol-ecules inter-act with the carboxylic group of the respective anthranilic acid mol-ecules through N-H⋯O and O-H⋯N hydrogen bonds, forming a cyclic hydrogen-bonded motif R(2) (2)(8). The pyrimidine mol-ecules also form base pairs via a pair of N-H⋯N hydrogen bonds, forming another R(2) (2)(8) motif. The typical intra-molecular N-H⋯O hydrogen bond is observed in the anthranilic acid mol-ecules. Furthermore, the crystal structure is stabilized by C-H⋯O hydrogen bonds.

Background: Trimethoprim [2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine] is an antifolate drug. It selectively inhibits the bacterial dihydrofolate reductase (DHFR) enzyme., Results: In the crystal structures of trimethoprim (TMP)-hydrogen phthalate (1) and trimethoprim-hydrogen adipate (2), one of the N atoms of the pyrimidine ring is protonated and it interacts with the deprotonated carboxylate oxygens through a pair of nearly parallel N-H...O hydrogen bonds to form a fork-like interaction. In the compound 1, the pyrimidine moieties of the TMP cations are centrosymmetrically paired through a pair of N-H...N hydrogen bonds involving 4-amino group and the N (N3) atom of the pyrimidine rings to form a 8-membered hydrogen bonded ring [R2(2)(8)]. The 4-amino group of one TMP moiety and 2-amino group of another TMP moiety (both moieties are members of a base pair) are bridged by the carbonyl oxygen of the phthalate moiety through N-H...O hydrogen bonds forming 8-membered hydrogen-bonded ring [R2(2)(8)]. The characteristic hydrogen-bonded rings observed in the structure aggregate into a supramolecular ladder consisting of a pair of chains, each of which is built up of alternate TMP and hydrogen phthalate ions. In the compound 2, two TMP cations and two hydrogen adipate anions are arranged about an inversion center so that the complementary DDAA (D = donor, A = acceptor) arrays of quadruple hydrogen-bonding patterns are formed. The head-to-tail arrangement of the hydrogen adipate ions leads to a hydrogen-bonded supramolecular chain. From crystal engineering point of view, it is interesting to note that the compound 1 has a hydrogen-bonded network remarkably identical with its aliphatic analogue, trimethoprim hydrogen maleate. Similarly the compound 2, resembles its homolog trimethoprim hydrogen glutarate., Conclusion: In the crystal structure of trimethoprim hydrogen phthalate, the hydrogen-bonded network is remarkably identical with its aliphatic analogue, trimethoprim hydrogen maleate. Similarly in the crystal structure of trimethoprim hydrogen adipate the hydrogen bonded network resembles its homolog trimethoprim hydrogen glutarate.

In the title compound, C6H10N3+.HSO4-, the asymmetric unit consists of a hydrogen sulfate anion and a 2-amino-4,6-dimethylpyrimidinium cation. The hydrogen sulfate anions self-assemble through O-H...O hydrogen bonds, forming supramolecular chains along the b axis, while the organic cations form base pairs via N-H...N hydrogen bonds. The aminopyrimidinium cations join to the sulfate anions via a pair of hydrogen bonds donated from the pyrimidinium protonation site and from the exo amine group cis to the protonated site.

The title compound, trimethoprim (TMP) formate [systematic name: 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium formate], C(14)H(19)N(4)O(3)(+).CHO(2)(-), reveals a pseudo-quadruple hydrogen-bonding motif consisting of six N-H.O hydrogen bonds involving two unpaired TMP cations and two formate anions which are symmetrically disposed. The hydrogen-bonding motif is strikingly comparable with that observed in other TMP salts where the aminopyrimidine moieties of the TMP cations are centrosymmetrically paired. These conserved hydrogen-bonding motifs may serve as robust synthons in crystal engineering and design. The characteristic pseudo-quadruple hydrogen-bonding motif and other intermolecular hydrogen bonds operating in the crystal form a two-dimensional supramolecular sheet structure.