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Different packing motifs of isomeric (E)-N'-(halo-phenyl-methyl-idene)-N-methyl-2-(thio-phen-2-yl)acetohydrazides controlled by C-H?O inter-actions.

ABSTRACT: The crystal structures of three isomeric (E)-N'-(chloro-phenyl-methyl-idene)-N-methyl-2-(thio-phen-2-yl)acetohydrazides (C14H13ClN2OS) are described, with the Cl atom in ortho (I), meta (III) and para (IV) positions in the benzene ring. The ortho-bromo derivative (II) (C14H13BrN2OS), which is isostructural with its chloro congener (I), is also reported. Mol-ecules (I)-(III) have similar conformations, which approximate to l-shapes, as indicated by their N-C-C-Ct (t = thio-phene) torsion angles of -90.1?(3), -91.44?(18) and -90.7?(9)°, respectively. The conformation of (IV) is different, with an equivalent torsion angle of -170.75?(11)° corresponding to a more extended shape for the mol-ecule. The thio-phene ring in each structure features 'flip' rotational disorder. The packing for (I) and (II) features inversion dimers, linked by pairs of C-H?O inter-actions, which generate R22(14) loops. In the crystal of (III), [010] C(8) chains arise, with adjacent mol-ecules linked by pairs of C-H?O hydrogen bonds. The packing for (IV) features unusually short C-H?O inter-actions arising from an H atom attached to the benzene ring (H?O = 2.18?Å), which lead to C(9) [301] chains. Hirshfeld fingerprint percentage contact contributions are similar for the four title compounds.

SUBMITTER: Cardoso LNF

PROVIDER: S-EPMC5947793 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Different weak inter-actions in the crystals of three isomeric (E)-N-methyl-N'-(nitro-benzyl-idene)-2-(thio-phen-2-yl)acetohydrazides.

Project description:The crystal structures of three isomeric (E)-N-methyl-N'-(nitro-benzyl-idene)-2-(thio-phen-2-yl)acetohydrazides (formula C14H13N3O3S) are described, with the nitro group in ortho, meta and para positions in the benzene ring. In each crystal structure, mol-ecules are linked by various weak inter-actions (C-H?O and C-H?? bonds, and ?-? stacking), leading to three-dimensional networks in each case, but with little similarity between them.

| S-EPMC5137586 | biostudies-literature

Different packing motifs mediated by weak inter-actions and polymorphism in the crystal structures of five 2-(benzyl-idene)benzosuberone derivatives.

Project description:The syntheses and crystal structures of five 2-benzyl-idene-1-benzosuberone [1-benzosuberone is 6,7,8,9-tetra-hydro-5H-benzo[7]annulen-5-one] derivatives, viz. 2-(4-meth-oxy-benzyl-idene)-1-benzosuberone, C19H18O2, (I), 2-(4-eth-oxy-benzyl-idene)-1-benzosuberone, C20H20O2, (II), 2-(4-benzyl-benzyl-idene)-1-benzosuberone, C25H22O2, (III), 2-(4-chloro-benzyl-idene)-1-benzosuberone, C18H15ClO, (IV) and 2-(4-cyano-benzyl-idene)-1-benzosuberone, C19H15NO, (V), are described. The conformations of the benzosuberone fused six- plus seven-membered ring fragments are very similar in each case, but the dihedral angles between the fused benzene ring and the pendant benzene ring differ somewhat, with values of 23.79?(3) for (I), 24.60?(4) for (II), 33.72?(4) for (III), 29.93?(8) for (IV) and 21.81?(7)° for (V). Key features of the packing include pairwise C-H?O hydrogen bonds for (II) and (IV), and pairwise C-H?N hydrogen bonds for (V), which generate inversion dimers in each case. The packing for (I) and (III) feature C-H?O hydrogen bonds, which lead to [010] and [100] chains, respectively. Weak C-H?? inter-actions consolidate the structures and weak aromatic ?-? stacking is seen in (II) [centroid-centroid separation = 3.8414?(7)?Å] and (III) [3.9475?(7)?Å]. A polymorph of (I) crystallized from a different solvent has been reported previously [Dimmock et al. (1999 ?) J. Med. Chem. 42, 1358-1366] in the same space group but with a packing motif based on inversion dimers resembling that seen in (IV) in the present study. The Hirshfeld surfaces and fingerprint plots for (I) and its polymorph are com-pared and structural features of the 2-benzyl-idene-1-benzosuberone family of phases are surveyed.

| S-EPMC6829743 | biostudies-literature

C-H⋯π packing inter-actions in 2-[5,5-bis-(4-benzyl-oxyphen-yl)-3-cyano-4-methyl-2,5-dihydro-furan-2-yl-idene]malononitrile.

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| S-EPMC3247440 | biostudies-literature

Crystal structure of two N'-(1-phenyl-benzyl-idene)-2-(thio-phen-3-yl)acetohydrazides.

Project description:The synthesis, spectroscopic data, crystal and mol-ecular structures of two N'-(1-phenyl-benzyl-idene)-2-(thio-phen-3-yl)acetohydrazides, namely N'-[1-(4-hy-droxy-phen-yl)benzyl-idene]-2-(thio-phen-3-yl)acetohydrazide, C13H10N2O2S, (3a), and N'-[1-(4-meth-oxy-phen-yl)benzyl-idene]-2-(thio-phen-3-yl)acetohydrazide, C14H14N2O2S, (3b), are described. Both compounds differ in the substituent at the para position of the phenyl ring: -OH for (3a) and -OCH3 for (3b). In (3a), the thio-phene ring is disordered over two orientations with occupancies of 0.762 (3) and 0.238 (3). The configuration about the C=N bond is E. The thio-phene and phenyl rings are inclined by 84.0 (3) and 87.0 (9)° for the major- and minor-occupancy disorder components in (3a), and by 85.89 (12)° in (3b). Although these dihedral angles are similar, the conformation of the linker between the two rings is different [the C-C-C-N torsion angle is -ac for (3a) and -sc for (3b), while the C6-C7-N9-N10 torsion angle is +ap for (3a) and -sp for (3b)]. A common feature in the crystal packing of (3a) and (3b) is the presence of N-H⋯O hydrogen bonds, resulting in the formation of chains of mol-ecules running along the b-axis direction in the case of (3a), or inversion dimers for (3b). The most prominent contributions to the surface contacts are those in which H atoms are involved, as confirmed by an analysis of the Hirshfeld surface.

| S-EPMC6690450 | biostudies-literature

4-Methyl-1-(3-pyridyl-methyl-idene)thio-semicarbazide.

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| S-EPMC3011564 | biostudies-literature

Crystal structures and Hirshfeld surfaces of differently substituted (E)-N'-benzyl-idene-N-methyl-2-(thio-phen-2-yl)acetohydrazides.

Project description:The syntheses and crystal structures of (E)-N'-(3-cyano-benzyl-idene)-N-methyl-2-(thio-phen-2-yl)acetohydrazide, C15H13N3OS, (I), and (E)-N'-(4-meth-oxy-benzyl-idene)-N-methyl-2-(thio-phen-2-yl)acetohydrazide, C15H16N2O2S, (II), with different substituents in the meta and para position of the benzene ring are described. Compounds (I) and (II) both crystallize with two mol-ecules in the asymmetric unit, with generally similar conformations [r.m.s. overlay fits for (I) and (II) of 0.334 and 0.280?Å, respectively] that approximate to L-shapes. The thio-phene rings in (I) are well ordered, whereas those in (II) exhibit 'flip' rotational disorder [occupancies 0.662?(2) and 0.338?(2) for mol-ecule 1, and 0.549?(3) and 0.451?(3) for mol-ecule 2]. The packing for (I) features short C-H?O inter-actions arising from the C-H grouping adjacent to the cyanide group and C-H?Nc (c = cyanide) links arising from the methine groups to generate [110] double chains. Weak C-H?? inter-actions inter-link the chains into a three-dimensional network. The packing for (II) features numerous C-H?O and C-H?? inter-actions arising from different donor groups to generate a three-dimensional network. Hirshfeld fingerprint plots indicate significant differences in the percentage contact surfaces for (I) and (II).

| S-EPMC5683480 | biostudies-literature

Methyl 3-(pyridin-4-yl-methyl-idene)di-thio-carbazate.

Project description:There are two independent mol-ecules in the asymmetric unit of the title mol-ecule, C8H9N3S2, both of which exhibit an E conformation with the pyridine ring and di-thio-carbazate fragment located on opposite sides of the C=N bond. The pyridine ring and di-thio-carbazate group are approximately coplanar, with dihedral angles of 4.74?(1) and 8.77?(1)° between their planes in the two mol-ecules. In the crystal, mol-ecules are linked to each other via N-H?N hydrogen bonds, forming zigzag chains parallel to [10-1].

| S-EPMC3648245 | biostudies-literature

4-Methyl-1-[4-(methyl-sulfan-yl)benzyl-idene]thio-semicarbazide.

Project description:The title compound, C(10)H(13)N(3)S(2), is roughly planar (r.m.s. deviation = 0.086?Å). In the crystal, N-H?S hydrogen bonds link the mol-ecules into (001) sheets.

| S-EPMC3213514 | biostudies-literature

2-[(5-Methyl-thio-phen-2-yl)methyl-idene]malono-nitrile.

Project description:There are two independent molecules in the asymmetric unit of the title compound, C9H6N2S, which is an inter-mediate compound of a cardiovascular drug. The two molecules are nearly planar, displaying dihedral angles of 3.5 (2) and 5.7 (2)° between the thiophene ring and the malononitrile moiety. In the crystal, C-H⋯N inter-actions lead to the formation of a sheet structure that packs in a parallel fashion.

| S-EPMC3772448 | biostudies-literature

Crystal structure of 4-methyl-benzyl N'-[(thio-phen-2-yl)methyl-idene]hydrazinecarbodi-thio-ate.

Project description:In the title compound, C15H16N2S3 {systematic name: [({[(4-methyl-phen-yl)meth-yl]sulfan-yl}methane-thio-yl)amino][1-(thio-phen-2-yl)ethyl-idene]amine}, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0061 Å) and forms dihedral angles of 7.39 (10) and 64.91 (5)° with the thienyl and p-tolyl rings, respectively; the dihedral angle between these rings is 57.52 (6)°. The non-thione S atoms are syn, and with respect to the thione S atom, the benzyl group is anti. In the crystal, centrosymmetrically related mol-ecules self-associate via eight-membered {⋯HNCS}2 synthons. The dimeric aggregates stack along the a axis and are are consolidated into a three-dimensional architecture via methyl-C-H⋯π(benzene) and benzene-C-H⋯π(thien-yl) inter-actions.

| S-EPMC4518925 | biostudies-literature

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