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1-{(E)-[4-(4-Hy-droxy-phen-yl)butan-2-yl-idene]amino}-3-phenyl-thio-urea: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: The title thio-urea derivative, C₁₇H₁₉N₃OS, adopts a U-shaped conformation with the dihedral angle between the terminal aromatic rings being 73.64 (5)°. The major twist in the mol-ecule occurs about the ethane bond with the C_i-C_e-C_e-C_b torsion angle being -78.12 (18)°; i = imine, e = ethane and b = benzene. The configuration about the imine bond is E, the N-bound H atoms lie on opposite sides of the mol-ecule and an intra-molecular amine-N-H⋯N(imine) hydrogen bond is evident. In the mol-ecular packing, hydroxyl-O-H⋯S(thione) and amine-N-H⋯O hydrogen bonding feature within a linear, supra-molecular chain. The chains are connected into a layer in the ab plane by a combination of methyl-ene-C-H⋯S(thione), methyl-ene-C-H⋯O(hydrox-yl), methyl-C-H⋯π(phen-yl) and phenyl-C-H⋯π(hy-droxy-benzene) inter-actions. The layers stack without directional inter-actions between them. The analysis of the calculated Hirshfeld surface highlights the presence of weak methyl-C-H⋯O(hydrox-yl) and H⋯H inter-actions in the inter-layer region. Computational chemistry indicates that dispersion energy is the major contributor to the overall stabilization of the mol-ecular packing.

SUBMITTER: Tan MY

PROVIDER: S-EPMC8340978 | biostudies-literature |

REPOSITORIES: biostudies-literature

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3-{(E)-[4-(4-Hy-droxy-3-meth-oxy-phen-yl)butan-2-yl-idene]amino}-1-phenyl-urea: crystal structure and Hirshfeld surface analysis.

Project description:Two independent mol-ecules (A and B) comprise the asymmetric unit of the title compound, C18H21N3O3. The urea moiety is disubstituted with one amine being linked to a phenyl ring, which is twisted out of the plane of the CN2O urea core [dihedral angles = 25.57?(11) (A) and 29.13?(10)° (B)]. The second amine is connected to an imine (E conformation), which is linked in turn to an ethane bridge that links a disubstituted benzene ring. Intra-molecular amine-N-H?N(imine) and hydroxyl-O-H?O(meth-oxy) hydrogen bonds close S(5) loops in each case. The mol-ecules have twisted conformations with the dihedral angles between the outer rings being 38.64?(81) (A) and 48.55?(7)° (B). In the crystal, amide-N-H?O(amide) hydrogen bonds link the mol-ecules A and B via an eight-membered {?HNCO}2 synthon. Further associations between mol-ecules, leading to supra-molecular layers in the ac plane, are hydrogen bonds of the type hydroxyl-O-H?N(imine) and phenyl-amine-N-H?O(meth-oxy). Connections between layers, leading to a three-dimensional architecture, comprise benzene-C-H?O(hy-droxy) inter-actions. A detailed analysis of the calculated Hirshfeld surfaces shows mol-ecules A and B participate in very similar inter-molecular inter-actions and that any variations relate to conformational differences between the mol-ecules.

| S-EPMC5778478 | biostudies-literature

3-{(E)-[1-(2-Hy-droxy-phen-yl)ethyl-idene]amino}-1-(2-methyl-phen-yl)thio-urea.

Project description:In the title thio-urea derivative, C(16)H(17)N(3)OS, the hy-droxy- and methyl-substituted benzene rings form dihedral angles of 9.62?(12) and 55.69?(6)°, respectively, with the central CN(3)S chromophore (r.m.s. deviation = 0.0117?Å). An intra-molecular O-H?N hydrogen bond ensures the coplanarity of the central atoms. The H atoms of the NH groups are syn and the conformation about the N=C double bond [1.295?(4)?Å] is E. In the crystal, helical supra-molecular chains sustained primarily by N-H?S hydrogen bonds are found. Additional stabilization is provided by C-H?? and ?-? [ring centroid(hy-droxy-benzene)?ring centroid(methyl-benzene) = 3.8524?(18)?Å] inter-actions.

| S-EPMC3089068 | biostudies-literature

1-(2-Hy-droxy-eth-yl)-3-phenyl-thio-urea.

Project description:The title compound, C(9)H(12)N(2)OS, was obtained unexpectedly in a multicomponent reaction of an equimolar ratio of phenyl isothio-cyanate, malononitrile and amino-ethanol. The -C(H(2))-N(H)-(C=S)-N(H)- methyl-thio-urea-methane group is almost normal to the phenyl ring, with a dihedral angle of 71.13?(9)°. The N-C-C-O torsion angle is 72.8?(2)°. In the crystal, mol-ecules are connected by N-H?O, O-H?S and N-H?O hydrogen bonds, forming a three-dimensional network.

| S-EPMC3344104 | biostudies-literature

1-Benzoyl-3-(4-hy-droxy-phen-yl)thio-urea.

Project description:In the title compound, C(14)H(12)N(2)O(2)S, the amino-phenol and the benzoyl groups adopt a syn-anti configuration with respect to the thiono C=S group across the thio-urea C-N. The dihedral angle between the mean planes of the benzoyl and hy-droxy-phenyl rings is 36.77?(8)°. The mol-ecules are stabilized by intra-molecular N-H?O hydrogen bonds. In the crystal, weak inter-molecular C-H?O, O-H?S and N-H?O hydrogen bonds link the mol-ecules into a chain along the c axis.

| S-EPMC3011591 | biostudies-literature

3-[2-Hy-droxy-3-(2,4,6-trimethyl-phen-yl)prop-yl]-3-methyl-1-phenyl-thio-urea.

Project description:In the title compound, C(20)H(26)N(2)OS, four non-H atoms of the thio-urea unit are approximately planar (r.m.s. deviation = 0.005?Å); the phenyl and benzene rings are twisted out of this plane by 28.55?(7) and 60.00?(7)°, respectively. An intra-molecular N-H?O hydrogen bond occurs. The hy-droxy group is hydrogen bonded to the double-bond S atom of an inversion-related mol-ecule, generating a hydrogen-bonded dimer in the crystal structure.

| S-EPMC3089238 | biostudies-literature

1-[3-(Hy-droxy-meth-yl)phen-yl]-3-phenyl-urea.

Project description:In the title compound, C(14)H(14)N(2)O(2), the dihedral angle between the benzene rings is 23.6?(1)°. The H atoms of the urea NH groups are positioned syn to each other. In the crystal, inter-molecular N-H?O and O-H?O hydrogen bonds link the mol-ecules into a three-dimensional network.

| S-EPMC3213536 | biostudies-literature

1-(4-Hy-droxy-phen-yl)-3-(3,4,5-tri-methoxy-phen-yl)thio-urea.

Project description:In the title compound, C(16)H(18)N(2)O(4)S, the dihedral angle between the hy-droxy-phenyl ring and the plane of the thio-urea moiety is 54.53?(8)°. The H atoms of the NH groups of thio-urea are positioned anti to each other. In the crystal, inter-molecular N-H?S, N-H?O, and O-H?S hydrogen bonds link the mol-ecules into a three-dimensional network.

| S-EPMC3011736 | biostudies-literature

1-(2-Hy-droxy-eth-yl)-3-(3-meth-oxy-phen-yl)thio-urea.

Project description:In the title compound, C(10)H(14)N(2)O(3)S, the 3-meth-oxy-phenyl unit is almost planar, with an r.m.s. deviation of 0.013?Å. The dihedral angle between the benzene ring and the plane of the thio-urea unit is 62.57?(4)°. In the crystal, N-H?O and O-H?S hydrogen bonds link the mol-ecules into a three-dimensional network.

| S-EPMC2983277 | biostudies-literature

1-{(E)-[4-(4-Meth-oxy-phen-yl)butan-2-yl-idene]amino}-3-methyl-thio-urea.

Project description:Two independent mol-ecules comprise the asymmetric unit of the title compound, C(13)H(19)N(3)OS, which differ in the conformations of the residues linking the thio-urea and the terminal benzene ring, as manifested in the C(m)-C(m)-C(a)-C(a) torsion angles [78.03?(16) and -93.64?(16)°, respectively; m = methyl-ene and a = aromatic]. The dihedral angles [84.40?(4) and 88.28?(5)°] formed between the thio-urea residue and the benzene ring indicate an almost orthogonal relationship. In each thio-urea residue, the N-H hydrogen atoms are anti, and the terminal N-H hydrogen atom forms an intra-molecular N-H?N hydrogen bond with the imine-N atom. In each case, the conformation about the imine C=N double bond [1.2812?(17) and 1.2801?(17)?Å] is E. In the crystal, the mol-ecules are connected by N-H?S hydrogen bonds and these are connected into four mol-ecule aggregates via N-H?O hydrogen bonds, which are assembled into a two-dimensional array parallel to (011) via C-H?? and ?-? inter-actions [ring centroid-centroid distance = 3.8344?(9)?Å].

| S-EPMC3344575 | biostudies-literature

4-(4-Hy-droxy-phen-yl)butan-2-one.

Project description:In the title compound, C(10)H(12)O(2), the substituted benzene ring is inclined at a dihedral angle of 75.9?(1)° to the almost planar butan-2-one substituent (r.m.s. deviation = 0.02?Å). In the crystal, inter-molecular O-H?O hydrogen bonds link the mol-ecules into chains along the a axis.

| S-EPMC3120435 | biostudies-literature

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