Browse
Submit Data
Databases
API
Help

Dataset Information

24 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

3,3-Bis(2-hydroxyethyl)-1-(4-nitrobenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: In the title compound, C12H15N3O5S, a trisubstituted thiourea derivative, the central CN2S chromophore is almost planar (r.m.s. deviation = 0.018?Å) and the pendant hydroxyethyl groups lie to either side of this plane. While to a first approximation the thione-S and carbonyl-O atoms lie to the same side of the molecule, the S—C—N—C torsion angle of ?47.8?(2)° indicates a considerable twist. As one of the hydroxyethyl groups is orientated towards the thioamide residue, an intramolecular N—H?O hydrogen bond is formed which leads to an S(7) loop. A further twist in the molecule is indicated by the dihedral angle of 65.87?(7)° between the planes through the CN2S chromophore and the 4-nitrobenzene ring. There is a close match between the experimental and gas-phase, geometry-optimized (DFT) molecular structures. In the crystal, O—H?O and O—H?S hydrogen bonds give rise to supramolecular layers propagating in the ab plane. The connections between layers to consolidate the three-dimensional architecture are of the type C—H?O, C—H?S and nitro-O??. The nature of the supramolecular association has been further analysed by a study of the calculated Hirshfeld surfaces, non-covalent interaction plots and computational chemistry, all of which point to the significant influence and energy of stabilization provided by the conventional hydrogen bonds.

SUBMITTER: Tan SL

PROVIDER: S-EPMC7001817 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

3,3-Bis(2-hy-droxy-eth-yl)-1-(4-methyl-benzoyl)thio-urea: crystal structure, Hirshfeld surface analysis and computational study.

Project description:In the title tri-substituted thio-urea derivative, C13H18N2O3S, the thione-S and carbonyl-O atoms lie, to a first approximation, to the same side of the mol-ecule [the S-C-N-C torsion angle is -49.3 (2)°]. The CN2S plane is almost planar (r.m.s. deviation = 0.018 Å) with the hy-droxy-ethyl groups lying to either side of this plane. One hy-droxy-ethyl group is orientated towards the thio-amide functionality enabling the formation of an intra-molecular N-H⋯O hydrogen bond leading to an S(7) loop. The dihedral angle [72.12 (9)°] between the planes through the CN2S atoms and the 4-tolyl ring indicates the mol-ecule is twisted. The experimental mol-ecular structure is close to the gas-phase, geometry-optimized structure calculated by DFT methods. In the mol-ecular packing, hydroxyl-O-H⋯O(hydrox-yl) and hydroxyl-O-H⋯S(thione) hydrogen bonds lead to the formation of a supra-molecular layer in the ab plane; no directional inter-actions are found between layers. The influence of the specified supra-molecular inter-actions is apparent in the calculated Hirshfeld surfaces and these are shown to be attractive in non-covalent inter-action plots; the inter-action energies point to the important stabilization provided by directional O-H⋯O hydrogen bonds.

| S-EPMC6775753 | 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-(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-(3,5-Dinitro-benzo-yl)-3,3-dipropyl-thio-urea.

Project description:The title thio-urea derivative, C(14)H(18)N(4)O(5)S, features two substantial twists between its component fragments: the dihedral angle between the SN(2)C (thio-urea) and ONC(2) (amide) residues is 48.89?(7)° and that between the benzene ring and the amide residue is 30.27?(7)°. In the crystal, mol-ecules are linked by bifurcated N-H?(O,S) hydrogen bonds, generating [001] supra-molecular chains.

| S-EPMC3089134 | biostudies-literature

N-[Eth-yl(2-hy-droxy-eth-yl)carbamo-thio-yl]-3-fluoro-benzamide.

Project description:In the title compound, C12H15FN2O2S, the mol-ecule adopts a cis configuration of the fluoro-benzoyl group with respect to the thiono group about their C-N bond. The dihedral angle between the fluoro-benzoyl group and the thio-urea N2CS fragment is 69.60?(11)°. An intra-molecular N-H?O hydrogen bond occurs. In the crystal, mol-ecules form chains along the b-axis direction via O-H?S and C-H?O hydrogen bonds.

| S-EPMC4011211 | biostudies-literature

N-[Eth-yl(2-hy-droxy-eth-yl)carbamo-thio-yl]-2-methyl-benzamide.

Project description:The title compound, C13H18N2O2S, adopts a cis conformation between the methyl-benzoyl and thiono groups across their thio-urea C-N bond. However, the methyl-benzoyl group and N2CS thio-urea moiety are twisted by 15.03?(3)°. In the molecule there is an N-H?O hydrogen bond. In the crystal, mol-ecules are linked by O-H?O inter-actions, generating chains extending along the c-axis direction.

| S-EPMC4011282 | biostudies-literature

1-(2-Hy-droxy-benzo-yl)thio-semicarbazide hemihydrate.

Project description:The asymmetric unit of the title compound, C(8)H(9)N(3)O(2)S·0.5H(2)O, contains two thiosemicarbazide mol-ecules with the short distance of 3.521?(3)?Å between the centroids of the benzene rings, and one water mol-ecule. In the two independent mol-ecules, the benzene rings and the thio-semicarbazone fragments are twisted at 9.2?(3) and 18.5?(3)°. An extensive three-dimensional hydrogen-bonding network, formed by inter-molecular N-H?O, N-H?S and O-H?O hydrogen bonds, consolidates the crystal packing.

| S-EPMC3011454 | biostudies-literature

2,4-Di-chloro-N-[eth-yl(2-hy-droxy-eth-yl)carbamo-thio-yl]benzamide.

Project description:In the title compound, C12H14Cl2N2O2S, the mol-ecule adopts a cis conformation with respect to the di-chloro-benzoyl group against the thiono group about the C-N bond. However, the di-chloro-benzene group and the thio-urea moiety are twisted by 75.41?(8)°. An intra-molecular N-H?O hydrogen bond occurs between the amido H atom and hydroxyl O atom. In the crystal, O-H?S and O-H?O hydrogen bonds link the molecules, forming chains along the b-axis direction.

| S-EPMC3914078 | biostudies-literature

1-(4-Nitro-benzo-yl)-3-(4-nitro-phen-yl)-thio-urea acetone hemisolvate.

Project description:In the title compound, C(14)H(10)N(4)O(5)S·0.5C(3)H(6)O, the nitro-benzoyl and nitro-phenyl groups have trans and cis configurations, respectively, with respect to the thio-urea S atom. The mol-ecular conformation is stabilized by intra-molecular N-H?O and C-H?S hydrogen bonds. The acetone solvent mol-ecule possesses a crystallographically imposed twofold axis. In the crystal packing, thio-urea mol-ecules are linked by inter-molecular C-H?O hydrogen-bond inter-actions to form chains running parallel to the c axis. The chains are further bridged via N-H?O and C-H?O hydrogen bonds involving the acetone mol-ecules.

| S-EPMC2959497 | 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