In the title compound, C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4)° with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)°. The conformation about the N-N bond is gauche [C-N-N-C = -117.48 (15)°]. Overall, the mol-ecule has the shape of the letter L. In the crystal packing, supra-molecular chains along the a axis are formed by N-H⋯S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered {⋯HNCS}2 and 10-membered {⋯HNNH⋯S}2 synthons. The chains are connected into layers by phen-yl-tolyl C-H⋯π inter-actions; the layers stack along the c axis with no specific inter-actions between them.
In the title compound, C13H16N2O2S, the pyrrolidine ring has a twisted conformation on the central -CH2-CH2- bond. Its mean plane is inclined to the 4-meth-oxy-benzoyl ring by 72.79 (15)°. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds to the same O-atom acceptor, forming chains along [001]. The chains are linked via slipped parallel π-π inter-actions [inter-centroid distance = 3.7578 (13) Å], forming undulating slabs parallel to (100).
Two independent mol-ecules (A and B) comprise the asymmetric unit of the title compound, C21H18O4. There are significant conformational differences between the mol-ecules relating in particular to the relative orientation of the 3-oxo-2-(phenyl-methyl-idene)but-oxy substituent with respect to the superimposable chromen-2-one residues. To a first approximation, the substituents are mirror images; both are approximately perpendicular to the chromen-2-one fused ring system with dihedral angles of 88.50 (7) (A) and 81.96 (7)° (B). Another difference between the independent mol-ecules is noted in the dihedral angles between the adjacent phenyl and but-3-en-2-one groups of 8.72 (12) (A) and 27.70 (10)° (B). The conformation about the ethene bond in both mol-ecules is E. The crystal packing features C-H⋯O, C-H⋯π(ar-yl) and π-π [Cg⋯Cg = 3.6657 (8) and 3.7778 (8) Å] stacking inter-actions, which generate a three-dimensional network.
The asymmetric unit of the title complex, [Pd(C15H13FNO)2], contains one half of the mol-ecule with the Pd(II) cation lying on an inversion centre and is coordinated by the bidentate Schiff base anion. The geometry around the cationic Pd(II) centre is distorted square planar, chelated by the imine N- and phenolate O-donor atoms of the two Schiff base ligands. The N- and O-donor atoms of the two ligands are mutually trans, with Pd-N and Pd-O bond lengths of 2.028 (2) and 1.9770 (18) Å, respectively. The fluoro-phenyl ring is tilted away from the coordination plane and makes a dihedral angle of 66.2 (2)° with the phenolate ring. In the crystal, mol-ecules are linked into chains along the [101] direction by weak C-H⋯O hydrogen bonds. Weak π-π inter-actions with centroid-centroid distances of 4.079 (2) Å stack the mol-ecules along c.
The title salt, C5H11N2S(+)·C7H4ClO2 (-), comprises a 2-amino-3-ethyl-4,5-di-hydro-1,3-thia-zol-3-ium cation in which the five-membered ring adopts an envelope conformation with the methyl-ene C adjacent to the S atom being the flap, and a planar 3-chloro-benzoate anion (r.m.s. deviation for the 10 non-H atoms = 0.021 Å). The most prominent feature of the crystal packing are N-H⋯O hydrogen bonds whereby the two amine H atoms bridge two carboxyl-ate O atoms resulting in the formation of a centrosymmetric 12-membered {⋯HNH⋯OCO}2 synthon involving two cations and two anions. These aggregates are linked by C-H⋯O inter-actions to form a supra-molecular chain along the a-axis direction.
The asymmetric unit of the title compound, [Co(C2H6N5)2(H2O)4][Co(C7H3NO4)2]2·2H2O, features 1.5 Co(II) ions (one anionic complex and one half cationic complex) and one water mol-ecule. In the cationic complex, the Co(II) atom is located on an inversion centre and is coordinated by two triazolium cations and four water mol-ecules, adopting an octa-hedral geometry where the N atoms of the two triazolium cations occupy the axial positions and the O atoms of the four water mol-ecules the equatorial positions. The two triazole ligands are parallel offset (with a distance of 1.38 Å between their planes). In the anionic complex, the Co(II) ion is six-coordinated by two N and four O atoms of the two pyridine-2,6-di-carboxyl-ate anions, exhibiting a slightly distorted octa-hedral coordination geometry in which the mean plane of the two pyridine-2,6-di-carboxyl-ate anions are almost perpendicular to each other, making a dihedral angle of 85.87 (2)°. In the crystal, mol-ecules are linked into a three-dimensional network via C-H⋯O, C-H⋯N, O-H⋯O and N-H⋯O hydrogen bonds.
In the solid state, the title compound, C12H16BrNO5 [systematic name: 4-bromo-2-((1E)-{[1,3-dihy-droxy-2-(hy-droxy-meth-yl)propan-2-yl]iminium-yl}meth-yl)-6-meth-oxy-benzen-1-olate], C12H16BrNO5, is found in the keto-amine tautomeric form, with an intra-molecular iminium-N-H⋯O(phenolate) hydrogen bond and an E conformation about the C=N bond. Both gauche (two) and anti relationships are found for the methyl-hydroxy groups. In the crystal, a supra-molecular layer in the bc plane is formed via hy-droxy-O-H⋯O(hy-droxy) and charge-assisted hy-droxy-O-H⋯O(phenolate) hydrogen-bonding inter-actions; various C-H⋯O inter-actions provide additional cohesion to the layers, which stack along the a axis with no directional inter-actions between them. A Hirshfeld surface analysis confirms the lack of specific inter-actions in the inter-layer region.
The crystal and mol-ecular structures of two di-phenyl-tin bis-(di-thio-carbamate)s, [Sn(C6H5)2(C5H10NOS2)2], (I), and [Sn(C6H5)2(C7H14NO2S2)2], (II), are described. In (I), in which the metal atom lies on a twofold rotation axis, the di-thio-carbamate ligand coordinates with approximately equal Sn-S bond lengths and the ipso-C atoms of the Sn-bound phenyl groups occupy cis-positions in the resulting octa-hedral C2S4 donor set. A quite distinct coordination geometry is noted in (II), arising as a result of quite disparate Sn-S bond lengths. Here, the four S-donors define a trapezoidal plane with the ipso-C atoms lying over the weaker of the Sn-S bonds so that the C2S4 donor set defines a skewed trapezoidal bipyramid. The packing of (I) features supra-molecular layers in the ab plane sustained by methyl-ene-C-H⋯π(Sn-ar-yl) inter-actions; these stack along the c-axis direction with no specific inter-actions between them. In (II), supra-molecular chains along the b-axis direction are formed by methyl-ene-C-O(ether) inter-actions; these pack with no directional inter-actions between them. A Hirshfeld surface analysis was conducted on both (I) and (II) and revealed the dominance of H⋯H inter-actions contributing to the respective surfaces, i.e. >60% in each case, and other features consistent with the description of the mol-ecular packing above.
The title aza-stilbene derivative, C14H13NO2 {systematic name: (E)-2-[(4-meth-oxy-benzyl-idene)amino]-phenol}, is a product of the condensation reaction between 4-meth-oxy-benzaldehyde and 2-amino-phenol. The mol-ecule adopts an E conformation with respect to the azomethine C=N bond and is almost planar, the dihedral angle between the two substituted benzene rings being 3.29 (4)°. The meth-oxy group is coplanar with the benzene ring to which it is attached, the Cmeth-yl-O-C-C torsion angle being -1.14 (12)°. There is an intra-molecular O-H⋯N hydrogen bond generating an S(5) ring motif. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming zigzag chains along [10-1]. The chains are linked via C-H⋯π inter-actions, forming a three-dimensional structure.
In the title hydrate, C9H12N4S·H2O (systematic name: 3-methyl-1-{(E)-[(3-methyl-pyridin-2-yl)methyl-idene]amino}-thio-urea monohydrate), a small twist is noted between the pyridine ring and the rest of the organic mol-ecule [dihedral angle = 6.96 (5)°]. The imine and pyridine N atoms are syn, and the amine H atoms are anti. The latter arrangement allows for the formation of an intra-molecular N-H⋯N(imine) hydrogen bond. Both the N-bonded H atoms form hydrogen bonds to symmetry-related water mol-ecules, and the latter forms O-H hydrogen bonds with the pyridine N and thione S atoms. These inter-actions lead to supra-molecular layers that stack along the a-axis direction with no specific inter-actions between them.
In the organic mol-ecule of the title hydrate, C11H15N3OS·H2O, {systematic name: 3-ethyl-1-{(E)-[1-(2-hy-droxy-phen-yl)ethyl-idene]amino}-thio-urea monohydrate}, a dihedral angle of 5.39 (2)° is formed between the hy-droxy-benzene ring and the non-H atoms comprising the side chain (r.m.s. deviation = 0.0625 Å), with the major deviation from planarity noted for the terminal ethyl group [the C-N-C-C torsion angle = -172.17 (13)°]. The N-H H atoms are syn and an intra-molecular hy-droxy-imine O-H⋯N hydrogen bond is noted. In the crystal, the N-bonded H atoms form hydrogen bonds to symmetry-related water mol-ecules, and the latter form donor inter-actions with the hy-droxy O atom and with a hy-droxy-benzene ring, forming a O-H⋯π inter-action. The hydrogen bonding leads to supra-molecular tubes aligned along the b axis. The tubes are connected into layers via C-H⋯O inter-actions, and these stack along the c axis with no directional inter-actions between them.
In the title compound, C25H26N2O2S2, the central CN2S2 atoms are almost coplanar (r.m.s. deviation = 0.0058 Å). One phenyl ring clearly lies to one side of the central plane, while the other is oriented in the plane but splayed. Despite the different relative orientations, the phenyl rings form similar dihedral angles of 64.90 (3) and 70.06 (3)° with the central plane, and 63.28 (4)° with each other. The benzene ring is twisted with respect to the central plane, forming a dihedral angle of 13.17 (7)°. The S2C=N, N-N and N-N=C bond lengths of 1.2919 (19), 1.4037 (17) and 1.2892 (19) Å, respectively, suggest limited conjugation over these atoms; the configuration about the N-N=C bond is E. An intra-molecular O-H⋯N hydrogen bond is noted. In the crystal, phen-yl-meth-oxy C-H⋯O and phen-yl-phenyl C-H⋯π inter-actions lead to supra-molecular double chains parallel to the b axis. These are connected into a layer via meth-yl-phenyl C-H⋯π inter-actions, and layers stack along the a axis, being connected by weak π-π inter-actions between phenyl rings [inter-centroid distance = 3.9915 (9) Å] so that a three-dimensional architecture ensues.
Two independent mol-ecules, A and B, comprise the asymmetric unit of the title compound, C20H21N3OSe. While the benzene ring directly bound to the central triazole ring is inclined to the same extent in both mol-ecules [dihedral angles = 40.41 (12) (mol-ecule A) and 44.14 (12)° (B)], greater differences are apparent in the dihedral angles between the Se-bound rings, i.e. 74.28 (12) (mol-ecule A) and 89.91 (11)° (B). Close intra-molecular Se⋯N inter-actions of 2.9311 (18) (mol-ecule A) and 2.9482 (18) Å (B) are noted. In the crystal, supra-molecular chains along the a axis are formed via O-H⋯N hydrogen bonding. These are connected into layers via C-H⋯O and C-H⋯N inter-actions; these stack along (01-1) without directional inter-molecular inter-actions between them.
In the title compound, C10H11BrS2, the 1,3-di-thiane ring has a chair conformation with the 1,4-disposed C atoms being above and below the remaining four atoms. The bromo-benzene ring occupies an equatorial position and forms a dihedral angle of 86.38 (12)° with the least-squares plane through the 1,3-di-thiane ring. Thus, to a first approximation the mol-ecule has mirror symmetry with the mirror containing the bromo-benzene ring and the 1,4-disposed C atoms of the 1,3-di-thiane ring. In the crystal, mol-ecules associate via weak methyl-ene-bromo-benzene C-H⋯π and π-π [Cg⋯Cg = 3.7770 (14) Å for centrosymmetrically related bromo-benzene rings] inter-actions, forming supra-molecular layers parallel to [10-1]; these stack with no specific inter-molecular inter-actions between them.
In the title compound, C26H22N2O2, the dihedral angles between the 1-methyl-indole units (A and B) and the benzoic acid moiety (C) are A/B = 64.87 (7), A/C = 80.92 (8) and B/C = 75.05 (8)°. An intra-molecular C-H⋯O inter-action arising from the methyne group helps to establish the conformation. In the crystal, R22(8) carb-oxy-lic acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds are observed. A Hirshfeld surface analysis shows that the greatest contributions are from H⋯H, C⋯H/H⋯C and O⋯H/H⋯O contacts (percentage values = 54.6%, 29.6% and 10.1%, respectively).
The title compound, C16H15N5O2, adopts the shape of the letter L with the dihedral angle between the outer pyridyl rings being 78.37 (5)°; the dihedral angles between the central pyrazolyl ring (r.m.s. deviation = 0.0023 Å) and the methyl-ene-bound pyridyl and methyoxypyridyl rings are 77.68 (5) and 7.84 (10)°, respectively. Intra-molecular amide-N-H⋯N(pyrazol-yl) and pyridyl-C-H⋯O(amide) inter-actions are evident and these preclude the participation of the amide-N-H and O atoms in inter-molecular inter-actions. The most notable feature of the mol-ecular packing is the formation of linear supra-molecular chains aligned along the b-axis direction mediated by weak carbonyl-C=O⋯π(triazol-yl) inter-actions. An analysis of the calculated Hirshfeld surfaces point to the importance of H⋯H (46.4%), C⋯H (22.4%), O⋯H (11.9%) and N⋯H (11.1%) contacts in the crystal.
In the title di-thio-carbazate ester, C16H17N3S2 (systematic name: (Z)-{[(benzyl-sulfan-yl)methane-thio-yl]amino}[1-(6-methyl-pyridin-2-yl)ethyl-idene]amine), the central methyl-idenehydrazinecarbodi-thio-ate (C2N2S2) core is almost planar (r.m.s. deviation = 0.0111 Å) and forms dihedral angles of 71.67 (3)° with the approximately orthogonally inclined thio-ester phenyl ring, and 7.16 (7)° with the approximately coplanar substituted pyridyl ring. The latter arrangement and the Z configuration about the imine-C=N bond allows for the formation of an intra-molecular hydrazine-N-H⋯N(pyrid-yl) hydrogen bond that closes an S(6) loop. In the crystal, phenyl-C-H⋯S(thione), methyl-ene-C-H⋯π(pyrid-yl), methyl-ene- and phenyl-C-H⋯π(phen-yl) contacts connect mol-ecules into supra-molecular layers propagating in the bc plane; the layers stack along the a axis with no directional inter-actions between them. The analysis of the Hirshfeld surface indicates the relative importance of an intra-layer phenyl-H⋯H(pyrid-yl) contact upon the mol-ecular packing.
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 Ci-Ce-Ce-Cb 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.
The title zinc bis-(thio-semicarbazone) complex, [Zn(C22H17N4O2S)2], comprises two N,S-donor anions, leading to a distorted tetra-hedral N2S2 donor set. The resultant five-membered chelate rings are nearly planar and form a dihedral angle of 73.28 (3)°. The configurations about the endocyclic- and exocyclic-imine bonds are Z and E, respectively, and that about the ethyl-ene bond is E. The major differences in the conformations of the ligands are seen in the dihedral angles between the chelate ring and nitro-benzene rings [40.48 (6) cf. 13.18 (4)°] and the N-bound phenyl and nitro-benzene ring [43.23 (8) and 22.64 (4)°]. In the crystal, a linear supra-molecular chain along the b-axis direction features amine-N-H⋯O(nitro) hydrogen bonding. The chains assemble along the 21-screw axis through a combination of phenyl-C-H⋯O(nitro) and π(chelate ring)-π(phen-yl) contacts. The double chains are linked into a three-dimensional architecture through phenyl-C-H⋯O(nitro) and nitro-O⋯π(phen-yl) inter-actions.