scholarly journals [(Z)-N-(3-Fluorophenyl)-O-methylthiocarbamato-κS](triphenylphosphane-κP)gold(I): crystal structure, Hirshfeld surface analysis and computational study

2020 ◽  
Vol 76 (8) ◽  
pp. 1284-1290
Author(s):  
Chien Ing Yeo ◽  
Sang Loon Tan ◽  
Huey Chong Kwong ◽  
Edward R. T. Tiekink
Keyword(s):  
Computational Study ◽  
Close Contact ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Thiolate Ligand ◽  
Intermolecular Contacts ◽  
Stabilization Energies ◽  
Type C ◽  
Dimeric Aggregates ◽  
Linear Geometry

The title phosphanegold(I) thiolate, C26H22AuFNOPS or [Au(C8H7FNOS)(C18H15P)], has the AuI centre coordinated by phosphane-P [2.2494 (8) Å] and thiolate-S [2.3007 (8) Å] atoms to define a close to linear geometry [P—Au—S = 176.10 (3)°]. The thiolate ligand is orientated so that the methoxy-O atom is directed towards the Au atom, forming an Au...O close contact of 2.986 (2) Å. In the crystal, a variety of intermolecular contacts are discerned with fluorobenzene-C—H...O(methoxy) and phenyl-C—H...F interactions leading to dimeric aggregates. These are assembled into a three-dimensional architecture by phenyl-C—H...S(thiolate) and phenyl-C—H...π(fluorobenzene, phenyl) interactions. Accordingly, the analysis of the calculated Hirshfeld surface shows 30.8% of all contacts are of the type C...H/H...C but this is less than the H...H contacts, at 44.9%. Other significant contributions to the surface come from H...F/F...H [8.1%], H...S/S...H [6.9%] and H...O/O...H [3.2%] contacts. Two major stabilization energies have contributions from the phenyl-C—H...π(fluorobenzene) and fluorobenzene-C—H...C(imine) interactions (−37.2 kcal mol−1), and from the fluorobenzene-C—H...F and phenyl-C—H...O interactions (−34.9 kcal mol−1), the latter leading to the dimeric aggregate.

scholarly journals New monoclinic form of {O-EthylN-(4-nitrophenyl)thiocarbamato-κS}(tri-4-tolylphosphane-κP)gold(I): crystal structure and Hirshfeld surface analysis

2017 ◽  
Vol 73 (10) ◽  
pp. 1465-1471 ◽  
Author(s):  
Fong Sheen Kuan ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Close Contact ◽  
Gold Atom ◽  
Hirshfeld Surface ◽  
Acta Cryst ◽  
Monoclinic Form ◽  
Hirshfeld Surfaces ◽  
Thiolate Ligand ◽  
Intermolecular Contacts ◽  
Supramolecular Chains ◽  
Linear Geometry

The title phosphanegold(I) thiolate compound, [Au(C9H9N2O3S)(C21H21P)], is a second monoclinic polymorph (space groupP21/c) that complements a previously reportedCcpolymorph [Broker & Tiekink (2008).Acta Cryst. E64, m1582]. An SP donor set defines an approximately linear geometry about the gold atom in both forms. The key distinguishing feature between the present structure and the previously reported polymorph rests with the relative disposition of the thiolate ligand. In the title compound, the orientation is such to place the oxygen atom in close contact with the gold atom [Au...O = 2.915 (2) Å], in contrast to the aryl ring in the original polymorph. In the crystal, linear supramolecular chains along thea-axis direction mediated by C–H...π and nitro-O...π interactions are found. These pack with no directional interactions between them. The analysis of the Hirshfeld surfaces for both forms of [Au(C9H9N3O3S)(C21H21P)] indicates quite distinctive interaction profiles relating to the differences in intermolecular contacts found in their respective crystals.

scholarly journals 2,2′-(Disulfanediyl)dibenzoic acid N,N-dimethylformamide monosolvate: crystal structure, Hirshfeld surface analysis and computational study

2020 ◽  
Vol 76 (7) ◽  
pp. 1150-1157
Author(s):  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Benzene Ring ◽  
Computational Study ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Title 1 ◽  
Torsion Angles ◽  
Carboxylic Acid Groups ◽  
Hirshfeld Surfaces ◽  
Intermolecular Contacts ◽  
Benzene Rings

The title 1:1 solvate, C14H10O4S2·C3H7NO, features a twisted molecule of 2,2′-dithiodibenzoic acid (DTBA), with the central C—S—S—C torsion angle being −88.57 (6)°, and a molecule of dimethylformamide (DMF). The carboxylic acid groups are, respectively, close to co-planar and twisted with respect to the benzene rings to which they are connected as seen in the CO2/C6 torsion angles of 1.03 (19) and 7.4 (2)°. Intramolecular, hypervalent S←O interactions are noted [S...O = 2.6140 (9) and 2.6827 (9) Å]. In the crystal, four-molecule aggregates are formed via DTBA-O—H...O(DMF) and DTBA-O—H...O(DTBA) hydrogen bonding, the latter via an eight-membered {...OHCO}2 homosynthon. These are linked into supramolecular layers parallel to (011) via benzene-C—H...O(DTBA) and DTBA-C=O...π(benzene) interactions, with the connections between these, giving rise to a three-dimensional architecture, being of the type benzene-C—H...π(benzene). An analysis of the calculated Hirshfeld surfaces indicates, in addition to the aforementioned intermolecular contacts, the presence of stabilizing interactions between a benzene ring and a quasi-π-system defined by O—H...O hydrogen bonds between a DTBA dimer, i.e. the eight-membered {...OCOH}2 ring system, and between a benzene ring and a quasi-π(OCOH...OCH) system arising from the DTBA-O—H...O(DMF) hydrogen bond. The inter-centroid separations are 3.65 and 3.49 Å, respectively.

scholarly journals 4-Benzyl-1-(4-nitrophenyl)-1H-1,2,3-triazole: crystal structure and Hirshfeld analysis

2017 ◽  
Vol 73 (11) ◽  
pp. 1716-1720 ◽  
Author(s):  
Julio Zukerman-Schpector ◽  
Sofia Dallasta Pedroso ◽  
Lucas Sousa Madureira ◽  
Márcio Weber Paixão ◽  
Akbar Ali ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Torsion Angle ◽  
Title Compound ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Aromatic Rings ◽  
Compound C ◽  
Centroid Distance ◽  
Hirshfeld Analysis ◽  
Intermolecular Contacts

The molecule in the title compound, C15H12N4O2, has a twistedL-shape with the dihedral angle between the aromatic rings of the N-bound benzene and C-bound benzyl groups being 70.60 (9)°. The nitro group is co-planar with the benzene ring to which it is connected [C—C—N—O torsion angle = 0.4 (3)°]. The three-dimensional packing is stabilized by a combination of methylene-C—H...O(nitro), methylene-C—H...π(phenyl), phenyl-C—H...π(triazolyl) and nitro-O...π(nitrobenzene) interactions, along with weak π(triazolyl)–π(nitrobenzene) contacts [inter-centroid distance = 3.8386 (10) Å]. The importance of the specified intermolecular contacts has been verified by an analysis of the calculated Hirshfeld surface.

scholarly journals A cinnamaldehyde Schiff base ofS-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study

2017 ◽  
Vol 73 (4) ◽  
pp. 543-549 ◽  
Author(s):  
Enis Nadia Md Yusof ◽  
Mohamed I. M. Tahir ◽  
Thahira B. S. A. Ravoof ◽  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Mirror Symmetry ◽  
Computational Study ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Hydrogen Atoms ◽  
Benzyl Substituent

The title dithiocarbazate ester (I), C18H18N2S2[systematic name: (E)-4-methylbenzyl 2-[(E)-3-phenylallylidene]hydrazinecarbodithioate, comprises an almost planar central CN2S2residue [r.m.s. deviation = 0.0131 Å]. The methylene(tolyl-4) group forms a dihedral angle of 72.25 (4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586 Å] so the molecule approximates mirror symmetry with the 4-tolyl group bisected by the plane. The configuration about both double bonds in the N—N=C—C=C chain isE; the chain has an alltransconformation. In the crystal, eight-membered centrosymmetric thioamide synthons, {...HNCS}2, are formedviaN—H...S(thione) hydrogen bonds. Connections between the dimersviaC—H...π interactions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an interaction profile similar to that of a closely related analogue with anS-bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connectedviaN—H...S hydrogen bonds is about 0.94 kcal mol−1more stable than that in (I).

scholarly journals The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

2020 ◽  
Vol 76 (1) ◽  
pp. 102-110 ◽  
Author(s):  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Hydrogen Bonds ◽  
Benzoic Acid ◽  
Computational Study ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Molecular Structures ◽  
Amide Hydrogen ◽  
Title 1 ◽  
Crystal And Molecular Structures ◽  
Hirshfeld Surfaces

The crystal and molecular structures of the title 1:2 co-crystal, C14H14N4O2·2C7H6O2, are described. The oxalamide molecule has a (+)-antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central, almost planar C2N2O2 chromophore (r.m.s. deviation = 0.0555 Å). The benzoic acid molecules have equivalent, close to planar conformations [C6/CO2 dihedral angle = 6.33 (14) and 3.43 (10)°]. The formation of hydroxy-O—H...N(pyridyl) hydrogen bonds between the benzoic acid molecules and the pyridyl residues of the diamide leads to a three-molecule aggregate. Centrosymmetrically related aggregates assemble into a six-molecule aggregate via amide-N—H...O(amide) hydrogen bonds through a 10-membered {...HNC2O}2 synthon. These are linked into a supramolecular tape via amide-N—H...O(carbonyl) hydrogen bonds and 22-membered {...HOCO...NC4NH}2 synthons. The contacts between tapes to consolidate the three-dimensional architecture are of the type methylene-C—H...O(amide) and pyridyl-C—H...O(carbonyl). These interactions are largely electrostatic in nature. Additional non-covalent contacts are identified from an analysis of the calculated Hirshfeld surfaces.

scholarly journals Crystal structure and Hirshfeld surface analysis of 2-(4-nitrophenyl)-2-oxoethyl 2-chlorobenzoate

2019 ◽  
Vol 75 (11) ◽  
pp. 1792-1796
Author(s):  
S. N. Sheshadri ◽  
C. S. Chidan Kumar ◽  
S. Naveen ◽  
M. K. Veeraiah ◽  
Kakarla Raghava Reddy ◽  
...  
Keyword(s):  
Supramolecular Structure ◽  
Three Dimensional ◽  
Shape Index ◽  
Hirshfeld Surface ◽  
Aromatic Rings ◽  
Bond Forming ◽  
Surface Patches ◽  
Compound C ◽  
Intermolecular Contacts ◽  
Two Sides

The title compound, C15H10ClNO5, is relatively planar with the two aromatic rings being inclined to each other by 3.56 (11)°. The central —C(=O)—C–O—C(=O)— bridge is slightly twisted, with a C—C—O—C torsion angle of 164.95 (16)°. In the crystal, molecules are linked by C—H...O and C—H...Cl hydrogen bonds, forming layers parallel to the (101) plane. The layers are linked by a further C—H...O hydrogen bond, forming a three-dimensional supramolecular structure. There are a number of offset π–π interactions present between the layers [intercentroid distances vary from 3.8264 (15) to 3.9775 (14) Å]. Hirshfeld surface analyses, the d norm surfaces, electrostatic potential and two-dimensional fingerprint plots were examined to verify the contributions of the different intermolecular contacts within the supramolecular structure. The shape-index surface shows that two sides of the molecule are involved in the same contacts with neighbouring molecules, and the curvedness plot shows flat surface patches that are characteristic of planar stacking.

scholarly journals (N,N-Diisopropyldithiocarbamato)triphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

2019 ◽  
Vol 75 (10) ◽  
pp. 1479-1485 ◽  
Author(s):  
Farah Natasha Haezam ◽  
Normah Awang ◽  
Nurul Farahana Kamaludin ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Computational Study ◽  
Close Approach ◽  
Molecular Geometry ◽  
Hirshfeld Surface ◽  
Molecular Structures ◽  
Crystal And Molecular Structures ◽  
Dithiocarbamate Ligand ◽  
Dimeric Aggregates

The crystal and molecular structures of the title triorganotin dithiocarbamate, [Sn(C6H5)3(C7H14NS2)], are described. The molecular geometry about the metal atom is highly distorted being based on a C3S tetrahedron as the dithiocarbamate ligand is asymmetrically chelating to the tin centre. The close approach of the second thione-S atom [Sn...S = 2.9264 (4) Å] is largely responsible for the distortion. The molecular packing is almost devoid of directional interactions with only weak phenyl-C—H...C(phenyl) interactions, leading to centrosymmetric dimeric aggregates, being noted. An analysis of the calculated Hirshfeld surface points to the significance of H...H contacts, which contribute 66.6% of all contacts to the surface, with C...H/H...C [26.8%] and S...H/H...H [6.6%] contacts making up the balance.

scholarly journals Bis[2-(4,5-diphenyl-1H-imidazol-2-yl)-4-nitrophenolato]copper(II) dihydrate: crystal structure and Hirshfeld surface analysis

2019 ◽  
Vol 75 (11) ◽  
pp. 1664-1671 ◽  
Author(s):  
Sailesh Chettri ◽  
Dhiraj Brahman ◽  
Biswajit Sinha ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Chelate Ring ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Molecular Structures ◽  
Coordination Geometry ◽  
Bidentate Ligands ◽  
Metal Centre ◽  
Hirshfeld Surfaces ◽  
Square Planar ◽  
Intermolecular Contacts

The crystal and molecular structures of the title CuII complex, isolated as a dihydrate, [Cu(C21H14N3O3)2]·2H2O, reveals a highly distorted coordination geometry intermediate between square-planar and tetrahedral defined by an N2O2 donor set derived from two mono-anionic bidentate ligands. Furthermore, each six-membered chelate ring adopts an envelope conformation with the Cu atom being the flap. In the crystal, imidazolyl-amine-N—H...O(water), water-O—H...O(coordinated, nitro and water), phenyl-C—H...O(nitro) and π(imidazolyl)–π(nitrobenzene) [inter-centroid distances = 3.7452 (14) and 3.6647 (13) Å] contacts link the components into a supramolecular layer lying parallel to (101). The connections between layers forming a three-dimensional architecture are of the types nitrobenzene-C—H...O(nitro) and phenyl-C—H...π(phenyl). The distorted coordination geometry for the CuII atom is highlighted in an analysis of the Hirshfeld surface calculated for the metal centre alone. The significance of the intermolecular contacts is also revealed in a study of the calculated Hirshfeld surfaces; the dominant contacts in the crystal are H...H (41.0%), O...H/H...O (27.1%) and C...H/H...C (19.6%).

scholarly journals A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

2019 ◽  
Vol 75 (1) ◽  
pp. 1-7 ◽  
Author(s):  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Benzoic Acid ◽  
Dihedral Angle ◽  
Computational Study ◽  
Three Dimensional ◽  
Acid Group ◽  
Hirshfeld Surface ◽  
Carboxylic Acid Group ◽  
Title 1 ◽  
Axis Of Symmetry ◽  
Ring Centroid

The asymmetric unit of the title 1:2 co-crystal, C14H10O4S2·2C7H6O2, comprises half a molecule of dithiodibenzoic acid [systematic name: 2-[(2-carboxyphenyl)disulfanyl]benzoic acid, DTBA], as the molecule is located about a twofold axis of symmetry, and a molecule of benzoic acid (BA). The DTBA molecule is twisted about the disulfide bond [the C—S—S—C torsion angle is −83.19 (8)°] resulting in a near perpendicular relationship between the benzene rings [dihedral angle = 71.19 (4)°]. The carboxylic acid group is almost co-planar with the benzene ring to which it is bonded [dihedral angle = 4.82 (12)°]. A similar near co-planar relationship pertains for the BA molecule [dihedral angle = 3.65 (15)°]. Three-molecule aggregates are formed in the crystal whereby two BA molecules are connected to a DTBA molecule via hydroxy-O—H...O(hydroxy) hydrogen bonds and eight-membered {...HOC=O}2 synthons. These are connected into a supramolecular layer in the ab plane through C—H...O interactions. The interactions between layers to consolidate the three-dimensional architecture are π–π stacking interactions between DTBA and BA rings [inter-centroid separation = 3.8093 (10) Å] and parallel DTBA-hydroxy-O...π(BA) contacts [O...ring centroid separation = 3.9049 (14) Å]. The importance of the specified interactions as well as other weaker contacts, e.g. π–π and C—H...S, are indicated in the analysis of the calculated Hirshfeld surface and interaction energies.

scholarly journals Secondary bonding in dimethylbis(morpholine-4-carbodithioato-κ2S,S′)tin(IV): crystal structure and Hirshfeld surface analysis

2017 ◽  
Vol 73 (6) ◽  
pp. 842-848 ◽  
Author(s):  
Nordiyana Binti Zaldi ◽  
Rusnah Syahila Duali Hussen ◽  
See Mun Lee ◽  
Nathan R. Halcovitch ◽  
Mukesh M. Jotani ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Title Compound ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Methyl Groups ◽  
Coordination Geometry ◽  
Intermolecular Contacts ◽  
Centrosymmetric Dimers ◽  
Secondary Bonding

The title compound, [Sn(CH3)2(C5H8NOS2)2], has the SnIVatom bound by two methyl groups which lie over the weaker Sn—S bonds formed by two asymmetrically chelating dithiocarbamate ligands so that the coordination geometry is skew-trapezoidal bipyramidal. The most prominent feature of the molecular packing are secondary Sn...S interactions [Sn...S = 3.5654 (7) Å] that lead to centrosymmetric dimers. These are connected into a three-dimensional architectureviamethylene-C—H...S and methyl-C—H...O(morpholino) interactions. The Sn...S interactions are clearly evident in the Hirshfeld surface analysis of the title compound along with a number of other intermolecular contacts.

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