Non-bonded Interactions Involving Oxygen in 2-Nitrobenzenethiolato Compounds: Structures of 2,4-(O2N)2C6H3SX (X= NMe2or C6H4NO2-2) and Ph3MSC6H4NO2-2 (M= Ge, Sn or Pb)

Aupers, John H.; Cox, Philip; Doidge-Harrison, Solange M.S.V.; Howie, R. Α.; Low, John N.; Wardell, Jámes L.

doi:10.1080/13583149912331338961

Cited by 11 publications

(17 citation statements)

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“…There are also several recently reported structures for related molecules which have conformations remote from that corresponding to the global energy minimum: in every case these conformations are associated with well developed intermolecular interactions, particularly the formation of CÐ HÁ Á ÁO hydrogen bonds. Thus, in 2-O 2 NC 6 H 4 SSnPh 3 (Aupers et al, 1999) the conformation is close to that of the local energy minimum, with the nitro group rotated out of the plane of the adjacent aryl ring by $50 , associated with a CÐCÐSÐ Sn torsional angle of $68 : the molecules are linked into C(9) chains by means of CÐHÁ Á ÁO hydrogen bonds (Fig. 12).…”

Section: Comparisons With Related Compoundsmentioning

confidence: 81%

“…The ®ndings described above (xx3.1±3.3) for (1)±(3) prompt re-evaluation of the conformational properties of closely related species, retrieved in many cases from the Cambridge Structural Database (Allen & Kennard, 1993). Both 2-O 2 NC 6 H 4 SNMe 2 (Ruostesuo et al, 1989) and 2,4-(O 2 N) 2 C 6 H 3 SNMe 2 (Aupers et al, 1999) adopt conformations in the solid state which are identical, in the case of the mononitro compounds, and close to, in the case of the dinitro derivative, the global energy minimum; there are no intermolecular hydrogen bonds in either compound. N-(2-Nitrophenylthio)phthalimide (Iwasaki & Masuko, 1986) is a close analogue of (3), and the entire molecule is virtually planar except for the near-orthogonal phthalimido group, corresponding to the global minimum; nonetheless, there is extensive intermolecular hydrogen bonding involving both the phthalimido O atoms and one of the nitro-group O atoms, just as in (3).…”

Section: Comparisons With Related Compoundsmentioning

confidence: 96%

“…11 and 13 were drawn using coordinates retrieved from the Cambridge Structural Database (Allen & Kennard, 1993); Figs. 12 and 14 were drawn using coordinates given by Aupers et al (1999). Selected molecular dimensions are presented in Tables 2 and 3, calculated net charges in Table 4, and details of the hydrogen bonding in Tables 5 and 6.…”

Section: Data Collection Structure Solution and Refinementmentioning

confidence: 99%

“…Atoms marked with an asterisk or hash symbol are in molecules at (1 + x, y, z) and (1 À x, 1 À y, 1 À z), respectively. Sudha et al, 1996;Jones et al, 1996;Aupers et al, 1999). The heterocyclic ring in (3) is slightly non-planar, doubtless as a consequence of the perfectly eclipsed CÐH bonds which would occur in a strictly planar pyrrolidinedione ring.…”

Section: Figurementioning

confidence: 99%

“…Hence, when an electropositive atom X is placed ortho to the nitro group, it is to be expected that there will be an attractive electrostatic interaction between X and the neighbouring O atom. For example, when X is S, it is commonly observed that the shortest intramolecular SÁ Á ÁO distance is signi®cantly shorter than the sum of the van der Waals radii (Aupers et al, 1999;Kucsman et al, 1984;Kucsman & Kapovits, 1985).…”

Section: Introductionmentioning

confidence: 99%

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Conformational preferences in 2-nitrophenylthiolates: interplay between intra- and intermolecular forces; structures of (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene, S-(2-nitrophenyl)benzenecarbothiolate and 1-(2-nitrophenylthio)-2,5-pyrrolidinedione

Low

Storey

McCarron

et al. 2000

Acta Crystallogr Sect B

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In (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene, C15H13NO2S (1) (orthorhombic Pbca), the nitro group is almost coplanar with the adjacent aryl ring, but the dihedral angles between the nitro-aryl and styryl fragments is approximately 121 degrees. The molecules are linked by paired C-H...O hydrogen bonds in a chain of rings. In S-(2-nitrophenyl)benzenecarbothiolate, C13H9NO3S (2) (monoclinic P2(1)/a), the nitro group is rotated by 33.0 (2) degrees out of the plane of the adjacent aryl ring and the thiobenzoate group is strongly twisted away from the plane of the disubstituted aryl ring. The molecules of (2) are linked into chains by C--H...O hydrogen bonds, and each chain is linked to two neighbouring chains by means of aromatic pi... pi stacking interactions. In 1-(2-nitrophenylthio)-2,5-pyrrolidinedione, C10H8N2O4S (3) (monoclinic P2(1)/a), the nitro group is again almost coplanar with the adjacent aryl ring, but the pyrrolidinedione unit is almost orthogonal to the O2NC6H4SN plane. There are three types of C-H...O hydrogen bond in the structure, and these link the molecules into a two-dimensional net. The conformations of these molecules have been investigated by SCF calculations and two energy minima have been identified for each: the molecules of (1) and (3) adopt conformations in their crystals which are close to those at the overall energy minima calculated for isolated molecules, while molecules of (2) adopt a conformation in the crystal close to that calculated for the local energy minimum. Comparisons are made with the structures of some related compounds and it is concluded that, while the nature of the two conformational minima is determined by intramolecular forces, the choice between them is determined primarily by intermolecular forces.

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Section: Comparisons With Related Compoundsmentioning

confidence: 81%

Section: Comparisons With Related Compoundsmentioning

confidence: 96%

Section: Data Collection Structure Solution and Refinementmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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