Structure of bis(2-amino-5-benzoylphenyl) diselenide

Warin, V.; Abdelhalim, Mohamed Anwar K; Baert, F.; Galet, V.; Houssin, Raymond; Lesieur, D.

doi:10.1107/s0108270193003506

Cited by 4 publications

(3 citation statements)

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“…The orientation adopted by each amine group is such that one of them is able to form a hydrogen-bond interaction with the Se atom [SeÁ Á ÁH1B = 2.72 (5) Å and SeÁ Á ÁH2B = 2.76 ( 4) Å ]. A search of the CSD for phenylselenium derivatives containing an ortho NH 2 substituent gave four hits [EXUHIP (Helios et al, 2011), HALNIR (Warin et al, 1993), QEBBEH (Silva et al, 2017), and RAQNIJ (Singh et al, 2017)]. In these structures, the SeÁ Á Á(N)H distances range from 2.63 (2) (QEBBEH; Silva et al, 2017) to 2.97 (5) Å (HALNIR; Warin et al, 1993).…”

Section: Figurementioning

confidence: 99%

“…A search of the CSD for phenylselenium derivatives containing an ortho NH 2 substituent gave four hits [EXUHIP (Helios et al, 2011), HALNIR (Warin et al, 1993), QEBBEH (Silva et al, 2017), and RAQNIJ (Singh et al, 2017)]. In these structures, the SeÁ Á Á(N)H distances range from 2.63 (2) (QEBBEH; Silva et al, 2017) to 2.97 (5) Å (HALNIR; Warin et al, 1993). Further evidence that such an interaction is real comes from the fact that, in each case, the displacement parameters for the interacting H atom are lower than those for the non-interacting H atoms (and this is also the case in the example structures quoted below).…”

Section: Figurementioning

confidence: 99%

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Bis(2-nitrophenyl) selenide, bis(2-aminophenyl) selenide and bis(2-aminophenyl) telluride: structural and theoretical analysis

2021

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Three organoselenium and organotellurium compounds containing ortho substitutents, namely, bis(2-nitrophenyl) selenide, C12H8N2O4Se, 2, bis(2-aminophenyl) selenide, C12H12N2Se, 3, and bis(2-aminophenyl) telluride, C12H12N2Te, 7, have been investigated by both structural and theoretical methods. In the structures of all three compounds, there are intramolecular contacts between both Se and Te with the ortho substituents. In the case of 2, this is achieved by rotation of the nitro group from the arene plane. For 3, both amino groups exhibit pyramidal geometry and are involved in intramolecular N—H...Se interactions, with one also participating in intermolecular N—H...N hydrogen bonding. While 3 and 7 are structurally similar, there are some significant differences. In addition to both intramolecular N—H...Te interactions and intermolecular N—H...N hydrogen bonding, 7 also exhibits intramolecular N—H...N hydrogen bonding. In the packing of these molecules, for 2, there are weak intermolecular C—H...O contacts and these, along with the O...N interactions mentioned above, link the molecules into a three-dimensional array. For 3, in addition to the N—H...N and N—H...Se interactions, there are also weak intermolecular C—H...Se interactions, which also link the molecules into a three-dimensional array. On the other hand, 7 shows intermolecular N—H...N interactions linking the molecules into R 2 2(16) centrosymmetric dimers. In the theoretical studies, for compound 2, AIM (atoms in molecules) analysis revealed critical points in the Se...O interactions with values of 0.017 and 0.026 a.u. These values are suggestive of weak interactions present between Se and O atoms. For 3 and 7, the molecular structures displayed intramolecular, as well as intermolecular, hydrogen-bond interactions of the N—H...N type. The strength of this hydrogen-bond interaction was calculated by AIM analysis. Here, the intermolecular (N—H...N) hydrogen bond is stronger than the intramolecular hydrogen bond. This was confirmed by the electron densities for 3 and 7 [ρ(r) = 0.015 and 0.011, respectively].

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Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Bis(2-nitrophenyl) selenide, bis(2-aminophenyl) selenide and bis(2-aminophenyl) telluride: structural and theoretical analysis

2021

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“…For the structure of the sulfido compound, see: Tommasi et al (1999). For related structures of other bisaryl diselenides, see: Jones & Ramírez de Arellano (1996); Meyers et al (1995); Warin et al (1993); Wojtowicz et al (2003). = 101.636 (5) V = 2013.0 (6) Å 3 Z = 2 Mo K radiation = 1.88 mm À1 T = 130 K 0.20 Â 0.17 Â 0.06 mm…”

Section: Related Literaturementioning

confidence: 99%

Bis{2-[(Triphenylmethyl)amino]phenyl} diselenide acetonitrile monosolvate

Neuba¹,

Schneider²,

Flörke³

et al. 2014

Acta Cryst E

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The molecular structure of the title compound, C50H40N2Se2·C2H3N, shows a syn conformation of the benzene rings bound to the Se atoms, with an Se—Se bond length of 2.3529 (6) Å and a C—Se—Se—C torsion angle of 93.53 (14)°. The two Se-bonded aromatic ring planes make a dihedral angle of 18.42 (16)°. Intramolecular N—H⋯Se hydrogen bonds are noted. Intermolecular C—H⋯Se interactions give rise to supramolecular chains extended along [100]. One severely disordered acetonitrile solvent molecule per asymmetric unit was treated with SQUEEZE in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]; the crystal data take the presence of this molecule into account.

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