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1-Butyl-1-chloro-3-methyl-3 H -2,1 λ 4 -benzoxa ­ tellurole: crystal structure and Hirshfeld analysis

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ABSTRACT

Two independent mol­ecules comprise the asymmetric unit in the title benzoxatellurole compound, C12H17ClOTe. The mol­ecules, with the same chirality at the methine C atom, are connected into a loosely associated dimer by Te⋯O inter­actions, leading to a {⋯Te—O}2 core. The resultant C2ClO2 donor set approximates a square pyramid with the lone pair of electrons projected to occupy a position trans to the n-butyl substituent. Inter­estingly, the TeIV atoms exhibit opposite chirality. The major difference between the independent mol­ecules relates to the conformation of the five-membered chelate rings, which is an envelope with the O atom being the flap, in one mol­ecule and is twisted about the O—C(methine) bond in the other. No directional inter­molecular inter­actions are noted in the mol­ecular packing beyond the aforementioned Te⋯O secondary bonding. The analysis of the Hirshfeld surface reveals the dominance of H⋯H contacts, i.e. contributing about 70% to the overall surface, and clearly differentiates the immediate crystalline environments of the two independent mol­ecules in terms of both H⋯H and H⋯Cl/Cl⋯H contacts.

No MeSH data available.


An overlay diagram of the Te1- and Te2-containing mol­ecules, shown as red and blue images, respectively. The mol­ecules have been overlapped so that the phenyl rings are coincident.
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fig2: An overlay diagram of the Te1- and Te2-containing mol­ecules, shown as red and blue images, respectively. The mol­ecules have been overlapped so that the phenyl rings are coincident.

Mentions: The central {⋯Te—O}2 core of the dimeric aggregate, Fig. 1 ▸, is almost planar (r.m.s. deviation = 0.0106 Å) and has the form of a parallelogram with distinctive edge lengths of approximately 2.0 and 3.0 Å, reflecting the disparity of the Te⋯O inter­actions. To a first approximation, the fused phenyl ring in each mol­ecule, (C3–C8) and (C13–C20), is co-planar with the core, forming dihedral angles of 14.2 (2) and 13.6 (3)°, respectively; the dihedral angle between the phenyl rings is 8.3 (3)°. As the n-butyl groups lie to either side of the dimeric aggregate, there is a suggestion that the independent mol­ecules are related across a pseudo centre of inversion. However, the configuration of the chiral-C2 and C13 atoms in the Te1- and Te-mol­ecules, respectively, is R. This is highlighted in the overlay diagram shown in Fig. 2 ▸. Also highlighted is that the tellurium atoms have opposite chirality. When projected down the Te—C(n-but­yl) bond, the chirality about the Te1 atom is S and that about Te2, R.


1-Butyl-1-chloro-3-methyl-3 H -2,1 λ 4 -benzoxa ­ tellurole: crystal structure and Hirshfeld analysis
An overlay diagram of the Te1- and Te2-containing mol­ecules, shown as red and blue images, respectively. The mol­ecules have been overlapped so that the phenyl rings are coincident.
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Related In: Results  -  Collection

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fig2: An overlay diagram of the Te1- and Te2-containing mol­ecules, shown as red and blue images, respectively. The mol­ecules have been overlapped so that the phenyl rings are coincident.
Mentions: The central {⋯Te—O}2 core of the dimeric aggregate, Fig. 1 ▸, is almost planar (r.m.s. deviation = 0.0106 Å) and has the form of a parallelogram with distinctive edge lengths of approximately 2.0 and 3.0 Å, reflecting the disparity of the Te⋯O inter­actions. To a first approximation, the fused phenyl ring in each mol­ecule, (C3–C8) and (C13–C20), is co-planar with the core, forming dihedral angles of 14.2 (2) and 13.6 (3)°, respectively; the dihedral angle between the phenyl rings is 8.3 (3)°. As the n-butyl groups lie to either side of the dimeric aggregate, there is a suggestion that the independent mol­ecules are related across a pseudo centre of inversion. However, the configuration of the chiral-C2 and C13 atoms in the Te1- and Te-mol­ecules, respectively, is R. This is highlighted in the overlay diagram shown in Fig. 2 ▸. Also highlighted is that the tellurium atoms have opposite chirality. When projected down the Te—C(n-but­yl) bond, the chirality about the Te1 atom is S and that about Te2, R.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

Two independent mol­ecules comprise the asymmetric unit in the title benzoxatellurole compound, C12H17ClOTe. The mol­ecules, with the same chirality at the methine C atom, are connected into a loosely associated dimer by Te⋯O inter­actions, leading to a {⋯Te—O}2 core. The resultant C2ClO2 donor set approximates a square pyramid with the lone pair of electrons projected to occupy a position trans to the n-butyl substituent. Inter­estingly, the TeIV atoms exhibit opposite chirality. The major difference between the independent mol­ecules relates to the conformation of the five-membered chelate rings, which is an envelope with the O atom being the flap, in one mol­ecule and is twisted about the O—C(methine) bond in the other. No directional inter­molecular inter­actions are noted in the mol­ecular packing beyond the aforementioned Te⋯O secondary bonding. The analysis of the Hirshfeld surface reveals the dominance of H⋯H contacts, i.e. contributing about 70% to the overall surface, and clearly differentiates the immediate crystalline environments of the two independent mol­ecules in terms of both H⋯H and H⋯Cl/Cl⋯H contacts.

No MeSH data available.