Dataset Information

[N'-(4-Dec-yloxy-2-oxido-benzyl-idene)-3-hy-droxy-2-naphtho-hydrazidato-?³N,O,O']di-methyl-tin(IV): crystal structure and Hirshfeld surface analysis.

ABSTRACT: The title diorganotin compound, [Sn(CH₃)₂(C₂₈H₃₂N₂O₄)], features a distorted SnC₂NO₂ coordination geometry almost inter-mediate between ideal trigonal-bipyramidal and square-pyramidal. The dianionic Schiff base ligand coordinates in a tridentate fashion via two alkoxide O and hydrazinyl N atoms; an intra-molecular hy-droxy-O-H?N(hydrazin-yl) hydrogen bond is noted. The alk-oxy chain has an all-trans conformation, and to the first approximation, the mol-ecule has local mirror symmetry relating the two Sn-bound methyl groups. Supra-molecular layers sustained by imine-C-H?O(hy-droxy), ?-? [between dec-yloxy-substituted benzene rings with an inter-centroid separation of 3.7724?(13)?Å], C-H??(arene) and C-H??(chelate ring) inter-actions are formed in the crystal; layers stack along the c axis with no directional inter-actions between them. The presence of C-H??(chelate ring) inter-actions in the crystal is clearly evident from an analysis of the calculated Hirshfeld surface.

SUBMITTER: Rosely SN

PROVIDER: S-EPMC5347062 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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[N'-(4-Dec-yloxy-2-oxido-benzyl-idene)-3-hy-droxy-2-naphtho-hydrazidato-κ3N,O,O']di-methyl-tin(IV): crystal structure and Hirshfeld surface analysis.

Rosely Siti Nadiah Binti Mohd SN Hussen Rusnah Syahila Duali RS Lee See Mun SM Halcovitch Nathan R NR Jotani Mukesh M MM Tiekink Edward R T ER

Acta crystallographica. Section E, Crystallographic communications 20170217 Pt 3

The title diorganotin compound, [Sn(CH3)2(C28H32N2O4)], features a distorted SnC2NO2 coordination geometry almost inter-mediate between ideal trigonal-bipyramidal and square-pyramidal. The dianionic Schiff base ligand coordinates in a tridentate fashion via two alkoxide O and hydrazinyl N atoms; an intra-molecular hy-droxy-O-H⋯N(hydrazin-yl) hydrogen bond is noted. The alk-oxy chain has an all-trans ...[more]

PMID: 28316817

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Project description:The asymmetric unit of the title compound, [{Sn(C4H9)2(C6H5COO)}2O]2, consists of two half molecules, completed by application of inversion symmetry. Both mol-ecules adopt a ladder structure typical for this class of dimeric tetra-organodistannoxane di-carboxyl-ates characterized by a centrosymmetric four-membered (Sn-O)2 ring of rhomboidal shape that is extended on both sides by folded six-membered Sn-O-C rings. To a first approximation, both kinds of Sn atoms (Sn i and Sn o ) are trigonal-bipyramidally coordinated. The bond angles between the n-butyl groups are widened [135.64 (7)-146.20 (7)°] in comparison with an ideal trigonal bipyramid. Sn-O bond lengths within the {R2SnO3} coordination sphere depend strongly on the position of the corresponding O atom - axial (ax) or equatorial (eq) - as well as on the functionality of the carboxyl-ate groups which exhibit μ2 (-COO i ) and μ1 (-COO o ) coordination modes, respectively. In summary, the following sequence of distances [mean values] is found: d(Sn o -Oμ3) eq [2.024 (2) Å] < d(Sn i -Oμ3) eq [2.044 (2) Å] < d(Sn i -Oμ3) ax [2.158 (6) Å] < d(Sn o -Oμ1-carb) ax [2.182 (6) Å] < d(Sn i -Oμ2-carb) ax [2.250 (2) Å] ≃ d(Sn o -Oμ2-carb) ax [2.247 (12) Å]. The n-butyl groups adopt an anti-anti conformation with exception of two disordered outer n-butyl groups of the second mol-ecule which exhibit gauche-anti and anti-gauche conformations. Weak intra-molecular Sn⋯O inter-actions between the different O atoms of the outer carboxyl groups with the inner, as well as outer, Sn atoms give rise to a strongly distorted octa-hedral coordination at these Sn atoms. Inter-molecular inter-actions between the individual mol-ecules are restricted to van der Waals and O⋯H-C inter-actions of which a nearly linear very short C-H⋯O contact between the H atom of the phenyl group of one of the mol-ecules with the outer non-coordinating C=O group of the other molecule is the most prominent. It gives rise to a chain-like arrangement of the mol-ecules along [111]. The two n-butyl groups attached to the outer Sn atom of one mol-ecule are disordered over two sets of sites with occupancies of 0.806 (3)/0.194 (3) and 0.702 (3)/0.298 (3).

Dataset Information

[N'-(4-Dec-yloxy-2-oxido-benzyl-idene)-3-hy-droxy-2-naphtho-hydrazidato-?³N,O,O']di-methyl-tin(IV): crystal structure and Hirshfeld surface analysis.

Publications

[<i>N</i>'-(4-Dec-yloxy-2-oxido-benzyl-idene)-3-hy-droxy-2-naphtho-hydrazidato-κ<sup>3</sup><i>N</i>,<i>O</i>,<i>O</i>']di-methyl-tin(IV): crystal structure and Hirshfeld surface analysis.

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OmicsDI is part of the ELIXIR infrastructure

Dataset Information

[N'-(4-Dec-yloxy-2-oxido-benzyl-idene)-3-hy-droxy-2-naphtho-hydrazidato-?3N,O,O']di-methyl-tin(IV): crystal structure and Hirshfeld surface analysis.

Publications

[<i>N</i>'-(4-Dec-yloxy-2-oxido-benzyl-idene)-3-hy-droxy-2-naphtho-hydrazidato-κ<sup>3</sup><i>N</i>,<i>O</i>,<i>O</i>']di-methyl-tin(IV): crystal structure and Hirshfeld surface analysis.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

[N'-(4-Dec-yloxy-2-oxido-benzyl-idene)-3-hy-droxy-2-naphtho-hydrazidato-?³N,O,O']di-methyl-tin(IV): crystal structure and Hirshfeld surface analysis.