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Crystal structure of 3,5-di-methyl-phenyl 2-nitro-benzene-sulfonate.

Atanasova TP, Riley S, Biros SM, Staples RJ, Ngassa FN - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The mol-ecules form centrosymmetric dimers via π-π stacking inter-actions between 3,5-di-methyl-phenyl groups (centroid-centroid distance = 3.709 Å).An inter-molecular S=O⋯N inter-action between the sulfonyl and nitro groups, with an O⋯N distance of 2.9840 (18) Å, organizes the dimers into columns extending along [011].These columns are further assembled into (111) layers through C-H⋯O inter-actions.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Grand Valley State University, 1 Campus Dr., Allendale, MI 49401, USA.

ABSTRACT
The title compound, C14H13NO5S, was synthesized via a nucleophilic substitution reaction between 3,5-di-methyl-phenol and 2-nitro-benzene-sulfonyl chloride. The aromatic rings attached to the SO3 group are oriented in a gauche fashion around the ester S-O bond, with a C-S-O-C torsion angle of 84.68 (11)°. The mol-ecules form centrosymmetric dimers via π-π stacking inter-actions between 3,5-di-methyl-phenyl groups (centroid-centroid distance = 3.709 Å). An inter-molecular S=O⋯N inter-action between the sulfonyl and nitro groups, with an O⋯N distance of 2.9840 (18) Å, organizes the dimers into columns extending along [011]. These columns are further assembled into (111) layers through C-H⋯O inter-actions.

No MeSH data available.


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The mol­ecular structure of the title compound, with displacement ellipsoids shown at the 50% probability level. All H atoms have been omitted for clarity. Color codes: black C, blue N, red O and yellow S.
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fig2: The mol­ecular structure of the title compound, with displacement ellipsoids shown at the 50% probability level. All H atoms have been omitted for clarity. Color codes: black C, blue N, red O and yellow S.

Mentions: In the title mol­ecule (Fig. 2 ▸), the O1=S1=O2 and C1—S1—O3 bond angles of 119.41 (7) and 104.16 (6)° are typical for phenyl benzene­sulfonates with a gauche conformation around the ester S—O bond. The torsion angle C1—S1—O3—C7 around the ester bond is −84.68 (11)°. Owing to steric hindrance between the ortho substituents of the benzene ring, the nitro group is twisted relative to the benzene best plane by 39.91 (2)°, so that the shortest contact of 2.7941 (16) Å between the O atoms of these groups is close to the sum of the van der Waals radii.


Crystal structure of 3,5-di-methyl-phenyl 2-nitro-benzene-sulfonate.

Atanasova TP, Riley S, Biros SM, Staples RJ, Ngassa FN - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of the title compound, with displacement ellipsoids shown at the 50% probability level. All H atoms have been omitted for clarity. Color codes: black C, blue N, red O and yellow S.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4555383&req=5

fig2: The mol­ecular structure of the title compound, with displacement ellipsoids shown at the 50% probability level. All H atoms have been omitted for clarity. Color codes: black C, blue N, red O and yellow S.
Mentions: In the title mol­ecule (Fig. 2 ▸), the O1=S1=O2 and C1—S1—O3 bond angles of 119.41 (7) and 104.16 (6)° are typical for phenyl benzene­sulfonates with a gauche conformation around the ester S—O bond. The torsion angle C1—S1—O3—C7 around the ester bond is −84.68 (11)°. Owing to steric hindrance between the ortho substituents of the benzene ring, the nitro group is twisted relative to the benzene best plane by 39.91 (2)°, so that the shortest contact of 2.7941 (16) Å between the O atoms of these groups is close to the sum of the van der Waals radii.

Bottom Line: The mol-ecules form centrosymmetric dimers via π-π stacking inter-actions between 3,5-di-methyl-phenyl groups (centroid-centroid distance = 3.709 Å).An inter-molecular S=O⋯N inter-action between the sulfonyl and nitro groups, with an O⋯N distance of 2.9840 (18) Å, organizes the dimers into columns extending along [011].These columns are further assembled into (111) layers through C-H⋯O inter-actions.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Grand Valley State University, 1 Campus Dr., Allendale, MI 49401, USA.

ABSTRACT
The title compound, C14H13NO5S, was synthesized via a nucleophilic substitution reaction between 3,5-di-methyl-phenol and 2-nitro-benzene-sulfonyl chloride. The aromatic rings attached to the SO3 group are oriented in a gauche fashion around the ester S-O bond, with a C-S-O-C torsion angle of 84.68 (11)°. The mol-ecules form centrosymmetric dimers via π-π stacking inter-actions between 3,5-di-methyl-phenyl groups (centroid-centroid distance = 3.709 Å). An inter-molecular S=O⋯N inter-action between the sulfonyl and nitro groups, with an O⋯N distance of 2.9840 (18) Å, organizes the dimers into columns extending along [011]. These columns are further assembled into (111) layers through C-H⋯O inter-actions.

No MeSH data available.


Related in: MedlinePlus