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Crystal structure of 2,4-di-nitro-phenyl 4-methyl-benzene-sulfonate: a new polymorph.

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

Bottom Line: The title compound, C13H10N2O7S, was synthesized via a nucleophilic substitution reaction between 2,4-di-nitro-phenol and p-toluene-sulfonyl chloride.Acta Cryst, E59, o378-380].The aromatic substituents on the sulfonate group are oriented gauche to one another with a C-O-S-C torsion angle of -62.0 (3)°.

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

ABSTRACT
The title compound, C13H10N2O7S, was synthesized via a nucleophilic substitution reaction between 2,4-di-nitro-phenol and p-toluene-sulfonyl chloride. This crystal structure is a polymorph of CSD entry WUVYUH [Vembu et al. (2003). Acta Cryst, E59, o378-380]. The aromatic substituents on the sulfonate group are oriented gauche to one another with a C-O-S-C torsion angle of -62.0 (3)°. The supra-molecular features that contribute to the crystal stability are offset π-π [centroid-centroid distance = 3.729 (2) Å] and multiple C-H⋯O inter-actions.

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A drawing of a selection of the C—H⋯O inter­actions present in the crystal lattice using a ball and stick model. Symmetry codes: (i) −x + 1, −y + 1, z + ; (ii) −x + , y + , z − ; (iii) −x + 2, −y + 2, z − .
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fig3: A drawing of a selection of the C—H⋯O inter­actions present in the crystal lattice using a ball and stick model. Symmetry codes: (i) −x + 1, −y + 1, z + ; (ii) −x + , y + , z − ; (iii) −x + 2, −y + 2, z − .

Mentions: There are no classical hydrogen-bonding inter­actions in this crystal. There are, however, several inter­molecular C—H⋯O inter­actions with D⋯A distances less than 3.5 Å and D—H⋯A angles greater than 120° (Table 1 ▸, Fig. 3 ▸). An offset π–π stacking inter­action is present between the relatively electron-poor ring C8–C13 and the relatively electron-rich ring C2–C7v (Fig. 4 ▸). The centroid–centroid distance is 3.729 (2) Å, the C2–C7 ring is offset by 1.529 (5) Å and tilted 5.74 (12)° out of the plane defined by the C8–C13 ring [symmetry code: (v)  − x, − + y, − + z].


Crystal structure of 2,4-di-nitro-phenyl 4-methyl-benzene-sulfonate: a new polymorph.

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

A drawing of a selection of the C—H⋯O inter­actions present in the crystal lattice using a ball and stick model. Symmetry codes: (i) −x + 1, −y + 1, z + ; (ii) −x + , y + , z − ; (iii) −x + 2, −y + 2, z − .
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4555369&req=5

fig3: A drawing of a selection of the C—H⋯O inter­actions present in the crystal lattice using a ball and stick model. Symmetry codes: (i) −x + 1, −y + 1, z + ; (ii) −x + , y + , z − ; (iii) −x + 2, −y + 2, z − .
Mentions: There are no classical hydrogen-bonding inter­actions in this crystal. There are, however, several inter­molecular C—H⋯O inter­actions with D⋯A distances less than 3.5 Å and D—H⋯A angles greater than 120° (Table 1 ▸, Fig. 3 ▸). An offset π–π stacking inter­action is present between the relatively electron-poor ring C8–C13 and the relatively electron-rich ring C2–C7v (Fig. 4 ▸). The centroid–centroid distance is 3.729 (2) Å, the C2–C7 ring is offset by 1.529 (5) Å and tilted 5.74 (12)° out of the plane defined by the C8–C13 ring [symmetry code: (v)  − x, − + y, − + z].

Bottom Line: The title compound, C13H10N2O7S, was synthesized via a nucleophilic substitution reaction between 2,4-di-nitro-phenol and p-toluene-sulfonyl chloride.Acta Cryst, E59, o378-380].The aromatic substituents on the sulfonate group are oriented gauche to one another with a C-O-S-C torsion angle of -62.0 (3)°.

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, C13H10N2O7S, was synthesized via a nucleophilic substitution reaction between 2,4-di-nitro-phenol and p-toluene-sulfonyl chloride. This crystal structure is a polymorph of CSD entry WUVYUH [Vembu et al. (2003). Acta Cryst, E59, o378-380]. The aromatic substituents on the sulfonate group are oriented gauche to one another with a C-O-S-C torsion angle of -62.0 (3)°. The supra-molecular features that contribute to the crystal stability are offset π-π [centroid-centroid distance = 3.729 (2) Å] and multiple C-H⋯O inter-actions.

No MeSH data available.


Related in: MedlinePlus