N-(2-Formyl-phen-yl)-4-toluene-sulfonamide: a second monoclinic polymorph

Area of Science:

• Solid-state chemistry
• Crystallography
• Materials science

Background:

• Polymorphism is crucial in determining the physical and chemical properties of crystalline compounds.
• Understanding crystal packing and intermolecular forces is key to controlling material properties.
• Previous research identified a monoclinic polymorph of C(14)H(13)NO(3)S (II).

Purpose of the Study:

• To characterize a newly discovered second monoclinic polymorph of C(14)H(13)NO(3)S (I).
• To compare the crystal structure, molecular geometry, and intermolecular interactions of polymorph (I) with the previously reported polymorph (II).
• To elucidate the differences in crystal packing and stabilizing interactions between the two polymorphs.

Main Methods:

• Single-crystal X-ray diffraction was used to determine the crystal structure of the title compound (I).
• Analysis of crystallographic data, including space group, unit cell parameters, and molecular geometry.
• Comparison of dihedral angles, hydrogen bonding patterns, and crystal packing arrangements between polymorphs (I) and (II).

Main Results:

• The title compound (I) crystallizes in the monoclinic space group P2(1)/n with Z=4, distinct from polymorph (II) (P2(1)/c, Z=4).
• Polymorph (I) exhibits a dihedral angle of 75.9° between aromatic rings, compared to 81.9° in (II), with similar intramolecular hydrogen bonding.
• Significant differences in crystal packing were observed: polymorph (I) forms C(8) zigzag chains via C-H⋯O bonds and is stabilized by intermolecular C-H⋯π and π-π interactions, which are absent in polymorph (II) that forms C(7) chains.

Conclusions:

• A novel monoclinic polymorph (I) of C(14)H(13)NO(3)S has been identified and structurally characterized.
• The two polymorphs exhibit distinct crystal packing arrangements and intermolecular interactions, particularly C-H⋯π and π-π interactions in polymorph (I).
• These findings highlight the impact of subtle structural variations on crystal engineering and material properties.