A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π-π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates

Article abstract of DOI:10.1107/S2053229618008355

To explore the operational role of noncovalent interactions in supramolecular architectures with designed topologies, a series of solid-state structures of 2- and 4-formylphenyl 4-substituted benzenesulfonates was investigated. The compounds are 2-formylp

Full text of DOI:10.1107/S2053229618008355

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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Volume 74 (2018)
Supporting information for article:
A comparative experimental and theoretical investigation of
hydrogen, halogen and π–π interactions in the solid-state supra-
molecular assembly of 2- and 4-formylphenyl arylsulfonates
Hina Andleeb, Imtiaz Khan, Antonio Bauzá, Muhammad Nawaz Tahir, Jim
Simpson, Shahid Hameed and Antonio Frontera

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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SUPPORTING INFORMATION
A comparative experimental and theoretical investigation of hydrogen,
halogen and π···π interactions in the solid-state supramolecular assembly of
2- and 4-formylphenyl arylsulfonates
Hina Andleeb,a Imtiaz Khan,a,† Antonio Bauzá,b Muhammad Nawaz Tahir,c Jim Simpson,d
Shahid Hameeda,* and Antonio Fronterab,*
aDepartment of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan
bDepartament de Química, Universitat de les Illes Balears, Crta. de Valldemossa km 7.5, 07122
Palma de Mallorca (Baleares), Spain
cDepartment of Physics, University of Sargodha, Sargodha-40100, Pakistan
dDepartment of Chemistry, University of Otago, P.O. Box 56, Dunedin, 9054, New
Zealand
†School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, United
Kingdom
*Corresponding authors. E-mail: shameed@qau.edu.pk (S. Hameed); Tel.: +92 51 9064 2133;
Fax: +92 51 9064 2241; E-mail: toni.frontera@uib.es (A. Frontera); Tel: +34 971 259576; Fax:
+34 971 17 27 63

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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X-ray Crystallography
Figure S1 Sheets of 3a molecules in the ac plane.
Figure S2 Zig-zag chains of 3a molecules along c. In this and subsequent Figures, hydrogen bonds
are drawn as blue dashed lines.

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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Figure S3 Double chains of 3a molecules along b.
Figure S4 Overall packing for 3a viewed along the b axis direction. For clarity, only selected π…π
contacts are shown.
Figure S5 Linked inversion dimers of compound 3b.

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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Figure S6 Zig-zag chains of molecules of 3b form along the b axis.
Figure S7 Zig-zag chains of molecules of 3b along the c axis.

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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Figure S8 Overall packing for 3b viewed along the c axis direction.
Figure S9 Double C(6) chains of 3c molecules along a. The Br…π contacts are shown as dotted
green lines.

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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Figure S10 Inversion dimers of 3c molecules stacked along the a axis direction.
Figure S11 C(7) chains of 3c molecules along b.

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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(a)
(b)
Figure S12 Two views of the overall packing for 3c (a) along the b and (b) along the c axis
directions.
Figure S13 Double chains of molecules of 4b along c.

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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Figure S14 Chains of inversion dimers of 4b along the ac diagonal.
Figure S15 Overall packing for 4b viewed along the b axis direction.

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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Figure S16 Sheets of 4c molecules parallel to (0 1 2).
Figure S17 C6'-H6'...O41 4c inversion dimers stacked along b.

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Figure S18 C3-H3...O1 4c inversion dimers stacked along b.
Figure S19 Overall packing for 4c viewed along the a axis direction with only selected π…π and
C=O…π contacts shown.

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NMR Spectra

Acta Cryst. (2018). C74, doi:10.1107/S2053229618008355
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FTIR Spectra

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