Phenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

Manivannan, V.; Vembu, Nagarajan; Nallu, Maruthai; Sivakumar, K.; Fronczek, Frank R.

doi:10.1107/s1600536805001029

Cited by 8 publications

(12 citation statements)

References 23 publications

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“…A search of version 5.23 (July 2002 updates) of the Cambridge Structural Database (Allen, 2002) revealed 16 structures [refcodes KAWDAN (Niestroj et al, 1998), FIXCAQ (Chinnakali et al, 1999), NEDXUP, NEDYAW, NEDYIE (Gallucci et al, 1998), NUNCII (Goswami et al, 1998), RASSOT (Işik et al, 1997), RELVUZ (Bott et al, 1996), SIMVUF (Bindal et al, 1990), TCPTOS (Wieczorek & Galdecki, 1978), TEBFOV (Prince et al, 1991), TMPDTS (Wieczorek et al, 1975), TSMIPH (Sarkar & Gupta, 1980), WOHCUR (Meents et al, 2000), ZZZBDA10 (Wieczorek, 1980) and MIWHIJ (Lee et al, 2001)] that are closely related to the title compound in having benzene rings attached to the sulfonate group. The S-C, S-O and S O bond lengths (Table 1) are comparable to those found in related structures (Vembu et al, 2004, and references therein;Manivannan et al, 2005, and references therein).…”

Section: Commentsupporting

confidence: 84%

4-Bromophenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

et al. 2005

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In the crystal structure of the title compound, C13H11BrO3S, the dihedral angle between the mean planes of the 4‐tolyl and 4‐bromophenyl rings is 67.3 (2)°. There are weak C—H⋯O hydrogen bonds which generate rings of graph‐set motifs S(5), S(6), R12(4), R21(6) and R22(8). The supramolecular aggregation is completed by the presence of C—H⋯π interactions. An R22(7) motif formed by the combination of a C—H⋯O and a C—H⋯π interaction is a notable feature in the title compound.

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Section: Commentsupporting

confidence: 84%

4-Bromophenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

et al. 2005

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“…The dihedral angle between the mean planes of the phenyl and acetylaminophenyl C 6 rings of 71.58 (8)°shows that the two rings are not coplanar. This is similar to that reported by us for other aromatic sulfonates (Manivannan et al 2005 & references cited therein). The acetylamino group (N17 C18 O19 C20) is twisted by 16.3 (1)° from the mean plane of the phenyl ring (C11-C16) to which it is attached.…”

Section: And References Cited Therein)supporting

confidence: 93%

“…1 with selected geometric parameters provided in Table 1. The S-C, S-O and S=O bond lengths are comparable with those found in related structures previously reported by our research group (Manivannan et al 2005…”

Section: S1 Commentsupporting

confidence: 90%

4-(Acetylamino)phenyl benzenesulfonate

Vembu

Sparkes²,

Howard

2007

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 120 K; mean (C-C) = 0.002 Å; R factor = 0.038; wR factor = 0.104; data-to-parameter ratio = 15.8.The phenyl and acetylaminophenyl rings of the title compound, C 14 H 13 NO 4 S, are at an angle of 71.57 (5) , with the acetylamino group rotated by 16.3 (1) from coplanarity with the ring to which it is attached. The structure is stabilized by the presence of N-HÁ Á ÁO hydrogen bonds which create infinite one-dimensional chains along [010]; weak C-HÁ Á ÁO interactions are also present. Related literatureFor a detailed account of the molecular and supramolecular architectures of aromatic sulfonates, see Manivannan et al. (2005) and references cited therein. For related literature, see: Alford et al. ExperimentalCrystal data C 14 H 13 NO 4 S M r = 291.31 Monoclinic, P2 1 =n a = 11.9028 (14) Å b = 8.7768 (9) Å c = 13.7394 (15) Å = 110.144 (4) V = 1347.5 (3) Å 3 Z = 4 Mo K radiation = 0.25 mm À1 T = 120 (2) K 0.32 Â 0.28 Â 0.20 mm Data collection Bruker SMART CCD 1K area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1998) T min = 0.869, T max = 1.000 (expected range 0.922-0.951) 9274 measured reflections 3637 independent reflections 2983 reflections with I > 2(I) R int = 0.026

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“…The C2-S1-O10-C11 torsion angle of 60.6 (2)° corresponds to +synclinal conformation; as expected the dihedral angle between the mean planes of the phenyl and naphthyl rings of 47.57 (7)° shows that the two rings are not coplanar. This is similar to the situation reported by us for other aromatic sulfonates (Manivannan et al 2005 & references cited therein).…”

Section: And References Cited Therein)supporting

confidence: 92%

“…For a detailed account of the molecular and supramolecular architectures of aromatic sulfonates, see Manivannan et al (2005) and references cited therein.…”

Section: Related Literaturementioning

confidence: 99%

2-Naphthyl benzenesulfonate

Vembu

Shafna

Sparkes³

et al. 2007

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 120 K; mean (C-C) = 0.003 Å; R factor = 0.047; wR factor = 0.127; data-to-parameter ratio = 17.1.The phenyl and naphthyl ring systems are at an angle of 47.57 (9) in the title compound, C 16 H 12 O 3 S. Only weak C-HÁ Á ÁO interactions are present in the crystal structure. Related literatureFor a detailed account of the molecular and supramolecular architectures of aromatic sulfonates, see Manivannan et al. (2005) and references cited therein. For related literature, see: Alford et al. ExperimentalCrystal data C 16 H 12 O 3 S M r = 284.32 Orthorhombic, Pbcn a = 11.8910 (11) Å b = 10.8909 (12) Å c = 20.958 (2) Å V = 2714.1 (5) Å 3 Z = 8 Mo K radiation = 0.24 mm À1 T = 120 (2) K 0.24 Â 0.16 Â 0.08 mm Data collection Bruker SMART CCD 1K area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1998) T min = 0.814, T max = 1.000 (expected range = 0.922-0.951) 19056 measured reflections 3917 independent reflections 2262 reflections with I > 2(I) R int = 0.089

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Phenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

Abstract: Key indicatorsSingle-crystal X-ray study T = 173 K Mean (C-C) = 0.005 Å R factor = 0.067 wR factor = 0.177 Data-to-parameter ratio = 20.9For details of how these key indicators were automatically derived from the article, see

Cited by 8 publications

References 23 publications

4-Bromophenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

4-Bromophenyl 4-toluenesulfonate: supramolecular aggregation through weak C—H...O and C—H...π interactions

4-(Acetylamino)phenyl benzenesulfonate

2-Naphthyl benzenesulfonate

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