N,N-Diethyl-2-(4-methyl­benzene­sulfonamido)­benzamide

Altamura, M.; Fedi, V.; Nannicini, R.; Paoli, P.; Rossi, P.

doi:10.1107/S160053681204264X

Volume 68
Part 11
Pages o3144-o3145
November 2012

Received 20 September 2012
Accepted 11 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.118
Data-to-parameter ratio = 17.0
Details

N,N-Diethyl-2-(4-methylbenzenesulfonamido)benzamide

Maria Altamura,^a Valentina Fedi,^a Rossano Nannicini,^a Paola Paoli ^b ^* and Patrizia Rossi ^b

^aChemistry Department, Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy, and ^bDip. Energetica "Sergio Stecco", University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
Correspondence e-mail: paolapaoli@unifi.it

The asymmetric unit of the title compound, C₁₈H₂₂N₂O₃S, contains two molecules, exhibiting similar conformations [C-S-N-C torsion angles of -82.2 (2) and -70.4 (2)°, and dihedral angles between the mean planes of the aromatic rings of 56.6 (6) and 51.6 (6)° in molecules I and II, respectively]. However, the two independent molecules show distinctly different hydrogen-bonding patterns. In the crystal, molecules I form inversion dimers via pairs of N-HO hydrogen bonds, whereas for molecules II the N-HO hydrogen bond is intramolecular. The hydrogen-bonded dimers of I further propagate along the b-axis direction through [pi] - [pi] interactions [the distance between ring centroids is 3.8424 (8) Å].

Related literature

For the synthesis of the title compound, see: Bakker et al. (1997); Kaul et al. (2002). For the biological activity of compounds having the sulfonamide -SO₂NH- group, see: Lu & Tucker (2007); Tappe et al. (2008); Chegwidden et al. (2000); Purushottamachar et al. (2008). For structural and conformational studies of molecules featuring the sulfonamide moiety, see: Parkin et al. (2008); Perlovich et al. (2009, 2011); Altamura et al. (2009); Vega-Hissi et al. (2011).

Experimental

Crystal data

C₁₈H₂₂N₂O₃S
M_r = 346.43
Triclinic, $[P \overline 1]$
a = 9.4674 (6) Å
b = 12.2882 (9) Å
c = 16.0569 (12) Å
= 108.426 (7)°
= 97.357 (6)°
= 100.245 (6)°
V = 1709.7 (2) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 150 K
0.54 × 0.43 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer
Absorption correction: multi-scan (ABSPACK in CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.894, T_max = 1.000
17890 measured reflections
7512 independent reflections
4728 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.118
S = 0.96
7512 reflections
441 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.42 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1'-HN1'O3'	0.81 (2)	2.15 (2)	2.809 (2)	139 (2)
N1-HN1O3ⁱ	0.86 (2)	2.15 (2)	2.969 (2)	159 (2)
Symmetry code: (i) -x+2, -y, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2075 ).

Acknowledgements

The authors acknowledge the CRIST (Centro di Cristallografia Strutturale, University of Firenze), where the data collection was performed.

References

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organic compounds