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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 [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.118
Data-to-parameter ratio = 17.0
Details
Open access

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

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-H...O hydrogen bonds, whereas for molecules II the N-H...O 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[Bakker, W. I. I., Familoni, O. B., Padfield, J. & Snieckus, V. (1997). Synlett, 9, 1079-1080.]); Kaul et al. (2002[Kaul, S., Kumar, A., Sain, B. & Gupta, A. K. (2002). Synth. Commun. 32, 2885-2891.]). For the biological activity of compounds having the sulfonamide -SO2NH- group, see: Lu & Tucker (2007[Lu, R. J. & Tucker, J. A. (2007). J. Med. Chem. 50, 6535-6544.]); Tappe et al. (2008[Tappe, W., Zarfl, C., Kummer, S., Burauel, P., Vereecken, H. & Groeneweg, J. (2008). Chemosphere, 72, 836-843.]); Chegwidden et al. (2000[Chegwidden, W. R., Carter, N. D. & Edwards, Y. H. (2000). The Carbonic Anhydrases New Horizons. Basel: Birkhauser Verlag.]); Purushottamachar et al. (2008[Purushottamachar, P., Khandelwal, A., Vasaitis, T. S., Bruno, R. D., Gediya, L. K. & Njar, V. C. O. (2008). Bioorg. Med. Chem. 16, 3519-3529.]). For structural and conformational studies of molecules featuring the sulfonamide moiety, see: Parkin et al. (2008[Parkin, A., Collins, A., Gilmore, C. J. & Wilson, C. C. (2008). Acta Cryst. B64, 66-71.]); Perlovich et al. (2009[Perlovich, G. L., Tkachev, V. V., Strakhova, N. N., Kazachenko, V. P., Volkova, T. V., Surov, O. V., Schaper, K.-J. & Raevsky, O. A. (2009). J. Pharm. Sci. 98, 4738-4755.], 2011[Perlovich, G. L., Ryzhakov, A. M., Tkachev, T. T. & Hansen, L. K. (2011). Cryst. Growth Des. 11, 1067-1081.]); Altamura et al. (2009[Altamura, M., Fedi, V., Giannotti, D., Paoli, P. & Rossi, P. (2009). New J. Chem. 33, 2219-2231.]); Vega-Hissi et al. (2011[Vega-Hissi, E. G., Andrada, M. F., Zamarbide, G. N., Estrada, M. R. & Tomas-Vert, F. (2011). J. Mol. Model. 17, 1317-1323.]).

[Scheme 1]

Experimental

Crystal data
  • C18H22N2O3S

  • Mr = 346.43

  • Triclinic, [P \overline 1]

  • a = 9.4674 (6) Å

  • b = 12.2882 (9) Å

  • c = 16.0569 (12) Å

  • [alpha] = 108.426 (7)°

  • [beta] = 97.357 (6)°

  • [gamma] = 100.245 (6)°

  • V = 1709.7 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.894, Tmax = 1.000

  • 17890 measured reflections

  • 7512 independent reflections

  • 4728 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1'-HN1'...O3' 0.81 (2) 2.15 (2) 2.809 (2) 139 (2)
N1-HN1...O3i 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[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


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

Altamura, M., Fedi, V., Giannotti, D., Paoli, P. & Rossi, P. (2009). New J. Chem. 33, 2219-2231.  [ISI] [CSD] [CrossRef] [ChemPort]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bakker, W. I. I., Familoni, O. B., Padfield, J. & Snieckus, V. (1997). Synlett, 9, 1079-1080.  [CrossRef]
Chegwidden, W. R., Carter, N. D. & Edwards, Y. H. (2000). The Carbonic Anhydrases New Horizons. Basel: Birkhauser Verlag.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Kaul, S., Kumar, A., Sain, B. & Gupta, A. K. (2002). Synth. Commun. 32, 2885-2891.  [ISI] [CrossRef] [ChemPort]
Lu, R. J. & Tucker, J. A. (2007). J. Med. Chem. 50, 6535-6544.  [ISI] [CrossRef] [PubMed] [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Parkin, A., Collins, A., Gilmore, C. J. & Wilson, C. C. (2008). Acta Cryst. B64, 66-71.  [ISI] [CrossRef] [details]
Perlovich, G. L., Ryzhakov, A. M., Tkachev, T. T. & Hansen, L. K. (2011). Cryst. Growth Des. 11, 1067-1081.  [CrossRef] [ChemPort]
Perlovich, G. L., Tkachev, V. V., Strakhova, N. N., Kazachenko, V. P., Volkova, T. V., Surov, O. V., Schaper, K.-J. & Raevsky, O. A. (2009). J. Pharm. Sci. 98, 4738-4755.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Purushottamachar, P., Khandelwal, A., Vasaitis, T. S., Bruno, R. D., Gediya, L. K. & Njar, V. C. O. (2008). Bioorg. Med. Chem. 16, 3519-3529.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tappe, W., Zarfl, C., Kummer, S., Burauel, P., Vereecken, H. & Groeneweg, J. (2008). Chemosphere, 72, 836-843.  [ISI] [CrossRef] [PubMed] [ChemPort]
Vega-Hissi, E. G., Andrada, M. F., Zamarbide, G. N., Estrada, M. R. & Tomas-Vert, F. (2011). J. Mol. Model. 17, 1317-1323.  [ISI] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3144-o3145   [ doi:10.1107/S160053681204264X ]

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