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Volume 69 
Part 8 
Pages o1357-o1358  
August 2013  

Received 28 May 2013
Accepted 24 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.072
Data-to-parameter ratio = 9.7
Details
Open access

Quinoline-2-sulfonamide

aDepartment of Organic Chemistry, The Medical University of Silesia, Jagiellonska 4, 41-200 Sosnowiec, Poland, and bInstitute of Physics, University of Silesia, Uniwersytecka 4, 40-007 Katowice, Poland
Correspondence e-mail: kmarciniec@sum.edu.pl

In the title compound, C9H8N2O2S, the sulfamoyl -NH2 group is involved in intermolecular hydrogen bonding with the sulfonamide O and quinoline N atoms. In the crystal, molecules are linked into dimers via pairs of N-H...N hydrogen bonds, forming an R22(10) motif. The dimers are further assembled into chains parallel to the b axis through N-H...O hydrogen bonds, generating a C(4) motif. The crystal packing is additionally stabilized by intermolecular C-H...O interactions. The crystal studied was a non-merohedral twin with a domain ratio of 0.938 (2):0.062 (2). Density functional theory (DFT) calculations, at the B3LYP/6-31 G(d,p) level of theory, were used to optimize the molecular structure and to determine interaction energies for the title compound. The resulting interaction energy is ~4.4 kcal mol-1 per bridge for the C(4) chain and ~5.9 kcal mol-1 per bridge for the R22(10) motif.

Related literature

For the use of the quinolinesulfamoyl unit in medicinal chemistry, see: Kim et al. (2005[Kim, Y.-H., Shin, K.-J., Lee, T. G., Kim, E., Lee, M.-S., Ryu, S. H. & Suh, P.-G. (2005). Biochem. Pharmacol. 69, 1333-1341.]); Zajdel et al. (2012[Zajdel, P., Marciniec, K., Maslankiewicz, A., Satala, G., Duszynska, B., Bojarski, A. J., Partyka, A., Jastrzebska-Wiesek, M., Wróbel, D., Wesolowska, A. & Pawlowski, M. (2012). Bioorg. Med. Chem. 20, 1545-1556.], 2013[Zajdel, P., Marciniec, K., Grychowska, K., Maslankiewicz, A., Satala, G., Duszynska, B., Siwek, A., Nowak, G., Partyka, A., Wróbel, D., Jastrzebska-Wiesek, M., Bojarski, A. J., Wesolowska, A. & Pawlowski, M. (2013). Eur. J. Med. Chem. 60, 42-50.]). For related structures, see: Marciniec et al. (2012[Marciniec, K., Maslankiewicz, A., Nowak, M. & Kusz, J. (2012). Acta Cryst. E68, o2826.]). For the synthesis, see: Maslankiewicz et al. (2007[Maslankiewicz, A., Marciniec, K., Pawlowski, M. & Zajdel, P. (2007). Heterocycles, 71, 1975-1990.]). For hydrogen-bonding motifs in sufonamides, see: Adsmond & Grant (2001[Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.]). For graph-set notation of hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For general hydrogen-bond rules, see: Donohue (1952[Donohue, J. (1952). J. Phys. Chem. 56, 502-510.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]). For details of theoretical calculations, see: Frisch et al. (2009[Frisch, M. J., et al. (2009). GAUSSIAN09. Gaussian, Inc., Wallingford, CT, USA.]4); Parr & Yang (1989[Parr, R. G. & Yang, W. (1989). In Density Functional Theory of Atoms and Molecules. New York: Oxford University Press Inc.]). The twin matrix was been determined with ROTAX (Cooper et al., 2002[Cooper, R. I., Gould, R. O., Parsons, S. & Watkin, D. J. (2002). J. Appl. Cryst. 35, 168-174.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8N2O2S

  • Mr = 208.23

  • Monoclinic, P 21 /c

  • a = 8.5907 (1) Å

  • b = 5.1716 (1) Å

  • c = 20.0375 (3) Å

  • [beta] = 94.230 (1)°

  • V = 887.79 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 100 K

  • 0.27 × 0.23 × 0.05 mm

Data collection
  • Agilent SuperNova diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.919, Tmax = 1.000

  • 27311 measured reflections

  • 1552 independent reflections

  • 1530 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.072

  • S = 1.12

  • 1552 reflections

  • 160 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.35 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
N2-H2N2...O1i 0.84 (3) 2.09 (3) 2.922 (2) 171 (2)
N2-H1N2...N1ii 0.80 (3) 2.18 (3) 2.962 (2) 165 (2)
C6-H6...O1iii 0.93 (2) 2.66 (2) 3.431 (2) 141.5 (18)
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2577 ).


Acknowledgements

This research was supported in part by the Medical University of Silesia, grant No. KNW-1-006/P/2/0, and by PL-Grid Infrastructure, grant ID: plggkrzmarci1.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Cooper, R. I., Gould, R. O., Parsons, S. & Watkin, D. J. (2002). J. Appl. Cryst. 35, 168-174.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Donohue, J. (1952). J. Phys. Chem. 56, 502-510.  [CrossRef] [ChemPort] [Web of Science]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Frisch, M. J., et al. (2009). GAUSSIAN09. Gaussian, Inc., Wallingford, CT, USA.
Kim, Y.-H., Shin, K.-J., Lee, T. G., Kim, E., Lee, M.-S., Ryu, S. H. & Suh, P.-G. (2005). Biochem. Pharmacol. 69, 1333-1341.  [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Marciniec, K., Maslankiewicz, A., Nowak, M. & Kusz, J. (2012). Acta Cryst. E68, o2826.  [CrossRef] [IUCr Journals]
Maslankiewicz, A., Marciniec, K., Pawlowski, M. & Zajdel, P. (2007). Heterocycles, 71, 1975-1990.
Parr, R. G. & Yang, W. (1989). In Density Functional Theory of Atoms and Molecules. New York: Oxford University Press Inc.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zajdel, P., Marciniec, K., Grychowska, K., Maslankiewicz, A., Satala, G., Duszynska, B., Siwek, A., Nowak, G., Partyka, A., Wróbel, D., Jastrzebska-Wiesek, M., Bojarski, A. J., Wesolowska, A. & Pawlowski, M. (2013). Eur. J. Med. Chem. 60, 42-50.  [CrossRef] [ChemPort] [PubMed]
Zajdel, P., Marciniec, K., Maslankiewicz, A., Satala, G., Duszynska, B., Bojarski, A. J., Partyka, A., Jastrzebska-Wiesek, M., Wróbel, D., Wesolowska, A. & Pawlowski, M. (2012). Bioorg. Med. Chem. 20, 1545-1556.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1357-o1358   [ doi:10.1107/S160053681302062X ]

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