4-(3-Chloro-2,2-dimethyl­propanamido)­benzene­sulfonamide

Yalçın, Ş.P.; Akkurt, M.; Durgun, M.; Türkkan, B.; Türkmen, H.

doi:10.1107/S1600536812046806

Volume 68
Part 12
Page o3430
December 2012

Received 8 November 2012
Accepted 14 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.006 Å
R = 0.084
wR = 0.231
Data-to-parameter ratio = 24.2
Details

4-(3-Chloro-2,2-dimethylpropanamido)benzenesulfonamide

Serife Pinar Yalçin,^a,^b Mehmet Akkurt,^c ^* Mustafa Durgun,^d Baki Türkkan ^d and Hasan Türkmen ^d

^aDepartment of Physics, Faculty of Arts and Sciences, Harran University, 63300 Sanliurfa, Turkey,^bCentral Research Lab, Harran University, Osmanbey Campus, 63300 Sanliurfa, Turkey,^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dDepartment of Chemistry, Faculty of Arts and Sciences, Harran University, 63300 Sanliurfa, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C₁₁H₁₅ClN₂O₃S, the 3-chloro-2,2-dimethylpropanamide and sulfonamide substituents are arranged on opposite sides of the benzene ring plane. In the crystal, molecules are linked by N-HO and C-HO hydrogen bonds, forming a three-dimensional network.

Related literature

For the antibacterial, antimicrobial and antiglaucoma activity of sulfonamides and their derivatives and for their physical properties and pharmacological applications, see: Poulsen et al. (2005); Supuran & Scozzafava (2000). For related structures, see: Akkurt et al. (2010); Idemudia et al. (2012); Asiri et al. (2012). For the synthesis, see: Türkmen et al. (2011).

Experimental

Crystal data

C₁₁H₁₅ClN₂O₃S
M_r = 290.77
Monoclinic, P 2₁ /c
a = 20.4359 (11) Å
b = 7.2437 (4) Å
c = 9.4693 (5) Å
= 98.222 (3)°
V = 1387.35 (13) Å³
Z = 4
Mo K radiation
= 0.43 mm^-1
T = 294 K
0.31 × 0.14 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: refined from F (XABS2; Parkin et al., 1995) T_min = 0.931, T_max = 0.946
4240 measured reflections
4240 independent reflections
2054 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.084
wR(F²) = 0.231
S = 1.02
4240 reflections
175 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.88 (3)	2.57 (5)	3.035 (4)	114 (4)
N1-H1NO1ⁱⁱ	0.88 (3)	2.21 (4)	3.043 (5)	160 (5)
N1-H2NO1ⁱⁱⁱ	0.88 (2)	2.10 (4)	2.921 (4)	155 (5)
N2-H3NO3^iv	0.91 (6)	2.16 (6)	3.063 (5)	173 (5)
C11-H11BO3^iv	0.97	2.44	3.391 (5)	166
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5282 ).

Acknowledgements

The authors thank the Unit of Scientific Research Projects of Harran University, Turkey for a research grant (HUBAK project Nos. 874 and 1136).

References

Akkurt, M., Yalçin, S. P., Türkmen, H. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1559-o1560.
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.
Asiri, A. M., Faidallah, H. M., Alamry, K. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2258-o2259.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Idemudia, O. G., Sadimenko, A. P., Afolayan, A. J. & Hosten, E. C. (2012). Acta Cryst. E68, o1599.
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.
Poulsen, S., Bornaghi, L. F. & Healy, P. C. (2005). Bioorg. Med. Chem. Lett. 15, 5429-5433.
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Supuran, C. T. & Scozzafava, A. (2000). Exp. Opin. Ther. Pat. 10, 575-600.
Türkmen, H., Zengin, G. & Buyukkircali, B. (2011). Bioorg. Chem. 39 114-119.

organic compounds