4-(5-Chloro­penta­namido)­benzene­sulfonamide

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

doi:10.1107/S1600536812048118

Volume 68
Part 12
Pages o3475-o3476
December 2012

Received 20 November 2012
Accepted 22 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R = 0.065
wR = 0.169
Data-to-parameter ratio = 23.5
Details

4-(5-Chloropentanamido)benzenesulfonamide

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

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

The molecular conformation of the title compound, C₁₁H₁₅ClN₂O₃S, is stabilized by a C-HO hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by two pairs of inversion-related N-HO hydrogen bonds, generating R₂²(8) and R₂²(20) ring motifs, resulting in chains running along [0-11]. These chains are connected by N-HO hydrogen bonds along [100], forming layers parallel to (011). There are also C-H [pi] interactions between the layers, which consolidate the three-dimensional structure.

Related literature

Sulfonamides represent an important class of biologically active compounds. For their action as inhibitors of carbonic anhydrase enzyme, their antibacterial properties in chemotherapy, as antithyroid drugs, and for their antimicrobial properties, see: Maren (1987); Supuran (2008); Turkmen et al. (2005, 2011); Rami et al. (2011). For their antiviral properties, such as HIV protease inhibitors, see: De Clercq (2001) and as inhibitors of cysteine protease enzyme, see: Danial & Korsmeyer (2004). For related structures, see: Yalçin et al. (2012); Akkurt et al. (2010a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₁H₁₅ClN₂O₃S
M_r = 290.77
Triclinic, $[P \overline 1]$
a = 8.4872 (1) Å
b = 8.7730 (2) Å
c = 10.4572 (3) Å
= 73.711 (4)°
= 85.281 (4)°
= 63.393 (3)°
V = 667.37 (3) Å³
Z = 2
Mo K radiation
= 0.44 mm^-1
T = 294 K
0.24 × 0.15 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.901, T_max = 0.949
20164 measured reflections
4036 independent reflections
2815 reflections with I > 2(I)
R_int = 0.068

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.169
S = 1.05
4036 reflections
172 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.42 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
C5-H5O3	0.93	2.25	2.809 (4)	118
N1-H1NAO3ⁱ	0.87 (2)	1.99 (3)	2.865 (3)	176 (3)
N1-H1NBO1ⁱⁱ	0.87 (3)	2.11 (2)	2.963 (3)	166 (4)
N2-H2NO2ⁱⁱⁱ	0.88 (3)	2.17 (3)	3.021 (4)	166 (3)
C10-H10ACg1^iv	0.97	2.96	3.771 (3)	142
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y, -z+2; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1.

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: SU2531 ).

Acknowledgements

The authors thank the Unit of Scientific Research Projects of Harran University, Turkey for a research grant (HUBAK Project Nos. 295 and 1136).

References

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organic compounds