4-(5-Chloro-penta-namido)-benzene-sulfonamide.

The mol-ecular conformation of the title compound, C11H15ClN2O3S, is stabilized by a C-H⋯O hydrogen bond, forming an S(6) ring motif. In the crystal, mol-ecules are linked by two pairs of inversion-related N-H⋯O hydrogen bonds, generating R2(2)(8) and R2(2)(20) ring motifs, resulting in chains running along [0-11]. These chains are connected by N-H⋯O hydrogen bonds along [100], forming layers parallel to (011). There are also C-H⋯π inter-actions 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 ▶); n class="Chemical">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: Yalçın et al. (2012 ▶); Akkurt et al. (2010a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H15ClN2O3S

M = 290.77

Triclinic,

a = 8.4872 (1) Å

b = 8.7730 (2) Å

c = 10.4572 (3) Å

α = 73.711 (4)°

β = 85.281 (4)°

γ = 63.393 (3)°

V = 667.37 (3) Å3

Z = 2

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.169

S = 1.05

4036 reflections

172 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.35 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048118/su2531sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048118/su2531Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048118/su2531Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H15ClN2O3S	Z = 2
Mr = 290.77	F(000) = 304
Triclinic, P1	Dx = 1.447 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4872 (1) Å	Cell parameters from 3036 reflections
b = 8.7730 (2) Å	θ = 2.7–30.5°
c = 10.4572 (3) Å	µ = 0.44 mm−1
α = 73.711 (4)°	T = 294 K
β = 85.281 (4)°	Needle, pale yellow
γ = 63.393 (3)°	0.24 × 0.15 × 0.12 mm
V = 667.37 (3) Å3

Rigaku R-AXIS RAPID-S diffractometer	4036 independent reflections
Radiation source: Sealed Tube	2815 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.068
Detector resolution: 10.0000 pixels mm-1	θmax = 30.5°, θmin = 2.7°
dtprofit.ref scans	h = −12→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −12→12
Tmin = 0.901, Tmax = 0.949	l = −14→14
20164 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.2759P] where P = (Fo2 + 2Fc2)/3
4036 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.42 e Å−3
3 restraints	Δρmin = −0.35 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.72069 (11)	0.61911 (12)	−0.09175 (8)	0.0692 (3)
S1	−0.03920 (8)	0.03480 (8)	0.77585 (6)	0.0419 (2)
O1	0.0449 (2)	−0.1257 (2)	0.88113 (18)	0.0500 (6)
O2	−0.1417 (3)	0.0370 (3)	0.6723 (2)	0.0572 (7)
O3	0.3519 (2)	0.4839 (2)	0.35111 (19)	0.0552 (6)
N1	−0.1676 (3)	0.1842 (3)	0.8443 (2)	0.0535 (8)
N2	0.5163 (3)	0.2301 (3)	0.5050 (2)	0.0416 (6)
C1	0.1271 (3)	0.0902 (3)	0.6970 (2)	0.0398 (7)
C2	0.2959 (3)	0.0145 (3)	0.7555 (2)	0.0426 (7)
C3	0.4213 (3)	0.0629 (3)	0.6908 (2)	0.0434 (7)
C4	0.3823 (3)	0.1871 (3)	0.5670 (2)	0.0385 (7)
C5	0.2142 (4)	0.2581 (4)	0.5068 (3)	0.0586 (9)
C6	0.0901 (4)	0.2088 (4)	0.5723 (3)	0.0611 (10)
C7	0.4969 (3)	0.3716 (3)	0.4010 (2)	0.0389 (7)
C8	0.6648 (3)	0.3843 (3)	0.3549 (3)	0.0424 (7)
C9	0.6398 (3)	0.5164 (4)	0.2196 (3)	0.0479 (8)
C10	0.8041 (4)	0.5387 (4)	0.1751 (3)	0.0481 (8)
C11	0.7774 (5)	0.6762 (4)	0.0441 (3)	0.0614 (11)
H1NA	−0.226 (4)	0.288 (2)	0.788 (3)	0.0830*
H2	0.32410	−0.06880	0.83840	0.0510*
H1NB	−0.123 (4)	0.179 (5)	0.918 (2)	0.0830*
H2N	0.623 (2)	0.165 (4)	0.542 (3)	0.0830*
H3	0.53400	0.01160	0.73060	0.0520*
H5	0.18640	0.33860	0.42260	0.0700*
H6	−0.02150	0.25670	0.53150	0.0730*
H8A	0.75400	0.26840	0.35040	0.0510*
H8B	0.70720	0.41920	0.41990	0.0510*
H9A	0.60360	0.47760	0.15390	0.0570*
H9B	0.54550	0.63050	0.22290	0.0570*
H10A	0.84370	0.57130	0.24300	0.0580*
H10B	0.89650	0.42580	0.16730	0.0580*
H11A	0.88480	0.69000	0.02530	0.0740*
H11B	0.68420	0.78900	0.05110	0.0740*

	U11	U22	U33	U12	U13	U23
Cl1	0.0689 (5)	0.0792 (6)	0.0525 (4)	−0.0331 (4)	0.0030 (4)	−0.0072 (4)
S1	0.0379 (3)	0.0438 (3)	0.0432 (3)	−0.0228 (3)	−0.0011 (2)	−0.0018 (2)
O1	0.0490 (10)	0.0413 (9)	0.0534 (10)	−0.0225 (8)	−0.0011 (8)	0.0015 (8)
O2	0.0533 (11)	0.0741 (13)	0.0549 (11)	−0.0404 (10)	−0.0057 (9)	−0.0101 (10)
O3	0.0387 (10)	0.0531 (11)	0.0557 (11)	−0.0175 (9)	−0.0005 (8)	0.0077 (9)
N1	0.0487 (14)	0.0476 (13)	0.0476 (13)	−0.0144 (11)	0.0006 (11)	−0.0003 (10)
N2	0.0343 (10)	0.0437 (11)	0.0411 (11)	−0.0180 (9)	−0.0022 (8)	−0.0009 (9)
C1	0.0373 (12)	0.0411 (12)	0.0416 (12)	−0.0213 (10)	−0.0008 (10)	−0.0047 (10)
C2	0.0409 (13)	0.0424 (12)	0.0399 (12)	−0.0211 (11)	−0.0056 (10)	0.0023 (10)
C3	0.0342 (12)	0.0422 (12)	0.0455 (13)	−0.0153 (10)	−0.0078 (10)	0.0000 (10)
C4	0.0357 (12)	0.0432 (12)	0.0378 (11)	−0.0203 (10)	0.0003 (9)	−0.0076 (10)
C5	0.0488 (15)	0.0720 (18)	0.0456 (14)	−0.0362 (14)	−0.0149 (12)	0.0185 (13)
C6	0.0435 (15)	0.077 (2)	0.0528 (15)	−0.0348 (15)	−0.0160 (12)	0.0159 (14)
C7	0.0376 (12)	0.0420 (12)	0.0365 (11)	−0.0177 (10)	0.0035 (10)	−0.0101 (10)
C8	0.0365 (12)	0.0432 (12)	0.0464 (13)	−0.0186 (10)	0.0051 (10)	−0.0100 (10)
C9	0.0426 (14)	0.0565 (15)	0.0474 (14)	−0.0287 (12)	0.0048 (11)	−0.0076 (12)
C10	0.0458 (14)	0.0527 (15)	0.0517 (14)	−0.0292 (12)	0.0095 (12)	−0.0126 (12)
C11	0.0676 (19)	0.0628 (18)	0.0634 (18)	−0.0410 (16)	0.0158 (15)	−0.0143 (15)

Cl1—C11	1.797 (4)	C7—C8	1.508 (4)
S1—O1	1.4365 (18)	C8—C9	1.516 (4)
S1—O2	1.435 (2)	C9—C10	1.512 (5)
S1—N1	1.593 (2)	C10—C11	1.504 (4)
S1—C1	1.763 (3)	C2—H2	0.9300
O3—C7	1.220 (3)	C3—H3	0.9300
N2—C4	1.408 (4)	C5—H5	0.9300
N2—C7	1.356 (3)	C6—H6	0.9300
N1—H1NA	0.87 (2)	C8—H8A	0.9700
N1—H1NB	0.87 (3)	C8—H8B	0.9700
N2—H2N	0.88 (3)	C9—H9A	0.9700
C1—C2	1.390 (4)	C9—H9B	0.9700
C1—C6	1.377 (4)	C10—H10A	0.9700
C2—C3	1.377 (4)	C10—H10B	0.9700
C3—C4	1.389 (3)	C11—H11A	0.9700
C4—C5	1.397 (4)	C11—H11B	0.9700
C5—C6	1.374 (5)
O1—S1—O2	118.85 (13)	C1—C2—H2	120.00
O1—S1—N1	106.87 (11)	C3—C2—H2	120.00
O1—S1—C1	107.57 (11)	C2—C3—H3	120.00
O2—S1—N1	107.06 (14)	C4—C3—H3	119.00
O2—S1—C1	106.58 (13)	C4—C5—H5	120.00
N1—S1—C1	109.75 (13)	C6—C5—H5	120.00
C4—N2—C7	127.3 (2)	C1—C6—H6	119.00
S1—N1—H1NB	114 (3)	C5—C6—H6	119.00
H1NA—N1—H1NB	119 (3)	C7—C8—H8A	109.00
S1—N1—H1NA	114.0 (18)	C7—C8—H8B	109.00
C7—N2—H2N	115.5 (19)	C9—C8—H8A	109.00
C4—N2—H2N	116.9 (18)	C9—C8—H8B	109.00
S1—C1—C6	119.1 (2)	H8A—C8—H8B	108.00
S1—C1—C2	121.99 (17)	C8—C9—H9A	109.00
C2—C1—C6	118.9 (3)	C8—C9—H9B	109.00
C1—C2—C3	120.0 (2)	C10—C9—H9A	109.00
C2—C3—C4	121.1 (2)	C10—C9—H9B	109.00
C3—C4—C5	118.6 (3)	H9A—C9—H9B	108.00
N2—C4—C5	122.8 (2)	C9—C10—H10A	109.00
N2—C4—C3	118.6 (2)	C9—C10—H10B	109.00
C4—C5—C6	119.8 (3)	C11—C10—H10A	109.00
C1—C6—C5	121.5 (3)	C11—C10—H10B	109.00
O3—C7—C8	122.4 (2)	H10A—C10—H10B	108.00
N2—C7—C8	115.8 (2)	Cl1—C11—H11A	109.00
O3—C7—N2	121.8 (3)	Cl1—C11—H11B	109.00
C7—C8—C9	112.6 (2)	C10—C11—H11A	109.00
C8—C9—C10	113.4 (2)	C10—C11—H11B	109.00
C9—C10—C11	113.6 (3)	H11A—C11—H11B	108.00
Cl1—C11—C10	112.5 (3)
O1—S1—C1—C2	−15.8 (2)	C6—C1—C2—C3	2.2 (4)
O2—S1—C1—C2	−144.3 (2)	C1—C2—C3—C4	0.0 (4)
N1—S1—C1—C2	100.2 (2)	C2—C3—C4—N2	−179.4 (2)
O1—S1—C1—C6	162.6 (2)	C2—C3—C4—C5	−2.2 (4)
O2—S1—C1—C6	34.2 (3)	N2—C4—C5—C6	179.2 (3)
N1—S1—C1—C6	−81.5 (2)	C3—C4—C5—C6	2.1 (4)
C7—N2—C4—C3	−164.6 (2)	C4—C5—C6—C1	0.1 (5)
C7—N2—C4—C5	18.3 (4)	O3—C7—C8—C9	−16.5 (3)
C4—N2—C7—O3	2.2 (4)	N2—C7—C8—C9	165.7 (2)
C4—N2—C7—C8	180.0 (2)	C7—C8—C9—C10	176.7 (2)
S1—C1—C2—C3	−179.42 (18)	C8—C9—C10—C11	−177.1 (3)
S1—C1—C6—C5	179.3 (2)	C9—C10—C11—Cl1	−63.2 (3)
C2—C1—C6—C5	−2.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3	0.93	2.25	2.809 (4)	118
N1—H1NA···O3i	0.87 (2)	1.99 (3)	2.865 (3)	176 (3)
N1—H1NB···O1ii	0.87 (3)	2.11 (2)	2.963 (3)	166 (4)
N2—H2N···O2iii	0.88 (3)	2.17 (3)	3.021 (4)	166 (3)
C10—H10A···Cg1iv	0.97	2.96	3.771 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3	0.93	2.25	2.809 (4)	118
N1—H1NA⋯O3i	0.87 (2)	1.99 (3)	2.865 (3)	176 (3)
N1—H1NB⋯O1ii	0.87 (3)	2.11 (2)	2.963 (3)	166 (4)
N2—H2N⋯O2iii	0.88 (3)	2.17 (3)	3.021 (4)	166 (3)
C10—H10A⋯Cg1iv	0.97	2.96	3.771 (3)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .