N-[4-(4-Chloro-benzene-sulfonamido)-phenyl-sulfon-yl]acetamide.

In the title compound, C(14)H(13)ClN(2)O(5)S(2), the dihedral angles between the central benzene ring and the pendant chloro-benzene ring and the N-acetyl group are 82.35 (5) and 79.71 (6)°, respectively, and the overall conformation of the mol-ecule approximates to a U shape. Both the C-S-N-C conformations are gauche, but with opposite senses [torsion angles = -59.29 (15) and 63.68 (16)°]. An intra-molecular C-H⋯O inter-action generates an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(20) loops. A second N-H⋯O hydrogen bond links the dimers into (101) layers.

Related literature

For related structures, see: Ashfaq et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C14H13ClN2O5S2

M = 388.83

Monoclinic,

a = 9.7452 (2) Å

b = 9.9905 (2) Å

c = 17.3968 (3) Å

β = 99.870 (1)°

V = 1668.67 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 296 K

0.40 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.823, T max = 0.951

15966 measured reflections

4146 independent reflections

3267 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.03

4146 reflections

226 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023434/su2434sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023434/su2434Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023434/su2434Isup3.cml

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

C14H13ClN2O5S2	F(000) = 800
Mr = 388.83	Dx = 1.548 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5590 reflections
a = 9.7452 (2) Å	θ = 2.4–28.1°
b = 9.9905 (2) Å	µ = 0.51 mm−1
c = 17.3968 (3) Å	T = 296 K
β = 99.870 (1)°	Block, colourless
V = 1668.67 (6) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	4146 independent reflections
Radiation source: fine-focus sealed tube	3267 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.823, Tmax = 0.951	k = −13→13
15966 measured reflections	l = −21→23

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)] = 0.034	Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.5555P] where P = (Fo2 + 2Fc2)/3
4146 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
C1	0.20974 (17)	0.33396 (16)	0.55613 (9)	0.0306 (3)
C2	0.18774 (18)	0.44608 (18)	0.50941 (10)	0.0368 (4)
H2A	0.1078	0.4530	0.4718	0.044*
C3	0.2851 (2)	0.54835 (18)	0.51874 (11)	0.0415 (4)
H3	0.2711	0.6248	0.4879	0.050*
C4	0.40247 (19)	0.53498 (18)	0.57432 (11)	0.0402 (4)
C5	0.4280 (2)	0.4213 (2)	0.62017 (11)	0.0449 (5)
H5	0.5095	0.4135	0.6566	0.054*
C6	0.33066 (19)	0.31992 (19)	0.61088 (10)	0.0393 (4)
H6	0.3458	0.2427	0.6410	0.047*
C7	0.21126 (16)	0.06282 (15)	0.44896 (9)	0.0274 (3)
C8	0.30854 (19)	−0.03793 (17)	0.44559 (10)	0.0372 (4)
H8	0.3333	−0.0950	0.4879	0.045*
C9	0.3684 (2)	−0.05378 (18)	0.38001 (11)	0.0404 (4)
H9	0.4333	−0.1213	0.3779	0.048*
C10	0.33119 (17)	0.03193 (16)	0.31703 (9)	0.0315 (3)
C11	0.23330 (18)	0.13100 (17)	0.31958 (10)	0.0335 (4)
H11	0.2084	0.1875	0.2770	0.040*
C12	0.17231 (17)	0.14656 (17)	0.38490 (9)	0.0332 (4)
H12	0.1055	0.2126	0.3862	0.040*
C13	0.65205 (18)	0.12228 (19)	0.30551 (10)	0.0363 (4)
C14	0.7580 (2)	0.2294 (2)	0.30576 (12)	0.0545 (5)
H14A	0.7909	0.2578	0.3584	0.082*
H14B	0.7170	0.3041	0.2755	0.082*
H14C	0.8347	0.1955	0.2835	0.082*
N1	0.15644 (15)	0.07329 (14)	0.51825 (8)	0.0311 (3)
H1	0.202 (2)	0.029 (2)	0.5560 (13)	0.050 (6)*
N2	0.53926 (15)	0.12827 (16)	0.24656 (8)	0.0345 (3)
H2	0.531 (2)	0.191 (2)	0.2111 (12)	0.046 (6)*
O1	0.06025 (14)	0.17153 (13)	0.62438 (7)	0.0432 (3)
O2	−0.03065 (12)	0.24552 (13)	0.48970 (7)	0.0414 (3)
O3	0.46830 (16)	−0.11310 (14)	0.23297 (9)	0.0538 (4)
O4	0.31838 (14)	0.06823 (17)	0.16787 (7)	0.0557 (4)
O5	0.66166 (14)	0.03331 (15)	0.35379 (8)	0.0496 (3)
S1	0.08358 (4)	0.20587 (4)	0.54746 (2)	0.03105 (11)
S2	0.41012 (5)	0.01756 (5)	0.23429 (2)	0.03680 (12)
Cl1	0.52276 (6)	0.66492 (5)	0.58794 (4)	0.06056 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0309 (8)	0.0310 (8)	0.0301 (8)	0.0009 (6)	0.0061 (7)	−0.0060 (6)
C2	0.0343 (9)	0.0359 (9)	0.0386 (9)	0.0022 (7)	0.0018 (7)	−0.0008 (7)
C3	0.0452 (10)	0.0318 (9)	0.0481 (11)	0.0008 (8)	0.0099 (8)	0.0002 (8)
C4	0.0373 (10)	0.0349 (9)	0.0499 (11)	−0.0063 (7)	0.0119 (8)	−0.0139 (8)
C5	0.0354 (10)	0.0495 (11)	0.0452 (11)	−0.0022 (8)	−0.0062 (8)	−0.0064 (8)
C6	0.0397 (10)	0.0391 (9)	0.0368 (9)	0.0019 (8)	−0.0002 (8)	0.0023 (7)
C7	0.0270 (8)	0.0265 (7)	0.0285 (8)	−0.0034 (6)	0.0041 (6)	−0.0032 (6)
C8	0.0440 (10)	0.0324 (9)	0.0369 (9)	0.0080 (8)	0.0118 (8)	0.0081 (7)
C9	0.0444 (10)	0.0335 (9)	0.0462 (10)	0.0103 (8)	0.0160 (8)	0.0034 (7)
C10	0.0316 (8)	0.0331 (8)	0.0305 (8)	−0.0031 (7)	0.0075 (7)	−0.0047 (6)
C11	0.0358 (9)	0.0357 (9)	0.0276 (8)	0.0016 (7)	0.0013 (7)	0.0011 (7)
C12	0.0319 (9)	0.0347 (9)	0.0322 (8)	0.0064 (7)	0.0028 (7)	−0.0001 (7)
C13	0.0341 (9)	0.0478 (10)	0.0278 (8)	−0.0007 (8)	0.0072 (7)	−0.0003 (7)
C14	0.0464 (12)	0.0745 (15)	0.0419 (11)	−0.0209 (11)	0.0057 (9)	−0.0011 (10)
N1	0.0337 (8)	0.0299 (7)	0.0298 (7)	0.0027 (6)	0.0062 (6)	0.0004 (6)
N2	0.0376 (8)	0.0401 (8)	0.0254 (7)	−0.0053 (6)	0.0040 (6)	0.0051 (6)
O1	0.0490 (8)	0.0476 (7)	0.0375 (7)	−0.0043 (6)	0.0200 (6)	−0.0056 (6)
O2	0.0283 (6)	0.0455 (7)	0.0485 (7)	0.0045 (5)	0.0015 (5)	−0.0062 (6)
O3	0.0631 (10)	0.0419 (8)	0.0630 (9)	−0.0060 (7)	0.0300 (7)	−0.0204 (7)
O4	0.0457 (8)	0.0911 (12)	0.0276 (7)	−0.0079 (8)	−0.0012 (6)	−0.0068 (7)
O5	0.0469 (8)	0.0599 (9)	0.0397 (7)	0.0029 (7)	0.0007 (6)	0.0163 (6)
S1	0.0282 (2)	0.0340 (2)	0.0318 (2)	0.00023 (16)	0.00766 (16)	−0.00486 (16)
S2	0.0377 (2)	0.0439 (3)	0.0297 (2)	−0.00666 (19)	0.00829 (17)	−0.01026 (17)
Cl1	0.0523 (3)	0.0466 (3)	0.0847 (4)	−0.0174 (2)	0.0175 (3)	−0.0224 (3)

C1—C2	1.379 (2)	C10—C11	1.381 (2)
C1—C6	1.389 (2)	C10—S2	1.7504 (16)
C1—S1	1.7630 (17)	C11—C12	1.379 (2)
C2—C3	1.385 (3)	C11—H11	0.9300
C2—H2A	0.9300	C12—H12	0.9300
C3—C4	1.372 (3)	C13—O5	1.215 (2)
C3—H3	0.9300	C13—N2	1.370 (2)
C4—C5	1.386 (3)	C13—C14	1.487 (3)
C4—Cl1	1.7380 (18)	C14—H14A	0.9600
C5—C6	1.378 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	N1—S1	1.6249 (14)
C7—C8	1.391 (2)	N1—H1	0.85 (2)
C7—C12	1.393 (2)	N2—S2	1.6615 (15)
C7—N1	1.404 (2)	N2—H2	0.87 (2)
C8—C9	1.377 (2)	O1—S1	1.4369 (13)
C8—H8	0.9300	O2—S1	1.4220 (13)
C9—C10	1.389 (2)	O3—S2	1.4249 (15)
C9—H9	0.9300	O4—S2	1.4270 (15)
C2—C1—C6	120.93 (16)	C10—C11—H11	119.8
C2—C1—S1	120.23 (13)	C11—C12—C7	119.66 (15)
C6—C1—S1	118.84 (13)	C11—C12—H12	120.2
C1—C2—C3	119.74 (17)	C7—C12—H12	120.2
C1—C2—H2A	120.1	O5—C13—N2	120.40 (17)
C3—C2—H2A	120.1	O5—C13—C14	123.58 (17)
C4—C3—C2	118.85 (17)	N2—C13—C14	116.01 (16)
C4—C3—H3	120.6	C13—C14—H14A	109.5
C2—C3—H3	120.6	C13—C14—H14B	109.5
C3—C4—C5	122.09 (17)	H14A—C14—H14B	109.5
C3—C4—Cl1	119.00 (15)	C13—C14—H14C	109.5
C5—C4—Cl1	118.91 (15)	H14A—C14—H14C	109.5
C6—C5—C4	118.85 (17)	H14B—C14—H14C	109.5
C6—C5—H5	120.6	C7—N1—S1	125.47 (12)
C4—C5—H5	120.6	C7—N1—H1	113.3 (15)
C5—C6—C1	119.49 (17)	S1—N1—H1	112.5 (15)
C5—C6—H6	120.3	C13—N2—S2	124.05 (13)
C1—C6—H6	120.3	C13—N2—H2	121.7 (14)
C8—C7—C12	119.68 (14)	S2—N2—H2	114.3 (14)
C8—C7—N1	116.91 (14)	O2—S1—O1	119.66 (8)
C12—C7—N1	123.41 (14)	O2—S1—N1	109.71 (8)
C9—C8—C7	120.46 (16)	O1—S1—N1	104.12 (8)
C9—C8—H8	119.8	O2—S1—C1	107.95 (8)
C7—C8—H8	119.8	O1—S1—C1	108.23 (8)
C8—C9—C10	119.48 (16)	N1—S1—C1	106.43 (7)
C8—C9—H9	120.3	O3—S2—O4	120.51 (9)
C10—C9—H9	120.3	O3—S2—N2	108.49 (8)
C11—C10—C9	120.35 (15)	O4—S2—N2	102.91 (8)
C11—C10—S2	119.25 (13)	O3—S2—C10	108.70 (8)
C9—C10—S2	120.39 (13)	O4—S2—C10	109.52 (8)
C12—C11—C10	120.35 (16)	N2—S2—C10	105.64 (8)
C12—C11—H11	119.8
C6—C1—C2—C3	−2.2 (3)	C12—C7—N1—S1	−21.5 (2)
S1—C1—C2—C3	177.56 (13)	O5—C13—N2—S2	−1.1 (3)
C1—C2—C3—C4	0.5 (3)	C14—C13—N2—S2	178.90 (14)
C2—C3—C4—C5	1.4 (3)	C7—N1—S1—O2	57.26 (15)
C2—C3—C4—Cl1	−178.37 (14)	C7—N1—S1—O1	−173.53 (13)
C3—C4—C5—C6	−1.6 (3)	C7—N1—S1—C1	−59.29 (15)
Cl1—C4—C5—C6	178.15 (14)	C2—C1—S1—O2	−1.39 (16)
C4—C5—C6—C1	0.0 (3)	C6—C1—S1—O2	178.34 (13)
C2—C1—C6—C5	1.9 (3)	C2—C1—S1—O1	−132.27 (14)
S1—C1—C6—C5	−177.80 (14)	C6—C1—S1—O1	47.46 (16)
C12—C7—C8—C9	1.2 (3)	C2—C1—S1—N1	116.33 (14)
N1—C7—C8—C9	−179.22 (16)	C6—C1—S1—N1	−63.94 (15)
C7—C8—C9—C10	0.1 (3)	C13—N2—S2—O3	−52.72 (16)
C8—C9—C10—C11	−1.0 (3)	C13—N2—S2—O4	178.53 (15)
C8—C9—C10—S2	177.83 (14)	C13—N2—S2—C10	63.68 (16)
C9—C10—C11—C12	0.5 (3)	C11—C10—S2—O3	−160.62 (14)
S2—C10—C11—C12	−178.32 (13)	C9—C10—S2—O3	20.54 (17)
C10—C11—C12—C7	0.8 (3)	C11—C10—S2—O4	−27.10 (16)
C8—C7—C12—C11	−1.7 (2)	C9—C10—S2—O4	154.06 (15)
N1—C7—C12—C11	178.78 (15)	C11—C10—S2—N2	83.11 (15)
C8—C7—N1—S1	159.00 (13)	C9—C10—S2—N2	−95.73 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5i	0.85 (2)	1.97 (2)	2.8070 (19)	166 (2)
N2—H2···O1ii	0.87 (2)	2.10 (2)	2.9510 (19)	166.3 (19)
C12—H12···O2	0.93	2.44	3.074 (2)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5i	0.85 (2)	1.97 (2)	2.8070 (19)	166 (2)
N2—H2⋯O1ii	0.87 (2)	2.10 (2)	2.9510 (19)	166.3 (19)
C12—H12⋯O2	0.93	2.44	3.074 (2)	126

Symmetry codes: (i) ; (ii) .