N-[4-(p-Toluenesulfonamido)phen-ylsulfon-yl]acetamide.

In the title compound, C(15)H(16)N(2)O(5)S(2), the dihedral between the two aromatic rings is 81.33 (6)°. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers, which are further connected via N-H⋯O hydrogen bonds into a chain running along [01].

Related literature

For the synthesis and biological activity of the title compound, see: Deng & Mani (2006 ▶). For a related structure, see: Ashfaq et al. (2009 ▶).

Experimental

Crystal data

C15H16N2O5S2

M = 368.42

Monoclinic,

a = 9.8077 (4) Å

b = 10.0782 (4) Å

c = 17.3081 (7) Å

β = 100.290 (2)°

V = 1683.28 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 296 K

0.48 × 0.14 × 0.05 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.852, T max = 0.981

16294 measured reflections

3715 independent reflections

2787 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.114

S = 1.02

3715 reflections

225 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.31 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055706/bt5152sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055706/bt5152Isup2.hkl

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

C15H16N2O5S2	F(000) = 768
Mr = 368.42	Dx = 1.454 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4606 reflections
a = 9.8077 (4) Å	θ = 2.4–26.8°
b = 10.0782 (4) Å	µ = 0.34 mm−1
c = 17.3081 (7) Å	T = 296 K
β = 100.290 (2)°	Needle, red
V = 1683.28 (12) Å3	0.48 × 0.14 × 0.05 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3715 independent reflections
Radiation source: fine-focus sealed tube	2787 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 27.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→12
Tmin = 0.852, Tmax = 0.981	k = −12→12
16294 measured reflections	l = −22→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.5119P] where P = (Fo2 + 2Fc2)/3
3715 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.58372 (5)	0.79324 (5)	1.04610 (3)	0.03142 (15)
S2	0.91252 (5)	0.97819 (6)	0.73350 (3)	0.03660 (16)
O1	0.55834 (15)	0.82933 (16)	1.12253 (9)	0.0429 (4)
O2	0.47119 (14)	0.75141 (16)	0.98763 (9)	0.0422 (4)
O3	0.82154 (16)	0.9285 (2)	0.66630 (9)	0.0553 (5)
O4	0.96901 (18)	1.10836 (16)	0.73294 (11)	0.0532 (5)
O5	1.16225 (16)	0.96040 (18)	0.85525 (9)	0.0501 (4)
N1	0.65425 (17)	0.92526 (18)	1.01581 (10)	0.0315 (4)
H1N	0.693 (2)	0.971 (2)	1.0518 (14)	0.038*
N2	1.04204 (18)	0.86957 (19)	0.74560 (10)	0.0341 (4)
H2N	1.034 (2)	0.811 (2)	0.7122 (14)	0.041*
C1	0.9121 (2)	0.4715 (2)	1.08120 (15)	0.0427 (5)
C2	0.9326 (2)	0.5914 (2)	1.12183 (15)	0.0470 (6)
H2	1.0146	0.6052	1.1572	0.056*
C3	0.8338 (2)	0.6893 (2)	1.11050 (13)	0.0413 (5)
H3	0.8485	0.7686	1.1382	0.050*
C4	0.7115 (2)	0.6690 (2)	1.05720 (12)	0.0316 (4)
C5	0.6907 (2)	0.5522 (2)	1.01500 (13)	0.0382 (5)
H5	0.6100	0.5395	0.9784	0.046*
C6	0.7907 (2)	0.4546 (2)	1.02772 (15)	0.0436 (5)
H6	0.7761	0.3756	0.9997	0.052*
C7	0.71121 (19)	0.93381 (19)	0.94715 (11)	0.0278 (4)
C8	0.8064 (2)	1.0347 (2)	0.94356 (13)	0.0404 (5)
H8	0.8291	1.0927	0.9856	0.048*
C9	0.8672 (2)	1.0495 (2)	0.87847 (14)	0.0422 (5)
H9	0.9305	1.1176	0.8764	0.051*
C10	0.83393 (19)	0.9629 (2)	0.81628 (12)	0.0306 (4)
C11	0.7379 (2)	0.8629 (2)	0.81853 (12)	0.0330 (5)
H11	0.7152	0.8055	0.7761	0.040*
C12	0.6760 (2)	0.8483 (2)	0.88342 (12)	0.0326 (5)
H12	0.6110	0.7815	0.8847	0.039*
C13	1.1547 (2)	0.8753 (2)	0.80521 (12)	0.0354 (5)
C14	1.2619 (3)	0.7714 (3)	0.80379 (15)	0.0567 (7)
H14A	1.3395	0.8090	0.7847	0.085*
H14B	1.2234	0.7003	0.7698	0.085*
H14C	1.2921	0.7377	0.8559	0.085*
C15	1.0205 (3)	0.3644 (3)	1.09553 (19)	0.0622 (8)
H15A	1.1045	0.3959	1.0806	0.093*
H15B	0.9882	0.2876	1.0649	0.093*
H15C	1.0381	0.3414	1.1502	0.093*

	U11	U22	U33	U12	U13	U23
S1	0.0265 (2)	0.0369 (3)	0.0317 (3)	−0.0007 (2)	0.00741 (19)	0.0050 (2)
S2	0.0365 (3)	0.0453 (3)	0.0291 (3)	0.0072 (2)	0.0089 (2)	0.0104 (2)
O1	0.0458 (9)	0.0506 (10)	0.0363 (9)	0.0046 (7)	0.0186 (7)	0.0054 (7)
O2	0.0288 (7)	0.0490 (9)	0.0467 (9)	−0.0064 (7)	0.0012 (7)	0.0068 (7)
O3	0.0435 (9)	0.0934 (14)	0.0263 (8)	0.0096 (9)	−0.0005 (7)	0.0080 (9)
O4	0.0615 (11)	0.0412 (9)	0.0638 (11)	0.0059 (8)	0.0301 (9)	0.0200 (9)
O5	0.0470 (9)	0.0621 (11)	0.0386 (9)	−0.0020 (8)	0.0001 (7)	−0.0165 (8)
N1	0.0343 (9)	0.0320 (10)	0.0286 (9)	−0.0029 (7)	0.0069 (7)	−0.0014 (7)
N2	0.0366 (9)	0.0396 (11)	0.0259 (9)	0.0044 (8)	0.0051 (7)	−0.0057 (8)
C1	0.0388 (12)	0.0384 (13)	0.0519 (14)	0.0012 (10)	0.0107 (10)	0.0152 (11)
C2	0.0344 (11)	0.0510 (15)	0.0502 (15)	0.0006 (10)	−0.0070 (10)	0.0055 (12)
C3	0.0388 (12)	0.0413 (13)	0.0412 (13)	−0.0034 (10)	0.0004 (9)	−0.0022 (10)
C4	0.0293 (10)	0.0340 (11)	0.0314 (11)	−0.0024 (8)	0.0054 (8)	0.0043 (9)
C5	0.0334 (11)	0.0390 (12)	0.0408 (12)	−0.0047 (9)	0.0024 (9)	0.0011 (10)
C6	0.0458 (13)	0.0312 (12)	0.0541 (15)	−0.0019 (10)	0.0095 (11)	−0.0002 (11)
C7	0.0261 (9)	0.0279 (10)	0.0294 (10)	0.0036 (8)	0.0048 (7)	0.0034 (8)
C8	0.0468 (12)	0.0374 (12)	0.0399 (13)	−0.0130 (10)	0.0157 (10)	−0.0106 (10)
C9	0.0472 (12)	0.0362 (12)	0.0474 (14)	−0.0133 (10)	0.0203 (10)	−0.0059 (10)
C10	0.0299 (10)	0.0337 (11)	0.0290 (10)	0.0040 (8)	0.0077 (8)	0.0049 (9)
C11	0.0343 (10)	0.0363 (12)	0.0270 (10)	−0.0003 (9)	0.0014 (8)	−0.0019 (9)
C12	0.0298 (10)	0.0345 (11)	0.0328 (11)	−0.0069 (8)	0.0035 (8)	−0.0002 (9)
C13	0.0328 (10)	0.0478 (13)	0.0260 (11)	0.0016 (9)	0.0069 (8)	0.0010 (10)
C14	0.0453 (14)	0.080 (2)	0.0434 (14)	0.0217 (13)	0.0050 (11)	−0.0013 (13)
C15	0.0514 (15)	0.0450 (15)	0.092 (2)	0.0109 (12)	0.0188 (14)	0.0226 (15)

S1—O2	1.4215 (15)	C5—C6	1.379 (3)
S1—O1	1.4359 (15)	C5—H5	0.9300
S1—N1	1.6289 (18)	C6—H6	0.9300
S1—C4	1.758 (2)	C7—C8	1.389 (3)
S2—O3	1.4244 (17)	C7—C12	1.394 (3)
S2—O4	1.4247 (18)	C8—C9	1.374 (3)
S2—N2	1.6615 (18)	C8—H8	0.9300
S2—C10	1.751 (2)	C9—C10	1.379 (3)
O5—C13	1.211 (3)	C9—H9	0.9300
N1—C7	1.403 (2)	C10—C11	1.385 (3)
N1—H1N	0.81 (2)	C11—C12	1.377 (3)
N2—C13	1.372 (3)	C11—H11	0.9300
N2—H2N	0.82 (2)	C12—H12	0.9300
C1—C6	1.382 (3)	C13—C14	1.488 (3)
C1—C2	1.394 (4)	C14—H14A	0.9600
C1—C15	1.504 (3)	C14—H14B	0.9600
C2—C3	1.372 (3)	C14—H14C	0.9600
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.392 (3)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.381 (3)
O2—S1—O1	119.38 (9)	C1—C6—H6	119.3
O2—S1—N1	109.48 (9)	C8—C7—C12	119.38 (18)
O1—S1—N1	104.07 (9)	C8—C7—N1	117.08 (18)
O2—S1—C4	108.32 (10)	C12—C7—N1	123.53 (18)
O1—S1—C4	108.50 (9)	C9—C8—C7	120.7 (2)
N1—S1—C4	106.35 (9)	C9—C8—H8	119.7
O3—S2—O4	120.38 (11)	C7—C8—H8	119.7
O3—S2—N2	102.99 (10)	C8—C9—C10	119.6 (2)
O4—S2—N2	108.54 (10)	C8—C9—H9	120.2
O3—S2—C10	109.52 (10)	C10—C9—H9	120.2
O4—S2—C10	108.37 (10)	C9—C10—C11	120.42 (19)
N2—S2—C10	106.09 (9)	C9—C10—S2	120.36 (16)
C7—N1—S1	125.38 (15)	C11—C10—S2	119.22 (16)
C7—N1—H1N	114.3 (17)	C12—C11—C10	120.14 (19)
S1—N1—H1N	112.5 (17)	C12—C11—H11	119.9
C13—N2—S2	124.19 (16)	C10—C11—H11	119.9
C13—N2—H2N	121.9 (17)	C11—C12—C7	119.76 (19)
S2—N2—H2N	113.9 (17)	C11—C12—H12	120.1
C6—C1—C2	118.3 (2)	C7—C12—H12	120.1
C6—C1—C15	121.4 (2)	O5—C13—N2	120.4 (2)
C2—C1—C15	120.3 (2)	O5—C13—C14	123.8 (2)
C3—C2—C1	121.1 (2)	N2—C13—C14	115.8 (2)
C3—C2—H2	119.5	C13—C14—H14A	109.5
C1—C2—H2	119.5	C13—C14—H14B	109.5
C2—C3—C4	119.5 (2)	H14A—C14—H14B	109.5
C2—C3—H3	120.2	C13—C14—H14C	109.5
C4—C3—H3	120.2	H14A—C14—H14C	109.5
C5—C4—C3	120.3 (2)	H14B—C14—H14C	109.5
C5—C4—S1	120.96 (16)	C1—C15—H15A	109.5
C3—C4—S1	118.77 (17)	C1—C15—H15B	109.5
C6—C5—C4	119.3 (2)	H15A—C15—H15B	109.5
C6—C5—H5	120.3	C1—C15—H15C	109.5
C4—C5—H5	120.3	H15A—C15—H15C	109.5
C5—C6—C1	121.5 (2)	H15B—C15—H15C	109.5
C5—C6—H6	119.3
O2—S1—N1—C7	−58.48 (18)	C15—C1—C6—C5	179.4 (2)
O1—S1—N1—C7	172.83 (16)	S1—N1—C7—C8	−158.64 (16)
C4—S1—N1—C7	58.34 (18)	S1—N1—C7—C12	22.1 (3)
O3—S2—N2—C13	−178.58 (18)	C12—C7—C8—C9	−0.9 (3)
O4—S2—N2—C13	52.8 (2)	N1—C7—C8—C9	179.8 (2)
C10—S2—N2—C13	−63.5 (2)	C7—C8—C9—C10	−0.3 (4)
C6—C1—C2—C3	1.4 (4)	C8—C9—C10—C11	1.2 (3)
C15—C1—C2—C3	−178.9 (2)	C8—C9—C10—S2	−178.87 (18)
C1—C2—C3—C4	−0.4 (4)	O3—S2—C10—C9	−151.90 (18)
C2—C3—C4—C5	−1.1 (3)	O4—S2—C10—C9	−18.8 (2)
C2—C3—C4—S1	177.79 (18)	N2—S2—C10—C9	97.58 (19)
O2—S1—C4—C5	−2.5 (2)	O3—S2—C10—C11	28.04 (19)
O1—S1—C4—C5	128.50 (18)	O4—S2—C10—C11	161.13 (16)
N1—S1—C4—C5	−120.07 (18)	N2—S2—C10—C11	−82.47 (17)
O2—S1—C4—C3	178.62 (17)	C9—C10—C11—C12	−0.8 (3)
O1—S1—C4—C3	−50.4 (2)	S2—C10—C11—C12	179.30 (16)
N1—S1—C4—C3	61.02 (19)	C10—C11—C12—C7	−0.5 (3)
C3—C4—C5—C6	1.7 (3)	C8—C7—C12—C11	1.3 (3)
S1—C4—C5—C6	−177.20 (17)	N1—C7—C12—C11	−179.41 (18)
C4—C5—C6—C1	−0.7 (3)	S2—N2—C13—O5	2.9 (3)
C2—C1—C6—C5	−0.8 (4)	S2—N2—C13—C14	−177.73 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5i	0.81 (2)	2.06 (2)	2.848 (2)	162 (2)
N2—H2N···O1ii	0.82 (2)	2.15 (2)	2.950 (2)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O5i	0.81 (2)	2.06 (2)	2.848 (2)	162 (2)
N2—H2N⋯O1ii	0.82 (2)	2.15 (2)	2.950 (2)	167 (2)

Symmetry codes: (i) ; (ii) .