N-[3-(Benzene-sulfonamido)-prop-yl]benzene-sulfonamide.

In the title compound, C(15)H(18)N(2)O(4)S(2), the dihedral angle between the aromatic rings is 71.8 (2)°. The conformation of the central N-C-C-C-N fragment is gauche-gauche [torsion angles = 72.5 (5) and 65.7 (5)°]. Both N atoms adopt pyramidal geometries. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating (001) sheets, and weak C-H⋯O inter-actions consolidate the packing.

Related literature

For a related structure, see: Linden & Bienz (1999 ▶).

Experimental

Crystal data

C15H18N2O4S2

M = 354.43

Orthorhombic,

a = 9.2650 (13) Å

b = 16.402 (2) Å

c = 22.740 (3) Å

V = 3455.5 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

13896 measured reflections

3393 independent reflections

1607 reflections with I > 2σ(I)

R int = 0.091

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.181

S = 1.03

3393 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.35 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/S1600536811020150/om2431sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020150/om2431Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020150/om2431Isup3.cml

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

C15H18N2O4S2	F(000) = 1488
Mr = 354.43	Dx = 1.363 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2014 reflections
a = 9.2650 (13) Å	θ = 2.6–21.2°
b = 16.402 (2) Å	µ = 0.33 mm−1
c = 22.740 (3) Å	T = 296 K
V = 3455.5 (8) Å3	Prism, colourless
Z = 8	0.40 × 0.20 × 0.20 mm

Bruker APEXII CCD diffractometer	1607 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.091
graphite	θmax = 26.0°, θmin = 2.5°
ω scans	h = −5→11
13896 measured reflections	k = −18→20
3393 independent reflections	l = −28→27

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)] = 0.069	Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F2) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0722P)2 + 0.3591P] where P = (Fo2 + 2Fc2)/3
3393 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.35 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
C1	0.1983 (7)	0.4365 (4)	0.3462 (2)	0.0749 (16)
C2	0.0703 (9)	0.4669 (4)	0.3255 (3)	0.102 (2)
H2A	0.0580	0.5230	0.3219	0.123*
C3	−0.0417 (9)	0.4144 (6)	0.3098 (3)	0.124 (3)
H3A	−0.1276	0.4354	0.2950	0.148*
C4	−0.0255 (10)	0.3346 (5)	0.3158 (3)	0.118 (3)
H4A	−0.1004	0.2997	0.3053	0.141*
C5	0.0988 (12)	0.3034 (4)	0.3372 (3)	0.118 (3)
H5	0.1090	0.2473	0.3414	0.142*
C6	0.2110 (8)	0.3546 (4)	0.3528 (3)	0.102 (2)
H6	0.2958	0.3327	0.3679	0.123*
C7	0.1906 (5)	0.5379 (3)	0.4664 (2)	0.0624 (13)
H7A	0.1191	0.4948	0.4645	0.075*
H7B	0.1539	0.5845	0.4447	0.075*
C8	0.2153 (5)	0.5616 (3)	0.5296 (2)	0.0603 (13)
H8A	0.1224	0.5666	0.5489	0.072*
H8B	0.2677	0.5179	0.5489	0.072*
C9	0.2973 (4)	0.6398 (2)	0.5381 (2)	0.0556 (12)
H9A	0.3180	0.6476	0.5795	0.067*
H9B	0.3883	0.6371	0.5171	0.067*
C10	0.3019 (4)	0.8225 (2)	0.5942 (2)	0.0490 (11)
C11	0.4299 (5)	0.7968 (3)	0.6201 (2)	0.0680 (14)
H11	0.5002	0.7705	0.5980	0.082*
C12	0.4507 (8)	0.8108 (4)	0.6785 (3)	0.096 (2)
H12	0.5355	0.7930	0.6963	0.116*
C13	0.3495 (10)	0.8504 (5)	0.7115 (3)	0.106 (2)
H13	0.3650	0.8589	0.7514	0.128*
C14	0.2258 (8)	0.8775 (3)	0.6857 (3)	0.095 (2)
H14	0.1585	0.9061	0.7079	0.114*
C15	0.1992 (6)	0.8627 (3)	0.6261 (3)	0.0738 (15)
H15	0.1136	0.8798	0.6087	0.089*
S1	0.33690 (18)	0.50195 (11)	0.36927 (6)	0.0851 (5)
S2	0.27067 (10)	0.79981 (7)	0.52013 (5)	0.0495 (4)
N1	0.3261 (4)	0.5097 (3)	0.43942 (19)	0.0622 (12)
H1	0.349 (5)	0.466 (3)	0.455 (2)	0.064 (17)*
N2	0.2115 (3)	0.7085 (2)	0.51605 (18)	0.0547 (10)
H2	0.135 (5)	0.708 (3)	0.525 (2)	0.066*
O1	0.3051 (5)	0.5811 (3)	0.34561 (18)	0.1226 (17)
O2	0.4721 (5)	0.4642 (3)	0.35702 (17)	0.1228 (17)
O3	0.4064 (3)	0.8029 (2)	0.49056 (13)	0.0654 (9)
O4	0.1556 (3)	0.85005 (18)	0.49911 (14)	0.0637 (9)

	U11	U22	U33	U12	U13	U23
C1	0.106 (5)	0.064 (4)	0.054 (3)	−0.007 (3)	0.002 (3)	0.011 (3)
C2	0.140 (6)	0.064 (4)	0.104 (5)	−0.017 (4)	−0.029 (5)	0.018 (3)
C3	0.137 (7)	0.110 (7)	0.125 (6)	−0.012 (5)	−0.049 (5)	−0.002 (5)
C4	0.170 (8)	0.086 (6)	0.097 (5)	−0.031 (6)	−0.025 (5)	−0.008 (4)
C5	0.202 (9)	0.059 (5)	0.093 (5)	−0.010 (6)	−0.022 (6)	−0.010 (4)
C6	0.144 (6)	0.072 (5)	0.090 (4)	0.001 (5)	−0.016 (4)	−0.009 (4)
C7	0.051 (3)	0.048 (3)	0.088 (4)	−0.005 (2)	−0.003 (3)	−0.006 (3)
C8	0.053 (3)	0.045 (3)	0.083 (4)	−0.003 (2)	0.002 (3)	0.005 (2)
C9	0.044 (2)	0.046 (3)	0.077 (3)	0.005 (2)	−0.013 (2)	0.000 (2)
C10	0.045 (3)	0.033 (2)	0.068 (3)	0.0005 (19)	0.009 (2)	0.000 (2)
C11	0.055 (3)	0.067 (4)	0.082 (4)	0.005 (3)	−0.008 (3)	−0.011 (3)
C12	0.103 (5)	0.098 (5)	0.088 (5)	−0.012 (4)	−0.021 (4)	−0.020 (4)
C13	0.144 (7)	0.089 (5)	0.086 (5)	−0.015 (5)	−0.001 (5)	−0.005 (4)
C14	0.122 (6)	0.063 (4)	0.099 (5)	−0.010 (4)	0.045 (5)	−0.017 (4)
C15	0.069 (4)	0.055 (4)	0.098 (4)	0.001 (3)	0.017 (3)	0.006 (3)
S1	0.0949 (12)	0.0843 (12)	0.0762 (10)	−0.0253 (10)	0.0100 (8)	0.0154 (9)
S2	0.0281 (5)	0.0490 (7)	0.0714 (8)	0.0022 (5)	0.0015 (5)	0.0115 (6)
N1	0.062 (3)	0.049 (3)	0.075 (3)	−0.004 (2)	−0.002 (2)	0.005 (2)
N2	0.0289 (17)	0.048 (2)	0.087 (3)	0.0049 (18)	−0.001 (2)	0.007 (2)
O1	0.176 (5)	0.095 (3)	0.098 (3)	−0.049 (3)	−0.024 (3)	0.050 (3)
O2	0.091 (3)	0.169 (5)	0.108 (3)	−0.015 (3)	0.045 (3)	−0.021 (3)
O3	0.0318 (15)	0.090 (2)	0.075 (2)	−0.0012 (16)	0.0080 (15)	0.0128 (18)
O4	0.0395 (16)	0.057 (2)	0.095 (2)	0.0091 (15)	−0.0078 (16)	0.0255 (17)

C1—C6	1.357 (7)	C9—H9B	0.9700
C1—C2	1.370 (8)	C10—C15	1.368 (6)
C1—S1	1.754 (6)	C10—C11	1.390 (6)
C2—C3	1.395 (9)	C10—S2	1.748 (5)
C2—H2A	0.9300	C11—C12	1.362 (7)
C3—C4	1.325 (9)	C11—H11	0.9300
C3—H3A	0.9300	C12—C13	1.365 (9)
C4—C5	1.351 (9)	C12—H12	0.9300
C4—H4A	0.9300	C13—C14	1.362 (9)
C5—C6	1.382 (9)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.398 (7)
C6—H6	0.9300	C14—H14	0.9300
C7—N1	1.471 (6)	C15—H15	0.9300
C7—C8	1.506 (6)	S1—O2	1.424 (4)
C7—H7A	0.9700	S1—O1	1.435 (4)
C7—H7B	0.9700	S1—N1	1.603 (4)
C8—C9	1.503 (6)	S2—O3	1.427 (3)
C8—H8A	0.9700	S2—O4	1.430 (3)
C8—H8B	0.9700	S2—N2	1.597 (4)
C9—N2	1.468 (5)	N1—H1	0.82 (4)
C9—H9A	0.9700	N2—H2	0.74 (4)
C6—C1—C2	118.3 (6)	C15—C10—C11	120.9 (5)
C6—C1—S1	120.7 (5)	C15—C10—S2	120.0 (4)
C2—C1—S1	120.9 (5)	C11—C10—S2	119.1 (4)
C1—C2—C3	120.4 (6)	C12—C11—C10	118.9 (5)
C1—C2—H2A	119.8	C12—C11—H11	120.5
C3—C2—H2A	119.8	C10—C11—H11	120.5
C4—C3—C2	120.0 (8)	C11—C12—C13	121.2 (6)
C4—C3—H3A	120.0	C11—C12—H12	119.4
C2—C3—H3A	120.0	C13—C12—H12	119.4
C3—C4—C5	120.5 (8)	C14—C13—C12	119.8 (6)
C3—C4—H4A	119.7	C14—C13—H13	120.1
C5—C4—H4A	119.7	C12—C13—H13	120.1
C4—C5—C6	120.3 (7)	C13—C14—C15	120.6 (6)
C4—C5—H5	119.9	C13—C14—H14	119.7
C6—C5—H5	119.9	C15—C14—H14	119.7
C1—C6—C5	120.5 (7)	C10—C15—C14	118.4 (5)
C1—C6—H6	119.7	C10—C15—H15	120.8
C5—C6—H6	119.7	C14—C15—H15	120.8
N1—C7—C8	110.4 (4)	O2—S1—O1	120.0 (3)
N1—C7—H7A	109.6	O2—S1—N1	106.5 (3)
C8—C7—H7A	109.6	O1—S1—N1	106.8 (3)
N1—C7—H7B	109.6	O2—S1—C1	108.6 (3)
C8—C7—H7B	109.6	O1—S1—C1	106.9 (3)
H7A—C7—H7B	108.1	N1—S1—C1	107.4 (2)
C9—C8—C7	114.8 (4)	O3—S2—O4	118.66 (18)
C9—C8—H8A	108.6	O3—S2—N2	107.9 (2)
C7—C8—H8A	108.6	O4—S2—N2	105.36 (18)
C9—C8—H8B	108.6	O3—S2—C10	107.48 (19)
C7—C8—H8B	108.6	O4—S2—C10	108.8 (2)
H8A—C8—H8B	107.6	N2—S2—C10	108.2 (2)
N2—C9—C8	109.8 (3)	C7—N1—S1	119.5 (4)
N2—C9—H9A	109.7	C7—N1—H1	108 (3)
C8—C9—H9A	109.7	S1—N1—H1	110 (3)
N2—C9—H9B	109.7	C9—N2—S2	121.0 (3)
C8—C9—H9B	109.7	C9—N2—H2	115 (4)
H9A—C9—H9B	108.2	S2—N2—H2	109 (4)
C6—C1—C2—C3	−2.1 (9)	C2—C1—S1—O2	−147.7 (5)
S1—C1—C2—C3	−177.1 (5)	C6—C1—S1—O1	168.2 (5)
C1—C2—C3—C4	1.2 (11)	C2—C1—S1—O1	−16.9 (6)
C2—C3—C4—C5	0.0 (12)	C6—C1—S1—N1	−77.5 (5)
C3—C4—C5—C6	−0.2 (12)	C2—C1—S1—N1	97.4 (5)
C2—C1—C6—C5	1.9 (9)	C15—C10—S2—O3	147.5 (4)
S1—C1—C6—C5	176.9 (5)	C11—C10—S2—O3	−34.5 (4)
C4—C5—C6—C1	−0.8 (10)	C15—C10—S2—O4	17.8 (4)
N1—C7—C8—C9	72.5 (5)	C11—C10—S2—O4	−164.2 (3)
C7—C8—C9—N2	65.7 (5)	C15—C10—S2—N2	−96.2 (4)
C15—C10—C11—C12	1.4 (7)	C11—C10—S2—N2	81.8 (4)
S2—C10—C11—C12	−176.6 (4)	C8—C7—N1—S1	−165.2 (3)
C10—C11—C12—C13	−1.0 (9)	O2—S1—N1—C7	−173.0 (4)
C11—C12—C13—C14	−0.8 (10)	O1—S1—N1—C7	57.7 (4)
C12—C13—C14—C15	2.2 (10)	C1—S1—N1—C7	−56.7 (4)
C11—C10—C15—C14	0.0 (7)	C8—C9—N2—S2	179.2 (3)
S2—C10—C15—C14	178.0 (4)	O3—S2—N2—C9	56.7 (4)
C13—C14—C15—C10	−1.8 (8)	O4—S2—N2—C9	−175.6 (3)
C6—C1—S1—O2	37.4 (5)	C10—S2—N2—C9	−59.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.82 (4)	2.15 (5)	2.954 (6)	164 (4)
N2—H2···O3ii	0.74 (4)	2.15 (4)	2.836 (4)	154 (5)
C9—H9B···O4iii	0.97	2.51	3.430 (5)	158
C13—H13···O1iv	0.93	2.42	3.276 (8)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.82 (4)	2.15 (5)	2.954 (6)	164 (4)
N2—H2⋯O3ii	0.74 (4)	2.15 (4)	2.836 (4)	154 (5)
C9—H9B⋯O4iii	0.97	2.51	3.430 (5)	158
C13—H13⋯O1iv	0.93	2.42	3.276 (8)	153

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