N,N'-(Propane-1,3-di-yl)bis-(p-toluene-sulfonamide).

The complete mol-ecule of the title compound, C(17)H(22)N(2)O(4)S(2), is generated by crystallographic twofold symmetry, with one C atom lying on the rotation axis. The dihedral angle between the benzene rings is 44.04 (7)° and the conformation of the central N-C-C-C group is gauche. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating corrugated (010) sheets, and weak C-H⋯O inter-actions consolidate the packing.

Related literature

For the related structure of N,n class="Chemical">N′-ethyl­enebis(p-toluene­sulfonamide), see: Gajadhar-Plummer et al. (2001 ▶).

Experimental

Crystal data

C17H22N2O4S2

M = 382.49

Orthorhombic,

a = 12.3169 (9) Å

b = 18.0787 (15) Å

c = 8.3819 (5) Å

V = 1866.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.52 × 0.46 × 0.36 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.856, T max = 0.897

4996 measured reflections

1625 independent reflections

1472 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.078

S = 1.07

1625 reflections

119 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 372 Friedel pairs

Flack parameter: 0.12 (11)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (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/S1600536811030820/om2455sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030820/om2455Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030820/om2455Isup3.cml

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

C17H22N2O4S2	F(000) = 808
Mr = 382.49	Dx = 1.361 Mg m−3
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 2756 reflections
a = 12.3169 (9) Å	θ = 2.8–28.3°
b = 18.0787 (15) Å	µ = 0.31 mm−1
c = 8.3819 (5) Å	T = 296 K
V = 1866.4 (2) Å3	Block, colourless
Z = 4	0.52 × 0.46 × 0.36 mm

Bruker APEXII CCD diffractometer	1625 independent reflections
Radiation source: fine-focus sealed tube	1472 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 28.4°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→16
Tmin = 0.856, Tmax = 0.897	k = −24→23
4996 measured reflections	l = −11→6

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0475P)2 + 0.2164P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1625 reflections	Δρmax = 0.21 e Å−3
119 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983), 372 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.12 (11)

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	0.65494 (18)	0.85229 (12)	0.6032 (3)	0.0505 (5)
C2	0.7458 (2)	0.80891 (11)	0.5798 (3)	0.0568 (6)
H2	0.8048	0.8285	0.5251	0.068*
C3	0.75132 (18)	0.73752 (11)	0.6352 (3)	0.0510 (5)
H3	0.8135	0.7094	0.6189	0.061*
C4	0.66317 (14)	0.70786 (10)	0.7158 (3)	0.0384 (4)
C5	0.57086 (16)	0.75001 (10)	0.7395 (3)	0.0455 (5)
H5	0.5114	0.7303	0.7931	0.055*
C6	0.56785 (17)	0.82139 (11)	0.6830 (3)	0.0500 (5)
H6	0.5056	0.8496	0.6988	0.060*
C7	0.6512 (2)	0.93096 (14)	0.5432 (4)	0.0782 (9)
H7A	0.6955	0.9354	0.4495	0.117*
H7B	0.6780	0.9637	0.6244	0.117*
H7C	0.5776	0.9439	0.5175	0.117*
C8	0.52239 (18)	0.56829 (12)	0.5701 (3)	0.0480 (5)
H8A	0.5160	0.6123	0.5044	0.058*
H8B	0.4701	0.5718	0.6562	0.058*
C9	0.5000	0.5000	0.4707 (4)	0.0535 (8)
H9	0.4379	0.5094	0.4025	0.064*
S1	0.66864 (4)	0.61578 (2)	0.78225 (9)	0.04287 (14)
O1	0.59049 (15)	0.60730 (8)	0.9065 (2)	0.0615 (4)
O2	0.77949 (13)	0.59791 (8)	0.8137 (2)	0.0610 (5)
N1	0.63280 (15)	0.56284 (9)	0.6355 (2)	0.0414 (4)
H1	0.6771 (18)	0.5633 (14)	0.563 (3)	0.050*

	U11	U22	U33	U12	U13	U23
C1	0.0603 (13)	0.0396 (11)	0.0515 (13)	−0.0102 (9)	−0.0112 (10)	0.0031 (10)
C2	0.0545 (12)	0.0483 (11)	0.0675 (15)	−0.0129 (10)	0.0095 (13)	0.0028 (10)
C3	0.0442 (11)	0.0476 (10)	0.0613 (14)	−0.0010 (9)	0.0072 (11)	−0.0025 (10)
C4	0.0426 (11)	0.0346 (8)	0.0380 (9)	−0.0006 (7)	−0.0039 (9)	−0.0005 (7)
C5	0.0437 (10)	0.0421 (10)	0.0506 (13)	0.0009 (8)	0.0023 (9)	0.0025 (8)
C6	0.0481 (12)	0.0426 (10)	0.0594 (14)	0.0052 (9)	−0.0083 (10)	−0.0010 (9)
C7	0.094 (2)	0.0443 (13)	0.097 (2)	−0.0174 (12)	−0.0219 (18)	0.0166 (14)
C8	0.0488 (12)	0.0433 (10)	0.0519 (12)	−0.0037 (8)	−0.0063 (10)	0.0068 (9)
C9	0.0573 (19)	0.065 (2)	0.0387 (14)	−0.0183 (15)	0.000	0.000
S1	0.0551 (3)	0.0375 (2)	0.0360 (2)	0.00355 (18)	−0.0046 (3)	0.0038 (2)
O1	0.0904 (12)	0.0516 (9)	0.0425 (8)	−0.0022 (8)	0.0158 (9)	0.0068 (7)
O2	0.0633 (10)	0.0568 (9)	0.0627 (13)	0.0121 (7)	−0.0238 (9)	0.0014 (8)
N1	0.0462 (10)	0.0378 (8)	0.0403 (9)	0.0000 (7)	0.0016 (8)	−0.0001 (7)

C1—C2	1.380 (3)	C7—H7B	0.9600
C1—C6	1.382 (3)	C7—H7C	0.9600
C1—C7	1.509 (3)	C8—N1	1.470 (3)
C2—C3	1.373 (3)	C8—C9	1.515 (3)
C2—H2	0.9300	C8—H8A	0.9700
C3—C4	1.387 (3)	C8—H8B	0.9700
C3—H3	0.9300	C9—C8i	1.515 (3)
C4—C5	1.383 (2)	C9—H9	0.9700
C4—S1	1.7567 (19)	S1—O1	1.4265 (17)
C5—C6	1.375 (3)	S1—O2	1.4276 (16)
C5—H5	0.9300	S1—N1	1.6199 (18)
C6—H6	0.9300	N1—H1	0.82 (3)
C7—H7A	0.9600
C2—C1—C6	117.9 (2)	C1—C7—H7C	109.5
C2—C1—C7	120.9 (2)	H7A—C7—H7C	109.5
C6—C1—C7	121.2 (2)	H7B—C7—H7C	109.5
C3—C2—C1	121.8 (2)	N1—C8—C9	108.60 (16)
C3—C2—H2	119.1	N1—C8—H8A	110.0
C1—C2—H2	119.1	C9—C8—H8A	110.0
C2—C3—C4	119.3 (2)	N1—C8—H8B	110.0
C2—C3—H3	120.4	C9—C8—H8B	110.0
C4—C3—H3	120.4	H8A—C8—H8B	108.4
C5—C4—C3	120.04 (19)	C8—C9—C8i	113.3 (3)
C5—C4—S1	120.55 (14)	C8—C9—H9	109.0
C3—C4—S1	119.40 (15)	C8i—C9—H9	108.8
C6—C5—C4	119.33 (19)	O1—S1—O2	119.10 (12)
C6—C5—H5	120.3	O1—S1—N1	107.88 (10)
C4—C5—H5	120.3	O2—S1—N1	105.50 (10)
C5—C6—C1	121.67 (19)	O1—S1—C4	107.90 (9)
C5—C6—H6	119.2	O2—S1—C4	108.04 (9)
C1—C6—H6	119.2	N1—S1—C4	107.97 (10)
C1—C7—H7A	109.5	C8—N1—S1	119.73 (14)
C1—C7—H7B	109.5	C8—N1—H1	109.8 (17)
H7A—C7—H7B	109.5	S1—N1—H1	112.2 (18)
C6—C1—C2—C3	−0.9 (4)	C5—C4—S1—O1	−22.6 (2)
C7—C1—C2—C3	179.2 (3)	C3—C4—S1—O1	159.14 (18)
C1—C2—C3—C4	0.5 (4)	C5—C4—S1—O2	−152.60 (18)
C2—C3—C4—C5	0.1 (3)	C3—C4—S1—O2	29.1 (2)
C2—C3—C4—S1	178.35 (19)	C5—C4—S1—N1	93.76 (19)
C3—C4—C5—C6	−0.3 (3)	C3—C4—S1—N1	−84.50 (19)
S1—C4—C5—C6	−178.50 (17)	C9—C8—N1—S1	−163.87 (15)
C4—C5—C6—C1	−0.2 (3)	O1—S1—N1—C8	53.02 (18)
C2—C1—C6—C5	0.7 (4)	O2—S1—N1—C8	−178.68 (15)
C7—C1—C6—C5	−179.4 (2)	C4—S1—N1—C8	−63.35 (17)
N1—C8—C9—C8i	75.53 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ii	0.82 (3)	2.24 (3)	2.974 (2)	149 (2)
C7—H7C···O1iii	0.96	2.45	3.264 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.82 (3)	2.24 (3)	2.974 (2)	149 (2)
C7—H7C⋯O1ii	0.96	2.45	3.264 (3)	142

Symmetry codes: (i) ; (ii) .