N,N'-Bis[(2-methyl-phenyl)sulfon-yl]adipamide.

The asymmetric unit of the title compound, C(20)H(24)N(2)O(6)S(2), comprises one half-mol-ecule, the remaining portion being generated via an inversion centre. The dihedral angle between the plane of the benzene ring and the SO(2)-NH-C(O)-C-C segment is 89.9 (1)°. In the crystal, inter-molecular N-H⋯O(S) hydrogen bonds link the mol-ecules into infinite chains in [101].

Related literature

For related structures, see: Gowda et al. (2007 ▶, 2010 ▶).

Experimental

Crystal data

C20H24N2O6S2

M = 452.53

Monoclinic,

a = 11.928 (2) Å

b = 5.523 (1) Å

c = 16.447 (4) Å

β = 96.05 (2)°

V = 1077.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.48 × 0.12 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.875, T max = 0.989

3521 measured reflections

2135 independent reflections

1571 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.147

S = 1.31

2135 reflections

140 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007203/vm2082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007203/vm2082Isup2.hkl

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

C20H24N2O6S2	F(000) = 476
Mr = 452.53	Dx = 1.395 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1186 reflections
a = 11.928 (2) Å	θ = 2.9–27.9°
b = 5.523 (1) Å	µ = 0.29 mm−1
c = 16.447 (4) Å	T = 293 K
β = 96.05 (2)°	Needle, colourless
V = 1077.5 (4) Å3	0.48 × 0.12 × 0.04 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2135 independent reflections
Radiation source: fine-focus sealed tube	1571 reflections with I > 2σ(I)
graphite	Rint = 0.037
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→13
Tmin = 0.875, Tmax = 0.989	k = −5→6
3521 measured reflections	l = −14→20

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.31	w = 1/[σ2(Fo2) + (0.0079P)2 + 2.6127P] where P = (Fo2 + 2Fc2)/3
2135 reflections	(Δ/σ)max = 0.001
140 parameters	Δρmax = 0.52 e Å−3
1 restraint	Δρmin = −0.28 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
S1	−0.08049 (9)	−0.2084 (2)	0.23912 (6)	0.0351 (3)
O1	−0.1885 (2)	−0.2313 (6)	0.19216 (18)	0.0455 (8)
O2	−0.0301 (3)	−0.4181 (6)	0.27714 (19)	0.0516 (9)
O3	0.0740 (2)	0.0040 (6)	0.37419 (19)	0.0477 (9)
N1	−0.1032 (3)	−0.0087 (7)	0.3094 (2)	0.0369 (9)
H1N	−0.165 (2)	0.064 (7)	0.300 (3)	0.044*
C1	0.0160 (3)	−0.0737 (8)	0.1790 (3)	0.0369 (10)
C2	−0.0143 (4)	0.1150 (9)	0.1259 (3)	0.0482 (12)
C3	0.0713 (5)	0.2137 (13)	0.0847 (4)	0.0775 (19)
H3	0.0547	0.3411	0.0485	0.093*
C4	0.1795 (6)	0.1268 (15)	0.0966 (4)	0.092 (2)
H4	0.2356	0.1986	0.0696	0.110*
C5	0.2054 (5)	−0.0632 (15)	0.1476 (4)	0.082 (2)
H5	0.2783	−0.1248	0.1535	0.098*
C6	0.1249 (4)	−0.1647 (11)	0.1902 (3)	0.0589 (15)
H6	0.1428	−0.2924	0.2261	0.071*
C7	−0.0216 (3)	0.0753 (8)	0.3696 (2)	0.0324 (9)
C8	−0.0659 (3)	0.2492 (8)	0.4283 (2)	0.0345 (10)
H8A	−0.1013	0.1582	0.4691	0.041*
H8B	−0.1233	0.3495	0.3989	0.041*
C9	0.0242 (3)	0.4117 (8)	0.4713 (2)	0.0361 (10)
H91	0.0808	0.3124	0.5021	0.043*
H92	0.0608	0.5012	0.4308	0.043*
C10	−0.1313 (4)	0.2174 (11)	0.1094 (3)	0.0661 (16)
H10A	−0.1779	0.1063	0.0761	0.079*
H10B	−0.1282	0.3693	0.0814	0.079*
H10C	−0.1625	0.2418	0.1603	0.079*

	U11	U22	U33	U12	U13	U23
S1	0.0338 (5)	0.0381 (6)	0.0326 (5)	−0.0040 (5)	−0.0005 (4)	−0.0031 (5)
O1	0.0365 (16)	0.055 (2)	0.0431 (17)	−0.0145 (16)	−0.0039 (13)	−0.0087 (16)
O2	0.064 (2)	0.041 (2)	0.049 (2)	0.0036 (17)	0.0004 (16)	0.0035 (17)
O3	0.0293 (16)	0.059 (2)	0.053 (2)	0.0087 (15)	−0.0038 (13)	−0.0119 (17)
N1	0.0268 (18)	0.049 (2)	0.0343 (19)	0.0053 (17)	−0.0021 (15)	−0.0065 (18)
C1	0.031 (2)	0.045 (3)	0.035 (2)	−0.005 (2)	0.0055 (18)	−0.008 (2)
C2	0.055 (3)	0.047 (3)	0.042 (3)	−0.002 (2)	0.006 (2)	−0.002 (2)
C3	0.087 (4)	0.081 (5)	0.068 (4)	−0.008 (4)	0.030 (3)	0.020 (4)
C4	0.069 (4)	0.114 (6)	0.099 (5)	−0.029 (4)	0.044 (4)	0.007 (5)
C5	0.043 (3)	0.125 (6)	0.082 (5)	−0.003 (4)	0.023 (3)	−0.013 (5)
C6	0.041 (3)	0.083 (4)	0.054 (3)	0.007 (3)	0.007 (2)	−0.001 (3)
C7	0.030 (2)	0.037 (2)	0.029 (2)	−0.0020 (19)	−0.0008 (17)	0.0015 (19)
C8	0.029 (2)	0.044 (3)	0.030 (2)	0.0057 (19)	−0.0005 (16)	−0.002 (2)
C9	0.034 (2)	0.041 (3)	0.033 (2)	−0.001 (2)	−0.0007 (17)	−0.004 (2)
C10	0.072 (4)	0.061 (4)	0.065 (4)	0.015 (3)	0.006 (3)	0.016 (3)

S1—O2	1.419 (3)	C4—H4	0.9300
S1—O1	1.436 (3)	C5—C6	1.368 (8)
S1—N1	1.641 (4)	C5—H5	0.9300
S1—C1	1.760 (4)	C6—H6	0.9300
O3—C7	1.201 (5)	C7—C8	1.497 (6)
N1—C7	1.393 (5)	C8—C9	1.516 (6)
N1—H1N	0.843 (19)	C8—H8A	0.9700
C1—C2	1.383 (7)	C8—H8B	0.9700
C1—C6	1.387 (6)	C9—C9i	1.514 (8)
C2—C3	1.394 (7)	C9—H91	0.9700
C2—C10	1.504 (7)	C9—H92	0.9700
C3—C4	1.372 (9)	C10—H10A	0.9600
C3—H3	0.9300	C10—H10B	0.9600
C4—C5	1.358 (10)	C10—H10C	0.9600
O2—S1—O1	118.7 (2)	C5—C6—C1	118.7 (6)
O2—S1—N1	109.39 (19)	C5—C6—H6	120.6
O1—S1—N1	103.45 (18)	C1—C6—H6	120.6
O2—S1—C1	108.7 (2)	O3—C7—N1	121.6 (4)
O1—S1—C1	109.7 (2)	O3—C7—C8	124.5 (4)
N1—S1—C1	106.1 (2)	N1—C7—C8	113.9 (3)
C7—N1—S1	124.7 (3)	C7—C8—C9	113.6 (3)
C7—N1—H1N	120 (3)	C7—C8—H8A	108.8
S1—N1—H1N	114 (3)	C9—C8—H8A	108.8
C2—C1—C6	122.4 (4)	C7—C8—H8B	108.8
C2—C1—S1	122.1 (3)	C9—C8—H8B	108.8
C6—C1—S1	115.5 (4)	H8A—C8—H8B	107.7
C1—C2—C3	116.5 (5)	C9i—C9—C8	112.0 (4)
C1—C2—C10	124.9 (4)	C9i—C9—H91	109.2
C3—C2—C10	118.6 (5)	C8—C9—H91	109.2
C4—C3—C2	121.4 (6)	C9i—C9—H92	109.2
C4—C3—H3	119.3	C8—C9—H92	109.2
C2—C3—H3	119.3	H91—C9—H92	107.9
C5—C4—C3	120.5 (6)	C2—C10—H10A	109.5
C5—C4—H4	119.8	C2—C10—H10B	109.5
C3—C4—H4	119.8	H10A—C10—H10B	109.5
C4—C5—C6	120.5 (6)	C2—C10—H10C	109.5
C4—C5—H5	119.7	H10A—C10—H10C	109.5
C6—C5—H5	119.7	H10B—C10—H10C	109.5
O2—S1—N1—C7	53.4 (4)	C1—C2—C3—C4	0.1 (9)
O1—S1—N1—C7	−179.3 (4)	C10—C2—C3—C4	−179.4 (6)
C1—S1—N1—C7	−63.7 (4)	C2—C3—C4—C5	1.7 (11)
O2—S1—C1—C2	171.1 (4)	C3—C4—C5—C6	−2.5 (11)
O1—S1—C1—C2	39.9 (4)	C4—C5—C6—C1	1.5 (10)
N1—S1—C1—C2	−71.3 (4)	C2—C1—C6—C5	0.3 (8)
O2—S1—C1—C6	−10.7 (4)	S1—C1—C6—C5	−177.8 (5)
O1—S1—C1—C6	−141.9 (4)	S1—N1—C7—O3	−0.2 (6)
N1—S1—C1—C6	106.9 (4)	S1—N1—C7—C8	−177.5 (3)
C6—C1—C2—C3	−1.1 (7)	O3—C7—C8—C9	25.3 (6)
S1—C1—C2—C3	176.9 (4)	N1—C7—C8—C9	−157.5 (4)
C6—C1—C2—C10	178.4 (5)	C7—C8—C9—C9i	178.8 (4)
S1—C1—C2—C10	−3.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ii	0.84 (2)	2.09 (2)	2.917 (4)	166 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.09 (2)	2.917 (4)	166 (4)

Symmetry code: (i) .