N,N'-Bis[(4-methyl-phen-yl)sulfon-yl]adipamide.

In the centrosymmetric title compound, C(20)H(24)N(2)O(6)S(2), the N-H and C=O bonds are trans to each other. In the crystal, inter-molecular N-H⋯O(S) hydrogen bonds link the mol-ecules into zigzag chains running along the b axis. The O atom involved in the hydrogen bond has a longer S-O bond than the other O atom bonded to S [1.441 (2) versus 1.428 (2) Å].

Related literature

For our study of the effect of substituents on the structures of sulfonamides, see: Gowda et al. (2005 ▶, 2007 ▶); Rodrigues et al. (2011 ▶).

Experimental

Crystal data

C20H24N2O6S2

M = 452.53

Triclinic,

a = 6.0011 (9) Å

b = 8.765 (1) Å

c = 10.144 (2) Å

α = 90.04 (1)°

β = 92.35 (1)°

γ = 98.01 (1)°

V = 527.91 (14) Å3

Z = 1

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.48 × 0.12 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.872, T max = 0.974

3355 measured reflections

2122 independent reflections

1651 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.141

S = 1.08

2122 reflections

140 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.78 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data 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/S1600536811007756/bt5485sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007756/bt5485Isup2.hkl

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

C20H24N2O6S2	Z = 1
Mr = 452.53	F(000) = 238
Triclinic, P1	Dx = 1.423 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0011 (9) Å	Cell parameters from 1299 reflections
b = 8.765 (1) Å	θ = 3.1–28.0°
c = 10.144 (2) Å	µ = 0.29 mm−1
α = 90.04 (1)°	T = 293 K
β = 92.35 (1)°	Needle, colourless
γ = 98.01 (1)°	0.48 × 0.12 × 0.09 mm
V = 527.91 (14) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2122 independent reflections
Radiation source: fine-focus sealed tube	1651 reflections with I > 2σ(I)
graphite	Rint = 0.021
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→7
Tmin = 0.872, Tmax = 0.974	k = −10→7
3355 measured reflections	l = −12→12

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.6262P] where P = (Fo2 + 2Fc2)/3
2122 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.78 e Å−3
1 restraint	Δρmin = −0.28 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.3932 (5)	0.6198 (3)	0.3150 (3)	0.0359 (6)
C2	0.6161 (5)	0.6864 (4)	0.3058 (4)	0.0474 (8)
H2	0.6946	0.6720	0.2306	0.057*
C3	0.7186 (6)	0.7738 (4)	0.4098 (4)	0.0550 (9)
H3	0.8665	0.8208	0.4031	0.066*
C4	0.6072 (6)	0.7940 (4)	0.5246 (3)	0.0521 (9)
C5	0.3872 (6)	0.7224 (4)	0.5321 (3)	0.0550 (9)
H5	0.3107	0.7327	0.6088	0.066*
C6	0.2789 (5)	0.6363 (4)	0.4287 (3)	0.0457 (8)
H6	0.1308	0.5898	0.4353	0.055*
C7	0.1735 (4)	0.7710 (3)	0.0561 (3)	0.0366 (7)
C8	0.2257 (5)	0.8691 (3)	−0.0642 (3)	0.0392 (7)
H8A	0.0870	0.8975	−0.1030	0.047*
H8B	0.2921	0.8100	−0.1292	0.047*
C9	0.3879 (5)	1.0149 (4)	−0.0284 (4)	0.0483 (8)
H9A	0.4117	1.0770	−0.1070	0.058*
H9B	0.3184	1.0743	0.0350	0.058*
C10	0.7223 (9)	0.8915 (5)	0.6365 (4)	0.0829 (14)
H10A	0.7018	0.9971	0.6227	0.099*
H10B	0.8802	0.8831	0.6400	0.099*
H10C	0.6582	0.8565	0.7181	0.099*
N1	0.2657 (5)	0.6347 (3)	0.0575 (3)	0.0411 (6)
H1N	0.353 (5)	0.614 (4)	0.000 (3)	0.049*
O1	0.0322 (4)	0.4586 (3)	0.2128 (2)	0.0569 (7)
O2	0.3994 (5)	0.4024 (3)	0.1391 (2)	0.0585 (7)
O3	0.0681 (4)	0.8081 (3)	0.1472 (2)	0.0532 (6)
S1	0.25952 (14)	0.51241 (8)	0.18165 (8)	0.0417 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0382 (15)	0.0335 (14)	0.0367 (15)	0.0053 (12)	0.0077 (12)	0.0048 (12)
C2	0.0387 (17)	0.0537 (19)	0.0501 (19)	0.0044 (14)	0.0134 (14)	0.0067 (15)
C3	0.0404 (18)	0.054 (2)	0.066 (2)	−0.0062 (15)	−0.0037 (16)	0.0106 (18)
C4	0.069 (2)	0.0432 (17)	0.0413 (19)	0.0005 (16)	−0.0104 (16)	0.0102 (14)
C5	0.066 (2)	0.063 (2)	0.0354 (18)	0.0029 (18)	0.0114 (16)	0.0021 (16)
C6	0.0414 (17)	0.0514 (18)	0.0431 (18)	−0.0008 (14)	0.0121 (14)	0.0065 (14)
C7	0.0255 (14)	0.0381 (15)	0.0443 (17)	−0.0019 (12)	−0.0001 (12)	0.0011 (13)
C8	0.0376 (16)	0.0394 (15)	0.0398 (17)	0.0035 (12)	−0.0015 (13)	0.0027 (13)
C9	0.0439 (18)	0.0456 (18)	0.054 (2)	0.0022 (14)	0.0027 (15)	0.0095 (15)
C10	0.113 (4)	0.066 (3)	0.059 (3)	−0.015 (3)	−0.024 (2)	0.006 (2)
N1	0.0521 (16)	0.0372 (13)	0.0349 (14)	0.0079 (12)	0.0069 (11)	0.0008 (11)
O1	0.0529 (14)	0.0520 (14)	0.0595 (15)	−0.0161 (11)	0.0062 (11)	0.0040 (11)
O2	0.0910 (19)	0.0375 (12)	0.0521 (15)	0.0215 (12)	0.0213 (13)	0.0053 (10)
O3	0.0475 (13)	0.0578 (14)	0.0580 (15)	0.0152 (11)	0.0218 (11)	0.0072 (12)
S1	0.0516 (5)	0.0318 (4)	0.0411 (4)	0.0018 (3)	0.0091 (3)	0.0013 (3)

C1—C6	1.383 (4)	C7—C8	1.511 (4)
C1—C2	1.389 (4)	C8—C9	1.529 (4)
C1—S1	1.749 (3)	C8—H8A	0.9700
C2—C3	1.376 (5)	C8—H8B	0.9700
C2—H2	0.9300	C9—C9i	1.498 (6)
C3—C4	1.390 (5)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.386 (5)	C10—H10A	0.9600
C4—C10	1.505 (5)	C10—H10B	0.9600
C5—C6	1.378 (5)	C10—H10C	0.9600
C5—H5	0.9300	N1—S1	1.653 (3)
C6—H6	0.9300	N1—H1N	0.837 (18)
C7—O3	1.210 (4)	O1—S1	1.428 (2)
C7—N1	1.385 (4)	O2—S1	1.441 (2)
C6—C1—C2	120.6 (3)	C7—C8—H8B	109.4
C6—C1—S1	120.3 (2)	C9—C8—H8B	109.4
C2—C1—S1	119.1 (2)	H8A—C8—H8B	108.0
C3—C2—C1	118.8 (3)	C9i—C9—C8	114.2 (3)
C3—C2—H2	120.6	C9i—C9—H9A	108.7
C1—C2—H2	120.6	C8—C9—H9A	108.7
C2—C3—C4	121.8 (3)	C9i—C9—H9B	108.7
C2—C3—H3	119.1	C8—C9—H9B	108.7
C4—C3—H3	119.1	H9A—C9—H9B	107.6
C5—C4—C3	117.9 (3)	C4—C10—H10A	109.5
C5—C4—C10	121.3 (4)	C4—C10—H10B	109.5
C3—C4—C10	120.8 (4)	H10A—C10—H10B	109.5
C6—C5—C4	121.6 (3)	C4—C10—H10C	109.5
C6—C5—H5	119.2	H10A—C10—H10C	109.5
C4—C5—H5	119.2	H10B—C10—H10C	109.5
C5—C6—C1	119.2 (3)	C7—N1—S1	125.4 (2)
C5—C6—H6	120.4	C7—N1—H1N	122 (2)
C1—C6—H6	120.4	S1—N1—H1N	112 (2)
O3—C7—N1	121.5 (3)	O1—S1—O2	118.77 (16)
O3—C7—C8	124.2 (3)	O1—S1—N1	110.32 (15)
N1—C7—C8	114.2 (3)	O2—S1—N1	103.00 (14)
C7—C8—C9	111.2 (3)	O1—S1—C1	109.01 (15)
C7—C8—H8A	109.4	O2—S1—C1	109.75 (15)
C9—C8—H8A	109.4	N1—S1—C1	105.04 (13)
C6—C1—C2—C3	−2.4 (5)	C7—C8—C9—C9i	61.1 (5)
S1—C1—C2—C3	178.4 (3)	O3—C7—N1—S1	−3.7 (4)
C1—C2—C3—C4	1.7 (5)	C8—C7—N1—S1	173.6 (2)
C2—C3—C4—C5	0.2 (5)	C7—N1—S1—O1	58.8 (3)
C2—C3—C4—C10	−179.4 (3)	C7—N1—S1—O2	−173.4 (3)
C3—C4—C5—C6	−1.3 (5)	C7—N1—S1—C1	−58.5 (3)
C10—C4—C5—C6	178.3 (3)	C6—C1—S1—O1	2.0 (3)
C4—C5—C6—C1	0.5 (5)	C2—C1—S1—O1	−178.8 (2)
C2—C1—C6—C5	1.4 (5)	C6—C1—S1—O2	−129.6 (3)
S1—C1—C6—C5	−179.5 (3)	C2—C1—S1—O2	49.5 (3)
O3—C7—C8—C9	67.3 (4)	C6—C1—S1—N1	120.3 (3)
N1—C7—C8—C9	−109.9 (3)	C2—C1—S1—N1	−60.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ii	0.84 (2)	2.11 (2)	2.938 (4)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (2)	2.11 (2)	2.938 (4)	170 (3)

Symmetry code: (i) .