N,N'-Bis(4-methyl-phenyl-sulfon-yl)-suberamide.

In the crystal structure of the title compound, C(22)H(28)N(2)O(6)S(2), the asymmetric unit contains one half mol-ecule with a center of symmetry at the mid-point of the central C-C bond. The conformations of all the N-H, C= O and C-H bonds in the central amide and aliphatic segments are anti to their adjacent bonds. The mol-ecule is bent at the S atom with an C-SO(2)-NH-C(O) torsion angle of -76.4 (3)°. The dihedral angle between the benzene ring and the SO(2)-NH-C(O) segment in the two halves of the mol-ecule is 67.2 (1)°. In the crystal, N-H⋯O(C) inter-molecular hydrogen bonds link the mol-ecules into chains along the b axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004 ▶); Gowda et al. (1999 ▶, 2006 ▶); for N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶); and for N-(aryl­sulfon­yl)-amides, see: Rodrigues et al. (2011 ▶)

Experimental

Crystal data

C22H28N2O6S2

M = 480.58

Monoclinic,

a = 8.025 (1) Å

b = 15.835 (2) Å

c = 10.106 (1) Å

β = 112.31 (1)°

V = 1188.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.22 × 0.20 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.944, T max = 0.984

4285 measured reflections

2174 independent reflections

1326 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.139

S = 1.04

2174 reflections

149 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.18 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 datablock(s) I, global. DOI: 10.1107/S1600536811029783/nc2239sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029783/nc2239Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029783/nc2239Isup3.cml

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

C22H28N2O6S2	F(000) = 508
Mr = 480.58	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1291 reflections
a = 8.025 (1) Å	θ = 2.6–27.9°
b = 15.835 (2) Å	µ = 0.26 mm−1
c = 10.106 (1) Å	T = 293 K
β = 112.31 (1)°	Plate, colourless
V = 1188.1 (2) Å3	0.22 × 0.20 × 0.06 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2174 independent reflections
Radiation source: fine-focus sealed tube	1326 reflections with I > 2σ(I)
graphite	Rint = 0.027
Rotation method data acquisition using ω and φ scans	θmax = 25.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→9
Tmin = 0.944, Tmax = 0.984	k = −18→19
4285 measured reflections	l = −12→5

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0552P)2 + 0.6042P] where P = (Fo2 + 2Fc2)/3
2174 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.18 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
C1	0.5932 (5)	0.5531 (2)	0.2952 (4)	0.0497 (9)
C2	0.6538 (6)	0.5479 (3)	0.4421 (4)	0.0737 (13)
H2	0.6270	0.5905	0.4942	0.088*
C3	0.7543 (6)	0.4790 (3)	0.5116 (4)	0.0764 (13)
H3	0.7974	0.4766	0.6109	0.092*
C4	0.7924 (5)	0.4137 (3)	0.4374 (4)	0.0618 (10)
C5	0.7280 (6)	0.4193 (3)	0.2923 (5)	0.0729 (12)
H5	0.7494	0.3752	0.2401	0.088*
C6	0.6318 (5)	0.4888 (3)	0.2201 (4)	0.0659 (11)
H6	0.5933	0.4920	0.1211	0.079*
C7	0.6778 (4)	0.7666 (2)	0.3447 (3)	0.0426 (8)
C8	0.7768 (5)	0.8427 (2)	0.3252 (4)	0.0514 (9)
H8A	0.6928	0.8786	0.2525	0.062*
H8B	0.8681	0.8245	0.2902	0.062*
C9	0.8661 (5)	0.8942 (2)	0.4590 (3)	0.0502 (9)
H9A	0.9560	0.8596	0.5299	0.060*
H9B	0.7765	0.9099	0.4974	0.060*
C10	0.9552 (5)	0.9732 (2)	0.4338 (3)	0.0472 (9)
H10A	0.8651	1.0072	0.3619	0.057*
H10B	1.0450	0.9572	0.3958	0.057*
C11	0.8969 (6)	0.3379 (3)	0.5150 (5)	0.0877 (14)
H11A	0.8168	0.2989	0.5336	0.132*
H11B	0.9882	0.3555	0.6040	0.132*
H11C	0.9525	0.3109	0.4572	0.132*
N1	0.6017 (4)	0.71857 (18)	0.2220 (3)	0.0503 (8)
H1N	0.622 (5)	0.730 (2)	0.147 (3)	0.060*
O1	0.3945 (4)	0.62103 (16)	0.0532 (2)	0.0675 (8)
O2	0.3391 (3)	0.66139 (16)	0.2692 (3)	0.0676 (8)
O3	0.6643 (3)	0.74728 (14)	0.4557 (2)	0.0530 (7)
S1	0.46037 (13)	0.63862 (6)	0.20264 (10)	0.0530 (3)

	U11	U22	U33	U12	U13	U23
C1	0.058 (2)	0.046 (2)	0.046 (2)	−0.0189 (18)	0.0211 (19)	−0.0049 (17)
C2	0.121 (4)	0.052 (3)	0.048 (2)	−0.004 (3)	0.032 (2)	−0.005 (2)
C3	0.115 (4)	0.061 (3)	0.044 (2)	−0.007 (3)	0.020 (2)	0.001 (2)
C4	0.060 (2)	0.064 (3)	0.064 (3)	−0.009 (2)	0.026 (2)	0.000 (2)
C5	0.083 (3)	0.074 (3)	0.067 (3)	0.013 (3)	0.034 (2)	−0.009 (2)
C6	0.077 (3)	0.073 (3)	0.046 (2)	0.005 (2)	0.022 (2)	−0.006 (2)
C7	0.050 (2)	0.038 (2)	0.040 (2)	−0.0043 (17)	0.0181 (17)	−0.0070 (15)
C8	0.065 (2)	0.043 (2)	0.047 (2)	−0.0127 (18)	0.0215 (18)	−0.0077 (16)
C9	0.057 (2)	0.039 (2)	0.049 (2)	−0.0055 (18)	0.0142 (17)	−0.0054 (16)
C10	0.049 (2)	0.038 (2)	0.047 (2)	−0.0009 (17)	0.0093 (17)	−0.0032 (15)
C11	0.084 (3)	0.081 (4)	0.096 (4)	0.018 (3)	0.033 (3)	0.018 (3)
N1	0.072 (2)	0.0452 (17)	0.0398 (16)	−0.0234 (16)	0.0283 (16)	−0.0108 (14)
O1	0.0841 (19)	0.0595 (18)	0.0454 (14)	−0.0210 (14)	0.0091 (13)	−0.0094 (12)
O2	0.0662 (17)	0.0630 (18)	0.0816 (19)	−0.0098 (14)	0.0372 (16)	0.0012 (14)
O3	0.0784 (18)	0.0485 (15)	0.0385 (13)	−0.0094 (13)	0.0292 (13)	−0.0069 (11)
S1	0.0622 (6)	0.0473 (6)	0.0471 (5)	−0.0178 (5)	0.0179 (4)	−0.0062 (4)

C1—C6	1.374 (5)	C8—H8A	0.9700
C1—C2	1.378 (5)	C8—H8B	0.9700
C1—S1	1.757 (4)	C9—C10	1.510 (4)
C2—C3	1.379 (6)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.379 (5)	C10—C10i	1.515 (6)
C3—H3	0.9300	C10—H10A	0.9700
C4—C5	1.360 (5)	C10—H10B	0.9700
C4—C11	1.503 (6)	C11—H11A	0.9600
C5—C6	1.383 (6)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—H6	0.9300	N1—S1	1.661 (3)
C7—O3	1.206 (3)	N1—H1N	0.851 (18)
C7—N1	1.384 (4)	O1—S1	1.425 (2)
C7—C8	1.498 (4)	O2—S1	1.423 (3)
C8—C9	1.507 (4)
C6—C1—C2	119.3 (4)	C8—C9—C10	113.0 (3)
C6—C1—S1	119.7 (3)	C8—C9—H9A	109.0
C2—C1—S1	121.0 (3)	C10—C9—H9A	109.0
C3—C2—C1	119.7 (4)	C8—C9—H9B	109.0
C3—C2—H2	120.2	C10—C9—H9B	109.0
C1—C2—H2	120.2	H9A—C9—H9B	107.8
C2—C3—C4	121.6 (4)	C9—C10—C10i	114.3 (3)
C2—C3—H3	119.2	C9—C10—H10A	108.7
C4—C3—H3	119.2	C10i—C10—H10A	108.7
C5—C4—C3	117.7 (4)	C9—C10—H10B	108.7
C5—C4—C11	121.6 (4)	C10i—C10—H10B	108.7
C3—C4—C11	120.7 (4)	H10A—C10—H10B	107.6
C4—C5—C6	121.9 (4)	C4—C11—H11A	109.5
C4—C5—H5	119.0	C4—C11—H11B	109.5
C6—C5—H5	119.0	H11A—C11—H11B	109.5
C1—C6—C5	119.7 (4)	C4—C11—H11C	109.5
C1—C6—H6	120.1	H11A—C11—H11C	109.5
C5—C6—H6	120.1	H11B—C11—H11C	109.5
O3—C7—N1	122.0 (3)	C7—N1—S1	125.0 (2)
O3—C7—C8	124.5 (3)	C7—N1—H1N	121 (2)
N1—C7—C8	113.6 (3)	S1—N1—H1N	114 (2)
C7—C8—C9	114.3 (3)	O2—S1—O1	120.31 (18)
C7—C8—H8A	108.7	O2—S1—N1	108.08 (15)
C9—C8—H8A	108.7	O1—S1—N1	103.64 (15)
C7—C8—H8B	108.7	O2—S1—C1	109.20 (16)
C9—C8—H8B	108.7	O1—S1—C1	108.66 (17)
H8A—C8—H8B	107.6	N1—S1—C1	105.98 (16)
C6—C1—C2—C3	1.0 (6)	C8—C9—C10—C10i	179.5 (4)
S1—C1—C2—C3	178.5 (3)	O3—C7—N1—S1	9.4 (5)
C1—C2—C3—C4	−1.7 (7)	C8—C7—N1—S1	−170.9 (3)
C2—C3—C4—C5	0.3 (6)	C7—N1—S1—O2	40.5 (3)
C2—C3—C4—C11	−177.9 (4)	C7—N1—S1—O1	169.2 (3)
C3—C4—C5—C6	1.8 (6)	C7—N1—S1—C1	−76.5 (3)
C11—C4—C5—C6	180.0 (4)	C6—C1—S1—O2	139.5 (3)
C2—C1—C6—C5	1.0 (6)	C2—C1—S1—O2	−38.0 (4)
S1—C1—C6—C5	−176.5 (3)	C6—C1—S1—O1	6.5 (3)
C4—C5—C6—C1	−2.4 (6)	C2—C1—S1—O1	−170.9 (3)
O3—C7—C8—C9	1.7 (5)	C6—C1—S1—N1	−104.3 (3)
N1—C7—C8—C9	−178.0 (3)	C2—C1—S1—N1	78.2 (3)
C7—C8—C9—C10	−176.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ii	0.85 (2)	2.12 (2)	2.968 (3)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.85 (2)	2.12 (2)	2.968 (3)	177 (3)

Symmetry code: (i) .