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ISSN: 2056-9890

N,N′-Bis[(2-methyl­phenyl)sulfon­yl]adipamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 22 February 2011; accepted 25 February 2011; online 5 March 2011)

The asymmetric unit of the title compound, C20H24N2O6S2, comprises one half-mol­ecule, the remaining portion being generated via an inversion centre. The dihedral angle between the plane of the benzene ring and the SO2—NH—C(O)—C—C segment is 89.9 (1)°. In the crystal, inter­molecular N—H⋯O(S) hydrogen bonds link the mol­ecules into infinite chains in [101].

Related literature

For related structures, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.], 2010a[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010a). Acta Cryst. E66, o181.],b[Gowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010b). Acta Cryst. E66, o1363.]).

[Scheme 1]

Experimental

Crystal data
  • C20H24N2O6S2

  • Mr = 452.53

  • Monoclinic, P 21 /n

  • 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[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.875, Tmax = 0.989

  • 3521 measured reflections

  • 2135 independent reflections

  • 1571 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.076

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.84 (2) 2.09 (2) 2.917 (4) 166 (4)
Symmetry code: (i) [-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The sulfonamide moiety is an important constituent of many biologically important compounds. As a part of studying the substituent effects on the structures of this class of compounds (Gowda et al., 2007, 2010a,b), in the present work, the structure of N,N-bis(2-methylphenylsulfonyl)-adipamide has been determined (Fig.1). The asymmetric unit comprises half of a molecule, the remaining portion being generated via an inversion centre. The conformation of the N—H and C=O bonds in the C—SO2—NH—C(O)—C—C segment is anti to each other and the amide O atom is also anti to the H atoms attached to the adjacent C atom. Further, the conformation of the N—H bond in the amide fragment is syn to the ortho-methyl group in the adjacent benzene ring. The molecule is bent at the S atom with the C—SO2—NH—C(O) torsion angle of -63.7 (4)°. Further, the S1—N1—C7—C8 and C7—N1—S1—O1 segments are nearly linear. The torsion angles C2—C1—S1—N1 and C6—C1—S1—N1 are -71.3 (4)° and 106.9 (4)°, respectively.

The dihedral angle between the planes of the benzene ring and the SO2—NH—C(O)—C—C segment is 89.9 (1)°.

N—H···O1(S) H-bond formation results in an S=O1 bond longer than the S=O2 bond. A series of N—H···O(S) intermolecular hydrogen bonds (Table 1) link the molecules into infinite chains running in the [101] direction (Fig. 2).

Related literature top

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

Experimental top

N,N-Bis(2-methylphenylsulfonyl)-adipamide was prepared by refluxing a mixture of adipic acid (0.01 mol) with o-toluenesulfonamide (0.02 mol) and POCl3 for 1 hr on a water bath. The reaction mixture was allowed to cool and added ether to it. The solid product obtained was filtered, washed thoroughly with ether and hot ethanol. The compound was recrystallized to the constant melting point and was characterized by its infrared and NMR spectra.

Needle like colorless single crystals used in the X-ray diffraction studies were grown by a slow evaporation of a solution of the compound in ethanol at room temperature.

Refinement top

The H atom of the NH group was located in a difference map and later restrained to the distance N—H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with ring C—H distance = 0.93 Å, methylene C—H = 0.97 Å and methyl C—H = 0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
N,N'-Bis[(2-methylphenyl)sulfonyl]hexanediamide top
Crystal data top
C20H24N2O6S2F(000) = 476
Mr = 452.53Dx = 1.395 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1186 reflections
a = 11.928 (2) Åθ = 2.9–27.9°
b = 5.523 (1) ŵ = 0.29 mm1
c = 16.447 (4) ÅT = 293 K
β = 96.05 (2)°Needle, colourless
V = 1077.5 (4) Å30.48 × 0.12 × 0.04 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2135 independent reflections
Radiation source: fine-focus sealed tube1571 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1413
Tmin = 0.875, Tmax = 0.989k = 56
3521 measured reflectionsl = 1420
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H 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 parametersΔρmax = 0.52 e Å3
1 restraintΔρmin = 0.29 e Å3
Crystal data top
C20H24N2O6S2V = 1077.5 (4) Å3
Mr = 452.53Z = 2
Monoclinic, P21/nMo Kα radiation
a = 11.928 (2) ŵ = 0.29 mm1
b = 5.523 (1) ÅT = 293 K
c = 16.447 (4) Å0.48 × 0.12 × 0.04 mm
β = 96.05 (2)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2135 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1571 reflections with I > 2σ(I)
Tmin = 0.875, Tmax = 0.989Rint = 0.037
3521 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0761 restraint
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.31Δρmax = 0.52 e Å3
2135 reflectionsΔρmin = 0.29 e Å3
140 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.08049 (9)0.2084 (2)0.23912 (6)0.0351 (3)
O10.1885 (2)0.2313 (6)0.19216 (18)0.0455 (8)
O20.0301 (3)0.4181 (6)0.27714 (19)0.0516 (9)
O30.0740 (2)0.0040 (6)0.37419 (19)0.0477 (9)
N10.1032 (3)0.0087 (7)0.3094 (2)0.0369 (9)
H1N0.165 (2)0.064 (7)0.300 (3)0.044*
C10.0160 (3)0.0737 (8)0.1790 (3)0.0369 (10)
C20.0143 (4)0.1150 (9)0.1259 (3)0.0482 (12)
C30.0713 (5)0.2137 (13)0.0847 (4)0.0775 (19)
H30.05470.34110.04850.093*
C40.1795 (6)0.1268 (15)0.0966 (4)0.092 (2)
H40.23560.19860.06960.110*
C50.2054 (5)0.0632 (15)0.1476 (4)0.082 (2)
H50.27830.12480.15350.098*
C60.1249 (4)0.1647 (11)0.1902 (3)0.0589 (15)
H60.14280.29240.22610.071*
C70.0216 (3)0.0753 (8)0.3696 (2)0.0324 (9)
C80.0659 (3)0.2492 (8)0.4283 (2)0.0345 (10)
H8A0.10130.15820.46910.041*
H8B0.12330.34950.39890.041*
C90.0242 (3)0.4117 (8)0.4713 (2)0.0361 (10)
H910.08080.31240.50210.043*
H920.06080.50120.43080.043*
C100.1313 (4)0.2174 (11)0.1094 (3)0.0661 (16)
H10A0.17790.10630.07610.079*
H10B0.12820.36930.08140.079*
H10C0.16250.24180.16030.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0338 (5)0.0381 (6)0.0326 (5)0.0040 (5)0.0005 (4)0.0031 (5)
O10.0365 (16)0.055 (2)0.0431 (17)0.0145 (16)0.0039 (13)0.0087 (16)
O20.064 (2)0.041 (2)0.049 (2)0.0036 (17)0.0004 (16)0.0035 (17)
O30.0293 (16)0.059 (2)0.053 (2)0.0087 (15)0.0038 (13)0.0119 (17)
N10.0268 (18)0.049 (2)0.0343 (19)0.0053 (17)0.0021 (15)0.0065 (18)
C10.031 (2)0.045 (3)0.035 (2)0.005 (2)0.0055 (18)0.008 (2)
C20.055 (3)0.047 (3)0.042 (3)0.002 (2)0.006 (2)0.002 (2)
C30.087 (4)0.081 (5)0.068 (4)0.008 (4)0.030 (3)0.020 (4)
C40.069 (4)0.114 (6)0.099 (5)0.029 (4)0.044 (4)0.007 (5)
C50.043 (3)0.125 (6)0.082 (5)0.003 (4)0.023 (3)0.013 (5)
C60.041 (3)0.083 (4)0.054 (3)0.007 (3)0.007 (2)0.001 (3)
C70.030 (2)0.037 (2)0.029 (2)0.0020 (19)0.0008 (17)0.0015 (19)
C80.029 (2)0.044 (3)0.030 (2)0.0057 (19)0.0005 (16)0.002 (2)
C90.034 (2)0.041 (3)0.033 (2)0.001 (2)0.0007 (17)0.004 (2)
C100.072 (4)0.061 (4)0.065 (4)0.015 (3)0.006 (3)0.016 (3)
Geometric parameters (Å, º) top
S1—O21.419 (3)C4—H40.9300
S1—O11.436 (3)C5—C61.368 (8)
S1—N11.641 (4)C5—H50.9300
S1—C11.760 (4)C6—H60.9300
O3—C71.201 (5)C7—C81.497 (6)
N1—C71.393 (5)C8—C91.516 (6)
N1—H1N0.843 (19)C8—H8A0.9700
C1—C21.383 (7)C8—H8B0.9700
C1—C61.387 (6)C9—C9i1.514 (8)
C2—C31.394 (7)C9—H910.9700
C2—C101.504 (7)C9—H920.9700
C3—C41.372 (9)C10—H10A0.9600
C3—H30.9300C10—H10B0.9600
C4—C51.358 (10)C10—H10C0.9600
O2—S1—O1118.7 (2)C5—C6—C1118.7 (6)
O2—S1—N1109.39 (19)C5—C6—H6120.6
O1—S1—N1103.45 (18)C1—C6—H6120.6
O2—S1—C1108.7 (2)O3—C7—N1121.6 (4)
O1—S1—C1109.7 (2)O3—C7—C8124.5 (4)
N1—S1—C1106.1 (2)N1—C7—C8113.9 (3)
C7—N1—S1124.7 (3)C7—C8—C9113.6 (3)
C7—N1—H1N120 (3)C7—C8—H8A108.8
S1—N1—H1N114 (3)C9—C8—H8A108.8
C2—C1—C6122.4 (4)C7—C8—H8B108.8
C2—C1—S1122.1 (3)C9—C8—H8B108.8
C6—C1—S1115.5 (4)H8A—C8—H8B107.7
C1—C2—C3116.5 (5)C9i—C9—C8112.0 (4)
C1—C2—C10124.9 (4)C9i—C9—H91109.2
C3—C2—C10118.6 (5)C8—C9—H91109.2
C4—C3—C2121.4 (6)C9i—C9—H92109.2
C4—C3—H3119.3C8—C9—H92109.2
C2—C3—H3119.3H91—C9—H92107.9
C5—C4—C3120.5 (6)C2—C10—H10A109.5
C5—C4—H4119.8C2—C10—H10B109.5
C3—C4—H4119.8H10A—C10—H10B109.5
C4—C5—C6120.5 (6)C2—C10—H10C109.5
C4—C5—H5119.7H10A—C10—H10C109.5
C6—C5—H5119.7H10B—C10—H10C109.5
O2—S1—N1—C753.4 (4)C1—C2—C3—C40.1 (9)
O1—S1—N1—C7179.3 (4)C10—C2—C3—C4179.4 (6)
C1—S1—N1—C763.7 (4)C2—C3—C4—C51.7 (11)
O2—S1—C1—C2171.1 (4)C3—C4—C5—C62.5 (11)
O1—S1—C1—C239.9 (4)C4—C5—C6—C11.5 (10)
N1—S1—C1—C271.3 (4)C2—C1—C6—C50.3 (8)
O2—S1—C1—C610.7 (4)S1—C1—C6—C5177.8 (5)
O1—S1—C1—C6141.9 (4)S1—N1—C7—O30.2 (6)
N1—S1—C1—C6106.9 (4)S1—N1—C7—C8177.5 (3)
C6—C1—C2—C31.1 (7)O3—C7—C8—C925.3 (6)
S1—C1—C2—C3176.9 (4)N1—C7—C8—C9157.5 (4)
C6—C1—C2—C10178.4 (5)C7—C8—C9—C9i178.8 (4)
S1—C1—C2—C103.6 (7)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1ii0.84 (2)2.09 (2)2.917 (4)166 (4)
Symmetry code: (ii) x1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC20H24N2O6S2
Mr452.53
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)11.928 (2), 5.523 (1), 16.447 (4)
β (°) 96.05 (2)
V3)1077.5 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.29
Crystal size (mm)0.48 × 0.12 × 0.04
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.875, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
3521, 2135, 1571
Rint0.037
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.076, 0.147, 1.31
No. of reflections2135
No. of parameters140
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.52, 0.29

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.843 (19)2.09 (2)2.917 (4)166 (4)
Symmetry code: (i) x1/2, y+1/2, z+1/2.
 

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship.

References

First citationGowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010a). Acta Cryst. E66, o181.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010b). Acta Cryst. E66, o1363.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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