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ISSN: 2056-9890

N,N′-Bis[(4-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 28 February 2011; accepted 1 March 2011; online 5 March 2011)

In the centrosymmetric title compound, C20H24N2O6S2, the N—H and C=O bonds are trans to each other. In the crystal, inter­molecular N—H⋯O(S) hydrogen bonds link the mol­ecules 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[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.], 2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.]); Rodrigues et al. (2011[Rodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o789.]).

[Scheme 1]

Experimental

Crystal data
  • C20H24N2O6S2

  • Mr = 452.53

  • Triclinic, [P \overline 1]

  • 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[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.872, Tmax = 0.974

  • 3355 measured reflections

  • 2122 independent reflections

  • 1651 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O2i 0.84 (2) 2.11 (2) 2.938 (4) 170 (3)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, 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 a constituent of many biologically significant compounds. As a part of studying the effect of substituents on the structures of this class of compounds (Gowda et al., 2005, 2007; Rodrigues et al., 2011), in the present work, the structure of N,N-bis(4-methylphenylsulfonyl)-adipamide (I) has been determined (Fig.1). The asymmetric unit comprises half of a molecule, the remaining portion being generated via an inversion centre, similar to that observed in N,N-bis(2-methylphenylsulfonyl)-adipamide (II) (Rodrigues et al., 2011). 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. The molecule is bent at the S atom with the C—SO2—NH—C(O) torsion angle of -58.5 (3)°, compared to the value of -63.7 (4)° in (II). Further, the S1—N1—C7—C8 and C7—N1—S1—O2 segments are nearly linear. The torsion angles C2—C1—S1—N1 and C6—C1—S1—N1 are, respectively, -60.6 (3)° and 120.3 (3)°. The corresponding values in (II) 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 in (I) is 72.0 (1)°, compared to the value of 89.9 (1)° in (II).

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

Related literature top

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

Experimental top

N,N-Bis(4-methylphenylsulfonyl)-adipamide was prepared by refluxing a mixture of adipic acid (0.01 mol) with p-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. All other H atoms were positioned with idealized geometry using a riding model with aromatic 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 the title compound, showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound with hydrogen bonding shown as dashed lines.
N,N'-Bis[(4-methylphenyl)sulfonyl]adipamide top
Crystal data top
C20H24N2O6S2Z = 1
Mr = 452.53F(000) = 238
Triclinic, P1Dx = 1.423 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.0011 (9) ÅCell parameters from 1299 reflections
b = 8.765 (1) Åθ = 3.1–28.0°
c = 10.144 (2) ŵ = 0.29 mm1
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
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2122 independent reflections
Radiation source: fine-focus sealed tube1651 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 67
Tmin = 0.872, Tmax = 0.974k = 107
3355 measured reflectionsl = 1212
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H 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 parametersΔρmax = 0.78 e Å3
1 restraintΔρmin = 0.28 e Å3
Crystal data top
C20H24N2O6S2γ = 98.01 (1)°
Mr = 452.53V = 527.91 (14) Å3
Triclinic, P1Z = 1
a = 6.0011 (9) ÅMo Kα radiation
b = 8.765 (1) ŵ = 0.29 mm1
c = 10.144 (2) ÅT = 293 K
α = 90.04 (1)°0.48 × 0.12 × 0.09 mm
β = 92.35 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2122 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1651 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 0.974Rint = 0.021
3355 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0571 restraint
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.78 e Å3
2122 reflectionsΔρmin = 0.28 e Å3
140 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3932 (5)0.6198 (3)0.3150 (3)0.0359 (6)
C20.6161 (5)0.6864 (4)0.3058 (4)0.0474 (8)
H20.69460.67200.23060.057*
C30.7186 (6)0.7738 (4)0.4098 (4)0.0550 (9)
H30.86650.82080.40310.066*
C40.6072 (6)0.7940 (4)0.5246 (3)0.0521 (9)
C50.3872 (6)0.7224 (4)0.5321 (3)0.0550 (9)
H50.31070.73270.60880.066*
C60.2789 (5)0.6363 (4)0.4287 (3)0.0457 (8)
H60.13080.58980.43530.055*
C70.1735 (4)0.7710 (3)0.0561 (3)0.0366 (7)
C80.2257 (5)0.8691 (3)0.0642 (3)0.0392 (7)
H8A0.08700.89750.10300.047*
H8B0.29210.81000.12920.047*
C90.3879 (5)1.0149 (4)0.0284 (4)0.0483 (8)
H9A0.41171.07700.10700.058*
H9B0.31841.07430.03500.058*
C100.7223 (9)0.8915 (5)0.6365 (4)0.0829 (14)
H10A0.70180.99710.62270.099*
H10B0.88020.88310.64000.099*
H10C0.65820.85650.71810.099*
N10.2657 (5)0.6347 (3)0.0575 (3)0.0411 (6)
H1N0.353 (5)0.614 (4)0.000 (3)0.049*
O10.0322 (4)0.4586 (3)0.2128 (2)0.0569 (7)
O20.3994 (5)0.4024 (3)0.1391 (2)0.0585 (7)
O30.0681 (4)0.8081 (3)0.1472 (2)0.0532 (6)
S10.25952 (14)0.51241 (8)0.18165 (8)0.0417 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0382 (15)0.0335 (14)0.0367 (15)0.0053 (12)0.0077 (12)0.0048 (12)
C20.0387 (17)0.0537 (19)0.0501 (19)0.0044 (14)0.0134 (14)0.0067 (15)
C30.0404 (18)0.054 (2)0.066 (2)0.0062 (15)0.0037 (16)0.0106 (18)
C40.069 (2)0.0432 (17)0.0413 (19)0.0005 (16)0.0104 (16)0.0102 (14)
C50.066 (2)0.063 (2)0.0354 (18)0.0029 (18)0.0114 (16)0.0021 (16)
C60.0414 (17)0.0514 (18)0.0431 (18)0.0008 (14)0.0121 (14)0.0065 (14)
C70.0255 (14)0.0381 (15)0.0443 (17)0.0019 (12)0.0001 (12)0.0011 (13)
C80.0376 (16)0.0394 (15)0.0398 (17)0.0035 (12)0.0015 (13)0.0027 (13)
C90.0439 (18)0.0456 (18)0.054 (2)0.0022 (14)0.0027 (15)0.0095 (15)
C100.113 (4)0.066 (3)0.059 (3)0.015 (3)0.024 (2)0.006 (2)
N10.0521 (16)0.0372 (13)0.0349 (14)0.0079 (12)0.0069 (11)0.0008 (11)
O10.0529 (14)0.0520 (14)0.0595 (15)0.0161 (11)0.0062 (11)0.0040 (11)
O20.0910 (19)0.0375 (12)0.0521 (15)0.0215 (12)0.0213 (13)0.0053 (10)
O30.0475 (13)0.0578 (14)0.0580 (15)0.0152 (11)0.0218 (11)0.0072 (12)
S10.0516 (5)0.0318 (4)0.0411 (4)0.0018 (3)0.0091 (3)0.0013 (3)
Geometric parameters (Å, º) top
C1—C61.383 (4)C7—C81.511 (4)
C1—C21.389 (4)C8—C91.529 (4)
C1—S11.749 (3)C8—H8A0.9700
C2—C31.376 (5)C8—H8B0.9700
C2—H20.9300C9—C9i1.498 (6)
C3—C41.390 (5)C9—H9A0.9700
C3—H30.9300C9—H9B0.9700
C4—C51.386 (5)C10—H10A0.9600
C4—C101.505 (5)C10—H10B0.9600
C5—C61.378 (5)C10—H10C0.9600
C5—H50.9300N1—S11.653 (3)
C6—H60.9300N1—H1N0.837 (18)
C7—O31.210 (4)O1—S11.428 (2)
C7—N11.385 (4)O2—S11.441 (2)
C6—C1—C2120.6 (3)C7—C8—H8B109.4
C6—C1—S1120.3 (2)C9—C8—H8B109.4
C2—C1—S1119.1 (2)H8A—C8—H8B108.0
C3—C2—C1118.8 (3)C9i—C9—C8114.2 (3)
C3—C2—H2120.6C9i—C9—H9A108.7
C1—C2—H2120.6C8—C9—H9A108.7
C2—C3—C4121.8 (3)C9i—C9—H9B108.7
C2—C3—H3119.1C8—C9—H9B108.7
C4—C3—H3119.1H9A—C9—H9B107.6
C5—C4—C3117.9 (3)C4—C10—H10A109.5
C5—C4—C10121.3 (4)C4—C10—H10B109.5
C3—C4—C10120.8 (4)H10A—C10—H10B109.5
C6—C5—C4121.6 (3)C4—C10—H10C109.5
C6—C5—H5119.2H10A—C10—H10C109.5
C4—C5—H5119.2H10B—C10—H10C109.5
C5—C6—C1119.2 (3)C7—N1—S1125.4 (2)
C5—C6—H6120.4C7—N1—H1N122 (2)
C1—C6—H6120.4S1—N1—H1N112 (2)
O3—C7—N1121.5 (3)O1—S1—O2118.77 (16)
O3—C7—C8124.2 (3)O1—S1—N1110.32 (15)
N1—C7—C8114.2 (3)O2—S1—N1103.00 (14)
C7—C8—C9111.2 (3)O1—S1—C1109.01 (15)
C7—C8—H8A109.4O2—S1—C1109.75 (15)
C9—C8—H8A109.4N1—S1—C1105.04 (13)
C6—C1—C2—C32.4 (5)C7—C8—C9—C9i61.1 (5)
S1—C1—C2—C3178.4 (3)O3—C7—N1—S13.7 (4)
C1—C2—C3—C41.7 (5)C8—C7—N1—S1173.6 (2)
C2—C3—C4—C50.2 (5)C7—N1—S1—O158.8 (3)
C2—C3—C4—C10179.4 (3)C7—N1—S1—O2173.4 (3)
C3—C4—C5—C61.3 (5)C7—N1—S1—C158.5 (3)
C10—C4—C5—C6178.3 (3)C6—C1—S1—O12.0 (3)
C4—C5—C6—C10.5 (5)C2—C1—S1—O1178.8 (2)
C2—C1—C6—C51.4 (5)C6—C1—S1—O2129.6 (3)
S1—C1—C6—C5179.5 (3)C2—C1—S1—O249.5 (3)
O3—C7—C8—C967.3 (4)C6—C1—S1—N1120.3 (3)
N1—C7—C8—C9109.9 (3)C2—C1—S1—N160.6 (3)
Symmetry code: (i) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2ii0.84 (2)2.11 (2)2.938 (4)170 (3)
Symmetry code: (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC20H24N2O6S2
Mr452.53
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.0011 (9), 8.765 (1), 10.144 (2)
α, β, γ (°)90.04 (1), 92.35 (1), 98.01 (1)
V3)527.91 (14)
Z1
Radiation typeMo Kα
µ (mm1)0.29
Crystal size (mm)0.48 × 0.12 × 0.09
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.872, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
3355, 2122, 1651
Rint0.021
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.141, 1.08
No. of reflections2122
No. of parameters140
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.78, 0.28

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···O2i0.837 (18)2.109 (19)2.938 (4)170 (3)
Symmetry code: (i) x+1, y+1, z.
 

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., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106–112.  CAS Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationRodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o789.  Web of Science CSD CrossRef IUCr Journals 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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