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

Rodrigues, V.Z.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811007203

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o789

doi:10.1107/S1600536811007203

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

Vinola Z. Rodrigues,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^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 , 2010a ,b ).

Experimental

Crystal data

C₂₀H₂₄N₂O₆S₂
M_r = 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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[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
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

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

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

checkCIF report

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.

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

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

N,N'-Bis[(2-methylphenyl)sulfonyl]hexanediamide top

Crystal data top

C₂₀H₂₄N₂O₆S₂	F(000) = 476
M_r = 452.53	D_x = 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

Data collection top

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 monochromator	R_int = 0.037
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→13
T_min = 0.875, T_max = 0.989	k = −5→6
3521 measured reflections	l = −14→20

Refinement top

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(F_o²) + (0.0079P)² + 2.6127P] where P = (F_o² + 2F_c²)/3
2135 reflections	(Δ/σ)_max = 0.001
140 parameters	Δρ_max = 0.52 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₀H₂₄N₂O₆S₂	V = 1077.5 (4) Å³
M_r = 452.53	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.928 (2) Å	µ = 0.29 mm⁻¹
b = 5.523 (1) Å	T = 293 K
c = 16.447 (4) Å	0.48 × 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)
T_min = 0.875, T_max = 0.989	R_int = 0.037
3521 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	1 restraint
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.31	Δρ_max = 0.52 e Å⁻³
2135 reflections	Δρ_min = −0.29 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (ii) −x−1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄N₂O₆S₂
M_r	452.53
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.928 (2), 5.523 (1), 16.447 (4)
β (°)	96.05 (2)
V (Å³)	1077.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.48 × 0.12 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.875, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	3521, 2135, 1571
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.147, 1.31
No. of reflections	2135
No. of parameters	140
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.843 (19)	2.09 (2)	2.917 (4)	166 (4)

Symmetry code: (i) −x−1/2, 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

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