N,N′-Bis[(4-methyl­phen­yl)sulfon­yl]adipamide

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

doi:10.1107/S1600536811007756

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o788

doi:10.1107/S1600536811007756

Open

access

N,N′-Bis[(4-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 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 , 2007 ); Rodrigues et al. (2011 ).

Experimental

Crystal data

C₂₀H₂₄N₂O₆S₂
M_r = 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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[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
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.28 e Å⁻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) -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 ); 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/S1600536811007756/bt5485sup1.cif

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

checkCIF report

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.

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 the title compound, showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	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

C₂₀H₂₄N₂O₆S₂	Z = 1
M_r = 452.53	F(000) = 238
Triclinic, P1	D_x = 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

Data collection top

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 monochromator	R_int = 0.021
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→7
T_min = 0.872, T_max = 0.974	k = −10→7
3355 measured reflections	l = −12→12

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)] = 0.057	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(F_o²) + (0.0507P)² + 0.6262P] where P = (F_o² + 2F_c²)/3
2122 reflections	(Δ/σ)_max < 0.001
140 parameters	Δρ_max = 0.78 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₀H₂₄N₂O₆S₂	γ = 98.01 (1)°
M_r = 452.53	V = 527.91 (14) Å³
Triclinic, P1	Z = 1
a = 6.0011 (9) Å	Mo Kα radiation
b = 8.765 (1) Å	µ = 0.29 mm⁻¹
c = 10.144 (2) Å	T = 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)
T_min = 0.872, T_max = 0.974	R_int = 0.021
3355 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	1 restraint
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.78 e Å⁻³
2122 reflections	Δρ_min = −0.28 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄N₂O₆S₂
M_r	452.53
Crystal system, space group	Triclinic, 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)
V (Å³)	527.91 (14)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.48 × 0.12 × 0.09

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	0.872, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	3355, 2122, 1651
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.141, 1.08
No. of reflections	2122
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)	0.78, −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···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.837 (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

Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106–112. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Rodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o789. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar