N,N′-Bis(2-chloro­phenyl­sulfon­yl)adipamide

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

doi:10.1107/S1600536811008464

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o837

doi:10.1107/S1600536811008464

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N,N′-Bis(2-chlorophenylsulfonyl)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 1 March 2011; accepted 6 March 2011; online 12 March 2011)

In the centrosymmetric title compound, C₁₈H₁₈Cl₂N₂O₆S₂, 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. The dihedral angle between the planes of the benzene ring and the central part of the molecule is 89.6 (2)°. In the crystal, intermolecular N—H⋯O(S) hydrogen bonds link the molecules into sheets along the b axis.

Related literature

For the effect of substituents on the structures of amides and sulfonamides, see: Gowda et al. (2000 , 2005 ); Rodrigues et al. (2011 ).

Experimental

Crystal data

C₁₈H₁₈Cl₂N₂O₆S₂
M_r = 493.36
Monoclinic, P 2₁ /n
a = 11.899 (2) Å
b = 5.564 (1) Å
c = 16.333 (3) Å
β = 96.56 (2)°
V = 1074.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 293 K
0.44 × 0.08 × 0.01 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 = 0.799, T_max = 0.995
3439 measured reflections
1971 independent reflections
1120 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.089
wR(F²) = 0.143
S = 1.26
1971 reflections
139 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.30 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 (3)	2.08 (3)	2.901 (6)	168 (6)
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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/S1600536811008464/bq2284sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008464/bq2284Isup2.hkl

checkCIF report

Comment top

The amide and sulfonamide moieties are important constituents 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., 2000, 2005; Rodrigues et al., 2011), in the present work, the structure of N,N-bis(2-chlorophenylsulfonyl)-adipamide (I) has been determined (Fig.1). The asymmetric unit comprises half of a molecule, the remaining portion is generated through 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 -65.1 (6)°, compared to the value of -63.7 (4)° in (II). 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 -69.5 (6)° and 108.8 (5)°, respectively. The corresponding values in (II) are -71.3 (4)° and 106.9 (4)°.

The dihedral angle between the planes of the benzene ring and the SO₂—NH—C(O)—C—C segment in (I) is 89.6 (2)°, compared to the value of 89.9 (1)° in (II).

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 sheets running in the direction of b axis (Fig. 2).

Related literature top

For the effect of substituents on the structures of amides and sulfonamides, see: Gowda et al. (2000, 2005); Rodrigues et al. (2011).

Experimental top

N,N-Bis(2-chlorophenylsulfonyl)-adipamide was prepared by refluxing a mixture of adipic acid (0.01 mol) with 2-chlorobenzenesulfonamide (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 the 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 labeling 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-chlorophenylsulfonyl)heptanediamide top

Crystal data top

C₁₈H₁₈Cl₂N₂O₆S₂	F(000) = 508
M_r = 493.36	D_x = 1.525 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 660 reflections
a = 11.899 (2) Å	θ = 2.9–27.9°
b = 5.564 (1) Å	µ = 0.54 mm⁻¹
c = 16.333 (3) Å	T = 293 K
β = 96.56 (2)°	Needle, colourless
V = 1074.3 (3) Å³	0.44 × 0.08 × 0.01 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1971 independent reflections
Radiation source: fine-focus sealed tube	1120 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Rotation method data acquisition using ω scans.	θ_max = 25.7°, θ_min = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→14
T_min = 0.799, T_max = 0.995	k = −6→6
3439 measured reflections	l = −19→17

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)] = 0.089	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ²(F_o²) + (0.0112P)² + 2.7686P] where P = (F_o² + 2F_c²)/3
1971 reflections	(Δ/σ)_max = 0.004
139 parameters	Δρ_max = 0.34 e Å⁻³
2 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₁₈Cl₂N₂O₆S₂	V = 1074.3 (3) Å³
M_r = 493.36	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.899 (2) Å	µ = 0.54 mm⁻¹
b = 5.564 (1) Å	T = 293 K
c = 16.333 (3) Å	0.44 × 0.08 × 0.01 mm
β = 96.56 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1971 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1120 reflections with I > 2σ(I)
T_min = 0.799, T_max = 0.995	R_int = 0.049
3439 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.089	2 restraints
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	Δρ_max = 0.34 e Å⁻³
1971 reflections	Δρ_min = −0.30 e Å⁻³
139 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
Cl1	−0.14610 (17)	0.2330 (4)	0.10849 (12)	0.0762 (7)
S1	−0.08046 (13)	−0.2093 (3)	0.23869 (9)	0.0378 (4)
O1	−0.1884 (3)	−0.2383 (8)	0.1916 (2)	0.0465 (12)
O2	−0.0261 (4)	−0.4127 (8)	0.2782 (3)	0.0538 (13)
O3	0.0751 (3)	0.0106 (9)	0.3729 (2)	0.0498 (13)
N1	−0.1028 (4)	−0.0070 (10)	0.3079 (3)	0.0365 (13)
H1N	−0.166 (3)	0.059 (10)	0.302 (3)	0.044*
C1	0.0147 (5)	−0.0762 (12)	0.1772 (3)	0.0361 (15)
C2	−0.0119 (6)	0.1105 (12)	0.1239 (4)	0.0470 (18)
C3	0.0707 (8)	0.2089 (17)	0.0807 (5)	0.081 (3)
H3	0.0530	0.3363	0.0447	0.098*
C4	0.1783 (9)	0.119 (2)	0.0912 (6)	0.098 (3)
H4	0.2336	0.1867	0.0627	0.118*
C5	0.2053 (7)	−0.069 (2)	0.1429 (6)	0.087 (3)
H5	0.2783	−0.1315	0.1486	0.105*
C6	0.1249 (6)	−0.1668 (15)	0.1864 (4)	0.060 (2)
H6	0.1437	−0.2941	0.2222	0.072*
C7	−0.0219 (5)	0.0781 (11)	0.3683 (4)	0.0349 (15)
C8	−0.0660 (4)	0.2510 (12)	0.4273 (3)	0.0375 (15)
H8A	−0.1021	0.1608	0.4679	0.045*
H8B	−0.1233	0.3515	0.3973	0.045*
C9	0.0245 (5)	0.4113 (11)	0.4718 (3)	0.0389 (16)
H9A	0.0803	0.3122	0.5039	0.047*
H9B	0.0625	0.4984	0.4315	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0866 (15)	0.0669 (15)	0.0744 (14)	0.0315 (13)	0.0064 (11)	0.0128 (12)
S1	0.0402 (9)	0.0383 (10)	0.0347 (9)	−0.0033 (8)	0.0034 (7)	−0.0051 (9)
O1	0.033 (2)	0.056 (3)	0.048 (3)	−0.014 (2)	−0.0038 (19)	−0.013 (2)
O2	0.076 (3)	0.035 (3)	0.049 (3)	0.002 (3)	0.001 (2)	0.003 (2)
O3	0.036 (2)	0.061 (3)	0.051 (3)	0.008 (2)	−0.005 (2)	−0.016 (2)
N1	0.028 (3)	0.047 (4)	0.035 (3)	0.002 (3)	0.002 (2)	−0.008 (3)
C1	0.038 (4)	0.039 (4)	0.031 (4)	−0.005 (3)	0.006 (3)	−0.005 (3)
C2	0.059 (4)	0.035 (4)	0.048 (4)	0.006 (3)	0.011 (4)	−0.003 (4)
C3	0.108 (8)	0.072 (6)	0.070 (6)	−0.004 (6)	0.036 (5)	0.022 (5)
C4	0.084 (7)	0.120 (10)	0.101 (8)	−0.021 (7)	0.054 (6)	0.008 (7)
C5	0.052 (5)	0.124 (9)	0.091 (7)	0.005 (6)	0.030 (5)	−0.006 (7)
C6	0.050 (4)	0.080 (6)	0.051 (5)	0.005 (4)	0.014 (4)	0.004 (4)
C7	0.030 (3)	0.039 (4)	0.036 (4)	−0.002 (3)	0.003 (3)	0.009 (3)
C8	0.039 (3)	0.045 (4)	0.028 (3)	0.002 (3)	0.005 (3)	−0.006 (3)
C9	0.041 (4)	0.038 (4)	0.036 (4)	0.006 (3)	−0.004 (3)	−0.006 (3)

Geometric parameters (Å, º) top

Cl1—C2	1.728 (7)	C4—C5	1.359 (12)
S1—O2	1.421 (4)	C4—H4	0.9300
S1—O1	1.429 (4)	C5—C6	1.367 (10)
S1—N1	1.638 (5)	C5—H5	0.9300
S1—C1	1.760 (6)	C6—H6	0.9300
O3—C7	1.208 (6)	C7—C8	1.499 (8)
N1—C7	1.381 (7)	C8—C9	1.518 (7)
N1—H1N	0.84 (3)	C8—H8A	0.9700
C1—C2	1.370 (8)	C8—H8B	0.9700
C1—C6	1.397 (8)	C9—C9ⁱ	1.511 (11)
C2—C3	1.386 (9)	C9—H9A	0.9700
C3—C4	1.367 (11)	C9—H9B	0.9700
C3—H3	0.9300

O2—S1—O1	119.3 (3)	C4—C5—C6	119.9 (9)
O2—S1—N1	109.6 (3)	C4—C5—H5	120.1
O1—S1—N1	104.0 (2)	C6—C5—H5	120.1
O2—S1—C1	107.7 (3)	C5—C6—C1	120.4 (8)
O1—S1—C1	109.7 (3)	C5—C6—H6	119.8
N1—S1—C1	105.7 (3)	C1—C6—H6	119.8
C7—N1—S1	125.0 (4)	O3—C7—N1	121.4 (6)
C7—N1—H1N	119 (4)	O3—C7—C8	124.2 (5)
S1—N1—H1N	116 (4)	N1—C7—C8	114.4 (5)
C2—C1—C6	119.2 (6)	C7—C8—C9	113.8 (4)
C2—C1—S1	124.4 (5)	C7—C8—H8A	108.8
C6—C1—S1	116.4 (5)	C9—C8—H8A	108.8
C1—C2—C3	119.8 (7)	C7—C8—H8B	108.8
C1—C2—Cl1	122.3 (5)	C9—C8—H8B	108.8
C3—C2—Cl1	117.9 (6)	H8A—C8—H8B	107.7
C4—C3—C2	119.9 (8)	C9ⁱ—C9—C8	112.0 (6)
C4—C3—H3	120.0	C9ⁱ—C9—H9A	109.2
C2—C3—H3	120.0	C8—C9—H9A	109.2
C5—C4—C3	120.8 (8)	C9ⁱ—C9—H9B	109.2
C5—C4—H4	119.6	C8—C9—H9B	109.2
C3—C4—H4	119.6	H9A—C9—H9B	107.9

O2—S1—N1—C7	50.8 (6)	C1—C2—C3—C4	0.3 (12)
O1—S1—N1—C7	179.4 (5)	Cl1—C2—C3—C4	179.7 (7)
C1—S1—N1—C7	−65.1 (6)	C2—C3—C4—C5	0.8 (15)
O2—S1—C1—C2	173.5 (5)	C3—C4—C5—C6	−1.4 (16)
O1—S1—C1—C2	42.1 (6)	C4—C5—C6—C1	0.8 (13)
N1—S1—C1—C2	−69.5 (6)	C2—C1—C6—C5	0.3 (11)
O2—S1—C1—C6	−8.2 (6)	S1—C1—C6—C5	−178.1 (6)
O1—S1—C1—C6	−139.6 (5)	S1—N1—C7—O3	2.1 (9)
N1—S1—C1—C6	108.8 (5)	S1—N1—C7—C8	−176.2 (5)
C6—C1—C2—C3	−0.9 (10)	O3—C7—C8—C9	23.4 (9)
S1—C1—C2—C3	177.3 (6)	N1—C7—C8—C9	−158.5 (5)
C6—C1—C2—Cl1	179.8 (5)	C7—C8—C9—C9ⁱ	177.9 (6)
S1—C1—C2—Cl1	−1.9 (8)

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 (3)	2.08 (3)	2.901 (6)	168 (6)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈Cl₂N₂O₆S₂
M_r	493.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.899 (2), 5.564 (1), 16.333 (3)
β (°)	96.56 (2)
V (Å³)	1074.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.44 × 0.08 × 0.01

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	0.799, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	3439, 1971, 1120
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.089, 0.143, 1.26
No. of reflections	1971
No. of parameters	139
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.30

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	0.84 (3)	2.08 (3)	2.901 (6)	168 (6)

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 award of a research fellowship.

References

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