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

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

doi:10.1107/S1600536811009196

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o884

doi:10.1107/S1600536811009196

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

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 8 March 2011; accepted 10 March 2011; online 15 March 2011)

In the crystal of the title compound, C₂₀H₂₂Cl₂N₂O₆S₂, the asymmetric unit comprises half of a molecule, the remaining portion is generated via an inversion centre. The conformation of the N—H and C=O bonds in the SO₂–NH–C(O)–C segment is anti. The molecule is bent at the S atom with the C–SO₂–NH–C(O) torsion angle being 68.16 (19)°. The dihedral angle between the plane of the benzene ring and the SO₂–NH–C(O)–C segment is 77.5 (1)°. Hydrogen bonds of the type N—H⋯O(C) link molecules into supramolecular chains along the b axis.

Related literature

For the study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000 ). For the effect of substituents in N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ). For the effect of substituents on the structures of N-(arylsulfonyl)-amides, see: Rodrigues et al. (2011 ).

Experimental

Crystal data

C₂₀H₂₂Cl₂N₂O₆S₂
M_r = 521.42
Monoclinic, P 2₁ /c
a = 7.8737 (9) Å
b = 9.717 (1) Å
c = 14.616 (2) Å
β = 94.575 (9)°
V = 1114.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 293 K
0.36 × 0.22 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.835, T_max = 0.950
4126 measured reflections
2276 independent reflections
1744 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.104
S = 1.05
2276 reflections
148 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.83 (2)	2.20 (2)	3.020 (2)	172 (2)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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/S1600536811009196/tk2727sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009196/tk2727Isup2.hkl

checkCIF report

Comment top

The amide and sulfonamide moieties are important constituents of many biologically significant compounds. As part of an investigation 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)-suberamide (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-chlorophenylsulfonyl)-adipamide (II) (Rodrigues et al., 2011). The conformation of the N—H and C═O bonds in the SO₂—NH—C(═O)—C segment is anti. The molecule is bent at the S atom with the C—SO₂—NH—C(═O) torsion angle being 68.16 (19) °, compared to the value of -65.1 (6)° in (II). The torsion angles C2—C1—S1—N1 and C6—C1—S1—N1 are, respectively, 70.6 (2)° and -113.32 (17)°. The corresponding values in (II) are -69.5 (6) ° and 108.8 (5) °, respectively. The dihedral angle between the planes of the benzene ring and the SO₂—NH—C(═O)—C segment in (I) is 77.5 (1) °, compared to the value of 89.6 (2) ° in (II).

A series of N—H···O(C) intermolecular hydrogen bonds (Table 1) link the molecules into chains running along the b axis (Fig. 2).

Related literature top

For the study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000). For the effect of substituents in N-(aryl)-arylsulfonamides, see: Gowda et al. (2005). For the effect of substituents on the structures of N-(arylsulfonyl)-amides, see: Rodrigues et al. (2011).

Experimental top

Compound (I) was prepared by refluxing a mixture of suberic acid (0.01 mol) with 2-chlorobenzenesulfonamide (0.02 mol) and POCl₃ for 1 h on a water bath. The reaction mixture was allowed to cool and diethyl ether added. The solid product obtained was filtered, washed thoroughly with ether and hot ethanol. The compound was recrystallized to a constant melting point. Colourless prisms were grown by the slow evaporation of its ethanol solution 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 at the 50% probability level.
	Fig. 2. Molecular packing of (I) viewed in projection down the a axis and with hydrogen bonding shown as dashed lines.

N,N'-Bis(2-chlorophenylsulfonyl)octanediamide top

Crystal data top

C₂₀H₂₂Cl₂N₂O₆S₂	F(000) = 540
M_r = 521.42	D_x = 1.553 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1476 reflections
a = 7.8737 (9) Å	θ = 2.6–27.7°
b = 9.717 (1) Å	µ = 0.52 mm⁻¹
c = 14.616 (2) Å	T = 293 K
β = 94.575 (9)°	Prism, colourless
V = 1114.7 (2) Å³	0.36 × 0.22 × 0.10 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2276 independent reflections
Radiation source: fine-focus sealed tube	1744 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
T_min = 0.835, T_max = 0.950	k = −11→12
4126 measured reflections	l = −18→8

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0588P)² + 0.1117P] where P = (F_o² + 2F_c²)/3
2276 reflections	(Δ/σ)_max = 0.001
148 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₀H₂₂Cl₂N₂O₆S₂	V = 1114.7 (2) Å³
M_r = 521.42	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8737 (9) Å	µ = 0.52 mm⁻¹
b = 9.717 (1) Å	T = 293 K
c = 14.616 (2) Å	0.36 × 0.22 × 0.10 mm
β = 94.575 (9)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2276 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1744 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.950	R_int = 0.018
4126 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.32 e Å⁻³
2276 reflections	Δρ_min = −0.33 e Å⁻³
148 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	0.3294 (3)	−0.0856 (2)	0.61075 (13)	0.0301 (5)
C2	0.2763 (3)	−0.0520 (2)	0.52035 (14)	0.0329 (5)
C3	0.3042 (3)	−0.1437 (3)	0.45110 (15)	0.0449 (6)
H3	0.2664	−0.1228	0.3908	0.054*
C4	0.3873 (4)	−0.2654 (3)	0.47050 (17)	0.0499 (7)
H4	0.4073	−0.3258	0.4232	0.060*
C5	0.4412 (3)	−0.2986 (3)	0.55920 (18)	0.0479 (6)
H5	0.4977	−0.3813	0.5719	0.057*
C6	0.4118 (3)	−0.2096 (2)	0.62958 (16)	0.0381 (5)
H6	0.4473	−0.2327	0.6898	0.046*
C7	0.0104 (3)	−0.0734 (2)	0.75061 (14)	0.0306 (5)
C8	−0.1521 (3)	−0.0352 (2)	0.79001 (14)	0.0347 (5)
H8A	−0.2460	−0.0863	0.7594	0.042*
H8B	−0.1743	0.0622	0.7808	0.042*
C9	−0.1371 (3)	−0.0685 (2)	0.89303 (14)	0.0385 (6)
H9A	−0.2477	−0.0554	0.9167	0.046*
H9B	−0.1066	−0.1647	0.9011	0.046*
C10	−0.0071 (3)	0.0185 (3)	0.94906 (14)	0.0394 (6)
H10A	−0.0384	0.1147	0.9422	0.047*
H10B	0.1034	0.0065	0.9252	0.047*
N1	0.1046 (2)	0.03505 (19)	0.72033 (12)	0.0316 (4)
H1N	0.066 (3)	0.1134 (18)	0.7259 (16)	0.038*
O1	0.3959 (2)	−0.03761 (18)	0.78343 (10)	0.0456 (4)
O2	0.3555 (2)	0.16371 (17)	0.68236 (10)	0.0415 (4)
O3	0.0630 (2)	−0.19135 (16)	0.74794 (11)	0.0437 (4)
Cl1	0.17624 (9)	0.10214 (7)	0.49044 (4)	0.0505 (2)
S1	0.31012 (7)	0.02626 (6)	0.70503 (3)	0.03155 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0299 (11)	0.0338 (12)	0.0268 (10)	−0.0019 (9)	0.0051 (8)	−0.0017 (9)
C2	0.0336 (12)	0.0347 (12)	0.0305 (11)	−0.0013 (10)	0.0026 (9)	0.0015 (9)
C3	0.0513 (15)	0.0557 (16)	0.0275 (11)	−0.0037 (13)	0.0025 (11)	−0.0034 (11)
C4	0.0576 (17)	0.0482 (16)	0.0459 (14)	−0.0019 (13)	0.0167 (12)	−0.0152 (12)
C5	0.0488 (16)	0.0374 (14)	0.0586 (16)	0.0075 (11)	0.0113 (13)	−0.0039 (12)
C6	0.0377 (13)	0.0377 (13)	0.0390 (12)	0.0018 (10)	0.0038 (10)	0.0024 (10)
C7	0.0389 (12)	0.0300 (12)	0.0232 (9)	−0.0026 (10)	0.0040 (9)	−0.0009 (9)
C8	0.0356 (12)	0.0334 (12)	0.0353 (12)	−0.0025 (10)	0.0045 (9)	0.0021 (10)
C9	0.0441 (14)	0.0399 (14)	0.0329 (12)	−0.0059 (11)	0.0123 (10)	−0.0002 (10)
C10	0.0453 (14)	0.0409 (14)	0.0335 (12)	−0.0062 (11)	0.0125 (10)	−0.0010 (10)
N1	0.0384 (11)	0.0264 (10)	0.0310 (9)	0.0014 (8)	0.0092 (8)	0.0012 (8)
O1	0.0493 (11)	0.0561 (11)	0.0298 (8)	0.0067 (8)	−0.0074 (7)	−0.0001 (8)
O2	0.0447 (10)	0.0362 (9)	0.0440 (9)	−0.0111 (7)	0.0068 (7)	−0.0030 (7)
O3	0.0529 (11)	0.0277 (9)	0.0527 (10)	0.0006 (8)	0.0187 (8)	−0.0006 (7)
Cl1	0.0632 (4)	0.0445 (4)	0.0418 (3)	0.0062 (3)	−0.0077 (3)	0.0065 (3)
S1	0.0340 (3)	0.0352 (3)	0.0253 (3)	−0.0016 (2)	0.0016 (2)	−0.0017 (2)

Geometric parameters (Å, º) top

C1—C6	1.385 (3)	C7—C8	1.492 (3)
C1—C2	1.393 (3)	C8—C9	1.535 (3)
C1—S1	1.771 (2)	C8—H8A	0.9700
C2—C3	1.379 (3)	C8—H8B	0.9700
C2—Cl1	1.732 (2)	C9—C10	1.516 (3)
C3—C4	1.370 (4)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.370 (4)	C10—C10ⁱ	1.527 (4)
C4—H4	0.9300	C10—H10A	0.9700
C5—C6	1.378 (3)	C10—H10B	0.9700
C5—H5	0.9300	N1—S1	1.6532 (19)
C6—H6	0.9300	N1—H1N	0.826 (16)
C7—O3	1.221 (3)	O1—S1	1.4250 (16)
C7—N1	1.381 (3)	O2—S1	1.4282 (17)

C6—C1—C2	119.5 (2)	C7—C8—H8B	109.9
C6—C1—S1	116.55 (16)	C9—C8—H8B	109.9
C2—C1—S1	123.79 (17)	H8A—C8—H8B	108.3
C3—C2—C1	119.4 (2)	C10—C9—C8	114.08 (18)
C3—C2—Cl1	118.01 (18)	C10—C9—H9A	108.7
C1—C2—Cl1	122.59 (17)	C8—C9—H9A	108.7
C4—C3—C2	120.5 (2)	C10—C9—H9B	108.7
C4—C3—H3	119.8	C8—C9—H9B	108.7
C2—C3—H3	119.8	H9A—C9—H9B	107.6
C5—C4—C3	120.4 (2)	C9—C10—C10ⁱ	112.9 (2)
C5—C4—H4	119.8	C9—C10—H10A	109.0
C3—C4—H4	119.8	C10ⁱ—C10—H10A	109.0
C4—C5—C6	120.1 (2)	C9—C10—H10B	109.0
C4—C5—H5	120.0	C10ⁱ—C10—H10B	109.0
C6—C5—H5	120.0	H10A—C10—H10B	107.8
C5—C6—C1	120.1 (2)	C7—N1—S1	124.07 (16)
C5—C6—H6	119.9	C7—N1—H1N	117.4 (17)
C1—C6—H6	119.9	S1—N1—H1N	115.6 (17)
O3—C7—N1	120.9 (2)	O1—S1—O2	118.86 (10)
O3—C7—C8	123.3 (2)	O1—S1—N1	108.65 (10)
N1—C7—C8	115.66 (19)	O2—S1—N1	104.39 (10)
C7—C8—C9	108.97 (18)	O1—S1—C1	107.08 (11)
C7—C8—H8A	109.9	O2—S1—C1	110.79 (10)
C9—C8—H8A	109.9	N1—S1—C1	106.41 (10)

C6—C1—C2—C3	1.0 (3)	C7—C8—C9—C10	66.2 (3)
S1—C1—C2—C3	176.93 (18)	C8—C9—C10—C10ⁱ	−179.1 (2)
C6—C1—C2—Cl1	−178.69 (17)	O3—C7—N1—S1	−17.2 (3)
S1—C1—C2—Cl1	−2.8 (3)	C8—C7—N1—S1	160.00 (15)
C1—C2—C3—C4	−1.7 (4)	C7—N1—S1—O1	−46.8 (2)
Cl1—C2—C3—C4	178.1 (2)	C7—N1—S1—O2	−174.61 (16)
C2—C3—C4—C5	1.1 (4)	C7—N1—S1—C1	68.16 (19)
C3—C4—C5—C6	0.1 (4)	C6—C1—S1—O1	2.7 (2)
C4—C5—C6—C1	−0.7 (4)	C2—C1—S1—O1	−173.29 (18)
C2—C1—C6—C5	0.2 (3)	C6—C1—S1—O2	133.79 (17)
S1—C1—C6—C5	−176.03 (19)	C2—C1—S1—O2	−42.2 (2)
O3—C7—C8—C9	64.1 (3)	C6—C1—S1—N1	−113.32 (17)
N1—C7—C8—C9	−113.0 (2)	C2—C1—S1—N1	70.6 (2)

Symmetry code: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱⁱ	0.83 (2)	2.20 (2)	3.020 (2)	172 (2)

Symmetry code: (ii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂Cl₂N₂O₆S₂
M_r	521.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.8737 (9), 9.717 (1), 14.616 (2)
β (°)	94.575 (9)
V (Å³)	1114.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.36 × 0.22 × 0.10

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	0.835, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	4126, 2276, 1744
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.104, 1.05
No. of reflections	2276
No. of parameters	148
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)	0.32, −0.33

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···O3ⁱ	0.826 (16)	2.200 (16)	3.020 (2)	172 (2)

Symmetry code: (i) −x, y+1/2, −z+3/2.

Acknowledgements

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

References

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