N,N′-Bis(4-chloro­phenyl­sulfon­yl)suberamide

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

doi:10.1107/S1600536811028662

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2101

doi:10.1107/S1600536811028662

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N,N′-Bis(4-chlorophenylsulfonyl)suberamide

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

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 15 July 2011; accepted 17 July 2011; online 23 July 2011)

The asymmetric unit of the title compound, C₂₀H₂₂Cl₂N₂O₆S₂, contains one half-molecule with a center of symmetry at the mid-point of the central C—C bond. The conformations of all the N—H, C=O and C—H bonds in the central amide and aliphatic segments are anti to their adjacent bonds. The molecule is bent at the S atom with a C—SO₂—NH—C(O) torsion angle of −80.6 (4)°. The dihedral angle between the benzene ring and the SO₂—NH—C(O)—CH₂—CH₂—CH₂ segment is 79.5 (2)°. In the crystal, intermolecular N—H⋯O(C) and N—H⋯O(S) hydrogen bonds link the molecules into chains along the b axis.

Related literature

For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000 , 2007 ), on N-(arylsulfonyl)-amides, see: Rodrigues et al. (2011a ,b ) and on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ).

Experimental

Crystal data

C₂₀H₂₂Cl₂N₂O₆S₂
M_r = 521.42
Monoclinic, P 2₁ /c
a = 21.925 (4) Å
b = 5.5855 (8) Å
c = 9.381 (1) Å
β = 93.91 (1)°
V = 1146.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 293 K
0.48 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with 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 = 0.793, T_max = 0.970
3854 measured reflections
2081 independent reflections
1522 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.115
S = 1.18
2081 reflections
148 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.85 (2)	2.19 (3)	2.975 (4)	153 (4)
N1—H1N⋯O3ⁱ	0.85 (2)	2.57 (3)	3.227 (4)	135 (3)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811028662/sj6195sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028662/sj6195Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028662/sj6195Isup3.cml

checkCIF report

Comment top

The amide moiety is an important constituent of many biologically significant compounds. As part of our studies on the effects of ring and side chain substitutions on the structures of N-(aryl)-amides (Gowda et al., 2000, 2007), N-(arylsulfonyl)-amides (Rodrigues et al., 2011a,b) and N-(aryl)- arylsulfonamides (Gowda et al., 2005), the crystal structure of N,N-bis(4-chlorophenylsulfonyl)-suberamide has been determined (I) (Fig. 1).

In the two C—SO₂—NH—CO—CH₂—CH₂—CH₂— central amide and aliphatic segments of the structure, all the N—H, C=O and C—H bonds in the amide and aliphatic segments are anti to the adjacent bonds, similar to that observed in N,N-bis(2-chlorophenylsulfonyl)-suberamide (II) (Rodrigues et al., 2011b) and N,N-bis(2-chlorophenylsulfonyl)-adipamide (III) (Rodrigues et al., 2011a). The orientations of sulfonamide groups with respect to the attached phenyl rings are given by the torsion angles of C2—C1—S1—N1 = -113.9 (4)° and C6—C1—S1—N1 = 67.2 (3)°. The molecule is bent at the S atom with the C1—S1—N1—C7 torsion angle of -80.6 (4)°, compared to the values of 68.2 (2)° in (II) and -65.1 (6)° in (III). In (I), the aliphatic chain is linear with the C7—C8—C9—C10 torsion angle of -179.4 (4)°.

The dihedral angle between the benzene ring and the SO₂—NH—C(O)—CH₂—CH₂—CH₂ segment in the two halves of the molecule is 79.5 (2)°, compared to the values of 77.5 (1)° in (II) and 89.6 (2)° in (III).

The structure shows simultaneous of N—H···O(C) and N—H···O(S) intermolecular hydrogen bonds (Table 1), which link the molecules into infinite chains along the b-axis.

Related literature top

For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000, 2007), on N-(arylsulfonyl)-amides, see: Rodrigues et al. (2011a,b) and on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005).

Experimental top

N,N-Bis(4-chlorophenylsulfonyl)-suberamide was prepared by refluxing a mixture of suberic acid (octanedioic acid) (0.01 mol) with 4-chlorobenzenesulfonamide (0.02 mol) and POCl₃ for 1 hr on a water bath. The reaction mixture was allowed to cool and ether added to it. The solid product was filtered and washed thoroughly with ether and hot ethanol. The compound was recrystallized to the constant melting point and 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. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

N,N'-Bis(4-chlorophenylsulfonyl)suberamide top

Crystal data top

C₂₀H₂₂Cl₂N₂O₆S₂	F(000) = 540
M_r = 521.42	D_x = 1.511 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1226 reflections
a = 21.925 (4) Å	θ = 2.8–27.9°
b = 5.5855 (8) Å	µ = 0.51 mm⁻¹
c = 9.381 (1) Å	T = 293 K
β = 93.91 (1)°	Needle, colourless
V = 1146.1 (3) Å³	0.48 × 0.14 × 0.06 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2081 independent reflections
Radiation source: fine-focus sealed tube	1522 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Rotation method data acquisition using ω scans.	θ_max = 25.3°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −24→26
T_min = 0.793, T_max = 0.970	k = −6→5
3854 measured reflections	l = −11→9

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ²(F_o²) + (0.P)² + 2.6128P] where P = (F_o² + 2F_c²)/3
2081 reflections	(Δ/σ)_max = 0.009
148 parameters	Δρ_max = 0.29 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₀H₂₂Cl₂N₂O₆S₂	V = 1146.1 (3) Å³
M_r = 521.42	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.925 (4) Å	µ = 0.51 mm⁻¹
b = 5.5855 (8) Å	T = 293 K
c = 9.381 (1) Å	0.48 × 0.14 × 0.06 mm
β = 93.91 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2081 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1522 reflections with I > 2σ(I)
T_min = 0.793, T_max = 0.970	R_int = 0.029
3854 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	1 restraint
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.29 e Å⁻³
2081 reflections	Δρ_min = −0.32 e Å⁻³
148 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
Cl1	0.04045 (6)	0.7957 (3)	0.3395 (2)	0.1014 (6)
S1	0.26694 (5)	0.1182 (2)	0.39060 (10)	0.0397 (3)
O1	0.25535 (13)	−0.0692 (5)	0.4882 (3)	0.0482 (8)
O2	0.28271 (13)	0.0610 (5)	0.2497 (3)	0.0486 (8)
O3	0.35809 (14)	0.4648 (6)	0.2761 (3)	0.0608 (10)
N1	0.32305 (15)	0.2771 (6)	0.4690 (3)	0.0397 (8)
H1N	0.3190 (18)	0.284 (7)	0.559 (2)	0.048*
C1	0.20287 (18)	0.3113 (8)	0.3787 (4)	0.0405 (10)
C2	0.1531 (2)	0.2614 (9)	0.4551 (5)	0.0573 (13)
H2	0.1534	0.1285	0.5148	0.069*
C3	0.1026 (2)	0.4101 (10)	0.4425 (6)	0.0694 (15)
H3	0.0686	0.3776	0.4932	0.083*
C4	0.1034 (2)	0.6059 (9)	0.3547 (6)	0.0596 (13)
C5	0.1531 (2)	0.6559 (9)	0.2780 (5)	0.0551 (12)
H5	0.1527	0.7886	0.2181	0.066*
C6	0.2034 (2)	0.5079 (8)	0.2906 (4)	0.0470 (11)
H6	0.2374	0.5407	0.2399	0.056*
C7	0.35867 (17)	0.4445 (8)	0.4041 (4)	0.0378 (10)
C8	0.39757 (17)	0.5930 (8)	0.5078 (4)	0.0389 (10)
H8A	0.4223	0.4876	0.5703	0.047*
H8B	0.3713	0.6846	0.5665	0.047*
C9	0.43924 (18)	0.7634 (8)	0.4345 (4)	0.0409 (10)
H9A	0.4651	0.6715	0.3749	0.049*
H9B	0.4144	0.8693	0.3726	0.049*
C10	0.47944 (17)	0.9135 (8)	0.5373 (4)	0.0394 (10)
H10A	0.5048	0.8079	0.5984	0.047*
H10B	0.4537	1.0041	0.5978	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0516 (8)	0.0761 (11)	0.1751 (18)	0.0094 (8)	−0.0036 (9)	−0.0021 (11)
S1	0.0432 (6)	0.0422 (6)	0.0343 (5)	−0.0088 (5)	0.0065 (4)	−0.0047 (5)
O1	0.0551 (18)	0.0452 (19)	0.0447 (16)	−0.0108 (15)	0.0069 (14)	0.0030 (14)
O2	0.0577 (19)	0.054 (2)	0.0353 (15)	−0.0070 (15)	0.0085 (13)	−0.0108 (14)
O3	0.063 (2)	0.086 (3)	0.0328 (16)	−0.0361 (19)	0.0026 (14)	0.0065 (16)
N1	0.0386 (18)	0.052 (2)	0.0298 (16)	−0.0161 (17)	0.0076 (15)	−0.0034 (17)
C1	0.042 (2)	0.043 (3)	0.036 (2)	−0.010 (2)	0.0002 (18)	−0.005 (2)
C2	0.044 (3)	0.064 (3)	0.065 (3)	−0.009 (3)	0.013 (2)	0.011 (3)
C3	0.041 (3)	0.078 (4)	0.091 (4)	−0.008 (3)	0.018 (3)	0.006 (3)
C4	0.040 (3)	0.054 (3)	0.083 (3)	−0.007 (2)	−0.009 (2)	−0.010 (3)
C5	0.063 (3)	0.044 (3)	0.057 (3)	−0.010 (2)	−0.004 (2)	0.004 (2)
C6	0.044 (3)	0.050 (3)	0.047 (2)	−0.008 (2)	0.007 (2)	−0.006 (2)
C7	0.028 (2)	0.050 (3)	0.036 (2)	−0.0030 (19)	0.0049 (17)	−0.0005 (19)
C8	0.035 (2)	0.049 (3)	0.034 (2)	−0.005 (2)	0.0056 (17)	−0.004 (2)
C9	0.040 (2)	0.044 (3)	0.038 (2)	−0.010 (2)	0.0075 (17)	−0.0012 (19)
C10	0.035 (2)	0.047 (3)	0.036 (2)	−0.005 (2)	0.0071 (17)	−0.0043 (19)

Geometric parameters (Å, º) top

Cl1—C4	1.738 (5)	C4—C5	1.375 (6)
S1—O1	1.425 (3)	C5—C6	1.377 (6)
S1—O2	1.425 (3)	C5—H5	0.9300
S1—N1	1.649 (3)	C6—H6	0.9300
S1—C1	1.769 (4)	C7—C8	1.499 (5)
O3—C7	1.205 (4)	C8—C9	1.516 (5)
N1—C7	1.386 (5)	C8—H8A	0.9700
N1—H1N	0.852 (18)	C8—H8B	0.9700
C1—C2	1.374 (5)	C9—C10	1.515 (5)
C1—C6	1.375 (6)	C9—H9A	0.9700
C2—C3	1.382 (7)	C9—H9B	0.9700
C2—H2	0.9300	C10—C10ⁱ	1.525 (7)
C3—C4	1.370 (7)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700

O1—S1—O2	119.75 (18)	C5—C6—C1	119.4 (4)
O1—S1—N1	105.61 (17)	C5—C6—H6	120.3
O2—S1—N1	108.29 (17)	C1—C6—H6	120.3
O1—S1—C1	108.25 (18)	O3—C7—N1	122.2 (4)
O2—S1—C1	108.65 (18)	O3—C7—C8	124.1 (4)
N1—S1—C1	105.37 (19)	N1—C7—C8	113.6 (3)
C7—N1—S1	126.4 (3)	C7—C8—C9	112.8 (3)
C7—N1—H1N	120 (3)	C7—C8—H8A	109.0
S1—N1—H1N	110 (3)	C9—C8—H8A	109.0
C2—C1—C6	121.0 (4)	C7—C8—H8B	109.0
C2—C1—S1	119.9 (4)	C9—C8—H8B	109.0
C6—C1—S1	119.1 (3)	H8A—C8—H8B	107.8
C1—C2—C3	119.6 (5)	C10—C9—C8	113.6 (3)
C1—C2—H2	120.2	C10—C9—H9A	108.8
C3—C2—H2	120.2	C8—C9—H9A	108.8
C4—C3—C2	119.3 (4)	C10—C9—H9B	108.8
C4—C3—H3	120.4	C8—C9—H9B	108.8
C2—C3—H3	120.4	H9A—C9—H9B	107.7
C3—C4—C5	121.2 (5)	C9—C10—C10ⁱ	113.2 (4)
C3—C4—Cl1	119.7 (4)	C9—C10—H10A	108.9
C5—C4—Cl1	119.1 (4)	C10ⁱ—C10—H10A	108.9
C6—C5—C4	119.5 (4)	C9—C10—H10B	108.9
C6—C5—H5	120.3	C10ⁱ—C10—H10B	108.9
C4—C5—H5	120.3	H10A—C10—H10B	107.7

O1—S1—N1—C7	165.0 (3)	C2—C3—C4—Cl1	−179.4 (4)
O2—S1—N1—C7	35.6 (4)	C3—C4—C5—C6	−0.7 (7)
C1—S1—N1—C7	−80.6 (4)	Cl1—C4—C5—C6	179.3 (3)
O1—S1—C1—C2	−1.3 (4)	C4—C5—C6—C1	0.6 (7)
O2—S1—C1—C2	130.2 (3)	C2—C1—C6—C5	−0.5 (6)
N1—S1—C1—C2	−113.9 (4)	S1—C1—C6—C5	178.4 (3)
O1—S1—C1—C6	179.8 (3)	S1—N1—C7—O3	−11.8 (6)
O2—S1—C1—C6	−48.7 (4)	S1—N1—C7—C8	168.7 (3)
N1—S1—C1—C6	67.1 (3)	O3—C7—C8—C9	−3.3 (6)
C6—C1—C2—C3	0.5 (7)	N1—C7—C8—C9	176.2 (3)
S1—C1—C2—C3	−178.5 (4)	C7—C8—C9—C10	−179.4 (3)
C1—C2—C3—C4	−0.5 (8)	C8—C9—C10—C10ⁱ	−179.2 (4)
C2—C3—C4—C5	0.6 (8)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱⁱ	0.85 (2)	2.19 (3)	2.975 (4)	153 (4)
N1—H1N···O3ⁱⁱ	0.85 (2)	2.57 (3)	3.227 (4)	135 (3)

Symmetry code: (ii) x, −y+1/2, z+1/2.

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)	21.925 (4), 5.5855 (8), 9.381 (1)
β (°)	93.91 (1)
V (Å³)	1146.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.48 × 0.14 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.793, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	3854, 2081, 1522
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.115, 1.18
No. of reflections	2081
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)	0.29, −0.32

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	0.852 (18)	2.19 (3)	2.975 (4)	153 (4)
N1—H1N···O3ⁱ	0.852 (18)	2.57 (3)	3.227 (4)	135 (3)

Symmetry code: (i) x, −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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