2,2′,5,5′-Tetra­chloro-N,N′-diethyl-N,N′-[benzene-1,3-diylbis(methyl­ene)]dibenzene­sulfonamide

Ejaz; Khan, I.U.; Sheikh, T.A.; Harrison, W.T.A.

doi:10.1107/S1600536811045326

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o15

doi:10.1107/S1600536811045326

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2,2′,5,5′-Tetrachloro-N,N′-diethyl-N,N′-[benzene-1,3-diylbis(methylene)]dibenzenesulfonamide

Ejaz,^a Islam Ullah Khan,^a ^* Tahir Ali Sheikh ^a and William T. A. Harrison ^b

^aMaterials Chemistry Laboratry, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: iuklodhi@yahoo.com

(Received 25 October 2011; accepted 28 October 2011; online 3 December 2011)

In the title compound, C₂₄H₂₄Cl₄N₂O₄S₂, the dihedral angles between the central benzene ring and the pendant rings are 58.09 (10) and 62.59 (10)°. The dihedral angle between the pendant rings is 81.64 (9)°. Both sulfonamide groups lie to the same side of the central ring but the C—S—N—C torsion angles [73.09 (16) and −117.35 (14)] and S—N—C—C torsion angles [−143.80 (14) and −111.45 (16)°] differ significantly for the two pendant chains. The N atoms are close to planar (bond angle sums = 356.4 and 359.5°). In the crystal, weak C—H⋯O and C—H⋯Cl interactions link the molecules.

Related literature

For related structures, see: Ejaz et al. (2011a ,b ).

Experimental

Crystal data

C₂₄H₂₄Cl₄N₂O₄S₂
M_r = 610.37
Triclinic, $[P \overline 1]$
a = 8.0396 (2) Å
b = 11.1512 (3) Å
c = 15.5723 (3) Å
α = 87.454 (1)°
β = 83.378 (1)°
γ = 87.995 (1)°
V = 1384.77 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 296 K
0.50 × 0.35 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
25271 measured reflections
6905 independent reflections
5380 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.04
6905 reflections
327 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O3ⁱ	0.97	2.59	3.511 (2)	158
C17—H17B⋯O1ⁱⁱ	0.97	2.58	3.516 (3)	164
C24—H24⋯Cl1ⁱⁱ	0.93	2.83	3.738 (2)	166
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811045326/su2337sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811045326/su2337Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811045326/su2337Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of symmetrical aryl sulfonamides (Ejaz et al., 2011a,b), the synthesis and structure of the title compound are described herein.

In the title compound (Fig. 1), the dihedral angles between the central (C1-C6) benzene ring and the pendant (C10-C15) and (C19-C24) rings are 58.09 (1) and 62.59 (10)°, respectively. The equivalent angle between the pendant rings is 81.64 (9)°. Both sulfonamide groups lie to the same side of the central ring, but the C10—S1—N1—C7 and C19—S2—N2—C16 torsion angles [73.09 (16) and -117.35 (14)°, respectively] and the S1—N1—C7—C2 and S2—N2—C16—C6 torsion angles [-143.80 (14) and -111.45 (16)°, respectively] differ significantly for the two pendant chains. The conformations of the ethyl side chains are also different: the S1—N1—C8—C9 and S2—N2—C17—C18 torsion angles are -89.6 (2) and -126.57 (19)°, respectively. The nitrogen atoms are close to planar (bond angle sums = 356.4 and 359.5° for N1 and N2, respectively), which seems to indicate a valence state close to sp² hybridization, as also seen in a related structure (Ejaz et al., 2011a).

In the crystal, weak C—H···O and C—H···Cl interactions link the molecules (Table 1).

Related literature top

For related structures, see: Ejaz et al. (2011a,b).

Experimental top

A mixture of N,N'-(benzene-1,3-diyldimethanediyl)bis(2,5-dichlorobenzenesulfonamide) (0.3 g; 0.5 mmol), sodium hydride (0.25 g; 0.9 mmol) and N,N-dimethylformamide (10.0 ml) was stirred in a 100-ml round bottom flask at room temperature for half an hour followed by the addition of ethyl iodide (0.15 g; 0.9 mmol). The reaction mixture was further stirred for five hours, and its completion was monitored by TLC. After completion, the contents were poured over crushed ice. The precipitated product was isolated, washed and crystallized from methanol to yield colourless block-like crystals of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, showing 50% displacement ellipsoids and the numbering scheme.

2,2',5,5'-Tetrachloro-N,N'-diethyl-N,N'- [benzene-1,3-diylbis(methylene)]dibenzenesulfonamide top

Crystal data top

C₂₄H₂₄Cl₄N₂O₄S₂	Z = 2
M_r = 610.37	F(000) = 628
Triclinic, P1	D_x = 1.464 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0396 (2) Å	Cell parameters from 6905 reflections
b = 11.1512 (3) Å	θ = 2.2–28.1°
c = 15.5723 (3) Å	µ = 0.61 mm⁻¹
α = 87.454 (1)°	T = 296 K
β = 83.378 (1)°	Chnnk, colourless
γ = 87.995 (1)°	0.50 × 0.35 × 0.30 mm
V = 1384.77 (6) Å³

Data collection top

Bruker APEXII CCD diffractometer	5380 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 28.4°, θ_min = 3.0°
ω scans	h = −8→10
25271 measured reflections	k = −14→14
6905 independent reflections	l = −20→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0462P)² + 0.4193P] where P = (F_o² + 2F_c²)/3
6905 reflections	(Δ/σ)_max = 0.001
327 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₄H₂₄Cl₄N₂O₄S₂	γ = 87.995 (1)°
M_r = 610.37	V = 1384.77 (6) Å³
Triclinic, P1	Z = 2
a = 8.0396 (2) Å	Mo Kα radiation
b = 11.1512 (3) Å	µ = 0.61 mm⁻¹
c = 15.5723 (3) Å	T = 296 K
α = 87.454 (1)°	0.50 × 0.35 × 0.30 mm
β = 83.378 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5380 reflections with I > 2σ(I)
25271 measured reflections	R_int = 0.020
6905 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
6905 reflections	Δρ_min = −0.38 e Å⁻³
327 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
C1	0.6756 (2)	0.63163 (16)	0.43821 (11)	0.0454 (4)
H1	0.5623	0.6242	0.4333	0.055*
C2	0.7280 (3)	0.63672 (17)	0.51940 (12)	0.0502 (4)
C3	0.8970 (3)	0.6480 (2)	0.52549 (15)	0.0695 (6)
H3	0.9340	0.6525	0.5797	0.083*
C4	1.0103 (3)	0.6527 (3)	0.45304 (17)	0.0776 (7)
H4	1.1236	0.6594	0.4583	0.093*
C5	0.9572 (3)	0.6475 (2)	0.37192 (14)	0.0622 (5)
H5	1.0347	0.6509	0.3228	0.075*
C6	0.7890 (2)	0.63737 (16)	0.36384 (11)	0.0452 (4)
C7	0.6016 (3)	0.63174 (18)	0.59876 (12)	0.0579 (5)
H7A	0.4935	0.6113	0.5825	0.069*
H7B	0.6359	0.5696	0.6392	0.069*
C8	0.5407 (3)	0.85534 (19)	0.58997 (13)	0.0571 (5)
H8A	0.6171	0.8607	0.5371	0.069*
H8B	0.5553	0.9256	0.6225	0.069*
C9	0.3646 (4)	0.8577 (3)	0.5668 (2)	0.0967 (9)
H9A	0.3463	0.9274	0.5304	0.145*
H9B	0.2875	0.8603	0.6187	0.145*
H9C	0.3473	0.7867	0.5367	0.145*
C10	0.75316 (19)	0.69614 (16)	0.77750 (10)	0.0395 (3)
C11	0.8994 (2)	0.75963 (17)	0.75576 (12)	0.0462 (4)
C12	1.0466 (2)	0.71855 (19)	0.78590 (14)	0.0567 (5)
H12	1.1438	0.7614	0.7717	0.068*
C13	1.0506 (2)	0.6145 (2)	0.83684 (14)	0.0578 (5)
H13	1.1499	0.5873	0.8574	0.069*
C14	0.9069 (2)	0.55140 (17)	0.85701 (12)	0.0476 (4)
C15	0.7572 (2)	0.59124 (16)	0.82812 (11)	0.0417 (4)
H15	0.6605	0.5479	0.8426	0.050*
C16	0.7269 (2)	0.63890 (16)	0.27608 (11)	0.0462 (4)
H16A	0.8216	0.6338	0.2317	0.055*
H16B	0.6586	0.5697	0.2724	0.055*
C17	0.7074 (3)	0.86554 (18)	0.26202 (15)	0.0604 (5)
H17A	0.7458	0.8739	0.3182	0.073*
H17B	0.6251	0.9295	0.2538	0.073*
C18	0.8521 (4)	0.8787 (3)	0.1935 (2)	0.0934 (9)
H18A	0.8894	0.9598	0.1910	0.140*
H18B	0.8181	0.8602	0.1386	0.140*
H18C	0.9419	0.8246	0.2069	0.140*
C19	0.4012 (2)	0.80340 (16)	0.14908 (10)	0.0414 (4)
C20	0.4657 (2)	0.74445 (17)	0.07480 (11)	0.0470 (4)
C21	0.4306 (3)	0.7893 (2)	−0.00540 (12)	0.0597 (5)
H21	0.4722	0.7489	−0.0547	0.072*
C22	0.3354 (3)	0.8928 (2)	−0.01335 (13)	0.0620 (5)
H22	0.3119	0.9223	−0.0676	0.074*
C23	0.2751 (2)	0.95234 (18)	0.05987 (12)	0.0514 (4)
C24	0.3068 (2)	0.90861 (17)	0.14088 (11)	0.0458 (4)
H24	0.2649	0.9497	0.1898	0.055*
S1	0.55636 (5)	0.74464 (4)	0.74476 (3)	0.04106 (11)
S2	0.42957 (6)	0.74915 (4)	0.25594 (3)	0.04402 (11)
N1	0.5864 (2)	0.74805 (14)	0.64078 (9)	0.0489 (4)
N2	0.62753 (19)	0.74925 (13)	0.26098 (10)	0.0475 (3)
O1	0.51855 (17)	0.86403 (12)	0.77167 (9)	0.0560 (3)
O2	0.44311 (14)	0.65269 (12)	0.77704 (8)	0.0515 (3)
O3	0.37690 (17)	0.62781 (12)	0.26631 (9)	0.0563 (3)
O4	0.34712 (19)	0.83655 (14)	0.31150 (8)	0.0622 (4)
Cl1	0.90284 (7)	0.88984 (5)	0.69119 (4)	0.06287 (14)
Cl2	0.91046 (7)	0.41825 (5)	0.91822 (4)	0.06768 (16)
Cl3	0.59191 (7)	0.61629 (5)	0.07875 (3)	0.06285 (15)
Cl4	0.15880 (8)	1.08554 (5)	0.05174 (4)	0.07195 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0522 (10)	0.0428 (10)	0.0418 (9)	−0.0030 (7)	−0.0065 (7)	−0.0035 (7)
C2	0.0699 (12)	0.0418 (10)	0.0399 (9)	0.0025 (8)	−0.0106 (8)	−0.0043 (7)
C3	0.0735 (14)	0.0824 (16)	0.0571 (13)	0.0149 (12)	−0.0270 (11)	−0.0146 (11)
C4	0.0519 (12)	0.107 (2)	0.0773 (16)	0.0142 (12)	−0.0204 (11)	−0.0194 (14)
C5	0.0492 (11)	0.0776 (15)	0.0591 (12)	0.0081 (10)	−0.0047 (9)	−0.0072 (11)
C6	0.0494 (9)	0.0430 (10)	0.0429 (9)	0.0052 (7)	−0.0054 (7)	−0.0032 (7)
C7	0.0879 (15)	0.0477 (11)	0.0384 (9)	−0.0080 (10)	−0.0066 (9)	−0.0019 (8)
C8	0.0692 (13)	0.0528 (11)	0.0463 (10)	0.0054 (9)	−0.0006 (9)	0.0103 (9)
C9	0.0856 (19)	0.106 (2)	0.099 (2)	0.0127 (16)	−0.0304 (16)	0.0276 (18)
C10	0.0340 (7)	0.0486 (10)	0.0360 (8)	−0.0002 (7)	−0.0017 (6)	−0.0088 (7)
C11	0.0416 (9)	0.0473 (10)	0.0486 (10)	−0.0037 (7)	0.0021 (7)	−0.0083 (8)
C12	0.0345 (8)	0.0634 (13)	0.0716 (13)	−0.0056 (8)	−0.0007 (8)	−0.0081 (10)
C13	0.0368 (9)	0.0688 (13)	0.0688 (13)	0.0047 (8)	−0.0101 (8)	−0.0098 (10)
C14	0.0446 (9)	0.0508 (11)	0.0478 (10)	0.0054 (8)	−0.0077 (7)	−0.0067 (8)
C15	0.0363 (8)	0.0506 (10)	0.0383 (8)	−0.0013 (7)	−0.0034 (6)	−0.0068 (7)
C16	0.0526 (10)	0.0469 (10)	0.0382 (9)	0.0034 (8)	−0.0012 (7)	−0.0060 (7)
C17	0.0711 (13)	0.0451 (11)	0.0688 (13)	−0.0084 (9)	−0.0234 (11)	0.0018 (9)
C18	0.098 (2)	0.0845 (19)	0.097 (2)	−0.0371 (16)	−0.0047 (16)	0.0179 (16)
C19	0.0412 (8)	0.0490 (10)	0.0340 (8)	−0.0053 (7)	−0.0023 (6)	−0.0035 (7)
C20	0.0479 (9)	0.0528 (11)	0.0394 (9)	−0.0017 (8)	0.0001 (7)	−0.0069 (8)
C21	0.0703 (13)	0.0731 (14)	0.0347 (9)	0.0004 (11)	−0.0004 (8)	−0.0085 (9)
C22	0.0715 (13)	0.0772 (15)	0.0375 (10)	0.0008 (11)	−0.0103 (9)	0.0033 (9)
C23	0.0531 (10)	0.0530 (11)	0.0486 (10)	−0.0030 (8)	−0.0100 (8)	0.0023 (8)
C24	0.0452 (9)	0.0519 (11)	0.0406 (9)	−0.0028 (8)	−0.0044 (7)	−0.0054 (8)
S1	0.0364 (2)	0.0499 (3)	0.0361 (2)	0.00241 (17)	−0.00185 (15)	−0.00196 (17)
S2	0.0484 (2)	0.0491 (3)	0.0329 (2)	−0.00132 (18)	0.00197 (16)	−0.00125 (17)
N1	0.0683 (10)	0.0431 (8)	0.0353 (7)	0.0015 (7)	−0.0079 (7)	0.0006 (6)
N2	0.0529 (8)	0.0411 (8)	0.0501 (8)	−0.0039 (6)	−0.0123 (7)	−0.0002 (6)
O1	0.0568 (8)	0.0580 (8)	0.0521 (8)	0.0143 (6)	−0.0022 (6)	−0.0118 (6)
O2	0.0339 (6)	0.0686 (9)	0.0508 (7)	−0.0053 (6)	−0.0034 (5)	0.0098 (6)
O3	0.0571 (8)	0.0549 (8)	0.0549 (8)	−0.0138 (6)	0.0022 (6)	0.0074 (6)
O4	0.0727 (9)	0.0730 (10)	0.0378 (7)	0.0149 (7)	0.0046 (6)	−0.0090 (6)
Cl1	0.0584 (3)	0.0556 (3)	0.0720 (3)	−0.0115 (2)	0.0042 (2)	0.0037 (2)
Cl2	0.0640 (3)	0.0647 (3)	0.0758 (4)	0.0053 (2)	−0.0212 (3)	0.0105 (3)
Cl3	0.0713 (3)	0.0645 (3)	0.0507 (3)	0.0141 (3)	0.0007 (2)	−0.0128 (2)
Cl4	0.0829 (4)	0.0666 (4)	0.0675 (3)	0.0136 (3)	−0.0205 (3)	0.0039 (3)

Geometric parameters (Å, º) top

C1—C2	1.382 (2)	C14—C15	1.385 (2)
C1—C6	1.389 (3)	C14—Cl2	1.730 (2)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.383 (3)	C16—N2	1.468 (2)
C2—C7	1.507 (3)	C16—H16A	0.9700
C3—C4	1.366 (3)	C16—H16B	0.9700
C3—H3	0.9300	C17—N2	1.469 (2)
C4—C5	1.383 (3)	C17—C18	1.491 (4)
C4—H4	0.9300	C17—H17A	0.9700
C5—C6	1.381 (3)	C17—H17B	0.9700
C5—H5	0.9300	C18—H18A	0.9600
C6—C16	1.507 (2)	C18—H18B	0.9600
C7—N1	1.474 (2)	C18—H18C	0.9600
C7—H7A	0.9700	C19—C24	1.384 (2)
C7—H7B	0.9700	C19—C20	1.394 (2)
C8—N1	1.465 (2)	C19—S2	1.7820 (17)
C8—C9	1.499 (3)	C20—C21	1.380 (3)
C8—H8A	0.9700	C20—Cl3	1.726 (2)
C8—H8B	0.9700	C21—C22	1.371 (3)
C9—H9A	0.9600	C21—H21	0.9300
C9—H9B	0.9600	C22—C23	1.376 (3)
C9—H9C	0.9600	C22—H22	0.9300
C10—C15	1.383 (2)	C23—C24	1.380 (3)
C10—C11	1.394 (2)	C23—Cl4	1.735 (2)
C10—S1	1.7769 (16)	C24—H24	0.9300
C11—C12	1.379 (3)	S1—O1	1.4256 (14)
C11—Cl1	1.7282 (19)	S1—O2	1.4307 (13)
C12—C13	1.378 (3)	S1—N1	1.6082 (15)
C12—H12	0.9300	S2—O4	1.4267 (14)
C13—C14	1.372 (3)	S2—O3	1.4286 (14)
C13—H13	0.9300	S2—N2	1.6025 (16)

C2—C1—C6	121.26 (18)	N2—C16—C6	110.74 (14)
C2—C1—H1	119.4	N2—C16—H16A	109.5
C6—C1—H1	119.4	C6—C16—H16A	109.5
C1—C2—C3	118.56 (19)	N2—C16—H16B	109.5
C1—C2—C7	119.97 (19)	C6—C16—H16B	109.5
C3—C2—C7	121.47 (18)	H16A—C16—H16B	108.1
C4—C3—C2	120.9 (2)	N2—C17—C18	112.5 (2)
C4—C3—H3	119.6	N2—C17—H17A	109.1
C2—C3—H3	119.6	C18—C17—H17A	109.1
C3—C4—C5	120.3 (2)	N2—C17—H17B	109.1
C3—C4—H4	119.8	C18—C17—H17B	109.1
C5—C4—H4	119.8	H17A—C17—H17B	107.8
C6—C5—C4	120.1 (2)	C17—C18—H18A	109.5
C6—C5—H5	120.0	C17—C18—H18B	109.5
C4—C5—H5	120.0	H18A—C18—H18B	109.5
C5—C6—C1	118.91 (17)	C17—C18—H18C	109.5
C5—C6—C16	121.04 (17)	H18A—C18—H18C	109.5
C1—C6—C16	119.97 (16)	H18B—C18—H18C	109.5
N1—C7—C2	110.85 (16)	C24—C19—C20	119.20 (16)
N1—C7—H7A	109.5	C24—C19—S2	117.24 (13)
C2—C7—H7A	109.5	C20—C19—S2	123.55 (14)
N1—C7—H7B	109.5	C21—C20—C19	119.87 (18)
C2—C7—H7B	109.5	C21—C20—Cl3	117.85 (15)
H7A—C7—H7B	108.1	C19—C20—Cl3	122.28 (14)
N1—C8—C9	114.22 (19)	C22—C21—C20	120.85 (19)
N1—C8—H8A	108.7	C22—C21—H21	119.6
C9—C8—H8A	108.7	C20—C21—H21	119.6
N1—C8—H8B	108.7	C21—C22—C23	119.20 (18)
C9—C8—H8B	108.7	C21—C22—H22	120.4
H8A—C8—H8B	107.6	C23—C22—H22	120.4
C8—C9—H9A	109.5	C22—C23—C24	121.06 (19)
C8—C9—H9B	109.5	C22—C23—Cl4	120.31 (15)
H9A—C9—H9B	109.5	C24—C23—Cl4	118.63 (16)
C8—C9—H9C	109.5	C23—C24—C19	119.79 (17)
H9A—C9—H9C	109.5	C23—C24—H24	120.1
H9B—C9—H9C	109.5	C19—C24—H24	120.1
C15—C10—C11	119.74 (15)	O1—S1—O2	118.08 (8)
C15—C10—S1	117.14 (12)	O1—S1—N1	108.23 (8)
C11—C10—S1	123.11 (14)	O2—S1—N1	110.99 (8)
C12—C11—C10	119.87 (18)	O1—S1—C10	109.11 (8)
C12—C11—Cl1	118.30 (15)	O2—S1—C10	105.20 (8)
C10—C11—Cl1	121.83 (14)	N1—S1—C10	104.35 (8)
C13—C12—C11	120.47 (18)	O4—S2—O3	118.77 (9)
C13—C12—H12	119.8	O4—S2—N2	109.82 (9)
C11—C12—H12	119.8	O3—S2—N2	108.25 (8)
C14—C13—C12	119.45 (18)	O4—S2—C19	105.17 (9)
C14—C13—H13	120.3	O3—S2—C19	108.50 (8)
C12—C13—H13	120.3	N2—S2—C19	105.53 (8)
C13—C14—C15	121.21 (18)	C8—N1—C7	118.50 (15)
C13—C14—Cl2	120.22 (15)	C8—N1—S1	120.83 (13)
C15—C14—Cl2	118.56 (15)	C7—N1—S1	117.12 (12)
C10—C15—C14	119.25 (16)	C16—N2—C17	118.81 (16)
C10—C15—H15	120.4	C16—N2—S2	122.54 (12)
C14—C15—H15	120.4	C17—N2—S2	118.14 (13)

C6—C1—C2—C3	0.1 (3)	C22—C23—C24—C19	0.2 (3)
C6—C1—C2—C7	179.28 (17)	Cl4—C23—C24—C19	−179.11 (14)
C1—C2—C3—C4	−0.7 (3)	C20—C19—C24—C23	1.3 (3)
C7—C2—C3—C4	−179.9 (2)	S2—C19—C24—C23	−177.43 (14)
C2—C3—C4—C5	0.7 (4)	C15—C10—S1—O1	124.12 (14)
C3—C4—C5—C6	−0.1 (4)	C11—C10—S1—O1	−54.76 (16)
C4—C5—C6—C1	−0.5 (3)	C15—C10—S1—O2	−3.50 (15)
C4—C5—C6—C16	176.4 (2)	C11—C10—S1—O2	177.63 (14)
C2—C1—C6—C5	0.5 (3)	C15—C10—S1—N1	−120.40 (14)
C2—C1—C6—C16	−176.41 (17)	C11—C10—S1—N1	60.73 (16)
C1—C2—C7—N1	−111.1 (2)	C24—C19—S2—O4	−2.36 (16)
C3—C2—C7—N1	68.0 (2)	C20—C19—S2—O4	178.98 (15)
C15—C10—C11—C12	−1.0 (3)	C24—C19—S2—O3	125.71 (14)
S1—C10—C11—C12	177.85 (15)	C20—C19—S2—O3	−52.96 (17)
C15—C10—C11—Cl1	178.88 (13)	C24—C19—S2—N2	−118.46 (14)
S1—C10—C11—Cl1	−2.3 (2)	C20—C19—S2—N2	62.87 (17)
C10—C11—C12—C13	0.5 (3)	C9—C8—N1—C7	68.6 (3)
Cl1—C11—C12—C13	−179.33 (16)	C9—C8—N1—S1	−89.6 (2)
C11—C12—C13—C14	0.4 (3)	C2—C7—N1—C8	57.3 (2)
C12—C13—C14—C15	−0.9 (3)	C2—C7—N1—S1	−143.80 (14)
C12—C13—C14—Cl2	178.11 (16)	O1—S1—N1—C8	−12.41 (18)
C11—C10—C15—C14	0.5 (3)	O2—S1—N1—C8	118.67 (16)
S1—C10—C15—C14	−178.43 (13)	C10—S1—N1—C8	−128.51 (16)
C13—C14—C15—C10	0.5 (3)	O1—S1—N1—C7	−170.82 (15)
Cl2—C14—C15—C10	−178.57 (13)	O2—S1—N1—C7	−39.74 (17)
C5—C6—C16—N2	−111.2 (2)	C10—S1—N1—C7	73.09 (16)
C1—C6—C16—N2	65.6 (2)	C6—C16—N2—C17	60.2 (2)
C24—C19—C20—C21	−2.0 (3)	C6—C16—N2—S2	−111.45 (16)
S2—C19—C20—C21	176.64 (16)	C18—C17—N2—C16	61.4 (2)
C24—C19—C20—Cl3	177.23 (14)	C18—C17—N2—S2	−126.57 (19)
S2—C19—C20—Cl3	−4.1 (2)	O4—S2—N2—C16	129.76 (14)
C19—C20—C21—C22	1.2 (3)	O3—S2—N2—C16	−1.35 (16)
Cl3—C20—C21—C22	−178.04 (17)	C19—S2—N2—C16	−117.35 (14)
C20—C21—C22—C23	0.3 (3)	O4—S2—N2—C17	−41.94 (17)
C21—C22—C23—C24	−1.0 (3)	O3—S2—N2—C17	−173.06 (14)
C21—C22—C23—Cl4	178.31 (17)	C19—S2—N2—C17	70.94 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O3ⁱ	0.97	2.59	3.511 (2)	158
C17—H17B···O1ⁱⁱ	0.97	2.58	3.516 (3)	164
C24—H24···Cl1ⁱⁱ	0.93	2.83	3.738 (2)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₄Cl₄N₂O₄S₂
M_r	610.37
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.0396 (2), 11.1512 (3), 15.5723 (3)
α, β, γ (°)	87.454 (1), 83.378 (1), 87.995 (1)
V (Å³)	1384.77 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.50 × 0.35 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	25271, 6905, 5380
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.102, 1.04
No. of reflections	6905
No. of parameters	327
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.38

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O3ⁱ	0.97	2.59	3.511 (2)	158
C17—H17B···O1ⁱⁱ	0.97	2.58	3.516 (3)	164
C24—H24···Cl1ⁱⁱ	0.93	2.83	3.738 (2)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Acknowledgements

IUK thanks the Higher Education Commission of Pakistan for its financial support under the project to strengthen the Materials Chemistry Laboratory at GCUL.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ejaz, Khan, I. U., Ahmad, H. & Harrison, W. T. A. (2011a). Acta Cryst. E67, o3037. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ejaz, Khan, I. U., Ahmad, H., Harrison, W. T. A. & Sheikh, T. A. (2011b). Acta Cryst. E67, o3038. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 1| January 2012| Page o15

doi:10.1107/S1600536811045326

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′,5,5′-Tetra­chloro-N,N′-di­ethyl-N,N′-[benzene-1,3-diylbis(methyl­ene)]di­benzene­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′,5,5′-Tetrachloro-N,N′-diethyl-N,N′-[benzene-1,3-diylbis(methylene)]dibenzenesulfonamide