(E)-N,N′-Bis[2-(5-bromo-1H-indol-3-yl)eth­yl]-N,N′-(but-2-ene-1,4-di­yl)bis­(4-methyl­benzene­sulfonamide)

Lou, Y.

doi:10.1107/S1600536811041791

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2987

doi:10.1107/S1600536811041791

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(E)-N,N′-Bis[2-(5-bromo-1H-indol-3-yl)ethyl]-N,N′-(but-2-ene-1,4-diyl)bis(4-methylbenzenesulfonamide)

Yongbing Lou ^a ^*

^aSchool of Chemistry and Chemical Engineering, Southeast University, Southeast University Road 2, Jiangning District, 211189 Nanjing, People's Republic of China
^*Correspondence e-mail: lou@seu.edu.cn

(Received 10 October 2011; accepted 11 October 2011; online 22 October 2011)

In the title compound, C₃₈H₃₈Br₂N₄O₄S₂, there is a crystallographic inversion center located at the mid-point of the alkene bond. The dihedral angle between the aromatic ring systems in the asymmetric unit is 87.69 (19)°. In the crystal, adjacent molecules are linked by pairs of N—H⋯O hydrogen bonds, generating R₂²(16) loops within [1 $[\overline{1}]$ 0] chains. Short Br⋯Br contacts [3.6148 (9) Å] are observed between adjacent molecules.

Related literature

For background to sulfonamides, see: Ozbek et al. (2007 ). For related structures, see: Abbassi et al. (2011 ); Akkurt et al. (2011 ).

Experimental

Crystal data

C₃₈H₃₈Br₂N₄O₄S₂
M_r = 838.66
Triclinic, $[P \overline 1]$
a = 5.9222 (8) Å
b = 10.4859 (13) Å
c = 15.601 (2) Å
α = 79.528 (2)°
β = 87.824 (2)°
γ = 75.186 (2)°
V = 921.0 (2) Å³
Z = 1
Mo Kα radiation
μ = 2.36 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.538, T_max = 0.625
5033 measured reflections
3545 independent reflections
2966 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.152
S = 1.02
3545 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 1.60 e Å⁻³
Δρ_min = −1.07 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.05	2.865 (4)	158
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811041791/hb6445sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041791/hb6445Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041791/hb6445Isup3.cml

checkCIF report

Comment top

Sulfonamides exhibit a broad area of biological activites (e.g. Ozbek et al., 2007). As part of our studies in this area, we now describe the stucture of the title compound, (I) (Fig. 1). For related structures, see: Abbassi et al.(2011); Akkurt et al.. (2011).

In the title molecule the S atom has a distorted tetrahedral geometry [maximum deviation: O1—S1—O2 =119.82 (19)°] which is possible due to the two S=O double bonds electron repulsion. In the crystal structure, the molecules are linked by four N—H···O hydrogen bonds with adjacent molecules. There also exists weak Br···Br Van der waals interaction to link adjacent molecules.

Related literature top

For background to sulfonamides, see: Ozbek et al. (2007). For related structures, see: Abbassi et al. (2011); Akkurt et al. (2011).

Experimental top

A solution of 5-bromo tryptamine 1 in (6.68 g, 28.1 mmol) in dichloromethane (100 ml) was cooled in an ice bath, then triethyl amine (8.51 g, 84.3 mmol) and p-toluenesulfonyl chloride (5.90 g, 30.9 mmol) were added. The mixture was stirred for 30 min, successively washed with water, brine and dried over MgSO₄. The solvent was removed in high vacuum, and the tosyl protected tryptamine 2 was obtained in 95% yield (8.38 g, 26.7 mmol) by flash chromatography.

A three-necked flask was charged with tosyl protected tryptamine 2 (8.38 g, 26.7 mmol), acetone (60 ml) and water (60 ml). Then sodium hydroxide (1.60 g, 40.1 mmol) was added. After the solid was dissolved, allyl bromide (3.52 g, 29.4 mmol) was added slowly. The mixture was stirred overnight and evaporated under reduced pressure to remove acetone. The aqueous layer was extracted with CH₂Cl₂ (3 × 50 ml). The combined organic phase was washed with brine, separated, dried over Na₂SO₄, filtrated, and evaporated under reduced pressure. The residue was purified by recrystallization in ethyl acetate to afford the corresponding allyl indolyl compound 3 as a white solid in 84% yield (7.94 g, 22.4 mol).

A solution of 3 (2.00 g, 5.65 mmol) and methyl vinyl ketone (1.19 g, 16.95 mmol) in 1,2-dichloride ethane (40 ml) was heated to 60 ?, then ruthenium catalyst Zhan-1B (83 mg, 0.113 mmol) was added in one portion. The mixture was stirred for 2 days and evaporated under reduced pressure. The residue was purified by flash chromatography to afford compound 4 in 13% yield (615 mg, 0.73 mmol). Colourless blocks of (I) were grown from ethyl acetate and petroleum solution.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Synthetic route for the title compound.
	Fig. 2. A view of the compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 3. Partial packing view showing the hydrogen bonds network. Hydrogen bonds are shown as dashed lines. For the sake of clarity, the H atoms not involved in the motif have been omitted.

(E)-N,N'-Bis[2-(5-bromo-1H-indol-3-yl)ethyl]- N,N'-(but-2-ene-1,4-diyl)bis(4-methylbenzenesulfonamide) top

Crystal data top

C₃₈H₃₈Br₂N₄O₄S₂	Z = 1
M_r = 838.66	F(000) = 428
Triclinic, P1	D_x = 1.512 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9222 (8) Å	Cell parameters from 2384 reflections
b = 10.4859 (13) Å	θ = 2.3–26.0°
c = 15.601 (2) Å	µ = 2.36 mm⁻¹
α = 79.528 (2)°	T = 293 K
β = 87.824 (2)°	Block, colorless
γ = 75.186 (2)°	0.30 × 0.25 × 0.22 mm
V = 921.0 (2) Å³

Data collection top

Bruker SMART CCD diffractometer	3545 independent reflections
Radiation source: fine-focus sealed tube	2966 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→7
T_min = 0.538, T_max = 0.625	k = −10→12
5033 measured reflections	l = −16→19

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.083P)² + 0.8618P] where P = (F_o² + 2F_c²)/3
3545 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 1.60 e Å⁻³
0 restraints	Δρ_min = −1.07 e Å⁻³

Crystal data top

C₃₈H₃₈Br₂N₄O₄S₂	γ = 75.186 (2)°
M_r = 838.66	V = 921.0 (2) Å³
Triclinic, P1	Z = 1
a = 5.9222 (8) Å	Mo Kα radiation
b = 10.4859 (13) Å	µ = 2.36 mm⁻¹
c = 15.601 (2) Å	T = 293 K
α = 79.528 (2)°	0.30 × 0.25 × 0.22 mm
β = 87.824 (2)°

Data collection top

Bruker SMART CCD diffractometer	3545 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2966 reflections with I > 2σ(I)
T_min = 0.538, T_max = 0.625	R_int = 0.015
5033 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	Δρ_max = 1.60 e Å⁻³
3545 reflections	Δρ_min = −1.07 e Å⁻³
227 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
Br1	0.15272 (10)	0.49667 (5)	0.09883 (3)	0.0891 (2)
N1	0.8181 (5)	0.1266 (3)	0.3655 (2)	0.0546 (7)
H1A	0.9610	0.0811	0.3642	0.065*
N2	0.4685 (5)	0.2797 (3)	0.60309 (17)	0.0434 (6)
O1	0.7636 (5)	0.0735 (3)	0.65693 (19)	0.0708 (8)
O2	0.8105 (5)	0.2919 (3)	0.68103 (19)	0.0727 (8)
S1	0.66462 (14)	0.20402 (9)	0.67719 (6)	0.0494 (2)
C1	0.3047 (6)	0.3533 (4)	0.2667 (2)	0.0544 (8)
H1	0.1549	0.3920	0.2843	0.065*
C2	0.3727 (8)	0.3809 (4)	0.1820 (3)	0.0619 (10)
C3	0.5973 (8)	0.3269 (5)	0.1534 (3)	0.0703 (11)
H3	0.6363	0.3497	0.0953	0.084*
C4	0.7594 (7)	0.2406 (4)	0.2104 (3)	0.0640 (10)
H4	0.9097	0.2041	0.1924	0.077*
C5	0.6929 (6)	0.2093 (3)	0.2959 (2)	0.0493 (8)
C6	0.4690 (6)	0.2647 (3)	0.3259 (2)	0.0458 (7)
C7	0.4638 (6)	0.2129 (3)	0.4174 (2)	0.0460 (7)
C8	0.6779 (6)	0.1281 (3)	0.4379 (2)	0.0486 (7)
H8	0.7230	0.0783	0.4930	0.058*
C9	0.2626 (6)	0.2467 (4)	0.4774 (2)	0.0549 (8)
H9A	0.1424	0.2056	0.4636	0.066*
H9B	0.1978	0.3430	0.4658	0.066*
C10	0.3192 (6)	0.2036 (4)	0.5728 (2)	0.0506 (8)
H10A	0.1750	0.2159	0.6055	0.061*
H10B	0.3981	0.1089	0.5842	0.061*
C11	0.3567 (7)	0.4221 (3)	0.6048 (2)	0.0529 (8)
H11A	0.4049	0.4450	0.6576	0.063*
H11B	0.1886	0.4349	0.6068	0.063*
C12	0.4160 (6)	0.5150 (3)	0.5278 (2)	0.0504 (8)
H12	0.3245	0.6028	0.5184	0.061*
C13	0.5233 (6)	0.1823 (3)	0.7782 (2)	0.0478 (7)
C14	0.5337 (8)	0.2638 (5)	0.8365 (3)	0.0664 (10)
H14	0.6181	0.3284	0.8238	0.080*
C15	0.4170 (9)	0.2487 (5)	0.9144 (3)	0.0724 (11)
H15	0.4258	0.3030	0.9545	0.087*
C16	0.2897 (8)	0.1565 (4)	0.9343 (2)	0.0652 (10)
C17	0.2818 (11)	0.0765 (5)	0.8747 (3)	0.0921 (17)
H17	0.1944	0.0134	0.8871	0.110*
C18	0.3998 (10)	0.0870 (4)	0.7972 (3)	0.0762 (13)
H18	0.3958	0.0302	0.7582	0.091*
C19	0.1589 (11)	0.1434 (6)	1.0195 (3)	0.0955 (17)
H19A	0.1990	0.1994	1.0557	0.143*
H19B	0.2010	0.0518	1.0489	0.143*
H19C	−0.0061	0.1708	1.0079	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1095 (4)	0.0846 (4)	0.0707 (3)	−0.0269 (3)	−0.0398 (3)	0.0043 (2)
N1	0.0450 (15)	0.0586 (17)	0.0567 (17)	−0.0009 (13)	0.0016 (13)	−0.0193 (14)
N2	0.0465 (14)	0.0387 (13)	0.0438 (14)	−0.0101 (11)	0.0100 (11)	−0.0069 (11)
O1	0.0679 (17)	0.0645 (16)	0.0630 (16)	0.0152 (13)	0.0095 (13)	−0.0149 (13)
O2	0.0514 (15)	0.110 (2)	0.0691 (17)	−0.0390 (15)	0.0163 (13)	−0.0249 (16)
S1	0.0411 (4)	0.0573 (5)	0.0472 (5)	−0.0077 (3)	0.0108 (3)	−0.0115 (4)
C1	0.0528 (19)	0.055 (2)	0.057 (2)	−0.0102 (16)	−0.0079 (16)	−0.0168 (16)
C2	0.077 (3)	0.060 (2)	0.050 (2)	−0.0206 (19)	−0.0198 (18)	−0.0068 (17)
C3	0.085 (3)	0.089 (3)	0.044 (2)	−0.033 (2)	0.0050 (19)	−0.0152 (19)
C4	0.062 (2)	0.082 (3)	0.053 (2)	−0.020 (2)	0.0110 (17)	−0.0262 (19)
C5	0.0509 (18)	0.0518 (18)	0.0494 (18)	−0.0128 (15)	0.0015 (14)	−0.0200 (15)
C6	0.0475 (17)	0.0461 (17)	0.0480 (17)	−0.0144 (14)	−0.0007 (13)	−0.0156 (14)
C7	0.0445 (17)	0.0477 (17)	0.0487 (17)	−0.0122 (13)	−0.0004 (13)	−0.0146 (14)
C8	0.0507 (18)	0.0459 (17)	0.0478 (18)	−0.0077 (14)	−0.0003 (14)	−0.0113 (14)
C9	0.0424 (17)	0.069 (2)	0.057 (2)	−0.0168 (16)	0.0026 (15)	−0.0164 (17)
C10	0.0465 (18)	0.0556 (19)	0.0532 (19)	−0.0203 (15)	0.0140 (15)	−0.0111 (15)
C11	0.059 (2)	0.0409 (17)	0.0545 (19)	−0.0064 (15)	0.0200 (16)	−0.0102 (14)
C12	0.0581 (19)	0.0362 (16)	0.0542 (19)	−0.0094 (14)	0.0124 (15)	−0.0070 (14)
C13	0.0492 (18)	0.0492 (18)	0.0422 (17)	−0.0088 (14)	0.0061 (13)	−0.0073 (14)
C14	0.076 (3)	0.078 (3)	0.057 (2)	−0.037 (2)	0.0149 (19)	−0.022 (2)
C15	0.089 (3)	0.082 (3)	0.055 (2)	−0.030 (2)	0.018 (2)	−0.028 (2)
C16	0.081 (3)	0.064 (2)	0.047 (2)	−0.018 (2)	0.0192 (19)	−0.0066 (17)
C17	0.137 (5)	0.091 (3)	0.068 (3)	−0.069 (3)	0.040 (3)	−0.017 (3)
C18	0.119 (4)	0.068 (3)	0.057 (2)	−0.049 (3)	0.024 (2)	−0.018 (2)
C19	0.123 (4)	0.100 (4)	0.064 (3)	−0.035 (3)	0.043 (3)	−0.016 (3)

Geometric parameters (Å, º) top

Br1—C2	1.898 (4)	C9—H9A	0.9700
N1—C5	1.367 (5)	C9—H9B	0.9700
N1—C8	1.377 (4)	C10—H10A	0.9700
N1—H1A	0.8600	C10—H10B	0.9700
N2—C10	1.474 (4)	C11—C12	1.495 (5)
N2—C11	1.476 (4)	C11—H11A	0.9700
N2—S1	1.616 (3)	C11—H11B	0.9700
O1—S1	1.431 (3)	C12—C12ⁱ	1.309 (7)
O2—S1	1.425 (3)	C12—H12	0.9300
S1—C13	1.762 (3)	C13—C18	1.368 (5)
C1—C2	1.368 (6)	C13—C14	1.369 (5)
C1—C6	1.398 (5)	C14—C15	1.379 (6)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.397 (6)	C15—C16	1.358 (6)
C3—C4	1.364 (6)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.370 (7)
C4—C5	1.382 (5)	C16—C19	1.515 (5)
C4—H4	0.9300	C17—C18	1.375 (6)
C5—C6	1.404 (5)	C17—H17	0.9300
C6—C7	1.435 (5)	C18—H18	0.9300
C7—C8	1.361 (5)	C19—H19A	0.9600
C7—C9	1.497 (5)	C19—H19B	0.9600
C8—H8	0.9300	C19—H19C	0.9600
C9—C10	1.500 (5)

C5—N1—C8	108.8 (3)	H9A—C9—H9B	107.5
C5—N1—H1A	125.6	N2—C10—C9	112.3 (3)
C8—N1—H1A	125.6	N2—C10—H10A	109.1
C10—N2—C11	115.7 (3)	C9—C10—H10A	109.1
C10—N2—S1	119.1 (2)	N2—C10—H10B	109.1
C11—N2—S1	116.5 (2)	C9—C10—H10B	109.1
O2—S1—O1	119.82 (19)	H10A—C10—H10B	107.9
O2—S1—N2	106.80 (17)	N2—C11—C12	113.2 (3)
O1—S1—N2	106.20 (16)	N2—C11—H11A	108.9
O2—S1—C13	107.97 (17)	C12—C11—H11A	108.9
O1—S1—C13	107.36 (17)	N2—C11—H11B	108.9
N2—S1—C13	108.24 (15)	C12—C11—H11B	108.9
C2—C1—C6	117.5 (3)	H11A—C11—H11B	107.8
C2—C1—H1	121.3	C12ⁱ—C12—C11	126.4 (4)
C6—C1—H1	121.3	C12ⁱ—C12—H12	116.8
C1—C2—C3	123.0 (4)	C11—C12—H12	116.8
C1—C2—Br1	118.9 (3)	C18—C13—C14	120.5 (3)
C3—C2—Br1	118.1 (3)	C18—C13—S1	120.1 (3)
C4—C3—C2	120.1 (4)	C14—C13—S1	119.4 (3)
C4—C3—H3	120.0	C13—C14—C15	119.0 (4)
C2—C3—H3	120.0	C13—C14—H14	120.5
C3—C4—C5	117.8 (4)	C15—C14—H14	120.5
C3—C4—H4	121.1	C16—C15—C14	121.8 (4)
C5—C4—H4	121.1	C16—C15—H15	119.1
N1—C5—C4	129.9 (3)	C14—C15—H15	119.1
N1—C5—C6	107.5 (3)	C15—C16—C17	118.0 (4)
C4—C5—C6	122.6 (4)	C15—C16—C19	120.9 (4)
C1—C6—C5	119.0 (3)	C17—C16—C19	121.1 (4)
C1—C6—C7	133.6 (3)	C16—C17—C18	121.7 (4)
C5—C6—C7	107.4 (3)	C16—C17—H17	119.1
C8—C7—C6	106.0 (3)	C18—C17—H17	119.1
C8—C7—C9	127.5 (3)	C13—C18—C17	119.0 (4)
C6—C7—C9	126.5 (3)	C13—C18—H18	120.5
C7—C8—N1	110.3 (3)	C17—C18—H18	120.5
C7—C8—H8	124.9	C16—C19—H19A	109.5
N1—C8—H8	124.9	C16—C19—H19B	109.5
C7—C9—C10	115.5 (3)	H19A—C19—H19B	109.5
C7—C9—H9A	108.4	C16—C19—H19C	109.5
C10—C9—H9A	108.4	H19A—C19—H19C	109.5
C7—C9—H9B	108.4	H19B—C19—H19C	109.5
C10—C9—H9B	108.4

C10—N2—S1—O2	168.7 (2)	C9—C7—C8—N1	−178.1 (3)
C11—N2—S1—O2	−45.2 (3)	C5—N1—C8—C7	−1.3 (4)
C10—N2—S1—O1	39.7 (3)	C8—C7—C9—C10	13.0 (5)
C11—N2—S1—O1	−174.1 (2)	C6—C7—C9—C10	−166.7 (3)
C10—N2—S1—C13	−75.3 (3)	C11—N2—C10—C9	69.3 (3)
C11—N2—S1—C13	70.9 (3)	S1—N2—C10—C9	−144.2 (3)
C6—C1—C2—C3	−1.3 (6)	C7—C9—C10—N2	68.5 (4)
C6—C1—C2—Br1	178.3 (2)	C10—N2—C11—C12	−99.8 (4)
C1—C2—C3—C4	1.1 (6)	S1—N2—C11—C12	112.9 (3)
Br1—C2—C3—C4	−178.4 (3)	N2—C11—C12—C12ⁱ	−14.2 (7)
C2—C3—C4—C5	0.3 (6)	O2—S1—C13—C18	−170.1 (4)
C8—N1—C5—C4	179.5 (4)	O1—S1—C13—C18	−39.7 (4)
C8—N1—C5—C6	0.5 (4)	N2—S1—C13—C18	74.6 (4)
C3—C4—C5—N1	179.7 (4)	O2—S1—C13—C14	11.4 (4)
C3—C4—C5—C6	−1.4 (6)	O1—S1—C13—C14	141.9 (3)
C2—C1—C6—C5	0.1 (5)	N2—S1—C13—C14	−103.8 (3)
C2—C1—C6—C7	179.9 (4)	C18—C13—C14—C15	−0.2 (7)
N1—C5—C6—C1	−179.7 (3)	S1—C13—C14—C15	178.2 (4)
C4—C5—C6—C1	1.2 (5)	C13—C14—C15—C16	−0.9 (8)
N1—C5—C6—C7	0.5 (4)	C14—C15—C16—C17	0.8 (8)
C4—C5—C6—C7	−178.6 (3)	C14—C15—C16—C19	−178.8 (5)
C1—C6—C7—C8	178.9 (4)	C15—C16—C17—C18	0.5 (9)
C5—C6—C7—C8	−1.3 (4)	C19—C16—C17—C18	−179.9 (6)
C1—C6—C7—C9	−1.3 (6)	C14—C13—C18—C17	1.5 (7)
C5—C6—C7—C9	178.4 (3)	S1—C13—C18—C17	−176.9 (4)
C6—C7—C8—N1	1.6 (4)	C16—C17—C18—C13	−1.7 (9)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱⁱ	0.86	2.05	2.865 (4)	158

Symmetry code: (ii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₈H₃₈Br₂N₄O₄S₂
M_r	838.66
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.9222 (8), 10.4859 (13), 15.601 (2)
α, β, γ (°)	79.528 (2), 87.824 (2), 75.186 (2)
V (Å³)	921.0 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.36
Crystal size (mm)	0.30 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.538, 0.625
No. of measured, independent and observed [I > 2σ(I)] reflections	5033, 3545, 2966
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.152, 1.02
No. of reflections	3545
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.60, −1.07

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.05	2.865 (4)	158

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

This project was sponsored by the National Science Foundation of Jiangsu Province (No. BK2009262) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry.

References

Abbassi, N., Rakib, E. M. & Zouihri, H. (2011). Acta Cryst. E67, o1354. Web of Science CSD CrossRef IUCr Journals Google Scholar
Akkurt, M., Mariam, I., Naseer, I., Khan, I. U. & Sharif, S. (2011). Acta Cryst. E67, o186. Web of Science CrossRef IUCr Journals Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ozbek, N., Katircioglu, H., Karacan, N. & Baykal, T. (2007). Bioorg. Med. Chem. 15, 5105–5109. Web of Science CrossRef PubMed 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 67| Part 11| November 2011| Page o2987

doi:10.1107/S1600536811041791

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

(E)-N,N′-Bis[2-(5-bromo-1H-indol-3-yl)eth­yl]-N,N′-(but-2-ene-1,4-di­yl)bis­­(4-methyl­benzene­sulfonamide)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N,N′-Bis[2-(5-bromo-1H-indol-3-yl)ethyl]-N,N′-(but-2-ene-1,4-diyl)bis(4-methylbenzenesulfonamide)