(E)-N,N'-Bis[2-(5-bromo-1H-indol-3-yl)eth-yl]-N,N'-(but-2-ene-1,4-di-yl)bis-(4-methyl-benzene-sulfonamide).

In the title compound, C(38)H(38)Br(2)N(4)O(4)S(2), 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 mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, generating R(2) (2)(16) loops within [1[Formula: see text]0] chains. Short Br⋯Br contacts [3.6148 (9) Å] are observed between adjacent mol-ecules.

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 = 838.66

Triclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.152

S = 1.02

3545 reflections

227 parameters

H-atom parameters constrained

Δρmax = 1.60 e Å−3

Δρmin = −1.07 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041791/hb6445sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811041791/hb6445Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C38H38Br2N4O4S2	Z = 1
Mr = 838.66	F(000) = 428
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.083P)2 + 0.8618P] where P = (Fo2 + 2Fc2)/3
3545 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 1.60 e Å−3
0 restraints	Δρmin = −1.07 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .