4-Bromo-2-(5-bromo-thio-phen-2-yl)-1-[(5-bromo-thio-phen-2-yl)meth-yl]-5,6-dimethyl-1H-benzimidazole.

The title compound, C18H13Br3N2S2, was obtained via the reaction of N-bromo-succinamide with 5,6-dimethyl-2-(thio-phen-2-yl)-1-[(thio-phen-2-yl)meth-yl]-1H-benzimidazole. The compound exhibits rotational disorder of the 5-bromo-thio-phen-2-yl substituent with a refined major:minor occupancy ratio of 0.876 (7):0.124 (7). The 5-bromo-thio-phen-2-yl mean plane is canted to the benzimidazole plane by 20.0 (4) and 21 (4)° in the major and minor components, respectively. In the crystal, weak C-H⋯N inter-actions link the mol-ecules into infinite C(7) chains along the 21 axes.

Related literature

Bromination of thio­phenes using N-bromo­succinamide has been reported by Arsenyan et al. (2010 ▶). For the structure of 5,6-di­methyl­benzimidazole, see: Lee & Scheidt (1986 ▶). For the structure of 2-(thio­phen-2-yl)-1-(thio­phen-2-ylmeth­yl)-1H-benzimidazole, see: Geiger et al. (2012 ▶). For the 5-chloro derivative, see: Geiger & Nellist (2013a ▶), for the 6-chloro derivative, see: Geiger & Nellist (2013b ▶) and for the 6-bromo derivative, see: Geiger & Destefano (2012 ▶). For a discussion of the biological activity of benzimidazole derivatives, see: López-Rodríguez et al. (1999 ▶); Horton et al. (2003 ▶).

Experimental

Crystal data

C18H13Br3N2S2

M = 561.15

Monoclinic,

a = 13.6796 (13) Å

b = 9.6144 (8) Å

c = 14.8093 (15) Å

β = 98.305 (3)°

V = 1927.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 6.50 mm−1

T = 200 K

0.60 × 0.40 × 0.10 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.35, T max = 0.56

12301 measured reflections

3561 independent reflections

2810 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.179

S = 1.06

3561 reflections

247 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −1.90 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400628X/rz5112sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400628X/rz5112Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400628X/rz5112Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400628X/rz5112Isup4.cml

CCDC reference: 992876

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H13Br3N2S2	F(000) = 1088
Mr = 561.15	Dx = 1.934 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4288 reflections
a = 13.6796 (13) Å	θ = 2.5–25.0°
b = 9.6144 (8) Å	µ = 6.50 mm−1
c = 14.8093 (15) Å	T = 200 K
β = 98.305 (3)°	Plate, clear colourless
V = 1927.3 (3) Å3	0.60 × 0.40 × 0.10 mm
Z = 4

Bruker SMART X2S benchtop diffractometer	3561 independent reflections
Radiation source: sealed microfocus tube	2810 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.036
Detector resolution: 8.3330 pixels mm-1	θmax = 25.5°, θmin = 1.9°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→11
Tmin = 0.35, Tmax = 0.56	l = −17→11
12301 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0876P)2 + 13.3538P] where P = (Fo2 + 2Fc2)/3
3561 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.87 e Å−3
16 restraints	Δρmin = −1.90 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	Occ. (<1)
C1	0.6567 (5)	0.4489 (7)	0.0616 (5)	0.0297 (15)
C2	0.5806 (5)	0.3747 (7)	0.0935 (5)	0.0291 (15)
C3	0.5164 (5)	0.2979 (7)	0.0299 (5)	0.0328 (16)
C4	0.5271 (6)	0.2972 (7)	−0.0623 (5)	0.0345 (17)
C5	0.6069 (6)	0.3752 (9)	−0.0909 (5)	0.0388 (18)
C6	0.6698 (6)	0.4519 (8)	−0.0296 (5)	0.0341 (16)
H6	0.7211	0.5058	−0.0491	0.041*
C41	0.4614 (7)	0.2091 (9)	−0.1300 (6)	0.048 (2)
H41A	0.4983	0.1275	−0.146	0.071*
H41B	0.4395	0.2637	−0.185	0.071*
H41C	0.4037	0.1787	−0.1029	0.071*
C51	0.6220 (7)	0.3744 (12)	−0.1887 (5)	0.055 (2)
H51A	0.6732	0.442	−0.1979	0.083*
H51B	0.56	0.3992	−0.2271	0.083*
H51C	0.6426	0.2813	−0.2053	0.083*
Br3	0.41595 (6)	0.19379 (9)	0.07516 (6)	0.0461 (3)
N1	0.7086 (4)	0.5125 (6)	0.1385 (4)	0.0291 (13)
C7	0.6621 (5)	0.4710 (7)	0.2112 (5)	0.0282 (15)
N2	0.5860 (4)	0.3888 (6)	0.1866 (4)	0.0284 (13)
C8	0.6925 (12)	0.5165 (15)	0.3059 (6)	0.0252 (18)	0.876 (7)
C9	0.7801 (11)	0.5660 (14)	0.3497 (7)	0.031 (2)	0.876 (7)
H9	0.8365	0.5803	0.3203	0.037*	0.876 (7)
C10	0.7787 (8)	0.5937 (9)	0.4431 (6)	0.030 (2)	0.876 (7)
H10	0.8334	0.6288	0.4835	0.036*	0.876 (7)
C11	0.6903 (8)	0.5643 (9)	0.4674 (5)	0.032 (2)	0.876 (7)
S1	0.6069 (8)	0.5018 (9)	0.3795 (3)	0.0336 (12)	0.876 (7)
Br1	0.65371 (11)	0.5955 (3)	0.58337 (8)	0.0544 (5)	0.876 (7)
C80	0.685 (8)	0.502 (10)	0.302 (3)	0.0252 (18)	0.124 (7)
C90	0.775 (7)	0.543 (11)	0.347 (4)	0.031 (2)	0.124 (7)
H90	0.8304	0.5603	0.3166	0.037*	0.124 (7)
C100	0.777 (5)	0.557 (9)	0.442 (4)	0.030 (2)	0.124 (7)
H100	0.8338	0.5836	0.4829	0.036*	0.124 (7)
C110	0.689 (4)	0.529 (7)	0.4662 (19)	0.032 (2)	0.124 (7)
S10	0.602 (6)	0.480 (8)	0.377 (2)	0.0336 (12)	0.124 (7)
Br10	0.6580 (9)	0.530 (2)	0.5862 (6)	0.0544 (5)	0.124 (7)
C12	0.7869 (5)	0.6148 (7)	0.1354 (5)	0.0312 (16)
H12A	0.7851	0.6824	0.1856	0.037*
H12B	0.7734	0.6666	0.0772	0.037*
C13	0.8884 (5)	0.5541 (7)	0.1435 (4)	0.0267 (15)
C14	0.9740 (6)	0.6115 (9)	0.1828 (5)	0.0399 (18)
H14	0.9773	0.6971	0.2151	0.048*
C15	1.0593 (6)	0.5319 (9)	0.1713 (6)	0.0426 (19)
H15	1.1251	0.5573	0.195	0.051*
C16	1.0341 (6)	0.4152 (8)	0.1220 (5)	0.0387 (18)
S2	0.90879 (16)	0.3984 (2)	0.09103 (14)	0.0396 (5)
Br2	1.11809 (9)	0.28087 (11)	0.08705 (7)	0.0637 (4)

	U11	U22	U33	U12	U13	U23
C1	0.036 (4)	0.020 (3)	0.032 (4)	0.003 (3)	0.005 (3)	0.001 (3)
C2	0.034 (4)	0.021 (3)	0.032 (4)	0.009 (3)	0.003 (3)	0.003 (3)
C3	0.033 (4)	0.025 (4)	0.037 (4)	0.003 (3)	−0.005 (3)	0.003 (3)
C4	0.037 (4)	0.029 (4)	0.035 (4)	0.015 (3)	−0.004 (3)	−0.001 (3)
C5	0.040 (4)	0.046 (5)	0.029 (4)	0.019 (4)	0.002 (3)	0.004 (3)
C6	0.038 (4)	0.035 (4)	0.029 (4)	0.005 (3)	0.007 (3)	0.002 (3)
C41	0.049 (5)	0.050 (5)	0.039 (4)	0.007 (4)	−0.010 (4)	−0.009 (4)
C51	0.049 (5)	0.086 (7)	0.030 (4)	0.023 (5)	0.000 (4)	0.001 (4)
Br3	0.0447 (5)	0.0381 (5)	0.0518 (5)	−0.0119 (4)	−0.0055 (4)	0.0037 (4)
N1	0.034 (3)	0.026 (3)	0.027 (3)	−0.006 (3)	0.004 (2)	−0.002 (2)
C7	0.033 (4)	0.021 (3)	0.031 (4)	0.002 (3)	0.006 (3)	0.001 (3)
N2	0.031 (3)	0.021 (3)	0.032 (3)	−0.002 (2)	0.002 (2)	0.001 (2)
C8	0.030 (5)	0.017 (4)	0.029 (3)	−0.003 (3)	0.007 (3)	0.002 (3)
C9	0.030 (4)	0.029 (6)	0.033 (4)	−0.007 (4)	0.005 (3)	−0.001 (3)
C10	0.036 (4)	0.023 (6)	0.029 (4)	−0.006 (4)	0.000 (3)	0.001 (4)
C11	0.050 (5)	0.019 (5)	0.027 (4)	−0.002 (4)	0.006 (3)	0.003 (3)
S1	0.0328 (17)	0.038 (4)	0.0307 (10)	−0.0099 (19)	0.0077 (9)	−0.0001 (11)
Br1	0.0781 (7)	0.0542 (15)	0.0354 (5)	−0.0216 (8)	0.0230 (5)	−0.0079 (6)
C80	0.030 (5)	0.017 (4)	0.029 (3)	−0.003 (3)	0.007 (3)	0.002 (3)
C90	0.030 (4)	0.029 (6)	0.033 (4)	−0.007 (4)	0.005 (3)	−0.001 (3)
C100	0.036 (4)	0.023 (6)	0.029 (4)	−0.006 (4)	0.000 (3)	0.001 (4)
C110	0.050 (5)	0.019 (5)	0.027 (4)	−0.002 (4)	0.006 (3)	0.003 (3)
S10	0.0328 (17)	0.038 (4)	0.0307 (10)	−0.0099 (19)	0.0077 (9)	−0.0001 (11)
Br10	0.0781 (7)	0.0542 (15)	0.0354 (5)	−0.0216 (8)	0.0230 (5)	−0.0079 (6)
C12	0.039 (4)	0.025 (3)	0.031 (4)	−0.006 (3)	0.008 (3)	0.003 (3)
C13	0.035 (4)	0.023 (3)	0.024 (3)	0.001 (3)	0.009 (3)	0.001 (3)
C14	0.044 (5)	0.037 (4)	0.039 (4)	0.000 (4)	0.007 (4)	−0.006 (3)
C15	0.032 (4)	0.052 (5)	0.046 (5)	0.000 (4)	0.011 (3)	−0.002 (4)
C16	0.041 (5)	0.042 (4)	0.036 (4)	0.009 (4)	0.014 (3)	0.005 (3)
S2	0.0445 (11)	0.0302 (10)	0.0444 (11)	0.0010 (9)	0.0071 (9)	−0.0083 (8)
Br2	0.0795 (7)	0.0563 (6)	0.0619 (6)	0.0217 (5)	0.0329 (5)	0.0114 (5)

C1—C6	1.389 (10)	C9—C10	1.410 (10)
C1—N1	1.393 (9)	C9—H9	0.95
C1—C2	1.399 (10)	C10—C11	1.341 (11)
C2—N2	1.376 (9)	C10—H10	0.95
C2—C3	1.402 (10)	C11—S1	1.711 (8)
C3—C4	1.394 (11)	C11—Br1	1.882 (8)
C3—Br3	1.899 (8)	C80—C90	1.36 (2)
C4—C5	1.439 (12)	C80—S10	1.717 (19)
C4—C41	1.506 (11)	C90—C100	1.41 (2)
C5—C6	1.372 (11)	C90—H90	0.95
C5—C51	1.492 (11)	C100—C110	1.34 (2)
C6—H6	0.95	C100—H100	0.95
C41—H41A	0.98	C110—S10	1.710 (19)
C41—H41B	0.98	C110—Br10	1.884 (18)
C41—H41C	0.98	C12—C13	1.494 (10)
C51—H51A	0.98	C12—H12A	0.99
C51—H51B	0.98	C12—H12B	0.99
C51—H51C	0.98	C13—C14	1.349 (11)
N1—C7	1.387 (9)	C13—S2	1.728 (7)
N1—C12	1.460 (9)	C14—C15	1.426 (11)
C7—N2	1.317 (9)	C14—H14	0.95
C7—C80	1.37 (5)	C15—C16	1.356 (12)
C7—C8	1.470 (11)	C15—H15	0.95
C8—C9	1.363 (10)	C16—S2	1.717 (8)
C8—S1	1.717 (7)	C16—Br2	1.852 (8)
C6—C1—N1	131.5 (7)	C8—C9—C10	113.4 (7)
C6—C1—C2	123.1 (7)	C8—C9—H9	123.3
N1—C1—C2	105.3 (6)	C10—C9—H9	123.3
N2—C2—C1	110.7 (6)	C11—C10—C9	111.3 (7)
N2—C2—C3	131.5 (7)	C11—C10—H10	124.4
C1—C2—C3	117.8 (7)	C9—C10—H10	124.4
C4—C3—C2	121.1 (7)	C10—C11—S1	113.5 (6)
C4—C3—Br3	121.7 (6)	C10—C11—Br1	125.5 (6)
C2—C3—Br3	117.1 (5)	S1—C11—Br1	120.9 (5)
C3—C4—C5	118.5 (7)	C11—S1—C8	90.7 (4)
C3—C4—C41	121.2 (8)	C90—C80—C7	127 (6)
C5—C4—C41	120.2 (7)	C90—C80—S10	111.0 (17)
C6—C5—C4	121.0 (7)	C7—C80—S10	122 (6)
C6—C5—C51	118.9 (8)	C80—C90—C100	114 (2)
C4—C5—C51	120.0 (8)	C80—C90—H90	123.2
C5—C6—C1	118.4 (7)	C100—C90—H90	123.2
C5—C6—H6	120.8	C110—C100—C90	111 (2)
C1—C6—H6	120.8	C110—C100—H100	124.5
C4—C41—H41A	109.5	C90—C100—H100	124.5
C4—C41—H41B	109.5	C100—C110—S10	113.7 (16)
H41A—C41—H41B	109.5	C100—C110—Br10	126 (2)
C4—C41—H41C	109.5	S10—C110—Br10	120 (2)
H41A—C41—H41C	109.5	C110—S10—C80	90.7 (13)
H41B—C41—H41C	109.5	N1—C12—C13	114.3 (6)
C5—C51—H51A	109.5	N1—C12—H12A	108.7
C5—C51—H51B	109.5	C13—C12—H12A	108.7
H51A—C51—H51B	109.5	N1—C12—H12B	108.7
C5—C51—H51C	109.5	C13—C12—H12B	108.7
H51A—C51—H51C	109.5	H12A—C12—H12B	107.6
H51B—C51—H51C	109.5	C14—C13—C12	127.9 (7)
C7—N1—C1	105.8 (6)	C14—C13—S2	111.2 (6)
C7—N1—C12	129.7 (6)	C12—C13—S2	120.7 (5)
C1—N1—C12	124.1 (6)	C13—C14—C15	113.8 (7)
N2—C7—C80	118 (4)	C13—C14—H14	123.1
N2—C7—N1	113.0 (6)	C15—C14—H14	123.1
C80—C7—N1	129 (4)	C16—C15—C14	111.1 (7)
N2—C7—C8	123.1 (7)	C16—C15—H15	124.5
N1—C7—C8	123.9 (7)	C14—C15—H15	124.5
C7—N2—C2	105.2 (6)	C15—C16—S2	112.9 (6)
C9—C8—C7	131.8 (10)	C15—C16—Br2	127.4 (6)
C9—C8—S1	111.1 (6)	S2—C16—Br2	119.7 (5)
C7—C8—S1	117.1 (8)	C16—S2—C13	91.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N2i	0.95	2.57	3.461 (10)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N2i	0.95	2.57	3.461 (10)	156

Symmetry code: (i) .