2-n-Butyl-6-chloro-1-(2,4-dimethyl-phenyl-sulfon-yl)-1H-benzimidazole-2-n-butyl-5-chloro-1-(2,4-dimethyl-phenyl-sulfon-yl)-1H-benzimidazole (0.759/0.241).

The title compound, 0.759C(19)H(21)ClN(2)O(2)S·0.241C(19)H(21)ClN(2)O(2)S, was synthesized by aryl-sulfonyl-ation of 2-n-butyl-5-chloro-1H-benzimidazole in the presence of triethyl-amine. The crystal structure is composed of two mol-ecules, 2-n-butyl-6-chloro-1-(2,4-dimethylphenyl-sulfon-yl)-1H-benzimidazole and 1-(2,4-dimethylphenyl-sulfon-yl)-2-n-butyl-5-chloro-1H-benz-imidazole, in the refined ratio of 0.759 (4):0.241 (4) disordered at the same position in the unit cell. The mol-ecule has three essentially planar fragments viz. benzimidazole, dimethyl-benzene and n-butyl (r.m.s. deviations of 0.009, 0.024 and 0.003 Å, respectively). The angle between the benzimidazole and dimethyl-benzene fragments is 86.0 (1)°. In the crystal, pairs of inter-molecular C-H⋯π inter-actions form centrosymmetrical dimers, which are linked by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the biological and pharmaceutical properties of benz­imid­azole derivatives, see: Koči et al. (2002 ▶); Matsuno et al. (2000 ▶); Garuti et al. (1999 ▶). For the synthesis, biological activity and related structures of 2-n-butyl­benzimidazole derivatives, see: Kubo et al. (1993a ▶,b ▶); For the aryl­sulfonyl­ation of benzimidazole derivatives, see: Abdireimov et al. (2010 ▶).

Experimental

Crystal data

0.759C19H21ClN2O2S·0.241C19H21ClN2O2S

M = 376.89

Triclinic,

a = 8.7340 (17) Å

b = 10.251 (2) Å

c = 11.390 (2) Å

α = 71.29 (3)°

β = 78.38 (3)°

γ = 76.75 (3)°

V = 931.1 (3) Å3

Z = 2

Cu Kα radiation

μ = 2.98 mm−1

T = 290 K

0.68 × 0.45 × 0.20 mm

Data collection

Stoe Stadi-4 four-circle diffractometer

Absorption correction: ψ scan (X-RED; Stoe & Cie, 1997 ▶) T min = 0.250, T max = 0.551

2722 measured reflections

2714 independent reflections

2460 reflections with I > 2σ(I)

θmax = 60.0°

3 standard reflections every 60 min intensity decay: 10.4%

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.191

S = 1.12

2714 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.45 e Å−3

Data collection: STADI4 (Stoe & Cie, 1997 ▶); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047957/im2330sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047957/im2330Isup2.hkl

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

0.7590.241C19H21ClN2O2S·0.2410.241C19H21ClN2O2S	Z = 2
Mr = 376.89	F(000) = 396
Triclinic, P1	Dx = 1.344 Mg m−3
Hall symbol: -P 1	Melting point < 381(9) K
a = 8.7340 (17) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.251 (2) Å	Cell parameters from 13 reflections
c = 11.390 (2) Å	θ = 10–20°
α = 71.29 (3)°	µ = 2.98 mm−1
β = 78.38 (3)°	T = 290 K
γ = 76.75 (3)°	Prizmatic, colorless
V = 931.1 (3) Å3	0.68 × 0.45 × 0.20 mm

Stoe Stadi-4 four-circle diffractometer	2460 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
graphite	θmax = 60.0°, θmin = 4.1°
Scan width (ω) = 1.56 – 1.80, scan ratio 2θ:ω = 1.00 I(Net) and sigma(I) calculated according to Blessing (1987)	h = −9→9
Absorption correction: ψ scan (X-RED; Stoe & Cie, 1997)	k = −10→11
Tmin = 0.250, Tmax = 0.551	l = 0→12
2722 measured reflections	3 standard reflections every 60 min
2714 independent reflections	intensity decay: 10.4%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069	H-atom parameters constrained
wR(F2) = 0.191	w = 1/[σ2(Fo2) + (0.0919P)2 + 1.1929P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2714 reflections	Δρmax = 0.35 e Å−3
240 parameters	Δρmin = −0.45 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (3)

Experimental. Empirical absorption correction using ψ Scan. Reflections used Mu * R = 0.00 H K L, θ, χ, Imin/Imax: -1 -2 4 45.0 82.7 0.4551H NMR (400 MHz, CDCl~3~): 1-(2,4-dimethylbenzenesulfonyl)-2-n-butyl-6- chloro-1H-benzimidazole (A). 7.97 (1H, d, J═2.1 Hz, H-7), 7.49 (1H, d, J═8.3 Hz, H-17), 7.49 (1H, d, J═8.5 Hz, H-4), 7.37 (2H, d, J═7.9 Hz, H-14, 16), 7.29 (1H, dd, J═2.o, J═8.5 H-5), 3.08 (2H, m, CH2-8), 2.34 (6H, s, CH3-18, 19), 1.73 (2H, m, CH2-9), 1.37 (2H, m, CH2-10), 0.89 (3H, t, J═7.3 Hz, CH3-11).1-(2,4-dimethylbenzenesulfonyl)-2-n-butyl-5-chloro- 1H-benzimidazole (B). 7.95 (1H, d, J═8.7 Hz, H-7), 7.78 (1H, d, J═8.3 Hz, H-17), 7.52 (1H, d, J═2.0 Hz, H-4), 7.35 (2H, d, J═7.9 Hz, H-14, 16), 7.31 (1H, dd, J═2.o, J═8.5 H-6), 3.08 (2H, m, CH2-8), 2.34 (6H, s, CH3-18, 19), 1.73 (2H, m, CH2-9), 1.37 (2H, m, CH2-10), 0.90 (3H, t, J═7.5 Hz, CH3-11).

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)
S1	0.25613 (12)	0.65554 (11)	0.19565 (9)	0.0537 (4)
O1	0.2520 (4)	0.5625 (3)	0.1267 (3)	0.0660 (9)
O2	0.1230 (4)	0.7622 (3)	0.2077 (3)	0.0647 (9)
N1	0.2783 (4)	0.5558 (3)	0.3424 (3)	0.0511 (8)
N3	0.3767 (4)	0.3796 (4)	0.4993 (3)	0.0606 (10)
C2	0.3863 (5)	0.4310 (4)	0.3785 (4)	0.0552 (10)
C3A	0.2567 (5)	0.4705 (4)	0.5479 (4)	0.0552 (10)
C4	0.1997 (6)	0.4606 (5)	0.6731 (4)	0.0688 (13)
H4A	0.2428	0.3874	0.7370	0.083*
C5	0.0780 (6)	0.5624 (5)	0.6986 (4)	0.0658 (12)
H5A	0.0377	0.5584	0.7815	0.079*	0.759 (4)
C6	0.0142 (5)	0.6701 (5)	0.6052 (4)	0.0604 (11)
H6A	−0.0684	0.7372	0.6269	0.072*	0.241 (4)
C7	0.0675 (5)	0.6835 (5)	0.4791 (4)	0.0573 (11)
H7A	0.0226	0.7564	0.4158	0.069*
C7A	0.1909 (5)	0.5817 (4)	0.4545 (4)	0.0498 (10)
C8	0.4990 (5)	0.3662 (5)	0.2876 (4)	0.0606 (11)
H8A	0.5704	0.4300	0.2385	0.073*
H8B	0.4397	0.3519	0.2306	0.073*
C9	0.5963 (6)	0.2267 (5)	0.3510 (4)	0.0640 (12)
H9A	0.6586	0.2409	0.4061	0.077*
H9B	0.5255	0.1631	0.4016	0.077*
C10	0.7063 (7)	0.1625 (5)	0.2552 (5)	0.0754 (14)
H10A	0.7774	0.2261	0.2052	0.090*
H10B	0.6439	0.1496	0.1997	0.090*
C11	0.8036 (7)	0.0226 (6)	0.3163 (6)	0.0918 (18)
H11A	0.8725	−0.0141	0.2528	0.138*
H11B	0.7337	−0.0417	0.3638	0.138*
H11C	0.8662	0.0349	0.3710	0.138*
C12	0.4289 (5)	0.7259 (4)	0.1379 (4)	0.0498 (10)
C13	0.4696 (5)	0.8270 (4)	0.1800 (4)	0.0553 (11)
C14	0.6081 (6)	0.8746 (4)	0.1239 (4)	0.0603 (11)
H14A	0.6356	0.9413	0.1512	0.072*
C15	0.7100 (5)	0.8296 (5)	0.0291 (4)	0.0615 (11)
C16	0.6664 (6)	0.7320 (5)	−0.0118 (4)	0.0657 (12)
H16A	0.7317	0.6998	−0.0757	0.079*
C17	0.5288 (6)	0.6823 (5)	0.0405 (4)	0.0609 (11)
H17A	0.5009	0.6178	0.0105	0.073*
C18	0.3722 (6)	0.8773 (5)	0.2876 (5)	0.0702 (13)
H18A	0.4075	0.9581	0.2906	0.105*
H18B	0.3850	0.8043	0.3646	0.105*
H18C	0.2623	0.9014	0.2761	0.105*
C19	0.8634 (6)	0.8809 (7)	−0.0233 (6)	0.0881 (16)
H19A	0.9019	0.8631	−0.1029	0.132*
H19B	0.9399	0.8329	0.0331	0.132*
H19C	0.8471	0.9796	−0.0340	0.132*
Cl1	−0.1412 (2)	0.79798 (18)	0.64266 (16)	0.0782 (7)	0.759 (4)
Cl1'	0.0475 (7)	0.5668 (7)	0.8540 (5)	0.081 (2)	0.241 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0575 (7)	0.0540 (7)	0.0473 (6)	−0.0039 (5)	−0.0118 (5)	−0.0129 (5)
O1	0.077 (2)	0.073 (2)	0.0594 (18)	−0.0196 (16)	−0.0128 (15)	−0.0283 (16)
O2	0.0621 (18)	0.0621 (18)	0.0554 (18)	0.0096 (14)	−0.0143 (14)	−0.0076 (14)
N1	0.056 (2)	0.0460 (18)	0.0433 (18)	−0.0003 (15)	−0.0038 (15)	−0.0104 (15)
N3	0.068 (2)	0.053 (2)	0.054 (2)	0.0043 (17)	−0.0096 (17)	−0.0153 (17)
C2	0.056 (2)	0.049 (2)	0.059 (3)	0.0009 (19)	−0.0074 (19)	−0.020 (2)
C3A	0.058 (2)	0.050 (2)	0.054 (2)	0.0005 (19)	−0.0065 (19)	−0.0173 (19)
C4	0.082 (3)	0.066 (3)	0.049 (3)	0.000 (2)	−0.008 (2)	−0.013 (2)
C5	0.073 (3)	0.070 (3)	0.049 (2)	−0.009 (2)	0.002 (2)	−0.019 (2)
C6	0.054 (2)	0.062 (3)	0.063 (3)	−0.006 (2)	0.001 (2)	−0.025 (2)
C7	0.053 (2)	0.056 (2)	0.056 (3)	0.0005 (19)	−0.0031 (19)	−0.016 (2)
C7A	0.051 (2)	0.049 (2)	0.046 (2)	−0.0048 (18)	−0.0043 (17)	−0.0128 (18)
C8	0.063 (3)	0.058 (3)	0.058 (3)	0.003 (2)	−0.004 (2)	−0.024 (2)
C9	0.063 (3)	0.060 (3)	0.065 (3)	0.006 (2)	−0.008 (2)	−0.025 (2)
C10	0.084 (3)	0.058 (3)	0.078 (3)	0.011 (2)	−0.008 (3)	−0.028 (3)
C11	0.082 (4)	0.075 (4)	0.112 (5)	0.023 (3)	−0.021 (3)	−0.041 (3)
C12	0.057 (2)	0.045 (2)	0.045 (2)	−0.0020 (18)	−0.0097 (18)	−0.0132 (17)
C13	0.067 (3)	0.045 (2)	0.053 (2)	0.001 (2)	−0.015 (2)	−0.0169 (19)
C14	0.071 (3)	0.049 (2)	0.063 (3)	−0.011 (2)	−0.021 (2)	−0.011 (2)
C15	0.063 (3)	0.062 (3)	0.053 (2)	−0.008 (2)	−0.013 (2)	−0.006 (2)
C16	0.071 (3)	0.068 (3)	0.054 (3)	−0.013 (2)	0.002 (2)	−0.016 (2)
C17	0.076 (3)	0.057 (3)	0.051 (2)	−0.010 (2)	−0.004 (2)	−0.021 (2)
C18	0.085 (3)	0.065 (3)	0.065 (3)	−0.004 (2)	−0.009 (2)	−0.033 (2)
C19	0.076 (4)	0.096 (4)	0.086 (4)	−0.026 (3)	−0.013 (3)	−0.010 (3)
Cl1	0.0714 (11)	0.0803 (12)	0.0733 (11)	0.0080 (8)	0.0057 (8)	−0.0333 (9)
Cl1'	0.077 (4)	0.100 (4)	0.069 (3)	−0.018 (3)	0.010 (3)	−0.039 (3)

S1—O2	1.419 (3)	C9—H9A	0.9700
S1—O1	1.427 (3)	C9—H9B	0.9700
S1—N1	1.679 (3)	C10—C11	1.517 (7)
S1—C12	1.739 (4)	C10—H10A	0.9700
N1—C2	1.401 (5)	C10—H10B	0.9700
N1—C7A	1.420 (5)	C11—H11A	0.9600
N3—C2	1.298 (6)	C11—H11B	0.9600
N3—C3A	1.387 (5)	C11—H11C	0.9600
C2—C8	1.488 (6)	C12—C17	1.394 (6)
C3A—C7A	1.389 (6)	C12—C13	1.410 (6)
C3A—C4	1.392 (6)	C13—C14	1.366 (6)
C4—C5	1.366 (7)	C13—C18	1.508 (6)
C4—H4A	0.9300	C14—C15	1.383 (7)
C5—C6	1.365 (7)	C14—H14A	0.9300
C5—Cl1'	1.750 (7)	C15—C16	1.382 (7)
C5—H5A	0.9300	C15—C19	1.493 (7)
C6—C7	1.390 (6)	C16—C17	1.362 (7)
C6—Cl1	1.747 (5)	C16—H16A	0.9300
C6—H6A	0.9300	C17—H17A	0.9300
C7—C7A	1.371 (6)	C18—H18A	0.9600
C7—H7A	0.9300	C18—H18B	0.9600
C8—C9	1.522 (6)	C18—H18C	0.9600
C8—H8A	0.9700	C19—H19A	0.9600
C8—H8B	0.9700	C19—H19B	0.9600
C9—C10	1.515 (6)	C19—H19C	0.9600
O2—S1—O1	119.5 (2)	C8—C9—H9B	109.4
O2—S1—N1	105.51 (18)	H9A—C9—H9B	108.0
O1—S1—N1	106.36 (18)	C9—C10—C11	112.0 (5)
O2—S1—C12	110.7 (2)	C9—C10—H10A	109.2
O1—S1—C12	108.22 (19)	C11—C10—H10A	109.2
N1—S1—C12	105.50 (18)	C9—C10—H10B	109.2
C2—N1—C7A	106.4 (3)	C11—C10—H10B	109.2
C2—N1—S1	126.9 (3)	H10A—C10—H10B	107.9
C7A—N1—S1	126.7 (3)	C10—C11—H11A	109.5
C2—N3—C3A	105.6 (3)	C10—C11—H11B	109.5
N3—C2—N1	112.4 (4)	H11A—C11—H11B	109.5
N3—C2—C8	124.4 (4)	C10—C11—H11C	109.5
N1—C2—C8	123.2 (4)	H11A—C11—H11C	109.5
N3—C3A—C7A	112.1 (4)	H11B—C11—H11C	109.5
N3—C3A—C4	128.0 (4)	C17—C12—C13	118.9 (4)
C7A—C3A—C4	119.9 (4)	C17—C12—S1	116.9 (3)
C5—C4—C3A	117.5 (4)	C13—C12—S1	124.2 (3)
C5—C4—H4A	121.3	C14—C13—C12	117.5 (4)
C3A—C4—H4A	121.3	C14—C13—C18	119.6 (4)
C6—C5—C4	121.5 (4)	C12—C13—C18	122.8 (4)
C6—C5—Cl1'	122.7 (4)	C13—C14—C15	124.2 (4)
C4—C5—Cl1'	114.0 (4)	C13—C14—H14A	117.9
C6—C5—H5A	119.2	C15—C14—H14A	117.9
C4—C5—H5A	119.2	C16—C15—C14	117.3 (4)
C5—C6—C7	122.8 (4)	C16—C15—C19	121.5 (5)
C5—C6—Cl1	119.8 (4)	C14—C15—C19	121.2 (5)
C7—C6—Cl1	117.4 (4)	C17—C16—C15	120.8 (4)
C5—C6—H6A	118.6	C17—C16—H16A	119.6
C7—C6—H6A	118.6	C15—C16—H16A	119.6
C7A—C7—C6	115.2 (4)	C16—C17—C12	121.4 (4)
C7A—C7—H7A	122.4	C16—C17—H17A	119.3
C6—C7—H7A	122.4	C12—C17—H17A	119.3
C7—C7A—C3A	123.0 (4)	C13—C18—H18A	109.5
C7—C7A—N1	133.5 (4)	C13—C18—H18B	109.5
C3A—C7A—N1	103.5 (3)	H18A—C18—H18B	109.5
C2—C8—C9	112.6 (4)	C13—C18—H18C	109.5
C2—C8—H8A	109.1	H18A—C18—H18C	109.5
C9—C8—H8A	109.1	H18B—C18—H18C	109.5
C2—C8—H8B	109.1	C15—C19—H19A	109.5
C9—C8—H8B	109.1	C15—C19—H19B	109.5
H8A—C8—H8B	107.8	H19A—C19—H19B	109.5
C10—C9—C8	111.0 (4)	C15—C19—H19C	109.5
C10—C9—H9A	109.4	H19A—C19—H19C	109.5
C8—C9—H9A	109.4	H19B—C19—H19C	109.5
C10—C9—H9B	109.4
O2—S1—N1—C2	174.6 (3)	C4—C3A—C7A—N1	180.0 (4)
O1—S1—N1—C2	46.7 (4)	C2—N1—C7A—C7	−177.5 (5)
C12—S1—N1—C2	−68.1 (4)	S1—N1—C7A—C7	2.5 (7)
O2—S1—N1—C7A	−5.4 (4)	C2—N1—C7A—C3A	0.9 (4)
O1—S1—N1—C7A	−133.3 (3)	S1—N1—C7A—C3A	−179.1 (3)
C12—S1—N1—C7A	111.9 (4)	N3—C2—C8—C9	3.6 (7)
C3A—N3—C2—N1	1.0 (5)	N1—C2—C8—C9	−176.6 (4)
C3A—N3—C2—C8	−179.2 (4)	C2—C8—C9—C10	178.5 (4)
C7A—N1—C2—N3	−1.2 (5)	C8—C9—C10—C11	−179.4 (5)
S1—N1—C2—N3	178.8 (3)	O2—S1—C12—C17	−133.0 (3)
C7A—N1—C2—C8	179.0 (4)	O1—S1—C12—C17	−0.2 (4)
S1—N1—C2—C8	−1.0 (6)	N1—S1—C12—C17	113.3 (3)
C2—N3—C3A—C7A	−0.4 (5)	O2—S1—C12—C13	44.3 (4)
C2—N3—C3A—C4	179.3 (5)	O1—S1—C12—C13	177.1 (3)
N3—C3A—C4—C5	−179.1 (5)	N1—S1—C12—C13	−69.4 (4)
C7A—C3A—C4—C5	0.6 (7)	C17—C12—C13—C14	−1.5 (6)
C3A—C4—C5—C6	0.0 (8)	S1—C12—C13—C14	−178.7 (3)
C3A—C4—C5—Cl1'	−164.9 (4)	C17—C12—C13—C18	−177.9 (4)
C4—C5—C6—C7	0.1 (8)	S1—C12—C13—C18	4.9 (6)
Cl1'—C5—C6—C7	163.8 (4)	C12—C13—C14—C15	0.0 (7)
C4—C5—C6—Cl1	−179.9 (4)	C18—C13—C14—C15	176.5 (4)
Cl1'—C5—C6—Cl1	−16.3 (7)	C13—C14—C15—C16	1.0 (7)
C5—C6—C7—C7A	−0.9 (7)	C13—C14—C15—C19	−176.8 (4)
Cl1—C6—C7—C7A	179.2 (3)	C14—C15—C16—C17	−0.4 (7)
C6—C7—C7A—C3A	1.5 (6)	C19—C15—C16—C17	177.4 (5)
C6—C7—C7A—N1	179.6 (4)	C15—C16—C17—C12	−1.1 (7)
N3—C3A—C7A—C7	178.3 (4)	C13—C12—C17—C16	2.1 (7)
C4—C3A—C7A—C7	−1.4 (7)	S1—C12—C17—C16	179.5 (4)
N3—C3A—C7A—N1	−0.3 (5)

Cg3 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···O2i	0.96	2.62	3.554 (7)	165
C4—H4A···Cg3ii	0.93	2.76	3.665 (8)	163

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19B⋯O2i	0.96	2.62	3.554 (7)	165
C4—H4A⋯Cg3ii	0.93	2.76	3.665 (8)	163

Symmetry codes: (i) ; (ii) .