2-n-Butyl-6-chloro-1-(2,4-dimethyl­phenyl­sulfon­yl)-1H-benzimidazole–2-n-butyl-5-chloro-1-(2,4-dimethyl­phenyl­sulfon­yl)-1H-benzimidazole (0.759/0.241)

Abdireymov, K.B.; Mukhamedov, N.S.; Okmanov, R.Y.; Ayimbetov, M.J.; Tashkhodjaev, B.

doi:10.1107/S1600536811047957

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3345-o3346

https://doi.org/10.1107/S1600536811047957

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2-n-Butyl-6-chloro-1-(2,4-dimethylphenylsulfonyl)-1H-benzimidazole–2-n-butyl-5-chloro-1-(2,4-dimethylphenylsulfonyl)-1H-benzimidazole (0.759/0.241)

K. B. Abdireymov,^a ^* N. S. Mukhamedov,^a R. Ya. Okmanov,^a M. J. Ayimbetov ^b and B. Tashkhodjaev ^a

^aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str., 77, Tashkent 100170, Uzbekistan, and ^bKara-Kalpak State University, Acad. Abdirov Str., 1, Nukus 742000, Uzbekistan
^*Correspondence e-mail: abdireymovqudaybergen@mail.ru

(Received 18 October 2011; accepted 11 November 2011; online 19 November 2011)

The title compound, 0.759C₁₉H₂₁ClN₂O₂S·0.241C₁₉H₂₁ClN₂O₂S, was synthesized by arylsulfonylation of 2-n-butyl-5-chloro-1H-benzimidazole in the presence of triethylamine. The crystal structure is composed of two molecules, 2-n-butyl-6-chloro-1-(2,4-dimethylphenylsulfonyl)-1H-benzimidazole and 1-(2,4-dimethylphenylsulfonyl)-2-n-butyl-5-chloro-1H-benzimidazole, in the refined ratio of 0.759 (4):0.241 (4) disordered at the same position in the unit cell. The molecule has three essentially planar fragments viz. benzimidazole, dimethylbenzene and n-butyl (r.m.s. deviations of 0.009, 0.024 and 0.003 Å, respectively). The angle between the benzimidazole and dimethylbenzene fragments is 86.0 (1)°. In the crystal, pairs of intermolecular C—H⋯π interactions form centrosymmetrical dimers, which are linked by weak intermolecular 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_r = 376.89
Triclinic, $[P \overline 1]$
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)
θ_max = 60.0°
3 standard reflections every 60 min intensity decay: 10.4%

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.191
S = 1.12
2714 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.45 e Å⁻³

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) x+1, y, z; (ii) -x+1, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047957/im2330sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047957/im2330Isup2.hkl

checkCIF report

Comment top

Benzimidazole (Koči et al., 2002; Matsuno et al., 2000; Garuti et al., 1999) and 2-n-butylbenzimidazole (Kubo et al., 1993a; 1993b) derivatives are important heterocyclic compounds which have attracted great attention due to their biological and pharmaceutical activities.

Reaction of 2-1n-butyl-5-chloro-1H-benzimidazole with 2,4-dimethylbenzenesulfonyl chloride in the presence of triethylamine results in a mixture of 1-(2,4-dimethylbenzenesulfonyl)-2-n-butyl-6-chloro-1H-benzimidazole and 1-(2,4-dimethylbenzenesulfonyl)-2-n-butyl-5-chloro-1H-benzimidazole, in the refined ratio of 0.759 (4):0.241 (4) (Abdireimov et al., 2010). The structure of the received product is investigated by ¹H NMR and X-ray diffraction.

As a whole the molecule consists of three flat fragments: benzimidazole (N1/C2/N3/C3A–C7A), dimethylbenzene (C12–C19) and n-butyl (C8–C11) (r.m.s. deviations are 0.009, 0.024 and 0.003 Å, respectively). The angle between flat benzimidazole and dimethylbenzene fragment is 86.0 (1)°, and between benzimidazole and n-butyl is 4.4 (2)° (Fig. 1).

The crystal structure is stabilized by intermolecular C—H···π interactions observed between the atoms of two benzene rings of neighboring molecules with distance C4—H···Cg3ⁱ = 3.665 (2) Å [symmetry code: (i) 1 - x, 1 - y, 1 - z; Cg3 is centroid of the C12–C17 benzene ring]. Observable C—H···π interactions form centrosymmetric dimers, another weak intermolecular H-bond such as C19—H···O2 sew these dimers (Table 1).

Related literature top

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 top

In the three-necked round-bottomed flask, supplied with a mechanical mixer, dropping funnel and backflow condenser, were placed 2.04 g (10 mmol) 2,4-dimethylbenzenesulfonyl chloride in 15 ml of acetone and was added a solution of 2.08 g (10 mmol) 2-1n-butyl-5-chloro-1H-benzimidazole and 1.01 g (10 mmol) triethylamine in 30 ml acetone by stirring and cooling. The reaction mixture was stirred at room temperature for 4 h. Afterwards acetone is evaporated. The residual product was washed with 100 ml of the water, obtained crystals were filtered and recrystallized from ethanol. 2.18 g (56%) mixed crystals of 1-(2,4-dimethylbenzenesulfonyl)-2-n-butyl-6-chloro-1H-benzimidazole (A) and 1-(2,4-dimethylbenzenesulfonyl)-2-n-butyl-5-chloro-1H-benzimidazole (B), melting in the temperature range of 108–117°C were obtained.

Colorless crystals suitable for XRD have been received from ethanol at room temperature.

Structure description top

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).

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4 (Stoe & Cie, 1997); 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).

Figures top

Fig. 1. Molecular structure of the title compound, displacement ellipsoids are drawn at the 30% probability level.

2-n-Butyl-6-chloro-1-(2,4-dimethylphenylsulfonyl)-1H- benzimidazole–2-n-butyl-5-chloro-1-(2,4-dimethylphenylsulfonyl)- 1H-benzimidazole (0.759/0.241) top

Crystal data top

0.7590.241C₁₉H₂₁ClN₂O₂S·0.2410.241C₁₉H₂₁ClN₂O₂S	Z = 2
M_r = 376.89	F(000) = 396
Triclinic, P1	D_x = 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

Data collection top

Stoe Stadi-4 four-circle diffractometer	2460 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 60.0°, θ_min = 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
T_min = 0.250, T_max = 0.551	l = 0→12
2722 measured reflections	3 standard reflections every 60 min
2714 independent reflections	intensity decay: 10.4%

Refinement top

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(F_o²) + (0.0919P)² + 1.1929P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2714 reflections	Δρ_max = 0.35 e Å⁻³
240 parameters	Δρ_min = −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)

Crystal data top

0.7590.241C₁₉H₂₁ClN₂O₂S·0.2410.241C₁₉H₂₁ClN₂O₂S	γ = 76.75 (3)°
M_r = 376.89	V = 931.1 (3) Å³
Triclinic, P1	Z = 2
a = 8.7340 (17) Å	Cu Kα radiation
b = 10.251 (2) Å	µ = 2.98 mm⁻¹
c = 11.390 (2) Å	T = 290 K
α = 71.29 (3)°	0.68 × 0.45 × 0.20 mm
β = 78.38 (3)°

Data collection top

Stoe Stadi-4 four-circle diffractometer	2460 reflections with I > 2σ(I)
Absorption correction: ψ scan (X-RED; Stoe & Cie, 1997)	R_int = 0.000
T_min = 0.250, T_max = 0.551	θ_max = 60.0°
2722 measured reflections	3 standard reflections every 60 min
2714 independent reflections	intensity decay: 10.4%

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.12	Δρ_max = 0.35 e Å⁻³
2714 reflections	Δρ_min = −0.45 e Å⁻³
240 parameters

Special details top

Experimental. Empirical absorption correction using ψ Scan. Reflections used Mu * R = 0.00

H K L, θ, χ, I_min/I_max: -1 -2 4 45.0 82.7 0.455

¹H 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	0.7590.241C₁₉H₂₁ClN₂O₂S·0.2410.241C₁₉H₂₁ClN₂O₂S
M_r	376.89
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	8.7340 (17), 10.251 (2), 11.390 (2)
α, β, γ (°)	71.29 (3), 78.38 (3), 76.75 (3)
V (Å³)	931.1 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.98
Crystal size (mm)	0.68 × 0.45 × 0.20

Data collection
Diffractometer	Stoe Stadi-4 four-circle
Absorption correction	ψ scan (X-RED; Stoe & Cie, 1997)
T_min, T_max	0.250, 0.551
No. of measured, independent and observed [I > 2σ(I)] reflections	2722, 2714, 2460
R_int	0.000
θ_max (°)	60.0
(sin θ/λ)_max (Å⁻¹)	0.562

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.191, 1.12
No. of reflections	2714
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.45

Computer programs: STADI4 (Stoe & Cie, 1997), X-RED (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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	2.619	3.554 (7)	165
C4—H4A···Cg3ⁱⁱ	0.93	2.760	3.665 (8)	163

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

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grants FA-F3-T045 and FA-A6-T114).

References

Abdireimov, K. B., Mukhamedov, N. S., Aiymbetov, M. Zh. & Shakhidoyatov, Kh. M. (2010). Chem. Heterocycl. Compd, 46, 941–946. Web of Science CrossRef CAS Google Scholar
Garuti, L., Roberti, M. & Cermelli, C. (1999). Bioorg. Med. Chem. Lett. 9, 2525–2530. Web of Science CrossRef PubMed CAS Google Scholar
Koči, J., Klimešová, V., Waisser, K., Kaustová, J., Dahse, H. M. & Möllmann, U. (2002). Bioorg. Med. Chem. Lett. 12, 3275–3278. Web of Science PubMed Google Scholar
Kubo, K., Inada, Y., Koharo, Y., Sugiura, Y., Ojima, M., Itoh, K., Furukawa, Y., Nashikawa, K. & Naka, T. (1993a). J. Med. Chem. 36, 1772–1784. CSD CrossRef CAS PubMed Web of Science Google Scholar
Kubo, K., Kohara, Y., Yoshimura, Y., Inada, Y., Shibouta, Y., Furukawa, Y., Kato, T., Nashikawa, K. & Naka, T. (1993b). J. Med. Chem. 36, 2343–2349. CSD CrossRef CAS PubMed Web of Science Google Scholar
Matsuno, T., Kato, M., Sasahara, H., Watanabe, T., Inaba, M., Takahashi, M., Yaguchi, S. I., Yoshioka, K., Sakato, M. & Kawashima, S. (2000). Chem. Pharm. Bull. 48, 1778–1781. CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1997). STADI4 and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 12| December 2011| Pages o3345-o3346

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

2-n-Butyl-6-chloro-1-(2,4-di­methyl­phenyl­sulfon­yl)-1H-benzimidazole–2-n-butyl-5-chloro-1-(2,4-di­methyl­phenyl­sulfon­yl)-1H-benzimidazole (0.759/0.241)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-n-Butyl-6-chloro-1-(2,4-dimethylphenylsulfonyl)-1H-benzimidazole–2-n-butyl-5-chloro-1-(2,4-dimethylphenylsulfonyl)-1H-benzimidazole (0.759/0.241)