1-[(4-tert-Butyl-phen-yl)sulfon-yl]-1H-benzimidazole.

The title compound, C(17)H(18)N(2)O(2)S, was synthesized by aryl-sulfonyl-ation of 1-hy-droxy-methyl-1H-benzimidazole in the presence of triethyl-amine. The benzimidazole and benzene rings form a dihedral angle of 84.1 (1)°. The tert-butyl group was treated as rotationally disordered over two orientations in a 0.51 (2):0.49 (2) ratio. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [010].

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 related structures, see: Rashid et al. (2006 ▶, 2007 ▶). For the aryl­sulfonyl­ation of benzimidazole derivatives, see: Abdireimov et al. (2010 ▶).

Experimental

Crystal data

C17H18N2O2S

M = 314.39

Monoclinic,

a = 12.142 (2) Å

b = 8.8940 (18) Å

c = 15.324 (3) Å

β = 96.78 (3)°

V = 1643.3 (6) Å3

Z = 4

Cu Kα radiation

μ = 1.82 mm−1

T = 302 K

0.60 × 0.25 × 0.22 mm

Data collection

Stoe Stadi-4 four-circle diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.609, T max = 0.670

2727 measured reflections

2429 independent reflections

1813 reflections with I > 2σ(I)

R int = 0.044

θmax = 60.0°

3 standard reflections every 60 min intensity decay: 5.2%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.150

S = 1.12

2429 reflections

234 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.27 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 (Bruker, 1998 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005551/cv5052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005551/cv5052Isup2.hkl

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

C17H18N2O2S	F(000) = 664
Mr = 314.39	Dx = 1.271 Mg m−3
Monoclinic, P21/n	Melting point: 395(1) K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54184 Å
a = 12.142 (2) Å	Cell parameters from 14 reflections
b = 8.8940 (18) Å	θ = 10–20°
c = 15.324 (3) Å	µ = 1.82 mm−1
β = 96.78 (3)°	T = 302 K
V = 1643.3 (6) Å3	Prism, colourless
Z = 4	0.60 × 0.25 × 0.22 mm

Stoe Stadi-4 four-circle diffractometer	1813 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 60.0°, θmin = 4.4°
Scan width (ω) = 1.56 – 1.80, scan ratio 2θ:ω = 1.00 I(Net) and sigma(I) calculated according to Blessing (1987)	h = −13→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.609, Tmax = 0.670	l = 0→17
2727 measured reflections	3 standard reflections every 60 min
2429 independent reflections	intensity decay: 5.2%

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0478P)2 + 1.1618P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2429 reflections	Δρmax = 0.15 e Å−3
234 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0054 (4)

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	0.15656 (9)	0.56256 (13)	0.30146 (7)	0.0817 (4)
O1	0.2287 (3)	0.6147 (4)	0.24143 (18)	0.1059 (11)
O2	0.0939 (3)	0.4275 (3)	0.2866 (2)	0.1116 (11)
N1	0.2366 (2)	0.5318 (4)	0.39620 (19)	0.0695 (8)
N3	0.2705 (3)	0.4528 (4)	0.5352 (3)	0.0882 (11)
C2	0.2092 (4)	0.4382 (5)	0.4623 (3)	0.0855 (12)
H2B	0.1509	0.3700	0.4542	0.103*
C3A	0.3453 (3)	0.5650 (4)	0.5199 (3)	0.0678 (10)
C4	0.4313 (4)	0.6232 (5)	0.5767 (3)	0.0857 (12)
H4A	0.4460	0.5875	0.6340	0.103*
C5	0.4939 (4)	0.7339 (6)	0.5467 (4)	0.0924 (13)
H5A	0.5514	0.7757	0.5845	0.111*
C6	0.4741 (4)	0.7862 (5)	0.4611 (4)	0.0907 (13)
H6A	0.5189	0.8618	0.4425	0.109*
C7	0.3901 (3)	0.7286 (4)	0.4032 (3)	0.0764 (11)
H7A	0.3773	0.7625	0.3455	0.092*
C7A	0.3259 (3)	0.6188 (4)	0.4344 (2)	0.0621 (9)
C8	0.0676 (3)	0.7078 (4)	0.3232 (2)	0.0593 (9)
C9	−0.0313 (3)	0.6758 (4)	0.3528 (2)	0.0639 (9)
H9A	−0.0507	0.5766	0.3627	0.077*
C10	−0.1020 (3)	0.7904 (4)	0.3678 (2)	0.0635 (9)
H10A	−0.1696	0.7674	0.3875	0.076*
C11	−0.0760 (3)	0.9392 (4)	0.3545 (2)	0.0542 (8)
C12	0.0251 (3)	0.9681 (4)	0.3244 (2)	0.0673 (10)
H12A	0.0450	1.0670	0.3146	0.081*
C13	0.0966 (3)	0.8541 (4)	0.3086 (2)	0.0672 (10)
H13A	0.1640	0.8759	0.2883	0.081*
C14	−0.1562 (3)	1.0652 (5)	0.3703 (3)	0.0709 (10)
C15	−0.2610 (16)	1.044 (3)	0.3059 (11)	0.131 (7)	0.51 (2)
H15A	−0.3100	1.1275	0.3104	0.197*	0.51 (2)
H15B	−0.2974	0.9526	0.3196	0.197*	0.51 (2)
H15C	−0.2413	1.0382	0.2471	0.197*	0.51 (2)
C16	−0.113 (2)	1.2215 (18)	0.361 (3)	0.234 (18)	0.51 (2)
H16A	−0.0440	1.2326	0.3985	0.351*	0.51 (2)
H16B	−0.1658	1.2926	0.3788	0.351*	0.51 (2)
H16C	−0.1015	1.2394	0.3015	0.351*	0.51 (2)
C17	−0.1958 (18)	1.047 (2)	0.4597 (8)	0.142 (10)	0.51 (2)
H17A	−0.1330	1.0447	0.5041	0.214*	0.51 (2)
H17B	−0.2367	0.9549	0.4613	0.214*	0.51 (2)
H17C	−0.2428	1.1302	0.4706	0.214*	0.51 (2)
C15A	−0.0948 (12)	1.1855 (16)	0.4249 (10)	0.093 (5)	0.49 (2)
H15D	−0.1469	1.2544	0.4454	0.140*	0.49 (2)
H15E	−0.0470	1.2386	0.3899	0.140*	0.49 (2)
H15F	−0.0511	1.1403	0.4743	0.140*	0.49 (2)
C16A	−0.248 (2)	1.013 (2)	0.415 (3)	0.233 (19)	0.49 (2)
H16D	−0.2963	1.0962	0.4239	0.350*	0.49 (2)
H16E	−0.2204	0.9706	0.4708	0.350*	0.49 (2)
H16F	−0.2894	0.9380	0.3797	0.350*	0.49 (2)
C17A	−0.192 (3)	1.141 (3)	0.2816 (11)	0.150 (10)	0.49 (2)
H17D	−0.2465	1.2174	0.2891	0.226*	0.49 (2)
H17E	−0.2240	1.0676	0.2403	0.226*	0.49 (2)
H17F	−0.1290	1.1865	0.2600	0.226*	0.49 (2)

	U11	U22	U33	U12	U13	U23
S1	0.0854 (7)	0.0894 (8)	0.0698 (6)	0.0210 (6)	0.0072 (5)	−0.0219 (6)
O1	0.112 (2)	0.145 (3)	0.0660 (17)	0.044 (2)	0.0306 (16)	−0.0054 (18)
O2	0.116 (2)	0.087 (2)	0.126 (3)	0.0087 (19)	−0.012 (2)	−0.0552 (19)
N1	0.0673 (19)	0.069 (2)	0.0716 (19)	0.0118 (16)	0.0044 (16)	0.0041 (16)
N3	0.083 (2)	0.086 (3)	0.096 (3)	0.001 (2)	0.014 (2)	0.026 (2)
C2	0.080 (3)	0.067 (3)	0.112 (4)	0.000 (2)	0.020 (3)	0.016 (3)
C3A	0.061 (2)	0.068 (2)	0.075 (2)	0.0119 (19)	0.0132 (19)	0.008 (2)
C4	0.082 (3)	0.095 (3)	0.079 (3)	0.012 (3)	0.007 (2)	0.006 (2)
C5	0.071 (3)	0.094 (3)	0.111 (4)	0.004 (3)	0.003 (3)	−0.015 (3)
C6	0.073 (3)	0.075 (3)	0.128 (4)	−0.003 (2)	0.023 (3)	0.006 (3)
C7	0.075 (3)	0.070 (3)	0.087 (3)	0.012 (2)	0.024 (2)	0.019 (2)
C7A	0.059 (2)	0.059 (2)	0.070 (2)	0.0141 (18)	0.0141 (17)	0.0043 (18)
C8	0.057 (2)	0.070 (2)	0.0502 (19)	0.0035 (18)	0.0041 (15)	−0.0080 (17)
C9	0.060 (2)	0.058 (2)	0.071 (2)	−0.0046 (18)	0.0000 (18)	−0.0060 (18)
C10	0.050 (2)	0.071 (2)	0.069 (2)	−0.0058 (18)	0.0079 (16)	−0.0093 (19)
C11	0.0482 (18)	0.062 (2)	0.0502 (18)	−0.0012 (16)	−0.0024 (14)	−0.0048 (16)
C12	0.067 (2)	0.059 (2)	0.076 (2)	−0.0038 (19)	0.0100 (19)	0.0078 (19)
C13	0.058 (2)	0.081 (3)	0.065 (2)	−0.002 (2)	0.0149 (17)	0.005 (2)
C14	0.063 (2)	0.074 (3)	0.074 (2)	0.011 (2)	0.0002 (18)	−0.006 (2)
C15	0.100 (10)	0.177 (19)	0.106 (11)	0.076 (11)	−0.037 (8)	−0.032 (11)
C16	0.17 (2)	0.069 (9)	0.49 (6)	0.027 (10)	0.14 (3)	0.05 (2)
C17	0.20 (2)	0.153 (18)	0.071 (8)	0.102 (16)	0.023 (8)	−0.007 (8)
C15A	0.095 (7)	0.057 (8)	0.122 (9)	0.014 (7)	−0.010 (7)	−0.037 (7)
C16A	0.157 (18)	0.104 (11)	0.48 (5)	−0.015 (13)	0.23 (3)	−0.07 (2)
C17A	0.18 (2)	0.153 (18)	0.105 (10)	0.096 (16)	−0.050 (13)	−0.022 (11)

S1—O1	1.421 (3)	C12—C13	1.375 (5)
S1—O2	1.426 (3)	C12—H12A	0.9300
S1—N1	1.671 (3)	C13—H13A	0.9300
S1—C8	1.742 (3)	C14—C16A	1.455 (17)
N1—C2	1.381 (5)	C14—C16	1.498 (17)
N1—C7A	1.402 (5)	C14—C15A	1.501 (12)
N3—C2	1.274 (5)	C14—C17	1.513 (15)
N3—C3A	1.387 (5)	C14—C15	1.527 (15)
C2—H2B	0.9300	C14—C17A	1.535 (18)
C3A—C4	1.379 (5)	C15—H15A	0.9600
C3A—C7A	1.389 (5)	C15—H15B	0.9600
C4—C5	1.357 (6)	C15—H15C	0.9600
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.386 (6)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.369 (6)	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—C7A	1.371 (5)	C17—H17C	0.9600
C7—H7A	0.9300	C15A—H15D	0.9600
C8—C9	1.363 (5)	C15A—H15E	0.9600
C8—C13	1.373 (5)	C15A—H15F	0.9600
C9—C10	1.369 (5)	C16A—H16D	0.9600
C9—H9A	0.9300	C16A—H16E	0.9600
C10—C11	1.381 (5)	C16A—H16F	0.9600
C10—H10A	0.9300	C17A—H17D	0.9600
C11—C12	1.385 (5)	C17A—H17E	0.9600
C11—C14	1.523 (5)	C17A—H17F	0.9600
O1—S1—O2	122.0 (2)	C13—C12—H12A	119.2
O1—S1—N1	106.03 (18)	C11—C12—H12A	119.2
O2—S1—N1	104.21 (19)	C8—C13—C12	119.4 (3)
O1—S1—C8	109.00 (19)	C8—C13—H13A	120.3
O2—S1—C8	108.89 (18)	C12—C13—H13A	120.3
N1—S1—C8	105.39 (15)	C16A—C14—C15A	109.0 (13)
C2—N1—C7A	105.5 (3)	C16—C14—C17	109.4 (14)
C2—N1—S1	124.7 (3)	C16A—C14—C11	112.5 (8)
C7A—N1—S1	127.9 (3)	C16—C14—C11	115.5 (8)
C2—N3—C3A	104.6 (4)	C15A—C14—C11	109.1 (6)
N3—C2—N1	114.5 (4)	C17—C14—C11	110.1 (7)
N3—C2—H2B	122.7	C16—C14—C15	109.3 (12)
N1—C2—H2B	122.7	C17—C14—C15	104.1 (10)
C4—C3A—N3	128.7 (4)	C11—C14—C15	107.8 (7)
C4—C3A—C7A	119.9 (4)	C16A—C14—C17A	113.7 (12)
N3—C3A—C7A	111.4 (4)	C15A—C14—C17A	104.5 (10)
C5—C4—C3A	118.1 (4)	C11—C14—C17A	107.7 (7)
C5—C4—H4A	120.9	C14—C15—H15A	109.5
C3A—C4—H4A	120.9	C14—C15—H15B	109.5
C4—C5—C6	121.5 (4)	C14—C15—H15C	109.5
C4—C5—H5A	119.2	C14—C16—H16A	109.5
C6—C5—H5A	119.2	C14—C16—H16B	109.5
C7—C6—C5	121.4 (4)	C14—C16—H16C	109.5
C7—C6—H6A	119.3	C14—C17—H17A	109.5
C5—C6—H6A	119.3	C14—C17—H17B	109.5
C6—C7—C7A	116.8 (4)	C14—C17—H17C	109.5
C6—C7—H7A	121.6	C14—C15A—H15D	109.5
C7A—C7—H7A	121.6	C14—C15A—H15E	109.5
C7—C7A—C3A	122.3 (4)	H15D—C15A—H15E	109.5
C7—C7A—N1	133.7 (4)	C14—C15A—H15F	109.5
C3A—C7A—N1	104.0 (3)	H15D—C15A—H15F	109.5
C9—C8—C13	120.4 (3)	H15E—C15A—H15F	109.5
C9—C8—S1	120.0 (3)	C14—C16A—H16D	109.5
C13—C8—S1	119.7 (3)	C14—C16A—H16E	109.5
C8—C9—C10	119.6 (3)	H16D—C16A—H16E	109.5
C8—C9—H9A	120.2	C14—C16A—H16F	109.5
C10—C9—H9A	120.2	H16D—C16A—H16F	109.5
C9—C10—C11	122.0 (3)	H16E—C16A—H16F	109.5
C9—C10—H10A	119.0	C14—C17A—H17D	109.5
C11—C10—H10A	119.0	C14—C17A—H17E	109.5
C10—C11—C12	117.0 (3)	H17D—C17A—H17E	109.5
C10—C11—C14	121.3 (3)	C14—C17A—H17F	109.5
C12—C11—C14	121.7 (3)	H17D—C17A—H17F	109.5
C13—C12—C11	121.7 (3)	H17E—C17A—H17F	109.5
O1—S1—N1—C2	−158.3 (3)	O2—S1—C8—C9	22.1 (3)
O2—S1—N1—C2	−28.4 (4)	N1—S1—C8—C9	−89.2 (3)
C8—S1—N1—C2	86.2 (3)	O1—S1—C8—C13	−21.3 (3)
O1—S1—N1—C7A	39.6 (4)	O2—S1—C8—C13	−156.6 (3)
O2—S1—N1—C7A	169.5 (3)	N1—S1—C8—C13	92.1 (3)
C8—S1—N1—C7A	−75.9 (3)	C13—C8—C9—C10	0.2 (5)
C3A—N3—C2—N1	0.6 (5)	S1—C8—C9—C10	−178.5 (3)
C7A—N1—C2—N3	−1.4 (5)	C8—C9—C10—C11	−0.5 (5)
S1—N1—C2—N3	−166.9 (3)	C9—C10—C11—C12	0.5 (5)
C2—N3—C3A—C4	−178.8 (4)	C9—C10—C11—C14	179.2 (3)
C2—N3—C3A—C7A	0.5 (5)	C10—C11—C12—C13	−0.2 (5)
N3—C3A—C4—C5	−179.9 (4)	C14—C11—C12—C13	−178.8 (3)
C7A—C3A—C4—C5	0.8 (6)	C9—C8—C13—C12	0.1 (5)
C3A—C4—C5—C6	−1.2 (7)	S1—C8—C13—C12	178.8 (3)
C4—C5—C6—C7	0.3 (7)	C11—C12—C13—C8	−0.1 (5)
C5—C6—C7—C7A	0.9 (6)	C10—C11—C14—C16A	10.7 (19)
C6—C7—C7A—C3A	−1.2 (5)	C12—C11—C14—C16A	−170.7 (19)
C6—C7—C7A—N1	−178.1 (4)	C10—C11—C14—C16	174 (2)
C4—C3A—C7A—C7	0.4 (6)	C12—C11—C14—C16	−7(2)
N3—C3A—C7A—C7	−179.0 (3)	C10—C11—C14—C15A	131.8 (8)
C4—C3A—C7A—N1	178.0 (3)	C12—C11—C14—C15A	−49.7 (8)
N3—C3A—C7A—N1	−1.3 (4)	C10—C11—C14—C17	49.9 (10)
C2—N1—C7A—C7	178.8 (4)	C12—C11—C14—C17	−131.5 (10)
S1—N1—C7A—C7	−16.3 (6)	C10—C11—C14—C15	−63.0 (13)
C2—N1—C7A—C3A	1.6 (4)	C12—C11—C14—C15	115.6 (13)
S1—N1—C7A—C3A	166.4 (3)	C10—C11—C14—C17A	−115.3 (15)
O1—S1—C8—C9	157.3 (3)	C12—C11—C14—C17A	63.2 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2i	0.93	2.56	3.430 (5)	156
C13—H13A···O1i	0.93	2.56	3.292 (5)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2i	0.93	2.56	3.430 (5)	156
C13—H13A⋯O1i	0.93	2.56	3.292 (5)	136

Symmetry code: (i) .