2,5,7-Trimethyl-3-(4-methyl-phenyl-sulfon-yl)-1-benzofuran.

In the title compound, C(18)H(18)O(3)S, the 4-methyl-phenyl ring makes a dihedral angle of 86.35 (3)° with the mean plane [mean deviation = 0.006 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions. The crystal structure also exhibits weak π-π inter-actions between the furan and benzene rings of neighbouring benzofuran systems [centroid-centroid distance = 3.685 (2), inter-planar distance = 3.572 (2) and slippage = 0.906 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2010 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C18H18O3S

M = 314.38

Monoclinic,

a = 9.7666 (2) Å

b = 19.4511 (5) Å

c = 8.2979 (2) Å

β = 98.541 (1)°

V = 1558.88 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.41 × 0.39 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.916, T max = 0.958

15446 measured reflections

3868 independent reflections

3258 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.04

3868 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202020X/sj5234sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202020X/sj5234Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202020X/sj5234Isup3.cml

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

C18H18O3S	F(000) = 664
Mr = 314.38	Dx = 1.340 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5168 reflections
a = 9.7666 (2) Å	θ = 2.4–28.2°
b = 19.4511 (5) Å	µ = 0.22 mm−1
c = 8.2979 (2) Å	T = 173 K
β = 98.541 (1)°	Block, colourless
V = 1558.88 (6) Å3	0.41 × 0.39 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3868 independent reflections
Radiation source: rotating anode	3258 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.1°
φ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −21→25
Tmin = 0.916, Tmax = 0.958	l = −11→10
15446 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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.5651P] where P = (Fo2 + 2Fc2)/3
3868 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.77821 (4)	0.617621 (19)	0.95912 (5)	0.03124 (12)
O1	0.44316 (10)	0.54239 (6)	0.69953 (13)	0.0335 (3)
O2	0.73376 (14)	0.68604 (6)	0.99116 (16)	0.0445 (3)
O3	0.84855 (13)	0.57685 (6)	1.09059 (14)	0.0401 (3)
C1	0.63766 (15)	0.56994 (7)	0.86672 (18)	0.0281 (3)
C2	0.62873 (14)	0.49571 (7)	0.86149 (17)	0.0259 (3)
C3	0.70807 (15)	0.44093 (8)	0.93316 (18)	0.0295 (3)
H3	0.7907	0.4490	1.0067	0.035*
C4	0.66347 (16)	0.37470 (8)	0.8946 (2)	0.0328 (3)
C5	0.54034 (16)	0.36373 (8)	0.7862 (2)	0.0342 (3)
H5	0.5122	0.3177	0.7612	0.041*
C6	0.45823 (15)	0.41655 (9)	0.71436 (19)	0.0321 (3)
C7	0.50737 (14)	0.48180 (8)	0.75612 (18)	0.0276 (3)
C8	0.52485 (16)	0.59479 (8)	0.7677 (2)	0.0329 (3)
C9	0.7482 (2)	0.31384 (9)	0.9655 (3)	0.0463 (4)
H9A	0.7937	0.2924	0.8806	0.069*
H9B	0.6873	0.2803	1.0071	0.069*
H9C	0.8185	0.3294	1.0547	0.069*
C10	0.32615 (17)	0.40458 (11)	0.5996 (2)	0.0438 (4)
H10A	0.3180	0.3557	0.5713	0.066*
H10B	0.3273	0.4318	0.5003	0.066*
H10C	0.2471	0.4185	0.6522	0.066*
C11	0.4770 (2)	0.66466 (10)	0.7171 (3)	0.0498 (5)
H11A	0.4870	0.6718	0.6026	0.075*
H11B	0.5328	0.6987	0.7849	0.075*
H11C	0.3795	0.6698	0.7305	0.075*
C12	0.88605 (15)	0.62242 (7)	0.80711 (18)	0.0281 (3)
C15	1.04793 (16)	0.62512 (9)	0.55823 (19)	0.0355 (4)
C16	0.97063 (16)	0.68243 (9)	0.5909 (2)	0.0360 (4)
H16	0.9738	0.7228	0.5273	0.043*
C17	0.88939 (16)	0.68161 (8)	0.71428 (19)	0.0323 (3)
H17	0.8369	0.7209	0.7350	0.039*
C18	1.1300 (2)	0.62519 (11)	0.4184 (2)	0.0504 (5)
H18A	1.0714	0.6089	0.3196	0.076*
H18B	1.2102	0.5948	0.4439	0.076*
H18C	1.1617	0.6720	0.4006	0.076*
C13	0.96346 (15)	0.56489 (8)	0.77825 (19)	0.0317 (3)
H13	0.9609	0.5247	0.8426	0.038*
C14	1.04408 (16)	0.56690 (8)	0.6550 (2)	0.0355 (3)
H14	1.0979	0.5279	0.6359	0.043*

	U11	U22	U33	U12	U13	U23
S1	0.0373 (2)	0.0257 (2)	0.0299 (2)	−0.00632 (14)	0.00250 (15)	−0.00488 (14)
O1	0.0277 (5)	0.0347 (6)	0.0360 (6)	0.0051 (4)	−0.0020 (4)	−0.0004 (5)
O2	0.0568 (7)	0.0282 (6)	0.0508 (7)	−0.0068 (5)	0.0156 (6)	−0.0142 (5)
O3	0.0457 (6)	0.0439 (7)	0.0279 (6)	−0.0111 (5)	−0.0041 (5)	0.0011 (5)
C1	0.0300 (7)	0.0248 (7)	0.0295 (7)	−0.0007 (5)	0.0039 (6)	−0.0024 (6)
C2	0.0259 (6)	0.0257 (7)	0.0256 (7)	−0.0019 (5)	0.0022 (5)	−0.0022 (5)
C3	0.0268 (6)	0.0281 (7)	0.0321 (8)	−0.0014 (5)	−0.0005 (5)	0.0012 (6)
C4	0.0333 (7)	0.0275 (8)	0.0373 (8)	−0.0011 (6)	0.0046 (6)	0.0016 (6)
C5	0.0350 (8)	0.0270 (7)	0.0410 (9)	−0.0067 (6)	0.0072 (6)	−0.0072 (6)
C6	0.0263 (7)	0.0385 (9)	0.0314 (8)	−0.0060 (6)	0.0040 (6)	−0.0091 (6)
C7	0.0242 (6)	0.0306 (7)	0.0273 (7)	0.0022 (5)	0.0016 (5)	−0.0013 (6)
C8	0.0334 (7)	0.0299 (8)	0.0355 (8)	0.0045 (6)	0.0051 (6)	−0.0001 (6)
C9	0.0503 (10)	0.0282 (9)	0.0590 (12)	0.0037 (7)	0.0032 (8)	0.0053 (8)
C10	0.0293 (7)	0.0596 (11)	0.0405 (9)	−0.0081 (7)	−0.0009 (7)	−0.0155 (8)
C11	0.0514 (10)	0.0350 (9)	0.0611 (12)	0.0153 (8)	0.0022 (9)	0.0067 (9)
C12	0.0283 (7)	0.0251 (7)	0.0287 (7)	−0.0043 (5)	−0.0030 (5)	−0.0012 (6)
C15	0.0278 (7)	0.0457 (9)	0.0311 (8)	−0.0095 (6)	−0.0021 (6)	−0.0032 (7)
C16	0.0346 (8)	0.0359 (8)	0.0349 (8)	−0.0085 (6)	−0.0028 (6)	0.0068 (7)
C17	0.0312 (7)	0.0262 (7)	0.0375 (8)	−0.0023 (6)	−0.0018 (6)	0.0019 (6)
C18	0.0444 (10)	0.0665 (13)	0.0418 (10)	−0.0132 (9)	0.0108 (8)	−0.0055 (9)
C13	0.0313 (7)	0.0272 (7)	0.0342 (8)	−0.0014 (5)	−0.0033 (6)	0.0018 (6)
C14	0.0305 (7)	0.0343 (8)	0.0400 (9)	0.0008 (6)	−0.0008 (6)	−0.0046 (7)

S1—O2	1.4369 (12)	C9—H9C	0.9800
S1—O3	1.4382 (12)	C10—H10A	0.9800
S1—C1	1.7377 (15)	C10—H10B	0.9800
S1—C12	1.7617 (16)	C10—H10C	0.9800
O1—C8	1.3643 (19)	C11—H11A	0.9800
O1—C7	1.3840 (17)	C11—H11B	0.9800
C1—C8	1.361 (2)	C11—H11C	0.9800
C1—C2	1.447 (2)	C12—C17	1.388 (2)
C2—C7	1.3909 (19)	C12—C13	1.391 (2)
C2—C3	1.397 (2)	C15—C14	1.392 (2)
C3—C4	1.382 (2)	C15—C16	1.395 (2)
C3—H3	0.9500	C15—C18	1.505 (2)
C4—C5	1.407 (2)	C16—C17	1.385 (2)
C4—C9	1.513 (2)	C16—H16	0.9500
C5—C6	1.383 (2)	C17—H17	0.9500
C5—H5	0.9500	C18—H18A	0.9800
C6—C7	1.383 (2)	C18—H18B	0.9800
C6—C10	1.504 (2)	C18—H18C	0.9800
C8—C11	1.478 (2)	C13—C14	1.381 (2)
C9—H9A	0.9800	C13—H13	0.9500
C9—H9B	0.9800	C14—H14	0.9500
O2—S1—O3	119.59 (8)	C6—C10—H10A	109.5
O2—S1—C1	109.59 (7)	C6—C10—H10B	109.5
O3—S1—C1	107.30 (7)	H10A—C10—H10B	109.5
O2—S1—C12	108.21 (7)	C6—C10—H10C	109.5
O3—S1—C12	107.66 (7)	H10A—C10—H10C	109.5
C1—S1—C12	103.27 (7)	H10B—C10—H10C	109.5
C8—O1—C7	106.73 (11)	C8—C11—H11A	109.5
C8—C1—C2	107.24 (13)	C8—C11—H11B	109.5
C8—C1—S1	126.32 (12)	H11A—C11—H11B	109.5
C2—C1—S1	125.87 (11)	C8—C11—H11C	109.5
C7—C2—C3	119.08 (13)	H11A—C11—H11C	109.5
C7—C2—C1	104.77 (12)	H11B—C11—H11C	109.5
C3—C2—C1	136.15 (13)	C17—C12—C13	120.90 (15)
C4—C3—C2	118.45 (13)	C17—C12—S1	120.47 (12)
C4—C3—H3	120.8	C13—C12—S1	118.59 (11)
C2—C3—H3	120.8	C14—C15—C16	118.43 (15)
C3—C4—C5	119.97 (14)	C14—C15—C18	120.57 (16)
C3—C4—C9	120.27 (15)	C16—C15—C18	120.97 (16)
C5—C4—C9	119.75 (15)	C17—C16—C15	121.36 (15)
C6—C5—C4	123.28 (14)	C17—C16—H16	119.3
C6—C5—H5	118.4	C15—C16—H16	119.3
C4—C5—H5	118.4	C16—C17—C12	118.87 (15)
C7—C6—C5	114.61 (13)	C16—C17—H17	120.6
C7—C6—C10	122.29 (16)	C12—C17—H17	120.6
C5—C6—C10	123.10 (15)	C15—C18—H18A	109.5
C6—C7—O1	125.01 (13)	C15—C18—H18B	109.5
C6—C7—C2	124.59 (14)	H18A—C18—H18B	109.5
O1—C7—C2	110.40 (13)	C15—C18—H18C	109.5
C1—C8—O1	110.86 (13)	H18A—C18—H18C	109.5
C1—C8—C11	133.75 (16)	H18B—C18—H18C	109.5
O1—C8—C11	115.37 (14)	C14—C13—C12	119.27 (14)
C4—C9—H9A	109.5	C14—C13—H13	120.4
C4—C9—H9B	109.5	C12—C13—H13	120.4
H9A—C9—H9B	109.5	C13—C14—C15	121.17 (15)
C4—C9—H9C	109.5	C13—C14—H14	119.4
H9A—C9—H9C	109.5	C15—C14—H14	119.4
H9B—C9—H9C	109.5
O2—S1—C1—C8	30.29 (16)	C1—C2—C7—C6	179.59 (14)
O3—S1—C1—C8	161.58 (14)	C3—C2—C7—O1	179.33 (13)
C12—S1—C1—C8	−84.84 (15)	C1—C2—C7—O1	−0.47 (16)
O2—S1—C1—C2	−159.46 (13)	C2—C1—C8—O1	0.35 (17)
O3—S1—C1—C2	−28.17 (15)	S1—C1—C8—O1	172.09 (11)
C12—S1—C1—C2	85.40 (14)	C2—C1—C8—C11	−177.50 (19)
C8—C1—C2—C7	0.08 (16)	S1—C1—C8—C11	−5.8 (3)
S1—C1—C2—C7	−171.71 (11)	C7—O1—C8—C1	−0.64 (17)
C8—C1—C2—C3	−179.68 (17)	C7—O1—C8—C11	177.64 (14)
S1—C1—C2—C3	8.5 (3)	O2—S1—C12—C17	−14.89 (14)
C7—C2—C3—C4	0.8 (2)	O3—S1—C12—C17	−145.45 (12)
C1—C2—C3—C4	−179.43 (16)	C1—S1—C12—C17	101.24 (13)
C2—C3—C4—C5	−0.4 (2)	O2—S1—C12—C13	167.49 (12)
C2—C3—C4—C9	178.24 (15)	O3—S1—C12—C13	36.93 (13)
C3—C4—C5—C6	−0.4 (3)	C1—S1—C12—C13	−76.38 (13)
C9—C4—C5—C6	−179.01 (16)	C14—C15—C16—C17	−1.3 (2)
C4—C5—C6—C7	0.6 (2)	C18—C15—C16—C17	176.77 (15)
C4—C5—C6—C10	−179.54 (16)	C15—C16—C17—C12	0.3 (2)
C5—C6—C7—O1	179.95 (14)	C13—C12—C17—C16	0.5 (2)
C10—C6—C7—O1	0.1 (2)	S1—C12—C17—C16	−177.10 (11)
C5—C6—C7—C2	−0.1 (2)	C17—C12—C13—C14	−0.3 (2)
C10—C6—C7—C2	−179.97 (15)	S1—C12—C13—C14	177.35 (11)
C8—O1—C7—C6	−179.37 (15)	C12—C13—C14—C15	−0.7 (2)
C8—O1—C7—C2	0.69 (16)	C16—C15—C14—C13	1.5 (2)
C3—C2—C7—C6	−0.6 (2)	C18—C15—C14—C13	−176.57 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O3i	0.98	2.46	3.310 (2)	146
C9—H9C···Cg1ii	0.98	2.93	3.907 (2)	179
C10—H10B···Cg2iii	0.98	2.92	3.800 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C12–C17 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯O3i	0.98	2.46	3.310 (2)	146
C9—H9C⋯Cg1ii	0.98	2.93	3.907 (2)	179
C10—H10B⋯Cg2iii	0.98	2.92	3.800 (2)	150

Symmetry codes: (i) ; (ii) ; (iii) .