Crystal structure of 2,5-dimethyl-3-(3-methyl-phenyl-sulfon-yl)-1-benzo-furan.

In the title compound, C17H16O3S, the dihedral angle between the plane of the benzo-furan ring system [r.m.s. deviation = 0.010 (1) Å] and that of the 3-methyl-phenyl ring is 79.09 (5)°. Intra-molecular C-H⋯O hydrogen bonds are observed. In the crystal, mol-ecules are connected into a chain along the c-axis direction by two different pairs of inversion-generated inter-actions: C-H⋯π hydrogen bonds between the methyl groups and the benzene rings of the 3-methyl-phenyl fragments and π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.673 (2) Å].

Related literature

For the pharmacological properties of compounds containing a benzo­furan moiety, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Howlett et al. (1999 ▶); Khan et al. (2005 ▶); Ono et al. (2002 ▶). For natural products with a benzo­furan ring, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the synthesis of the starting material, 2,5-dimethyl-3-(3-methyl­phenyl­sulfan­yl)-1-benzo­furan, see: Choi et al. (1999 ▶). For a related structure, see: Choi et al. (2013 ▶).

Experimental

Crystal data

C17H16O3S

M = 300.36

Monoclinic,

a = 9.8769 (2) Å

b = 11.3190 (2) Å

c = 13.1320 (2) Å

β = 101.951 (1)°

V = 1436.29 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.33 × 0.29 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.927, T max = 0.947

13810 measured reflections

3589 independent reflections

2861 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.128

S = 1.08

3589 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.39 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814019369/fy2118sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019369/fy2118Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814019369/fy2118Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814019369/fy2118fig1.tif

The mol­ecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Click here for additional data file.

x y z x y z . DOI: 10.1107/S1600536814019369/fy2118fig2.tif

A view of the C–H⋯O, C–H⋯π and π–π inter­actions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) − x + 1, − y + 1, − z + 1; (ii) − x + 1, − y + 1, − z.]

CCDC reference: 1021292

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

C17H16O3S	F(000) = 632
Mr = 300.36	Dx = 1.389 Mg m−3
Monoclinic, P21/n	Melting point = 378–379 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.8769 (2) Å	Cell parameters from 3458 reflections
b = 11.3190 (2) Å	θ = 2.4–25.7°
c = 13.1320 (2) Å	µ = 0.23 mm−1
β = 101.951 (1)°	T = 173 K
V = 1436.29 (4) Å3	Block, colourless
Z = 4	0.33 × 0.29 × 0.23 mm

Bruker SMART APEXII CCD diffractometer	3589 independent reflections
Radiation source: rotating anode	2861 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.4°
φ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→15
Tmin = 0.927, Tmax = 0.947	l = −17→17
13810 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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.128	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0639P)2 + 0.4013P] where P = (Fo2 + 2Fc2)/3
3589 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 7.77-7.83 (m, 2H), 7.67 (s, 1H), 7.34-7.41 (m, 2H), 7.29 (d, J = 8.56 Hz, 1H), 7.10 (dd, J = 8.56 Hz and 1.72 Hz, 1H), 2.78 (s, 3H), 2.45 (s, 3H), 2.40 (s, 3H).

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	0.29608 (4)	0.36272 (4)	0.17488 (3)	0.02967 (14)
O1	0.66012 (13)	0.37182 (11)	0.09943 (10)	0.0345 (3)
O2	0.20801 (13)	0.46348 (11)	0.14867 (10)	0.0366 (3)
O3	0.24998 (14)	0.24951 (11)	0.13176 (10)	0.0384 (3)
C1	0.45457 (18)	0.39515 (16)	0.14324 (12)	0.0287 (4)
C2	0.52013 (17)	0.51022 (15)	0.14998 (12)	0.0273 (4)
C3	0.48710 (18)	0.62452 (15)	0.17608 (13)	0.0297 (4)
H3	0.4006	0.6408	0.1940	0.036*
C4	0.58250 (19)	0.71390 (16)	0.17537 (13)	0.0306 (4)
C5	0.70909 (19)	0.68878 (18)	0.14708 (14)	0.0356 (4)
H5	0.7734	0.7511	0.1468	0.043*
C6	0.74318 (19)	0.57618 (17)	0.11965 (14)	0.0361 (4)
H6	0.8287	0.5597	0.1003	0.043*
C7	0.64635 (19)	0.48979 (16)	0.12196 (13)	0.0306 (4)
C8	0.54295 (19)	0.31645 (16)	0.11373 (13)	0.0315 (4)
C9	0.5504 (2)	0.83842 (17)	0.20414 (15)	0.0385 (4)
H9A	0.4861	0.8749	0.1458	0.058*
H9B	0.6362	0.8845	0.2199	0.058*
H9C	0.5082	0.8367	0.2654	0.058*
C10	0.5398 (2)	0.18729 (17)	0.09586 (16)	0.0410 (5)
H10A	0.6052	0.1485	0.1523	0.062*
H10B	0.5660	0.1704	0.0293	0.062*
H10C	0.4463	0.1574	0.0941	0.062*
C11	0.33565 (18)	0.34750 (15)	0.31193 (14)	0.0293 (4)
C12	0.3862 (2)	0.24005 (16)	0.35446 (15)	0.0350 (4)
H12	0.3997	0.1762	0.3107	0.042*
C13	0.4166 (2)	0.22735 (18)	0.46169 (15)	0.0405 (5)
H13	0.4527	0.1549	0.4922	0.049*
C14	0.3941 (2)	0.32033 (18)	0.52383 (15)	0.0383 (4)
H14	0.4147	0.3104	0.5973	0.046*
C15	0.34268 (18)	0.42744 (16)	0.48270 (14)	0.0321 (4)
C16	0.31430 (18)	0.44131 (16)	0.37446 (14)	0.0306 (4)
H16	0.2806	0.5146	0.3441	0.037*
C17	0.3154 (2)	0.52658 (18)	0.55131 (15)	0.0387 (4)
H17A	0.2158	0.5323	0.5488	0.058*
H17B	0.3486	0.6009	0.5270	0.058*
H17C	0.3641	0.5114	0.6230	0.058*

	U11	U22	U33	U12	U13	U23
S1	0.0298 (2)	0.0263 (2)	0.0322 (2)	−0.00279 (17)	0.00464 (17)	−0.00376 (16)
O1	0.0356 (7)	0.0348 (7)	0.0345 (6)	0.0044 (5)	0.0105 (5)	−0.0018 (5)
O2	0.0326 (7)	0.0328 (7)	0.0437 (7)	0.0038 (5)	0.0062 (6)	0.0015 (6)
O3	0.0415 (8)	0.0308 (7)	0.0403 (7)	−0.0082 (6)	0.0027 (6)	−0.0085 (6)
C1	0.0305 (9)	0.0286 (9)	0.0259 (8)	−0.0005 (7)	0.0036 (7)	−0.0013 (6)
C2	0.0276 (8)	0.0302 (9)	0.0230 (7)	0.0000 (7)	0.0026 (6)	0.0015 (6)
C3	0.0278 (9)	0.0307 (9)	0.0301 (8)	−0.0001 (7)	0.0050 (7)	−0.0002 (7)
C4	0.0318 (9)	0.0306 (9)	0.0272 (8)	−0.0003 (7)	0.0008 (7)	0.0040 (7)
C5	0.0327 (9)	0.0371 (11)	0.0367 (9)	−0.0059 (8)	0.0066 (7)	0.0085 (8)
C6	0.0315 (9)	0.0431 (11)	0.0355 (9)	0.0018 (8)	0.0109 (7)	0.0062 (8)
C7	0.0340 (9)	0.0333 (10)	0.0247 (8)	0.0047 (8)	0.0064 (7)	0.0024 (7)
C8	0.0349 (9)	0.0317 (10)	0.0268 (8)	0.0014 (8)	0.0035 (7)	−0.0018 (7)
C9	0.0408 (11)	0.0325 (10)	0.0415 (10)	−0.0034 (8)	0.0066 (8)	0.0004 (8)
C10	0.0458 (11)	0.0337 (11)	0.0427 (10)	0.0065 (9)	0.0075 (9)	−0.0075 (8)
C11	0.0277 (9)	0.0279 (9)	0.0330 (8)	−0.0063 (7)	0.0078 (7)	−0.0021 (7)
C12	0.0384 (10)	0.0289 (10)	0.0391 (9)	−0.0042 (8)	0.0112 (8)	−0.0014 (8)
C13	0.0472 (12)	0.0335 (11)	0.0416 (10)	−0.0008 (9)	0.0115 (9)	0.0056 (8)
C14	0.0392 (10)	0.0424 (11)	0.0348 (9)	−0.0034 (9)	0.0110 (8)	0.0037 (8)
C15	0.0263 (8)	0.0358 (10)	0.0357 (9)	−0.0053 (7)	0.0098 (7)	−0.0051 (8)
C16	0.0282 (9)	0.0282 (9)	0.0359 (9)	−0.0032 (7)	0.0079 (7)	−0.0016 (7)
C17	0.0403 (11)	0.0411 (11)	0.0363 (9)	−0.0004 (9)	0.0115 (8)	−0.0036 (8)

S1—O2	1.4324 (13)	C9—H9B	0.9800
S1—O3	1.4364 (13)	C9—H9C	0.9800
S1—C1	1.7399 (18)	C10—H10A	0.9800
S1—C11	1.7693 (18)	C10—H10B	0.9800
O1—C8	1.363 (2)	C10—H10C	0.9800
O1—C7	1.380 (2)	C11—C16	1.385 (2)
C1—C8	1.359 (2)	C11—C12	1.387 (3)
C1—C2	1.449 (2)	C12—C13	1.385 (3)
C2—C7	1.390 (2)	C12—H12	0.9500
C2—C3	1.394 (2)	C13—C14	1.378 (3)
C3—C4	1.384 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.381 (3)
C4—C5	1.405 (3)	C14—H14	0.9500
C4—C9	1.510 (3)	C15—C16	1.399 (2)
C5—C6	1.385 (3)	C15—C17	1.498 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.372 (3)	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C8—C10	1.480 (3)	C17—H17C	0.9800
C9—H9A	0.9800
O2—S1—O3	119.24 (8)	C4—C9—H9C	109.5
O2—S1—C1	107.84 (8)	H9A—C9—H9C	109.5
O3—S1—C1	108.75 (9)	H9B—C9—H9C	109.5
O2—S1—C11	108.50 (8)	C8—C10—H10A	109.5
O3—S1—C11	107.42 (8)	C8—C10—H10B	109.5
C1—S1—C11	104.08 (8)	H10A—C10—H10B	109.5
C8—O1—C7	106.93 (14)	C8—C10—H10C	109.5
C8—C1—C2	107.54 (16)	H10A—C10—H10C	109.5
C8—C1—S1	126.36 (15)	H10B—C10—H10C	109.5
C2—C1—S1	125.99 (13)	C16—C11—C12	121.31 (17)
C7—C2—C3	119.19 (17)	C16—C11—S1	119.99 (14)
C7—C2—C1	104.37 (15)	C12—C11—S1	118.70 (13)
C3—C2—C1	136.45 (16)	C13—C12—C11	118.97 (17)
C4—C3—C2	118.84 (17)	C13—C12—H12	120.5
C4—C3—H3	120.6	C11—C12—H12	120.5
C2—C3—H3	120.6	C14—C13—C12	119.69 (19)
C3—C4—C5	119.88 (17)	C14—C13—H13	120.2
C3—C4—C9	120.16 (17)	C12—C13—H13	120.2
C5—C4—C9	119.95 (17)	C13—C14—C15	122.04 (18)
C6—C5—C4	122.18 (17)	C13—C14—H14	119.0
C6—C5—H5	118.9	C15—C14—H14	119.0
C4—C5—H5	118.9	C14—C15—C16	118.42 (17)
C7—C6—C5	116.23 (17)	C14—C15—C17	121.33 (17)
C7—C6—H6	121.9	C16—C15—C17	120.24 (17)
C5—C6—H6	121.9	C11—C16—C15	119.54 (17)
C6—C7—O1	125.76 (17)	C11—C16—H16	120.2
C6—C7—C2	123.67 (18)	C15—C16—H16	120.2
O1—C7—C2	110.56 (16)	C15—C17—H17A	109.5
C1—C8—O1	110.60 (16)	C15—C17—H17B	109.5
C1—C8—C10	134.37 (18)	H17A—C17—H17B	109.5
O1—C8—C10	115.02 (16)	C15—C17—H17C	109.5
C4—C9—H9A	109.5	H17A—C17—H17C	109.5
C4—C9—H9B	109.5	H17B—C17—H17C	109.5
H9A—C9—H9B	109.5
O2—S1—C1—C8	−150.31 (15)	C1—C2—C7—O1	−0.07 (18)
O3—S1—C1—C8	−19.69 (18)	C2—C1—C8—O1	−0.81 (19)
C11—S1—C1—C8	94.58 (16)	S1—C1—C8—O1	−177.28 (12)
O2—S1—C1—C2	33.86 (17)	C2—C1—C8—C10	178.18 (19)
O3—S1—C1—C2	164.48 (14)	S1—C1—C8—C10	1.7 (3)
C11—S1—C1—C2	−81.25 (16)	C7—O1—C8—C1	0.77 (18)
C8—C1—C2—C7	0.53 (18)	C7—O1—C8—C10	−178.44 (15)
S1—C1—C2—C7	177.01 (12)	O2—S1—C11—C16	−16.89 (17)
C8—C1—C2—C3	−179.26 (19)	O3—S1—C11—C16	−147.04 (14)
S1—C1—C2—C3	−2.8 (3)	C1—S1—C11—C16	97.75 (15)
C7—C2—C3—C4	−1.3 (2)	O2—S1—C11—C12	162.26 (14)
C1—C2—C3—C4	178.44 (18)	O3—S1—C11—C12	32.11 (17)
C2—C3—C4—C5	1.0 (3)	C1—S1—C11—C12	−83.10 (15)
C2—C3—C4—C9	−179.47 (15)	C16—C11—C12—C13	−0.5 (3)
C3—C4—C5—C6	−0.2 (3)	S1—C11—C12—C13	−179.62 (15)
C9—C4—C5—C6	−179.74 (17)	C11—C12—C13—C14	1.1 (3)
C4—C5—C6—C7	−0.2 (3)	C12—C13—C14—C15	−0.5 (3)
C5—C6—C7—O1	−178.79 (16)	C13—C14—C15—C16	−0.7 (3)
C5—C6—C7—C2	−0.1 (3)	C13—C14—C15—C17	178.39 (19)
C8—O1—C7—C6	178.39 (17)	C12—C11—C16—C15	−0.7 (3)
C8—O1—C7—C2	−0.41 (18)	S1—C11—C16—C15	178.42 (13)
C3—C2—C7—C6	0.9 (3)	C14—C15—C16—C11	1.3 (3)
C1—C2—C7—C6	−178.90 (16)	C17—C15—C16—C11	−177.82 (16)
C3—C2—C7—O1	179.76 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O3	0.98	2.34	3.078 (3)	131
C17—H17B···Cg1i	0.98	2.88	3.478 (2)	121

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 3-methyl­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯O3	0.98	2.34	3.078 (3)	131
C17—H17B⋯Cg1i	0.98	2.88	3.478 (2)	121

Symmetry code: (i) .