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

In the title compound, C17H16O2S, the dihedral angle between the benzo-furan ring system [r.m.s. deviation = 0.009 (1) Å] and the 2-methyl-phenyl ring is 86.72 (4)°. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into columns along the b-axis direction.

Related literature

For the pharmacological properties of benzo­furan compounds, see: Aslam et al. (2009 ▸); Galal et al. (2009 ▸); Howlett et al. (1999 ▸); Wahab Khan et al. (2005 ▸); Ono et al. (2002 ▸). For natural products with a benzo­furan ring, see: Akgul & Anil (2003 ▸); Soekamto et al. (2003 ▸). For a related structure, see: Choi et al. (2012 ▸). For further synthetic details, see: Choi et al. (1999 ▸).

Experimental

Crystal data

C17H16O2S

M = 284.36

Monoclinic,

a = 10.8458 (2) Å

b = 8.0139 (1) Å

c = 16.4295 (2) Å

β = 96.709 (1)°

V = 1418.23 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.44 × 0.33 × 0.30 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.692, T max = 0.746

25176 measured reflections

3529 independent reflections

3091 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 1.05

3529 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and DIAMOND (Brandenburg, 1998 ▸); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015012773/cv5492sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012773/cv5492Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015012773/cv5492Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015012773/cv5492fig1.tif

The mol­ecular structure of the title compound, showing 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 x y z x y z . DOI: 10.1107/S2056989015012773/cv5492fig2.tif

A view of the C—H⋯O hydrogen bonds (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 + , y − , − z + ; (ii) x, y − 1, z; (iii) − x + , y + , − z + ; (iv) x, y + 1, z.]

CCDC reference: 1410058

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

C17H16O2S	F(000) = 600
Mr = 284.36	Dx = 1.332 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.8458 (2) Å	Cell parameters from 9125 reflections
b = 8.0139 (1) Å	θ = 2.5–28.1°
c = 16.4295 (2) Å	µ = 0.23 mm−1
β = 96.709 (1)°	T = 173 K
V = 1418.23 (4) Å3	Block, colourless
Z = 4	0.44 × 0.33 × 0.30 mm

Bruker SMART APEXII CCD diffractometer	3529 independent reflections
Radiation source: rotating anode	3091 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.033
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.1°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.692, Tmax = 0.746	l = −21→20
25176 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.5244P] where P = (Fo2 + 2Fc2)/3
3529 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.35 (d, J = 7.88 Hz, 1H), 7.53–7.57 (m, 1H), 7.38–7.42 (m, 1H), 7.26 (d, J = 7.02 Hz, 1H), 7.15 (d, J = 7.52 Hz, 1H), 6.98–7.03 (m, 2H), 2.73 (s, 3H), 2.25 (s, 3H), 2.13 (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.

	x	y	z	Uiso*/Ueq
S1	0.17973 (3)	0.37549 (4)	0.52324 (2)	0.02675 (11)
O1	0.17654 (10)	0.24730 (14)	0.75315 (6)	0.0349 (2)
O2	0.21361 (11)	0.55407 (13)	0.51308 (6)	0.0381 (3)
C1	0.21664 (12)	0.31930 (17)	0.62666 (8)	0.0250 (3)
C2	0.33439 (12)	0.30795 (16)	0.67783 (8)	0.0236 (3)
C3	0.45906 (12)	0.33131 (16)	0.66789 (8)	0.0255 (3)
H3	0.4825	0.3619	0.6160	0.031*
C4	0.54881 (13)	0.30933 (18)	0.73475 (9)	0.0307 (3)
C5	0.51194 (15)	0.2614 (2)	0.81059 (9)	0.0363 (3)
H5	0.5740	0.2456	0.8557	0.044*
C6	0.38937 (16)	0.23627 (19)	0.82225 (9)	0.0355 (3)
H6	0.3656	0.2031	0.8737	0.043*
C7	0.30345 (13)	0.26225 (18)	0.75471 (8)	0.0287 (3)
C8	0.12638 (13)	0.28335 (19)	0.67489 (9)	0.0304 (3)
C9	0.68418 (15)	0.3366 (2)	0.72713 (11)	0.0434 (4)
H9A	0.6941	0.3692	0.6708	0.065*
H9B	0.7301	0.2331	0.7408	0.065*
H9C	0.7165	0.4252	0.7648	0.065*
C10	−0.01086 (15)	0.2761 (3)	0.65979 (11)	0.0452 (4)
H10A	−0.0380	0.3087	0.6030	0.068*
H10B	−0.0466	0.3527	0.6972	0.068*
H10C	−0.0388	0.1622	0.6691	0.068*
C11	0.29473 (12)	0.25559 (17)	0.47850 (7)	0.0236 (3)
C12	0.38520 (14)	0.34425 (18)	0.44408 (8)	0.0297 (3)
H12	0.3893	0.4622	0.4493	0.036*
C13	0.46993 (15)	0.2599 (2)	0.40181 (9)	0.0365 (3)
H13	0.5331	0.3197	0.3788	0.044*
C14	0.46160 (15)	0.0895 (2)	0.39362 (9)	0.0363 (3)
H14	0.5183	0.0315	0.3639	0.044*
C15	0.37125 (14)	0.00203 (19)	0.42834 (9)	0.0338 (3)
H15	0.3675	−0.1159	0.4225	0.041*
C16	0.28551 (13)	0.08234 (18)	0.47168 (8)	0.0285 (3)
C17	0.18974 (17)	−0.0156 (2)	0.50997 (12)	0.0464 (4)
H17A	0.2083	−0.0119	0.5698	0.070*
H17B	0.1907	−0.1318	0.4914	0.070*
H17C	0.1075	0.0326	0.4938	0.070*

	U11	U22	U33	U12	U13	U23
S1	0.02608 (18)	0.03273 (19)	0.02139 (17)	0.00435 (12)	0.00261 (12)	0.00056 (12)
O1	0.0357 (6)	0.0446 (6)	0.0266 (5)	−0.0031 (5)	0.0128 (4)	0.0039 (4)
O2	0.0555 (7)	0.0288 (5)	0.0317 (5)	0.0098 (5)	0.0130 (5)	0.0029 (4)
C1	0.0253 (6)	0.0285 (6)	0.0219 (6)	0.0001 (5)	0.0053 (5)	0.0000 (5)
C2	0.0290 (6)	0.0229 (6)	0.0194 (6)	0.0002 (5)	0.0046 (5)	−0.0003 (4)
C3	0.0266 (6)	0.0280 (6)	0.0220 (6)	−0.0007 (5)	0.0026 (5)	−0.0005 (5)
C4	0.0314 (7)	0.0304 (7)	0.0292 (7)	0.0008 (5)	−0.0014 (6)	−0.0019 (5)
C5	0.0433 (8)	0.0393 (8)	0.0238 (7)	0.0031 (6)	−0.0064 (6)	0.0009 (6)
C6	0.0515 (9)	0.0353 (8)	0.0198 (6)	0.0018 (7)	0.0052 (6)	0.0032 (5)
C7	0.0331 (7)	0.0312 (7)	0.0230 (6)	−0.0009 (5)	0.0084 (5)	0.0008 (5)
C8	0.0289 (7)	0.0362 (7)	0.0275 (7)	−0.0020 (5)	0.0089 (5)	−0.0005 (5)
C9	0.0293 (8)	0.0558 (10)	0.0424 (9)	−0.0019 (7)	−0.0066 (7)	−0.0019 (7)
C10	0.0281 (8)	0.0646 (11)	0.0451 (9)	−0.0056 (7)	0.0132 (7)	−0.0002 (8)
C11	0.0245 (6)	0.0286 (7)	0.0171 (5)	0.0019 (5)	0.0003 (5)	−0.0007 (4)
C12	0.0344 (7)	0.0309 (7)	0.0249 (6)	−0.0023 (5)	0.0073 (5)	−0.0004 (5)
C13	0.0363 (8)	0.0450 (9)	0.0304 (7)	0.0001 (6)	0.0128 (6)	0.0006 (6)
C14	0.0373 (8)	0.0457 (9)	0.0263 (7)	0.0124 (7)	0.0049 (6)	−0.0039 (6)
C15	0.0418 (8)	0.0299 (7)	0.0285 (7)	0.0069 (6)	−0.0015 (6)	−0.0039 (5)
C16	0.0313 (7)	0.0300 (7)	0.0232 (6)	−0.0014 (5)	−0.0011 (5)	−0.0005 (5)
C17	0.0526 (10)	0.0321 (8)	0.0570 (11)	−0.0126 (7)	0.0168 (8)	−0.0016 (7)

S1—O2	1.4918 (11)	C9—H9B	0.9800
S1—C1	1.7580 (13)	C9—H9C	0.9800
S1—C11	1.7982 (13)	C10—H10A	0.9800
O1—C8	1.3671 (18)	C10—H10B	0.9800
O1—C7	1.3789 (17)	C10—H10C	0.9800
C1—C8	1.3604 (18)	C11—C12	1.3846 (19)
C1—C2	1.4476 (18)	C11—C16	1.3955 (19)
C2—C7	1.3932 (17)	C12—C13	1.390 (2)
C2—C3	1.3934 (18)	C12—H12	0.9500
C3—C4	1.3912 (19)	C13—C14	1.375 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.406 (2)	C14—C15	1.381 (2)
C4—C9	1.504 (2)	C14—H14	0.9500
C5—C6	1.380 (2)	C15—C16	1.393 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.379 (2)	C16—C17	1.498 (2)
C6—H6	0.9500	C17—H17A	0.9800
C8—C10	1.481 (2)	C17—H17B	0.9800
C9—H9A	0.9800	C17—H17C	0.9800
O2—S1—C1	108.82 (6)	H9A—C9—H9C	109.5
O2—S1—C11	105.97 (6)	H9B—C9—H9C	109.5
C1—S1—C11	99.66 (6)	C8—C10—H10A	109.5
C8—O1—C7	106.61 (10)	C8—C10—H10B	109.5
C8—C1—C2	107.12 (12)	H10A—C10—H10B	109.5
C8—C1—S1	121.27 (11)	C8—C10—H10C	109.5
C2—C1—S1	131.55 (10)	H10A—C10—H10C	109.5
C7—C2—C3	118.78 (12)	H10B—C10—H10C	109.5
C7—C2—C1	104.68 (11)	C12—C11—C16	121.69 (12)
C3—C2—C1	136.54 (12)	C12—C11—S1	116.82 (10)
C4—C3—C2	119.30 (13)	C16—C11—S1	121.19 (10)
C4—C3—H3	120.3	C11—C12—C13	119.74 (14)
C2—C3—H3	120.3	C11—C12—H12	120.1
C3—C4—C5	119.29 (13)	C13—C12—H12	120.1
C3—C4—C9	121.04 (14)	C14—C13—C12	119.48 (14)
C5—C4—C9	119.67 (14)	C14—C13—H13	120.3
C6—C5—C4	122.77 (13)	C12—C13—H13	120.3
C6—C5—H5	118.6	C13—C14—C15	120.36 (14)
C4—C5—H5	118.6	C13—C14—H14	119.8
C7—C6—C5	115.96 (13)	C15—C14—H14	119.8
C7—C6—H6	122.0	C14—C15—C16	121.67 (14)
C5—C6—H6	122.0	C14—C15—H15	119.2
O1—C7—C6	125.53 (13)	C16—C15—H15	119.2
O1—C7—C2	110.59 (12)	C15—C16—C11	117.05 (13)
C6—C7—C2	123.88 (14)	C15—C16—C17	120.63 (14)
C1—C8—O1	110.99 (12)	C11—C16—C17	122.31 (13)
C1—C8—C10	133.48 (14)	C16—C17—H17A	109.5
O1—C8—C10	115.53 (12)	C16—C17—H17B	109.5
C4—C9—H9A	109.5	H17A—C17—H17B	109.5
C4—C9—H9B	109.5	C16—C17—H17C	109.5
H9A—C9—H9B	109.5	H17A—C17—H17C	109.5
C4—C9—H9C	109.5	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.45	3.3772 (18)	166
C17—H17B···O2ii	0.98	2.55	3.458 (2)	154

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6O2i	0.95	2.45	3.3772(18)	166
C17H17BO2ii	0.98	2.55	3.458(2)	154

Symmetry codes: (i) ; (ii) .