5-Isopropyl-2-methyl-3-phenyl-sulfonyl-1-benzofuran.

The title compound, C(18)H(18)O(3)S, was prepared by the oxidation of 5-isopropyl-2-methyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 79.37 (6)° with the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π-π stacking inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.762 (3) Å]. In addition, the stacked mol-ecules exhibit C-H⋯π and intra-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 2-methyl-3-phenyl­sulfonyl-1-benzofuran compounds, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C18H18O3S

M = 314.38

Monoclinic,

a = 10.736 (1) Å

b = 13.024 (1) Å

c = 11.729 (1) Å

β = 99.655 (2)°

V = 1616.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 173 (2) K

0.60 × 0.40 × 0.40 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

9705 measured reflections

3505 independent reflections

3008 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.127

S = 0.98

3505 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.53 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808017224/rt2021sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017224/rt2021Isup2.hkl

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

C18H18O3S	F000 = 664
Mr = 314.38	Dx = 1.292 Mg m−3
Monoclinic, P21/c	Melting point = 386–387 K
Hall symbol: -p 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 10.736 (1) Å	Cell parameters from 5849 reflections
b = 13.024 (1) Å	θ = 2.4–28.1º
c = 11.729 (1) Å	µ = 0.21 mm−1
β = 99.655 (2)º	T = 173 (2) K
V = 1616.8 (2) Å3	Block, colorless
Z = 4	0.60 × 0.40 × 0.40 mm

Bruker SMART CCD diffractometer	3505 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.066
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 173(2) K	θmin = 2.5º
φ and ω scans	h = −13→13
Absorption correction: none	k = −15→16
9705 measured reflections	l = −13→14

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.061P)2 + 1.3518P] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
3505 reflections	Δρmax = 0.25 e Å−3
200 parameters	Δρmin = −0.53 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S	0.83554 (4)	0.69176 (3)	0.55320 (4)	0.02524 (15)
O1	0.46657 (13)	0.66684 (10)	0.47014 (12)	0.0288 (3)
O2	0.84305 (15)	0.79303 (10)	0.60360 (13)	0.0360 (4)
O3	0.90954 (14)	0.66788 (11)	0.46512 (12)	0.0328 (3)
C1	0.67826 (18)	0.66590 (13)	0.49602 (15)	0.0239 (4)
C2	0.63435 (17)	0.58971 (13)	0.40821 (15)	0.0224 (4)
C3	0.68980 (17)	0.52023 (13)	0.34157 (16)	0.0247 (4)
H3	0.7791	0.5153	0.3493	0.030*
C4	0.61150 (18)	0.45785 (14)	0.26310 (17)	0.0273 (4)
C5	0.47968 (19)	0.46738 (15)	0.25280 (17)	0.0294 (4)
H5	0.4275	0.4251	0.1986	0.035*
C6	0.42262 (18)	0.53572 (14)	0.31820 (17)	0.0285 (4)
H6	0.3334	0.5417	0.3101	0.034*
C7	0.50303 (17)	0.59463 (13)	0.39592 (15)	0.0241 (4)
C8	0.5751 (2)	0.70820 (14)	0.53031 (17)	0.0285 (4)
C9	0.87264 (17)	0.60205 (13)	0.66639 (15)	0.0231 (4)
C10	0.85507 (18)	0.62898 (15)	0.77698 (16)	0.0287 (4)
H10	0.8269	0.6959	0.7924	0.034*
C11	0.8793 (2)	0.55655 (17)	0.86501 (17)	0.0330 (4)
H11	0.8657	0.5732	0.9408	0.040*
C12	0.92341 (19)	0.45979 (16)	0.84182 (18)	0.0327 (4)
H12	0.9401	0.4105	0.9022	0.039*
C13	0.94327 (18)	0.43436 (15)	0.73172 (17)	0.0300 (4)
H13	0.9752	0.3684	0.7172	0.036*
C14	0.91658 (17)	0.50522 (14)	0.64226 (16)	0.0255 (4)
H14	0.9281	0.4879	0.5661	0.031*
C15	0.6668 (2)	0.38118 (17)	0.1882 (2)	0.0391 (5)
H15	0.5962	0.3356	0.1517	0.047*
C16	0.7664 (3)	0.3128 (2)	0.2585 (3)	0.0692 (9)
H16A	0.7283	0.2745	0.3158	0.083*
H16B	0.8356	0.3554	0.2982	0.083*
H16C	0.7993	0.2645	0.2068	0.083*
C17	0.7186 (3)	0.4350 (2)	0.0905 (3)	0.0668 (9)
H17A	0.7851	0.4833	0.1234	0.080*
H17B	0.6503	0.4725	0.0420	0.080*
H17C	0.7538	0.3839	0.0435	0.080*
C18	0.5557 (2)	0.78612 (17)	0.6181 (2)	0.0409 (5)
H18A	0.6374	0.8155	0.6525	0.061*
H18B	0.5166	0.7536	0.6786	0.061*
H18C	0.5004	0.8407	0.5810	0.061*

	U11	U22	U33	U12	U13	U23
S	0.0298 (3)	0.0207 (2)	0.0246 (2)	−0.00658 (17)	0.00273 (18)	−0.00024 (16)
O1	0.0279 (7)	0.0279 (7)	0.0305 (7)	0.0059 (5)	0.0044 (5)	0.0014 (5)
O2	0.0483 (9)	0.0211 (7)	0.0376 (8)	−0.0101 (6)	0.0040 (7)	−0.0042 (6)
O3	0.0331 (8)	0.0362 (8)	0.0300 (7)	−0.0074 (6)	0.0079 (6)	0.0017 (6)
C1	0.0303 (9)	0.0194 (8)	0.0213 (8)	−0.0009 (7)	0.0017 (7)	0.0027 (6)
C2	0.0253 (9)	0.0193 (8)	0.0218 (8)	−0.0015 (7)	0.0013 (7)	0.0044 (6)
C3	0.0221 (8)	0.0225 (8)	0.0290 (9)	−0.0016 (7)	0.0025 (7)	−0.0006 (7)
C4	0.0283 (10)	0.0225 (9)	0.0305 (10)	−0.0037 (7)	0.0036 (8)	−0.0014 (7)
C5	0.0286 (10)	0.0273 (9)	0.0303 (10)	−0.0069 (8)	−0.0007 (8)	0.0002 (7)
C6	0.0216 (9)	0.0305 (9)	0.0322 (10)	−0.0010 (7)	0.0007 (8)	0.0058 (8)
C7	0.0262 (9)	0.0224 (8)	0.0237 (9)	0.0042 (7)	0.0040 (7)	0.0062 (7)
C8	0.0355 (10)	0.0223 (9)	0.0268 (9)	0.0028 (7)	0.0029 (8)	0.0039 (7)
C9	0.0216 (8)	0.0241 (8)	0.0228 (9)	−0.0049 (7)	0.0018 (7)	0.0001 (7)
C10	0.0284 (10)	0.0299 (9)	0.0261 (9)	−0.0010 (8)	−0.0004 (7)	−0.0044 (7)
C11	0.0319 (10)	0.0440 (11)	0.0212 (9)	0.0011 (9)	−0.0012 (8)	−0.0002 (8)
C12	0.0284 (10)	0.0388 (11)	0.0289 (10)	0.0025 (8)	−0.0015 (8)	0.0076 (8)
C13	0.0231 (9)	0.0305 (10)	0.0359 (10)	0.0026 (7)	0.0039 (8)	0.0028 (8)
C14	0.0217 (8)	0.0286 (9)	0.0266 (9)	−0.0023 (7)	0.0048 (7)	−0.0018 (7)
C15	0.0326 (11)	0.0333 (11)	0.0517 (13)	−0.0065 (8)	0.0078 (10)	−0.0198 (9)
C16	0.0556 (17)	0.0461 (15)	0.101 (2)	0.0171 (13)	−0.0013 (17)	−0.0282 (15)
C17	0.080 (2)	0.0640 (18)	0.0664 (18)	−0.0203 (15)	0.0404 (16)	−0.0332 (15)
C18	0.0482 (13)	0.0337 (11)	0.0420 (12)	0.0074 (10)	0.0111 (10)	−0.0087 (9)

S—O3	1.439 (2)	C10—C11	1.390 (3)
S—O2	1.442 (1)	C10—H10	0.9500
S—C1	1.742 (2)	C11—C12	1.389 (3)
S—C9	1.763 (2)	C11—H11	0.9500
O1—C8	1.367 (2)	C12—C13	1.384 (3)
O1—C7	1.382 (2)	C12—H12	0.9500
C1—C8	1.357 (3)	C13—C14	1.391 (3)
C1—C2	1.451 (2)	C13—H13	0.9500
C2—C7	1.394 (3)	C14—H14	0.9500
C2—C3	1.393 (3)	C15—C16	1.524 (4)
C3—C4	1.398 (3)	C15—C17	1.525 (4)
C3—H3	0.9500	C15—H15	1.0000
C4—C5	1.406 (3)	C16—H16A	0.9800
C4—C15	1.515 (3)	C16—H16B	0.9800
C5—C6	1.383 (3)	C16—H16C	0.9800
C5—H5	0.9500	C17—H17A	0.9800
C6—C7	1.379 (3)	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800
C8—C18	1.485 (3)	C18—H18A	0.9800
C9—C10	1.387 (3)	C18—H18B	0.9800
C9—C14	1.392 (3)	C18—H18C	0.9800
O3—S—O2	119.50 (9)	C10—C11—C12	119.8 (2)
O3—S—C1	107.34 (9)	C10—C11—H11	120.1
O2—S—C1	108.58 (9)	C12—C11—H11	120.1
O3—S—C9	108.37 (9)	C13—C12—C11	120.7 (2)
O2—S—C9	107.90 (9)	C13—C12—H12	119.6
C1—S—C9	104.11 (8)	C11—C12—H12	119.6
C8—O1—C7	106.6 (2)	C12—C13—C14	120.1 (2)
C8—C1—C2	107.7 (2)	C12—C13—H13	120.0
C8—C1—S	126.5 (2)	C14—C13—H13	120.0
C2—C1—S	125.7 (1)	C13—C14—C9	118.8 (2)
C7—C2—C3	119.5 (2)	C13—C14—H14	120.6
C7—C2—C1	104.2 (2)	C9—C14—H14	120.6
C3—C2—C1	136.4 (2)	C4—C15—C16	112.2 (2)
C2—C3—C4	118.7 (2)	C4—C15—C17	111.1 (2)
C2—C3—H3	120.6	C16—C15—C17	111.4 (3)
C4—C3—H3	120.6	C4—C15—H15	107.3
C5—C4—C3	119.4 (2)	C16—C15—H15	107.3
C5—C4—C15	119.7 (2)	C17—C15—H15	107.3
C3—C4—C15	120.9 (2)	C15—C16—H16A	109.5
C6—C5—C4	122.8 (2)	C15—C16—H16B	109.5
C6—C5—H5	118.6	H16A—C16—H16B	109.5
C4—C5—H5	118.6	C15—C16—H16C	109.5
C5—C6—C7	116.0 (2)	H16A—C16—H16C	109.5
C5—C6—H6	122.0	H16B—C16—H16C	109.5
C7—C6—H6	122.0	C15—C17—H17A	109.5
C6—C7—O1	125.7 (2)	C15—C17—H17B	109.5
C6—C7—C2	123.6 (2)	H17A—C17—H17B	109.5
O1—C7—C2	110.8 (2)	C15—C17—H17C	109.5
C1—C8—O1	110.8 (2)	H17A—C17—H17C	109.5
C1—C8—C18	134.4 (2)	H17B—C17—H17C	109.5
O1—C8—C18	114.9 (2)	C8—C18—H18A	109.5
C10—C9—C14	121.6 (2)	C8—C18—H18B	109.5
C10—C9—S	119.2 (1)	H18A—C18—H18B	109.5
C14—C9—S	119.3 (1)	C8—C18—H18C	109.5
C9—C10—C11	119.0 (2)	H18A—C18—H18C	109.5
C9—C10—H10	120.5	H18B—C18—H18C	109.5
C11—C10—H10	120.5
O3—S—C1—C8	−155.70 (16)	C2—C1—C8—O1	−1.1 (2)
O2—S—C1—C8	−25.23 (19)	S—C1—C8—O1	−177.24 (12)
C9—S—C1—C8	89.53 (18)	C2—C1—C8—C18	177.6 (2)
O3—S—C1—C2	28.81 (17)	S—C1—C8—C18	1.5 (3)
O2—S—C1—C2	159.29 (15)	C7—O1—C8—C1	0.7 (2)
C9—S—C1—C2	−85.95 (16)	C7—O1—C8—C18	−178.25 (16)
C8—C1—C2—C7	0.97 (19)	O3—S—C9—C10	154.95 (15)
S—C1—C2—C7	177.16 (13)	O2—S—C9—C10	24.22 (18)
C8—C1—C2—C3	−178.7 (2)	C1—S—C9—C10	−91.01 (16)
S—C1—C2—C3	−2.5 (3)	O3—S—C9—C14	−26.26 (17)
C7—C2—C3—C4	0.6 (3)	O2—S—C9—C14	−156.99 (14)
C1—C2—C3—C4	−179.76 (19)	C1—S—C9—C14	87.77 (16)
C2—C3—C4—C5	0.5 (3)	C14—C9—C10—C11	−1.5 (3)
C2—C3—C4—C15	179.81 (18)	S—C9—C10—C11	177.28 (15)
C3—C4—C5—C6	−0.7 (3)	C9—C10—C11—C12	1.6 (3)
C15—C4—C5—C6	−179.93 (19)	C10—C11—C12—C13	−0.2 (3)
C4—C5—C6—C7	−0.4 (3)	C11—C12—C13—C14	−1.3 (3)
C5—C6—C7—O1	−179.49 (16)	C12—C13—C14—C9	1.4 (3)
C5—C6—C7—C2	1.6 (3)	C10—C9—C14—C13	0.0 (3)
C8—O1—C7—C6	−179.09 (17)	S—C9—C14—C13	−178.78 (14)
C8—O1—C7—C2	−0.08 (19)	C5—C4—C15—C16	−129.9 (2)
C3—C2—C7—C6	−1.8 (3)	C3—C4—C15—C16	50.8 (3)
C1—C2—C7—C6	178.49 (17)	C5—C4—C15—C17	104.7 (2)
C3—C2—C7—O1	179.20 (15)	C3—C4—C15—C17	−74.6 (3)
C1—C2—C7—O1	−0.54 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg3i	0.95	2.65	3.516 (3)	152
C18—H18A···O2	0.98	2.39	3.119 (3)	131
C10—H10···O2	0.95	2.58	2.938 (2)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg3i	0.95	2.65	3.516 (3)	152
C18—H18A⋯O2	0.98	2.39	3.119 (3)	131
C10—H10⋯O2	0.95	2.58	2.938 (2)	103

Symmetry code: (i) . Cg3 is the centroid of the C9—C14 phenyl ring.