5-Cyclo-pentyl-2-(4-methyl-phen-yl)-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C(21)H(22)O(2)S, the cyclo-pentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The benzofuran unit is essentially planar, with a mean deviation from the least-squares plane defined by the nine constituent ring atoms of 0.008 (2) Å. In the crystal, mol-ecules are linked via pairs of C-H⋯π inter-actions, forming inversion dimers. In the ring of the 4-methyl-phenyl group, four C atoms and their attached H atoms are disordered over two sets of sites, with site-ccupancy factors of 0.899 (5) and 0.10.

Related literature

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

Experimental

Crystal data

C21H22O2S

M = 338.45

Monoclinic,

a = 15.2869 (5) Å

b = 7.2881 (3) Å

c = 15.3608 (6) Å

β = 97.599 (2)°

V = 1696.35 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.29 × 0.23 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.653, T max = 0.746

12919 measured reflections

2994 independent reflections

2154 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.173

S = 1.07

2994 reflections

212 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.36 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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812042249/hg5259sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042249/hg5259Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042249/hg5259Isup3.cml

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

C21H22O2S	F(000) = 720
Mr = 338.45	Dx = 1.325 Mg m−3
Monoclinic, P21/c	Melting point = 424–425 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.2869 (5) Å	Cell parameters from 2479 reflections
b = 7.2881 (3) Å	θ = 2.7–28.1°
c = 15.3608 (6) Å	µ = 0.20 mm−1
β = 97.599 (2)°	T = 173 K
V = 1696.35 (11) Å3	Block, colourless
Z = 4	0.29 × 0.23 × 0.17 mm

Bruker SMART APEXII CCD diffractometer	2994 independent reflections
Radiation source: rotating anode	2154 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.043
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.7°
φ– and ω–scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
Tmin = 0.653, Tmax = 0.746	l = −16→18
12919 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)] = 0.059	Hydrogen site location: difference Fourier map
wR(F2) = 0.173	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0828P)2 + 1.5926P] where P = (Fo2 + 2Fc2)/3
2994 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.86 e Å−3
14 restraints	Δρmin = −0.36 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	Occ. (<1)
S1	0.39884 (5)	0.23817 (10)	0.27487 (5)	0.0298 (3)
O2	0.33603 (17)	0.1030 (4)	0.22826 (15)	0.0577 (7)
O1	0.37504 (12)	0.2498 (2)	0.52846 (12)	0.0243 (5)
C1	0.36912 (17)	0.2579 (3)	0.38147 (18)	0.0231 (6)
C2	0.27970 (17)	0.2531 (3)	0.40194 (18)	0.0214 (6)
C3	0.19556 (17)	0.2513 (3)	0.35376 (18)	0.0230 (6)
H3	0.1885	0.2516	0.2914	0.028*
C4	0.12236 (18)	0.2493 (3)	0.39841 (19)	0.0228 (6)
C5	0.13432 (18)	0.2478 (3)	0.49058 (18)	0.0248 (6)
H5	0.0837	0.2471	0.5204	0.030*
C6	0.21657 (18)	0.2473 (3)	0.53943 (18)	0.0253 (6)
H6	0.2239	0.2459	0.6018	0.030*
C7	0.28779 (17)	0.2491 (3)	0.49274 (18)	0.0224 (6)
C8	0.42346 (17)	0.2554 (3)	0.45874 (18)	0.0224 (6)
C9	0.03109 (17)	0.2503 (3)	0.34703 (19)	0.0244 (6)
H9	0.0380	0.2472	0.2832	0.029*
C10	−0.02605 (17)	0.4168 (4)	0.36192 (19)	0.0309 (7)
H10A	−0.0044	0.5284	0.3349	0.037*
H10B	−0.0269	0.4391	0.4254	0.037*
C11	−0.11767 (18)	0.3623 (5)	0.3166 (2)	0.0388 (8)
H11A	−0.1260	0.4038	0.2547	0.047*
H11B	−0.1643	0.4178	0.3472	0.047*
C12	−0.12123 (18)	0.1522 (5)	0.3216 (2)	0.0382 (8)
H12A	−0.1347	0.0988	0.2621	0.046*
H12B	−0.1672	0.1126	0.3573	0.046*
C13	−0.02941 (17)	0.0915 (4)	0.3647 (2)	0.0319 (7)
H13A	−0.0288	0.0722	0.4285	0.038*
H13B	−0.0111	−0.0235	0.3379	0.038*
C14A	0.51894 (17)	0.2566 (3)	0.48277 (18)	0.0232 (7)	0.899 (5)
C15A	0.57418 (15)	0.3215 (5)	0.4245 (2)	0.0300 (5)	0.899 (5)
H15A	0.5495	0.3688	0.3690	0.036*	0.899 (5)
C16A	0.66532 (18)	0.3175 (5)	0.4470 (2)	0.0300 (5)	0.899 (5)
H16A	0.7022	0.3584	0.4057	0.036*	0.899 (5)
C17A	0.70343 (17)	0.2548 (3)	0.52866 (19)	0.0262 (7)	0.899 (5)
C18A	0.64777 (15)	0.1982 (5)	0.5875 (2)	0.0300 (5)	0.899 (5)
H18A	0.6724	0.1585	0.6444	0.036*	0.899 (5)
C19A	0.55714 (18)	0.1983 (5)	0.5653 (2)	0.0300 (5)	0.899 (5)
H19A	0.5205	0.1581	0.6069	0.036*	0.899 (5)
C14B	0.51894 (17)	0.2566 (3)	0.48277 (18)	0.0232 (7)	0.10
C15B	0.5736 (12)	0.174 (4)	0.4248 (19)	0.0300 (5)	0.10
H15B	0.5489	0.1184	0.3711	0.036*	0.101 (5)
C16B	0.6644 (13)	0.178 (4)	0.4502 (10)	0.0300 (5)	0.10
H16B	0.7016	0.1261	0.4119	0.036*	0.101 (5)
C17B	0.70343 (17)	0.2548 (3)	0.52866 (19)	0.0262 (7)	0.10
C18B	0.6487 (11)	0.308 (4)	0.5890 (11)	0.0300 (5)	0.10
H18B	0.6734	0.3435	0.6465	0.036*	0.101 (5)
C19B	0.5582 (12)	0.309 (4)	0.5658 (8)	0.0300 (5)	0.10
H19B	0.5217	0.3468	0.6080	0.036*	0.101 (5)
C20	0.80136 (18)	0.2528 (4)	0.5536 (2)	0.0351 (8)
H20A	0.8300	0.2983	0.5044	0.053*
H20B	0.8210	0.1271	0.5678	0.053*
H20C	0.8172	0.3317	0.6049	0.053*
C21	0.3672 (2)	0.4541 (5)	0.2339 (2)	0.0483 (9)
H21A	0.3689	0.4564	0.1704	0.072*
H21B	0.4078	0.5468	0.2623	0.072*
H21C	0.3072	0.4808	0.2460	0.072*

	U11	U22	U33	U12	U13	U23
S1	0.0305 (4)	0.0384 (5)	0.0214 (4)	0.0008 (3)	0.0067 (3)	−0.0013 (3)
O2	0.0737 (17)	0.0619 (17)	0.0379 (14)	−0.0226 (14)	0.0086 (12)	−0.0090 (13)
O1	0.0240 (10)	0.0286 (11)	0.0196 (10)	0.0005 (8)	0.0007 (8)	−0.0009 (8)
C1	0.0226 (13)	0.0249 (14)	0.0223 (14)	0.0016 (11)	0.0048 (11)	0.0017 (11)
C2	0.0262 (14)	0.0185 (13)	0.0201 (14)	0.0004 (10)	0.0051 (11)	−0.0009 (11)
C3	0.0275 (14)	0.0231 (14)	0.0180 (14)	0.0003 (11)	0.0020 (11)	0.0003 (11)
C4	0.0236 (14)	0.0192 (14)	0.0253 (15)	0.0000 (10)	0.0022 (11)	0.0004 (11)
C5	0.0246 (14)	0.0259 (15)	0.0243 (15)	−0.0008 (11)	0.0052 (11)	0.0002 (12)
C6	0.0293 (15)	0.0285 (15)	0.0183 (14)	0.0000 (11)	0.0035 (11)	−0.0002 (12)
C7	0.0225 (14)	0.0212 (14)	0.0227 (15)	−0.0008 (11)	−0.0002 (11)	−0.0013 (11)
C8	0.0250 (14)	0.0205 (14)	0.0224 (14)	0.0000 (11)	0.0052 (11)	−0.0015 (11)
C9	0.0249 (14)	0.0268 (15)	0.0209 (14)	−0.0005 (11)	0.0008 (11)	−0.0003 (12)
C10	0.0300 (15)	0.0300 (16)	0.0318 (17)	0.0035 (12)	0.0008 (12)	−0.0011 (13)
C11	0.0247 (16)	0.049 (2)	0.0411 (19)	0.0059 (14)	0.0006 (13)	0.0031 (16)
C12	0.0257 (16)	0.050 (2)	0.0375 (18)	−0.0083 (14)	0.0003 (13)	−0.0014 (15)
C13	0.0301 (15)	0.0291 (16)	0.0354 (17)	−0.0051 (12)	−0.0001 (13)	−0.0006 (13)
C14A	0.0244 (14)	0.0200 (14)	0.0243 (15)	0.0000 (11)	0.0002 (11)	−0.0019 (11)
C15A	0.0283 (9)	0.0332 (11)	0.0279 (9)	−0.0013 (7)	0.0020 (7)	0.0012 (8)
C16A	0.0283 (9)	0.0332 (11)	0.0279 (9)	−0.0013 (7)	0.0020 (7)	0.0012 (8)
C17A	0.0247 (14)	0.0206 (14)	0.0322 (17)	0.0009 (11)	−0.0006 (12)	−0.0041 (12)
C18A	0.0283 (9)	0.0332 (11)	0.0279 (9)	−0.0013 (7)	0.0020 (7)	0.0012 (8)
C19A	0.0283 (9)	0.0332 (11)	0.0279 (9)	−0.0013 (7)	0.0020 (7)	0.0012 (8)
C14B	0.0244 (14)	0.0200 (14)	0.0243 (15)	0.0000 (11)	0.0002 (11)	−0.0019 (11)
C15B	0.0283 (9)	0.0332 (11)	0.0279 (9)	−0.0013 (7)	0.0020 (7)	0.0012 (8)
C16B	0.0283 (9)	0.0332 (11)	0.0279 (9)	−0.0013 (7)	0.0020 (7)	0.0012 (8)
C17B	0.0247 (14)	0.0206 (14)	0.0322 (17)	0.0009 (11)	−0.0006 (12)	−0.0041 (12)
C18B	0.0283 (9)	0.0332 (11)	0.0279 (9)	−0.0013 (7)	0.0020 (7)	0.0012 (8)
C19B	0.0283 (9)	0.0332 (11)	0.0279 (9)	−0.0013 (7)	0.0020 (7)	0.0012 (8)
C20	0.0241 (15)	0.0390 (18)	0.0413 (19)	−0.0006 (13)	0.0007 (13)	0.0002 (14)
C21	0.068 (2)	0.052 (2)	0.0264 (18)	0.0205 (18)	0.0108 (16)	0.0108 (16)

S1—O2	1.491 (2)	C12—H12A	0.9900
S1—C21	1.740 (3)	C12—H12B	0.9900
S1—C1	1.762 (3)	C13—H13A	0.9900
O1—C7	1.374 (3)	C13—H13B	0.9900
O1—C8	1.381 (3)	C14A—C19A	1.390 (4)
C1—C8	1.356 (4)	C14A—C15A	1.393 (3)
C1—C2	1.443 (4)	C15A—C16A	1.391 (3)
C2—C7	1.384 (4)	C15A—H15A	0.9500
C2—C3	1.397 (4)	C16A—C17A	1.389 (4)
C3—C4	1.388 (4)	C16A—H16A	0.9500
C3—H3	0.9500	C17A—C18A	1.384 (3)
C4—C5	1.403 (4)	C17A—C20	1.496 (4)
C4—C9	1.510 (4)	C18A—C19A	1.382 (3)
C5—C6	1.376 (4)	C18A—H18A	0.9500
C5—H5	0.9500	C19A—H19A	0.9500
C6—C7	1.381 (4)	C15B—C16B	1.392 (3)
C6—H6	0.9500	C15B—H15B	0.9500
C8—C14A	1.458 (4)	C16B—H16B	0.9500
C9—C13	1.528 (4)	C18B—C19B	1.383 (3)
C9—C10	1.529 (4)	C18B—H18B	0.9500
C9—H9	1.0000	C19B—H19B	0.9500
C10—C11	1.532 (4)	C20—H20A	0.9800
C10—H10A	0.9900	C20—H20B	0.9800
C10—H10B	0.9900	C20—H20C	0.9800
C11—C12	1.534 (5)	C21—H21A	0.9800
C11—H11A	0.9900	C21—H21B	0.9800
C11—H11B	0.9900	C21—H21C	0.9800
C12—C13	1.536 (4)
O2—S1—C21	107.08 (17)	C11—C12—C13	105.8 (2)
O2—S1—C1	105.74 (13)	C11—C12—H12A	110.6
C21—S1—C1	99.72 (14)	C13—C12—H12A	110.6
C7—O1—C8	106.4 (2)	C11—C12—H12B	110.6
C8—C1—C2	107.3 (2)	C13—C12—H12B	110.6
C8—C1—S1	127.5 (2)	H12A—C12—H12B	108.7
C2—C1—S1	124.6 (2)	C9—C13—C12	104.2 (2)
C7—C2—C3	119.1 (2)	C9—C13—H13A	110.9
C7—C2—C1	105.0 (2)	C12—C13—H13A	110.9
C3—C2—C1	135.8 (3)	C9—C13—H13B	110.9
C4—C3—C2	119.0 (2)	C12—C13—H13B	110.9
C4—C3—H3	120.5	H13A—C13—H13B	108.9
C2—C3—H3	120.5	C19A—C14A—C15A	118.2 (3)
C3—C4—C5	119.5 (3)	C19A—C14A—C8	121.0 (2)
C3—C4—C9	119.4 (2)	C15A—C14A—C8	120.8 (3)
C5—C4—C9	121.0 (2)	C16A—C15A—C14A	120.4 (3)
C6—C5—C4	122.5 (3)	C16A—C15A—H15A	119.8
C6—C5—H5	118.7	C14A—C15A—H15A	119.8
C4—C5—H5	118.7	C17A—C16A—C15A	121.2 (3)
C5—C6—C7	116.3 (3)	C17A—C16A—H16A	119.4
C5—C6—H6	121.9	C15A—C16A—H16A	119.4
C7—C6—H6	121.9	C18A—C17A—C16A	117.9 (3)
O1—C7—C6	125.7 (2)	C18A—C17A—C20	120.7 (3)
O1—C7—C2	110.8 (2)	C16A—C17A—C20	121.4 (3)
C6—C7—C2	123.5 (3)	C19A—C18A—C17A	121.4 (3)
C1—C8—O1	110.5 (2)	C19A—C18A—H18A	119.3
C1—C8—C14A	134.3 (3)	C17A—C18A—H18A	119.3
O1—C8—C14A	115.2 (2)	C18A—C19A—C14A	120.8 (3)
C4—C9—C13	116.3 (2)	C18A—C19A—H19A	119.6
C4—C9—C10	115.6 (2)	C14A—C19A—H19A	119.6
C13—C9—C10	101.7 (2)	C16B—C15B—H15B	121.4
C4—C9—H9	107.6	C15B—C16B—H16B	118.3
C13—C9—H9	107.6	C19B—C18B—H18B	119.9
C10—C9—H9	107.6	C18B—C19B—H19B	119.0
C9—C10—C11	103.4 (2)	C17A—C20—H20A	109.5
C9—C10—H10A	111.1	C17A—C20—H20B	109.5
C11—C10—H10A	111.1	H20A—C20—H20B	109.5
C9—C10—H10B	111.1	C17A—C20—H20C	109.5
C11—C10—H10B	111.1	H20A—C20—H20C	109.5
H10A—C10—H10B	109.0	H20B—C20—H20C	109.5
C10—C11—C12	105.8 (2)	S1—C21—H21A	109.5
C10—C11—H11A	110.6	S1—C21—H21B	109.5
C12—C11—H11A	110.6	H21A—C21—H21B	109.5
C10—C11—H11B	110.6	S1—C21—H21C	109.5
C12—C11—H11B	110.6	H21A—C21—H21C	109.5
H11A—C11—H11B	108.7	H21B—C21—H21C	109.5
O2—S1—C1—C8	133.7 (3)	C7—O1—C8—C1	−0.1 (3)
C21—S1—C1—C8	−115.4 (3)	C7—O1—C8—C14A	−179.9 (2)
O2—S1—C1—C2	−36.8 (3)	C3—C4—C9—C13	123.0 (3)
C21—S1—C1—C2	74.2 (3)	C5—C4—C9—C13	−57.6 (3)
C8—C1—C2—C7	0.4 (3)	C3—C4—C9—C10	−117.8 (3)
S1—C1—C2—C7	172.45 (19)	C5—C4—C9—C10	61.6 (3)
C8—C1—C2—C3	−179.4 (3)	C4—C9—C10—C11	−169.5 (2)
S1—C1—C2—C3	−7.3 (4)	C13—C9—C10—C11	−42.5 (3)
C7—C2—C3—C4	1.3 (4)	C9—C10—C11—C12	28.5 (3)
C1—C2—C3—C4	−179.0 (3)	C10—C11—C12—C13	−3.3 (3)
C2—C3—C4—C5	−0.4 (4)	C4—C9—C13—C12	167.1 (2)
C2—C3—C4—C9	179.1 (2)	C10—C9—C13—C12	40.5 (3)
C3—C4—C5—C6	−0.4 (4)	C11—C12—C13—C9	−23.1 (3)
C9—C4—C5—C6	−179.8 (2)	C1—C8—C14A—C19A	−160.3 (3)
C4—C5—C6—C7	0.2 (4)	O1—C8—C14A—C19A	19.4 (4)
C8—O1—C7—C6	−178.8 (2)	C1—C8—C14A—C15A	21.6 (4)
C8—O1—C7—C2	0.3 (3)	O1—C8—C14A—C15A	−158.7 (3)
C5—C6—C7—O1	179.7 (2)	C19A—C14A—C15A—C16A	3.6 (4)
C5—C6—C7—C2	0.7 (4)	C8—C14A—C15A—C16A	−178.2 (3)
C3—C2—C7—O1	179.4 (2)	C14A—C15A—C16A—C17A	−2.1 (5)
C1—C2—C7—O1	−0.4 (3)	C15A—C16A—C17A—C18A	−0.7 (5)
C3—C2—C7—C6	−1.5 (4)	C15A—C16A—C17A—C20	−179.1 (3)
C1—C2—C7—C6	178.7 (2)	C16A—C17A—C18A—C19A	2.0 (5)
C2—C1—C8—O1	−0.2 (3)	C20—C17A—C18A—C19A	−179.6 (3)
S1—C1—C8—O1	−171.98 (18)	C17A—C18A—C19A—C14A	−0.4 (5)
C2—C1—C8—C14A	179.6 (3)	C15A—C14A—C19A—C18A	−2.4 (5)
S1—C1—C8—C14A	7.8 (4)	C8—C14A—C19A—C18A	179.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···Cgi	0.98	2.78	3.665 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯Cg i	0.98	2.78	3.665 (2)	150

Symmetry code: (i) .